# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'SooYoung Park' _publ_contact_author_email PARKSY@SNU.AC.KR _publ_section_title ; Comment on 'Aggregation-induced phosphorescent emission (AIPE) of iridium(III) complexes': origin of the enhanced phosphorescence ; loop_ _publ_author_name 'SooYoung Park.' 'Hyun Sue Huh.' 'Kil Suk Kim.' 'Dongho Kim.' 'Soon W. Lee' ; Youngmin You ; # Attachment '3rdRSCCIF.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 684918' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H23 Cl3 F4 Ir N3 O' _chemical_formula_weight 888.12 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' 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 '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 12.6771(5) _cell_length_b 28.1017(11) _cell_length_c 9.8656(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.082(2) _cell_angle_gamma 90.00 _cell_volume 3393.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9154 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.20 _exptl_crystal_description BLOCK _exptl_crystal_colour orange _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 4.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2827 _exptl_absorpt_correction_T_max 0.7285 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 55116 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.55 _reflns_number_total 8413 _reflns_number_gt 7095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0703P)^2^+4.9977P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8413 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.231708(14) 0.117188(6) 0.463307(18) 0.03438(8) Uani 1 1 d . . . F1 F 0.5430(5) 0.15378(15) 0.9386(5) 0.116(2) Uani 1 1 d . . . F2 F 0.5157(5) -0.00148(15) 0.7692(6) 0.113(2) Uani 1 1 d . . . F3 F 0.5480(5) 0.10046(17) 0.1930(7) 0.108(2) Uani 1 1 d . . . F4 F 0.4821(5) 0.25161(15) 0.3474(7) 0.1097(18) Uani 1 1 d . . . O1 O 0.1183(3) 0.12770(15) 0.2665(4) 0.0481(8) Uani 1 1 d . . . N1 N 0.0977(3) 0.09771(15) 0.5465(4) 0.0405(8) Uani 1 1 d . . . N2 N 0.2515(3) 0.04641(14) 0.4351(4) 0.0383(8) Uani 1 1 d . . . N3 N 0.2272(3) 0.18881(14) 0.4979(5) 0.0420(9) Uani 1 1 d . . . C1 C 0.0133(4) 0.12641(19) 0.2369(6) 0.0444(11) Uani 1 1 d . . . C2 C -0.0456(5) 0.1364(3) 0.0961(7) 0.0650(16) Uani 1 1 d . . . H2 H -0.0078 0.1432 0.0294 0.078 Uiso 1 1 calc R . . C3 C -0.1584(6) 0.1361(3) 0.0578(8) 0.082(2) Uani 1 1 d . . . H3 H -0.1949 0.1425 -0.0351 0.099 Uiso 1 1 calc R . . C4 C -0.2182(5) 0.1267(3) 0.1521(9) 0.079(2) Uani 1 1 d . . . H4 H -0.2940 0.1287 0.1252 0.095 Uiso 1 1 calc R . . C5 C -0.1647(5) 0.1142(3) 0.2868(8) 0.0683(19) Uani 1 1 d . . . H5 H -0.2053 0.1058 0.3491 0.082 Uiso 1 1 calc R . . C6 C -0.0481(4) 0.1139(2) 0.3341(6) 0.0491(12) Uani 1 1 d . . . C7 C -0.0039(4) 0.0985(2) 0.4755(6) 0.0474(11) Uani 1 1 d . . . H7 H -0.0541 0.0877 0.5224 0.057 Uiso 1 1 calc R . . C8 C 0.1203(4) 0.0760(2) 0.6838(5) 0.0474(12) Uani 1 1 d . . . C9 C 0.1057(7) 0.0281(2) 0.6950(7) 0.075(2) Uani 1 1 d . . . H9 H 0.0783 0.0097 0.6151 0.090 Uiso 1 1 calc R . . C10 C 0.1321(9) 0.0070(3) 0.8273(8) 0.101(3) Uani 1 1 d . . . H10 H 0.1235 -0.0257 0.8346 0.121 Uiso 1 1 calc R . . C11 C 0.1693(9) 0.0325(3) 0.9432(8) 0.095(3) Uani 1 1 d . . . H11 H 0.1864 0.0178 1.0307 0.114 Uiso 1 1 calc R . . C12 C 0.1824(10) 0.0806(3) 0.9323(8) 0.105(3) Uani 1 1 d . . . H12 H 0.2042 0.0989 1.0133 0.125 Uiso 1 1 calc R . . C13 C 0.1635(8) 0.1023(3) 0.8027(7) 0.077(2) Uani 1 1 d . . . H13 H 0.1799 0.1343 0.7959 0.093 Uiso 1 1 calc R . . C14 C 0.1894(5) 0.02093(19) 0.3272(6) 0.0496(12) Uani 1 1 d . . . H14 H 0.1334 0.0363 0.2623 0.060 Uiso 1 1 calc R . . C15 C 0.2058(7) -0.0274(2) 0.3092(7) 0.0680(18) Uani 1 1 d . . . H15 H 0.1630 -0.0440 0.2330 0.082 Uiso 1 1 calc R . . C16 C 0.2866(7) -0.0496(2) 0.4066(8) 0.076(2) Uani 1 1 d . . . H16 H 0.2988 -0.0820 0.3977 0.091 Uiso 1 1 calc R . . C17 C 0.3509(6) -0.0246(2) 0.5192(7) 0.0639(17) Uani 1 1 d . . . H17 H 0.4064 -0.0399 0.5849 0.077 Uiso 1 1 calc R . . C18 C 0.3315(5) 0.02396(17) 0.5333(6) 0.0460(11) Uani 1 1 d . . . C19 C 0.3898(4) 0.05594(17) 0.6449(6) 0.0460(11) Uani 1 1 d . . . C20 C 0.3514(4) 0.10379(17) 0.6365(5) 0.0388(10) Uani 1 1 d . . . C21 C 0.4050(5) 0.13639(19) 0.7353(6) 0.0516(13) Uani 1 1 d . . . H21 H 0.3824 0.1680 0.7307 0.062 Uiso 1 1 calc R . . C22 C 0.4924(7) 0.1213(2) 0.8407(8) 0.073(2) Uani 1 1 d . . . C23 C 0.5280(6) 0.0753(2) 0.8579(8) 0.082(2) Uani 1 1 d . . . H23 H 0.5830 0.0657 0.9354 0.098 Uiso 1 1 calc R . . C24 C 0.4787(6) 0.0441(2) 0.7555(7) 0.0668(18) Uani 1 1 d . . . C25 C 0.1564(5) 0.2100(2) 0.5575(7) 0.0564(14) Uani 1 1 d . . . H25 H 0.1020 0.1918 0.5800 0.068 Uiso 1 1 calc R . . C26 C 0.1616(6) 0.2586(2) 0.5871(8) 0.0711(19) Uani 1 1 d . . . H26 H 0.1131 0.2726 0.6316 0.085 Uiso 1 1 calc R . . C27 C 0.2391(8) 0.2853(2) 0.5494(8) 0.080(2) Uani 1 1 d . . . H27 H 0.2433 0.3178 0.5670 0.096 Uiso 1 1 calc R . . C28 C 0.3111(7) 0.2640(2) 0.4855(7) 0.0687(19) Uani 1 1 d . . . H28 H 0.3644 0.2822 0.4604 0.082 Uiso 1 1 calc R . . C29 C 0.3046(5) 0.21560(19) 0.4582(6) 0.0492(12) Uani 1 1 d . . . C30 C 0.3738(4) 0.18786(17) 0.3903(6) 0.0469(12) Uani 1 1 d . . . C31 C 0.3504(4) 0.13809(17) 0.3782(5) 0.0380(10) Uani 1 1 d . . . C32 C 0.4098(5) 0.1101(2) 0.3102(7) 0.0524(13) Uani 1 1 d . . . H32 H 0.3958 0.0776 0.3000 0.063 Uiso 1 1 calc R . . C33 C 0.4892(6) 0.1299(2) 0.2580(9) 0.070(2) Uani 1 1 d . . . C34 C 0.5166(6) 0.1772(3) 0.2709(10) 0.083(2) Uani 1 1 d . . . H34 H 0.5724 0.1896 0.2360 0.100 Uiso 1 1 calc R . . C35 C 0.4571(6) 0.2056(2) 0.3384(8) 0.0684(18) Uani 1 1 d . . . C36 C -0.1940(16) 0.2523(8) -0.343(2) 0.185(7) Uiso 1 1 d . . . H36 H -0.2041 0.2840 -0.3862 0.222 Uiso 1 1 calc R . . Cl1 Cl -0.3182(6) 0.2053(3) -0.3103(8) 0.262(3) Uiso 1 1 d . . . Cl2 Cl -0.0824(9) 0.2322(4) -0.2075(12) 0.334(5) Uiso 1 1 d . . . Cl3 Cl -0.1660(14) 0.1916(6) -0.4326(18) 0.501(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.03139(11) 0.03396(11) 0.03563(11) 0.00354(6) 0.00485(7) 0.00039(6) F1 0.139(4) 0.062(2) 0.091(3) -0.010(2) -0.070(3) 0.009(3) F2 0.142(5) 0.057(2) 0.103(4) -0.002(2) -0.038(3) 0.049(3) F3 0.113(4) 0.075(3) 0.178(6) 0.028(3) 0.111(4) 0.021(3) F4 0.106(4) 0.055(2) 0.181(6) 0.013(3) 0.063(4) -0.030(2) O1 0.0363(19) 0.064(2) 0.042(2) 0.0065(17) 0.0074(15) -0.0061(16) N1 0.042(2) 0.043(2) 0.037(2) 0.0012(17) 0.0114(17) -0.0012(17) N2 0.045(2) 0.0357(19) 0.0367(19) 0.0008(15) 0.0143(17) -0.0029(16) N3 0.044(2) 0.035(2) 0.041(2) 0.0031(16) 0.0004(18) 0.0079(16) C1 0.037(3) 0.049(3) 0.042(3) 0.002(2) 0.001(2) 0.002(2) C2 0.047(3) 0.091(5) 0.050(3) 0.017(3) 0.000(3) -0.001(3) C3 0.055(4) 0.117(6) 0.058(4) 0.026(4) -0.016(3) -0.001(4) C4 0.033(3) 0.121(6) 0.075(5) 0.006(4) -0.003(3) -0.005(3) C5 0.037(3) 0.098(5) 0.066(4) 0.010(3) 0.007(3) -0.007(3) C6 0.032(2) 0.061(3) 0.051(3) -0.001(2) 0.007(2) 0.002(2) C7 0.044(3) 0.052(3) 0.051(3) -0.002(2) 0.020(2) -0.004(2) C8 0.049(3) 0.056(3) 0.041(3) -0.001(2) 0.017(2) -0.005(2) C9 0.124(6) 0.053(3) 0.045(3) 0.005(3) 0.017(4) -0.015(4) C10 0.180(10) 0.057(4) 0.060(4) 0.011(3) 0.019(5) -0.017(5) C11 0.166(9) 0.077(5) 0.043(4) 0.008(3) 0.028(4) 0.000(5) C12 0.179(10) 0.088(6) 0.039(3) 0.009(4) 0.016(5) 0.007(6) C13 0.128(7) 0.063(4) 0.043(3) -0.002(3) 0.024(4) -0.012(4) C14 0.055(3) 0.046(3) 0.048(3) -0.007(2) 0.013(2) -0.012(2) C15 0.098(5) 0.052(3) 0.051(3) -0.011(3) 0.014(3) -0.015(3) C16 0.123(6) 0.034(3) 0.079(5) -0.010(3) 0.040(5) -0.008(3) C17 0.086(5) 0.038(3) 0.063(4) -0.001(3) 0.011(3) 0.008(3) C18 0.057(3) 0.033(2) 0.048(3) 0.004(2) 0.012(2) 0.002(2) C19 0.051(3) 0.034(2) 0.047(3) 0.006(2) 0.003(2) 0.004(2) C20 0.036(2) 0.034(2) 0.042(3) 0.0080(18) 0.0026(19) 0.0053(18) C21 0.050(3) 0.036(2) 0.058(3) 0.004(2) -0.005(2) 0.002(2) C22 0.074(5) 0.055(4) 0.062(4) -0.001(3) -0.031(4) -0.002(3) C23 0.083(5) 0.059(4) 0.073(5) 0.004(3) -0.034(4) 0.014(3) C24 0.074(4) 0.040(3) 0.069(4) 0.011(3) -0.011(3) 0.016(3) C25 0.060(4) 0.050(3) 0.058(3) 0.002(3) 0.014(3) 0.015(3) C26 0.081(5) 0.058(4) 0.071(4) -0.002(3) 0.015(4) 0.028(3) C27 0.113(6) 0.040(3) 0.080(5) 0.003(3) 0.015(4) 0.012(4) C28 0.096(5) 0.036(3) 0.065(4) -0.003(3) 0.006(4) -0.010(3) C29 0.050(3) 0.041(3) 0.048(3) 0.006(2) -0.001(2) -0.001(2) C30 0.042(3) 0.038(2) 0.057(3) 0.011(2) 0.007(2) -0.005(2) C31 0.034(2) 0.036(2) 0.041(2) 0.0105(18) 0.0041(18) -0.0025(17) C32 0.047(3) 0.045(3) 0.070(4) 0.010(2) 0.024(3) 0.005(2) C33 0.061(4) 0.059(4) 0.105(6) 0.027(4) 0.048(4) 0.016(3) C34 0.054(4) 0.073(4) 0.140(7) 0.028(4) 0.057(4) -0.005(3) C35 0.065(4) 0.047(3) 0.096(5) 0.018(3) 0.025(4) -0.012(3) _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 C31 1.993(5) . ? Ir1 C20 2.003(5) . ? Ir1 N2 2.033(4) . ? Ir1 N3 2.045(4) . ? Ir1 O1 2.115(4) . ? Ir1 N1 2.141(4) . ? F1 C22 1.363(7) . ? F2 C24 1.358(7) . ? F3 C33 1.378(8) . ? F4 C35 1.328(7) . ? O1 C1 1.287(6) . ? N1 C7 1.296(7) . ? N1 C8 1.445(7) . ? N2 C14 1.353(7) . ? N2 C18 1.361(7) . ? N3 C25 1.334(7) . ? N3 C29 1.372(7) . ? C1 C2 1.423(8) . ? C1 C6 1.428(8) . ? C2 C3 1.381(9) . ? C2 H2 0.9300 . ? C3 C4 1.371(12) . ? C3 H3 0.9300 . ? C4 C5 1.370(11) . ? C4 H4 0.9300 . ? C5 C6 1.429(8) . ? C5 H5 0.9300 . ? C6 C7 1.429(8) . ? C7 H7 0.9300 . ? C8 C9 1.368(8) . ? C8 C13 1.374(9) . ? C9 C10 1.392(10) . ? C9 H9 0.9300 . ? C10 C11 1.327(11) . ? C10 H10 0.9300 . ? C11 C12 1.370(12) . ? C11 H11 0.9300 . ? C12 C13 1.380(10) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.393(8) . ? C14 H14 0.9300 . ? C15 C16 1.360(11) . ? C15 H15 0.9300 . ? C16 C17 1.386(10) . ? C16 H16 0.9300 . ? C17 C18 1.399(7) . ? C17 H17 0.9300 . ? C18 C19 1.464(7) . ? C19 C24 1.389(8) . ? C19 C20 1.426(7) . ? C20 C21 1.381(8) . ? C21 C22 1.374(8) . ? C21 H21 0.9300 . ? C22 C23 1.366(9) . ? C23 C24 1.360(10) . ? C23 H23 0.9300 . ? C25 C26 1.396(9) . ? C25 H25 0.9300 . ? C26 C27 1.362(12) . ? C26 H26 0.9300 . ? C27 C28 1.374(12) . ? C27 H27 0.9300 . ? C28 C29 1.386(8) . ? C28 H28 0.9300 . ? C29 C30 1.460(8) . ? C30 C35 1.381(8) . ? C30 C31 1.428(7) . ? C31 C32 1.378(8) . ? C32 C33 1.363(8) . ? C32 H32 0.9300 . ? C33 C34 1.373(10) . ? C34 C35 1.383(11) . ? C34 H34 0.9300 . ? C36 Cl2 1.77(2) . ? C36 Cl3 1.99(2) . ? C36 Cl1 2.14(2) . ? C36 H36 0.9800 . ? 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 C31 Ir1 C20 85.8(2) . . ? C31 Ir1 N2 95.56(18) . . ? C20 Ir1 N2 80.78(18) . . ? C31 Ir1 N3 80.64(19) . . ? C20 Ir1 N3 95.21(18) . . ? N2 Ir1 N3 174.70(17) . . ? C31 Ir1 O1 88.80(17) . . ? C20 Ir1 O1 172.91(18) . . ? N2 Ir1 O1 95.14(16) . . ? N3 Ir1 O1 88.50(16) . . ? C31 Ir1 N1 176.51(16) . . ? C20 Ir1 N1 97.21(18) . . ? N2 Ir1 N1 86.62(16) . . ? N3 Ir1 N1 97.36(17) . . ? O1 Ir1 N1 88.29(15) . . ? C1 O1 Ir1 128.3(3) . . ? C7 N1 C8 116.1(4) . . ? C7 N1 Ir1 124.4(4) . . ? C8 N1 Ir1 118.9(3) . . ? C14 N2 C18 119.2(4) . . ? C14 N2 Ir1 123.9(4) . . ? C18 N2 Ir1 116.8(3) . . ? C25 N3 C29 119.6(5) . . ? C25 N3 Ir1 124.3(4) . . ? C29 N3 Ir1 116.0(4) . . ? O1 C1 C2 117.7(5) . . ? O1 C1 C6 124.6(5) . . ? C2 C1 C6 117.6(5) . . ? C3 C2 C1 120.6(6) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 122.1(6) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C5 C4 C3 119.0(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.8(7) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 118.5(6) . . ? C1 C6 C7 125.9(5) . . ? C5 C6 C7 115.5(5) . . ? N1 C7 C6 127.9(5) . . ? N1 C7 H7 116.0 . . ? C6 C7 H7 116.0 . . ? C9 C8 C13 119.5(6) . . ? C9 C8 N1 119.6(5) . . ? C13 C8 N1 120.8(5) . . ? C8 C9 C10 119.3(7) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 121.6(7) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 119.2(7) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C13 120.9(8) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C8 C13 C12 119.3(7) . . ? C8 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N2 C14 C15 122.7(6) . . ? N2 C14 H14 118.6 . . ? C15 C14 H14 118.6 . . ? C16 C15 C14 117.9(6) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C15 C16 C17 120.7(6) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 119.5(6) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? N2 C18 C17 119.9(5) . . ? N2 C18 C19 112.8(4) . . ? C17 C18 C19 127.3(5) . . ? C24 C19 C20 117.9(5) . . ? C24 C19 C18 126.2(5) . . ? C20 C19 C18 115.9(4) . . ? C21 C20 C19 119.1(5) . . ? C21 C20 Ir1 127.0(4) . . ? C19 C20 Ir1 113.5(4) . . ? C22 C21 C20 118.8(5) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? F1 C22 C23 117.9(6) . . ? F1 C22 C21 117.9(6) . . ? C23 C22 C21 124.2(6) . . ? C24 C23 C22 116.4(6) . . ? C24 C23 H23 121.8 . . ? C22 C23 H23 121.8 . . ? F2 C24 C23 117.0(5) . . ? F2 C24 C19 119.5(6) . . ? C23 C24 C19 123.4(5) . . ? N3 C25 C26 121.9(6) . . ? N3 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C27 C26 C25 118.7(7) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C28 120.0(6) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C29 120.2(7) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? N3 C29 C28 119.6(6) . . ? N3 C29 C30 113.4(4) . . ? C28 C29 C30 126.9(6) . . ? C35 C30 C31 119.0(5) . . ? C35 C30 C29 125.8(5) . . ? C31 C30 C29 115.1(5) . . ? C32 C31 C30 118.1(5) . . ? C32 C31 Ir1 127.2(4) . . ? C30 C31 Ir1 114.6(4) . . ? C33 C32 C31 120.2(6) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 123.7(6) . . ? C32 C33 F3 118.3(6) . . ? C34 C33 F3 118.0(6) . . ? C33 C34 C35 116.6(5) . . ? C33 C34 H34 121.7 . . ? C35 C34 H34 121.7 . . ? F4 C35 C30 121.3(7) . . ? F4 C35 C34 116.3(6) . . ? C30 C35 C34 122.4(6) . . ? Cl2 C36 Cl3 82.1(10) . . ? Cl2 C36 Cl1 99.4(11) . . ? Cl3 C36 Cl1 76.3(9) . . ? Cl2 C36 H36 127.3 . . ? Cl3 C36 H36 127.3 . . ? Cl1 C36 H36 127.3 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.55 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 2.930 _refine_diff_density_min -0.948 _refine_diff_density_rms 0.134 #=============================================================END data_2 _database_code_depnum_ccdc_archive 'CCDC 684919' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H26 F4 Ir N3 O' _chemical_formula_weight 892.89 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 Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' 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' _cell_length_a 13.5267(6) _cell_length_b 24.8476(11) _cell_length_c 23.8083(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8002.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9973 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 22.23 _exptl_crystal_description BLOCK _exptl_crystal_colour orange _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3504 _exptl_absorpt_coefficient_mu 3.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3440 _exptl_absorpt_correction_T_max 0.7731 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 76093 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.41 _reflns_number_total 18234 _reflns_number_gt 9221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0402P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.525(9) _refine_ls_number_reflns 18234 _refine_ls_number_parameters 974 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.68375(3) 0.589877(18) 0.239683(15) 0.04779(13) Uani 1 1 d . . . Ir2 Ir 1.06758(3) 0.409461(18) 0.205196(15) 0.04666(12) Uani 1 1 d . . . F1 F 0.8697(7) 0.5437(5) 0.0455(4) 0.145(4) Uani 1 1 d . . . F2 F 0.5234(7) 0.5373(4) 0.0468(3) 0.125(4) Uani 1 1 d . . . F3 F 0.5704(5) 0.7819(3) 0.1530(4) 0.096(3) Uani 1 1 d . . . F4 F 0.8862(6) 0.7702(4) 0.2294(5) 0.118(4) Uani 1 1 d . . . F5 F 1.1794(6) 0.2187(4) 0.2929(4) 0.103(3) Uani 1 1 d . . . F6 F 0.8634(6) 0.2296(3) 0.2153(4) 0.095(3) Uani 1 1 d . . . F7 F 0.8760(7) 0.4595(4) 0.3981(4) 0.123(3) Uani 1 1 d . . . F8 F 1.2220(7) 0.4599(4) 0.4006(3) 0.107(3) Uani 1 1 d . . . O1 O 0.6870(5) 0.5068(3) 0.2638(3) 0.057(2) Uani 1 1 d . . . O2 O 1.0657(5) 0.4918(3) 0.1814(4) 0.060(3) Uani 1 1 d . . . N1 N 0.6612(6) 0.6063(4) 0.3281(4) 0.047(2) Uani 1 1 d . . . N2 N 0.5397(8) 0.5810(4) 0.2198(4) 0.054(4) Uani 1 1 d . . . N3 N 0.8289(8) 0.6034(4) 0.2538(4) 0.062(4) Uani 1 1 d . . . N4 N 1.0900(6) 0.3928(4) 0.1190(5) 0.051(3) Uani 1 1 d . . . N5 N 0.9193(6) 0.3987(3) 0.1910(4) 0.042(3) Uani 1 1 d . . . N6 N 1.2137(8) 0.4195(4) 0.2270(5) 0.059(4) Uani 1 1 d . . . C1 C 0.6613(8) 0.4857(5) 0.3134(5) 0.048(3) Uani 1 1 d . . . C2 C 0.6567(14) 0.4288(7) 0.3168(8) 0.067(5) Uani 1 1 d . . . H2 H 0.6701 0.4090 0.2845 0.081 Uiso 1 1 calc R . . C3 C 0.6349(10) 0.4025(5) 0.3622(7) 0.074(4) Uani 1 1 d . . . H3 H 0.6389 0.3651 0.3629 0.089 Uiso 1 1 calc R . . C4 C 0.6057(13) 0.4305(6) 0.4100(6) 0.094(5) Uani 1 1 d . . . H4 H 0.5857 0.4128 0.4425 0.113 Uiso 1 1 calc R . . C5 C 0.6079(12) 0.4862(6) 0.4064(7) 0.087(5) Uani 1 1 d . . . H5 H 0.5884 0.5053 0.4382 0.105 Uiso 1 1 calc R . . C6 C 0.6358(8) 0.5152(5) 0.3612(5) 0.058(3) Uani 1 1 d . . . C7 C 0.6437(8) 0.5704(5) 0.3677(6) 0.052(3) Uani 1 1 d . . . H7 H 0.6358 0.5837 0.4039 0.062 Uiso 1 1 calc R . . C8 C 0.6785(7) 0.6607(5) 0.3455(5) 0.046(3) Uani 1 1 d . . . C9 C 0.6147(8) 0.7017(5) 0.3330(5) 0.052(3) Uani 1 1 d . . . H9 H 0.5567 0.6936 0.3137 0.062 Uiso 1 1 calc R . . C10 C 0.6330(15) 0.7555(6) 0.3479(8) 0.055(6) Uani 1 1 d . . . H10 H 0.5834 0.7811 0.3436 0.066 Uiso 1 1 calc R . . C11 C 0.7229(13) 0.7706(6) 0.3689(6) 0.066(4) Uani 1 1 d . . . C12 C 0.7763(14) 0.8209(8) 0.3886(7) 0.071(5) Uani 1 1 d . . . C13 C 0.7445(11) 0.8719(6) 0.3829(5) 0.079(4) Uani 1 1 d . . . H13 H 0.6832 0.8797 0.3673 0.094 Uiso 1 1 calc R . . C14 C 0.8072(12) 0.9125(6) 0.4013(6) 0.087(4) Uani 1 1 d . . . H14 H 0.7869 0.9482 0.3989 0.104 Uiso 1 1 calc R . . C15 C 0.8993(12) 0.9007(6) 0.4231(6) 0.101(5) Uani 1 1 d . . . H15 H 0.9407 0.9280 0.4357 0.121 Uiso 1 1 calc R . . C16 C 0.9318(12) 0.8424(9) 0.4264(9) 0.080(7) Uani 1 1 d . . . H16 H 0.9932 0.8326 0.4407 0.096 Uiso 1 1 calc R . . C17 C 0.8662(9) 0.8052(5) 0.4072(5) 0.060(3) Uani 1 1 d . . . C18 C 0.8812(18) 0.7475(5) 0.3993(8) 0.065(7) Uani 1 1 d . . . C19 C 0.7908(8) 0.7264(6) 0.3841(5) 0.048(3) Uani 1 1 d . . . C20 C 0.7759(13) 0.6693(7) 0.3766(7) 0.063(5) Uani 1 1 d . . . C21 C 0.8451(7) 0.6353(5) 0.3917(4) 0.048(3) Uani 1 1 d . . . H21 H 0.8394 0.5983 0.3864 0.058 Uiso 1 1 calc R . . C22 C 0.9309(11) 0.6598(8) 0.4172(8) 0.067(6) Uani 1 1 d . . . H22 H 0.9805 0.6361 0.4281 0.081 Uiso 1 1 calc R . . C23 C 0.9486(9) 0.7105(6) 0.4270(5) 0.068(4) Uani 1 1 d . . . H23 H 1.0001 0.7221 0.4499 0.081 Uiso 1 1 calc R . . C24 C 0.6984(10) 0.5715(6) 0.1607(6) 0.054(4) Uani 1 1 d . . . C25 C 0.7873(10) 0.5657(6) 0.1275(6) 0.075(4) Uani 1 1 d . . . H25 H 0.8485 0.5725 0.1439 0.090 Uiso 1 1 calc R . . C26 C 0.7829(12) 0.5506(6) 0.0729(6) 0.083(5) Uani 1 1 d . . . C27 C 0.6961(18) 0.5409(8) 0.0453(8) 0.112(7) Uani 1 1 d . . . H27 H 0.6959 0.5309 0.0077 0.134 Uiso 1 1 calc R . . C28 C 0.6067(14) 0.5463(7) 0.0754(7) 0.085(5) Uani 1 1 d . . . C29 C 0.6043(14) 0.5595(7) 0.1321(8) 0.061(5) Uani 1 1 d . . . C30 C 0.5215(10) 0.5659(5) 0.1644(6) 0.059(3) Uani 1 1 d . . . C31 C 0.4241(11) 0.5582(7) 0.1480(8) 0.105(6) Uani 1 1 d . . . H31 H 0.4110 0.5507 0.1105 0.126 Uiso 1 1 calc R . . C32 C 0.3451(13) 0.5612(6) 0.1855(9) 0.107(7) Uani 1 1 d . . . H32 H 0.2810 0.5529 0.1745 0.128 Uiso 1 1 calc R . . C33 C 0.3649(9) 0.5762(6) 0.2362(13) 0.109(7) Uani 1 1 d . . . H33 H 0.3128 0.5812 0.2611 0.131 Uiso 1 1 calc R . . C34 C 0.4662(12) 0.5857(6) 0.2561(8) 0.069(5) Uani 1 1 d . . . H34 H 0.4784 0.5948 0.2934 0.083 Uiso 1 1 calc R . . C35 C 0.6959(8) 0.6660(5) 0.2170(5) 0.047(3) Uani 1 1 d . . . C36 C 0.6200(9) 0.6983(5) 0.1907(5) 0.060(3) Uani 1 1 d . . . H36 H 0.5592 0.6836 0.1808 0.072 Uiso 1 1 calc R . . C37 C 0.6412(16) 0.7520(4) 0.1810(8) 0.049(6) Uani 1 1 d . . . C38 C 0.7270(11) 0.7754(6) 0.1933(8) 0.096(6) Uani 1 1 d . . . H38 H 0.7393 0.8108 0.1828 0.115 Uiso 1 1 calc R . . C39 C 0.7960(13) 0.7467(4) 0.2215(8) 0.048(5) Uani 1 1 d . . . C40 C 0.7849(7) 0.6915(5) 0.2254(4) 0.052(3) Uani 1 1 d . . . C41 C 0.8632(7) 0.6546(4) 0.2465(5) 0.052(3) Uani 1 1 d . . . C42 C 0.9629(8) 0.6666(5) 0.2560(5) 0.065(4) Uani 1 1 d . . . H42 H 0.9866 0.7014 0.2506 0.078 Uiso 1 1 calc R . . C43 C 1.0254(9) 0.6262(6) 0.2734(6) 0.078(4) Uani 1 1 d . . . H43 H 1.0914 0.6340 0.2806 0.093 Uiso 1 1 calc R . . C44 C 0.9927(11) 0.5757(6) 0.2802(7) 0.072(5) Uani 1 1 d . . . H44 H 1.0361 0.5485 0.2907 0.086 Uiso 1 1 calc R . . C45 C 0.8898(12) 0.5638(6) 0.2710(6) 0.066(4) Uani 1 1 d . . . H45 H 0.8657 0.5292 0.2770 0.079 Uiso 1 1 calc R . . C46 C 1.0892(8) 0.5138(5) 0.1365(6) 0.054(3) Uani 1 1 d . . . C47 C 1.0896(11) 0.5701(7) 0.1328(8) 0.057(5) Uani 1 1 d . . . H47 H 1.0704 0.5900 0.1640 0.068 Uiso 1 1 calc R . . C48 C 1.1181(12) 0.5977(6) 0.0836(6) 0.083(4) Uani 1 1 d . . . H48 H 1.1188 0.6352 0.0832 0.099 Uiso 1 1 calc R . . C49 C 1.1452(12) 0.5694(7) 0.0354(7) 0.086(5) Uani 1 1 d . . . H49 H 1.1666 0.5882 0.0039 0.104 Uiso 1 1 calc R . . C50 C 1.1411(11) 0.5143(6) 0.0337(6) 0.078(4) Uani 1 1 d . . . H50 H 1.1563 0.4957 0.0009 0.093 Uiso 1 1 calc R . . C51 C 1.1117(8) 0.4849(5) 0.0853(5) 0.055(3) Uani 1 1 d . . . C52 C 1.1039(8) 0.4267(5) 0.0796(5) 0.051(3) Uani 1 1 d . . . H52 H 1.1097 0.4128 0.0435 0.061 Uiso 1 1 calc R . . C53 C 1.0695(7) 0.3388(5) 0.0992(5) 0.048(3) Uani 1 1 d . . . C54 C 1.1324(8) 0.2979(5) 0.1125(5) 0.050(3) Uani 1 1 d . . . H54 H 1.1941 0.3063 0.1274 0.060 Uiso 1 1 calc R . . C55 C 1.1084(15) 0.2448(5) 0.1049(9) 0.053(6) Uani 1 1 d . . . H55 H 1.1500 0.2175 0.1175 0.063 Uiso 1 1 calc R . . C56 C 1.0181(10) 0.2326(6) 0.0771(5) 0.048(3) Uani 1 1 d . . . C57 C 0.9715(12) 0.1813(6) 0.0653(6) 0.047(4) Uani 1 1 d . . . C58 C 0.9975(11) 0.1278(6) 0.0657(6) 0.081(4) Uani 1 1 d . . . H58 H 1.0593 0.1167 0.0783 0.097 Uiso 1 1 calc R . . C59 C 0.9249(16) 0.0894(6) 0.0457(6) 0.103(6) Uani 1 1 d . . . H59 H 0.9386 0.0528 0.0485 0.123 Uiso 1 1 calc R . . C60 C 0.8375(12) 0.1052(8) 0.0231(6) 0.085(5) Uani 1 1 d . . . H60 H 0.7945 0.0791 0.0094 0.102 Uiso 1 1 calc R . . C61 C 0.8138(13) 0.1518(9) 0.0202(9) 0.073(6) Uani 1 1 d . . . H61 H 0.7523 0.1599 0.0049 0.088 Uiso 1 1 calc R . . C62 C 0.8739(11) 0.1952(7) 0.0388(5) 0.079(4) Uani 1 1 d . . . C63 C 0.8703(14) 0.2541(5) 0.0332(7) 0.037(4) Uani 1 1 d . . . C64 C 0.9544(9) 0.2738(6) 0.0635(5) 0.051(3) Uani 1 1 d . . . C65 C 0.9793(10) 0.3258(6) 0.0729(5) 0.032(3) Uani 1 1 d . . . C66 C 0.9029(9) 0.3655(6) 0.0525(5) 0.063(3) Uani 1 1 d . . . H66 H 0.9149 0.4021 0.0574 0.076 Uiso 1 1 calc R . . C67 C 0.8202(12) 0.3506(8) 0.0281(8) 0.066(5) Uani 1 1 d . . . H67 H 0.7753 0.3761 0.0151 0.079 Uiso 1 1 calc R . . C68 C 0.7992(9) 0.2897(6) 0.0213(5) 0.069(4) Uani 1 1 d . . . H68 H 0.7375 0.2779 0.0091 0.083 Uiso 1 1 calc R . . C69 C 1.0565(7) 0.3325(5) 0.2307(5) 0.052(3) Uani 1 1 d . . . C70 C 1.1279(9) 0.3006(5) 0.2537(5) 0.063(4) Uani 1 1 d . . . H70 H 1.1914 0.3143 0.2580 0.076 Uiso 1 1 calc R . . C71 C 1.108(2) 0.2475(6) 0.2710(12) 0.095(9) Uani 1 1 d . . . C72 C 1.0240(11) 0.2228(5) 0.2552(6) 0.068(4) Uani 1 1 d . . . H72 H 1.0181 0.1856 0.2562 0.082 Uiso 1 1 calc R . . C73 C 0.9498(17) 0.2540(6) 0.2380(11) 0.089(8) Uani 1 1 d . . . C74 C 0.9629(7) 0.3097(4) 0.2184(5) 0.057(3) Uani 1 1 d . . . C75 C 0.8863(7) 0.3457(4) 0.1990(6) 0.056(3) Uani 1 1 d . . . C76 C 0.7875(8) 0.3354(5) 0.1894(5) 0.061(4) Uani 1 1 d . . . H76 H 0.7633 0.3006 0.1935 0.074 Uiso 1 1 calc R . . C77 C 0.7254(9) 0.3756(6) 0.1741(5) 0.065(3) Uani 1 1 d . . . H77 H 0.6588 0.3683 0.1685 0.078 Uiso 1 1 calc R . . C78 C 0.7610(12) 0.4286(6) 0.1667(6) 0.064(4) Uani 1 1 d . . . H78 H 0.7195 0.4568 0.1565 0.077 Uiso 1 1 calc R . . C79 C 0.8565(10) 0.4357(5) 0.1751(6) 0.051(3) Uani 1 1 d . . . H79 H 0.8814 0.4701 0.1691 0.061 Uiso 1 1 calc R . . C80 C 1.0504(12) 0.4322(6) 0.2876(6) 0.060(4) Uani 1 1 d . . . C81 C 0.9632(10) 0.4349(5) 0.3141(6) 0.063(4) Uani 1 1 d . . . H81 H 0.9048 0.4261 0.2956 0.075 Uiso 1 1 calc R . . C82 C 0.9621(12) 0.4515(6) 0.3706(7) 0.090(5) Uani 1 1 d . . . C83 C 1.0476(13) 0.4575(7) 0.3980(6) 0.089(5) Uani 1 1 d . . . H83 H 1.0467 0.4653 0.4362 0.106 Uiso 1 1 calc R . . C84 C 1.1344(11) 0.4526(7) 0.3718(8) 0.084(5) Uani 1 1 d . . . C85 C 1.1376(14) 0.4381(8) 0.3172(8) 0.060(5) Uani 1 1 d . . . C86 C 1.2309(9) 0.4331(5) 0.2811(7) 0.060(4) Uani 1 1 d . . . C87 C 1.3296(12) 0.4391(5) 0.2985(6) 0.082(5) Uani 1 1 d . . . H87 H 1.3444 0.4481 0.3355 0.098 Uiso 1 1 calc R . . C88 C 1.4052(10) 0.4313(6) 0.2593(8) 0.090(5) Uani 1 1 d . . . H88 H 1.4707 0.4347 0.2707 0.108 Uiso 1 1 calc R . . C89 C 1.3846(11) 0.4187(6) 0.2043(9) 0.073(4) Uani 1 1 d . . . H89 H 1.4344 0.4135 0.1779 0.088 Uiso 1 1 calc R . . C90 C 1.2919(11) 0.4147(6) 0.1914(7) 0.067(5) Uani 1 1 d . . . H90 H 1.2772 0.4077 0.1539 0.080 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 Ir1 0.0475(3) 0.0488(2) 0.0472(3) -0.0017(5) -0.0052(2) -0.0008(2) Ir2 0.0484(3) 0.0498(2) 0.0418(3) -0.0004(5) -0.0048(2) -0.0027(2) F1 0.130(7) 0.234(12) 0.070(6) -0.035(6) 0.042(5) 0.001(7) F2 0.127(8) 0.179(10) 0.070(6) -0.018(6) -0.038(6) -0.051(7) F3 0.086(6) 0.078(7) 0.124(9) 0.033(6) -0.007(5) 0.028(4) F4 0.084(6) 0.067(5) 0.202(12) 0.009(7) 0.000(6) -0.023(5) F5 0.104(7) 0.085(7) 0.121(9) 0.039(6) -0.010(5) 0.024(5) F6 0.074(5) 0.069(4) 0.143(9) 0.015(6) 0.002(5) -0.030(5) F7 0.103(6) 0.190(10) 0.075(6) -0.016(6) 0.025(5) 0.007(6) F8 0.119(7) 0.135(8) 0.068(6) -0.013(5) -0.044(5) -0.019(6) O1 0.078(5) 0.043(5) 0.049(7) -0.006(4) 0.000(4) -0.001(3) O2 0.072(5) 0.055(5) 0.053(7) 0.006(4) -0.004(4) -0.001(4) N1 0.049(5) 0.055(6) 0.037(6) -0.014(5) 0.000(5) 0.007(5) N2 0.053(6) 0.051(6) 0.058(11) 0.000(5) -0.013(5) 0.009(5) N3 0.071(7) 0.062(7) 0.052(9) 0.008(5) 0.012(6) 0.023(6) N4 0.052(5) 0.041(6) 0.061(7) 0.011(5) 0.001(5) -0.005(5) N5 0.039(5) 0.051(6) 0.037(8) -0.006(4) -0.013(4) 0.000(4) N6 0.057(6) 0.059(7) 0.060(11) 0.000(5) -0.009(6) -0.009(5) C1 0.045(6) 0.058(8) 0.042(8) 0.001(7) -0.013(6) -0.009(6) C2 0.112(14) 0.049(10) 0.041(11) 0.004(8) -0.012(10) 0.007(9) C3 0.093(11) 0.047(9) 0.083(12) -0.006(8) 0.006(9) -0.006(7) C4 0.172(16) 0.066(10) 0.045(9) 0.016(8) 0.026(10) -0.015(11) C5 0.112(13) 0.072(11) 0.078(12) -0.012(9) 0.022(9) -0.001(9) C6 0.075(9) 0.042(7) 0.058(9) 0.000(7) 0.014(7) -0.013(6) C7 0.044(7) 0.052(8) 0.059(9) -0.002(7) 0.013(6) 0.005(6) C8 0.052(7) 0.051(8) 0.035(7) -0.015(6) 0.001(5) 0.002(5) C9 0.033(6) 0.057(8) 0.065(9) -0.009(6) 0.000(5) 0.008(6) C10 0.042(10) 0.079(12) 0.043(10) -0.029(7) -0.006(8) 0.016(6) C11 0.098(13) 0.047(9) 0.052(9) -0.011(8) 0.004(8) 0.014(9) C12 0.095(12) 0.084(12) 0.034(10) -0.010(9) -0.005(8) 0.019(10) C13 0.112(12) 0.067(9) 0.057(9) -0.005(8) 0.004(8) -0.024(9) C14 0.103(11) 0.076(9) 0.081(11) -0.007(8) 0.001(9) -0.020(10) C15 0.125(14) 0.090(11) 0.088(12) -0.020(8) 0.013(9) -0.067(10) C16 0.070(11) 0.101(14) 0.068(12) 0.003(10) 0.010(9) -0.043(10) C17 0.061(8) 0.063(9) 0.056(9) -0.016(7) 0.010(6) -0.021(7) C18 0.080(13) 0.076(13) 0.039(11) -0.034(7) 0.002(9) -0.002(7) C19 0.037(8) 0.069(10) 0.040(8) -0.004(7) -0.002(5) 0.004(7) C20 0.062(10) 0.064(10) 0.063(10) -0.001(8) 0.013(7) -0.008(8) C21 0.039(7) 0.065(8) 0.041(7) 0.000(6) -0.009(5) 0.015(6) C22 0.050(10) 0.086(13) 0.066(12) 0.008(9) -0.004(8) 0.034(9) C23 0.051(8) 0.103(11) 0.049(8) -0.016(8) -0.008(6) -0.023(7) C24 0.054(8) 0.054(7) 0.055(9) 0.020(7) -0.018(7) -0.009(6) C25 0.069(11) 0.098(10) 0.058(11) 0.007(9) -0.007(7) -0.007(7) C26 0.104(13) 0.107(12) 0.037(10) -0.005(8) 0.023(8) -0.002(9) C27 0.165(19) 0.112(16) 0.058(12) 0.009(11) -0.033(14) -0.021(15) C28 0.121(14) 0.096(13) 0.039(11) -0.017(10) -0.007(9) -0.023(10) C29 0.076(12) 0.057(11) 0.052(12) 0.010(8) -0.014(9) -0.023(8) C30 0.072(10) 0.051(7) 0.055(10) 0.005(7) -0.017(8) -0.003(7) C31 0.040(8) 0.137(15) 0.138(16) 0.026(11) -0.011(10) 0.014(9) C32 0.089(13) 0.082(11) 0.149(17) -0.020(11) -0.089(12) -0.002(9) C33 0.021(7) 0.094(13) 0.21(2) -0.006(17) 0.002(13) 0.005(7) C34 0.059(10) 0.056(9) 0.092(15) -0.010(8) -0.008(8) -0.004(8) C35 0.047(6) 0.056(7) 0.039(9) -0.003(5) 0.006(5) 0.007(5) C36 0.073(8) 0.062(8) 0.046(9) -0.001(6) -0.004(6) -0.008(7) C37 0.060(13) 0.050(12) 0.037(10) 0.008(5) 0.018(8) 0.002(6) C38 0.072(10) 0.065(10) 0.151(17) 0.028(12) 0.021(11) 0.009(9) C39 0.065(10) 0.045(8) 0.034(9) 0.005(4) -0.002(7) -0.004(6) C40 0.051(7) 0.060(7) 0.046(9) -0.004(6) 0.002(5) -0.005(6) C41 0.055(6) 0.056(7) 0.043(7) -0.005(6) -0.005(6) -0.009(5) C42 0.054(8) 0.070(8) 0.071(10) 0.000(7) -0.006(6) -0.007(6) C43 0.058(8) 0.079(10) 0.096(11) -0.015(9) -0.013(8) -0.016(8) C44 0.040(8) 0.091(12) 0.085(12) -0.029(10) -0.022(8) 0.016(8) C45 0.081(10) 0.065(9) 0.052(9) -0.014(8) 0.003(8) 0.008(8) C46 0.049(7) 0.050(8) 0.063(10) 0.001(7) -0.008(6) -0.005(6) C47 0.056(9) 0.055(10) 0.060(12) -0.020(8) -0.005(8) -0.011(7) C48 0.141(14) 0.062(10) 0.046(10) 0.006(8) -0.002(9) -0.003(9) C49 0.093(11) 0.087(13) 0.079(13) 0.030(10) -0.001(10) -0.006(10) C50 0.120(13) 0.071(11) 0.042(9) 0.026(8) -0.004(8) 0.000(9) C51 0.051(7) 0.069(9) 0.046(9) -0.003(8) -0.017(6) 0.003(6) C52 0.057(7) 0.060(9) 0.035(8) -0.010(7) -0.016(6) -0.005(6) C53 0.055(8) 0.051(8) 0.039(8) 0.011(6) 0.010(5) -0.005(6) C54 0.040(6) 0.056(8) 0.054(8) -0.008(6) 0.000(6) -0.013(6) C55 0.041(10) 0.058(10) 0.058(12) 0.014(6) 0.001(8) 0.015(6) C56 0.054(9) 0.058(8) 0.032(8) 0.002(7) 0.011(6) -0.001(7) C57 0.064(9) 0.038(7) 0.039(8) -0.019(6) 0.007(6) -0.019(6) C58 0.081(11) 0.070(10) 0.092(11) -0.009(8) 0.004(8) -0.014(8) C59 0.158(16) 0.067(9) 0.083(12) -0.040(8) 0.045(12) -0.046(12) C60 0.076(10) 0.119(15) 0.061(9) -0.020(9) 0.014(8) -0.027(10) C61 0.088(14) 0.068(11) 0.064(12) -0.038(10) 0.013(9) -0.016(10) C62 0.079(10) 0.107(13) 0.050(9) -0.031(9) 0.005(7) -0.020(10) C63 0.039(8) 0.065(10) 0.008(7) 0.002(5) 0.007(5) -0.013(5) C64 0.048(9) 0.064(10) 0.042(8) 0.000(7) -0.004(6) -0.002(7) C65 0.041(6) 0.047(7) 0.008(6) -0.001(5) -0.010(5) 0.013(5) C66 0.062(9) 0.080(10) 0.047(8) -0.009(7) 0.011(6) 0.001(7) C67 0.066(11) 0.072(10) 0.059(11) 0.000(8) -0.003(8) -0.004(8) C68 0.055(9) 0.096(11) 0.058(8) -0.001(7) 0.005(6) 0.007(7) C69 0.048(7) 0.062(8) 0.047(9) -0.008(6) -0.004(6) -0.013(5) C70 0.056(7) 0.056(8) 0.078(11) -0.007(7) -0.012(7) 0.021(6) C71 0.09(2) 0.063(16) 0.13(2) 0.028(9) -0.024(15) 0.007(8) C72 0.083(10) 0.037(7) 0.085(12) 0.017(8) -0.004(8) 0.001(8) C73 0.082(13) 0.082(13) 0.103(18) -0.026(10) 0.059(11) -0.015(8) C74 0.057(7) 0.052(6) 0.063(10) 0.016(6) 0.008(6) 0.008(6) C75 0.054(6) 0.050(6) 0.063(8) -0.014(7) 0.004(7) 0.003(5) C76 0.053(7) 0.062(7) 0.069(10) -0.002(6) 0.001(6) -0.005(6) C77 0.052(7) 0.097(11) 0.046(8) -0.024(8) -0.015(6) 0.012(8) C78 0.068(10) 0.069(10) 0.055(10) -0.005(8) -0.001(8) 0.003(8) C79 0.041(7) 0.037(7) 0.075(10) -0.014(7) -0.015(7) -0.005(6) C80 0.074(10) 0.051(8) 0.056(10) 0.003(7) -0.012(8) 0.000(8) C81 0.078(11) 0.066(8) 0.044(9) -0.013(7) 0.002(7) -0.016(7) C82 0.090(12) 0.094(11) 0.086(13) -0.004(9) -0.014(10) -0.002(9) C83 0.093(12) 0.127(15) 0.047(10) -0.024(10) 0.022(10) 0.006(11) C84 0.070(11) 0.098(13) 0.085(14) 0.007(11) -0.022(10) -0.009(9) C85 0.062(11) 0.075(12) 0.043(11) 0.006(9) 0.009(8) 0.012(9) C86 0.045(8) 0.063(8) 0.073(11) -0.001(8) -0.016(7) -0.018(6) C87 0.101(12) 0.082(10) 0.062(10) -0.010(8) -0.042(9) -0.028(9) C88 0.048(9) 0.102(11) 0.119(15) 0.010(10) -0.002(9) -0.006(7) C89 0.063(9) 0.091(11) 0.065(11) 0.001(11) -0.021(11) -0.023(8) C90 0.058(11) 0.099(12) 0.043(11) -0.006(8) -0.003(7) 0.009(9) _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 C24 1.945(15) . ? Ir1 C35 1.975(11) . ? Ir1 N2 2.017(11) . ? Ir1 N3 2.020(11) . ? Ir1 O1 2.142(7) . ? Ir1 N1 2.165(9) . ? Ir2 C69 2.012(12) . ? Ir2 N5 2.051(8) . ? Ir2 C80 2.054(16) . ? Ir2 N6 2.059(11) . ? Ir2 N4 2.114(11) . ? Ir2 O2 2.122(8) . ? F1 C26 1.354(15) . ? F2 C28 1.336(17) . ? F3 C37 1.38(2) . ? F4 C39 1.367(17) . ? F5 C71 1.31(2) . ? F6 C73 1.42(2) . ? F7 C82 1.351(16) . ? F8 C84 1.381(15) . ? O1 C1 1.339(13) . ? O2 C46 1.244(13) . ? N1 C7 1.319(14) . ? N1 C8 1.433(13) . ? N2 C34 1.323(18) . ? N2 C30 1.392(17) . ? N3 C45 1.348(16) . ? N3 C41 1.365(13) . ? N4 C52 1.275(14) . ? N4 C53 1.449(14) . ? N5 C79 1.308(13) . ? N5 C75 1.403(12) . ? N6 C86 1.351(17) . ? N6 C90 1.361(17) . ? C1 C6 1.396(15) . ? C1 C2 1.42(2) . ? C2 C3 1.30(2) . ? C2 H2 0.9300 . ? C3 C4 1.39(2) . ? C3 H3 0.9300 . ? C4 C5 1.39(2) . ? C4 H4 0.9300 . ? C5 C6 1.351(17) . ? C5 H5 0.9300 . ? C6 C7 1.385(15) . ? C7 H7 0.9300 . ? C8 C9 1.368(14) . ? C8 C20 1.526(19) . ? C9 C10 1.406(15) . ? C9 H9 0.9300 . ? C10 C11 1.37(3) . ? C10 H10 0.9300 . ? C11 C19 1.478(19) . ? C11 C12 1.52(2) . ? C12 C13 1.35(2) . ? C12 C17 1.35(2) . ? C13 C14 1.389(17) . ? C13 H13 0.9300 . ? C14 C15 1.382(19) . ? C14 H14 0.9300 . ? C15 C16 1.52(2) . ? C15 H15 0.9300 . ? C16 C17 1.360(19) . ? C16 H16 0.9300 . ? C17 C18 1.459(15) . ? C18 C19 1.38(3) . ? C18 C23 1.45(2) . ? C19 C20 1.44(2) . ? C20 C21 1.312(19) . ? C21 C22 1.44(2) . ? C21 H21 0.9300 . ? C22 C23 1.30(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.446(18) . ? C24 C29 1.48(2) . ? C25 C26 1.356(18) . ? C25 H25 0.9300 . ? C26 C27 1.37(2) . ? C27 C28 1.41(2) . ? C27 H27 0.9300 . ? C28 C29 1.39(2) . ? C29 C30 1.37(2) . ? C30 C31 1.387(18) . ? C31 C32 1.39(2) . ? C31 H31 0.9300 . ? C32 C33 1.29(3) . ? C32 H32 0.9300 . ? C33 C34 1.47(2) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C40 1.376(13) . ? C35 C36 1.445(16) . ? C36 C37 1.385(15) . ? C36 H36 0.9300 . ? C37 C38 1.33(3) . ? C38 C39 1.35(2) . ? C38 H38 0.9300 . ? C39 C40 1.382(14) . ? C40 C41 1.488(14) . ? C41 C42 1.400(13) . ? C42 C43 1.378(16) . ? C42 H42 0.9300 . ? C43 C44 1.340(19) . ? C43 H43 0.9300 . ? C44 C45 1.44(2) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C47 1.40(2) . ? C46 C51 1.448(15) . ? C47 C48 1.41(2) . ? C47 H47 0.9300 . ? C48 C49 1.39(2) . ? C48 H48 0.9300 . ? C49 C50 1.37(2) . ? C49 H49 0.9300 . ? C50 C51 1.482(16) . ? C50 H50 0.9300 . ? C51 C52 1.456(16) . ? C52 H52 0.9300 . ? C53 C54 1.364(15) . ? C53 C65 1.409(16) . ? C54 C55 1.371(15) . ? C54 H54 0.9300 . ? C55 C56 1.42(3) . ? C55 H55 0.9300 . ? C56 C64 1.377(18) . ? C56 C57 1.45(2) . ? C57 C58 1.373(19) . ? C57 C62 1.50(2) . ? C58 C59 1.451(19) . ? C58 H58 0.9300 . ? C59 C60 1.36(2) . ? C59 H59 0.9300 . ? C60 C61 1.20(2) . ? C60 H60 0.9300 . ? C61 C62 1.42(2) . ? C61 H61 0.9300 . ? C62 C63 1.472(17) . ? C63 C68 1.336(19) . ? C63 C64 1.43(2) . ? C64 C65 1.354(19) . ? C65 C66 1.510(18) . ? C66 C67 1.314(19) . ? C66 H66 0.9300 . ? C67 C68 1.55(2) . ? C67 H67 0.9300 . ? C68 H68 0.9300 . ? C69 C70 1.363(15) . ? C69 C74 1.418(13) . ? C70 C71 1.409(18) . ? C70 H70 0.9300 . ? C71 C72 1.34(3) . ? C72 C73 1.33(2) . ? C72 H72 0.9300 . ? C73 C74 1.471(19) . ? C74 C75 1.445(14) . ? C75 C76 1.380(14) . ? C76 C77 1.354(15) . ? C76 H76 0.9300 . ? C77 C78 1.412(18) . ? C77 H77 0.9300 . ? C78 C79 1.320(19) . ? C78 H78 0.9300 . ? C79 H79 0.9300 . ? C80 C81 1.340(17) . ? C80 C85 1.38(2) . ? C81 C82 1.408(19) . ? C81 H81 0.9300 . ? C82 C83 1.336(19) . ? C83 C84 1.34(2) . ? C83 H83 0.9300 . ? C84 C85 1.35(2) . ? C85 C86 1.53(2) . ? C86 C87 1.407(17) . ? C87 C88 1.40(2) . ? C87 H87 0.9300 . ? C88 C89 1.38(2) . ? C88 H88 0.9300 . ? C89 C90 1.30(2) . ? C89 H89 0.9300 . ? C90 H90 0.9300 . ? 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 C24 Ir1 C35 87.2(5) . . ? C24 Ir1 N2 81.1(5) . . ? C35 Ir1 N2 97.0(4) . . ? C24 Ir1 N3 95.8(5) . . ? C35 Ir1 N3 78.8(4) . . ? N2 Ir1 N3 174.9(4) . . ? C24 Ir1 O1 91.8(5) . . ? C35 Ir1 O1 174.0(4) . . ? N2 Ir1 O1 88.7(3) . . ? N3 Ir1 O1 95.5(3) . . ? C24 Ir1 N1 176.5(5) . . ? C35 Ir1 N1 95.6(4) . . ? N2 Ir1 N1 96.5(4) . . ? N3 Ir1 N1 86.8(4) . . ? O1 Ir1 N1 85.6(3) . . ? C69 Ir2 N5 81.6(4) . . ? C69 Ir2 C80 88.0(5) . . ? N5 Ir2 C80 94.7(5) . . ? C69 Ir2 N6 96.3(4) . . ? N5 Ir2 N6 174.9(4) . . ? C80 Ir2 N6 80.5(5) . . ? C69 Ir2 N4 96.7(4) . . ? N5 Ir2 N4 87.4(3) . . ? C80 Ir2 N4 175.0(5) . . ? N6 Ir2 N4 97.5(4) . . ? C69 Ir2 O2 174.6(4) . . ? N5 Ir2 O2 94.0(3) . . ? C80 Ir2 O2 89.3(5) . . ? N6 Ir2 O2 87.8(3) . . ? N4 Ir2 O2 86.1(3) . . ? C1 O1 Ir1 127.5(7) . . ? C46 O2 Ir2 130.6(8) . . ? C7 N1 C8 117.3(10) . . ? C7 N1 Ir1 126.4(8) . . ? C8 N1 Ir1 115.9(7) . . ? C34 N2 C30 120.7(13) . . ? C34 N2 Ir1 124.2(10) . . ? C30 N2 Ir1 115.0(9) . . ? C45 N3 C41 120.8(12) . . ? C45 N3 Ir1 121.5(10) . . ? C41 N3 Ir1 117.7(7) . . ? C52 N4 C53 113.6(10) . . ? C52 N4 Ir2 127.3(9) . . ? C53 N4 Ir2 118.0(7) . . ? C79 N5 C75 119.5(9) . . ? C79 N5 Ir2 126.2(8) . . ? C75 N5 Ir2 114.3(6) . . ? C86 N6 C90 118.9(12) . . ? C86 N6 Ir2 115.9(9) . . ? C90 N6 Ir2 125.3(10) . . ? O1 C1 C6 125.2(11) . . ? O1 C1 C2 116.9(13) . . ? C6 C1 C2 117.8(13) . . ? C3 C2 C1 124.0(17) . . ? C3 C2 H2 118.0 . . ? C1 C2 H2 118.0 . . ? C2 C3 C4 119.7(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 116.3(14) . . ? C5 C4 H4 121.8 . . ? C3 C4 H4 121.8 . . ? C6 C5 C4 125.9(14) . . ? C6 C5 H5 117.0 . . ? C4 C5 H5 117.0 . . ? C5 C6 C7 117.5(13) . . ? C5 C6 C1 116.0(11) . . ? C7 C6 C1 126.3(12) . . ? N1 C7 C6 127.1(12) . . ? N1 C7 H7 116.5 . . ? C6 C7 H7 116.5 . . ? C9 C8 N1 122.4(10) . . ? C9 C8 C20 123.1(11) . . ? N1 C8 C20 114.4(10) . . ? C8 C9 C10 122.9(13) . . ? C8 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 120.6(15) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C19 116.1(15) . . ? C10 C11 C12 139.6(14) . . ? C19 C11 C12 103.9(15) . . ? C13 C12 C17 126.3(18) . . ? C13 C12 C11 126.3(16) . . ? C17 C12 C11 106.9(15) . . ? C12 C13 C14 117.2(16) . . ? C12 C13 H13 121.4 . . ? C14 C13 H13 121.4 . . ? C15 C14 C13 120.9(15) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 119.0(13) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 116.3(16) . . ? C17 C16 H16 121.8 . . ? C15 C16 H16 121.8 . . ? C12 C17 C16 120.0(16) . . ? C12 C17 C18 111.5(15) . . ? C16 C17 C18 128.3(17) . . ? C19 C18 C23 115.7(13) . . ? C19 C18 C17 106.5(17) . . ? C23 C18 C17 130.6(17) . . ? C18 C19 C20 122.1(13) . . ? C18 C19 C11 109.4(15) . . ? C20 C19 C11 127.8(16) . . ? C21 C20 C19 119.9(15) . . ? C21 C20 C8 131.2(15) . . ? C19 C20 C8 108.6(13) . . ? C20 C21 C22 114.7(14) . . ? C20 C21 H21 122.7 . . ? C22 C21 H21 122.7 . . ? C23 C22 C21 129.0(14) . . ? C23 C22 H22 115.5 . . ? C21 C22 H22 115.5 . . ? C22 C23 C18 114.6(13) . . ? C22 C23 H23 122.7 . . ? C18 C23 H23 122.7 . . ? C25 C24 C29 116.4(14) . . ? C25 C24 Ir1 129.5(10) . . ? C29 C24 Ir1 114.0(12) . . ? C26 C25 C24 121.0(13) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? F1 C26 C25 117.3(15) . . ? F1 C26 C27 119.5(16) . . ? C25 C26 C27 123.2(15) . . ? C26 C27 C28 118.5(17) . . ? C26 C27 H27 120.8 . . ? C28 C27 H27 120.8 . . ? F2 C28 C29 120.9(18) . . ? F2 C28 C27 116.7(15) . . ? C29 C28 C27 122.3(18) . . ? C30 C29 C28 126.4(18) . . ? C30 C29 C24 115.0(16) . . ? C28 C29 C24 118.4(18) . . ? C29 C30 C31 127.0(16) . . ? C29 C30 N2 114.8(14) . . ? C31 C30 N2 118.2(15) . . ? C30 C31 C32 122.7(17) . . ? C30 C31 H31 118.7 . . ? C32 C31 H31 118.7 . . ? C33 C32 C31 117.0(16) . . ? C33 C32 H32 121.5 . . ? C31 C32 H32 121.5 . . ? C32 C33 C34 122.8(19) . . ? C32 C33 H33 118.6 . . ? C34 C33 H33 118.6 . . ? N2 C34 C33 118.3(18) . . ? N2 C34 H34 120.8 . . ? C33 C34 H34 120.8 . . ? C40 C35 C36 115.5(10) . . ? C40 C35 Ir1 118.2(9) . . ? C36 C35 Ir1 126.3(8) . . ? C37 C36 C35 117.4(14) . . ? C37 C36 H36 121.3 . . ? C35 C36 H36 121.3 . . ? C38 C37 F3 118.4(12) . . ? C38 C37 C36 124.3(17) . . ? F3 C37 C36 117.1(16) . . ? C37 C38 C39 118.8(15) . . ? C37 C38 H38 120.6 . . ? C39 C38 H38 120.6 . . ? C38 C39 F4 117.2(13) . . ? C38 C39 C40 118.8(14) . . ? F4 C39 C40 120.8(13) . . ? C35 C40 C39 122.7(12) . . ? C35 C40 C41 112.9(10) . . ? C39 C40 C41 123.8(11) . . ? N3 C41 C42 120.4(11) . . ? N3 C41 C40 112.0(9) . . ? C42 C41 C40 127.5(10) . . ? C43 C42 C41 118.9(11) . . ? C43 C42 H42 120.5 . . ? C41 C42 H42 120.5 . . ? C44 C43 C42 121.1(12) . . ? C44 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? C43 C44 C45 119.5(13) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? N3 C45 C44 119.2(14) . . ? N3 C45 H45 120.4 . . ? C44 C45 H45 120.4 . . ? O2 C46 C47 119.6(14) . . ? O2 C46 C51 124.1(12) . . ? C47 C46 C51 116.2(14) . . ? C46 C47 C48 122.6(16) . . ? C46 C47 H47 118.7 . . ? C48 C47 H47 118.7 . . ? C49 C48 C47 120.5(15) . . ? C49 C48 H48 119.7 . . ? C47 C48 H48 119.7 . . ? C50 C49 C48 121.2(15) . . ? C50 C49 H49 119.4 . . ? C48 C49 H49 119.4 . . ? C49 C50 C51 118.6(14) . . ? C49 C50 H50 120.7 . . ? C51 C50 H50 120.7 . . ? C46 C51 C52 123.7(11) . . ? C46 C51 C50 120.6(12) . . ? C52 C51 C50 115.6(11) . . ? N4 C52 C51 126.8(12) . . ? N4 C52 H52 116.6 . . ? C51 C52 H52 116.6 . . ? C54 C53 C65 118.1(11) . . ? C54 C53 N4 119.7(10) . . ? C65 C53 N4 121.6(10) . . ? C53 C54 C55 122.6(13) . . ? C53 C54 H54 118.7 . . ? C55 C54 H54 118.7 . . ? C54 C55 C56 118.1(14) . . ? C54 C55 H55 121.0 . . ? C56 C55 H55 121.0 . . ? C64 C56 C55 119.2(16) . . ? C64 C56 C57 109.6(15) . . ? C55 C56 C57 130.7(13) . . ? C58 C57 C56 137.5(15) . . ? C58 C57 C62 116.8(12) . . ? C56 C57 C62 105.1(13) . . ? C57 C58 C59 117.5(15) . . ? C57 C58 H58 121.3 . . ? C59 C58 H58 121.3 . . ? C60 C59 C58 121.9(16) . . ? C60 C59 H59 119.0 . . ? C58 C59 H59 119.0 . . ? C61 C60 C59 122.3(18) . . ? C61 C60 H60 118.8 . . ? C59 C60 H60 118.8 . . ? C60 C61 C62 124(2) . . ? C60 C61 H61 118.0 . . ? C62 C61 H61 118.0 . . ? C61 C62 C63 135.0(17) . . ? C61 C62 C57 117.3(16) . . ? C63 C62 C57 107.2(13) . . ? C68 C63 C64 116.9(12) . . ? C68 C63 C62 134.5(15) . . ? C64 C63 C62 105.5(14) . . ? C65 C64 C56 121.0(16) . . ? C65 C64 C63 127.4(12) . . ? C56 C64 C63 111.2(15) . . ? C64 C65 C53 120.6(12) . . ? C64 C65 C66 113.6(12) . . ? C53 C65 C66 125.8(12) . . ? C67 C66 C65 122.8(15) . . ? C67 C66 H66 118.6 . . ? C65 C66 H66 118.6 . . ? C66 C67 C68 118.5(16) . . ? C66 C67 H67 120.7 . . ? C68 C67 H67 120.7 . . ? C63 C68 C67 119.4(13) . . ? C63 C68 H68 120.3 . . ? C67 C68 H68 120.3 . . ? C70 C69 C74 118.9(11) . . ? C70 C69 Ir2 128.4(9) . . ? C74 C69 Ir2 112.6(8) . . ? C69 C70 C71 121.8(16) . . ? C69 C70 H70 119.1 . . ? C71 C70 H70 119.1 . . ? F5 C71 C72 119.0(14) . . ? F5 C71 C70 119(2) . . ? C72 C71 C70 120(2) . . ? C73 C72 C71 117.3(15) . . ? C73 C72 H72 121.4 . . ? C71 C72 H72 121.4 . . ? C72 C73 F6 119.3(13) . . ? C72 C73 C74 123.6(16) . . ? F6 C73 C74 112.2(19) . . ? C69 C74 C75 117.2(10) . . ? C69 C74 C73 114.7(13) . . ? C75 C74 C73 126.8(13) . . ? C76 C75 N5 117.4(10) . . ? C76 C75 C74 129.2(10) . . ? N5 C75 C74 113.4(9) . . ? C77 C76 C75 120.5(11) . . ? C77 C76 H76 119.7 . . ? C75 C76 H76 119.7 . . ? C76 C77 C78 120.7(12) . . ? C76 C77 H77 119.7 . . ? C78 C77 H77 119.7 . . ? C79 C78 C77 116.1(13) . . ? C79 C78 H78 122.0 . . ? C77 C78 H78 122.0 . . ? N5 C79 C78 125.8(13) . . ? N5 C79 H79 117.1 . . ? C78 C79 H79 117.1 . . ? C81 C80 C85 120.4(15) . . ? C81 C80 Ir2 124.3(11) . . ? C85 C80 Ir2 114.8(13) . . ? C80 C81 C82 118.3(13) . . ? C80 C81 H81 120.8 . . ? C82 C81 H81 120.8 . . ? C83 C82 F7 119.6(15) . . ? C83 C82 C81 119.4(14) . . ? F7 C82 C81 121.0(13) . . ? C84 C83 C82 121.5(16) . . ? C84 C83 H83 119.3 . . ? C82 C83 H83 119.3 . . ? C83 C84 C85 120.3(16) . . ? C83 C84 F8 120.6(18) . . ? C85 C84 F8 119.0(17) . . ? C84 C85 C80 119.5(16) . . ? C84 C85 C86 126.1(17) . . ? C80 C85 C86 114.1(16) . . ? N6 C86 C87 118.1(14) . . ? N6 C86 C85 114.4(12) . . ? C87 C86 C85 127.5(15) . . ? C88 C87 C86 118.9(14) . . ? C88 C87 H87 120.6 . . ? C86 C87 H87 120.6 . . ? C89 C88 C87 121.3(15) . . ? C89 C88 H88 119.3 . . ? C87 C88 H88 119.3 . . ? C90 C89 C88 116.0(19) . . ? C90 C89 H89 122.0 . . ? C88 C89 H89 122.0 . . ? C89 C90 N6 126.7(17) . . ? C89 C90 H90 116.6 . . ? N6 C90 H90 116.6 . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.152 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.107