# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Guogang Shan' 'Haibin Li' 'Zhong-Min Su' 'Yi Liao' _publ_contact_author_name 'Guo-Gang Shan' _publ_contact_author_email shangg187@nenu.edu.cn data_3 _database_code_depnum_ccdc_archive 'CCDC 843779' #TrackingRef '- 843779.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H22 F10 Ir N8 P' _chemical_formula_sum 'C32 H22 F10 Ir N8 P' _chemical_formula_weight 931.75 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' 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 tetragonal _symmetry_space_group_name_H-M I4(1)cd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x+1/2, z+1/4' 'y, -x+1/2, z+1/4' '-x, y, z+1/2' 'x, -y, z+1/2' 'y+1/2, x, z+1/4' '-y+1/2, -x, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1, z+3/4' 'y+1/2, -x+1, z+3/4' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' 'y+1, x+1/2, z+3/4' '-y+1, -x+1/2, z+3/4' _cell_length_a 18.452(5) _cell_length_b 18.452(5) _cell_length_c 41.756(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 14217(6) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 34814 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 25.54 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7232 _exptl_absorpt_coefficient_mu 3.890 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.206 _exptl_absorpt_correction_T_max 0.396 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 34814 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.54 _reflns_number_total 6501 _reflns_number_gt 4938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0617P)^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 SHELXL _refine_ls_extinction_coef 0.000039(10) _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 0.034(12) _refine_ls_number_reflns 6501 _refine_ls_number_parameters 473 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 1.70296(2) 1.39426(2) 1.874461(17) 0.03564(13) Uani 1 1 d . . . N1 N 1.7650(6) 1.4602(5) 1.8179(2) 0.041(3) Uani 1 1 d . . . N7 N 1.6591(6) 1.6088(6) 1.9139(3) 0.051(3) Uani 1 1 d . . . N8 N 1.7058(6) 1.5736(6) 1.9344(3) 0.054(3) Uani 1 1 d . . . C23 C 1.7624(7) 1.4491(7) 1.9374(3) 0.044(3) Uani 1 1 d . . . C5 C 1.6515(6) 1.4106(6) 1.8339(3) 0.039(3) Uani 1 1 d . . . C19 C 1.8032(7) 1.3330(7) 1.9294(3) 0.057(3) Uani 1 1 d . . . H19 H 1.8057 1.2922 1.9164 0.068 Uiso 1 1 calc R . . N5 N 1.7646(5) 1.3908(5) 1.9187(2) 0.041(2) Uani 1 1 d . . . N3 N 1.6204(5) 1.3377(6) 1.8961(2) 0.049(3) Uani 1 1 d . . . N2 N 1.7827(5) 1.4421(5) 1.8488(2) 0.040(2) Uani 1 1 d . . . N6 N 1.6820(5) 1.4954(5) 1.8973(2) 0.041(2) Uani 1 1 d . . . C24 C 1.7182(7) 1.5066(7) 1.9242(2) 0.044(3) Uani 1 1 d . . . C27 C 1.7385(8) 1.6150(7) 1.9600(3) 0.058(3) Uani 1 1 d . . . C4 C 1.5786(6) 1.3898(7) 1.8243(3) 0.047(3) Uani 1 1 d . . . H4 H 1.5491 1.3625 1.8378 0.056 Uiso 1 1 calc R . . C15 C 1.6751(7) 1.2400(6) 1.8687(3) 0.050(3) Uani 1 1 d . . . C8 C 1.8796(9) 1.4785(9) 1.8231(4) 0.075(5) Uani 1 1 d . . . H8 H 1.9279 1.4889 1.8186 0.090 Uiso 1 1 calc R . . C22 C 1.7959(8) 1.4498(7) 1.9666(3) 0.058(4) Uani 1 1 d . . . H22 H 1.7926 1.4905 1.9796 0.070 Uiso 1 1 calc R . . C21 C 1.8361(8) 1.3878(7) 1.9771(3) 0.065(4) Uani 1 1 d . . . H21 H 1.8599 1.3875 1.9967 0.078 Uiso 1 1 calc R . . C9 C 1.8526(8) 1.4567(7) 1.8519(3) 0.059(3) Uani 1 1 d . . . H9 H 1.8792 1.4528 1.8707 0.071 Uiso 1 1 calc R . . N4 N 1.6177(6) 1.2669(6) 1.8890(2) 0.051(3) Uani 1 1 d . . . C14 C 1.7259(6) 1.2951(6) 1.8582(3) 0.043(3) Uani 1 1 d . . . C20 C 1.8380(8) 1.3308(8) 1.9576(3) 0.064(4) Uani 1 1 d . . . H20 H 1.8634 1.2894 1.9636 0.077 Uiso 1 1 calc R . . C1 C 1.6637(7) 1.4632(7) 1.7808(3) 0.053(3) Uani 1 1 d . . . C29 C 1.8291(12) 1.6979(10) 1.9776(5) 0.103(6) Uani 1 1 d . . . H29 H 1.8734 1.7207 1.9743 0.123 Uiso 1 1 calc R . . C2 C 1.5907(8) 1.4488(9) 1.7722(3) 0.072(5) Uani 1 1 d . . . H2 H 1.5700 1.4636 1.7530 0.087 Uiso 1 1 calc R . . C16 C 1.5557(8) 1.2381(9) 1.9034(4) 0.076(5) Uani 1 1 d . . . H16 H 1.5396 1.1906 1.9014 0.091 Uiso 1 1 calc R . . C28 C 1.7998(8) 1.6516(8) 1.9552(3) 0.069(4) Uani 1 1 d . . . H28 H 1.8239 1.6457 1.9358 0.083 Uiso 1 1 calc R . . C30 C 1.7892(12) 1.7086(9) 2.0055(4) 0.089(6) Uani 1 1 d . . . H30 H 1.8022 1.7453 2.0196 0.107 Uiso 1 1 calc R . . C31 C 1.7299(13) 1.6646(13) 2.0121(5) 0.125(9) Uani 1 1 d . . . H31 H 1.7093 1.6656 2.0324 0.149 Uiso 1 1 calc R . . C10 C 1.6833(8) 1.1689(7) 1.8598(3) 0.065(4) Uani 1 1 d . . . C3 C 1.5548(7) 1.4120(8) 1.7946(3) 0.061(4) Uani 1 1 d . . . C6 C 1.6914(6) 1.4450(6) 1.8095(3) 0.040(3) Uani 1 1 d . . . C17 C 1.5239(9) 1.2897(9) 1.9204(5) 0.092(6) Uani 1 1 d . . . H17 H 1.4831 1.2850 1.9333 0.110 Uiso 1 1 calc R . . F4 F 1.6348(5) 1.1199(4) 1.8716(3) 0.106(3) Uani 1 1 d . . . F2 F 1.7029(5) 1.4995(5) 1.75864(19) 0.082(2) Uani 1 1 d . . . F1 F 1.4824(5) 1.3901(6) 1.7886(2) 0.093(3) Uani 1 1 d . . . F3 F 1.8378(5) 1.1776(5) 1.8093(2) 0.084(3) Uani 1 1 d . . . C26 C 1.5937(7) 1.5702(7) 1.8655(3) 0.059(4) Uani 1 1 d . . . H26A H 1.5761 1.6189 1.8675 0.088 Uiso 1 1 calc R . . H26B H 1.5539 1.5369 1.8673 0.088 Uiso 1 1 calc R . . H26C H 1.6167 1.5641 1.8451 0.088 Uiso 1 1 calc R . . C12 C 1.7856(8) 1.1986(8) 1.8299(3) 0.060(4) Uani 1 1 d . . . C11 C 1.7375(8) 1.1446(7) 1.8397(3) 0.060(4) Uani 1 1 d . . . H11 H 1.7416 1.0966 1.8332 0.072 Uiso 1 1 calc R . . C13 C 1.7813(7) 1.2704(7) 1.8387(3) 0.053(3) Uani 1 1 d . . . H13 H 1.8161 1.3028 1.8314 0.064 Uiso 1 1 calc R . . C7 C 1.8211(7) 1.4825(7) 1.8010(3) 0.057(4) Uani 1 1 d . . . H7 H 1.8221 1.4974 1.7797 0.068 Uiso 1 1 calc R . . C32 C 1.7004(10) 1.6184(10) 1.9884(4) 0.098(6) Uani 1 1 d . . . H32 H 1.6582 1.5919 1.9917 0.117 Uiso 1 1 calc R . . C18 C 1.5634(7) 1.3512(9) 1.9149(3) 0.062(4) Uani 1 1 d . . . H18 H 1.5520 1.3966 1.9232 0.075 Uiso 1 1 calc R . . C25 C 1.6467(7) 1.5556(8) 1.8914(3) 0.056(3) Uani 1 1 d . . . P1 P 1.5000 1.0000 1.92237(12) 0.0595(13) Uani 1 2 d S . . P2 P 1.5000 1.5000 1.98208(13) 0.0745(16) Uani 1 2 d S . . F8 F 1.5821(6) 1.0211(7) 1.9221(3) 0.112(4) Uani 1 1 d . . . F9 F 1.4923(9) 1.4145(6) 1.9803(3) 0.149(6) Uani 1 1 d . . . F10 F 1.5783(11) 1.4969(13) 1.9915(12) 0.45(3) Uani 1 1 d . . . F6 F 1.5000 1.0000 1.9579(4) 0.188(10) Uani 1 2 d S . . F5 F 1.5242(8) 0.9210(7) 1.9218(5) 0.187(7) Uani 1 1 d . . . F7 F 1.5000 1.0000 1.8853(4) 0.213(12) Uani 1 2 d S . . F11 F 1.5000 1.5000 1.9487(5) 0.37(3) Uani 1 2 d S . . F12 F 1.5000 1.5000 2.0170(10) 0.291(15) Uani 1 2 d SU . . 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 0.0378(2) 0.0367(2) 0.03251(19) -0.0044(2) -0.0012(2) -0.00193(18) N1 0.053(7) 0.033(5) 0.038(6) 0.000(4) -0.001(5) 0.006(5) N7 0.057(7) 0.047(6) 0.049(6) -0.010(5) -0.006(5) 0.009(5) N8 0.065(7) 0.050(6) 0.048(6) -0.018(5) -0.006(6) 0.001(6) C23 0.051(8) 0.046(7) 0.033(6) 0.010(6) 0.001(6) -0.008(6) C5 0.042(7) 0.034(7) 0.041(7) -0.011(5) 0.002(5) 0.008(5) C19 0.074(9) 0.051(8) 0.046(7) -0.012(6) -0.008(7) -0.011(7) N5 0.039(5) 0.045(6) 0.038(6) -0.001(5) -0.004(4) 0.005(5) N3 0.048(6) 0.054(7) 0.045(6) -0.010(5) 0.006(5) -0.003(5) N2 0.035(5) 0.036(5) 0.047(6) -0.006(4) 0.000(4) 0.000(4) N6 0.035(5) 0.042(6) 0.044(6) -0.005(5) -0.009(4) 0.003(4) C24 0.069(8) 0.039(7) 0.024(6) -0.005(5) -0.002(5) -0.005(6) C27 0.074(9) 0.049(8) 0.050(8) -0.009(6) 0.002(7) 0.004(7) C4 0.038(7) 0.049(7) 0.053(8) -0.012(6) 0.006(6) -0.010(6) C15 0.066(7) 0.040(6) 0.045(9) 0.016(6) -0.007(6) 0.000(6) C8 0.065(11) 0.084(11) 0.076(11) -0.016(9) 0.043(9) -0.031(9) C22 0.085(10) 0.048(8) 0.042(7) -0.014(6) -0.014(7) -0.029(8) C21 0.093(11) 0.048(8) 0.055(8) -0.016(7) -0.028(8) -0.001(8) C9 0.060(9) 0.050(8) 0.068(9) -0.012(7) 0.003(7) -0.007(7) N4 0.060(7) 0.040(6) 0.053(6) 0.000(5) 0.008(5) -0.002(5) C14 0.041(6) 0.050(7) 0.038(6) 0.003(5) -0.003(5) -0.004(5) C20 0.084(10) 0.052(8) 0.056(8) 0.020(7) -0.007(8) -0.007(8) C1 0.066(9) 0.048(8) 0.044(7) 0.003(6) 0.007(7) 0.010(7) C29 0.122(16) 0.086(13) 0.099(15) 0.009(12) -0.046(13) -0.036(11) C2 0.069(10) 0.101(12) 0.047(8) 0.033(8) -0.025(7) -0.016(9) C16 0.066(10) 0.078(11) 0.084(11) 0.020(9) -0.004(9) -0.040(9) C28 0.079(11) 0.079(10) 0.049(8) -0.020(8) -0.023(8) -0.005(9) C30 0.125(16) 0.077(12) 0.066(11) -0.036(9) -0.033(11) 0.010(11) C31 0.16(2) 0.16(2) 0.062(12) -0.064(13) 0.013(12) -0.049(18) C10 0.082(10) 0.043(7) 0.071(9) 0.005(7) -0.012(8) -0.018(7) C3 0.047(8) 0.076(10) 0.060(9) -0.027(8) -0.034(7) 0.016(7) C6 0.040(7) 0.044(7) 0.035(6) -0.001(5) -0.007(5) 0.002(6) C17 0.072(11) 0.079(12) 0.124(15) 0.013(11) 0.047(11) -0.006(9) F4 0.140(8) 0.052(5) 0.126(8) 0.005(6) 0.036(9) -0.029(5) F2 0.100(6) 0.089(6) 0.058(5) 0.030(5) 0.001(4) -0.005(5) F1 0.067(6) 0.119(9) 0.092(7) 0.008(6) -0.035(5) -0.011(5) F3 0.090(6) 0.081(6) 0.082(6) -0.021(5) 0.014(5) 0.036(5) C26 0.066(8) 0.051(7) 0.059(9) 0.000(6) -0.030(7) 0.000(6) C12 0.078(10) 0.062(9) 0.039(7) -0.016(7) -0.002(7) 0.020(8) C11 0.086(11) 0.041(8) 0.054(9) -0.007(7) 0.002(8) 0.005(8) C13 0.059(8) 0.051(8) 0.049(7) -0.005(6) 0.005(6) 0.006(6) C7 0.054(8) 0.055(8) 0.062(9) 0.003(7) 0.019(7) -0.025(7) C32 0.120(15) 0.101(13) 0.072(11) -0.032(10) 0.013(10) -0.036(11) C18 0.047(8) 0.095(12) 0.044(8) -0.009(8) 0.012(6) 0.001(8) C25 0.052(8) 0.065(9) 0.052(7) -0.003(7) 0.000(6) -0.005(7) P1 0.060(3) 0.075(4) 0.044(3) 0.000 0.000 -0.004(3) P2 0.085(5) 0.089(5) 0.049(3) 0.000 0.000 0.006(4) F8 0.087(7) 0.150(10) 0.099(7) 0.019(7) -0.020(6) -0.040(7) F9 0.215(15) 0.079(8) 0.154(11) 0.024(8) 0.058(11) 0.010(9) F10 0.156(17) 0.20(2) 1.01(9) 0.21(4) -0.24(3) -0.077(16) F6 0.186(19) 0.31(3) 0.070(10) 0.000 0.000 -0.12(2) F5 0.137(11) 0.101(9) 0.32(2) -0.054(12) -0.044(13) 0.005(8) F7 0.049(8) 0.48(4) 0.112(17) 0.000 0.000 0.016(17) F11 0.91(9) 0.102(15) 0.115(16) 0.000 0.000 0.18(3) F12 0.291(15) 0.291(15) 0.291(15) 0.000 0.000 0.0003(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 Ir1 C5 1.964(12) . ? Ir1 C14 1.997(12) . ? Ir1 N2 2.023(9) . ? Ir1 N3 2.055(10) . ? Ir1 N6 2.131(9) . ? Ir1 N5 2.171(10) . ? N1 C7 1.319(15) . ? N1 N2 1.374(13) . ? N1 C6 1.430(15) . ? N7 N8 1.378(15) . ? N7 C25 1.378(16) . ? N8 C24 1.327(15) . ? N8 C27 1.445(17) . ? C23 N5 1.330(15) . ? C23 C22 1.365(17) . ? C23 C24 1.449(17) . ? C5 C6 1.410(16) . ? C5 C4 1.454(17) . ? C19 C20 1.341(17) . ? C19 N5 1.359(16) . ? C19 H19 0.9300 . ? N3 C18 1.337(15) . ? N3 N4 1.340(14) . ? N2 C9 1.324(16) . ? N6 C25 1.311(16) . ? N6 C24 1.323(13) . ? C27 C28 1.33(2) . ? C27 C32 1.38(2) . ? C4 C3 1.379(19) . ? C4 H4 0.9300 . ? C15 C10 1.371(18) . ? C15 C14 1.450(16) . ? C15 N4 1.447(16) . ? C8 C9 1.36(2) . ? C8 C7 1.42(2) . ? C8 H8 0.9300 . ? C22 C21 1.432(19) . ? C22 H22 0.9300 . ? C21 C20 1.330(18) . ? C21 H21 0.9300 . ? C9 H9 0.9300 . ? N4 C16 1.396(17) . ? C14 C13 1.383(16) . ? C20 H20 0.9300 . ? C1 C6 1.345(16) . ? C1 F2 1.352(14) . ? C1 C2 1.419(19) . ? C29 C28 1.38(2) . ? C29 C30 1.39(3) . ? C29 H29 0.9300 . ? C2 C3 1.33(2) . ? C2 H2 0.9300 . ? C16 C17 1.32(2) . ? C16 H16 0.9300 . ? C28 H28 0.9300 . ? C30 C31 1.39(3) . ? C30 H30 0.9300 . ? C31 C32 1.42(2) . ? C31 H31 0.9300 . ? C10 F4 1.366(15) . ? C10 C11 1.381(19) . ? C3 F1 1.418(16) . ? C17 C18 1.37(2) . ? C17 H17 0.9300 . ? F3 C12 1.349(15) . ? C26 C25 1.482(16) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C12 C13 1.376(18) . ? C12 C11 1.39(2) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C7 H7 0.9300 . ? C32 H32 0.9300 . ? C18 H18 0.9300 . ? P1 F5 1.525(13) 2_875 ? P1 F5 1.525(13) . ? P1 F6 1.482(17) . ? P1 F7 1.547(16) . ? P1 F8 1.563(10) . ? P1 F8 1.563(10) 2_875 ? P2 F12 1.46(4) . ? P2 F11 1.39(2) . ? P2 F10 1.497(17) 2_885 ? P2 F10 1.497(17) . ? P2 F9 1.586(12) . ? P2 F9 1.586(12) 2_885 ? 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 C5 Ir1 C14 87.1(4) . . ? C5 Ir1 N2 80.1(5) . . ? C14 Ir1 N2 93.7(4) . . ? C5 Ir1 N3 95.6(5) . . ? C14 Ir1 N3 80.9(4) . . ? N2 Ir1 N3 173.4(4) . . ? C5 Ir1 N6 99.4(4) . . ? C14 Ir1 N6 173.2(4) . . ? N2 Ir1 N6 89.2(4) . . ? N3 Ir1 N6 96.6(4) . . ? C5 Ir1 N5 172.5(4) . . ? C14 Ir1 N5 98.7(4) . . ? N2 Ir1 N5 94.7(4) . . ? N3 Ir1 N5 90.0(4) . . ? N6 Ir1 N5 74.9(4) . . ? C7 N1 N2 113.0(11) . . ? C7 N1 C6 132.5(11) . . ? N2 N1 C6 114.2(10) . . ? N8 N7 C25 101.0(10) . . ? C24 N8 N7 110.3(10) . . ? C24 N8 C27 131.2(12) . . ? N7 N8 C27 118.1(10) . . ? N5 C23 C22 121.1(12) . . ? N5 C23 C24 112.7(10) . . ? C22 C23 C24 126.1(12) . . ? C6 C5 C4 113.7(11) . . ? C6 C5 Ir1 116.1(9) . . ? C4 C5 Ir1 130.1(9) . . ? C20 C19 N5 124.3(13) . . ? C20 C19 H19 117.9 . . ? N5 C19 H19 117.9 . . ? C23 N5 C19 117.2(10) . . ? C23 N5 Ir1 117.4(8) . . ? C19 N5 Ir1 125.3(8) . . ? C18 N3 N4 106.3(11) . . ? C18 N3 Ir1 138.3(10) . . ? N4 N3 Ir1 115.3(7) . . ? C9 N2 N1 105.9(10) . . ? C9 N2 Ir1 138.3(9) . . ? N1 N2 Ir1 115.5(7) . . ? C25 N6 C24 106.1(10) . . ? C25 N6 Ir1 138.4(8) . . ? C24 N6 Ir1 115.2(8) . . ? N6 C24 N8 109.4(11) . . ? N6 C24 C23 119.6(11) . . ? N8 C24 C23 131.0(11) . . ? C28 C27 C32 122.6(14) . . ? C28 C27 N8 120.8(12) . . ? C32 C27 N8 116.5(14) . . ? C3 C4 C5 117.7(12) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C10 C15 C14 121.2(12) . . ? C10 C15 N4 124.6(11) . . ? C14 C15 N4 114.2(10) . . ? C9 C8 C7 108.0(13) . . ? C9 C8 H8 126.0 . . ? C7 C8 H8 126.0 . . ? C23 C22 C21 120.1(12) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C20 C21 C22 117.2(13) . . ? C20 C21 H21 121.4 . . ? C22 C21 H21 121.4 . . ? N2 C9 C8 109.4(14) . . ? N2 C9 H9 125.3 . . ? C8 C9 H9 125.3 . . ? N3 N4 C16 107.9(11) . . ? N3 N4 C15 115.8(10) . . ? C16 N4 C15 136.2(12) . . ? C13 C14 C15 115.0(11) . . ? C13 C14 Ir1 131.2(9) . . ? C15 C14 Ir1 113.7(8) . . ? C19 C20 C21 120.0(14) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C6 C1 F2 122.0(12) . . ? C6 C1 C2 122.6(12) . . ? F2 C1 C2 115.4(11) . . ? C28 C29 C30 116.7(18) . . ? C28 C29 H29 121.6 . . ? C30 C29 H29 121.6 . . ? C3 C2 C1 113.0(11) . . ? C3 C2 H2 123.5 . . ? C1 C2 H2 123.5 . . ? C17 C16 N4 108.7(14) . . ? C17 C16 H16 125.7 . . ? N4 C16 H16 125.7 . . ? C27 C28 C29 123.0(16) . . ? C27 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? C31 C30 C29 120.0(15) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 121.0(18) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? F4 C10 C11 118.6(13) . . ? F4 C10 C15 117.6(13) . . ? C11 C10 C15 123.7(13) . . ? C2 C3 C4 128.7(12) . . ? C2 C3 F1 119.3(12) . . ? C4 C3 F1 112.0(14) . . ? C1 C6 C5 124.0(12) . . ? C1 C6 N1 122.0(11) . . ? C5 C6 N1 114.0(10) . . ? C16 C17 C18 105.7(14) . . ? C16 C17 H17 127.1 . . ? C18 C17 H17 127.1 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? F3 C12 C13 119.2(14) . . ? F3 C12 C11 115.8(12) . . ? C13 C12 C11 125.0(13) . . ? C10 C11 C12 113.9(12) . . ? C10 C11 H11 123.0 . . ? C12 C11 H11 123.0 . . ? C12 C13 C14 121.1(13) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? N1 C7 C8 103.5(12) . . ? N1 C7 H7 128.2 . . ? C8 C7 H7 128.2 . . ? C27 C32 C31 115.7(17) . . ? C27 C32 H32 122.2 . . ? C31 C32 H32 122.2 . . ? N3 C18 C17 111.2(14) . . ? N3 C18 H18 124.4 . . ? C17 C18 H18 124.4 . . ? N6 C25 N7 113.2(11) . . ? N6 C25 C26 128.3(12) . . ? N7 C25 C26 118.4(12) . . ? F5 P1 F5 178.3(16) 2_875 . ? F5 P1 F6 90.8(8) 2_875 . ? F5 P1 F6 90.8(8) . . ? F5 P1 F7 89.2(8) 2_875 . ? F5 P1 F7 89.2(8) . . ? F6 P1 F7 180.000(14) . . ? F5 P1 F8 92.6(8) 2_875 . ? F5 P1 F8 87.4(8) . . ? F6 P1 F8 90.3(4) . . ? F7 P1 F8 89.7(4) . . ? F5 P1 F8 87.4(8) 2_875 2_875 ? F5 P1 F8 92.6(8) . 2_875 ? F6 P1 F8 90.3(4) . 2_875 ? F7 P1 F8 89.7(4) . 2_875 ? F8 P1 F8 179.3(9) . 2_875 ? F12 P2 F11 180.00(3) . . ? F12 P2 F10 75(2) . 2_885 ? F11 P2 F10 105(2) . 2_885 ? F12 P2 F10 75(2) . . ? F11 P2 F10 105(2) . . ? F10 P2 F10 150(4) 2_885 . ? F12 P2 F9 92.7(5) . . ? F11 P2 F9 87.3(5) . . ? F10 P2 F9 88.0(10) 2_885 . ? F10 P2 F9 93.4(11) . . ? F12 P2 F9 92.7(5) . 2_885 ? F11 P2 F9 87.3(5) . 2_885 ? F10 P2 F9 93.4(11) 2_885 2_885 ? F10 P2 F9 88.0(10) . 2_885 ? F9 P2 F9 174.6(11) . 2_885 ? 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 C25 N7 N8 C24 0.0(14) . . . . ? C25 N7 N8 C27 173.2(12) . . . . ? C14 Ir1 C5 C6 -95.0(9) . . . . ? N2 Ir1 C5 C6 -0.7(8) . . . . ? N3 Ir1 C5 C6 -175.6(9) . . . . ? N6 Ir1 C5 C6 86.8(9) . . . . ? N5 Ir1 C5 C6 46(4) . . . . ? C14 Ir1 C5 C4 82.0(11) . . . . ? N2 Ir1 C5 C4 176.3(11) . . . . ? N3 Ir1 C5 C4 1.5(11) . . . . ? N6 Ir1 C5 C4 -96.2(11) . . . . ? N5 Ir1 C5 C4 -137(3) . . . . ? C22 C23 N5 C19 -1.9(18) . . . . ? C24 C23 N5 C19 -178.3(11) . . . . ? C22 C23 N5 Ir1 175.9(10) . . . . ? C24 C23 N5 Ir1 -0.6(14) . . . . ? C20 C19 N5 C23 1(2) . . . . ? C20 C19 N5 Ir1 -176.5(10) . . . . ? C5 Ir1 N5 C23 40(4) . . . . ? C14 Ir1 N5 C23 -179.2(9) . . . . ? N2 Ir1 N5 C23 86.3(9) . . . . ? N3 Ir1 N5 C23 -98.5(9) . . . . ? N6 Ir1 N5 C23 -1.7(9) . . . . ? C5 Ir1 N5 C19 -143(3) . . . . ? C14 Ir1 N5 C19 -1.7(11) . . . . ? N2 Ir1 N5 C19 -96.2(10) . . . . ? N3 Ir1 N5 C19 79.1(10) . . . . ? N6 Ir1 N5 C19 175.9(11) . . . . ? C5 Ir1 N3 C18 -92.1(13) . . . . ? C14 Ir1 N3 C18 -178.2(14) . . . . ? N2 Ir1 N3 C18 -142(3) . . . . ? N6 Ir1 N3 C18 8.1(13) . . . . ? N5 Ir1 N3 C18 82.9(13) . . . . ? C5 Ir1 N3 N4 83.6(9) . . . . ? C14 Ir1 N3 N4 -2.6(8) . . . . ? N2 Ir1 N3 N4 33(4) . . . . ? N6 Ir1 N3 N4 -176.2(8) . . . . ? N5 Ir1 N3 N4 -101.4(8) . . . . ? C7 N1 N2 C9 2.7(13) . . . . ? C6 N1 N2 C9 177.4(10) . . . . ? C7 N1 N2 Ir1 -171.8(8) . . . . ? C6 N1 N2 Ir1 2.8(11) . . . . ? C5 Ir1 N2 C9 -173.3(13) . . . . ? C14 Ir1 N2 C9 -86.9(12) . . . . ? N3 Ir1 N2 C9 -122(3) . . . . ? N6 Ir1 N2 C9 87.0(12) . . . . ? N5 Ir1 N2 C9 12.2(12) . . . . ? C5 Ir1 N2 N1 -1.2(7) . . . . ? C14 Ir1 N2 N1 85.2(7) . . . . ? N3 Ir1 N2 N1 50(4) . . . . ? N6 Ir1 N2 N1 -100.9(7) . . . . ? N5 Ir1 N2 N1 -175.7(7) . . . . ? C5 Ir1 N6 C25 1.6(14) . . . . ? C14 Ir1 N6 C25 -163(3) . . . . ? N2 Ir1 N6 C25 81.5(13) . . . . ? N3 Ir1 N6 C25 -95.2(13) . . . . ? N5 Ir1 N6 C25 176.6(14) . . . . ? C5 Ir1 N6 C24 -171.1(8) . . . . ? C14 Ir1 N6 C24 25(4) . . . . ? N2 Ir1 N6 C24 -91.2(8) . . . . ? N3 Ir1 N6 C24 92.1(8) . . . . ? N5 Ir1 N6 C24 3.9(8) . . . . ? C25 N6 C24 N8 -0.8(14) . . . . ? Ir1 N6 C24 N8 174.2(8) . . . . ? C25 N6 C24 C23 179.3(11) . . . . ? Ir1 N6 C24 C23 -5.7(14) . . . . ? N7 N8 C24 N6 0.5(14) . . . . ? C27 N8 C24 N6 -171.5(13) . . . . ? N7 N8 C24 C23 -179.5(12) . . . . ? C27 N8 C24 C23 8(2) . . . . ? N5 C23 C24 N6 4.2(17) . . . . ? C22 C23 C24 N6 -172.0(12) . . . . ? N5 C23 C24 N8 -175.7(13) . . . . ? C22 C23 C24 N8 8(2) . . . . ? C24 N8 C27 C28 84.7(19) . . . . ? N7 N8 C27 C28 -86.8(16) . . . . ? C24 N8 C27 C32 -99.6(18) . . . . ? N7 N8 C27 C32 89.0(17) . . . . ? C6 C5 C4 C3 -6.4(16) . . . . ? Ir1 C5 C4 C3 176.5(9) . . . . ? N5 C23 C22 C21 2(2) . . . . ? C24 C23 C22 C21 177.9(13) . . . . ? C23 C22 C21 C20 -1(2) . . . . ? N1 N2 C9 C8 -4.3(14) . . . . ? Ir1 N2 C9 C8 168.3(10) . . . . ? C7 C8 C9 N2 4.3(17) . . . . ? C18 N3 N4 C16 1.7(14) . . . . ? Ir1 N3 N4 C16 -175.3(9) . . . . ? C18 N3 N4 C15 -179.9(10) . . . . ? Ir1 N3 N4 C15 3.1(13) . . . . ? C10 C15 N4 N3 177.3(12) . . . . ? C14 C15 N4 N3 -1.9(15) . . . . ? C10 C15 N4 C16 -5(2) . . . . ? C14 C15 N4 C16 176.0(14) . . . . ? C10 C15 C14 C13 0.8(17) . . . . ? N4 C15 C14 C13 -180.0(10) . . . . ? C10 C15 C14 Ir1 -179.5(10) . . . . ? N4 C15 C14 Ir1 -0.3(13) . . . . ? C5 Ir1 C14 C13 84.9(12) . . . . ? N2 Ir1 C14 C13 5.0(12) . . . . ? N3 Ir1 C14 C13 -178.9(12) . . . . ? N6 Ir1 C14 C13 -111(3) . . . . ? N5 Ir1 C14 C13 -90.4(12) . . . . ? C5 Ir1 C14 C15 -94.7(9) . . . . ? N2 Ir1 C14 C15 -174.6(8) . . . . ? N3 Ir1 C14 C15 1.5(8) . . . . ? N6 Ir1 C14 C15 70(4) . . . . ? N5 Ir1 C14 C15 90.0(8) . . . . ? N5 C19 C20 C21 0(2) . . . . ? C22 C21 C20 C19 0(2) . . . . ? C6 C1 C2 C3 -4(2) . . . . ? F2 C1 C2 C3 178.9(13) . . . . ? N3 N4 C16 C17 -3.4(17) . . . . ? C15 N4 C16 C17 178.7(15) . . . . ? C32 C27 C28 C29 -2(3) . . . . ? N8 C27 C28 C29 173.1(15) . . . . ? C30 C29 C28 C27 -4(3) . . . . ? C28 C29 C30 C31 11(3) . . . . ? C29 C30 C31 C32 -12(4) . . . . ? C14 C15 C10 F4 177.6(12) . . . . ? N4 C15 C10 F4 -1.6(19) . . . . ? C14 C15 C10 C11 -3(2) . . . . ? N4 C15 C10 C11 178.3(13) . . . . ? C1 C2 C3 C4 3(2) . . . . ? C1 C2 C3 F1 -176.4(12) . . . . ? C5 C4 C3 C2 2(2) . . . . ? C5 C4 C3 F1 -178.3(10) . . . . ? F2 C1 C6 C5 176.6(11) . . . . ? C2 C1 C6 C5 0(2) . . . . ? F2 C1 C6 N1 -2.7(19) . . . . ? C2 C1 C6 N1 -179.7(13) . . . . ? C4 C5 C6 C1 5.6(17) . . . . ? Ir1 C5 C6 C1 -176.9(10) . . . . ? C4 C5 C6 N1 -175.1(9) . . . . ? Ir1 C5 C6 N1 2.4(13) . . . . ? C7 N1 C6 C1 -11(2) . . . . ? N2 N1 C6 C1 176.0(10) . . . . ? C7 N1 C6 C5 169.9(12) . . . . ? N2 N1 C6 C5 -3.4(14) . . . . ? N4 C16 C17 C18 4(2) . . . . ? F4 C10 C11 C12 -177.8(13) . . . . ? C15 C10 C11 C12 2(2) . . . . ? F3 C12 C11 C10 -177.7(12) . . . . ? C13 C12 C11 C10 -1(2) . . . . ? F3 C12 C13 C14 175.9(11) . . . . ? C11 C12 C13 C14 -1(2) . . . . ? C15 C14 C13 C12 0.9(18) . . . . ? Ir1 C14 C13 C12 -178.7(9) . . . . ? N2 N1 C7 C8 -0.1(15) . . . . ? C6 N1 C7 C8 -173.5(13) . . . . ? C9 C8 C7 N1 -2.5(17) . . . . ? C28 C27 C32 C31 1(3) . . . . ? N8 C27 C32 C31 -174.3(17) . . . . ? C30 C31 C32 C27 6(3) . . . . ? N4 N3 C18 C17 0.5(16) . . . . ? Ir1 N3 C18 C17 176.4(12) . . . . ? C16 C17 C18 N3 -3(2) . . . . ? C24 N6 C25 N7 0.8(15) . . . . ? Ir1 N6 C25 N7 -172.4(9) . . . . ? C24 N6 C25 C26 -174.9(13) . . . . ? Ir1 N6 C25 C26 12(2) . . . . ? N8 N7 C25 N6 -0.5(14) . . . . ? N8 N7 C25 C26 175.6(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.904 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.126