# ja9923890.cif _publ_section_abstract 'see manuscript' _publ_author_address 'see manuscript' #---------------------------------------------------------------------- # # Person for contact _publ_contact_author ; Dr. Fernando J. Lahoz Departamento de Qu\'imica Inorg\'anica Facultad de Ciencias Universidad de Zaragoza 50009 Zaragoza, Spain ; _publ_contact_author_email lahoz@posta.unizar.es #---------------------------------------------------------------------- #Publication details loop_ _publ_author_name 'Torres, F.' 'Sola, E.' 'Mart\'in, M.' 'L\'opez, J.A.' 'Lahoz, F.J.' 'Oro, L.A.' _publ_requested_journal 'J. Am. Chem. Soc.' _journal_name_full 'Journal of the American Chemical Society' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year 1999 data_compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; dihydride-triisopropylphosphine-1,3,5-trimethylbenzene-iridium(III) tetrafluoro borate ; _chemical_formula_moiety 'C18 H35 Ir P 1+, B F4 1-' _chemical_formula_sum 'C18 H35 B F4 Ir P' _chemical_formula_weight 561.44 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' 'B' 'B' 0.0013 0.0007 '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' 'P' 'P' 0.1023 0.0942 '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 2(1) 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1477(7) _cell_length_b 13.8943(12) _cell_length_c 10.1659(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.454(10) _cell_angle_gamma 90.00 _cell_volume 1085.14(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 15 _cell_measurement_theta_max 20 _exptl_crystal_description 'irregular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 6.258 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2116 _exptl_absorpt_correction_T_max 0.3988 _exptl_absorpt_process_details ; Azimuthal psi-scans of 30 reflections (15 + Friedel pairs) at 10\% intervals. Data corrected with the program: XPREP, SHELXTL v. 5 (Siemens) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal focus Mo sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w-2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 4286 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3842 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS v. 2.1 (Siemens)' _computing_cell_refinement 'XSCANS v. 2.1 (Siemens)' _computing_data_reduction 'XSCANS v. 2.1 (Siemens)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, SHELXTL v.5 (Siemens)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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. All hydrogen atoms (except the metal hydrides) were introduced in calculated positions, and refined riding on the corresponding carbon atoms with a fixed geometry but with variable C-H lenghts, and torsion angle for the methyl groups (AFIX 14, AFIX 44 and AFIX 138 in Shelxl-97). Four common isotropic displacement parameters were refined for 'organic' hydrogens. The two hydride ligands were found in a difference-fourier map with low-angle data (less than 40 degrees) and their positional parameters were refined with this low-angle data. In the final cycles of refinement the positional parameters were refined with all data riding on the iridium atom with two independent isotropic displacement parameters. ; _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^)+(0.0377P)^2^+8.8796P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.026(14) _refine_ls_number_reflns 3842 _refine_ls_number_parameters 255 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.690 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.090 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.996 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 Ir Ir 0.23111(4) 0.85638(3) 0.13483(3) 0.02283(12) Uani 1 1 d . . . H0 H 0.1056 0.7950 0.0275 0.02(2) Uiso 1 1 d R . . H1 H 0.3190 0.7997 0.0513 0.02(2) Uiso 1 1 d R . . P P 0.2234(3) 0.92004(15) -0.0727(2) 0.0200(4) Uani 1 1 d . . . C1 C 0.0546(11) 0.8453(11) 0.2695(8) 0.026(2) Uani 1 1 d . . . C2 C 0.2039(13) 0.7920(7) 0.3291(10) 0.028(2) Uani 1 1 d . . . H2 H 0.1949 0.7251 0.3446 0.05(2) Uiso 1 1 calc R . . C3 C 0.3728(12) 0.8364(8) 0.3681(9) 0.031(3) Uani 1 1 d . . . C4 C 0.3827(13) 0.9372(8) 0.3412(10) 0.030(2) Uani 1 1 d . . . H4 H 0.495(16) 0.969(5) 0.367(4) 0.05(2) Uiso 1 1 calc R . . C5 C 0.2302(13) 0.9905(7) 0.2783(10) 0.030(2) Uani 1 1 d . . . C6 C 0.0674(13) 0.9440(6) 0.2444(9) 0.026(2) Uani 1 1 d . . . H6 H -0.026(15) 0.977(5) 0.208(6) 0.05(2) Uiso 1 1 calc R . . C7 C -0.1208(13) 0.7970(7) 0.2360(11) 0.035(2) Uani 1 1 d . . . H7A H -0.120(5) 0.759(7) 0.305(8) 0.10(2) Uiso 1 1 calc R . . H7B H -0.143(7) 0.763(7) 0.159(9) 0.10(2) Uiso 1 1 calc R . . H7C H -0.202(8) 0.841(4) 0.224(11) 0.10(2) Uiso 1 1 calc R . . C8 C 0.5345(14) 0.7793(9) 0.4403(11) 0.042(3) Uani 1 1 d . . . H8A H 0.543(8) 0.769(7) 0.536(9) 0.10(2) Uiso 1 1 calc R . . H8B H 0.635(9) 0.814(5) 0.437(10) 0.10(2) Uiso 1 1 calc R . . H8C H 0.529(7) 0.719(6) 0.394(8) 0.10(2) Uiso 1 1 calc R . . C9 C 0.2410(18) 1.0976(8) 0.2603(13) 0.047(3) Uani 1 1 d . . . H9A H 0.227(14) 1.133(3) 0.347(9) 0.10(2) Uiso 1 1 calc R . . H9B H 0.141(12) 1.120(2) 0.170(10) 0.10(2) Uiso 1 1 calc R . . H9C H 0.362(11) 1.1150(19) 0.251(11) 0.10(2) Uiso 1 1 calc R . . C10 C 0.2679(12) 0.8272(6) -0.1867(9) 0.027(2) Uani 1 1 d . . . H10 H 0.1956 0.7701 -0.1815 0.05(2) Uiso 1 1 calc R . . C11 C 0.2129(13) 0.855(2) -0.3430(8) 0.044(2) Uani 1 1 d . . . H11A H 0.241(9) 0.919(5) -0.3510(10) 0.049(8) Uiso 1 1 calc R . . H11B H 0.093(7) 0.847(6) -0.384(3) 0.049(8) Uiso 1 1 calc R . . H11C H 0.271(9) 0.816(4) -0.388(3) 0.049(8) Uiso 1 1 calc R . . C12 C 0.4556(14) 0.7923(8) -0.1390(12) 0.041(2) Uani 1 1 d . . . H12A H 0.465(2) 0.737(5) -0.193(6) 0.049(8) Uiso 1 1 calc R . . H12B H 0.491(4) 0.775(5) -0.042(7) 0.049(8) Uiso 1 1 calc R . . H12C H 0.530(5) 0.843(4) -0.152(6) 0.049(8) Uiso 1 1 calc R . . C13 C 0.3689(11) 1.0251(7) -0.0557(10) 0.0260(19) Uani 1 1 d . . . H13 H 0.321(6) 1.076(7) -0.013(6) 0.05(2) Uiso 1 1 calc R . . C14 C 0.5560(13) 1.0065(8) 0.0450(11) 0.040(2) Uani 1 1 d . . . H14A H 0.618(5) 0.967(5) -0.001(4) 0.049(8) Uiso 1 1 calc R . . H14B H 0.5507(13) 0.974(5) 0.128(7) 0.049(8) Uiso 1 1 calc R . . H14C H 0.616(5) 1.067(4) 0.071(6) 0.049(8) Uiso 1 1 calc R . . C15 C 0.3769(13) 1.0670(7) -0.1928(11) 0.034(2) Uani 1 1 d . . . H15A H 0.429(10) 1.128(5) -0.176(2) 0.049(8) Uiso 1 1 calc R . . H15B H 0.264(8) 1.072(5) -0.257(5) 0.049(8) Uiso 1 1 calc R . . H15C H 0.443(9) 1.026(4) -0.229(5) 0.049(8) Uiso 1 1 calc R . . C16 C 0.0068(12) 0.9668(7) -0.1792(10) 0.030(2) Uani 1 1 d . . . H16 H 0.0148(17) 0.986(3) -0.256(12) 0.05(2) Uiso 1 1 calc R . . C17 C -0.1284(13) 0.8864(8) -0.2122(12) 0.046(3) Uani 1 1 d . . . H17A H -0.147(7) 0.866(4) -0.127(5) 0.049(8) Uiso 1 1 calc R . . H17B H -0.087(5) 0.832(4) -0.253(8) 0.049(8) Uiso 1 1 calc R . . H17C H -0.237(7) 0.910(2) -0.278(7) 0.049(8) Uiso 1 1 calc R . . C18 C -0.0534(14) 1.0521(8) -0.1132(12) 0.041(3) Uani 1 1 d . . . H18A H -0.165(9) 1.076(4) -0.177(5) 0.049(8) Uiso 1 1 calc R . . H18B H 0.034(7) 1.104(4) -0.095(7) 0.049(8) Uiso 1 1 calc R . . H18C H -0.068(9) 1.032(2) -0.025(7) 0.049(8) Uiso 1 1 calc R . . B B -0.1661(16) 1.0762(8) -0.5638(12) 0.036(3) Uani 1 1 d . . . F1 F -0.1701(9) 0.9759(4) -0.5687(7) 0.0498(16) Uani 1 1 d . . . F2 F -0.1515(12) 1.1116(5) -0.6871(7) 0.066(2) Uani 1 1 d . . . F3 F -0.0248(10) 1.1082(6) -0.4568(7) 0.059(2) Uani 1 1 d . . . F4 F -0.3162(11) 1.1114(6) -0.5492(12) 0.088(3) Uani 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 Ir 0.03379(17) 0.02031(15) 0.01674(15) 0.0008(3) 0.01153(11) -0.0008(3) P 0.0222(11) 0.0216(10) 0.0172(10) 0.0014(8) 0.0078(8) -0.0003(8) C1 0.033(4) 0.029(7) 0.020(3) 0.001(5) 0.012(3) -0.010(5) C2 0.041(5) 0.022(5) 0.024(5) -0.001(4) 0.017(4) 0.000(4) C3 0.032(4) 0.048(11) 0.012(4) 0.007(4) 0.005(3) 0.008(5) C4 0.030(5) 0.039(6) 0.023(5) -0.013(4) 0.011(4) -0.019(5) C5 0.046(6) 0.027(5) 0.027(5) -0.012(4) 0.024(4) -0.011(4) C6 0.042(6) 0.021(5) 0.021(4) 0.001(3) 0.019(4) 0.007(4) C7 0.030(5) 0.031(5) 0.047(6) -0.001(4) 0.017(5) -0.005(4) C8 0.033(6) 0.062(7) 0.028(5) 0.007(5) 0.006(5) 0.003(5) C9 0.071(8) 0.028(5) 0.047(7) -0.008(5) 0.027(6) -0.011(5) C10 0.032(5) 0.027(5) 0.025(4) -0.001(3) 0.014(4) 0.001(3) C11 0.065(6) 0.048(5) 0.026(4) -0.012(10) 0.025(4) -0.010(11) C12 0.046(6) 0.044(6) 0.040(6) -0.009(5) 0.022(5) 0.004(5) C13 0.023(4) 0.027(4) 0.028(5) 0.000(4) 0.010(4) -0.006(4) C14 0.032(5) 0.047(6) 0.038(6) 0.003(5) 0.008(5) -0.006(5) C15 0.036(5) 0.033(5) 0.037(6) 0.011(4) 0.016(4) -0.003(4) C16 0.024(5) 0.038(5) 0.024(5) 0.010(4) 0.003(4) 0.006(4) C17 0.023(5) 0.051(7) 0.054(7) 0.005(5) -0.001(4) -0.006(4) C18 0.036(6) 0.041(6) 0.047(6) 0.013(5) 0.015(5) 0.016(5) B 0.039(6) 0.030(6) 0.032(6) -0.009(5) 0.001(5) 0.003(5) F1 0.060(4) 0.032(3) 0.062(4) -0.004(3) 0.026(3) -0.001(3) F2 0.107(6) 0.047(4) 0.037(4) 0.004(3) 0.015(4) 0.015(4) F3 0.054(4) 0.057(4) 0.044(4) -0.003(4) -0.013(3) -0.007(3) F4 0.058(5) 0.065(5) 0.155(9) -0.055(6) 0.055(6) -0.016(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 Ir C2 2.246(9) . ? Ir P 2.270(2) . ? Ir C3 2.282(8) . ? Ir C1 2.297(8) . ? Ir C4 2.337(9) . ? Ir C6 2.343(9) . ? Ir C5 2.367(9) . ? Ir H0 1.4903 . ? Ir H1 1.5030 . ? P C10 1.849(9) . ? P C13 1.852(9) . ? P C16 1.854(9) . ? C1 C2 1.380(15) . ? C1 C6 1.404(17) . ? C1 C7 1.512(13) . ? C2 C3 1.438(14) . ? C2 H2 0.9500 . ? C3 C4 1.434(17) . ? C3 C8 1.504(15) . ? C4 C5 1.405(15) . ? C4 H4 0.9666 . ? C5 C6 1.411(14) . ? C5 C9 1.506(14) . ? C6 H6 0.8597 . ? C7 H7A 0.8823 . ? C7 H7B 0.8823 . ? C7 H7C 0.8823 . ? C8 H8A 0.9591 . ? C8 H8B 0.9591 . ? C8 H8C 0.9591 . ? C9 H9A 1.0501 . ? C9 H9B 1.0501 . ? C9 H9C 1.0501 . ? C10 C12 1.521(14) . ? C10 C11 1.550(14) . ? C10 H10 1.0000 . ? C11 H11A 0.9331 . ? C11 H11B 0.9331 . ? C11 H11C 0.9331 . ? C12 H12A 0.9660 . ? C12 H12B 0.9660 . ? C12 H12C 0.9660 . ? C13 C15 1.532(13) . ? C13 C14 1.549(13) . ? C13 H13 0.9767 . ? C14 H14A 0.9691 . ? C14 H14B 0.9691 . ? C14 H14C 0.9691 . ? C15 H15A 0.9348 . ? C15 H15B 0.9348 . ? C15 H15C 0.9348 . ? C16 C18 1.522(14) . ? C16 C17 1.525(14) . ? C16 H16 0.8502 . ? C17 H17A 0.9715 . ? C17 H17B 0.9715 . ? C17 H17C 0.9715 . ? C18 H18A 0.9848 . ? C18 H18B 0.9848 . ? C18 H18C 0.9848 . ? B F3 1.368(13) . ? B F4 1.371(14) . ? B F2 1.388(15) . ? B F1 1.395(13) . ? 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 Ir P 173.1(3) . . ? C2 Ir C3 37.0(4) . . ? P Ir C3 149.5(3) . . ? C2 Ir C1 35.3(4) . . ? P Ir C1 138.7(3) . . ? C3 Ir C1 64.7(3) . . ? C2 Ir C4 65.1(4) . . ? P Ir C4 119.4(3) . . ? C3 Ir C4 36.1(4) . . ? C1 Ir C4 75.3(4) . . ? C2 Ir C6 63.3(3) . . ? P Ir C6 113.3(2) . . ? C3 Ir C6 74.9(4) . . ? C1 Ir C6 35.2(4) . . ? C4 Ir C6 62.5(4) . . ? C2 Ir C5 75.5(3) . . ? P Ir C5 105.1(2) . . ? C3 Ir C5 63.9(4) . . ? C1 Ir C5 63.5(4) . . ? C4 Ir C5 34.7(4) . . ? C6 Ir C5 34.9(3) . . ? C2 Ir H0 99.9 . . ? P Ir H0 75.1 . . ? C3 Ir H0 132.7 . . ? C1 Ir H0 89.2 . . ? C4 Ir H0 164.0 . . ? C6 Ir H0 106.6 . . ? C5 Ir H0 139.4 . . ? C2 Ir H1 119.6 . . ? P Ir H1 63.3 . . ? C3 Ir H1 110.6 . . ? C1 Ir H1 144.3 . . ? C4 Ir H1 123.4 . . ? C6 Ir H1 174.0 . . ? C5 Ir H1 149.3 . . ? H0 Ir H1 68.0 . . ? C10 P C13 110.8(4) . . ? C10 P C16 103.1(4) . . ? C13 P C16 103.5(4) . . ? C10 P Ir 111.1(3) . . ? C13 P Ir 113.7(3) . . ? C16 P Ir 113.9(3) . . ? C2 C1 C6 119.7(9) . . ? C2 C1 C7 119.3(12) . . ? C6 C1 C7 120.9(10) . . ? C2 C1 Ir 70.3(5) . . ? C6 C1 Ir 74.2(5) . . ? C7 C1 Ir 128.9(7) . . ? C1 C2 C3 120.9(9) . . ? C1 C2 Ir 74.4(5) . . ? C3 C2 Ir 72.9(5) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? Ir C2 H2 124.8 . . ? C4 C3 C2 118.4(9) . . ? C4 C3 C8 120.8(9) . . ? C2 C3 C8 120.7(10) . . ? C4 C3 Ir 74.0(5) . . ? C2 C3 Ir 70.1(5) . . ? C8 C3 Ir 129.0(7) . . ? C5 C4 C3 120.2(9) . . ? C5 C4 Ir 73.8(5) . . ? C3 C4 Ir 69.8(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? Ir C4 H4 128.7 . . ? C4 C5 C6 119.1(9) . . ? C4 C5 C9 119.8(9) . . ? C6 C5 C9 120.8(10) . . ? C4 C5 Ir 71.5(5) . . ? C6 C5 Ir 71.6(5) . . ? C9 C5 Ir 133.7(7) . . ? C1 C6 C5 121.5(9) . . ? C1 C6 Ir 70.6(5) . . ? C5 C6 Ir 73.5(5) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? Ir C6 H6 129.1 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 C10 C11 108.9(8) . . ? C12 C10 P 114.1(7) . . ? C11 C10 P 114.7(11) . . ? C12 C10 H10 106.2 . . ? C11 C10 H10 106.2 . . ? P C10 H10 106.2 . . ? 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 . . ? C15 C13 C14 109.5(8) . . ? C15 C13 P 115.8(7) . . ? C14 C13 P 112.9(7) . . ? C15 C13 H13 106.0 . . ? C14 C13 H13 106.0 . . ? P C13 H13 106.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C17 110.6(9) . . ? C18 C16 P 113.5(7) . . ? C17 C16 P 110.5(7) . . ? C18 C16 H16 107.3 . . ? C17 C16 H16 107.3 . . ? P C16 H16 107.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F3 B F4 110.0(9) . . ? F3 B F2 107.5(10) . . ? F4 B F2 108.6(10) . . ? F3 B F1 110.9(9) . . ? F4 B F1 110.5(10) . . ? F2 B F1 109.2(9) . . ?