# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jose Fuentes' 'Matthew Clarke' 'Marcia B. France' 'A Slawin' _publ_contact_author_name 'Jose Fuentes' _publ_contact_author_email JAF14@ST-ANDREWS.AC.UK _publ_section_title ; Iridium complexes of chiral diamines containing carbon and nitrogen stereocentres: synthesis, structure and evaluation as transfer hydrogenation catalysts ; # Attachment 'Complex 4.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 708595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C34 H49 Cl Ir N2,B F4,2(C H Cl3)' _chemical_formula_sum 'C36 H51 B Cl7 F4 Ir N2' _chemical_formula_weight 1038.95 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.5451(7) _cell_length_b 17.3548(10) _cell_length_c 18.4163(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4329.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 16971 _cell_measurement_theta_min 1.8662 _cell_measurement_theta_max 28.6183 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2072 _exptl_absorpt_coefficient_mu 3.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7678 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28479 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.36 _reflns_number_total 7939 _reflns_number_gt 7663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The NH hydrogen atoms were located from a difference map and refined isotropically subject to a distance constraint. ; _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^)+(0.0192P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.011(4) _refine_ls_number_reflns 7939 _refine_ls_number_parameters 474 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0570 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.007 _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 0.296685(12) 0.645809(9) 0.072499(9) 0.01477(6) Uani 1 1 d . . . Cl1 Cl 0.42691(8) 0.71811(7) 0.01391(6) 0.0221(3) Uani 1 1 d . . . N1 N 0.3714(2) 0.6472(2) 0.17732(17) 0.0145(7) Uani 1 1 d D . . H1N H 0.320(2) 0.630(2) 0.2107(16) 0.014(11) Uiso 1 1 d D . . C1 C 0.3960(3) 0.7291(2) 0.1986(2) 0.0167(10) Uani 1 1 d . . . H1A H 0.4485 0.7495 0.1656 0.020 Uiso 1 1 calc R . . C2 C 0.3007(4) 0.7754(2) 0.1872(2) 0.0163(9) Uani 1 1 d . . . H2A H 0.2494 0.7558 0.2216 0.020 Uiso 1 1 calc R . . N2 N 0.2648(3) 0.7632(2) 0.1108(2) 0.0189(9) Uani 1 1 d D . . H2N H 0.312(3) 0.788(3) 0.078(2) 0.043(15) Uiso 1 1 d D . . C3 C 0.3208(3) 0.8597(2) 0.2045(2) 0.0210(10) Uani 1 1 d . . . H3A H 0.2600 0.8901 0.1960 0.025 Uiso 1 1 calc R . . H3B H 0.3726 0.8794 0.1714 0.025 Uiso 1 1 calc R . . C4 C 0.3543(4) 0.8706(2) 0.2834(2) 0.0243(11) Uani 1 1 d . . . H4A H 0.3732 0.9259 0.2896 0.029 Uiso 1 1 calc R . . C5 C 0.4468(4) 0.8215(3) 0.2990(3) 0.0261(12) Uani 1 1 d . . . H5A H 0.4570 0.8221 0.3527 0.031 Uiso 1 1 calc R . . C6 C 0.4296(4) 0.7373(2) 0.2770(3) 0.0209(10) Uani 1 1 d . . . H6A H 0.4916 0.7080 0.2839 0.025 Uiso 1 1 calc R . . H6B H 0.3790 0.7145 0.3094 0.025 Uiso 1 1 calc R . . C7 C 0.4526(3) 0.5880(3) 0.1869(2) 0.0192(10) Uani 1 1 d . . . H7A H 0.4284 0.5403 0.1623 0.023 Uiso 1 1 calc R . . C8 C 0.4682(3) 0.5660(2) 0.2663(2) 0.0193(10) Uani 1 1 d . . . C9 C 0.3893(4) 0.5514(2) 0.3127(3) 0.0224(11) Uani 1 1 d . . . H9A H 0.3238 0.5546 0.2944 0.027 Uiso 1 1 calc R . . C10 C 0.4037(4) 0.5327(3) 0.3842(3) 0.0280(12) Uani 1 1 d . . . H10A H 0.3484 0.5250 0.4151 0.034 Uiso 1 1 calc R . . C11 C 0.4982(4) 0.5249(3) 0.4115(3) 0.0318(13) Uani 1 1 d . . . H11A H 0.5081 0.5117 0.4611 0.038 Uiso 1 1 calc R . . C12 C 0.5777(4) 0.5363(3) 0.3667(3) 0.0300(12) Uani 1 1 d . . . H12A H 0.6428 0.5294 0.3849 0.036 Uiso 1 1 calc R . . C13 C 0.5633(4) 0.5579(3) 0.2947(3) 0.0255(11) Uani 1 1 d . . . H13A H 0.6189 0.5672 0.2645 0.031 Uiso 1 1 calc R . . C14 C 0.5467(4) 0.6113(3) 0.1466(3) 0.0318(12) Uani 1 1 d . . . H14A H 0.5974 0.5717 0.1538 0.048 Uiso 1 1 calc R . . H14B H 0.5706 0.6607 0.1655 0.048 Uiso 1 1 calc R . . H14C H 0.5323 0.6164 0.0947 0.048 Uiso 1 1 calc R . . C15 C 0.1630(3) 0.7978(3) 0.0952(2) 0.0180(10) Uani 1 1 d . . . H15A H 0.1348 0.7676 0.0538 0.022 Uiso 1 1 calc R . . C16 C 0.1730(3) 0.8808(2) 0.0682(3) 0.0188(10) Uani 1 1 d . . . C17 C 0.1196(3) 0.9415(3) 0.0996(3) 0.0222(11) Uani 1 1 d . . . H17A H 0.0768 0.9315 0.1394 0.027 Uiso 1 1 calc R . . C18 C 0.1289(3) 1.0156(3) 0.0731(3) 0.0284(11) Uani 1 1 d . . . H18A H 0.0920 1.0563 0.0944 0.034 Uiso 1 1 calc R . . C19 C 0.1916(4) 1.0309(3) 0.0158(3) 0.0322(12) Uani 1 1 d . . . H19A H 0.1994 1.0822 -0.0011 0.039 Uiso 1 1 calc R . . C20 C 0.2432(4) 0.9713(3) -0.0171(3) 0.0302(12) Uani 1 1 d . . . H20A H 0.2850 0.9816 -0.0574 0.036 Uiso 1 1 calc R . . C21 C 0.2336(4) 0.8966(3) 0.0088(3) 0.0263(12) Uani 1 1 d . . . H21A H 0.2687 0.8559 -0.0140 0.032 Uiso 1 1 calc R . . C22 C 0.0925(3) 0.7868(3) 0.1590(2) 0.0223(11) Uani 1 1 d . . . H22A H 0.0904 0.7322 0.1724 0.033 Uiso 1 1 calc R . . H22B H 0.0262 0.8039 0.1450 0.033 Uiso 1 1 calc R . . H22C H 0.1156 0.8172 0.2005 0.033 Uiso 1 1 calc R . . C23 C 0.2701(4) 0.8537(3) 0.3362(3) 0.0384(13) Uani 1 1 d . . . H23A H 0.2131 0.8859 0.3240 0.058 Uiso 1 1 calc R . . H23B H 0.2917 0.8651 0.3859 0.058 Uiso 1 1 calc R . . H23C H 0.2516 0.7992 0.3326 0.058 Uiso 1 1 calc R . . C24 C 0.5387(4) 0.8535(3) 0.2653(3) 0.0337(12) Uani 1 1 d . . . H24A H 0.5948 0.8203 0.2774 0.050 Uiso 1 1 calc R . . H24B H 0.5507 0.9055 0.2840 0.050 Uiso 1 1 calc R . . H24C H 0.5307 0.8555 0.2124 0.050 Uiso 1 1 calc R . . C25 C 0.2250(3) 0.5338(2) 0.0852(2) 0.0185(10) Uani 1 1 d . . . C26 C 0.1551(3) 0.5884(2) 0.0577(2) 0.0186(10) Uani 1 1 d . . . C27 C 0.1915(3) 0.6164(2) -0.0113(2) 0.0187(10) Uani 1 1 d . . . C28 C 0.2820(3) 0.5771(2) -0.0261(2) 0.0189(10) Uani 1 1 d . . . C29 C 0.3052(4) 0.5274(2) 0.0330(2) 0.0195(10) Uani 1 1 d . . . C30 C 0.2139(4) 0.4858(3) 0.1519(2) 0.0267(11) Uani 1 1 d . . . H30A H 0.1879 0.4350 0.1386 0.040 Uiso 1 1 calc R . . H30B H 0.1682 0.5111 0.1855 0.040 Uiso 1 1 calc R . . H30C H 0.2784 0.4796 0.1753 0.040 Uiso 1 1 calc R . . C31 C 0.0553(3) 0.6045(3) 0.0904(3) 0.0240(11) Uani 1 1 d . . . H31A H 0.0088 0.5641 0.0757 0.036 Uiso 1 1 calc R . . H31B H 0.0313 0.6546 0.0732 0.036 Uiso 1 1 calc R . . H31C H 0.0607 0.6053 0.1434 0.036 Uiso 1 1 calc R . . C32 C 0.1376(3) 0.6677(3) -0.0650(3) 0.0250(11) Uani 1 1 d . . . H32A H 0.1123 0.6363 -0.1051 0.038 Uiso 1 1 calc R . . H32B H 0.1832 0.7066 -0.0840 0.038 Uiso 1 1 calc R . . H32C H 0.0824 0.6933 -0.0405 0.038 Uiso 1 1 calc R . . C33 C 0.3411(4) 0.5841(3) -0.0941(2) 0.0267(11) Uani 1 1 d . . . H33A H 0.3149 0.5487 -0.1308 0.040 Uiso 1 1 calc R . . H33B H 0.4101 0.5711 -0.0839 0.040 Uiso 1 1 calc R . . H33C H 0.3371 0.6371 -0.1122 0.040 Uiso 1 1 calc R . . C34 C 0.3886(4) 0.4719(3) 0.0352(3) 0.0260(11) Uani 1 1 d . . . H34A H 0.3764 0.4302 0.0005 0.039 Uiso 1 1 calc R . . H34B H 0.3944 0.4503 0.0842 0.039 Uiso 1 1 calc R . . H34C H 0.4500 0.4984 0.0224 0.039 Uiso 1 1 calc R . . B1 B 0.1133(4) 0.6261(3) 0.3161(3) 0.0291(14) Uani 1 1 d . . . F1 F 0.0526(2) 0.69037(18) 0.31897(17) 0.0448(8) Uani 1 1 d . . . F2 F 0.1646(3) 0.6179(2) 0.38014(16) 0.0599(11) Uani 1 1 d . . . F3 F 0.18006(18) 0.63505(16) 0.25939(13) 0.0309(7) Uani 1 1 d . . . F4 F 0.0566(2) 0.5619(2) 0.3023(2) 0.0549(10) Uani 1 1 d . . . C35 C 0.5123(7) 0.7157(4) 0.5414(4) 0.077(2) Uani 1 1 d . . . H35A H 0.5229 0.7585 0.5770 0.092 Uiso 1 1 calc R . . Cl2 Cl 0.3958(2) 0.72822(19) 0.50113(13) 0.1264(11) Uani 1 1 d . . . Cl3 Cl 0.51675(15) 0.63011(11) 0.58769(10) 0.0769(6) Uani 1 1 d . . . Cl4 Cl 0.6058(2) 0.72128(13) 0.47446(13) 0.0978(7) Uani 1 1 d . . . C36 C 0.8515(4) 0.6475(3) 0.2420(3) 0.0409(13) Uani 1 1 d . . . H36A H 0.9222 0.6518 0.2571 0.049 Uiso 1 1 calc R . . Cl5 Cl 0.77694(13) 0.68466(9) 0.31281(9) 0.0563(4) Uani 1 1 d . . . Cl6 Cl 0.83584(11) 0.69901(9) 0.16191(8) 0.0471(4) Uani 1 1 d . . . Cl7 Cl 0.82486(11) 0.54932(8) 0.22643(8) 0.0467(4) 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 Ir1 0.01554(8) 0.01530(8) 0.01349(9) -0.00204(8) 0.00021(7) -0.00166(7) Cl1 0.0218(6) 0.0268(6) 0.0177(6) 0.0001(5) 0.0037(5) -0.0073(5) N1 0.0151(18) 0.0124(17) 0.0159(18) 0.0001(18) -0.0003(14) -0.0019(17) C1 0.023(2) 0.013(2) 0.014(2) 0.0005(19) -0.0014(19) -0.0013(19) C2 0.021(2) 0.021(2) 0.007(2) 0.0019(18) -0.002(2) 0.004(2) N2 0.027(2) 0.0148(19) 0.015(2) -0.0007(16) -0.0036(17) 0.0001(16) C3 0.030(3) 0.011(2) 0.022(2) -0.004(2) -0.0032(19) 0.000(2) C4 0.041(3) 0.012(2) 0.020(2) -0.003(2) -0.005(2) -0.004(2) C5 0.037(3) 0.019(2) 0.021(3) -0.006(2) -0.005(2) -0.008(2) C6 0.028(3) 0.018(2) 0.017(3) 0.004(2) -0.005(2) -0.005(2) C7 0.021(2) 0.019(2) 0.018(3) -0.001(2) -0.0043(19) 0.0041(19) C8 0.027(3) 0.008(2) 0.023(3) -0.0024(19) -0.006(2) 0.0014(19) C9 0.019(2) 0.014(2) 0.034(3) 0.003(2) -0.004(2) 0.000(2) C10 0.040(3) 0.020(2) 0.024(3) 0.006(2) 0.002(2) -0.006(2) C11 0.051(4) 0.021(3) 0.023(3) 0.005(2) -0.010(3) -0.006(2) C12 0.033(3) 0.024(3) 0.033(3) 0.001(2) -0.017(3) 0.003(2) C13 0.029(3) 0.022(2) 0.026(3) -0.001(2) -0.004(2) 0.002(2) C14 0.021(3) 0.048(3) 0.026(3) 0.004(3) 0.005(2) 0.007(2) C15 0.020(2) 0.020(2) 0.014(2) -0.0034(19) -0.0022(18) 0.0065(19) C16 0.023(2) 0.017(2) 0.016(2) 0.004(2) -0.010(2) -0.0014(17) C17 0.026(3) 0.016(2) 0.026(3) 0.001(2) -0.005(2) -0.001(2) C18 0.033(3) 0.028(3) 0.025(3) -0.005(3) -0.009(3) 0.000(2) C19 0.047(3) 0.022(3) 0.028(3) 0.004(2) -0.015(3) -0.001(3) C20 0.038(3) 0.036(3) 0.016(3) 0.006(2) -0.004(2) -0.004(2) C21 0.035(3) 0.024(3) 0.020(3) 0.002(2) -0.006(2) 0.000(2) C22 0.023(3) 0.022(2) 0.022(3) 0.000(2) -0.002(2) 0.001(2) C23 0.054(4) 0.041(3) 0.021(3) -0.008(3) -0.004(2) 0.002(3) C24 0.035(3) 0.034(3) 0.032(3) 0.000(3) -0.008(2) -0.013(3) C25 0.024(3) 0.015(2) 0.017(2) -0.0089(19) 0.0013(19) -0.0083(18) C26 0.017(2) 0.016(2) 0.023(3) -0.009(2) 0.003(2) -0.0049(18) C27 0.017(2) 0.020(2) 0.020(2) -0.0059(19) -0.006(2) 0.0000(19) C28 0.022(3) 0.020(2) 0.015(2) -0.0086(19) -0.003(2) -0.003(2) C29 0.022(2) 0.018(2) 0.018(2) -0.0079(19) -0.005(2) 0.001(2) C30 0.034(3) 0.022(2) 0.024(3) 0.003(2) 0.001(2) -0.010(2) C31 0.017(2) 0.024(2) 0.031(3) -0.008(2) 0.005(2) -0.0058(19) C32 0.023(2) 0.028(3) 0.023(3) -0.002(2) -0.004(2) 0.0036(19) C33 0.028(3) 0.033(3) 0.019(3) -0.006(2) 0.005(2) 0.003(2) C34 0.026(3) 0.026(3) 0.026(3) -0.008(2) -0.001(2) 0.006(2) B1 0.030(3) 0.036(4) 0.021(3) 0.004(3) 0.005(3) 0.004(3) F1 0.043(2) 0.0464(19) 0.045(2) -0.0094(16) 0.0038(16) 0.0164(16) F2 0.059(2) 0.095(3) 0.0259(18) 0.0195(18) -0.0047(15) 0.009(2) F3 0.0263(15) 0.0404(16) 0.0261(14) 0.0109(13) 0.0092(11) 0.0051(13) F4 0.043(2) 0.044(2) 0.078(3) 0.0122(19) 0.0071(18) -0.0195(17) C35 0.129(7) 0.058(5) 0.043(4) -0.006(4) -0.010(5) 0.010(5) Cl2 0.136(2) 0.176(3) 0.0681(15) -0.0028(16) -0.0096(15) 0.082(2) Cl3 0.0882(13) 0.0699(12) 0.0726(13) 0.0007(10) -0.0238(10) -0.0095(10) Cl4 0.127(2) 0.0814(14) 0.0845(15) -0.0172(13) 0.0130(15) -0.0287(15) C36 0.036(3) 0.042(3) 0.045(3) 0.006(3) 0.006(2) -0.003(3) Cl5 0.0673(12) 0.0467(8) 0.0549(10) -0.0051(7) 0.0135(8) -0.0024(8) Cl6 0.0496(9) 0.0482(9) 0.0435(9) 0.0104(7) -0.0090(7) -0.0055(7) Cl7 0.0485(9) 0.0402(8) 0.0512(9) 0.0044(7) 0.0038(7) -0.0002(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 C27 2.161(4) . ? Ir1 C26 2.179(4) . ? Ir1 N1 2.179(3) . ? Ir1 C28 2.182(4) . ? Ir1 C29 2.182(4) . ? Ir1 C25 2.185(4) . ? Ir1 N2 2.199(4) . ? Ir1 Cl1 2.4187(11) . ? N1 C1 1.512(5) . ? N1 C7 1.515(5) . ? N1 H1N 0.978(5) . ? C1 C6 1.522(6) . ? C1 C2 1.534(6) . ? C1 H1A 1.0000 . ? C2 N2 1.504(5) . ? C2 C3 1.521(6) . ? C2 H2A 1.0000 . ? N2 C15 1.532(5) . ? N2 H2N 0.978(5) . ? C3 C4 1.535(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C23 1.527(7) . ? C4 C5 1.541(7) . ? C4 H4A 1.0000 . ? C5 C24 1.497(7) . ? C5 C6 1.534(6) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.525(6) . ? C7 C14 1.529(7) . ? C7 H7A 1.0000 . ? C8 C9 1.392(6) . ? C8 C13 1.398(7) . ? C9 C10 1.370(6) . ? C9 H9A 0.9500 . ? C10 C11 1.383(7) . ? C10 H10A 0.9500 . ? C11 C12 1.371(7) . ? C11 H11A 0.9500 . ? C12 C13 1.391(7) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C22 1.527(6) . ? C15 C16 1.529(6) . ? C15 H15A 1.0000 . ? C16 C21 1.394(6) . ? C16 C17 1.402(6) . ? C17 C18 1.383(6) . ? C17 H17A 0.9500 . ? C18 C19 1.379(7) . ? C18 H18A 0.9500 . ? C19 C20 1.388(7) . ? C19 H19A 0.9500 . ? C20 C21 1.387(7) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.432(6) . ? C25 C29 1.455(6) . ? C25 C30 1.492(6) . ? C26 C27 1.447(6) . ? C26 C31 1.506(6) . ? C27 C28 1.429(6) . ? C27 C32 1.518(6) . ? C28 C29 1.424(6) . ? C28 C33 1.491(6) . ? C29 C34 1.485(6) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? B1 F4 1.377(7) . ? B1 F2 1.376(7) . ? B1 F1 1.387(6) . ? B1 F3 1.389(6) . ? C35 Cl3 1.713(7) . ? C35 Cl2 1.757(9) . ? C35 Cl4 1.771(9) . ? C35 H35A 1.0000 . ? C36 Cl6 1.738(6) . ? C36 Cl7 1.764(6) . ? C36 Cl5 1.772(6) . ? C36 H36A 1.0000 . ? 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 C27 Ir1 C26 38.96(17) . . ? C27 Ir1 N1 160.22(14) . . ? C26 Ir1 N1 121.64(15) . . ? C27 Ir1 C28 38.41(16) . . ? C26 Ir1 C28 64.23(16) . . ? N1 Ir1 C28 141.79(15) . . ? C27 Ir1 C29 64.84(16) . . ? C26 Ir1 C29 64.81(17) . . ? N1 Ir1 C29 106.32(15) . . ? C28 Ir1 C29 38.08(16) . . ? C27 Ir1 C25 64.76(16) . . ? C26 Ir1 C25 38.31(16) . . ? N1 Ir1 C25 96.97(15) . . ? C28 Ir1 C25 64.03(16) . . ? C29 Ir1 C25 38.92(16) . . ? C27 Ir1 N2 108.55(14) . . ? C26 Ir1 N2 106.92(15) . . ? N1 Ir1 N2 78.27(13) . . ? C28 Ir1 N2 139.07(15) . . ? C29 Ir1 N2 171.71(16) . . ? C25 Ir1 N2 134.63(14) . . ? C27 Ir1 Cl1 106.53(12) . . ? C26 Ir1 Cl1 145.44(12) . . ? N1 Ir1 Cl1 92.92(9) . . ? C28 Ir1 Cl1 88.80(12) . . ? C29 Ir1 Cl1 107.52(13) . . ? C25 Ir1 Cl1 146.43(11) . . ? N2 Ir1 Cl1 78.79(10) . . ? C1 N1 C7 116.5(3) . . ? C1 N1 Ir1 110.0(2) . . ? C7 N1 Ir1 115.7(2) . . ? C1 N1 H1N 106(2) . . ? C7 N1 H1N 104(2) . . ? Ir1 N1 H1N 103(2) . . ? N1 C1 C6 113.5(3) . . ? N1 C1 C2 105.8(3) . . ? C6 C1 C2 109.4(4) . . ? N1 C1 H1A 109.3 . . ? C6 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N2 C2 C3 112.9(3) . . ? N2 C2 C1 109.1(3) . . ? C3 C2 C1 109.0(4) . . ? N2 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C2 N2 C15 114.4(3) . . ? C2 N2 Ir1 111.5(3) . . ? C15 N2 Ir1 118.7(3) . . ? C2 N2 H2N 108(3) . . ? C15 N2 H2N 108(3) . . ? Ir1 N2 H2N 95(3) . . ? C2 C3 C4 111.7(4) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C23 C4 C3 111.0(4) . . ? C23 C4 C5 112.5(4) . . ? C3 C4 C5 110.4(4) . . ? C23 C4 H4A 107.6 . . ? C3 C4 H4A 107.6 . . ? C5 C4 H4A 107.6 . . ? C24 C5 C6 111.7(4) . . ? C24 C5 C4 113.2(4) . . ? C6 C5 C4 110.7(4) . . ? C24 C5 H5A 106.9 . . ? C6 C5 H5A 106.9 . . ? C4 C5 H5A 106.9 . . ? C1 C6 C5 112.6(4) . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N1 C7 C8 112.5(3) . . ? N1 C7 C14 111.7(4) . . ? C8 C7 C14 114.6(4) . . ? N1 C7 H7A 105.7 . . ? C8 C7 H7A 105.7 . . ? C14 C7 H7A 105.7 . . ? C9 C8 C13 117.3(4) . . ? C9 C8 C7 121.8(4) . . ? C13 C8 C7 120.8(4) . . ? C10 C9 C8 121.6(5) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 120.4(5) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 119.6(5) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C11 C12 C13 120.1(5) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C8 120.9(5) . . ? C12 C13 H13A 119.5 . . ? C8 C13 H13A 119.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C22 C15 C16 115.1(4) . . ? C22 C15 N2 111.7(4) . . ? C16 C15 N2 110.5(3) . . ? C22 C15 H15A 106.3 . . ? C16 C15 H15A 106.3 . . ? N2 C15 H15A 106.3 . . ? C21 C16 C17 118.7(4) . . ? C21 C16 C15 119.5(4) . . ? C17 C16 C15 121.8(4) . . ? C18 C17 C16 120.4(5) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C19 C18 C17 120.3(5) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C18 C19 C20 120.1(4) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C21 C20 C19 119.9(5) . . ? C21 C20 H20A 120.1 . . ? C19 C20 H20A 120.1 . . ? C20 C21 C16 120.6(5) . . ? C20 C21 H21A 119.7 . . ? C16 C21 H21A 119.7 . . ? C15 C22 H22A 109.5 . . ? C15 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C15 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C4 C23 H23A 109.5 . . ? C4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 C24 H24A 109.5 . . ? C5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C29 108.1(4) . . ? C26 C25 C30 126.5(4) . . ? C29 C25 C30 125.2(4) . . ? C26 C25 Ir1 70.6(2) . . ? C29 C25 Ir1 70.4(2) . . ? C30 C25 Ir1 129.0(3) . . ? C25 C26 C27 107.9(4) . . ? C25 C26 C31 125.1(4) . . ? C27 C26 C31 126.5(4) . . ? C25 C26 Ir1 71.1(2) . . ? C27 C26 Ir1 69.9(2) . . ? C31 C26 Ir1 130.9(3) . . ? C28 C27 C26 107.4(4) . . ? C28 C27 C32 124.7(4) . . ? C26 C27 C32 127.2(4) . . ? C28 C27 Ir1 71.6(2) . . ? C26 C27 Ir1 71.2(2) . . ? C32 C27 Ir1 130.1(3) . . ? C29 C28 C27 109.5(4) . . ? C29 C28 C33 124.9(4) . . ? C27 C28 C33 125.6(4) . . ? C29 C28 Ir1 71.0(2) . . ? C27 C28 Ir1 70.0(2) . . ? C33 C28 Ir1 127.2(3) . . ? C28 C29 C25 107.1(4) . . ? C28 C29 C34 125.6(4) . . ? C25 C29 C34 126.8(4) . . ? C28 C29 Ir1 70.9(2) . . ? C25 C29 Ir1 70.7(2) . . ? C34 C29 Ir1 130.0(3) . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? F4 B1 F2 110.9(5) . . ? F4 B1 F1 109.1(5) . . ? F2 B1 F1 110.4(4) . . ? F4 B1 F3 108.4(4) . . ? F2 B1 F3 109.1(4) . . ? F1 B1 F3 108.9(4) . . ? Cl3 C35 Cl2 110.4(5) . . ? Cl3 C35 Cl4 111.6(5) . . ? Cl2 C35 Cl4 109.9(4) . . ? Cl3 C35 H35A 108.2 . . ? Cl2 C35 H35A 108.2 . . ? Cl4 C35 H35A 108.2 . . ? Cl6 C36 Cl7 109.5(3) . . ? Cl6 C36 Cl5 111.6(3) . . ? Cl7 C36 Cl5 110.8(3) . . ? Cl6 C36 H36A 108.3 . . ? Cl7 C36 H36A 108.3 . . ? Cl5 C36 H36A 108.3 . . ? 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 C27 Ir1 N1 C1 -136.4(4) . . . . ? C26 Ir1 N1 C1 -126.6(3) . . . . ? C28 Ir1 N1 C1 145.8(3) . . . . ? C29 Ir1 N1 C1 163.3(3) . . . . ? C25 Ir1 N1 C1 -158.1(3) . . . . ? N2 Ir1 N1 C1 -23.8(3) . . . . ? Cl1 Ir1 N1 C1 54.1(3) . . . . ? C27 Ir1 N1 C7 89.0(5) . . . . ? C26 Ir1 N1 C7 98.8(3) . . . . ? C28 Ir1 N1 C7 11.2(4) . . . . ? C29 Ir1 N1 C7 28.7(3) . . . . ? C25 Ir1 N1 C7 67.3(3) . . . . ? N2 Ir1 N1 C7 -158.5(3) . . . . ? Cl1 Ir1 N1 C7 -80.5(3) . . . . ? C7 N1 C1 C6 -57.3(5) . . . . ? Ir1 N1 C1 C6 168.6(3) . . . . ? C7 N1 C1 C2 -177.2(3) . . . . ? Ir1 N1 C1 C2 48.6(3) . . . . ? N1 C1 C2 N2 -54.0(4) . . . . ? C6 C1 C2 N2 -176.6(3) . . . . ? N1 C1 C2 C3 -177.6(3) . . . . ? C6 C1 C2 C3 59.8(4) . . . . ? C3 C2 N2 C15 -66.3(5) . . . . ? C1 C2 N2 C15 172.4(3) . . . . ? C3 C2 N2 Ir1 155.6(3) . . . . ? C1 C2 N2 Ir1 34.3(4) . . . . ? C27 Ir1 N2 C2 154.8(3) . . . . ? C26 Ir1 N2 C2 113.8(3) . . . . ? N1 Ir1 N2 C2 -5.9(3) . . . . ? C28 Ir1 N2 C2 -176.2(3) . . . . ? C25 Ir1 N2 C2 82.3(4) . . . . ? Cl1 Ir1 N2 C2 -101.3(3) . . . . ? C27 Ir1 N2 C15 18.7(3) . . . . ? C26 Ir1 N2 C15 -22.3(3) . . . . ? N1 Ir1 N2 C15 -142.1(3) . . . . ? C28 Ir1 N2 C15 47.7(4) . . . . ? C25 Ir1 N2 C15 -53.8(4) . . . . ? Cl1 Ir1 N2 C15 122.5(3) . . . . ? N2 C2 C3 C4 178.3(4) . . . . ? C1 C2 C3 C4 -60.4(5) . . . . ? C2 C3 C4 C23 -68.6(5) . . . . ? C2 C3 C4 C5 56.9(5) . . . . ? C23 C4 C5 C24 -161.5(4) . . . . ? C3 C4 C5 C24 73.9(5) . . . . ? C23 C4 C5 C6 72.2(5) . . . . ? C3 C4 C5 C6 -52.4(5) . . . . ? N1 C1 C6 C5 -175.8(4) . . . . ? C2 C1 C6 C5 -57.9(5) . . . . ? C24 C5 C6 C1 -72.9(5) . . . . ? C4 C5 C6 C1 54.3(5) . . . . ? C1 N1 C7 C8 75.0(5) . . . . ? Ir1 N1 C7 C8 -153.4(3) . . . . ? C1 N1 C7 C14 -55.5(5) . . . . ? Ir1 N1 C7 C14 76.1(4) . . . . ? N1 C7 C8 C9 44.0(6) . . . . ? C14 C7 C8 C9 173.0(4) . . . . ? N1 C7 C8 C13 -137.5(4) . . . . ? C14 C7 C8 C13 -8.5(6) . . . . ? C13 C8 C9 C10 2.4(7) . . . . ? C7 C8 C9 C10 -179.1(4) . . . . ? C8 C9 C10 C11 -2.5(7) . . . . ? C9 C10 C11 C12 0.2(7) . . . . ? C10 C11 C12 C13 2.0(7) . . . . ? C11 C12 C13 C8 -2.0(7) . . . . ? C9 C8 C13 C12 -0.2(7) . . . . ? C7 C8 C13 C12 -178.7(4) . . . . ? C2 N2 C15 C22 -39.6(5) . . . . ? Ir1 N2 C15 C22 95.4(4) . . . . ? C2 N2 C15 C16 89.9(4) . . . . ? Ir1 N2 C15 C16 -135.2(3) . . . . ? C22 C15 C16 C21 -178.3(4) . . . . ? N2 C15 C16 C21 54.1(5) . . . . ? C22 C15 C16 C17 -1.0(6) . . . . ? N2 C15 C16 C17 -128.6(4) . . . . ? C21 C16 C17 C18 -1.5(7) . . . . ? C15 C16 C17 C18 -178.8(4) . . . . ? C16 C17 C18 C19 -0.6(7) . . . . ? C17 C18 C19 C20 2.2(7) . . . . ? C18 C19 C20 C21 -1.7(7) . . . . ? C19 C20 C21 C16 -0.4(7) . . . . ? C17 C16 C21 C20 1.9(7) . . . . ? C15 C16 C21 C20 179.3(4) . . . . ? C27 Ir1 C25 C26 -37.8(2) . . . . ? N1 Ir1 C25 C26 134.2(2) . . . . ? C28 Ir1 C25 C26 -80.6(3) . . . . ? C29 Ir1 C25 C26 -118.4(4) . . . . ? N2 Ir1 C25 C26 53.9(3) . . . . ? Cl1 Ir1 C25 C26 -119.7(3) . . . . ? C27 Ir1 C25 C29 80.6(3) . . . . ? C26 Ir1 C25 C29 118.4(4) . . . . ? N1 Ir1 C25 C29 -107.4(2) . . . . ? C28 Ir1 C25 C29 37.8(2) . . . . ? N2 Ir1 C25 C29 172.2(2) . . . . ? Cl1 Ir1 C25 C29 -1.3(4) . . . . ? C27 Ir1 C25 C30 -159.5(5) . . . . ? C26 Ir1 C25 C30 -121.7(5) . . . . ? N1 Ir1 C25 C30 12.5(4) . . . . ? C28 Ir1 C25 C30 157.7(5) . . . . ? C29 Ir1 C25 C30 119.9(5) . . . . ? N2 Ir1 C25 C30 -67.9(5) . . . . ? Cl1 Ir1 C25 C30 118.6(4) . . . . ? C29 C25 C26 C27 -0.3(4) . . . . ? C30 C25 C26 C27 -174.8(4) . . . . ? Ir1 C25 C26 C27 60.5(3) . . . . ? C29 C25 C26 C31 172.0(4) . . . . ? C30 C25 C26 C31 -2.5(7) . . . . ? Ir1 C25 C26 C31 -127.3(4) . . . . ? C29 C25 C26 Ir1 -60.7(3) . . . . ? C30 C25 C26 Ir1 124.8(4) . . . . ? C27 Ir1 C26 C25 118.1(3) . . . . ? N1 Ir1 C26 C25 -56.6(3) . . . . ? C28 Ir1 C26 C25 80.0(3) . . . . ? C29 Ir1 C26 C25 37.7(2) . . . . ? N2 Ir1 C26 C25 -143.1(2) . . . . ? Cl1 Ir1 C26 C25 122.1(2) . . . . ? N1 Ir1 C26 C27 -174.8(2) . . . . ? C28 Ir1 C26 C27 -38.1(2) . . . . ? C29 Ir1 C26 C27 -80.5(3) . . . . ? C25 Ir1 C26 C27 -118.1(3) . . . . ? N2 Ir1 C26 C27 98.8(2) . . . . ? Cl1 Ir1 C26 C27 4.0(4) . . . . ? C27 Ir1 C26 C31 -121.4(5) . . . . ? N1 Ir1 C26 C31 63.9(5) . . . . ? C28 Ir1 C26 C31 -159.5(5) . . . . ? C29 Ir1 C26 C31 158.2(5) . . . . ? C25 Ir1 C26 C31 120.5(5) . . . . ? N2 Ir1 C26 C31 -22.6(5) . . . . ? Cl1 Ir1 C26 C31 -117.4(4) . . . . ? C25 C26 C27 C28 1.6(4) . . . . ? C31 C26 C27 C28 -170.5(4) . . . . ? Ir1 C26 C27 C28 62.8(3) . . . . ? C25 C26 C27 C32 172.2(4) . . . . ? C31 C26 C27 C32 0.1(7) . . . . ? Ir1 C26 C27 C32 -126.6(4) . . . . ? C25 C26 C27 Ir1 -61.2(3) . . . . ? C31 C26 C27 Ir1 126.6(4) . . . . ? C26 Ir1 C27 C28 -116.5(3) . . . . ? N1 Ir1 C27 C28 -103.3(5) . . . . ? C29 Ir1 C27 C28 -36.2(3) . . . . ? C25 Ir1 C27 C28 -79.4(3) . . . . ? N2 Ir1 C27 C28 149.3(2) . . . . ? Cl1 Ir1 C27 C28 65.8(2) . . . . ? N1 Ir1 C27 C26 13.2(6) . . . . ? C28 Ir1 C27 C26 116.5(3) . . . . ? C29 Ir1 C27 C26 80.4(3) . . . . ? C25 Ir1 C27 C26 37.2(2) . . . . ? N2 Ir1 C27 C26 -94.2(2) . . . . ? Cl1 Ir1 C27 C26 -177.6(2) . . . . ? C26 Ir1 C27 C32 123.3(5) . . . . ? N1 Ir1 C27 C32 136.5(4) . . . . ? C28 Ir1 C27 C32 -120.2(5) . . . . ? C29 Ir1 C27 C32 -156.4(5) . . . . ? C25 Ir1 C27 C32 160.4(5) . . . . ? N2 Ir1 C27 C32 29.1(4) . . . . ? Cl1 Ir1 C27 C32 -54.4(4) . . . . ? C26 C27 C28 C29 -2.3(5) . . . . ? C32 C27 C28 C29 -173.2(4) . . . . ? Ir1 C27 C28 C29 60.2(3) . . . . ? C26 C27 C28 C33 175.4(4) . . . . ? C32 C27 C28 C33 4.4(7) . . . . ? Ir1 C27 C28 C33 -122.1(4) . . . . ? C26 C27 C28 Ir1 -62.6(3) . . . . ? C32 C27 C28 Ir1 126.5(4) . . . . ? C27 Ir1 C28 C29 -120.0(4) . . . . ? C26 Ir1 C28 C29 -81.4(3) . . . . ? N1 Ir1 C28 C29 27.8(4) . . . . ? C25 Ir1 C28 C29 -38.6(3) . . . . ? N2 Ir1 C28 C29 -167.7(3) . . . . ? Cl1 Ir1 C28 C29 121.0(3) . . . . ? C26 Ir1 C28 C27 38.7(3) . . . . ? N1 Ir1 C28 C27 147.8(2) . . . . ? C29 Ir1 C28 C27 120.0(4) . . . . ? C25 Ir1 C28 C27 81.4(3) . . . . ? N2 Ir1 C28 C27 -47.7(4) . . . . ? Cl1 Ir1 C28 C27 -119.0(2) . . . . ? C27 Ir1 C28 C33 120.1(5) . . . . ? C26 Ir1 C28 C33 158.7(4) . . . . ? N1 Ir1 C28 C33 -92.1(4) . . . . ? C29 Ir1 C28 C33 -119.9(5) . . . . ? C25 Ir1 C28 C33 -158.5(4) . . . . ? N2 Ir1 C28 C33 72.4(5) . . . . ? Cl1 Ir1 C28 C33 1.1(4) . . . . ? C27 C28 C29 C25 2.1(5) . . . . ? C33 C28 C29 C25 -175.6(4) . . . . ? Ir1 C28 C29 C25 61.8(3) . . . . ? C27 C28 C29 C34 174.3(4) . . . . ? C33 C28 C29 C34 -3.4(7) . . . . ? Ir1 C28 C29 C34 -126.1(4) . . . . ? C27 C28 C29 Ir1 -59.7(3) . . . . ? C33 C28 C29 Ir1 122.6(4) . . . . ? C26 C25 C29 C28 -1.1(5) . . . . ? C30 C25 C29 C28 173.5(4) . . . . ? Ir1 C25 C29 C28 -62.0(3) . . . . ? C26 C25 C29 C34 -173.1(4) . . . . ? C30 C25 C29 C34 1.5(7) . . . . ? Ir1 C25 C29 C34 126.0(4) . . . . ? C26 C25 C29 Ir1 60.8(3) . . . . ? C30 C25 C29 Ir1 -124.6(4) . . . . ? C27 Ir1 C29 C28 36.5(3) . . . . ? C26 Ir1 C29 C28 79.7(3) . . . . ? N1 Ir1 C29 C28 -162.5(2) . . . . ? C25 Ir1 C29 C28 116.8(4) . . . . ? Cl1 Ir1 C29 C28 -64.0(3) . . . . ? C27 Ir1 C29 C25 -80.3(3) . . . . ? C26 Ir1 C29 C25 -37.1(3) . . . . ? N1 Ir1 C29 C25 80.7(3) . . . . ? C28 Ir1 C29 C25 -116.8(4) . . . . ? Cl1 Ir1 C29 C25 179.2(2) . . . . ? C27 Ir1 C29 C34 157.4(5) . . . . ? C26 Ir1 C29 C34 -159.4(5) . . . . ? N1 Ir1 C29 C34 -41.6(4) . . . . ? C28 Ir1 C29 C34 120.9(5) . . . . ? C25 Ir1 C29 C34 -122.3(5) . . . . ? Cl1 Ir1 C29 C34 56.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N F3 0.978(5) 2.093(18) 3.007(4) 155(3) . N2 H2N Cl1 0.978(5) 2.30(4) 2.936(4) 122(4) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.234 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.094