# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_yuichi2 _database_code_depnum_ccdc_archive 'CCDC 901377' #TrackingRef '13949_web_deposit_cif_file_0_HiroshiKatagiri_1347542220.yuichi2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H33 F4 Ir N4 O2' _chemical_formula_sum 'C33 H33 F4 Ir N4 O2' _chemical_formula_weight 785.83 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 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.5479(18) _cell_length_b 10.9047(10) _cell_length_c 17.9038(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.448(4) _cell_angle_gamma 90.00 _cell_volume 3142.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5760 _cell_measurement_theta_min 2.9940 _cell_measurement_theta_max 25.2080 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 4.309 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.7283 _exptl_absorpt_correction_T_max 0.8153 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 93 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 5882 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34707 _diffrn_reflns_av_R_equivalents 0.0732 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.13 _reflns_number_total 5566 _reflns_number_gt 5192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Kabuto et al., 2009)' _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^)+(0.0060P)^2^+9.2376P] 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 5566 _refine_ls_number_parameters 407 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.240 _refine_ls_restrained_S_all 1.240 _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 0.0000 0.44318(3) 0.2500 0.01497(9) Uani 1 2 d S . . Ir2 Ir 0.5000 -0.00988(3) 0.2500 0.01661(9) Uani 1 2 d S . . C1 C -0.0506(3) 0.5752(5) 0.2997(3) 0.0142(12) Uani 1 1 d . . . C2 C -0.1195(3) 0.6489(5) 0.2668(3) 0.0199(13) Uani 1 1 d . . . H2 H -0.1511 0.6349 0.2160 0.024 Uiso 1 1 calc R . . C3 C -0.1392(4) 0.7419(6) 0.3111(4) 0.0254(15) Uani 1 1 d . . . N1 N -0.1029(3) 0.7694(4) 0.3832(3) 0.0250(12) Uani 1 1 d . . . C4 C -0.0385(4) 0.6979(6) 0.4134(3) 0.0243(14) Uani 1 1 d . . . C5 C -0.0079(3) 0.6042(5) 0.3764(3) 0.0176(13) Uani 1 1 d . . . F1 F -0.2041(2) 0.8170(3) 0.2793(2) 0.0314(9) Uani 1 1 d . . . F2 F -0.0019(2) 0.7276(3) 0.48724(19) 0.0335(9) Uani 1 1 d . . . C6 C 0.0687(3) 0.5326(5) 0.4064(3) 0.0172(13) Uani 1 1 d . . . N2 N 0.0849(3) 0.4512(4) 0.3536(3) 0.0158(11) Uani 1 1 d . . . C7 C 0.1552(4) 0.3856(5) 0.3702(3) 0.0220(14) Uani 1 1 d . . . H7 H 0.1644 0.3264 0.3341 0.026 Uiso 1 1 calc R . . C8 C 0.2147(3) 0.4009(5) 0.4377(3) 0.0219(14) Uani 1 1 d . . . H8 H 0.2642 0.3536 0.4471 0.026 Uiso 1 1 calc R . . C9 C 0.2021(4) 0.4856(5) 0.4922(3) 0.0180(13) Uani 1 1 d . . . C10 C 0.1264(3) 0.5485(5) 0.4765(3) 0.0167(13) Uani 1 1 d . . . H10 H 0.1140 0.6026 0.5139 0.020 Uiso 1 1 calc R . . C11 C 0.2714(4) 0.5098(5) 0.5641(3) 0.0201(14) Uani 1 1 d . . . C12 C 0.2430(4) 0.5923(6) 0.6214(4) 0.0372(18) Uani 1 1 d . . . H12 H 0.2285 0.6732 0.5984 0.056 Uiso 1 1 calc R . . H12A H 0.2879 0.6007 0.6677 0.056 Uiso 1 1 calc R . . H12B H 0.1942 0.5561 0.6352 0.056 Uiso 1 1 calc R . . C13 C 0.3450(4) 0.5685(6) 0.5395(4) 0.0338(17) Uani 1 1 d . . . H13 H 0.3644 0.5135 0.5040 0.051 Uiso 1 1 calc R . . H13A H 0.3902 0.5828 0.5848 0.051 Uiso 1 1 calc R . . H13B H 0.3277 0.6468 0.5138 0.051 Uiso 1 1 calc R . . C14 C 0.3011(4) 0.3863(6) 0.6036(3) 0.0303(16) Uani 1 1 d . . . H14 H 0.2538 0.3430 0.6156 0.046 Uiso 1 1 calc R . . H14A H 0.3431 0.4018 0.6512 0.046 Uiso 1 1 calc R . . H14B H 0.3254 0.3360 0.5691 0.046 Uiso 1 1 calc R . . O1 O -0.0616(2) 0.3030(4) 0.2986(2) 0.0207(9) Uani 1 1 d . . . C15 C -0.0497(4) 0.1880(6) 0.2930(3) 0.0219(14) Uani 1 1 d . . . C16 C 0.0000 0.1325(8) 0.2500 0.0212(19) Uani 1 2 d S . . H16 H 0.0000 0.0453 0.2500 0.025 Uiso 1 2 calc SR . . C17 C -0.0979(4) 0.1105(6) 0.3380(4) 0.0324(16) Uani 1 1 d . . . H17 H -0.0798 0.1302 0.3928 0.049 Uiso 1 1 calc R . . H17A H -0.0877 0.0234 0.3302 0.049 Uiso 1 1 calc R . . H17B H -0.1574 0.1277 0.3202 0.049 Uiso 1 1 calc R . . C18 C 0.5451(3) 0.1189(5) 0.1929(3) 0.0158(12) Uani 1 1 d . . . C19 C 0.6114(4) 0.1983(5) 0.2181(3) 0.0216(14) Uani 1 1 d . . . H19 H 0.6427 0.1960 0.2698 0.026 Uiso 1 1 calc R . . C20 C 0.6308(4) 0.2794(6) 0.1671(3) 0.0250(14) Uani 1 1 d . . . N3 N 0.5935(3) 0.2918(4) 0.0929(3) 0.0234(12) Uani 1 1 d . . . C21 C 0.5303(4) 0.2165(6) 0.0700(3) 0.0247(14) Uani 1 1 d . . . C22 C 0.5007(3) 0.1316(5) 0.1144(3) 0.0175(13) Uani 1 1 d . . . F3 F 0.6933(2) 0.3610(3) 0.19103(19) 0.0321(9) Uani 1 1 d . . . F4 F 0.4935(2) 0.2271(3) -0.00588(19) 0.0336(9) Uani 1 1 d . . . C23 C 0.4218(3) 0.0631(5) 0.0924(3) 0.0159(13) Uani 1 1 d . . . N4 N 0.4072(3) -0.0056(4) 0.1524(3) 0.0187(11) Uani 1 1 d . . . C24 C 0.3340(3) -0.0609(5) 0.1446(3) 0.0194(13) Uani 1 1 d . . . H24 H 0.3241 -0.1071 0.1866 0.023 Uiso 1 1 calc R . . C25 C 0.2718(4) -0.0543(5) 0.0781(3) 0.0200(13) Uani 1 1 d . . . H25 H 0.2202 -0.0944 0.0755 0.024 Uiso 1 1 calc R . . C26 C 0.2843(3) 0.0107(5) 0.0153(3) 0.0166(13) Uani 1 1 d . . . C27 C 0.3610(3) 0.0685(5) 0.0231(3) 0.0182(13) Uani 1 1 d . . . H27 H 0.3723 0.1124 -0.0191 0.022 Uiso 1 1 calc R . . C28 C 0.2166(4) 0.0214(5) -0.0600(3) 0.0194(13) Uani 1 1 d . . . C29 C 0.1960(4) 0.1579(6) -0.0770(4) 0.0325(16) Uani 1 1 d . . . H29 H 0.1782 0.1949 -0.0336 0.049 Uiso 1 1 calc R . . H29A H 0.1512 0.1651 -0.1235 0.049 Uiso 1 1 calc R . . H29B H 0.2455 0.2007 -0.0848 0.049 Uiso 1 1 calc R . . C30 C 0.2503(4) -0.0346(6) -0.1253(3) 0.0323(16) Uani 1 1 d . . . H30 H 0.2994 0.0112 -0.1311 0.048 Uiso 1 1 calc R . . H30A H 0.2074 -0.0305 -0.1734 0.048 Uiso 1 1 calc R . . H30B H 0.2655 -0.1205 -0.1133 0.048 Uiso 1 1 calc R . . C31 C 0.1370(4) -0.0445(6) -0.0543(4) 0.0314(16) Uani 1 1 d . . . H31 H 0.1491 -0.1311 -0.0420 0.047 Uiso 1 1 calc R . . H31A H 0.0961 -0.0381 -0.1035 0.047 Uiso 1 1 calc R . . H31B H 0.1145 -0.0066 -0.0138 0.047 Uiso 1 1 calc R . . O2 O 0.5581(2) -0.1487(4) 0.1974(2) 0.0214(9) Uani 1 1 d . . . C32 C 0.5503(4) -0.2644(6) 0.2067(3) 0.0243(14) Uani 1 1 d U . . C33 C 0.6020(4) -0.3439(6) 0.1668(4) 0.0346(17) Uani 1 1 d U . . H33 H 0.6180 -0.2968 0.1259 0.052 Uiso 1 1 calc R . . H33A H 0.5696 -0.4157 0.1446 0.052 Uiso 1 1 calc R . . H33B H 0.6521 -0.3708 0.2041 0.052 Uiso 1 1 calc R . . C34 C 0.5000 -0.3214(8) 0.2500 0.026(2) Uani 1 2 d SU . . H34 H 0.5000 -0.4085 0.2500 0.031 Uiso 1 2 calc SR . . 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 0.01448(17) 0.01454(19) 0.01452(18) 0.000 0.00056(13) 0.000 Ir2 0.01651(18) 0.0190(2) 0.01259(18) 0.000 -0.00005(13) 0.000 C1 0.017(3) 0.015(3) 0.013(3) 0.003(2) 0.010(2) -0.004(2) C2 0.018(3) 0.022(4) 0.019(3) 0.005(3) 0.003(2) 0.001(3) C3 0.019(3) 0.025(4) 0.031(4) 0.010(3) 0.004(3) 0.006(3) N1 0.023(3) 0.020(3) 0.031(3) -0.004(2) 0.004(2) 0.004(2) C4 0.020(3) 0.030(4) 0.021(3) -0.002(3) 0.000(3) 0.001(3) C5 0.015(3) 0.016(3) 0.022(3) -0.001(2) 0.005(2) -0.005(2) F1 0.030(2) 0.031(2) 0.033(2) 0.0025(16) 0.0075(16) 0.0151(16) F2 0.031(2) 0.039(2) 0.027(2) -0.0161(17) -0.0011(16) 0.0073(17) C6 0.018(3) 0.014(3) 0.019(3) -0.001(2) 0.005(2) 0.000(2) N2 0.018(3) 0.013(3) 0.016(3) -0.001(2) 0.004(2) 0.000(2) C7 0.028(3) 0.021(4) 0.018(3) -0.004(3) 0.007(3) 0.004(3) C8 0.015(3) 0.029(4) 0.018(3) -0.002(3) -0.003(2) 0.006(3) C9 0.022(3) 0.015(3) 0.016(3) 0.002(2) 0.003(3) -0.004(2) C10 0.020(3) 0.020(3) 0.011(3) 0.000(2) 0.004(2) 0.001(2) C11 0.020(3) 0.021(4) 0.019(3) 0.002(3) 0.002(3) -0.003(3) C12 0.034(4) 0.051(5) 0.022(4) -0.007(3) -0.005(3) 0.003(3) C13 0.029(4) 0.032(4) 0.037(4) 0.007(3) 0.002(3) -0.008(3) C14 0.028(4) 0.037(4) 0.019(3) 0.010(3) -0.009(3) -0.004(3) O1 0.027(2) 0.016(2) 0.017(2) 0.0045(17) -0.0008(17) -0.0023(18) C15 0.019(3) 0.024(4) 0.017(3) 0.005(3) -0.008(3) -0.003(3) C16 0.023(5) 0.028(5) 0.010(4) 0.000 -0.001(4) 0.000 C17 0.038(4) 0.027(4) 0.030(4) 0.007(3) 0.003(3) -0.013(3) C18 0.015(3) 0.017(3) 0.015(3) -0.004(2) 0.003(2) 0.006(2) C19 0.023(3) 0.026(4) 0.014(3) -0.004(3) 0.003(3) -0.003(3) C20 0.024(3) 0.025(4) 0.026(4) -0.004(3) 0.005(3) -0.004(3) N3 0.022(3) 0.024(3) 0.024(3) 0.003(2) 0.006(2) -0.004(2) C21 0.025(3) 0.033(4) 0.015(3) 0.004(3) 0.000(3) 0.001(3) C22 0.017(3) 0.014(3) 0.020(3) -0.003(2) 0.002(2) 0.000(2) F3 0.031(2) 0.038(2) 0.026(2) -0.0071(17) 0.0043(16) -0.0193(17) F4 0.031(2) 0.049(3) 0.0180(19) 0.0095(16) -0.0004(16) -0.0154(17) C23 0.014(3) 0.017(3) 0.017(3) -0.002(2) 0.003(2) 0.001(2) N4 0.021(3) 0.020(3) 0.014(3) 0.001(2) 0.001(2) -0.001(2) C24 0.019(3) 0.016(3) 0.022(3) 0.004(2) 0.002(3) -0.004(2) C25 0.019(3) 0.015(3) 0.025(3) -0.001(3) 0.002(3) -0.004(2) C26 0.021(3) 0.012(3) 0.015(3) -0.003(2) 0.002(2) 0.001(2) C27 0.015(3) 0.021(3) 0.017(3) 0.003(2) 0.000(2) 0.001(2) C28 0.025(3) 0.015(3) 0.015(3) -0.001(2) -0.001(3) -0.003(3) C29 0.027(4) 0.028(4) 0.035(4) 0.002(3) -0.009(3) 0.001(3) C30 0.032(4) 0.044(5) 0.017(3) -0.004(3) -0.002(3) -0.002(3) C31 0.024(4) 0.047(5) 0.020(4) 0.002(3) 0.000(3) -0.002(3) O2 0.025(2) 0.021(2) 0.016(2) -0.0008(18) 0.0008(17) 0.0023(18) C32 0.026(3) 0.025(4) 0.015(3) -0.003(3) -0.009(3) 0.006(3) C33 0.047(4) 0.026(4) 0.026(4) -0.004(3) -0.001(3) 0.008(3) C34 0.030(5) 0.011(4) 0.032(5) 0.000 -0.004(4) 0.000 _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 C1 1.978(5) 2 ? Ir1 C1 1.978(5) . ? Ir1 N2 2.052(4) . ? Ir1 N2 2.052(4) 2 ? Ir1 O1 2.131(4) 2 ? Ir1 O1 2.131(4) . ? Ir2 C18 1.983(6) . ? Ir2 C18 1.983(6) 2_655 ? Ir2 N4 2.042(4) 2_655 ? Ir2 N4 2.042(4) . ? Ir2 O2 2.127(4) . ? Ir2 O2 2.127(4) 2_655 ? C1 C2 1.408(7) . ? C1 C5 1.427(7) . ? C2 C3 1.372(8) . ? C2 H2 0.9500 . ? C3 N1 1.325(8) . ? C3 F1 1.365(6) . ? N1 C4 1.329(7) . ? C4 F2 1.360(6) . ? C4 C5 1.376(8) . ? C5 C6 1.478(8) . ? C6 N2 1.368(7) . ? C6 C10 1.401(7) . ? N2 C7 1.338(7) . ? C7 C8 1.381(8) . ? C7 H7 0.9500 . ? C8 C9 1.393(8) . ? C8 H8 0.9500 . ? C9 C10 1.398(8) . ? C9 C11 1.534(8) . ? C10 H10 0.9500 . ? C11 C12 1.519(8) . ? C11 C13 1.531(8) . ? C11 C14 1.547(8) . ? C12 H12 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 H13 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 H14 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? O1 C15 1.278(7) . ? C15 C16 1.389(7) . ? C15 C17 1.517(8) . ? C16 C15 1.389(7) 2 ? C16 H16 0.9500 . ? C17 H17 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C19 1.388(8) . ? C18 C22 1.433(7) . ? C19 C20 1.362(8) . ? C19 H19 0.9500 . ? C20 N3 1.336(7) . ? C20 F3 1.355(6) . ? N3 C21 1.318(7) . ? C21 F4 1.358(6) . ? C21 C22 1.382(8) . ? C22 C23 1.477(7) . ? C23 N4 1.377(7) . ? C23 C27 1.404(7) . ? N4 C24 1.330(7) . ? C24 C25 1.383(8) . ? C24 H24 0.9500 . ? C25 C26 1.385(8) . ? C25 H25 0.9500 . ? C26 C27 1.395(8) . ? C26 C28 1.543(7) . ? C27 H27 0.9500 . ? C28 C31 1.525(8) . ? C28 C30 1.535(8) . ? C28 C29 1.542(8) . ? C29 H29 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C30 H30 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C31 H31 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? O2 C32 1.283(7) . ? C32 C34 1.406(7) . ? C32 C33 1.510(8) . ? C33 H33 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C34 C32 1.406(7) 2_655 ? C34 H34 0.9500 . ? 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 C1 Ir1 C1 86.6(3) 2 . ? C1 Ir1 N2 95.9(2) 2 . ? C1 Ir1 N2 80.5(2) . . ? C1 Ir1 N2 80.5(2) 2 2 ? C1 Ir1 N2 95.9(2) . 2 ? N2 Ir1 N2 175.1(2) . 2 ? C1 Ir1 O1 92.61(18) 2 2 ? C1 Ir1 O1 176.47(19) . 2 ? N2 Ir1 O1 96.15(16) . 2 ? N2 Ir1 O1 87.36(16) 2 2 ? C1 Ir1 O1 176.47(18) 2 . ? C1 Ir1 O1 92.61(18) . . ? N2 Ir1 O1 87.36(16) . . ? N2 Ir1 O1 96.15(16) 2 . ? O1 Ir1 O1 88.4(2) 2 . ? C18 Ir2 C18 89.8(3) . 2_655 ? C18 Ir2 N4 97.3(2) . 2_655 ? C18 Ir2 N4 80.8(2) 2_655 2_655 ? C18 Ir2 N4 80.8(2) . . ? C18 Ir2 N4 97.3(2) 2_655 . ? N4 Ir2 N4 177.4(3) 2_655 . ? C18 Ir2 O2 90.72(19) . . ? C18 Ir2 O2 174.70(18) 2_655 . ? N4 Ir2 O2 93.87(16) 2_655 . ? N4 Ir2 O2 87.99(16) . . ? C18 Ir2 O2 174.70(18) . 2_655 ? C18 Ir2 O2 90.72(19) 2_655 2_655 ? N4 Ir2 O2 87.99(16) 2_655 2_655 ? N4 Ir2 O2 93.87(16) . 2_655 ? O2 Ir2 O2 89.2(2) . 2_655 ? C2 C1 C5 116.6(5) . . ? C2 C1 Ir1 127.9(4) . . ? C5 C1 Ir1 115.3(4) . . ? C3 C2 C1 117.3(5) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? N1 C3 F1 113.9(5) . . ? N1 C3 C2 128.0(5) . . ? F1 C3 C2 118.1(5) . . ? C3 N1 C4 113.7(5) . . ? N1 C4 F2 112.9(5) . . ? N1 C4 C5 126.2(5) . . ? F2 C4 C5 120.9(5) . . ? C4 C5 C1 118.1(5) . . ? C4 C5 C6 126.8(5) . . ? C1 C5 C6 115.0(5) . . ? N2 C6 C10 119.8(5) . . ? N2 C6 C5 112.4(5) . . ? C10 C6 C5 127.4(5) . . ? C7 N2 C6 119.6(5) . . ? C7 N2 Ir1 123.7(4) . . ? C6 N2 Ir1 116.7(4) . . ? N2 C7 C8 122.4(5) . . ? N2 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C7 C8 C9 120.1(5) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 117.2(5) . . ? C8 C9 C11 119.8(5) . . ? C10 C9 C11 122.9(5) . . ? C9 C10 C6 120.8(5) . . ? C9 C10 H10 119.6 . . ? C6 C10 H10 119.6 . . ? C12 C11 C13 109.8(5) . . ? C12 C11 C9 112.4(5) . . ? C13 C11 C9 108.6(5) . . ? C12 C11 C14 108.8(5) . . ? C13 C11 C14 107.8(5) . . ? C9 C11 C14 109.3(5) . . ? C11 C12 H12 109.5 . . ? C11 C12 H12A 109.5 . . ? H12 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C13 H13 109.5 . . ? C11 C13 H13A 109.5 . . ? H13 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C14 H14 109.5 . . ? C11 C14 H14A 109.5 . . ? H14 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 O1 Ir1 125.1(4) . . ? O1 C15 C16 126.4(6) . . ? O1 C15 C17 113.3(5) . . ? C16 C15 C17 120.3(6) . . ? C15 C16 C15 128.3(8) . 2 ? C15 C16 H16 115.8 . . ? C15 C16 H16 115.8 2 . ? C15 C17 H17 109.5 . . ? C15 C17 H17A 109.5 . . ? H17 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C19 C18 C22 116.4(5) . . ? C19 C18 Ir2 129.6(4) . . ? C22 C18 Ir2 113.9(4) . . ? C20 C19 C18 118.6(5) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? N3 C20 F3 113.0(5) . . ? N3 C20 C19 127.3(6) . . ? F3 C20 C19 119.8(5) . . ? C21 N3 C20 113.4(5) . . ? N3 C21 F4 113.4(5) . . ? N3 C21 C22 126.9(5) . . ? F4 C21 C22 119.7(5) . . ? C21 C22 C18 117.3(5) . . ? C21 C22 C23 126.5(5) . . ? C18 C22 C23 115.6(5) . . ? N4 C23 C27 119.5(5) . . ? N4 C23 C22 111.8(5) . . ? C27 C23 C22 128.4(5) . . ? C24 N4 C23 119.1(5) . . ? C24 N4 Ir2 124.4(4) . . ? C23 N4 Ir2 116.5(4) . . ? N4 C24 C25 123.0(5) . . ? N4 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? C24 C25 C26 120.2(5) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C27 117.0(5) . . ? C25 C26 C28 122.2(5) . . ? C27 C26 C28 120.8(5) . . ? C26 C27 C23 121.2(5) . . ? C26 C27 H27 119.4 . . ? C23 C27 H27 119.4 . . ? C31 C28 C30 109.6(5) . . ? C31 C28 C29 108.2(5) . . ? C30 C28 C29 109.7(5) . . ? C31 C28 C26 111.7(5) . . ? C30 C28 C26 108.5(5) . . ? C29 C28 C26 109.2(4) . . ? C28 C29 H29 109.5 . . ? C28 C29 H29A 109.5 . . ? H29 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C30 H30 109.5 . . ? C28 C30 H30A 109.5 . . ? H30 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C31 H31 109.5 . . ? C28 C31 H31A 109.5 . . ? H31 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C32 O2 Ir2 124.9(4) . . ? O2 C32 C34 126.7(6) . . ? O2 C32 C33 114.7(6) . . ? C34 C32 C33 118.7(6) . . ? C32 C33 H33 109.5 . . ? C32 C33 H33A 109.5 . . ? H33 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C34 C32 127.5(8) . 2_655 ? C32 C34 H34 116.2 . . ? C32 C34 H34 116.2 2_655 . ? 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 C1 Ir1 C1 C2 76.7(5) 2 . . . ? N2 Ir1 C1 C2 173.3(5) . . . . ? N2 Ir1 C1 C2 -3.4(5) 2 . . . ? O1 Ir1 C1 C2 154(3) 2 . . . ? O1 Ir1 C1 C2 -99.8(5) . . . . ? C1 Ir1 C1 C5 -98.3(4) 2 . . . ? N2 Ir1 C1 C5 -1.7(4) . . . . ? N2 Ir1 C1 C5 -178.4(4) 2 . . . ? O1 Ir1 C1 C5 -21(3) 2 . . . ? O1 Ir1 C1 C5 85.2(4) . . . . ? C5 C1 C2 C3 0.2(8) . . . . ? Ir1 C1 C2 C3 -174.7(4) . . . . ? C1 C2 C3 N1 -2.6(10) . . . . ? C1 C2 C3 F1 177.9(5) . . . . ? F1 C3 N1 C4 -178.6(5) . . . . ? C2 C3 N1 C4 1.9(9) . . . . ? C3 N1 C4 F2 179.8(5) . . . . ? C3 N1 C4 C5 1.3(9) . . . . ? N1 C4 C5 C1 -3.4(9) . . . . ? F2 C4 C5 C1 178.1(5) . . . . ? N1 C4 C5 C6 173.0(6) . . . . ? F2 C4 C5 C6 -5.4(9) . . . . ? C2 C1 C5 C4 2.4(8) . . . . ? Ir1 C1 C5 C4 178.0(4) . . . . ? C2 C1 C5 C6 -174.4(5) . . . . ? Ir1 C1 C5 C6 1.2(6) . . . . ? C4 C5 C6 N2 -175.9(6) . . . . ? C1 C5 C6 N2 0.6(7) . . . . ? C4 C5 C6 C10 -2.4(10) . . . . ? C1 C5 C6 C10 174.1(5) . . . . ? C10 C6 N2 C7 1.3(8) . . . . ? C5 C6 N2 C7 175.4(5) . . . . ? C10 C6 N2 Ir1 -176.1(4) . . . . ? C5 C6 N2 Ir1 -2.0(6) . . . . ? C1 Ir1 N2 C7 -89.7(5) 2 . . . ? C1 Ir1 N2 C7 -175.2(5) . . . . ? N2 Ir1 N2 C7 -132.2(4) 2 . . . ? O1 Ir1 N2 C7 3.6(5) 2 . . . ? O1 Ir1 N2 C7 91.7(5) . . . . ? C1 Ir1 N2 C6 87.7(4) 2 . . . ? C1 Ir1 N2 C6 2.1(4) . . . . ? N2 Ir1 N2 C6 45.1(4) 2 . . . ? O1 Ir1 N2 C6 -179.0(4) 2 . . . ? O1 Ir1 N2 C6 -90.9(4) . . . . ? C6 N2 C7 C8 -3.2(9) . . . . ? Ir1 N2 C7 C8 174.1(4) . . . . ? N2 C7 C8 C9 1.1(9) . . . . ? C7 C8 C9 C10 2.7(9) . . . . ? C7 C8 C9 C11 -175.0(5) . . . . ? C8 C9 C10 C6 -4.4(8) . . . . ? C11 C9 C10 C6 173.2(5) . . . . ? N2 C6 C10 C9 2.5(8) . . . . ? C5 C6 C10 C9 -170.6(5) . . . . ? C8 C9 C11 C12 -172.8(6) . . . . ? C10 C9 C11 C12 9.6(8) . . . . ? C8 C9 C11 C13 65.4(7) . . . . ? C10 C9 C11 C13 -112.1(6) . . . . ? C8 C9 C11 C14 -51.9(7) . . . . ? C10 C9 C11 C14 130.5(6) . . . . ? C1 Ir1 O1 C15 109(3) 2 . . . ? C1 Ir1 O1 C15 -174.1(4) . . . . ? N2 Ir1 O1 C15 -93.7(4) . . . . ? N2 Ir1 O1 C15 89.7(4) 2 . . . ? O1 Ir1 O1 C15 2.5(3) 2 . . . ? Ir1 O1 C15 C16 -5.3(7) . . . . ? Ir1 O1 C15 C17 176.0(4) . . . . ? O1 C15 C16 C15 3.0(4) . . . 2 ? C17 C15 C16 C15 -178.3(5) . . . 2 ? C18 Ir2 C18 C19 71.6(5) 2_655 . . . ? N4 Ir2 C18 C19 -9.1(5) 2_655 . . . ? N4 Ir2 C18 C19 169.0(5) . . . . ? O2 Ir2 C18 C19 -103.1(5) . . . . ? O2 Ir2 C18 C19 167.3(17) 2_655 . . . ? C18 Ir2 C18 C22 -107.2(4) 2_655 . . . ? N4 Ir2 C18 C22 172.1(4) 2_655 . . . ? N4 Ir2 C18 C22 -9.8(4) . . . . ? O2 Ir2 C18 C22 78.1(4) . . . . ? O2 Ir2 C18 C22 -11(2) 2_655 . . . ? C22 C18 C19 C20 -1.5(8) . . . . ? Ir2 C18 C19 C20 179.7(4) . . . . ? C18 C19 C20 N3 -1.0(10) . . . . ? C18 C19 C20 F3 177.5(5) . . . . ? F3 C20 N3 C21 -177.2(5) . . . . ? C19 C20 N3 C21 1.4(9) . . . . ? C20 N3 C21 F4 -178.5(5) . . . . ? C20 N3 C21 C22 0.9(9) . . . . ? N3 C21 C22 C18 -3.2(9) . . . . ? F4 C21 C22 C18 176.1(5) . . . . ? N3 C21 C22 C23 168.5(6) . . . . ? F4 C21 C22 C23 -12.2(9) . . . . ? C19 C18 C22 C21 3.4(8) . . . . ? Ir2 C18 C22 C21 -177.7(4) . . . . ? C19 C18 C22 C23 -169.3(5) . . . . ? Ir2 C18 C22 C23 9.7(6) . . . . ? C21 C22 C23 N4 -174.3(6) . . . . ? C18 C22 C23 N4 -2.4(7) . . . . ? C21 C22 C23 C27 0.2(10) . . . . ? C18 C22 C23 C27 172.0(5) . . . . ? C27 C23 N4 C24 -3.0(8) . . . . ? C22 C23 N4 C24 172.0(5) . . . . ? C27 C23 N4 Ir2 179.1(4) . . . . ? C22 C23 N4 Ir2 -5.9(6) . . . . ? C18 Ir2 N4 C24 -168.8(5) . . . . ? C18 Ir2 N4 C24 -80.2(5) 2_655 . . . ? N4 Ir2 N4 C24 -124.4(5) 2_655 . . . ? O2 Ir2 N4 C24 100.1(5) . . . . ? O2 Ir2 N4 C24 11.0(5) 2_655 . . . ? C18 Ir2 N4 C23 8.9(4) . . . . ? C18 Ir2 N4 C23 97.5(4) 2_655 . . . ? N4 Ir2 N4 C23 53.4(4) 2_655 . . . ? O2 Ir2 N4 C23 -82.1(4) . . . . ? O2 Ir2 N4 C23 -171.2(4) 2_655 . . . ? C23 N4 C24 C25 1.0(9) . . . . ? Ir2 N4 C24 C25 178.7(4) . . . . ? N4 C24 C25 C26 0.9(9) . . . . ? C24 C25 C26 C27 -0.6(8) . . . . ? C24 C25 C26 C28 -179.7(5) . . . . ? C25 C26 C27 C23 -1.4(8) . . . . ? C28 C26 C27 C23 177.6(5) . . . . ? N4 C23 C27 C26 3.3(8) . . . . ? C22 C23 C27 C26 -170.8(5) . . . . ? C25 C26 C28 C31 1.4(8) . . . . ? C27 C26 C28 C31 -177.6(5) . . . . ? C25 C26 C28 C30 -119.5(6) . . . . ? C27 C26 C28 C30 61.5(7) . . . . ? C25 C26 C28 C29 121.0(6) . . . . ? C27 C26 C28 C29 -58.0(7) . . . . ? C18 Ir2 O2 C32 -176.0(4) . . . . ? C18 Ir2 O2 C32 88(2) 2_655 . . . ? N4 Ir2 O2 C32 86.6(4) 2_655 . . . ? N4 Ir2 O2 C32 -95.2(4) . . . . ? O2 Ir2 O2 C32 -1.3(3) 2_655 . . . ? Ir2 O2 C32 C34 2.8(7) . . . . ? Ir2 O2 C32 C33 -176.5(4) . . . . ? O2 C32 C34 C32 -1.6(4) . . . 2_655 ? C33 C32 C34 C32 177.7(5) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.289 _refine_diff_density_min -1.145 _refine_diff_density_rms 0.129