# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Marcus Weck' 'Alpay Kimyonok' 'Xian-Yong Wang.' _publ_contact_author_name 'Prof Marcus Weck' _publ_contact_author_address ; School of Chemistry & Biochemistry Georgia Institute of Technology 770 State Street, Boggs Bldg. Atlanta GA 30332 0400 UNITED STATES OF AMERICA ; _publ_contact_author_email MARCUS.WECK@CHEMISTRY.GATECH.EDU _publ_section_title ; Functionalization of polymers with phosphorescent iridium complexes via click chemistry ; # Attachment 'XYW01s.cif' data_xyw01s _database_code_depnum_ccdc_archive 'CCDC 614840' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H36 Ir N3 O2' _chemical_formula_sum 'C48 H36 Ir N3 O2' _chemical_formula_weight 879.00 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.351(3) _cell_length_b 9.5276(14) _cell_length_c 18.051(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.153(3) _cell_angle_gamma 90.00 _cell_volume 3650.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2090 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 19.86 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 3.703 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5246 _exptl_absorpt_correction_T_max 0.8970 _exptl_absorpt_process_details 'SADABS V2.10, Sheldrick 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52112 _diffrn_reflns_av_R_equivalents 0.1582 _diffrn_reflns_av_sigmaI/netI 0.1218 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.33 _reflns_number_total 9083 _reflns_number_gt 5350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0550P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9083 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2981(4) 0.1906(9) 0.4855(4) 0.039(2) Uani 1 1 d . . . C2 C 0.2705(4) 0.0814(10) 0.4410(5) 0.050(2) Uani 1 1 d . . . H2 H 0.2312 0.0961 0.4121 0.060 Uiso 1 1 calc R . . C3 C 0.3003(5) -0.0487(10) 0.4391(5) 0.055(3) Uani 1 1 d . . . H3 H 0.2822 -0.1207 0.4073 0.066 Uiso 1 1 calc R . . C4 C 0.3566(5) -0.0729(11) 0.4837(6) 0.059(3) Uani 1 1 d . . . H4 H 0.3762 -0.1623 0.4829 0.071 Uiso 1 1 calc R . . C5 C 0.3837(4) 0.0301(12) 0.5285(5) 0.052(2) Uani 1 1 d . . . H5 H 0.4222 0.0122 0.5586 0.062 Uiso 1 1 calc R . . C6 C 0.3554(4) 0.1613(10) 0.5303(5) 0.044(2) Uani 1 1 d . . . C7 C 0.3820(4) 0.2694(11) 0.5767(5) 0.052(2) Uani 1 1 d . . . H7 H 0.4210 0.2553 0.6064 0.063 Uiso 1 1 calc R . . C8 C 0.3514(4) 0.3936(11) 0.5788(5) 0.054(3) Uani 1 1 d . . . H8 H 0.3689 0.4664 0.6105 0.064 Uiso 1 1 calc R . . C9 C 0.2936(4) 0.4162(10) 0.5341(4) 0.0396(19) Uani 1 1 d . . . C10 C 0.2588(4) 0.5482(9) 0.5352(5) 0.043(2) Uani 1 1 d . . . C11 C 0.2739(5) 0.6515(11) 0.5908(5) 0.050(2) Uani 1 1 d . . . H11 H 0.3079 0.6369 0.6284 0.061 Uiso 1 1 calc R . . C12 C 0.2388(5) 0.7732(10) 0.5898(5) 0.055(3) Uani 1 1 d . . . H12 H 0.2470 0.8402 0.6286 0.066 Uiso 1 1 calc R . . C13 C 0.1919(4) 0.7979(10) 0.5327(6) 0.054(3) Uani 1 1 d . . . H13 H 0.1683 0.8825 0.5316 0.064 Uiso 1 1 calc R . . C14 C 0.1792(4) 0.6980(9) 0.4762(5) 0.045(2) Uani 1 1 d . . . H14 H 0.1478 0.7184 0.4363 0.054 Uiso 1 1 calc R . . C15 C 0.2106(4) 0.5700(8) 0.4763(4) 0.036(2) Uani 1 1 d . . . C16 C 0.0906(4) 0.2780(8) 0.4995(4) 0.038(2) Uani 1 1 d . . . C17 C 0.1391(4) 0.2156(9) 0.5460(5) 0.046(2) Uani 1 1 d . . . H17 H 0.1818 0.2338 0.5389 0.055 Uiso 1 1 calc R . . C18 C 0.1248(5) 0.1275(9) 0.6024(5) 0.052(3) Uani 1 1 d . . . H18 H 0.1582 0.0859 0.6339 0.062 Uiso 1 1 calc R . . C19 C 0.0635(5) 0.0980(10) 0.6145(6) 0.058(3) Uani 1 1 d . . . H19 H 0.0551 0.0375 0.6540 0.070 Uiso 1 1 calc R . . C20 C 0.0156(5) 0.1552(10) 0.5700(6) 0.058(3) Uani 1 1 d . . . H20 H -0.0265 0.1324 0.5776 0.070 Uiso 1 1 calc R . . C21 C 0.0273(4) 0.2495(10) 0.5119(5) 0.044(2) Uani 1 1 d . . . C22 C -0.0219(4) 0.3155(10) 0.4669(5) 0.050(2) Uani 1 1 d . . . H22 H -0.0645 0.2948 0.4729 0.061 Uiso 1 1 calc R . . C23 C -0.0076(4) 0.4096(10) 0.4144(5) 0.044(2) Uani 1 1 d . . . H23 H -0.0404 0.4597 0.3860 0.053 Uiso 1 1 calc R . . C24 C 0.0563(4) 0.4332(8) 0.4018(4) 0.036(2) Uani 1 1 d . . . C25 C 0.0731(4) 0.5257(8) 0.3434(4) 0.0340(19) Uani 1 1 d . . . C26 C 0.0295(4) 0.6110(8) 0.3013(5) 0.041(2) Uani 1 1 d . . . H26 H -0.0131 0.6117 0.3119 0.049 Uiso 1 1 calc R . . C27 C 0.0472(4) 0.6937(9) 0.2452(5) 0.048(2) Uani 1 1 d . . . H27 H 0.0173 0.7511 0.2166 0.058 Uiso 1 1 calc R . . C28 C 0.1096(4) 0.6917(9) 0.2310(5) 0.048(2) Uani 1 1 d . . . H28 H 0.1223 0.7463 0.1912 0.057 Uiso 1 1 calc R . . C29 C 0.1539(4) 0.6113(9) 0.2740(5) 0.043(2) Uani 1 1 d . . . H29 H 0.1966 0.6142 0.2639 0.052 Uiso 1 1 calc R . . C30 C 0.1372(4) 0.5254(8) 0.3324(4) 0.0310(18) Uani 1 1 d . . . C31 C 0.1375(4) 0.1515(9) 0.3167(5) 0.045(2) Uani 1 1 d . . . H31 H 0.1072 0.1539 0.3516 0.054 Uiso 1 1 calc R . . C32 C 0.1332(4) 0.0467(9) 0.2628(5) 0.047(2) Uani 1 1 d . . . H32 H 0.1010 -0.0223 0.2610 0.056 Uiso 1 1 calc R . . C33 C 0.1763(5) 0.0460(10) 0.2129(5) 0.057(3) Uani 1 1 d . . . H33 H 0.1742 -0.0246 0.1756 0.068 Uiso 1 1 calc R . . C34 C 0.2238(4) 0.1475(9) 0.2156(5) 0.048(2) Uani 1 1 d . . . H34 H 0.2539 0.1466 0.1805 0.058 Uiso 1 1 calc R . . C35 C 0.2259(4) 0.2509(9) 0.2713(4) 0.040(2) Uani 1 1 d . . . C36 C 0.2726(4) 0.3636(8) 0.2825(4) 0.0345(19) Uani 1 1 d . . . C37 C 0.3187(4) 0.3840(9) 0.2358(5) 0.046(2) Uani 1 1 d . . . H37 H 0.3189 0.3277 0.1925 0.055 Uiso 1 1 calc R . . C38 C 0.3643(4) 0.4845(9) 0.2509(5) 0.046(2) Uani 1 1 d . . . H38 H 0.3958 0.4990 0.2183 0.055 Uiso 1 1 calc R . . C39 C 0.3633(4) 0.5634(9) 0.3144(5) 0.041(2) Uani 1 1 d . . . C40 C 0.3168(4) 0.5451(9) 0.3606(4) 0.036(2) Uani 1 1 d . . . H40 H 0.3176 0.6016 0.4041 0.043 Uiso 1 1 calc R . . C41 C 0.2682(4) 0.4468(8) 0.3463(4) 0.0342(19) Uani 1 1 d . . . C42 C 0.4162(4) 0.6682(9) 0.3352(5) 0.045(2) Uani 1 1 d . . . H42A H 0.4230 0.6795 0.3900 0.053 Uiso 1 1 calc R . . H42B H 0.4558 0.6345 0.3176 0.053 Uiso 1 1 calc R . . C43 C 0.4399(4) 0.9036(10) 0.3125(5) 0.047(2) Uani 1 1 d . . . C44 C 0.4228(6) 1.0286(11) 0.2720(6) 0.078(4) Uani 1 1 d . . . H44A H 0.3773 1.0463 0.2736 0.094 Uiso 1 1 calc R . . H44B H 0.4300 1.0147 0.2192 0.094 Uiso 1 1 calc R . . C45 C 0.4613(5) 1.1622(11) 0.3035(5) 0.060(3) Uani 1 1 d . . . H45A H 0.5067 1.1392 0.3111 0.072 Uiso 1 1 calc R . . H45B H 0.4553 1.2396 0.2669 0.072 Uiso 1 1 calc R . . C46 C 0.4402(5) 1.2076(11) 0.3745(6) 0.064(3) Uani 1 1 d . . . H46A H 0.4373 1.1259 0.4079 0.077 Uiso 1 1 calc R . . H46B H 0.3980 1.2516 0.3657 0.077 Uiso 1 1 calc R . . C47 C 0.4871(7) 1.3112(15) 0.4094(7) 0.086(4) Uani 1 1 d . . . C48 C 0.5214(8) 1.3920(16) 0.4399(8) 0.107(5) Uani 1 1 d . . . H48 H 0.5496 1.4581 0.4649 0.129 Uiso 1 1 calc R . . Ir1 Ir 0.194905(15) 0.41123(3) 0.403184(17) 0.03222(11) Uani 1 1 d . . . N1 N 0.2675(3) 0.3190(7) 0.4860(3) 0.0376(17) Uani 1 1 d . . . N2 N 0.1036(3) 0.3702(7) 0.4429(3) 0.0346(16) Uani 1 1 d . . . N3 N 0.1830(3) 0.2496(7) 0.3213(3) 0.0341(15) Uani 1 1 d . . . O1 O 0.3977(3) 0.8012(7) 0.3002(3) 0.0528(17) Uani 1 1 d . . . O2 O 0.4890(3) 0.8891(7) 0.3502(4) 0.0613(18) 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 C1 0.037(5) 0.049(6) 0.032(4) 0.002(4) 0.007(4) 0.000(4) C2 0.041(5) 0.055(6) 0.054(6) 0.002(5) 0.007(4) 0.001(5) C3 0.062(7) 0.045(6) 0.059(6) 0.003(5) 0.011(5) -0.002(5) C4 0.069(7) 0.055(7) 0.057(6) 0.023(6) 0.025(5) 0.014(6) C5 0.032(5) 0.076(7) 0.048(6) 0.017(5) 0.006(4) 0.008(5) C6 0.037(5) 0.058(6) 0.038(5) 0.006(4) 0.003(4) 0.004(5) C7 0.036(5) 0.076(7) 0.044(5) 0.011(5) 0.001(4) 0.005(5) C8 0.050(6) 0.071(7) 0.040(5) 0.002(5) 0.004(4) -0.013(6) C9 0.031(4) 0.054(5) 0.035(4) 0.003(4) 0.010(4) 0.001(5) C10 0.044(5) 0.053(6) 0.036(5) -0.003(4) 0.019(4) -0.009(4) C11 0.052(6) 0.065(7) 0.035(5) -0.010(5) 0.006(4) -0.009(5) C12 0.067(7) 0.052(6) 0.049(6) -0.018(5) 0.017(5) -0.013(6) C13 0.045(6) 0.046(6) 0.074(7) -0.021(5) 0.024(5) -0.006(5) C14 0.040(5) 0.043(5) 0.055(6) -0.010(4) 0.018(4) -0.006(4) C15 0.037(5) 0.039(5) 0.034(4) -0.012(4) 0.016(4) -0.013(4) C16 0.044(5) 0.033(5) 0.039(5) -0.013(4) 0.017(4) -0.003(4) C17 0.048(6) 0.050(6) 0.040(5) 0.001(4) 0.010(4) 0.000(5) C18 0.060(6) 0.051(6) 0.047(5) 0.006(4) 0.023(5) 0.000(5) C19 0.066(7) 0.050(6) 0.066(6) 0.014(5) 0.035(6) 0.008(6) C20 0.058(7) 0.053(6) 0.070(7) -0.001(5) 0.035(6) -0.014(5) C21 0.045(5) 0.042(5) 0.050(5) -0.011(4) 0.019(4) -0.012(5) C22 0.037(5) 0.059(6) 0.057(6) -0.008(5) 0.012(5) -0.015(5) C23 0.032(5) 0.051(5) 0.050(5) -0.014(5) 0.008(4) 0.002(5) C24 0.032(5) 0.034(5) 0.041(5) -0.018(4) 0.002(4) -0.004(4) C25 0.035(5) 0.031(4) 0.035(4) -0.011(4) 0.002(4) -0.006(4) C26 0.036(5) 0.037(5) 0.049(5) -0.011(4) -0.002(4) 0.003(4) C27 0.056(6) 0.037(5) 0.050(6) 0.004(4) -0.005(5) 0.010(5) C28 0.055(6) 0.035(5) 0.054(6) 0.002(4) 0.008(5) 0.009(5) C29 0.042(5) 0.043(6) 0.044(5) -0.009(4) 0.008(4) -0.010(4) C30 0.027(4) 0.029(4) 0.037(4) -0.008(4) 0.003(3) 0.000(4) C31 0.032(5) 0.041(5) 0.060(6) -0.006(5) 0.003(4) 0.002(4) C32 0.042(6) 0.039(5) 0.058(6) -0.010(4) -0.002(5) -0.002(4) C33 0.065(7) 0.051(6) 0.055(6) -0.029(5) 0.011(5) -0.010(5) C34 0.055(6) 0.045(5) 0.046(5) -0.018(4) 0.009(5) 0.003(5) C35 0.036(5) 0.042(5) 0.039(5) -0.002(4) 0.001(4) 0.004(4) C36 0.034(5) 0.034(5) 0.036(4) -0.001(3) 0.006(4) 0.001(4) C37 0.046(6) 0.049(6) 0.046(5) -0.009(4) 0.020(4) 0.000(4) C38 0.036(5) 0.047(6) 0.058(6) -0.009(5) 0.021(4) -0.011(4) C39 0.036(5) 0.044(6) 0.045(5) 0.000(4) 0.011(4) -0.003(4) C40 0.033(5) 0.049(5) 0.028(4) -0.004(4) 0.010(3) -0.002(4) C41 0.036(5) 0.031(5) 0.036(4) 0.001(3) 0.005(4) 0.003(4) C42 0.040(5) 0.046(6) 0.050(5) 0.011(4) 0.013(4) -0.002(4) C43 0.045(6) 0.045(5) 0.051(5) -0.002(5) 0.003(4) -0.004(5) C44 0.103(10) 0.044(6) 0.082(9) 0.001(6) -0.015(7) 0.008(7) C45 0.057(7) 0.064(7) 0.063(7) 0.014(5) 0.023(5) 0.006(6) C46 0.065(7) 0.054(7) 0.078(8) 0.000(6) 0.024(6) 0.011(6) C47 0.091(10) 0.082(10) 0.084(9) 0.006(8) -0.005(8) -0.003(8) C48 0.116(13) 0.103(12) 0.104(11) -0.010(9) 0.015(10) -0.021(10) Ir1 0.02973(17) 0.03457(17) 0.03356(16) -0.00412(17) 0.00892(11) -0.00199(19) N1 0.046(4) 0.039(4) 0.030(4) -0.006(3) 0.014(3) -0.003(3) N2 0.041(4) 0.030(4) 0.032(4) -0.010(3) 0.007(3) -0.002(3) N3 0.032(4) 0.032(4) 0.038(4) 0.001(3) 0.007(3) 0.005(3) O1 0.052(4) 0.049(4) 0.054(4) -0.001(3) -0.007(3) -0.007(3) O2 0.051(4) 0.056(5) 0.074(5) 0.006(4) -0.011(4) -0.005(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 C1 N1 1.387(10) . ? C1 C2 1.404(12) . ? C1 C6 1.421(11) . ? C2 C3 1.395(12) . ? C2 H2 0.9500 . ? C3 C4 1.391(13) . ? C3 H3 0.9500 . ? C4 C5 1.361(13) . ? C4 H4 0.9500 . ? C5 C6 1.391(13) . ? C5 H5 0.9500 . ? C6 C7 1.409(13) . ? C7 C8 1.354(13) . ? C7 H7 0.9500 . ? C8 C9 1.417(12) . ? C8 H8 0.9500 . ? C9 N1 1.347(10) . ? C9 C10 1.461(12) . ? C10 C15 1.415(11) . ? C10 C11 1.417(12) . ? C11 C12 1.379(13) . ? C11 H11 0.9500 . ? C12 C13 1.379(13) . ? C12 H12 0.9500 . ? C13 C14 1.399(11) . ? C13 H13 0.9500 . ? C14 C15 1.391(11) . ? C14 H14 0.9500 . ? C15 Ir1 2.011(7) . ? C16 C17 1.395(11) . ? C16 N2 1.398(10) . ? C16 C21 1.420(11) . ? C17 C18 1.379(11) . ? C17 H17 0.9500 . ? C18 C19 1.377(12) . ? C18 H18 0.9500 . ? C19 C20 1.345(13) . ? C19 H19 0.9500 . ? C20 C21 1.422(12) . ? C20 H20 0.9500 . ? C21 C22 1.405(12) . ? C22 C23 1.362(12) . ? C22 H22 0.9500 . ? C23 C24 1.426(11) . ? C23 H23 0.9500 . ? C24 N2 1.330(10) . ? C24 C25 1.448(11) . ? C25 C26 1.397(11) . ? C25 C30 1.404(11) . ? C26 C27 1.368(11) . ? C26 H26 0.9500 . ? C27 C28 1.383(12) . ? C27 H27 0.9500 . ? C28 C29 1.388(11) . ? C28 H28 0.9500 . ? C29 C30 1.409(11) . ? C29 H29 0.9500 . ? C30 Ir1 1.999(8) . ? C31 N3 1.345(10) . ? C31 C32 1.391(11) . ? C31 H31 0.9500 . ? C32 C33 1.354(12) . ? C32 H32 0.9500 . ? C33 C34 1.398(12) . ? C33 H33 0.9500 . ? C34 C35 1.405(11) . ? C34 H34 0.9500 . ? C35 N3 1.353(10) . ? C35 C36 1.464(11) . ? C36 C37 1.375(11) . ? C36 C41 1.410(11) . ? C37 C38 1.371(11) . ? C37 H37 0.9500 . ? C38 C39 1.372(11) . ? C38 H38 0.9500 . ? C39 C40 1.376(10) . ? C39 C42 1.524(11) . ? C40 C41 1.401(10) . ? C40 H40 0.9500 . ? C41 Ir1 1.990(8) . ? C42 O1 1.452(10) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 O2 1.195(10) . ? C43 O1 1.331(10) . ? C43 C44 1.424(13) . ? C44 C45 1.587(14) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.468(13) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.496(16) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.161(17) . ? C48 H48 0.9500 . ? Ir1 N3 2.130(6) . ? Ir1 N2 2.183(7) . ? Ir1 N1 2.217(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 119.3(8) . . ? N1 C1 C6 123.1(8) . . ? C2 C1 C6 117.5(8) . . ? C3 C2 C1 120.5(9) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.1(10) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.7(10) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.2(9) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 121.5(9) . . ? C5 C6 C1 120.9(9) . . ? C7 C6 C1 117.5(9) . . ? C8 C7 C6 119.4(9) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.7(9) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? N1 C9 C8 122.5(9) . . ? N1 C9 C10 115.2(7) . . ? C8 C9 C10 122.4(9) . . ? C15 C10 C11 121.4(9) . . ? C15 C10 C9 116.5(8) . . ? C11 C10 C9 122.0(9) . . ? C12 C11 C10 119.6(9) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.1(9) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.8(9) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 122.7(9) . . ? C15 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C14 C15 C10 116.2(7) . . ? C14 C15 Ir1 127.8(6) . . ? C10 C15 Ir1 116.0(6) . . ? C17 C16 N2 121.0(7) . . ? C17 C16 C21 118.8(8) . . ? N2 C16 C21 120.2(8) . . ? C18 C17 C16 119.7(9) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 122.0(10) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C20 C19 C18 119.8(9) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.9(9) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C22 C21 C16 119.1(8) . . ? C22 C21 C20 122.1(9) . . ? C16 C21 C20 118.8(9) . . ? C23 C22 C21 119.3(8) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 120.2(9) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? N2 C24 C23 121.5(8) . . ? N2 C24 C25 116.7(7) . . ? C23 C24 C25 121.8(8) . . ? C26 C25 C30 121.8(8) . . ? C26 C25 C24 123.2(8) . . ? C30 C25 C24 115.0(7) . . ? C27 C26 C25 121.2(8) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 118.5(8) . . ? C26 C27 H27 120.8 . . ? C28 C27 H27 120.8 . . ? C27 C28 C29 121.1(9) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C30 121.8(8) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C25 C30 C29 115.7(7) . . ? C25 C30 Ir1 117.0(6) . . ? C29 C30 Ir1 127.3(6) . . ? N3 C31 C32 122.4(8) . . ? N3 C31 H31 118.8 . . ? C32 C31 H31 118.8 . . ? C33 C32 C31 118.1(9) . . ? C33 C32 H32 121.0 . . ? C31 C32 H32 121.0 . . ? C32 C33 C34 121.0(8) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C35 118.5(8) . . ? C33 C34 H34 120.7 . . ? C35 C34 H34 120.7 . . ? N3 C35 C34 119.9(8) . . ? N3 C35 C36 114.5(7) . . ? C34 C35 C36 125.6(8) . . ? C37 C36 C41 122.4(8) . . ? C37 C36 C35 122.7(7) . . ? C41 C36 C35 114.8(7) . . ? C38 C37 C36 121.1(8) . . ? C38 C37 H37 119.4 . . ? C36 C37 H37 119.4 . . ? C37 C38 C39 118.3(8) . . ? C37 C38 H38 120.9 . . ? C39 C38 H38 120.9 . . ? C38 C39 C40 120.9(8) . . ? C38 C39 C42 119.2(7) . . ? C40 C39 C42 119.8(7) . . ? C39 C40 C41 122.8(7) . . ? C39 C40 H40 118.6 . . ? C41 C40 H40 118.6 . . ? C40 C41 C36 114.4(7) . . ? C40 C41 Ir1 128.8(6) . . ? C36 C41 Ir1 116.8(6) . . ? O1 C42 C39 107.7(7) . . ? O1 C42 H42A 110.2 . . ? C39 C42 H42A 110.2 . . ? O1 C42 H42B 110.2 . . ? C39 C42 H42B 110.2 . . ? H42A C42 H42B 108.5 . . ? O2 C43 O1 123.2(9) . . ? O2 C43 C44 123.4(10) . . ? O1 C43 C44 113.3(9) . . ? C43 C44 C45 113.1(9) . . ? C43 C44 H44A 109.0 . . ? C45 C44 H44A 109.0 . . ? C43 C44 H44B 109.0 . . ? C45 C44 H44B 109.0 . . ? H44A C44 H44B 107.8 . . ? C46 C45 C44 110.7(9) . . ? C46 C45 H45A 109.5 . . ? C44 C45 H45A 109.5 . . ? C46 C45 H45B 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 108.1 . . ? C45 C46 C47 107.9(9) . . ? C45 C46 H46A 110.1 . . ? C47 C46 H46A 110.1 . . ? C45 C46 H46B 110.1 . . ? C47 C46 H46B 110.1 . . ? H46A C46 H46B 108.4 . . ? C48 C47 C46 176.1(16) . . ? C47 C48 H48 180.0 . . ? C41 Ir1 C30 92.4(3) . . ? C41 Ir1 C15 97.2(3) . . ? C30 Ir1 C15 93.3(3) . . ? C41 Ir1 N3 78.9(3) . . ? C30 Ir1 N3 86.0(3) . . ? C15 Ir1 N3 176.0(3) . . ? C41 Ir1 N2 168.2(3) . . ? C30 Ir1 N2 78.3(3) . . ? C15 Ir1 N2 90.6(3) . . ? N3 Ir1 N2 93.1(2) . . ? C41 Ir1 N1 83.3(3) . . ? C30 Ir1 N1 170.2(3) . . ? C15 Ir1 N1 78.5(3) . . ? N3 Ir1 N1 101.8(2) . . ? N2 Ir1 N1 107.0(2) . . ? C9 N1 C1 116.7(7) . . ? C9 N1 Ir1 111.9(5) . . ? C1 N1 Ir1 129.8(5) . . ? C24 N2 C16 119.5(7) . . ? C24 N2 Ir1 112.8(5) . . ? C16 N2 Ir1 127.4(5) . . ? C31 N3 C35 120.1(7) . . ? C31 N3 Ir1 125.2(5) . . ? C35 N3 Ir1 114.7(5) . . ? C43 O1 C42 114.8(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.7(8) . . . . ? C6 C1 C2 C3 -2.8(12) . . . . ? C1 C2 C3 C4 2.7(14) . . . . ? C2 C3 C4 C5 -1.3(14) . . . . ? C3 C4 C5 C6 0.1(14) . . . . ? C4 C5 C6 C7 179.2(9) . . . . ? C4 C5 C6 C1 -0.3(13) . . . . ? N1 C1 C6 C5 179.1(7) . . . . ? C2 C1 C6 C5 1.6(12) . . . . ? N1 C1 C6 C7 -0.4(12) . . . . ? C2 C1 C6 C7 -177.9(8) . . . . ? C5 C6 C7 C8 -177.4(8) . . . . ? C1 C6 C7 C8 2.1(13) . . . . ? C6 C7 C8 C9 -0.8(13) . . . . ? C7 C8 C9 N1 -2.4(13) . . . . ? C7 C8 C9 C10 179.4(8) . . . . ? N1 C9 C10 C15 -12.9(10) . . . . ? C8 C9 C10 C15 165.4(7) . . . . ? N1 C9 C10 C11 169.2(7) . . . . ? C8 C9 C10 C11 -12.4(12) . . . . ? C15 C10 C11 C12 3.3(13) . . . . ? C9 C10 C11 C12 -179.0(8) . . . . ? C10 C11 C12 C13 -3.8(14) . . . . ? C11 C12 C13 C14 1.1(14) . . . . ? C12 C13 C14 C15 2.4(13) . . . . ? C13 C14 C15 C10 -2.9(12) . . . . ? C13 C14 C15 Ir1 176.3(6) . . . . ? C11 C10 C15 C14 0.1(11) . . . . ? C9 C10 C15 C14 -177.8(7) . . . . ? C11 C10 C15 Ir1 -179.2(6) . . . . ? C9 C10 C15 Ir1 2.9(9) . . . . ? N2 C16 C17 C18 178.6(7) . . . . ? C21 C16 C17 C18 0.5(12) . . . . ? C16 C17 C18 C19 0.2(14) . . . . ? C17 C18 C19 C20 0.5(15) . . . . ? C18 C19 C20 C21 -1.9(15) . . . . ? C17 C16 C21 C22 177.9(8) . . . . ? N2 C16 C21 C22 -0.2(12) . . . . ? C17 C16 C21 C20 -1.8(12) . . . . ? N2 C16 C21 C20 -180.0(7) . . . . ? C19 C20 C21 C22 -177.1(9) . . . . ? C19 C20 C21 C16 2.6(14) . . . . ? C16 C21 C22 C23 -2.7(13) . . . . ? C20 C21 C22 C23 177.0(9) . . . . ? C21 C22 C23 C24 4.5(13) . . . . ? C22 C23 C24 N2 -3.4(12) . . . . ? C22 C23 C24 C25 176.1(8) . . . . ? N2 C24 C25 C26 -172.5(7) . . . . ? C23 C24 C25 C26 7.9(12) . . . . ? N2 C24 C25 C30 6.5(10) . . . . ? C23 C24 C25 C30 -173.0(7) . . . . ? C30 C25 C26 C27 3.0(12) . . . . ? C24 C25 C26 C27 -178.0(7) . . . . ? C25 C26 C27 C28 -0.4(13) . . . . ? C26 C27 C28 C29 -1.9(13) . . . . ? C27 C28 C29 C30 1.8(13) . . . . ? C26 C25 C30 C29 -3.0(11) . . . . ? C24 C25 C30 C29 177.9(7) . . . . ? C26 C25 C30 Ir1 174.4(6) . . . . ? C24 C25 C30 Ir1 -4.7(9) . . . . ? C28 C29 C30 C25 0.7(11) . . . . ? C28 C29 C30 Ir1 -176.5(6) . . . . ? N3 C31 C32 C33 -0.9(14) . . . . ? C31 C32 C33 C34 0.0(15) . . . . ? C32 C33 C34 C35 0.0(15) . . . . ? C33 C34 C35 N3 0.7(13) . . . . ? C33 C34 C35 C36 179.4(8) . . . . ? N3 C35 C36 C37 -178.0(8) . . . . ? C34 C35 C36 C37 3.2(13) . . . . ? N3 C35 C36 C41 4.2(10) . . . . ? C34 C35 C36 C41 -174.6(8) . . . . ? C41 C36 C37 C38 2.3(13) . . . . ? C35 C36 C37 C38 -175.4(8) . . . . ? C36 C37 C38 C39 0.7(14) . . . . ? C37 C38 C39 C40 -1.8(14) . . . . ? C37 C38 C39 C42 175.6(8) . . . . ? C38 C39 C40 C41 0.0(13) . . . . ? C42 C39 C40 C41 -177.5(7) . . . . ? C39 C40 C41 C36 2.8(12) . . . . ? C39 C40 C41 Ir1 -176.8(6) . . . . ? C37 C36 C41 C40 -3.9(12) . . . . ? C35 C36 C41 C40 173.9(7) . . . . ? C37 C36 C41 Ir1 175.7(6) . . . . ? C35 C36 C41 Ir1 -6.5(9) . . . . ? C38 C39 C42 O1 89.6(9) . . . . ? C40 C39 C42 O1 -93.0(9) . . . . ? O2 C43 C44 C45 -21.4(15) . . . . ? O1 C43 C44 C45 163.1(8) . . . . ? C43 C44 C45 C46 -72.8(12) . . . . ? C44 C45 C46 C47 167.4(9) . . . . ? C45 C46 C47 C48 -178(100) . . . . ? C40 C41 Ir1 C30 98.9(7) . . . . ? C36 C41 Ir1 C30 -80.6(6) . . . . ? C40 C41 Ir1 C15 5.3(8) . . . . ? C36 C41 Ir1 C15 -174.3(6) . . . . ? C40 C41 Ir1 N3 -175.6(8) . . . . ? C36 C41 Ir1 N3 4.8(6) . . . . ? C40 C41 Ir1 N2 136.6(12) . . . . ? C36 C41 Ir1 N2 -43.0(16) . . . . ? C40 C41 Ir1 N1 -72.2(7) . . . . ? C36 C41 Ir1 N1 108.3(6) . . . . ? C25 C30 Ir1 C41 174.2(6) . . . . ? C29 C30 Ir1 C41 -8.8(7) . . . . ? C25 C30 Ir1 C15 -88.5(6) . . . . ? C29 C30 Ir1 C15 88.6(7) . . . . ? C25 C30 Ir1 N3 95.5(6) . . . . ? C29 C30 Ir1 N3 -87.4(7) . . . . ? C25 C30 Ir1 N2 1.5(6) . . . . ? C29 C30 Ir1 N2 178.6(7) . . . . ? C25 C30 Ir1 N1 -121.8(15) . . . . ? C29 C30 Ir1 N1 55.3(19) . . . . ? C14 C15 Ir1 C41 103.2(7) . . . . ? C10 C15 Ir1 C41 -77.6(6) . . . . ? C14 C15 Ir1 C30 10.3(7) . . . . ? C10 C15 Ir1 C30 -170.4(6) . . . . ? C14 C15 Ir1 N3 91(4) . . . . ? C10 C15 Ir1 N3 -90(4) . . . . ? C14 C15 Ir1 N2 -67.9(7) . . . . ? C10 C15 Ir1 N2 111.3(6) . . . . ? C14 C15 Ir1 N1 -175.2(7) . . . . ? C10 C15 Ir1 N1 4.1(5) . . . . ? C8 C9 N1 C1 4.0(11) . . . . ? C10 C9 N1 C1 -177.7(6) . . . . ? C8 C9 N1 Ir1 -162.8(6) . . . . ? C10 C9 N1 Ir1 15.5(8) . . . . ? C2 C1 N1 C9 174.8(7) . . . . ? C6 C1 N1 C9 -2.6(11) . . . . ? C2 C1 N1 Ir1 -21.2(11) . . . . ? C6 C1 N1 Ir1 161.4(6) . . . . ? C41 Ir1 N1 C9 87.9(5) . . . . ? C30 Ir1 N1 C9 23.1(18) . . . . ? C15 Ir1 N1 C9 -10.9(5) . . . . ? N3 Ir1 N1 C9 165.0(5) . . . . ? N2 Ir1 N1 C9 -98.1(5) . . . . ? C41 Ir1 N1 C1 -76.7(7) . . . . ? C30 Ir1 N1 C1 -141.5(15) . . . . ? C15 Ir1 N1 C1 -175.5(7) . . . . ? N3 Ir1 N1 C1 0.4(7) . . . . ? N2 Ir1 N1 C1 97.4(7) . . . . ? C23 C24 N2 C16 0.4(11) . . . . ? C25 C24 N2 C16 -179.1(6) . . . . ? C23 C24 N2 Ir1 174.4(6) . . . . ? C25 C24 N2 Ir1 -5.1(8) . . . . ? C17 C16 N2 C24 -176.8(7) . . . . ? C21 C16 N2 C24 1.3(11) . . . . ? C17 C16 N2 Ir1 10.3(10) . . . . ? C21 C16 N2 Ir1 -171.6(6) . . . . ? C41 Ir1 N2 C24 -36.5(15) . . . . ? C30 Ir1 N2 C24 2.1(5) . . . . ? C15 Ir1 N2 C24 95.3(5) . . . . ? N3 Ir1 N2 C24 -83.2(5) . . . . ? N1 Ir1 N2 C24 173.5(5) . . . . ? C41 Ir1 N2 C16 136.8(13) . . . . ? C30 Ir1 N2 C16 175.4(6) . . . . ? C15 Ir1 N2 C16 -91.4(6) . . . . ? N3 Ir1 N2 C16 90.1(6) . . . . ? N1 Ir1 N2 C16 -13.2(6) . . . . ? C32 C31 N3 C35 1.6(12) . . . . ? C32 C31 N3 Ir1 -178.5(6) . . . . ? C34 C35 N3 C31 -1.5(12) . . . . ? C36 C35 N3 C31 179.7(7) . . . . ? C34 C35 N3 Ir1 178.6(6) . . . . ? C36 C35 N3 Ir1 -0.2(9) . . . . ? C41 Ir1 N3 C31 177.6(7) . . . . ? C30 Ir1 N3 C31 -89.1(7) . . . . ? C15 Ir1 N3 C31 -170(4) . . . . ? N2 Ir1 N3 C31 -11.1(7) . . . . ? N1 Ir1 N3 C31 97.0(7) . . . . ? C41 Ir1 N3 C35 -2.5(6) . . . . ? C30 Ir1 N3 C35 90.8(6) . . . . ? C15 Ir1 N3 C35 10(4) . . . . ? N2 Ir1 N3 C35 168.8(5) . . . . ? N1 Ir1 N3 C35 -83.1(6) . . . . ? O2 C43 O1 C42 -0.9(13) . . . . ? C44 C43 O1 C42 174.6(8) . . . . ? C39 C42 O1 C43 -179.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.026 _refine_diff_density_min -1.013 _refine_diff_density_rms 0.172