# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chen, Tsun-Ren' _publ_contact_author_email trchen@mail.npue.edu.tw _publ_section_title ; An 18+\^I' Iridium Dimer Releasing Metalloradical Spontaneously ; loop_ _publ_author_name T.-R.Chen H.-P.Lee J.-D.Chen K.H.-C.Chen # Attachment '- 1.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 778557' #TrackingRef '- 1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H24 Cl F8 Ir2 N4 O4, 4(C H2 Cl2)' _chemical_formula_sum 'C56 H32 Cl9 F8 Ir2 N4 O4' _chemical_formula_weight 1680.31 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A b a 2' _symmetry_int_tables_number 41 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1, z+1/2' 'x+1/2, -y+1, z+1/2' _cell_length_a 21.8706(4) _cell_length_b 14.4783(3) _cell_length_c 16.9835(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5377.81(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18102 _cell_measurement_theta_min 2.6124 _cell_measurement_theta_max 29.1567 _exptl_crystal_description parallelepiped _exptl_crystal_colour orange _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.075 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3228 _exptl_absorpt_coefficient_mu 5.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49853 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25544 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 29.28 _reflns_number_total 6320 _reflns_number_gt 5846 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0247P)^2^+24.9548P] 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 constro _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 0.028(6) _refine_ls_number_reflns 6320 _refine_ls_number_parameters 375 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0647 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.993582(6) 0.395350(11) 0.72552(2) 0.01082(5) Uani 1 1 d . . . Cl1 Cl 1.0000 0.5000 0.61127(11) 0.0135(3) Uani 1 2 d S . . Cl2 Cl 0.76740(8) 0.22092(13) 0.54419(11) 0.0368(4) Uani 1 1 d . . . Cl3 Cl 0.78751(7) 0.32083(12) 0.39864(10) 0.0308(4) Uani 1 1 d . . . Cl4 Cl 1.09002(9) -0.02547(13) 0.7280(2) 0.0515(4) Uani 1 1 d . . . Cl5 Cl 1.08311(9) 0.02771(13) 0.89204(13) 0.0409(4) Uani 1 1 d . . . F1 F 1.06320(17) 0.0617(2) 0.5144(2) 0.0268(8) Uani 1 1 d . . . F2 F 0.90482(15) 0.2305(3) 0.6288(2) 0.0229(8) Uani 1 1 d . . . F3 F 0.89574(16) 0.1417(3) 0.99072(19) 0.0252(8) Uani 1 1 d . . . F4 F 1.06800(15) 0.2685(3) 0.8688(2) 0.0262(8) Uani 1 1 d . . . O1 O 1.16938(16) 0.3043(3) 0.6965(2) 0.0165(8) Uani 1 1 d . . . O2 O 0.81147(17) 0.3405(3) 0.7627(2) 0.0139(8) Uani 1 1 d . . . N1 N 1.08522(19) 0.3779(3) 0.7371(3) 0.0107(10) Uani 1 1 d . . . N2 N 0.89965(18) 0.3956(3) 0.7154(4) 0.0119(10) Uani 1 1 d . . . C1 C 1.1340(2) 0.4090(4) 0.7829(3) 0.0138(11) Uani 1 1 d . . . C2 C 1.1370(3) 0.4676(4) 0.8476(3) 0.0148(11) Uani 1 1 d . . . H2A H 1.1016 0.4967 0.8687 0.018 Uiso 1 1 calc R . . C3 C 1.1935(4) 0.4810(5) 0.8790(5) 0.0218(17) Uani 1 1 d . . . H3A H 1.1974 0.5207 0.9233 0.026 Uiso 1 1 calc R . . C4 C 1.2456(3) 0.4395(4) 0.8494(3) 0.0223(13) Uani 1 1 d . . . H4A H 1.2839 0.4530 0.8731 0.027 Uiso 1 1 calc R . . C5 C 1.2437(3) 0.3790(4) 0.7864(4) 0.0193(12) Uani 1 1 d . . . H5A H 1.2790 0.3492 0.7659 0.023 Uiso 1 1 calc R . . C6 C 1.1855(3) 0.3657(4) 0.7558(3) 0.0153(11) Uani 1 1 d . . . C7 C 1.1089(2) 0.3156(4) 0.6897(3) 0.0123(10) Uani 1 1 d . . . C8 C 1.0683(2) 0.2574(4) 0.6436(3) 0.0124(10) Uani 1 1 d . . . C9 C 1.0895(3) 0.1863(4) 0.5974(3) 0.0179(11) Uani 1 1 d . . . H9A H 1.1320 0.1756 0.5899 0.021 Uiso 1 1 calc R . . C10 C 1.0452(3) 0.1309(4) 0.5624(3) 0.0198(12) Uani 1 1 d . . . C11 C 0.9837(3) 0.1456(4) 0.5733(3) 0.0200(12) Uani 1 1 d . . . H11A H 0.9542 0.1065 0.5493 0.024 Uiso 1 1 calc R . . C12 C 0.9661(3) 0.2187(4) 0.6202(3) 0.0164(11) Uani 1 1 d . . . C13 C 1.0061(2) 0.2793(4) 0.6578(3) 0.0140(10) Uani 1 1 d . . . C14 C 0.8518(2) 0.4278(4) 0.6665(3) 0.0148(11) Uani 1 1 d . . . C15 C 0.8499(3) 0.4832(4) 0.5996(4) 0.0167(12) Uani 1 1 d . . . H15A H 0.8863 0.5056 0.5759 0.020 Uiso 1 1 calc R . . C16 C 0.7939(4) 0.5042(4) 0.5691(5) 0.0193(16) Uani 1 1 d . . . H16A H 0.7913 0.5415 0.5231 0.023 Uiso 1 1 calc R . . C17 C 0.7388(3) 0.4710(4) 0.6053(4) 0.0220(13) Uani 1 1 d . . . H17A H 0.7003 0.4880 0.5838 0.026 Uiso 1 1 calc R . . C18 C 0.7408(3) 0.4149(4) 0.6707(3) 0.0196(12) Uani 1 1 d . . . H18A H 0.7048 0.3916 0.6950 0.024 Uiso 1 1 calc R . . C19 C 0.7980(3) 0.3949(4) 0.6983(3) 0.0155(11) Uani 1 1 d . . . C20 C 0.8727(2) 0.3453(4) 0.7692(3) 0.0109(10) Uani 1 1 d . . . C21 C 0.9080(2) 0.2979(4) 0.8272(3) 0.0142(11) Uani 1 1 d . . . C22 C 0.8805(3) 0.2423(4) 0.8839(3) 0.0175(12) Uani 1 1 d . . . H22A H 0.8373 0.2357 0.8874 0.021 Uiso 1 1 calc R . . C23 C 0.9196(3) 0.1973(4) 0.9347(3) 0.0191(12) Uani 1 1 d . . . C24 C 0.9818(3) 0.2060(4) 0.9287(4) 0.0215(12) Uani 1 1 d . . . H24A H 1.0080 0.1728 0.9632 0.026 Uiso 1 1 calc R . . C25 C 1.0059(2) 0.2634(4) 0.8723(3) 0.0174(11) Uani 1 1 d . . . C26 C 0.9713(3) 0.3128(4) 0.8182(3) 0.0136(10) Uani 1 1 d . . . C27 C 0.8221(3) 0.2649(5) 0.4792(4) 0.0267(14) Uani 1 1 d . . . H27A H 0.8481 0.2138 0.4597 0.032 Uiso 1 1 calc R . . H27B H 0.8487 0.3092 0.5075 0.032 Uiso 1 1 calc R . . C28 C 1.0776(4) 0.0643(6) 0.7941(5) 0.0425(18) Uani 1 1 d . . . H28A H 1.1080 0.1137 0.7845 0.051 Uiso 1 1 calc R . . H28B H 1.0364 0.0907 0.7850 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir 0.01350(8) 0.00854(7) 0.01042(8) 0.00076(14) -0.0001(2) -0.00099(6) Cl1 0.0164(9) 0.0125(8) 0.0114(8) 0.000 0.000 -0.0030(7) Cl2 0.0346(9) 0.0418(10) 0.0341(10) -0.0001(8) 0.0110(7) -0.0113(7) Cl3 0.0327(9) 0.0313(9) 0.0286(9) 0.0027(7) -0.0070(6) 0.0052(7) Cl4 0.0616(11) 0.0406(9) 0.0523(12) -0.0109(17) -0.0070(17) -0.0002(7) Cl5 0.0422(10) 0.0306(9) 0.0498(12) 0.0063(9) 0.0070(9) -0.0001(8) F1 0.041(2) 0.0184(18) 0.0207(19) -0.0088(15) 0.0010(15) 0.0044(16) F2 0.0191(17) 0.0232(19) 0.026(2) -0.0128(16) -0.0051(14) -0.0046(14) F3 0.034(2) 0.0268(19) 0.0149(19) 0.0102(15) -0.0008(14) -0.0075(16) F4 0.0200(18) 0.034(2) 0.025(2) 0.0123(16) -0.0070(14) -0.0010(15) O1 0.0133(18) 0.017(2) 0.019(2) -0.0007(15) 0.0003(13) 0.0030(15) O2 0.019(2) 0.011(2) 0.0122(19) 0.0038(15) -0.0010(15) -0.0054(15) N1 0.0171(19) 0.010(2) 0.005(3) 0.0013(17) 0.0015(16) -0.0018(14) N2 0.0171(17) 0.0100(17) 0.009(3) 0.006(2) 0.002(2) 0.0010(16) C1 0.018(3) 0.011(3) 0.013(3) 0.001(2) -0.0018(19) -0.001(2) C2 0.024(3) 0.015(3) 0.006(3) 0.002(2) 0.001(2) -0.001(2) C3 0.036(4) 0.009(3) 0.020(4) 0.002(3) -0.006(3) -0.005(3) C4 0.024(3) 0.020(3) 0.023(3) 0.003(3) -0.013(2) -0.009(2) C5 0.019(3) 0.012(3) 0.027(3) 0.002(2) -0.002(2) 0.002(2) C6 0.021(3) 0.006(2) 0.019(3) 0.003(2) 0.001(2) -0.002(2) C7 0.019(3) 0.009(2) 0.009(2) 0.004(2) 0.001(2) 0.000(2) C8 0.021(3) 0.009(3) 0.008(3) 0.002(2) -0.0029(19) 0.000(2) C9 0.023(3) 0.020(3) 0.011(3) 0.004(2) -0.001(2) 0.004(2) C10 0.040(4) 0.007(2) 0.013(3) -0.004(2) 0.004(2) 0.002(2) C11 0.029(3) 0.015(3) 0.016(3) -0.004(2) -0.004(2) -0.008(2) C12 0.025(3) 0.014(3) 0.011(3) 0.001(2) -0.002(2) -0.002(2) C13 0.020(3) 0.015(2) 0.008(2) -0.0001(19) -0.002(2) -0.001(2) C14 0.017(3) 0.013(3) 0.015(3) -0.005(2) -0.003(2) -0.001(2) C15 0.026(3) 0.005(3) 0.019(3) 0.003(2) 0.004(2) 0.000(2) C16 0.024(4) 0.019(3) 0.015(3) 0.002(3) -0.007(3) -0.004(3) C17 0.022(3) 0.020(3) 0.024(3) 0.002(3) -0.007(2) 0.002(2) C18 0.017(3) 0.018(3) 0.023(3) -0.002(2) -0.003(2) -0.005(2) C19 0.023(3) 0.009(3) 0.014(3) 0.000(2) -0.0010(18) -0.004(2) C20 0.020(3) 0.009(3) 0.003(2) -0.0033(19) 0.0012(19) -0.005(2) C21 0.022(3) 0.012(3) 0.009(3) -0.001(2) -0.001(2) -0.002(2) C22 0.019(3) 0.018(3) 0.016(3) 0.002(2) 0.000(2) -0.004(2) C23 0.034(3) 0.014(3) 0.010(3) 0.005(2) -0.001(2) -0.006(2) C24 0.032(3) 0.014(3) 0.019(3) 0.005(2) -0.007(2) -0.001(2) C25 0.016(3) 0.017(3) 0.019(3) 0.005(2) -0.001(2) -0.002(2) C26 0.026(3) 0.008(2) 0.007(2) -0.004(2) -0.001(2) -0.003(2) C27 0.018(3) 0.031(4) 0.031(4) 0.010(3) -0.002(2) -0.001(2) C28 0.054(5) 0.040(4) 0.034(4) 0.007(4) 0.002(4) -0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir N1 2.030(4) . ? Ir C26 2.036(5) . ? Ir C13 2.055(6) . ? Ir N2 2.062(4) . ? Ir Cl1 2.4658(14) . ? Ir Ir 3.0433(3) 2_765 ? Cl1 Ir 2.4658(14) 2_765 ? Cl2 C27 1.748(6) . ? Cl3 C27 1.760(6) . ? Cl4 C28 1.739(9) . ? Cl5 C28 1.750(8) . ? F1 C10 1.350(6) . ? F2 C12 1.360(7) . ? F3 C23 1.352(6) . ? F4 C25 1.362(6) . ? O1 C7 1.338(6) . ? O1 C6 1.389(7) . ? O2 C20 1.346(6) . ? O2 C19 1.379(6) . ? N1 C7 1.314(7) . ? N1 C1 1.395(7) . ? N2 C20 1.308(7) . ? N2 C14 1.414(7) . ? C1 C6 1.369(8) . ? C1 C2 1.390(8) . ? C2 C3 1.361(10) . ? C2 H2A 0.9500 . ? C3 C4 1.382(11) . ? C3 H3A 0.9500 . ? C4 C5 1.385(8) . ? C4 H4A 0.9500 . ? C5 C6 1.388(8) . ? C5 H5A 0.9500 . ? C7 C8 1.453(7) . ? C8 C9 1.375(8) . ? C8 C13 1.417(8) . ? C9 C10 1.392(8) . ? C9 H9A 0.9500 . ? C10 C11 1.374(9) . ? C11 C12 1.379(8) . ? C11 H11A 0.9500 . ? C12 C13 1.394(8) . ? C14 C19 1.380(8) . ? C14 C15 1.392(8) . ? C15 C16 1.364(10) . ? C15 H15A 0.9500 . ? C16 C17 1.436(10) . ? C16 H16A 0.9500 . ? C17 C18 1.377(8) . ? C17 H17A 0.9500 . ? C18 C19 1.369(8) . ? C18 H18A 0.9500 . ? C20 C21 1.428(7) . ? C21 C22 1.392(8) . ? C21 C26 1.410(8) . ? C22 C23 1.379(8) . ? C22 H22A 0.9500 . ? C23 C24 1.370(8) . ? C24 C25 1.373(8) . ? C24 H24A 0.9500 . ? C25 C26 1.388(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 Ir C26 95.1(2) . . ? N1 Ir C13 79.7(2) . . ? C26 Ir C13 89.1(2) . . ? N1 Ir N2 172.91(16) . . ? C26 Ir N2 80.1(2) . . ? C13 Ir N2 95.0(2) . . ? N1 Ir Cl1 95.53(13) . . ? C26 Ir Cl1 169.40(16) . . ? C13 Ir Cl1 93.10(15) . . ? N2 Ir Cl1 89.42(16) . . ? N1 Ir Ir 91.88(11) . 2_765 ? C26 Ir Ir 127.37(15) . 2_765 ? C13 Ir Ir 143.30(15) . 2_765 ? N2 Ir Ir 95.17(12) . 2_765 ? Cl1 Ir Ir 51.90(3) . 2_765 ? Ir Cl1 Ir 76.21(5) 2_765 . ? C7 O1 C6 103.5(4) . . ? C20 O2 C19 104.3(4) . . ? C7 N1 C1 105.2(4) . . ? C7 N1 Ir 114.5(4) . . ? C1 N1 Ir 140.2(4) . . ? C20 N2 C14 105.1(4) . . ? C20 N2 Ir 112.9(4) . . ? C14 N2 Ir 141.9(4) . . ? C6 C1 N1 107.0(5) . . ? C6 C1 C2 120.5(5) . . ? N1 C1 C2 132.4(5) . . ? C3 C2 C1 116.1(6) . . ? C3 C2 H2A 122.0 . . ? C1 C2 H2A 122.0 . . ? C2 C3 C4 123.0(7) . . ? C2 C3 H3A 118.5 . . ? C4 C3 H3A 118.5 . . ? C3 C4 C5 122.1(6) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? C6 C5 C4 113.9(5) . . ? C6 C5 H5A 123.0 . . ? C4 C5 H5A 123.0 . . ? C1 C6 C5 124.4(5) . . ? C1 C6 O1 109.2(5) . . ? C5 C6 O1 126.3(5) . . ? N1 C7 O1 114.9(5) . . ? N1 C7 C8 119.2(5) . . ? O1 C7 C8 125.3(5) . . ? C9 C8 C13 126.0(5) . . ? C9 C8 C7 122.4(5) . . ? C13 C8 C7 111.4(5) . . ? C8 C9 C10 116.1(5) . . ? C8 C9 H9A 121.9 . . ? C10 C9 H9A 121.9 . . ? F1 C10 C11 118.8(5) . . ? F1 C10 C9 118.8(5) . . ? C11 C10 C9 122.3(5) . . ? C12 C11 C10 118.0(5) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? F2 C12 C11 115.7(5) . . ? F2 C12 C13 119.4(5) . . ? C11 C12 C13 124.9(5) . . ? C12 C13 C8 112.6(5) . . ? C12 C13 Ir 133.4(4) . . ? C8 C13 Ir 114.0(4) . . ? C19 C14 C15 119.5(5) . . ? C19 C14 N2 106.7(5) . . ? C15 C14 N2 133.8(5) . . ? C16 C15 C14 117.8(6) . . ? C16 C15 H15A 121.1 . . ? C14 C15 H15A 121.1 . . ? C15 C16 C17 121.0(7) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C16 121.1(6) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C19 C18 C17 115.4(5) . . ? C19 C18 H18A 122.3 . . ? C17 C18 H18A 122.3 . . ? C18 C19 O2 125.9(5) . . ? C18 C19 C14 125.0(5) . . ? O2 C19 C14 109.0(5) . . ? N2 C20 O2 114.8(5) . . ? N2 C20 C21 120.4(5) . . ? O2 C20 C21 124.7(5) . . ? C22 C21 C26 126.1(5) . . ? C22 C21 C20 121.5(5) . . ? C26 C21 C20 112.5(5) . . ? C23 C22 C21 115.9(5) . . ? C23 C22 H22A 122.1 . . ? C21 C22 H22A 122.1 . . ? F3 C23 C24 119.4(5) . . ? F3 C23 C22 118.8(5) . . ? C24 C23 C22 121.8(5) . . ? C23 C24 C25 119.3(5) . . ? C23 C24 H24A 120.4 . . ? C25 C24 H24A 120.4 . . ? F4 C25 C24 116.5(5) . . ? F4 C25 C26 119.1(5) . . ? C24 C25 C26 124.3(5) . . ? C25 C26 C21 112.6(5) . . ? C25 C26 Ir 133.1(4) . . ? C21 C26 Ir 114.1(4) . . ? Cl2 C27 Cl3 111.4(3) . . ? Cl2 C27 H27A 109.4 . . ? Cl3 C27 H27A 109.4 . . ? Cl2 C27 H27B 109.4 . . ? Cl3 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? Cl5 C28 Cl4 112.1(5) . . ? Cl5 C28 H28A 109.2 . . ? Cl4 C28 H28A 109.2 . . ? Cl5 C28 H28B 109.2 . . ? Cl4 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.099 _refine_diff_density_min -1.045 _refine_diff_density_rms 0.140 # Attachment '- 4.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 778558' #TrackingRef '- 4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C41 H23 F4 Ir N2 O4' _chemical_formula_sum 'C41 H23 F4 Ir N2 O4' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour brown _diffrn_ambient_temperature 120(2) _chemical_formula_weight 875.81 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.0381(3) _cell_length_b 14.6705(4) _cell_length_c 19.5320(5) _cell_angle_alpha 102.358(2) _cell_angle_beta 95.205(2) _cell_angle_gamma 94.203(2) _cell_volume 3340.35(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14506 _cell_measurement_theta_min 2.7624 _cell_measurement_theta_max 29.2931 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 4.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70376 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29949 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 29.38 _reflns_number_total 15412 _reflns_number_gt 9910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0534P)^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 constro _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15412 _refine_ls_number_parameters 911 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _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 0.88470(2) -0.755321(17) -0.443354(14) 0.02384(10) Uani 1 1 d . . . F1 F 1.3021(3) -0.9116(3) -0.5698(2) 0.0485(12) Uani 1 1 d . . . F2 F 1.0373(3) -0.6934(3) -0.5665(2) 0.0384(10) Uani 1 1 d . . . F3 F 1.1190(4) -0.3966(3) -0.2416(2) 0.0468(11) Uani 1 1 d . . . F4 F 1.0800(3) -0.7238(3) -0.3002(2) 0.0401(10) Uani 1 1 d . . . O1 O 1.0339(4) -0.9715(3) -0.3816(3) 0.0355(12) Uani 1 1 d . . . O2 O 0.8479(4) -0.4932(3) -0.4775(3) 0.0354(12) Uani 1 1 d . . . O3 O 0.7911(4) -0.8585(3) -0.5219(2) 0.0305(11) Uani 1 1 d . . . O4 O 0.7350(4) -0.7283(3) -0.3953(2) 0.0278(10) Uani 1 1 d . . . N1 N 0.9246(4) -0.8582(4) -0.3925(3) 0.0253(12) Uani 1 1 d . . . N2 N 0.8493(4) -0.6474(4) -0.4908(3) 0.0252(12) Uani 1 1 d . . . C1 C 0.8860(6) -0.8991(5) -0.3401(4) 0.0299(16) Uani 1 1 d . . . C2 C 0.8027(6) -0.8837(5) -0.2977(4) 0.0389(18) Uani 1 1 d . . . H2A H 0.7577 -0.8334 -0.2993 0.047 Uiso 1 1 calc R . . C3 C 0.7846(7) -0.9416(6) -0.2525(4) 0.048(2) Uani 1 1 d . . . H3A H 0.7263 -0.9318 -0.2228 0.058 Uiso 1 1 calc R . . C4 C 0.8528(7) -1.0169(6) -0.2499(5) 0.052(2) Uani 1 1 d . . . H4A H 0.8377 -1.0577 -0.2194 0.062 Uiso 1 1 calc R . . C5 C 0.9396(7) -1.0311(6) -0.2904(4) 0.048(2) Uani 1 1 d . . . H5A H 0.9873 -1.0793 -0.2878 0.057 Uiso 1 1 calc R . . C6 C 0.9537(6) -0.9712(5) -0.3354(4) 0.0349(17) Uani 1 1 d . . . C7 C 1.0096(5) -0.9017(4) -0.4141(4) 0.0266(15) Uani 1 1 d . . . C8 C 1.0704(5) -0.8712(5) -0.4655(4) 0.0296(16) Uani 1 1 d . . . C9 C 1.1633(6) -0.9127(5) -0.4929(4) 0.0324(16) Uani 1 1 d . . . H9A H 1.1916 -0.9648 -0.4778 0.039 Uiso 1 1 calc R . . C10 C 1.2107(6) -0.8742(5) -0.5423(4) 0.0391(19) Uani 1 1 d . . . C11 C 1.1714(5) -0.8004(4) -0.5667(3) 0.0260(15) Uani 1 1 d . . . H11A H 1.2070 -0.7752 -0.6010 0.031 Uiso 1 1 calc R . . C12 C 1.0771(5) -0.7639(4) -0.5392(4) 0.0280(15) Uani 1 1 d . . . C13 C 1.0227(5) -0.7950(4) -0.4879(3) 0.0254(15) Uani 1 1 d . . . C14 C 0.7867(5) -0.6328(5) -0.5515(4) 0.0274(15) Uani 1 1 d . . . C15 C 0.7368(6) -0.6911(5) -0.6127(4) 0.0331(17) Uani 1 1 d . . . H15A H 0.7382 -0.7572 -0.6209 0.040 Uiso 1 1 calc R . . C16 C 0.6843(6) -0.6489(6) -0.6621(4) 0.044(2) Uani 1 1 d . . . H16A H 0.6486 -0.6873 -0.7050 0.053 Uiso 1 1 calc R . . C17 C 0.6819(6) -0.5507(6) -0.6508(4) 0.047(2) Uani 1 1 d . . . H17A H 0.6441 -0.5244 -0.6857 0.056 Uiso 1 1 calc R . . C18 C 0.7338(6) -0.4931(5) -0.5898(4) 0.0410(19) Uani 1 1 d . . . H18A H 0.7330 -0.4269 -0.5811 0.049 Uiso 1 1 calc R . . C19 C 0.7876(6) -0.5366(5) -0.5415(4) 0.0347(17) Uani 1 1 d . . . C20 C 0.8831(6) -0.5651(4) -0.4507(4) 0.0289(16) Uani 1 1 d . . . C21 C 0.9533(6) -0.5565(5) -0.3858(4) 0.0290(15) Uani 1 1 d . . . C22 C 1.0007(6) -0.4723(5) -0.3433(4) 0.0336(17) Uani 1 1 d . . . H22A H 0.9849 -0.4139 -0.3537 0.040 Uiso 1 1 calc R . . C23 C 1.0712(6) -0.4771(5) -0.2857(4) 0.0351(17) Uani 1 1 d . . . C24 C 1.0993(6) -0.5614(5) -0.2708(4) 0.0334(17) Uani 1 1 d . . . H24A H 1.1505 -0.5633 -0.2313 0.040 Uiso 1 1 calc R . . C25 C 1.0498(6) -0.6421(5) -0.3161(4) 0.0306(16) Uani 1 1 d . . . C26 C 0.9719(5) -0.6469(5) -0.3746(4) 0.0287(16) Uani 1 1 d . . . C27 C 0.5371(6) -0.9942(5) -0.6072(4) 0.0307(16) Uani 1 1 d . . . H27A H 0.4901 -0.9852 -0.5702 0.037 Uiso 1 1 calc R . . C28 C 0.4999(7) -1.0563(5) -0.6701(4) 0.045(2) Uani 1 1 d . . . H28A H 0.4290 -1.0916 -0.6755 0.054 Uiso 1 1 calc R . . C29 C 0.5648(8) -1.0674(6) -0.7249(4) 0.050(2) Uani 1 1 d . . . H29A H 0.5376 -1.1084 -0.7688 0.060 Uiso 1 1 calc R . . C30 C 0.6695(7) -1.0190(6) -0.7164(4) 0.047(2) Uani 1 1 d . . . H30A H 0.7151 -1.0270 -0.7541 0.056 Uiso 1 1 calc R . . C31 C 0.7077(6) -0.9589(5) -0.6525(4) 0.0386(18) Uani 1 1 d . . . H31A H 0.7805 -0.9266 -0.6464 0.046 Uiso 1 1 calc R . . C32 C 0.6417(6) -0.9449(4) -0.5970(4) 0.0289(15) Uani 1 1 d . . . C33 C 0.6852(5) -0.8754(4) -0.5299(4) 0.0274(15) Uani 1 1 d . . . C34 C 0.6118(5) -0.8329(5) -0.4847(3) 0.0266(15) Uani 1 1 d . . . H34A H 0.5343 -0.8516 -0.4986 0.032 Uiso 1 1 calc R . . C35 C 0.6377(5) -0.7663(4) -0.4213(3) 0.0236(14) Uani 1 1 d . . . C36 C 0.5456(6) -0.7334(4) -0.3773(4) 0.0287(16) Uani 1 1 d . . . C37 C 0.4303(6) -0.7573(5) -0.4033(4) 0.0359(17) Uani 1 1 d . . . H37A H 0.4099 -0.7940 -0.4497 0.043 Uiso 1 1 calc R . . C38 C 0.3481(6) -0.7268(5) -0.3608(4) 0.0388(18) Uani 1 1 d . . . H38A H 0.2713 -0.7429 -0.3781 0.047 Uiso 1 1 calc R . . C39 C 0.3769(6) -0.6740(6) -0.2945(4) 0.045(2) Uani 1 1 d . . . H39A H 0.3200 -0.6544 -0.2655 0.054 Uiso 1 1 calc R . . C40 C 0.4849(7) -0.6492(7) -0.2696(5) 0.065(3) Uani 1 1 d . . . H40A H 0.5040 -0.6111 -0.2236 0.078 Uiso 1 1 calc R . . C41 C 0.5686(7) -0.6792(6) -0.3110(5) 0.056(3) Uani 1 1 d . . . H41A H 0.6446 -0.6612 -0.2924 0.067 Uiso 1 1 calc R . . Ir2 Ir 0.78260(3) -0.28167(2) -0.137126(15) 0.03174(13) Uani 0.8999(14) 1 d P A 1 Ir2' Ir 0.7304(2) -0.2499(2) -0.09111(14) 0.03174(13) Uani 0.10 1 d P A 2 F5 F 0.9198(5) -0.6877(3) -0.1834(3) 0.0683(15) Uani 1 1 d . A . F6 F 0.9287(5) -0.3959(4) -0.0286(2) 0.0728(17) Uani 1 1 d . A . F7 F 1.2506(5) -0.0815(5) -0.1426(4) 0.111(2) Uani 1 1 d . A . F8 F 0.9381(4) -0.2676(3) -0.2718(2) 0.0584(13) Uani 1 1 d . A . O5 O 0.7130(4) -0.4700(4) -0.3274(3) 0.0439(13) Uani 1 1 d . A . O6 O 0.9797(6) -0.1428(5) 0.0425(3) 0.076(2) Uani 1 1 d . A . O7 O 0.6262(5) -0.3349(4) -0.1186(3) 0.0524(15) Uani 1 1 d . . . O8 O 0.7192(4) -0.1518(4) -0.1348(3) 0.0452(14) Uani 1 1 d . . . N3 N 0.7311(5) -0.3425(5) -0.2392(3) 0.0402(16) Uani 1 1 d . . . N4 N 0.8404(6) -0.2259(5) -0.0348(3) 0.0477(18) Uani 1 1 d . . . C42 C 0.6681(6) -0.3236(6) -0.2984(4) 0.0384(18) Uani 1 1 d . A . C43 C 0.6185(6) -0.2405(6) -0.3074(4) 0.0399(19) Uani 1 1 d . . . H43A H 0.6232 -0.1850 -0.2714 0.048 Uiso 1 1 calc R A . C44 C 0.5626(6) -0.2500(6) -0.3748(5) 0.047(2) Uani 1 1 d . A . H44A H 0.5283 -0.1974 -0.3851 0.056 Uiso 1 1 calc R . . C45 C 0.5539(6) -0.3280(7) -0.4259(4) 0.048(2) Uani 1 1 d . . . H45A H 0.5123 -0.3277 -0.4695 0.057 Uiso 1 1 calc R A . C46 C 0.6022(6) -0.4097(6) -0.4192(4) 0.050(2) Uani 1 1 d . A . H46A H 0.5972 -0.4646 -0.4558 0.060 Uiso 1 1 calc R . . C47 C 0.6591(6) -0.4007(6) -0.3517(4) 0.0397(18) Uani 1 1 d . . . C48 C 0.7525(6) -0.4290(6) -0.2590(4) 0.0404(19) Uani 1 1 d . A . C49 C 0.8121(6) -0.4728(6) -0.2104(4) 0.0402(18) Uani 1 1 d . . . C50 C 0.8382(6) -0.5663(5) -0.2246(4) 0.0409(19) Uani 1 1 d . A . H50A H 0.8189 -0.6063 -0.2700 0.049 Uiso 1 1 calc R . . C51 C 0.8911(7) -0.5969(6) -0.1722(5) 0.048(2) Uani 1 1 d . . . C52 C 0.9212(7) -0.5419(6) -0.1063(5) 0.053(2) Uani 1 1 d . A . H52A H 0.9579 -0.5661 -0.0698 0.064 Uiso 1 1 calc R . . C53 C 0.8958(7) -0.4490(6) -0.0946(4) 0.052(2) Uani 1 1 d . . . C54 C 0.8367(7) -0.4111(6) -0.1439(4) 0.0411(19) Uani 1 1 d . A . C55 C 0.8111(8) -0.2257(6) 0.0319(4) 0.050(2) Uani 1 1 d . A . C56 C 0.7192(8) -0.2640(6) 0.0577(4) 0.055(2) Uani 1 1 d . . . H56A H 0.6585 -0.2996 0.0266 0.066 Uiso 1 1 calc R A . C57 C 0.7186(10) -0.2489(8) 0.1287(5) 0.077(3) Uani 1 1 d . A . H57A H 0.6564 -0.2742 0.1475 0.093 Uiso 1 1 calc R . . C58 C 0.8059(12) -0.1979(8) 0.1738(5) 0.082(4) Uani 1 1 d . . . H58A H 0.8020 -0.1888 0.2231 0.098 Uiso 1 1 calc R A . C59 C 0.8962(11) -0.1604(8) 0.1514(6) 0.079(3) Uani 1 1 d . A . H59A H 0.9571 -0.1264 0.1832 0.095 Uiso 1 1 calc R . . C60 C 0.8957(9) -0.1737(7) 0.0808(5) 0.065(3) Uani 1 1 d . . . C61 C 0.9386(8) -0.1770(6) -0.0265(4) 0.052(2) Uani 1 1 d . A . C62 C 0.9961(7) -0.1726(6) -0.0871(5) 0.053(2) Uani 1 1 d . . . C63 C 1.1006(9) -0.1233(7) -0.0824(6) 0.070(3) Uani 1 1 d . A . H63A H 1.1372 -0.0874 -0.0388 0.084 Uiso 1 1 calc R . . C64 C 1.1478(8) -0.1292(8) -0.1441(7) 0.079(3) Uani 1 1 d . . . C65 C 1.0953(8) -0.1788(7) -0.2075(5) 0.060(3) Uani 1 1 d . A . H65A H 1.1296 -0.1830 -0.2499 0.072 Uiso 1 1 calc R . . C66 C 0.9884(7) -0.2232(5) -0.2071(4) 0.0418(19) Uani 1 1 d . . . C67 C 0.9332(7) -0.2227(5) -0.1478(4) 0.043(2) Uani 1 1 d . A . C68 C 0.3335(9) -0.3157(9) -0.1026(6) 0.0861(14) Uani 1 1 d . A . H68A H 0.3254 -0.2578 -0.1158 0.103 Uiso 1 1 calc R . . C69 C 0.2407(9) -0.3650(9) -0.0900(6) 0.0861(14) Uani 1 1 d . . . H69A H 0.1694 -0.3423 -0.0961 0.103 Uiso 1 1 calc R . . C70 C 0.2492(9) -0.4456(9) -0.0691(6) 0.0861(14) Uani 1 1 d . . . H70A H 0.1860 -0.4770 -0.0553 0.103 Uiso 1 1 calc R . . C71 C 0.3520(9) -0.4823(9) -0.0679(6) 0.0861(14) Uani 1 1 d . . . H71A H 0.3579 -0.5427 -0.0584 0.103 Uiso 1 1 calc R . . C72 C 0.4486(9) -0.4299(9) -0.0810(6) 0.0861(14) Uani 1 1 d . A . H72A H 0.5197 -0.4539 -0.0785 0.103 Uiso 1 1 calc R . . C73 C 0.4383(9) -0.3455(9) -0.0970(6) 0.0861(14) Uani 1 1 d . . . C74 C 0.5439(7) -0.2902(6) -0.1072(4) 0.046(2) Uani 1 1 d . A . C75 C 0.5404(7) -0.1928(7) -0.1015(4) 0.056(2) Uani 1 1 d . . . H75A H 0.4727 -0.1676 -0.0891 0.067 Uiso 1 1 calc R A 2 C76 C 0.6267(7) -0.1297(6) -0.1122(4) 0.047(2) Uani 1 1 d . A . C77 C 0.6136(8) -0.0273(7) -0.0987(5) 0.058(3) Uani 1 1 d . . . C78 C 0.5093(9) 0.0070(8) -0.0947(5) 0.074(3) Uani 1 1 d . A . H78A H 0.4441 -0.0360 -0.1017 0.089 Uiso 1 1 calc R . . C79 C 0.4982(10) 0.1008(7) -0.0810(6) 0.075(3) Uani 1 1 d . . . H79A H 0.4265 0.1235 -0.0784 0.090 Uiso 1 1 calc R A . C80 C 0.5972(11) 0.1638(8) -0.0707(5) 0.077(4) Uani 1 1 d . A . H80A H 0.5911 0.2294 -0.0623 0.092 Uiso 1 1 calc R . . C81 C 0.6991(11) 0.1320(8) -0.0726(6) 0.088(4) Uani 1 1 d . . . H81A H 0.7651 0.1741 -0.0649 0.106 Uiso 1 1 calc R A . C82 C 0.7050(9) 0.0351(7) -0.0864(5) 0.065(3) Uani 1 1 d . A . H82A H 0.7768 0.0121 -0.0870 0.078 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 0.01819(14) 0.02274(15) 0.03430(18) 0.01220(12) 0.00407(11) 0.00747(11) F1 0.032(2) 0.053(3) 0.068(3) 0.015(2) 0.020(2) 0.028(2) F2 0.037(2) 0.034(2) 0.056(3) 0.025(2) 0.020(2) 0.0136(19) F3 0.047(3) 0.036(2) 0.049(3) -0.005(2) -0.005(2) 0.003(2) F4 0.040(2) 0.034(2) 0.047(3) 0.0127(19) -0.008(2) 0.012(2) O1 0.035(3) 0.030(3) 0.047(3) 0.017(2) 0.004(2) 0.015(2) O2 0.039(3) 0.025(2) 0.047(3) 0.018(2) 0.003(2) 0.009(2) O3 0.025(3) 0.025(2) 0.045(3) 0.013(2) 0.005(2) 0.006(2) O4 0.024(2) 0.026(2) 0.035(3) 0.007(2) 0.008(2) 0.008(2) N1 0.020(3) 0.024(3) 0.035(3) 0.013(2) 0.001(2) 0.003(2) N2 0.015(3) 0.030(3) 0.035(3) 0.015(3) 0.005(2) 0.006(2) C1 0.028(4) 0.025(4) 0.039(4) 0.016(3) -0.002(3) 0.001(3) C2 0.025(4) 0.043(4) 0.058(5) 0.030(4) 0.004(4) 0.006(3) C3 0.036(4) 0.067(6) 0.050(5) 0.033(4) 0.004(4) 0.003(4) C4 0.053(5) 0.053(5) 0.057(6) 0.035(4) -0.004(5) 0.001(4) C5 0.056(6) 0.040(5) 0.053(5) 0.023(4) 0.000(4) 0.006(4) C6 0.036(4) 0.032(4) 0.037(4) 0.015(3) -0.007(3) 0.003(3) C7 0.024(3) 0.022(3) 0.034(4) 0.008(3) -0.003(3) 0.006(3) C8 0.022(3) 0.030(4) 0.036(4) 0.004(3) 0.000(3) 0.009(3) C9 0.025(4) 0.024(4) 0.048(4) 0.009(3) -0.002(3) 0.009(3) C10 0.021(4) 0.039(4) 0.055(5) 0.000(4) 0.009(4) 0.010(3) C11 0.022(3) 0.025(3) 0.033(4) 0.008(3) 0.007(3) 0.005(3) C12 0.021(3) 0.023(3) 0.040(4) 0.007(3) 0.003(3) 0.004(3) C13 0.020(3) 0.023(3) 0.033(4) 0.005(3) 0.004(3) 0.000(3) C14 0.023(3) 0.031(4) 0.036(4) 0.019(3) 0.011(3) 0.011(3) C15 0.030(4) 0.039(4) 0.037(4) 0.020(3) 0.008(3) 0.008(3) C16 0.033(4) 0.058(5) 0.046(5) 0.026(4) 0.003(4) 0.003(4) C17 0.035(4) 0.063(6) 0.054(5) 0.040(4) 0.003(4) 0.011(4) C18 0.040(4) 0.040(4) 0.054(5) 0.030(4) 0.008(4) 0.016(4) C19 0.034(4) 0.033(4) 0.046(5) 0.021(3) 0.012(4) 0.015(3) C20 0.028(4) 0.020(3) 0.044(4) 0.015(3) 0.009(3) 0.007(3) C21 0.024(3) 0.030(4) 0.035(4) 0.010(3) 0.005(3) 0.007(3) C22 0.038(4) 0.024(4) 0.040(4) 0.008(3) 0.009(4) 0.002(3) C23 0.031(4) 0.032(4) 0.041(4) 0.005(3) 0.005(4) 0.000(3) C24 0.025(4) 0.042(4) 0.030(4) 0.003(3) 0.000(3) 0.008(3) C25 0.026(4) 0.032(4) 0.038(4) 0.014(3) 0.004(3) 0.011(3) C26 0.023(4) 0.032(4) 0.037(4) 0.015(3) 0.012(3) 0.010(3) C27 0.029(4) 0.031(4) 0.036(4) 0.014(3) 0.003(3) 0.011(3) C28 0.039(5) 0.035(4) 0.063(6) 0.018(4) -0.005(4) 0.001(4) C29 0.069(6) 0.039(5) 0.035(5) -0.002(4) -0.008(4) 0.005(4) C30 0.052(5) 0.046(5) 0.042(5) 0.007(4) 0.011(4) 0.008(4) C31 0.035(4) 0.034(4) 0.049(5) 0.010(4) 0.010(4) 0.010(3) C32 0.025(4) 0.026(4) 0.041(4) 0.017(3) 0.003(3) 0.011(3) C33 0.023(4) 0.026(3) 0.040(4) 0.021(3) 0.000(3) 0.002(3) C34 0.016(3) 0.036(4) 0.031(4) 0.014(3) 0.004(3) 0.007(3) C35 0.018(3) 0.030(4) 0.029(4) 0.021(3) -0.002(3) 0.007(3) C36 0.028(4) 0.022(3) 0.041(4) 0.012(3) 0.010(3) 0.010(3) C37 0.028(4) 0.048(5) 0.035(4) 0.013(3) 0.005(3) 0.011(4) C38 0.028(4) 0.042(4) 0.050(5) 0.013(4) 0.010(4) 0.014(3) C39 0.027(4) 0.059(5) 0.055(5) 0.015(4) 0.018(4) 0.017(4) C40 0.037(5) 0.085(7) 0.060(6) -0.014(5) 0.014(5) 0.010(5) C41 0.026(4) 0.049(5) 0.078(7) -0.006(5) -0.022(4) 0.005(4) Ir2 0.0342(2) 0.0397(2) 0.02470(19) 0.01188(15) 0.00121(14) 0.01426(16) Ir2' 0.0342(2) 0.0397(2) 0.02470(19) 0.01188(15) 0.00121(14) 0.01426(16) F5 0.082(4) 0.049(3) 0.080(4) 0.027(3) 0.000(3) 0.024(3) F6 0.107(5) 0.073(4) 0.039(3) 0.012(3) -0.017(3) 0.042(3) F7 0.050(4) 0.148(6) 0.154(6) 0.088(5) -0.010(4) -0.012(4) F8 0.071(3) 0.063(3) 0.049(3) 0.022(2) 0.018(3) 0.020(3) O5 0.042(3) 0.052(3) 0.040(3) 0.014(3) 0.005(3) 0.011(3) O6 0.080(5) 0.092(5) 0.048(4) 0.010(4) -0.023(4) 0.011(4) O7 0.050(4) 0.067(4) 0.043(3) 0.013(3) 0.001(3) 0.027(3) O8 0.040(3) 0.050(3) 0.047(3) 0.014(3) -0.002(3) 0.014(3) N3 0.038(4) 0.059(4) 0.025(3) 0.012(3) -0.005(3) 0.011(3) N4 0.057(5) 0.058(4) 0.026(3) 0.007(3) -0.008(3) 0.017(4) C42 0.025(4) 0.061(5) 0.037(4) 0.026(4) 0.001(3) 0.014(4) C43 0.031(4) 0.056(5) 0.037(4) 0.023(4) -0.004(3) 0.012(4) C44 0.026(4) 0.061(6) 0.064(6) 0.040(5) -0.003(4) 0.005(4) C45 0.030(4) 0.079(6) 0.041(5) 0.028(5) 0.000(4) 0.014(4) C46 0.033(4) 0.072(6) 0.051(5) 0.026(5) 0.005(4) 0.010(4) C47 0.029(4) 0.053(5) 0.044(5) 0.025(4) 0.003(4) 0.016(4) C48 0.037(4) 0.048(5) 0.037(4) 0.010(4) 0.001(4) 0.015(4) C49 0.033(4) 0.052(5) 0.042(5) 0.018(4) 0.006(4) 0.014(4) C50 0.037(4) 0.044(5) 0.042(5) 0.013(4) -0.002(4) 0.009(4) C51 0.052(5) 0.043(5) 0.058(6) 0.022(4) 0.016(4) 0.026(4) C52 0.055(6) 0.066(6) 0.051(5) 0.031(5) 0.008(4) 0.030(5) C53 0.057(6) 0.067(6) 0.038(5) 0.016(4) 0.007(4) 0.025(5) C54 0.043(5) 0.049(5) 0.034(4) 0.013(4) 0.002(4) 0.012(4) C55 0.071(6) 0.054(5) 0.032(4) 0.009(4) 0.007(4) 0.039(5) C56 0.068(6) 0.069(6) 0.036(5) 0.027(4) -0.001(4) 0.028(5) C57 0.104(9) 0.095(8) 0.052(6) 0.033(6) 0.024(6) 0.067(7) C58 0.123(11) 0.096(9) 0.030(5) 0.007(6) 0.001(6) 0.069(8) C59 0.093(9) 0.093(9) 0.052(7) 0.018(6) -0.004(6) 0.025(7) C60 0.070(7) 0.077(7) 0.047(6) 0.010(5) -0.002(5) 0.032(6) C61 0.051(6) 0.059(6) 0.043(5) 0.006(4) -0.006(4) 0.018(5) C62 0.045(5) 0.061(6) 0.055(6) 0.018(5) -0.009(5) 0.014(5) C63 0.063(7) 0.080(7) 0.068(7) 0.031(6) -0.014(6) 0.003(6) C64 0.044(6) 0.096(8) 0.114(10) 0.064(8) -0.003(7) 0.009(6) C65 0.058(6) 0.073(7) 0.071(7) 0.047(5) 0.016(5) 0.033(5) C66 0.047(5) 0.041(4) 0.043(5) 0.018(4) -0.002(4) 0.022(4) C67 0.051(5) 0.044(5) 0.040(4) 0.016(4) 0.001(4) 0.029(4) C68 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C69 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C70 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C71 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C72 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C73 0.059(3) 0.117(4) 0.093(3) 0.050(3) 0.008(3) 0.003(3) C74 0.048(5) 0.061(5) 0.038(5) 0.018(4) 0.016(4) 0.024(5) C75 0.039(5) 0.086(7) 0.053(5) 0.029(5) 0.009(4) 0.034(5) C76 0.052(5) 0.054(5) 0.039(5) 0.016(4) 0.005(4) 0.023(5) C77 0.066(6) 0.075(7) 0.047(5) 0.029(5) 0.015(5) 0.035(6) C78 0.073(7) 0.094(8) 0.062(6) 0.018(6) 0.009(5) 0.057(6) C79 0.080(8) 0.065(7) 0.089(8) 0.022(6) 0.015(7) 0.049(6) C80 0.121(10) 0.073(7) 0.042(5) 0.007(5) 0.004(6) 0.064(8) C81 0.116(10) 0.060(7) 0.078(8) -0.008(6) -0.006(7) 0.031(7) C82 0.073(7) 0.060(6) 0.056(6) 0.002(5) -0.002(5) 0.011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C26 2.005(7) . ? Ir1 C13 2.010(6) . ? Ir1 N1 2.039(5) . ? Ir1 N2 2.050(5) . ? Ir1 O3 2.087(5) . ? Ir1 O4 2.130(4) . ? F1 C10 1.367(7) . ? F2 C12 1.358(7) . ? F3 C23 1.358(8) . ? F4 C25 1.366(7) . ? O1 C7 1.351(8) . ? O1 C6 1.379(9) . ? O2 C20 1.351(8) . ? O2 C19 1.386(9) . ? O3 C33 1.270(7) . ? O4 C35 1.271(7) . ? N1 C7 1.300(8) . ? N1 C1 1.390(8) . ? N2 C20 1.306(8) . ? N2 C14 1.410(8) . ? C1 C2 1.358(9) . ? C1 C6 1.395(9) . ? C2 C3 1.371(10) . ? C2 H2A 0.9500 . ? C3 C4 1.431(11) . ? C3 H3A 0.9500 . ? C4 C5 1.368(11) . ? C4 H4A 0.9500 . ? C5 C6 1.382(10) . ? C5 H5A 0.9500 . ? C7 C8 1.422(9) . ? C8 C9 1.407(9) . ? C8 C13 1.425(9) . ? C9 C10 1.364(10) . ? C9 H9A 0.9500 . ? C10 C11 1.370(10) . ? C11 C12 1.394(8) . ? C11 H11A 0.9500 . ? C12 C13 1.383(9) . ? C14 C15 1.370(10) . ? C14 C19 1.382(9) . ? C15 C16 1.383(10) . ? C15 H15A 0.9500 . ? C16 C17 1.413(11) . ? C16 H16A 0.9500 . ? C17 C18 1.370(11) . ? C17 H17A 0.9500 . ? C18 C19 1.388(10) . ? C18 H18A 0.9500 . ? C20 C21 1.435(10) . ? C21 C22 1.383(9) . ? C21 C26 1.419(9) . ? C22 C23 1.364(10) . ? C22 H22A 0.9500 . ? C23 C24 1.387(10) . ? C24 C25 1.376(9) . ? C24 H24A 0.9500 . ? C25 C26 1.397(10) . ? C27 C32 1.381(9) . ? C27 C28 1.380(10) . ? C27 H27A 0.9500 . ? C28 C29 1.370(11) . ? C28 H28A 0.9500 . ? C29 C30 1.379(11) . ? C29 H29A 0.9500 . ? C30 C31 1.383(10) . ? C30 H30A 0.9500 . ? C31 C32 1.390(9) . ? C31 H31A 0.9500 . ? C32 C33 1.502(9) . ? C33 C34 1.392(9) . ? C34 C35 1.397(9) . ? C34 H34A 0.9500 . ? C35 C36 1.509(9) . ? C36 C41 1.359(10) . ? C36 C37 1.425(10) . ? C37 C38 1.387(9) . ? C37 H37A 0.9500 . ? C38 C39 1.359(10) . ? C38 H38A 0.9500 . ? C39 C40 1.341(11) . ? C39 H39A 0.9500 . ? C40 C41 1.387(11) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? Ir2 C67 1.998(9) . ? Ir2 N3 2.022(6) . ? Ir2 C54 2.034(8) . ? Ir2 N4 2.028(6) . ? Ir2 O7 2.078(6) . ? Ir2 O8 2.097(5) . ? Ir2' N4 1.609(7) . ? Ir2' O7 1.668(7) . ? Ir2' O8 1.830(6) . ? Ir2' C74 2.255(9) . ? Ir2' C76 2.318(8) . ? Ir2' C55 2.451(9) . ? Ir2' C75 2.498(8) . ? F5 C51 1.379(8) . ? F6 C53 1.364(9) . ? F7 C64 1.371(11) . ? F8 C66 1.357(9) . ? O5 C48 1.367(9) . ? O5 C47 1.388(8) . ? O6 C61 1.366(10) . ? O6 C60 1.416(12) . ? O7 C74 1.238(9) . ? O8 C76 1.273(9) . ? N3 C48 1.297(9) . ? N3 C42 1.414(9) . ? N4 C61 1.316(11) . ? N4 C55 1.379(10) . ? C42 C47 1.352(10) . ? C42 C43 1.432(10) . ? C43 C44 1.398(10) . ? C43 H43A 0.9500 . ? C44 C45 1.338(11) . ? C44 H44A 0.9500 . ? C45 C46 1.395(11) . ? C45 H45A 0.9500 . ? C46 C47 1.404(10) . ? C46 H46A 0.9500 . ? C48 C49 1.427(10) . ? C49 C50 1.404(10) . ? C49 C54 1.408(10) . ? C50 C51 1.333(11) . ? C50 H50A 0.9500 . ? C51 C52 1.366(11) . ? C52 C53 1.394(11) . ? C52 H52A 0.9500 . ? C53 C54 1.380(11) . ? C55 C60 1.389(13) . ? C55 C56 1.387(12) . ? C56 C57 1.358(12) . ? C56 H56A 0.9500 . ? C57 C58 1.369(15) . ? C57 H57A 0.9500 . ? C58 C59 1.332(16) . ? C58 H58A 0.9500 . ? C59 C60 1.350(13) . ? C59 H59A 0.9500 . ? C61 C62 1.434(12) . ? C62 C63 1.390(13) . ? C62 C67 1.379(11) . ? C63 C64 1.366(14) . ? C63 H63A 0.9500 . ? C64 C65 1.368(14) . ? C65 C66 1.401(12) . ? C65 H65A 0.9500 . ? C66 C67 1.385(11) . ? C68 C69 1.356(14) . ? C68 C73 1.367(14) . ? C68 H68A 0.9500 . ? C69 C70 1.339(15) . ? C69 H69A 0.9500 . ? C70 C71 1.386(14) . ? C70 H70A 0.9500 . ? C71 C72 1.419(14) . ? C71 H71A 0.9500 . ? C72 C73 1.352(15) . ? C72 H72A 0.9500 . ? C73 C74 1.510(13) . ? C74 C75 1.413(12) . ? C75 C76 1.400(12) . ? C75 H75A 0.9500 . ? C76 C77 1.492(12) . ? C77 C82 1.348(13) . ? C77 C78 1.389(12) . ? C78 C79 1.363(13) . ? C78 H78A 0.9500 . ? C79 C80 1.425(15) . ? C79 H79A 0.9500 . ? C80 C81 1.346(14) . ? C80 H80A 0.9500 . ? C81 C82 1.398(13) . ? C81 H81A 0.9500 . ? C82 H82A 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 C26 Ir1 C13 92.2(2) . . ? C26 Ir1 N1 97.9(2) . . ? C13 Ir1 N1 79.5(2) . . ? C26 Ir1 N2 79.4(2) . . ? C13 Ir1 N2 100.4(2) . . ? N1 Ir1 N2 177.3(2) . . ? C26 Ir1 O3 173.9(2) . . ? C13 Ir1 O3 88.0(2) . . ? N1 Ir1 O3 88.10(19) . . ? N2 Ir1 O3 94.6(2) . . ? C26 Ir1 O4 91.7(2) . . ? C13 Ir1 O4 174.0(2) . . ? N1 Ir1 O4 95.38(19) . . ? N2 Ir1 O4 84.83(18) . . ? O3 Ir1 O4 88.68(17) . . ? C7 O1 C6 103.7(5) . . ? C20 O2 C19 104.1(5) . . ? C33 O3 Ir1 126.2(4) . . ? C35 O4 Ir1 124.8(4) . . ? C7 N1 C1 107.0(6) . . ? C7 N1 Ir1 114.4(4) . . ? C1 N1 Ir1 138.5(4) . . ? C20 N2 C14 107.3(5) . . ? C20 N2 Ir1 112.9(4) . . ? C14 N2 Ir1 139.2(4) . . ? C2 C1 N1 134.6(6) . . ? C2 C1 C6 119.8(7) . . ? N1 C1 C6 105.5(6) . . ? C1 C2 C3 119.0(7) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C2 C3 C4 120.4(8) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 121.2(8) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C4 C5 C6 116.1(8) . . ? C4 C5 H5A 122.0 . . ? C6 C5 H5A 122.0 . . ? O1 C6 C5 127.1(7) . . ? O1 C6 C1 109.4(6) . . ? C5 C6 C1 123.4(7) . . ? N1 C7 O1 114.3(6) . . ? N1 C7 C8 119.6(6) . . ? O1 C7 C8 126.1(6) . . ? C9 C8 C13 124.0(6) . . ? C9 C8 C7 124.7(6) . . ? C13 C8 C7 111.3(6) . . ? C10 C9 C8 116.4(6) . . ? C10 C9 H9A 121.8 . . ? C8 C9 H9A 121.8 . . ? F1 C10 C9 118.4(7) . . ? F1 C10 C11 117.7(7) . . ? C9 C10 C11 123.8(6) . . ? C10 C11 C12 117.2(6) . . ? C10 C11 H11A 121.4 . . ? C12 C11 H11A 121.4 . . ? F2 C12 C13 119.3(5) . . ? F2 C12 C11 115.9(6) . . ? C13 C12 C11 124.7(6) . . ? C12 C13 C8 113.8(6) . . ? C12 C13 Ir1 131.2(5) . . ? C8 C13 Ir1 115.0(5) . . ? C15 C14 C19 120.9(7) . . ? C15 C14 N2 133.9(6) . . ? C19 C14 N2 105.0(6) . . ? C14 C15 C16 116.7(7) . . ? C14 C15 H15A 121.6 . . ? C16 C15 H15A 121.6 . . ? C15 C16 C17 122.2(8) . . ? C15 C16 H16A 118.9 . . ? C17 C16 H16A 118.9 . . ? C18 C17 C16 120.5(7) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C19 C18 C17 116.4(7) . . ? C19 C18 H18A 121.8 . . ? C17 C18 H18A 121.8 . . ? C18 C19 O2 126.9(7) . . ? C18 C19 C14 123.1(7) . . ? O2 C19 C14 110.0(6) . . ? N2 C20 O2 113.6(6) . . ? N2 C20 C21 120.6(6) . . ? O2 C20 C21 125.8(6) . . ? C22 C21 C26 125.7(7) . . ? C22 C21 C20 124.4(6) . . ? C26 C21 C20 109.9(6) . . ? C23 C22 C21 116.8(7) . . ? C23 C22 H22A 121.6 . . ? C21 C22 H22A 121.6 . . ? F3 C23 C22 119.3(6) . . ? F3 C23 C24 117.8(7) . . ? C22 C23 C24 122.8(7) . . ? C25 C24 C23 116.9(7) . . ? C25 C24 H24A 121.6 . . ? C23 C24 H24A 121.6 . . ? F4 C25 C24 115.3(6) . . ? F4 C25 C26 118.7(6) . . ? C24 C25 C26 125.9(6) . . ? C25 C26 C21 111.8(6) . . ? C25 C26 Ir1 132.2(5) . . ? C21 C26 Ir1 116.0(5) . . ? C32 C27 C28 121.0(7) . . ? C32 C27 H27A 119.5 . . ? C28 C27 H27A 119.5 . . ? C29 C28 C27 120.3(8) . . ? C29 C28 H28A 119.9 . . ? C27 C28 H28A 119.9 . . ? C30 C29 C28 120.0(7) . . ? C30 C29 H29A 120.0 . . ? C28 C29 H29A 120.0 . . ? C29 C30 C31 119.4(7) . . ? C29 C30 H30A 120.3 . . ? C31 C30 H30A 120.3 . . ? C30 C31 C32 121.3(7) . . ? C30 C31 H31A 119.4 . . ? C32 C31 H31A 119.4 . . ? C27 C32 C31 118.0(7) . . ? C27 C32 C33 123.0(6) . . ? C31 C32 C33 119.0(6) . . ? O3 C33 C34 125.8(6) . . ? O3 C33 C32 113.4(6) . . ? C34 C33 C32 120.7(6) . . ? C35 C34 C33 128.1(6) . . ? C35 C34 H34A 115.9 . . ? C33 C34 H34A 115.9 . . ? O4 C35 C34 126.0(6) . . ? O4 C35 C36 114.2(6) . . ? C34 C35 C36 119.9(6) . . ? C41 C36 C37 116.8(6) . . ? C41 C36 C35 121.6(6) . . ? C37 C36 C35 121.6(6) . . ? C38 C37 C36 119.9(7) . . ? C38 C37 H37A 120.1 . . ? C36 C37 H37A 120.1 . . ? C39 C38 C37 120.3(7) . . ? C39 C38 H38A 119.8 . . ? C37 C38 H38A 119.8 . . ? C38 C39 C40 120.7(7) . . ? C38 C39 H39A 119.7 . . ? C40 C39 H39A 119.7 . . ? C39 C40 C41 120.0(8) . . ? C39 C40 H40A 120.0 . . ? C41 C40 H40A 120.0 . . ? C40 C41 C36 122.3(7) . . ? C40 C41 H41A 118.9 . . ? C36 C41 H41A 118.9 . . ? C67 Ir2 N3 99.6(3) . . ? C67 Ir2 C54 93.5(3) . . ? N3 Ir2 C54 79.0(3) . . ? C67 Ir2 N4 79.3(3) . . ? N3 Ir2 N4 176.9(3) . . ? C54 Ir2 N4 98.1(3) . . ? C67 Ir2 O7 175.4(3) . . ? N3 Ir2 O7 84.5(2) . . ? C54 Ir2 O7 89.1(3) . . ? N4 Ir2 O7 96.6(3) . . ? C67 Ir2 O8 88.6(2) . . ? N3 Ir2 O8 98.0(2) . . ? C54 Ir2 O8 176.6(3) . . ? N4 Ir2 O8 84.9(2) . . ? O7 Ir2 O8 89.0(2) . . ? N4 Ir2' O7 138.6(4) . . ? N4 Ir2' O8 108.0(4) . . ? O7 Ir2' O8 113.4(3) . . ? N4 Ir2' C74 145.4(4) . . ? O7 Ir2' C74 32.7(3) . . ? O8 Ir2' C74 93.3(3) . . ? N4 Ir2' C76 119.5(4) . . ? O7 Ir2' C76 95.6(3) . . ? O8 Ir2' C76 33.2(3) . . ? C74 Ir2' C76 66.6(3) . . ? N4 Ir2' C55 31.9(3) . . ? O7 Ir2' C55 116.6(3) . . ? O8 Ir2' C55 121.5(3) . . ? C74 Ir2' C55 113.5(3) . . ? C76 Ir2' C55 113.2(3) . . ? N4 Ir2' C75 136.3(3) . . ? O7 Ir2' C75 65.8(3) . . ? O8 Ir2' C75 64.5(3) . . ? C74 Ir2' C75 34.1(3) . . ? C76 Ir2' C75 33.5(3) . . ? C55 Ir2' C75 112.2(3) . . ? C48 O5 C47 104.3(6) . . ? C61 O6 C60 104.3(7) . . ? C74 O7 Ir2' 100.7(6) . . ? C74 O7 Ir2 126.3(6) . . ? Ir2' O7 Ir2 34.50(15) . . ? C76 O8 Ir2' 95.0(5) . . ? C76 O8 Ir2 124.5(5) . . ? Ir2' O8 Ir2 34.05(12) . . ? C48 N3 C42 104.7(6) . . ? C48 N3 Ir2 115.1(5) . . ? C42 N3 Ir2 139.9(5) . . ? C61 N4 C55 106.7(7) . . ? C61 N4 Ir2' 138.1(7) . . ? C55 N4 Ir2' 109.9(7) . . ? C61 N4 Ir2 113.5(6) . . ? C55 N4 Ir2 139.8(7) . . ? Ir2' N4 Ir2 35.47(16) . . ? C47 C42 N3 108.6(7) . . ? C47 C42 C43 121.1(7) . . ? N3 C42 C43 130.3(7) . . ? C44 C43 C42 112.7(7) . . ? C44 C43 H43A 123.6 . . ? C42 C43 H43A 123.6 . . ? C45 C44 C43 124.5(8) . . ? C45 C44 H44A 117.7 . . ? C43 C44 H44A 117.7 . . ? C44 C45 C46 124.2(8) . . ? C44 C45 H45A 117.9 . . ? C46 C45 H45A 117.9 . . ? C45 C46 C47 111.7(8) . . ? C45 C46 H46A 124.2 . . ? C47 C46 H46A 124.2 . . ? C42 C47 O5 108.2(6) . . ? C42 C47 C46 125.8(7) . . ? O5 C47 C46 126.0(7) . . ? N3 C48 O5 114.2(7) . . ? N3 C48 C49 119.8(7) . . ? O5 C48 C49 126.0(7) . . ? C50 C49 C54 123.6(7) . . ? C50 C49 C48 125.4(7) . . ? C54 C49 C48 110.8(7) . . ? C51 C50 C49 117.5(7) . . ? C51 C50 H50A 121.2 . . ? C49 C50 H50A 121.2 . . ? C50 C51 C52 123.4(7) . . ? C50 C51 F5 120.0(8) . . ? C52 C51 F5 116.6(7) . . ? C51 C52 C53 117.4(8) . . ? C51 C52 H52A 121.3 . . ? C53 C52 H52A 121.3 . . ? F6 C53 C54 120.0(7) . . ? F6 C53 C52 115.8(8) . . ? C54 C53 C52 124.2(8) . . ? C53 C54 C49 113.7(7) . . ? C53 C54 Ir2 131.1(6) . . ? C49 C54 Ir2 115.2(6) . . ? C60 C55 C56 117.5(8) . . ? C60 C55 N4 108.4(9) . . ? C56 C55 N4 134.1(9) . . ? C60 C55 Ir2' 142.6(8) . . ? C56 C55 Ir2' 97.6(6) . . ? N4 C55 Ir2' 38.1(4) . . ? C57 C56 C55 117.9(10) . . ? C57 C56 H56A 121.1 . . ? C55 C56 H56A 121.1 . . ? C58 C57 C56 121.4(11) . . ? C58 C57 H57A 119.3 . . ? C56 C57 H57A 119.3 . . ? C59 C58 C57 122.8(10) . . ? C59 C58 H58A 118.6 . . ? C57 C58 H58A 118.6 . . ? C58 C59 C60 115.8(11) . . ? C58 C59 H59A 122.1 . . ? C60 C59 H59A 122.1 . . ? C59 C60 C55 124.6(11) . . ? C59 C60 O6 128.2(10) . . ? C55 C60 O6 107.2(8) . . ? N4 C61 O6 113.5(8) . . ? N4 C61 C62 119.5(8) . . ? O6 C61 C62 126.7(9) . . ? C63 C62 C67 126.7(9) . . ? C63 C62 C61 122.7(9) . . ? C67 C62 C61 110.6(8) . . ? C64 C63 C62 116.3(10) . . ? C64 C63 H63A 121.9 . . ? C62 C63 H63A 121.9 . . ? F7 C64 C63 118.7(11) . . ? F7 C64 C65 118.6(11) . . ? C63 C64 C65 122.7(10) . . ? C64 C65 C66 116.7(9) . . ? C64 C65 H65A 121.6 . . ? C66 C65 H65A 121.6 . . ? F8 C66 C65 114.2(8) . . ? F8 C66 C67 120.3(8) . . ? C65 C66 C67 125.5(8) . . ? C62 C67 C66 112.1(8) . . ? C62 C67 Ir2 117.0(6) . . ? C66 C67 Ir2 131.0(6) . . ? C69 C68 C73 123.2(12) . . ? C69 C68 H68A 118.4 . . ? C73 C68 H68A 118.4 . . ? C70 C69 C68 120.2(12) . . ? C70 C69 H69A 119.9 . . ? C68 C69 H69A 119.9 . . ? C69 C70 C71 118.6(11) . . ? C69 C70 H70A 120.7 . . ? C71 C70 H70A 120.7 . . ? C70 C71 C72 120.2(12) . . ? C70 C71 H71A 119.9 . . ? C72 C71 H71A 119.9 . . ? C73 C72 C71 119.2(11) . . ? C73 C72 H72A 120.4 . . ? C71 C72 H72A 120.4 . . ? C72 C73 C68 118.1(11) . . ? C72 C73 C74 117.5(10) . . ? C68 C73 C74 124.4(11) . . ? O7 C74 C75 126.4(8) . . ? O7 C74 C73 116.2(9) . . ? C75 C74 C73 117.4(8) . . ? O7 C74 Ir2' 46.6(4) . . ? C75 C74 Ir2' 82.4(5) . . ? C73 C74 Ir2' 154.0(7) . . ? C76 C75 C74 126.6(7) . . ? C76 C75 Ir2' 66.2(5) . . ? C74 C75 Ir2' 63.5(5) . . ? C76 C75 H75A 116.7 . . ? C74 C75 H75A 116.7 . . ? Ir2' C75 H75A 161.2 . . ? O8 C76 C75 125.4(8) . . ? O8 C76 C77 114.2(8) . . ? C75 C76 C77 120.4(8) . . ? O8 C76 Ir2' 51.8(4) . . ? C75 C76 Ir2' 80.3(5) . . ? C77 C76 Ir2' 148.6(7) . . ? C82 C77 C78 118.1(10) . . ? C82 C77 C76 119.9(8) . . ? C78 C77 C76 121.9(10) . . ? C79 C78 C77 121.6(12) . . ? C79 C78 H78A 119.2 . . ? C77 C78 H78A 119.2 . . ? C78 C79 C80 118.2(10) . . ? C78 C79 H79A 120.9 . . ? C80 C79 H79A 120.9 . . ? C81 C80 C79 121.1(10) . . ? C81 C80 H80A 119.5 . . ? C79 C80 H80A 119.5 . . ? C80 C81 C82 118.0(12) . . ? C80 C81 H81A 121.0 . . ? C82 C81 H81A 121.0 . . ? C77 C82 C81 123.0(11) . . ? C77 C82 H82A 118.5 . . ? C81 C82 H82A 118.5 . . ? _diffrn_measured_fraction_theta_max 0.838 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.243 _refine_diff_density_min -7.492 _refine_diff_density_rms 0.170 # Attachment '- 5.CIF' data_5 _database_code_depnum_ccdc_archive 'CCDC 778559' #TrackingRef '- 5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C33 H15 Br2 F4 Ir N2 O3' _chemical_formula_sum 'C33 H15 Br2 F4 Ir N2 O3' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 110(2) _chemical_formula_weight 915.49 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' Br Br -0.2901 2.4595 '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 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5053(3) _cell_length_b 12.1682(3) _cell_length_c 16.3047(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.514(2) _cell_angle_gamma 90.00 _cell_volume 2809.47(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8671 _cell_measurement_theta_min 2.8735 _cell_measurement_theta_max 29.1200 _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 7.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.38349 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13799 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.20 _reflns_number_total 6500 _reflns_number_gt 5122 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.0204P)^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_number_reflns 6500 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0494 _refine_ls_wR_factor_gt 0.0484 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Ir Ir 0.400420(9) -0.093020(12) -0.785610(8) 0.00718(4) Uani 1 1 d . . . Br1 Br 0.34373(3) -0.42849(3) -1.05429(2) 0.01774(9) Uani 1 1 d . . . Br2 Br 0.09384(3) -0.06480(3) -1.08576(2) 0.02169(10) Uani 1 1 d . . . F1 F 0.43206(16) 0.31921(18) -1.00600(13) 0.0225(5) Uani 1 1 d . . . F2 F 0.25779(14) 0.13614(19) -0.83876(13) 0.0191(5) Uani 1 1 d . . . F3 F 0.54729(16) 0.19823(19) -0.46693(12) 0.0235(6) Uani 1 1 d . . . F4 F 0.62701(14) -0.02008(19) -0.67681(12) 0.0181(5) Uani 1 1 d . . . O1 O 0.63140(17) -0.0293(2) -0.88633(15) 0.0149(6) Uani 1 1 d . . . O2 O 0.22988(17) 0.0323(2) -0.63595(14) 0.0124(6) Uani 1 1 d . . . O3 O 0.40764(18) -0.3202(2) -0.70619(15) 0.0168(5) Uani 1 1 d . . . N1 N 0.52226(19) -0.1085(3) -0.82866(16) 0.0100(7) Uani 1 1 d . . . N2 N 0.2856(2) -0.0543(3) -0.73530(17) 0.0104(7) Uani 1 1 d . . . C1 C 0.5992(2) -0.1800(3) -0.8181(2) 0.0103(8) Uani 1 1 d . . . C2 C 0.6161(3) -0.2834(3) -0.7806(2) 0.0154(8) Uani 1 1 d . . . H2A H 0.5700 -0.3201 -0.7573 0.018 Uiso 1 1 calc R . . C3 C 0.7036(3) -0.3296(4) -0.7791(2) 0.0172(9) Uani 1 1 d . . . H3A H 0.7177 -0.4000 -0.7545 0.021 Uiso 1 1 calc R . . C4 C 0.7717(3) -0.2753(4) -0.8128(2) 0.0228(10) Uani 1 1 d . . . H4A H 0.8316 -0.3090 -0.8086 0.027 Uiso 1 1 calc R . . C5 C 0.7547(3) -0.1735(4) -0.8525(2) 0.0200(9) Uani 1 1 d . . . H5A H 0.8000 -0.1372 -0.8771 0.024 Uiso 1 1 calc R . . C6 C 0.6664(3) -0.1298(3) -0.8530(2) 0.0150(8) Uani 1 1 d . . . C7 C 0.5440(2) -0.0233(3) -0.8687(2) 0.0104(8) Uani 1 1 d . . . C8 C 0.4808(3) 0.0679(3) -0.8878(2) 0.0119(8) Uani 1 1 d . . . C9 C 0.4956(3) 0.1559(3) -0.9391(2) 0.0148(8) Uani 1 1 d . . . H9A H 0.5510 0.1621 -0.9610 0.018 Uiso 1 1 calc R . . C10 C 0.4236(3) 0.2334(3) -0.9554(2) 0.0178(9) Uani 1 1 d . . . C11 C 0.3438(3) 0.2270(3) -0.9224(2) 0.0153(8) Uani 1 1 d . . . H11A H 0.2953 0.2809 -0.9349 0.018 Uiso 1 1 calc R . . C12 C 0.3372(3) 0.1394(3) -0.8705(2) 0.0127(8) Uani 1 1 d . . . C13 C 0.4017(2) 0.0539(3) -0.8518(2) 0.0099(8) Uani 1 1 d . . . C14 C 0.1897(2) -0.0828(3) -0.7466(2) 0.0111(8) Uani 1 1 d . . . C15 C 0.1310(3) -0.1526(3) -0.8012(2) 0.0138(8) Uani 1 1 d . . . H15A H 0.1525 -0.1919 -0.8438 0.017 Uiso 1 1 calc R . . C16 C 0.0384(3) -0.1625(3) -0.7905(2) 0.0167(9) Uani 1 1 d . . . H16A H -0.0039 -0.2096 -0.8272 0.020 Uiso 1 1 calc R . . C17 C 0.0054(3) -0.1058(3) -0.7281(2) 0.0176(9) Uani 1 1 d . . . H17A H -0.0584 -0.1147 -0.7237 0.021 Uiso 1 1 calc R . . C18 C 0.0650(3) -0.0359(3) -0.6718(2) 0.0139(8) Uani 1 1 d . . . H18A H 0.0440 0.0028 -0.6286 0.017 Uiso 1 1 calc R . . C19 C 0.1562(3) -0.0274(3) -0.6835(2) 0.0120(8) Uani 1 1 d . . . C20 C 0.3059(3) 0.0103(3) -0.6695(2) 0.0111(8) Uani 1 1 d . . . C21 C 0.3993(3) 0.0453(3) -0.6354(2) 0.0112(8) Uani 1 1 d . . . C22 C 0.4240(3) 0.1142(3) -0.5641(2) 0.0141(8) Uani 1 1 d . . . H22A H 0.3778 0.1454 -0.5378 0.017 Uiso 1 1 calc R . . C23 C 0.5184(3) 0.1333(3) -0.5354(2) 0.0161(9) Uani 1 1 d . . . C24 C 0.5875(3) 0.0878(3) -0.5718(2) 0.0159(8) Uani 1 1 d . . . H24A H 0.6528 0.1006 -0.5495 0.019 Uiso 1 1 calc R . . C25 C 0.5571(3) 0.0229(3) -0.6421(2) 0.0133(8) Uani 1 1 d . . . C26 C 0.4646(3) -0.0017(3) -0.6769(2) 0.0110(8) Uani 1 1 d . . . C27 C 0.3249(2) -0.1595(3) -0.9005(2) 0.0085(7) Uani 1 1 d . . . C28 C 0.3530(2) -0.2570(3) -0.9342(2) 0.0118(8) Uani 1 1 d . . . H28A H 0.4059 -0.2969 -0.9040 0.014 Uiso 1 1 calc R . . C29 C 0.3034(3) -0.2952(3) -1.0116(2) 0.0125(8) Uani 1 1 d . . . C30 C 0.2263(2) -0.2410(3) -1.0594(2) 0.0134(8) Uani 1 1 d . . . H30A H 0.1935 -0.2681 -1.1124 0.016 Uiso 1 1 calc R . . C31 C 0.1999(2) -0.1449(3) -1.0253(2) 0.0135(8) Uani 1 1 d . . . C32 C 0.2467(2) -0.1029(3) -0.9479(2) 0.0120(8) Uani 1 1 d . . . H32A H 0.2260 -0.0363 -0.9274 0.014 Uiso 1 1 calc R . . C33 C 0.4061(3) -0.2343(3) -0.7342(2) 0.0168(5) 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 Ir 0.00599(6) 0.00730(7) 0.00858(6) -0.00059(6) 0.00228(5) -0.00044(7) Br1 0.01828(19) 0.0159(2) 0.01880(18) -0.00771(16) 0.00350(15) 0.00124(18) Br2 0.0179(2) 0.0185(2) 0.0230(2) -0.00087(16) -0.00801(16) 0.00417(18) F1 0.0342(14) 0.0126(13) 0.0222(12) 0.0081(10) 0.0093(10) 0.0004(11) F2 0.0134(11) 0.0189(13) 0.0269(12) 0.0030(10) 0.0087(10) 0.0062(10) F3 0.0322(14) 0.0192(14) 0.0169(11) -0.0113(10) 0.0009(10) -0.0059(12) F4 0.0091(10) 0.0226(14) 0.0221(12) -0.0063(10) 0.0025(9) -0.0008(10) O1 0.0105(13) 0.0134(15) 0.0233(14) -0.0025(12) 0.0089(11) -0.0019(12) O2 0.0108(13) 0.0118(15) 0.0166(13) -0.0021(11) 0.0076(11) 0.0018(12) O3 0.0163(11) 0.0131(12) 0.0224(12) 0.0044(9) 0.0075(9) 0.0001(11) N1 0.0068(14) 0.0116(18) 0.0107(14) -0.0005(13) -0.0001(12) -0.0005(14) N2 0.0107(15) 0.0085(16) 0.0133(15) -0.0007(12) 0.0057(12) 0.0012(14) C1 0.0099(18) 0.011(2) 0.0097(17) -0.0013(15) 0.0027(14) 0.0003(17) C2 0.019(2) 0.012(2) 0.0147(18) 0.0002(16) 0.0034(16) 0.0043(18) C3 0.0115(19) 0.020(2) 0.020(2) -0.0005(17) 0.0021(16) 0.0041(19) C4 0.016(2) 0.026(3) 0.026(2) -0.0041(19) 0.0055(18) 0.007(2) C5 0.011(2) 0.023(2) 0.026(2) -0.0061(18) 0.0052(17) 0.0005(19) C6 0.0113(19) 0.016(2) 0.0179(19) -0.0041(16) 0.0034(16) -0.0018(18) C7 0.0048(17) 0.018(2) 0.0095(17) -0.0030(15) 0.0034(14) -0.0022(17) C8 0.0136(18) 0.011(2) 0.0105(17) -0.0014(14) 0.0004(14) 0.0026(17) C9 0.0152(19) 0.011(2) 0.0183(19) 0.0020(16) 0.0042(16) -0.0013(18) C10 0.030(2) 0.008(2) 0.0144(19) -0.0004(16) 0.0031(17) -0.0029(19) C11 0.017(2) 0.009(2) 0.0191(19) -0.0033(16) 0.0034(16) -0.0020(18) C12 0.0117(19) 0.009(2) 0.0165(19) -0.0027(15) 0.0023(16) 0.0000(17) C13 0.0095(18) 0.0063(18) 0.0127(17) -0.0001(14) 0.0000(14) 0.0002(16) C14 0.0092(17) 0.009(2) 0.0161(17) 0.0045(15) 0.0045(14) 0.0019(17) C15 0.0136(19) 0.013(2) 0.0157(19) -0.0012(16) 0.0043(16) -0.0052(18) C16 0.0135(19) 0.019(2) 0.017(2) 0.0022(17) 0.0025(16) 0.0007(19) C17 0.0131(18) 0.022(2) 0.0176(18) 0.0075(18) 0.0038(15) 0.0022(19) C18 0.0105(18) 0.012(2) 0.019(2) 0.0043(16) 0.0045(16) 0.0012(17) C19 0.0126(19) 0.008(2) 0.0152(19) -0.0007(15) 0.0035(15) -0.0009(17) C20 0.0154(19) 0.0053(19) 0.0138(18) 0.0031(15) 0.0055(15) 0.0025(17) C21 0.0122(18) 0.0084(19) 0.0143(18) 0.0027(15) 0.0055(15) -0.0007(17) C22 0.022(2) 0.008(2) 0.0136(18) -0.0008(15) 0.0049(16) -0.0030(17) C23 0.024(2) 0.013(2) 0.0102(18) -0.0025(15) 0.0023(16) -0.0057(19) C24 0.0187(19) 0.012(2) 0.0151(17) -0.0018(17) 0.0006(15) -0.0059(19) C25 0.0131(19) 0.013(2) 0.0145(19) 0.0016(15) 0.0051(16) -0.0004(18) C26 0.0173(19) 0.009(2) 0.0078(17) 0.0031(14) 0.0048(15) 0.0012(17) C27 0.0083(17) 0.010(2) 0.0085(17) 0.0013(14) 0.0047(14) -0.0012(16) C28 0.0121(18) 0.013(2) 0.0115(16) -0.0004(15) 0.0064(15) -0.0009(17) C29 0.0120(18) 0.009(2) 0.0189(19) -0.0021(16) 0.0077(15) 0.0001(17) C30 0.0126(18) 0.015(2) 0.0125(18) -0.0005(15) 0.0021(15) -0.0045(18) C31 0.0094(18) 0.015(2) 0.0145(18) 0.0042(16) -0.0013(15) 0.0030(17) C32 0.0115(17) 0.013(2) 0.0122(17) -0.0007(16) 0.0041(14) -0.0043(18) C33 0.0163(11) 0.0131(12) 0.0224(12) 0.0044(9) 0.0075(9) 0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir C33 1.906(4) . ? Ir N1 2.047(3) . ? Ir N2 2.065(3) . ? Ir C13 2.090(4) . ? Ir C27 2.114(3) . ? Ir C26 2.128(3) . ? Br1 C29 1.906(4) . ? Br2 C31 1.906(4) . ? F1 C10 1.352(4) . ? F2 C12 1.362(4) . ? F3 C23 1.357(4) . ? F4 C25 1.368(4) . ? O1 C7 1.361(4) . ? O1 C6 1.389(5) . ? O2 C20 1.360(4) . ? O2 C19 1.383(4) . ? O3 C33 1.140(4) . ? N1 C7 1.299(4) . ? N1 C1 1.396(4) . ? N2 C20 1.311(4) . ? N2 C14 1.406(4) . ? C1 C6 1.375(5) . ? C1 C2 1.396(5) . ? C2 C3 1.383(5) . ? C2 H2A 0.9500 . ? C3 C4 1.396(5) . ? C3 H3A 0.9500 . ? C4 C5 1.394(6) . ? C4 H4A 0.9500 . ? C5 C6 1.385(5) . ? C5 H5A 0.9500 . ? C7 C8 1.431(5) . ? C8 C9 1.404(5) . ? C8 C13 1.407(5) . ? C9 C10 1.390(5) . ? C9 H9A 0.9500 . ? C10 C11 1.381(5) . ? C11 C12 1.377(5) . ? C11 H11A 0.9500 . ? C12 C13 1.389(5) . ? C14 C15 1.382(5) . ? C14 C19 1.401(5) . ? C15 C16 1.396(5) . ? C15 H15A 0.9500 . ? C16 C17 1.397(5) . ? C16 H16A 0.9500 . ? C17 C18 1.403(5) . ? C17 H17A 0.9500 . ? C18 C19 1.382(5) . ? C18 H18A 0.9500 . ? C20 C21 1.414(5) . ? C21 C26 1.399(5) . ? C21 C22 1.416(5) . ? C22 C23 1.367(5) . ? C22 H22A 0.9500 . ? C23 C24 1.387(5) . ? C24 C25 1.384(5) . ? C24 H24A 0.9500 . ? C25 C26 1.372(5) . ? C27 C28 1.405(5) . ? C27 C32 1.407(5) . ? C28 C29 1.391(5) . ? C28 H28A 0.9500 . ? C29 C30 1.385(5) . ? C30 C31 1.384(5) . ? C30 H30A 0.9500 . ? C31 C32 1.393(5) . ? C32 H32A 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 C33 Ir N1 96.30(14) . . ? C33 Ir N2 89.58(14) . . ? N1 Ir N2 171.23(12) . . ? C33 Ir C13 173.60(15) . . ? N1 Ir C13 78.26(13) . . ? N2 Ir C13 96.22(13) . . ? C33 Ir C27 90.51(15) . . ? N1 Ir C27 88.91(12) . . ? N2 Ir C27 97.56(12) . . ? C13 Ir C27 86.05(13) . . ? C33 Ir C26 97.77(15) . . ? N1 Ir C26 94.56(13) . . ? N2 Ir C26 78.16(13) . . ? C13 Ir C26 86.10(13) . . ? C27 Ir C26 170.60(14) . . ? C7 O1 C6 104.1(3) . . ? C20 O2 C19 105.5(3) . . ? C7 N1 C1 106.5(3) . . ? C7 N1 Ir 114.9(2) . . ? C1 N1 Ir 137.8(2) . . ? C20 N2 C14 107.2(3) . . ? C20 N2 Ir 113.8(2) . . ? C14 N2 Ir 138.8(2) . . ? C6 C1 N1 106.9(3) . . ? C6 C1 C2 120.5(4) . . ? N1 C1 C2 132.5(3) . . ? C3 C2 C1 116.6(4) . . ? C3 C2 H2A 121.7 . . ? C1 C2 H2A 121.7 . . ? C2 C3 C4 121.7(4) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 122.3(4) . . ? C5 C4 H4A 118.9 . . ? C3 C4 H4A 118.9 . . ? C6 C5 C4 114.4(4) . . ? C6 C5 H5A 122.8 . . ? C4 C5 H5A 122.8 . . ? C1 C6 C5 124.4(4) . . ? C1 C6 O1 108.7(3) . . ? C5 C6 O1 126.9(4) . . ? N1 C7 O1 113.7(3) . . ? N1 C7 C8 121.0(3) . . ? O1 C7 C8 125.3(3) . . ? C9 C8 C13 125.9(3) . . ? C9 C8 C7 123.2(3) . . ? C13 C8 C7 110.9(3) . . ? C10 C9 C8 115.2(3) . . ? C10 C9 H9A 122.4 . . ? C8 C9 H9A 122.4 . . ? F1 C10 C11 118.4(4) . . ? F1 C10 C9 118.5(3) . . ? C11 C10 C9 123.1(4) . . ? C12 C11 C10 117.3(4) . . ? C12 C11 H11A 121.3 . . ? C10 C11 H11A 121.3 . . ? F2 C12 C11 115.7(3) . . ? F2 C12 C13 118.7(3) . . ? C11 C12 C13 125.6(4) . . ? C12 C13 C8 112.8(3) . . ? C12 C13 Ir 132.3(3) . . ? C8 C13 Ir 114.8(3) . . ? C15 C14 C19 120.3(3) . . ? C15 C14 N2 133.6(3) . . ? C19 C14 N2 106.0(3) . . ? C14 C15 C16 116.6(3) . . ? C14 C15 H15A 121.7 . . ? C16 C15 H15A 121.7 . . ? C15 C16 C17 122.5(4) . . ? C15 C16 H16A 118.7 . . ? C17 C16 H16A 118.7 . . ? C16 C17 C18 121.2(4) . . ? C16 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? C19 C18 C17 115.3(4) . . ? C19 C18 H18A 122.4 . . ? C17 C18 H18A 122.4 . . ? C18 C19 O2 127.5(3) . . ? C18 C19 C14 124.1(3) . . ? O2 C19 C14 108.4(3) . . ? N2 C20 O2 112.9(3) . . ? N2 C20 C21 122.0(3) . . ? O2 C20 C21 125.0(3) . . ? C26 C21 C20 112.2(3) . . ? C26 C21 C22 124.2(3) . . ? C20 C21 C22 123.5(3) . . ? C23 C22 C21 116.0(3) . . ? C23 C22 H22A 122.0 . . ? C21 C22 H22A 122.0 . . ? F3 C23 C22 119.3(3) . . ? F3 C23 C24 117.4(3) . . ? C22 C23 C24 123.3(3) . . ? C25 C24 C23 116.8(3) . . ? C25 C24 H24A 121.6 . . ? C23 C24 H24A 121.6 . . ? F4 C25 C26 119.5(3) . . ? F4 C25 C24 115.4(3) . . ? C26 C25 C24 125.1(4) . . ? C25 C26 C21 114.5(3) . . ? C25 C26 Ir 132.1(3) . . ? C21 C26 Ir 113.4(3) . . ? C28 C27 C32 117.8(3) . . ? C28 C27 Ir 122.1(3) . . ? C32 C27 Ir 120.1(3) . . ? C29 C28 C27 120.0(3) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C30 C29 C28 123.2(3) . . ? C30 C29 Br1 118.3(3) . . ? C28 C29 Br1 118.5(3) . . ? C31 C30 C29 115.9(3) . . ? C31 C30 H30A 122.1 . . ? C29 C30 H30A 122.1 . . ? C30 C31 C32 123.4(3) . . ? C30 C31 Br2 119.1(3) . . ? C32 C31 Br2 117.5(3) . . ? C31 C32 C27 119.7(3) . . ? C31 C32 H32A 120.2 . . ? C27 C32 H32A 120.2 . . ? O3 C33 Ir 177.5(4) . . ? _diffrn_measured_fraction_theta_max 0.855 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.270 _refine_diff_density_min -1.108 _refine_diff_density_rms 0.138