# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Luisa De Cola' _publ_contact_author_email DECOLA@UNI-MUENSTER.DE _publ_section_title ; 1,2,3-Triazolyl-Pyridine Derivatives as Chelating Ligands for Blue Iridium(III) Complexes. Photophysics and Electroluminescent Devices ; loop_ _publ_author_name 'Luisa De Cola' 'Rodrigo Q Albuquerque' 'P. Michel Fransen' 'Roland Frohlich' 'Henk M. Janssen' ; E.Orselli ; # Attachment 'complex3.cif' data_fro4435 _database_code_depnum_ccdc_archive 'CCDC 678024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H21 Cl2 F6 Ir N6' _chemical_formula_weight 914.69 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' 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 C2/c 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' '-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 26.1732(2) _cell_length_b 15.7673(2) _cell_length_c 18.1899(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.8320(10) _cell_angle_gamma 90.00 _cell_volume 6638.26(14) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6490 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3552 _exptl_absorpt_coefficient_mu 4.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3770 _exptl_absorpt_correction_T_max 0.6586 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22679 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28.29 _reflns_number_total 8192 _reflns_number_gt 6738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0468P)^2^+20.4566P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8192 _refine_ls_number_parameters 461 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.006 _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 Ir Ir -0.305571(6) 0.442018(9) 1.112632(8) 0.02166(6) Uani 1 1 d . . . N1 N -0.25807(15) 0.4370(2) 1.2472(2) 0.0229(7) Uani 1 1 d . . . C2 C -0.28176(19) 0.4279(3) 1.2986(3) 0.0291(9) Uani 1 1 d . . . H2 H -0.3219 0.4203 1.2756 0.035 Uiso 1 1 calc R . . C3 C -0.2488(2) 0.4293(3) 1.3843(3) 0.0309(9) Uani 1 1 d . . . H3 H -0.2664 0.4230 1.4187 0.037 Uiso 1 1 calc R . . C4 C -0.1894(2) 0.4403(3) 1.4189(3) 0.0300(9) Uani 1 1 d . . . H4 H -0.1663 0.4416 1.4769 0.036 Uiso 1 1 calc R . . C5 C -0.16459(19) 0.4493(3) 1.3664(3) 0.0294(9) Uani 1 1 d . . . H5 H -0.1244 0.4563 1.3885 0.035 Uiso 1 1 calc R . . C6 C -0.19993(18) 0.4479(2) 1.2807(2) 0.0238(8) Uani 1 1 d . . . C7 C -0.17929(17) 0.4602(3) 1.2199(2) 0.0249(8) Uani 1 1 d . . . N8 N -0.21971(15) 0.4706(2) 1.1391(2) 0.0244(7) Uani 1 1 d . . . N9 N -0.19320(16) 0.4861(2) 1.0936(2) 0.0316(8) Uani 1 1 d . . . N10 N -0.13581(16) 0.4851(3) 1.1427(2) 0.0379(9) Uani 1 1 d . . . C11 C -0.12572(18) 0.4687(3) 1.2220(3) 0.0294(9) Uani 1 1 d . . . C12 C -0.06740(19) 0.4561(3) 1.2918(3) 0.0339(10) Uani 1 1 d . . . C13 C -0.0442(2) 0.3752(4) 1.3095(3) 0.0507(13) Uani 1 1 d . . . H13 H -0.0646 0.3291 1.2759 0.061 Uiso 1 1 calc R . . C14 C 0.0093(3) 0.3634(4) 1.3771(4) 0.0599(16) Uani 1 1 d . . . F14 F 0.0310(2) 0.2831(3) 1.3939(3) 0.1110(18) Uani 1 1 d . . . C15 C 0.0416(2) 0.4281(4) 1.4280(4) 0.0534(15) Uani 1 1 d . . . H15 H 0.0784 0.4187 1.4731 0.064 Uiso 1 1 calc R . . C16 C 0.0173(2) 0.5063(4) 1.4094(4) 0.0563(15) Uani 1 1 d . . . F16 F 0.04767(19) 0.5710(3) 1.4591(3) 0.1007(18) Uani 1 1 d . . . C17 C -0.0357(2) 0.5231(4) 1.3438(3) 0.0497(13) Uani 1 1 d . . . H17 H -0.0506 0.5786 1.3338 0.060 Uiso 1 1 calc R . . N21 N -0.33012(15) 0.5627(2) 1.1209(2) 0.0250(7) Uani 1 1 d . . . C22 C -0.2983(2) 0.6320(3) 1.1268(3) 0.0323(10) Uani 1 1 d . . . H22 H -0.2612 0.6244 1.1319 0.039 Uiso 1 1 calc R . . C23 C -0.3177(2) 0.7131(3) 1.1256(3) 0.0398(11) Uani 1 1 d . . . H23 H -0.2944 0.7601 1.1299 0.048 Uiso 1 1 calc R . . C24 C -0.3729(2) 0.7240(3) 1.1180(3) 0.0439(12) Uani 1 1 d . . . H24 H -0.3874 0.7788 1.1165 0.053 Uiso 1 1 calc R . . C25 C -0.4058(2) 0.6543(3) 1.1126(3) 0.0370(10) Uani 1 1 d . . . H25 H -0.4428 0.6613 1.1081 0.044 Uiso 1 1 calc R . . C26 C -0.38439(18) 0.5727(3) 1.1138(2) 0.0264(8) Uani 1 1 d . . . C27 C -0.41417(17) 0.4919(3) 1.1063(2) 0.0264(9) Uani 1 1 d . . . C28 C -0.46827(19) 0.4818(3) 1.1022(3) 0.0321(9) Uani 1 1 d . . . F28 F -0.49747(12) 0.55092(18) 1.10743(19) 0.0443(7) Uani 1 1 d . . . C29 C -0.4943(2) 0.4041(3) 1.0940(3) 0.0381(11) Uani 1 1 d . . . H29 H -0.5307 0.3988 1.0919 0.046 Uiso 1 1 calc R . . C30 C -0.4644(2) 0.3349(3) 1.0893(3) 0.0398(11) Uani 1 1 d . . . F30 F -0.48970(14) 0.2574(2) 1.0800(2) 0.0616(9) Uani 1 1 d . . . C31 C -0.41069(19) 0.3393(3) 1.0927(3) 0.0328(9) Uani 1 1 d . . . H31 H -0.3922 0.2898 1.0886 0.039 Uiso 1 1 calc R . . C32 C -0.38421(17) 0.4183(3) 1.1023(2) 0.0244(8) Uani 1 1 d . . . N41 N -0.29236(15) 0.3187(2) 1.0916(2) 0.0268(7) Uani 1 1 d . . . C42 C -0.2625(2) 0.2619(3) 1.1518(3) 0.0372(10) Uani 1 1 d . . . H42 H -0.2444 0.2805 1.2073 0.045 Uiso 1 1 calc R . . C43 C -0.2572(2) 0.1783(3) 1.1361(3) 0.0435(12) Uani 1 1 d . . . H43 H -0.2365 0.1403 1.1799 0.052 Uiso 1 1 calc R . . C44 C -0.2830(2) 0.1511(3) 1.0542(3) 0.0445(12) Uani 1 1 d . . . H44 H -0.2799 0.0942 1.0414 0.053 Uiso 1 1 calc R . . C45 C -0.3134(2) 0.2088(3) 0.9916(3) 0.0392(11) Uani 1 1 d . . . H45 H -0.3312 0.1907 0.9359 0.047 Uiso 1 1 calc R . . C46 C -0.31794(19) 0.2929(3) 1.0100(3) 0.0298(9) Uani 1 1 d . . . C47 C -0.34661(19) 0.3624(3) 0.9519(2) 0.0295(9) Uani 1 1 d . . . C48 C -0.3746(2) 0.3559(3) 0.8653(3) 0.0397(11) Uani 1 1 d . . . F48 F -0.37865(16) 0.2798(2) 0.82850(18) 0.0618(9) Uani 1 1 d . . . C49 C -0.3996(2) 0.4240(4) 0.8133(3) 0.0454(13) Uani 1 1 d . . . H49 H -0.4195 0.4180 0.7552 0.054 Uiso 1 1 calc R . . C50 C -0.3938(2) 0.5010(3) 0.8514(3) 0.0384(11) Uani 1 1 d . . . F50 F -0.41711(16) 0.5700(2) 0.80138(18) 0.0568(9) Uani 1 1 d . . . C51 C -0.36655(18) 0.5130(3) 0.9361(3) 0.0305(9) Uani 1 1 d . . . H51 H -0.3638 0.5674 0.9588 0.037 Uiso 1 1 calc R . . C52 C -0.34309(17) 0.4428(2) 0.9876(2) 0.0234(8) Uani 1 1 d . . . Cl1A Cl -0.1446(2) 0.7063(3) 1.2286(3) 0.1393(11) Uani 0.731(3) 1 d PDU A 1 Cl2A Cl -0.1734(2) 0.7363(3) 1.0699(2) 0.1393(11) Uani 0.731(3) 1 d PDU A 1 C61A C -0.1089(4) 0.7096(9) 1.1700(5) 0.161(5) Uani 0.731(3) 1 d PDU A 1 H61A H -0.0919 0.6548 1.1681 0.194 Uiso 0.731(3) 1 calc PR A 1 H61B H -0.0793 0.7541 1.1884 0.194 Uiso 0.731(3) 1 calc PR A 1 Cl1B Cl -0.1831(4) 0.7364(7) 1.1473(7) 0.1393(11) Uani 0.269(3) 1 d PDU A 2 Cl2B Cl -0.1186(6) 0.7381(7) 1.0759(6) 0.1393(11) Uani 0.269(3) 1 d PDU A 2 C61B C -0.1089(4) 0.7096(9) 1.1700(5) 0.161(5) Uani 0.269(3) 1 d PDU A 2 H61C H -0.0798 0.7442 1.2148 0.194 Uiso 0.269(3) 1 calc PR A 2 H61D H -0.1001 0.6492 1.1816 0.194 Uiso 0.269(3) 1 calc PR A 2 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 0.01975(9) 0.02526(9) 0.01651(8) -0.00057(5) 0.00557(6) -0.00041(6) N1 0.0214(16) 0.0284(17) 0.0157(15) 0.0000(12) 0.0060(13) 0.0003(13) C2 0.025(2) 0.035(2) 0.027(2) 0.0014(16) 0.0113(18) -0.0001(17) C3 0.035(2) 0.037(2) 0.024(2) 0.0005(17) 0.0170(19) 0.0007(19) C4 0.033(2) 0.033(2) 0.0190(19) -0.0008(16) 0.0084(17) 0.0002(18) C5 0.022(2) 0.037(2) 0.0211(19) -0.0022(16) 0.0039(17) -0.0007(17) C6 0.024(2) 0.0261(19) 0.0187(18) -0.0006(14) 0.0075(16) -0.0006(16) C7 0.022(2) 0.031(2) 0.0177(18) -0.0019(15) 0.0051(16) -0.0016(16) N8 0.0237(17) 0.0316(17) 0.0175(15) -0.0015(13) 0.0094(14) -0.0015(14) N9 0.0297(19) 0.044(2) 0.0231(17) -0.0007(15) 0.0140(15) -0.0020(17) N10 0.0262(19) 0.060(3) 0.0263(19) -0.0029(18) 0.0111(16) -0.0026(19) C11 0.024(2) 0.039(2) 0.025(2) -0.0018(17) 0.0113(17) -0.0015(18) C12 0.023(2) 0.051(3) 0.029(2) 0.0007(19) 0.0137(19) -0.0022(19) C13 0.037(3) 0.055(3) 0.049(3) -0.004(3) 0.010(2) 0.001(2) C14 0.042(3) 0.061(4) 0.064(4) 0.014(3) 0.014(3) 0.017(3) F14 0.071(3) 0.074(3) 0.128(4) 0.011(3) -0.003(3) 0.032(2) C15 0.023(2) 0.077(4) 0.045(3) 0.010(3) 0.004(2) 0.003(3) C16 0.031(3) 0.071(4) 0.045(3) -0.009(3) 0.000(2) -0.011(3) F16 0.057(3) 0.081(3) 0.089(3) -0.023(2) -0.029(2) -0.007(2) C17 0.034(3) 0.051(3) 0.044(3) -0.003(2) 0.002(2) 0.001(2) N21 0.0269(18) 0.0260(17) 0.0188(16) -0.0028(12) 0.0080(14) -0.0006(14) C22 0.032(2) 0.034(2) 0.032(2) -0.0036(18) 0.0162(19) -0.0050(19) C23 0.047(3) 0.030(2) 0.041(3) -0.001(2) 0.020(2) -0.006(2) C24 0.054(3) 0.027(2) 0.052(3) -0.001(2) 0.026(3) 0.008(2) C25 0.035(3) 0.038(3) 0.037(2) 0.0006(19) 0.016(2) 0.008(2) C26 0.026(2) 0.032(2) 0.0174(18) 0.0000(15) 0.0072(16) 0.0013(17) C27 0.0191(19) 0.037(2) 0.0178(18) 0.0019(16) 0.0043(15) 0.0005(17) C28 0.023(2) 0.045(3) 0.022(2) -0.0018(18) 0.0061(17) 0.0031(19) F28 0.0295(15) 0.0555(18) 0.0483(17) -0.0076(13) 0.0184(13) 0.0046(13) C29 0.022(2) 0.056(3) 0.034(2) 0.000(2) 0.0120(19) -0.005(2) C30 0.033(2) 0.041(3) 0.038(2) 0.001(2) 0.010(2) -0.012(2) F30 0.0481(19) 0.0482(18) 0.091(3) -0.0005(17) 0.0349(19) -0.0187(15) C31 0.027(2) 0.033(2) 0.033(2) 0.0034(18) 0.0099(18) -0.0006(18) C32 0.0200(19) 0.033(2) 0.0167(17) 0.0013(15) 0.0061(15) -0.0013(16) N41 0.0265(17) 0.0269(17) 0.0241(16) -0.0011(14) 0.0094(14) -0.0001(14) C42 0.042(3) 0.034(2) 0.031(2) 0.0015(18) 0.013(2) 0.009(2) C43 0.053(3) 0.036(2) 0.039(3) 0.007(2) 0.019(2) 0.012(2) C44 0.062(3) 0.030(2) 0.048(3) -0.003(2) 0.032(3) 0.002(2) C45 0.051(3) 0.034(2) 0.034(2) -0.0081(19) 0.022(2) -0.005(2) C46 0.031(2) 0.031(2) 0.027(2) -0.0039(17) 0.0126(18) -0.0055(18) C47 0.030(2) 0.035(2) 0.0208(19) -0.0040(16) 0.0095(17) -0.0025(18) C48 0.046(3) 0.042(3) 0.027(2) -0.0096(19) 0.015(2) -0.007(2) F48 0.086(3) 0.0527(19) 0.0321(15) -0.0180(14) 0.0149(16) -0.0028(17) C49 0.048(3) 0.061(3) 0.021(2) -0.003(2) 0.010(2) -0.003(3) C50 0.036(3) 0.053(3) 0.025(2) 0.012(2) 0.013(2) 0.007(2) F50 0.070(2) 0.063(2) 0.0288(15) 0.0182(13) 0.0164(15) 0.0219(17) C51 0.025(2) 0.039(2) 0.027(2) 0.0037(18) 0.0116(18) 0.0012(18) C52 0.0179(18) 0.035(2) 0.0140(16) 0.0007(15) 0.0046(14) 0.0004(16) Cl1A 0.169(3) 0.1188(18) 0.1092(17) -0.0134(14) 0.0474(18) 0.0208(18) Cl2A 0.169(3) 0.1188(18) 0.1092(17) -0.0134(14) 0.0474(18) 0.0208(18) C61A 0.176(8) 0.127(7) 0.185(8) 0.027(6) 0.087(6) 0.013(6) Cl1B 0.169(3) 0.1188(18) 0.1092(17) -0.0134(14) 0.0474(18) 0.0208(18) Cl2B 0.169(3) 0.1188(18) 0.1092(17) -0.0134(14) 0.0474(18) 0.0208(18) C61B 0.176(8) 0.127(7) 0.185(8) 0.027(6) 0.087(6) 0.013(6) _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 C32 2.012(4) . ? Ir C52 2.012(4) . ? Ir N21 2.036(3) . ? Ir N41 2.042(3) . ? Ir N8 2.115(3) . ? Ir N1 2.168(3) . ? N1 C2 1.350(5) . ? N1 C6 1.360(5) . ? C2 C3 1.385(6) . ? C3 C4 1.389(7) . ? C4 C5 1.388(6) . ? C5 C6 1.394(6) . ? C6 C7 1.452(6) . ? C7 N8 1.362(5) . ? C7 C11 1.392(6) . ? N8 N9 1.328(5) . ? N9 N10 1.342(5) . ? N10 C11 1.364(5) . ? C11 C12 1.474(6) . ? C12 C13 1.384(7) . ? C12 C17 1.402(7) . ? C13 C14 1.378(8) . ? C14 F14 1.363(7) . ? C14 C15 1.372(9) . ? C15 C16 1.357(8) . ? C16 F16 1.348(7) . ? C16 C17 1.369(7) . ? N21 C22 1.347(6) . ? N21 C26 1.374(6) . ? C22 C23 1.373(7) . ? C23 C24 1.396(7) . ? C24 C25 1.371(7) . ? C25 C26 1.399(6) . ? C26 C27 1.467(6) . ? C27 C28 1.392(6) . ? C27 C32 1.421(6) . ? C28 F28 1.360(5) . ? C28 C29 1.375(7) . ? C29 C30 1.368(7) . ? C30 F30 1.362(6) . ? C30 C31 1.381(7) . ? C31 C32 1.396(6) . ? N41 C42 1.347(5) . ? N41 C46 1.374(5) . ? C42 C43 1.369(7) . ? C43 C44 1.386(7) . ? C44 C45 1.383(7) . ? C45 C46 1.387(6) . ? C46 C47 1.463(6) . ? C47 C48 1.395(6) . ? C47 C52 1.408(6) . ? C48 F48 1.353(5) . ? C48 C49 1.378(7) . ? C49 C50 1.372(7) . ? C50 F50 1.366(5) . ? C50 C51 1.376(6) . ? C51 C52 1.394(6) . ? Cl1A C61A 1.716(8) . ? Cl2A C61A 1.864(8) . ? 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 C32 Ir C52 87.53(16) . . ? C32 Ir N21 80.58(16) . . ? C52 Ir N21 94.23(14) . . ? C32 Ir N41 93.48(16) . . ? C52 Ir N41 80.19(15) . . ? N21 Ir N41 172.07(13) . . ? C32 Ir N8 172.90(14) . . ? C52 Ir N8 99.34(14) . . ? N21 Ir N8 97.04(14) . . ? N41 Ir N8 89.47(14) . . ? C32 Ir N1 96.97(14) . . ? C52 Ir N1 174.77(14) . . ? N21 Ir N1 89.14(12) . . ? N41 Ir N1 96.84(12) . . ? N8 Ir N1 76.24(13) . . ? C2 N1 C6 118.9(3) . . ? C2 N1 Ir 125.4(3) . . ? C6 N1 Ir 115.6(3) . . ? N1 C2 C3 122.1(4) . . ? C2 C3 C4 119.3(4) . . ? C5 C4 C3 119.0(4) . . ? C4 C5 C6 119.3(4) . . ? N1 C6 C5 121.5(4) . . ? N1 C6 C7 114.3(3) . . ? C5 C6 C7 124.1(4) . . ? N8 C7 C11 106.4(3) . . ? N8 C7 C6 117.4(4) . . ? C11 C7 C6 136.1(4) . . ? N9 N8 C7 109.0(3) . . ? N9 N8 Ir 134.9(3) . . ? C7 N8 Ir 115.3(3) . . ? N8 N9 N10 109.3(3) . . ? N9 N10 C11 108.0(3) . . ? N10 C11 C7 107.1(4) . . ? N10 C11 C12 123.3(4) . . ? C7 C11 C12 129.4(4) . . ? C13 C12 C17 118.7(5) . . ? C13 C12 C11 119.4(4) . . ? C17 C12 C11 121.9(4) . . ? C14 C13 C12 119.0(5) . . ? F14 C14 C15 118.6(5) . . ? F14 C14 C13 118.0(6) . . ? C15 C14 C13 123.4(6) . . ? C16 C15 C14 116.0(5) . . ? F16 C16 C15 117.4(5) . . ? F16 C16 C17 118.6(6) . . ? C15 C16 C17 124.0(5) . . ? C16 C17 C12 118.8(5) . . ? C22 N21 C26 119.1(4) . . ? C22 N21 Ir 124.0(3) . . ? C26 N21 Ir 116.7(3) . . ? N21 C22 C23 123.0(4) . . ? C22 C23 C24 118.3(4) . . ? C25 C24 C23 119.6(4) . . ? C24 C25 C26 120.2(5) . . ? N21 C26 C25 119.7(4) . . ? N21 C26 C27 112.9(4) . . ? C25 C26 C27 127.3(4) . . ? C28 C27 C32 118.4(4) . . ? C28 C27 C26 125.9(4) . . ? C32 C27 C26 115.6(4) . . ? F28 C28 C29 117.1(4) . . ? F28 C28 C27 119.7(4) . . ? C29 C28 C27 123.2(4) . . ? C30 C29 C28 116.7(4) . . ? F30 C30 C29 117.8(4) . . ? F30 C30 C31 118.4(5) . . ? C29 C30 C31 123.8(4) . . ? C30 C31 C32 119.1(4) . . ? C31 C32 C27 118.7(4) . . ? C31 C32 Ir 127.2(3) . . ? C27 C32 Ir 114.1(3) . . ? C42 N41 C46 119.2(4) . . ? C42 N41 Ir 124.4(3) . . ? C46 N41 Ir 116.4(3) . . ? N41 C42 C43 123.2(4) . . ? C42 C43 C44 118.5(5) . . ? C45 C44 C43 119.1(4) . . ? C44 C45 C46 120.8(4) . . ? N41 C46 C45 119.3(4) . . ? N41 C46 C47 112.7(4) . . ? C45 C46 C47 127.9(4) . . ? C48 C47 C52 118.3(4) . . ? C48 C47 C46 125.6(4) . . ? C52 C47 C46 116.0(4) . . ? F48 C48 C49 116.6(4) . . ? F48 C48 C47 120.2(4) . . ? C49 C48 C47 123.2(4) . . ? C50 C49 C48 116.0(4) . . ? F50 C50 C49 117.3(4) . . ? F50 C50 C51 118.3(5) . . ? C49 C50 C51 124.4(5) . . ? C50 C51 C52 118.7(4) . . ? C51 C52 C47 119.4(4) . . ? C51 C52 Ir 126.4(3) . . ? C47 C52 Ir 114.2(3) . . ? Cl1A C61A Cl2A 96.1(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 C32 Ir N1 C2 -5.0(3) . . . . ? C52 Ir N1 C2 -154.4(15) . . . . ? N21 Ir N1 C2 75.4(3) . . . . ? N41 Ir N1 C2 -99.4(3) . . . . ? N8 Ir N1 C2 172.8(3) . . . . ? C32 Ir N1 C6 178.0(3) . . . . ? C52 Ir N1 C6 28.6(17) . . . . ? N21 Ir N1 C6 -101.6(3) . . . . ? N41 Ir N1 C6 83.6(3) . . . . ? N8 Ir N1 C6 -4.2(3) . . . . ? C6 N1 C2 C3 0.1(6) . . . . ? Ir N1 C2 C3 -176.8(3) . . . . ? N1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C2 N1 C6 C5 0.3(6) . . . . ? Ir N1 C6 C5 177.5(3) . . . . ? C2 N1 C6 C7 -177.8(3) . . . . ? Ir N1 C6 C7 -0.6(4) . . . . ? C4 C5 C6 N1 -0.6(6) . . . . ? C4 C5 C6 C7 177.3(4) . . . . ? N1 C6 C7 N8 8.3(5) . . . . ? C5 C6 C7 N8 -169.7(4) . . . . ? N1 C6 C7 C11 -175.5(5) . . . . ? C5 C6 C7 C11 6.4(8) . . . . ? C11 C7 N8 N9 -1.0(5) . . . . ? C6 C7 N8 N9 176.2(3) . . . . ? C11 C7 N8 Ir 170.7(3) . . . . ? C6 C7 N8 Ir -12.0(5) . . . . ? C32 Ir N8 N9 -165.0(11) . . . . ? C52 Ir N8 N9 0.4(4) . . . . ? N21 Ir N8 N9 -95.0(4) . . . . ? N41 Ir N8 N9 80.4(4) . . . . ? N1 Ir N8 N9 177.6(4) . . . . ? C32 Ir N8 C7 26.0(13) . . . . ? C52 Ir N8 C7 -168.5(3) . . . . ? N21 Ir N8 C7 96.0(3) . . . . ? N41 Ir N8 C7 -88.6(3) . . . . ? N1 Ir N8 C7 8.6(3) . . . . ? C7 N8 N9 N10 0.8(5) . . . . ? Ir N8 N9 N10 -168.7(3) . . . . ? N8 N9 N10 C11 -0.3(5) . . . . ? N9 N10 C11 C7 -0.4(5) . . . . ? N9 N10 C11 C12 175.0(4) . . . . ? N8 C7 C11 N10 0.9(5) . . . . ? C6 C7 C11 N10 -175.6(5) . . . . ? N8 C7 C11 C12 -174.1(4) . . . . ? C6 C7 C11 C12 9.5(9) . . . . ? N10 C11 C12 C13 -89.9(6) . . . . ? C7 C11 C12 C13 84.4(6) . . . . ? N10 C11 C12 C17 93.3(6) . . . . ? C7 C11 C12 C17 -92.4(7) . . . . ? C17 C12 C13 C14 -0.4(8) . . . . ? C11 C12 C13 C14 -177.2(5) . . . . ? C12 C13 C14 F14 179.2(6) . . . . ? C12 C13 C14 C15 -0.8(10) . . . . ? F14 C14 C15 C16 -178.6(6) . . . . ? C13 C14 C15 C16 1.4(10) . . . . ? C14 C15 C16 F16 179.0(6) . . . . ? C14 C15 C16 C17 -0.9(10) . . . . ? F16 C16 C17 C12 180.0(6) . . . . ? C15 C16 C17 C12 -0.2(10) . . . . ? C13 C12 C17 C16 0.8(8) . . . . ? C11 C12 C17 C16 177.6(5) . . . . ? C32 Ir N21 C22 -176.9(4) . . . . ? C52 Ir N21 C22 -90.1(3) . . . . ? N41 Ir N21 C22 -135.0(9) . . . . ? N8 Ir N21 C22 9.9(3) . . . . ? N1 Ir N21 C22 85.9(3) . . . . ? C32 Ir N21 C26 -1.8(3) . . . . ? C52 Ir N21 C26 85.0(3) . . . . ? N41 Ir N21 C26 40.0(11) . . . . ? N8 Ir N21 C26 -175.0(3) . . . . ? N1 Ir N21 C26 -99.0(3) . . . . ? C26 N21 C22 C23 -0.3(6) . . . . ? Ir N21 C22 C23 174.6(3) . . . . ? N21 C22 C23 C24 0.0(7) . . . . ? C22 C23 C24 C25 0.6(8) . . . . ? C23 C24 C25 C26 -0.7(7) . . . . ? C22 N21 C26 C25 0.2(6) . . . . ? Ir N21 C26 C25 -175.2(3) . . . . ? C22 N21 C26 C27 178.8(3) . . . . ? Ir N21 C26 C27 3.5(4) . . . . ? C24 C25 C26 N21 0.4(7) . . . . ? C24 C25 C26 C27 -178.1(4) . . . . ? N21 C26 C27 C28 176.7(4) . . . . ? C25 C26 C27 C28 -4.7(7) . . . . ? N21 C26 C27 C32 -3.8(5) . . . . ? C25 C26 C27 C32 174.7(4) . . . . ? C32 C27 C28 F28 178.8(3) . . . . ? C26 C27 C28 F28 -1.8(6) . . . . ? C32 C27 C28 C29 -0.3(6) . . . . ? C26 C27 C28 C29 179.2(4) . . . . ? F28 C28 C29 C30 -179.6(4) . . . . ? C27 C28 C29 C30 -0.5(7) . . . . ? C28 C29 C30 F30 -179.0(4) . . . . ? C28 C29 C30 C31 0.4(7) . . . . ? F30 C30 C31 C32 -180.0(4) . . . . ? C29 C30 C31 C32 0.6(7) . . . . ? C30 C31 C32 C27 -1.4(6) . . . . ? C30 C31 C32 Ir 177.9(3) . . . . ? C28 C27 C32 C31 1.3(6) . . . . ? C26 C27 C32 C31 -178.2(4) . . . . ? C28 C27 C32 Ir -178.1(3) . . . . ? C26 C27 C32 Ir 2.4(4) . . . . ? C52 Ir C32 C31 85.5(4) . . . . ? N21 Ir C32 C31 -179.7(4) . . . . ? N41 Ir C32 C31 5.5(4) . . . . ? N8 Ir C32 C31 -108.8(12) . . . . ? N1 Ir C32 C31 -91.8(4) . . . . ? C52 Ir C32 C27 -95.1(3) . . . . ? N21 Ir C32 C27 -0.4(3) . . . . ? N41 Ir C32 C27 -175.1(3) . . . . ? N8 Ir C32 C27 70.5(12) . . . . ? N1 Ir C32 C27 87.6(3) . . . . ? C32 Ir N41 C42 -96.8(4) . . . . ? C52 Ir N41 C42 176.3(4) . . . . ? N21 Ir N41 C42 -138.1(9) . . . . ? N8 Ir N41 C42 76.7(4) . . . . ? N1 Ir N41 C42 0.6(4) . . . . ? C32 Ir N41 C46 80.7(3) . . . . ? C52 Ir N41 C46 -6.2(3) . . . . ? N21 Ir N41 C46 39.5(11) . . . . ? N8 Ir N41 C46 -105.8(3) . . . . ? N1 Ir N41 C46 178.2(3) . . . . ? C46 N41 C42 C43 -1.5(7) . . . . ? Ir N41 C42 C43 176.0(4) . . . . ? N41 C42 C43 C44 1.1(8) . . . . ? C42 C43 C44 C45 -0.5(8) . . . . ? C43 C44 C45 C46 0.3(8) . . . . ? C42 N41 C46 C45 1.3(6) . . . . ? Ir N41 C46 C45 -176.4(3) . . . . ? C42 N41 C46 C47 -177.5(4) . . . . ? Ir N41 C46 C47 4.8(5) . . . . ? C44 C45 C46 N41 -0.7(7) . . . . ? C44 C45 C46 C47 177.9(5) . . . . ? N41 C46 C47 C48 177.9(4) . . . . ? C45 C46 C47 C48 -0.8(8) . . . . ? N41 C46 C47 C52 0.6(6) . . . . ? C45 C46 C47 C52 -178.1(5) . . . . ? C52 C47 C48 F48 179.6(4) . . . . ? C46 C47 C48 F48 2.4(8) . . . . ? C52 C47 C48 C49 -0.9(8) . . . . ? C46 C47 C48 C49 -178.1(5) . . . . ? F48 C48 C49 C50 -178.2(5) . . . . ? C47 C48 C49 C50 2.3(8) . . . . ? C48 C49 C50 F50 178.8(5) . . . . ? C48 C49 C50 C51 -1.9(8) . . . . ? F50 C50 C51 C52 179.4(4) . . . . ? C49 C50 C51 C52 0.0(7) . . . . ? C50 C51 C52 C47 1.5(6) . . . . ? C50 C51 C52 Ir -176.1(3) . . . . ? C48 C47 C52 C51 -1.1(6) . . . . ? C46 C47 C52 C51 176.4(4) . . . . ? C48 C47 C52 Ir 176.8(3) . . . . ? C46 C47 C52 Ir -5.7(5) . . . . ? C32 Ir C52 C51 90.0(4) . . . . ? N21 Ir C52 C51 9.6(4) . . . . ? N41 Ir C52 C51 -176.0(4) . . . . ? N8 Ir C52 C51 -88.2(4) . . . . ? N1 Ir C52 C51 -120.4(15) . . . . ? C32 Ir C52 C47 -87.7(3) . . . . ? N21 Ir C52 C47 -168.1(3) . . . . ? N41 Ir C52 C47 6.3(3) . . . . ? N8 Ir C52 C47 94.1(3) . . . . ? N1 Ir C52 C47 61.9(17) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.352 _refine_diff_density_min -1.874 _refine_diff_density_rms 0.127 # Attachment 'complex2.cif' data_fro4438 _database_code_depnum_ccdc_archive 'CCDC 678025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H24 F9 Ir N6 O' _chemical_formula_weight 955.84 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' 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' 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 C2/c 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' '-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 25.9847(2) _cell_length_b 16.2224(2) _cell_length_c 18.3429(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.537(1) _cell_angle_gamma 90.00 _cell_volume 6917.54(13) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7346 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3728 _exptl_absorpt_coefficient_mu 3.953 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3935 _exptl_absorpt_correction_T_max 0.6833 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotataing anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23852 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.28 _reflns_number_total 8466 _reflns_number_gt 6911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (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. ; _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^)+(0.0264P)^2^+9.5981P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8466 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Ir Ir -0.302115(4) 0.557059(7) 0.615203(6) 0.02315(4) Uani 1 1 d . . . N1 N -0.25706(10) 0.56106(13) 0.74688(14) 0.0241(5) Uani 1 1 d . . . C2 C -0.28169(13) 0.56925(18) 0.79737(19) 0.0313(7) Uani 1 1 d . . . H2 H -0.3218 0.5763 0.7746 0.038 Uiso 1 1 calc R . . C3 C -0.25063(14) 0.56769(19) 0.88098(19) 0.0341(7) Uani 1 1 d . . . H3 H -0.2694 0.5733 0.9143 0.041 Uiso 1 1 calc R . . C4 C -0.19168(14) 0.55787(18) 0.9153(2) 0.0330(7) Uani 1 1 d . . . H4 H -0.1697 0.5563 0.9722 0.040 Uiso 1 1 calc R . . C5 C -0.16559(13) 0.55039(18) 0.86426(18) 0.0299(6) Uani 1 1 d . . . H5 H -0.1254 0.5447 0.8863 0.036 Uiso 1 1 calc R . . C6 C -0.19898(12) 0.55131(16) 0.78030(17) 0.0246(6) Uani 1 1 d . . . C7 C -0.17652(12) 0.54123(18) 0.72126(17) 0.0278(6) Uani 1 1 d . . . N8 N -0.21493(10) 0.53409(15) 0.64162(14) 0.0284(5) Uani 1 1 d . . . N9 N -0.18656(11) 0.52420(18) 0.59690(16) 0.0371(6) Uani 1 1 d . . . N10 N -0.12962(11) 0.5258(2) 0.64646(17) 0.0429(7) Uani 1 1 d . . . C11 C -0.12241(13) 0.5361(2) 0.72392(19) 0.0355(7) Uani 1 1 d . . . C12 C -0.06479(13) 0.5455(2) 0.7941(2) 0.0375(8) Uani 1 1 d . . . C13 C -0.03720(16) 0.6207(3) 0.8135(3) 0.0633(12) Uani 1 1 d . . . F13 F -0.06142(12) 0.68543(19) 0.7656(2) 0.1287(15) Uani 1 1 d . . . C14 C 0.01509(17) 0.6325(3) 0.8812(3) 0.0730(14) Uani 1 1 d . . . F14 F 0.03950(14) 0.7071(2) 0.8978(2) 0.1389(17) Uani 1 1 d . . . C15 C 0.04112(15) 0.5676(2) 0.9312(2) 0.0511(10) Uani 1 1 d . . . F15 F 0.09103(9) 0.57826(17) 0.99761(15) 0.0730(7) Uani 1 1 d . . . C16 C 0.01532(15) 0.4925(3) 0.9147(2) 0.0491(9) Uani 1 1 d . . . F16 F 0.04029(12) 0.42942(15) 0.96580(16) 0.0820(9) Uani 1 1 d . . . C17 C -0.03716(15) 0.4821(2) 0.8475(2) 0.0456(9) Uani 1 1 d . . . F17 F -0.06235(12) 0.40875(16) 0.83625(16) 0.0900(10) Uani 1 1 d . . . N21 N -0.32493(11) 0.43836(14) 0.62312(14) 0.0275(5) Uani 1 1 d . . . C22 C -0.29152(14) 0.3723(2) 0.62945(18) 0.0373(8) Uani 1 1 d . . . H22 H -0.2545 0.3807 0.6338 0.045 Uiso 1 1 calc R . . C23 C -0.31018(17) 0.2932(2) 0.6298(2) 0.0476(9) Uani 1 1 d . . . H23 H -0.2863 0.2482 0.6337 0.057 Uiso 1 1 calc R . . C24 C -0.36426(18) 0.2805(2) 0.6242(2) 0.0535(10) Uani 1 1 d . . . H24 H -0.3775 0.2266 0.6243 0.064 Uiso 1 1 calc R . . C25 C -0.39870(16) 0.3469(2) 0.6185(2) 0.0458(9) Uani 1 1 d . . . H25 H -0.4355 0.3385 0.6151 0.055 Uiso 1 1 calc R . . C26 C -0.37877(13) 0.42722(18) 0.61775(18) 0.0307(7) Uani 1 1 d . . . C27 C -0.41051(12) 0.5039(2) 0.60942(17) 0.0310(7) Uani 1 1 d . . . C28 C -0.46496(13) 0.5117(2) 0.6047(2) 0.0397(8) Uani 1 1 d . . . F28 F -0.49311(9) 0.44316(13) 0.61083(15) 0.0579(6) Uani 1 1 d . . . C29 C -0.49304(14) 0.5859(2) 0.5948(2) 0.0460(9) Uani 1 1 d . . . H29 H -0.5300 0.5895 0.5920 0.055 Uiso 1 1 calc R . . C30 C -0.46411(14) 0.6540(2) 0.5892(2) 0.0461(9) Uani 1 1 d . . . F30 F -0.49102(10) 0.72818(14) 0.57824(18) 0.0751(8) Uani 1 1 d . . . C31 C -0.40961(13) 0.6519(2) 0.5942(2) 0.0371(7) Uani 1 1 d . . . H31 H -0.3916 0.7008 0.5903 0.045 Uiso 1 1 calc R . . C32 C -0.38160(12) 0.57670(19) 0.60497(17) 0.0277(6) Uani 1 1 d . . . N41 N -0.29066(10) 0.67803(15) 0.59520(15) 0.0298(5) Uani 1 1 d . . . C42 C -0.26444(15) 0.7338(2) 0.6543(2) 0.0402(8) Uani 1 1 d . . . H42 H -0.2476 0.7160 0.7088 0.048 Uiso 1 1 calc R . . C43 C -0.26116(16) 0.8159(2) 0.6384(2) 0.0505(9) Uani 1 1 d . . . H43 H -0.2429 0.8536 0.6813 0.061 Uiso 1 1 calc R . . C44 C -0.28516(16) 0.8422(2) 0.5584(2) 0.0492(9) Uani 1 1 d . . . H44 H -0.2832 0.8980 0.5460 0.059 Uiso 1 1 calc R . . C45 C -0.31185(15) 0.7858(2) 0.4973(2) 0.0433(8) Uani 1 1 d . . . H45 H -0.3286 0.8031 0.4426 0.052 Uiso 1 1 calc R . . C46 C -0.31431(12) 0.70268(19) 0.51567(19) 0.0332(7) Uani 1 1 d . . . C47 C -0.34051(13) 0.63522(19) 0.45814(18) 0.0324(7) Uani 1 1 d . . . C48 C -0.36679(15) 0.6419(2) 0.3733(2) 0.0444(8) Uani 1 1 d . . . F48 F -0.36805(12) 0.71525(14) 0.33806(13) 0.0706(7) Uani 1 1 d . . . C49 C -0.39127(16) 0.5763(3) 0.3221(2) 0.0498(9) Uani 1 1 d . . . H49 H -0.4090 0.5822 0.2651 0.060 Uiso 1 1 calc R . . C50 C -0.38832(14) 0.5017(2) 0.3587(2) 0.0430(8) Uani 1 1 d . . . F50 F -0.41222(11) 0.43549(14) 0.30897(13) 0.0656(7) Uani 1 1 d . . . C51 C -0.36273(13) 0.4898(2) 0.44144(19) 0.0343(7) Uani 1 1 d . . . H51 H -0.3615 0.4370 0.4632 0.041 Uiso 1 1 calc R . . C52 C -0.33851(12) 0.55689(17) 0.49286(17) 0.0267(6) Uani 1 1 d . . . O61 O -0.18538(14) 0.2574(2) 0.6351(2) 0.0789(9) Uani 1 1 d . . . C62 C -0.1741(3) 0.2707(4) 0.5698(3) 0.1020(19) Uani 1 1 d . . . H62A H -0.1936 0.3210 0.5412 0.122 Uiso 1 1 calc R . . H62B H -0.1887 0.2244 0.5316 0.122 Uiso 1 1 calc R . . C63 C -0.1131(3) 0.2788(5) 0.5978(5) 0.126(3) Uani 1 1 d . . . H63A H -0.0981 0.2314 0.5802 0.151 Uiso 1 1 calc R . . H63B H -0.1044 0.3291 0.5758 0.151 Uiso 1 1 calc R . . C64 C -0.0876(2) 0.2825(5) 0.6848(5) 0.125(3) Uani 1 1 d . . . H64A H -0.0668 0.3345 0.7046 0.150 Uiso 1 1 calc R . . H64B H -0.0607 0.2367 0.7089 0.150 Uiso 1 1 calc R . . C65 C -0.1372(3) 0.2764(4) 0.7063(3) 0.0990(19) Uani 1 1 d . . . H65A H -0.1298 0.2332 0.7471 0.119 Uiso 1 1 calc R . . H65B H -0.1426 0.3289 0.7284 0.119 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 Ir 0.01687(6) 0.03226(7) 0.01812(6) 0.00275(4) 0.00583(4) 0.00252(4) N1 0.0214(12) 0.0302(13) 0.0191(11) 0.0023(9) 0.0077(9) 0.0029(9) C2 0.0261(15) 0.0407(17) 0.0306(16) -0.0017(13) 0.0158(13) 0.0007(12) C3 0.0343(17) 0.0440(18) 0.0280(16) -0.0011(13) 0.0176(14) 0.0000(13) C4 0.0344(17) 0.0413(18) 0.0206(14) -0.0011(13) 0.0099(13) -0.0015(13) C5 0.0228(14) 0.0423(17) 0.0196(14) 0.0031(12) 0.0049(12) 0.0041(12) C6 0.0213(13) 0.0312(15) 0.0194(13) 0.0036(11) 0.0072(11) 0.0007(11) C7 0.0182(13) 0.0409(17) 0.0216(14) 0.0059(12) 0.0063(11) 0.0043(11) N8 0.0210(12) 0.0436(14) 0.0201(12) 0.0048(10) 0.0089(10) 0.0047(10) N9 0.0257(13) 0.0624(17) 0.0255(13) 0.0064(12) 0.0134(11) 0.0077(12) N10 0.0229(13) 0.074(2) 0.0308(15) 0.0079(14) 0.0115(12) 0.0089(13) C11 0.0222(15) 0.0556(19) 0.0273(16) 0.0077(14) 0.0099(13) 0.0064(13) C12 0.0198(15) 0.060(2) 0.0310(17) 0.0106(15) 0.0102(13) 0.0087(14) C13 0.033(2) 0.069(3) 0.065(3) 0.034(2) 0.0006(19) -0.0005(18) F13 0.0701(19) 0.094(2) 0.132(3) 0.070(2) -0.0350(18) -0.0189(16) C14 0.036(2) 0.075(3) 0.077(3) 0.024(2) -0.002(2) -0.017(2) F14 0.080(2) 0.099(2) 0.144(3) 0.050(2) -0.034(2) -0.0454(18) C15 0.0203(16) 0.079(3) 0.042(2) 0.0111(19) 0.0032(15) 0.0022(17) F15 0.0313(12) 0.1073(19) 0.0517(14) 0.0129(13) -0.0071(11) -0.0049(12) C16 0.0350(19) 0.067(3) 0.0326(19) 0.0082(17) 0.0037(15) 0.0176(18) F16 0.0701(18) 0.0730(16) 0.0547(15) 0.0149(12) -0.0155(13) 0.0215(13) C17 0.0386(19) 0.049(2) 0.038(2) -0.0009(16) 0.0072(16) 0.0069(16) F17 0.087(2) 0.0543(15) 0.0691(18) 0.0077(13) -0.0181(15) -0.0002(14) N21 0.0267(13) 0.0327(13) 0.0214(12) 0.0007(10) 0.0093(10) 0.0038(10) C22 0.0384(18) 0.047(2) 0.0286(17) 0.0077(14) 0.0166(14) 0.0109(14) C23 0.058(2) 0.044(2) 0.042(2) -0.0009(16) 0.0242(19) 0.0119(17) C24 0.067(3) 0.038(2) 0.058(2) -0.0014(17) 0.030(2) -0.0075(18) C25 0.044(2) 0.049(2) 0.048(2) -0.0008(17) 0.0240(17) -0.0088(16) C26 0.0278(15) 0.0416(18) 0.0210(14) 0.0000(12) 0.0094(12) -0.0050(12) C27 0.0232(15) 0.0475(18) 0.0199(14) -0.0023(13) 0.0075(12) -0.0040(13) C28 0.0254(16) 0.060(2) 0.0310(17) -0.0004(15) 0.0107(14) -0.0095(15) F28 0.0321(11) 0.0771(16) 0.0669(16) 0.0054(11) 0.0242(11) -0.0112(10) C29 0.0235(16) 0.070(2) 0.045(2) -0.0007(18) 0.0151(15) 0.0097(16) C30 0.0311(18) 0.057(2) 0.049(2) -0.0019(17) 0.0173(16) 0.0128(16) F30 0.0460(13) 0.0659(15) 0.115(2) -0.0011(14) 0.0378(14) 0.0246(11) C31 0.0258(16) 0.0431(18) 0.0405(18) -0.0015(14) 0.0131(14) 0.0043(13) C32 0.0187(13) 0.0430(17) 0.0189(13) 0.0002(12) 0.0061(11) 0.0046(12) N41 0.0215(12) 0.0342(13) 0.0305(13) 0.0041(11) 0.0087(10) 0.0037(10) C42 0.0392(19) 0.0354(18) 0.0389(19) -0.0003(14) 0.0112(15) -0.0054(14) C43 0.052(2) 0.041(2) 0.054(2) -0.0061(17) 0.0197(19) -0.0039(17) C44 0.055(2) 0.0332(18) 0.065(3) 0.0094(18) 0.032(2) 0.0076(16) C45 0.045(2) 0.0432(19) 0.045(2) 0.0144(16) 0.0227(17) 0.0138(16) C46 0.0256(15) 0.0380(17) 0.0367(17) 0.0111(13) 0.0144(13) 0.0083(12) C47 0.0277(15) 0.0435(18) 0.0244(15) 0.0091(13) 0.0103(13) 0.0086(13) C48 0.044(2) 0.057(2) 0.0311(18) 0.0174(16) 0.0151(16) 0.0147(17) F48 0.0972(19) 0.0674(15) 0.0397(12) 0.0283(11) 0.0238(13) 0.0203(13) C49 0.043(2) 0.079(3) 0.0220(16) 0.0061(17) 0.0099(15) 0.0090(19) C50 0.0337(18) 0.066(2) 0.0286(17) -0.0096(16) 0.0134(15) -0.0022(16) F50 0.0714(17) 0.0868(17) 0.0299(11) -0.0201(11) 0.0148(11) -0.0183(12) C51 0.0263(16) 0.0491(19) 0.0286(16) -0.0004(14) 0.0133(13) -0.0007(14) C52 0.0183(13) 0.0410(17) 0.0195(13) 0.0047(12) 0.0074(11) 0.0036(12) O61 0.061(2) 0.103(2) 0.075(2) -0.0063(19) 0.0335(18) -0.0127(17) C62 0.087(4) 0.156(6) 0.075(4) 0.009(4) 0.046(3) 0.001(4) C63 0.082(5) 0.175(7) 0.142(7) 0.034(6) 0.070(5) 0.012(5) C64 0.052(3) 0.154(6) 0.147(7) -0.062(5) 0.025(4) -0.017(4) C65 0.093(4) 0.123(5) 0.062(3) -0.015(3) 0.019(3) -0.035(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 C52 2.009(3) . ? Ir C32 2.014(3) . ? Ir N21 2.039(2) . ? Ir N41 2.043(2) . ? Ir N8 2.127(2) . ? Ir N1 2.164(2) . ? N1 C2 1.347(4) . ? N1 C6 1.361(4) . ? C2 C3 1.378(4) . ? C3 C4 1.381(5) . ? C4 C5 1.385(4) . ? C5 C6 1.390(4) . ? C6 C7 1.451(4) . ? C7 N8 1.357(4) . ? C7 C11 1.388(4) . ? N8 N9 1.335(3) . ? N9 N10 1.347(4) . ? N10 C11 1.358(4) . ? C11 C12 1.483(4) . ? C12 C13 1.378(5) . ? C12 C17 1.381(5) . ? C13 F13 1.332(4) . ? C13 C14 1.385(5) . ? C14 F14 1.336(5) . ? C14 C15 1.361(5) . ? C15 F15 1.335(4) . ? C15 C16 1.359(5) . ? C16 F16 1.342(4) . ? C16 C17 1.380(5) . ? C17 F17 1.329(5) . ? N21 C22 1.352(4) . ? N21 C26 1.370(4) . ? C22 C23 1.372(5) . ? C23 C24 1.378(5) . ? C24 C25 1.373(5) . ? C25 C26 1.405(4) . ? C26 C27 1.463(4) . ? C27 C28 1.384(4) . ? C27 C32 1.421(4) . ? C28 F28 1.364(4) . ? C28 C29 1.376(5) . ? C29 C30 1.365(5) . ? C30 F30 1.361(4) . ? C30 C31 1.379(4) . ? C31 C32 1.389(4) . ? N41 C42 1.341(4) . ? N41 C46 1.366(4) . ? C42 C43 1.375(5) . ? C43 C44 1.381(5) . ? C44 C45 1.371(5) . ? C45 C46 1.398(4) . ? C46 C47 1.460(4) . ? C47 C48 1.396(4) . ? C47 C52 1.412(4) . ? C48 F48 1.348(4) . ? C48 C49 1.373(5) . ? C49 C50 1.369(5) . ? C50 F50 1.366(4) . ? C50 C51 1.371(4) . ? C51 C52 1.393(4) . ? O61 C62 1.372(6) . ? O61 C65 1.380(6) . ? C62 C63 1.438(8) . ? C63 C64 1.429(9) . ? C64 C65 1.511(8) . ? 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 C52 Ir C32 86.83(11) . . ? C52 Ir N21 94.10(10) . . ? C32 Ir N21 80.64(11) . . ? C52 Ir N41 80.46(11) . . ? C32 Ir N41 93.27(11) . . ? N21 Ir N41 172.09(9) . . ? C52 Ir N8 100.15(10) . . ? C32 Ir N8 172.93(10) . . ? N21 Ir N8 97.61(10) . . ? N41 Ir N8 89.04(9) . . ? C52 Ir N1 175.63(10) . . ? C32 Ir N1 96.90(10) . . ? N21 Ir N1 88.76(9) . . ? N41 Ir N1 97.01(9) . . ? N8 Ir N1 76.17(9) . . ? C2 N1 C6 118.3(2) . . ? C2 N1 Ir 125.7(2) . . ? C6 N1 Ir 115.94(18) . . ? N1 C2 C3 122.8(3) . . ? C2 C3 C4 119.2(3) . . ? C3 C4 C5 118.7(3) . . ? C4 C5 C6 119.8(3) . . ? N1 C6 C5 121.2(3) . . ? N1 C6 C7 114.3(2) . . ? C5 C6 C7 124.5(3) . . ? N8 C7 C11 106.2(3) . . ? N8 C7 C6 117.8(2) . . ? C11 C7 C6 136.0(3) . . ? N9 N8 C7 109.2(2) . . ? N9 N8 Ir 134.85(19) . . ? C7 N8 Ir 115.25(19) . . ? N8 N9 N10 108.9(2) . . ? N9 N10 C11 107.8(2) . . ? N10 C11 C7 107.8(3) . . ? N10 C11 C12 122.3(3) . . ? C7 C11 C12 129.7(3) . . ? C13 C12 C17 115.5(3) . . ? C13 C12 C11 121.5(3) . . ? C17 C12 C11 122.9(3) . . ? F13 C13 C12 119.3(3) . . ? F13 C13 C14 117.9(4) . . ? C12 C13 C14 122.9(3) . . ? F14 C14 C15 120.3(4) . . ? F14 C14 C13 120.3(4) . . ? C15 C14 C13 119.4(4) . . ? F15 C15 C16 120.0(3) . . ? F15 C15 C14 120.2(4) . . ? C16 C15 C14 119.8(3) . . ? F16 C16 C15 119.4(3) . . ? F16 C16 C17 120.5(4) . . ? C15 C16 C17 120.1(3) . . ? F17 C17 C16 118.0(3) . . ? F17 C17 C12 119.5(3) . . ? C16 C17 C12 122.4(4) . . ? C22 N21 C26 119.8(3) . . ? C22 N21 Ir 124.0(2) . . ? C26 N21 Ir 116.08(19) . . ? N21 C22 C23 121.8(3) . . ? C22 C23 C24 119.3(3) . . ? C25 C24 C23 119.8(3) . . ? C24 C25 C26 119.8(3) . . ? N21 C26 C25 119.4(3) . . ? N21 C26 C27 113.9(3) . . ? C25 C26 C27 126.7(3) . . ? C28 C27 C32 118.2(3) . . ? C28 C27 C26 126.7(3) . . ? C32 C27 C26 115.1(3) . . ? F28 C28 C29 116.8(3) . . ? F28 C28 C27 119.4(3) . . ? C29 C28 C27 123.7(3) . . ? C30 C29 C28 116.1(3) . . ? F30 C30 C29 117.6(3) . . ? F30 C30 C31 118.4(3) . . ? C29 C30 C31 124.0(3) . . ? C30 C31 C32 119.2(3) . . ? C31 C32 C27 118.8(3) . . ? C31 C32 Ir 127.0(2) . . ? C27 C32 Ir 114.2(2) . . ? C42 N41 C46 119.4(3) . . ? C42 N41 Ir 124.4(2) . . ? C46 N41 Ir 116.2(2) . . ? N41 C42 C43 122.6(3) . . ? C42 C43 C44 118.9(3) . . ? C45 C44 C43 119.1(3) . . ? C44 C45 C46 120.5(3) . . ? N41 C46 C45 119.5(3) . . ? N41 C46 C47 113.2(3) . . ? C45 C46 C47 127.2(3) . . ? C48 C47 C52 118.2(3) . . ? C48 C47 C46 125.8(3) . . ? C52 C47 C46 115.9(3) . . ? F48 C48 C49 116.8(3) . . ? F48 C48 C47 119.8(3) . . ? C49 C48 C47 123.3(3) . . ? C50 C49 C48 116.2(3) . . ? F50 C50 C49 117.3(3) . . ? F50 C50 C51 118.7(3) . . ? C49 C50 C51 124.1(3) . . ? C50 C51 C52 119.3(3) . . ? C51 C52 C47 118.9(3) . . ? C51 C52 Ir 127.1(2) . . ? C47 C52 Ir 114.0(2) . . ? C62 O61 C65 109.5(4) . . ? O61 C62 C63 109.5(5) . . ? C64 C63 C62 106.9(5) . . ? C63 C64 C65 105.3(5) . . ? O61 C65 C64 106.7(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 C52 Ir N1 C2 152.3(12) . . . . ? C32 Ir N1 C2 3.6(2) . . . . ? N21 Ir N1 C2 -76.8(2) . . . . ? N41 Ir N1 C2 97.8(2) . . . . ? N8 Ir N1 C2 -174.9(2) . . . . ? C52 Ir N1 C6 -30.3(14) . . . . ? C32 Ir N1 C6 -178.89(19) . . . . ? N21 Ir N1 C6 100.70(19) . . . . ? N41 Ir N1 C6 -84.71(19) . . . . ? N8 Ir N1 C6 2.56(18) . . . . ? C6 N1 C2 C3 -0.4(4) . . . . ? Ir N1 C2 C3 177.0(2) . . . . ? N1 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C2 N1 C6 C5 -0.5(4) . . . . ? Ir N1 C6 C5 -178.1(2) . . . . ? C2 N1 C6 C7 178.7(2) . . . . ? Ir N1 C6 C7 1.1(3) . . . . ? C4 C5 C6 N1 1.3(4) . . . . ? C4 C5 C6 C7 -177.9(3) . . . . ? N1 C6 C7 N8 -6.6(4) . . . . ? C5 C6 C7 N8 172.6(3) . . . . ? N1 C6 C7 C11 173.8(3) . . . . ? C5 C6 C7 C11 -7.0(5) . . . . ? C11 C7 N8 N9 0.6(3) . . . . ? C6 C7 N8 N9 -179.1(2) . . . . ? C11 C7 N8 Ir -171.4(2) . . . . ? C6 C7 N8 Ir 8.8(3) . . . . ? C52 Ir N8 N9 2.2(3) . . . . ? C32 Ir N8 N9 172.9(8) . . . . ? N21 Ir N8 N9 97.8(3) . . . . ? N41 Ir N8 N9 -78.0(3) . . . . ? N1 Ir N8 N9 -175.4(3) . . . . ? C52 Ir N8 C7 171.6(2) . . . . ? C32 Ir N8 C7 -17.8(10) . . . . ? N21 Ir N8 C7 -92.9(2) . . . . ? N41 Ir N8 C7 91.4(2) . . . . ? N1 Ir N8 C7 -6.0(2) . . . . ? C7 N8 N9 N10 -0.8(3) . . . . ? Ir N8 N9 N10 169.0(2) . . . . ? N8 N9 N10 C11 0.6(4) . . . . ? N9 N10 C11 C7 -0.2(4) . . . . ? N9 N10 C11 C12 -176.4(3) . . . . ? N8 C7 C11 N10 -0.2(4) . . . . ? C6 C7 C11 N10 179.5(3) . . . . ? N8 C7 C11 C12 175.5(3) . . . . ? C6 C7 C11 C12 -4.8(6) . . . . ? N10 C11 C12 C13 83.0(5) . . . . ? C7 C11 C12 C13 -92.2(5) . . . . ? N10 C11 C12 C17 -101.9(4) . . . . ? C7 C11 C12 C17 82.9(5) . . . . ? C17 C12 C13 F13 -179.1(4) . . . . ? C11 C12 C13 F13 -3.6(6) . . . . ? C17 C12 C13 C14 0.8(7) . . . . ? C11 C12 C13 C14 176.2(4) . . . . ? F13 C13 C14 F14 0.8(8) . . . . ? C12 C13 C14 F14 -179.0(5) . . . . ? F13 C13 C14 C15 -179.8(5) . . . . ? C12 C13 C14 C15 0.4(8) . . . . ? F14 C14 C15 F15 0.6(8) . . . . ? C13 C14 C15 F15 -178.8(4) . . . . ? F14 C14 C15 C16 178.7(5) . . . . ? C13 C14 C15 C16 -0.7(7) . . . . ? F15 C15 C16 F16 0.4(6) . . . . ? C14 C15 C16 F16 -177.7(4) . . . . ? F15 C15 C16 C17 177.9(4) . . . . ? C14 C15 C16 C17 -0.2(6) . . . . ? F16 C16 C17 F17 1.3(6) . . . . ? C15 C16 C17 F17 -176.2(4) . . . . ? F16 C16 C17 C12 179.0(3) . . . . ? C15 C16 C17 C12 1.4(6) . . . . ? C13 C12 C17 F17 175.9(4) . . . . ? C11 C12 C17 F17 0.6(5) . . . . ? C13 C12 C17 C16 -1.7(6) . . . . ? C11 C12 C17 C16 -177.0(3) . . . . ? C52 Ir N21 C22 91.3(2) . . . . ? C32 Ir N21 C22 177.4(3) . . . . ? N41 Ir N21 C22 137.5(6) . . . . ? N8 Ir N21 C22 -9.5(2) . . . . ? N1 Ir N21 C22 -85.4(2) . . . . ? C52 Ir N21 C26 -85.7(2) . . . . ? C32 Ir N21 C26 0.4(2) . . . . ? N41 Ir N21 C26 -39.4(8) . . . . ? N8 Ir N21 C26 173.5(2) . . . . ? N1 Ir N21 C26 97.6(2) . . . . ? C26 N21 C22 C23 0.8(4) . . . . ? Ir N21 C22 C23 -176.1(2) . . . . ? N21 C22 C23 C24 -0.6(5) . . . . ? C22 C23 C24 C25 -0.1(6) . . . . ? C23 C24 C25 C26 0.5(6) . . . . ? C22 N21 C26 C25 -0.3(4) . . . . ? Ir N21 C26 C25 176.8(2) . . . . ? C22 N21 C26 C27 -178.7(3) . . . . ? Ir N21 C26 C27 -1.7(3) . . . . ? C24 C25 C26 N21 -0.3(5) . . . . ? C24 C25 C26 C27 177.9(3) . . . . ? N21 C26 C27 C28 -178.4(3) . . . . ? C25 C26 C27 C28 3.4(5) . . . . ? N21 C26 C27 C32 2.4(4) . . . . ? C25 C26 C27 C32 -175.9(3) . . . . ? C32 C27 C28 F28 -178.4(3) . . . . ? C26 C27 C28 F28 2.4(5) . . . . ? C32 C27 C28 C29 0.9(5) . . . . ? C26 C27 C28 C29 -178.3(3) . . . . ? F28 C28 C29 C30 179.6(3) . . . . ? C27 C28 C29 C30 0.3(5) . . . . ? C28 C29 C30 F30 179.1(3) . . . . ? C28 C29 C30 C31 -1.0(6) . . . . ? F30 C30 C31 C32 -179.7(3) . . . . ? C29 C30 C31 C32 0.4(5) . . . . ? C30 C31 C32 C27 0.9(5) . . . . ? C30 C31 C32 Ir -179.3(2) . . . . ? C28 C27 C32 C31 -1.5(4) . . . . ? C26 C27 C32 C31 177.8(3) . . . . ? C28 C27 C32 Ir 178.7(2) . . . . ? C26 C27 C32 Ir -2.0(3) . . . . ? C52 Ir C32 C31 -84.2(3) . . . . ? N21 Ir C32 C31 -178.9(3) . . . . ? N41 Ir C32 C31 -4.0(3) . . . . ? N8 Ir C32 C31 104.9(9) . . . . ? N1 Ir C32 C31 93.5(3) . . . . ? C52 Ir C32 C27 95.6(2) . . . . ? N21 Ir C32 C27 0.9(2) . . . . ? N41 Ir C32 C27 175.8(2) . . . . ? N8 Ir C32 C27 -75.2(9) . . . . ? N1 Ir C32 C27 -86.7(2) . . . . ? C52 Ir N41 C42 -179.2(3) . . . . ? C32 Ir N41 C42 94.6(3) . . . . ? N21 Ir N41 C42 133.9(6) . . . . ? N8 Ir N41 C42 -78.7(3) . . . . ? N1 Ir N41 C42 -2.8(3) . . . . ? C52 Ir N41 C46 4.2(2) . . . . ? C32 Ir N41 C46 -82.0(2) . . . . ? N21 Ir N41 C46 -42.7(8) . . . . ? N8 Ir N41 C46 104.7(2) . . . . ? N1 Ir N41 C46 -179.4(2) . . . . ? C46 N41 C42 C43 1.3(5) . . . . ? Ir N41 C42 C43 -175.2(3) . . . . ? N41 C42 C43 C44 -0.8(6) . . . . ? C42 C43 C44 C45 0.4(6) . . . . ? C43 C44 C45 C46 -0.5(5) . . . . ? C42 N41 C46 C45 -1.3(4) . . . . ? Ir N41 C46 C45 175.5(2) . . . . ? C42 N41 C46 C47 179.1(3) . . . . ? Ir N41 C46 C47 -4.1(3) . . . . ? C44 C45 C46 N41 1.0(5) . . . . ? C44 C45 C46 C47 -179.5(3) . . . . ? N41 C46 C47 C48 -178.7(3) . . . . ? C45 C46 C47 C48 1.8(5) . . . . ? N41 C46 C47 C52 1.3(4) . . . . ? C45 C46 C47 C52 -178.3(3) . . . . ? C52 C47 C48 F48 -178.1(3) . . . . ? C46 C47 C48 F48 1.8(5) . . . . ? C52 C47 C48 C49 0.7(5) . . . . ? C46 C47 C48 C49 -179.4(3) . . . . ? F48 C48 C49 C50 178.3(3) . . . . ? C47 C48 C49 C50 -0.5(5) . . . . ? C48 C49 C50 F50 -179.8(3) . . . . ? C48 C49 C50 C51 -0.2(5) . . . . ? F50 C50 C51 C52 -179.6(3) . . . . ? C49 C50 C51 C52 0.8(5) . . . . ? C50 C51 C52 C47 -0.7(4) . . . . ? C50 C51 C52 Ir 176.9(2) . . . . ? C48 C47 C52 C51 -0.1(4) . . . . ? C46 C47 C52 C51 180.0(3) . . . . ? C48 C47 C52 Ir -177.9(2) . . . . ? C46 C47 C52 Ir 2.2(3) . . . . ? C32 Ir C52 C51 -87.1(3) . . . . ? N21 Ir C52 C51 -6.7(3) . . . . ? N41 Ir C52 C51 179.1(3) . . . . ? N8 Ir C52 C51 91.8(3) . . . . ? N1 Ir C52 C51 124.1(12) . . . . ? C32 Ir C52 C47 90.5(2) . . . . ? N21 Ir C52 C47 170.9(2) . . . . ? N41 Ir C52 C47 -3.3(2) . . . . ? N8 Ir C52 C47 -90.6(2) . . . . ? N1 Ir C52 C47 -58.3(14) . . . . ? C65 O61 C62 C63 14.8(7) . . . . ? O61 C62 C63 C64 -8.7(9) . . . . ? C62 C63 C64 C65 -0.2(9) . . . . ? C62 O61 C65 C64 -14.5(7) . . . . ? C63 C64 C65 O61 8.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.363 _refine_diff_density_min -1.148 _refine_diff_density_rms 0.095