data_2a _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonyj01 _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 Cl N Rh' _chemical_formula_sum 'C20 H27 Cl N Rh' _chemical_formula_weight 419.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5294(10) _cell_length_b 8.7262(11) _cell_length_c 15.273(2) _cell_angle_alpha 90.179(2) _cell_angle_beta 95.679(2) _cell_angle_gamma 115.261(2) _cell_volume 901.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3774 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 37.65 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7492 _exptl_absorpt_correction_T_max 0.8619 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32444 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 37.03 _reflns_number_total 9079 _reflns_number_gt 7821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.2417P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9079 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.208218(17) 0.105007(15) 0.289687(7) 0.02163(4) Uani 1 1 d . . . Cl1 Cl 0.16511(7) -0.15807(5) 0.35758(3) 0.02907(8) Uani 1 1 d . . . N1 N 0.4971(2) 0.23125(19) 0.35300(9) 0.0247(2) Uani 1 1 d . . . C1 C 0.3626(2) 0.0403(2) 0.19841(10) 0.0254(3) Uani 1 1 d . . . H1A H 0.4486 -0.0031 0.2340 0.030 Uiso 1 1 calc R . . C2 C 0.4989(2) 0.1979(2) 0.16083(11) 0.0261(3) Uani 1 1 d . . . C3 C 0.4986(3) 0.2215(3) 0.06984(11) 0.0314(3) Uani 1 1 d . . . H3A H 0.4045 0.1346 0.0299 0.038 Uiso 1 1 calc R . . C4 C 0.6335(3) 0.3699(3) 0.03712(13) 0.0359(4) Uani 1 1 d . . . H4A H 0.6277 0.3842 -0.0246 0.043 Uiso 1 1 calc R . . C5 C 0.7764(3) 0.4969(3) 0.09375(14) 0.0371(4) Uani 1 1 d . . . H5A H 0.8690 0.5974 0.0711 0.045 Uiso 1 1 calc R . . C6 C 0.7826(3) 0.4754(3) 0.18412(13) 0.0323(3) Uani 1 1 d . . . H6A H 0.8827 0.5598 0.2233 0.039 Uiso 1 1 calc R . . C7 C 0.6420(2) 0.3300(2) 0.21745(11) 0.0266(3) Uani 1 1 d . . . C8 C 0.6475(2) 0.3192(2) 0.31287(11) 0.0269(3) Uani 1 1 d . . . H8A H 0.7704 0.3811 0.3475 0.032 Uiso 1 1 calc R . . C9 C 0.5267(3) 0.2240(3) 0.44861(11) 0.0300(3) Uani 1 1 d . . . H9A H 0.6679 0.2837 0.4691 0.045 Uiso 1 1 calc R . . H9B H 0.4772 0.1053 0.4644 0.045 Uiso 1 1 calc R . . H9C H 0.4548 0.2782 0.4764 0.045 Uiso 1 1 calc R . . C10 C -0.0911(2) 0.0499(2) 0.23761(11) 0.0259(3) Uani 1 1 d . . . C11 C -0.0750(2) 0.0966(2) 0.33045(10) 0.0252(3) Uani 1 1 d . . . C12 C 0.0717(2) 0.2630(2) 0.34666(12) 0.0281(3) Uani 1 1 d . . . C13 C 0.1516(3) 0.3226(2) 0.26390(13) 0.0310(3) Uani 1 1 d . . . C14 C 0.0391(3) 0.1943(2) 0.19634(11) 0.0295(3) Uani 1 1 d . . . C15 C -0.2417(3) -0.1133(3) 0.19217(15) 0.0386(4) Uani 1 1 d . . . H15A H -0.3659 -0.1039 0.1764 0.058 Uiso 1 1 calc R . . H15B H -0.2643 -0.2064 0.2318 0.058 Uiso 1 1 calc R . . H15C H -0.1931 -0.1360 0.1387 0.058 Uiso 1 1 calc R . . C16 C -0.1976(3) -0.0179(3) 0.39446(13) 0.0349(4) Uani 1 1 d . . . H16A H -0.3359 -0.0388 0.3796 0.052 Uiso 1 1 calc R . . H16B H -0.1511 0.0353 0.4540 0.052 Uiso 1 1 calc R . . H16C H -0.1866 -0.1257 0.3921 0.052 Uiso 1 1 calc R . . C17 C 0.1348(3) 0.3691(3) 0.43128(15) 0.0414(5) Uani 1 1 d . . . H17A H 0.0929 0.4610 0.4259 0.062 Uiso 1 1 calc R . . H17B H 0.2790 0.4174 0.4438 0.062 Uiso 1 1 calc R . . H17C H 0.0738 0.2982 0.4794 0.062 Uiso 1 1 calc R . . C18 C 0.3034(3) 0.4976(3) 0.2508(2) 0.0474(6) Uani 1 1 d . . . H18A H 0.2399 0.5749 0.2444 0.071 Uiso 1 1 calc R . . H18B H 0.3657 0.4966 0.1976 0.071 Uiso 1 1 calc R . . H18C H 0.4041 0.5360 0.3019 0.071 Uiso 1 1 calc R . . C19 C 0.0461(4) 0.2140(4) 0.09952(13) 0.0437(5) Uani 1 1 d . . . H19A H -0.0452 0.2615 0.0770 0.066 Uiso 1 1 calc R . . H19B H 0.0074 0.1029 0.0698 0.066 Uiso 1 1 calc R . . H19C H 0.1806 0.2904 0.0881 0.066 Uiso 1 1 calc R . . C20 C 0.2270(3) -0.1040(3) 0.13484(13) 0.0342(4) Uani 1 1 d . . . H20A H 0.3059 -0.1384 0.0989 0.051 Uiso 1 1 calc R . . H20B H 0.1417 -0.0672 0.0965 0.051 Uiso 1 1 calc R . . H20C H 0.1452 -0.2003 0.1678 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.02478(6) 0.02560(6) 0.01901(5) -0.00158(4) -0.00115(4) 0.01586(4) Cl1 0.03806(19) 0.03035(18) 0.02546(16) 0.00336(13) 0.00319(14) 0.02109(16) N1 0.0286(6) 0.0294(6) 0.0207(5) -0.0031(5) -0.0032(4) 0.0181(5) C1 0.0311(7) 0.0293(7) 0.0211(6) -0.0015(5) 0.0010(5) 0.0186(6) C2 0.0301(7) 0.0316(7) 0.0228(6) 0.0002(5) 0.0019(5) 0.0194(6) C3 0.0379(8) 0.0385(9) 0.0232(7) 0.0006(6) 0.0030(6) 0.0215(7) C4 0.0457(10) 0.0427(10) 0.0262(7) 0.0068(7) 0.0076(7) 0.0248(9) C5 0.0429(10) 0.0373(9) 0.0355(9) 0.0077(7) 0.0097(8) 0.0200(8) C6 0.0311(8) 0.0328(8) 0.0353(8) 0.0013(7) 0.0041(6) 0.0157(7) C7 0.0272(7) 0.0307(7) 0.0263(7) 0.0005(6) 0.0008(5) 0.0170(6) C8 0.0277(7) 0.0307(7) 0.0265(7) -0.0022(6) -0.0022(5) 0.0176(6) C9 0.0351(8) 0.0391(9) 0.0205(6) -0.0028(6) -0.0040(6) 0.0217(7) C10 0.0267(6) 0.0308(7) 0.0239(6) -0.0060(5) -0.0039(5) 0.0174(6) C11 0.0267(6) 0.0300(7) 0.0239(6) -0.0024(5) -0.0005(5) 0.0177(6) C12 0.0278(7) 0.0318(8) 0.0296(7) -0.0080(6) -0.0040(5) 0.0191(6) C13 0.0278(7) 0.0304(8) 0.0412(9) 0.0049(7) 0.0029(6) 0.0188(6) C14 0.0348(8) 0.0399(9) 0.0251(7) 0.0050(6) 0.0020(6) 0.0270(7) C15 0.0298(8) 0.0429(10) 0.0443(10) -0.0201(8) -0.0090(7) 0.0197(8) C16 0.0336(8) 0.0457(10) 0.0321(8) 0.0063(7) 0.0079(7) 0.0225(8) C17 0.0399(9) 0.0476(11) 0.0432(10) -0.0239(9) -0.0137(8) 0.0290(9) C18 0.0368(10) 0.0309(9) 0.0802(18) 0.0142(10) 0.0111(10) 0.0189(8) C19 0.0565(12) 0.0682(15) 0.0278(8) 0.0151(9) 0.0076(8) 0.0463(12) C20 0.0372(9) 0.0335(9) 0.0337(8) -0.0051(7) -0.0016(7) 0.0179(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 N1 2.1003(14) . ? Rh1 C1 2.1185(16) . ? Rh1 C13 2.1455(17) . ? Rh1 C10 2.1587(16) . ? Rh1 C14 2.1809(16) . ? Rh1 C11 2.2517(16) . ? Rh1 C12 2.2572(16) . ? Rh1 Cl1 2.4282(5) . ? N1 C8 1.283(2) . ? N1 C9 1.461(2) . ? C1 C2 1.480(2) . ? C1 C20 1.507(2) . ? C1 H1A 1.0000 . ? C2 C3 1.405(2) . ? C2 C7 1.410(2) . ? C3 C4 1.393(3) . ? C3 H3A 0.9500 . ? C4 C5 1.388(3) . ? C4 H4A 0.9500 . ? C5 C6 1.392(3) . ? C5 H5A 0.9500 . ? C6 C7 1.398(3) . ? C6 H6A 0.9500 . ? C7 C8 1.458(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C14 1.421(3) . ? C10 C11 1.453(2) . ? C10 C15 1.502(3) . ? C11 C12 1.402(2) . ? C11 C16 1.484(3) . ? C12 C13 1.455(3) . ? C12 C17 1.499(2) . ? C13 C14 1.430(3) . ? C13 C18 1.496(3) . ? C14 C19 1.493(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Rh1 C1 80.55(6) . . ? N1 Rh1 C13 98.39(6) . . ? C1 Rh1 C13 117.06(7) . . ? N1 Rh1 C10 161.64(6) . . ? C1 Rh1 C10 112.72(6) . . ? C13 Rh1 C10 64.65(7) . . ? N1 Rh1 C14 130.63(7) . . ? C1 Rh1 C14 97.92(6) . . ? C13 Rh1 C14 38.59(7) . . ? C10 Rh1 C14 38.22(7) . . ? N1 Rh1 C11 129.03(6) . . ? C1 Rh1 C11 150.39(6) . . ? C13 Rh1 C11 63.19(7) . . ? C10 Rh1 C11 38.40(6) . . ? C14 Rh1 C11 63.18(6) . . ? N1 Rh1 C12 99.32(6) . . ? C1 Rh1 C12 155.51(7) . . ? C13 Rh1 C12 38.49(7) . . ? C10 Rh1 C12 63.23(6) . . ? C14 Rh1 C12 63.41(6) . . ? C11 Rh1 C12 36.22(6) . . ? N1 Rh1 Cl1 91.55(4) . . ? C1 Rh1 Cl1 85.98(5) . . ? C13 Rh1 Cl1 156.04(5) . . ? C10 Rh1 Cl1 101.70(5) . . ? C14 Rh1 Cl1 137.78(5) . . ? C11 Rh1 Cl1 93.67(4) . . ? C12 Rh1 Cl1 118.44(5) . . ? C8 N1 C9 118.25(14) . . ? C8 N1 Rh1 123.70(11) . . ? C9 N1 Rh1 118.01(11) . . ? C2 C1 C20 117.48(15) . . ? C2 C1 Rh1 108.51(11) . . ? C20 C1 Rh1 112.48(12) . . ? C2 C1 H1A 105.8 . . ? C20 C1 H1A 105.8 . . ? Rh1 C1 H1A 105.8 . . ? C3 C2 C7 117.26(17) . . ? C3 C2 C1 123.14(16) . . ? C7 C2 C1 119.55(15) . . ? C4 C3 C2 121.28(18) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C5 C4 C3 120.64(18) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.27(19) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C5 C6 C7 120.23(18) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C2 121.20(16) . . ? C6 C7 C8 117.91(16) . . ? C2 C7 C8 120.89(16) . . ? N1 C8 C7 124.17(15) . . ? N1 C8 H8A 117.9 . . ? C7 C8 H8A 117.9 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C14 C10 C11 107.82(15) . . ? C14 C10 C15 126.42(17) . . ? C11 C10 C15 125.14(17) . . ? C14 C10 Rh1 71.74(9) . . ? C11 C10 Rh1 74.26(9) . . ? C15 C10 Rh1 126.78(12) . . ? C12 C11 C10 108.45(15) . . ? C12 C11 C16 127.73(16) . . ? C10 C11 C16 123.82(16) . . ? C12 C11 Rh1 72.10(9) . . ? C10 C11 Rh1 67.34(9) . . ? C16 C11 Rh1 126.26(12) . . ? C11 C12 C13 107.61(15) . . ? C11 C12 C17 128.16(19) . . ? C13 C12 C17 124.18(18) . . ? C11 C12 Rh1 71.68(9) . . ? C13 C12 Rh1 66.60(9) . . ? C17 C12 Rh1 128.80(12) . . ? C14 C13 C12 107.95(16) . . ? C14 C13 C18 126.4(2) . . ? C12 C13 C18 125.0(2) . . ? C14 C13 Rh1 72.05(10) . . ? C12 C13 Rh1 74.91(10) . . ? C18 C13 Rh1 125.91(13) . . ? C10 C14 C13 107.68(15) . . ? C10 C14 C19 126.19(19) . . ? C13 C14 C19 126.0(2) . . ? C10 C14 Rh1 70.04(9) . . ? C13 C14 Rh1 69.36(9) . . ? C19 C14 Rh1 129.62(13) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 C20 H20A 109.5 . . ? C1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C8 43.73(14) . . . . ? C13 Rh1 N1 C8 -72.48(15) . . . . ? C10 Rh1 N1 C8 -94.1(2) . . . . ? C14 Rh1 N1 C8 -48.63(16) . . . . ? C11 Rh1 N1 C8 -134.62(13) . . . . ? C12 Rh1 N1 C8 -111.45(14) . . . . ? Cl1 Rh1 N1 C8 129.39(13) . . . . ? C1 Rh1 N1 C9 -138.85(13) . . . . ? C13 Rh1 N1 C9 104.94(13) . . . . ? C10 Rh1 N1 C9 83.3(2) . . . . ? C14 Rh1 N1 C9 128.80(12) . . . . ? C11 Rh1 N1 C9 42.80(15) . . . . ? C12 Rh1 N1 C9 65.98(13) . . . . ? Cl1 Rh1 N1 C9 -53.18(12) . . . . ? N1 Rh1 C1 C2 -63.56(11) . . . . ? C13 Rh1 C1 C2 31.08(13) . . . . ? C10 Rh1 C1 C2 103.19(11) . . . . ? C14 Rh1 C1 C2 66.48(12) . . . . ? C11 Rh1 C1 C2 113.84(14) . . . . ? C12 Rh1 C1 C2 28.2(2) . . . . ? Cl1 Rh1 C1 C2 -155.81(10) . . . . ? N1 Rh1 C1 C20 164.74(13) . . . . ? C13 Rh1 C1 C20 -100.61(13) . . . . ? C10 Rh1 C1 C20 -28.51(14) . . . . ? C14 Rh1 C1 C20 -65.22(13) . . . . ? C11 Rh1 C1 C20 -17.9(2) . . . . ? C12 Rh1 C1 C20 -103.50(18) . . . . ? Cl1 Rh1 C1 C20 72.50(12) . . . . ? C20 C1 C2 C3 3.9(2) . . . . ? Rh1 C1 C2 C3 -125.02(15) . . . . ? C20 C1 C2 C7 -173.67(15) . . . . ? Rh1 C1 C2 C7 57.38(17) . . . . ? C7 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C4 -178.01(17) . . . . ? C2 C3 C4 C5 1.9(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C4 C5 C6 C7 -2.2(3) . . . . ? C5 C6 C7 C2 3.8(3) . . . . ? C5 C6 C7 C8 -176.06(17) . . . . ? C3 C2 C7 C6 -2.5(2) . . . . ? C1 C2 C7 C6 175.26(15) . . . . ? C3 C2 C7 C8 177.37(15) . . . . ? C1 C2 C7 C8 -4.9(2) . . . . ? C9 N1 C8 C7 176.39(15) . . . . ? Rh1 N1 C8 C7 -6.2(2) . . . . ? C6 C7 C8 N1 153.94(17) . . . . ? C2 C7 C8 N1 -25.9(3) . . . . ? N1 Rh1 C10 C14 61.0(2) . . . . ? C1 Rh1 C10 C14 -73.13(11) . . . . ? C13 Rh1 C10 C14 37.21(10) . . . . ? C11 Rh1 C10 C14 115.33(14) . . . . ? C12 Rh1 C10 C14 80.23(11) . . . . ? Cl1 Rh1 C10 C14 -163.64(9) . . . . ? N1 Rh1 C10 C11 -54.3(2) . . . . ? C1 Rh1 C10 C11 171.54(10) . . . . ? C13 Rh1 C10 C11 -78.13(11) . . . . ? C14 Rh1 C10 C11 -115.33(14) . . . . ? C12 Rh1 C10 C11 -35.10(10) . . . . ? Cl1 Rh1 C10 C11 81.03(9) . . . . ? N1 Rh1 C10 C15 -176.74(17) . . . . ? C1 Rh1 C10 C15 49.14(19) . . . . ? C13 Rh1 C10 C15 159.47(19) . . . . ? C14 Rh1 C10 C15 122.3(2) . . . . ? C11 Rh1 C10 C15 -122.4(2) . . . . ? C12 Rh1 C10 C15 -157.50(19) . . . . ? Cl1 Rh1 C10 C15 -41.38(17) . . . . ? C14 C10 C11 C12 -3.73(17) . . . . ? C15 C10 C11 C12 -175.14(16) . . . . ? Rh1 C10 C11 C12 60.63(11) . . . . ? C14 C10 C11 C16 176.18(15) . . . . ? C15 C10 C11 C16 4.8(3) . . . . ? Rh1 C10 C11 C16 -119.45(15) . . . . ? C14 C10 C11 Rh1 -64.37(11) . . . . ? C15 C10 C11 Rh1 124.23(17) . . . . ? N1 Rh1 C11 C12 41.08(12) . . . . ? C1 Rh1 C11 C12 -135.62(13) . . . . ? C13 Rh1 C11 C12 -37.43(10) . . . . ? C10 Rh1 C11 C12 -119.69(14) . . . . ? C14 Rh1 C11 C12 -80.89(11) . . . . ? Cl1 Rh1 C11 C12 136.06(9) . . . . ? N1 Rh1 C11 C10 160.77(10) . . . . ? C1 Rh1 C11 C10 -15.94(18) . . . . ? C13 Rh1 C11 C10 82.26(11) . . . . ? C14 Rh1 C11 C10 38.80(10) . . . . ? C12 Rh1 C11 C10 119.69(14) . . . . ? Cl1 Rh1 C11 C10 -104.25(9) . . . . ? N1 Rh1 C11 C16 -83.02(17) . . . . ? C1 Rh1 C11 C16 100.28(18) . . . . ? C13 Rh1 C11 C16 -161.52(17) . . . . ? C10 Rh1 C11 C16 116.21(19) . . . . ? C14 Rh1 C11 C16 155.02(17) . . . . ? C12 Rh1 C11 C16 -124.10(19) . . . . ? Cl1 Rh1 C11 C16 11.96(15) . . . . ? C10 C11 C12 C13 -0.64(17) . . . . ? C16 C11 C12 C13 179.44(16) . . . . ? Rh1 C11 C12 C13 57.04(11) . . . . ? C10 C11 C12 C17 176.92(16) . . . . ? C16 C11 C12 C17 -3.0(3) . . . . ? Rh1 C11 C12 C17 -125.40(17) . . . . ? C10 C11 C12 Rh1 -57.68(11) . . . . ? C16 C11 C12 Rh1 122.41(17) . . . . ? N1 Rh1 C12 C11 -148.85(10) . . . . ? C1 Rh1 C12 C11 123.51(15) . . . . ? C13 Rh1 C12 C11 119.38(14) . . . . ? C10 Rh1 C12 C11 37.19(10) . . . . ? C14 Rh1 C12 C11 80.17(11) . . . . ? Cl1 Rh1 C12 C11 -51.95(10) . . . . ? N1 Rh1 C12 C13 91.78(10) . . . . ? C1 Rh1 C12 C13 4.13(19) . . . . ? C10 Rh1 C12 C13 -82.19(11) . . . . ? C14 Rh1 C12 C13 -39.20(11) . . . . ? C11 Rh1 C12 C13 -119.38(14) . . . . ? Cl1 Rh1 C12 C13 -171.33(9) . . . . ? N1 Rh1 C12 C17 -24.2(2) . . . . ? C1 Rh1 C12 C17 -111.8(2) . . . . ? C13 Rh1 C12 C17 -116.0(2) . . . . ? C10 Rh1 C12 C17 161.9(2) . . . . ? C14 Rh1 C12 C17 -155.2(2) . . . . ? C11 Rh1 C12 C17 124.7(2) . . . . ? Cl1 Rh1 C12 C17 72.7(2) . . . . ? C11 C12 C13 C14 4.76(18) . . . . ? C17 C12 C13 C14 -172.92(15) . . . . ? Rh1 C12 C13 C14 64.98(11) . . . . ? C11 C12 C13 C18 176.22(16) . . . . ? C17 C12 C13 C18 -1.5(3) . . . . ? Rh1 C12 C13 C18 -123.57(17) . . . . ? C11 C12 C13 Rh1 -60.22(11) . . . . ? C17 C12 C13 Rh1 122.10(16) . . . . ? N1 Rh1 C13 C14 150.53(10) . . . . ? C1 Rh1 C13 C14 66.90(12) . . . . ? C10 Rh1 C13 C14 -36.85(10) . . . . ? C11 Rh1 C13 C14 -79.78(11) . . . . ? C12 Rh1 C13 C14 -115.02(14) . . . . ? Cl1 Rh1 C13 C14 -95.96(16) . . . . ? N1 Rh1 C13 C12 -94.46(10) . . . . ? C1 Rh1 C13 C12 -178.08(9) . . . . ? C10 Rh1 C13 C12 78.16(10) . . . . ? C14 Rh1 C13 C12 115.02(14) . . . . ? C11 Rh1 C13 C12 35.24(9) . . . . ? Cl1 Rh1 C13 C12 19.05(19) . . . . ? N1 Rh1 C13 C18 28.1(2) . . . . ? C1 Rh1 C13 C18 -55.5(2) . . . . ? C10 Rh1 C13 C18 -159.2(2) . . . . ? C14 Rh1 C13 C18 -122.4(2) . . . . ? C11 Rh1 C13 C18 157.8(2) . . . . ? C12 Rh1 C13 C18 122.6(2) . . . . ? Cl1 Rh1 C13 C18 141.65(17) . . . . ? C11 C10 C14 C13 6.66(18) . . . . ? C15 C10 C14 C13 177.92(16) . . . . ? Rh1 C10 C14 C13 -59.38(11) . . . . ? C11 C10 C14 C19 -168.86(16) . . . . ? C15 C10 C14 C19 2.4(3) . . . . ? Rh1 C10 C14 C19 125.10(17) . . . . ? C11 C10 C14 Rh1 66.04(10) . . . . ? C15 C10 C14 Rh1 -122.69(17) . . . . ? C12 C13 C14 C10 -7.07(18) . . . . ? C18 C13 C14 C10 -178.37(16) . . . . ? Rh1 C13 C14 C10 59.81(11) . . . . ? C12 C13 C14 C19 168.46(16) . . . . ? C18 C13 C14 C19 -2.8(3) . . . . ? Rh1 C13 C14 C19 -124.66(17) . . . . ? C12 C13 C14 Rh1 -66.88(11) . . . . ? C18 C13 C14 Rh1 121.81(18) . . . . ? N1 Rh1 C14 C10 -158.72(9) . . . . ? C1 Rh1 C14 C10 116.97(10) . . . . ? C13 Rh1 C14 C10 -118.82(14) . . . . ? C11 Rh1 C14 C10 -38.99(9) . . . . ? C12 Rh1 C14 C10 -79.71(10) . . . . ? Cl1 Rh1 C14 C10 24.23(13) . . . . ? N1 Rh1 C14 C13 -39.90(13) . . . . ? C1 Rh1 C14 C13 -124.21(11) . . . . ? C10 Rh1 C14 C13 118.82(14) . . . . ? C11 Rh1 C14 C13 79.83(11) . . . . ? C12 Rh1 C14 C13 39.11(10) . . . . ? Cl1 Rh1 C14 C13 143.05(9) . . . . ? N1 Rh1 C14 C19 80.3(2) . . . . ? C1 Rh1 C14 C19 -4.0(2) . . . . ? C13 Rh1 C14 C19 120.2(3) . . . . ? C10 Rh1 C14 C19 -121.0(2) . . . . ? C11 Rh1 C14 C19 -160.0(2) . . . . ? C12 Rh1 C14 C19 159.3(2) . . . . ? Cl1 Rh1 C14 C19 -96.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 37.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.249 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.116 _publ_section_references ; Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2009). APEX2 V2009.9-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _vrf_PLAT094_jonyj01 ; PROBLEM: _B Ratio of Maximum / Minimum Residual Density .... 6.24 RESPONSE: The maximum residual density peak of 2.25 electrons per \%A^3^, located at 0.49 \%A from H20C, has no chemical meaning. ; #===end data_4a _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll58 _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 Cl N Rh' _chemical_formula_sum 'C23 H27 Cl N Rh' _chemical_formula_weight 455.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7511(9) _cell_length_b 7.2007(4) _cell_length_c 17.3962(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.321(1) _cell_angle_gamma 90.00 _cell_volume 1967.45(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3774 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 37.92 _exptl_crystal_description block _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7651 _exptl_absorpt_correction_T_max 0.8715 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46481 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 37.78 _reflns_number_total 10480 _reflns_number_gt 8936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.3145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10480 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.286398(5) -0.038956(12) 0.455082(5) 0.01042(3) Uani 1 1 d . . . Cl1 Cl 0.387006(19) 0.13014(4) 0.539777(17) 0.01725(5) Uani 1 1 d . . . N1 N 0.33869(6) 0.07530(14) 0.35829(6) 0.01182(15) Uani 1 1 d . . . C1 C 0.21690(8) 0.21185(17) 0.44659(7) 0.01424(19) Uani 1 1 d . . . H1 H 0.2594 0.3125 0.4396 0.017 Uiso 1 1 calc R . . C2 C 0.16248(7) 0.20156(17) 0.37352(7) 0.01471(19) Uani 1 1 d . . . C3 C 0.07351(8) 0.2203(2) 0.37156(8) 0.0218(2) Uani 1 1 d . . . H3 H 0.0476 0.2400 0.4185 0.026 Uiso 1 1 calc R . . C4 C 0.02227(9) 0.2108(3) 0.30292(9) 0.0273(3) Uani 1 1 d . . . H4 H -0.0378 0.2223 0.3036 0.033 Uiso 1 1 calc R . . C5 C 0.05854(9) 0.1845(2) 0.23381(9) 0.0265(3) Uani 1 1 d . . . H5 H 0.0237 0.1781 0.1869 0.032 Uiso 1 1 calc R . . C6 C 0.14645(8) 0.1675(2) 0.23375(8) 0.0194(2) Uani 1 1 d . . . H6 H 0.1715 0.1505 0.1863 0.023 Uiso 1 1 calc R . . C7 C 0.19867(7) 0.17511(17) 0.30229(7) 0.01430(19) Uani 1 1 d . . . C8 C 0.29165(7) 0.15410(16) 0.29828(6) 0.01244(18) Uani 1 1 d . . . C9 C 0.33139(8) 0.21391(18) 0.23333(7) 0.0161(2) Uani 1 1 d . . . H9 H 0.2987 0.2722 0.1920 0.019 Uiso 1 1 calc R . . C10 C 0.41802(8) 0.18870(19) 0.22893(7) 0.0175(2) Uani 1 1 d . . . H10 H 0.4448 0.2252 0.1842 0.021 Uiso 1 1 calc R . . C11 C 0.46493(8) 0.10942(19) 0.29093(7) 0.0164(2) Uani 1 1 d . . . H11 H 0.5246 0.0916 0.2897 0.020 Uiso 1 1 calc R . . C12 C 0.42341(8) 0.05659(17) 0.35477(7) 0.01399(19) Uani 1 1 d . . . H12 H 0.4559 0.0051 0.3978 0.017 Uiso 1 1 calc R . . C13 C 0.22583(8) -0.28106(17) 0.40394(7) 0.01436(19) Uani 1 1 d . . . C14 C 0.18366(8) -0.23530(17) 0.47144(8) 0.0164(2) Uani 1 1 d . . . C15 C 0.24586(9) -0.24211(18) 0.53555(7) 0.0176(2) Uani 1 1 d . . . C16 C 0.32488(8) -0.31311(17) 0.50797(7) 0.0160(2) Uani 1 1 d . . . C17 C 0.31280(8) -0.33621(16) 0.42812(7) 0.01411(19) Uani 1 1 d . . . C18 C 0.18385(10) -0.2974(2) 0.32404(8) 0.0222(2) Uani 1 1 d . . . H18A H 0.1588 -0.4214 0.3170 0.033 Uiso 1 1 calc R . . H18B H 0.2263 -0.2781 0.2864 0.033 Uiso 1 1 calc R . . H18C H 0.1390 -0.2034 0.3165 0.033 Uiso 1 1 calc R . . C19 C 0.09064(9) -0.1992(2) 0.47367(10) 0.0266(3) Uani 1 1 d . . . H19A H 0.0598 -0.3176 0.4723 0.040 Uiso 1 1 calc R . . H19B H 0.0707 -0.1238 0.4290 0.040 Uiso 1 1 calc R . . H19C H 0.0803 -0.1326 0.5212 0.040 Uiso 1 1 calc R . . C20 C 0.23137(12) -0.2092(2) 0.61836(8) 0.0294(3) Uani 1 1 d . . . H20A H 0.2203 -0.3279 0.6433 0.044 Uiso 1 1 calc R . . H20B H 0.1823 -0.1268 0.6218 0.044 Uiso 1 1 calc R . . H20C H 0.2820 -0.1513 0.6443 0.044 Uiso 1 1 calc R . . C21 C 0.40466(10) -0.3534(2) 0.55672(9) 0.0254(3) Uani 1 1 d . . . H21A H 0.4079 -0.4866 0.5681 0.038 Uiso 1 1 calc R . . H21B H 0.4046 -0.2835 0.6051 0.038 Uiso 1 1 calc R . . H21C H 0.4539 -0.3165 0.5291 0.038 Uiso 1 1 calc R . . C22 C 0.37811(9) -0.4022(2) 0.37648(9) 0.0226(3) Uani 1 1 d . . . H22A H 0.3743 -0.5375 0.3711 0.034 Uiso 1 1 calc R . . H22B H 0.4350 -0.3682 0.3988 0.034 Uiso 1 1 calc R . . H22C H 0.3679 -0.3442 0.3257 0.034 Uiso 1 1 calc R . . C23 C 0.17374(9) 0.2601(2) 0.51895(8) 0.0208(2) Uani 1 1 d . . . H23A H 0.1460 0.3816 0.5125 0.031 Uiso 1 1 calc R . . H23B H 0.2163 0.2646 0.5630 0.031 Uiso 1 1 calc R . . H23C H 0.1309 0.1655 0.5282 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01168(4) 0.01104(4) 0.00860(4) 0.00045(3) 0.00114(3) -0.00047(3) Cl1 0.01972(12) 0.01700(12) 0.01440(11) -0.00259(9) -0.00282(9) -0.00157(10) N1 0.0125(4) 0.0123(4) 0.0108(4) 0.0002(3) 0.0013(3) -0.0003(3) C1 0.0156(5) 0.0141(4) 0.0133(4) 0.0002(4) 0.0031(4) 0.0015(4) C2 0.0134(4) 0.0158(5) 0.0150(5) 0.0026(4) 0.0022(4) 0.0018(4) C3 0.0146(5) 0.0296(7) 0.0217(6) 0.0063(5) 0.0040(4) 0.0042(5) C4 0.0137(5) 0.0401(8) 0.0277(7) 0.0077(6) -0.0009(5) 0.0027(5) C5 0.0177(6) 0.0377(8) 0.0229(6) 0.0049(6) -0.0054(5) 0.0018(5) C6 0.0179(5) 0.0248(6) 0.0151(5) 0.0032(4) -0.0015(4) 0.0010(4) C7 0.0137(4) 0.0160(5) 0.0131(4) 0.0026(4) -0.0002(3) 0.0002(4) C8 0.0136(4) 0.0132(4) 0.0105(4) 0.0007(3) 0.0007(3) 0.0001(3) C9 0.0183(5) 0.0187(5) 0.0113(4) 0.0027(4) 0.0018(4) -0.0013(4) C10 0.0189(5) 0.0203(5) 0.0142(5) 0.0011(4) 0.0059(4) -0.0025(4) C11 0.0141(5) 0.0189(5) 0.0167(5) -0.0001(4) 0.0049(4) -0.0016(4) C12 0.0127(4) 0.0157(5) 0.0137(5) 0.0005(4) 0.0015(4) -0.0004(4) C13 0.0157(5) 0.0136(4) 0.0136(4) 0.0003(4) 0.0001(4) -0.0023(4) C14 0.0157(5) 0.0149(5) 0.0191(5) 0.0015(4) 0.0049(4) -0.0026(4) C15 0.0253(6) 0.0157(5) 0.0121(5) 0.0025(4) 0.0044(4) -0.0037(4) C16 0.0194(5) 0.0127(4) 0.0154(5) 0.0029(4) -0.0024(4) -0.0017(4) C17 0.0149(4) 0.0122(4) 0.0152(5) -0.0008(4) 0.0011(4) -0.0011(3) C18 0.0276(6) 0.0210(6) 0.0168(5) -0.0014(4) -0.0069(5) -0.0044(5) C19 0.0167(5) 0.0246(6) 0.0396(8) 0.0021(6) 0.0103(5) -0.0020(5) C20 0.0500(10) 0.0255(7) 0.0139(5) 0.0018(5) 0.0101(6) -0.0063(7) C21 0.0291(7) 0.0186(6) 0.0263(7) 0.0054(5) -0.0120(5) -0.0006(5) C22 0.0214(6) 0.0176(5) 0.0299(7) -0.0052(5) 0.0093(5) 0.0001(5) C23 0.0247(6) 0.0215(6) 0.0169(5) -0.0015(4) 0.0069(4) 0.0047(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate ropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 N1 2.0974(10) . ? Rh1 C1 2.1112(12) . ? Rh1 C13 2.1478(12) . ? Rh1 C15 2.1545(12) . ? Rh1 C14 2.1836(12) . ? Rh1 C17 2.2369(12) . ? Rh1 C16 2.2421(12) . ? Rh1 Cl1 2.4110(3) . ? N1 C12 1.3472(15) . ? N1 C8 1.3581(15) . ? C1 C2 1.4805(17) . ? C1 C23 1.5156(17) . ? C1 H1 1.0000 . ? C2 C3 1.4057(17) . ? C2 C7 1.4153(17) . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.3902(19) . ? C5 H5 0.9500 . ? C6 C7 1.3976(17) . ? C6 H6 0.9500 . ? C7 C8 1.4793(16) . ? C8 C9 1.4001(16) . ? C9 C10 1.3844(18) . ? C9 H9 0.9500 . ? C10 C11 1.3838(19) . ? C10 H10 0.9500 . ? C11 C12 1.3838(17) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.4305(17) . ? C13 C17 1.4576(17) . ? C13 C18 1.4981(17) . ? C14 C15 1.4289(18) . ? C14 C19 1.4913(19) . ? C15 C16 1.4597(19) . ? C15 C20 1.4942(19) . ? C16 C17 1.3978(18) . ? C16 C21 1.4905(18) . ? C17 C22 1.4934(18) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Rh1 C1 80.86(4) . . ? N1 Rh1 C13 100.07(4) . . ? C1 Rh1 C13 116.97(5) . . ? N1 Rh1 C15 160.29(5) . . ? C1 Rh1 C15 116.67(5) . . ? C13 Rh1 C15 64.78(5) . . ? N1 Rh1 C14 134.29(4) . . ? C1 Rh1 C14 100.23(5) . . ? C13 Rh1 C14 38.56(5) . . ? C15 Rh1 C14 38.46(5) . . ? N1 Rh1 C17 96.69(4) . . ? C1 Rh1 C17 155.16(5) . . ? C13 Rh1 C17 38.76(4) . . ? C15 Rh1 C17 63.60(5) . . ? C14 Rh1 C17 63.84(5) . . ? N1 Rh1 C16 124.36(4) . . ? C1 Rh1 C16 154.77(5) . . ? C13 Rh1 C16 63.47(5) . . ? C15 Rh1 C16 38.71(5) . . ? C14 Rh1 C16 63.68(5) . . ? C17 Rh1 C16 36.37(5) . . ? N1 Rh1 Cl1 90.73(3) . . ? C1 Rh1 Cl1 85.65(3) . . ? C13 Rh1 Cl1 156.07(3) . . ? C15 Rh1 Cl1 99.16(4) . . ? C14 Rh1 Cl1 134.98(4) . . ? C17 Rh1 Cl1 119.17(3) . . ? C16 Rh1 Cl1 92.81(3) . . ? C12 N1 C8 119.45(10) . . ? C12 N1 Rh1 116.59(8) . . ? C8 N1 Rh1 123.81(8) . . ? C2 C1 C23 117.23(11) . . ? C2 C1 Rh1 106.31(8) . . ? C23 C1 Rh1 113.63(8) . . ? C2 C1 H1 106.3 . . ? C23 C1 H1 106.3 . . ? Rh1 C1 H1 106.3 . . ? C3 C2 C7 117.27(11) . . ? C3 C2 C1 121.85(11) . . ? C7 C2 C1 120.87(10) . . ? C4 C3 C2 121.92(13) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 120.14(13) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.32(13) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C7 121.20(13) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C2 120.15(11) . . ? C6 C7 C8 118.48(11) . . ? C2 C7 C8 121.37(10) . . ? N1 C8 C9 119.85(11) . . ? N1 C8 C7 119.42(10) . . ? C9 C8 C7 120.73(10) . . ? C10 C9 C8 120.45(11) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 118.79(11) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 C11 C10 118.82(11) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N1 C12 C11 122.59(11) . . ? N1 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C14 C13 C17 108.08(10) . . ? C14 C13 C18 125.44(11) . . ? C17 C13 C18 125.87(11) . . ? C14 C13 Rh1 72.07(7) . . ? C17 C13 Rh1 73.92(7) . . ? C18 C13 Rh1 126.81(9) . . ? C15 C14 C13 107.42(11) . . ? C15 C14 C19 127.08(12) . . ? C13 C14 C19 125.41(12) . . ? C15 C14 Rh1 69.67(7) . . ? C13 C14 Rh1 69.37(7) . . ? C19 C14 Rh1 129.04(10) . . ? C14 C15 C16 107.88(11) . . ? C14 C15 C20 126.97(13) . . ? C16 C15 C20 124.64(13) . . ? C14 C15 Rh1 71.87(7) . . ? C16 C15 Rh1 73.89(7) . . ? C20 C15 Rh1 126.37(10) . . ? C17 C16 C15 108.22(11) . . ? C17 C16 C21 126.02(13) . . ? C15 C16 C21 125.75(12) . . ? C17 C16 Rh1 71.61(7) . . ? C15 C16 Rh1 67.40(7) . . ? C21 C16 Rh1 126.51(9) . . ? C16 C17 C13 108.00(11) . . ? C16 C17 C22 125.97(12) . . ? C13 C17 C22 126.02(12) . . ? C16 C17 Rh1 72.02(7) . . ? C13 C17 Rh1 67.31(7) . . ? C22 C17 Rh1 125.31(9) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 C23 H23A 109.5 . . ? C1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C12 138.73(9) . . . . ? C13 Rh1 N1 C12 -105.29(9) . . . . ? C15 Rh1 N1 C12 -67.25(17) . . . . ? C14 Rh1 N1 C12 -125.86(9) . . . . ? C17 Rh1 N1 C12 -66.24(9) . . . . ? C16 Rh1 N1 C12 -40.65(10) . . . . ? Cl1 Rh1 N1 C12 53.25(8) . . . . ? C1 Rh1 N1 C8 -45.71(9) . . . . ? C13 Rh1 N1 C8 70.27(10) . . . . ? C15 Rh1 N1 C8 108.32(15) . . . . ? C14 Rh1 N1 C8 49.70(12) . . . . ? C17 Rh1 N1 C8 109.32(10) . . . . ? C16 Rh1 N1 C8 134.91(9) . . . . ? Cl1 Rh1 N1 C8 -131.19(9) . . . . ? N1 Rh1 C1 C2 65.83(8) . . . . ? C13 Rh1 C1 C2 -30.88(9) . . . . ? C15 Rh1 C1 C2 -104.66(8) . . . . ? C14 Rh1 C1 C2 -67.78(8) . . . . ? C17 Rh1 C1 C2 -20.36(15) . . . . ? C16 Rh1 C1 C2 -115.38(11) . . . . ? Cl1 Rh1 C1 C2 157.27(8) . . . . ? N1 Rh1 C1 C23 -163.74(10) . . . . ? C13 Rh1 C1 C23 99.55(10) . . . . ? C15 Rh1 C1 C23 25.77(11) . . . . ? C14 Rh1 C1 C23 62.66(10) . . . . ? C17 Rh1 C1 C23 110.07(12) . . . . ? C16 Rh1 C1 C23 15.05(17) . . . . ? Cl1 Rh1 C1 C23 -72.30(9) . . . . ? C23 C1 C2 C3 -5.17(18) . . . . ? Rh1 C1 C2 C3 123.18(12) . . . . ? C23 C1 C2 C7 173.84(12) . . . . ? Rh1 C1 C2 C7 -57.81(13) . . . . ? C7 C2 C3 C4 0.9(2) . . . . ? C1 C2 C3 C4 179.96(14) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C2 -0.4(2) . . . . ? C5 C6 C7 C8 179.35(13) . . . . ? C3 C2 C7 C6 -0.31(19) . . . . ? C1 C2 C7 C6 -179.37(12) . . . . ? C3 C2 C7 C8 179.96(12) . . . . ? C1 C2 C7 C8 0.90(18) . . . . ? C12 N1 C8 C9 0.39(17) . . . . ? Rh1 N1 C8 C9 -175.05(9) . . . . ? C12 N1 C8 C7 -179.82(11) . . . . ? Rh1 N1 C8 C7 4.74(15) . . . . ? C6 C7 C8 N1 -149.14(12) . . . . ? C2 C7 C8 N1 30.60(17) . . . . ? C6 C7 C8 C9 30.65(18) . . . . ? C2 C7 C8 C9 -149.62(12) . . . . ? N1 C8 C9 C10 1.77(19) . . . . ? C7 C8 C9 C10 -178.02(12) . . . . ? C8 C9 C10 C11 -2.2(2) . . . . ? C9 C10 C11 C12 0.62(19) . . . . ? C8 N1 C12 C11 -2.09(18) . . . . ? Rh1 N1 C12 C11 173.68(10) . . . . ? C10 C11 C12 N1 1.58(19) . . . . ? N1 Rh1 C13 C14 -156.21(7) . . . . ? C1 Rh1 C13 C14 -71.40(8) . . . . ? C15 Rh1 C13 C14 37.07(7) . . . . ? C17 Rh1 C13 C14 115.64(10) . . . . ? C16 Rh1 C13 C14 80.28(8) . . . . ? Cl1 Rh1 C13 C14 88.19(10) . . . . ? N1 Rh1 C13 C17 88.16(7) . . . . ? C1 Rh1 C13 C17 172.96(7) . . . . ? C15 Rh1 C13 C17 -78.56(8) . . . . ? C14 Rh1 C13 C17 -115.64(10) . . . . ? C16 Rh1 C13 C17 -35.35(7) . . . . ? Cl1 Rh1 C13 C17 -27.44(12) . . . . ? N1 Rh1 C13 C18 -34.93(12) . . . . ? C1 Rh1 C13 C18 49.87(13) . . . . ? C15 Rh1 C13 C18 158.35(13) . . . . ? C14 Rh1 C13 C18 121.27(14) . . . . ? C17 Rh1 C13 C18 -123.09(14) . . . . ? C16 Rh1 C13 C18 -158.44(13) . . . . ? Cl1 Rh1 C13 C18 -150.53(9) . . . . ? C17 C13 C14 C15 6.16(14) . . . . ? C18 C13 C14 C15 177.60(12) . . . . ? Rh1 C13 C14 C15 -59.53(9) . . . . ? C17 C13 C14 C19 -170.40(12) . . . . ? C18 C13 C14 C19 1.1(2) . . . . ? Rh1 C13 C14 C19 123.92(13) . . . . ? C17 C13 C14 Rh1 65.68(8) . . . . ? C18 C13 C14 Rh1 -122.87(13) . . . . ? N1 Rh1 C14 C15 152.43(7) . . . . ? C1 Rh1 C14 C15 -120.41(8) . . . . ? C13 Rh1 C14 C15 118.72(11) . . . . ? C17 Rh1 C14 C15 79.75(8) . . . . ? C16 Rh1 C14 C15 39.03(8) . . . . ? Cl1 Rh1 C14 C15 -26.32(9) . . . . ? N1 Rh1 C14 C13 33.71(10) . . . . ? C1 Rh1 C14 C13 120.87(7) . . . . ? C15 Rh1 C14 C13 -118.72(11) . . . . ? C17 Rh1 C14 C13 -38.97(7) . . . . ? C16 Rh1 C14 C13 -79.69(8) . . . . ? Cl1 Rh1 C14 C13 -145.04(6) . . . . ? N1 Rh1 C14 C19 -85.75(14) . . . . ? C1 Rh1 C14 C19 1.42(14) . . . . ? C13 Rh1 C14 C19 -119.45(16) . . . . ? C15 Rh1 C14 C19 121.83(16) . . . . ? C17 Rh1 C14 C19 -158.42(15) . . . . ? C16 Rh1 C14 C19 160.85(15) . . . . ? Cl1 Rh1 C14 C19 95.51(13) . . . . ? C13 C14 C15 C16 -6.31(14) . . . . ? C19 C14 C15 C16 170.17(13) . . . . ? Rh1 C14 C15 C16 -65.64(8) . . . . ? C13 C14 C15 C20 -178.36(13) . . . . ? C19 C14 C15 C20 -1.9(2) . . . . ? Rh1 C14 C15 C20 122.31(14) . . . . ? C13 C14 C15 Rh1 59.33(9) . . . . ? C19 C14 C15 Rh1 -124.19(14) . . . . ? N1 Rh1 C15 C14 -79.30(16) . . . . ? C1 Rh1 C15 C14 71.76(8) . . . . ? C13 Rh1 C15 C14 -37.17(7) . . . . ? C17 Rh1 C15 C14 -80.42(8) . . . . ? C16 Rh1 C15 C14 -115.52(10) . . . . ? Cl1 Rh1 C15 C14 161.48(7) . . . . ? N1 Rh1 C15 C16 36.22(17) . . . . ? C1 Rh1 C15 C16 -172.72(7) . . . . ? C13 Rh1 C15 C16 78.35(8) . . . . ? C14 Rh1 C15 C16 115.52(10) . . . . ? C17 Rh1 C15 C16 35.10(7) . . . . ? Cl1 Rh1 C15 C16 -83.00(7) . . . . ? N1 Rh1 C15 C20 157.69(13) . . . . ? C1 Rh1 C15 C20 -51.25(15) . . . . ? C13 Rh1 C15 C20 -160.19(15) . . . . ? C14 Rh1 C15 C20 -123.01(17) . . . . ? C17 Rh1 C15 C20 156.57(15) . . . . ? C16 Rh1 C15 C20 121.47(16) . . . . ? Cl1 Rh1 C15 C20 38.47(14) . . . . ? C14 C15 C16 C17 4.10(14) . . . . ? C20 C15 C16 C17 176.38(13) . . . . ? Rh1 C15 C16 C17 -60.21(9) . . . . ? C14 C15 C16 C21 -176.05(12) . . . . ? C20 C15 C16 C21 -3.8(2) . . . . ? Rh1 C15 C16 C21 119.63(12) . . . . ? C14 C15 C16 Rh1 64.31(8) . . . . ? C20 C15 C16 Rh1 -123.41(13) . . . . ? N1 Rh1 C16 C17 -46.34(9) . . . . ? C1 Rh1 C16 C17 135.11(11) . . . . ? C13 Rh1 C16 C17 37.66(7) . . . . ? C15 Rh1 C16 C17 119.69(10) . . . . ? C14 Rh1 C16 C17 80.93(8) . . . . ? Cl1 Rh1 C16 C17 -139.14(7) . . . . ? N1 Rh1 C16 C15 -166.03(7) . . . . ? C1 Rh1 C16 C15 15.41(14) . . . . ? C13 Rh1 C16 C15 -82.04(8) . . . . ? C14 Rh1 C16 C15 -38.77(7) . . . . ? C17 Rh1 C16 C15 -119.69(10) . . . . ? Cl1 Rh1 C16 C15 101.17(7) . . . . ? N1 Rh1 C16 C21 75.33(13) . . . . ? C1 Rh1 C16 C21 -103.23(15) . . . . ? C13 Rh1 C16 C21 159.32(14) . . . . ? C15 Rh1 C16 C21 -118.64(15) . . . . ? C14 Rh1 C16 C21 -157.41(14) . . . . ? C17 Rh1 C16 C21 121.67(16) . . . . ? Cl1 Rh1 C16 C21 -17.47(13) . . . . ? C15 C16 C17 C13 -0.27(14) . . . . ? C21 C16 C17 C13 179.88(12) . . . . ? Rh1 C16 C17 C13 -57.87(8) . . . . ? C15 C16 C17 C22 178.61(12) . . . . ? C21 C16 C17 C22 -1.2(2) . . . . ? Rh1 C16 C17 C22 121.01(12) . . . . ? C15 C16 C17 Rh1 57.60(8) . . . . ? C21 C16 C17 Rh1 -122.25(13) . . . . ? C14 C13 C17 C16 -3.65(14) . . . . ? C18 C13 C17 C16 -175.05(12) . . . . ? Rh1 C13 C17 C16 60.81(9) . . . . ? C14 C13 C17 C22 177.47(12) . . . . ? C18 C13 C17 C22 6.1(2) . . . . ? Rh1 C13 C17 C22 -118.07(12) . . . . ? C14 C13 C17 Rh1 -64.47(8) . . . . ? C18 C13 C17 Rh1 124.13(13) . . . . ? N1 Rh1 C17 C16 143.04(7) . . . . ? C1 Rh1 C17 C16 -134.27(11) . . . . ? C13 Rh1 C17 C16 -119.20(10) . . . . ? C15 Rh1 C17 C16 -37.34(8) . . . . ? C14 Rh1 C17 C16 -80.44(8) . . . . ? Cl1 Rh1 C17 C16 48.44(8) . . . . ? N1 Rh1 C17 C13 -97.76(7) . . . . ? C1 Rh1 C17 C13 -15.07(14) . . . . ? C15 Rh1 C17 C13 81.86(8) . . . . ? C14 Rh1 C17 C13 38.76(7) . . . . ? C16 Rh1 C17 C13 119.20(10) . . . . ? Cl1 Rh1 C17 C13 167.64(6) . . . . ? N1 Rh1 C17 C22 21.25(12) . . . . ? C1 Rh1 C17 C22 103.95(14) . . . . ? C13 Rh1 C17 C22 119.02(14) . . . . ? C15 Rh1 C17 C22 -159.13(13) . . . . ? C14 Rh1 C17 C22 157.78(13) . . . . ? C16 Rh1 C17 C22 -121.79(14) . . . . ? Cl1 Rh1 C17 C22 -73.34(12) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.267 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.115 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_4b _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll59 _chemical_melting_point ? _chemical_formula_moiety 'C24 H29 Cl N Rh' _chemical_formula_sum 'C24 H29 Cl N Rh' _chemical_formula_weight 469.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7242(6) _cell_length_b 12.0445(9) _cell_length_c 19.9275(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.271(1) _cell_angle_gamma 90.00 _cell_volume 2085.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4017 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 37.38 _exptl_crystal_description block _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8319 _exptl_absorpt_correction_T_max 0.8621 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50000 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 37.78 _reflns_number_total 11047 _reflns_number_gt 7364 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+1.0117P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11047 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.072341(15) 0.753230(12) 0.109845(7) 0.02028(4) Uani 1 1 d . . . Cl1 Cl -0.12548(5) 0.61345(4) 0.10676(3) 0.02901(10) Uani 1 1 d . . . N1 N 0.24433(18) 0.63084(13) 0.10713(8) 0.0222(3) Uani 1 1 d . . . C1 C 0.1111(2) 0.71748(17) 0.21372(9) 0.0222(3) Uani 1 1 d . . . H1 H 0.1142 0.6347 0.2176 0.027 Uiso 1 1 calc R . . C2 C 0.2691(2) 0.75684(15) 0.23495(9) 0.0207(3) Uani 1 1 d . . . C3 C 0.3014(2) 0.83768(17) 0.28484(10) 0.0255(4) Uani 1 1 d . . . H3 H 0.2189 0.8677 0.3070 0.031 Uiso 1 1 calc R . . C4 C 0.4493(2) 0.87521(18) 0.30291(10) 0.0286(4) Uani 1 1 d . . . H4 H 0.4667 0.9309 0.3365 0.034 Uiso 1 1 calc R . . C5 C 0.5728(2) 0.83151(18) 0.27194(11) 0.0286(4) Uani 1 1 d . . . H5 H 0.6747 0.8567 0.2842 0.034 Uiso 1 1 calc R . . C6 C 0.5446(2) 0.75072(16) 0.22294(10) 0.0245(3) Uani 1 1 d . . . H6 H 0.6285 0.7202 0.2019 0.029 Uiso 1 1 calc R . . C7 C 0.3952(2) 0.71303(16) 0.20370(9) 0.0209(3) Uani 1 1 d . . . C8 C 0.3735(2) 0.62899(15) 0.15000(9) 0.0207(3) Uani 1 1 d . . . C9 C 0.4867(2) 0.54910(17) 0.14226(10) 0.0255(4) Uani 1 1 d . . . H9 H 0.5764 0.5469 0.1731 0.031 Uiso 1 1 calc R . . C10 C 0.4688(3) 0.47345(18) 0.09018(11) 0.0302(4) Uani 1 1 d . . . H10 H 0.5464 0.4199 0.0843 0.036 Uiso 1 1 calc R . . C11 C 0.3360(3) 0.47700(18) 0.04661(11) 0.0299(4) Uani 1 1 d . . . H11 H 0.3209 0.4262 0.0102 0.036 Uiso 1 1 calc R . . C12 C 0.2265(2) 0.55544(17) 0.05707(10) 0.0273(4) Uani 1 1 d . . . H12 H 0.1342 0.5566 0.0278 0.033 Uiso 1 1 calc R . . C13 C 0.1883(2) 0.89587(17) 0.07444(11) 0.0278(4) Uani 1 1 d . . . C14 C 0.0711(2) 0.93490(17) 0.11350(9) 0.0262(4) Uani 1 1 d . . . C15 C -0.0720(2) 0.89518(19) 0.08253(11) 0.0299(4) Uani 1 1 d . . . C16 C -0.0434(3) 0.84233(18) 0.01982(11) 0.0322(4) Uani 1 1 d . . . C17 C 0.1136(3) 0.84242(18) 0.01438(10) 0.0310(4) Uani 1 1 d . . . C18 C 0.3567(3) 0.9195(2) 0.08659(16) 0.0483(7) Uani 1 1 d . . . H18A H 0.3834 0.9815 0.0580 0.073 Uiso 1 1 calc R . . H18B H 0.4152 0.8535 0.0757 0.073 Uiso 1 1 calc R . . H18C H 0.3820 0.9391 0.1340 0.073 Uiso 1 1 calc R . . C19 C 0.0929(4) 1.0104(2) 0.17273(12) 0.0447(6) Uani 1 1 d . . . H19A H 0.0926 1.0876 0.1572 0.067 Uiso 1 1 calc R . . H19B H 0.1915 0.9940 0.1984 0.067 Uiso 1 1 calc R . . H19C H 0.0091 0.9993 0.2016 0.067 Uiso 1 1 calc R . . C20 C -0.2280(3) 0.9148(3) 0.10589(17) 0.0534(8) Uani 1 1 d . . . H20A H -0.2808 0.9732 0.0784 0.080 Uiso 1 1 calc R . . H20B H -0.2171 0.9379 0.1532 0.080 Uiso 1 1 calc R . . H20C H -0.2883 0.8461 0.1013 0.080 Uiso 1 1 calc R . . C21 C -0.1679(4) 0.7950(3) -0.02886(15) 0.0543(8) Uani 1 1 d . . . H21A H -0.2124 0.8542 -0.0582 0.081 Uiso 1 1 calc R . . H21B H -0.2483 0.7622 -0.0038 0.081 Uiso 1 1 calc R . . H21C H -0.1242 0.7376 -0.0563 0.081 Uiso 1 1 calc R . . C22 C 0.1943(4) 0.7929(3) -0.04182(15) 0.0567(9) Uani 1 1 d . . . H22A H 0.1927 0.8459 -0.0792 0.085 Uiso 1 1 calc R . . H22B H 0.1418 0.7244 -0.0574 0.085 Uiso 1 1 calc R . . H22C H 0.3012 0.7760 -0.0256 0.085 Uiso 1 1 calc R . . C23 C -0.0177(2) 0.75570(18) 0.25420(10) 0.0267(4) Uani 1 1 d . . . H23A H -0.1174 0.7428 0.2275 0.032 Uiso 1 1 calc R . . H23B H -0.0072 0.8366 0.2623 0.032 Uiso 1 1 calc R . . C24 C -0.0189(3) 0.6965(2) 0.32164(11) 0.0372(5) Uani 1 1 d . . . H24A H -0.1002 0.7279 0.3467 0.056 Uiso 1 1 calc R . . H24B H 0.0810 0.7064 0.3477 0.056 Uiso 1 1 calc R . . H24C H -0.0382 0.6172 0.3139 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01874(6) 0.02526(7) 0.01671(6) 0.00220(5) 0.00085(4) -0.00232(5) Cl1 0.02313(19) 0.0329(2) 0.0296(2) 0.00817(18) -0.00506(16) -0.00666(17) N1 0.0235(7) 0.0251(7) 0.0185(6) -0.0010(5) 0.0043(5) -0.0054(6) C1 0.0166(7) 0.0310(8) 0.0190(7) 0.0021(6) 0.0017(6) -0.0009(6) C2 0.0176(6) 0.0264(8) 0.0179(7) 0.0025(6) 0.0009(5) 0.0006(6) C3 0.0240(8) 0.0315(10) 0.0209(8) -0.0022(7) 0.0016(6) 0.0013(7) C4 0.0286(9) 0.0314(10) 0.0249(9) -0.0042(7) -0.0031(7) -0.0022(8) C5 0.0212(8) 0.0331(10) 0.0307(10) -0.0006(8) -0.0028(7) -0.0042(7) C6 0.0168(7) 0.0301(9) 0.0266(8) 0.0005(7) 0.0011(6) -0.0008(7) C7 0.0177(7) 0.0236(8) 0.0215(7) 0.0000(6) 0.0027(6) -0.0020(6) C8 0.0195(7) 0.0250(8) 0.0184(7) 0.0005(6) 0.0051(6) -0.0025(6) C9 0.0230(8) 0.0289(9) 0.0256(9) 0.0013(7) 0.0070(7) 0.0008(7) C10 0.0351(10) 0.0272(9) 0.0303(10) -0.0002(7) 0.0140(8) 0.0014(8) C11 0.0385(11) 0.0277(9) 0.0250(9) -0.0036(7) 0.0106(8) -0.0041(8) C12 0.0315(9) 0.0294(9) 0.0210(8) -0.0021(7) 0.0031(7) -0.0062(8) C13 0.0254(8) 0.0275(9) 0.0311(10) 0.0080(8) 0.0056(7) -0.0027(7) C14 0.0319(9) 0.0249(8) 0.0217(8) 0.0025(7) 0.0021(7) -0.0003(7) C15 0.0253(9) 0.0327(10) 0.0320(10) 0.0136(8) 0.0037(7) 0.0018(7) C16 0.0387(11) 0.0295(10) 0.0263(9) 0.0096(8) -0.0080(8) -0.0047(8) C17 0.0442(12) 0.0276(9) 0.0223(9) 0.0062(7) 0.0098(8) 0.0027(8) C18 0.0264(10) 0.0438(14) 0.074(2) 0.0269(13) 0.0016(11) -0.0064(10) C19 0.0784(19) 0.0295(11) 0.0255(10) 0.0010(8) 0.0005(11) 0.0041(12) C20 0.0294(11) 0.0554(16) 0.078(2) 0.0359(15) 0.0179(12) 0.0139(11) C21 0.0646(18) 0.0462(15) 0.0454(15) 0.0179(12) -0.0311(14) -0.0161(14) C22 0.093(2) 0.0441(15) 0.0386(14) 0.0086(12) 0.0359(15) 0.0141(16) C23 0.0200(7) 0.0401(11) 0.0206(7) 0.0030(8) 0.0049(6) 0.0013(7) C24 0.0342(11) 0.0501(14) 0.0288(10) 0.0088(10) 0.0112(9) 0.0031(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 N1 2.1077(17) . ? Rh1 C1 2.1110(18) . ? Rh1 C13 2.1456(19) . ? Rh1 C15 2.163(2) . ? Rh1 C14 2.189(2) . ? Rh1 C17 2.2423(19) . ? Rh1 C16 2.249(2) . ? Rh1 Cl1 2.4077(5) . ? N1 C12 1.348(2) . ? N1 C8 1.350(2) . ? C1 C2 1.482(3) . ? C1 C23 1.513(3) . ? C1 H1 1.0000 . ? C2 C3 1.402(3) . ? C2 C7 1.415(2) . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.393(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.400(3) . ? C6 H6 0.9500 . ? C7 C8 1.473(3) . ? C8 C9 1.397(3) . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.421(3) . ? C13 C17 1.459(3) . ? C13 C18 1.495(3) . ? C14 C15 1.423(3) . ? C14 C19 1.488(3) . ? C15 C16 1.444(3) . ? C15 C20 1.498(3) . ? C16 C17 1.384(3) . ? C16 C21 1.501(3) . ? C17 C22 1.500(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.522(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Rh1 C1 80.34(7) . . ? N1 Rh1 C13 101.15(7) . . ? C1 Rh1 C13 116.61(8) . . ? N1 Rh1 C15 161.03(7) . . ? C1 Rh1 C15 116.43(8) . . ? C13 Rh1 C15 64.24(8) . . ? N1 Rh1 C14 134.89(7) . . ? C1 Rh1 C14 99.91(8) . . ? C13 Rh1 C14 38.25(8) . . ? C15 Rh1 C14 38.17(8) . . ? N1 Rh1 C17 98.23(7) . . ? C1 Rh1 C17 154.94(8) . . ? C13 Rh1 C17 38.76(8) . . ? C15 Rh1 C17 62.80(8) . . ? C14 Rh1 C17 63.33(7) . . ? N1 Rh1 C16 125.58(8) . . ? C1 Rh1 C16 154.08(8) . . ? C13 Rh1 C16 63.01(8) . . ? C15 Rh1 C16 38.16(9) . . ? C14 Rh1 C16 63.01(8) . . ? C17 Rh1 C16 35.89(8) . . ? N1 Rh1 Cl1 91.18(4) . . ? C1 Rh1 Cl1 86.12(5) . . ? C13 Rh1 Cl1 155.50(6) . . ? C15 Rh1 Cl1 98.45(6) . . ? C14 Rh1 Cl1 133.93(5) . . ? C17 Rh1 Cl1 118.94(6) . . ? C16 Rh1 Cl1 92.59(6) . . ? C12 N1 C8 119.36(17) . . ? C12 N1 Rh1 117.14(14) . . ? C8 N1 Rh1 123.37(13) . . ? C2 C1 C23 117.83(17) . . ? C2 C1 Rh1 106.00(12) . . ? C23 C1 Rh1 113.63(13) . . ? C2 C1 H1 106.2 . . ? C23 C1 H1 106.2 . . ? Rh1 C1 H1 106.2 . . ? C3 C2 C7 117.20(16) . . ? C3 C2 C1 123.10(16) . . ? C7 C2 C1 119.70(16) . . ? C4 C3 C2 122.27(18) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 120.13(19) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.93(18) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.43(18) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C2 120.03(17) . . ? C6 C7 C8 118.45(16) . . ? C2 C7 C8 121.51(16) . . ? N1 C8 C9 119.91(17) . . ? N1 C8 C7 119.52(16) . . ? C9 C8 C7 120.56(17) . . ? C10 C9 C8 120.40(19) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 118.71(19) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N1 C12 C11 122.8(2) . . ? N1 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? C14 C13 C17 107.81(18) . . ? C14 C13 C18 126.5(2) . . ? C17 C13 C18 125.1(2) . . ? C14 C13 Rh1 72.55(11) . . ? C17 C13 Rh1 74.21(12) . . ? C18 C13 Rh1 125.84(15) . . ? C13 C14 C15 107.33(18) . . ? C13 C14 C19 126.2(2) . . ? C15 C14 C19 126.3(2) . . ? C13 C14 Rh1 69.20(12) . . ? C15 C14 Rh1 69.91(12) . . ? C19 C14 Rh1 129.52(14) . . ? C14 C15 C16 107.99(18) . . ? C14 C15 C20 126.7(2) . . ? C16 C15 C20 125.0(2) . . ? C14 C15 Rh1 71.92(12) . . ? C16 C15 Rh1 74.12(12) . . ? C20 C15 Rh1 124.84(15) . . ? C17 C16 C15 108.58(19) . . ? C17 C16 C21 127.8(2) . . ? C15 C16 C21 123.7(2) . . ? C17 C16 Rh1 71.81(12) . . ? C15 C16 Rh1 67.71(11) . . ? C21 C16 Rh1 125.41(16) . . ? C16 C17 C13 107.86(18) . . ? C16 C17 C22 126.4(2) . . ? C13 C17 C22 125.7(2) . . ? C16 C17 Rh1 72.30(12) . . ? C13 C17 Rh1 67.03(11) . . ? C22 C17 Rh1 124.46(16) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 C23 C24 113.20(17) . . ? C1 C23 H23A 108.9 . . ? C24 C23 H23A 108.9 . . ? C1 C23 H23B 108.9 . . ? C24 C23 H23B 108.9 . . ? H23A C23 H23B 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C12 139.02(15) . . . . ? C13 Rh1 N1 C12 -105.54(14) . . . . ? C15 Rh1 N1 C12 -67.6(3) . . . . ? C14 Rh1 N1 C12 -126.57(14) . . . . ? C17 Rh1 N1 C12 -66.31(15) . . . . ? C16 Rh1 N1 C12 -40.87(17) . . . . ? Cl1 Rh1 N1 C12 53.16(13) . . . . ? C1 Rh1 N1 C8 -45.14(14) . . . . ? C13 Rh1 N1 C8 70.30(15) . . . . ? C15 Rh1 N1 C8 108.2(2) . . . . ? C14 Rh1 N1 C8 49.27(18) . . . . ? C17 Rh1 N1 C8 109.53(15) . . . . ? C16 Rh1 N1 C8 134.97(14) . . . . ? Cl1 Rh1 N1 C8 -131.00(14) . . . . ? N1 Rh1 C1 C2 67.12(13) . . . . ? C13 Rh1 C1 C2 -30.59(16) . . . . ? C15 Rh1 C1 C2 -103.50(14) . . . . ? C14 Rh1 C1 C2 -67.06(14) . . . . ? C17 Rh1 C1 C2 -21.7(3) . . . . ? C16 Rh1 C1 C2 -113.08(18) . . . . ? Cl1 Rh1 C1 C2 158.99(13) . . . . ? N1 Rh1 C1 C23 -161.91(15) . . . . ? C13 Rh1 C1 C23 100.38(15) . . . . ? C15 Rh1 C1 C23 27.46(17) . . . . ? C14 Rh1 C1 C23 63.91(15) . . . . ? C17 Rh1 C1 C23 109.3(2) . . . . ? C16 Rh1 C1 C23 17.9(3) . . . . ? Cl1 Rh1 C1 C23 -70.05(14) . . . . ? C23 C1 C2 C3 -8.2(3) . . . . ? Rh1 C1 C2 C3 120.36(17) . . . . ? C23 C1 C2 C7 172.55(17) . . . . ? Rh1 C1 C2 C7 -58.92(19) . . . . ? C7 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C4 -178.50(19) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C2 -0.6(3) . . . . ? C5 C6 C7 C8 178.45(19) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C1 C2 C7 C6 179.28(17) . . . . ? C3 C2 C7 C8 -179.07(17) . . . . ? C1 C2 C7 C8 0.3(3) . . . . ? C12 N1 C8 C9 -0.2(3) . . . . ? Rh1 N1 C8 C9 -175.96(13) . . . . ? C12 N1 C8 C7 178.43(16) . . . . ? Rh1 N1 C8 C7 2.7(2) . . . . ? C6 C7 C8 N1 -146.09(18) . . . . ? C2 C7 C8 N1 32.9(3) . . . . ? C6 C7 C8 C9 32.5(3) . . . . ? C2 C7 C8 C9 -148.43(18) . . . . ? N1 C8 C9 C10 1.4(3) . . . . ? C7 C8 C9 C10 -177.25(18) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C8 N1 C12 C11 -1.3(3) . . . . ? Rh1 N1 C12 C11 174.75(15) . . . . ? C10 C11 C12 N1 1.5(3) . . . . ? N1 Rh1 C13 C14 -155.75(11) . . . . ? C1 Rh1 C13 C14 -71.06(13) . . . . ? C15 Rh1 C13 C14 37.06(12) . . . . ? C17 Rh1 C13 C14 114.96(17) . . . . ? C16 Rh1 C13 C14 79.84(13) . . . . ? Cl1 Rh1 C13 C14 85.36(18) . . . . ? N1 Rh1 C13 C17 89.28(12) . . . . ? C1 Rh1 C13 C17 173.98(12) . . . . ? C15 Rh1 C13 C17 -77.90(13) . . . . ? C14 Rh1 C13 C17 -114.96(17) . . . . ? C16 Rh1 C13 C17 -35.12(12) . . . . ? Cl1 Rh1 C13 C17 -29.6(2) . . . . ? N1 Rh1 C13 C18 -32.9(2) . . . . ? C1 Rh1 C13 C18 51.8(2) . . . . ? C15 Rh1 C13 C18 159.9(2) . . . . ? C14 Rh1 C13 C18 122.8(3) . . . . ? C17 Rh1 C13 C18 -122.2(3) . . . . ? C16 Rh1 C13 C18 -157.3(3) . . . . ? Cl1 Rh1 C13 C18 -151.83(18) . . . . ? C17 C13 C14 C15 6.6(2) . . . . ? C18 C13 C14 C15 178.2(2) . . . . ? Rh1 C13 C14 C15 -59.78(14) . . . . ? C17 C13 C14 C19 -169.2(2) . . . . ? C18 C13 C14 C19 2.4(3) . . . . ? Rh1 C13 C14 C19 124.4(2) . . . . ? C17 C13 C14 Rh1 66.39(14) . . . . ? C18 C13 C14 Rh1 -122.1(2) . . . . ? N1 Rh1 C14 C13 34.66(16) . . . . ? C1 Rh1 C14 C13 120.85(12) . . . . ? C15 Rh1 C14 C13 -118.56(17) . . . . ? C17 Rh1 C14 C13 -39.43(12) . . . . ? C16 Rh1 C14 C13 -79.82(13) . . . . ? Cl1 Rh1 C14 C13 -144.97(10) . . . . ? N1 Rh1 C14 C15 153.22(11) . . . . ? C1 Rh1 C14 C15 -120.59(12) . . . . ? C13 Rh1 C14 C15 118.56(17) . . . . ? C17 Rh1 C14 C15 79.13(13) . . . . ? C16 Rh1 C14 C15 38.74(12) . . . . ? Cl1 Rh1 C14 C15 -26.41(14) . . . . ? N1 Rh1 C14 C19 -85.7(2) . . . . ? C1 Rh1 C14 C19 0.5(2) . . . . ? C13 Rh1 C14 C19 -120.3(3) . . . . ? C15 Rh1 C14 C19 121.1(3) . . . . ? C17 Rh1 C14 C19 -159.8(2) . . . . ? C16 Rh1 C14 C19 159.8(2) . . . . ? Cl1 Rh1 C14 C19 94.7(2) . . . . ? C13 C14 C15 C16 -6.6(2) . . . . ? C19 C14 C15 C16 169.2(2) . . . . ? Rh1 C14 C15 C16 -65.89(14) . . . . ? C13 C14 C15 C20 179.7(2) . . . . ? C19 C14 C15 C20 -4.5(3) . . . . ? Rh1 C14 C15 C20 120.4(2) . . . . ? C13 C14 C15 Rh1 59.33(14) . . . . ? C19 C14 C15 Rh1 -124.9(2) . . . . ? N1 Rh1 C15 C14 -79.1(3) . . . . ? C1 Rh1 C15 C14 71.26(13) . . . . ? C13 Rh1 C15 C14 -37.14(11) . . . . ? C17 Rh1 C15 C14 -80.62(13) . . . . ? C16 Rh1 C15 C14 -115.50(17) . . . . ? Cl1 Rh1 C15 C14 161.11(10) . . . . ? N1 Rh1 C15 C16 36.4(3) . . . . ? C1 Rh1 C15 C16 -173.24(12) . . . . ? C13 Rh1 C15 C16 78.37(13) . . . . ? C14 Rh1 C15 C16 115.50(17) . . . . ? C17 Rh1 C15 C16 34.88(12) . . . . ? Cl1 Rh1 C15 C16 -83.39(12) . . . . ? N1 Rh1 C15 C20 158.2(2) . . . . ? C1 Rh1 C15 C20 -51.4(3) . . . . ? C13 Rh1 C15 C20 -159.8(3) . . . . ? C14 Rh1 C15 C20 -122.6(3) . . . . ? C17 Rh1 C15 C20 156.7(3) . . . . ? C16 Rh1 C15 C20 121.9(3) . . . . ? Cl1 Rh1 C15 C20 38.5(2) . . . . ? C14 C15 C16 C17 4.0(2) . . . . ? C20 C15 C16 C17 177.8(2) . . . . ? Rh1 C15 C16 C17 -60.42(15) . . . . ? C14 C15 C16 C21 -176.9(2) . . . . ? C20 C15 C16 C21 -3.1(3) . . . . ? Rh1 C15 C16 C21 118.6(2) . . . . ? C14 C15 C16 Rh1 64.43(14) . . . . ? C20 C15 C16 Rh1 -121.7(2) . . . . ? N1 Rh1 C16 C17 -46.49(16) . . . . ? C1 Rh1 C16 C17 133.76(18) . . . . ? C13 Rh1 C16 C17 37.91(13) . . . . ? C15 Rh1 C16 C17 119.80(18) . . . . ? C14 Rh1 C16 C17 81.05(14) . . . . ? Cl1 Rh1 C16 C17 -139.80(12) . . . . ? N1 Rh1 C16 C15 -166.29(11) . . . . ? C1 Rh1 C16 C15 14.0(2) . . . . ? C13 Rh1 C16 C15 -81.89(13) . . . . ? C14 Rh1 C16 C15 -38.75(12) . . . . ? C17 Rh1 C16 C15 -119.80(18) . . . . ? Cl1 Rh1 C16 C15 100.40(12) . . . . ? N1 Rh1 C16 C21 77.4(3) . . . . ? C1 Rh1 C16 C21 -102.4(3) . . . . ? C13 Rh1 C16 C21 161.8(3) . . . . ? C15 Rh1 C16 C21 -116.3(3) . . . . ? C14 Rh1 C16 C21 -155.1(3) . . . . ? C17 Rh1 C16 C21 123.9(3) . . . . ? Cl1 Rh1 C16 C21 -15.9(3) . . . . ? C15 C16 C17 C13 0.1(2) . . . . ? C21 C16 C17 C13 -178.9(2) . . . . ? Rh1 C16 C17 C13 -57.78(14) . . . . ? C15 C16 C17 C22 178.1(2) . . . . ? C21 C16 C17 C22 -1.0(4) . . . . ? Rh1 C16 C17 C22 120.2(2) . . . . ? C15 C16 C17 Rh1 57.89(14) . . . . ? C21 C16 C17 Rh1 -121.1(2) . . . . ? C14 C13 C17 C16 -4.2(2) . . . . ? C18 C13 C17 C16 -175.9(2) . . . . ? Rh1 C13 C17 C16 61.09(15) . . . . ? C14 C13 C17 C22 177.8(2) . . . . ? C18 C13 C17 C22 6.1(3) . . . . ? Rh1 C13 C17 C22 -116.9(2) . . . . ? C14 C13 C17 Rh1 -65.28(14) . . . . ? C18 C13 C17 Rh1 123.0(2) . . . . ? N1 Rh1 C17 C16 143.41(13) . . . . ? C1 Rh1 C17 C16 -131.80(19) . . . . ? C13 Rh1 C17 C16 -119.00(18) . . . . ? C15 Rh1 C17 C16 -37.07(13) . . . . ? C14 Rh1 C17 C16 -80.09(14) . . . . ? Cl1 Rh1 C17 C16 47.46(14) . . . . ? N1 Rh1 C17 C13 -97.59(12) . . . . ? C1 Rh1 C17 C13 -12.8(2) . . . . ? C15 Rh1 C17 C13 81.93(13) . . . . ? C14 Rh1 C17 C13 38.91(12) . . . . ? C16 Rh1 C17 C13 119.00(18) . . . . ? Cl1 Rh1 C17 C13 166.46(10) . . . . ? N1 Rh1 C17 C22 20.9(3) . . . . ? C1 Rh1 C17 C22 105.7(3) . . . . ? C13 Rh1 C17 C22 118.5(3) . . . . ? C15 Rh1 C17 C22 -159.6(3) . . . . ? C14 Rh1 C17 C22 157.4(3) . . . . ? C16 Rh1 C17 C22 -122.5(3) . . . . ? Cl1 Rh1 C17 C22 -75.0(3) . . . . ? C2 C1 C23 C24 -75.4(2) . . . . ? Rh1 C1 C23 C24 159.73(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.178 _refine_diff_density_min -1.118 _refine_diff_density_rms 0.116 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_2c _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll09 _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 Cl N O Rh' _chemical_formula_sum 'C19 H23 Cl N O Rh' _chemical_formula_weight 419.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9391(13) _cell_length_b 8.3631(7) _cell_length_c 14.2215(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.611(1) _cell_angle_gamma 90.00 _cell_volume 1761.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4052 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 32.60 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7436 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30913 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 32.57 _reflns_number_total 6316 _reflns_number_gt 5218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+1.7455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6316 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0674 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.715386(10) 0.163962(17) 0.928650(10) 0.01372(4) Uani 1 1 d . . . Cl1 Cl 0.63257(3) -0.03466(6) 0.82914(3) 0.02225(10) Uani 1 1 d . . . C1 C 0.80575(13) 0.1942(2) 0.84003(14) 0.0177(4) Uani 1 1 d . . . O1 O 0.84903(10) 0.08523(18) 0.81202(11) 0.0239(3) Uani 1 1 d . . . C2 C 0.83038(13) 0.3641(2) 0.81929(13) 0.0174(4) Uani 1 1 d . . . C3 C 0.92036(14) 0.3967(3) 0.80794(15) 0.0213(4) Uani 1 1 d . . . H3A H 0.9628 0.3116 0.8118 0.026 Uiso 1 1 calc R . . C4 C 0.94836(15) 0.5499(3) 0.79131(16) 0.0247(4) Uani 1 1 d . . . H4A H 1.0098 0.5696 0.7845 0.030 Uiso 1 1 calc R . . C5 C 0.88695(15) 0.6760(3) 0.78449(15) 0.0229(4) Uani 1 1 d . . . H5A H 0.9064 0.7817 0.7736 0.027 Uiso 1 1 calc R . . C6 C 0.79733(14) 0.6462(2) 0.79360(14) 0.0199(4) Uani 1 1 d . . . H6A H 0.7549 0.7314 0.7869 0.024 Uiso 1 1 calc R . . C7 C 0.76859(13) 0.4909(2) 0.81259(13) 0.0168(3) Uani 1 1 d . . . C8 C 0.67274(13) 0.4699(2) 0.82093(13) 0.0176(4) Uani 1 1 d . . . H8A H 0.6323 0.5527 0.7974 0.021 Uiso 1 1 calc R . . N1 N 0.63974(11) 0.3473(2) 0.85774(11) 0.0166(3) Uani 1 1 d . . . C9 C 0.54107(13) 0.3380(3) 0.85398(15) 0.0217(4) Uani 1 1 d . . . H9A H 0.5134 0.4331 0.8220 0.033 Uiso 1 1 calc R . . H9B H 0.5253 0.3327 0.9186 0.033 Uiso 1 1 calc R . . H9C H 0.5188 0.2421 0.8188 0.033 Uiso 1 1 calc R . . C10 C 0.82606(13) 0.1554(2) 1.04613(13) 0.0177(3) Uani 1 1 d . . . C11 C 0.77870(13) 0.0072(2) 1.03913(13) 0.0176(4) Uani 1 1 d . . . C12 C 0.68845(14) 0.0358(2) 1.06624(14) 0.0186(4) Uani 1 1 d . . . C13 C 0.67919(14) 0.1992(2) 1.08131(13) 0.0188(4) Uani 1 1 d . . . C14 C 0.76296(14) 0.2774(2) 1.06286(14) 0.0190(4) Uani 1 1 d . . . C15 C 0.92451(14) 0.1766(3) 1.03779(16) 0.0254(4) Uani 1 1 d . . . H15A H 0.9607 0.1462 1.0977 0.038 Uiso 1 1 calc R . . H15B H 0.9363 0.2888 1.0237 0.038 Uiso 1 1 calc R . . H15C H 0.9409 0.1088 0.9865 0.038 Uiso 1 1 calc R . . C16 C 0.81759(16) -0.1527(2) 1.02107(16) 0.0247(4) Uani 1 1 d . . . H16A H 0.8413 -0.2025 1.0816 0.037 Uiso 1 1 calc R . . H16B H 0.8666 -0.1396 0.9822 0.037 Uiso 1 1 calc R . . H16C H 0.7704 -0.2209 0.9875 0.037 Uiso 1 1 calc R . . C17 C 0.62066(16) -0.0937(3) 1.07255(16) 0.0269(5) Uani 1 1 d . . . H17A H 0.6436 -0.1685 1.1231 0.040 Uiso 1 1 calc R . . H17B H 0.6100 -0.1509 1.0120 0.040 Uiso 1 1 calc R . . H17C H 0.5639 -0.0466 1.0867 0.040 Uiso 1 1 calc R . . C18 C 0.60043(16) 0.2865(3) 1.11157(16) 0.0286(5) Uani 1 1 d . . . H18A H 0.6162 0.3252 1.1767 0.043 Uiso 1 1 calc R . . H18B H 0.5486 0.2140 1.1087 0.043 Uiso 1 1 calc R . . H18C H 0.5849 0.3775 1.0691 0.043 Uiso 1 1 calc R . . C19 C 0.78256(17) 0.4521(2) 1.07628(16) 0.0269(5) Uani 1 1 d . . . H19A H 0.7963 0.4757 1.1442 0.040 Uiso 1 1 calc R . . H19B H 0.7297 0.5142 1.0492 0.040 Uiso 1 1 calc R . . H19C H 0.8345 0.4809 1.0443 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01324(7) 0.01481(7) 0.01289(6) 0.00093(5) 0.00092(4) -0.00010(5) Cl1 0.0240(2) 0.0212(2) 0.0199(2) -0.00263(18) -0.00330(18) -0.00233(18) C1 0.0159(8) 0.0204(9) 0.0165(8) 0.0002(7) 0.0008(7) -0.0001(7) O1 0.0259(8) 0.0203(7) 0.0269(8) -0.0013(6) 0.0082(6) 0.0026(6) C2 0.0185(9) 0.0190(9) 0.0154(8) -0.0016(7) 0.0041(7) 0.0000(7) C3 0.0196(9) 0.0224(9) 0.0228(10) -0.0002(8) 0.0067(8) 0.0017(8) C4 0.0215(10) 0.0261(11) 0.0271(11) -0.0019(9) 0.0056(8) -0.0039(8) C5 0.0257(10) 0.0205(9) 0.0231(10) -0.0004(8) 0.0057(8) -0.0054(8) C6 0.0230(9) 0.0178(9) 0.0192(9) 0.0015(7) 0.0038(7) 0.0007(7) C7 0.0162(8) 0.0190(9) 0.0151(8) -0.0004(7) 0.0020(7) -0.0001(7) C8 0.0172(9) 0.0198(9) 0.0155(8) 0.0015(7) 0.0011(7) 0.0026(7) N1 0.0150(7) 0.0190(8) 0.0156(7) 0.0018(6) 0.0012(6) 0.0018(6) C9 0.0141(8) 0.0278(10) 0.0232(9) 0.0051(8) 0.0025(7) 0.0025(8) C10 0.0175(8) 0.0185(9) 0.0158(8) 0.0029(7) -0.0031(6) -0.0006(7) C11 0.0202(9) 0.0170(8) 0.0144(8) 0.0017(7) -0.0019(7) -0.0014(7) C12 0.0206(9) 0.0200(9) 0.0145(8) 0.0032(7) 0.0004(7) -0.0021(7) C13 0.0228(10) 0.0205(9) 0.0127(8) 0.0009(7) 0.0010(7) 0.0023(7) C14 0.0252(10) 0.0153(8) 0.0151(9) -0.0003(7) -0.0020(7) -0.0005(7) C15 0.0179(9) 0.0287(11) 0.0276(11) 0.0033(9) -0.0042(8) -0.0038(8) C16 0.0328(11) 0.0173(9) 0.0233(10) 0.0012(8) 0.0002(8) 0.0044(8) C17 0.0285(11) 0.0276(11) 0.0244(10) 0.0051(9) 0.0024(9) -0.0109(9) C18 0.0318(12) 0.0364(12) 0.0180(10) -0.0020(9) 0.0051(9) 0.0098(10) C19 0.0389(12) 0.0155(9) 0.0244(10) -0.0012(8) -0.0035(9) -0.0015(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C1 1.981(2) . ? Rh1 N1 2.0842(16) . ? Rh1 C14 2.1652(19) . ? Rh1 C11 2.1652(19) . ? Rh1 C10 2.1906(19) . ? Rh1 C12 2.3126(19) . ? Rh1 C13 2.3245(19) . ? Rh1 Cl1 2.4144(5) . ? C1 O1 1.215(2) . ? C1 C2 1.507(3) . ? C2 C7 1.401(3) . ? C2 C3 1.402(3) . ? C3 C4 1.378(3) . ? C3 H3A 0.9500 . ? C4 C5 1.393(3) . ? C4 H4A 0.9500 . ? C5 C6 1.385(3) . ? C5 H5A 0.9500 . ? C6 C7 1.405(3) . ? C6 H6A 0.9500 . ? C7 C8 1.463(3) . ? C8 N1 1.279(2) . ? C8 H8A 0.9500 . ? N1 C9 1.470(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.424(3) . ? C10 C14 1.430(3) . ? C10 C15 1.502(3) . ? C11 C12 1.470(3) . ? C11 C16 1.494(3) . ? C12 C13 1.393(3) . ? C12 C17 1.493(3) . ? C13 C14 1.466(3) . ? C13 C18 1.496(3) . ? C14 C19 1.498(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 N1 88.27(7) . . ? C1 Rh1 C14 109.46(8) . . ? N1 Rh1 C14 101.41(7) . . ? C1 Rh1 C11 105.66(8) . . ? N1 Rh1 C11 162.43(7) . . ? C14 Rh1 C11 64.20(8) . . ? C1 Rh1 C10 88.87(8) . . ? N1 Rh1 C10 134.37(7) . . ? C14 Rh1 C10 38.33(8) . . ? C11 Rh1 C10 38.16(7) . . ? C1 Rh1 C12 143.80(8) . . ? N1 Rh1 C12 127.33(7) . . ? C14 Rh1 C12 62.01(7) . . ? C11 Rh1 C12 38.15(7) . . ? C10 Rh1 C12 62.47(7) . . ? C1 Rh1 C13 147.17(8) . . ? N1 Rh1 C13 100.39(7) . . ? C14 Rh1 C13 37.91(7) . . ? C11 Rh1 C13 62.12(7) . . ? C10 Rh1 C13 62.44(7) . . ? C12 Rh1 C13 34.96(7) . . ? C1 Rh1 Cl1 93.12(6) . . ? N1 Rh1 Cl1 91.13(5) . . ? C14 Rh1 Cl1 154.29(6) . . ? C11 Rh1 Cl1 98.59(5) . . ? C10 Rh1 Cl1 134.50(5) . . ? C12 Rh1 Cl1 92.52(5) . . ? C13 Rh1 Cl1 118.04(5) . . ? O1 C1 C2 119.28(18) . . ? O1 C1 Rh1 123.37(15) . . ? C2 C1 Rh1 116.70(13) . . ? C7 C2 C3 118.59(18) . . ? C7 C2 C1 123.47(17) . . ? C3 C2 C1 117.93(18) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C7 120.54(19) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C2 C7 C6 119.82(18) . . ? C2 C7 C8 123.13(18) . . ? C6 C7 C8 117.01(18) . . ? N1 C8 C7 124.35(18) . . ? N1 C8 H8A 117.8 . . ? C7 C8 H8A 117.8 . . ? C8 N1 C9 117.81(17) . . ? C8 N1 Rh1 125.02(14) . . ? C9 N1 Rh1 117.10(13) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C14 107.46(17) . . ? C11 C10 C15 125.47(19) . . ? C14 C10 C15 127.06(19) . . ? C11 C10 Rh1 69.96(11) . . ? C14 C10 Rh1 69.88(11) . . ? C15 C10 Rh1 125.74(14) . . ? C10 C11 C12 107.73(17) . . ? C10 C11 C16 126.17(18) . . ? C12 C11 C16 125.58(18) . . ? C10 C11 Rh1 71.88(11) . . ? C12 C11 Rh1 76.36(11) . . ? C16 C11 Rh1 124.04(14) . . ? C13 C12 C11 108.25(17) . . ? C13 C12 C17 128.3(2) . . ? C11 C12 C17 123.41(19) . . ? C13 C12 Rh1 72.99(11) . . ? C11 C12 Rh1 65.49(10) . . ? C17 C12 Rh1 125.62(14) . . ? C12 C13 C14 107.78(18) . . ? C12 C13 C18 128.4(2) . . ? C14 C13 C18 123.82(19) . . ? C12 C13 Rh1 72.05(11) . . ? C14 C13 Rh1 65.14(10) . . ? C18 C13 Rh1 128.30(14) . . ? C10 C14 C13 107.99(17) . . ? C10 C14 C19 126.5(2) . . ? C13 C14 C19 124.70(19) . . ? C10 C14 Rh1 71.80(11) . . ? C13 C14 Rh1 76.95(11) . . ? C19 C14 Rh1 125.13(14) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Rh1 C1 O1 -145.50(18) . . . . ? C14 Rh1 C1 O1 113.00(17) . . . . ? C11 Rh1 C1 O1 45.36(19) . . . . ? C10 Rh1 C1 O1 80.05(18) . . . . ? C12 Rh1 C1 O1 44.1(2) . . . . ? C13 Rh1 C1 O1 107.88(19) . . . . ? Cl1 Rh1 C1 O1 -54.47(17) . . . . ? N1 Rh1 C1 C2 43.82(14) . . . . ? C14 Rh1 C1 C2 -57.68(16) . . . . ? C11 Rh1 C1 C2 -125.32(14) . . . . ? C10 Rh1 C1 C2 -90.63(15) . . . . ? C12 Rh1 C1 C2 -126.58(15) . . . . ? C13 Rh1 C1 C2 -62.8(2) . . . . ? Cl1 Rh1 C1 C2 134.85(14) . . . . ? O1 C1 C2 C7 153.38(19) . . . . ? Rh1 C1 C2 C7 -35.5(2) . . . . ? O1 C1 C2 C3 -27.9(3) . . . . ? Rh1 C1 C2 C3 143.22(16) . . . . ? C7 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 C4 -178.29(19) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C4 C5 C6 C7 2.0(3) . . . . ? C3 C2 C7 C6 0.8(3) . . . . ? C1 C2 C7 C6 179.59(18) . . . . ? C3 C2 C7 C8 178.44(18) . . . . ? C1 C2 C7 C8 -2.8(3) . . . . ? C5 C6 C7 C2 -2.1(3) . . . . ? C5 C6 C7 C8 -179.87(18) . . . . ? C2 C7 C8 N1 18.3(3) . . . . ? C6 C7 C8 N1 -164.02(19) . . . . ? C7 C8 N1 C9 -175.17(18) . . . . ? C7 C8 N1 Rh1 7.9(3) . . . . ? C1 Rh1 N1 C8 -34.15(17) . . . . ? C14 Rh1 N1 C8 75.35(17) . . . . ? C11 Rh1 N1 C8 108.9(3) . . . . ? C10 Rh1 N1 C8 52.6(2) . . . . ? C12 Rh1 N1 C8 138.73(15) . . . . ? C13 Rh1 N1 C8 113.97(17) . . . . ? Cl1 Rh1 N1 C8 -127.23(16) . . . . ? C1 Rh1 N1 C9 148.89(15) . . . . ? C14 Rh1 N1 C9 -101.61(15) . . . . ? C11 Rh1 N1 C9 -68.1(3) . . . . ? C10 Rh1 N1 C9 -124.39(15) . . . . ? C12 Rh1 N1 C9 -38.23(17) . . . . ? C13 Rh1 N1 C9 -62.99(15) . . . . ? Cl1 Rh1 N1 C9 55.80(14) . . . . ? C1 Rh1 C10 C11 -117.51(12) . . . . ? N1 Rh1 C10 C11 156.01(11) . . . . ? C14 Rh1 C10 C11 118.29(17) . . . . ? C12 Rh1 C10 C11 39.47(11) . . . . ? C13 Rh1 C10 C11 79.08(12) . . . . ? Cl1 Rh1 C10 C11 -24.25(15) . . . . ? C1 Rh1 C10 C14 124.20(12) . . . . ? N1 Rh1 C10 C14 37.72(15) . . . . ? C11 Rh1 C10 C14 -118.29(17) . . . . ? C12 Rh1 C10 C14 -78.82(12) . . . . ? C13 Rh1 C10 C14 -39.21(11) . . . . ? Cl1 Rh1 C10 C14 -142.54(10) . . . . ? C1 Rh1 C10 C15 2.39(18) . . . . ? N1 Rh1 C10 C15 -84.1(2) . . . . ? C14 Rh1 C10 C15 -121.8(2) . . . . ? C11 Rh1 C10 C15 119.9(2) . . . . ? C12 Rh1 C10 C15 159.4(2) . . . . ? C13 Rh1 C10 C15 -161.0(2) . . . . ? Cl1 Rh1 C10 C15 95.65(18) . . . . ? C14 C10 C11 C12 -8.5(2) . . . . ? C15 C10 C11 C12 171.19(18) . . . . ? Rh1 C10 C11 C12 -68.59(13) . . . . ? C14 C10 C11 C16 179.46(18) . . . . ? C15 C10 C11 C16 -0.9(3) . . . . ? Rh1 C10 C11 C16 119.4(2) . . . . ? C14 C10 C11 Rh1 60.09(13) . . . . ? C15 C10 C11 Rh1 -120.2(2) . . . . ? C1 Rh1 C11 C10 67.06(13) . . . . ? N1 Rh1 C11 C10 -74.3(3) . . . . ? C14 Rh1 C11 C10 -37.34(12) . . . . ? C12 Rh1 C11 C10 -114.15(16) . . . . ? C13 Rh1 C11 C10 -79.98(12) . . . . ? Cl1 Rh1 C11 C10 162.77(11) . . . . ? C1 Rh1 C11 C12 -178.79(11) . . . . ? N1 Rh1 C11 C12 39.8(3) . . . . ? C14 Rh1 C11 C12 76.80(12) . . . . ? C10 Rh1 C11 C12 114.15(16) . . . . ? C13 Rh1 C11 C12 34.17(11) . . . . ? Cl1 Rh1 C11 C12 -83.09(11) . . . . ? C1 Rh1 C11 C16 -54.84(18) . . . . ? N1 Rh1 C11 C16 163.8(2) . . . . ? C14 Rh1 C11 C16 -159.2(2) . . . . ? C10 Rh1 C11 C16 -121.9(2) . . . . ? C12 Rh1 C11 C16 124.0(2) . . . . ? C13 Rh1 C11 C16 158.12(19) . . . . ? Cl1 Rh1 C11 C16 40.87(17) . . . . ? C10 C11 C12 C13 4.8(2) . . . . ? C16 C11 C12 C13 176.95(19) . . . . ? Rh1 C11 C12 C13 -60.73(14) . . . . ? C10 C11 C12 C17 -176.65(18) . . . . ? C16 C11 C12 C17 -4.5(3) . . . . ? Rh1 C11 C12 C17 117.77(19) . . . . ? C10 C11 C12 Rh1 65.58(13) . . . . ? C16 C11 C12 Rh1 -122.3(2) . . . . ? C1 Rh1 C12 C13 121.93(15) . . . . ? N1 Rh1 C12 C13 -45.97(15) . . . . ? C14 Rh1 C12 C13 36.94(12) . . . . ? C11 Rh1 C12 C13 119.96(17) . . . . ? C10 Rh1 C12 C13 80.49(13) . . . . ? Cl1 Rh1 C12 C13 -139.31(12) . . . . ? C1 Rh1 C12 C11 1.97(18) . . . . ? N1 Rh1 C12 C11 -165.93(11) . . . . ? C14 Rh1 C12 C11 -83.02(12) . . . . ? C10 Rh1 C12 C11 -39.47(11) . . . . ? C13 Rh1 C12 C11 -119.96(17) . . . . ? Cl1 Rh1 C12 C11 100.72(11) . . . . ? C1 Rh1 C12 C17 -112.7(2) . . . . ? N1 Rh1 C12 C17 79.4(2) . . . . ? C14 Rh1 C12 C17 162.3(2) . . . . ? C11 Rh1 C12 C17 -114.7(2) . . . . ? C10 Rh1 C12 C17 -154.2(2) . . . . ? C13 Rh1 C12 C17 125.3(2) . . . . ? Cl1 Rh1 C12 C17 -13.97(19) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C17 C12 C13 C14 -177.70(19) . . . . ? Rh1 C12 C13 C14 -55.40(13) . . . . ? C11 C12 C13 C18 -178.83(19) . . . . ? C17 C12 C13 C18 2.8(3) . . . . ? Rh1 C12 C13 C18 125.1(2) . . . . ? C11 C12 C13 Rh1 56.10(13) . . . . ? C17 C12 C13 Rh1 -122.3(2) . . . . ? C1 Rh1 C13 C12 -112.38(16) . . . . ? N1 Rh1 C13 C12 144.47(12) . . . . ? C14 Rh1 C13 C12 -120.25(17) . . . . ? C11 Rh1 C13 C12 -37.26(12) . . . . ? C10 Rh1 C13 C12 -80.60(13) . . . . ? Cl1 Rh1 C13 C12 47.56(13) . . . . ? C1 Rh1 C13 C14 7.9(2) . . . . ? N1 Rh1 C13 C14 -95.28(12) . . . . ? C11 Rh1 C13 C14 82.99(12) . . . . ? C10 Rh1 C13 C14 39.65(11) . . . . ? C12 Rh1 C13 C14 120.25(17) . . . . ? Cl1 Rh1 C13 C14 167.81(10) . . . . ? C1 Rh1 C13 C18 122.4(2) . . . . ? N1 Rh1 C13 C18 19.3(2) . . . . ? C14 Rh1 C13 C18 114.6(2) . . . . ? C11 Rh1 C13 C18 -162.4(2) . . . . ? C10 Rh1 C13 C18 154.2(2) . . . . ? C12 Rh1 C13 C18 -125.2(3) . . . . ? Cl1 Rh1 C13 C18 -77.6(2) . . . . ? C11 C10 C14 C13 9.0(2) . . . . ? C15 C10 C14 C13 -170.72(19) . . . . ? Rh1 C10 C14 C13 69.10(13) . . . . ? C11 C10 C14 C19 179.18(19) . . . . ? C15 C10 C14 C19 -0.5(3) . . . . ? Rh1 C10 C14 C19 -120.7(2) . . . . ? C11 C10 C14 Rh1 -60.14(13) . . . . ? C15 C10 C14 Rh1 120.2(2) . . . . ? C12 C13 C14 C10 -6.0(2) . . . . ? C18 C13 C14 C10 173.57(18) . . . . ? Rh1 C13 C14 C10 -65.64(13) . . . . ? C12 C13 C14 C19 -176.43(19) . . . . ? C18 C13 C14 C19 3.1(3) . . . . ? Rh1 C13 C14 C19 123.9(2) . . . . ? C12 C13 C14 Rh1 59.65(14) . . . . ? C18 C13 C14 Rh1 -120.79(19) . . . . ? C1 Rh1 C14 C10 -61.28(13) . . . . ? N1 Rh1 C14 C10 -153.50(11) . . . . ? C11 Rh1 C14 C10 37.18(11) . . . . ? C12 Rh1 C14 C10 80.11(12) . . . . ? C13 Rh1 C14 C10 114.20(16) . . . . ? Cl1 Rh1 C14 C10 88.76(17) . . . . ? C1 Rh1 C14 C13 -175.49(11) . . . . ? N1 Rh1 C14 C13 92.30(12) . . . . ? C11 Rh1 C14 C13 -77.03(12) . . . . ? C10 Rh1 C14 C13 -114.20(16) . . . . ? C12 Rh1 C14 C13 -34.09(11) . . . . ? Cl1 Rh1 C14 C13 -25.4(2) . . . . ? C1 Rh1 C14 C19 61.1(2) . . . . ? N1 Rh1 C14 C19 -31.2(2) . . . . ? C11 Rh1 C14 C19 159.5(2) . . . . ? C10 Rh1 C14 C19 122.3(2) . . . . ? C12 Rh1 C14 C19 -157.6(2) . . . . ? C13 Rh1 C14 C19 -123.5(2) . . . . ? Cl1 Rh1 C14 C19 -148.91(14) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 32.57 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.321 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.102 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Blessing, R. (1995). SADABS V2.10, Acta Cryst. A51, 33-38. Bruker (2000). SHELXTL V6.14, Bruker AXS, Inc., Madison, WI, USA. Bruker (2006). SAINT V7.34a, Bruker AXS, Inc., Madison, WI, USA. Bruker (2006). APEX2 V2.1-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (1997). SHELXL-97, University of G\"ottingen, Germany. ; #===end data_1d _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonyj06 _chemical_melting_point ? _chemical_formula_moiety 'C23 H32 Ir N2, Cl, H2 O' _chemical_formula_sum 'C23 H34 Cl Ir N2 O' _chemical_formula_weight 582.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.623(2) _cell_length_b 15.255(3) _cell_length_c 15.900(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.486(4) _cell_angle_gamma 90.00 _cell_volume 2332.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4058 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 29.19 _exptl_crystal_description needle _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 5.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3872 _exptl_absorpt_correction_T_max 0.7584 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54755 _diffrn_reflns_av_R_equivalents 0.1144 _diffrn_reflns_av_sigmaI/netI 0.0882 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 34.97 _reflns_number_total 10243 _reflns_number_gt 6517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXTL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen atoms on the co-crystallized water molecule were found from the difference Fourier map at low resolution (~1.2 \%A) and refined relative to the oxygen atom in both positional and isotropic displacement parameters. Since it was observed that the hydrogen atom directed at the water molecule across the inversion center was too close to its symmetry equivalent, a second position was introduced for that hydrogen atom to avoid the close contact. Thus the hydrogen atoms were given occupancies of 1.0 (H1A), 0.5 (H1B), and 0.5 (H1B'). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0104P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10243 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.65143(2) 0.521433(13) 0.274218(11) 0.01885(6) Uani 1 1 d . . . N1 N 0.7985(5) 0.4260(3) 0.2507(3) 0.0219(9) Uani 1 1 d . . . N2 N 0.8471(5) 0.6055(3) 0.4103(3) 0.0244(9) Uani 1 1 d . . . C1 C 0.6017(5) 0.4240(3) 0.3574(3) 0.0204(10) Uani 1 1 d . . . C2 C 0.5015(6) 0.4250(4) 0.4176(3) 0.0267(11) Uani 1 1 d . . . H2 H 0.4462 0.4758 0.4246 0.032 Uiso 1 1 calc R . . C3 C 0.4821(6) 0.3520(4) 0.4673(4) 0.0286(12) Uani 1 1 d . . . H3 H 0.4149 0.3542 0.5093 0.034 Uiso 1 1 calc R . . C4 C 0.5579(6) 0.2755(4) 0.4577(4) 0.0281(12) Uani 1 1 d . . . H4 H 0.5401 0.2254 0.4911 0.034 Uiso 1 1 calc R . . C5 C 0.6603(6) 0.2732(4) 0.3985(3) 0.0249(11) Uani 1 1 d . . . H5 H 0.7151 0.2222 0.3914 0.030 Uiso 1 1 calc R . . C6 C 0.6803(6) 0.3474(3) 0.3502(3) 0.0214(10) Uani 1 1 d . . . C7 C 0.7887(6) 0.3530(4) 0.2909(3) 0.0226(10) Uani 1 1 d . . . H7 H 0.8499 0.3054 0.2818 0.027 Uiso 1 1 calc R . . C8 C 0.9084(6) 0.4382(4) 0.1924(4) 0.0273(11) Uani 1 1 d . . . H8A H 0.9828 0.3957 0.2048 0.041 Uiso 1 1 calc R . . H8B H 0.9456 0.4978 0.1983 0.041 Uiso 1 1 calc R . . H8C H 0.8711 0.4294 0.1347 0.041 Uiso 1 1 calc R . . C9 C 0.7750(5) 0.5721(3) 0.3593(3) 0.0209(9) Uani 1 1 d . . . C10 C 0.9495(7) 0.6577(4) 0.4588(4) 0.0342(14) Uani 1 1 d . . . C11 C 0.9423(10) 0.7487(5) 0.4227(5) 0.053(2) Uani 1 1 d . . . H11A H 0.9649 0.7469 0.3632 0.080 Uiso 1 1 calc R . . H11B H 1.0092 0.7865 0.4537 0.080 Uiso 1 1 calc R . . H11C H 0.8482 0.7722 0.4278 0.080 Uiso 1 1 calc R . . C12 C 1.0901(7) 0.6145(5) 0.4479(4) 0.0432(17) Uani 1 1 d . . . H12A H 1.0910 0.5564 0.4743 0.065 Uiso 1 1 calc R . . H12B H 1.1635 0.6509 0.4746 0.065 Uiso 1 1 calc R . . H12C H 1.1065 0.6084 0.3878 0.065 Uiso 1 1 calc R . . C13 C 0.9136(7) 0.6574(4) 0.5503(4) 0.0350(14) Uani 1 1 d . . . H13A H 0.9239 0.5979 0.5730 0.052 Uiso 1 1 calc R . . H13B H 0.8173 0.6769 0.5553 0.052 Uiso 1 1 calc R . . H13C H 0.9763 0.6971 0.5821 0.052 Uiso 1 1 calc R . . C14 C 0.6284(5) 0.5892(4) 0.1483(3) 0.0231(10) Uani 1 1 d . . . C15 C 0.5322(6) 0.5158(4) 0.1522(3) 0.0254(11) Uani 1 1 d . . . C16 C 0.4378(6) 0.5335(4) 0.2166(4) 0.0260(11) Uani 1 1 d . . . C17 C 0.4789(5) 0.6138(4) 0.2568(3) 0.0232(10) Uani 1 1 d . . . C18 C 0.5951(5) 0.6484(3) 0.2122(3) 0.0215(10) Uani 1 1 d . . . C19 C 0.7334(6) 0.6045(4) 0.0839(3) 0.0276(11) Uani 1 1 d . . . H19A H 0.7016 0.6520 0.0462 0.041 Uiso 1 1 calc R . . H19B H 0.7454 0.5508 0.0512 0.041 Uiso 1 1 calc R . . H19C H 0.8224 0.6209 0.1119 0.041 Uiso 1 1 calc R . . C20 C 0.5284(7) 0.4365(4) 0.0961(4) 0.0376(15) Uani 1 1 d . . . H20A H 0.4503 0.4416 0.0548 0.056 Uiso 1 1 calc R . . H20B H 0.5166 0.3838 0.1303 0.056 Uiso 1 1 calc R . . H20C H 0.6157 0.4325 0.0668 0.056 Uiso 1 1 calc R . . C21 C 0.3142(7) 0.4804(4) 0.2364(4) 0.0343(13) Uani 1 1 d . . . H21A H 0.2308 0.5065 0.2091 0.051 Uiso 1 1 calc R . . H21B H 0.3043 0.4793 0.2974 0.051 Uiso 1 1 calc R . . H21C H 0.3259 0.4205 0.2157 0.051 Uiso 1 1 calc R . . C22 C 0.3984(6) 0.6610(4) 0.3208(4) 0.0303(12) Uani 1 1 d . . . H22A H 0.3119 0.6837 0.2943 0.045 Uiso 1 1 calc R . . H22B H 0.4539 0.7099 0.3440 0.045 Uiso 1 1 calc R . . H22C H 0.3765 0.6206 0.3662 0.045 Uiso 1 1 calc R . . C23 C 0.6646(6) 0.7339(4) 0.2302(4) 0.0271(11) Uani 1 1 d . . . H23A H 0.6196 0.7797 0.1955 0.041 Uiso 1 1 calc R . . H23B H 0.7630 0.7297 0.2171 0.041 Uiso 1 1 calc R . . H23C H 0.6570 0.7484 0.2899 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.95336(18) 0.15745(11) 0.29605(11) 0.0399(4) Uani 1 1 d . . . O1 O 0.8785(4) 0.0678(3) 0.4560(3) 0.0357(10) Uani 1 1 d . . . H1A H 0.9112 0.0887 0.4114 0.043 Uiso 1 1 d R . . H1B H 0.9396 0.0335 0.4778 0.043 Uiso 0.50 1 d PR A 1 H1B' H 0.8065 0.0889 0.4776 0.043 Uiso 0.50 1 d PR B 5 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01633(9) 0.01794(9) 0.02180(9) -0.00102(8) -0.00459(6) 0.00111(8) N1 0.018(2) 0.023(2) 0.0242(19) -0.0037(17) -0.0046(16) 0.0016(17) N2 0.018(2) 0.026(2) 0.028(2) -0.0040(18) -0.0019(17) 0.0003(18) C1 0.025(2) 0.018(2) 0.017(2) -0.0031(17) -0.0059(17) -0.0006(19) C2 0.025(3) 0.026(3) 0.029(3) 0.002(2) -0.002(2) 0.002(2) C3 0.022(3) 0.037(3) 0.027(3) 0.000(2) -0.001(2) -0.002(2) C4 0.026(3) 0.027(3) 0.031(3) 0.006(2) -0.003(2) -0.002(2) C5 0.022(3) 0.024(3) 0.028(3) 0.001(2) -0.007(2) 0.000(2) C6 0.020(2) 0.021(2) 0.022(2) 0.0001(18) -0.0047(18) -0.0013(19) C7 0.020(2) 0.023(2) 0.024(2) -0.0033(19) -0.0055(19) 0.002(2) C8 0.022(3) 0.024(3) 0.036(3) -0.002(2) 0.005(2) -0.002(2) C9 0.018(2) 0.020(2) 0.024(2) 0.0007(18) 0.0024(18) 0.0055(19) C10 0.028(3) 0.038(4) 0.036(3) -0.008(3) -0.001(2) -0.011(3) C11 0.074(6) 0.038(4) 0.047(4) -0.006(3) -0.005(4) -0.025(4) C12 0.023(3) 0.064(5) 0.042(4) -0.019(3) -0.001(3) -0.012(3) C13 0.032(3) 0.040(4) 0.032(3) -0.011(3) -0.007(2) -0.004(3) C14 0.017(2) 0.025(3) 0.027(2) 0.0037(19) -0.0046(19) -0.0007(19) C15 0.028(3) 0.023(3) 0.025(2) 0.002(2) -0.009(2) 0.000(2) C16 0.019(2) 0.021(3) 0.037(3) 0.005(2) -0.008(2) 0.0029(19) C17 0.018(2) 0.020(2) 0.031(3) 0.001(2) -0.0056(19) 0.006(2) C18 0.016(2) 0.023(2) 0.026(2) 0.0074(19) 0.0024(18) 0.0044(19) C19 0.025(3) 0.031(3) 0.027(3) 0.000(2) -0.004(2) 0.004(2) C20 0.044(4) 0.030(3) 0.037(3) -0.001(3) -0.015(3) -0.003(3) C21 0.022(3) 0.033(3) 0.047(3) 0.009(3) -0.010(2) -0.002(3) C22 0.027(3) 0.030(3) 0.034(3) 0.005(2) 0.001(2) 0.007(2) C23 0.029(3) 0.021(3) 0.031(3) -0.003(2) -0.006(2) 0.001(2) Cl1 0.0322(8) 0.0367(8) 0.0500(9) -0.0016(7) -0.0056(7) 0.0058(7) O1 0.020(2) 0.050(3) 0.037(2) -0.021(2) 0.0067(17) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C9 1.924(5) . ? Ir1 C1 2.060(5) . ? Ir1 N1 2.076(5) . ? Ir1 C17 2.186(5) . ? Ir1 C15 2.213(5) . ? Ir1 C16 2.222(5) . ? Ir1 C18 2.230(5) . ? Ir1 C14 2.256(5) . ? N1 C7 1.288(7) . ? N1 C8 1.448(7) . ? N2 C9 1.161(6) . ? N2 C10 1.461(7) . ? C1 C2 1.388(8) . ? C1 C6 1.400(7) . ? C2 C3 1.383(8) . ? C2 H2 0.9500 . ? C3 C4 1.387(9) . ? C3 H3 0.9500 . ? C4 C5 1.394(8) . ? C4 H4 0.9500 . ? C5 C6 1.385(8) . ? C5 H5 0.9500 . ? C6 C7 1.438(8) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.503(10) . ? C10 C13 1.510(9) . ? C10 C12 1.521(10) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C18 1.406(8) . ? C14 C15 1.456(8) . ? C14 C19 1.488(8) . ? C15 C16 1.424(9) . ? C15 C20 1.502(8) . ? C16 C17 1.430(8) . ? C16 C21 1.484(9) . ? C17 C18 1.449(8) . ? C17 C22 1.491(8) . ? C18 C23 1.487(8) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1 H1A 0.8499 . ? O1 H1B 0.8500 . ? O1 H1B' 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Ir1 C1 89.6(2) . . ? C9 Ir1 N1 90.18(19) . . ? C1 Ir1 N1 77.8(2) . . ? C9 Ir1 C17 105.8(2) . . ? C1 Ir1 C17 110.5(2) . . ? N1 Ir1 C17 161.68(18) . . ? C9 Ir1 C15 156.0(2) . . ? C1 Ir1 C15 114.1(2) . . ? N1 Ir1 C15 98.41(19) . . ? C17 Ir1 C15 63.4(2) . . ? C9 Ir1 C16 142.1(2) . . ? C1 Ir1 C16 95.0(2) . . ? N1 Ir1 C16 127.56(19) . . ? C17 Ir1 C16 37.9(2) . . ? C15 Ir1 C16 37.5(2) . . ? C9 Ir1 C18 95.3(2) . . ? C1 Ir1 C18 148.4(2) . . ? N1 Ir1 C18 133.17(19) . . ? C17 Ir1 C18 38.3(2) . . ? C15 Ir1 C18 62.5(2) . . ? C16 Ir1 C18 62.8(2) . . ? C9 Ir1 C14 118.3(2) . . ? C1 Ir1 C14 152.13(18) . . ? N1 Ir1 C14 101.72(19) . . ? C17 Ir1 C14 63.1(2) . . ? C15 Ir1 C14 38.0(2) . . ? C16 Ir1 C14 62.8(2) . . ? C18 Ir1 C14 36.53(19) . . ? C7 N1 C8 120.0(5) . . ? C7 N1 Ir1 116.8(4) . . ? C8 N1 Ir1 123.2(4) . . ? C9 N2 C10 167.5(6) . . ? C2 C1 C6 117.4(5) . . ? C2 C1 Ir1 128.5(4) . . ? C6 C1 Ir1 114.1(4) . . ? C3 C2 C1 120.0(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 122.0(6) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 119.0(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 118.3(5) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 123.2(5) . . ? C5 C6 C7 122.3(5) . . ? C1 C6 C7 114.4(5) . . ? N1 C7 C6 116.6(5) . . ? N1 C7 H7 121.7 . . ? C6 C7 H7 121.7 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 Ir1 177.6(5) . . ? N2 C10 C11 106.5(5) . . ? N2 C10 C13 109.3(5) . . ? C11 C10 C13 111.2(6) . . ? N2 C10 C12 106.7(5) . . ? C11 C10 C12 112.5(6) . . ? C13 C10 C12 110.5(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C18 C14 C15 107.3(5) . . ? C18 C14 C19 125.4(5) . . ? C15 C14 C19 127.0(5) . . ? C18 C14 Ir1 70.7(3) . . ? C15 C14 Ir1 69.4(3) . . ? C19 C14 Ir1 129.7(4) . . ? C16 C15 C14 108.1(5) . . ? C16 C15 C20 125.4(5) . . ? C14 C15 C20 126.4(6) . . ? C16 C15 Ir1 71.6(3) . . ? C14 C15 Ir1 72.6(3) . . ? C20 C15 Ir1 123.4(4) . . ? C15 C16 C17 108.1(5) . . ? C15 C16 C21 126.3(5) . . ? C17 C16 C21 125.6(6) . . ? C15 C16 Ir1 70.9(3) . . ? C17 C16 Ir1 69.7(3) . . ? C21 C16 Ir1 127.1(4) . . ? C16 C17 C18 107.3(5) . . ? C16 C17 C22 125.2(5) . . ? C18 C17 C22 126.4(5) . . ? C16 C17 Ir1 72.4(3) . . ? C18 C17 Ir1 72.5(3) . . ? C22 C17 Ir1 129.7(4) . . ? C14 C18 C17 109.0(5) . . ? C14 C18 C23 126.0(5) . . ? C17 C18 C23 125.1(5) . . ? C14 C18 Ir1 72.7(3) . . ? C17 C18 Ir1 69.2(3) . . ? C23 C18 Ir1 125.2(4) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? H1A O1 H1B 107.3 . . ? H1A O1 H1B' 122.1 . . ? H1B O1 H1B' 129.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 Ir1 N1 C7 93.4(4) . . . . ? C1 Ir1 N1 C7 3.9(4) . . . . ? C17 Ir1 N1 C7 -115.3(6) . . . . ? C15 Ir1 N1 C7 -109.1(4) . . . . ? C16 Ir1 N1 C7 -83.1(4) . . . . ? C18 Ir1 N1 C7 -169.1(3) . . . . ? C14 Ir1 N1 C7 -147.6(4) . . . . ? C9 Ir1 N1 C8 -86.6(4) . . . . ? C1 Ir1 N1 C8 -176.1(4) . . . . ? C17 Ir1 N1 C8 64.7(8) . . . . ? C15 Ir1 N1 C8 70.9(4) . . . . ? C16 Ir1 N1 C8 96.9(4) . . . . ? C18 Ir1 N1 C8 10.9(5) . . . . ? C14 Ir1 N1 C8 32.4(4) . . . . ? C9 Ir1 C1 C2 85.7(5) . . . . ? N1 Ir1 C1 C2 176.0(5) . . . . ? C17 Ir1 C1 C2 -21.0(5) . . . . ? C15 Ir1 C1 C2 -90.1(5) . . . . ? C16 Ir1 C1 C2 -56.6(5) . . . . ? C18 Ir1 C1 C2 -13.8(7) . . . . ? C14 Ir1 C1 C2 -91.9(6) . . . . ? C9 Ir1 C1 C6 -94.8(4) . . . . ? N1 Ir1 C1 C6 -4.5(3) . . . . ? C17 Ir1 C1 C6 158.4(3) . . . . ? C15 Ir1 C1 C6 89.3(4) . . . . ? C16 Ir1 C1 C6 122.9(4) . . . . ? C18 Ir1 C1 C6 165.7(4) . . . . ? C14 Ir1 C1 C6 87.5(6) . . . . ? C6 C1 C2 C3 -0.3(8) . . . . ? Ir1 C1 C2 C3 179.2(4) . . . . ? C1 C2 C3 C4 -1.7(9) . . . . ? C2 C3 C4 C5 2.5(9) . . . . ? C3 C4 C5 C6 -1.3(8) . . . . ? C4 C5 C6 C1 -0.7(8) . . . . ? C4 C5 C6 C7 176.3(5) . . . . ? C2 C1 C6 C5 1.5(7) . . . . ? Ir1 C1 C6 C5 -178.0(4) . . . . ? C2 C1 C6 C7 -175.8(4) . . . . ? Ir1 C1 C6 C7 4.7(5) . . . . ? C8 N1 C7 C6 177.5(4) . . . . ? Ir1 N1 C7 C6 -2.5(6) . . . . ? C5 C6 C7 N1 -178.8(5) . . . . ? C1 C6 C7 N1 -1.5(7) . . . . ? C10 N2 C9 Ir1 -70(12) . . . . ? C1 Ir1 C9 N2 -125(12) . . . . ? N1 Ir1 C9 N2 157(12) . . . . ? C17 Ir1 C9 N2 -14(12) . . . . ? C15 Ir1 C9 N2 45(12) . . . . ? C16 Ir1 C9 N2 -28(12) . . . . ? C18 Ir1 C9 N2 23(12) . . . . ? C14 Ir1 C9 N2 53(12) . . . . ? C9 N2 C10 C11 42(3) . . . . ? C9 N2 C10 C13 162(2) . . . . ? C9 N2 C10 C12 -78(3) . . . . ? C9 Ir1 C14 C18 -56.7(4) . . . . ? C1 Ir1 C14 C18 120.6(5) . . . . ? N1 Ir1 C14 C18 -153.4(3) . . . . ? C17 Ir1 C14 C18 37.5(3) . . . . ? C15 Ir1 C14 C18 117.9(5) . . . . ? C16 Ir1 C14 C18 80.2(3) . . . . ? C9 Ir1 C14 C15 -174.7(3) . . . . ? C1 Ir1 C14 C15 2.7(6) . . . . ? N1 Ir1 C14 C15 88.7(3) . . . . ? C17 Ir1 C14 C15 -80.4(4) . . . . ? C16 Ir1 C14 C15 -37.7(3) . . . . ? C18 Ir1 C14 C15 -117.9(5) . . . . ? C9 Ir1 C14 C19 63.8(6) . . . . ? C1 Ir1 C14 C19 -118.9(6) . . . . ? N1 Ir1 C14 C19 -32.9(5) . . . . ? C17 Ir1 C14 C19 158.0(6) . . . . ? C15 Ir1 C14 C19 -121.6(7) . . . . ? C16 Ir1 C14 C19 -159.3(6) . . . . ? C18 Ir1 C14 C19 120.5(6) . . . . ? C18 C14 C15 C16 2.4(6) . . . . ? C19 C14 C15 C16 -171.9(5) . . . . ? Ir1 C14 C15 C16 63.3(4) . . . . ? C18 C14 C15 C20 -179.9(5) . . . . ? C19 C14 C15 C20 5.8(9) . . . . ? Ir1 C14 C15 C20 -119.0(6) . . . . ? C18 C14 C15 Ir1 -60.9(3) . . . . ? C19 C14 C15 Ir1 124.9(5) . . . . ? C9 Ir1 C15 C16 -105.0(6) . . . . ? C1 Ir1 C15 C16 64.8(4) . . . . ? N1 Ir1 C15 C16 145.1(3) . . . . ? C17 Ir1 C15 C16 -37.1(3) . . . . ? C18 Ir1 C15 C16 -80.3(3) . . . . ? C14 Ir1 C15 C16 -116.6(5) . . . . ? C9 Ir1 C15 C14 11.6(7) . . . . ? C1 Ir1 C15 C14 -178.6(3) . . . . ? N1 Ir1 C15 C14 -98.3(3) . . . . ? C17 Ir1 C15 C14 79.5(3) . . . . ? C16 Ir1 C15 C14 116.6(5) . . . . ? C18 Ir1 C15 C14 36.3(3) . . . . ? C9 Ir1 C15 C20 134.2(6) . . . . ? C1 Ir1 C15 C20 -56.0(6) . . . . ? N1 Ir1 C15 C20 24.3(5) . . . . ? C17 Ir1 C15 C20 -157.9(6) . . . . ? C16 Ir1 C15 C20 -120.8(7) . . . . ? C18 Ir1 C15 C20 158.9(6) . . . . ? C14 Ir1 C15 C20 122.6(7) . . . . ? C14 C15 C16 C17 -3.9(6) . . . . ? C20 C15 C16 C17 178.4(5) . . . . ? Ir1 C15 C16 C17 60.0(4) . . . . ? C14 C15 C16 C21 173.6(5) . . . . ? C20 C15 C16 C21 -4.1(9) . . . . ? Ir1 C15 C16 C21 -122.5(5) . . . . ? C14 C15 C16 Ir1 -63.9(3) . . . . ? C20 C15 C16 Ir1 118.4(5) . . . . ? C9 Ir1 C16 C15 140.2(4) . . . . ? C1 Ir1 C16 C15 -124.0(3) . . . . ? N1 Ir1 C16 C15 -45.5(4) . . . . ? C17 Ir1 C16 C15 118.6(5) . . . . ? C18 Ir1 C16 C15 79.5(3) . . . . ? C14 Ir1 C16 C15 38.3(3) . . . . ? C9 Ir1 C16 C17 21.5(5) . . . . ? C1 Ir1 C16 C17 117.3(3) . . . . ? N1 Ir1 C16 C17 -164.2(3) . . . . ? C15 Ir1 C16 C17 -118.6(5) . . . . ? C18 Ir1 C16 C17 -39.1(3) . . . . ? C14 Ir1 C16 C17 -80.3(3) . . . . ? C9 Ir1 C16 C21 -98.3(6) . . . . ? C1 Ir1 C16 C21 -2.5(6) . . . . ? N1 Ir1 C16 C21 76.0(6) . . . . ? C17 Ir1 C16 C21 -119.9(7) . . . . ? C15 Ir1 C16 C21 121.5(7) . . . . ? C18 Ir1 C16 C21 -158.9(6) . . . . ? C14 Ir1 C16 C21 159.8(6) . . . . ? C15 C16 C17 C18 3.8(6) . . . . ? C21 C16 C17 C18 -173.7(5) . . . . ? Ir1 C16 C17 C18 64.6(3) . . . . ? C15 C16 C17 C22 172.5(5) . . . . ? C21 C16 C17 C22 -5.0(8) . . . . ? Ir1 C16 C17 C22 -126.7(5) . . . . ? C15 C16 C17 Ir1 -60.8(4) . . . . ? C21 C16 C17 Ir1 121.7(5) . . . . ? C9 Ir1 C17 C16 -166.4(3) . . . . ? C1 Ir1 C17 C16 -70.8(4) . . . . ? N1 Ir1 C17 C16 43.5(8) . . . . ? C15 Ir1 C17 C16 36.7(3) . . . . ? C18 Ir1 C17 C16 115.3(5) . . . . ? C14 Ir1 C17 C16 79.5(4) . . . . ? C9 Ir1 C17 C18 78.3(3) . . . . ? C1 Ir1 C17 C18 173.9(3) . . . . ? N1 Ir1 C17 C18 -71.8(7) . . . . ? C15 Ir1 C17 C18 -78.6(3) . . . . ? C16 Ir1 C17 C18 -115.3(5) . . . . ? C14 Ir1 C17 C18 -35.8(3) . . . . ? C9 Ir1 C17 C22 -44.9(6) . . . . ? C1 Ir1 C17 C22 50.7(6) . . . . ? N1 Ir1 C17 C22 165.1(5) . . . . ? C15 Ir1 C17 C22 158.3(6) . . . . ? C16 Ir1 C17 C22 121.6(7) . . . . ? C18 Ir1 C17 C22 -123.2(7) . . . . ? C14 Ir1 C17 C22 -159.0(6) . . . . ? C15 C14 C18 C17 0.0(6) . . . . ? C19 C14 C18 C17 174.4(5) . . . . ? Ir1 C14 C18 C17 -60.0(3) . . . . ? C15 C14 C18 C23 -178.6(5) . . . . ? C19 C14 C18 C23 -4.2(8) . . . . ? Ir1 C14 C18 C23 121.4(5) . . . . ? C15 C14 C18 Ir1 60.0(3) . . . . ? C19 C14 C18 Ir1 -125.6(5) . . . . ? C16 C17 C18 C14 -2.4(6) . . . . ? C22 C17 C18 C14 -170.9(5) . . . . ? Ir1 C17 C18 C14 62.2(4) . . . . ? C16 C17 C18 C23 176.3(5) . . . . ? C22 C17 C18 C23 7.7(8) . . . . ? Ir1 C17 C18 C23 -119.2(5) . . . . ? C16 C17 C18 Ir1 -64.6(3) . . . . ? C22 C17 C18 Ir1 126.9(5) . . . . ? C9 Ir1 C18 C14 132.3(3) . . . . ? C1 Ir1 C18 C14 -129.8(4) . . . . ? N1 Ir1 C18 C14 37.0(4) . . . . ? C17 Ir1 C18 C14 -118.8(4) . . . . ? C15 Ir1 C18 C14 -37.8(3) . . . . ? C16 Ir1 C18 C14 -80.2(3) . . . . ? C9 Ir1 C18 C17 -108.9(3) . . . . ? C1 Ir1 C18 C17 -11.0(5) . . . . ? N1 Ir1 C18 C17 155.8(3) . . . . ? C15 Ir1 C18 C17 81.0(3) . . . . ? C16 Ir1 C18 C17 38.6(3) . . . . ? C14 Ir1 C18 C17 118.8(5) . . . . ? C9 Ir1 C18 C23 10.1(5) . . . . ? C1 Ir1 C18 C23 108.0(5) . . . . ? N1 Ir1 C18 C23 -85.2(5) . . . . ? C17 Ir1 C18 C23 119.0(6) . . . . ? C15 Ir1 C18 C23 -160.0(5) . . . . ? C16 Ir1 C18 C23 157.6(5) . . . . ? C14 Ir1 C18 C23 -122.2(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A Cl1 0.85 2.17 3.003(5) 167.8 . O1 H1B O1 0.85 2.53 3.379(10) 179.5 3_756 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.391 _refine_diff_density_min -2.187 _refine_diff_density_rms 0.260 _publ_section_references ; Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2010). APEX2 V2010.3-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _vrf_PLAT420_jonyj06 ; PROBLEM: _B D-H Without Acceptor .. O1 - *H1B' ... ? RESPONSE: The hydrogen atoms on the co-crystallized water molecule were found from the difference Fourier map at low resolution (~1.2 \%A) and refined relative to the oxygen atom in both positional and isotropic displacement parameters. Since it was observed that the hydrogen atom directed at the water molecule across the inversion center was too close to its symmetry equivalent, a second position was introduced for that hydrogen atom to avoid the close contact. Thus the hydrogen atoms were given occupancies of 1.0 (H1A), 0.5 (H1B), and 0.5 (H1B'). ; #===end data_3e _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll60 _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 Cl Ir N' _chemical_formula_sum 'C23 H25 Cl Ir N' _chemical_formula_weight 543.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.154(2) _cell_length_b 14.4567(19) _cell_length_c 8.3482(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.430(3) _cell_angle_gamma 90.00 _cell_volume 1949.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3870 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 37.80 _exptl_crystal_description block _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 6.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1232 _exptl_absorpt_correction_T_max 0.3710 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46111 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 37.78 _reflns_number_total 10288 _reflns_number_gt 8503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The structure refined as a pseudomerohedral twin (87:13), a monoclinic packing that approximated orthorhombic symmetry. Application of twin law, [1 0 0 / 0 -1 0 / 0 0 -1], a 180 deg rotation around direct lattice [1 0 0], reduced the R1 residual from 0.0897 to 0.0397. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+14.3043P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10288 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.284982(12) -0.029499(10) 0.90219(2) 0.01293(4) Uani 1 1 d . . . Cl1 Cl 0.38132(9) -0.03526(9) 1.12583(15) 0.0206(2) Uani 1 1 d . . . N1 N 0.3086(3) 0.1136(3) 0.8802(5) 0.0169(7) Uani 1 1 d . . . C1 C 0.2009(3) 0.0056(4) 1.0729(6) 0.0192(9) Uani 1 1 d . . . H1A H 0.2079 -0.0239 1.1738 0.023 Uiso 1 1 calc R . . C2 C 0.1374(4) 0.0644(4) 1.0622(7) 0.0223(10) Uani 1 1 d . . . H2A H 0.1078 0.0778 1.1573 0.027 Uiso 1 1 calc R . . C3 C 0.1101(3) 0.1101(3) 0.9130(7) 0.0194(8) Uani 1 1 d . . . C4 C 0.0247(3) 0.1087(4) 0.8782(9) 0.0261(11) Uani 1 1 d . . . H4A H -0.0120 0.0833 0.9549 0.031 Uiso 1 1 calc R . . C5 C -0.0075(4) 0.1430(5) 0.7364(10) 0.0330(14) Uani 1 1 d . . . H5A H -0.0653 0.1393 0.7152 0.040 Uiso 1 1 calc R . . C6 C 0.0444(4) 0.1825(5) 0.6265(10) 0.0335(14) Uani 1 1 d . . . H6A H 0.0231 0.2049 0.5274 0.040 Uiso 1 1 calc R . . C7 C 0.1281(4) 0.1894(4) 0.6615(8) 0.0263(11) Uani 1 1 d . . . H7A H 0.1634 0.2192 0.5870 0.032 Uiso 1 1 calc R . . C8 C 0.1627(3) 0.1537(4) 0.8041(7) 0.0196(8) Uani 1 1 d . . . C9 C 0.2517(3) 0.1761(3) 0.8319(6) 0.0163(8) Uani 1 1 d . . . C10 C 0.2765(4) 0.2674(4) 0.7990(7) 0.0207(9) Uani 1 1 d . . . H10A H 0.2360 0.3122 0.7703 0.025 Uiso 1 1 calc R . . C11 C 0.3584(4) 0.2928(4) 0.8078(7) 0.0227(9) Uani 1 1 d . . . H11A H 0.3752 0.3540 0.7817 0.027 Uiso 1 1 calc R . . C12 C 0.4157(4) 0.2274(4) 0.8553(7) 0.0231(10) Uani 1 1 d . . . H12A H 0.4728 0.2428 0.8632 0.028 Uiso 1 1 calc R . . C13 C 0.3891(3) 0.1391(4) 0.8913(7) 0.0196(8) Uani 1 1 d . . . H13A H 0.4287 0.0945 0.9251 0.024 Uiso 1 1 calc R . . C14 C 0.2717(3) -0.0521(4) 0.6447(6) 0.0193(9) Uani 1 1 d . . . C15 C 0.2067(3) -0.0981(4) 0.7294(6) 0.0189(8) Uani 1 1 d . . . C16 C 0.2444(3) -0.1656(3) 0.8351(6) 0.0179(8) Uani 1 1 d . . . C17 C 0.3326(3) -0.1612(3) 0.8083(6) 0.0170(8) Uani 1 1 d . . . C18 C 0.3500(3) -0.0920(3) 0.6933(6) 0.0170(8) Uani 1 1 d . . . C19 C 0.2624(5) 0.0190(4) 0.5186(7) 0.0304(13) Uani 1 1 d . . . H19A H 0.2802 -0.0065 0.4157 0.046 Uiso 1 1 calc R . . H19B H 0.2965 0.0729 0.5458 0.046 Uiso 1 1 calc R . . H19C H 0.2042 0.0378 0.5106 0.046 Uiso 1 1 calc R . . C20 C 0.1152(4) -0.0880(5) 0.7015(9) 0.0283(12) Uani 1 1 d . . . H20A H 0.0954 -0.1388 0.6336 0.042 Uiso 1 1 calc R . . H20B H 0.1040 -0.0289 0.6483 0.042 Uiso 1 1 calc R . . H20C H 0.0865 -0.0898 0.8045 0.042 Uiso 1 1 calc R . . C21 C 0.2013(4) -0.2355(4) 0.9367(8) 0.0293(12) Uani 1 1 d . . . H21A H 0.1977 -0.2944 0.8786 0.044 Uiso 1 1 calc R . . H21B H 0.1455 -0.2135 0.9614 0.044 Uiso 1 1 calc R . . H21C H 0.2326 -0.2446 1.0365 0.044 Uiso 1 1 calc R . . C22 C 0.3942(4) -0.2226(4) 0.8901(8) 0.0275(11) Uani 1 1 d . . . H22B H 0.3978 -0.2815 0.8324 0.041 Uiso 1 1 calc R . . H22C H 0.3767 -0.2341 1.0004 0.041 Uiso 1 1 calc R . . H22D H 0.4486 -0.1925 0.8909 0.041 Uiso 1 1 calc R . . C23 C 0.4323(4) -0.0649(5) 0.6280(9) 0.0284(12) Uani 1 1 d . . . H23D H 0.4529 -0.1143 0.5584 0.043 Uiso 1 1 calc R . . H23A H 0.4714 -0.0551 0.7167 0.043 Uiso 1 1 calc R . . H23B H 0.4265 -0.0077 0.5662 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01388(7) 0.01160(6) 0.01331(6) -0.00014(6) -0.00026(5) -0.00089(6) Cl1 0.0224(5) 0.0211(5) 0.0181(5) 0.0002(4) -0.0047(4) -0.0002(4) N1 0.0195(17) 0.0133(15) 0.0178(17) -0.0037(13) -0.0033(13) 0.0012(13) C1 0.019(2) 0.022(2) 0.0162(19) -0.0029(16) 0.0023(15) -0.0021(16) C2 0.023(2) 0.019(2) 0.025(2) -0.0026(18) 0.0060(18) -0.0021(18) C3 0.0164(19) 0.0151(18) 0.027(2) -0.0013(17) 0.0023(18) 0.0004(14) C4 0.015(2) 0.022(2) 0.041(3) 0.002(2) 0.002(2) 0.0002(17) C5 0.017(2) 0.028(3) 0.054(4) 0.006(3) -0.004(2) 0.002(2) C6 0.026(3) 0.028(3) 0.047(4) 0.008(3) -0.015(3) -0.001(2) C7 0.021(2) 0.021(2) 0.037(3) 0.006(2) -0.007(2) -0.0005(18) C8 0.018(2) 0.017(2) 0.024(2) 0.0018(17) -0.0008(17) 0.0003(16) C9 0.0160(19) 0.0125(17) 0.020(2) -0.0007(15) 0.0000(15) -0.0002(14) C10 0.023(2) 0.0141(18) 0.025(2) 0.0011(16) 0.0012(19) -0.0013(17) C11 0.025(2) 0.015(2) 0.028(2) 0.0010(18) 0.001(2) -0.0059(18) C12 0.019(2) 0.020(2) 0.030(3) 0.0018(19) -0.0027(19) -0.0063(17) C13 0.0153(18) 0.020(2) 0.024(2) 0.0016(18) -0.0018(17) -0.0015(15) C14 0.024(2) 0.0166(19) 0.0171(18) -0.0053(15) 0.0004(16) 0.0026(16) C15 0.018(2) 0.020(2) 0.0188(18) -0.0045(16) -0.0019(16) -0.0011(16) C16 0.020(2) 0.0135(18) 0.020(2) 0.0000(15) 0.0028(16) -0.0011(15) C17 0.019(2) 0.0143(18) 0.0175(18) -0.0011(15) 0.0001(15) 0.0023(15) C18 0.0196(19) 0.0141(17) 0.0174(18) -0.0029(15) 0.0032(15) -0.0010(16) C19 0.048(4) 0.026(3) 0.018(2) 0.0053(19) 0.001(2) 0.009(2) C20 0.016(2) 0.031(3) 0.037(3) -0.012(3) -0.008(2) 0.003(2) C21 0.036(3) 0.020(2) 0.031(3) 0.001(2) 0.009(2) -0.012(2) C22 0.031(3) 0.023(2) 0.028(3) -0.001(2) -0.005(2) 0.011(2) C23 0.021(2) 0.026(3) 0.038(3) -0.012(2) 0.011(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.041(5) . ? Ir1 N1 2.112(4) . ? Ir1 C16 2.147(5) . ? Ir1 C15 2.153(5) . ? Ir1 C14 2.183(5) . ? Ir1 C17 2.201(5) . ? Ir1 C18 2.234(5) . ? Ir1 Cl1 2.4230(13) . ? N1 C9 1.348(7) . ? N1 C13 1.354(7) . ? C1 C2 1.334(8) . ? C1 H1A 0.9500 . ? C2 C3 1.474(8) . ? C2 H2A 0.9500 . ? C3 C8 1.399(8) . ? C3 C4 1.408(8) . ? C4 C5 1.382(10) . ? C4 H4A 0.9500 . ? C5 C6 1.372(11) . ? C5 H5A 0.9500 . ? C6 C7 1.386(9) . ? C6 H6A 0.9500 . ? C7 C8 1.410(8) . ? C7 H7A 0.9500 . ? C8 C9 1.491(7) . ? C9 C10 1.406(7) . ? C10 C11 1.375(8) . ? C10 H10A 0.9500 . ? C11 C12 1.380(8) . ? C11 H11A 0.9500 . ? C12 C13 1.381(8) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.434(8) . ? C14 C18 1.447(8) . ? C14 C19 1.478(8) . ? C15 C16 1.447(7) . ? C15 C20 1.502(8) . ? C16 C17 1.446(7) . ? C16 C21 1.495(8) . ? C17 C18 1.417(7) . ? C17 C22 1.494(8) . ? C18 C23 1.492(8) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 H22D 0.9800 . ? C23 H23D 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 86.5(2) . . ? C1 Ir1 C16 101.9(2) . . ? N1 Ir1 C16 158.45(18) . . ? C1 Ir1 C15 101.1(2) . . ? N1 Ir1 C15 119.91(18) . . ? C16 Ir1 C15 39.3(2) . . ? C1 Ir1 C14 131.6(2) . . ? N1 Ir1 C14 94.44(19) . . ? C16 Ir1 C14 65.1(2) . . ? C15 Ir1 C14 38.6(2) . . ? C1 Ir1 C17 134.5(2) . . ? N1 Ir1 C17 138.85(18) . . ? C16 Ir1 C17 38.82(19) . . ? C15 Ir1 C17 64.40(19) . . ? C14 Ir1 C17 63.39(19) . . ? C1 Ir1 C18 164.9(2) . . ? N1 Ir1 C18 104.02(18) . . ? C16 Ir1 C18 64.54(19) . . ? C15 Ir1 C18 64.40(19) . . ? C14 Ir1 C18 38.2(2) . . ? C17 Ir1 C18 37.25(19) . . ? C1 Ir1 Cl1 84.11(15) . . ? N1 Ir1 Cl1 89.16(12) . . ? C16 Ir1 Cl1 111.26(15) . . ? C15 Ir1 Cl1 150.56(15) . . ? C14 Ir1 Cl1 144.24(15) . . ? C17 Ir1 Cl1 91.16(14) . . ? C18 Ir1 Cl1 106.52(14) . . ? C9 N1 C13 119.3(4) . . ? C9 N1 Ir1 124.0(3) . . ? C13 N1 Ir1 115.8(3) . . ? C2 C1 Ir1 128.8(4) . . ? C2 C1 H1A 115.6 . . ? Ir1 C1 H1A 115.6 . . ? C1 C2 C3 124.5(5) . . ? C1 C2 H2A 117.7 . . ? C3 C2 H2A 117.7 . . ? C8 C3 C4 118.1(5) . . ? C8 C3 C2 124.8(5) . . ? C4 C3 C2 117.0(5) . . ? C5 C4 C3 122.3(6) . . ? C5 C4 H4A 118.9 . . ? C3 C4 H4A 118.9 . . ? C6 C5 C4 119.6(6) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C7 119.3(6) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C6 C7 C8 122.1(6) . . ? C6 C7 H7A 118.9 . . ? C8 C7 H7A 118.9 . . ? C3 C8 C7 118.4(5) . . ? C3 C8 C9 125.9(5) . . ? C7 C8 C9 115.3(5) . . ? N1 C9 C10 119.6(5) . . ? N1 C9 C8 123.7(4) . . ? C10 C9 C8 116.7(5) . . ? C11 C10 C9 121.0(5) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 118.4(5) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? C11 C12 C13 119.1(5) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? N1 C13 C12 122.5(5) . . ? N1 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? C15 C14 C18 108.6(5) . . ? C15 C14 C19 127.1(6) . . ? C18 C14 C19 124.1(5) . . ? C15 C14 Ir1 69.6(3) . . ? C18 C14 Ir1 72.8(3) . . ? C19 C14 Ir1 127.3(4) . . ? C14 C15 C16 107.9(5) . . ? C14 C15 C20 127.0(5) . . ? C16 C15 C20 124.7(5) . . ? C14 C15 Ir1 71.8(3) . . ? C16 C15 Ir1 70.1(3) . . ? C20 C15 Ir1 129.1(4) . . ? C17 C16 C15 106.7(4) . . ? C17 C16 C21 125.5(5) . . ? C15 C16 C21 127.3(5) . . ? C17 C16 Ir1 72.6(3) . . ? C15 C16 Ir1 70.6(3) . . ? C21 C16 Ir1 127.9(4) . . ? C18 C17 C16 109.7(4) . . ? C18 C17 C22 126.4(5) . . ? C16 C17 C22 123.9(5) . . ? C18 C17 Ir1 72.7(3) . . ? C16 C17 Ir1 68.6(3) . . ? C22 C17 Ir1 125.8(4) . . ? C17 C18 C14 107.1(4) . . ? C17 C18 C23 127.9(5) . . ? C14 C18 C23 125.0(5) . . ? C17 C18 Ir1 70.1(3) . . ? C14 C18 Ir1 69.0(3) . . ? C23 C18 Ir1 127.2(4) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C22 H22D 109.5 . . ? H22B C22 H22D 109.5 . . ? H22C C22 H22D 109.5 . . ? C18 C23 H23D 109.5 . . ? C18 C23 H23A 109.5 . . ? H23D C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23D C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C9 -62.7(4) . . . . ? C16 Ir1 N1 C9 51.3(7) . . . . ? C15 Ir1 N1 C9 38.0(5) . . . . ? C14 Ir1 N1 C9 68.8(4) . . . . ? C17 Ir1 N1 C9 122.3(4) . . . . ? C18 Ir1 N1 C9 106.3(4) . . . . ? Cl1 Ir1 N1 C9 -146.9(4) . . . . ? C1 Ir1 N1 C13 128.2(4) . . . . ? C16 Ir1 N1 C13 -117.8(6) . . . . ? C15 Ir1 N1 C13 -131.1(4) . . . . ? C14 Ir1 N1 C13 -100.4(4) . . . . ? C17 Ir1 N1 C13 -46.8(5) . . . . ? C18 Ir1 N1 C13 -62.8(4) . . . . ? Cl1 Ir1 N1 C13 44.0(4) . . . . ? N1 Ir1 C1 C2 54.4(5) . . . . ? C16 Ir1 C1 C2 -105.5(5) . . . . ? C15 Ir1 C1 C2 -65.4(6) . . . . ? C14 Ir1 C1 C2 -38.4(7) . . . . ? C17 Ir1 C1 C2 -130.2(5) . . . . ? C18 Ir1 C1 C2 -80.3(10) . . . . ? Cl1 Ir1 C1 C2 143.9(5) . . . . ? Ir1 C1 C2 C3 6.7(9) . . . . ? C1 C2 C3 C8 -46.7(9) . . . . ? C1 C2 C3 C4 132.8(6) . . . . ? C8 C3 C4 C5 4.5(9) . . . . ? C2 C3 C4 C5 -175.0(6) . . . . ? C3 C4 C5 C6 -2.0(11) . . . . ? C4 C5 C6 C7 -1.6(11) . . . . ? C5 C6 C7 C8 2.7(11) . . . . ? C4 C3 C8 C7 -3.3(8) . . . . ? C2 C3 C8 C7 176.1(5) . . . . ? C4 C3 C8 C9 169.1(5) . . . . ? C2 C3 C8 C9 -11.4(9) . . . . ? C6 C7 C8 C3 -0.1(9) . . . . ? C6 C7 C8 C9 -173.3(6) . . . . ? C13 N1 C9 C10 -2.1(7) . . . . ? Ir1 N1 C9 C10 -170.8(4) . . . . ? C13 N1 C9 C8 175.3(5) . . . . ? Ir1 N1 C9 C8 6.6(7) . . . . ? C3 C8 C9 N1 53.0(8) . . . . ? C7 C8 C9 N1 -134.4(6) . . . . ? C3 C8 C9 C10 -129.6(6) . . . . ? C7 C8 C9 C10 43.1(7) . . . . ? N1 C9 C10 C11 3.2(8) . . . . ? C8 C9 C10 C11 -174.4(5) . . . . ? C9 C10 C11 C12 -2.3(9) . . . . ? C10 C11 C12 C13 0.4(9) . . . . ? C9 N1 C13 C12 0.2(8) . . . . ? Ir1 N1 C13 C12 169.9(5) . . . . ? C11 C12 C13 N1 0.7(9) . . . . ? C1 Ir1 C14 C15 -45.5(4) . . . . ? N1 Ir1 C14 C15 -134.8(3) . . . . ? C16 Ir1 C14 C15 38.3(3) . . . . ? C17 Ir1 C14 C15 81.5(3) . . . . ? C18 Ir1 C14 C15 118.1(4) . . . . ? Cl1 Ir1 C14 C15 130.5(3) . . . . ? C1 Ir1 C14 C18 -163.7(3) . . . . ? N1 Ir1 C14 C18 107.1(3) . . . . ? C16 Ir1 C14 C18 -79.9(3) . . . . ? C15 Ir1 C14 C18 -118.1(4) . . . . ? C17 Ir1 C14 C18 -36.6(3) . . . . ? Cl1 Ir1 C14 C18 12.4(4) . . . . ? C1 Ir1 C14 C19 76.2(6) . . . . ? N1 Ir1 C14 C19 -13.1(6) . . . . ? C16 Ir1 C14 C19 160.0(6) . . . . ? C15 Ir1 C14 C19 121.7(7) . . . . ? C17 Ir1 C14 C19 -156.8(6) . . . . ? C18 Ir1 C14 C19 -120.2(7) . . . . ? Cl1 Ir1 C14 C19 -107.8(6) . . . . ? C18 C14 C15 C16 1.6(6) . . . . ? C19 C14 C15 C16 176.9(5) . . . . ? Ir1 C14 C15 C16 -61.1(3) . . . . ? C18 C14 C15 C20 -171.5(5) . . . . ? C19 C14 C15 C20 3.8(9) . . . . ? Ir1 C14 C15 C20 125.8(6) . . . . ? C18 C14 C15 Ir1 62.7(3) . . . . ? C19 C14 C15 Ir1 -122.0(6) . . . . ? C1 Ir1 C15 C14 147.0(3) . . . . ? N1 Ir1 C15 C14 54.7(4) . . . . ? C16 Ir1 C15 C14 -117.6(4) . . . . ? C17 Ir1 C15 C14 -78.7(3) . . . . ? C18 Ir1 C15 C14 -37.2(3) . . . . ? Cl1 Ir1 C15 C14 -115.3(3) . . . . ? C1 Ir1 C15 C16 -95.4(3) . . . . ? N1 Ir1 C15 C16 172.3(3) . . . . ? C14 Ir1 C15 C16 117.6(4) . . . . ? C17 Ir1 C15 C16 38.9(3) . . . . ? C18 Ir1 C15 C16 80.4(3) . . . . ? Cl1 Ir1 C15 C16 2.3(5) . . . . ? C1 Ir1 C15 C20 23.7(6) . . . . ? N1 Ir1 C15 C20 -68.6(6) . . . . ? C16 Ir1 C15 C20 119.1(7) . . . . ? C14 Ir1 C15 C20 -123.3(7) . . . . ? C17 Ir1 C15 C20 158.0(6) . . . . ? C18 Ir1 C15 C20 -160.5(6) . . . . ? Cl1 Ir1 C15 C20 121.4(5) . . . . ? C14 C15 C16 C17 -1.9(6) . . . . ? C20 C15 C16 C17 171.4(5) . . . . ? Ir1 C15 C16 C17 -64.1(3) . . . . ? C14 C15 C16 C21 -174.3(5) . . . . ? C20 C15 C16 C21 -1.0(9) . . . . ? Ir1 C15 C16 C21 123.4(6) . . . . ? C14 C15 C16 Ir1 62.2(3) . . . . ? C20 C15 C16 Ir1 -124.5(5) . . . . ? C1 Ir1 C16 C17 -151.6(3) . . . . ? N1 Ir1 C16 C17 97.1(5) . . . . ? C15 Ir1 C16 C17 115.4(4) . . . . ? C14 Ir1 C16 C17 77.9(3) . . . . ? C18 Ir1 C16 C17 35.4(3) . . . . ? Cl1 Ir1 C16 C17 -63.3(3) . . . . ? C1 Ir1 C16 C15 93.0(3) . . . . ? N1 Ir1 C16 C15 -18.4(7) . . . . ? C14 Ir1 C16 C15 -37.6(3) . . . . ? C17 Ir1 C16 C15 -115.4(4) . . . . ? C18 Ir1 C16 C15 -80.0(3) . . . . ? Cl1 Ir1 C16 C15 -178.8(3) . . . . ? C1 Ir1 C16 C21 -29.7(6) . . . . ? N1 Ir1 C16 C21 -141.1(6) . . . . ? C15 Ir1 C16 C21 -122.7(7) . . . . ? C14 Ir1 C16 C21 -160.3(6) . . . . ? C17 Ir1 C16 C21 121.9(6) . . . . ? C18 Ir1 C16 C21 157.3(6) . . . . ? Cl1 Ir1 C16 C21 58.5(6) . . . . ? C15 C16 C17 C18 1.5(6) . . . . ? C21 C16 C17 C18 174.1(5) . . . . ? Ir1 C16 C17 C18 -61.3(4) . . . . ? C15 C16 C17 C22 -177.7(5) . . . . ? C21 C16 C17 C22 -5.0(9) . . . . ? Ir1 C16 C17 C22 119.5(5) . . . . ? C15 C16 C17 Ir1 62.8(3) . . . . ? C21 C16 C17 Ir1 -124.6(6) . . . . ? C1 Ir1 C17 C18 160.8(3) . . . . ? N1 Ir1 C17 C18 -26.3(4) . . . . ? C16 Ir1 C17 C18 120.1(4) . . . . ? C15 Ir1 C17 C18 80.7(3) . . . . ? C14 Ir1 C17 C18 37.5(3) . . . . ? Cl1 Ir1 C17 C18 -116.3(3) . . . . ? C1 Ir1 C17 C16 40.7(4) . . . . ? N1 Ir1 C17 C16 -146.4(3) . . . . ? C15 Ir1 C17 C16 -39.4(3) . . . . ? C14 Ir1 C17 C16 -82.6(3) . . . . ? C18 Ir1 C17 C16 -120.1(4) . . . . ? Cl1 Ir1 C17 C16 123.6(3) . . . . ? C1 Ir1 C17 C22 -76.4(6) . . . . ? N1 Ir1 C17 C22 96.6(5) . . . . ? C16 Ir1 C17 C22 -117.1(6) . . . . ? C15 Ir1 C17 C22 -156.5(6) . . . . ? C14 Ir1 C17 C22 160.4(6) . . . . ? C18 Ir1 C17 C22 122.8(6) . . . . ? Cl1 Ir1 C17 C22 6.5(5) . . . . ? C16 C17 C18 C14 -0.5(6) . . . . ? C22 C17 C18 C14 178.6(5) . . . . ? Ir1 C17 C18 C14 -59.3(3) . . . . ? C16 C17 C18 C23 -179.0(5) . . . . ? C22 C17 C18 C23 0.1(9) . . . . ? Ir1 C17 C18 C23 122.2(5) . . . . ? C16 C17 C18 Ir1 58.8(4) . . . . ? C22 C17 C18 Ir1 -122.1(5) . . . . ? C15 C14 C18 C17 -0.7(5) . . . . ? C19 C14 C18 C17 -176.1(5) . . . . ? Ir1 C14 C18 C17 60.0(3) . . . . ? C15 C14 C18 C23 177.9(5) . . . . ? C19 C14 C18 C23 2.4(8) . . . . ? Ir1 C14 C18 C23 -121.4(5) . . . . ? C15 C14 C18 Ir1 -60.7(3) . . . . ? C19 C14 C18 Ir1 123.8(5) . . . . ? C1 Ir1 C18 C17 -64.4(9) . . . . ? N1 Ir1 C18 C17 162.5(3) . . . . ? C16 Ir1 C18 C17 -36.9(3) . . . . ? C15 Ir1 C18 C17 -80.7(3) . . . . ? C14 Ir1 C18 C17 -118.3(4) . . . . ? Cl1 Ir1 C18 C17 69.2(3) . . . . ? C1 Ir1 C18 C14 53.9(9) . . . . ? N1 Ir1 C18 C14 -79.2(3) . . . . ? C16 Ir1 C18 C14 81.4(3) . . . . ? C15 Ir1 C18 C14 37.6(3) . . . . ? C17 Ir1 C18 C14 118.3(4) . . . . ? Cl1 Ir1 C18 C14 -172.5(3) . . . . ? C1 Ir1 C18 C23 172.5(7) . . . . ? N1 Ir1 C18 C23 39.5(6) . . . . ? C16 Ir1 C18 C23 -160.0(6) . . . . ? C15 Ir1 C18 C23 156.2(6) . . . . ? C14 Ir1 C18 C23 118.6(6) . . . . ? C17 Ir1 C18 C23 -123.1(7) . . . . ? Cl1 Ir1 C18 C23 -53.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 3.587 _refine_diff_density_min -3.465 _refine_diff_density_rms 0.215 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_4e _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll61 _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 Cl N Rh' _chemical_formula_sum 'C23 H25 Cl N Rh' _chemical_formula_weight 453.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4386(17) _cell_length_b 14.676(3) _cell_length_c 16.346(3) _cell_angle_alpha 78.351(4) _cell_angle_beta 81.627(4) _cell_angle_gamma 90.045(4) _cell_volume 1960.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 193.0(5) _cell_measurement_reflns_used 7082 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 36.22 _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7374 _exptl_absorpt_correction_T_max 0.9324 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45549 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 29.35 _reflns_number_total 10685 _reflns_number_gt 8305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The structure was integrated and refined as a non-merohedral twin, with twin law, [-1 0 0 / 0 1 0 / 0 0.45 -1], a 180 degree rotation around direct lattice [0 1 0]. There were 2425 unique reflections in the first component, 2354 unique reflections in the second component, and 18606 overlapping reflections. The mass ratio of the two components refined to 50:50. The R1 residual decreased from 0.146 to 0.045 with the application of the twin law. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+2.1379P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10685 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.96779(6) 0.03787(3) 0.72026(3) 0.01872(11) Uani 1 1 d . . . Cl1 Cl 1.22402(18) 0.04431(12) 0.63219(11) 0.0312(3) Uani 1 1 d . . . N1 N 0.9531(6) 0.1848(4) 0.6935(3) 0.0208(10) Uani 1 1 d . . . C1 C 1.0934(8) 0.0567(5) 0.8104(4) 0.0238(14) Uani 1 1 d . . . H1A H 1.1980 0.0325 0.8065 0.029 Uiso 1 1 calc R . . C2 C 1.0518(8) 0.0980(4) 0.8747(4) 0.0247(14) Uani 1 1 d . . . H2A H 1.1296 0.1027 0.9103 0.030 Uiso 1 1 calc R . . C3 C 0.8954(8) 0.1371(4) 0.8953(4) 0.0239(13) Uani 1 1 d . . . C4 C 0.8213(9) 0.1155(5) 0.9793(4) 0.0319(16) Uani 1 1 d . . . H4A H 0.8769 0.0789 1.0202 0.038 Uiso 1 1 calc R . . C5 C 0.6712(10) 0.1451(5) 1.0052(5) 0.0389(19) Uani 1 1 d . . . H5A H 0.6232 0.1269 1.0625 0.047 Uiso 1 1 calc R . . C6 C 0.5910(10) 0.2010(6) 0.9479(5) 0.0389(18) Uani 1 1 d . . . H6A H 0.4868 0.2212 0.9650 0.047 Uiso 1 1 calc R . . C7 C 0.6625(8) 0.2270(5) 0.8661(4) 0.0265(14) Uani 1 1 d . . . H7A H 0.6083 0.2680 0.8274 0.032 Uiso 1 1 calc R . . C8 C 0.8127(7) 0.1956(4) 0.8369(4) 0.0230(13) Uani 1 1 d . . . C9 C 0.8817(7) 0.2368(4) 0.7479(4) 0.0213(12) Uani 1 1 d . . . C10 C 0.8695(8) 0.3338(5) 0.7204(5) 0.0297(14) Uani 1 1 d . . . H10A H 0.8187 0.3695 0.7586 0.036 Uiso 1 1 calc R . . C11 C 0.9296(9) 0.3772(5) 0.6394(4) 0.0333(15) Uani 1 1 d . . . H11A H 0.9196 0.4423 0.6209 0.040 Uiso 1 1 calc R . . C12 C 1.0058(7) 0.3238(5) 0.5850(4) 0.0300(14) Uani 1 1 d . . . H12A H 1.0525 0.3520 0.5291 0.036 Uiso 1 1 calc R . . C13 C 1.0120(7) 0.2289(5) 0.6140(4) 0.0261(12) Uani 1 1 d . . . H13A H 1.0605 0.1925 0.5758 0.031 Uiso 1 1 calc R . . C14 C 0.7165(7) -0.0024(4) 0.7512(4) 0.0223(13) Uani 1 1 d . . . C15 C 0.8050(8) -0.0670(4) 0.8018(4) 0.0244(14) Uani 1 1 d . . . C16 C 0.9162(8) -0.1070(4) 0.7448(4) 0.0240(13) Uani 1 1 d . . . C17 C 0.8776(8) -0.0748(5) 0.6609(4) 0.0247(14) Uani 1 1 d . . . C18 C 0.7607(7) -0.0105(4) 0.6634(4) 0.0227(12) Uani 1 1 d . . . C19 C 0.5750(8) 0.0491(6) 0.7824(5) 0.0382(19) Uani 1 1 d . . . H19A H 0.4772 0.0229 0.7692 0.057 Uiso 1 1 calc R . . H19B H 0.5879 0.1150 0.7548 0.057 Uiso 1 1 calc R . . H19C H 0.5672 0.0431 0.8437 0.057 Uiso 1 1 calc R . . C20 C 0.7820(9) -0.0924(5) 0.8965(4) 0.0313(16) Uani 1 1 d . . . H20A H 0.7305 -0.1544 0.9156 0.047 Uiso 1 1 calc R . . H20B H 0.7142 -0.0468 0.9198 0.047 Uiso 1 1 calc R . . H20C H 0.8865 -0.0926 0.9161 0.047 Uiso 1 1 calc R . . C21 C 1.0289(9) -0.1824(5) 0.7703(6) 0.043(2) Uani 1 1 d . . . H21A H 0.9789 -0.2430 0.7712 0.065 Uiso 1 1 calc R . . H21B H 1.0536 -0.1805 0.8267 0.065 Uiso 1 1 calc R . . H21C H 1.1280 -0.1732 0.7297 0.065 Uiso 1 1 calc R . . C22 C 0.9593(10) -0.1111(6) 0.5863(5) 0.040(2) Uani 1 1 d . . . H22A H 0.9371 -0.1782 0.5953 0.060 Uiso 1 1 calc R . . H22B H 1.0751 -0.0992 0.5800 0.060 Uiso 1 1 calc R . . H22C H 0.9187 -0.0795 0.5351 0.060 Uiso 1 1 calc R . . C23 C 0.6832(8) 0.0418(6) 0.5923(5) 0.0379(16) Uani 1 1 d . . . H23A H 0.5669 0.0309 0.6054 0.057 Uiso 1 1 calc R . . H23B H 0.7235 0.0202 0.5404 0.057 Uiso 1 1 calc R . . H23C H 0.7085 0.1085 0.5845 0.057 Uiso 1 1 calc R . . Rh2 Rh 0.46789(6) 0.58297(3) 0.71845(3) 0.01792(10) Uani 1 1 d . A 1 Cl2 Cl 0.7203(2) 0.60717(12) 0.62596(12) 0.0336(4) Uani 1 1 d . A 1 N2 N 0.4376(6) 0.4467(3) 0.6962(3) 0.0202(10) Uani 1 1 d . A 1 C24 C 0.5988(8) 0.5235(5) 0.8082(4) 0.0254(14) Uani 1 1 d . A 1 H24A H 0.7047 0.5481 0.8033 0.030 Uiso 1 1 calc R A 1 C25 C 0.5530(8) 0.4541(5) 0.8729(4) 0.0280(15) Uani 1 1 d . A 1 H25A H 0.6314 0.4318 0.9077 0.034 Uiso 1 1 calc R A 1 C26 C 0.3949(8) 0.4082(5) 0.8965(4) 0.0242(13) Uani 1 1 d . A 1 C27 C 0.3236(10) 0.3964(5) 0.9821(4) 0.0356(18) Uani 1 1 d . A 1 H27A H 0.3818 0.4172 1.0208 0.043 Uiso 1 1 calc R A 1 C28 C 0.1739(10) 0.3564(6) 1.0113(5) 0.0395(19) Uani 1 1 d . A 1 H28A H 0.1287 0.3509 1.0688 0.047 Uiso 1 1 calc R A 1 C29 C 0.0897(9) 0.3240(5) 0.9563(5) 0.0398(19) Uani 1 1 d . A 1 H29A H -0.0140 0.2959 0.9755 0.048 Uiso 1 1 calc R A 1 C30 C 0.1576(9) 0.3329(5) 0.8733(5) 0.0353(16) Uani 1 1 d . A 1 H30A H 0.0991 0.3100 0.8359 0.042 Uiso 1 1 calc R A 1 C31 C 0.3103(8) 0.3747(4) 0.8416(4) 0.0239(13) Uani 1 1 d . A 1 C32 C 0.3707(7) 0.3723(4) 0.7511(4) 0.0231(13) Uani 1 1 d . A 1 C33 C 0.3508(8) 0.2889(4) 0.7264(4) 0.0241(13) Uani 1 1 d . A 1 H33A H 0.3062 0.2362 0.7672 0.029 Uiso 1 1 calc R A 1 C34 C 0.3941(8) 0.2807(5) 0.6443(5) 0.0308(15) Uani 1 1 d . A 1 H34A H 0.3805 0.2231 0.6276 0.037 Uiso 1 1 calc R A 1 C35 C 0.4576(9) 0.3579(5) 0.5869(4) 0.0321(16) Uani 1 1 d . A 1 H35A H 0.4839 0.3562 0.5287 0.039 Uiso 1 1 calc R A 1 C36 C 0.4824(8) 0.4384(5) 0.6154(4) 0.0298(13) Uani 1 1 d . A 1 H36A H 0.5336 0.4905 0.5763 0.036 Uiso 1 1 calc R A 1 C37 C 0.2171(7) 0.6146(4) 0.7491(4) 0.0255(14) Uani 1 1 d . A 1 C38 C 0.3102(7) 0.6531(4) 0.8007(4) 0.0227(13) Uani 1 1 d . A 1 C39 C 0.4236(8) 0.7179(4) 0.7457(4) 0.0255(14) Uani 1 1 d . A 1 C40 C 0.3885(8) 0.7247(5) 0.6595(4) 0.0277(14) Uani 1 1 d . A 1 C41 C 0.2649(8) 0.6609(5) 0.6618(4) 0.0281(14) Uani 1 1 d . A 1 C42 C 0.0759(8) 0.5494(6) 0.7779(5) 0.0407(19) Uani 1 1 d . A 1 H42A H -0.0226 0.5846 0.7755 0.061 Uiso 1 1 calc R A 1 H42B H 0.0789 0.5165 0.8361 0.061 Uiso 1 1 calc R A 1 H42C H 0.0783 0.5042 0.7410 0.061 Uiso 1 1 calc R A 1 C43 C 0.2847(9) 0.6380(6) 0.8939(5) 0.0388(19) Uani 1 1 d . A 1 H43A H 0.2133 0.6851 0.9120 0.058 Uiso 1 1 calc R A 1 H43B H 0.3879 0.6429 0.9138 0.058 Uiso 1 1 calc R A 1 H43C H 0.2361 0.5759 0.9178 0.058 Uiso 1 1 calc R A 1 C44 C 0.5408(10) 0.7781(5) 0.7712(5) 0.0423(19) Uani 1 1 d . A 1 H44A H 0.4935 0.8383 0.7753 0.063 Uiso 1 1 calc R A 1 H44B H 0.6376 0.7879 0.7289 0.063 Uiso 1 1 calc R A 1 H44C H 0.5688 0.7480 0.8262 0.063 Uiso 1 1 calc R A 1 C45 C 0.4715(9) 0.7921(5) 0.5847(4) 0.0400(18) Uani 1 1 d . A 1 H45A H 0.4408 0.8555 0.5892 0.060 Uiso 1 1 calc R A 1 H45B H 0.4405 0.7779 0.5330 0.060 Uiso 1 1 calc R A 1 H45C H 0.5877 0.7871 0.5828 0.060 Uiso 1 1 calc R A 1 C46 C 0.1847(9) 0.6437(7) 0.5904(5) 0.048(2) Uani 1 1 d . A 1 H46A H 0.0702 0.6555 0.6017 0.071 Uiso 1 1 calc R A 1 H46B H 0.1987 0.5789 0.5846 0.071 Uiso 1 1 calc R A 1 H46C H 0.2328 0.6853 0.5379 0.071 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.0117(2) 0.0171(2) 0.0275(3) -0.00509(18) -0.00248(18) 0.00053(17) Cl1 0.0164(7) 0.0363(8) 0.0406(9) -0.0129(7) 0.0035(6) -0.0021(6) N1 0.019(2) 0.026(3) 0.021(2) -0.0096(19) -0.0073(19) -0.0009(19) C1 0.010(3) 0.023(3) 0.039(4) -0.004(3) -0.008(3) 0.001(2) C2 0.021(3) 0.024(3) 0.030(4) -0.002(3) -0.010(3) 0.000(2) C3 0.027(3) 0.013(3) 0.033(4) -0.006(2) -0.005(3) -0.001(2) C4 0.041(4) 0.025(4) 0.029(4) -0.004(3) -0.007(3) 0.003(3) C5 0.057(5) 0.028(4) 0.029(4) -0.008(3) 0.009(3) 0.000(3) C6 0.039(4) 0.034(4) 0.040(4) -0.007(3) 0.006(3) 0.007(3) C7 0.028(3) 0.019(3) 0.030(3) -0.001(3) -0.002(3) 0.008(3) C8 0.021(3) 0.022(3) 0.027(3) -0.009(2) -0.003(2) 0.002(2) C9 0.023(3) 0.020(3) 0.020(3) -0.003(2) -0.004(2) 0.000(2) C10 0.025(3) 0.022(3) 0.044(4) -0.010(3) -0.009(3) 0.000(2) C11 0.041(4) 0.018(3) 0.041(4) 0.002(3) -0.019(3) -0.003(3) C12 0.026(3) 0.035(3) 0.027(3) -0.002(2) -0.006(2) -0.008(2) C13 0.021(3) 0.031(3) 0.026(3) -0.008(2) -0.001(2) -0.002(2) C14 0.011(3) 0.017(3) 0.037(4) -0.007(2) 0.001(2) -0.007(2) C15 0.019(3) 0.022(3) 0.031(3) -0.005(3) -0.001(3) -0.008(2) C16 0.021(3) 0.014(3) 0.035(4) -0.001(2) -0.005(3) -0.003(2) C17 0.021(3) 0.019(3) 0.036(4) -0.011(3) -0.002(3) -0.002(2) C18 0.018(3) 0.018(3) 0.032(3) -0.004(2) -0.006(2) -0.006(2) C19 0.016(3) 0.035(4) 0.067(6) -0.023(4) 0.001(3) 0.001(3) C20 0.035(4) 0.035(4) 0.020(3) -0.002(3) 0.003(3) -0.006(3) C21 0.031(4) 0.021(3) 0.077(6) -0.007(4) -0.012(4) 0.010(3) C22 0.038(4) 0.032(4) 0.051(5) -0.022(4) 0.011(4) -0.001(3) C23 0.027(4) 0.044(4) 0.041(4) 0.001(3) -0.012(3) -0.004(3) Rh2 0.0129(2) 0.0158(2) 0.0256(2) -0.00564(18) -0.00284(18) 0.00017(17) Cl2 0.0196(7) 0.0371(9) 0.0405(9) -0.0064(7) 0.0058(6) -0.0014(6) N2 0.019(2) 0.014(2) 0.032(3) -0.0139(19) -0.007(2) -0.0011(18) C24 0.019(3) 0.030(3) 0.033(4) -0.013(3) -0.011(3) 0.005(3) C25 0.025(4) 0.028(3) 0.038(4) -0.015(3) -0.017(3) 0.010(3) C26 0.029(4) 0.024(3) 0.021(3) -0.004(2) -0.009(3) 0.007(3) C27 0.053(5) 0.029(4) 0.026(4) -0.010(3) -0.005(3) 0.007(4) C28 0.054(5) 0.032(4) 0.028(4) -0.008(3) 0.010(3) -0.001(4) C29 0.038(4) 0.029(4) 0.046(4) -0.008(3) 0.018(3) -0.012(3) C30 0.029(4) 0.031(4) 0.043(4) -0.005(3) -0.001(3) -0.005(3) C31 0.027(3) 0.018(3) 0.027(3) -0.006(2) -0.003(3) 0.003(2) C32 0.015(3) 0.023(3) 0.032(3) -0.007(2) -0.008(2) 0.003(2) C33 0.024(3) 0.022(3) 0.026(3) -0.003(2) -0.005(2) -0.005(2) C34 0.033(4) 0.026(3) 0.038(4) -0.014(3) -0.012(3) 0.005(3) C35 0.043(4) 0.036(4) 0.021(3) -0.017(3) -0.005(3) 0.007(3) C36 0.038(3) 0.022(3) 0.029(3) -0.005(2) -0.005(3) 0.002(2) C37 0.014(3) 0.018(3) 0.044(4) -0.006(3) -0.005(3) 0.000(2) C38 0.016(3) 0.023(3) 0.029(3) -0.005(3) -0.002(2) 0.005(2) C39 0.019(3) 0.017(3) 0.040(4) -0.006(3) 0.000(3) -0.003(2) C40 0.027(3) 0.020(3) 0.034(4) -0.003(3) 0.000(3) 0.008(3) C41 0.018(3) 0.030(3) 0.040(4) -0.013(3) -0.012(3) 0.009(3) C42 0.019(4) 0.033(4) 0.068(6) -0.008(4) 0.000(3) 0.000(3) C43 0.037(4) 0.046(5) 0.037(4) -0.018(4) -0.002(3) 0.018(4) C44 0.040(5) 0.031(4) 0.059(5) -0.020(3) -0.002(4) -0.015(3) C45 0.053(5) 0.027(3) 0.033(4) 0.004(3) 0.003(3) 0.005(3) C46 0.035(4) 0.070(6) 0.049(5) -0.026(4) -0.026(4) 0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C1 1.997(7) . ? Rh1 C16 2.116(6) . ? Rh1 N1 2.120(5) . ? Rh1 C15 2.160(6) . ? Rh1 C14 2.160(6) . ? Rh1 C17 2.261(7) . ? Rh1 C18 2.271(6) . ? Rh1 Cl1 2.4072(17) . ? N1 C13 1.352(8) . ? N1 C9 1.363(8) . ? C1 C2 1.321(9) . ? C1 H1A 0.9500 . ? C2 C3 1.461(9) . ? C2 H2A 0.9500 . ? C3 C4 1.396(9) . ? C3 C8 1.413(9) . ? C4 C5 1.375(10) . ? C4 H4A 0.9500 . ? C5 C6 1.372(11) . ? C5 H5A 0.9500 . ? C6 C7 1.362(10) . ? C6 H6A 0.9500 . ? C7 C8 1.400(9) . ? C7 H7A 0.9500 . ? C8 C9 1.489(8) . ? C9 C10 1.412(9) . ? C10 C11 1.371(10) . ? C10 H10A 0.9500 . ? C11 C12 1.392(10) . ? C11 H11A 0.9500 . ? C12 C13 1.381(9) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.416(9) . ? C14 C18 1.458(9) . ? C14 C19 1.495(9) . ? C15 C16 1.436(9) . ? C15 C20 1.502(9) . ? C16 C17 1.441(10) . ? C16 C21 1.494(9) . ? C17 C18 1.368(9) . ? C17 C22 1.504(10) . ? C18 C23 1.493(9) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? Rh2 C24 2.022(7) . ? Rh2 N2 2.125(5) . ? Rh2 C39 2.138(7) . ? Rh2 C38 2.162(6) . ? Rh2 C37 2.175(6) . ? Rh2 C40 2.256(6) . ? Rh2 C41 2.266(6) . ? Rh2 Cl2 2.4071(17) . ? N2 C32 1.331(8) . ? N2 C36 1.349(8) . ? C24 C25 1.323(10) . ? C24 H24A 0.9500 . ? C25 C26 1.458(9) . ? C25 H25A 0.9500 . ? C26 C31 1.386(9) . ? C26 C27 1.417(9) . ? C27 C28 1.371(11) . ? C27 H27A 0.9500 . ? C28 C29 1.376(12) . ? C28 H28A 0.9500 . ? C29 C30 1.374(10) . ? C29 H29A 0.9500 . ? C30 C31 1.408(9) . ? C30 H30A 0.9500 . ? C31 C32 1.500(9) . ? C32 C33 1.381(9) . ? C33 C34 1.368(9) . ? C33 H33A 0.9500 . ? C34 C35 1.369(10) . ? C34 H34A 0.9500 . ? C35 C36 1.382(9) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 C38 1.426(9) . ? C37 C41 1.449(10) . ? C37 C42 1.486(9) . ? C38 C39 1.426(9) . ? C38 C43 1.479(10) . ? C39 C40 1.466(10) . ? C39 C44 1.484(9) . ? C40 C41 1.392(9) . ? C40 C45 1.491(9) . ? C41 C46 1.495(9) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 C16 105.1(3) . . ? C1 Rh1 N1 85.4(2) . . ? C16 Rh1 N1 164.6(2) . . ? C1 Rh1 C15 95.2(3) . . ? C16 Rh1 C15 39.2(2) . . ? N1 Rh1 C15 130.1(2) . . ? C1 Rh1 C14 120.5(3) . . ? C16 Rh1 C14 64.6(2) . . ? N1 Rh1 C14 100.4(2) . . ? C15 Rh1 C14 38.3(2) . . ? C1 Rh1 C17 141.8(3) . . ? C16 Rh1 C17 38.3(3) . . ? N1 Rh1 C17 132.8(2) . . ? C15 Rh1 C17 63.3(2) . . ? C14 Rh1 C17 62.1(2) . . ? C1 Rh1 C18 157.7(2) . . ? C16 Rh1 C18 62.9(2) . . ? N1 Rh1 C18 103.4(2) . . ? C15 Rh1 C18 63.4(2) . . ? C14 Rh1 C18 38.3(2) . . ? C17 Rh1 C18 35.1(2) . . ? C1 Rh1 Cl1 85.39(19) . . ? C16 Rh1 Cl1 99.87(18) . . ? N1 Rh1 Cl1 92.07(14) . . ? C15 Rh1 Cl1 137.79(19) . . ? C14 Rh1 Cl1 151.79(18) . . ? C17 Rh1 Cl1 90.91(18) . . ? C18 Rh1 Cl1 114.24(17) . . ? C13 N1 C9 118.1(5) . . ? C13 N1 Rh1 116.4(4) . . ? C9 N1 Rh1 125.4(4) . . ? C2 C1 Rh1 129.2(5) . . ? C2 C1 H1A 115.4 . . ? Rh1 C1 H1A 115.4 . . ? C1 C2 C3 125.1(6) . . ? C1 C2 H2A 117.5 . . ? C3 C2 H2A 117.5 . . ? C4 C3 C8 117.1(6) . . ? C4 C3 C2 117.7(6) . . ? C8 C3 C2 125.2(6) . . ? C5 C4 C3 122.7(7) . . ? C5 C4 H4A 118.7 . . ? C3 C4 H4A 118.7 . . ? C6 C5 C4 119.8(7) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C7 C6 C5 119.2(7) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C6 C7 C8 122.6(7) . . ? C6 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C7 C8 C3 118.6(6) . . ? C7 C8 C9 116.3(6) . . ? C3 C8 C9 124.7(6) . . ? N1 C9 C10 120.0(6) . . ? N1 C9 C8 122.7(5) . . ? C10 C9 C8 117.3(6) . . ? C11 C10 C9 121.0(6) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 118.5(6) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? C13 C12 C11 118.5(6) . . ? C13 C12 H12A 120.8 . . ? C11 C12 H12A 120.8 . . ? N1 C13 C12 123.9(6) . . ? N1 C13 H13A 118.1 . . ? C12 C13 H13A 118.1 . . ? C15 C14 C18 108.4(5) . . ? C15 C14 C19 126.1(6) . . ? C18 C14 C19 124.1(6) . . ? C15 C14 Rh1 70.9(3) . . ? C18 C14 Rh1 75.0(3) . . ? C19 C14 Rh1 130.9(5) . . ? C14 C15 C16 106.6(6) . . ? C14 C15 C20 126.9(6) . . ? C16 C15 C20 126.4(6) . . ? C14 C15 Rh1 70.9(3) . . ? C16 C15 Rh1 68.7(3) . . ? C20 C15 Rh1 127.5(5) . . ? C15 C16 C17 107.5(6) . . ? C15 C16 C21 125.4(7) . . ? C17 C16 C21 126.1(7) . . ? C15 C16 Rh1 72.0(4) . . ? C17 C16 Rh1 76.3(4) . . ? C21 C16 Rh1 126.2(5) . . ? C18 C17 C16 109.3(6) . . ? C18 C17 C22 128.8(7) . . ? C16 C17 C22 121.9(7) . . ? C18 C17 Rh1 72.8(4) . . ? C16 C17 Rh1 65.4(3) . . ? C22 C17 Rh1 127.9(5) . . ? C17 C18 C14 107.7(6) . . ? C17 C18 C23 128.5(6) . . ? C14 C18 C23 123.8(6) . . ? C17 C18 Rh1 72.1(4) . . ? C14 C18 Rh1 66.7(3) . . ? C23 C18 Rh1 128.0(4) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C24 Rh2 N2 86.1(2) . . ? C24 Rh2 C39 103.2(3) . . ? N2 Rh2 C39 163.2(2) . . ? C24 Rh2 C38 95.2(3) . . ? N2 Rh2 C38 127.6(2) . . ? C39 Rh2 C38 38.7(2) . . ? C24 Rh2 C37 122.0(3) . . ? N2 Rh2 C37 98.9(2) . . ? C39 Rh2 C37 64.3(2) . . ? C38 Rh2 C37 38.4(2) . . ? C24 Rh2 C40 139.8(3) . . ? N2 Rh2 C40 134.0(2) . . ? C39 Rh2 C40 38.9(3) . . ? C38 Rh2 C40 63.7(2) . . ? C37 Rh2 C40 62.4(2) . . ? C24 Rh2 C41 158.4(3) . . ? N2 Rh2 C41 103.2(2) . . ? C39 Rh2 C41 63.4(2) . . ? C38 Rh2 C41 63.6(2) . . ? C37 Rh2 C41 38.0(2) . . ? C40 Rh2 C41 35.9(2) . . ? C24 Rh2 Cl2 85.2(2) . . ? N2 Rh2 Cl2 91.96(15) . . ? C39 Rh2 Cl2 102.58(17) . . ? C38 Rh2 Cl2 140.41(18) . . ? C37 Rh2 Cl2 151.13(18) . . ? C40 Rh2 Cl2 90.95(17) . . ? C41 Rh2 Cl2 113.45(19) . . ? C32 N2 C36 117.8(5) . . ? C32 N2 Rh2 127.4(4) . . ? C36 N2 Rh2 114.7(4) . . ? C25 C24 Rh2 127.1(5) . . ? C25 C24 H24A 116.5 . . ? Rh2 C24 H24A 116.5 . . ? C24 C25 C26 126.8(6) . . ? C24 C25 H25A 116.6 . . ? C26 C25 H25A 116.6 . . ? C31 C26 C27 117.8(7) . . ? C31 C26 C25 124.9(6) . . ? C27 C26 C25 117.3(6) . . ? C28 C27 C26 122.6(7) . . ? C28 C27 H27A 118.7 . . ? C26 C27 H27A 118.7 . . ? C27 C28 C29 119.3(7) . . ? C27 C28 H28A 120.3 . . ? C29 C28 H28A 120.3 . . ? C30 C29 C28 119.2(7) . . ? C30 C29 H29A 120.4 . . ? C28 C29 H29A 120.4 . . ? C29 C30 C31 122.6(7) . . ? C29 C30 H30A 118.7 . . ? C31 C30 H30A 118.7 . . ? C26 C31 C30 118.4(6) . . ? C26 C31 C32 126.0(6) . . ? C30 C31 C32 115.4(6) . . ? N2 C32 C33 121.0(6) . . ? N2 C32 C31 122.3(6) . . ? C33 C32 C31 116.7(6) . . ? C34 C33 C32 121.3(6) . . ? C34 C33 H33A 119.4 . . ? C32 C33 H33A 119.4 . . ? C33 C34 C35 118.0(6) . . ? C33 C34 H34A 121.0 . . ? C35 C34 H34A 121.0 . . ? C34 C35 C36 118.5(6) . . ? C34 C35 H35A 120.7 . . ? C36 C35 H35A 120.7 . . ? N2 C36 C35 123.3(6) . . ? N2 C36 H36A 118.4 . . ? C35 C36 H36A 118.4 . . ? C38 C37 C41 108.7(5) . . ? C38 C37 C42 127.2(6) . . ? C41 C37 C42 123.4(6) . . ? C38 C37 Rh2 70.3(3) . . ? C41 C37 Rh2 74.4(4) . . ? C42 C37 Rh2 128.9(5) . . ? C37 C38 C39 107.3(6) . . ? C37 C38 C43 127.3(6) . . ? C39 C38 C43 125.1(7) . . ? C37 C38 Rh2 71.3(4) . . ? C39 C38 Rh2 69.7(4) . . ? C43 C38 Rh2 129.3(5) . . ? C38 C39 C40 107.6(6) . . ? C38 C39 C44 126.5(7) . . ? C40 C39 C44 125.3(6) . . ? C38 C39 Rh2 71.6(4) . . ? C40 C39 Rh2 74.9(4) . . ? C44 C39 Rh2 125.7(5) . . ? C41 C40 C39 108.3(6) . . ? C41 C40 C45 127.9(7) . . ? C39 C40 C45 123.8(6) . . ? C41 C40 Rh2 72.5(4) . . ? C39 C40 Rh2 66.2(3) . . ? C45 C40 Rh2 128.2(5) . . ? C40 C41 C37 107.9(6) . . ? C40 C41 C46 128.2(7) . . ? C37 C41 C46 123.8(7) . . ? C40 C41 Rh2 71.7(4) . . ? C37 C41 Rh2 67.6(3) . . ? C46 C41 Rh2 128.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C13 122.0(5) . . . . ? C16 Rh1 N1 C13 -104.3(9) . . . . ? C15 Rh1 N1 C13 -145.1(4) . . . . ? C14 Rh1 N1 C13 -117.8(4) . . . . ? C17 Rh1 N1 C13 -56.3(5) . . . . ? C18 Rh1 N1 C13 -78.7(5) . . . . ? Cl1 Rh1 N1 C13 36.8(4) . . . . ? C1 Rh1 N1 C9 -61.9(5) . . . . ? C16 Rh1 N1 C9 71.7(10) . . . . ? C15 Rh1 N1 C9 31.0(6) . . . . ? C14 Rh1 N1 C9 58.3(5) . . . . ? C17 Rh1 N1 C9 119.7(5) . . . . ? C18 Rh1 N1 C9 97.4(5) . . . . ? Cl1 Rh1 N1 C9 -147.1(5) . . . . ? C16 Rh1 C1 C2 -110.9(6) . . . . ? N1 Rh1 C1 C2 57.7(6) . . . . ? C15 Rh1 C1 C2 -72.2(7) . . . . ? C14 Rh1 C1 C2 -41.7(7) . . . . ? C17 Rh1 C1 C2 -124.3(6) . . . . ? C18 Rh1 C1 C2 -57.0(10) . . . . ? Cl1 Rh1 C1 C2 150.1(6) . . . . ? Rh1 C1 C2 C3 2.4(10) . . . . ? C1 C2 C3 C4 133.0(7) . . . . ? C1 C2 C3 C8 -47.2(10) . . . . ? C8 C3 C4 C5 3.1(10) . . . . ? C2 C3 C4 C5 -177.1(6) . . . . ? C3 C4 C5 C6 -2.4(11) . . . . ? C4 C5 C6 C7 -0.6(12) . . . . ? C5 C6 C7 C8 2.9(12) . . . . ? C6 C7 C8 C3 -2.1(11) . . . . ? C6 C7 C8 C9 -174.7(7) . . . . ? C4 C3 C8 C7 -0.9(9) . . . . ? C2 C3 C8 C7 179.4(6) . . . . ? C4 C3 C8 C9 171.0(6) . . . . ? C2 C3 C8 C9 -8.7(10) . . . . ? C13 N1 C9 C10 0.7(9) . . . . ? Rh1 N1 C9 C10 -175.3(4) . . . . ? C13 N1 C9 C8 -180.0(5) . . . . ? Rh1 N1 C9 C8 4.0(8) . . . . ? C7 C8 C9 N1 -136.0(6) . . . . ? C3 C8 C9 N1 52.0(9) . . . . ? C7 C8 C9 C10 43.4(8) . . . . ? C3 C8 C9 C10 -128.7(7) . . . . ? N1 C9 C10 C11 -0.6(10) . . . . ? C8 C9 C10 C11 -179.9(6) . . . . ? C9 C10 C11 C12 -1.0(10) . . . . ? C10 C11 C12 C13 2.4(10) . . . . ? C9 N1 C13 C12 0.8(9) . . . . ? Rh1 N1 C13 C12 177.2(5) . . . . ? C11 C12 C13 N1 -2.4(10) . . . . ? C1 Rh1 C14 C15 -54.7(4) . . . . ? C16 Rh1 C14 C15 38.4(4) . . . . ? N1 Rh1 C14 C15 -145.5(4) . . . . ? C17 Rh1 C14 C15 81.3(4) . . . . ? C18 Rh1 C14 C15 116.0(5) . . . . ? Cl1 Rh1 C14 C15 99.6(5) . . . . ? C1 Rh1 C14 C18 -170.7(4) . . . . ? C16 Rh1 C14 C18 -77.6(4) . . . . ? N1 Rh1 C14 C18 98.5(3) . . . . ? C15 Rh1 C14 C18 -116.0(5) . . . . ? C17 Rh1 C14 C18 -34.7(3) . . . . ? Cl1 Rh1 C14 C18 -16.4(6) . . . . ? C1 Rh1 C14 C19 66.9(7) . . . . ? C16 Rh1 C14 C19 160.0(7) . . . . ? N1 Rh1 C14 C19 -23.9(7) . . . . ? C15 Rh1 C14 C19 121.6(8) . . . . ? C17 Rh1 C14 C19 -157.1(8) . . . . ? C18 Rh1 C14 C19 -122.4(8) . . . . ? Cl1 Rh1 C14 C19 -138.8(6) . . . . ? C18 C14 C15 C16 6.4(6) . . . . ? C19 C14 C15 C16 173.1(6) . . . . ? Rh1 C14 C15 C16 -59.7(4) . . . . ? C18 C14 C15 C20 -170.8(6) . . . . ? C19 C14 C15 C20 -4.2(10) . . . . ? Rh1 C14 C15 C20 123.1(7) . . . . ? C18 C14 C15 Rh1 66.1(4) . . . . ? C19 C14 C15 Rh1 -127.2(6) . . . . ? C1 Rh1 C15 C14 135.1(4) . . . . ? C16 Rh1 C15 C14 -117.4(5) . . . . ? N1 Rh1 C15 C14 46.8(4) . . . . ? C17 Rh1 C15 C14 -78.0(4) . . . . ? C18 Rh1 C15 C14 -38.5(4) . . . . ? Cl1 Rh1 C15 C14 -136.1(3) . . . . ? C1 Rh1 C15 C16 -107.5(4) . . . . ? N1 Rh1 C15 C16 164.1(3) . . . . ? C14 Rh1 C15 C16 117.4(5) . . . . ? C17 Rh1 C15 C16 39.4(4) . . . . ? C18 Rh1 C15 C16 78.9(4) . . . . ? Cl1 Rh1 C15 C16 -18.7(5) . . . . ? C1 Rh1 C15 C20 12.7(6) . . . . ? C16 Rh1 C15 C20 120.3(8) . . . . ? N1 Rh1 C15 C20 -75.6(7) . . . . ? C14 Rh1 C15 C20 -122.3(8) . . . . ? C17 Rh1 C15 C20 159.6(7) . . . . ? C18 Rh1 C15 C20 -160.9(7) . . . . ? Cl1 Rh1 C15 C20 101.6(6) . . . . ? C14 C15 C16 C17 -7.6(7) . . . . ? C20 C15 C16 C17 169.6(6) . . . . ? Rh1 C15 C16 C17 -68.8(4) . . . . ? C14 C15 C16 C21 -176.8(6) . . . . ? C20 C15 C16 C21 0.5(11) . . . . ? Rh1 C15 C16 C21 122.1(7) . . . . ? C14 C15 C16 Rh1 61.1(4) . . . . ? C20 C15 C16 Rh1 -121.6(7) . . . . ? C1 Rh1 C16 C15 79.5(4) . . . . ? N1 Rh1 C16 C15 -52.1(10) . . . . ? C14 Rh1 C16 C15 -37.5(4) . . . . ? C17 Rh1 C16 C15 -113.8(5) . . . . ? C18 Rh1 C16 C15 -80.4(4) . . . . ? Cl1 Rh1 C16 C15 167.4(3) . . . . ? C1 Rh1 C16 C17 -166.6(4) . . . . ? N1 Rh1 C16 C17 61.7(10) . . . . ? C15 Rh1 C16 C17 113.8(5) . . . . ? C14 Rh1 C16 C17 76.4(4) . . . . ? C18 Rh1 C16 C17 33.5(4) . . . . ? Cl1 Rh1 C16 C17 -78.8(4) . . . . ? C1 Rh1 C16 C21 -41.6(7) . . . . ? N1 Rh1 C16 C21 -173.3(7) . . . . ? C15 Rh1 C16 C21 -121.2(8) . . . . ? C14 Rh1 C16 C21 -158.7(7) . . . . ? C17 Rh1 C16 C21 125.0(8) . . . . ? C18 Rh1 C16 C21 158.5(7) . . . . ? Cl1 Rh1 C16 C21 46.2(7) . . . . ? C15 C16 C17 C18 6.1(7) . . . . ? C21 C16 C17 C18 175.2(6) . . . . ? Rh1 C16 C17 C18 -59.7(5) . . . . ? C15 C16 C17 C22 -173.5(6) . . . . ? C21 C16 C17 C22 -4.5(10) . . . . ? Rh1 C16 C17 C22 120.7(6) . . . . ? C15 C16 C17 Rh1 65.8(4) . . . . ? C21 C16 C17 Rh1 -125.1(7) . . . . ? C1 Rh1 C17 C18 142.6(4) . . . . ? C16 Rh1 C17 C18 121.4(6) . . . . ? N1 Rh1 C17 C18 -40.0(5) . . . . ? C15 Rh1 C17 C18 81.1(4) . . . . ? C14 Rh1 C17 C18 37.8(4) . . . . ? Cl1 Rh1 C17 C18 -133.7(4) . . . . ? C1 Rh1 C17 C16 21.2(6) . . . . ? N1 Rh1 C17 C16 -161.5(3) . . . . ? C15 Rh1 C17 C16 -40.4(4) . . . . ? C14 Rh1 C17 C16 -83.6(4) . . . . ? C18 Rh1 C17 C16 -121.4(6) . . . . ? Cl1 Rh1 C17 C16 104.9(4) . . . . ? C1 Rh1 C17 C22 -91.2(8) . . . . ? C16 Rh1 C17 C22 -112.4(8) . . . . ? N1 Rh1 C17 C22 86.2(7) . . . . ? C15 Rh1 C17 C22 -152.7(7) . . . . ? C14 Rh1 C17 C22 164.0(8) . . . . ? C18 Rh1 C17 C22 126.2(8) . . . . ? Cl1 Rh1 C17 C22 -7.5(7) . . . . ? C16 C17 C18 C14 -2.1(7) . . . . ? C22 C17 C18 C14 177.5(7) . . . . ? Rh1 C17 C18 C14 -57.4(4) . . . . ? C16 C17 C18 C23 179.9(6) . . . . ? C22 C17 C18 C23 -0.5(11) . . . . ? Rh1 C17 C18 C23 124.7(6) . . . . ? C16 C17 C18 Rh1 55.3(4) . . . . ? C22 C17 C18 Rh1 -125.2(7) . . . . ? C15 C14 C18 C17 -2.7(7) . . . . ? C19 C14 C18 C17 -169.7(6) . . . . ? Rh1 C14 C18 C17 60.7(4) . . . . ? C15 C14 C18 C23 175.4(6) . . . . ? C19 C14 C18 C23 8.4(9) . . . . ? Rh1 C14 C18 C23 -121.2(6) . . . . ? C15 C14 C18 Rh1 -63.4(4) . . . . ? C19 C14 C18 Rh1 129.6(6) . . . . ? C1 Rh1 C18 C17 -97.6(7) . . . . ? C16 Rh1 C18 C17 -36.4(4) . . . . ? N1 Rh1 C18 C17 151.0(4) . . . . ? C15 Rh1 C18 C17 -80.6(4) . . . . ? C14 Rh1 C18 C17 -119.1(5) . . . . ? Cl1 Rh1 C18 C17 52.4(4) . . . . ? C1 Rh1 C18 C14 21.5(8) . . . . ? C16 Rh1 C18 C14 82.7(4) . . . . ? N1 Rh1 C18 C14 -89.9(4) . . . . ? C15 Rh1 C18 C14 38.5(3) . . . . ? C17 Rh1 C18 C14 119.1(5) . . . . ? Cl1 Rh1 C18 C14 171.6(3) . . . . ? C1 Rh1 C18 C23 137.1(7) . . . . ? C16 Rh1 C18 C23 -161.7(7) . . . . ? N1 Rh1 C18 C23 25.7(6) . . . . ? C15 Rh1 C18 C23 154.1(7) . . . . ? C14 Rh1 C18 C23 115.6(7) . . . . ? C17 Rh1 C18 C23 -125.2(8) . . . . ? Cl1 Rh1 C18 C23 -72.8(6) . . . . ? C24 Rh2 N2 C32 59.7(5) . . . . ? C39 Rh2 N2 C32 -65.2(10) . . . . ? C38 Rh2 N2 C32 -34.0(6) . . . . ? C37 Rh2 N2 C32 -62.2(5) . . . . ? C40 Rh2 N2 C32 -122.1(5) . . . . ? C41 Rh2 N2 C32 -100.7(5) . . . . ? Cl2 Rh2 N2 C32 144.7(5) . . . . ? C24 Rh2 N2 C36 -125.1(5) . . . . ? C39 Rh2 N2 C36 110.0(9) . . . . ? C38 Rh2 N2 C36 141.2(4) . . . . ? C37 Rh2 N2 C36 113.0(5) . . . . ? C40 Rh2 N2 C36 53.1(6) . . . . ? C41 Rh2 N2 C36 74.5(5) . . . . ? Cl2 Rh2 N2 C36 -40.1(4) . . . . ? N2 Rh2 C24 C25 -55.6(6) . . . . ? C39 Rh2 C24 C25 110.3(6) . . . . ? C38 Rh2 C24 C25 71.9(6) . . . . ? C37 Rh2 C24 C25 42.5(7) . . . . ? C40 Rh2 C24 C25 126.4(6) . . . . ? C41 Rh2 C24 C25 61.3(10) . . . . ? Cl2 Rh2 C24 C25 -147.9(6) . . . . ? Rh2 C24 C25 C26 -3.5(11) . . . . ? C24 C25 C26 C31 49.5(10) . . . . ? C24 C25 C26 C27 -131.1(7) . . . . ? C31 C26 C27 C28 -2.1(10) . . . . ? C25 C26 C27 C28 178.4(7) . . . . ? C26 C27 C28 C29 1.5(11) . . . . ? C27 C28 C29 C30 -0.2(12) . . . . ? C28 C29 C30 C31 -0.5(12) . . . . ? C27 C26 C31 C30 1.4(9) . . . . ? C25 C26 C31 C30 -179.2(6) . . . . ? C27 C26 C31 C32 -173.9(6) . . . . ? C25 C26 C31 C32 5.4(10) . . . . ? C29 C30 C31 C26 -0.1(11) . . . . ? C29 C30 C31 C32 175.7(7) . . . . ? C36 N2 C32 C33 1.2(9) . . . . ? Rh2 N2 C32 C33 176.3(4) . . . . ? C36 N2 C32 C31 -177.5(6) . . . . ? Rh2 N2 C32 C31 -2.4(8) . . . . ? C26 C31 C32 N2 -50.5(9) . . . . ? C30 C31 C32 N2 134.1(7) . . . . ? C26 C31 C32 C33 130.8(7) . . . . ? C30 C31 C32 C33 -44.7(8) . . . . ? N2 C32 C33 C34 -2.2(10) . . . . ? C31 C32 C33 C34 176.5(6) . . . . ? C32 C33 C34 C35 -0.2(11) . . . . ? C33 C34 C35 C36 3.4(11) . . . . ? C32 N2 C36 C35 2.2(10) . . . . ? Rh2 N2 C36 C35 -173.5(6) . . . . ? C34 C35 C36 N2 -4.5(11) . . . . ? C24 Rh2 C37 C38 51.9(4) . . . . ? N2 Rh2 C37 C38 142.9(3) . . . . ? C39 Rh2 C37 C38 -38.0(4) . . . . ? C40 Rh2 C37 C38 -81.7(4) . . . . ? C41 Rh2 C37 C38 -117.0(5) . . . . ? Cl2 Rh2 C37 C38 -106.3(4) . . . . ? C24 Rh2 C37 C41 168.9(4) . . . . ? N2 Rh2 C37 C41 -100.1(4) . . . . ? C39 Rh2 C37 C41 78.9(4) . . . . ? C38 Rh2 C37 C41 117.0(5) . . . . ? C40 Rh2 C37 C41 35.3(4) . . . . ? Cl2 Rh2 C37 C41 10.7(6) . . . . ? C24 Rh2 C37 C42 -70.5(7) . . . . ? N2 Rh2 C37 C42 20.5(7) . . . . ? C39 Rh2 C37 C42 -160.4(7) . . . . ? C38 Rh2 C37 C42 -122.4(8) . . . . ? C40 Rh2 C37 C42 155.9(8) . . . . ? C41 Rh2 C37 C42 120.7(8) . . . . ? Cl2 Rh2 C37 C42 131.3(6) . . . . ? C41 C37 C38 C39 -4.3(7) . . . . ? C42 C37 C38 C39 -174.9(6) . . . . ? Rh2 C37 C38 C39 60.7(4) . . . . ? C41 C37 C38 C43 169.3(6) . . . . ? C42 C37 C38 C43 -1.2(11) . . . . ? Rh2 C37 C38 C43 -125.6(7) . . . . ? C41 C37 C38 Rh2 -65.0(4) . . . . ? C42 C37 C38 Rh2 124.4(7) . . . . ? C24 Rh2 C38 C37 -137.9(4) . . . . ? N2 Rh2 C38 C37 -48.8(4) . . . . ? C39 Rh2 C38 C37 117.4(5) . . . . ? C40 Rh2 C38 C37 78.0(4) . . . . ? C41 Rh2 C38 C37 37.8(4) . . . . ? Cl2 Rh2 C38 C37 133.3(3) . . . . ? C24 Rh2 C38 C39 104.7(4) . . . . ? N2 Rh2 C38 C39 -166.1(4) . . . . ? C37 Rh2 C38 C39 -117.4(5) . . . . ? C40 Rh2 C38 C39 -39.4(4) . . . . ? C41 Rh2 C38 C39 -79.6(4) . . . . ? Cl2 Rh2 C38 C39 16.0(5) . . . . ? C24 Rh2 C38 C43 -14.6(7) . . . . ? N2 Rh2 C38 C43 74.5(7) . . . . ? C39 Rh2 C38 C43 -119.3(8) . . . . ? C37 Rh2 C38 C43 123.3(8) . . . . ? C40 Rh2 C38 C43 -158.7(7) . . . . ? C41 Rh2 C38 C43 161.1(7) . . . . ? Cl2 Rh2 C38 C43 -103.3(6) . . . . ? C37 C38 C39 C40 5.1(7) . . . . ? C43 C38 C39 C40 -168.7(6) . . . . ? Rh2 C38 C39 C40 66.8(4) . . . . ? C37 C38 C39 C44 177.0(7) . . . . ? C43 C38 C39 C44 3.2(11) . . . . ? Rh2 C38 C39 C44 -121.3(7) . . . . ? C37 C38 C39 Rh2 -61.8(4) . . . . ? C43 C38 C39 Rh2 124.4(6) . . . . ? C24 Rh2 C39 C38 -81.7(4) . . . . ? N2 Rh2 C39 C38 41.0(10) . . . . ? C37 Rh2 C39 C38 37.7(4) . . . . ? C40 Rh2 C39 C38 114.8(5) . . . . ? C41 Rh2 C39 C38 80.2(4) . . . . ? Cl2 Rh2 C39 C38 -169.6(3) . . . . ? C24 Rh2 C39 C40 163.4(4) . . . . ? N2 Rh2 C39 C40 -73.8(9) . . . . ? C38 Rh2 C39 C40 -114.8(5) . . . . ? C37 Rh2 C39 C40 -77.1(4) . . . . ? C41 Rh2 C39 C40 -34.6(4) . . . . ? Cl2 Rh2 C39 C40 75.5(4) . . . . ? C24 Rh2 C39 C44 40.5(7) . . . . ? N2 Rh2 C39 C44 163.3(7) . . . . ? C38 Rh2 C39 C44 122.2(8) . . . . ? C37 Rh2 C39 C44 159.9(7) . . . . ? C40 Rh2 C39 C44 -122.9(8) . . . . ? C41 Rh2 C39 C44 -157.5(7) . . . . ? Cl2 Rh2 C39 C44 -47.4(6) . . . . ? C38 C39 C40 C41 -4.1(7) . . . . ? C44 C39 C40 C41 -176.1(6) . . . . ? Rh2 C39 C40 C41 60.5(5) . . . . ? C38 C39 C40 C45 174.2(6) . . . . ? C44 C39 C40 C45 2.2(11) . . . . ? Rh2 C39 C40 C45 -121.2(6) . . . . ? C38 C39 C40 Rh2 -64.6(4) . . . . ? C44 C39 C40 Rh2 123.4(7) . . . . ? C24 Rh2 C40 C41 -145.3(5) . . . . ? N2 Rh2 C40 C41 37.4(5) . . . . ? C39 Rh2 C40 C41 -119.9(5) . . . . ? C38 Rh2 C40 C41 -80.6(4) . . . . ? C37 Rh2 C40 C41 -37.4(4) . . . . ? Cl2 Rh2 C40 C41 131.0(4) . . . . ? C24 Rh2 C40 C39 -25.4(6) . . . . ? N2 Rh2 C40 C39 157.3(3) . . . . ? C38 Rh2 C40 C39 39.3(4) . . . . ? C37 Rh2 C40 C39 82.5(4) . . . . ? C41 Rh2 C40 C39 119.9(5) . . . . ? Cl2 Rh2 C40 C39 -109.1(3) . . . . ? C24 Rh2 C40 C45 89.8(7) . . . . ? N2 Rh2 C40 C45 -87.4(7) . . . . ? C39 Rh2 C40 C45 115.3(8) . . . . ? C38 Rh2 C40 C45 154.6(7) . . . . ? C37 Rh2 C40 C45 -162.2(7) . . . . ? C41 Rh2 C40 C45 -124.8(8) . . . . ? Cl2 Rh2 C40 C45 6.2(7) . . . . ? C39 C40 C41 C37 1.4(7) . . . . ? C45 C40 C41 C37 -176.8(6) . . . . ? Rh2 C40 C41 C37 58.1(4) . . . . ? C39 C40 C41 C46 178.3(7) . . . . ? C45 C40 C41 C46 0.2(11) . . . . ? Rh2 C40 C41 C46 -125.0(7) . . . . ? C39 C40 C41 Rh2 -56.7(4) . . . . ? C45 C40 C41 Rh2 125.2(7) . . . . ? C38 C37 C41 C40 1.8(7) . . . . ? C42 C37 C41 C40 172.8(6) . . . . ? Rh2 C37 C41 C40 -60.6(5) . . . . ? C38 C37 C41 C46 -175.3(6) . . . . ? C42 C37 C41 C46 -4.3(10) . . . . ? Rh2 C37 C41 C46 122.3(6) . . . . ? C38 C37 C41 Rh2 62.4(4) . . . . ? C42 C37 C41 Rh2 -126.6(7) . . . . ? C24 Rh2 C41 C40 92.7(8) . . . . ? N2 Rh2 C41 C40 -153.3(4) . . . . ? C39 Rh2 C41 C40 37.5(4) . . . . ? C38 Rh2 C41 C40 81.0(4) . . . . ? C37 Rh2 C41 C40 119.1(6) . . . . ? Cl2 Rh2 C41 C40 -55.3(4) . . . . ? C24 Rh2 C41 C37 -26.4(9) . . . . ? N2 Rh2 C41 C37 87.5(4) . . . . ? C39 Rh2 C41 C37 -81.6(4) . . . . ? C38 Rh2 C41 C37 -38.2(4) . . . . ? C40 Rh2 C41 C37 -119.1(6) . . . . ? Cl2 Rh2 C41 C37 -174.4(3) . . . . ? C24 Rh2 C41 C46 -142.6(8) . . . . ? N2 Rh2 C41 C46 -28.6(7) . . . . ? C39 Rh2 C41 C46 162.2(8) . . . . ? C38 Rh2 C41 C46 -154.3(8) . . . . ? C37 Rh2 C41 C46 -116.2(8) . . . . ? C40 Rh2 C41 C46 124.7(9) . . . . ? Cl2 Rh2 C41 C46 69.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 29.35 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.055 _refine_diff_density_min -0.958 _refine_diff_density_rms 0.134 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.53A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2008). APEX2 V2008.3-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). TWINABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_1f _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll10 _chemical_melting_point ? _chemical_formula_moiety 'C68 H70 Ir2 N2' _chemical_formula_sum 'C68 H70 Ir2 N2' _chemical_formula_weight 1299.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 20.891(3) _cell_length_b 20.891(3) _cell_length_c 34.563(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 15084(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173.0(5) _cell_measurement_reflns_used 4015 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.78 _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5168 _exptl_absorpt_coefficient_mu 3.557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5669 _exptl_absorpt_correction_T_max 0.8708 _exptl_absorpt_process_details 'SADABS (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 91015 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7728 _reflns_number_gt 5367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+139.3253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7728 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2137 _refine_ls_wR_factor_gt 0.1996 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.73470(2) -0.05499(2) 0.378658(10) 0.06441(19) Uani 1 1 d . . . N1 N 0.7054(5) -0.0103(5) 0.4289(3) 0.076(2) Uani 1 1 d . . . C1 C 0.8066(5) -0.0849(5) 0.4168(2) 0.057(2) Uani 1 1 d . . . C2 C 0.8374(5) -0.0537(5) 0.3848(3) 0.059(2) Uani 1 1 d . . . C3 C 0.8148(5) 0.0091(5) 0.3745(3) 0.066(3) Uani 1 1 d . . . H3A H 0.8251 0.0202 0.3471 0.080 Uiso 1 1 calc R . . C4 C 0.8209(6) 0.0657(5) 0.4010(3) 0.070(3) Uani 1 1 d . . . C5 C 0.8667(7) 0.1110(7) 0.3898(4) 0.096(4) Uani 1 1 d . . . H5A H 0.8899 0.1058 0.3664 0.115 Uiso 1 1 calc R . . C6 C 0.8777(9) 0.1638(8) 0.4135(5) 0.118(5) Uani 1 1 d . . . H6A H 0.9078 0.1957 0.4063 0.141 Uiso 1 1 calc R . . C7 C 0.8434(10) 0.1689(8) 0.4481(5) 0.119(6) Uani 1 1 d . . . H7A H 0.8532 0.2031 0.4652 0.143 Uiso 1 1 calc R . . C8 C 0.7977(9) 0.1279(7) 0.4581(4) 0.105(5) Uani 1 1 d . . . H8A H 0.7737 0.1346 0.4811 0.126 Uiso 1 1 calc R . . C9 C 0.7855(7) 0.0756(6) 0.4351(3) 0.083(4) Uani 1 1 d . . . C10 C 0.7321(6) 0.0360(6) 0.4474(4) 0.084(3) Uani 1 1 d . . . H10A H 0.7148 0.0453 0.4722 0.101 Uiso 1 1 calc R . . C11 C 0.7291(5) -0.0926(5) 0.3189(3) 0.066(3) Uani 1 1 d . . . C12 C 0.6877(5) -0.0387(6) 0.3217(3) 0.069(3) Uani 1 1 d . . . C13 C 0.6403(6) -0.0531(7) 0.3499(3) 0.081(3) Uani 1 1 d . . . C14 C 0.6517(6) -0.1190(6) 0.3631(3) 0.081(3) Uani 1 1 d . . . C15 C 0.7067(6) -0.1417(6) 0.3450(3) 0.078(3) Uani 1 1 d . . . C16 C 0.7807(6) -0.0968(6) 0.2894(3) 0.077(3) Uani 1 1 d . . . H16A H 0.7627 -0.1120 0.2649 0.115 Uiso 1 1 calc R . . H16B H 0.8136 -0.1269 0.2983 0.115 Uiso 1 1 calc R . . H16C H 0.7999 -0.0545 0.2856 0.115 Uiso 1 1 calc R . . C17 C 0.6912(6) 0.0200(6) 0.2978(3) 0.077(3) Uani 1 1 d . . . H17A H 0.6717 0.0118 0.2725 0.115 Uiso 1 1 calc R . . H17B H 0.7361 0.0323 0.2943 0.115 Uiso 1 1 calc R . . H17C H 0.6681 0.0547 0.3108 0.115 Uiso 1 1 calc R . . C18 C 0.5836(6) -0.0114(8) 0.3583(4) 0.099(4) Uani 1 1 d . . . H18A H 0.5530 -0.0143 0.3369 0.148 Uiso 1 1 calc R . . H18B H 0.5977 0.0331 0.3612 0.148 Uiso 1 1 calc R . . H18C H 0.5630 -0.0257 0.3823 0.148 Uiso 1 1 calc R . . C19 C 0.6045(6) -0.1546(8) 0.3874(4) 0.099(5) Uani 1 1 d . . . H19A H 0.5706 -0.1719 0.3708 0.148 Uiso 1 1 calc R . . H19B H 0.5857 -0.1254 0.4065 0.148 Uiso 1 1 calc R . . H19C H 0.6261 -0.1898 0.4008 0.148 Uiso 1 1 calc R . . C20 C 0.7338(7) -0.2088(6) 0.3485(4) 0.092(4) Uani 1 1 d . . . H20A H 0.7096 -0.2378 0.3316 0.138 Uiso 1 1 calc R . . H20B H 0.7302 -0.2234 0.3753 0.138 Uiso 1 1 calc R . . H20C H 0.7789 -0.2086 0.3407 0.138 Uiso 1 1 calc R . . C21 C 0.8118(5) -0.1154(5) 0.4503(2) 0.060(2) Uani 1 1 d . . . H21A H 0.7750 -0.1375 0.4593 0.072 Uiso 1 1 calc R . . C22 C 0.8670(5) -0.1178(5) 0.4736(3) 0.063(2) Uani 1 1 d . . . C23 C 0.9230(6) -0.0855(6) 0.4641(3) 0.080(3) Uani 1 1 d . . . H23A H 0.9245 -0.0601 0.4413 0.097 Uiso 1 1 calc R . . C24 C 0.9787(6) -0.0902(8) 0.4882(3) 0.095(4) Uani 1 1 d . . . H24A H 1.0152 -0.0643 0.4832 0.113 Uiso 1 1 calc R . . C25 C 0.9788(7) -0.1333(8) 0.5192(4) 0.100(5) Uani 1 1 d . . . H25A H 1.0169 -0.1416 0.5333 0.119 Uiso 1 1 calc R . . C26 C 0.9217(8) -0.1637(7) 0.5289(3) 0.095(4) Uani 1 1 d . . . H26A H 0.9210 -0.1892 0.5517 0.113 Uiso 1 1 calc R . . C27 C 0.8653(6) -0.1589(4) 0.5071(3) 0.071(3) Uani 1 1 d . . . H27A H 0.8277 -0.1817 0.5141 0.086 Uiso 1 1 calc R . . C28 C 0.8818(4) -0.0916(5) 0.3600(2) 0.054(2) Uani 1 1 d . . . C29 C 0.9193(5) -0.0592(5) 0.3328(3) 0.067(3) Uani 1 1 d . . . H29A H 0.9167 -0.0140 0.3306 0.080 Uiso 1 1 calc R . . C30 C 0.9607(5) -0.0941(6) 0.3089(3) 0.074(3) Uani 1 1 d . . . H30A H 0.9860 -0.0720 0.2904 0.089 Uiso 1 1 calc R . . C31 C 0.9656(5) -0.1617(6) 0.3119(3) 0.070(3) Uani 1 1 d . . . H31A H 0.9934 -0.1854 0.2955 0.084 Uiso 1 1 calc R . . C32 C 0.9281(5) -0.1918(5) 0.3398(3) 0.068(3) Uani 1 1 d . . . H32A H 0.9298 -0.2371 0.3422 0.081 Uiso 1 1 calc R . . C33 C 0.8888(5) -0.1579(5) 0.3639(3) 0.063(2) Uani 1 1 d . . . H33A H 0.8659 -0.1797 0.3836 0.076 Uiso 1 1 calc R . . C34 C 0.6538(6) -0.0423(8) 0.4498(3) 0.091(4) Uani 1 1 d . . . H34B H 0.6444 -0.0186 0.4736 0.136 Uiso 1 1 calc R . . H34C H 0.6669 -0.0860 0.4563 0.136 Uiso 1 1 calc R . . H34D H 0.6154 -0.0437 0.4335 0.136 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0706(3) 0.0878(3) 0.0349(2) 0.00662(16) -0.01176(15) -0.0111(2) N1 0.083(6) 0.098(7) 0.048(5) -0.002(5) -0.016(4) 0.004(5) C1 0.060(5) 0.075(6) 0.037(4) -0.006(4) -0.010(4) -0.006(5) C2 0.061(6) 0.064(6) 0.052(5) 0.005(4) -0.009(4) -0.023(5) C3 0.075(7) 0.075(6) 0.049(5) 0.002(4) -0.025(5) 0.007(5) C4 0.087(8) 0.066(6) 0.058(6) -0.002(5) -0.023(5) -0.002(6) C5 0.118(11) 0.094(9) 0.075(8) -0.002(7) -0.042(8) 0.000(8) C6 0.144(14) 0.101(11) 0.108(12) -0.009(9) -0.043(11) -0.021(10) C7 0.189(18) 0.089(10) 0.080(10) -0.028(8) -0.027(11) -0.001(11) C8 0.162(15) 0.076(9) 0.075(8) -0.012(7) -0.047(9) 0.002(9) C9 0.114(10) 0.080(8) 0.054(6) -0.015(5) -0.031(6) 0.022(7) C10 0.093(9) 0.101(9) 0.057(6) 0.002(6) -0.002(6) 0.008(8) C11 0.077(7) 0.080(7) 0.042(5) 0.005(4) -0.017(4) -0.006(6) C12 0.076(7) 0.092(8) 0.040(5) 0.007(5) -0.014(4) -0.008(6) C13 0.076(7) 0.113(10) 0.054(6) -0.003(6) -0.010(5) -0.023(7) C14 0.087(8) 0.103(9) 0.052(6) 0.020(6) -0.009(6) -0.034(7) C15 0.095(9) 0.097(8) 0.043(5) 0.009(5) -0.023(5) -0.023(7) C16 0.107(9) 0.082(7) 0.042(5) -0.010(5) -0.016(5) 0.002(6) C17 0.084(8) 0.089(8) 0.058(6) 0.012(5) -0.013(5) -0.004(6) C18 0.077(8) 0.149(13) 0.069(7) 0.015(8) -0.015(6) 0.015(8) C19 0.070(7) 0.153(13) 0.072(7) 0.030(8) -0.027(6) -0.046(8) C20 0.121(11) 0.079(8) 0.077(8) 0.016(6) -0.032(7) -0.016(8) C21 0.076(6) 0.064(6) 0.041(4) -0.011(4) -0.002(4) 0.003(5) C22 0.074(7) 0.067(6) 0.048(5) -0.011(4) 0.002(4) 0.015(5) C23 0.076(7) 0.116(10) 0.050(6) -0.012(6) -0.003(5) -0.011(7) C24 0.086(9) 0.140(12) 0.057(7) -0.022(7) 0.008(6) -0.007(8) C25 0.090(9) 0.150(13) 0.059(7) -0.039(8) -0.024(6) 0.038(9) C26 0.121(11) 0.114(11) 0.049(6) -0.009(6) -0.010(7) 0.003(9) C27 0.128(10) 0.048(5) 0.038(5) -0.004(4) -0.003(5) 0.009(6) C28 0.055(5) 0.075(6) 0.032(4) -0.004(4) 0.004(3) -0.010(4) C29 0.069(6) 0.073(7) 0.057(5) 0.003(5) -0.007(5) -0.013(5) C30 0.076(7) 0.096(8) 0.051(6) 0.014(5) -0.001(5) -0.009(6) C31 0.078(7) 0.086(8) 0.046(5) -0.002(5) -0.009(5) 0.022(6) C32 0.088(7) 0.068(6) 0.047(5) 0.002(4) -0.016(5) -0.009(5) C33 0.073(6) 0.079(7) 0.037(4) 0.009(4) -0.005(4) -0.014(5) C34 0.073(7) 0.153(12) 0.046(5) -0.001(7) -0.003(5) 0.008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N1 2.063(10) . ? Ir1 C1 2.093(9) . ? Ir1 C3 2.148(12) . ? Ir1 C2 2.155(10) . ? Ir1 C13 2.210(11) . ? Ir1 C11 2.212(10) . ? Ir1 C12 2.225(9) . ? Ir1 C15 2.229(11) . ? Ir1 C14 2.254(11) . ? N1 C10 1.287(16) . ? N1 C34 1.461(15) . ? C1 C21 1.325(13) . ? C1 C2 1.435(13) . ? C2 C3 1.439(14) . ? C2 C28 1.490(14) . ? C3 C4 1.500(14) . ? C3 H3A 1.0000 . ? C4 C5 1.398(18) . ? C4 C9 1.409(17) . ? C5 C6 1.394(19) . ? C5 H5A 0.9500 . ? C6 C7 1.40(2) . ? C6 H6A 0.9500 . ? C7 C8 1.33(2) . ? C7 H7A 0.9500 . ? C8 C9 1.375(16) . ? C8 H8A 0.9500 . ? C9 C10 1.452(19) . ? C10 H10A 0.9500 . ? C11 C12 1.423(16) . ? C11 C15 1.445(15) . ? C11 C16 1.487(15) . ? C12 C13 1.421(15) . ? C12 C17 1.480(15) . ? C13 C14 1.471(18) . ? C13 C18 1.498(18) . ? C14 C15 1.390(18) . ? C14 C19 1.494(16) . ? C15 C20 1.517(17) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.410(14) . ? C21 H21A 0.9500 . ? C22 C23 1.389(15) . ? C22 C27 1.442(14) . ? C23 C24 1.434(17) . ? C23 H23A 0.9500 . ? C24 C25 1.40(2) . ? C24 H24A 0.9500 . ? C25 C26 1.39(2) . ? C25 H25A 0.9500 . ? C26 C27 1.404(17) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 C33 1.399(14) . ? C28 C29 1.399(13) . ? C29 C30 1.400(15) . ? C29 H29A 0.9500 . ? C30 C31 1.421(16) . ? C30 H30A 0.9500 . ? C31 C32 1.394(15) . ? C31 H31A 0.9500 . ? C32 C33 1.367(15) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C34 H34D 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C1 79.6(4) . . ? N1 Ir1 C3 90.3(4) . . ? C1 Ir1 C3 70.7(4) . . ? N1 Ir1 C2 101.9(4) . . ? C1 Ir1 C2 39.5(3) . . ? C3 Ir1 C2 39.1(4) . . ? N1 Ir1 C13 96.1(4) . . ? C1 Ir1 C13 158.3(4) . . ? C3 Ir1 C13 130.9(4) . . ? C2 Ir1 C13 158.8(4) . . ? N1 Ir1 C11 158.4(4) . . ? C1 Ir1 C11 121.3(4) . . ? C3 Ir1 C11 101.6(4) . . ? C2 Ir1 C11 98.6(4) . . ? C13 Ir1 C11 62.5(4) . . ? N1 Ir1 C12 122.9(4) . . ? C1 Ir1 C12 156.8(4) . . ? C3 Ir1 C12 100.9(4) . . ? C2 Ir1 C12 121.6(4) . . ? C13 Ir1 C12 37.4(4) . . ? C11 Ir1 C12 37.4(4) . . ? N1 Ir1 C15 136.7(4) . . ? C1 Ir1 C15 105.9(4) . . ? C3 Ir1 C15 132.5(4) . . ? C2 Ir1 C15 108.8(4) . . ? C13 Ir1 C15 63.0(5) . . ? C11 Ir1 C15 38.0(4) . . ? C12 Ir1 C15 63.1(4) . . ? N1 Ir1 C14 103.9(4) . . ? C1 Ir1 C14 121.6(4) . . ? C3 Ir1 C14 162.4(4) . . ? C2 Ir1 C14 142.7(5) . . ? C13 Ir1 C14 38.5(5) . . ? C11 Ir1 C14 61.7(4) . . ? C12 Ir1 C14 62.7(4) . . ? C15 Ir1 C14 36.1(5) . . ? C10 N1 C34 114.6(10) . . ? C10 N1 Ir1 129.0(9) . . ? C34 N1 Ir1 115.4(8) . . ? C21 C1 C2 148.6(10) . . ? C21 C1 Ir1 138.8(8) . . ? C2 C1 Ir1 72.6(5) . . ? C1 C2 C3 117.2(10) . . ? C1 C2 C28 118.7(9) . . ? C3 C2 C28 123.1(9) . . ? C1 C2 Ir1 67.9(5) . . ? C3 C2 Ir1 70.2(6) . . ? C28 C2 Ir1 123.8(6) . . ? C2 C3 C4 122.8(8) . . ? C2 C3 Ir1 70.7(6) . . ? C4 C3 Ir1 121.2(8) . . ? C2 C3 H3A 112.1 . . ? C4 C3 H3A 112.1 . . ? Ir1 C3 H3A 112.1 . . ? C5 C4 C9 119.4(11) . . ? C5 C4 C3 115.0(11) . . ? C9 C4 C3 125.5(11) . . ? C6 C5 C4 119.0(15) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C5 C6 C7 118.6(16) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C8 C7 C6 122.9(14) . . ? C8 C7 H7A 118.6 . . ? C6 C7 H7A 118.6 . . ? C7 C8 C9 119.6(16) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C8 C9 C4 120.3(14) . . ? C8 C9 C10 115.2(13) . . ? C4 C9 C10 124.4(11) . . ? N1 C10 C9 128.0(12) . . ? N1 C10 H10A 116.0 . . ? C9 C10 H10A 116.0 . . ? C12 C11 C15 108.8(10) . . ? C12 C11 C16 122.4(9) . . ? C15 C11 C16 128.4(11) . . ? C12 C11 Ir1 71.8(6) . . ? C15 C11 Ir1 71.7(6) . . ? C16 C11 Ir1 128.5(7) . . ? C13 C12 C11 107.6(10) . . ? C13 C12 C17 126.3(12) . . ? C11 C12 C17 125.9(10) . . ? C13 C12 Ir1 70.7(6) . . ? C11 C12 Ir1 70.8(5) . . ? C17 C12 Ir1 126.8(7) . . ? C12 C13 C14 107.3(11) . . ? C12 C13 C18 124.1(12) . . ? C14 C13 C18 127.8(11) . . ? C12 C13 Ir1 71.9(6) . . ? C14 C13 Ir1 72.4(7) . . ? C18 C13 Ir1 129.0(9) . . ? C15 C14 C13 108.3(10) . . ? C15 C14 C19 129.0(13) . . ? C13 C14 C19 122.2(13) . . ? C15 C14 Ir1 71.0(7) . . ? C13 C14 Ir1 69.1(6) . . ? C19 C14 Ir1 132.0(8) . . ? C14 C15 C11 107.9(11) . . ? C14 C15 C20 126.0(11) . . ? C11 C15 C20 125.8(12) . . ? C14 C15 Ir1 72.9(7) . . ? C11 C15 Ir1 70.4(6) . . ? C20 C15 Ir1 127.8(7) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 C21 C22 125.7(10) . . ? C1 C21 H21A 117.1 . . ? C22 C21 H21A 117.1 . . ? C23 C22 C21 122.5(10) . . ? C23 C22 C27 120.0(10) . . ? C21 C22 C27 117.4(10) . . ? C22 C23 C24 120.9(12) . . ? C22 C23 H23A 119.6 . . ? C24 C23 H23A 119.6 . . ? C25 C24 C23 119.2(13) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? C26 C25 C24 118.6(12) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? C25 C26 C27 123.8(12) . . ? C25 C26 H26A 118.1 . . ? C27 C26 H26A 118.1 . . ? C26 C27 C22 117.0(12) . . ? C26 C27 H27A 121.5 . . ? C22 C27 H27A 121.5 . . ? C33 C28 C29 118.9(9) . . ? C33 C28 C2 122.5(8) . . ? C29 C28 C2 118.6(9) . . ? C28 C29 C30 119.5(10) . . ? C28 C29 H29A 120.3 . . ? C30 C29 H29A 120.3 . . ? C29 C30 C31 121.3(10) . . ? C29 C30 H30A 119.4 . . ? C31 C30 H30A 119.4 . . ? C32 C31 C30 117.2(10) . . ? C32 C31 H31A 121.4 . . ? C30 C31 H31A 121.4 . . ? C33 C32 C31 121.7(10) . . ? C33 C32 H32A 119.1 . . ? C31 C32 H32A 119.1 . . ? C32 C33 C28 121.2(9) . . ? C32 C33 H33A 119.4 . . ? C28 C33 H33A 119.4 . . ? N1 C34 H34B 109.5 . . ? N1 C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N1 C34 H34D 109.5 . . ? H34B C34 H34D 109.5 . . ? H34C C34 H34D 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C10 68.0(11) . . . . ? C3 Ir1 N1 C10 -2.3(11) . . . . ? C2 Ir1 N1 C10 35.3(11) . . . . ? C13 Ir1 N1 C10 -133.5(11) . . . . ? C11 Ir1 N1 C10 -126.1(13) . . . . ? C12 Ir1 N1 C10 -105.5(11) . . . . ? C15 Ir1 N1 C10 170.1(10) . . . . ? C14 Ir1 N1 C10 -171.8(10) . . . . ? C1 Ir1 N1 C34 -100.3(8) . . . . ? C3 Ir1 N1 C34 -170.6(8) . . . . ? C2 Ir1 N1 C34 -133.0(8) . . . . ? C13 Ir1 N1 C34 58.2(8) . . . . ? C11 Ir1 N1 C34 65.6(14) . . . . ? C12 Ir1 N1 C34 86.2(9) . . . . ? C15 Ir1 N1 C34 1.9(11) . . . . ? C14 Ir1 N1 C34 20.0(9) . . . . ? N1 Ir1 C1 C21 56.7(11) . . . . ? C3 Ir1 C1 C21 150.7(12) . . . . ? C2 Ir1 C1 C21 -179.7(14) . . . . ? C13 Ir1 C1 C21 -23.4(19) . . . . ? C11 Ir1 C1 C21 -117.3(11) . . . . ? C12 Ir1 C1 C21 -137.3(11) . . . . ? C15 Ir1 C1 C21 -79.2(11) . . . . ? C14 Ir1 C1 C21 -43.4(13) . . . . ? N1 Ir1 C1 C2 -123.7(6) . . . . ? C3 Ir1 C1 C2 -29.7(6) . . . . ? C13 Ir1 C1 C2 156.3(11) . . . . ? C11 Ir1 C1 C2 62.3(7) . . . . ? C12 Ir1 C1 C2 42.4(12) . . . . ? C15 Ir1 C1 C2 100.5(6) . . . . ? C14 Ir1 C1 C2 136.3(6) . . . . ? C21 C1 C2 C3 -128.7(17) . . . . ? Ir1 C1 C2 C3 51.7(7) . . . . ? C21 C1 C2 C28 62(2) . . . . ? Ir1 C1 C2 C28 -117.6(8) . . . . ? C21 C1 C2 Ir1 179.6(18) . . . . ? N1 Ir1 C2 C1 56.8(6) . . . . ? C3 Ir1 C2 C1 132.1(8) . . . . ? C13 Ir1 C2 C1 -155.7(11) . . . . ? C11 Ir1 C2 C1 -130.1(6) . . . . ? C12 Ir1 C2 C1 -161.8(6) . . . . ? C15 Ir1 C2 C1 -92.4(6) . . . . ? C14 Ir1 C2 C1 -76.4(8) . . . . ? N1 Ir1 C2 C3 -75.4(6) . . . . ? C1 Ir1 C2 C3 -132.1(8) . . . . ? C13 Ir1 C2 C3 72.2(14) . . . . ? C11 Ir1 C2 C3 97.8(6) . . . . ? C12 Ir1 C2 C3 66.1(7) . . . . ? C15 Ir1 C2 C3 135.5(6) . . . . ? C14 Ir1 C2 C3 151.4(6) . . . . ? N1 Ir1 C2 C28 167.4(8) . . . . ? C1 Ir1 C2 C28 110.6(10) . . . . ? C3 Ir1 C2 C28 -117.3(10) . . . . ? C13 Ir1 C2 C28 -45.1(16) . . . . ? C11 Ir1 C2 C28 -19.5(8) . . . . ? C12 Ir1 C2 C28 -51.2(9) . . . . ? C15 Ir1 C2 C28 18.3(9) . . . . ? C14 Ir1 C2 C28 34.2(11) . . . . ? C1 C2 C3 C4 64.6(14) . . . . ? C28 C2 C3 C4 -126.6(11) . . . . ? Ir1 C2 C3 C4 115.3(11) . . . . ? C1 C2 C3 Ir1 -50.6(7) . . . . ? C28 C2 C3 Ir1 118.1(8) . . . . ? N1 Ir1 C3 C2 108.8(6) . . . . ? C1 Ir1 C3 C2 30.0(5) . . . . ? C13 Ir1 C3 C2 -153.0(6) . . . . ? C11 Ir1 C3 C2 -89.4(6) . . . . ? C12 Ir1 C3 C2 -127.6(6) . . . . ? C15 Ir1 C3 C2 -64.2(7) . . . . ? C14 Ir1 C3 C2 -107.0(15) . . . . ? N1 Ir1 C3 C4 -8.5(8) . . . . ? C1 Ir1 C3 C4 -87.3(8) . . . . ? C2 Ir1 C3 C4 -117.3(10) . . . . ? C13 Ir1 C3 C4 89.7(9) . . . . ? C11 Ir1 C3 C4 153.3(7) . . . . ? C12 Ir1 C3 C4 115.1(8) . . . . ? C15 Ir1 C3 C4 178.5(7) . . . . ? C14 Ir1 C3 C4 135.7(15) . . . . ? C2 C3 C4 C5 107.7(13) . . . . ? Ir1 C3 C4 C5 -166.3(8) . . . . ? C2 C3 C4 C9 -71.6(15) . . . . ? Ir1 C3 C4 C9 14.4(14) . . . . ? C9 C4 C5 C6 2.2(18) . . . . ? C3 C4 C5 C6 -177.2(11) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C5 C6 C7 C8 -5(3) . . . . ? C6 C7 C8 C9 4(3) . . . . ? C7 C8 C9 C4 0(2) . . . . ? C7 C8 C9 C10 -176.4(13) . . . . ? C5 C4 C9 C8 -2.8(17) . . . . ? C3 C4 C9 C8 176.5(11) . . . . ? C5 C4 C9 C10 172.9(11) . . . . ? C3 C4 C9 C10 -7.8(17) . . . . ? C34 N1 C10 C9 178.1(11) . . . . ? Ir1 N1 C10 C9 9.7(19) . . . . ? C8 C9 C10 N1 170.3(12) . . . . ? C4 C9 C10 N1 -6(2) . . . . ? N1 Ir1 C11 C12 29.1(14) . . . . ? C1 Ir1 C11 C12 -167.2(6) . . . . ? C3 Ir1 C11 C12 -92.9(6) . . . . ? C2 Ir1 C11 C12 -132.5(6) . . . . ? C13 Ir1 C11 C12 37.4(7) . . . . ? C15 Ir1 C11 C12 117.8(10) . . . . ? C14 Ir1 C11 C12 81.1(7) . . . . ? N1 Ir1 C11 C15 -88.7(13) . . . . ? C1 Ir1 C11 C15 75.0(8) . . . . ? C3 Ir1 C11 C15 149.3(7) . . . . ? C2 Ir1 C11 C15 109.7(7) . . . . ? C13 Ir1 C11 C15 -80.4(8) . . . . ? C12 Ir1 C11 C15 -117.8(10) . . . . ? C14 Ir1 C11 C15 -36.7(7) . . . . ? N1 Ir1 C11 C16 146.4(11) . . . . ? C1 Ir1 C11 C16 -49.9(11) . . . . ? C3 Ir1 C11 C16 24.4(10) . . . . ? C2 Ir1 C11 C16 -15.2(10) . . . . ? C13 Ir1 C11 C16 154.6(11) . . . . ? C12 Ir1 C11 C16 117.3(12) . . . . ? C15 Ir1 C11 C16 -124.9(13) . . . . ? C14 Ir1 C11 C16 -161.6(12) . . . . ? C15 C11 C12 C13 1.0(11) . . . . ? C16 C11 C12 C13 173.9(9) . . . . ? Ir1 C11 C12 C13 -61.5(7) . . . . ? C15 C11 C12 C17 -175.4(10) . . . . ? C16 C11 C12 C17 -2.5(15) . . . . ? Ir1 C11 C12 C17 122.1(10) . . . . ? C15 C11 C12 Ir1 62.5(7) . . . . ? C16 C11 C12 Ir1 -124.6(9) . . . . ? N1 Ir1 C12 C13 -50.2(9) . . . . ? C1 Ir1 C12 C13 146.1(10) . . . . ? C3 Ir1 C12 C13 -147.7(8) . . . . ? C2 Ir1 C12 C13 176.4(7) . . . . ? C11 Ir1 C12 C13 117.5(10) . . . . ? C15 Ir1 C12 C13 79.9(8) . . . . ? C14 Ir1 C12 C13 39.1(8) . . . . ? N1 Ir1 C12 C11 -167.7(6) . . . . ? C1 Ir1 C12 C11 28.7(13) . . . . ? C3 Ir1 C12 C11 94.8(7) . . . . ? C2 Ir1 C12 C11 58.9(7) . . . . ? C13 Ir1 C12 C11 -117.5(10) . . . . ? C15 Ir1 C12 C11 -37.6(7) . . . . ? C14 Ir1 C12 C11 -78.3(7) . . . . ? N1 Ir1 C12 C17 71.3(11) . . . . ? C1 Ir1 C12 C17 -92.4(14) . . . . ? C3 Ir1 C12 C17 -26.2(11) . . . . ? C2 Ir1 C12 C17 -62.2(12) . . . . ? C13 Ir1 C12 C17 121.5(14) . . . . ? C11 Ir1 C12 C17 -121.0(13) . . . . ? C15 Ir1 C12 C17 -158.6(12) . . . . ? C14 Ir1 C12 C17 160.6(12) . . . . ? C11 C12 C13 C14 -2.7(11) . . . . ? C17 C12 C13 C14 173.8(10) . . . . ? Ir1 C12 C13 C14 -64.2(7) . . . . ? C11 C12 C13 C18 -173.2(10) . . . . ? C17 C12 C13 C18 3.3(17) . . . . ? Ir1 C12 C13 C18 125.3(11) . . . . ? C11 C12 C13 Ir1 61.5(7) . . . . ? C17 C12 C13 Ir1 -122.0(10) . . . . ? N1 Ir1 C13 C12 139.5(7) . . . . ? C1 Ir1 C13 C12 -143.6(10) . . . . ? C3 Ir1 C13 C12 43.9(10) . . . . ? C2 Ir1 C13 C12 -8.6(16) . . . . ? C11 Ir1 C13 C12 -37.4(7) . . . . ? C15 Ir1 C13 C12 -80.3(8) . . . . ? C14 Ir1 C13 C12 -115.6(10) . . . . ? N1 Ir1 C13 C14 -104.8(7) . . . . ? C1 Ir1 C13 C14 -27.9(15) . . . . ? C3 Ir1 C13 C14 159.5(7) . . . . ? C2 Ir1 C13 C14 107.0(13) . . . . ? C11 Ir1 C13 C14 78.2(7) . . . . ? C12 Ir1 C13 C14 115.6(10) . . . . ? C15 Ir1 C13 C14 35.3(6) . . . . ? N1 Ir1 C13 C18 19.9(12) . . . . ? C1 Ir1 C13 C18 96.8(16) . . . . ? C3 Ir1 C13 C18 -75.7(12) . . . . ? C2 Ir1 C13 C18 -128.3(12) . . . . ? C11 Ir1 C13 C18 -157.0(13) . . . . ? C12 Ir1 C13 C18 -119.6(15) . . . . ? C15 Ir1 C13 C18 160.1(13) . . . . ? C14 Ir1 C13 C18 124.7(14) . . . . ? C12 C13 C14 C15 3.4(12) . . . . ? C18 C13 C14 C15 173.5(11) . . . . ? Ir1 C13 C14 C15 -60.4(8) . . . . ? C12 C13 C14 C19 -168.8(10) . . . . ? C18 C13 C14 C19 1.3(18) . . . . ? Ir1 C13 C14 C19 127.4(11) . . . . ? C12 C13 C14 Ir1 63.9(7) . . . . ? C18 C13 C14 Ir1 -126.1(12) . . . . ? N1 Ir1 C14 C15 -158.8(6) . . . . ? C1 Ir1 C14 C15 -72.6(7) . . . . ? C3 Ir1 C14 C15 58.2(18) . . . . ? C2 Ir1 C14 C15 -26.1(9) . . . . ? C13 Ir1 C14 C15 119.1(9) . . . . ? C11 Ir1 C14 C15 38.6(6) . . . . ? C12 Ir1 C14 C15 81.1(7) . . . . ? N1 Ir1 C14 C13 82.1(7) . . . . ? C1 Ir1 C14 C13 168.3(6) . . . . ? C3 Ir1 C14 C13 -60.9(18) . . . . ? C2 Ir1 C14 C13 -145.2(7) . . . . ? C11 Ir1 C14 C13 -80.5(7) . . . . ? C12 Ir1 C14 C13 -38.0(7) . . . . ? C15 Ir1 C14 C13 -119.1(9) . . . . ? N1 Ir1 C14 C19 -33.0(15) . . . . ? C1 Ir1 C14 C19 53.2(16) . . . . ? C3 Ir1 C14 C19 -175.9(13) . . . . ? C2 Ir1 C14 C19 99.7(15) . . . . ? C13 Ir1 C14 C19 -115.1(17) . . . . ? C11 Ir1 C14 C19 164.4(16) . . . . ? C12 Ir1 C14 C19 -153.1(16) . . . . ? C15 Ir1 C14 C19 125.8(17) . . . . ? C13 C14 C15 C11 -2.8(12) . . . . ? C19 C14 C15 C11 168.7(11) . . . . ? Ir1 C14 C15 C11 -62.1(7) . . . . ? C13 C14 C15 C20 -176.0(10) . . . . ? C19 C14 C15 C20 -4.5(18) . . . . ? Ir1 C14 C15 C20 124.7(10) . . . . ? C13 C14 C15 Ir1 59.3(8) . . . . ? C19 C14 C15 Ir1 -129.2(12) . . . . ? C12 C11 C15 C14 1.2(11) . . . . ? C16 C11 C15 C14 -171.2(10) . . . . ? Ir1 C11 C15 C14 63.7(8) . . . . ? C12 C11 C15 C20 174.4(9) . . . . ? C16 C11 C15 C20 2.0(17) . . . . ? Ir1 C11 C15 C20 -123.0(10) . . . . ? C12 C11 C15 Ir1 -62.6(7) . . . . ? C16 C11 C15 Ir1 125.0(10) . . . . ? N1 Ir1 C15 C14 30.8(9) . . . . ? C1 Ir1 C15 C14 122.3(6) . . . . ? C3 Ir1 C15 C14 -159.5(6) . . . . ? C2 Ir1 C15 C14 163.6(6) . . . . ? C13 Ir1 C15 C14 -37.6(6) . . . . ? C11 Ir1 C15 C14 -116.8(10) . . . . ? C12 Ir1 C15 C14 -79.7(7) . . . . ? N1 Ir1 C15 C11 147.5(6) . . . . ? C1 Ir1 C15 C11 -120.9(7) . . . . ? C3 Ir1 C15 C11 -42.8(9) . . . . ? C2 Ir1 C15 C11 -79.6(7) . . . . ? C13 Ir1 C15 C11 79.2(7) . . . . ? C12 Ir1 C15 C11 37.0(6) . . . . ? C14 Ir1 C15 C11 116.8(10) . . . . ? N1 Ir1 C15 C20 -91.9(13) . . . . ? C1 Ir1 C15 C20 -0.3(12) . . . . ? C3 Ir1 C15 C20 77.8(12) . . . . ? C2 Ir1 C15 C20 41.0(12) . . . . ? C13 Ir1 C15 C20 -160.3(13) . . . . ? C11 Ir1 C15 C20 120.6(15) . . . . ? C12 Ir1 C15 C20 157.6(13) . . . . ? C14 Ir1 C15 C20 -122.7(14) . . . . ? C2 C1 C21 C22 15(2) . . . . ? Ir1 C1 C21 C22 -166.1(8) . . . . ? C1 C21 C22 C23 2.2(16) . . . . ? C1 C21 C22 C27 -173.7(9) . . . . ? C21 C22 C23 C24 -178.7(10) . . . . ? C27 C22 C23 C24 -2.9(16) . . . . ? C22 C23 C24 C25 7.1(18) . . . . ? C23 C24 C25 C26 -8.8(18) . . . . ? C24 C25 C26 C27 6.8(19) . . . . ? C25 C26 C27 C22 -2.5(17) . . . . ? C23 C22 C27 C26 0.5(14) . . . . ? C21 C22 C27 C26 176.6(9) . . . . ? C1 C2 C28 C33 7.7(13) . . . . ? C3 C2 C28 C33 -160.9(9) . . . . ? Ir1 C2 C28 C33 -73.7(11) . . . . ? C1 C2 C28 C29 -170.1(8) . . . . ? C3 C2 C28 C29 21.3(13) . . . . ? Ir1 C2 C28 C29 108.4(9) . . . . ? C33 C28 C29 C30 2.9(14) . . . . ? C2 C28 C29 C30 -179.1(9) . . . . ? C28 C29 C30 C31 -0.3(15) . . . . ? C29 C30 C31 C32 -0.7(15) . . . . ? C30 C31 C32 C33 -1.1(15) . . . . ? C31 C32 C33 C28 3.8(15) . . . . ? C29 C28 C33 C32 -4.7(14) . . . . ? C2 C28 C33 C32 177.4(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 4.985 _refine_diff_density_min -2.124 _refine_diff_density_rms 0.152 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Blessing, R. (1995). SADABS V2.10, Acta Cryst. A51, 33-38. Bruker (2000). SHELXTL V6.14, Bruker AXS, Inc., Madison, WI, USA. Bruker (2003). SAINT V7.06A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2004). APEX2 V1.0-22, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (1997). SHELXL-97, University of G\"ottingen, Germany. Spek, A. L. (2003). PLATON V300106, J. Appl. Cryst. 36, 7-13. ; _vrf_PLAT083_jonll10 ; PROBLEM: _A SHELXL Second Parameter in WGHT unusually Large, 139.00. RESPONSE: See below. ; _vrf_PLAT602_jonll10 ; PROBLEM: _A VERY LARGE Solvent Accessible VOID(S) in Structure! RESPONSE: The counterion(s) and solvent are highly disordered over a crystallographic two-fold axis. The counterions appear to be a disorder of Cp*IrCl3(-) and Cl(-), both with half occupancies. Unknown solvent appears to be part of the disorder as well. The reflection contributions from the disordered species were removed using program PLATON, function SQUEEZE (Spek, 2003), which determined there to be 1980 electrons in 5222 A**3 removed per unit cell. Since the counterions were removed and the structure is of poor quality anyway, this structure may be used for connectivity purposes only, as supporting information for independent characterization techniques. Because the molecular formula and atom list only contain the cation, all calculated values determined from these are known to be incorrect. ; #===end data_2g _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll66 _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 N O2 Rh, Cl' _chemical_formula_sum 'C24 H30 Cl N O2 Rh' _chemical_formula_weight 502.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.3248(14) _cell_length_b 13.1132(12) _cell_length_c 12.2913(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.318(2) _cell_angle_gamma 90.00 _cell_volume 2194.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4069 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 29.15 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8374 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21144 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.1099 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 33.14 _reflns_number_total 8262 _reflns_number_gt 5937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), 4062 Friedel pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 8262 _refine_ls_number_parameters 270 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.43568(4) 0.78878(2) 0.19112(4) 0.01805(8) Uani 1 1 d . . . Cl1 Cl 0.02217(14) 0.90971(12) 0.29996(14) 0.0431(4) Uani 1 1 d . . . N1 N 0.6044(4) 0.6185(4) 0.2415(4) 0.0245(10) Uani 1 1 d . . . C1 C 0.5888(6) 0.8121(6) 0.2343(7) 0.0267(18) Uani 1 1 d . . . C2 C 0.5592(6) 0.8854(6) 0.3005(6) 0.0271(16) Uani 1 1 d . . . C3 C 0.5380(5) 0.8269(4) 0.3847(6) 0.0178(12) Uani 1 1 d . . . C4 C 0.5075(5) 0.8567(5) 0.4740(6) 0.0238(13) Uani 1 1 d . . . H4A H 0.4998 0.9268 0.4872 0.029 Uiso 1 1 calc R . . C5 C 0.4899(4) 0.7849(4) 0.5387(5) 0.0292(11) Uani 1 1 d . . . H5A H 0.4714 0.8046 0.5996 0.035 Uiso 1 1 calc R . . C6 C 0.4985(4) 0.6767(4) 0.5173(5) 0.0280(11) Uani 1 1 d . . . H6A H 0.4838 0.6274 0.5631 0.034 Uiso 1 1 calc R . . C7 C 0.5271(4) 0.6450(4) 0.4336(5) 0.0225(10) Uani 1 1 d . . . H7A H 0.5318 0.5744 0.4199 0.027 Uiso 1 1 calc R . . C8 C 0.5499(6) 0.7203(5) 0.3663(7) 0.0203(14) Uani 1 1 d . . . C9 C 0.5840(7) 0.7091(5) 0.2763(7) 0.0218(16) Uani 1 1 d . . . C10 C 0.3341(6) 0.7995(5) -0.0016(6) 0.0240(14) Uani 1 1 d . . . C11 C 0.3060(5) 0.8738(5) 0.0635(6) 0.0188(13) Uani 1 1 d . . . C12 C 0.2835(6) 0.8169(5) 0.1469(6) 0.0179(15) Uani 1 1 d . . . C13 C 0.2964(7) 0.7105(5) 0.1302(7) 0.0209(15) Uani 1 1 d . . . C14 C 0.3267(7) 0.7018(5) 0.0379(7) 0.0253(17) Uani 1 1 d . . . C15 C 0.3636(6) 0.8282(6) -0.0995(6) 0.0335(18) Uani 1 1 d . . . H15A H 0.3050 0.8464 -0.1750 0.050 Uiso 1 1 calc R . . H15B H 0.3965 0.7701 -0.1154 0.050 Uiso 1 1 calc R . . H15C H 0.4086 0.8865 -0.0716 0.050 Uiso 1 1 calc R . . C16 C 0.2988(5) 0.9874(5) 0.0456(6) 0.0270(13) Uani 1 1 d . . . H16A H 0.2361 1.0046 -0.0248 0.041 Uiso 1 1 calc R . . H16B H 0.3530 1.0112 0.0306 0.041 Uiso 1 1 calc R . . H16C H 0.3028 1.0204 0.1192 0.041 Uiso 1 1 calc R . . C17 C 0.2542(6) 0.8600(6) 0.2374(8) 0.0295(17) Uani 1 1 d . . . H17A H 0.1837 0.8491 0.2085 0.044 Uiso 1 1 calc R . . H17B H 0.2684 0.9332 0.2469 0.044 Uiso 1 1 calc R . . H17C H 0.2912 0.8259 0.3165 0.044 Uiso 1 1 calc R . . C18 C 0.2798(4) 0.6253(4) 0.1983(6) 0.0264(11) Uani 1 1 d . . . H18A H 0.2107 0.6044 0.1560 0.040 Uiso 1 1 calc R . . H18B H 0.2961 0.6478 0.2815 0.040 Uiso 1 1 calc R . . H18C H 0.3217 0.5674 0.2024 0.040 Uiso 1 1 calc R . . C19 C 0.3436(4) 0.6015(5) -0.0109(6) 0.0309(12) Uani 1 1 d . . . H19A H 0.2802 0.5719 -0.0679 0.046 Uiso 1 1 calc R . . H19B H 0.3784 0.5543 0.0573 0.046 Uiso 1 1 calc R . . H19C H 0.3832 0.6135 -0.0537 0.046 Uiso 1 1 calc R . . C20 C 0.6263(6) 0.8486(6) 0.1488(6) 0.0229(14) Uani 1 1 d . . . O1 O 0.5888(3) 0.9147(3) 0.0751(4) 0.0318(9) Uani 1 1 d . . . O2 O 0.7130(3) 0.8065(3) 0.1772(4) 0.0327(9) Uani 1 1 d . . . C21 C 0.7612(5) 0.8414(5) 0.1047(6) 0.0426(15) Uani 1 1 d . . . H21A H 0.7427 0.9132 0.0795 0.051 Uiso 1 1 calc R . . H21B H 0.8334 0.8385 0.1553 0.051 Uiso 1 1 calc R . . C22 C 0.7320(8) 0.7774(5) -0.0042(8) 0.060(2) Uani 1 1 d . . . H22A H 0.7554 0.8083 -0.0587 0.091 Uiso 1 1 calc R . . H22B H 0.6603 0.7717 -0.0473 0.091 Uiso 1 1 calc R . . H22C H 0.7609 0.7094 0.0205 0.091 Uiso 1 1 calc R . . C23 C 0.5589(5) 0.9991(5) 0.2931(6) 0.0337(16) Uani 1 1 d . . . H23A H 0.6258 1.0249 0.3421 0.051 Uiso 1 1 calc R . . H23B H 0.5158 1.0271 0.3249 0.051 Uiso 1 1 calc R . . H23C H 0.5350 1.0200 0.2076 0.051 Uiso 1 1 calc R . . C24 C 0.6039(4) 0.6064(4) 0.1244(5) 0.0295(12) Uani 1 1 d . . . H24A H 0.5776 0.5390 0.0907 0.044 Uiso 1 1 calc R . . H24B H 0.6711 0.6125 0.1351 0.044 Uiso 1 1 calc R . . H24C H 0.5627 0.6594 0.0681 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01631(13) 0.01893(13) 0.01575(13) 0.0031(2) 0.00464(10) 0.0002(3) Cl1 0.0563(10) 0.0441(9) 0.0308(7) -0.0075(6) 0.0218(7) -0.0039(8) N1 0.026(2) 0.029(2) 0.020(2) 0.0074(19) 0.012(2) 0.0042(18) C1 0.015(4) 0.036(4) 0.022(4) 0.011(3) 0.002(3) 0.000(3) C2 0.021(3) 0.030(3) 0.018(3) 0.007(2) -0.002(2) -0.001(2) C3 0.018(3) 0.011(3) 0.018(2) -0.006(2) 0.004(2) 0.003(2) C4 0.021(3) 0.028(3) 0.017(2) -0.002(2) 0.004(2) 0.001(2) C5 0.035(3) 0.033(3) 0.020(2) -0.006(2) 0.013(2) -0.002(2) C6 0.032(3) 0.028(3) 0.021(2) 0.009(2) 0.009(2) 0.002(2) C7 0.025(3) 0.016(2) 0.021(2) 0.0029(18) 0.006(2) 0.0004(19) C8 0.015(3) 0.027(3) 0.016(3) 0.005(2) 0.004(2) 0.000(2) C9 0.017(3) 0.023(3) 0.021(3) 0.003(2) 0.005(2) 0.004(2) C10 0.024(3) 0.021(3) 0.022(3) 0.002(2) 0.005(2) -0.002(2) C11 0.020(3) 0.017(3) 0.020(3) 0.010(2) 0.009(2) 0.003(2) C12 0.018(4) 0.017(3) 0.015(3) 0.008(3) 0.006(3) 0.002(3) C13 0.015(3) 0.024(3) 0.021(3) -0.002(2) 0.005(2) 0.000(2) C14 0.017(3) 0.023(3) 0.025(3) -0.001(2) 0.000(2) 0.000(2) C15 0.033(4) 0.047(4) 0.019(3) 0.003(3) 0.011(3) -0.005(3) C16 0.021(3) 0.021(3) 0.029(3) 0.009(2) 0.003(2) -0.001(2) C17 0.022(4) 0.032(4) 0.036(4) 0.006(3) 0.014(3) 0.002(3) C18 0.028(3) 0.027(3) 0.026(3) 0.004(2) 0.014(3) -0.004(2) C19 0.026(3) 0.027(3) 0.030(3) -0.007(2) 0.005(2) -0.001(2) C20 0.022(3) 0.026(3) 0.023(3) 0.002(2) 0.013(3) 0.002(3) O1 0.035(2) 0.029(2) 0.028(2) 0.0109(16) 0.0118(18) 0.0041(17) O2 0.028(2) 0.039(2) 0.038(2) 0.0085(17) 0.0212(18) 0.0085(17) C21 0.037(4) 0.049(4) 0.053(4) 0.012(3) 0.031(3) 0.003(3) C22 0.109(8) 0.039(4) 0.068(5) 0.007(3) 0.071(6) 0.020(4) C23 0.032(4) 0.031(3) 0.027(3) 0.001(3) 0.004(3) -0.011(3) C24 0.036(3) 0.024(3) 0.028(3) 0.001(2) 0.013(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C2 2.159(8) . ? Rh1 C10 2.161(7) . ? Rh1 C13 2.169(9) . ? Rh1 C12 2.170(8) . ? Rh1 C1 2.177(9) . ? Rh1 C14 2.179(8) . ? Rh1 C11 2.189(6) . ? Rh1 C3 2.223(6) . ? Rh1 C8 2.246(7) . ? Rh1 C9 2.274(9) . ? N1 C9 1.347(8) . ? N1 C24 1.444(7) . ? C1 C9 1.459(10) . ? C1 C2 1.459(12) . ? C1 C20 1.490(11) . ? C2 C3 1.440(10) . ? C2 C23 1.494(11) . ? C3 C4 1.431(9) . ? C3 C8 1.440(8) . ? C4 C5 1.337(8) . ? C4 H4A 0.9500 . ? C5 C6 1.460(8) . ? C5 H5A 0.9500 . ? C6 C7 1.354(8) . ? C6 H6A 0.9500 . ? C7 C8 1.431(8) . ? C7 H7A 0.9500 . ? C8 C9 1.432(13) . ? C10 C14 1.393(9) . ? C10 C11 1.446(9) . ? C10 C15 1.515(10) . ? C11 C12 1.431(9) . ? C11 C16 1.502(9) . ? C12 C13 1.438(9) . ? C12 C17 1.489(11) . ? C13 C14 1.414(13) . ? C13 C18 1.487(9) . ? C14 C19 1.517(9) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O1 1.194(8) . ? C20 O2 1.328(9) . ? O2 C21 1.467(7) . ? C21 C22 1.466(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Rh1 C10 129.0(3) . . ? C2 Rh1 C13 159.3(3) . . ? C10 Rh1 C13 63.4(3) . . ? C2 Rh1 C12 126.2(3) . . ? C10 Rh1 C12 64.1(3) . . ? C13 Rh1 C12 38.7(3) . . ? C2 Rh1 C1 39.3(3) . . ? C10 Rh1 C1 114.3(3) . . ? C13 Rh1 C1 158.6(3) . . ? C12 Rh1 C1 162.11(16) . . ? C2 Rh1 C14 161.9(3) . . ? C10 Rh1 C14 37.4(2) . . ? C13 Rh1 C14 38.0(3) . . ? C12 Rh1 C14 64.1(3) . . ? C1 Rh1 C14 126.7(3) . . ? C2 Rh1 C11 113.3(2) . . ? C10 Rh1 C11 38.8(2) . . ? C13 Rh1 C11 64.4(3) . . ? C12 Rh1 C11 38.3(2) . . ? C1 Rh1 C11 128.7(3) . . ? C14 Rh1 C11 64.1(3) . . ? C2 Rh1 C3 38.3(2) . . ? C10 Rh1 C3 163.3(2) . . ? C13 Rh1 C3 125.1(3) . . ? C12 Rh1 C3 112.3(3) . . ? C1 Rh1 C3 63.6(3) . . ? C14 Rh1 C3 157.9(3) . . ? C11 Rh1 C3 127.9(2) . . ? C2 Rh1 C8 64.1(3) . . ? C10 Rh1 C8 158.3(2) . . ? C13 Rh1 C8 110.6(3) . . ? C12 Rh1 C8 125.7(3) . . ? C1 Rh1 C8 62.9(3) . . ? C14 Rh1 C8 124.8(2) . . ? C11 Rh1 C8 160.4(3) . . ? C3 Rh1 C8 37.6(2) . . ? C2 Rh1 C9 65.0(3) . . ? C10 Rh1 C9 126.8(3) . . ? C13 Rh1 C9 124.01(17) . . ? C12 Rh1 C9 157.9(3) . . ? C1 Rh1 C9 38.2(3) . . ? C14 Rh1 C9 111.4(3) . . ? C11 Rh1 C9 162.0(3) . . ? C3 Rh1 C9 63.0(3) . . ? C8 Rh1 C9 36.9(3) . . ? C9 N1 C24 121.1(5) . . ? C9 C1 C2 109.5(7) . . ? C9 C1 C20 130.1(8) . . ? C2 C1 C20 120.1(7) . . ? C9 C1 Rh1 74.5(5) . . ? C2 C1 Rh1 69.7(5) . . ? C20 C1 Rh1 126.5(5) . . ? C3 C2 C1 106.3(6) . . ? C3 C2 C23 125.5(7) . . ? C1 C2 C23 128.0(7) . . ? C3 C2 Rh1 73.3(4) . . ? C1 C2 Rh1 71.0(5) . . ? C23 C2 Rh1 124.8(5) . . ? C4 C3 C8 119.7(6) . . ? C4 C3 C2 131.8(6) . . ? C8 C3 C2 108.5(6) . . ? C4 C3 Rh1 124.3(5) . . ? C8 C3 Rh1 72.1(4) . . ? C2 C3 Rh1 68.4(4) . . ? C5 C4 C3 119.3(6) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 121.1(5) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C7 C6 C5 121.5(5) . . ? C7 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C6 C7 C8 118.5(5) . . ? C6 C7 H7A 120.7 . . ? C8 C7 H7A 120.7 . . ? C7 C8 C9 130.5(6) . . ? C7 C8 C3 119.7(7) . . ? C9 C8 C3 109.8(6) . . ? C7 C8 Rh1 122.7(5) . . ? C9 C8 Rh1 72.6(5) . . ? C3 C8 Rh1 70.3(4) . . ? N1 C9 C8 123.7(6) . . ? N1 C9 C1 130.4(8) . . ? C8 C9 C1 105.9(6) . . ? N1 C9 Rh1 126.0(6) . . ? C8 C9 Rh1 70.5(5) . . ? C1 C9 Rh1 67.3(4) . . ? C14 C10 C11 109.5(7) . . ? C14 C10 C15 127.4(7) . . ? C11 C10 C15 123.1(6) . . ? C14 C10 Rh1 72.0(4) . . ? C11 C10 Rh1 71.6(4) . . ? C15 C10 Rh1 124.0(6) . . ? C12 C11 C10 106.1(6) . . ? C12 C11 C16 126.6(6) . . ? C10 C11 C16 127.3(6) . . ? C12 C11 Rh1 70.1(4) . . ? C10 C11 Rh1 69.6(4) . . ? C16 C11 Rh1 126.2(5) . . ? C11 C12 C13 108.0(6) . . ? C11 C12 C17 126.3(6) . . ? C13 C12 C17 125.7(6) . . ? C11 C12 Rh1 71.5(4) . . ? C13 C12 Rh1 70.6(5) . . ? C17 C12 Rh1 122.3(5) . . ? C14 C13 C12 108.0(6) . . ? C14 C13 C18 126.6(6) . . ? C12 C13 C18 125.4(7) . . ? C14 C13 Rh1 71.4(5) . . ? C12 C13 Rh1 70.7(4) . . ? C18 C13 Rh1 123.8(5) . . ? C10 C14 C13 108.4(6) . . ? C10 C14 C19 127.1(8) . . ? C13 C14 C19 124.5(6) . . ? C10 C14 Rh1 70.6(4) . . ? C13 C14 Rh1 70.6(5) . . ? C19 C14 Rh1 126.4(6) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 O2 125.3(7) . . ? O1 C20 C1 124.1(7) . . ? O2 C20 C1 110.1(6) . . ? C20 O2 C21 115.5(5) . . ? C22 C21 O2 110.4(6) . . ? C22 C21 H21A 109.6 . . ? O2 C21 H21A 109.6 . . ? C22 C21 H21B 109.6 . . ? O2 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N1 C24 H24A 109.5 . . ? N1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 Rh1 C1 C9 118.2(6) . . . . ? C10 Rh1 C1 C9 -119.3(4) . . . . ? C13 Rh1 C1 C9 -40.4(9) . . . . ? C12 Rh1 C1 C9 159.9(9) . . . . ? C14 Rh1 C1 C9 -77.9(5) . . . . ? C11 Rh1 C1 C9 -162.1(4) . . . . ? C3 Rh1 C1 C9 79.1(4) . . . . ? C8 Rh1 C1 C9 36.8(4) . . . . ? C10 Rh1 C1 C2 122.5(4) . . . . ? C13 Rh1 C1 C2 -158.6(7) . . . . ? C12 Rh1 C1 C2 41.7(13) . . . . ? C14 Rh1 C1 C2 164.0(4) . . . . ? C11 Rh1 C1 C2 79.7(4) . . . . ? C3 Rh1 C1 C2 -39.1(4) . . . . ? C8 Rh1 C1 C2 -81.4(4) . . . . ? C9 Rh1 C1 C2 -118.2(6) . . . . ? C2 Rh1 C1 C20 -113.0(9) . . . . ? C10 Rh1 C1 C20 9.5(8) . . . . ? C13 Rh1 C1 C20 88.4(10) . . . . ? C12 Rh1 C1 C20 -71.3(14) . . . . ? C14 Rh1 C1 C20 50.9(8) . . . . ? C11 Rh1 C1 C20 -33.3(9) . . . . ? C3 Rh1 C1 C20 -152.1(8) . . . . ? C8 Rh1 C1 C20 165.6(8) . . . . ? C9 Rh1 C1 C20 128.8(9) . . . . ? C9 C1 C2 C3 1.0(9) . . . . ? C20 C1 C2 C3 -173.4(7) . . . . ? Rh1 C1 C2 C3 65.3(5) . . . . ? C9 C1 C2 C23 175.9(7) . . . . ? C20 C1 C2 C23 1.4(12) . . . . ? Rh1 C1 C2 C23 -119.8(8) . . . . ? C9 C1 C2 Rh1 -64.3(6) . . . . ? C20 C1 C2 Rh1 121.3(7) . . . . ? C10 Rh1 C2 C3 164.4(4) . . . . ? C13 Rh1 C2 C3 43.4(10) . . . . ? C12 Rh1 C2 C3 80.3(4) . . . . ? C1 Rh1 C2 C3 -114.4(6) . . . . ? C14 Rh1 C2 C3 -159.9(8) . . . . ? C11 Rh1 C2 C3 122.3(4) . . . . ? C8 Rh1 C2 C3 -36.3(4) . . . . ? C9 Rh1 C2 C3 -77.4(4) . . . . ? C10 Rh1 C2 C1 -81.3(5) . . . . ? C13 Rh1 C2 C1 157.8(7) . . . . ? C12 Rh1 C2 C1 -165.3(4) . . . . ? C14 Rh1 C2 C1 -45.5(11) . . . . ? C11 Rh1 C2 C1 -123.3(4) . . . . ? C3 Rh1 C2 C1 114.4(6) . . . . ? C8 Rh1 C2 C1 78.1(4) . . . . ? C9 Rh1 C2 C1 37.0(4) . . . . ? C10 Rh1 C2 C23 42.4(8) . . . . ? C13 Rh1 C2 C23 -78.6(10) . . . . ? C12 Rh1 C2 C23 -41.7(8) . . . . ? C1 Rh1 C2 C23 123.7(8) . . . . ? C14 Rh1 C2 C23 78.2(13) . . . . ? C11 Rh1 C2 C23 0.3(8) . . . . ? C3 Rh1 C2 C23 -122.0(9) . . . . ? C8 Rh1 C2 C23 -158.3(8) . . . . ? C9 Rh1 C2 C23 160.7(8) . . . . ? C1 C2 C3 C4 178.9(8) . . . . ? C23 C2 C3 C4 3.8(13) . . . . ? Rh1 C2 C3 C4 -117.4(8) . . . . ? C1 C2 C3 C8 -2.6(8) . . . . ? C23 C2 C3 C8 -177.6(7) . . . . ? Rh1 C2 C3 C8 61.2(5) . . . . ? C1 C2 C3 Rh1 -63.8(5) . . . . ? C23 C2 C3 Rh1 121.2(7) . . . . ? C2 Rh1 C3 C4 126.7(7) . . . . ? C10 Rh1 C3 C4 79.9(14) . . . . ? C13 Rh1 C3 C4 -36.1(6) . . . . ? C12 Rh1 C3 C4 5.9(6) . . . . ? C1 Rh1 C3 C4 166.8(6) . . . . ? C14 Rh1 C3 C4 -69.8(10) . . . . ? C11 Rh1 C3 C4 46.9(6) . . . . ? C8 Rh1 C3 C4 -114.2(7) . . . . ? C9 Rh1 C3 C4 -150.2(6) . . . . ? C2 Rh1 C3 C8 -119.2(6) . . . . ? C10 Rh1 C3 C8 -165.9(11) . . . . ? C13 Rh1 C3 C8 78.1(5) . . . . ? C12 Rh1 C3 C8 120.1(5) . . . . ? C1 Rh1 C3 C8 -79.0(5) . . . . ? C14 Rh1 C3 C8 44.3(8) . . . . ? C11 Rh1 C3 C8 161.0(4) . . . . ? C9 Rh1 C3 C8 -36.1(5) . . . . ? C10 Rh1 C3 C2 -46.8(14) . . . . ? C13 Rh1 C3 C2 -162.8(4) . . . . ? C12 Rh1 C3 C2 -120.7(4) . . . . ? C1 Rh1 C3 C2 40.1(4) . . . . ? C14 Rh1 C3 C2 163.5(8) . . . . ? C11 Rh1 C3 C2 -79.8(4) . . . . ? C8 Rh1 C3 C2 119.2(6) . . . . ? C9 Rh1 C3 C2 83.1(5) . . . . ? C8 C3 C4 C5 -0.4(10) . . . . ? C2 C3 C4 C5 178.0(7) . . . . ? Rh1 C3 C4 C5 87.3(7) . . . . ? C3 C4 C5 C6 -1.8(10) . . . . ? C4 C5 C6 C7 1.7(9) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? C6 C7 C8 C9 178.0(8) . . . . ? C6 C7 C8 C3 -2.8(10) . . . . ? C6 C7 C8 Rh1 -87.4(6) . . . . ? C4 C3 C8 C7 2.7(10) . . . . ? C2 C3 C8 C7 -176.1(6) . . . . ? Rh1 C3 C8 C7 -117.2(7) . . . . ? C4 C3 C8 C9 -177.9(7) . . . . ? C2 C3 C8 C9 3.3(9) . . . . ? Rh1 C3 C8 C9 62.2(6) . . . . ? C4 C3 C8 Rh1 119.9(7) . . . . ? C2 C3 C8 Rh1 -58.9(5) . . . . ? C2 Rh1 C8 C7 150.4(7) . . . . ? C10 Rh1 C8 C7 -77.5(11) . . . . ? C13 Rh1 C8 C7 -7.8(6) . . . . ? C12 Rh1 C8 C7 33.1(7) . . . . ? C1 Rh1 C8 C7 -165.4(7) . . . . ? C14 Rh1 C8 C7 -48.0(8) . . . . ? C11 Rh1 C8 C7 63.5(10) . . . . ? C3 Rh1 C8 C7 113.4(8) . . . . ? C9 Rh1 C8 C7 -127.4(7) . . . . ? C2 Rh1 C8 C9 -82.2(5) . . . . ? C10 Rh1 C8 C9 49.9(10) . . . . ? C13 Rh1 C8 C9 119.6(4) . . . . ? C12 Rh1 C8 C9 160.4(4) . . . . ? C1 Rh1 C8 C9 -38.0(4) . . . . ? C14 Rh1 C8 C9 79.4(6) . . . . ? C11 Rh1 C8 C9 -169.1(7) . . . . ? C3 Rh1 C8 C9 -119.2(6) . . . . ? C2 Rh1 C8 C3 37.0(4) . . . . ? C10 Rh1 C8 C3 169.1(8) . . . . ? C13 Rh1 C8 C3 -121.2(4) . . . . ? C12 Rh1 C8 C3 -80.3(5) . . . . ? C1 Rh1 C8 C3 81.2(5) . . . . ? C14 Rh1 C8 C3 -161.3(4) . . . . ? C11 Rh1 C8 C3 -49.9(9) . . . . ? C9 Rh1 C8 C3 119.2(6) . . . . ? C24 N1 C9 C8 157.4(7) . . . . ? C24 N1 C9 C1 -21.4(13) . . . . ? C24 N1 C9 Rh1 68.1(9) . . . . ? C7 C8 C9 N1 -2.4(15) . . . . ? C3 C8 C9 N1 178.3(7) . . . . ? Rh1 C8 C9 N1 -120.9(9) . . . . ? C7 C8 C9 C1 176.7(8) . . . . ? C3 C8 C9 C1 -2.6(10) . . . . ? Rh1 C8 C9 C1 58.2(6) . . . . ? C7 C8 C9 Rh1 118.4(9) . . . . ? C3 C8 C9 Rh1 -60.8(6) . . . . ? C2 C1 C9 N1 180.0(8) . . . . ? C20 C1 C9 N1 -6.4(15) . . . . ? Rh1 C1 C9 N1 118.7(9) . . . . ? C2 C1 C9 C8 1.0(10) . . . . ? C20 C1 C9 C8 174.6(8) . . . . ? Rh1 C1 C9 C8 -60.3(6) . . . . ? C2 C1 C9 Rh1 61.3(6) . . . . ? C20 C1 C9 Rh1 -125.0(9) . . . . ? C2 Rh1 C9 N1 -162.4(8) . . . . ? C10 Rh1 C9 N1 -41.2(8) . . . . ? C13 Rh1 C9 N1 39.0(9) . . . . ? C12 Rh1 C9 N1 71.9(11) . . . . ? C1 Rh1 C9 N1 -124.4(9) . . . . ? C14 Rh1 C9 N1 -1.8(8) . . . . ? C11 Rh1 C9 N1 -73.7(11) . . . . ? C3 Rh1 C9 N1 154.8(8) . . . . ? C8 Rh1 C9 N1 118.1(8) . . . . ? C2 Rh1 C9 C8 79.5(4) . . . . ? C10 Rh1 C9 C8 -159.3(4) . . . . ? C13 Rh1 C9 C8 -79.0(5) . . . . ? C12 Rh1 C9 C8 -46.2(9) . . . . ? C1 Rh1 C9 C8 117.6(6) . . . . ? C14 Rh1 C9 C8 -119.8(5) . . . . ? C11 Rh1 C9 C8 168.2(7) . . . . ? C3 Rh1 C9 C8 36.7(4) . . . . ? C2 Rh1 C9 C1 -38.1(4) . . . . ? C10 Rh1 C9 C1 83.1(5) . . . . ? C13 Rh1 C9 C1 163.4(4) . . . . ? C12 Rh1 C9 C1 -163.7(7) . . . . ? C14 Rh1 C9 C1 122.6(5) . . . . ? C11 Rh1 C9 C1 50.6(10) . . . . ? C3 Rh1 C9 C1 -80.9(5) . . . . ? C8 Rh1 C9 C1 -117.6(6) . . . . ? C2 Rh1 C10 C14 162.6(5) . . . . ? C13 Rh1 C10 C14 -37.2(5) . . . . ? C12 Rh1 C10 C14 -80.5(5) . . . . ? C1 Rh1 C10 C14 119.2(6) . . . . ? C11 Rh1 C10 C14 -118.5(7) . . . . ? C3 Rh1 C10 C14 -161.8(11) . . . . ? C8 Rh1 C10 C14 41.8(9) . . . . ? C9 Rh1 C10 C14 76.8(6) . . . . ? C2 Rh1 C10 C11 -78.8(4) . . . . ? C13 Rh1 C10 C11 81.4(4) . . . . ? C12 Rh1 C10 C11 38.0(4) . . . . ? C1 Rh1 C10 C11 -122.3(4) . . . . ? C14 Rh1 C10 C11 118.5(7) . . . . ? C3 Rh1 C10 C11 -43.3(14) . . . . ? C8 Rh1 C10 C11 160.4(7) . . . . ? C9 Rh1 C10 C11 -164.6(4) . . . . ? C2 Rh1 C10 C15 39.2(7) . . . . ? C13 Rh1 C10 C15 -160.6(7) . . . . ? C12 Rh1 C10 C15 156.1(6) . . . . ? C1 Rh1 C10 C15 -4.2(7) . . . . ? C14 Rh1 C10 C15 -123.4(8) . . . . ? C11 Rh1 C10 C15 118.1(7) . . . . ? C3 Rh1 C10 C15 74.8(14) . . . . ? C8 Rh1 C10 C15 -81.6(9) . . . . ? C9 Rh1 C10 C15 -46.6(7) . . . . ? C14 C10 C11 C12 1.4(9) . . . . ? C15 C10 C11 C12 179.9(7) . . . . ? Rh1 C10 C11 C12 -61.0(5) . . . . ? C14 C10 C11 C16 -177.0(7) . . . . ? C15 C10 C11 C16 1.5(12) . . . . ? Rh1 C10 C11 C16 120.6(7) . . . . ? C14 C10 C11 Rh1 62.4(6) . . . . ? C15 C10 C11 Rh1 -119.1(7) . . . . ? C2 Rh1 C11 C12 -119.5(4) . . . . ? C10 Rh1 C11 C12 116.7(6) . . . . ? C13 Rh1 C11 C12 37.9(4) . . . . ? C1 Rh1 C11 C12 -162.3(4) . . . . ? C14 Rh1 C11 C12 80.3(5) . . . . ? C3 Rh1 C11 C12 -77.8(5) . . . . ? C8 Rh1 C11 C12 -41.6(9) . . . . ? C9 Rh1 C11 C12 160.0(8) . . . . ? C2 Rh1 C11 C10 123.9(4) . . . . ? C13 Rh1 C11 C10 -78.7(4) . . . . ? C12 Rh1 C11 C10 -116.7(6) . . . . ? C1 Rh1 C11 C10 81.1(5) . . . . ? C14 Rh1 C11 C10 -36.4(4) . . . . ? C3 Rh1 C11 C10 165.5(5) . . . . ? C8 Rh1 C11 C10 -158.2(7) . . . . ? C9 Rh1 C11 C10 43.3(10) . . . . ? C2 Rh1 C11 C16 1.9(7) . . . . ? C10 Rh1 C11 C16 -121.9(7) . . . . ? C13 Rh1 C11 C16 159.3(7) . . . . ? C12 Rh1 C11 C16 121.4(7) . . . . ? C1 Rh1 C11 C16 -40.8(7) . . . . ? C14 Rh1 C11 C16 -158.3(7) . . . . ? C3 Rh1 C11 C16 43.6(7) . . . . ? C8 Rh1 C11 C16 79.8(10) . . . . ? C9 Rh1 C11 C16 -78.6(10) . . . . ? C10 C11 C12 C13 -0.9(9) . . . . ? C16 C11 C12 C13 177.5(6) . . . . ? Rh1 C11 C12 C13 -61.5(6) . . . . ? C10 C11 C12 C17 177.7(8) . . . . ? C16 C11 C12 C17 -3.9(12) . . . . ? Rh1 C11 C12 C17 117.0(8) . . . . ? C10 C11 C12 Rh1 60.6(5) . . . . ? C16 C11 C12 Rh1 -121.0(7) . . . . ? C2 Rh1 C12 C11 82.2(4) . . . . ? C10 Rh1 C12 C11 -38.5(4) . . . . ? C13 Rh1 C12 C11 -117.6(6) . . . . ? C1 Rh1 C12 C11 50.7(13) . . . . ? C14 Rh1 C12 C11 -80.3(4) . . . . ? C3 Rh1 C12 C11 123.6(4) . . . . ? C8 Rh1 C12 C11 164.1(4) . . . . ? C9 Rh1 C12 C11 -163.7(6) . . . . ? C2 Rh1 C12 C13 -160.2(4) . . . . ? C10 Rh1 C12 C13 79.1(4) . . . . ? C1 Rh1 C12 C13 168.3(10) . . . . ? C14 Rh1 C12 C13 37.3(4) . . . . ? C11 Rh1 C12 C13 117.6(6) . . . . ? C3 Rh1 C12 C13 -118.8(4) . . . . ? C8 Rh1 C12 C13 -78.3(5) . . . . ? C9 Rh1 C12 C13 -46.1(8) . . . . ? C2 Rh1 C12 C17 -39.6(7) . . . . ? C10 Rh1 C12 C17 -160.3(6) . . . . ? C13 Rh1 C12 C17 120.6(7) . . . . ? C1 Rh1 C12 C17 -71.1(13) . . . . ? C14 Rh1 C12 C17 157.9(6) . . . . ? C11 Rh1 C12 C17 -121.8(7) . . . . ? C3 Rh1 C12 C17 1.8(6) . . . . ? C8 Rh1 C12 C17 42.3(7) . . . . ? C9 Rh1 C12 C17 74.5(10) . . . . ? C11 C12 C13 C14 0.2(10) . . . . ? C17 C12 C13 C14 -178.4(8) . . . . ? Rh1 C12 C13 C14 -62.0(6) . . . . ? C11 C12 C13 C18 -179.5(7) . . . . ? C17 C12 C13 C18 1.9(13) . . . . ? Rh1 C12 C13 C18 118.3(8) . . . . ? C11 C12 C13 Rh1 62.1(5) . . . . ? C17 C12 C13 Rh1 -116.5(8) . . . . ? C2 Rh1 C13 C14 168.5(7) . . . . ? C10 Rh1 C13 C14 36.7(4) . . . . ? C12 Rh1 C13 C14 117.7(6) . . . . ? C1 Rh1 C13 C14 -52.5(9) . . . . ? C11 Rh1 C13 C14 80.1(4) . . . . ? C3 Rh1 C13 C14 -160.1(4) . . . . ? C8 Rh1 C13 C14 -120.5(5) . . . . ? C9 Rh1 C13 C14 -81.4(6) . . . . ? C2 Rh1 C13 C12 50.8(10) . . . . ? C10 Rh1 C13 C12 -81.0(4) . . . . ? C1 Rh1 C13 C12 -170.2(8) . . . . ? C14 Rh1 C13 C12 -117.7(6) . . . . ? C11 Rh1 C13 C12 -37.6(4) . . . . ? C3 Rh1 C13 C12 82.2(4) . . . . ? C8 Rh1 C13 C12 121.8(4) . . . . ? C9 Rh1 C13 C12 160.9(4) . . . . ? C2 Rh1 C13 C18 -69.5(10) . . . . ? C10 Rh1 C13 C18 158.7(7) . . . . ? C12 Rh1 C13 C18 -120.3(8) . . . . ? C1 Rh1 C13 C18 69.6(11) . . . . ? C14 Rh1 C13 C18 122.1(8) . . . . ? C11 Rh1 C13 C18 -157.8(7) . . . . ? C3 Rh1 C13 C18 -38.1(7) . . . . ? C8 Rh1 C13 C18 1.6(7) . . . . ? C9 Rh1 C13 C18 40.6(8) . . . . ? C11 C10 C14 C13 -1.3(10) . . . . ? C15 C10 C14 C13 -179.7(8) . . . . ? Rh1 C10 C14 C13 60.9(6) . . . . ? C11 C10 C14 C19 176.3(7) . . . . ? C15 C10 C14 C19 -2.1(14) . . . . ? Rh1 C10 C14 C19 -121.5(9) . . . . ? C11 C10 C14 Rh1 -62.2(5) . . . . ? C15 C10 C14 Rh1 119.4(8) . . . . ? C12 C13 C14 C10 0.7(10) . . . . ? C18 C13 C14 C10 -179.6(7) . . . . ? Rh1 C13 C14 C10 -60.8(6) . . . . ? C12 C13 C14 C19 -177.0(7) . . . . ? C18 C13 C14 C19 2.7(15) . . . . ? Rh1 C13 C14 C19 121.5(8) . . . . ? C12 C13 C14 Rh1 61.5(6) . . . . ? C18 C13 C14 Rh1 -118.8(9) . . . . ? C2 Rh1 C14 C10 -48.3(12) . . . . ? C13 Rh1 C14 C10 118.5(7) . . . . ? C12 Rh1 C14 C10 80.5(5) . . . . ? C1 Rh1 C14 C10 -82.7(6) . . . . ? C11 Rh1 C14 C10 37.7(4) . . . . ? C3 Rh1 C14 C10 166.2(8) . . . . ? C8 Rh1 C14 C10 -162.5(4) . . . . ? C9 Rh1 C14 C10 -123.2(5) . . . . ? C2 Rh1 C14 C13 -166.9(9) . . . . ? C10 Rh1 C14 C13 -118.5(7) . . . . ? C12 Rh1 C14 C13 -38.0(4) . . . . ? C1 Rh1 C14 C13 158.8(4) . . . . ? C11 Rh1 C14 C13 -80.8(5) . . . . ? C3 Rh1 C14 C13 47.7(10) . . . . ? C8 Rh1 C14 C13 78.9(6) . . . . ? C9 Rh1 C14 C13 118.3(4) . . . . ? C2 Rh1 C14 C19 74.0(11) . . . . ? C10 Rh1 C14 C19 122.4(10) . . . . ? C13 Rh1 C14 C19 -119.1(8) . . . . ? C12 Rh1 C14 C19 -157.1(7) . . . . ? C1 Rh1 C14 C19 39.7(8) . . . . ? C11 Rh1 C14 C19 160.1(8) . . . . ? C3 Rh1 C14 C19 -71.4(12) . . . . ? C8 Rh1 C14 C19 -40.2(9) . . . . ? C9 Rh1 C14 C19 -0.8(7) . . . . ? C9 C1 C20 O1 141.3(9) . . . . ? C2 C1 C20 O1 -45.6(12) . . . . ? Rh1 C1 C20 O1 40.4(11) . . . . ? C9 C1 C20 O2 -46.6(11) . . . . ? C2 C1 C20 O2 126.5(7) . . . . ? Rh1 C1 C20 O2 -147.5(6) . . . . ? O1 C20 O2 C21 -4.1(10) . . . . ? C1 C20 O2 C21 -176.1(6) . . . . ? C20 O2 C21 C22 -89.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.782 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.148 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2008). SAINT V7.60A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2009). APEX2 V2009.1-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_3g _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll57b _chemical_melting_point ? _chemical_formula_moiety 'C27 H31 Cl Ir N O2' _chemical_formula_sum 'C27 H31 Cl Ir N O2' _chemical_formula_weight 629.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0411(9) _cell_length_b 16.0222(13) _cell_length_c 16.1837(13) _cell_angle_alpha 63.1430(10) _cell_angle_beta 87.654(2) _cell_angle_gamma 72.193(2) _cell_volume 2415.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3991 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 36.39 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 5.661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4089 _exptl_absorpt_correction_T_max 0.5614 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53539 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 35.63 _reflns_number_total 21873 _reflns_number_gt 14955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.8527P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 21873 _refine_ls_number_parameters 591 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.548755(13) 0.813681(10) 0.354839(9) 0.01503(3) Uani 1 1 d . . . Cl1 Cl 0.69167(9) 0.90982(7) 0.29753(7) 0.02616(19) Uani 1 1 d . . . N1 N 0.4479(3) 0.9159(2) 0.4026(2) 0.0173(6) Uani 1 1 d . . . C1 C 0.6615(4) 0.7386(3) 0.4820(3) 0.0201(7) Uani 1 1 d . . . C2 C 0.6229(4) 0.6969(3) 0.5668(3) 0.0220(7) Uani 1 1 d . . . C3 C 0.4872(4) 0.7023(3) 0.5796(3) 0.0210(7) Uani 1 1 d . . . C4 C 0.4605(4) 0.6158(3) 0.6390(3) 0.0265(8) Uani 1 1 d . . . H4 H 0.5295 0.5556 0.6682 0.032 Uiso 1 1 calc R . . C5 C 0.3373(5) 0.6150(3) 0.6566(3) 0.0310(10) Uani 1 1 d . . . H5 H 0.3228 0.5549 0.6976 0.037 Uiso 1 1 calc R . . C6 C 0.2349(5) 0.7016(3) 0.6146(3) 0.0297(9) Uani 1 1 d . . . H6 H 0.1497 0.7012 0.6250 0.036 Uiso 1 1 calc R . . C7 C 0.2588(4) 0.7886(3) 0.5574(3) 0.0251(8) Uani 1 1 d . . . H7 H 0.1891 0.8485 0.5296 0.030 Uiso 1 1 calc R . . C8 C 0.3833(4) 0.7907(3) 0.5393(3) 0.0202(7) Uani 1 1 d . . . C9 C 0.3939(4) 0.8909(3) 0.4833(3) 0.0189(7) Uani 1 1 d . . . C10 C 0.4190(4) 0.7405(3) 0.3439(3) 0.0202(7) Uani 1 1 d . . . C11 C 0.5478(4) 0.6837(3) 0.3461(3) 0.0224(7) Uani 1 1 d . . . C12 C 0.5998(4) 0.7424(3) 0.2674(3) 0.0239(8) Uani 1 1 d . . . C13 C 0.4999(4) 0.8359(3) 0.2131(3) 0.0234(8) Uani 1 1 d . . . C14 C 0.3907(4) 0.8345(3) 0.2606(3) 0.0215(7) Uani 1 1 d . . . C15 C 0.3200(5) 0.7018(4) 0.4004(3) 0.0324(10) Uani 1 1 d . . . H15A H 0.2839 0.6712 0.3715 0.049 Uiso 1 1 calc R . . H15B H 0.2517 0.7564 0.4028 0.049 Uiso 1 1 calc R . . H15C H 0.3595 0.6525 0.4637 0.049 Uiso 1 1 calc R . . C16 C 0.6137(5) 0.5797(3) 0.4188(3) 0.0359(11) Uani 1 1 d . . . H16A H 0.5905 0.5337 0.4032 0.054 Uiso 1 1 calc R . . H16B H 0.5871 0.5715 0.4798 0.054 Uiso 1 1 calc R . . H16C H 0.7067 0.5660 0.4208 0.054 Uiso 1 1 calc R . . C17 C 0.7303(4) 0.7114(4) 0.2388(4) 0.0402(12) Uani 1 1 d . . . H17A H 0.7220 0.7054 0.1818 0.060 Uiso 1 1 calc R . . H17B H 0.7821 0.6475 0.2887 0.060 Uiso 1 1 calc R . . H17C H 0.7719 0.7610 0.2272 0.060 Uiso 1 1 calc R . . C18 C 0.5145(5) 0.9169(4) 0.1241(3) 0.0393(12) Uani 1 1 d . . . H18A H 0.5033 0.9026 0.0727 0.059 Uiso 1 1 calc R . . H18B H 0.6001 0.9222 0.1274 0.059 Uiso 1 1 calc R . . H18C H 0.4497 0.9794 0.1136 0.059 Uiso 1 1 calc R . . C19 C 0.2657(4) 0.9157(4) 0.2327(3) 0.0339(10) Uani 1 1 d . . . H19A H 0.2071 0.9051 0.1973 0.051 Uiso 1 1 calc R . . H19B H 0.2792 0.9792 0.1939 0.051 Uiso 1 1 calc R . . H19C H 0.2285 0.9161 0.2886 0.051 Uiso 1 1 calc R . . C20 C 0.8007(4) 0.7274(3) 0.4779(3) 0.0241(8) Uani 1 1 d . . . O1 O 0.8585(3) 0.7641(2) 0.5075(2) 0.0321(7) Uani 1 1 d . . . O2 O 0.8595(3) 0.6719(2) 0.4365(2) 0.0239(6) Uani 1 1 d . . . C21 C 0.9934(4) 0.6624(4) 0.4268(4) 0.0347(11) Uani 1 1 d . . . H21A H 1.0422 0.6326 0.4888 0.042 Uiso 1 1 calc R . . H21B H 1.0028 0.7283 0.3884 0.042 Uiso 1 1 calc R . . C22 C 1.0443(4) 0.5972(4) 0.3803(4) 0.0347(10) Uani 1 1 d . . . H22A H 1.1359 0.5875 0.3756 0.052 Uiso 1 1 calc R . . H22B H 0.9985 0.6289 0.3177 0.052 Uiso 1 1 calc R . . H22C H 1.0316 0.5331 0.4174 0.052 Uiso 1 1 calc R . . C23 C 0.7135(4) 0.6369(3) 0.6561(3) 0.0325(10) Uani 1 1 d . . . H23A H 0.7944 0.6514 0.6450 0.049 Uiso 1 1 calc R . . H23B H 0.7298 0.5663 0.6768 0.049 Uiso 1 1 calc R . . H23C H 0.6749 0.6540 0.7043 0.049 Uiso 1 1 calc R . . C24 C 0.3371(4) 0.9615(3) 0.5131(3) 0.0227(8) Uani 1 1 d . . . H24 H 0.3034 0.9423 0.5714 0.027 Uiso 1 1 calc R . . C25 C 0.3294(4) 1.0593(3) 0.4591(3) 0.0263(8) Uani 1 1 d . . . H25 H 0.2919 1.1074 0.4798 0.032 Uiso 1 1 calc R . . C26 C 0.3773(4) 1.0850(3) 0.3748(3) 0.0267(8) Uani 1 1 d . . . H26 H 0.3702 1.1519 0.3346 0.032 Uiso 1 1 calc R . . C27 C 0.4362(4) 1.0123(3) 0.3493(3) 0.0226(7) Uani 1 1 d . . . H27 H 0.4702 1.0308 0.2911 0.027 Uiso 1 1 calc R . . Ir2 Ir 0.239526(12) 0.741344(9) 0.988821(9) 0.01505(3) Uani 1 1 d . . . Cl2 Cl 0.21790(10) 0.70938(7) 1.14919(6) 0.02558(19) Uani 1 1 d . . . N2 N 0.1621(3) 0.8950(2) 0.9457(2) 0.0180(6) Uani 1 1 d . . . C28 C 0.0527(3) 0.7442(3) 0.9783(3) 0.0189(7) Uani 1 1 d . . . C29 C -0.0371(4) 0.8005(3) 0.9039(3) 0.0202(7) Uani 1 1 d . . . C30 C -0.0082(3) 0.8656(3) 0.8109(3) 0.0195(7) Uani 1 1 d . . . C31 C -0.0468(4) 0.8571(3) 0.7342(3) 0.0263(8) Uani 1 1 d . . . H31 H -0.0874 0.8093 0.7448 0.032 Uiso 1 1 calc R . . C32 C -0.0280(4) 0.9152(4) 0.6445(3) 0.0317(10) Uani 1 1 d . . . H32 H -0.0535 0.9065 0.5944 0.038 Uiso 1 1 calc R . . C33 C 0.0286(4) 0.9869(3) 0.6279(3) 0.0309(9) Uani 1 1 d . . . H33 H 0.0418 1.0279 0.5663 0.037 Uiso 1 1 calc R . . C34 C 0.0656(4) 0.9979(3) 0.7015(3) 0.0245(8) Uani 1 1 d . . . H34 H 0.1025 1.0481 0.6894 0.029 Uiso 1 1 calc R . . C35 C 0.0505(3) 0.9374(3) 0.7941(3) 0.0182(7) Uani 1 1 d . . . C36 C 0.0871(3) 0.9637(3) 0.8644(3) 0.0186(7) Uani 1 1 d . . . C37 C 0.3461(3) 0.7315(3) 0.8762(3) 0.0186(7) Uani 1 1 d . . . C38 C 0.3188(3) 0.6413(3) 0.9312(3) 0.0186(7) Uani 1 1 d . . . C39 C 0.3772(3) 0.5987(3) 1.0248(3) 0.0193(7) Uani 1 1 d . . . C40 C 0.4491(3) 0.6612(3) 1.0258(3) 0.0183(7) Uani 1 1 d . . . C41 C 0.4290(3) 0.7419(3) 0.9361(3) 0.0183(7) Uani 1 1 d . . . C42 C 0.3219(4) 0.7917(3) 0.7723(3) 0.0248(8) Uani 1 1 d . . . H42A H 0.3918 0.7633 0.7439 0.037 Uiso 1 1 calc R . . H42B H 0.3171 0.8598 0.7550 0.037 Uiso 1 1 calc R . . H42C H 0.2408 0.7915 0.7500 0.037 Uiso 1 1 calc R . . C43 C 0.2437(4) 0.5996(3) 0.8943(3) 0.0259(8) Uani 1 1 d . . . H43A H 0.3005 0.5608 0.8671 0.039 Uiso 1 1 calc R . . H43B H 0.1755 0.6536 0.8464 0.039 Uiso 1 1 calc R . . H43C H 0.2058 0.5569 0.9453 0.039 Uiso 1 1 calc R . . C44 C 0.3792(4) 0.5024(3) 1.1047(3) 0.0246(8) Uani 1 1 d . . . H44A H 0.4611 0.4518 1.1124 0.037 Uiso 1 1 calc R . . H44B H 0.3091 0.4826 1.0922 0.037 Uiso 1 1 calc R . . H44C H 0.3687 0.5095 1.1618 0.037 Uiso 1 1 calc R . . C45 C 0.5269(4) 0.6434(3) 1.1094(3) 0.0278(9) Uani 1 1 d . . . H45A H 0.6174 0.6110 1.1079 0.042 Uiso 1 1 calc R . . H45B H 0.4976 0.6009 1.1663 0.042 Uiso 1 1 calc R . . H45C H 0.5167 0.7066 1.1088 0.042 Uiso 1 1 calc R . . C46 C 0.4833(4) 0.8249(3) 0.9048(3) 0.0279(9) Uani 1 1 d . . . H46A H 0.5572 0.8126 0.8713 0.042 Uiso 1 1 calc R . . H46B H 0.5104 0.8293 0.9592 0.042 Uiso 1 1 calc R . . H46C H 0.4179 0.8871 0.8633 0.042 Uiso 1 1 calc R . . C47 C 0.0103(4) 0.6746(3) 1.0631(3) 0.0211(7) Uani 1 1 d . . . O3 O -0.0628(3) 0.6960(2) 1.1131(2) 0.0337(7) Uani 1 1 d . . . O4 O 0.0585(3) 0.58073(19) 1.07621(19) 0.0218(5) Uani 1 1 d . . . C48 C 0.0172(4) 0.5093(3) 1.1551(3) 0.0282(9) Uani 1 1 d . . . H48A H -0.0775 0.5298 1.1504 0.034 Uiso 1 1 calc R . . H48B H 0.0498 0.5037 1.2141 0.034 Uiso 1 1 calc R . . C49 C 0.0704(4) 0.4117(3) 1.1531(3) 0.0320(10) Uani 1 1 d . . . H49A H 0.0464 0.3608 1.2066 0.048 Uiso 1 1 calc R . . H49B H 0.1639 0.3931 1.1562 0.048 Uiso 1 1 calc R . . H49C H 0.0355 0.4177 1.0953 0.048 Uiso 1 1 calc R . . C50 C -0.1728(4) 0.7942(3) 0.9068(3) 0.0282(9) Uani 1 1 d . . . H50A H -0.2148 0.8130 0.9532 0.042 Uiso 1 1 calc R . . H50B H -0.1688 0.7264 0.9237 0.042 Uiso 1 1 calc R . . H50C H -0.2219 0.8392 0.8453 0.042 Uiso 1 1 calc R . . C51 C 0.0474(4) 1.0632(3) 0.8424(3) 0.0218(7) Uani 1 1 d . . . H51 H -0.0059 1.1104 0.7859 0.026 Uiso 1 1 calc R . . C52 C 0.0837(4) 1.0951(3) 0.9007(3) 0.0247(8) Uani 1 1 d . . . H52 H 0.0547 1.1631 0.8859 0.030 Uiso 1 1 calc R . . C53 C 0.1636(4) 1.0250(3) 0.9814(3) 0.0263(8) Uani 1 1 d . . . H53 H 0.1929 1.0441 1.0225 0.032 Uiso 1 1 calc R . . C54 C 0.2002(4) 0.9268(3) 1.0015(3) 0.0227(8) Uani 1 1 d . . . H54 H 0.2548 0.8791 1.0573 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01570(6) 0.01409(6) 0.01638(6) -0.00781(5) 0.00365(5) -0.00522(5) Cl1 0.0229(4) 0.0230(4) 0.0351(5) -0.0122(4) 0.0089(4) -0.0133(4) N1 0.0185(14) 0.0147(13) 0.0196(14) -0.0088(11) 0.0031(11) -0.0052(11) C1 0.0187(17) 0.0187(16) 0.0237(18) -0.0127(14) -0.0011(14) -0.0018(13) C2 0.0238(18) 0.0166(16) 0.0194(17) -0.0073(14) -0.0029(14) 0.0007(14) C3 0.0270(19) 0.0198(17) 0.0169(16) -0.0103(14) 0.0026(14) -0.0058(14) C4 0.036(2) 0.0220(18) 0.0183(17) -0.0083(15) 0.0058(16) -0.0068(16) C5 0.051(3) 0.026(2) 0.0213(19) -0.0108(16) 0.0154(19) -0.020(2) C6 0.036(2) 0.035(2) 0.026(2) -0.0171(18) 0.0150(18) -0.0191(19) C7 0.0255(19) 0.030(2) 0.0228(19) -0.0153(16) 0.0074(15) -0.0078(16) C8 0.0218(17) 0.0232(18) 0.0182(16) -0.0115(14) 0.0039(13) -0.0079(14) C9 0.0187(16) 0.0181(16) 0.0212(17) -0.0124(14) -0.0006(13) -0.0017(13) C10 0.0265(19) 0.0220(17) 0.0187(16) -0.0130(14) 0.0060(14) -0.0114(15) C11 0.0275(19) 0.0200(17) 0.0266(19) -0.0154(15) 0.0021(15) -0.0091(15) C12 0.0223(18) 0.033(2) 0.029(2) -0.0226(18) 0.0092(15) -0.0128(16) C13 0.0246(19) 0.034(2) 0.0190(17) -0.0138(16) 0.0084(14) -0.0167(16) C14 0.0200(17) 0.0251(18) 0.0225(18) -0.0131(15) 0.0057(14) -0.0086(14) C15 0.041(3) 0.049(3) 0.028(2) -0.025(2) 0.0183(19) -0.033(2) C16 0.046(3) 0.0169(18) 0.043(3) -0.0157(19) -0.004(2) -0.0028(18) C17 0.025(2) 0.068(4) 0.051(3) -0.048(3) 0.013(2) -0.014(2) C18 0.049(3) 0.053(3) 0.022(2) -0.015(2) 0.013(2) -0.030(3) C19 0.023(2) 0.042(3) 0.035(2) -0.020(2) -0.0027(18) -0.0042(18) C20 0.0218(18) 0.0196(17) 0.029(2) -0.0124(16) -0.0003(15) -0.0013(14) O1 0.0199(14) 0.0319(16) 0.051(2) -0.0280(16) -0.0016(13) -0.0023(12) O2 0.0180(13) 0.0236(14) 0.0332(15) -0.0177(12) 0.0031(11) -0.0034(10) C21 0.0179(19) 0.034(2) 0.061(3) -0.029(2) 0.010(2) -0.0096(17) C22 0.0198(19) 0.039(3) 0.053(3) -0.029(2) 0.0130(19) -0.0086(18) C23 0.032(2) 0.030(2) 0.023(2) -0.0062(17) -0.0062(17) -0.0017(18) C24 0.0215(18) 0.0232(18) 0.029(2) -0.0190(16) 0.0023(15) -0.0036(14) C25 0.0231(19) 0.0240(19) 0.039(2) -0.0217(18) 0.0002(17) -0.0046(15) C26 0.0231(19) 0.0165(17) 0.041(2) -0.0148(17) -0.0013(17) -0.0033(14) C27 0.0240(19) 0.0170(16) 0.0253(19) -0.0079(14) 0.0033(15) -0.0077(14) Ir2 0.01512(6) 0.01268(6) 0.01488(6) -0.00624(5) 0.00355(5) -0.00167(5) Cl2 0.0300(5) 0.0236(4) 0.0173(4) -0.0088(3) 0.0051(3) -0.0023(4) N2 0.0165(14) 0.0159(13) 0.0200(14) -0.0087(11) 0.0039(11) -0.0030(11) C28 0.0186(16) 0.0151(15) 0.0212(17) -0.0094(13) 0.0074(13) -0.0022(13) C29 0.0190(17) 0.0182(16) 0.0275(19) -0.0133(15) 0.0084(14) -0.0077(13) C30 0.0148(15) 0.0186(16) 0.0230(18) -0.0095(14) 0.0023(13) -0.0030(13) C31 0.0223(19) 0.026(2) 0.030(2) -0.0131(17) 0.0003(16) -0.0062(15) C32 0.023(2) 0.044(3) 0.024(2) -0.0163(19) -0.0024(16) -0.0038(18) C33 0.022(2) 0.037(2) 0.0201(19) -0.0057(17) -0.0004(15) -0.0047(17) C34 0.0207(18) 0.0225(18) 0.0226(18) -0.0050(15) 0.0023(14) -0.0055(14) C35 0.0133(15) 0.0159(15) 0.0207(17) -0.0064(13) 0.0014(13) -0.0017(12) C36 0.0154(15) 0.0151(15) 0.0220(17) -0.0077(13) 0.0047(13) -0.0020(12) C37 0.0147(15) 0.0216(17) 0.0181(16) -0.0095(13) 0.0056(13) -0.0040(13) C38 0.0150(15) 0.0181(16) 0.0233(17) -0.0121(14) 0.0084(13) -0.0030(12) C39 0.0175(16) 0.0143(15) 0.0227(17) -0.0087(13) 0.0054(13) -0.0006(12) C40 0.0144(15) 0.0165(15) 0.0201(16) -0.0073(13) 0.0022(13) -0.0016(12) C41 0.0147(15) 0.0162(15) 0.0212(17) -0.0084(13) 0.0052(13) -0.0021(12) C42 0.0204(18) 0.028(2) 0.0193(17) -0.0088(15) 0.0040(14) -0.0025(15) C43 0.0222(19) 0.029(2) 0.037(2) -0.0250(19) 0.0079(16) -0.0086(16) C44 0.0244(19) 0.0146(16) 0.027(2) -0.0065(14) 0.0053(15) -0.0021(14) C45 0.028(2) 0.0218(19) 0.026(2) -0.0087(16) -0.0066(16) 0.0001(16) C46 0.026(2) 0.0230(19) 0.032(2) -0.0099(17) 0.0049(17) -0.0091(16) C47 0.0216(18) 0.0178(16) 0.0250(18) -0.0109(14) 0.0079(14) -0.0067(14) O3 0.0419(19) 0.0266(15) 0.0414(18) -0.0218(14) 0.0287(15) -0.0159(14) O4 0.0242(14) 0.0151(12) 0.0252(14) -0.0093(10) 0.0072(11) -0.0061(10) C48 0.033(2) 0.0232(19) 0.026(2) -0.0071(16) 0.0074(17) -0.0123(17) C49 0.034(2) 0.0197(19) 0.037(2) -0.0071(17) -0.0014(19) -0.0100(17) C50 0.0175(18) 0.027(2) 0.040(2) -0.0162(18) 0.0058(17) -0.0067(15) C51 0.0164(16) 0.0142(15) 0.029(2) -0.0069(14) 0.0044(14) -0.0033(13) C52 0.0262(19) 0.0158(16) 0.035(2) -0.0141(16) 0.0098(16) -0.0067(14) C53 0.030(2) 0.0239(19) 0.032(2) -0.0186(17) 0.0096(17) -0.0099(16) C54 0.0249(19) 0.0197(17) 0.0246(19) -0.0133(15) 0.0026(15) -0.0037(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.071(4) . ? Ir1 N1 2.116(3) . ? Ir1 C12 2.150(4) . ? Ir1 C11 2.154(4) . ? Ir1 C10 2.166(4) . ? Ir1 C14 2.209(4) . ? Ir1 C13 2.218(4) . ? Ir1 Cl1 2.4081(10) . ? N1 C27 1.352(5) . ? N1 C9 1.353(5) . ? C1 C2 1.346(6) . ? C1 C20 1.494(6) . ? C2 C3 1.486(6) . ? C2 C23 1.512(5) . ? C3 C4 1.397(6) . ? C3 C8 1.407(5) . ? C4 C5 1.381(6) . ? C4 H4 0.9500 . ? C5 C6 1.385(6) . ? C5 H5 0.9500 . ? C6 C7 1.382(6) . ? C6 H6 0.9500 . ? C7 C8 1.400(6) . ? C7 H7 0.9500 . ? C8 C9 1.484(5) . ? C9 C24 1.394(5) . ? C10 C11 1.427(5) . ? C10 C14 1.448(5) . ? C10 C15 1.495(6) . ? C11 C12 1.423(6) . ? C11 C16 1.498(6) . ? C12 C13 1.453(6) . ? C12 C17 1.501(6) . ? C13 C14 1.403(5) . ? C13 C18 1.485(6) . ? C14 C19 1.492(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O1 1.220(5) . ? C20 O2 1.344(5) . ? O2 C21 1.450(5) . ? C21 C22 1.513(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.383(6) . ? C24 H24 0.9500 . ? C25 C26 1.370(6) . ? C25 H25 0.9500 . ? C26 C27 1.378(5) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Ir2 C28 2.061(4) . ? Ir2 N2 2.119(3) . ? Ir2 C39 2.149(3) . ? Ir2 C38 2.152(3) . ? Ir2 C37 2.169(4) . ? Ir2 C40 2.228(3) . ? Ir2 C41 2.228(4) . ? Ir2 Cl2 2.4246(10) . ? N2 C54 1.352(5) . ? N2 C36 1.360(5) . ? C28 C29 1.347(5) . ? C28 C47 1.494(5) . ? C29 C30 1.484(5) . ? C29 C50 1.529(5) . ? C30 C31 1.405(6) . ? C30 C35 1.406(5) . ? C31 C32 1.375(6) . ? C31 H31 0.9500 . ? C32 C33 1.388(7) . ? C32 H32 0.9500 . ? C33 C34 1.374(6) . ? C33 H33 0.9500 . ? C34 C35 1.407(5) . ? C34 H34 0.9500 . ? C35 C36 1.486(5) . ? C36 C51 1.391(5) . ? C37 C38 1.433(5) . ? C37 C41 1.455(5) . ? C37 C42 1.498(5) . ? C38 C39 1.433(5) . ? C38 C43 1.494(5) . ? C39 C40 1.461(5) . ? C39 C44 1.494(5) . ? C40 C41 1.409(5) . ? C40 C45 1.499(5) . ? C41 C46 1.495(6) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 O3 1.205(4) . ? C47 O4 1.350(4) . ? O4 C48 1.449(5) . ? C48 C49 1.508(6) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.380(6) . ? C51 H51 0.9500 . ? C52 C53 1.382(6) . ? C52 H52 0.9500 . ? C53 C54 1.381(5) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 85.87(13) . . ? C1 Ir1 C12 113.78(15) . . ? N1 Ir1 C12 160.28(14) . . ? C1 Ir1 C11 95.85(15) . . ? N1 Ir1 C11 142.82(14) . . ? C12 Ir1 C11 38.61(16) . . ? C1 Ir1 C10 113.37(15) . . ? N1 Ir1 C10 107.21(13) . . ? C12 Ir1 C10 64.60(15) . . ? C11 Ir1 C10 38.58(15) . . ? C1 Ir1 C14 151.68(15) . . ? N1 Ir1 C14 98.29(13) . . ? C12 Ir1 C14 63.78(15) . . ? C11 Ir1 C14 64.17(15) . . ? C10 Ir1 C14 38.62(14) . . ? C1 Ir1 C13 152.36(15) . . ? N1 Ir1 C13 121.67(14) . . ? C12 Ir1 C13 38.83(16) . . ? C11 Ir1 C13 64.34(15) . . ? C10 Ir1 C13 63.81(14) . . ? C14 Ir1 C13 36.94(14) . . ? C1 Ir1 Cl1 87.34(12) . . ? N1 Ir1 Cl1 87.10(9) . . ? C12 Ir1 Cl1 95.12(11) . . ? C11 Ir1 Cl1 130.06(11) . . ? C10 Ir1 Cl1 155.11(10) . . ? C14 Ir1 Cl1 120.74(11) . . ? C13 Ir1 Cl1 91.40(11) . . ? C27 N1 C9 117.8(3) . . ? C27 N1 Ir1 118.2(3) . . ? C9 N1 Ir1 124.0(2) . . ? C2 C1 C20 117.3(3) . . ? C2 C1 Ir1 126.8(3) . . ? C20 C1 Ir1 116.0(3) . . ? C1 C2 C3 122.1(3) . . ? C1 C2 C23 123.4(4) . . ? C3 C2 C23 114.4(4) . . ? C4 C3 C8 117.5(4) . . ? C4 C3 C2 118.6(4) . . ? C8 C3 C2 123.9(4) . . ? C5 C4 C3 122.2(4) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 120.2(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 118.8(4) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 121.6(4) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 119.7(4) . . ? C7 C8 C9 115.0(3) . . ? C3 C8 C9 125.2(4) . . ? N1 C9 C24 120.4(4) . . ? N1 C9 C8 122.1(3) . . ? C24 C9 C8 117.4(4) . . ? C11 C10 C14 107.5(3) . . ? C11 C10 C15 126.1(4) . . ? C14 C10 C15 124.3(4) . . ? C11 C10 Ir1 70.2(2) . . ? C14 C10 Ir1 72.3(2) . . ? C15 C10 Ir1 135.7(3) . . ? C12 C11 C10 108.1(3) . . ? C12 C11 C16 127.0(4) . . ? C10 C11 C16 124.9(4) . . ? C12 C11 Ir1 70.6(2) . . ? C10 C11 Ir1 71.2(2) . . ? C16 C11 Ir1 124.6(3) . . ? C11 C12 C13 108.1(3) . . ? C11 C12 C17 126.8(4) . . ? C13 C12 C17 124.8(4) . . ? C11 C12 Ir1 70.8(2) . . ? C13 C12 Ir1 73.1(2) . . ? C17 C12 Ir1 126.3(3) . . ? C14 C13 C12 107.5(3) . . ? C14 C13 C18 127.5(4) . . ? C12 C13 C18 125.0(4) . . ? C14 C13 Ir1 71.2(2) . . ? C12 C13 Ir1 68.1(2) . . ? C18 C13 Ir1 125.7(3) . . ? C13 C14 C10 108.8(3) . . ? C13 C14 C19 126.8(4) . . ? C10 C14 C19 124.4(4) . . ? C13 C14 Ir1 71.9(2) . . ? C10 C14 Ir1 69.1(2) . . ? C19 C14 Ir1 124.2(3) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 O2 121.6(4) . . ? O1 C20 C1 125.4(4) . . ? O2 C20 C1 113.0(3) . . ? C20 O2 C21 115.3(3) . . ? O2 C21 C22 108.3(4) . . ? O2 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? O2 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C9 120.9(4) . . ? C25 C24 H24 119.5 . . ? C9 C24 H24 119.5 . . ? C26 C25 C24 118.1(4) . . ? C26 C25 H25 121.0 . . ? C24 C25 H25 121.0 . . ? C25 C26 C27 119.1(4) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? N1 C27 C26 123.5(4) . . ? N1 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C28 Ir2 N2 86.16(13) . . ? C28 Ir2 C39 113.24(14) . . ? N2 Ir2 C39 160.31(14) . . ? C28 Ir2 C38 96.73(14) . . ? N2 Ir2 C38 139.96(13) . . ? C39 Ir2 C38 38.92(14) . . ? C28 Ir2 C37 114.97(14) . . ? N2 Ir2 C37 104.40(13) . . ? C39 Ir2 C37 65.32(14) . . ? C38 Ir2 C37 38.75(14) . . ? C28 Ir2 C40 151.78(14) . . ? N2 Ir2 C40 121.94(13) . . ? C39 Ir2 C40 38.95(14) . . ? C38 Ir2 C40 64.18(14) . . ? C37 Ir2 C40 63.83(13) . . ? C28 Ir2 C41 153.39(14) . . ? N2 Ir2 C41 97.07(13) . . ? C39 Ir2 C41 64.19(14) . . ? C38 Ir2 C41 64.11(14) . . ? C37 Ir2 C41 38.62(14) . . ? C40 Ir2 C41 36.87(13) . . ? C28 Ir2 Cl2 87.47(11) . . ? N2 Ir2 Cl2 89.43(9) . . ? C39 Ir2 Cl2 94.52(10) . . ? C38 Ir2 Cl2 130.52(10) . . ? C37 Ir2 Cl2 153.96(10) . . ? C40 Ir2 Cl2 90.13(10) . . ? C41 Ir2 Cl2 118.87(10) . . ? C54 N2 C36 118.3(3) . . ? C54 N2 Ir2 115.8(2) . . ? C36 N2 Ir2 125.7(3) . . ? C29 C28 C47 115.0(3) . . ? C29 C28 Ir2 128.4(3) . . ? C47 C28 Ir2 116.6(3) . . ? C28 C29 C30 122.4(3) . . ? C28 C29 C50 122.4(4) . . ? C30 C29 C50 115.0(3) . . ? C31 C30 C35 118.1(4) . . ? C31 C30 C29 117.3(4) . . ? C35 C30 C29 124.5(3) . . ? C32 C31 C30 122.5(4) . . ? C32 C31 H31 118.7 . . ? C30 C31 H31 118.7 . . ? C31 C32 C33 119.3(4) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C34 C33 C32 119.4(4) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C35 122.2(4) . . ? C33 C34 H34 118.9 . . ? C35 C34 H34 118.9 . . ? C30 C35 C34 118.4(4) . . ? C30 C35 C36 126.0(3) . . ? C34 C35 C36 115.3(3) . . ? N2 C36 C51 120.0(4) . . ? N2 C36 C35 122.4(3) . . ? C51 C36 C35 117.5(3) . . ? C38 C37 C41 107.2(3) . . ? C38 C37 C42 126.7(4) . . ? C41 C37 C42 124.5(4) . . ? C38 C37 Ir2 70.0(2) . . ? C41 C37 Ir2 72.9(2) . . ? C42 C37 Ir2 133.2(3) . . ? C39 C38 C37 108.7(3) . . ? C39 C38 C43 126.8(4) . . ? C37 C38 C43 124.5(4) . . ? C39 C38 Ir2 70.4(2) . . ? C37 C38 Ir2 71.3(2) . . ? C43 C38 Ir2 125.2(3) . . ? C38 C39 C40 107.1(3) . . ? C38 C39 C44 127.3(4) . . ? C40 C39 C44 125.2(3) . . ? C38 C39 Ir2 70.66(19) . . ? C40 C39 Ir2 73.4(2) . . ? C44 C39 Ir2 126.8(3) . . ? C41 C40 C39 108.3(3) . . ? C41 C40 C45 126.3(4) . . ? C39 C40 C45 125.4(3) . . ? C41 C40 Ir2 71.6(2) . . ? C39 C40 Ir2 67.61(19) . . ? C45 C40 Ir2 125.0(3) . . ? C40 C41 C37 108.5(3) . . ? C40 C41 C46 127.1(4) . . ? C37 C41 C46 124.4(3) . . ? C40 C41 Ir2 71.5(2) . . ? C37 C41 Ir2 68.5(2) . . ? C46 C41 Ir2 126.3(3) . . ? C37 C42 H42A 109.5 . . ? C37 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C37 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C38 C43 H43A 109.5 . . ? C38 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C38 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C39 C44 H44A 109.5 . . ? C39 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C39 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C40 C45 H45A 109.5 . . ? C40 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C40 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C41 C46 H46A 109.5 . . ? C41 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C41 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O3 C47 O4 121.6(4) . . ? O3 C47 C28 126.8(4) . . ? O4 C47 C28 111.5(3) . . ? C47 O4 C48 114.8(3) . . ? O4 C48 C49 107.0(3) . . ? O4 C48 H48A 110.3 . . ? C49 C48 H48A 110.3 . . ? O4 C48 H48B 110.3 . . ? C49 C48 H48B 110.3 . . ? H48A C48 H48B 108.6 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C29 C50 H50A 109.5 . . ? C29 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C29 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C52 C51 C36 121.6(4) . . ? C52 C51 H51 119.2 . . ? C36 C51 H51 119.2 . . ? C51 C52 C53 117.8(4) . . ? C51 C52 H52 121.1 . . ? C53 C52 H52 121.1 . . ? C54 C53 C52 119.0(4) . . ? C54 C53 H53 120.5 . . ? C52 C53 H53 120.5 . . ? N2 C54 C53 123.3(4) . . ? N2 C54 H54 118.4 . . ? C53 C54 H54 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C27 124.8(3) . . . . ? C12 Ir1 N1 C27 -59.8(5) . . . . ? C11 Ir1 N1 C27 -141.0(3) . . . . ? C10 Ir1 N1 C27 -122.0(3) . . . . ? C14 Ir1 N1 C27 -83.4(3) . . . . ? C13 Ir1 N1 C27 -52.6(3) . . . . ? Cl1 Ir1 N1 C27 37.3(3) . . . . ? C1 Ir1 N1 C9 -55.5(3) . . . . ? C12 Ir1 N1 C9 119.9(4) . . . . ? C11 Ir1 N1 C9 38.8(4) . . . . ? C10 Ir1 N1 C9 57.7(3) . . . . ? C14 Ir1 N1 C9 96.4(3) . . . . ? C13 Ir1 N1 C9 127.1(3) . . . . ? Cl1 Ir1 N1 C9 -143.0(3) . . . . ? N1 Ir1 C1 C2 62.8(3) . . . . ? C12 Ir1 C1 C2 -115.5(3) . . . . ? C11 Ir1 C1 C2 -79.9(4) . . . . ? C10 Ir1 C1 C2 -44.2(4) . . . . ? C14 Ir1 C1 C2 -37.0(5) . . . . ? C13 Ir1 C1 C2 -122.0(4) . . . . ? Cl1 Ir1 C1 C2 150.1(3) . . . . ? N1 Ir1 C1 C20 -119.2(3) . . . . ? C12 Ir1 C1 C20 62.5(3) . . . . ? C11 Ir1 C1 C20 98.0(3) . . . . ? C10 Ir1 C1 C20 133.8(3) . . . . ? C14 Ir1 C1 C20 140.9(3) . . . . ? C13 Ir1 C1 C20 56.0(5) . . . . ? Cl1 Ir1 C1 C20 -32.0(3) . . . . ? C20 C1 C2 C3 -179.4(3) . . . . ? Ir1 C1 C2 C3 -1.5(6) . . . . ? C20 C1 C2 C23 -2.5(6) . . . . ? Ir1 C1 C2 C23 175.4(3) . . . . ? C1 C2 C3 C4 132.8(4) . . . . ? C23 C2 C3 C4 -44.4(5) . . . . ? C1 C2 C3 C8 -50.8(6) . . . . ? C23 C2 C3 C8 132.0(4) . . . . ? C8 C3 C4 C5 1.6(6) . . . . ? C2 C3 C4 C5 178.2(4) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C4 C5 C6 C7 -1.9(6) . . . . ? C5 C6 C7 C8 1.5(6) . . . . ? C6 C7 C8 C3 0.4(6) . . . . ? C6 C7 C8 C9 -174.9(4) . . . . ? C4 C3 C8 C7 -2.0(5) . . . . ? C2 C3 C8 C7 -178.4(4) . . . . ? C4 C3 C8 C9 172.9(4) . . . . ? C2 C3 C8 C9 -3.5(6) . . . . ? C27 N1 C9 C24 -5.0(5) . . . . ? Ir1 N1 C9 C24 175.3(3) . . . . ? C27 N1 C9 C8 170.2(3) . . . . ? Ir1 N1 C9 C8 -9.6(5) . . . . ? C7 C8 C9 N1 -123.9(4) . . . . ? C3 C8 C9 N1 61.0(5) . . . . ? C7 C8 C9 C24 51.4(5) . . . . ? C3 C8 C9 C24 -123.7(4) . . . . ? C1 Ir1 C10 C11 -68.7(2) . . . . ? N1 Ir1 C10 C11 -161.6(2) . . . . ? C12 Ir1 C10 C11 37.6(2) . . . . ? C14 Ir1 C10 C11 116.7(3) . . . . ? C13 Ir1 C10 C11 81.0(2) . . . . ? Cl1 Ir1 C10 C11 75.5(3) . . . . ? C1 Ir1 C10 C14 174.6(2) . . . . ? N1 Ir1 C10 C14 81.6(2) . . . . ? C12 Ir1 C10 C14 -79.1(2) . . . . ? C11 Ir1 C10 C14 -116.7(3) . . . . ? C13 Ir1 C10 C14 -35.8(2) . . . . ? Cl1 Ir1 C10 C14 -41.2(4) . . . . ? C1 Ir1 C10 C15 53.2(5) . . . . ? N1 Ir1 C10 C15 -39.8(5) . . . . ? C12 Ir1 C10 C15 159.5(5) . . . . ? C11 Ir1 C10 C15 121.9(5) . . . . ? C14 Ir1 C10 C15 -121.4(5) . . . . ? C13 Ir1 C10 C15 -157.1(5) . . . . ? Cl1 Ir1 C10 C15 -162.6(3) . . . . ? C14 C10 C11 C12 1.9(4) . . . . ? C15 C10 C11 C12 166.0(4) . . . . ? Ir1 C10 C11 C12 -61.3(3) . . . . ? C14 C10 C11 C16 -177.3(4) . . . . ? C15 C10 C11 C16 -13.1(6) . . . . ? Ir1 C10 C11 C16 119.6(4) . . . . ? C14 C10 C11 Ir1 63.1(3) . . . . ? C15 C10 C11 Ir1 -132.7(4) . . . . ? C1 Ir1 C11 C12 -121.4(2) . . . . ? N1 Ir1 C11 C12 147.7(2) . . . . ? C10 Ir1 C11 C12 117.9(3) . . . . ? C14 Ir1 C11 C12 79.6(2) . . . . ? C13 Ir1 C11 C12 38.4(2) . . . . ? Cl1 Ir1 C11 C12 -30.0(3) . . . . ? C1 Ir1 C11 C10 120.7(2) . . . . ? N1 Ir1 C11 C10 29.8(3) . . . . ? C12 Ir1 C11 C10 -117.9(3) . . . . ? C14 Ir1 C11 C10 -38.3(2) . . . . ? C13 Ir1 C11 C10 -79.5(2) . . . . ? Cl1 Ir1 C11 C10 -147.83(18) . . . . ? C1 Ir1 C11 C16 0.7(4) . . . . ? N1 Ir1 C11 C16 -90.2(4) . . . . ? C12 Ir1 C11 C16 122.1(5) . . . . ? C10 Ir1 C11 C16 -120.0(5) . . . . ? C14 Ir1 C11 C16 -158.3(4) . . . . ? C13 Ir1 C11 C16 160.5(4) . . . . ? Cl1 Ir1 C11 C16 92.2(4) . . . . ? C10 C11 C12 C13 -2.4(4) . . . . ? C16 C11 C12 C13 176.7(4) . . . . ? Ir1 C11 C12 C13 -64.1(3) . . . . ? C10 C11 C12 C17 -176.9(4) . . . . ? C16 C11 C12 C17 2.3(7) . . . . ? Ir1 C11 C12 C17 121.5(4) . . . . ? C10 C11 C12 Ir1 61.7(3) . . . . ? C16 C11 C12 Ir1 -119.2(4) . . . . ? C1 Ir1 C12 C11 68.1(3) . . . . ? N1 Ir1 C12 C11 -106.9(4) . . . . ? C10 Ir1 C12 C11 -37.6(2) . . . . ? C14 Ir1 C12 C11 -80.7(2) . . . . ? C13 Ir1 C12 C11 -116.7(3) . . . . ? Cl1 Ir1 C12 C11 157.4(2) . . . . ? C1 Ir1 C12 C13 -175.2(2) . . . . ? N1 Ir1 C12 C13 9.8(5) . . . . ? C11 Ir1 C12 C13 116.7(3) . . . . ? C10 Ir1 C12 C13 79.1(2) . . . . ? C14 Ir1 C12 C13 36.0(2) . . . . ? Cl1 Ir1 C12 C13 -85.9(2) . . . . ? C1 Ir1 C12 C17 -54.0(5) . . . . ? N1 Ir1 C12 C17 131.0(5) . . . . ? C11 Ir1 C12 C17 -122.1(5) . . . . ? C10 Ir1 C12 C17 -159.7(5) . . . . ? C14 Ir1 C12 C17 157.2(5) . . . . ? C13 Ir1 C12 C17 121.2(5) . . . . ? Cl1 Ir1 C12 C17 35.3(4) . . . . ? C11 C12 C13 C14 2.1(4) . . . . ? C17 C12 C13 C14 176.6(4) . . . . ? Ir1 C12 C13 C14 -60.5(3) . . . . ? C11 C12 C13 C18 -178.3(4) . . . . ? C17 C12 C13 C18 -3.7(7) . . . . ? Ir1 C12 C13 C18 119.1(4) . . . . ? C11 C12 C13 Ir1 62.6(3) . . . . ? C17 C12 C13 Ir1 -122.8(4) . . . . ? C1 Ir1 C13 C14 128.2(3) . . . . ? N1 Ir1 C13 C14 -57.4(3) . . . . ? C12 Ir1 C13 C14 118.7(3) . . . . ? C11 Ir1 C13 C14 80.5(3) . . . . ? C10 Ir1 C13 C14 37.4(2) . . . . ? Cl1 Ir1 C13 C14 -144.9(2) . . . . ? C1 Ir1 C13 C12 9.5(4) . . . . ? N1 Ir1 C13 C12 -176.1(2) . . . . ? C11 Ir1 C13 C12 -38.2(2) . . . . ? C10 Ir1 C13 C12 -81.3(2) . . . . ? C14 Ir1 C13 C12 -118.7(3) . . . . ? Cl1 Ir1 C13 C12 96.4(2) . . . . ? C1 Ir1 C13 C18 -108.6(5) . . . . ? N1 Ir1 C13 C18 65.8(4) . . . . ? C12 Ir1 C13 C18 -118.1(5) . . . . ? C11 Ir1 C13 C18 -156.3(4) . . . . ? C10 Ir1 C13 C18 160.6(4) . . . . ? C14 Ir1 C13 C18 123.2(5) . . . . ? Cl1 Ir1 C13 C18 -21.7(4) . . . . ? C12 C13 C14 C10 -0.9(4) . . . . ? C18 C13 C14 C10 179.5(4) . . . . ? Ir1 C13 C14 C10 -59.5(3) . . . . ? C12 C13 C14 C19 178.1(4) . . . . ? C18 C13 C14 C19 -1.5(7) . . . . ? Ir1 C13 C14 C19 119.6(4) . . . . ? C12 C13 C14 Ir1 58.6(3) . . . . ? C18 C13 C14 Ir1 -121.1(4) . . . . ? C11 C10 C14 C13 -0.6(4) . . . . ? C15 C10 C14 C13 -165.1(4) . . . . ? Ir1 C10 C14 C13 61.2(3) . . . . ? C11 C10 C14 C19 -179.6(4) . . . . ? C15 C10 C14 C19 15.9(6) . . . . ? Ir1 C10 C14 C19 -117.8(4) . . . . ? C11 C10 C14 Ir1 -61.8(3) . . . . ? C15 C10 C14 Ir1 133.7(4) . . . . ? C1 Ir1 C14 C13 -129.7(3) . . . . ? N1 Ir1 C14 C13 133.5(2) . . . . ? C12 Ir1 C14 C13 -37.8(2) . . . . ? C11 Ir1 C14 C13 -81.0(3) . . . . ? C10 Ir1 C14 C13 -119.2(3) . . . . ? Cl1 Ir1 C14 C13 42.0(3) . . . . ? C1 Ir1 C14 C10 -10.5(4) . . . . ? N1 Ir1 C14 C10 -107.3(2) . . . . ? C12 Ir1 C14 C10 81.4(2) . . . . ? C11 Ir1 C14 C10 38.2(2) . . . . ? C13 Ir1 C14 C10 119.2(3) . . . . ? Cl1 Ir1 C14 C10 161.19(18) . . . . ? C1 Ir1 C14 C19 107.6(4) . . . . ? N1 Ir1 C14 C19 10.9(4) . . . . ? C12 Ir1 C14 C19 -160.4(4) . . . . ? C11 Ir1 C14 C19 156.4(4) . . . . ? C10 Ir1 C14 C19 118.2(4) . . . . ? C13 Ir1 C14 C19 -122.6(5) . . . . ? Cl1 Ir1 C14 C19 -80.6(4) . . . . ? C2 C1 C20 O1 -66.7(6) . . . . ? Ir1 C1 C20 O1 115.1(4) . . . . ? C2 C1 C20 O2 113.7(4) . . . . ? Ir1 C1 C20 O2 -64.4(4) . . . . ? O1 C20 O2 C21 -2.3(6) . . . . ? C1 C20 O2 C21 177.3(4) . . . . ? C20 O2 C21 C22 179.4(4) . . . . ? N1 C9 C24 C25 3.1(6) . . . . ? C8 C9 C24 C25 -172.3(4) . . . . ? C9 C24 C25 C26 0.9(6) . . . . ? C24 C25 C26 C27 -2.9(6) . . . . ? C9 N1 C27 C26 3.0(6) . . . . ? Ir1 N1 C27 C26 -177.2(3) . . . . ? C25 C26 C27 N1 1.0(6) . . . . ? C28 Ir2 N2 C54 126.6(3) . . . . ? C39 Ir2 N2 C54 -62.7(5) . . . . ? C38 Ir2 N2 C54 -137.5(3) . . . . ? C37 Ir2 N2 C54 -118.5(3) . . . . ? C40 Ir2 N2 C54 -50.7(3) . . . . ? C41 Ir2 N2 C54 -79.9(3) . . . . ? Cl2 Ir2 N2 C54 39.1(3) . . . . ? C28 Ir2 N2 C36 -58.9(3) . . . . ? C39 Ir2 N2 C36 111.7(4) . . . . ? C38 Ir2 N2 C36 37.0(4) . . . . ? C37 Ir2 N2 C36 55.9(3) . . . . ? C40 Ir2 N2 C36 123.8(3) . . . . ? C41 Ir2 N2 C36 94.5(3) . . . . ? Cl2 Ir2 N2 C36 -146.4(3) . . . . ? N2 Ir2 C28 C29 55.8(3) . . . . ? C39 Ir2 C28 C29 -120.7(3) . . . . ? C38 Ir2 C28 C29 -84.1(4) . . . . ? C37 Ir2 C28 C29 -48.3(4) . . . . ? C40 Ir2 C28 C29 -129.0(4) . . . . ? C41 Ir2 C28 C29 -42.3(5) . . . . ? Cl2 Ir2 C28 C29 145.4(3) . . . . ? N2 Ir2 C28 C47 -124.9(3) . . . . ? C39 Ir2 C28 C47 58.5(3) . . . . ? C38 Ir2 C28 C47 95.2(3) . . . . ? C37 Ir2 C28 C47 131.0(3) . . . . ? C40 Ir2 C28 C47 50.3(4) . . . . ? C41 Ir2 C28 C47 137.0(3) . . . . ? Cl2 Ir2 C28 C47 -35.3(3) . . . . ? C47 C28 C29 C30 -173.1(3) . . . . ? Ir2 C28 C29 C30 6.2(5) . . . . ? C47 C28 C29 C50 0.7(5) . . . . ? Ir2 C28 C29 C50 180.0(3) . . . . ? C28 C29 C30 C31 128.9(4) . . . . ? C50 C29 C30 C31 -45.3(5) . . . . ? C28 C29 C30 C35 -53.6(5) . . . . ? C50 C29 C30 C35 132.1(4) . . . . ? C35 C30 C31 C32 0.7(6) . . . . ? C29 C30 C31 C32 178.3(4) . . . . ? C30 C31 C32 C33 -1.4(6) . . . . ? C31 C32 C33 C34 0.4(6) . . . . ? C32 C33 C34 C35 1.4(6) . . . . ? C31 C30 C35 C34 1.0(5) . . . . ? C29 C30 C35 C34 -176.4(3) . . . . ? C31 C30 C35 C36 174.2(3) . . . . ? C29 C30 C35 C36 -3.2(6) . . . . ? C33 C34 C35 C30 -2.1(6) . . . . ? C33 C34 C35 C36 -176.0(4) . . . . ? C54 N2 C36 C51 -2.6(5) . . . . ? Ir2 N2 C36 C51 -176.9(3) . . . . ? C54 N2 C36 C35 174.0(3) . . . . ? Ir2 N2 C36 C35 -0.3(5) . . . . ? C30 C35 C36 N2 53.8(5) . . . . ? C34 C35 C36 N2 -132.8(4) . . . . ? C30 C35 C36 C51 -129.6(4) . . . . ? C34 C35 C36 C51 43.8(5) . . . . ? C28 Ir2 C37 C38 -68.1(2) . . . . ? N2 Ir2 C37 C38 -160.5(2) . . . . ? C39 Ir2 C37 C38 37.3(2) . . . . ? C40 Ir2 C37 C38 80.6(2) . . . . ? C41 Ir2 C37 C38 116.2(3) . . . . ? Cl2 Ir2 C37 C38 79.3(3) . . . . ? C28 Ir2 C37 C41 175.7(2) . . . . ? N2 Ir2 C37 C41 83.2(2) . . . . ? C39 Ir2 C37 C41 -78.9(2) . . . . ? C38 Ir2 C37 C41 -116.2(3) . . . . ? C40 Ir2 C37 C41 -35.6(2) . . . . ? Cl2 Ir2 C37 C41 -36.9(4) . . . . ? C28 Ir2 C37 C42 54.1(4) . . . . ? N2 Ir2 C37 C42 -38.4(4) . . . . ? C39 Ir2 C37 C42 159.4(4) . . . . ? C38 Ir2 C37 C42 122.1(5) . . . . ? C40 Ir2 C37 C42 -157.3(4) . . . . ? C41 Ir2 C37 C42 -121.7(5) . . . . ? Cl2 Ir2 C37 C42 -158.6(3) . . . . ? C41 C37 C38 C39 3.1(4) . . . . ? C42 C37 C38 C39 169.7(3) . . . . ? Ir2 C37 C38 C39 -60.7(2) . . . . ? C41 C37 C38 C43 -175.8(3) . . . . ? C42 C37 C38 C43 -9.2(6) . . . . ? Ir2 C37 C38 C43 120.4(3) . . . . ? C41 C37 C38 Ir2 63.9(2) . . . . ? C42 C37 C38 Ir2 -129.6(4) . . . . ? C28 Ir2 C38 C39 -119.1(2) . . . . ? N2 Ir2 C38 C39 148.9(2) . . . . ? C37 Ir2 C38 C39 118.7(3) . . . . ? C40 Ir2 C38 C39 39.1(2) . . . . ? C41 Ir2 C38 C39 80.3(2) . . . . ? Cl2 Ir2 C38 C39 -26.7(3) . . . . ? C28 Ir2 C38 C37 122.2(2) . . . . ? N2 Ir2 C38 C37 30.1(3) . . . . ? C39 Ir2 C38 C37 -118.7(3) . . . . ? C40 Ir2 C38 C37 -79.6(2) . . . . ? C41 Ir2 C38 C37 -38.5(2) . . . . ? Cl2 Ir2 C38 C37 -145.42(18) . . . . ? C28 Ir2 C38 C43 2.7(4) . . . . ? N2 Ir2 C38 C43 -89.4(4) . . . . ? C39 Ir2 C38 C43 121.8(4) . . . . ? C37 Ir2 C38 C43 -119.5(4) . . . . ? C40 Ir2 C38 C43 160.9(4) . . . . ? C41 Ir2 C38 C43 -158.0(4) . . . . ? Cl2 Ir2 C38 C43 95.1(3) . . . . ? C37 C38 C39 C40 -3.7(4) . . . . ? C43 C38 C39 C40 175.2(3) . . . . ? Ir2 C38 C39 C40 -64.9(2) . . . . ? C37 C38 C39 C44 -176.7(3) . . . . ? C43 C38 C39 C44 2.1(6) . . . . ? Ir2 C38 C39 C44 122.0(4) . . . . ? C37 C38 C39 Ir2 61.3(2) . . . . ? C43 C38 C39 Ir2 -119.9(4) . . . . ? C28 Ir2 C39 C38 70.8(2) . . . . ? N2 Ir2 C39 C38 -99.0(4) . . . . ? C37 Ir2 C39 C38 -37.2(2) . . . . ? C40 Ir2 C39 C38 -115.4(3) . . . . ? C41 Ir2 C39 C38 -80.0(2) . . . . ? Cl2 Ir2 C39 C38 160.0(2) . . . . ? C28 Ir2 C39 C40 -173.8(2) . . . . ? N2 Ir2 C39 C40 16.4(5) . . . . ? C38 Ir2 C39 C40 115.4(3) . . . . ? C37 Ir2 C39 C40 78.3(2) . . . . ? C41 Ir2 C39 C40 35.4(2) . . . . ? Cl2 Ir2 C39 C40 -84.6(2) . . . . ? C28 Ir2 C39 C44 -51.9(4) . . . . ? N2 Ir2 C39 C44 138.4(4) . . . . ? C38 Ir2 C39 C44 -122.7(4) . . . . ? C37 Ir2 C39 C44 -159.8(4) . . . . ? C40 Ir2 C39 C44 121.9(4) . . . . ? C41 Ir2 C39 C44 157.3(4) . . . . ? Cl2 Ir2 C39 C44 37.3(3) . . . . ? C38 C39 C40 C41 2.8(4) . . . . ? C44 C39 C40 C41 176.1(3) . . . . ? Ir2 C39 C40 C41 -60.3(2) . . . . ? C38 C39 C40 C45 -179.0(3) . . . . ? C44 C39 C40 C45 -5.8(6) . . . . ? Ir2 C39 C40 C45 117.9(4) . . . . ? C38 C39 C40 Ir2 63.1(2) . . . . ? C44 C39 C40 Ir2 -123.7(4) . . . . ? C28 Ir2 C40 C41 131.8(3) . . . . ? N2 Ir2 C40 C41 -53.9(3) . . . . ? C39 Ir2 C40 C41 119.7(3) . . . . ? C38 Ir2 C40 C41 80.6(2) . . . . ? C37 Ir2 C40 C41 37.3(2) . . . . ? Cl2 Ir2 C40 C41 -143.3(2) . . . . ? C28 Ir2 C40 C39 12.1(4) . . . . ? N2 Ir2 C40 C39 -173.6(2) . . . . ? C38 Ir2 C40 C39 -39.1(2) . . . . ? C37 Ir2 C40 C39 -82.4(2) . . . . ? C41 Ir2 C40 C39 -119.7(3) . . . . ? Cl2 Ir2 C40 C39 97.0(2) . . . . ? C28 Ir2 C40 C45 -106.3(4) . . . . ? N2 Ir2 C40 C45 68.1(4) . . . . ? C39 Ir2 C40 C45 -118.4(4) . . . . ? C38 Ir2 C40 C45 -157.5(4) . . . . ? C37 Ir2 C40 C45 159.2(4) . . . . ? C41 Ir2 C40 C45 121.9(4) . . . . ? Cl2 Ir2 C40 C45 -21.4(3) . . . . ? C39 C40 C41 C37 -0.9(4) . . . . ? C45 C40 C41 C37 -179.0(3) . . . . ? Ir2 C40 C41 C37 -58.7(2) . . . . ? C39 C40 C41 C46 179.8(3) . . . . ? C45 C40 C41 C46 1.6(6) . . . . ? Ir2 C40 C41 C46 122.0(4) . . . . ? C39 C40 C41 Ir2 57.8(2) . . . . ? C45 C40 C41 Ir2 -120.3(4) . . . . ? C38 C37 C41 C40 -1.4(4) . . . . ? C42 C37 C41 C40 -168.3(3) . . . . ? Ir2 C37 C41 C40 60.6(2) . . . . ? C38 C37 C41 C46 178.0(3) . . . . ? C42 C37 C41 C46 11.0(6) . . . . ? Ir2 C37 C41 C46 -120.0(4) . . . . ? C38 C37 C41 Ir2 -62.0(2) . . . . ? C42 C37 C41 Ir2 131.1(4) . . . . ? C28 Ir2 C41 C40 -128.1(3) . . . . ? N2 Ir2 C41 C40 136.3(2) . . . . ? C39 Ir2 C41 C40 -37.4(2) . . . . ? C38 Ir2 C41 C40 -80.8(2) . . . . ? C37 Ir2 C41 C40 -119.4(3) . . . . ? Cl2 Ir2 C41 C40 43.0(2) . . . . ? C28 Ir2 C41 C37 -8.7(4) . . . . ? N2 Ir2 C41 C37 -104.3(2) . . . . ? C39 Ir2 C41 C37 82.1(2) . . . . ? C38 Ir2 C41 C37 38.6(2) . . . . ? C40 Ir2 C41 C37 119.4(3) . . . . ? Cl2 Ir2 C41 C37 162.47(18) . . . . ? C28 Ir2 C41 C46 109.0(4) . . . . ? N2 Ir2 C41 C46 13.4(3) . . . . ? C39 Ir2 C41 C46 -160.3(4) . . . . ? C38 Ir2 C41 C46 156.3(4) . . . . ? C37 Ir2 C41 C46 117.6(4) . . . . ? C40 Ir2 C41 C46 -122.9(4) . . . . ? Cl2 Ir2 C41 C46 -79.9(3) . . . . ? C29 C28 C47 O3 -71.7(6) . . . . ? Ir2 C28 C47 O3 108.9(4) . . . . ? C29 C28 C47 O4 104.6(4) . . . . ? Ir2 C28 C47 O4 -74.8(4) . . . . ? O3 C47 O4 C48 -1.0(6) . . . . ? C28 C47 O4 C48 -177.5(3) . . . . ? C47 O4 C48 C49 174.9(3) . . . . ? N2 C36 C51 C52 0.9(6) . . . . ? C35 C36 C51 C52 -175.8(4) . . . . ? C36 C51 C52 C53 1.4(6) . . . . ? C51 C52 C53 C54 -1.9(6) . . . . ? C36 N2 C54 C53 2.1(6) . . . . ? Ir2 N2 C54 C53 176.9(3) . . . . ? C52 C53 C54 N2 0.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 35.63 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.238 _refine_diff_density_min -3.051 _refine_diff_density_rms 0.214 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_4g _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll64 _chemical_melting_point ? _chemical_formula_moiety 'C27 H31 Cl N O2 Rh' _chemical_formula_sum 'C27 H31 Cl N O2 Rh' _chemical_formula_weight 539.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9998(6) _cell_length_b 16.0239(9) _cell_length_c 16.1639(9) _cell_angle_alpha 63.356(1) _cell_angle_beta 87.854(1) _cell_angle_gamma 72.148(1) _cell_volume 2407.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 7770 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 35.95 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8628 _exptl_absorpt_correction_T_max 0.9511 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43957 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 33.73 _reflns_number_total 18850 _reflns_number_gt 12438 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18850 _refine_ls_number_parameters 591 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.552003(19) 0.813457(16) 0.856463(15) 0.01784(5) Uani 1 1 d . . . Cl1 Cl 0.69534(7) 0.90851(6) 0.79824(6) 0.02991(16) Uani 1 1 d . . . N1 N 0.4469(2) 0.91465(17) 0.90461(17) 0.0196(4) Uani 1 1 d . . . C1 C 0.6638(3) 0.7369(2) 0.9835(2) 0.0224(6) Uani 1 1 d . . . C2 C 0.6231(3) 0.6963(2) 1.0670(2) 0.0256(6) Uani 1 1 d . . . C3 C 0.4875(3) 0.7021(2) 1.0791(2) 0.0237(6) Uani 1 1 d . . . C4 C 0.4602(3) 0.6147(2) 1.1381(2) 0.0290(6) Uani 1 1 d . . . H4 H 0.5294 0.5544 1.1672 0.035 Uiso 1 1 calc R . . C5 C 0.3365(4) 0.6139(3) 1.1550(2) 0.0337(7) Uani 1 1 d . . . H5 H 0.3219 0.5536 1.1947 0.040 Uiso 1 1 calc R . . C6 C 0.2339(3) 0.7005(3) 1.1146(2) 0.0317(7) Uani 1 1 d . . . H6 H 0.1484 0.7004 1.1250 0.038 Uiso 1 1 calc R . . C7 C 0.2583(3) 0.7876(2) 1.0585(2) 0.0265(6) Uani 1 1 d . . . H7 H 0.1884 0.8476 1.0316 0.032 Uiso 1 1 calc R . . C8 C 0.3826(3) 0.7898(2) 1.0402(2) 0.0234(6) Uani 1 1 d . . . C9 C 0.3927(3) 0.8902(2) 0.9851(2) 0.0203(5) Uani 1 1 d . . . C10 C 0.4207(3) 0.7420(2) 0.8429(2) 0.0219(5) Uani 1 1 d . . . C11 C 0.3947(3) 0.8351(2) 0.7594(2) 0.0234(6) Uani 1 1 d . . . C12 C 0.5060(3) 0.8339(2) 0.7148(2) 0.0262(6) Uani 1 1 d . . . C13 C 0.6046(3) 0.7403(2) 0.7707(2) 0.0272(6) Uani 1 1 d . . . C14 C 0.5496(3) 0.6830(2) 0.8479(2) 0.0246(6) Uani 1 1 d . . . C15 C 0.3189(3) 0.7062(3) 0.8974(3) 0.0355(8) Uani 1 1 d . . . H15A H 0.2809 0.6773 0.8675 0.053 Uiso 1 1 calc R . . H15B H 0.2520 0.7617 0.8997 0.053 Uiso 1 1 calc R . . H15C H 0.3570 0.6562 0.9610 0.053 Uiso 1 1 calc R . . C16 C 0.2698(3) 0.9169(3) 0.7301(3) 0.0365(8) Uani 1 1 d . . . H16A H 0.2084 0.9029 0.6999 0.055 Uiso 1 1 calc R . . H16B H 0.2829 0.9790 0.6862 0.055 Uiso 1 1 calc R . . H16C H 0.2359 0.9226 0.7849 0.055 Uiso 1 1 calc R . . C17 C 0.5237(4) 0.9124(3) 0.6252(2) 0.0442(9) Uani 1 1 d . . . H17A H 0.5198 0.8940 0.5754 0.066 Uiso 1 1 calc R . . H17B H 0.6075 0.9201 0.6310 0.066 Uiso 1 1 calc R . . H17C H 0.4554 0.9749 0.6103 0.066 Uiso 1 1 calc R . . C18 C 0.7354(3) 0.7086(3) 0.7427(3) 0.0446(10) Uani 1 1 d . . . H18A H 0.7271 0.7036 0.6851 0.067 Uiso 1 1 calc R . . H18B H 0.7866 0.6442 0.7923 0.067 Uiso 1 1 calc R . . H18C H 0.7781 0.7573 0.7325 0.067 Uiso 1 1 calc R . . C19 C 0.6130(4) 0.5794(2) 0.9211(3) 0.0390(8) Uani 1 1 d . . . H19A H 0.5921 0.5336 0.9038 0.059 Uiso 1 1 calc R . . H19B H 0.5821 0.5714 0.9810 0.059 Uiso 1 1 calc R . . H19C H 0.7064 0.5652 0.9265 0.059 Uiso 1 1 calc R . . C20 C 0.8035(3) 0.7266(2) 0.9792(2) 0.0268(6) Uani 1 1 d . . . O1 O 0.8609(2) 0.76215(18) 1.01008(19) 0.0367(6) Uani 1 1 d . . . O2 O 0.86207(19) 0.67046(16) 0.93824(16) 0.0266(5) Uani 1 1 d . . . C21 C 0.9968(3) 0.6618(3) 0.9281(3) 0.0370(8) Uani 1 1 d . . . H21A H 1.0459 0.6328 0.9901 0.044 Uiso 1 1 calc R . . H21B H 1.0050 0.7278 0.8896 0.044 Uiso 1 1 calc R . . C22 C 1.0492(3) 0.5966(3) 0.8822(3) 0.0371(8) Uani 1 1 d . . . H22A H 1.1423 0.5832 0.8823 0.056 Uiso 1 1 calc R . . H22B H 1.0081 0.6300 0.8178 0.056 Uiso 1 1 calc R . . H22C H 1.0312 0.5343 0.9166 0.056 Uiso 1 1 calc R . . C23 C 0.7137(3) 0.6352(3) 1.1573(2) 0.0362(8) Uani 1 1 d . . . H23A H 0.7965 0.6471 1.1465 0.054 Uiso 1 1 calc R . . H23B H 0.7268 0.5650 1.1787 0.054 Uiso 1 1 calc R . . H23C H 0.6762 0.6541 1.2048 0.054 Uiso 1 1 calc R . . C24 C 0.3353(3) 0.9607(2) 1.0151(2) 0.0254(6) Uani 1 1 d . . . H24 H 0.3006 0.9417 1.0729 0.030 Uiso 1 1 calc R . . C25 C 0.3284(3) 1.0580(2) 0.9614(2) 0.0299(7) Uani 1 1 d . . . H25 H 0.2905 1.1061 0.9820 0.036 Uiso 1 1 calc R . . C26 C 0.3776(3) 1.0833(2) 0.8777(3) 0.0305(7) Uani 1 1 d . . . H26 H 0.3714 1.1500 0.8380 0.037 Uiso 1 1 calc R . . C27 C 0.4361(3) 1.0108(2) 0.8519(2) 0.0257(6) Uani 1 1 d . . . H27 H 0.4709 1.0292 0.7941 0.031 Uiso 1 1 calc R . . Rh2 Rh 0.23782(2) 0.742766(16) 0.489186(15) 0.01841(5) Uani 1 1 d . . . Cl2 Cl 0.22053(8) 0.70745(6) 0.65065(5) 0.02957(16) Uani 1 1 d . . . N2 N 0.1603(2) 0.89652(17) 0.44359(17) 0.0205(5) Uani 1 1 d . . . C28 C 0.0517(3) 0.7448(2) 0.4773(2) 0.0215(5) Uani 1 1 d . . . C29 C -0.0365(3) 0.7998(2) 0.4032(2) 0.0230(6) Uani 1 1 d . . . C30 C -0.0088(3) 0.8650(2) 0.3106(2) 0.0227(6) Uani 1 1 d . . . C31 C -0.0464(3) 0.8552(2) 0.2338(2) 0.0293(7) Uani 1 1 d . . . H31 H -0.0860 0.8068 0.2446 0.035 Uiso 1 1 calc R . . C32 C -0.0282(3) 0.9128(3) 0.1442(2) 0.0335(7) Uani 1 1 d . . . H32 H -0.0522 0.9026 0.0945 0.040 Uiso 1 1 calc R . . C33 C 0.0253(3) 0.9856(3) 0.1271(2) 0.0322(7) Uani 1 1 d . . . H33 H 0.0363 1.0272 0.0652 0.039 Uiso 1 1 calc R . . C34 C 0.0626(3) 0.9977(2) 0.2004(2) 0.0261(6) Uani 1 1 d . . . H34 H 0.0994 1.0479 0.1880 0.031 Uiso 1 1 calc R . . C35 C 0.0479(2) 0.9381(2) 0.2924(2) 0.0211(5) Uani 1 1 d . . . C36 C 0.0852(2) 0.9645(2) 0.3626(2) 0.0206(5) Uani 1 1 d . . . C37 C 0.3443(3) 0.7321(2) 0.3771(2) 0.0220(5) Uani 1 1 d . . . C38 C 0.4284(3) 0.7426(2) 0.4364(2) 0.0221(5) Uani 1 1 d . . . C39 C 0.4493(3) 0.6638(2) 0.5252(2) 0.0217(5) Uani 1 1 d . . . C40 C 0.3770(3) 0.6008(2) 0.5247(2) 0.0214(5) Uani 1 1 d . . . C41 C 0.3185(3) 0.6422(2) 0.4316(2) 0.0220(5) Uani 1 1 d . . . C42 C 0.3195(3) 0.7916(2) 0.2735(2) 0.0273(6) Uani 1 1 d . . . H42A H 0.3906 0.7640 0.2452 0.041 Uiso 1 1 calc R . . H42B H 0.3125 0.8601 0.2561 0.041 Uiso 1 1 calc R . . H42C H 0.2390 0.7900 0.2512 0.041 Uiso 1 1 calc R . . C43 C 0.4813(3) 0.8265(2) 0.4037(2) 0.0318(7) Uani 1 1 d . . . H43A H 0.5541 0.8151 0.3689 0.048 Uiso 1 1 calc R . . H43B H 0.5102 0.8312 0.4577 0.048 Uiso 1 1 calc R . . H43C H 0.4141 0.8883 0.3632 0.048 Uiso 1 1 calc R . . C44 C 0.5281(3) 0.6454(2) 0.6086(2) 0.0294(6) Uani 1 1 d . . . H44A H 0.6173 0.6072 0.6099 0.044 Uiso 1 1 calc R . . H44B H 0.4936 0.6083 0.6652 0.044 Uiso 1 1 calc R . . H44C H 0.5250 0.7086 0.6052 0.044 Uiso 1 1 calc R . . C45 C 0.3791(3) 0.5051(2) 0.6050(2) 0.0298(7) Uani 1 1 d . . . H45A H 0.4606 0.4539 0.6122 0.045 Uiso 1 1 calc R . . H45B H 0.3075 0.4860 0.5933 0.045 Uiso 1 1 calc R . . H45C H 0.3705 0.5125 0.6621 0.045 Uiso 1 1 calc R . . C46 C 0.2446(3) 0.5986(3) 0.3957(2) 0.0309(7) Uani 1 1 d . . . H46A H 0.3026 0.5589 0.3697 0.046 Uiso 1 1 calc R . . H46B H 0.1762 0.6517 0.3470 0.046 Uiso 1 1 calc R . . H46C H 0.2064 0.5567 0.4469 0.046 Uiso 1 1 calc R . . C47 C 0.0102(3) 0.6757(2) 0.5614(2) 0.0239(6) Uani 1 1 d . . . O3 O -0.0639(2) 0.69713(18) 0.61112(19) 0.0396(6) Uani 1 1 d . . . O4 O 0.0595(2) 0.58157(15) 0.57544(15) 0.0250(4) Uani 1 1 d . . . C48 C 0.0182(3) 0.5105(2) 0.6543(2) 0.0318(7) Uani 1 1 d . . . H48A H -0.0769 0.5311 0.6493 0.038 Uiso 1 1 calc R . . H48B H 0.0508 0.5056 0.7132 0.038 Uiso 1 1 calc R . . C49 C 0.0719(4) 0.4127(3) 0.6532(3) 0.0385(8) Uani 1 1 d . . . H49A H 0.0481 0.3622 0.7070 0.058 Uiso 1 1 calc R . . H49B H 0.1658 0.3942 0.6562 0.058 Uiso 1 1 calc R . . H49C H 0.0366 0.4179 0.5956 0.058 Uiso 1 1 calc R . . C50 C -0.1736(3) 0.7949(2) 0.4055(3) 0.0310(7) Uani 1 1 d . . . H50A H -0.1703 0.7264 0.4269 0.047 Uiso 1 1 calc R . . H50B H -0.2206 0.8361 0.3428 0.047 Uiso 1 1 calc R . . H50C H -0.2175 0.8189 0.4483 0.047 Uiso 1 1 calc R . . C51 C 0.0449(3) 1.0649(2) 0.3401(2) 0.0259(6) Uani 1 1 d . . . H51 H -0.0084 1.1119 0.2833 0.031 Uiso 1 1 calc R . . C52 C 0.0809(3) 1.0966(2) 0.3982(2) 0.0291(7) Uani 1 1 d . . . H52 H 0.0523 1.1646 0.3830 0.035 Uiso 1 1 calc R . . C53 C 0.1604(3) 1.0264(2) 0.4800(2) 0.0279(6) Uani 1 1 d . . . H53 H 0.1889 1.0455 0.5216 0.033 Uiso 1 1 calc R . . C54 C 0.1970(3) 0.9285(2) 0.4998(2) 0.0265(6) Uani 1 1 d . . . H54 H 0.2510 0.8809 0.5561 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01719(10) 0.01936(10) 0.01895(11) -0.01010(9) 0.00481(7) -0.00679(8) Cl1 0.0248(3) 0.0291(4) 0.0382(4) -0.0145(3) 0.0103(3) -0.0143(3) N1 0.0176(10) 0.0206(11) 0.0221(12) -0.0116(10) 0.0032(9) -0.0057(9) C1 0.0213(13) 0.0190(13) 0.0275(15) -0.0132(12) -0.0004(11) -0.0029(10) C2 0.0258(14) 0.0252(14) 0.0230(15) -0.0117(13) -0.0012(11) -0.0031(12) C3 0.0286(14) 0.0263(14) 0.0169(13) -0.0116(12) 0.0014(11) -0.0068(12) C4 0.0381(17) 0.0252(15) 0.0197(15) -0.0082(13) 0.0035(12) -0.0084(13) C5 0.049(2) 0.0348(18) 0.0227(16) -0.0144(15) 0.0155(14) -0.0202(16) C6 0.0355(17) 0.0439(19) 0.0267(17) -0.0213(16) 0.0173(13) -0.0209(15) C7 0.0249(14) 0.0322(16) 0.0253(16) -0.0166(14) 0.0074(11) -0.0083(12) C8 0.0240(13) 0.0285(15) 0.0205(14) -0.0139(13) 0.0044(11) -0.0082(11) C9 0.0186(12) 0.0236(13) 0.0212(14) -0.0135(12) 0.0016(10) -0.0051(10) C10 0.0248(13) 0.0279(14) 0.0218(14) -0.0154(13) 0.0080(11) -0.0146(12) C11 0.0222(13) 0.0312(15) 0.0222(14) -0.0160(13) 0.0030(11) -0.0099(12) C12 0.0301(15) 0.0352(17) 0.0189(14) -0.0140(13) 0.0069(11) -0.0160(13) C13 0.0217(13) 0.0382(17) 0.0322(17) -0.0255(15) 0.0081(12) -0.0093(12) C14 0.0273(14) 0.0241(14) 0.0288(16) -0.0180(13) 0.0022(12) -0.0075(12) C15 0.0410(18) 0.054(2) 0.0344(19) -0.0287(18) 0.0184(15) -0.0332(18) C16 0.0277(16) 0.045(2) 0.0352(19) -0.0213(17) -0.0038(14) -0.0036(15) C17 0.059(2) 0.059(3) 0.0231(18) -0.0157(18) 0.0130(16) -0.036(2) C18 0.0253(16) 0.075(3) 0.061(3) -0.054(2) 0.0178(16) -0.0180(18) C19 0.050(2) 0.0224(16) 0.046(2) -0.0189(16) -0.0040(17) -0.0077(15) C20 0.0217(13) 0.0239(14) 0.0345(17) -0.0159(14) 0.0018(12) -0.0029(11) O1 0.0217(11) 0.0409(14) 0.0568(17) -0.0340(13) -0.0012(10) -0.0036(10) O2 0.0191(9) 0.0261(11) 0.0386(13) -0.0194(10) 0.0080(9) -0.0061(8) C21 0.0209(14) 0.0398(19) 0.061(2) -0.0315(19) 0.0123(15) -0.0111(14) C22 0.0246(15) 0.0384(19) 0.053(2) -0.0267(19) 0.0133(15) -0.0082(14) C23 0.0350(18) 0.0365(19) 0.0250(17) -0.0081(15) -0.0044(14) -0.0044(15) C24 0.0197(13) 0.0314(16) 0.0292(16) -0.0202(14) 0.0029(11) -0.0041(11) C25 0.0220(13) 0.0300(16) 0.046(2) -0.0270(16) -0.0001(13) -0.0035(12) C26 0.0273(15) 0.0221(14) 0.044(2) -0.0175(15) -0.0018(13) -0.0056(12) C27 0.0255(14) 0.0209(14) 0.0295(16) -0.0107(13) 0.0000(12) -0.0070(11) Rh2 0.01777(10) 0.01820(10) 0.01708(11) -0.00848(9) 0.00492(7) -0.00274(8) Cl2 0.0341(4) 0.0303(4) 0.0186(3) -0.0109(3) 0.0070(3) -0.0038(3) N2 0.0212(11) 0.0203(11) 0.0198(12) -0.0105(10) 0.0062(9) -0.0049(9) C28 0.0211(12) 0.0189(12) 0.0272(15) -0.0137(12) 0.0114(11) -0.0061(10) C29 0.0217(13) 0.0212(13) 0.0306(16) -0.0150(13) 0.0098(11) -0.0089(11) C30 0.0142(11) 0.0233(13) 0.0261(15) -0.0103(12) 0.0023(10) -0.0019(10) C31 0.0189(13) 0.0345(17) 0.0368(18) -0.0193(15) 0.0023(12) -0.0070(12) C32 0.0229(14) 0.049(2) 0.0290(18) -0.0207(17) -0.0023(12) -0.0066(14) C33 0.0190(13) 0.0435(19) 0.0227(16) -0.0085(15) 0.0002(11) -0.0055(13) C34 0.0177(12) 0.0287(15) 0.0229(15) -0.0053(13) 0.0019(11) -0.0060(11) C35 0.0137(11) 0.0233(13) 0.0216(14) -0.0088(12) 0.0022(10) -0.0022(10) C36 0.0142(11) 0.0213(13) 0.0247(14) -0.0101(12) 0.0058(10) -0.0050(10) C37 0.0169(12) 0.0249(14) 0.0206(14) -0.0108(12) 0.0067(10) -0.0022(10) C38 0.0178(12) 0.0239(14) 0.0234(14) -0.0124(12) 0.0050(10) -0.0029(10) C39 0.0185(12) 0.0220(13) 0.0203(14) -0.0096(12) 0.0030(10) -0.0011(10) C40 0.0196(12) 0.0196(13) 0.0228(14) -0.0106(12) 0.0061(10) -0.0025(10) C41 0.0179(12) 0.0246(14) 0.0242(15) -0.0149(12) 0.0048(10) -0.0023(10) C42 0.0237(14) 0.0352(17) 0.0195(15) -0.0123(13) 0.0068(11) -0.0058(12) C43 0.0299(16) 0.0283(16) 0.0349(19) -0.0113(15) 0.0026(13) -0.0112(13) C44 0.0280(15) 0.0289(16) 0.0241(16) -0.0100(14) -0.0041(12) -0.0023(13) C45 0.0270(15) 0.0229(14) 0.0301(17) -0.0090(13) 0.0065(12) -0.0012(12) C46 0.0273(15) 0.0378(18) 0.0376(19) -0.0260(16) 0.0089(13) -0.0108(13) C47 0.0241(13) 0.0232(14) 0.0273(16) -0.0146(13) 0.0095(11) -0.0077(11) O3 0.0471(15) 0.0338(13) 0.0478(16) -0.0251(13) 0.0326(12) -0.0191(11) O4 0.0261(10) 0.0217(10) 0.0254(11) -0.0098(9) 0.0079(8) -0.0078(8) C48 0.0371(17) 0.0279(16) 0.0278(17) -0.0082(14) 0.0083(13) -0.0150(14) C49 0.0401(19) 0.0261(16) 0.046(2) -0.0120(16) -0.0032(16) -0.0126(15) C50 0.0225(14) 0.0310(16) 0.043(2) -0.0197(16) 0.0077(13) -0.0099(13) C51 0.0205(13) 0.0219(14) 0.0319(17) -0.0117(13) 0.0065(11) -0.0039(11) C52 0.0275(15) 0.0220(14) 0.0394(19) -0.0167(14) 0.0128(13) -0.0069(12) C53 0.0289(15) 0.0298(16) 0.0310(17) -0.0197(14) 0.0093(12) -0.0091(13) C54 0.0262(14) 0.0282(15) 0.0283(16) -0.0174(14) 0.0072(12) -0.0063(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C1 2.058(3) . ? Rh1 N1 2.118(2) . ? Rh1 C13 2.147(3) . ? Rh1 C14 2.165(3) . ? Rh1 C10 2.170(3) . ? Rh1 C11 2.218(3) . ? Rh1 C12 2.219(3) . ? Rh1 Cl1 2.4015(8) . ? N1 C9 1.352(4) . ? N1 C27 1.353(4) . ? C1 C2 1.339(4) . ? C1 C20 1.496(4) . ? C2 C3 1.477(4) . ? C2 C23 1.519(4) . ? C3 C8 1.404(4) . ? C3 C4 1.413(4) . ? C4 C5 1.380(5) . ? C4 H4 0.9500 . ? C5 C6 1.382(5) . ? C5 H5 0.9500 . ? C6 C7 1.384(5) . ? C6 H6 0.9500 . ? C7 C8 1.396(4) . ? C7 H7 0.9500 . ? C8 C9 1.486(4) . ? C9 C24 1.393(4) . ? C10 C14 1.424(4) . ? C10 C11 1.446(4) . ? C10 C15 1.492(4) . ? C11 C12 1.398(4) . ? C11 C16 1.489(4) . ? C12 C13 1.450(5) . ? C12 C17 1.487(5) . ? C13 C14 1.422(4) . ? C13 C18 1.497(4) . ? C14 C19 1.494(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O1 1.214(3) . ? C20 O2 1.344(3) . ? O2 C21 1.455(4) . ? C21 C22 1.505(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.382(5) . ? C24 H24 0.9500 . ? C25 C26 1.369(5) . ? C25 H25 0.9500 . ? C26 C27 1.376(4) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? Rh2 C28 2.053(3) . ? Rh2 N2 2.114(2) . ? Rh2 C40 2.146(3) . ? Rh2 C41 2.158(3) . ? Rh2 C37 2.163(3) . ? Rh2 C38 2.233(3) . ? Rh2 C39 2.233(3) . ? Rh2 Cl2 2.4232(8) . ? N2 C54 1.351(4) . ? N2 C36 1.354(4) . ? C28 C29 1.330(4) . ? C28 C47 1.481(4) . ? C29 C30 1.477(4) . ? C29 C50 1.532(4) . ? C30 C35 1.404(4) . ? C30 C31 1.410(4) . ? C31 C32 1.372(5) . ? C31 H31 0.9500 . ? C32 C33 1.380(5) . ? C32 H32 0.9500 . ? C33 C34 1.378(4) . ? C33 H33 0.9500 . ? C34 C35 1.397(4) . ? C34 H34 0.9500 . ? C35 C36 1.487(4) . ? C36 C51 1.402(4) . ? C37 C41 1.422(4) . ? C37 C38 1.453(4) . ? C37 C42 1.493(4) . ? C38 C39 1.389(4) . ? C38 C43 1.498(4) . ? C39 C40 1.467(4) . ? C39 C44 1.492(4) . ? C40 C41 1.427(4) . ? C40 C45 1.494(4) . ? C41 C46 1.493(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 O3 1.206(3) . ? C47 O4 1.349(3) . ? O4 C48 1.449(4) . ? C48 C49 1.505(5) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.371(4) . ? C51 H51 0.9500 . ? C52 C53 1.388(5) . ? C52 H52 0.9500 . ? C53 C54 1.377(4) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 N1 86.81(10) . . ? C1 Rh1 C13 112.48(11) . . ? N1 Rh1 C13 160.41(11) . . ? C1 Rh1 C14 94.96(11) . . ? N1 Rh1 C14 141.01(10) . . ? C13 Rh1 C14 38.52(12) . . ? C1 Rh1 C10 113.25(12) . . ? N1 Rh1 C10 105.92(9) . . ? C13 Rh1 C10 64.25(11) . . ? C14 Rh1 C10 38.36(11) . . ? C1 Rh1 C11 151.53(12) . . ? N1 Rh1 C11 97.85(10) . . ? C13 Rh1 C11 63.65(11) . . ? C14 Rh1 C11 64.02(11) . . ? C10 Rh1 C11 38.45(11) . . ? C1 Rh1 C12 151.00(11) . . ? N1 Rh1 C12 122.15(11) . . ? C13 Rh1 C12 38.75(12) . . ? C14 Rh1 C12 64.08(12) . . ? C10 Rh1 C12 63.31(11) . . ? C11 Rh1 C12 36.72(11) . . ? C1 Rh1 Cl1 88.65(9) . . ? N1 Rh1 Cl1 88.97(7) . . ? C13 Rh1 Cl1 94.68(9) . . ? C14 Rh1 Cl1 129.98(8) . . ? C10 Rh1 Cl1 153.70(8) . . ? C11 Rh1 Cl1 119.38(8) . . ? C12 Rh1 Cl1 90.45(8) . . ? C9 N1 C27 117.5(2) . . ? C9 N1 Rh1 125.03(19) . . ? C27 N1 Rh1 117.4(2) . . ? C2 C1 C20 118.6(3) . . ? C2 C1 Rh1 126.2(2) . . ? C20 C1 Rh1 115.2(2) . . ? C1 C2 C3 123.0(3) . . ? C1 C2 C23 122.9(3) . . ? C3 C2 C23 114.1(3) . . ? C8 C3 C4 116.8(3) . . ? C8 C3 C2 124.5(3) . . ? C4 C3 C2 118.6(3) . . ? C5 C4 C3 122.3(3) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C6 C7 C8 122.0(3) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C7 C8 C3 120.0(3) . . ? C7 C8 C9 114.9(3) . . ? C3 C8 C9 124.9(3) . . ? N1 C9 C24 120.8(3) . . ? N1 C9 C8 121.2(2) . . ? C24 C9 C8 117.8(3) . . ? C14 C10 C11 108.1(3) . . ? C14 C10 C15 126.0(3) . . ? C11 C10 C15 123.9(3) . . ? C14 C10 Rh1 70.63(15) . . ? C11 C10 Rh1 72.60(15) . . ? C15 C10 Rh1 135.1(2) . . ? C12 C11 C10 108.2(3) . . ? C12 C11 C16 127.6(3) . . ? C10 C11 C16 124.2(3) . . ? C12 C11 Rh1 71.65(16) . . ? C10 C11 Rh1 68.95(15) . . ? C16 C11 Rh1 124.1(2) . . ? C11 C12 C13 107.9(3) . . ? C11 C12 C17 127.4(3) . . ? C13 C12 C17 124.6(3) . . ? C11 C12 Rh1 71.63(16) . . ? C13 C12 Rh1 67.97(16) . . ? C17 C12 Rh1 126.4(2) . . ? C14 C13 C12 108.1(3) . . ? C14 C13 C18 127.6(3) . . ? C12 C13 C18 123.9(3) . . ? C14 C13 Rh1 71.39(15) . . ? C12 C13 Rh1 73.28(16) . . ? C18 C13 Rh1 126.6(2) . . ? C13 C14 C10 107.5(3) . . ? C13 C14 C19 127.0(3) . . ? C10 C14 C19 125.5(3) . . ? C13 C14 Rh1 70.09(16) . . ? C10 C14 Rh1 71.01(15) . . ? C19 C14 Rh1 124.8(2) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 O2 122.3(3) . . ? O1 C20 C1 125.3(3) . . ? O2 C20 C1 112.4(2) . . ? C20 O2 C21 114.8(2) . . ? O2 C21 C22 108.7(3) . . ? O2 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? O2 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C9 120.6(3) . . ? C25 C24 H24 119.7 . . ? C9 C24 H24 119.7 . . ? C26 C25 C24 118.3(3) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? C25 C26 C27 119.1(3) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? N1 C27 C26 123.5(3) . . ? N1 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C28 Rh2 N2 86.68(10) . . ? C28 Rh2 C40 113.07(11) . . ? N2 Rh2 C40 159.68(10) . . ? C28 Rh2 C41 96.21(10) . . ? N2 Rh2 C41 138.91(10) . . ? C40 Rh2 C41 38.73(11) . . ? C28 Rh2 C37 114.16(11) . . ? N2 Rh2 C37 103.60(10) . . ? C40 Rh2 C37 64.89(11) . . ? C41 Rh2 C37 38.43(11) . . ? C28 Rh2 C38 152.57(11) . . ? N2 Rh2 C38 96.71(10) . . ? C40 Rh2 C38 63.65(11) . . ? C41 Rh2 C38 63.67(10) . . ? C37 Rh2 C38 38.56(10) . . ? C28 Rh2 C39 151.86(11) . . ? N2 Rh2 C39 121.43(10) . . ? C40 Rh2 C39 39.07(11) . . ? C41 Rh2 C39 64.02(10) . . ? C37 Rh2 C39 63.45(10) . . ? C38 Rh2 C39 36.24(11) . . ? C28 Rh2 Cl2 88.71(8) . . ? N2 Rh2 Cl2 91.78(7) . . ? C40 Rh2 Cl2 93.31(8) . . ? C41 Rh2 Cl2 129.18(8) . . ? C37 Rh2 Cl2 152.76(8) . . ? C38 Rh2 Cl2 118.27(8) . . ? C39 Rh2 Cl2 89.37(7) . . ? C54 N2 C36 118.2(2) . . ? C54 N2 Rh2 115.2(2) . . ? C36 N2 Rh2 126.51(18) . . ? C29 C28 C47 115.7(3) . . ? C29 C28 Rh2 128.1(2) . . ? C47 C28 Rh2 116.2(2) . . ? C28 C29 C30 123.3(3) . . ? C28 C29 C50 122.2(3) . . ? C30 C29 C50 114.3(3) . . ? C35 C30 C31 117.4(3) . . ? C35 C30 C29 125.4(3) . . ? C31 C30 C29 117.2(3) . . ? C32 C31 C30 122.7(3) . . ? C32 C31 H31 118.7 . . ? C30 C31 H31 118.7 . . ? C31 C32 C33 119.3(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C34 C33 C32 119.6(3) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 121.9(3) . . ? C33 C34 H34 119.0 . . ? C35 C34 H34 119.0 . . ? C34 C35 C30 119.1(3) . . ? C34 C35 C36 115.3(3) . . ? C30 C35 C36 125.4(3) . . ? N2 C36 C51 120.1(3) . . ? N2 C36 C35 122.6(2) . . ? C51 C36 C35 117.3(3) . . ? C41 C37 C38 107.4(3) . . ? C41 C37 C42 126.6(3) . . ? C38 C37 C42 124.3(3) . . ? C41 C37 Rh2 70.60(15) . . ? C38 C37 Rh2 73.33(15) . . ? C42 C37 Rh2 133.1(2) . . ? C39 C38 C37 108.9(3) . . ? C39 C38 C43 127.3(3) . . ? C37 C38 C43 123.8(3) . . ? C39 C38 Rh2 71.89(16) . . ? C37 C38 Rh2 68.11(15) . . ? C43 C38 Rh2 125.8(2) . . ? C38 C39 C40 108.0(2) . . ? C38 C39 C44 127.3(3) . . ? C40 C39 C44 124.8(3) . . ? C38 C39 Rh2 71.87(16) . . ? C40 C39 Rh2 67.26(15) . . ? C44 C39 Rh2 125.22(19) . . ? C41 C40 C39 107.1(3) . . ? C41 C40 C45 127.2(3) . . ? C39 C40 C45 125.3(3) . . ? C41 C40 Rh2 71.08(15) . . ? C39 C40 Rh2 73.67(15) . . ? C45 C40 Rh2 126.11(19) . . ? C37 C41 C40 108.5(2) . . ? C37 C41 C46 125.2(3) . . ? C40 C41 C46 126.4(3) . . ? C37 C41 Rh2 70.97(15) . . ? C40 C41 Rh2 70.19(15) . . ? C46 C41 Rh2 125.58(19) . . ? C37 C42 H42A 109.5 . . ? C37 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C37 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C38 C43 H43A 109.5 . . ? C38 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C38 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C39 C44 H44A 109.5 . . ? C39 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C39 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C40 C45 H45A 109.5 . . ? C40 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C40 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C41 C46 H46A 109.5 . . ? C41 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C41 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O3 C47 O4 121.2(3) . . ? O3 C47 C28 126.7(3) . . ? O4 C47 C28 112.0(2) . . ? C47 O4 C48 114.9(2) . . ? O4 C48 C49 107.3(3) . . ? O4 C48 H48A 110.3 . . ? C49 C48 H48A 110.3 . . ? O4 C48 H48B 110.3 . . ? C49 C48 H48B 110.3 . . ? H48A C48 H48B 108.5 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C29 C50 H50A 109.5 . . ? C29 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C29 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C52 C51 C36 121.3(3) . . ? C52 C51 H51 119.3 . . ? C36 C51 H51 119.3 . . ? C51 C52 C53 118.0(3) . . ? C51 C52 H52 121.0 . . ? C53 C52 H52 121.0 . . ? C54 C53 C52 118.7(3) . . ? C54 C53 H53 120.6 . . ? C52 C53 H53 120.6 . . ? N2 C54 C53 123.6(3) . . ? N2 C54 H54 118.2 . . ? C53 C54 H54 118.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C9 -53.8(2) . . . . ? C13 Rh1 N1 C9 116.3(4) . . . . ? C14 Rh1 N1 C9 40.1(3) . . . . ? C10 Rh1 N1 C9 59.4(2) . . . . ? C11 Rh1 N1 C9 97.9(2) . . . . ? C12 Rh1 N1 C9 127.6(2) . . . . ? Cl1 Rh1 N1 C9 -142.5(2) . . . . ? C1 Rh1 N1 C27 124.3(2) . . . . ? C13 Rh1 N1 C27 -65.5(4) . . . . ? C14 Rh1 N1 C27 -141.8(2) . . . . ? C10 Rh1 N1 C27 -122.4(2) . . . . ? C11 Rh1 N1 C27 -83.9(2) . . . . ? C12 Rh1 N1 C27 -54.3(2) . . . . ? Cl1 Rh1 N1 C27 35.6(2) . . . . ? N1 Rh1 C1 C2 60.8(3) . . . . ? C13 Rh1 C1 C2 -115.7(3) . . . . ? C14 Rh1 C1 C2 -80.2(3) . . . . ? C10 Rh1 C1 C2 -45.2(3) . . . . ? C11 Rh1 C1 C2 -39.8(4) . . . . ? C12 Rh1 C1 C2 -121.7(3) . . . . ? Cl1 Rh1 C1 C2 149.8(3) . . . . ? N1 Rh1 C1 C20 -119.5(2) . . . . ? C13 Rh1 C1 C20 64.0(2) . . . . ? C14 Rh1 C1 C20 99.5(2) . . . . ? C10 Rh1 C1 C20 134.52(19) . . . . ? C11 Rh1 C1 C20 139.9(2) . . . . ? C12 Rh1 C1 C20 58.0(3) . . . . ? Cl1 Rh1 C1 C20 -30.47(19) . . . . ? C20 C1 C2 C3 -180.0(3) . . . . ? Rh1 C1 C2 C3 -0.3(4) . . . . ? C20 C1 C2 C23 -3.7(4) . . . . ? Rh1 C1 C2 C23 176.0(2) . . . . ? C1 C2 C3 C8 -51.8(4) . . . . ? C23 C2 C3 C8 131.7(3) . . . . ? C1 C2 C3 C4 132.1(3) . . . . ? C23 C2 C3 C4 -44.5(4) . . . . ? C8 C3 C4 C5 2.0(4) . . . . ? C2 C3 C4 C5 178.4(3) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C7 -1.1(5) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? C6 C7 C8 C3 0.0(4) . . . . ? C6 C7 C8 C9 -175.2(3) . . . . ? C4 C3 C8 C7 -1.7(4) . . . . ? C2 C3 C8 C7 -177.9(3) . . . . ? C4 C3 C8 C9 173.0(3) . . . . ? C2 C3 C8 C9 -3.2(4) . . . . ? C27 N1 C9 C24 -4.0(4) . . . . ? Rh1 N1 C9 C24 174.1(2) . . . . ? C27 N1 C9 C8 170.9(3) . . . . ? Rh1 N1 C9 C8 -11.0(4) . . . . ? C7 C8 C9 N1 -124.4(3) . . . . ? C3 C8 C9 N1 60.7(4) . . . . ? C7 C8 C9 C24 50.7(4) . . . . ? C3 C8 C9 C24 -124.3(3) . . . . ? C1 Rh1 C10 C14 -66.96(19) . . . . ? N1 Rh1 C10 C14 -160.38(17) . . . . ? C13 Rh1 C10 C14 37.80(18) . . . . ? C11 Rh1 C10 C14 117.1(2) . . . . ? C12 Rh1 C10 C14 81.20(19) . . . . ? Cl1 Rh1 C10 C14 77.3(3) . . . . ? C1 Rh1 C10 C11 175.90(15) . . . . ? N1 Rh1 C10 C11 82.48(16) . . . . ? C13 Rh1 C10 C11 -79.34(18) . . . . ? C14 Rh1 C10 C11 -117.1(2) . . . . ? C12 Rh1 C10 C11 -35.95(16) . . . . ? Cl1 Rh1 C10 C11 -39.9(3) . . . . ? C1 Rh1 C10 C15 55.0(4) . . . . ? N1 Rh1 C10 C15 -38.4(4) . . . . ? C13 Rh1 C10 C15 159.8(4) . . . . ? C14 Rh1 C10 C15 122.0(4) . . . . ? C11 Rh1 C10 C15 -120.9(4) . . . . ? C12 Rh1 C10 C15 -156.8(4) . . . . ? Cl1 Rh1 C10 C15 -160.7(3) . . . . ? C14 C10 C11 C12 -0.8(3) . . . . ? C15 C10 C11 C12 -165.7(3) . . . . ? Rh1 C10 C11 C12 61.21(19) . . . . ? C14 C10 C11 C16 -179.7(3) . . . . ? C15 C10 C11 C16 15.5(4) . . . . ? Rh1 C10 C11 C16 -117.6(3) . . . . ? C14 C10 C11 Rh1 -62.06(18) . . . . ? C15 C10 C11 Rh1 133.1(3) . . . . ? C1 Rh1 C11 C12 -126.6(2) . . . . ? N1 Rh1 C11 C12 135.54(18) . . . . ? C13 Rh1 C11 C12 -37.67(19) . . . . ? C14 Rh1 C11 C12 -80.8(2) . . . . ? C10 Rh1 C11 C12 -118.7(2) . . . . ? Cl1 Rh1 C11 C12 42.3(2) . . . . ? C1 Rh1 C11 C10 -7.9(3) . . . . ? N1 Rh1 C11 C10 -105.76(16) . . . . ? C13 Rh1 C11 C10 81.03(18) . . . . ? C14 Rh1 C11 C10 37.90(16) . . . . ? C12 Rh1 C11 C10 118.7(2) . . . . ? Cl1 Rh1 C11 C10 160.99(13) . . . . ? C1 Rh1 C11 C16 109.9(3) . . . . ? N1 Rh1 C11 C16 12.0(3) . . . . ? C13 Rh1 C11 C16 -161.2(3) . . . . ? C14 Rh1 C11 C16 155.7(3) . . . . ? C10 Rh1 C11 C16 117.8(3) . . . . ? C12 Rh1 C11 C16 -123.5(4) . . . . ? Cl1 Rh1 C11 C16 -81.2(3) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C16 C11 C12 C13 177.8(3) . . . . ? Rh1 C11 C12 C13 58.47(19) . . . . ? C10 C11 C12 C17 178.2(3) . . . . ? C16 C11 C12 C17 -2.9(5) . . . . ? Rh1 C11 C12 C17 -122.2(3) . . . . ? C10 C11 C12 Rh1 -59.51(19) . . . . ? C16 C11 C12 Rh1 119.3(3) . . . . ? C1 Rh1 C12 C11 127.9(2) . . . . ? N1 Rh1 C12 C11 -55.0(2) . . . . ? C13 Rh1 C12 C11 119.0(3) . . . . ? C14 Rh1 C12 C11 80.62(19) . . . . ? C10 Rh1 C12 C11 37.63(18) . . . . ? Cl1 Rh1 C12 C11 -144.10(18) . . . . ? C1 Rh1 C12 C13 8.9(3) . . . . ? N1 Rh1 C12 C13 -174.01(16) . . . . ? C14 Rh1 C12 C13 -38.35(17) . . . . ? C10 Rh1 C12 C13 -81.34(19) . . . . ? C11 Rh1 C12 C13 -119.0(3) . . . . ? Cl1 Rh1 C12 C13 96.93(17) . . . . ? C1 Rh1 C12 C17 -108.7(4) . . . . ? N1 Rh1 C12 C17 68.4(3) . . . . ? C13 Rh1 C12 C17 -117.6(4) . . . . ? C14 Rh1 C12 C17 -155.9(3) . . . . ? C10 Rh1 C12 C17 161.1(3) . . . . ? C11 Rh1 C12 C17 123.4(4) . . . . ? Cl1 Rh1 C12 C17 -20.7(3) . . . . ? C11 C12 C13 C14 2.6(3) . . . . ? C17 C12 C13 C14 -176.8(3) . . . . ? Rh1 C12 C13 C14 63.32(19) . . . . ? C11 C12 C13 C18 176.0(3) . . . . ? C17 C12 C13 C18 -3.3(5) . . . . ? Rh1 C12 C13 C18 -123.2(3) . . . . ? C11 C12 C13 Rh1 -60.8(2) . . . . ? C17 C12 C13 Rh1 119.9(3) . . . . ? C1 Rh1 C13 C14 68.3(2) . . . . ? N1 Rh1 C13 C14 -101.1(4) . . . . ? C10 Rh1 C13 C14 -37.64(17) . . . . ? C11 Rh1 C13 C14 -80.64(19) . . . . ? C12 Rh1 C13 C14 -116.4(2) . . . . ? Cl1 Rh1 C13 C14 158.78(16) . . . . ? C1 Rh1 C13 C12 -175.34(17) . . . . ? N1 Rh1 C13 C12 15.3(4) . . . . ? C14 Rh1 C13 C12 116.4(2) . . . . ? C10 Rh1 C13 C12 78.71(18) . . . . ? C11 Rh1 C13 C12 35.71(17) . . . . ? Cl1 Rh1 C13 C12 -84.87(16) . . . . ? C1 Rh1 C13 C18 -55.2(4) . . . . ? N1 Rh1 C13 C18 135.4(3) . . . . ? C14 Rh1 C13 C18 -123.5(4) . . . . ? C10 Rh1 C13 C18 -161.2(4) . . . . ? C11 Rh1 C13 C18 155.8(4) . . . . ? C12 Rh1 C13 C18 120.1(4) . . . . ? Cl1 Rh1 C13 C18 35.2(3) . . . . ? C12 C13 C14 C10 -3.1(3) . . . . ? C18 C13 C14 C10 -176.2(3) . . . . ? Rh1 C13 C14 C10 61.50(18) . . . . ? C12 C13 C14 C19 176.3(3) . . . . ? C18 C13 C14 C19 3.2(5) . . . . ? Rh1 C13 C14 C19 -119.1(3) . . . . ? C12 C13 C14 Rh1 -64.55(19) . . . . ? C18 C13 C14 Rh1 122.3(3) . . . . ? C11 C10 C14 C13 2.4(3) . . . . ? C15 C10 C14 C13 166.8(3) . . . . ? Rh1 C10 C14 C13 -60.91(19) . . . . ? C11 C10 C14 C19 -177.0(3) . . . . ? C15 C10 C14 C19 -12.6(4) . . . . ? Rh1 C10 C14 C19 119.7(3) . . . . ? C11 C10 C14 Rh1 63.33(18) . . . . ? C15 C10 C14 Rh1 -132.3(3) . . . . ? C1 Rh1 C14 C13 -120.48(19) . . . . ? N1 Rh1 C14 C13 148.47(18) . . . . ? C10 Rh1 C14 C13 117.6(3) . . . . ? C11 Rh1 C14 C13 79.59(19) . . . . ? C12 Rh1 C14 C13 38.58(18) . . . . ? Cl1 Rh1 C14 C13 -28.1(2) . . . . ? C1 Rh1 C14 C10 121.94(18) . . . . ? N1 Rh1 C14 C10 30.9(3) . . . . ? C13 Rh1 C14 C10 -117.6(3) . . . . ? C11 Rh1 C14 C10 -37.99(17) . . . . ? C12 Rh1 C14 C10 -79.00(19) . . . . ? Cl1 Rh1 C14 C10 -145.67(14) . . . . ? C1 Rh1 C14 C19 1.4(3) . . . . ? N1 Rh1 C14 C19 -89.7(3) . . . . ? C13 Rh1 C14 C19 121.9(4) . . . . ? C10 Rh1 C14 C19 -120.5(4) . . . . ? C11 Rh1 C14 C19 -158.5(3) . . . . ? C12 Rh1 C14 C19 160.5(3) . . . . ? Cl1 Rh1 C14 C19 93.8(3) . . . . ? C2 C1 C20 O1 -65.0(4) . . . . ? Rh1 C1 C20 O1 115.2(3) . . . . ? C2 C1 C20 O2 113.5(3) . . . . ? Rh1 C1 C20 O2 -66.2(3) . . . . ? O1 C20 O2 C21 -4.2(5) . . . . ? C1 C20 O2 C21 177.2(3) . . . . ? C20 O2 C21 C22 179.6(3) . . . . ? N1 C9 C24 C25 2.4(4) . . . . ? C8 C9 C24 C25 -172.6(3) . . . . ? C9 C24 C25 C26 0.9(4) . . . . ? C24 C25 C26 C27 -2.5(4) . . . . ? C9 N1 C27 C26 2.5(4) . . . . ? Rh1 N1 C27 C26 -175.8(2) . . . . ? C25 C26 C27 N1 0.8(5) . . . . ? C28 Rh2 N2 C54 126.0(2) . . . . ? C40 Rh2 N2 C54 -67.1(4) . . . . ? C41 Rh2 N2 C54 -138.3(2) . . . . ? C37 Rh2 N2 C54 -119.9(2) . . . . ? C38 Rh2 N2 C54 -81.3(2) . . . . ? C39 Rh2 N2 C54 -52.9(2) . . . . ? Cl2 Rh2 N2 C54 37.4(2) . . . . ? C28 Rh2 N2 C36 -58.0(2) . . . . ? C40 Rh2 N2 C36 109.0(3) . . . . ? C41 Rh2 N2 C36 37.7(3) . . . . ? C37 Rh2 N2 C36 56.1(2) . . . . ? C38 Rh2 N2 C36 94.7(2) . . . . ? C39 Rh2 N2 C36 123.1(2) . . . . ? Cl2 Rh2 N2 C36 -146.6(2) . . . . ? N2 Rh2 C28 C29 55.0(2) . . . . ? C40 Rh2 C28 C29 -120.1(2) . . . . ? C41 Rh2 C28 C29 -83.9(3) . . . . ? C37 Rh2 C28 C29 -48.4(3) . . . . ? C38 Rh2 C28 C29 -43.2(4) . . . . ? C39 Rh2 C28 C29 -126.9(3) . . . . ? Cl2 Rh2 C28 C29 146.8(2) . . . . ? N2 Rh2 C28 C47 -125.74(19) . . . . ? C40 Rh2 C28 C47 59.2(2) . . . . ? C41 Rh2 C28 C47 95.4(2) . . . . ? C37 Rh2 C28 C47 130.83(19) . . . . ? C38 Rh2 C28 C47 136.1(2) . . . . ? C39 Rh2 C28 C47 52.4(3) . . . . ? Cl2 Rh2 C28 C47 -33.89(18) . . . . ? C47 C28 C29 C30 -173.4(2) . . . . ? Rh2 C28 C29 C30 5.9(4) . . . . ? C47 C28 C29 C50 2.2(4) . . . . ? Rh2 C28 C29 C50 -178.5(2) . . . . ? C28 C29 C30 C35 -53.5(4) . . . . ? C50 C29 C30 C35 130.6(3) . . . . ? C28 C29 C30 C31 128.7(3) . . . . ? C50 C29 C30 C31 -47.2(3) . . . . ? C35 C30 C31 C32 0.8(4) . . . . ? C29 C30 C31 C32 178.8(3) . . . . ? C30 C31 C32 C33 -2.1(5) . . . . ? C31 C32 C33 C34 1.7(5) . . . . ? C32 C33 C34 C35 0.0(5) . . . . ? C33 C34 C35 C30 -1.2(4) . . . . ? C33 C34 C35 C36 -176.3(3) . . . . ? C31 C30 C35 C34 0.8(4) . . . . ? C29 C30 C35 C34 -176.9(3) . . . . ? C31 C30 C35 C36 175.4(3) . . . . ? C29 C30 C35 C36 -2.4(4) . . . . ? C54 N2 C36 C51 -1.6(4) . . . . ? Rh2 N2 C36 C51 -177.5(2) . . . . ? C54 N2 C36 C35 175.1(2) . . . . ? Rh2 N2 C36 C35 -0.8(4) . . . . ? C34 C35 C36 N2 -132.9(3) . . . . ? C30 C35 C36 N2 52.4(4) . . . . ? C34 C35 C36 C51 43.9(3) . . . . ? C30 C35 C36 C51 -130.8(3) . . . . ? C28 Rh2 C37 C41 -68.00(19) . . . . ? N2 Rh2 C37 C41 -160.49(16) . . . . ? C40 Rh2 C37 C41 37.30(16) . . . . ? C38 Rh2 C37 C41 115.9(2) . . . . ? C39 Rh2 C37 C41 80.90(18) . . . . ? Cl2 Rh2 C37 C41 76.8(2) . . . . ? C28 Rh2 C37 C38 176.14(16) . . . . ? N2 Rh2 C37 C38 83.66(17) . . . . ? C40 Rh2 C37 C38 -78.55(17) . . . . ? C41 Rh2 C37 C38 -115.9(2) . . . . ? C39 Rh2 C37 C38 -34.96(16) . . . . ? Cl2 Rh2 C37 C38 -39.0(3) . . . . ? C28 Rh2 C37 C42 54.4(3) . . . . ? N2 Rh2 C37 C42 -38.1(3) . . . . ? C40 Rh2 C37 C42 159.7(3) . . . . ? C41 Rh2 C37 C42 122.4(4) . . . . ? C38 Rh2 C37 C42 -121.7(4) . . . . ? C39 Rh2 C37 C42 -156.7(3) . . . . ? Cl2 Rh2 C37 C42 -160.7(2) . . . . ? C41 C37 C38 C39 -2.2(3) . . . . ? C42 C37 C38 C39 -168.3(3) . . . . ? Rh2 C37 C38 C39 60.56(19) . . . . ? C41 C37 C38 C43 177.9(3) . . . . ? C42 C37 C38 C43 11.9(4) . . . . ? Rh2 C37 C38 C43 -119.3(3) . . . . ? C41 C37 C38 Rh2 -62.80(17) . . . . ? C42 C37 C38 Rh2 131.2(3) . . . . ? C28 Rh2 C38 C39 -127.6(2) . . . . ? N2 Rh2 C38 C39 136.69(16) . . . . ? C40 Rh2 C38 C39 -37.85(16) . . . . ? C41 Rh2 C38 C39 -81.27(18) . . . . ? C37 Rh2 C38 C39 -119.9(2) . . . . ? Cl2 Rh2 C38 C39 41.02(18) . . . . ? C28 Rh2 C38 C37 -7.7(3) . . . . ? N2 Rh2 C38 C37 -103.42(17) . . . . ? C40 Rh2 C38 C37 82.05(18) . . . . ? C41 Rh2 C38 C37 38.62(17) . . . . ? C39 Rh2 C38 C37 119.9(2) . . . . ? Cl2 Rh2 C38 C37 160.91(14) . . . . ? C28 Rh2 C38 C43 109.0(3) . . . . ? N2 Rh2 C38 C43 13.3(3) . . . . ? C40 Rh2 C38 C43 -161.2(3) . . . . ? C41 Rh2 C38 C43 155.3(3) . . . . ? C37 Rh2 C38 C43 116.7(3) . . . . ? C39 Rh2 C38 C43 -123.4(3) . . . . ? Cl2 Rh2 C38 C43 -82.4(3) . . . . ? C37 C38 C39 C40 -0.5(3) . . . . ? C43 C38 C39 C40 179.4(3) . . . . ? Rh2 C38 C39 C40 57.74(18) . . . . ? C37 C38 C39 C44 -179.1(3) . . . . ? C43 C38 C39 C44 0.7(5) . . . . ? Rh2 C38 C39 C44 -120.9(3) . . . . ? C37 C38 C39 Rh2 -58.24(18) . . . . ? C43 C38 C39 Rh2 121.6(3) . . . . ? C28 Rh2 C39 C38 129.2(2) . . . . ? N2 Rh2 C39 C38 -52.98(19) . . . . ? C40 Rh2 C39 C38 119.3(2) . . . . ? C41 Rh2 C39 C38 80.23(18) . . . . ? C37 Rh2 C39 C38 37.17(16) . . . . ? Cl2 Rh2 C39 C38 -144.69(16) . . . . ? C28 Rh2 C39 C40 9.9(3) . . . . ? N2 Rh2 C39 C40 -172.27(15) . . . . ? C41 Rh2 C39 C40 -39.05(16) . . . . ? C37 Rh2 C39 C40 -82.12(17) . . . . ? C38 Rh2 C39 C40 -119.3(2) . . . . ? Cl2 Rh2 C39 C40 96.03(15) . . . . ? C28 Rh2 C39 C44 -107.5(3) . . . . ? N2 Rh2 C39 C44 70.3(3) . . . . ? C40 Rh2 C39 C44 -117.4(3) . . . . ? C41 Rh2 C39 C44 -156.5(3) . . . . ? C37 Rh2 C39 C44 160.5(3) . . . . ? C38 Rh2 C39 C44 123.3(3) . . . . ? Cl2 Rh2 C39 C44 -21.4(3) . . . . ? C38 C39 C40 C41 3.0(3) . . . . ? C44 C39 C40 C41 -178.3(3) . . . . ? Rh2 C39 C40 C41 63.65(17) . . . . ? C38 C39 C40 C45 176.4(2) . . . . ? C44 C39 C40 C45 -5.0(4) . . . . ? Rh2 C39 C40 C45 -123.0(3) . . . . ? C38 C39 C40 Rh2 -60.62(19) . . . . ? C44 C39 C40 Rh2 118.1(3) . . . . ? C28 Rh2 C40 C41 69.94(19) . . . . ? N2 Rh2 C40 C41 -95.8(3) . . . . ? C37 Rh2 C40 C41 -37.03(17) . . . . ? C38 Rh2 C40 C41 -80.01(18) . . . . ? C39 Rh2 C40 C41 -115.1(2) . . . . ? Cl2 Rh2 C40 C41 159.94(16) . . . . ? C28 Rh2 C40 C39 -174.92(16) . . . . ? N2 Rh2 C40 C39 19.3(4) . . . . ? C41 Rh2 C40 C39 115.1(2) . . . . ? C37 Rh2 C40 C39 78.12(17) . . . . ? C38 Rh2 C40 C39 35.13(16) . . . . ? Cl2 Rh2 C40 C39 -84.92(15) . . . . ? C28 Rh2 C40 C45 -52.8(3) . . . . ? N2 Rh2 C40 C45 141.4(3) . . . . ? C41 Rh2 C40 C45 -122.7(3) . . . . ? C37 Rh2 C40 C45 -159.8(3) . . . . ? C38 Rh2 C40 C45 157.2(3) . . . . ? C39 Rh2 C40 C45 122.1(3) . . . . ? Cl2 Rh2 C40 C45 37.2(3) . . . . ? C38 C37 C41 C40 4.1(3) . . . . ? C42 C37 C41 C40 169.7(3) . . . . ? Rh2 C37 C41 C40 -60.46(18) . . . . ? C38 C37 C41 C46 -174.8(2) . . . . ? C42 C37 C41 C46 -9.1(4) . . . . ? Rh2 C37 C41 C46 120.7(3) . . . . ? C38 C37 C41 Rh2 64.60(18) . . . . ? C42 C37 C41 Rh2 -129.8(3) . . . . ? C39 C40 C41 C37 -4.4(3) . . . . ? C45 C40 C41 C37 -177.6(3) . . . . ? Rh2 C40 C41 C37 60.95(18) . . . . ? C39 C40 C41 C46 174.4(3) . . . . ? C45 C40 C41 C46 1.3(4) . . . . ? Rh2 C40 C41 C46 -120.2(3) . . . . ? C39 C40 C41 Rh2 -65.38(17) . . . . ? C45 C40 C41 Rh2 121.5(3) . . . . ? C28 Rh2 C41 C37 121.68(17) . . . . ? N2 Rh2 C41 C37 29.6(2) . . . . ? C40 Rh2 C41 C37 -118.7(2) . . . . ? C38 Rh2 C41 C37 -38.75(16) . . . . ? C39 Rh2 C41 C37 -79.29(18) . . . . ? Cl2 Rh2 C41 C37 -144.91(14) . . . . ? C28 Rh2 C41 C40 -119.62(18) . . . . ? N2 Rh2 C41 C40 148.30(17) . . . . ? C37 Rh2 C41 C40 118.7(2) . . . . ? C38 Rh2 C41 C40 79.95(18) . . . . ? C39 Rh2 C41 C40 39.40(17) . . . . ? Cl2 Rh2 C41 C40 -26.2(2) . . . . ? C28 Rh2 C41 C46 1.5(3) . . . . ? N2 Rh2 C41 C46 -90.5(3) . . . . ? C40 Rh2 C41 C46 121.2(3) . . . . ? C37 Rh2 C41 C46 -120.2(3) . . . . ? C38 Rh2 C41 C46 -158.9(3) . . . . ? C39 Rh2 C41 C46 160.6(3) . . . . ? Cl2 Rh2 C41 C46 94.9(3) . . . . ? C29 C28 C47 O3 -71.8(4) . . . . ? Rh2 C28 C47 O3 108.8(3) . . . . ? C29 C28 C47 O4 104.4(3) . . . . ? Rh2 C28 C47 O4 -74.9(3) . . . . ? O3 C47 O4 C48 -0.9(4) . . . . ? C28 C47 O4 C48 -177.4(2) . . . . ? C47 O4 C48 C49 174.5(3) . . . . ? N2 C36 C51 C52 0.6(4) . . . . ? C35 C36 C51 C52 -176.3(3) . . . . ? C36 C51 C52 C53 0.9(4) . . . . ? C51 C52 C53 C54 -1.3(4) . . . . ? C36 N2 C54 C53 1.1(4) . . . . ? Rh2 N2 C54 C53 177.5(2) . . . . ? C52 C53 C54 N2 0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.323 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.141 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_1'h _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll39b _chemical_melting_point ? _chemical_formula_moiety 'C29 H33 Cl Ir N O2' _chemical_formula_sum 'C29 H33 Cl Ir N O2' _chemical_formula_weight 655.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.747(6) _cell_length_b 10.059(3) _cell_length_c 16.216(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.107(4) _cell_angle_gamma 90.00 _cell_volume 2596.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 9985 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 32.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 5.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4505 _exptl_absorpt_correction_T_max 0.8168 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32903 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 32.03 _reflns_number_total 8981 _reflns_number_gt 5550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.9085P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8981 _refine_ls_number_parameters 319 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.745763(12) 0.207891(18) 0.398673(12) 0.01721(5) Uani 1 1 d . . . Cl1 Cl 0.66346(8) 0.08788(12) 0.27186(8) 0.0247(3) Uani 1 1 d . . . N1 N 0.8545(3) 0.1455(4) 0.3744(3) 0.0210(9) Uani 1 1 d . . . C1 C 0.7551(3) 0.0366(5) 0.4697(3) 0.0204(10) Uani 1 1 d . . . C2 C 0.8221(3) 0.0014(5) 0.5375(3) 0.0185(10) Uani 1 1 d . . . C3 C 0.9007(3) 0.0790(4) 0.5738(3) 0.0196(10) Uani 1 1 d . . . C4 C 0.9330(3) 0.0882(5) 0.6641(3) 0.0220(10) Uani 1 1 d . . . H4 H 0.9024 0.0491 0.6983 0.026 Uiso 1 1 calc R . . C5 C 1.0082(3) 0.1522(5) 0.7058(3) 0.0264(11) Uani 1 1 d . . . H5 H 1.0271 0.1600 0.7672 0.032 Uiso 1 1 calc R . . C6 C 1.0554(3) 0.2048(6) 0.6568(3) 0.0313(12) Uani 1 1 d . . . H6 H 1.1072 0.2483 0.6843 0.038 Uiso 1 1 calc R . . C7 C 1.0261(3) 0.1933(5) 0.5673(4) 0.0279(11) Uani 1 1 d . . . H7 H 1.0594 0.2262 0.5339 0.034 Uiso 1 1 calc R . . C8 C 0.9483(3) 0.1343(5) 0.5247(3) 0.0201(10) Uani 1 1 d . . . C9 C 0.9277(3) 0.1295(5) 0.4301(3) 0.0211(10) Uani 1 1 d . . . H9 H 0.9728 0.1130 0.4076 0.025 Uiso 1 1 calc R . . C10 C 0.7814(3) 0.3811(5) 0.4805(3) 0.0218(11) Uani 1 1 d . . . C11 C 0.7719(3) 0.4260(5) 0.3922(3) 0.0237(11) Uani 1 1 d . . . C12 C 0.6892(3) 0.4013(5) 0.3413(3) 0.0243(11) Uani 1 1 d . . . C13 C 0.6441(3) 0.3427(5) 0.3968(3) 0.0242(11) Uani 1 1 d . . . C14 C 0.7010(3) 0.3354(5) 0.4823(3) 0.0201(10) Uani 1 1 d . . . C15 C 0.8555(4) 0.4136(5) 0.5577(4) 0.0298(13) Uani 1 1 d . . . H15A H 0.8512 0.5058 0.5754 0.045 Uiso 1 1 calc R . . H15B H 0.9074 0.4026 0.5425 0.045 Uiso 1 1 calc R . . H15C H 0.8565 0.3538 0.6057 0.045 Uiso 1 1 calc R . . C16 C 0.8409(4) 0.4837(5) 0.3645(4) 0.0342(14) Uani 1 1 d . . . H16A H 0.8554 0.5718 0.3906 0.051 Uiso 1 1 calc R . . H16B H 0.8227 0.4918 0.3011 0.051 Uiso 1 1 calc R . . H16C H 0.8903 0.4256 0.3833 0.051 Uiso 1 1 calc R . . C17 C 0.6501(4) 0.4269(5) 0.2470(3) 0.0329(13) Uani 1 1 d . . . H17A H 0.6101 0.5005 0.2388 0.049 Uiso 1 1 calc R . . H17B H 0.6206 0.3469 0.2188 0.049 Uiso 1 1 calc R . . H17C H 0.6939 0.4501 0.2211 0.049 Uiso 1 1 calc R . . C18 C 0.5517(3) 0.3155(6) 0.3661(4) 0.0351(14) Uani 1 1 d . . . H18A H 0.5212 0.3986 0.3466 0.053 Uiso 1 1 calc R . . H18B H 0.5346 0.2779 0.4138 0.053 Uiso 1 1 calc R . . H18C H 0.5389 0.2522 0.3178 0.053 Uiso 1 1 calc R . . C19 C 0.6817(3) 0.2979(6) 0.5632(3) 0.0292(11) Uani 1 1 d . . . H19A H 0.6850 0.3770 0.5994 0.044 Uiso 1 1 calc R . . H19B H 0.7224 0.2316 0.5953 0.044 Uiso 1 1 calc R . . H19C H 0.6249 0.2605 0.5479 0.044 Uiso 1 1 calc R . . C20 C 0.6841(3) -0.0600(5) 0.4433(3) 0.0206(10) Uani 1 1 d . . . C21 C 0.6041(3) -0.0249(5) 0.4464(3) 0.0213(10) Uani 1 1 d . . . H21 H 0.5949 0.0621 0.4643 0.026 Uiso 1 1 calc R . . C22 C 0.5382(3) -0.1150(5) 0.4238(3) 0.0274(11) Uani 1 1 d . . . H22 H 0.4851 -0.0904 0.4285 0.033 Uiso 1 1 calc R . . C23 C 0.5494(4) -0.2404(5) 0.3944(4) 0.0316(13) Uani 1 1 d . . . H23 H 0.5039 -0.3015 0.3779 0.038 Uiso 1 1 calc R . . C24 C 0.6268(4) -0.2757(5) 0.3893(4) 0.0304(12) Uani 1 1 d . . . H24 H 0.6346 -0.3617 0.3689 0.037 Uiso 1 1 calc R . . C25 C 0.6941(3) -0.1873(5) 0.4136(3) 0.0247(11) Uani 1 1 d . . . H25 H 0.7474 -0.2138 0.4099 0.030 Uiso 1 1 calc R . . C26 C 0.8237(3) -0.1279(5) 0.5846(3) 0.0206(10) Uani 1 1 d . A . O1 O 0.8776(2) -0.2132(4) 0.5935(2) 0.0291(8) Uani 1 1 d . . . O2 O 0.7599(2) -0.1400(4) 0.6170(2) 0.0260(8) Uani 1 1 d . . . C27 C 0.7422(4) -0.2740(6) 0.6428(4) 0.0415(17) Uani 0.39(3) 1 d PD A 1 H27A H 0.7260 -0.3332 0.5915 0.050 Uiso 0.39(3) 1 calc PR A 1 H27B H 0.7931 -0.3112 0.6856 0.050 Uiso 0.39(3) 1 calc PR A 1 C28 C 0.6752(17) -0.267(4) 0.680(2) 0.049(5) Uani 0.39(3) 1 d PD A 1 H28A H 0.6575 -0.3566 0.6897 0.074 Uiso 0.39(3) 1 calc PR A 1 H28B H 0.6276 -0.2187 0.6405 0.074 Uiso 0.39(3) 1 calc PR A 1 H28C H 0.6946 -0.2193 0.7356 0.074 Uiso 0.39(3) 1 calc PR A 1 C27' C 0.7422(4) -0.2740(6) 0.6428(4) 0.0415(17) Uani 0.61(3) 1 d PD A 5 H27C H 0.7532 -0.3406 0.6026 0.050 Uiso 0.61(3) 1 calc PR A 5 H27D H 0.7795 -0.2938 0.7020 0.050 Uiso 0.61(3) 1 calc PR A 5 C28' C 0.6558(8) -0.282(2) 0.6407(17) 0.049(5) Uani 0.61(3) 1 d PD A 5 H28D H 0.6438 -0.3717 0.6571 0.074 Uiso 0.61(3) 1 calc PR A 5 H28E H 0.6191 -0.2619 0.5820 0.074 Uiso 0.61(3) 1 calc PR A 5 H28F H 0.6456 -0.2174 0.6816 0.074 Uiso 0.61(3) 1 calc PR A 5 C29 C 0.8519(4) 0.1367(6) 0.2818(3) 0.0277(12) Uani 1 1 d . . . H29D H 0.9089 0.1237 0.2788 0.042 Uiso 1 1 calc R . . H29A H 0.8285 0.2192 0.2517 0.042 Uiso 1 1 calc R . . H29B H 0.8165 0.0615 0.2540 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02100(9) 0.01551(8) 0.01596(8) 0.00038(9) 0.00697(6) 0.00043(10) Cl1 0.0315(7) 0.0220(6) 0.0187(6) -0.0009(5) 0.0052(5) -0.0038(5) N1 0.027(2) 0.018(2) 0.019(2) -0.0039(16) 0.0072(18) -0.0046(18) C1 0.024(3) 0.020(2) 0.022(3) -0.0033(19) 0.012(2) 0.001(2) C2 0.022(3) 0.020(2) 0.017(2) 0.0003(19) 0.012(2) 0.003(2) C3 0.021(3) 0.014(2) 0.024(3) 0.0002(18) 0.008(2) 0.0037(19) C4 0.022(3) 0.023(2) 0.022(3) 0.000(2) 0.008(2) 0.002(2) C5 0.032(3) 0.024(3) 0.019(3) 0.001(2) 0.002(2) -0.003(2) C6 0.028(3) 0.028(3) 0.032(3) 0.003(3) 0.001(2) -0.006(3) C7 0.023(3) 0.028(3) 0.033(3) 0.003(2) 0.009(2) -0.007(2) C8 0.023(3) 0.015(2) 0.022(2) 0.0013(19) 0.008(2) -0.0018(19) C9 0.023(3) 0.019(2) 0.024(3) 0.000(2) 0.012(2) -0.001(2) C10 0.028(3) 0.016(2) 0.026(3) 0.002(2) 0.015(2) 0.005(2) C11 0.035(3) 0.010(2) 0.029(3) -0.0015(19) 0.015(2) 0.001(2) C12 0.035(3) 0.014(2) 0.021(3) -0.0013(19) 0.004(2) 0.003(2) C13 0.025(3) 0.021(2) 0.027(3) -0.006(2) 0.007(2) 0.000(2) C14 0.031(3) 0.016(2) 0.013(2) 0.0012(17) 0.008(2) 0.0028(19) C15 0.035(3) 0.019(3) 0.034(3) -0.007(2) 0.008(3) -0.002(2) C16 0.052(4) 0.024(3) 0.032(3) -0.001(2) 0.021(3) -0.008(3) C17 0.051(4) 0.023(3) 0.022(3) 0.006(2) 0.008(3) 0.006(3) C18 0.023(3) 0.037(3) 0.045(3) -0.002(3) 0.009(3) 0.010(2) C19 0.032(3) 0.033(3) 0.026(3) -0.006(3) 0.015(2) -0.004(3) C20 0.022(3) 0.020(2) 0.022(2) 0.0048(19) 0.010(2) 0.000(2) C21 0.022(3) 0.023(2) 0.020(2) 0.0030(19) 0.007(2) 0.000(2) C22 0.021(3) 0.030(3) 0.032(3) 0.000(2) 0.010(2) -0.003(2) C23 0.030(3) 0.027(3) 0.038(3) -0.003(2) 0.009(3) -0.013(2) C24 0.036(3) 0.020(3) 0.031(3) -0.009(2) 0.005(2) -0.007(2) C25 0.027(3) 0.023(3) 0.023(3) -0.002(2) 0.006(2) 0.003(2) C26 0.021(3) 0.023(2) 0.018(2) 0.0015(19) 0.005(2) -0.004(2) O1 0.0266(19) 0.0252(18) 0.036(2) 0.0122(18) 0.0111(16) 0.0075(17) O2 0.0232(19) 0.0289(19) 0.027(2) 0.0138(15) 0.0093(17) 0.0026(16) C27 0.028(3) 0.032(4) 0.062(4) 0.031(3) 0.010(3) -0.004(3) C28 0.044(6) 0.037(7) 0.072(13) 0.023(12) 0.026(8) 0.007(7) C27' 0.028(3) 0.032(4) 0.062(4) 0.031(3) 0.010(3) -0.004(3) C28' 0.044(6) 0.037(7) 0.072(13) 0.023(12) 0.026(8) 0.007(7) C29 0.036(3) 0.032(3) 0.019(3) 0.002(2) 0.014(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.051(5) . ? Ir1 N1 2.076(4) . ? Ir1 C10 2.158(5) . ? Ir1 C14 2.163(5) . ? Ir1 C13 2.169(5) . ? Ir1 C12 2.236(5) . ? Ir1 C11 2.246(5) . ? Ir1 Cl1 2.4133(13) . ? N1 C9 1.286(6) . ? N1 C29 1.492(6) . ? C1 C2 1.352(7) . ? C1 C20 1.492(7) . ? C2 C3 1.485(7) . ? C2 C26 1.504(7) . ? C3 C4 1.397(7) . ? C3 C8 1.404(7) . ? C4 C5 1.388(7) . ? C4 H4 0.9500 . ? C5 C6 1.389(7) . ? C5 H5 0.9500 . ? C6 C7 1.385(7) . ? C6 H6 0.9500 . ? C7 C8 1.402(7) . ? C7 H7 0.9500 . ? C8 C9 1.466(7) . ? C9 H9 0.9500 . ? C10 C14 1.432(7) . ? C10 C11 1.461(7) . ? C10 C15 1.500(7) . ? C11 C12 1.397(7) . ? C11 C16 1.482(7) . ? C12 C13 1.466(7) . ? C12 C17 1.488(7) . ? C13 C14 1.419(7) . ? C13 C18 1.496(7) . ? C14 C19 1.494(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.397(7) . ? C20 C21 1.401(7) . ? C21 C22 1.386(7) . ? C21 H21 0.9500 . ? C22 C23 1.381(8) . ? C22 H22 0.9500 . ? C23 C24 1.371(8) . ? C23 H23 0.9500 . ? C24 C25 1.394(7) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 O1 1.220(6) . ? C26 O2 1.335(6) . ? O2 C27 1.469(6) . ? C27 C28 1.433(11) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C28' H28D 0.9800 . ? C28' H28E 0.9800 . ? C28' H28F 0.9800 . ? C29 H29D 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 86.20(17) . . ? C1 Ir1 C10 112.01(19) . . ? N1 Ir1 C10 105.59(17) . . ? C1 Ir1 C14 97.31(18) . . ? N1 Ir1 C14 142.50(18) . . ? C10 Ir1 C14 38.71(18) . . ? C1 Ir1 C13 117.12(19) . . ? N1 Ir1 C13 156.49(18) . . ? C10 Ir1 C13 64.53(19) . . ? C14 Ir1 C13 38.24(19) . . ? C1 Ir1 C12 155.9(2) . . ? N1 Ir1 C12 117.87(18) . . ? C10 Ir1 C12 63.51(19) . . ? C14 Ir1 C12 63.91(18) . . ? C13 Ir1 C12 38.83(19) . . ? C1 Ir1 C11 149.8(2) . . ? N1 Ir1 C11 95.23(17) . . ? C10 Ir1 C11 38.69(18) . . ? C14 Ir1 C11 63.93(18) . . ? C13 Ir1 C11 63.39(19) . . ? C12 Ir1 C11 36.33(19) . . ? C1 Ir1 Cl1 88.96(14) . . ? N1 Ir1 Cl1 89.42(12) . . ? C10 Ir1 Cl1 154.57(14) . . ? C14 Ir1 Cl1 127.84(14) . . ? C13 Ir1 Cl1 93.62(14) . . ? C12 Ir1 Cl1 91.42(13) . . ? C11 Ir1 Cl1 121.13(14) . . ? C9 N1 C29 115.0(4) . . ? C9 N1 Ir1 127.3(3) . . ? C29 N1 Ir1 117.1(3) . . ? C2 C1 C20 116.7(4) . . ? C2 C1 Ir1 125.2(4) . . ? C20 C1 Ir1 118.1(3) . . ? C1 C2 C3 126.4(4) . . ? C1 C2 C26 121.3(5) . . ? C3 C2 C26 112.3(4) . . ? C4 C3 C8 117.6(5) . . ? C4 C3 C2 117.2(4) . . ? C8 C3 C2 125.0(4) . . ? C5 C4 C3 122.6(5) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C4 C5 C6 119.3(5) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 119.2(5) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 121.6(5) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 119.5(5) . . ? C7 C8 C9 114.2(4) . . ? C3 C8 C9 126.2(5) . . ? N1 C9 C8 126.4(5) . . ? N1 C9 H9 116.8 . . ? C8 C9 H9 116.8 . . ? C14 C10 C11 107.6(4) . . ? C14 C10 C15 126.3(4) . . ? C11 C10 C15 124.1(5) . . ? C14 C10 Ir1 70.8(3) . . ? C11 C10 Ir1 73.9(3) . . ? C15 C10 Ir1 133.5(4) . . ? C12 C11 C10 108.0(5) . . ? C12 C11 C16 127.8(5) . . ? C10 C11 C16 124.1(5) . . ? C12 C11 Ir1 71.5(3) . . ? C10 C11 Ir1 67.4(3) . . ? C16 C11 Ir1 125.3(4) . . ? C11 C12 C13 108.3(4) . . ? C11 C12 C17 128.0(5) . . ? C13 C12 C17 123.7(5) . . ? C11 C12 Ir1 72.2(3) . . ? C13 C12 Ir1 68.1(3) . . ? C17 C12 Ir1 124.9(3) . . ? C14 C13 C12 107.7(4) . . ? C14 C13 C18 128.8(5) . . ? C12 C13 C18 123.1(5) . . ? C14 C13 Ir1 70.6(3) . . ? C12 C13 Ir1 73.0(3) . . ? C18 C13 Ir1 128.0(4) . . ? C13 C14 C10 108.2(4) . . ? C13 C14 C19 127.5(5) . . ? C10 C14 C19 124.1(5) . . ? C13 C14 Ir1 71.1(3) . . ? C10 C14 Ir1 70.5(3) . . ? C19 C14 Ir1 127.8(3) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 117.5(5) . . ? C25 C20 C1 121.7(4) . . ? C21 C20 C1 120.8(4) . . ? C22 C21 C20 121.1(5) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 120.4(5) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 119.3(5) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 121.0(5) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C24 C25 C20 120.6(5) . . ? C24 C25 H25 119.7 . . ? C20 C25 H25 119.7 . . ? O1 C26 O2 122.8(4) . . ? O1 C26 C2 124.4(4) . . ? O2 C26 C2 112.8(4) . . ? C26 O2 C27 116.9(4) . . ? C28 C27 O2 109.1(16) . . ? C28 C27 H27A 109.9 . . ? O2 C27 H27A 109.9 . . ? C28 C27 H27B 109.9 . . ? O2 C27 H27B 109.9 . . ? H27A C27 H27B 108.3 . . ? N1 C29 H29D 109.5 . . ? N1 C29 H29A 109.5 . . ? H29D C29 H29A 109.5 . . ? N1 C29 H29B 109.5 . . ? H29D C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C9 -63.9(4) . . . . ? C10 Ir1 N1 C9 47.9(4) . . . . ? C14 Ir1 N1 C9 33.1(5) . . . . ? C13 Ir1 N1 C9 109.3(5) . . . . ? C12 Ir1 N1 C9 115.8(4) . . . . ? C11 Ir1 N1 C9 85.8(4) . . . . ? Cl1 Ir1 N1 C9 -152.9(4) . . . . ? C1 Ir1 N1 C29 125.7(4) . . . . ? C10 Ir1 N1 C29 -122.5(4) . . . . ? C14 Ir1 N1 C29 -137.2(4) . . . . ? C13 Ir1 N1 C29 -61.0(6) . . . . ? C12 Ir1 N1 C29 -54.6(4) . . . . ? C11 Ir1 N1 C29 -84.5(4) . . . . ? Cl1 Ir1 N1 C29 36.7(3) . . . . ? N1 Ir1 C1 C2 57.2(4) . . . . ? C10 Ir1 C1 C2 -48.1(5) . . . . ? C14 Ir1 C1 C2 -85.3(4) . . . . ? C13 Ir1 C1 C2 -119.8(4) . . . . ? C12 Ir1 C1 C2 -122.1(5) . . . . ? C11 Ir1 C1 C2 -36.7(6) . . . . ? Cl1 Ir1 C1 C2 146.7(4) . . . . ? N1 Ir1 C1 C20 -120.6(4) . . . . ? C10 Ir1 C1 C20 134.1(4) . . . . ? C14 Ir1 C1 C20 96.9(4) . . . . ? C13 Ir1 C1 C20 62.4(4) . . . . ? C12 Ir1 C1 C20 60.0(6) . . . . ? C11 Ir1 C1 C20 145.5(4) . . . . ? Cl1 Ir1 C1 C20 -31.2(3) . . . . ? C20 C1 C2 C3 178.2(4) . . . . ? Ir1 C1 C2 C3 0.3(7) . . . . ? C20 C1 C2 C26 -0.9(7) . . . . ? Ir1 C1 C2 C26 -178.8(3) . . . . ? C1 C2 C3 C4 136.3(5) . . . . ? C26 C2 C3 C4 -44.5(6) . . . . ? C1 C2 C3 C8 -49.1(7) . . . . ? C26 C2 C3 C8 130.1(5) . . . . ? C8 C3 C4 C5 1.8(7) . . . . ? C2 C3 C4 C5 176.7(5) . . . . ? C3 C4 C5 C6 -2.7(8) . . . . ? C4 C5 C6 C7 0.6(8) . . . . ? C5 C6 C7 C8 2.5(9) . . . . ? C6 C7 C8 C3 -3.4(8) . . . . ? C6 C7 C8 C9 -179.5(5) . . . . ? C4 C3 C8 C7 1.3(7) . . . . ? C2 C3 C8 C7 -173.2(5) . . . . ? C4 C3 C8 C9 176.9(5) . . . . ? C2 C3 C8 C9 2.3(8) . . . . ? C29 N1 C9 C8 179.5(5) . . . . ? Ir1 N1 C9 C8 9.0(7) . . . . ? C7 C8 C9 N1 -142.9(5) . . . . ? C3 C8 C9 N1 41.3(8) . . . . ? C1 Ir1 C10 C14 -73.4(3) . . . . ? N1 Ir1 C10 C14 -165.7(3) . . . . ? C13 Ir1 C10 C14 37.2(3) . . . . ? C12 Ir1 C10 C14 80.6(3) . . . . ? C11 Ir1 C10 C14 115.7(4) . . . . ? Cl1 Ir1 C10 C14 70.1(4) . . . . ? C1 Ir1 C10 C11 170.8(3) . . . . ? N1 Ir1 C10 C11 78.6(3) . . . . ? C14 Ir1 C10 C11 -115.7(4) . . . . ? C13 Ir1 C10 C11 -78.5(3) . . . . ? C12 Ir1 C10 C11 -35.1(3) . . . . ? Cl1 Ir1 C10 C11 -45.6(5) . . . . ? C1 Ir1 C10 C15 48.9(5) . . . . ? N1 Ir1 C10 C15 -43.4(5) . . . . ? C14 Ir1 C10 C15 122.3(6) . . . . ? C13 Ir1 C10 C15 159.5(5) . . . . ? C12 Ir1 C10 C15 -157.1(6) . . . . ? C11 Ir1 C10 C15 -122.0(6) . . . . ? Cl1 Ir1 C10 C15 -167.6(3) . . . . ? C14 C10 C11 C12 -3.1(5) . . . . ? C15 C10 C11 C12 -167.8(5) . . . . ? Ir1 C10 C11 C12 60.1(3) . . . . ? C14 C10 C11 C16 178.4(5) . . . . ? C15 C10 C11 C16 13.7(8) . . . . ? Ir1 C10 C11 C16 -118.3(5) . . . . ? C14 C10 C11 Ir1 -63.2(3) . . . . ? C15 C10 C11 Ir1 132.1(5) . . . . ? C1 Ir1 C11 C12 -136.7(4) . . . . ? N1 Ir1 C11 C12 131.9(3) . . . . ? C10 Ir1 C11 C12 -119.6(4) . . . . ? C14 Ir1 C11 C12 -80.7(3) . . . . ? C13 Ir1 C11 C12 -37.9(3) . . . . ? Cl1 Ir1 C11 C12 39.4(3) . . . . ? C1 Ir1 C11 C10 -17.1(5) . . . . ? N1 Ir1 C11 C10 -108.5(3) . . . . ? C14 Ir1 C11 C10 38.8(3) . . . . ? C13 Ir1 C11 C10 81.7(3) . . . . ? C12 Ir1 C11 C10 119.6(4) . . . . ? Cl1 Ir1 C11 C10 159.0(2) . . . . ? C1 Ir1 C11 C16 99.6(5) . . . . ? N1 Ir1 C11 C16 8.2(5) . . . . ? C10 Ir1 C11 C16 116.7(6) . . . . ? C14 Ir1 C11 C16 155.5(5) . . . . ? C13 Ir1 C11 C16 -161.6(5) . . . . ? C12 Ir1 C11 C16 -123.7(6) . . . . ? Cl1 Ir1 C11 C16 -84.3(5) . . . . ? C10 C11 C12 C13 1.2(5) . . . . ? C16 C11 C12 C13 179.6(5) . . . . ? Ir1 C11 C12 C13 58.8(3) . . . . ? C10 C11 C12 C17 -178.4(5) . . . . ? C16 C11 C12 C17 0.0(9) . . . . ? Ir1 C11 C12 C17 -120.8(5) . . . . ? C10 C11 C12 Ir1 -57.6(3) . . . . ? C16 C11 C12 Ir1 120.8(5) . . . . ? C1 Ir1 C12 C11 122.3(5) . . . . ? N1 Ir1 C12 C11 -57.0(3) . . . . ? C10 Ir1 C12 C11 37.4(3) . . . . ? C14 Ir1 C12 C11 80.8(3) . . . . ? C13 Ir1 C12 C11 118.9(4) . . . . ? Cl1 Ir1 C12 C11 -147.1(3) . . . . ? C1 Ir1 C12 C13 3.4(6) . . . . ? N1 Ir1 C12 C13 -175.9(3) . . . . ? C10 Ir1 C12 C13 -81.5(3) . . . . ? C14 Ir1 C12 C13 -38.1(3) . . . . ? C11 Ir1 C12 C13 -118.9(4) . . . . ? Cl1 Ir1 C12 C13 94.0(3) . . . . ? C1 Ir1 C12 C17 -113.3(6) . . . . ? N1 Ir1 C12 C17 67.4(5) . . . . ? C10 Ir1 C12 C17 161.8(5) . . . . ? C14 Ir1 C12 C17 -154.8(5) . . . . ? C13 Ir1 C12 C17 -116.7(6) . . . . ? C11 Ir1 C12 C17 124.4(6) . . . . ? Cl1 Ir1 C12 C17 -22.7(5) . . . . ? C11 C12 C13 C14 1.2(6) . . . . ? C17 C12 C13 C14 -179.2(5) . . . . ? Ir1 C12 C13 C14 62.6(3) . . . . ? C11 C12 C13 C18 173.9(5) . . . . ? C17 C12 C13 C18 -6.5(8) . . . . ? Ir1 C12 C13 C18 -124.7(5) . . . . ? C11 C12 C13 Ir1 -61.4(3) . . . . ? C17 C12 C13 Ir1 118.3(5) . . . . ? C1 Ir1 C13 C14 65.2(3) . . . . ? N1 Ir1 C13 C14 -107.2(5) . . . . ? C10 Ir1 C13 C14 -37.6(3) . . . . ? C12 Ir1 C13 C14 -116.3(4) . . . . ? C11 Ir1 C13 C14 -80.9(3) . . . . ? Cl1 Ir1 C13 C14 155.9(3) . . . . ? C1 Ir1 C13 C12 -178.5(3) . . . . ? N1 Ir1 C13 C12 9.1(6) . . . . ? C10 Ir1 C13 C12 78.7(3) . . . . ? C14 Ir1 C13 C12 116.3(4) . . . . ? C11 Ir1 C13 C12 35.4(3) . . . . ? Cl1 Ir1 C13 C12 -87.8(3) . . . . ? C1 Ir1 C13 C18 -59.4(5) . . . . ? N1 Ir1 C13 C18 128.2(5) . . . . ? C10 Ir1 C13 C18 -162.3(6) . . . . ? C14 Ir1 C13 C18 -124.6(6) . . . . ? C12 Ir1 C13 C18 119.1(6) . . . . ? C11 Ir1 C13 C18 154.5(6) . . . . ? Cl1 Ir1 C13 C18 31.3(5) . . . . ? C12 C13 C14 C10 -3.1(5) . . . . ? C18 C13 C14 C10 -175.3(5) . . . . ? Ir1 C13 C14 C10 61.0(3) . . . . ? C12 C13 C14 C19 172.2(5) . . . . ? C18 C13 C14 C19 0.1(9) . . . . ? Ir1 C13 C14 C19 -123.6(5) . . . . ? C12 C13 C14 Ir1 -64.1(3) . . . . ? C18 C13 C14 Ir1 123.7(5) . . . . ? C11 C10 C14 C13 3.8(5) . . . . ? C15 C10 C14 C13 168.1(5) . . . . ? Ir1 C10 C14 C13 -61.4(3) . . . . ? C11 C10 C14 C19 -171.7(5) . . . . ? C15 C10 C14 C19 -7.4(8) . . . . ? Ir1 C10 C14 C19 123.0(5) . . . . ? C11 C10 C14 Ir1 65.3(3) . . . . ? C15 C10 C14 Ir1 -130.5(5) . . . . ? C1 Ir1 C14 C13 -125.4(3) . . . . ? N1 Ir1 C14 C13 141.3(3) . . . . ? C10 Ir1 C14 C13 118.2(4) . . . . ? C12 Ir1 C14 C13 38.7(3) . . . . ? C11 Ir1 C14 C13 79.4(3) . . . . ? Cl1 Ir1 C14 C13 -31.1(3) . . . . ? C1 Ir1 C14 C10 116.4(3) . . . . ? N1 Ir1 C14 C10 23.1(4) . . . . ? C13 Ir1 C14 C10 -118.2(4) . . . . ? C12 Ir1 C14 C10 -79.4(3) . . . . ? C11 Ir1 C14 C10 -38.8(3) . . . . ? Cl1 Ir1 C14 C10 -149.2(2) . . . . ? C1 Ir1 C14 C19 -2.2(5) . . . . ? N1 Ir1 C14 C19 -95.5(5) . . . . ? C10 Ir1 C14 C19 -118.6(6) . . . . ? C13 Ir1 C14 C19 123.2(6) . . . . ? C12 Ir1 C14 C19 162.0(5) . . . . ? C11 Ir1 C14 C19 -157.4(5) . . . . ? Cl1 Ir1 C14 C19 92.2(5) . . . . ? C2 C1 C20 C25 -62.3(6) . . . . ? Ir1 C1 C20 C25 115.7(5) . . . . ? C2 C1 C20 C21 118.6(5) . . . . ? Ir1 C1 C20 C21 -63.4(5) . . . . ? C25 C20 C21 C22 2.3(7) . . . . ? C1 C20 C21 C22 -178.6(5) . . . . ? C20 C21 C22 C23 -2.4(8) . . . . ? C21 C22 C23 C24 1.1(8) . . . . ? C22 C23 C24 C25 0.3(8) . . . . ? C23 C24 C25 C20 -0.4(8) . . . . ? C21 C20 C25 C24 -0.9(7) . . . . ? C1 C20 C25 C24 -180.0(5) . . . . ? C1 C2 C26 O1 122.8(6) . . . . ? C3 C2 C26 O1 -56.4(6) . . . . ? C1 C2 C26 O2 -57.8(6) . . . . ? C3 C2 C26 O2 123.0(4) . . . . ? O1 C26 O2 C27 -16.8(7) . . . . ? C2 C26 O2 C27 163.8(4) . . . . ? C26 O2 C27 C28 176.9(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.407 _refine_diff_density_min -1.727 _refine_diff_density_rms 0.203 _vrf_PLAT860_jonll39 ; PROBLEM: _G Note: Number of Least-Squares Restraints ....... 1 RESPONSE: The ethyl group is modeled as disordered over two positions (60:40). Thermal constraints and geometrical restraints were applied to the model. ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_3'h _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll67 _chemical_melting_point ? _chemical_formula_moiety 'C32 H33 Cl Ir N O2' _chemical_formula_sum 'C32 H33 Cl Ir N O2' _chemical_formula_weight 691.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.116(2) _cell_length_b 13.727(2) _cell_length_c 16.132(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.127(2) _cell_angle_gamma 90.00 _cell_volume 3054.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4024 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 31.14 _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 4.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5339 _exptl_absorpt_correction_T_max 0.8410 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53070 _diffrn_reflns_av_R_equivalents 0.1109 _diffrn_reflns_av_sigmaI/netI 0.1081 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 33.14 _reflns_number_total 11648 _reflns_number_gt 7082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11648 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1088 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.786849(17) 0.817004(17) 0.752176(14) 0.01980(7) Uani 1 1 d . . . Cl1 Cl 0.72566(12) 0.89220(12) 0.85375(10) 0.0279(3) Uani 1 1 d . . . N1 N 0.9279(4) 0.8536(4) 0.8483(3) 0.0211(10) Uani 1 1 d . . . C1 C 0.7861(4) 0.9510(5) 0.6952(3) 0.0208(11) Uani 1 1 d . . . C2 C 0.8467(4) 0.9790(4) 0.6588(4) 0.0213(12) Uani 1 1 d . . . C3 C 0.9293(4) 0.9220(4) 0.6568(4) 0.0213(11) Uani 1 1 d . . . C4 C 0.9431(4) 0.9207(4) 0.5766(4) 0.0216(12) Uani 1 1 d . . . H4A H 0.8994 0.9559 0.5256 0.026 Uiso 1 1 calc R . . C5 C 1.0182(5) 0.8698(5) 0.5686(4) 0.0234(12) Uani 1 1 d . . . H5A H 1.0243 0.8675 0.5123 0.028 Uiso 1 1 calc R . . C6 C 1.0839(5) 0.8226(5) 0.6439(4) 0.0245(12) Uani 1 1 d . . . H6A H 1.1367 0.7884 0.6402 0.029 Uiso 1 1 calc R . . C7 C 1.0733(4) 0.8249(4) 0.7240(4) 0.0217(11) Uani 1 1 d . . . H7A H 1.1193 0.7918 0.7752 0.026 Uiso 1 1 calc R . . C8 C 0.9973(5) 0.8740(4) 0.7328(4) 0.0211(11) Uani 1 1 d . . . C9 C 1.0013(5) 0.8818(4) 0.8262(4) 0.0207(11) Uani 1 1 d . . . C10 C 0.8016(5) 0.6992(4) 0.6690(4) 0.0244(13) Uani 1 1 d . . . C11 C 0.8038(4) 0.6544(4) 0.7509(4) 0.0205(12) Uani 1 1 d . . . C12 C 0.7145(5) 0.6758(5) 0.7572(4) 0.0274(13) Uani 1 1 d . . . C13 C 0.6571(5) 0.7341(5) 0.6793(4) 0.0291(14) Uani 1 1 d . . . C14 C 0.7089(5) 0.7438(5) 0.6242(4) 0.0320(15) Uani 1 1 d . . . C15 C 0.8726(6) 0.6767(5) 0.6287(5) 0.0381(18) Uani 1 1 d . . . H15A H 0.8498 0.6205 0.5881 0.057 Uiso 1 1 calc R . . H15B H 0.9359 0.6618 0.6774 0.057 Uiso 1 1 calc R . . H15C H 0.8787 0.7332 0.5942 0.057 Uiso 1 1 calc R . . C16 C 0.8849(5) 0.5946(5) 0.8159(5) 0.0312(14) Uani 1 1 d . . . H16A H 0.8821 0.5290 0.7911 0.047 Uiso 1 1 calc R . . H16B H 0.8788 0.5906 0.8740 0.047 Uiso 1 1 calc R . . H16C H 0.9469 0.6250 0.8254 0.047 Uiso 1 1 calc R . . C17 C 0.6845(6) 0.6434(6) 0.8294(5) 0.0345(16) Uani 1 1 d . . . H17A H 0.6384 0.5894 0.8067 0.052 Uiso 1 1 calc R . . H17B H 0.6536 0.6977 0.8469 0.052 Uiso 1 1 calc R . . H17C H 0.7415 0.6217 0.8823 0.052 Uiso 1 1 calc R . . C18 C 0.5550(6) 0.7631(6) 0.6606(6) 0.047(2) Uani 1 1 d . . . H18A H 0.5164 0.7046 0.6572 0.070 Uiso 1 1 calc R . . H18B H 0.5268 0.7983 0.6028 0.070 Uiso 1 1 calc R . . H18C H 0.5550 0.8052 0.7097 0.070 Uiso 1 1 calc R . . C19 C 0.6750(7) 0.7865(6) 0.5311(5) 0.050(2) Uani 1 1 d . . . H19A H 0.6777 0.7367 0.4887 0.074 Uiso 1 1 calc R . . H19B H 0.7169 0.8413 0.5319 0.074 Uiso 1 1 calc R . . H19C H 0.6081 0.8095 0.5117 0.074 Uiso 1 1 calc R . . C20 C 0.7098(5) 1.0228(5) 0.6925(4) 0.0235(12) Uani 1 1 d . . . C21 C 0.6130(5) 1.0063(6) 0.6408(5) 0.0354(16) Uani 1 1 d . . . H21A H 0.5927 0.9475 0.6073 0.043 Uiso 1 1 calc R . . C22 C 0.5452(6) 1.0758(6) 0.6379(5) 0.0423(18) Uani 1 1 d . . . H22A H 0.4787 1.0651 0.6001 0.051 Uiso 1 1 calc R . . C23 C 0.5720(6) 1.1595(6) 0.6883(6) 0.044(2) Uani 1 1 d . . . H23A H 0.5247 1.2062 0.6862 0.053 Uiso 1 1 calc R . . C24 C 0.6672(6) 1.1744(6) 0.7414(6) 0.0435(19) Uani 1 1 d . . . H24A H 0.6866 1.2310 0.7784 0.052 Uiso 1 1 calc R . . C25 C 0.7369(5) 1.1074(5) 0.7421(5) 0.0326(15) Uani 1 1 d . . . H25A H 0.8036 1.1204 0.7772 0.039 Uiso 1 1 calc R . . C26 C 0.8316(5) 1.0730(5) 0.6077(4) 0.0251(13) Uani 1 1 d . . . O1 O 0.8860(4) 1.1413(4) 0.6286(4) 0.0353(11) Uani 1 1 d . . . O2 O 0.7497(4) 1.0710(4) 0.5306(3) 0.0339(11) Uani 1 1 d . . . C27 C 0.7245(6) 1.1597(6) 0.4766(6) 0.044(2) Uani 1 1 d . . . H27A H 0.6753 1.1445 0.4150 0.052 Uiso 1 1 calc R . . H27B H 0.7828 1.1851 0.4704 0.052 Uiso 1 1 calc R . . C28 C 0.6855(7) 1.2366(7) 0.5185(7) 0.058(3) Uani 1 1 d . . . H28A H 0.6687 1.2947 0.4798 0.088 Uiso 1 1 calc R . . H28B H 0.7348 1.2535 0.5787 0.088 Uiso 1 1 calc R . . H28C H 0.6275 1.2120 0.5244 0.088 Uiso 1 1 calc R . . C29 C 1.0896(5) 0.9122(5) 0.8934(4) 0.0254(13) Uani 1 1 d . . . H29A H 1.1405 0.9318 0.8769 0.031 Uiso 1 1 calc R . . C30 C 1.1040(5) 0.9142(5) 0.9833(4) 0.0278(14) Uani 1 1 d . . . H30A H 1.1625 0.9385 1.0289 0.033 Uiso 1 1 calc R . . C31 C 1.0295(5) 0.8791(5) 1.0047(4) 0.0265(13) Uani 1 1 d . . . H31A H 1.0377 0.8754 1.0663 0.032 Uiso 1 1 calc R . . C32 C 0.9451(5) 0.8503(4) 0.9368(4) 0.0221(12) Uani 1 1 d . . . H32A H 0.8952 0.8264 0.9528 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02413(11) 0.02034(11) 0.01584(9) -0.00075(10) 0.00909(7) -0.00151(11) Cl1 0.0348(8) 0.0301(8) 0.0230(7) -0.0033(6) 0.0162(6) -0.0014(6) N1 0.022(3) 0.019(2) 0.020(2) 0.0002(19) 0.0072(19) -0.002(2) C1 0.021(3) 0.027(3) 0.011(2) -0.004(2) 0.004(2) -0.002(2) C2 0.026(3) 0.019(3) 0.019(3) 0.003(2) 0.010(2) 0.001(2) C3 0.028(3) 0.014(3) 0.023(3) 0.002(2) 0.011(2) 0.002(2) C4 0.027(3) 0.019(3) 0.022(3) 0.004(2) 0.013(2) -0.004(2) C5 0.033(3) 0.024(3) 0.016(2) 0.002(2) 0.012(2) 0.002(3) C6 0.030(3) 0.019(3) 0.029(3) 0.001(2) 0.016(2) -0.001(3) C7 0.025(3) 0.017(3) 0.022(3) 0.001(2) 0.009(2) 0.003(2) C8 0.029(3) 0.018(3) 0.019(3) 0.000(2) 0.012(2) -0.003(2) C9 0.031(3) 0.016(3) 0.017(2) -0.003(2) 0.012(2) -0.006(2) C10 0.034(3) 0.024(3) 0.019(3) -0.005(2) 0.014(2) -0.007(2) C11 0.026(3) 0.015(2) 0.021(3) -0.003(2) 0.011(2) -0.004(2) C12 0.027(3) 0.029(3) 0.030(3) -0.001(3) 0.015(2) -0.008(3) C13 0.024(3) 0.025(3) 0.027(3) -0.004(3) 0.001(2) -0.002(3) C14 0.050(4) 0.024(3) 0.014(3) -0.004(2) 0.005(3) -0.005(3) C15 0.062(5) 0.023(3) 0.050(4) -0.015(3) 0.044(4) -0.014(3) C16 0.031(4) 0.026(3) 0.034(4) -0.005(3) 0.012(3) -0.002(3) C17 0.038(4) 0.038(4) 0.037(4) -0.002(3) 0.025(3) -0.002(3) C18 0.032(4) 0.039(5) 0.056(5) -0.001(4) 0.004(4) 0.001(3) C19 0.086(7) 0.026(4) 0.024(3) -0.001(3) 0.008(4) 0.000(4) C20 0.028(3) 0.024(3) 0.019(3) 0.003(2) 0.010(2) -0.002(2) C21 0.027(4) 0.038(4) 0.038(4) 0.008(3) 0.010(3) 0.000(3) C22 0.027(4) 0.047(5) 0.049(5) 0.000(4) 0.012(3) 0.006(3) C23 0.032(4) 0.035(4) 0.071(6) -0.004(4) 0.025(4) 0.009(3) C24 0.033(4) 0.038(4) 0.059(5) -0.012(4) 0.019(3) 0.002(3) C25 0.026(3) 0.036(4) 0.034(3) -0.010(3) 0.011(3) 0.002(3) C26 0.029(3) 0.024(3) 0.029(3) 0.005(2) 0.019(3) 0.007(3) O1 0.030(3) 0.022(2) 0.055(3) 0.010(2) 0.017(2) 0.003(2) O2 0.040(3) 0.030(3) 0.026(2) 0.0089(19) 0.007(2) 0.001(2) C27 0.047(5) 0.034(4) 0.043(4) 0.026(3) 0.011(3) 0.003(3) C28 0.052(6) 0.041(5) 0.068(6) 0.020(4) 0.010(5) 0.005(4) C29 0.027(3) 0.026(3) 0.025(3) 0.002(2) 0.012(2) -0.002(3) C30 0.031(3) 0.030(3) 0.016(3) -0.002(2) 0.004(2) -0.002(3) C31 0.037(4) 0.024(3) 0.016(3) 0.000(2) 0.009(2) 0.001(3) C32 0.029(3) 0.016(3) 0.023(3) 0.001(2) 0.012(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.054(6) . ? Ir1 N1 2.121(5) . ? Ir1 C13 2.153(6) . ? Ir1 C14 2.161(6) . ? Ir1 C10 2.170(6) . ? Ir1 C12 2.243(6) . ? Ir1 C11 2.247(6) . ? Ir1 Cl1 2.4175(15) . ? N1 C32 1.344(7) . ? N1 C9 1.352(8) . ? C1 C2 1.331(8) . ? C1 C20 1.503(9) . ? C2 C3 1.485(8) . ? C2 C26 1.497(8) . ? C3 C4 1.393(8) . ? C3 C8 1.402(8) . ? C4 C5 1.383(9) . ? C4 H4A 0.9500 . ? C5 C6 1.377(8) . ? C5 H5A 0.9500 . ? C6 C7 1.365(8) . ? C6 H6A 0.9500 . ? C7 C8 1.388(8) . ? C7 H7A 0.9500 . ? C8 C9 1.487(8) . ? C9 C29 1.396(8) . ? C10 C14 1.426(10) . ? C10 C11 1.445(8) . ? C10 C15 1.496(9) . ? C11 C12 1.426(8) . ? C11 C16 1.491(9) . ? C12 C13 1.443(9) . ? C12 C17 1.480(9) . ? C13 C14 1.410(10) . ? C13 C18 1.501(10) . ? C14 C19 1.494(9) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.375(9) . ? C20 C25 1.375(9) . ? C21 C22 1.388(10) . ? C21 H21A 0.9500 . ? C22 C23 1.369(11) . ? C22 H22A 0.9500 . ? C23 C24 1.357(11) . ? C23 H23A 0.9500 . ? C24 C25 1.394(10) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 O1 1.201(8) . ? C26 O2 1.349(8) . ? O2 C27 1.454(8) . ? C27 C28 1.498(13) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.376(8) . ? C29 H29A 0.9500 . ? C30 C31 1.392(9) . ? C30 H30A 0.9500 . ? C31 C32 1.357(9) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 86.3(2) . . ? C1 Ir1 C13 113.1(2) . . ? N1 Ir1 C13 160.6(2) . . ? C1 Ir1 C14 95.0(2) . . ? N1 Ir1 C14 143.2(3) . . ? C13 Ir1 C14 38.1(3) . . ? C1 Ir1 C10 111.9(2) . . ? N1 Ir1 C10 107.6(2) . . ? C13 Ir1 C10 64.5(3) . . ? C14 Ir1 C10 38.5(3) . . ? C1 Ir1 C12 151.2(2) . . ? N1 Ir1 C12 122.5(2) . . ? C13 Ir1 C12 38.2(2) . . ? C14 Ir1 C12 63.2(2) . . ? C10 Ir1 C12 63.5(2) . . ? C1 Ir1 C11 149.9(2) . . ? N1 Ir1 C11 99.1(2) . . ? C13 Ir1 C11 63.4(2) . . ? C14 Ir1 C11 63.2(2) . . ? C10 Ir1 C11 38.1(2) . . ? C12 Ir1 C11 37.0(2) . . ? C1 Ir1 Cl1 89.26(16) . . ? N1 Ir1 Cl1 87.26(14) . . ? C13 Ir1 Cl1 94.6(2) . . ? C14 Ir1 Cl1 129.5(2) . . ? C10 Ir1 Cl1 154.40(17) . . ? C12 Ir1 Cl1 90.96(17) . . ? C11 Ir1 Cl1 120.47(15) . . ? C32 N1 C9 117.8(5) . . ? C32 N1 Ir1 117.9(4) . . ? C9 N1 Ir1 124.3(4) . . ? C2 C1 C20 117.1(6) . . ? C2 C1 Ir1 125.2(5) . . ? C20 C1 Ir1 117.6(4) . . ? C1 C2 C3 126.4(6) . . ? C1 C2 C26 121.0(6) . . ? C3 C2 C26 112.4(5) . . ? C4 C3 C8 118.1(6) . . ? C4 C3 C2 118.3(5) . . ? C8 C3 C2 123.5(5) . . ? C5 C4 C3 122.3(6) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C6 C5 C4 118.6(5) . . ? C6 C5 H5A 120.7 . . ? C4 C5 H5A 120.7 . . ? C7 C6 C5 120.2(6) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C8 122.0(6) . . ? C6 C7 H7A 119.0 . . ? C8 C7 H7A 119.0 . . ? C7 C8 C3 118.7(5) . . ? C7 C8 C9 116.5(5) . . ? C3 C8 C9 124.3(6) . . ? N1 C9 C29 120.6(5) . . ? N1 C9 C8 123.2(5) . . ? C29 C9 C8 116.0(5) . . ? C14 C10 C11 107.2(5) . . ? C14 C10 C15 126.9(6) . . ? C11 C10 C15 123.8(6) . . ? C14 C10 Ir1 70.4(3) . . ? C11 C10 Ir1 73.8(3) . . ? C15 C10 Ir1 134.1(5) . . ? C12 C11 C10 108.0(5) . . ? C12 C11 C16 126.3(6) . . ? C10 C11 C16 125.7(6) . . ? C12 C11 Ir1 71.3(4) . . ? C10 C11 Ir1 68.0(3) . . ? C16 C11 Ir1 127.2(4) . . ? C11 C12 C13 107.5(5) . . ? C11 C12 C17 126.8(6) . . ? C13 C12 C17 125.7(6) . . ? C11 C12 Ir1 71.6(3) . . ? C13 C12 Ir1 67.5(4) . . ? C17 C12 Ir1 126.8(5) . . ? C14 C13 C12 108.1(6) . . ? C14 C13 C18 129.7(6) . . ? C12 C13 C18 121.6(7) . . ? C14 C13 Ir1 71.2(4) . . ? C12 C13 Ir1 74.3(4) . . ? C18 C13 Ir1 127.0(5) . . ? C13 C14 C10 108.9(5) . . ? C13 C14 C19 128.3(7) . . ? C10 C14 C19 122.7(7) . . ? C13 C14 Ir1 70.6(4) . . ? C10 C14 Ir1 71.1(3) . . ? C19 C14 Ir1 127.4(5) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 118.8(6) . . ? C21 C20 C1 121.5(6) . . ? C25 C20 C1 119.7(6) . . ? C20 C21 C22 119.7(7) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? C23 C22 C21 121.5(7) . . ? C23 C22 H22A 119.3 . . ? C21 C22 H22A 119.3 . . ? C24 C23 C22 118.8(7) . . ? C24 C23 H23A 120.6 . . ? C22 C23 H23A 120.6 . . ? C23 C24 C25 120.6(7) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C20 C25 C24 120.6(7) . . ? C20 C25 H25A 119.7 . . ? C24 C25 H25A 119.7 . . ? O1 C26 O2 122.6(6) . . ? O1 C26 C2 125.8(6) . . ? O2 C26 C2 111.5(6) . . ? C26 O2 C27 116.9(6) . . ? O2 C27 C28 112.0(7) . . ? O2 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? O2 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C9 120.9(6) . . ? C30 C29 H29A 119.6 . . ? C9 C29 H29A 119.6 . . ? C29 C30 C31 117.4(6) . . ? C29 C30 H30A 121.3 . . ? C31 C30 H30A 121.3 . . ? C32 C31 C30 119.3(6) . . ? C32 C31 H31A 120.3 . . ? C30 C31 H31A 120.3 . . ? N1 C32 C31 123.9(6) . . ? N1 C32 H32A 118.1 . . ? C31 C32 H32A 118.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C32 124.5(5) . . . . ? C13 Ir1 N1 C32 -61.0(9) . . . . ? C14 Ir1 N1 C32 -142.1(5) . . . . ? C10 Ir1 N1 C32 -123.6(4) . . . . ? C12 Ir1 N1 C32 -54.3(5) . . . . ? C11 Ir1 N1 C32 -85.3(5) . . . . ? Cl1 Ir1 N1 C32 35.1(4) . . . . ? C1 Ir1 N1 C9 -54.2(5) . . . . ? C13 Ir1 N1 C9 120.2(7) . . . . ? C14 Ir1 N1 C9 39.2(7) . . . . ? C10 Ir1 N1 C9 57.6(5) . . . . ? C12 Ir1 N1 C9 126.9(5) . . . . ? C11 Ir1 N1 C9 95.9(5) . . . . ? Cl1 Ir1 N1 C9 -143.7(5) . . . . ? N1 Ir1 C1 C2 62.5(5) . . . . ? C13 Ir1 C1 C2 -115.5(5) . . . . ? C14 Ir1 C1 C2 -80.6(5) . . . . ? C10 Ir1 C1 C2 -44.9(6) . . . . ? C12 Ir1 C1 C2 -119.5(6) . . . . ? C11 Ir1 C1 C2 -39.1(7) . . . . ? Cl1 Ir1 C1 C2 149.8(5) . . . . ? N1 Ir1 C1 C20 -118.8(4) . . . . ? C13 Ir1 C1 C20 63.2(5) . . . . ? C14 Ir1 C1 C20 98.1(4) . . . . ? C10 Ir1 C1 C20 133.8(4) . . . . ? C12 Ir1 C1 C20 59.2(7) . . . . ? C11 Ir1 C1 C20 139.5(5) . . . . ? Cl1 Ir1 C1 C20 -31.5(4) . . . . ? C20 C1 C2 C3 177.6(5) . . . . ? Ir1 C1 C2 C3 -3.7(9) . . . . ? C20 C1 C2 C26 -7.2(8) . . . . ? Ir1 C1 C2 C26 171.5(4) . . . . ? C1 C2 C3 C4 136.8(6) . . . . ? C26 C2 C3 C4 -38.8(8) . . . . ? C1 C2 C3 C8 -47.0(9) . . . . ? C26 C2 C3 C8 137.5(6) . . . . ? C8 C3 C4 C5 3.4(9) . . . . ? C2 C3 C4 C5 179.8(6) . . . . ? C3 C4 C5 C6 -3.0(9) . . . . ? C4 C5 C6 C7 1.3(9) . . . . ? C5 C6 C7 C8 -0.1(9) . . . . ? C6 C7 C8 C3 0.5(9) . . . . ? C6 C7 C8 C9 -172.2(6) . . . . ? C4 C3 C8 C7 -2.1(9) . . . . ? C2 C3 C8 C7 -178.3(6) . . . . ? C4 C3 C8 C9 170.1(5) . . . . ? C2 C3 C8 C9 -6.2(10) . . . . ? C32 N1 C9 C29 -4.0(9) . . . . ? Ir1 N1 C9 C29 174.8(4) . . . . ? C32 N1 C9 C8 170.1(6) . . . . ? Ir1 N1 C9 C8 -11.1(8) . . . . ? C7 C8 C9 N1 -126.4(7) . . . . ? C3 C8 C9 N1 61.3(9) . . . . ? C7 C8 C9 C29 47.9(8) . . . . ? C3 C8 C9 C29 -124.3(7) . . . . ? C1 Ir1 C10 C14 -69.2(4) . . . . ? N1 Ir1 C10 C14 -162.3(4) . . . . ? C13 Ir1 C10 C14 36.8(4) . . . . ? C12 Ir1 C10 C14 79.5(4) . . . . ? C11 Ir1 C10 C14 115.5(5) . . . . ? Cl1 Ir1 C10 C14 74.7(6) . . . . ? C1 Ir1 C10 C11 175.3(3) . . . . ? N1 Ir1 C10 C11 82.2(4) . . . . ? C13 Ir1 C10 C11 -78.7(4) . . . . ? C14 Ir1 C10 C11 -115.5(5) . . . . ? C12 Ir1 C10 C11 -36.0(3) . . . . ? Cl1 Ir1 C10 C11 -40.8(6) . . . . ? C1 Ir1 C10 C15 53.6(7) . . . . ? N1 Ir1 C10 C15 -39.5(7) . . . . ? C13 Ir1 C10 C15 159.6(8) . . . . ? C14 Ir1 C10 C15 122.8(8) . . . . ? C12 Ir1 C10 C15 -157.7(8) . . . . ? C11 Ir1 C10 C15 -121.7(8) . . . . ? Cl1 Ir1 C10 C15 -162.4(5) . . . . ? C14 C10 C11 C12 -2.5(7) . . . . ? C15 C10 C11 C12 -167.0(6) . . . . ? Ir1 C10 C11 C12 60.4(4) . . . . ? C14 C10 C11 C16 176.3(6) . . . . ? C15 C10 C11 C16 11.8(10) . . . . ? Ir1 C10 C11 C16 -120.8(6) . . . . ? C14 C10 C11 Ir1 -62.9(4) . . . . ? C15 C10 C11 Ir1 132.6(6) . . . . ? C1 Ir1 C11 C12 -128.0(5) . . . . ? N1 Ir1 C11 C12 133.8(4) . . . . ? C13 Ir1 C11 C12 -37.4(4) . . . . ? C14 Ir1 C11 C12 -80.3(4) . . . . ? C10 Ir1 C11 C12 -119.3(5) . . . . ? Cl1 Ir1 C11 C12 41.6(4) . . . . ? C1 Ir1 C11 C10 -8.7(6) . . . . ? N1 Ir1 C11 C10 -106.9(4) . . . . ? C13 Ir1 C11 C10 81.9(4) . . . . ? C14 Ir1 C11 C10 39.0(4) . . . . ? C12 Ir1 C11 C10 119.3(5) . . . . ? Cl1 Ir1 C11 C10 160.9(3) . . . . ? C1 Ir1 C11 C16 110.2(6) . . . . ? N1 Ir1 C11 C16 11.9(6) . . . . ? C13 Ir1 C11 C16 -159.2(6) . . . . ? C14 Ir1 C11 C16 157.9(6) . . . . ? C10 Ir1 C11 C16 118.9(7) . . . . ? C12 Ir1 C11 C16 -121.9(7) . . . . ? Cl1 Ir1 C11 C16 -80.2(5) . . . . ? C10 C11 C12 C13 -0.1(7) . . . . ? C16 C11 C12 C13 -178.9(6) . . . . ? Ir1 C11 C12 C13 58.2(4) . . . . ? C10 C11 C12 C17 179.0(6) . . . . ? C16 C11 C12 C17 0.2(11) . . . . ? Ir1 C11 C12 C17 -122.7(7) . . . . ? C10 C11 C12 Ir1 -58.3(4) . . . . ? C16 C11 C12 Ir1 122.9(6) . . . . ? C1 Ir1 C12 C11 124.7(5) . . . . ? N1 Ir1 C12 C11 -57.7(4) . . . . ? C13 Ir1 C12 C11 118.7(5) . . . . ? C14 Ir1 C12 C11 80.2(4) . . . . ? C10 Ir1 C12 C11 37.0(4) . . . . ? Cl1 Ir1 C12 C11 -145.1(3) . . . . ? C1 Ir1 C12 C13 6.0(7) . . . . ? N1 Ir1 C12 C13 -176.4(4) . . . . ? C14 Ir1 C12 C13 -38.5(4) . . . . ? C10 Ir1 C12 C13 -81.7(4) . . . . ? C11 Ir1 C12 C13 -118.7(5) . . . . ? Cl1 Ir1 C12 C13 96.2(4) . . . . ? C1 Ir1 C12 C17 -112.6(7) . . . . ? N1 Ir1 C12 C17 64.9(7) . . . . ? C13 Ir1 C12 C17 -118.7(8) . . . . ? C14 Ir1 C12 C17 -157.1(7) . . . . ? C10 Ir1 C12 C17 159.7(7) . . . . ? C11 Ir1 C12 C17 122.6(8) . . . . ? Cl1 Ir1 C12 C17 -22.4(6) . . . . ? C11 C12 C13 C14 2.8(7) . . . . ? C17 C12 C13 C14 -176.3(6) . . . . ? Ir1 C12 C13 C14 63.6(5) . . . . ? C11 C12 C13 C18 175.1(6) . . . . ? C17 C12 C13 C18 -4.0(11) . . . . ? Ir1 C12 C13 C18 -124.1(7) . . . . ? C11 C12 C13 Ir1 -60.8(4) . . . . ? C17 C12 C13 Ir1 120.1(7) . . . . ? C1 Ir1 C13 C14 67.2(4) . . . . ? N1 Ir1 C13 C14 -106.8(7) . . . . ? C10 Ir1 C13 C14 -37.1(4) . . . . ? C12 Ir1 C13 C14 -115.9(6) . . . . ? C11 Ir1 C13 C14 -79.7(4) . . . . ? Cl1 Ir1 C13 C14 158.4(4) . . . . ? C1 Ir1 C13 C12 -176.8(4) . . . . ? N1 Ir1 C13 C12 9.2(9) . . . . ? C14 Ir1 C13 C12 115.9(6) . . . . ? C10 Ir1 C13 C12 78.9(4) . . . . ? C11 Ir1 C13 C12 36.2(4) . . . . ? Cl1 Ir1 C13 C12 -85.7(4) . . . . ? C1 Ir1 C13 C18 -58.8(7) . . . . ? N1 Ir1 C13 C18 127.2(7) . . . . ? C14 Ir1 C13 C18 -126.1(8) . . . . ? C10 Ir1 C13 C18 -163.1(7) . . . . ? C12 Ir1 C13 C18 118.0(8) . . . . ? C11 Ir1 C13 C18 154.2(7) . . . . ? Cl1 Ir1 C13 C18 32.3(7) . . . . ? C12 C13 C14 C10 -4.5(7) . . . . ? C18 C13 C14 C10 -175.9(7) . . . . ? Ir1 C13 C14 C10 61.1(4) . . . . ? C12 C13 C14 C19 171.6(7) . . . . ? C18 C13 C14 C19 0.1(12) . . . . ? Ir1 C13 C14 C19 -122.8(7) . . . . ? C12 C13 C14 Ir1 -65.6(5) . . . . ? C18 C13 C14 Ir1 122.9(8) . . . . ? C11 C10 C14 C13 4.3(7) . . . . ? C15 C10 C14 C13 168.2(6) . . . . ? Ir1 C10 C14 C13 -60.8(5) . . . . ? C11 C10 C14 C19 -172.0(6) . . . . ? C15 C10 C14 C19 -8.1(10) . . . . ? Ir1 C10 C14 C19 122.9(7) . . . . ? C11 C10 C14 Ir1 65.2(4) . . . . ? C15 C10 C14 Ir1 -131.0(6) . . . . ? C1 Ir1 C14 C13 -121.6(4) . . . . ? N1 Ir1 C14 C13 147.9(4) . . . . ? C10 Ir1 C14 C13 118.9(5) . . . . ? C12 Ir1 C14 C13 38.6(4) . . . . ? C11 Ir1 C14 C13 80.3(4) . . . . ? Cl1 Ir1 C14 C13 -28.4(5) . . . . ? C1 Ir1 C14 C10 119.5(4) . . . . ? N1 Ir1 C14 C10 29.0(6) . . . . ? C13 Ir1 C14 C10 -118.9(5) . . . . ? C12 Ir1 C14 C10 -80.3(4) . . . . ? C11 Ir1 C14 C10 -38.7(3) . . . . ? Cl1 Ir1 C14 C10 -147.3(3) . . . . ? C1 Ir1 C14 C19 2.3(8) . . . . ? N1 Ir1 C14 C19 -88.2(8) . . . . ? C13 Ir1 C14 C19 123.9(9) . . . . ? C10 Ir1 C14 C19 -117.2(9) . . . . ? C12 Ir1 C14 C19 162.5(8) . . . . ? C11 Ir1 C14 C19 -155.8(8) . . . . ? Cl1 Ir1 C14 C19 95.5(8) . . . . ? C2 C1 C20 C21 112.9(7) . . . . ? Ir1 C1 C20 C21 -65.8(7) . . . . ? C2 C1 C20 C25 -66.6(8) . . . . ? Ir1 C1 C20 C25 114.7(6) . . . . ? C25 C20 C21 C22 1.6(10) . . . . ? C1 C20 C21 C22 -177.9(6) . . . . ? C20 C21 C22 C23 -2.6(12) . . . . ? C21 C22 C23 C24 0.7(13) . . . . ? C22 C23 C24 C25 2.2(14) . . . . ? C21 C20 C25 C24 1.3(11) . . . . ? C1 C20 C25 C24 -179.2(7) . . . . ? C23 C24 C25 C20 -3.2(13) . . . . ? C1 C2 C26 O1 117.1(7) . . . . ? C3 C2 C26 O1 -67.1(8) . . . . ? C1 C2 C26 O2 -65.9(7) . . . . ? C3 C2 C26 O2 109.9(6) . . . . ? O1 C26 O2 C27 -5.5(10) . . . . ? C2 C26 O2 C27 177.4(6) . . . . ? C26 O2 C27 C28 -74.7(8) . . . . ? N1 C9 C29 C30 0.0(10) . . . . ? C8 C9 C29 C30 -174.5(6) . . . . ? C9 C29 C30 C31 3.9(10) . . . . ? C29 C30 C31 C32 -3.8(10) . . . . ? C9 N1 C32 C31 4.2(9) . . . . ? Ir1 N1 C32 C31 -174.7(5) . . . . ? C30 C31 C32 N1 -0.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 6.823 _refine_diff_density_min -1.753 _refine_diff_density_rms 0.231 _vrf_PLAT601_jonll67 ; PROBLEM: _A Structure Contains Solvent Accessible VOIDS of 256.00 A**3. RESPONSE: The reflection contributions from highly disordered co-crystallized solvent (dichloromethane and/or pentane) were removed using program PLATON, function SQUEEZE (Spek, 2003), which determined there to be 304 electrons in 513 A**3 removed per unit cell. Since the exact identity of the solvent is unknown, it was not included in the molecular formula or atom list. Thus values calculated from the molecular formula are known to be incorrect (e.g., F(000), density, etc.). ; _vrf_DIFMX01_jonll67 ; PROBLEM: _C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 6.823 RESPONSE: Two large residual peaks of electron density of 6.82 and 3.19 electrons per A**3 were found at distances of 2.47 and 2.56 A, respectively, from the iridium atom. No chemical meaning could be assigned to either, even with the consideration of possible disorder models. Although twinning seems the most likely cause, no systematic trends were found. ; _vrf_DIFMX02_jonll67 ; PROBLEM: _C The maximum difference density is > 0.1*ZMAX*0.75 RESPONSE: See above. ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_1'i _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll35b _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Cl F3 Ir N O2' _chemical_formula_sum 'C24 H28 Cl F3 Ir N O2' _chemical_formula_weight 647.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 26.006(6) _cell_length_b 13.287(3) _cell_length_c 14.461(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4997(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3947 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 33.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 5.493 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2793 _exptl_absorpt_correction_T_max 0.3363 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 86498 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 32.58 _reflns_number_total 9083 _reflns_number_gt 7323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0195P)^2^+2.4196P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9083 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.327253(3) 0.807809(6) 0.293794(6) 0.01188(3) Uani 1 1 d . . . Cl1 Cl 0.26175(2) 0.68147(4) 0.26458(4) 0.01819(11) Uani 1 1 d . . . N1 N 0.28309(7) 0.90604(15) 0.21245(13) 0.0147(4) Uani 1 1 d . . . C1 C 0.36462(9) 0.76629(17) 0.17356(16) 0.0151(4) Uani 1 1 d . . . C2 C 0.38678(9) 0.83011(17) 0.11265(16) 0.0148(4) Uani 1 1 d . . . C3 C 0.39359(9) 0.94052(17) 0.12628(15) 0.0143(4) Uani 1 1 d . . . C4 C 0.44288(9) 0.98093(18) 0.11121(16) 0.0178(5) Uani 1 1 d . . . H4 H 0.4705 0.9369 0.0969 0.021 Uiso 1 1 calc R . . C5 C 0.45203(10) 1.08410(19) 0.11673(18) 0.0218(5) Uani 1 1 d . . . H5 H 0.4858 1.1095 0.1076 0.026 Uiso 1 1 calc R . . C6 C 0.41205(10) 1.14940(18) 0.13553(17) 0.0209(5) Uani 1 1 d . . . H6 H 0.4181 1.2198 0.1386 0.025 Uiso 1 1 calc R . . C7 C 0.36314(10) 1.11148(18) 0.14989(16) 0.0176(4) Uani 1 1 d . . . H7 H 0.3355 1.1564 0.1619 0.021 Uiso 1 1 calc R . . C8 C 0.35381(9) 1.00728(17) 0.14697(15) 0.0147(4) Uani 1 1 d . . . C9 C 0.29980(9) 0.98012(17) 0.16429(15) 0.0151(4) Uani 1 1 d . . . H9 H 0.2745 1.0221 0.1367 0.018 Uiso 1 1 calc R . . C10 C 0.37710(9) 0.89999(18) 0.37781(16) 0.0164(4) Uani 1 1 d . . . C11 C 0.32592(9) 0.90589(18) 0.41774(16) 0.0160(4) Uani 1 1 d . . . C12 C 0.31064(10) 0.80862(18) 0.44598(16) 0.0174(4) Uani 1 1 d . . . C13 C 0.35239(9) 0.73928(17) 0.42265(16) 0.0166(4) Uani 1 1 d . . . C14 C 0.39372(9) 0.79659(17) 0.38433(17) 0.0160(4) Uani 1 1 d . . . C15 C 0.41080(10) 0.9880(2) 0.35564(18) 0.0232(5) Uani 1 1 d . . . H15A H 0.4286 1.0102 0.4118 0.035 Uiso 1 1 calc R . . H15B H 0.3897 1.0432 0.3316 0.035 Uiso 1 1 calc R . . H15C H 0.4362 0.9683 0.3090 0.035 Uiso 1 1 calc R . . C16 C 0.29552(11) 1.00121(19) 0.42611(18) 0.0233(5) Uani 1 1 d . . . H16A H 0.3118 1.0454 0.4718 0.035 Uiso 1 1 calc R . . H16B H 0.2604 0.9853 0.4460 0.035 Uiso 1 1 calc R . . H16C H 0.2945 1.0352 0.3660 0.035 Uiso 1 1 calc R . . C17 C 0.26063(10) 0.7780(2) 0.48888(18) 0.0244(5) Uani 1 1 d . . . H17A H 0.2651 0.7710 0.5559 0.037 Uiso 1 1 calc R . . H17B H 0.2495 0.7136 0.4627 0.037 Uiso 1 1 calc R . . H17C H 0.2346 0.8295 0.4761 0.037 Uiso 1 1 calc R . . C18 C 0.35228(12) 0.62988(19) 0.44596(19) 0.0264(6) Uani 1 1 d . . . H18A H 0.3535 0.6216 0.5133 0.040 Uiso 1 1 calc R . . H18B H 0.3824 0.5975 0.4181 0.040 Uiso 1 1 calc R . . H18C H 0.3209 0.5987 0.4218 0.040 Uiso 1 1 calc R . . C19 C 0.44567(10) 0.7586(2) 0.3580(2) 0.0257(6) Uani 1 1 d . . . H19A H 0.4693 0.7671 0.4101 0.039 Uiso 1 1 calc R . . H19B H 0.4584 0.7967 0.3047 0.039 Uiso 1 1 calc R . . H19C H 0.4434 0.6871 0.3418 0.039 Uiso 1 1 calc R . . C20 C 0.36982(10) 0.65536(19) 0.15256(17) 0.0187(5) Uani 1 1 d . . . F1 F 0.41262(6) 0.63133(11) 0.10371(11) 0.0255(3) Uani 1 1 d . . . F2 F 0.37317(6) 0.59856(11) 0.22964(10) 0.0220(3) Uani 1 1 d . . . F3 F 0.33038(6) 0.61672(11) 0.10278(10) 0.0229(3) Uani 1 1 d . . . C21 C 0.40675(9) 0.79679(17) 0.01880(16) 0.0159(4) Uani 1 1 d . . . O1 O 0.45089(7) 0.79750(13) -0.00712(12) 0.0199(4) Uani 1 1 d . . . O2 O 0.36643(7) 0.77135(13) -0.03474(12) 0.0186(3) Uani 1 1 d . . . C22 C 0.37763(11) 0.7358(2) -0.12779(17) 0.0231(5) Uani 1 1 d . . . H22A H 0.4098 0.7672 -0.1505 0.028 Uiso 1 1 calc R . . H22B H 0.3493 0.7549 -0.1701 0.028 Uiso 1 1 calc R . . C23 C 0.38348(13) 0.6229(2) -0.1263(2) 0.0350(7) Uani 1 1 d . . . H23A H 0.3878 0.5980 -0.1896 0.052 Uiso 1 1 calc R . . H23C H 0.3527 0.5925 -0.0989 0.052 Uiso 1 1 calc R . . H23D H 0.4137 0.6048 -0.0894 0.052 Uiso 1 1 calc R . . C24 C 0.22679(9) 0.9020(2) 0.22290(18) 0.0203(5) Uani 1 1 d . . . H24C H 0.2114 0.9621 0.1950 0.030 Uiso 1 1 calc R . . H24D H 0.2180 0.8994 0.2887 0.030 Uiso 1 1 calc R . . H24A H 0.2135 0.8418 0.1919 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01239(4) 0.01202(4) 0.01123(4) 0.00095(3) -0.00031(3) -0.00098(3) Cl1 0.0185(3) 0.0176(3) 0.0185(3) 0.0001(2) -0.0006(2) -0.0052(2) N1 0.0132(9) 0.0171(9) 0.0138(9) -0.0009(7) 0.0003(7) -0.0004(7) C1 0.0167(11) 0.0136(10) 0.0151(10) -0.0001(8) -0.0002(9) 0.0008(8) C2 0.0136(10) 0.0151(10) 0.0156(10) -0.0006(8) -0.0024(8) -0.0010(8) C3 0.0155(10) 0.0155(10) 0.0118(10) 0.0002(8) 0.0001(8) -0.0010(8) C4 0.0162(11) 0.0204(11) 0.0169(11) -0.0002(9) 0.0005(9) -0.0009(9) C5 0.0218(12) 0.0231(12) 0.0206(12) 0.0019(10) 0.0007(10) -0.0086(10) C6 0.0294(13) 0.0132(11) 0.0201(12) 0.0007(9) -0.0004(10) -0.0057(9) C7 0.0218(12) 0.0150(10) 0.0159(11) -0.0003(8) -0.0006(9) 0.0000(9) C8 0.0148(10) 0.0171(10) 0.0121(10) 0.0024(8) -0.0001(8) -0.0028(8) C9 0.0176(11) 0.0156(10) 0.0121(10) 0.0000(8) -0.0016(8) 0.0011(8) C10 0.0177(11) 0.0183(11) 0.0132(10) -0.0007(9) -0.0028(9) -0.0034(8) C11 0.0170(11) 0.0187(11) 0.0121(10) -0.0001(8) -0.0034(8) 0.0004(9) C12 0.0190(11) 0.0194(11) 0.0137(10) -0.0007(9) 0.0009(9) -0.0014(9) C13 0.0201(12) 0.0136(10) 0.0162(11) 0.0010(8) -0.0043(9) 0.0008(9) C14 0.0163(10) 0.0175(11) 0.0144(10) -0.0026(8) -0.0036(9) -0.0008(8) C15 0.0283(13) 0.0235(13) 0.0179(12) -0.0002(10) -0.0023(10) -0.0090(10) C16 0.0274(13) 0.0226(12) 0.0199(12) -0.0052(10) -0.0056(10) 0.0069(10) C17 0.0195(12) 0.0360(14) 0.0178(12) 0.0014(11) 0.0038(10) -0.0056(11) C18 0.0353(16) 0.0189(12) 0.0249(14) 0.0050(10) -0.0064(12) -0.0016(11) C19 0.0174(12) 0.0295(14) 0.0302(15) -0.0062(11) -0.0042(10) 0.0034(10) C20 0.0224(12) 0.0166(11) 0.0171(11) 0.0018(9) 0.0023(9) 0.0008(9) F1 0.0306(9) 0.0192(7) 0.0268(8) 0.0031(6) 0.0106(7) 0.0079(6) F2 0.0316(8) 0.0153(7) 0.0191(7) 0.0048(5) 0.0018(6) 0.0029(6) F3 0.0323(9) 0.0172(7) 0.0192(7) -0.0012(6) -0.0023(6) -0.0046(6) C21 0.0184(11) 0.0135(10) 0.0158(11) 0.0012(8) -0.0005(9) -0.0004(8) O1 0.0161(8) 0.0242(9) 0.0194(9) -0.0006(7) 0.0025(7) 0.0005(7) O2 0.0197(9) 0.0207(8) 0.0155(8) -0.0018(7) -0.0025(7) -0.0021(7) C22 0.0320(14) 0.0229(12) 0.0145(11) -0.0041(10) -0.0010(10) -0.0014(10) C23 0.0470(19) 0.0271(15) 0.0309(16) -0.0123(12) -0.0070(14) 0.0022(13) C24 0.0122(10) 0.0240(12) 0.0246(13) 0.0030(10) 0.0015(9) 0.0011(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.067(2) . ? Ir1 N1 2.0991(19) . ? Ir1 C10 2.158(2) . ? Ir1 C14 2.174(2) . ? Ir1 C13 2.175(2) . ? Ir1 C11 2.216(2) . ? Ir1 C12 2.243(2) . ? Ir1 Cl1 2.4286(7) . ? N1 C9 1.282(3) . ? N1 C24 1.473(3) . ? C1 C2 1.352(3) . ? C1 C20 1.511(3) . ? C2 C3 1.491(3) . ? C2 C21 1.519(3) . ? C3 C8 1.395(3) . ? C3 C4 1.407(3) . ? C4 C5 1.394(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(4) . ? C5 H5 0.9500 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.406(3) . ? C7 H7 0.9500 . ? C8 C9 1.472(3) . ? C9 H9 0.9500 . ? C10 C14 1.443(3) . ? C10 C11 1.453(3) . ? C10 C15 1.496(3) . ? C11 C12 1.412(3) . ? C11 C16 1.498(3) . ? C12 C13 1.463(3) . ? C12 C17 1.497(3) . ? C13 C14 1.429(3) . ? C13 C18 1.492(3) . ? C14 C19 1.492(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 F2 1.349(3) . ? C20 F3 1.354(3) . ? C20 F1 1.356(3) . ? C21 O1 1.208(3) . ? C21 O2 1.347(3) . ? O2 C22 1.456(3) . ? C22 C23 1.507(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23C 0.9800 . ? C23 H23D 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 87.23(8) . . ? C1 Ir1 C10 110.04(9) . . ? N1 Ir1 C10 106.93(8) . . ? C1 Ir1 C14 96.58(9) . . ? N1 Ir1 C14 144.62(8) . . ? C10 Ir1 C14 38.93(8) . . ? C1 Ir1 C13 117.89(9) . . ? N1 Ir1 C13 154.83(8) . . ? C10 Ir1 C13 64.82(9) . . ? C14 Ir1 C13 38.37(9) . . ? C1 Ir1 C11 147.63(9) . . ? N1 Ir1 C11 94.53(8) . . ? C10 Ir1 C11 38.77(9) . . ? C14 Ir1 C11 64.26(9) . . ? C13 Ir1 C11 63.76(9) . . ? C1 Ir1 C12 156.54(9) . . ? N1 Ir1 C12 116.20(8) . . ? C10 Ir1 C12 63.92(9) . . ? C14 Ir1 C12 64.05(9) . . ? C13 Ir1 C12 38.65(9) . . ? C11 Ir1 C12 36.92(9) . . ? C1 Ir1 Cl1 89.94(7) . . ? N1 Ir1 Cl1 87.05(6) . . ? C10 Ir1 Cl1 155.73(6) . . ? C14 Ir1 Cl1 127.97(6) . . ? C13 Ir1 Cl1 94.04(7) . . ? C11 Ir1 Cl1 122.42(6) . . ? C12 Ir1 Cl1 92.23(6) . . ? C9 N1 C24 114.9(2) . . ? C9 N1 Ir1 126.63(16) . . ? C24 N1 Ir1 117.63(15) . . ? C2 C1 C20 116.3(2) . . ? C2 C1 Ir1 125.54(18) . . ? C20 C1 Ir1 118.14(16) . . ? C1 C2 C3 125.6(2) . . ? C1 C2 C21 123.0(2) . . ? C3 C2 C21 111.37(19) . . ? C8 C3 C4 117.8(2) . . ? C8 C3 C2 124.5(2) . . ? C4 C3 C2 117.6(2) . . ? C5 C4 C3 121.5(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 119.5(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 120.8(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 120.3(2) . . ? C3 C8 C9 126.0(2) . . ? C7 C8 C9 113.6(2) . . ? N1 C9 C8 127.2(2) . . ? N1 C9 H9 116.4 . . ? C8 C9 H9 116.4 . . ? C14 C10 C11 107.4(2) . . ? C14 C10 C15 125.6(2) . . ? C11 C10 C15 125.4(2) . . ? C14 C10 Ir1 71.12(13) . . ? C11 C10 Ir1 72.79(13) . . ? C15 C10 Ir1 132.45(17) . . ? C12 C11 C10 108.9(2) . . ? C12 C11 C16 127.0(2) . . ? C10 C11 C16 124.1(2) . . ? C12 C11 Ir1 72.56(14) . . ? C10 C11 Ir1 68.44(13) . . ? C16 C11 Ir1 124.80(16) . . ? C11 C12 C13 107.5(2) . . ? C11 C12 C17 127.8(2) . . ? C13 C12 C17 124.7(2) . . ? C11 C12 Ir1 70.52(13) . . ? C13 C12 Ir1 68.15(13) . . ? C17 C12 Ir1 124.93(18) . . ? C14 C13 C12 108.2(2) . . ? C14 C13 C18 127.5(2) . . ? C12 C13 C18 124.0(2) . . ? C14 C13 Ir1 70.78(13) . . ? C12 C13 Ir1 73.20(13) . . ? C18 C13 Ir1 126.93(17) . . ? C13 C14 C10 107.9(2) . . ? C13 C14 C19 126.9(2) . . ? C10 C14 C19 125.2(2) . . ? C13 C14 Ir1 70.85(13) . . ? C10 C14 Ir1 69.95(13) . . ? C19 C14 Ir1 126.13(17) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F2 C20 F3 106.02(19) . . ? F2 C20 F1 104.22(19) . . ? F3 C20 F1 104.80(19) . . ? F2 C20 C1 112.7(2) . . ? F3 C20 C1 114.1(2) . . ? F1 C20 C1 114.1(2) . . ? O1 C21 O2 124.3(2) . . ? O1 C21 C2 126.9(2) . . ? O2 C21 C2 108.7(2) . . ? C21 O2 C22 117.21(19) . . ? O2 C22 C23 109.3(2) . . ? O2 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? O2 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? C22 C23 H23D 109.5 . . ? H23A C23 H23D 109.5 . . ? H23C C23 H23D 109.5 . . ? N1 C24 H24C 109.5 . . ? N1 C24 H24D 109.5 . . ? H24C C24 H24D 109.5 . . ? N1 C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? H24D C24 H24A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C9 -61.5(2) . . . . ? C10 Ir1 N1 C9 48.6(2) . . . . ? C14 Ir1 N1 C9 36.0(3) . . . . ? C13 Ir1 N1 C9 115.2(2) . . . . ? C11 Ir1 N1 C9 86.1(2) . . . . ? C12 Ir1 N1 C9 117.4(2) . . . . ? Cl1 Ir1 N1 C9 -151.6(2) . . . . ? C1 Ir1 N1 C24 129.79(17) . . . . ? C10 Ir1 N1 C24 -120.09(17) . . . . ? C14 Ir1 N1 C24 -132.74(18) . . . . ? C13 Ir1 N1 C24 -53.5(3) . . . . ? C11 Ir1 N1 C24 -82.60(17) . . . . ? C12 Ir1 N1 C24 -51.33(19) . . . . ? Cl1 Ir1 N1 C24 39.71(16) . . . . ? N1 Ir1 C1 C2 52.6(2) . . . . ? C10 Ir1 C1 C2 -54.4(2) . . . . ? C14 Ir1 C1 C2 -92.1(2) . . . . ? C13 Ir1 C1 C2 -125.8(2) . . . . ? C11 Ir1 C1 C2 -41.5(3) . . . . ? C12 Ir1 C1 C2 -124.9(2) . . . . ? Cl1 Ir1 C1 C2 139.6(2) . . . . ? N1 Ir1 C1 C20 -129.96(18) . . . . ? C10 Ir1 C1 C20 123.01(18) . . . . ? C14 Ir1 C1 C20 85.34(18) . . . . ? C13 Ir1 C1 C20 51.6(2) . . . . ? C11 Ir1 C1 C20 135.94(18) . . . . ? C12 Ir1 C1 C20 52.6(3) . . . . ? Cl1 Ir1 C1 C20 -42.91(17) . . . . ? C20 C1 C2 C3 -170.0(2) . . . . ? Ir1 C1 C2 C3 7.5(3) . . . . ? C20 C1 C2 C21 11.8(3) . . . . ? Ir1 C1 C2 C21 -170.72(17) . . . . ? C1 C2 C3 C8 -54.8(3) . . . . ? C21 C2 C3 C8 123.5(2) . . . . ? C1 C2 C3 C4 129.6(3) . . . . ? C21 C2 C3 C4 -52.0(3) . . . . ? C8 C3 C4 C5 0.1(3) . . . . ? C2 C3 C4 C5 176.0(2) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C4 C3 C8 C7 1.7(3) . . . . ? C2 C3 C8 C7 -173.9(2) . . . . ? C4 C3 C8 C9 179.5(2) . . . . ? C2 C3 C8 C9 4.0(4) . . . . ? C6 C7 C8 C3 -2.2(4) . . . . ? C6 C7 C8 C9 179.6(2) . . . . ? C24 N1 C9 C8 175.8(2) . . . . ? Ir1 N1 C9 C8 6.8(3) . . . . ? C3 C8 C9 N1 42.4(4) . . . . ? C7 C8 C9 N1 -139.6(2) . . . . ? C1 Ir1 C10 C14 -75.07(15) . . . . ? N1 Ir1 C10 C14 -168.36(13) . . . . ? C13 Ir1 C10 C14 37.18(14) . . . . ? C11 Ir1 C10 C14 115.95(19) . . . . ? C12 Ir1 C10 C14 80.24(15) . . . . ? Cl1 Ir1 C10 C14 68.7(2) . . . . ? C1 Ir1 C10 C11 168.98(13) . . . . ? N1 Ir1 C10 C11 75.69(14) . . . . ? C14 Ir1 C10 C11 -115.95(19) . . . . ? C13 Ir1 C10 C11 -78.77(15) . . . . ? C12 Ir1 C10 C11 -35.71(13) . . . . ? Cl1 Ir1 C10 C11 -47.3(2) . . . . ? C1 Ir1 C10 C15 46.4(3) . . . . ? N1 Ir1 C10 C15 -46.9(3) . . . . ? C14 Ir1 C10 C15 121.5(3) . . . . ? C13 Ir1 C10 C15 158.6(3) . . . . ? C11 Ir1 C10 C15 -122.6(3) . . . . ? C12 Ir1 C10 C15 -158.3(3) . . . . ? Cl1 Ir1 C10 C15 -169.88(16) . . . . ? C14 C10 C11 C12 -1.5(3) . . . . ? C15 C10 C11 C12 -168.1(2) . . . . ? Ir1 C10 C11 C12 61.61(17) . . . . ? C14 C10 C11 C16 178.6(2) . . . . ? C15 C10 C11 C16 12.0(4) . . . . ? Ir1 C10 C11 C16 -118.3(2) . . . . ? C14 C10 C11 Ir1 -63.11(16) . . . . ? C15 C10 C11 Ir1 130.3(2) . . . . ? C1 Ir1 C11 C12 -138.83(17) . . . . ? N1 Ir1 C11 C12 129.18(14) . . . . ? C10 Ir1 C11 C12 -119.2(2) . . . . ? C14 Ir1 C11 C12 -80.39(15) . . . . ? C13 Ir1 C11 C12 -37.50(14) . . . . ? Cl1 Ir1 C11 C12 39.80(15) . . . . ? C1 Ir1 C11 C10 -19.6(2) . . . . ? N1 Ir1 C11 C10 -111.58(14) . . . . ? C14 Ir1 C11 C10 38.85(13) . . . . ? C13 Ir1 C11 C10 81.74(15) . . . . ? C12 Ir1 C11 C10 119.2(2) . . . . ? Cl1 Ir1 C11 C10 159.04(11) . . . . ? C1 Ir1 C11 C16 97.8(2) . . . . ? N1 Ir1 C11 C16 5.8(2) . . . . ? C10 Ir1 C11 C16 117.4(3) . . . . ? C14 Ir1 C11 C16 156.2(2) . . . . ? C13 Ir1 C11 C16 -160.9(2) . . . . ? C12 Ir1 C11 C16 -123.4(3) . . . . ? Cl1 Ir1 C11 C16 -83.6(2) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C16 C11 C12 C13 179.1(2) . . . . ? Ir1 C11 C12 C13 58.29(16) . . . . ? C10 C11 C12 C17 -178.7(2) . . . . ? C16 C11 C12 C17 1.2(4) . . . . ? Ir1 C11 C12 C17 -119.6(3) . . . . ? C10 C11 C12 Ir1 -59.05(16) . . . . ? C16 C11 C12 Ir1 120.8(2) . . . . ? C1 Ir1 C12 C11 117.7(2) . . . . ? N1 Ir1 C12 C11 -59.45(16) . . . . ? C10 Ir1 C12 C11 37.47(13) . . . . ? C14 Ir1 C12 C11 81.00(15) . . . . ? C13 Ir1 C12 C11 119.1(2) . . . . ? Cl1 Ir1 C12 C11 -147.26(13) . . . . ? C1 Ir1 C12 C13 -1.3(3) . . . . ? N1 Ir1 C12 C13 -178.51(13) . . . . ? C10 Ir1 C12 C13 -81.58(15) . . . . ? C14 Ir1 C12 C13 -38.05(13) . . . . ? C11 Ir1 C12 C13 -119.1(2) . . . . ? Cl1 Ir1 C12 C13 93.68(13) . . . . ? C1 Ir1 C12 C17 -119.2(3) . . . . ? N1 Ir1 C12 C17 63.6(2) . . . . ? C10 Ir1 C12 C17 160.5(2) . . . . ? C14 Ir1 C12 C17 -156.0(2) . . . . ? C13 Ir1 C12 C17 -117.9(3) . . . . ? C11 Ir1 C12 C17 123.0(3) . . . . ? Cl1 Ir1 C12 C17 -24.2(2) . . . . ? C11 C12 C13 C14 2.8(3) . . . . ? C17 C12 C13 C14 -179.3(2) . . . . ? Ir1 C12 C13 C14 62.54(16) . . . . ? C11 C12 C13 C18 176.6(2) . . . . ? C17 C12 C13 C18 -5.4(4) . . . . ? Ir1 C12 C13 C18 -123.6(2) . . . . ? C11 C12 C13 Ir1 -59.78(17) . . . . ? C17 C12 C13 Ir1 118.2(2) . . . . ? C1 Ir1 C13 C14 62.64(16) . . . . ? N1 Ir1 C13 C14 -113.6(2) . . . . ? C10 Ir1 C13 C14 -37.72(13) . . . . ? C11 Ir1 C13 C14 -80.93(14) . . . . ? C12 Ir1 C13 C14 -116.77(19) . . . . ? Cl1 Ir1 C13 C14 154.71(12) . . . . ? C1 Ir1 C13 C12 179.41(13) . . . . ? N1 Ir1 C13 C12 3.2(3) . . . . ? C10 Ir1 C13 C12 79.05(15) . . . . ? C14 Ir1 C13 C12 116.77(19) . . . . ? C11 Ir1 C13 C12 35.84(13) . . . . ? Cl1 Ir1 C13 C12 -88.52(13) . . . . ? C1 Ir1 C13 C18 -60.3(2) . . . . ? N1 Ir1 C13 C18 123.5(2) . . . . ? C10 Ir1 C13 C18 -160.6(3) . . . . ? C14 Ir1 C13 C18 -122.9(3) . . . . ? C11 Ir1 C13 C18 156.1(3) . . . . ? C12 Ir1 C13 C18 120.3(3) . . . . ? Cl1 Ir1 C13 C18 31.8(2) . . . . ? C12 C13 C14 C10 -3.7(3) . . . . ? C18 C13 C14 C10 -177.3(2) . . . . ? Ir1 C13 C14 C10 60.43(16) . . . . ? C12 C13 C14 C19 174.6(2) . . . . ? C18 C13 C14 C19 1.0(4) . . . . ? Ir1 C13 C14 C19 -121.3(2) . . . . ? C12 C13 C14 Ir1 -64.11(16) . . . . ? C18 C13 C14 Ir1 122.3(3) . . . . ? C11 C10 C14 C13 3.2(3) . . . . ? C15 C10 C14 C13 169.8(2) . . . . ? Ir1 C10 C14 C13 -61.00(16) . . . . ? C11 C10 C14 C19 -175.1(2) . . . . ? C15 C10 C14 C19 -8.5(4) . . . . ? Ir1 C10 C14 C19 120.7(2) . . . . ? C11 C10 C14 Ir1 64.20(16) . . . . ? C15 C10 C14 Ir1 -129.2(2) . . . . ? C1 Ir1 C14 C13 -127.80(14) . . . . ? N1 Ir1 C14 C13 137.70(15) . . . . ? C10 Ir1 C14 C13 118.2(2) . . . . ? C11 Ir1 C14 C13 79.53(15) . . . . ? C12 Ir1 C14 C13 38.33(14) . . . . ? Cl1 Ir1 C14 C13 -32.72(16) . . . . ? C1 Ir1 C14 C10 113.97(14) . . . . ? N1 Ir1 C14 C10 19.5(2) . . . . ? C13 Ir1 C14 C10 -118.2(2) . . . . ? C11 Ir1 C14 C10 -38.69(13) . . . . ? C12 Ir1 C14 C10 -79.89(14) . . . . ? Cl1 Ir1 C14 C10 -150.94(11) . . . . ? C1 Ir1 C14 C19 -5.6(2) . . . . ? N1 Ir1 C14 C19 -100.1(2) . . . . ? C10 Ir1 C14 C19 -119.6(3) . . . . ? C13 Ir1 C14 C19 122.2(3) . . . . ? C11 Ir1 C14 C19 -158.3(2) . . . . ? C12 Ir1 C14 C19 160.5(2) . . . . ? Cl1 Ir1 C14 C19 89.5(2) . . . . ? C2 C1 C20 F2 146.7(2) . . . . ? Ir1 C1 C20 F2 -31.0(3) . . . . ? C2 C1 C20 F3 -92.3(3) . . . . ? Ir1 C1 C20 F3 90.0(2) . . . . ? C2 C1 C20 F1 28.1(3) . . . . ? Ir1 C1 C20 F1 -149.60(17) . . . . ? C1 C2 C21 O1 -115.2(3) . . . . ? C3 C2 C21 O1 66.4(3) . . . . ? C1 C2 C21 O2 68.6(3) . . . . ? C3 C2 C21 O2 -109.8(2) . . . . ? O1 C21 O2 C22 4.5(3) . . . . ? C2 C21 O2 C22 -179.18(19) . . . . ? C21 O2 C22 C23 90.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.216 _refine_diff_density_min -1.007 _refine_diff_density_rms 0.131 _vrf_PLAT601_jonll35 ; PROBLEM: _A Structure Contains Solvent Accessible VOIDS of 303.00 A**3. RESPONSE: Highly disordered solvent (dichloromethane, pentane, or both) was found in channels parallel to the c-axis. Reflection contributions from this solvent were removed using program PLATON, function SQUEEZE (Spek, 2003), which determined there to be 99 electrons in 607 A**3 removed per unit cell. The unknown solvent is not included in the chemical formula, so calculations deriving from that (density, F(000), etc.) are known to be incorrect. ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_2'i _publ_contact_author_name 'William D. Jones' _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll36b _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Cl F3 N O2 Rh' _chemical_formula_sum 'C24 H28 Cl F3 N O2 Rh' _chemical_formula_weight 557.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Rh' 'Rh' -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 25.927(6) _cell_length_b 13.338(3) _cell_length_c 14.438(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4992.8(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 3752 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 33.02 _exptl_crystal_description plate _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 0.833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7316 _exptl_absorpt_correction_T_max 0.9517 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 86131 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 32.58 _reflns_number_total 9077 _reflns_number_gt 7302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0049P)^2^+14.4397P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9077 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.326353(7) 0.806345(14) 0.291543(13) 0.01438(5) Uani 1 1 d . . . Cl1 Cl 0.26056(2) 0.68029(5) 0.26426(4) 0.02046(12) Uani 1 1 d . . . N1 N 0.28278(8) 0.90654(16) 0.21074(16) 0.0173(4) Uani 1 1 d . . . C1 C 0.36483(10) 0.76592(19) 0.17255(18) 0.0170(4) Uani 1 1 d . . . C2 C 0.38684(10) 0.82956(19) 0.11192(17) 0.0163(4) Uani 1 1 d . . . C3 C 0.39375(10) 0.93947(19) 0.12558(17) 0.0163(4) Uani 1 1 d . . . C4 C 0.44347(10) 0.9795(2) 0.11073(18) 0.0191(5) Uani 1 1 d . . . H4 H 0.4711 0.9352 0.0968 0.023 Uiso 1 1 calc R . . C5 C 0.45306(11) 1.0820(2) 0.11594(19) 0.0229(5) Uani 1 1 d . . . H5 H 0.4870 1.1068 0.1069 0.028 Uiso 1 1 calc R . . C6 C 0.41292(12) 1.1478(2) 0.1344(2) 0.0239(5) Uani 1 1 d . . . H6 H 0.4192 1.2178 0.1376 0.029 Uiso 1 1 calc R . . C7 C 0.36369(11) 1.1105(2) 0.14806(19) 0.0208(5) Uani 1 1 d . . . H7 H 0.3361 1.1558 0.1591 0.025 Uiso 1 1 calc R . . C8 C 0.35379(10) 1.00687(19) 0.14591(17) 0.0170(5) Uani 1 1 d . . . C9 C 0.29964(10) 0.98087(19) 0.16361(17) 0.0170(5) Uani 1 1 d . . . H9 H 0.2744 1.0239 0.1372 0.020 Uiso 1 1 calc R . . C10 C 0.37592(10) 0.89819(19) 0.37645(17) 0.0185(5) Uani 1 1 d . . . C11 C 0.32476(11) 0.9026(2) 0.41724(17) 0.0188(5) Uani 1 1 d . . . C12 C 0.31025(10) 0.8055(2) 0.44383(17) 0.0188(5) Uani 1 1 d . . . C13 C 0.35230(11) 0.7374(2) 0.41959(18) 0.0197(5) Uani 1 1 d . . . C14 C 0.39313(10) 0.7956(2) 0.38153(18) 0.0197(5) Uani 1 1 d . . . C15 C 0.40892(12) 0.9867(2) 0.35509(19) 0.0250(6) Uani 1 1 d . . . H15A H 0.4261 1.0094 0.4118 0.038 Uiso 1 1 calc R . . H15B H 0.3874 1.0410 0.3305 0.038 Uiso 1 1 calc R . . H15C H 0.4349 0.9680 0.3089 0.038 Uiso 1 1 calc R . . C16 C 0.29400(12) 0.9966(2) 0.4270(2) 0.0255(6) Uani 1 1 d . . . H16A H 0.3114 1.0420 0.4703 0.038 Uiso 1 1 calc R . . H16B H 0.2596 0.9803 0.4507 0.038 Uiso 1 1 calc R . . H16C H 0.2908 1.0293 0.3665 0.038 Uiso 1 1 calc R . . C17 C 0.26068(12) 0.7732(3) 0.4875(2) 0.0286(6) Uani 1 1 d . . . H17A H 0.2654 0.7669 0.5546 0.043 Uiso 1 1 calc R . . H17B H 0.2502 0.7083 0.4618 0.043 Uiso 1 1 calc R . . H17C H 0.2339 0.8232 0.4748 0.043 Uiso 1 1 calc R . . C18 C 0.35287(13) 0.6280(2) 0.4415(2) 0.0293(6) Uani 1 1 d . . . H18A H 0.3547 0.6187 0.5087 0.044 Uiso 1 1 calc R . . H18B H 0.3830 0.5967 0.4123 0.044 Uiso 1 1 calc R . . H18C H 0.3213 0.5967 0.4177 0.044 Uiso 1 1 calc R . . C19 C 0.44571(11) 0.7593(2) 0.3556(2) 0.0282(6) Uani 1 1 d . . . H19A H 0.4689 0.7657 0.4089 0.042 Uiso 1 1 calc R . . H19B H 0.4590 0.7995 0.3041 0.042 Uiso 1 1 calc R . . H19C H 0.4438 0.6888 0.3367 0.042 Uiso 1 1 calc R . . C20 C 0.36933(11) 0.6554(2) 0.15156(19) 0.0208(5) Uani 1 1 d . . . F1 F 0.41248(7) 0.63124(13) 0.10269(12) 0.0284(4) Uani 1 1 d . . . F2 F 0.37265(7) 0.59864(12) 0.22892(11) 0.0246(3) Uani 1 1 d . . . F3 F 0.33004(7) 0.61729(12) 0.10126(12) 0.0259(3) Uani 1 1 d . . . C21 C 0.40703(10) 0.79690(18) 0.01776(17) 0.0167(4) Uani 1 1 d . . . O1 O 0.45131(7) 0.79693(15) -0.00781(14) 0.0233(4) Uani 1 1 d . . . O2 O 0.36675(8) 0.77222(14) -0.03627(13) 0.0212(4) Uani 1 1 d . . . C22 C 0.37819(13) 0.7378(2) -0.1295(2) 0.0265(6) Uani 1 1 d . . . H22A H 0.4100 0.7707 -0.1523 0.032 Uiso 1 1 calc R . . H22B H 0.3495 0.7559 -0.1715 0.032 Uiso 1 1 calc R . . C23 C 0.38545(18) 0.6256(3) -0.1291(3) 0.0453(10) Uani 1 1 d . . . H23A H 0.3910 0.6020 -0.1926 0.068 Uiso 1 1 calc R . . H23C H 0.3546 0.5934 -0.1034 0.068 Uiso 1 1 calc R . . H23D H 0.4154 0.6084 -0.0909 0.068 Uiso 1 1 calc R . . C24 C 0.22644(10) 0.9026(2) 0.22250(19) 0.0218(5) Uani 1 1 d . . . H24C H 0.2108 0.9618 0.1938 0.033 Uiso 1 1 calc R . . H24D H 0.2181 0.9013 0.2887 0.033 Uiso 1 1 calc R . . H24A H 0.2130 0.8419 0.1928 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01486(8) 0.01387(8) 0.01442(8) 0.00255(7) -0.00039(7) -0.00091(7) Cl1 0.0205(3) 0.0184(3) 0.0225(3) 0.0010(2) -0.0004(2) -0.0049(2) N1 0.0155(9) 0.0180(9) 0.0185(9) -0.0007(8) -0.0015(8) -0.0002(7) C1 0.0160(11) 0.0160(11) 0.0189(11) 0.0014(9) -0.0022(9) 0.0013(9) C2 0.0164(11) 0.0168(11) 0.0157(11) 0.0005(8) -0.0015(8) 0.0015(8) C3 0.0172(11) 0.0173(11) 0.0144(10) 0.0005(8) 0.0001(9) -0.0017(9) C4 0.0188(12) 0.0207(12) 0.0179(11) -0.0007(9) 0.0006(9) -0.0028(9) C5 0.0229(13) 0.0237(13) 0.0222(13) 0.0026(10) 0.0013(10) -0.0071(10) C6 0.0317(15) 0.0156(12) 0.0244(13) -0.0007(10) 0.0016(11) -0.0051(10) C7 0.0252(13) 0.0165(11) 0.0208(12) 0.0030(9) 0.0007(10) 0.0009(10) C8 0.0183(11) 0.0184(11) 0.0145(11) 0.0012(9) -0.0011(9) -0.0031(9) C9 0.0177(11) 0.0174(11) 0.0160(11) 0.0012(9) -0.0006(9) 0.0021(9) C10 0.0218(12) 0.0189(11) 0.0148(11) 0.0005(9) -0.0019(9) -0.0021(9) C11 0.0222(12) 0.0209(12) 0.0134(10) 0.0009(9) -0.0038(9) 0.0007(10) C12 0.0217(11) 0.0222(12) 0.0127(10) 0.0025(9) 0.0023(8) -0.0023(10) C13 0.0235(13) 0.0185(12) 0.0170(11) 0.0029(9) -0.0051(10) -0.0006(10) C14 0.0191(11) 0.0214(12) 0.0187(11) 0.0001(9) -0.0056(9) -0.0004(10) C15 0.0319(15) 0.0239(13) 0.0193(12) 0.0003(10) -0.0050(11) -0.0084(11) C16 0.0294(14) 0.0260(14) 0.0209(12) -0.0018(11) -0.0020(11) 0.0070(11) C17 0.0263(14) 0.0375(16) 0.0221(13) 0.0035(12) 0.0024(11) -0.0040(12) C18 0.0370(17) 0.0209(13) 0.0298(15) 0.0080(11) -0.0081(13) -0.0015(12) C19 0.0189(13) 0.0323(15) 0.0334(16) -0.0033(12) -0.0025(11) 0.0038(11) C20 0.0235(13) 0.0176(11) 0.0212(12) 0.0044(10) 0.0017(10) -0.0016(10) F1 0.0334(9) 0.0207(8) 0.0312(9) 0.0028(7) 0.0117(7) 0.0085(7) F2 0.0338(9) 0.0173(7) 0.0227(8) 0.0060(6) 0.0019(7) 0.0034(6) F3 0.0357(9) 0.0178(7) 0.0244(8) -0.0003(6) -0.0037(7) -0.0050(7) C21 0.0189(11) 0.0140(10) 0.0173(11) 0.0019(9) 0.0005(9) -0.0004(9) O1 0.0203(9) 0.0265(10) 0.0231(9) -0.0017(8) 0.0032(7) -0.0007(8) O2 0.0240(9) 0.0200(9) 0.0196(9) -0.0014(7) -0.0018(7) -0.0025(7) C22 0.0355(16) 0.0234(13) 0.0205(13) -0.0043(11) -0.0038(11) 0.0000(12) C23 0.070(3) 0.0272(16) 0.0385(19) -0.0125(15) -0.0192(19) 0.0060(17) C24 0.0170(11) 0.0248(13) 0.0236(13) 0.0015(10) 0.0006(10) -0.0001(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C1 2.058(3) . ? Rh1 N1 2.103(2) . ? Rh1 C10 2.158(3) . ? Rh1 C14 2.169(3) . ? Rh1 C13 2.171(3) . ? Rh1 C11 2.224(3) . ? Rh1 C12 2.238(2) . ? Rh1 Cl1 2.4274(7) . ? N1 C9 1.279(3) . ? N1 C24 1.472(3) . ? C1 C2 1.346(4) . ? C1 C20 1.510(4) . ? C2 C3 1.490(3) . ? C2 C21 1.521(4) . ? C3 C8 1.403(4) . ? C3 C4 1.411(3) . ? C4 C5 1.392(4) . ? C4 H4 0.9500 . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 C7 1.384(4) . ? C6 H6 0.9500 . ? C7 C8 1.407(4) . ? C7 H7 0.9500 . ? C8 C9 1.468(3) . ? C9 H9 0.9500 . ? C10 C14 1.441(4) . ? C10 C11 1.452(4) . ? C10 C15 1.491(4) . ? C11 C12 1.403(4) . ? C11 C16 1.493(4) . ? C12 C13 1.461(4) . ? C12 C17 1.495(4) . ? C13 C14 1.423(4) . ? C13 C18 1.494(4) . ? C14 C19 1.494(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 F3 1.350(3) . ? C20 F2 1.352(3) . ? C20 F1 1.361(3) . ? C21 O1 1.206(3) . ? C21 O2 1.345(3) . ? O2 C22 1.452(3) . ? C22 C23 1.508(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23C 0.9800 . ? C23 H23D 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Rh1 N1 87.93(9) . . ? C1 Rh1 C10 109.53(10) . . ? N1 Rh1 C10 105.92(9) . . ? C1 Rh1 C14 95.49(10) . . ? N1 Rh1 C14 143.41(9) . . ? C10 Rh1 C14 38.92(10) . . ? C1 Rh1 C13 116.71(10) . . ? N1 Rh1 C13 155.18(10) . . ? C10 Rh1 C13 64.67(10) . . ? C14 Rh1 C13 38.27(10) . . ? C1 Rh1 C11 147.29(10) . . ? N1 Rh1 C11 94.34(9) . . ? C10 Rh1 C11 38.69(10) . . ? C14 Rh1 C11 64.17(10) . . ? C13 Rh1 C11 63.60(10) . . ? C1 Rh1 C12 155.36(10) . . ? N1 Rh1 C12 116.62(9) . . ? C10 Rh1 C12 63.64(10) . . ? C14 Rh1 C12 63.91(10) . . ? C13 Rh1 C12 38.66(10) . . ? C11 Rh1 C12 36.66(9) . . ? C1 Rh1 Cl1 91.36(7) . . ? N1 Rh1 Cl1 88.44(6) . . ? C10 Rh1 Cl1 154.70(7) . . ? C14 Rh1 Cl1 127.75(7) . . ? C13 Rh1 Cl1 93.59(7) . . ? C11 Rh1 Cl1 121.30(7) . . ? C12 Rh1 Cl1 91.41(7) . . ? C9 N1 C24 115.4(2) . . ? C9 N1 Rh1 127.15(18) . . ? C24 N1 Rh1 116.51(17) . . ? C2 C1 C20 116.9(2) . . ? C2 C1 Rh1 125.65(19) . . ? C20 C1 Rh1 117.44(18) . . ? C1 C2 C3 125.8(2) . . ? C1 C2 C21 123.1(2) . . ? C3 C2 C21 111.0(2) . . ? C8 C3 C4 117.7(2) . . ? C8 C3 C2 124.7(2) . . ? C4 C3 C2 117.5(2) . . ? C5 C4 C3 121.7(3) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C3 C8 C7 120.0(2) . . ? C3 C8 C9 126.2(2) . . ? C7 C8 C9 113.7(2) . . ? N1 C9 C8 127.0(2) . . ? N1 C9 H9 116.5 . . ? C8 C9 H9 116.5 . . ? C14 C10 C11 107.5(2) . . ? C14 C10 C15 125.8(2) . . ? C11 C10 C15 125.2(2) . . ? C14 C10 Rh1 70.99(14) . . ? C11 C10 Rh1 73.12(15) . . ? C15 C10 Rh1 132.40(19) . . ? C12 C11 C10 108.6(2) . . ? C12 C11 C16 127.3(3) . . ? C10 C11 C16 124.1(2) . . ? C12 C11 Rh1 72.23(15) . . ? C10 C11 Rh1 68.20(14) . . ? C16 C11 Rh1 124.91(18) . . ? C11 C12 C13 107.9(2) . . ? C11 C12 C17 127.7(3) . . ? C13 C12 C17 124.3(3) . . ? C11 C12 Rh1 71.11(14) . . ? C13 C12 Rh1 68.20(14) . . ? C17 C12 Rh1 125.21(19) . . ? C14 C13 C12 108.0(2) . . ? C14 C13 C18 127.4(3) . . ? C12 C13 C18 124.3(3) . . ? C14 C13 Rh1 70.79(15) . . ? C12 C13 Rh1 73.14(14) . . ? C18 C13 Rh1 126.65(19) . . ? C13 C14 C10 107.9(2) . . ? C13 C14 C19 126.8(3) . . ? C10 C14 C19 125.3(2) . . ? C13 C14 Rh1 70.94(15) . . ? C10 C14 Rh1 70.10(14) . . ? C19 C14 Rh1 126.8(2) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F3 C20 F2 106.4(2) . . ? F3 C20 F1 104.6(2) . . ? F2 C20 F1 104.1(2) . . ? F3 C20 C1 114.7(2) . . ? F2 C20 C1 112.7(2) . . ? F1 C20 C1 113.5(2) . . ? O1 C21 O2 124.2(2) . . ? O1 C21 C2 127.0(2) . . ? O2 C21 C2 108.7(2) . . ? C21 O2 C22 117.1(2) . . ? O2 C22 C23 109.6(3) . . ? O2 C22 H22A 109.7 . . ? C23 C22 H22A 109.7 . . ? O2 C22 H22B 109.7 . . ? C23 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? C22 C23 H23D 109.5 . . ? H23A C23 H23D 109.5 . . ? H23C C23 H23D 109.5 . . ? N1 C24 H24C 109.5 . . ? N1 C24 H24D 109.5 . . ? H24C C24 H24D 109.5 . . ? N1 C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? H24D C24 H24A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 N1 C9 -61.1(2) . . . . ? C10 Rh1 N1 C9 48.6(2) . . . . ? C14 Rh1 N1 C9 35.3(3) . . . . ? C13 Rh1 N1 C9 112.3(3) . . . . ? C11 Rh1 N1 C9 86.2(2) . . . . ? C12 Rh1 N1 C9 116.7(2) . . . . ? Cl1 Rh1 N1 C9 -152.5(2) . . . . ? C1 Rh1 N1 C24 130.78(19) . . . . ? C10 Rh1 N1 C24 -119.50(19) . . . . ? C14 Rh1 N1 C24 -132.8(2) . . . . ? C13 Rh1 N1 C24 -55.8(3) . . . . ? C11 Rh1 N1 C24 -81.91(19) . . . . ? C12 Rh1 N1 C24 -51.4(2) . . . . ? Cl1 Rh1 N1 C24 39.36(18) . . . . ? N1 Rh1 C1 C2 50.9(2) . . . . ? C10 Rh1 C1 C2 -55.3(2) . . . . ? C14 Rh1 C1 C2 -92.6(2) . . . . ? C13 Rh1 C1 C2 -126.1(2) . . . . ? C11 Rh1 C1 C2 -44.0(3) . . . . ? C12 Rh1 C1 C2 -124.4(3) . . . . ? Cl1 Rh1 C1 C2 139.2(2) . . . . ? N1 Rh1 C1 C20 -129.8(2) . . . . ? C10 Rh1 C1 C20 124.07(19) . . . . ? C14 Rh1 C1 C20 86.7(2) . . . . ? C13 Rh1 C1 C20 53.3(2) . . . . ? C11 Rh1 C1 C20 135.4(2) . . . . ? C12 Rh1 C1 C20 55.0(3) . . . . ? Cl1 Rh1 C1 C20 -41.39(19) . . . . ? C20 C1 C2 C3 -170.6(2) . . . . ? Rh1 C1 C2 C3 8.8(4) . . . . ? C20 C1 C2 C21 10.9(4) . . . . ? Rh1 C1 C2 C21 -169.71(18) . . . . ? C1 C2 C3 C8 -55.4(4) . . . . ? C21 C2 C3 C8 123.3(3) . . . . ? C1 C2 C3 C4 129.1(3) . . . . ? C21 C2 C3 C4 -52.2(3) . . . . ? C8 C3 C4 C5 0.1(4) . . . . ? C2 C3 C4 C5 175.8(2) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C8 1.6(4) . . . . ? C4 C3 C8 C7 2.0(4) . . . . ? C2 C3 C8 C7 -173.5(2) . . . . ? C4 C3 C8 C9 -180.0(2) . . . . ? C2 C3 C8 C9 4.6(4) . . . . ? C6 C7 C8 C3 -2.9(4) . . . . ? C6 C7 C8 C9 178.8(2) . . . . ? C24 N1 C9 C8 176.0(2) . . . . ? Rh1 N1 C9 C8 7.8(4) . . . . ? C3 C8 C9 N1 40.6(4) . . . . ? C7 C8 C9 N1 -141.2(3) . . . . ? C1 Rh1 C10 C14 -73.88(17) . . . . ? N1 Rh1 C10 C14 -167.39(15) . . . . ? C13 Rh1 C10 C14 37.21(15) . . . . ? C11 Rh1 C10 C14 115.9(2) . . . . ? C12 Rh1 C10 C14 80.35(16) . . . . ? Cl1 Rh1 C10 C14 70.1(2) . . . . ? C1 Rh1 C10 C11 170.20(14) . . . . ? N1 Rh1 C10 C11 76.69(15) . . . . ? C14 Rh1 C10 C11 -115.9(2) . . . . ? C13 Rh1 C10 C11 -78.71(16) . . . . ? C12 Rh1 C10 C11 -35.56(14) . . . . ? Cl1 Rh1 C10 C11 -45.8(2) . . . . ? C1 Rh1 C10 C15 47.7(3) . . . . ? N1 Rh1 C10 C15 -45.8(3) . . . . ? C14 Rh1 C10 C15 121.6(3) . . . . ? C13 Rh1 C10 C15 158.8(3) . . . . ? C11 Rh1 C10 C15 -122.5(3) . . . . ? C12 Rh1 C10 C15 -158.1(3) . . . . ? Cl1 Rh1 C10 C15 -168.31(18) . . . . ? C14 C10 C11 C12 -1.8(3) . . . . ? C15 C10 C11 C12 -168.4(2) . . . . ? Rh1 C10 C11 C12 61.24(18) . . . . ? C14 C10 C11 C16 178.7(2) . . . . ? C15 C10 C11 C16 12.1(4) . . . . ? Rh1 C10 C11 C16 -118.3(2) . . . . ? C14 C10 C11 Rh1 -63.08(17) . . . . ? C15 C10 C11 Rh1 130.4(3) . . . . ? C1 Rh1 C11 C12 -136.48(19) . . . . ? N1 Rh1 C11 C12 130.59(16) . . . . ? C10 Rh1 C11 C12 -119.2(2) . . . . ? C14 Rh1 C11 C12 -80.33(17) . . . . ? C13 Rh1 C11 C12 -37.52(16) . . . . ? Cl1 Rh1 C11 C12 39.78(17) . . . . ? C1 Rh1 C11 C10 -17.3(2) . . . . ? N1 Rh1 C11 C10 -110.19(15) . . . . ? C14 Rh1 C11 C10 38.88(15) . . . . ? C13 Rh1 C11 C10 81.70(16) . . . . ? C12 Rh1 C11 C10 119.2(2) . . . . ? Cl1 Rh1 C11 C10 159.00(12) . . . . ? C1 Rh1 C11 C16 99.9(3) . . . . ? N1 Rh1 C11 C16 7.0(2) . . . . ? C10 Rh1 C11 C16 117.2(3) . . . . ? C14 Rh1 C11 C16 156.1(3) . . . . ? C13 Rh1 C11 C16 -161.1(3) . . . . ? C12 Rh1 C11 C16 -123.6(3) . . . . ? Cl1 Rh1 C11 C16 -83.8(2) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C16 C11 C12 C13 179.2(2) . . . . ? Rh1 C11 C12 C13 58.45(17) . . . . ? C10 C11 C12 C17 -179.1(3) . . . . ? C16 C11 C12 C17 0.4(4) . . . . ? Rh1 C11 C12 C17 -120.4(3) . . . . ? C10 C11 C12 Rh1 -58.73(17) . . . . ? C16 C11 C12 Rh1 120.8(3) . . . . ? C1 Rh1 C12 C11 116.8(3) . . . . ? N1 Rh1 C12 C11 -57.89(17) . . . . ? C10 Rh1 C12 C11 37.50(15) . . . . ? C14 Rh1 C12 C11 81.10(17) . . . . ? C13 Rh1 C12 C11 119.2(2) . . . . ? Cl1 Rh1 C12 C11 -146.85(15) . . . . ? C1 Rh1 C12 C13 -2.4(3) . . . . ? N1 Rh1 C12 C13 -177.05(14) . . . . ? C10 Rh1 C12 C13 -81.66(16) . . . . ? C14 Rh1 C12 C13 -38.07(15) . . . . ? C11 Rh1 C12 C13 -119.2(2) . . . . ? Cl1 Rh1 C12 C13 93.99(15) . . . . ? C1 Rh1 C12 C17 -119.8(3) . . . . ? N1 Rh1 C12 C17 65.5(3) . . . . ? C10 Rh1 C12 C17 160.9(3) . . . . ? C14 Rh1 C12 C17 -155.5(3) . . . . ? C13 Rh1 C12 C17 -117.5(3) . . . . ? C11 Rh1 C12 C17 123.4(3) . . . . ? Cl1 Rh1 C12 C17 -23.5(2) . . . . ? C11 C12 C13 C14 2.3(3) . . . . ? C17 C12 C13 C14 -178.8(2) . . . . ? Rh1 C12 C13 C14 62.60(18) . . . . ? C11 C12 C13 C18 176.5(2) . . . . ? C17 C12 C13 C18 -4.6(4) . . . . ? Rh1 C12 C13 C18 -123.2(3) . . . . ? C11 C12 C13 Rh1 -60.27(18) . . . . ? C17 C12 C13 Rh1 118.6(3) . . . . ? C1 Rh1 C13 C14 62.29(18) . . . . ? N1 Rh1 C13 C14 -110.3(2) . . . . ? C10 Rh1 C13 C14 -37.83(15) . . . . ? C11 Rh1 C13 C14 -81.01(17) . . . . ? C12 Rh1 C13 C14 -116.6(2) . . . . ? Cl1 Rh1 C13 C14 155.62(15) . . . . ? C1 Rh1 C13 C12 178.90(14) . . . . ? N1 Rh1 C13 C12 6.3(3) . . . . ? C10 Rh1 C13 C12 78.78(16) . . . . ? C14 Rh1 C13 C12 116.6(2) . . . . ? C11 Rh1 C13 C12 35.60(15) . . . . ? Cl1 Rh1 C13 C12 -87.77(14) . . . . ? C1 Rh1 C13 C18 -60.5(3) . . . . ? N1 Rh1 C13 C18 126.9(3) . . . . ? C10 Rh1 C13 C18 -160.6(3) . . . . ? C14 Rh1 C13 C18 -122.8(3) . . . . ? C11 Rh1 C13 C18 156.2(3) . . . . ? C12 Rh1 C13 C18 120.6(3) . . . . ? Cl1 Rh1 C13 C18 32.8(3) . . . . ? C12 C13 C14 C10 -3.5(3) . . . . ? C18 C13 C14 C10 -177.4(3) . . . . ? Rh1 C13 C14 C10 60.67(18) . . . . ? C12 C13 C14 C19 173.6(3) . . . . ? C18 C13 C14 C19 -0.3(5) . . . . ? Rh1 C13 C14 C19 -122.2(3) . . . . ? C12 C13 C14 Rh1 -64.13(18) . . . . ? C18 C13 C14 Rh1 122.0(3) . . . . ? C11 C10 C14 C13 3.3(3) . . . . ? C15 C10 C14 C13 169.7(2) . . . . ? Rh1 C10 C14 C13 -61.21(18) . . . . ? C11 C10 C14 C19 -173.9(2) . . . . ? C15 C10 C14 C19 -7.5(4) . . . . ? Rh1 C10 C14 C19 121.6(3) . . . . ? C11 C10 C14 Rh1 64.48(17) . . . . ? C15 C10 C14 Rh1 -129.1(3) . . . . ? C1 Rh1 C14 C13 -127.40(16) . . . . ? N1 Rh1 C14 C13 138.68(17) . . . . ? C10 Rh1 C14 C13 118.1(2) . . . . ? C11 Rh1 C14 C13 79.40(17) . . . . ? C12 Rh1 C14 C13 38.46(16) . . . . ? Cl1 Rh1 C14 C13 -31.40(19) . . . . ? C1 Rh1 C14 C10 114.55(16) . . . . ? N1 Rh1 C14 C10 20.6(2) . . . . ? C13 Rh1 C14 C10 -118.1(2) . . . . ? C11 Rh1 C14 C10 -38.65(15) . . . . ? C12 Rh1 C14 C10 -79.60(16) . . . . ? Cl1 Rh1 C14 C10 -149.45(12) . . . . ? C1 Rh1 C14 C19 -5.2(3) . . . . ? N1 Rh1 C14 C19 -99.1(3) . . . . ? C10 Rh1 C14 C19 -119.7(3) . . . . ? C13 Rh1 C14 C19 122.2(3) . . . . ? C11 Rh1 C14 C19 -158.4(3) . . . . ? C12 Rh1 C14 C19 160.7(3) . . . . ? Cl1 Rh1 C14 C19 90.8(2) . . . . ? C2 C1 C20 F3 -91.3(3) . . . . ? Rh1 C1 C20 F3 89.3(2) . . . . ? C2 C1 C20 F2 146.8(2) . . . . ? Rh1 C1 C20 F2 -32.6(3) . . . . ? C2 C1 C20 F1 28.8(3) . . . . ? Rh1 C1 C20 F1 -150.60(18) . . . . ? C1 C2 C21 O1 -114.2(3) . . . . ? C3 C2 C21 O1 67.1(3) . . . . ? C1 C2 C21 O2 69.2(3) . . . . ? C3 C2 C21 O2 -109.6(2) . . . . ? O1 C21 O2 C22 3.9(4) . . . . ? C2 C21 O2 C22 -179.4(2) . . . . ? C21 O2 C22 C23 89.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.877 _refine_diff_density_min -1.508 _refine_diff_density_rms 0.107 _vrf_PLAT601_jonll36 ; PROBLEM: _A Structure Contains Solvent Accessible VOIDS of 299.00 A**3. RESPONSE: Highly disordered solvent (dichloromethane, pentane, or both) was found in channels parallel to the c-axis. Reflection contributions from this solvent were removed using program PLATON, function SQUEEZE (Spek, 2003), which determined there to be 117 electrons in 598 A**3 removed per unit cell. The unknown solvent is not included in the chemical formula, so calculations deriving from that (density, F(000), etc.) are known to be incorrect. ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end data_3'i _publ_contact_author_address 'Department of Chemistry, University of Rochester, Rochester, New York 14627' _publ_contact_author_email 'jones@chem.rochester.edu' _publ_requested_journal 'Organometallics' _publ_section_title ; Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M--C (M = Ir, Rh) Bonds of Cyclometallated Complexes ; loop_ _publ_author_name 'Ling Li' 'Yunzhe Jiao' 'William W. Brennessel' 'William D. Jones*' _publ_author_address ; Department of Chemistry, University of Rochester, Rochester, NY 14627; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common jonll65 _chemical_melting_point ? _chemical_formula_moiety 'C27 H28 Cl F3 Ir N O2, C H Cl3' _chemical_formula_sum 'C28 H29 Cl4 F3 Ir N O2' _chemical_formula_weight 802.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3278(3) _cell_length_b 12.0705(4) _cell_length_c 14.4230(5) _cell_angle_alpha 98.1720(10) _cell_angle_beta 105.6920(10) _cell_angle_gamma 110.0360(10) _cell_volume 1418.40(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 7723 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 37.72 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 5.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4386 _exptl_absorpt_correction_T_max 0.5979 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32868 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 36.32 _reflns_number_total 13473 _reflns_number_gt 11823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13473 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.156567(10) 0.275530(7) 0.288007(6) 0.01345(2) Uani 1 1 d . . . Cl1 Cl -0.01423(8) 0.32481(6) 0.15509(5) 0.02233(11) Uani 1 1 d . . . N1 N 0.1747(2) 0.15700(19) 0.17231(15) 0.0170(3) Uani 1 1 d . . . C1 C -0.0495(3) 0.1328(2) 0.28280(17) 0.0150(4) Uani 1 1 d . . . C2 C -0.0603(3) 0.0207(2) 0.29107(17) 0.0159(4) Uani 1 1 d . . . C3 C 0.0831(3) -0.0130(2) 0.31790(18) 0.0171(4) Uani 1 1 d . . . C4 C 0.1107(3) -0.0614(2) 0.40015(19) 0.0212(4) Uani 1 1 d . . . H4A H 0.0402 -0.0696 0.4378 0.025 Uiso 1 1 calc R . . C5 C 0.2384(3) -0.0976(3) 0.4283(2) 0.0257(5) Uani 1 1 d . . . H5A H 0.2533 -0.1319 0.4837 0.031 Uiso 1 1 calc R . . C6 C 0.3435(4) -0.0839(3) 0.3757(2) 0.0278(6) Uani 1 1 d . . . H6A H 0.4326 -0.1070 0.3954 0.033 Uiso 1 1 calc R . . C7 C 0.3185(3) -0.0362(2) 0.2938(2) 0.0227(5) Uani 1 1 d . . . H7A H 0.3906 -0.0280 0.2571 0.027 Uiso 1 1 calc R . . C8 C 0.1893(3) 0.0003(2) 0.26361(17) 0.0165(4) Uani 1 1 d . . . C9 C 0.1769(3) 0.0457(2) 0.17252(18) 0.0181(4) Uani 1 1 d . . . C10 C 0.3531(3) 0.3128(2) 0.42402(18) 0.0179(4) Uani 1 1 d . . . C11 C 0.4214(3) 0.3773(2) 0.35883(18) 0.0186(4) Uani 1 1 d . . . C12 C 0.3516(3) 0.4620(2) 0.33846(18) 0.0189(4) Uani 1 1 d . . . C13 C 0.2363(3) 0.4509(2) 0.39122(17) 0.0175(4) Uani 1 1 d . . . C14 C 0.2413(3) 0.3619(2) 0.44586(17) 0.0170(4) Uani 1 1 d . . . C15 C 0.4144(3) 0.2312(2) 0.4770(2) 0.0258(5) Uani 1 1 d . . . H15A H 0.5149 0.2811 0.5331 0.039 Uiso 1 1 calc R . . H15B H 0.4359 0.1766 0.4307 0.039 Uiso 1 1 calc R . . H15C H 0.3324 0.1826 0.5020 0.039 Uiso 1 1 calc R . . C16 C 0.5445(3) 0.3532(3) 0.3202(2) 0.0285(6) Uani 1 1 d . . . H16A H 0.6530 0.3978 0.3706 0.043 Uiso 1 1 calc R . . H16B H 0.5415 0.3805 0.2591 0.043 Uiso 1 1 calc R . . H16C H 0.5195 0.2655 0.3056 0.043 Uiso 1 1 calc R . . C17 C 0.3854(4) 0.5453(2) 0.2723(2) 0.0272(5) Uani 1 1 d . . . H17A H 0.4681 0.6257 0.3128 0.041 Uiso 1 1 calc R . . H17B H 0.2854 0.5535 0.2371 0.041 Uiso 1 1 calc R . . H17C H 0.4250 0.5111 0.2236 0.041 Uiso 1 1 calc R . . C18 C 0.1399(3) 0.5274(2) 0.3938(2) 0.0254(5) Uani 1 1 d . . . H18A H 0.2056 0.6036 0.4464 0.038 Uiso 1 1 calc R . . H18B H 0.0416 0.4825 0.4076 0.038 Uiso 1 1 calc R . . H18C H 0.1091 0.5461 0.3292 0.038 Uiso 1 1 calc R . . C19 C 0.1527(3) 0.3271(3) 0.5165(2) 0.0251(5) Uani 1 1 d . . . H19A H 0.2231 0.3750 0.5847 0.038 Uiso 1 1 calc R . . H19B H 0.1229 0.2400 0.5126 0.038 Uiso 1 1 calc R . . H19C H 0.0543 0.3435 0.4987 0.038 Uiso 1 1 calc R . . C20 C -0.2022(3) 0.1567(2) 0.27319(19) 0.0194(4) Uani 1 1 d . . . F1 F -0.30178(18) 0.13101(15) 0.17878(12) 0.0251(3) Uani 1 1 d . . . F2 F -0.29583(19) 0.09156(15) 0.32046(13) 0.0259(3) Uani 1 1 d . . . F3 F -0.16736(19) 0.27375(14) 0.31574(13) 0.0259(3) Uani 1 1 d . . . C21 C -0.2178(3) -0.0837(2) 0.27723(18) 0.0185(4) Uani 1 1 d . . . O1 O -0.2489(2) -0.13614(19) 0.33855(16) 0.0283(4) Uani 1 1 d . . . O2 O -0.3183(2) -0.11294(16) 0.18287(13) 0.0187(3) Uani 1 1 d . . . C22 C -0.4794(3) -0.2081(2) 0.1578(2) 0.0217(4) Uani 1 1 d . . . H22A H -0.5283 -0.1924 0.2086 0.026 Uiso 1 1 calc R . . H22B H -0.4736 -0.2889 0.1546 0.026 Uiso 1 1 calc R . . C23 C -0.5790(3) -0.2051(3) 0.0577(2) 0.0317(6) Uani 1 1 d . . . H23A H -0.6908 -0.2652 0.0390 0.048 Uiso 1 1 calc R . . H23B H -0.5322 -0.2248 0.0076 0.048 Uiso 1 1 calc R . . H23C H -0.5787 -0.1234 0.0611 0.048 Uiso 1 1 calc R . . C24 C 0.1854(3) -0.0249(3) 0.09020(19) 0.0227(5) Uani 1 1 d . . . H24A H 0.1797 -0.1051 0.0898 0.027 Uiso 1 1 calc R . . C25 C 0.2021(3) 0.0206(3) 0.0096(2) 0.0283(6) Uani 1 1 d . . . H25A H 0.2077 -0.0273 -0.0466 0.034 Uiso 1 1 calc R . . C26 C 0.2104(3) 0.1375(3) 0.0125(2) 0.0271(5) Uani 1 1 d . . . H26A H 0.2267 0.1732 -0.0404 0.032 Uiso 1 1 calc R . . C27 C 0.1947(3) 0.2013(3) 0.09358(19) 0.0221(5) Uani 1 1 d . . . H27A H 0.1980 0.2810 0.0942 0.026 Uiso 1 1 calc R . . C28 C 0.8102(10) 0.5402(8) 0.1248(6) 0.0308(14) Uani 0.50 1 d P A 1 H28A H 0.8361 0.4717 0.1454 0.037 Uiso 0.50 1 calc PR A 1 Cl2 Cl 0.8897(3) 0.66442(16) 0.22969(12) 0.0425(4) Uani 0.50 1 d P A 1 Cl3 Cl 0.8976(3) 0.5819(2) 0.03520(18) 0.0485(5) Uani 0.50 1 d P A 1 Cl4 Cl 0.5992(3) 0.4914(2) 0.0744(2) 0.0667(7) Uani 0.50 1 d P A 1 C28' C 0.8786(9) 0.5605(7) 0.1305(6) 0.0289(14) Uani 0.50 1 d P B 5 H28B H 0.8960 0.4868 0.1458 0.035 Uiso 0.50 1 calc PR B 5 Cl4' Cl 1.0663(3) 0.6857(2) 0.1724(2) 0.0724(8) Uani 0.50 1 d P B 5 Cl2' Cl 0.7610(6) 0.5943(5) 0.1937(3) 0.1208(18) Uani 0.50 1 d P B 5 Cl3' Cl 0.7967(5) 0.5352(2) 0.00274(18) 0.0756(9) Uani 0.50 1 d P B 5 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01272(4) 0.01429(4) 0.01339(4) 0.00269(3) 0.00493(3) 0.00547(3) Cl1 0.0235(3) 0.0250(3) 0.0194(2) 0.0073(2) 0.0042(2) 0.0126(2) N1 0.0156(8) 0.0202(9) 0.0152(8) 0.0030(7) 0.0065(7) 0.0070(7) C1 0.0136(8) 0.0168(9) 0.0143(9) 0.0023(7) 0.0051(7) 0.0064(7) C2 0.0139(9) 0.0172(9) 0.0152(9) 0.0028(7) 0.0049(7) 0.0053(7) C3 0.0153(9) 0.0141(9) 0.0180(10) 0.0022(7) 0.0018(7) 0.0050(7) C4 0.0220(11) 0.0181(10) 0.0214(11) 0.0070(8) 0.0059(9) 0.0059(9) C5 0.0262(12) 0.0241(12) 0.0216(12) 0.0078(9) 0.0001(9) 0.0094(10) C6 0.0285(13) 0.0277(13) 0.0264(13) 0.0023(10) 0.0000(10) 0.0192(11) C7 0.0213(11) 0.0256(11) 0.0216(11) 0.0031(9) 0.0046(9) 0.0131(9) C8 0.0170(9) 0.0166(9) 0.0169(9) 0.0023(7) 0.0045(8) 0.0096(8) C9 0.0152(9) 0.0217(10) 0.0166(10) 0.0012(8) 0.0048(8) 0.0084(8) C10 0.0167(9) 0.0164(9) 0.0175(10) 0.0030(8) 0.0026(8) 0.0060(8) C11 0.0142(9) 0.0178(10) 0.0188(10) 0.0008(8) 0.0035(8) 0.0037(8) C12 0.0182(10) 0.0165(9) 0.0188(10) 0.0039(8) 0.0072(8) 0.0030(8) C13 0.0193(10) 0.0165(9) 0.0157(9) 0.0012(7) 0.0054(8) 0.0077(8) C14 0.0171(9) 0.0170(9) 0.0135(9) 0.0014(7) 0.0040(7) 0.0045(8) C15 0.0266(12) 0.0201(11) 0.0218(11) 0.0019(9) -0.0035(9) 0.0096(10) C16 0.0173(11) 0.0320(14) 0.0336(14) 0.0013(11) 0.0099(10) 0.0090(10) C17 0.0305(13) 0.0206(11) 0.0258(13) 0.0091(10) 0.0095(11) 0.0036(10) C18 0.0263(12) 0.0224(11) 0.0275(13) 0.0006(10) 0.0073(10) 0.0134(10) C19 0.0287(12) 0.0269(12) 0.0176(11) 0.0038(9) 0.0112(10) 0.0069(10) C20 0.0144(9) 0.0195(10) 0.0234(11) 0.0018(8) 0.0081(8) 0.0058(8) F1 0.0173(7) 0.0277(8) 0.0271(8) 0.0036(6) 0.0016(6) 0.0113(6) F2 0.0189(7) 0.0290(8) 0.0320(8) 0.0053(7) 0.0154(6) 0.0081(6) F3 0.0192(7) 0.0212(7) 0.0352(9) -0.0021(6) 0.0094(6) 0.0095(6) C21 0.0172(9) 0.0190(10) 0.0183(10) 0.0035(8) 0.0067(8) 0.0061(8) O1 0.0233(9) 0.0310(10) 0.0255(10) 0.0125(8) 0.0093(8) 0.0023(8) O2 0.0147(7) 0.0188(7) 0.0180(8) 0.0030(6) 0.0053(6) 0.0024(6) C22 0.0154(9) 0.0192(10) 0.0267(12) 0.0018(9) 0.0082(9) 0.0032(8) C23 0.0175(11) 0.0355(15) 0.0341(15) 0.0020(12) 0.0027(10) 0.0086(11) C24 0.0228(11) 0.0282(12) 0.0189(11) 0.0004(9) 0.0070(9) 0.0146(10) C25 0.0268(13) 0.0392(15) 0.0189(11) -0.0006(10) 0.0089(10) 0.0155(12) C26 0.0265(12) 0.0411(15) 0.0167(11) 0.0074(10) 0.0109(9) 0.0144(11) C27 0.0223(11) 0.0293(12) 0.0182(10) 0.0073(9) 0.0101(9) 0.0115(10) C28 0.039(4) 0.033(4) 0.026(3) 0.005(3) 0.013(3) 0.022(4) Cl2 0.0635(12) 0.0360(8) 0.0279(7) 0.0017(6) 0.0066(8) 0.0295(8) Cl3 0.0795(15) 0.0540(12) 0.0456(11) 0.0293(10) 0.0412(11) 0.0441(12) Cl4 0.0476(11) 0.0595(13) 0.0757(16) -0.0204(12) 0.0148(11) 0.0211(10) C28' 0.030(3) 0.026(3) 0.032(3) 0.011(2) 0.008(3) 0.015(3) Cl4' 0.0507(12) 0.0352(10) 0.106(2) 0.0212(12) 0.0042(13) 0.0031(9) Cl2' 0.161(4) 0.206(5) 0.144(3) 0.128(4) 0.134(3) 0.153(4) Cl3' 0.124(3) 0.0478(13) 0.0373(11) 0.0088(10) 0.0026(14) 0.0336(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.070(2) . ? Ir1 N1 2.121(2) . ? Ir1 C10 2.157(2) . ? Ir1 C13 2.163(2) . ? Ir1 C14 2.164(2) . ? Ir1 C11 2.203(2) . ? Ir1 C12 2.218(2) . ? Ir1 Cl1 2.4266(6) . ? N1 C9 1.352(3) . ? N1 C27 1.352(3) . ? C1 C2 1.347(3) . ? C1 C20 1.522(3) . ? C2 C3 1.496(3) . ? C2 C21 1.512(3) . ? C3 C4 1.396(3) . ? C3 C8 1.403(3) . ? C4 C5 1.386(4) . ? C4 H4A 0.9500 . ? C5 C6 1.374(4) . ? C5 H5A 0.9500 . ? C6 C7 1.385(4) . ? C6 H6A 0.9500 . ? C7 C8 1.404(3) . ? C7 H7A 0.9500 . ? C8 C9 1.485(3) . ? C9 C24 1.397(3) . ? C10 C14 1.444(3) . ? C10 C11 1.445(3) . ? C10 C15 1.498(3) . ? C11 C12 1.412(3) . ? C11 C16 1.498(4) . ? C12 C13 1.458(3) . ? C12 C17 1.496(4) . ? C13 C14 1.426(3) . ? C13 C18 1.496(3) . ? C14 C19 1.496(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 F3 1.345(3) . ? C20 F1 1.346(3) . ? C20 F2 1.360(3) . ? C21 O1 1.200(3) . ? C21 O2 1.342(3) . ? O2 C22 1.454(3) . ? C22 C23 1.505(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.378(4) . ? C24 H24A 0.9500 . ? C25 C26 1.381(4) . ? C25 H25A 0.9500 . ? C26 C27 1.377(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 Cl4 1.748(8) . ? C28 Cl3 1.750(8) . ? C28 Cl2 1.753(8) . ? C28 H28A 1.0000 . ? C28' Cl2' 1.717(8) . ? C28' Cl3' 1.729(9) . ? C28' Cl4' 1.752(8) . ? C28' H28B 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 88.23(8) . . ? C1 Ir1 C10 109.98(9) . . ? N1 Ir1 C10 109.02(8) . . ? C1 Ir1 C13 119.13(9) . . ? N1 Ir1 C13 152.60(9) . . ? C10 Ir1 C13 64.98(9) . . ? C1 Ir1 C14 97.25(9) . . ? N1 Ir1 C14 147.39(8) . . ? C10 Ir1 C14 39.06(9) . . ? C13 Ir1 C14 38.50(9) . . ? C1 Ir1 C11 147.12(9) . . ? N1 Ir1 C11 94.15(8) . . ? C10 Ir1 C11 38.70(9) . . ? C13 Ir1 C11 64.03(9) . . ? C14 Ir1 C11 64.45(9) . . ? C1 Ir1 C12 157.99(9) . . ? N1 Ir1 C12 113.78(8) . . ? C10 Ir1 C12 64.22(9) . . ? C13 Ir1 C12 38.87(9) . . ? C14 Ir1 C12 64.45(9) . . ? C11 Ir1 C12 37.25(9) . . ? C1 Ir1 Cl1 88.40(6) . . ? N1 Ir1 Cl1 85.73(6) . . ? C10 Ir1 Cl1 156.25(6) . . ? C13 Ir1 Cl1 93.24(6) . . ? C14 Ir1 Cl1 126.38(6) . . ? C11 Ir1 Cl1 124.47(7) . . ? C12 Ir1 Cl1 93.06(7) . . ? C9 N1 C27 117.6(2) . . ? C9 N1 Ir1 126.37(16) . . ? C27 N1 Ir1 115.89(17) . . ? C2 C1 C20 116.2(2) . . ? C2 C1 Ir1 126.04(16) . . ? C20 C1 Ir1 117.75(16) . . ? C1 C2 C3 123.6(2) . . ? C1 C2 C21 123.6(2) . . ? C3 C2 C21 112.7(2) . . ? C4 C3 C8 118.6(2) . . ? C4 C3 C2 118.3(2) . . ? C8 C3 C2 123.1(2) . . ? C5 C4 C3 121.7(2) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C7 119.5(2) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C6 C7 C8 121.6(3) . . ? C6 C7 H7A 119.2 . . ? C8 C7 H7A 119.2 . . ? C3 C8 C7 118.7(2) . . ? C3 C8 C9 126.6(2) . . ? C7 C8 C9 114.7(2) . . ? N1 C9 C24 120.8(2) . . ? N1 C9 C8 121.3(2) . . ? C24 C9 C8 117.6(2) . . ? C14 C10 C11 107.4(2) . . ? C14 C10 C15 125.6(2) . . ? C11 C10 C15 125.7(2) . . ? C14 C10 Ir1 70.74(13) . . ? C11 C10 Ir1 72.39(13) . . ? C15 C10 Ir1 132.41(17) . . ? C12 C11 C10 109.0(2) . . ? C12 C11 C16 127.5(2) . . ? C10 C11 C16 123.5(2) . . ? C12 C11 Ir1 71.94(13) . . ? C10 C11 Ir1 68.92(13) . . ? C16 C11 Ir1 124.46(17) . . ? C11 C12 C13 107.5(2) . . ? C11 C12 C17 126.4(2) . . ? C13 C12 C17 126.1(2) . . ? C11 C12 Ir1 70.80(13) . . ? C13 C12 Ir1 68.53(13) . . ? C17 C12 Ir1 124.53(18) . . ? C14 C13 C12 108.2(2) . . ? C14 C13 C18 126.1(2) . . ? C12 C13 C18 125.5(2) . . ? C14 C13 Ir1 70.78(13) . . ? C12 C13 Ir1 72.60(13) . . ? C18 C13 Ir1 126.10(17) . . ? C13 C14 C10 107.9(2) . . ? C13 C14 C19 127.0(2) . . ? C10 C14 C19 125.1(2) . . ? C13 C14 Ir1 70.72(13) . . ? C10 C14 Ir1 70.21(13) . . ? C19 C14 Ir1 126.26(17) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? F3 C20 F1 106.6(2) . . ? F3 C20 F2 104.20(19) . . ? F1 C20 F2 105.46(19) . . ? F3 C20 C1 112.07(19) . . ? F1 C20 C1 114.6(2) . . ? F2 C20 C1 113.1(2) . . ? O1 C21 O2 124.3(2) . . ? O1 C21 C2 126.5(2) . . ? O2 C21 C2 109.2(2) . . ? C21 O2 C22 116.5(2) . . ? O2 C22 C23 106.4(2) . . ? O2 C22 H22A 110.5 . . ? C23 C22 H22A 110.5 . . ? O2 C22 H22B 110.5 . . ? C23 C22 H22B 110.5 . . ? H22A C22 H22B 108.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C9 120.7(3) . . ? C25 C24 H24A 119.6 . . ? C9 C24 H24A 119.6 . . ? C24 C25 C26 118.3(2) . . ? C24 C25 H25A 120.9 . . ? C26 C25 H25A 120.9 . . ? C27 C26 C25 118.7(3) . . ? C27 C26 H26A 120.6 . . ? C25 C26 H26A 120.6 . . ? N1 C27 C26 123.7(3) . . ? N1 C27 H27A 118.1 . . ? C26 C27 H27A 118.1 . . ? Cl4 C28 Cl3 109.9(5) . . ? Cl4 C28 Cl2 110.0(4) . . ? Cl3 C28 Cl2 110.0(5) . . ? Cl4 C28 H28A 108.9 . . ? Cl3 C28 H28A 108.9 . . ? Cl2 C28 H28A 108.9 . . ? Cl2' C28' Cl3' 113.5(5) . . ? Cl2' C28' Cl4' 107.7(5) . . ? Cl3' C28' Cl4' 107.6(5) . . ? Cl2' C28' H28B 109.3 . . ? Cl3' C28' H28B 109.3 . . ? Cl4' C28' H28B 109.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 N1 C9 -53.5(2) . . . . ? C10 Ir1 N1 C9 57.1(2) . . . . ? C13 Ir1 N1 C9 129.2(2) . . . . ? C14 Ir1 N1 C9 47.2(3) . . . . ? C11 Ir1 N1 C9 93.7(2) . . . . ? C12 Ir1 N1 C9 126.52(19) . . . . ? Cl1 Ir1 N1 C9 -142.01(19) . . . . ? C1 Ir1 N1 C27 130.32(18) . . . . ? C10 Ir1 N1 C27 -119.13(18) . . . . ? C13 Ir1 N1 C27 -47.0(3) . . . . ? C14 Ir1 N1 C27 -128.96(19) . . . . ? C11 Ir1 N1 C27 -82.52(18) . . . . ? C12 Ir1 N1 C27 -49.7(2) . . . . ? Cl1 Ir1 N1 C27 41.79(17) . . . . ? N1 Ir1 C1 C2 54.2(2) . . . . ? C10 Ir1 C1 C2 -55.4(2) . . . . ? C13 Ir1 C1 C2 -127.2(2) . . . . ? C14 Ir1 C1 C2 -93.5(2) . . . . ? C11 Ir1 C1 C2 -40.7(3) . . . . ? C12 Ir1 C1 C2 -125.8(3) . . . . ? Cl1 Ir1 C1 C2 140.0(2) . . . . ? N1 Ir1 C1 C20 -128.55(18) . . . . ? C10 Ir1 C1 C20 121.84(17) . . . . ? C13 Ir1 C1 C20 50.0(2) . . . . ? C14 Ir1 C1 C20 83.71(18) . . . . ? C11 Ir1 C1 C20 136.54(18) . . . . ? C12 Ir1 C1 C20 51.4(3) . . . . ? Cl1 Ir1 C1 C20 -42.77(17) . . . . ? C20 C1 C2 C3 -169.5(2) . . . . ? Ir1 C1 C2 C3 7.7(3) . . . . ? C20 C1 C2 C21 8.6(3) . . . . ? Ir1 C1 C2 C21 -174.15(17) . . . . ? C1 C2 C3 C4 124.2(3) . . . . ? C21 C2 C3 C4 -54.2(3) . . . . ? C1 C2 C3 C8 -56.7(3) . . . . ? C21 C2 C3 C8 124.9(2) . . . . ? C8 C3 C4 C5 -0.8(4) . . . . ? C2 C3 C4 C5 178.3(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C7 -1.3(4) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C4 C3 C8 C7 0.4(3) . . . . ? C2 C3 C8 C7 -178.8(2) . . . . ? C4 C3 C8 C9 177.8(2) . . . . ? C2 C3 C8 C9 -1.3(4) . . . . ? C6 C7 C8 C3 -0.4(4) . . . . ? C6 C7 C8 C9 -178.1(2) . . . . ? C27 N1 C9 C24 -5.4(3) . . . . ? Ir1 N1 C9 C24 178.44(17) . . . . ? C27 N1 C9 C8 167.6(2) . . . . ? Ir1 N1 C9 C8 -8.5(3) . . . . ? C3 C8 C9 N1 57.5(3) . . . . ? C7 C8 C9 N1 -125.0(2) . . . . ? C3 C8 C9 C24 -129.3(3) . . . . ? C7 C8 C9 C24 48.2(3) . . . . ? C1 Ir1 C10 C14 -76.41(14) . . . . ? N1 Ir1 C10 C14 -171.61(13) . . . . ? C13 Ir1 C10 C14 37.30(13) . . . . ? C11 Ir1 C10 C14 116.33(19) . . . . ? C12 Ir1 C10 C14 80.51(14) . . . . ? Cl1 Ir1 C10 C14 62.4(2) . . . . ? C1 Ir1 C10 C11 167.27(13) . . . . ? N1 Ir1 C10 C11 72.07(14) . . . . ? C13 Ir1 C10 C11 -79.03(14) . . . . ? C14 Ir1 C10 C11 -116.33(19) . . . . ? C12 Ir1 C10 C11 -35.82(13) . . . . ? Cl1 Ir1 C10 C11 -53.9(2) . . . . ? C1 Ir1 C10 C15 44.7(3) . . . . ? N1 Ir1 C10 C15 -50.5(3) . . . . ? C13 Ir1 C10 C15 158.4(3) . . . . ? C14 Ir1 C10 C15 121.1(3) . . . . ? C11 Ir1 C10 C15 -122.6(3) . . . . ? C12 Ir1 C10 C15 -158.4(3) . . . . ? Cl1 Ir1 C10 C15 -176.55(17) . . . . ? C14 C10 C11 C12 -1.4(3) . . . . ? C15 C10 C11 C12 -168.9(2) . . . . ? Ir1 C10 C11 C12 61.07(17) . . . . ? C14 C10 C11 C16 179.4(2) . . . . ? C15 C10 C11 C16 11.9(4) . . . . ? Ir1 C10 C11 C16 -118.2(2) . . . . ? C14 C10 C11 Ir1 -62.46(15) . . . . ? C15 C10 C11 Ir1 130.0(2) . . . . ? C1 Ir1 C11 C12 -141.91(17) . . . . ? N1 Ir1 C11 C12 124.92(14) . . . . ? C10 Ir1 C11 C12 -119.5(2) . . . . ? C13 Ir1 C11 C12 -37.79(14) . . . . ? C14 Ir1 C11 C12 -80.73(15) . . . . ? Cl1 Ir1 C11 C12 37.25(16) . . . . ? C1 Ir1 C11 C10 -22.4(2) . . . . ? N1 Ir1 C11 C10 -115.60(14) . . . . ? C13 Ir1 C11 C10 81.70(15) . . . . ? C14 Ir1 C11 C10 38.75(13) . . . . ? C12 Ir1 C11 C10 119.5(2) . . . . ? Cl1 Ir1 C11 C10 156.74(11) . . . . ? C1 Ir1 C11 C16 94.6(3) . . . . ? N1 Ir1 C11 C16 1.4(2) . . . . ? C10 Ir1 C11 C16 117.0(3) . . . . ? C13 Ir1 C11 C16 -161.3(3) . . . . ? C14 Ir1 C11 C16 155.7(3) . . . . ? C12 Ir1 C11 C16 -123.5(3) . . . . ? Cl1 Ir1 C11 C16 -86.3(2) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C16 C11 C12 C13 178.9(2) . . . . ? Ir1 C11 C12 C13 58.93(16) . . . . ? C10 C11 C12 C17 -178.5(2) . . . . ? C16 C11 C12 C17 0.7(4) . . . . ? Ir1 C11 C12 C17 -119.3(3) . . . . ? C10 C11 C12 Ir1 -59.19(16) . . . . ? C16 C11 C12 Ir1 120.0(3) . . . . ? C1 Ir1 C12 C11 116.7(2) . . . . ? N1 Ir1 C12 C11 -63.34(16) . . . . ? C10 Ir1 C12 C11 37.19(14) . . . . ? C13 Ir1 C12 C11 118.6(2) . . . . ? C14 Ir1 C12 C11 80.72(15) . . . . ? Cl1 Ir1 C12 C11 -150.02(13) . . . . ? C1 Ir1 C12 C13 -1.9(3) . . . . ? N1 Ir1 C12 C13 178.05(13) . . . . ? C10 Ir1 C12 C13 -81.43(15) . . . . ? C14 Ir1 C12 C13 -37.89(14) . . . . ? C11 Ir1 C12 C13 -118.6(2) . . . . ? Cl1 Ir1 C12 C13 91.37(13) . . . . ? C1 Ir1 C12 C17 -121.8(3) . . . . ? N1 Ir1 C12 C17 58.2(2) . . . . ? C10 Ir1 C12 C17 158.7(3) . . . . ? C13 Ir1 C12 C17 -119.8(3) . . . . ? C14 Ir1 C12 C17 -157.7(3) . . . . ? C11 Ir1 C12 C17 121.5(3) . . . . ? Cl1 Ir1 C12 C17 -28.5(2) . . . . ? C11 C12 C13 C14 1.8(3) . . . . ? C17 C12 C13 C14 -179.9(2) . . . . ? Ir1 C12 C13 C14 62.21(16) . . . . ? C11 C12 C13 C18 177.3(2) . . . . ? C17 C12 C13 C18 -4.5(4) . . . . ? Ir1 C12 C13 C18 -122.3(2) . . . . ? C11 C12 C13 Ir1 -60.37(16) . . . . ? C17 C12 C13 Ir1 117.8(2) . . . . ? C1 Ir1 C13 C14 62.05(16) . . . . ? N1 Ir1 C13 C14 -121.00(19) . . . . ? C10 Ir1 C13 C14 -37.83(14) . . . . ? C11 Ir1 C13 C14 -80.89(15) . . . . ? C12 Ir1 C13 C14 -117.1(2) . . . . ? Cl1 Ir1 C13 C14 152.03(13) . . . . ? C1 Ir1 C13 C12 179.17(13) . . . . ? N1 Ir1 C13 C12 -3.9(3) . . . . ? C10 Ir1 C13 C12 79.29(15) . . . . ? C14 Ir1 C13 C12 117.1(2) . . . . ? C11 Ir1 C13 C12 36.23(14) . . . . ? Cl1 Ir1 C13 C12 -90.85(13) . . . . ? C1 Ir1 C13 C18 -59.2(2) . . . . ? N1 Ir1 C13 C18 117.8(2) . . . . ? C10 Ir1 C13 C18 -159.0(3) . . . . ? C14 Ir1 C13 C18 -121.2(3) . . . . ? C11 Ir1 C13 C18 157.9(3) . . . . ? C12 Ir1 C13 C18 121.7(3) . . . . ? Cl1 Ir1 C13 C18 30.8(2) . . . . ? C12 C13 C14 C10 -2.7(3) . . . . ? C18 C13 C14 C10 -178.1(2) . . . . ? Ir1 C13 C14 C10 60.69(16) . . . . ? C12 C13 C14 C19 175.2(2) . . . . ? C18 C13 C14 C19 -0.2(4) . . . . ? Ir1 C13 C14 C19 -121.4(2) . . . . ? C12 C13 C14 Ir1 -63.39(16) . . . . ? C18 C13 C14 Ir1 121.2(2) . . . . ? C11 C10 C14 C13 2.5(3) . . . . ? C15 C10 C14 C13 170.1(2) . . . . ? Ir1 C10 C14 C13 -61.01(16) . . . . ? C11 C10 C14 C19 -175.4(2) . . . . ? C15 C10 C14 C19 -7.9(4) . . . . ? Ir1 C10 C14 C19 121.0(2) . . . . ? C11 C10 C14 Ir1 63.54(16) . . . . ? C15 C10 C14 Ir1 -128.9(2) . . . . ? C1 Ir1 C14 C13 -128.94(14) . . . . ? N1 Ir1 C14 C13 132.95(16) . . . . ? C10 Ir1 C14 C13 118.11(19) . . . . ? C11 Ir1 C14 C13 79.71(15) . . . . ? C12 Ir1 C14 C13 38.25(14) . . . . ? Cl1 Ir1 C14 C13 -35.57(16) . . . . ? C1 Ir1 C14 C10 112.95(14) . . . . ? N1 Ir1 C14 C10 14.8(2) . . . . ? C13 Ir1 C14 C10 -118.11(19) . . . . ? C11 Ir1 C14 C10 -38.40(13) . . . . ? C12 Ir1 C14 C10 -79.86(14) . . . . ? Cl1 Ir1 C14 C10 -153.68(11) . . . . ? C1 Ir1 C14 C19 -6.7(2) . . . . ? N1 Ir1 C14 C19 -104.8(2) . . . . ? C10 Ir1 C14 C19 -119.6(3) . . . . ? C13 Ir1 C14 C19 122.3(3) . . . . ? C11 Ir1 C14 C19 -158.0(2) . . . . ? C12 Ir1 C14 C19 160.5(2) . . . . ? Cl1 Ir1 C14 C19 86.7(2) . . . . ? C2 C1 C20 F3 147.5(2) . . . . ? Ir1 C1 C20 F3 -30.0(3) . . . . ? C2 C1 C20 F1 -90.8(3) . . . . ? Ir1 C1 C20 F1 91.7(2) . . . . ? C2 C1 C20 F2 30.1(3) . . . . ? Ir1 C1 C20 F2 -147.38(16) . . . . ? C1 C2 C21 O1 -118.6(3) . . . . ? C3 C2 C21 O1 59.8(3) . . . . ? C1 C2 C21 O2 63.8(3) . . . . ? C3 C2 C21 O2 -117.9(2) . . . . ? O1 C21 O2 C22 5.3(4) . . . . ? C2 C21 O2 C22 -177.03(19) . . . . ? C21 O2 C22 C23 167.9(2) . . . . ? N1 C9 C24 C25 4.1(4) . . . . ? C8 C9 C24 C25 -169.1(2) . . . . ? C9 C24 C25 C26 0.1(4) . . . . ? C24 C25 C26 C27 -2.8(4) . . . . ? C9 N1 C27 C26 2.7(4) . . . . ? Ir1 N1 C27 C26 179.3(2) . . . . ? C25 C26 C27 N1 1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 2.572 _refine_diff_density_min -1.366 _refine_diff_density_rms 0.164 _vrf_PLAT302_jonll65 ; PROBLEM: _G Anion/Solvent Disorder ......................... 50.00 Perc. RESPONSE: The co-crystallized chloroform solvent molecule is modeled as disordered over two positions (50:50, due to promixal crystallographic inversion center). ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2007). SAINT V7.46A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2007). APEX2 V2.2-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2007). SADABS V2007/4, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122. ; #===end