data_jl12m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 I O3' _chemical_formula_weight 456.26 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 10.8190(7) _cell_length_b 9.8363(7) _cell_length_c 18.3221(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.424(2) _cell_angle_gamma 90.00 _cell_volume 1948.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14200 _diffrn_reflns_av_R_equivalents 0.1129 _diffrn_reflns_av_sigmaI/netI 0.3250 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4836 _reflns_number_gt 1364 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0199P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4836 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1659 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 0.520 _refine_ls_restrained_S_all 0.520 _refine_ls_shift/su_max 0.063 _refine_ls_shift/su_mean 0.011 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 I1 I 0.84182(4) 0.31615(4) 0.085386(17) 0.05678(14) Uani 1 1 d . . . O1 O 1.4427(4) 0.1848(5) 0.12275(19) 0.0774(11) Uani 1 1 d . . . O2 O 0.4811(4) 0.3404(5) -0.15678(19) 0.0833(13) Uani 1 1 d . . . O3 O 1.2553(3) 0.0838(4) -0.26917(18) 0.0755(13) Uani 1 1 d . . . C1 C 0.8862(5) 0.2723(5) -0.0225(2) 0.0429(15) Uani 1 1 d . . . C2 C 0.7948(5) 0.2795(5) -0.0813(3) 0.0419(14) Uani 1 1 d . . . C3 C 0.8502(5) 0.2419(5) -0.1462(3) 0.0517(16) Uani 1 1 d . . . C4 C 0.9873(5) 0.2061(6) -0.1285(2) 0.0453(15) Uani 1 1 d . . . C5 C 0.9970(5) 0.2308(5) -0.0437(3) 0.0433(15) Uani 1 1 d . . . C6 C 1.1150(5) 0.2136(6) -0.0011(3) 0.0412(15) Uani 1 1 d . . . C7 C 1.1622(5) 0.3252(6) 0.0402(3) 0.0554(15) Uani 1 1 d . . . C8 C 1.2728(5) 0.3124(7) 0.0817(3) 0.0578(15) Uani 1 1 d . . . C9 C 1.3339(5) 0.1874(7) 0.0808(3) 0.0551(14) Uani 1 1 d . . . C10 C 1.2903(6) 0.0747(6) 0.0409(3) 0.0559(17) Uani 1 1 d . . . C11 C 1.1788(5) 0.0916(6) -0.0018(3) 0.0547(16) Uani 1 1 d . . . C12 C 1.0702(4) 0.3075(6) -0.1645(2) 0.0510(15) Uani 1 1 d . . . C13 C 1.1572(5) 0.2649(6) -0.2118(3) 0.0488(17) Uani 1 1 d . . . C14 C 1.1733(5) 0.1204(6) -0.2280(3) 0.0481(16) Uani 1 1 d . . . C15 C 1.0921(5) 0.0199(5) -0.1949(2) 0.0510(16) Uani 1 1 d . . . C16 C 1.0079(5) 0.0583(6) -0.1475(2) 0.0489(15) Uani 1 1 d . . . C17 C 0.7844(6) 0.2381(6) -0.2118(3) 0.0621(18) Uani 1 1 d . . . C18 C 0.6579(6) 0.2740(6) -0.2143(3) 0.075(2) Uani 1 1 d . . . C19 C 0.6060(5) 0.3097(7) -0.1482(3) 0.0650(16) Uani 1 1 d . . . C20 C 0.6690(5) 0.3147(6) -0.0803(3) 0.0513(13) Uani 1 1 d . . . C21 C 1.5094(5) 0.0607(7) 0.1300(3) 0.109(3) Uani 1 1 d . . . H21A H 1.5820 0.0745 0.1611 0.163 Uiso 1 1 calc R . . H21B H 1.5333 0.0309 0.0827 0.163 Uiso 1 1 calc R . . H21C H 1.4579 -0.0071 0.1510 0.163 Uiso 1 1 calc R . . C22 C 0.4183(5) 0.3863(6) -0.0949(3) 0.093(2) Uani 1 1 d . . . H22A H 0.3332 0.4036 -0.1087 0.140 Uiso 1 1 calc R . . H22B H 0.4562 0.4685 -0.0767 0.140 Uiso 1 1 calc R . . H22C H 0.4231 0.3179 -0.0576 0.140 Uiso 1 1 calc R . . H20 H 0.6264 0.3237 -0.0400 0.500 Uiso 1 1 d . . . H18 H 0.5920 0.2473 -0.2646 0.500 Uiso 1 1 d . . . H11 H 1.1534 0.0158 -0.0376 0.500 Uiso 1 1 d . . . H15 H 1.0972 -0.0960 -0.2113 0.500 Uiso 1 1 d . . . H10 H 1.3575 -0.0007 0.0449 0.500 Uiso 1 1 d . . . H12 H 1.0385 0.4184 -0.1579 0.500 Uiso 1 1 d . . . H17 H 0.8183 0.1735 -0.2516 0.500 Uiso 1 1 d . . . H8 H 1.3091 0.3806 0.1190 0.500 Uiso 1 1 d . . . H7 H 1.1052 0.4153 0.0427 0.500 Uiso 1 1 d . . . H13 H 1.2112 0.3298 -0.2341 0.500 Uiso 1 1 d . . . H16 H 0.9587 -0.0084 -0.1222 0.500 Uiso 1 1 d . . . 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 I1 0.0723(3) 0.0582(2) 0.04123(19) -0.0013(3) 0.01841(17) 0.0097(3) O1 0.081(3) 0.076(3) 0.074(3) -0.008(3) -0.013(2) 0.012(3) O2 0.065(3) 0.122(4) 0.063(3) -0.008(3) 0.001(2) 0.024(3) O3 0.078(3) 0.079(3) 0.073(3) 0.005(2) 0.043(2) 0.016(2) C1 0.059(4) 0.033(4) 0.038(3) -0.004(2) 0.013(3) 0.007(3) C2 0.052(4) 0.036(4) 0.037(3) 0.000(3) 0.003(3) 0.004(3) C3 0.050(4) 0.063(4) 0.043(4) -0.002(3) 0.013(3) 0.004(3) C4 0.047(4) 0.058(5) 0.032(3) -0.009(3) 0.012(3) 0.006(4) C5 0.058(4) 0.034(4) 0.039(3) 0.004(2) 0.008(3) -0.006(3) C6 0.047(4) 0.042(5) 0.035(3) -0.001(3) 0.013(3) 0.002(3) C7 0.073(4) 0.049(4) 0.045(3) 0.010(4) 0.010(3) -0.013(4) C8 0.064(4) 0.057(4) 0.052(4) 0.004(4) 0.003(3) 0.007(5) C9 0.042(4) 0.081(5) 0.042(3) 0.015(5) -0.007(3) 0.007(5) C10 0.056(5) 0.061(5) 0.052(4) 0.000(4) 0.011(3) 0.000(4) C11 0.051(4) 0.058(5) 0.056(4) 0.005(3) 0.013(3) 0.012(4) C12 0.051(4) 0.065(4) 0.038(3) 0.002(4) 0.001(3) -0.011(4) C13 0.048(4) 0.047(5) 0.051(4) 0.005(3) 0.002(3) 0.000(3) C14 0.049(4) 0.067(5) 0.029(3) -0.001(3) 0.009(3) 0.006(4) C15 0.062(4) 0.062(4) 0.030(3) 0.008(3) 0.018(3) 0.004(3) C16 0.063(4) 0.048(4) 0.036(3) -0.009(3) 0.010(3) 0.004(3) C17 0.069(4) 0.077(5) 0.041(4) -0.003(3) 0.002(3) 0.010(4) C18 0.067(5) 0.091(6) 0.067(4) -0.011(4) 0.018(4) 0.023(4) C19 0.038(4) 0.081(5) 0.076(4) -0.011(4) 0.002(4) 0.012(4) C20 0.050(4) 0.051(3) 0.051(3) 0.007(4) -0.011(3) 0.006(4) C21 0.086(6) 0.131(8) 0.105(6) -0.019(5) -0.042(4) 0.029(6) C22 0.058(4) 0.135(7) 0.087(5) -0.017(4) 0.005(4) 0.021(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 I1 C1 2.098(4) . ? O1 C9 1.379(6) . ? O1 C21 1.421(6) . ? O2 C19 1.387(5) . ? O2 C22 1.419(5) . ? O3 C14 1.242(5) . ? C1 C5 1.340(6) . ? C1 C2 1.432(6) . ? C2 C20 1.405(6) . ? C2 C3 1.403(6) . ? C3 C17 1.372(6) . ? C3 C4 1.545(6) . ? C4 C12 1.512(6) . ? C4 C16 1.514(7) . ? C4 C5 1.570(6) . ? C5 C6 1.478(6) . ? C6 C11 1.385(7) . ? C6 C7 1.417(7) . ? C7 C8 1.396(6) . ? C7 H7 1.0819 . ? C8 C9 1.397(7) . ? C8 H8 1.0236 . ? C9 C10 1.399(7) . ? C10 C11 1.419(6) . ? C10 H10 1.0387 . ? C11 H11 1.0223 . ? C12 C13 1.371(6) . ? C12 H12 1.1517 . ? C13 C14 1.463(6) . ? C13 H13 0.9680 . ? C14 C15 1.470(6) . ? C15 C16 1.340(6) . ? C15 H15 1.1812 . ? C16 H16 0.9741 . ? C17 C18 1.412(6) . ? C17 H17 1.0450 . ? C18 C19 1.401(6) . ? C18 H18 1.1718 . ? C19 C20 1.393(6) . ? C20 H20 0.8922 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O1 C21 119.1(5) . . ? C19 O2 C22 118.4(4) . . ? C5 C1 C2 113.2(4) . . ? C5 C1 I1 125.4(4) . . ? C2 C1 I1 121.4(4) . . ? C20 C2 C3 121.5(5) . . ? C20 C2 C1 129.9(5) . . ? C3 C2 C1 108.6(5) . . ? C17 C3 C2 121.7(5) . . ? C17 C3 C4 129.4(5) . . ? C2 C3 C4 108.8(5) . . ? C12 C4 C16 115.9(4) . . ? C12 C4 C3 109.9(4) . . ? C16 C4 C3 108.7(4) . . ? C12 C4 C5 108.3(4) . . ? C16 C4 C5 111.8(4) . . ? C3 C4 C5 101.3(4) . . ? C1 C5 C6 130.2(5) . . ? C1 C5 C4 108.1(4) . . ? C6 C5 C4 121.7(4) . . ? C11 C6 C7 120.5(5) . . ? C11 C6 C5 120.9(5) . . ? C7 C6 C5 118.5(5) . . ? C8 C7 C6 120.2(6) . . ? C8 C7 H7 121.9 . . ? C6 C7 H7 117.7 . . ? C7 C8 C9 117.9(6) . . ? C7 C8 H8 126.9 . . ? C9 C8 H8 114.6 . . ? O1 C9 C10 122.5(6) . . ? O1 C9 C8 113.8(6) . . ? C10 C9 C8 123.7(5) . . ? C9 C10 C11 117.1(5) . . ? C9 C10 H10 108.0 . . ? C11 C10 H10 134.3 . . ? C6 C11 C10 120.6(5) . . ? C6 C11 H11 121.1 . . ? C10 C11 H11 117.9 . . ? C13 C12 C4 120.7(5) . . ? C13 C12 H12 124.9 . . ? C4 C12 H12 113.2 . . ? C12 C13 C14 121.1(5) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 118.3 . . ? O3 C14 C13 120.0(5) . . ? O3 C14 C15 120.6(6) . . ? C13 C14 C15 119.4(5) . . ? C16 C15 C14 120.8(5) . . ? C16 C15 H15 118.5 . . ? C14 C15 H15 120.6 . . ? C15 C16 C4 122.0(5) . . ? C15 C16 H16 121.2 . . ? C4 C16 H16 116.7 . . ? C3 C17 C18 119.1(5) . . ? C3 C17 H17 116.3 . . ? C18 C17 H17 119.9 . . ? C17 C18 C19 117.3(5) . . ? C17 C18 H18 121.7 . . ? C19 C18 H18 118.9 . . ? O2 C19 C20 122.1(5) . . ? O2 C19 C18 112.4(5) . . ? C20 C19 C18 125.5(5) . . ? C2 C20 C19 114.7(5) . . ? C2 C20 H20 124.7 . . ? C19 C20 H20 119.5 . . ? O1 C21 H21A 109.5 . . ? O1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.567 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.072