#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:32:39 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270488 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060996.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7060996 loop_ _publ_author_name 'Li, Rong-Jian' 'Wang, Yang' 'Jin, Yan' 'Deng, Wei' 'Liu, Zhen-Jiang' 'Yao, Zi-Jian' _publ_section_title ; NHC ligand-based half-sandwich iridium complexes: synthesis, structure and catalytic activity in acceptorless dehydrogenation and transfer hydrogenation ; _journal_issue 40 _journal_name_full 'New Journal of Chemistry' _journal_page_first 19002 _journal_page_last 19010 _journal_paper_doi 10.1039/D1NJ03824A _journal_volume 45 _journal_year 2021 _chemical_formula_sum 'C21 H23 Br0.3 Cl0.7 Ir N3' _chemical_formula_weight 558.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-06-30 deposited with the CCDC. 2021-09-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.794(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.9625(14) _cell_length_b 15.3150(13) _cell_length_c 8.0607(7) _cell_measurement_reflns_used 9903 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 56.86 _cell_measurement_theta_min 3.49 _cell_volume 1960.5(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34138 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_unetI/netI 0.0439 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 28794 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 57.033 _diffrn_reflns_theta_min 4.845 _exptl_absorpt_coefficient_mu 9.809 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_correction_T_min 0.521 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.892 _exptl_crystal_description needle _exptl_crystal_F_000 1074 _exptl_crystal_size_max 0.330 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.955 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.138 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 242 _refine_ls_number_reflns 4007 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0342 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+3.4360P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.0801 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3256 _reflns_number_total 4007 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03824a2.cif _cod_data_source_block ga_210507da_a _cod_depositor_comments 'Adding full bibliography for 7060996--7060997.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C21 H23 Br0.30 Cl0.70 Ir N3' _cod_database_code 7060996 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.140 _shelx_estimated_absorpt_t_max 0.757 _shelx_res_file ; ga_210507da_a.res created by SHELXL-2014/7 TITL ga_210507da_a.res in P2(1)/c CELL 1.34138 15.9625 15.3150 8.0607 90.000 95.794 90.000 ZERR 4.000 0.0014 0.0013 0.0007 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H Cl Ir N Br UNIT 84 92 3 4 12 1 L.S. 5 ACTA BOND $H FMAP 2 PLAN 5 EADP Cl1 Br1 EXYZ Cl1 Br1 SIZE 0.03 0.07 0.33 CONF TEMP -100.150 WGHT 0.029400 3.436000 FVAR 0.20800 0.70393 IR1 4 0.779135 0.507548 0.517325 11.00000 0.02967 0.02609 = 0.02588 0.00006 -0.00393 0.00220 CL1 3 0.874546 0.524976 0.295647 21.00000 0.03901 0.04145 = 0.03560 0.00484 0.00777 0.00573 BR1 6 0.874546 0.524976 0.295647 -21.00000 0.03901 0.04145 = 0.03560 0.00484 0.00777 0.00573 N1 5 0.774248 0.696362 0.548588 11.00000 0.02961 0.02628 = 0.02530 -0.00645 -0.00083 0.00024 N2 5 0.882122 0.658087 0.710289 11.00000 0.03210 0.03476 = 0.03177 -0.00648 -0.00494 -0.00069 N3 5 0.475815 0.606744 -0.070175 11.00000 0.05498 0.06071 = 0.06094 0.01756 -0.02651 -0.01089 C1 1 0.696436 0.591030 0.385487 11.00000 0.02913 0.03023 = 0.02284 -0.00009 -0.00115 0.00008 C2 1 0.634485 0.572549 0.258882 11.00000 0.02792 0.03303 = 0.02877 0.00598 -0.00148 -0.00137 AFIX 43 H2 2 0.625896 0.513817 0.223226 11.00000 -1.20000 AFIX 0 C3 1 0.583836 0.638616 0.181534 11.00000 0.02761 0.03878 = 0.03153 0.00621 0.00141 -0.00331 C4 1 0.593540 0.725620 0.230074 11.00000 0.03544 0.04086 = 0.02860 0.00995 0.00295 0.00903 AFIX 43 H4 2 0.557511 0.769500 0.179276 11.00000 -1.20000 AFIX 0 C5 1 0.656728 0.746815 0.353782 11.00000 0.03913 0.02923 = 0.03353 0.00180 0.00767 0.00529 AFIX 43 H5 2 0.666088 0.805707 0.387746 11.00000 -1.20000 AFIX 0 C6 1 0.705640 0.680520 0.426342 11.00000 0.03115 0.03334 = 0.02012 -0.00016 0.00286 0.00238 C7 1 0.817866 0.625587 0.606929 11.00000 0.03128 0.03199 = 0.02680 0.00364 0.00603 0.00009 C8 1 0.877441 0.748139 0.713020 11.00000 0.03990 0.03387 = 0.03746 -0.01010 0.00048 -0.00421 AFIX 43 H8 2 0.915479 0.786034 0.776210 11.00000 -1.20000 AFIX 0 C9 1 0.810666 0.772641 0.612192 11.00000 0.04169 0.02912 = 0.03234 -0.00449 0.00827 0.00109 AFIX 43 H9 2 0.791863 0.830605 0.588706 11.00000 -1.20000 AFIX 0 C10 1 0.522492 0.618966 0.042791 11.00000 0.03291 0.03931 = 0.05091 0.01472 -0.00818 -0.00734 C11 1 0.948127 0.608031 0.802334 11.00000 0.03391 0.04243 = 0.05983 -0.00042 -0.01439 0.00099 AFIX 137 H11A 2 0.931645 0.594269 0.913245 11.00000 -1.50000 H11B 2 1.000303 0.642195 0.813713 11.00000 -1.50000 H11C 2 0.957172 0.553700 0.742435 11.00000 -1.50000 AFIX 0 C12 1 0.816310 0.410265 0.722906 11.00000 0.06380 0.02821 = 0.03778 0.00879 -0.01767 -0.00507 C13 1 0.730100 0.440198 0.722987 11.00000 0.06412 0.03013 = 0.03451 0.00815 0.01051 -0.00727 C14 1 0.684481 0.408754 0.568831 11.00000 0.03887 0.02990 = 0.04261 0.01115 -0.00144 -0.00289 C15 1 0.743390 0.368029 0.472017 11.00000 0.04932 0.02197 = 0.03692 0.00338 -0.00804 -0.00567 C16 1 0.824676 0.370121 0.570149 11.00000 0.04586 0.01665 = 0.05834 0.00553 -0.00777 0.00544 C17 1 0.881071 0.410425 0.871548 11.00000 0.10001 0.05804 = 0.05448 0.02166 -0.04049 -0.02136 AFIX 137 H17A 2 0.876679 0.356208 0.934662 11.00000 -1.50000 H17B 2 0.871368 0.460440 0.942996 11.00000 -1.50000 H17C 2 0.937436 0.414732 0.834009 11.00000 -1.50000 AFIX 0 C18 1 0.691747 0.479630 0.865686 11.00000 0.11455 0.05826 = 0.04146 0.00221 0.03487 -0.01195 AFIX 137 H18A 2 0.672507 0.433190 0.936398 11.00000 -1.50000 H18B 2 0.643722 0.516026 0.823731 11.00000 -1.50000 H18C 2 0.733700 0.515698 0.931111 11.00000 -1.50000 AFIX 0 C19 1 0.591086 0.414457 0.528844 11.00000 0.04250 0.06706 = 0.07113 0.02634 0.00596 -0.01241 AFIX 137 H19A 2 0.577227 0.413041 0.407632 11.00000 -1.50000 H19B 2 0.570595 0.469140 0.573294 11.00000 -1.50000 H19C 2 0.564242 0.364926 0.579406 11.00000 -1.50000 AFIX 0 C20 1 0.723654 0.324235 0.307052 11.00000 0.08118 0.04462 = 0.04527 -0.01333 -0.00777 -0.00530 AFIX 137 H20A 2 0.721726 0.260868 0.323143 11.00000 -1.50000 H20B 2 0.767367 0.338479 0.234355 11.00000 -1.50000 H20C 2 0.668925 0.344637 0.255464 11.00000 -1.50000 AFIX 0 C21 1 0.904731 0.332788 0.519319 11.00000 0.06173 0.03361 = 0.10067 -0.00274 -0.00323 0.01703 AFIX 137 H21A 2 0.951644 0.371880 0.555569 11.00000 -1.50000 H21B 2 0.900273 0.326608 0.397738 11.00000 -1.50000 H21C 2 0.914773 0.275396 0.571319 11.00000 -1.50000 AFIX 0 HKLF 4 REM ga_210507da_a.res in P2(1)/c REM R1 = 0.0342 for 3256 Fo > 4sig(Fo) and 0.0478 for all 4007 data REM 242 parameters refined using 0 restraints END WGHT 0.0298 3.3657 REM Highest difference peak 0.955, deepest hole -1.043, 1-sigma level 0.138 Q1 1 0.6601 0.5077 0.4453 11.00000 0.05 0.96 Q2 1 0.7201 0.4724 0.4981 11.00000 0.05 0.81 Q3 1 0.8093 0.5833 0.5486 11.00000 0.05 0.81 Q4 1 0.7534 0.4197 0.5039 11.00000 0.05 0.76 Q5 1 0.8414 0.5599 0.4872 11.00000 0.05 0.74 ; _shelx_res_checksum 65217 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.77913(2) 0.50755(2) 0.51733(2) 0.02767(9) Uani 1 1 d . . . . . Cl1 Cl 0.87455(7) 0.52498(6) 0.29565(12) 0.0384(4) Uani 0.704(5) 1 d . . P . . Br1 Br 0.87455(7) 0.52498(6) 0.29565(12) 0.0384(4) Uani 0.296(5) 1 d . . P . . N1 N 0.7742(3) 0.6964(3) 0.5486(5) 0.0273(9) Uani 1 1 d . . . . . N2 N 0.8821(3) 0.6581(3) 0.7103(5) 0.0334(10) Uani 1 1 d . . . . . N3 N 0.4758(4) 0.6067(4) -0.0702(7) 0.0611(16) Uani 1 1 d . . . . . C1 C 0.6964(3) 0.5910(3) 0.3855(6) 0.0277(11) Uani 1 1 d . . . . . C2 C 0.6345(3) 0.5725(3) 0.2589(6) 0.0302(11) Uani 1 1 d . . . . . H2 H 0.6259 0.5138 0.2232 0.036 Uiso 1 1 calc R U . . . C3 C 0.5838(3) 0.6386(3) 0.1815(6) 0.0327(12) Uani 1 1 d . . . . . C4 C 0.5935(4) 0.7256(4) 0.2301(6) 0.0350(12) Uani 1 1 d . . . . . H4 H 0.5575 0.7695 0.1793 0.042 Uiso 1 1 calc R U . . . C5 C 0.6567(4) 0.7468(3) 0.3538(6) 0.0337(12) Uani 1 1 d . . . . . H5 H 0.6661 0.8057 0.3877 0.040 Uiso 1 1 calc R U . . . C6 C 0.7056(3) 0.6805(3) 0.4263(6) 0.0282(11) Uani 1 1 d . . . . . C7 C 0.8179(3) 0.6256(3) 0.6069(6) 0.0298(11) Uani 1 1 d . . . . . C8 C 0.8774(4) 0.7481(3) 0.7130(7) 0.0373(13) Uani 1 1 d . . . . . H8 H 0.9155 0.7860 0.7762 0.045 Uiso 1 1 calc R U . . . C9 C 0.8107(4) 0.7726(3) 0.6122(6) 0.0341(12) Uani 1 1 d . . . . . H9 H 0.7919 0.8306 0.5887 0.041 Uiso 1 1 calc R U . . . C10 C 0.5225(4) 0.6190(4) 0.0428(8) 0.0419(14) Uani 1 1 d . . . . . C11 C 0.9481(4) 0.6080(4) 0.8023(8) 0.0467(15) Uani 1 1 d . . . . . H11A H 0.9316 0.5943 0.9132 0.070 Uiso 1 1 calc R U . . . H11B H 1.0003 0.6422 0.8137 0.070 Uiso 1 1 calc R U . . . H11C H 0.9572 0.5537 0.7424 0.070 Uiso 1 1 calc R U . . . C12 C 0.8163(4) 0.4103(4) 0.7229(7) 0.0448(16) Uani 1 1 d . . . . . C13 C 0.7301(4) 0.4402(4) 0.7230(7) 0.0425(15) Uani 1 1 d . . . . . C14 C 0.6845(4) 0.4088(3) 0.5688(7) 0.0375(13) Uani 1 1 d . . . . . C15 C 0.7434(4) 0.3680(3) 0.4720(7) 0.0369(13) Uani 1 1 d . . . . . C16 C 0.8247(4) 0.3701(3) 0.5701(8) 0.0412(14) Uani 1 1 d . . . . . C17 C 0.8811(6) 0.4104(5) 0.8715(9) 0.074(3) Uani 1 1 d . . . . . H17A H 0.8767 0.3562 0.9347 0.111 Uiso 1 1 calc R U . . . H17B H 0.8714 0.4604 0.9430 0.111 Uiso 1 1 calc R U . . . H17C H 0.9374 0.4147 0.8340 0.111 Uiso 1 1 calc R U . . . C18 C 0.6917(6) 0.4796(5) 0.8657(9) 0.070(2) Uani 1 1 d . . . . . H18A H 0.6725 0.4332 0.9364 0.104 Uiso 1 1 calc R U . . . H18B H 0.6437 0.5160 0.8237 0.104 Uiso 1 1 calc R U . . . H18C H 0.7337 0.5157 0.9311 0.104 Uiso 1 1 calc R U . . . C19 C 0.5911(4) 0.4145(5) 0.5288(9) 0.0602(19) Uani 1 1 d . . . . . H19A H 0.5772 0.4130 0.4076 0.090 Uiso 1 1 calc R U . . . H19B H 0.5706 0.4691 0.5733 0.090 Uiso 1 1 calc R U . . . H19C H 0.5642 0.3649 0.5794 0.090 Uiso 1 1 calc R U . . . C20 C 0.7237(5) 0.3242(4) 0.3071(8) 0.0580(19) Uani 1 1 d . . . . . H20A H 0.7217 0.2609 0.3231 0.087 Uiso 1 1 calc R U . . . H20B H 0.7674 0.3385 0.2344 0.087 Uiso 1 1 calc R U . . . H20C H 0.6689 0.3446 0.2555 0.087 Uiso 1 1 calc R U . . . C21 C 0.9047(5) 0.3328(4) 0.5193(10) 0.066(2) Uani 1 1 d . . . . . H21A H 0.9516 0.3719 0.5556 0.099 Uiso 1 1 calc R U . . . H21B H 0.9003 0.3266 0.3977 0.099 Uiso 1 1 calc R U . . . H21C H 0.9148 0.2754 0.5713 0.099 Uiso 1 1 calc R U . . . 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 0.02967(13) 0.02609(13) 0.02588(13) 0.00006(9) -0.00393(9) 0.00220(9) Cl1 0.0390(6) 0.0414(6) 0.0356(6) 0.0048(4) 0.0078(4) 0.0057(4) Br1 0.0390(6) 0.0414(6) 0.0356(6) 0.0048(4) 0.0078(4) 0.0057(4) N1 0.030(2) 0.026(2) 0.025(2) -0.0064(16) -0.0008(18) 0.0002(17) N2 0.032(3) 0.035(2) 0.032(2) -0.0065(18) -0.005(2) -0.0007(19) N3 0.055(4) 0.061(4) 0.061(4) 0.018(3) -0.027(3) -0.011(3) C1 0.029(3) 0.030(3) 0.023(2) -0.0001(19) -0.001(2) 0.000(2) C2 0.028(3) 0.033(3) 0.029(3) 0.006(2) -0.001(2) -0.001(2) C3 0.028(3) 0.039(3) 0.032(3) 0.006(2) 0.001(2) -0.003(2) C4 0.035(3) 0.041(3) 0.029(3) 0.010(2) 0.003(2) 0.009(2) C5 0.039(3) 0.029(3) 0.034(3) 0.002(2) 0.008(2) 0.005(2) C6 0.031(3) 0.033(3) 0.020(2) -0.0002(19) 0.003(2) 0.002(2) C7 0.031(3) 0.032(3) 0.027(3) 0.004(2) 0.006(2) 0.000(2) C8 0.040(3) 0.034(3) 0.037(3) -0.010(2) 0.000(3) -0.004(2) C9 0.042(3) 0.029(3) 0.032(3) -0.004(2) 0.008(2) 0.001(2) C10 0.033(3) 0.039(3) 0.051(4) 0.015(3) -0.008(3) -0.007(2) C11 0.034(3) 0.042(3) 0.060(4) 0.000(3) -0.014(3) 0.001(3) C12 0.064(4) 0.028(3) 0.038(3) 0.009(2) -0.018(3) -0.005(3) C13 0.064(4) 0.030(3) 0.035(3) 0.008(2) 0.011(3) -0.007(3) C14 0.039(3) 0.030(3) 0.043(3) 0.011(2) -0.001(3) -0.003(2) C15 0.049(4) 0.022(2) 0.037(3) 0.003(2) -0.008(3) -0.006(2) C16 0.046(4) 0.017(2) 0.058(4) 0.006(2) -0.008(3) 0.005(2) C17 0.100(7) 0.058(4) 0.054(4) 0.022(3) -0.040(4) -0.021(4) C18 0.115(7) 0.058(4) 0.041(4) 0.002(3) 0.035(4) -0.012(4) C19 0.043(4) 0.067(5) 0.071(5) 0.026(4) 0.006(3) -0.012(3) C20 0.081(6) 0.045(4) 0.045(4) -0.013(3) -0.008(4) -0.005(3) C21 0.062(5) 0.034(3) 0.101(6) -0.003(3) -0.003(4) 0.017(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -5.7005 5.2682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C7 Ir1 C1 77.6(2) . . ? C7 Ir1 C13 105.9(2) . . ? C1 Ir1 C13 115.4(2) . . ? C7 Ir1 C14 137.5(2) . . ? C1 Ir1 C14 96.2(2) . . ? C13 Ir1 C14 38.9(2) . . ? C7 Ir1 C15 168.23(19) . . ? C1 Ir1 C15 111.76(19) . . ? C13 Ir1 C15 64.1(2) . . ? C14 Ir1 C15 37.4(2) . . ? C7 Ir1 C16 133.4(2) . . ? C1 Ir1 C16 149.0(2) . . ? C13 Ir1 C16 62.9(2) . . ? C14 Ir1 C16 62.5(2) . . ? C15 Ir1 C16 37.7(2) . . ? C7 Ir1 C12 106.21(19) . . ? C1 Ir1 C12 153.6(2) . . ? C13 Ir1 C12 38.2(2) . . ? C14 Ir1 C12 62.9(2) . . ? C15 Ir1 C12 62.18(19) . . ? C16 Ir1 C12 36.0(2) . . ? C7 Ir1 Cl1 88.47(15) . . ? C1 Ir1 Cl1 88.26(14) . . ? C13 Ir1 Cl1 154.17(17) . . ? C14 Ir1 Cl1 133.80(16) . . ? C15 Ir1 Cl1 98.67(16) . . ? C16 Ir1 Cl1 91.54(17) . . ? C12 Ir1 Cl1 117.68(19) . . ? C7 N1 C9 111.6(4) . . ? C7 N1 C6 116.1(4) . . ? C9 N1 C6 132.0(4) . . ? C7 N2 C8 109.8(4) . . ? C7 N2 C11 126.2(5) . . ? C8 N2 C11 124.0(5) . . ? C2 C1 C6 115.0(5) . . ? C2 C1 Ir1 129.1(4) . . ? C6 C1 Ir1 115.9(4) . . ? C1 C2 C3 121.3(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 121.5(5) . . ? C4 C3 C10 117.7(5) . . ? C2 C3 C10 120.7(5) . . ? C5 C4 C3 118.6(5) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C6 C5 C4 118.3(5) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 125.1(5) . . ? C5 C6 N1 122.3(5) . . ? C1 C6 N1 112.5(4) . . ? N1 C7 N2 104.6(4) . . ? N1 C7 Ir1 117.8(4) . . ? N2 C7 Ir1 137.5(4) . . ? C9 C8 N2 108.3(5) . . ? C9 C8 H8 125.9 . . ? N2 C8 H8 125.9 . . ? C8 C9 N1 105.7(5) . . ? C8 C9 H9 127.2 . . ? N1 C9 H9 127.2 . . ? N3 C10 C3 176.7(6) . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C12 C13 108.4(5) . . ? C16 C12 C17 125.9(7) . . ? C13 C12 C17 125.2(7) . . ? C16 C12 Ir1 71.6(3) . . ? C13 C12 Ir1 67.3(3) . . ? C17 C12 Ir1 133.8(4) . . ? C12 C13 C14 106.7(5) . . ? C12 C13 C18 126.5(6) . . ? C14 C13 C18 125.8(7) . . ? C12 C13 Ir1 74.6(3) . . ? C14 C13 Ir1 72.1(3) . . ? C18 C13 Ir1 127.5(4) . . ? C15 C14 C13 108.1(5) . . ? C15 C14 C19 127.3(6) . . ? C13 C14 C19 124.5(6) . . ? C15 C14 Ir1 72.2(3) . . ? C13 C14 Ir1 69.0(3) . . ? C19 C14 Ir1 127.3(4) . . ? C14 C15 C16 107.2(5) . . ? C14 C15 C20 126.3(6) . . ? C16 C15 C20 126.3(6) . . ? C14 C15 Ir1 70.3(3) . . ? C16 C15 Ir1 71.9(3) . . ? C20 C15 Ir1 127.1(4) . . ? C12 C16 C15 109.3(6) . . ? C12 C16 C21 124.8(6) . . ? C15 C16 C21 125.8(6) . . ? C12 C16 Ir1 72.4(3) . . ? C15 C16 Ir1 70.4(3) . . ? C21 C16 Ir1 125.0(4) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C7 2.020(5) . ? Ir1 C1 2.055(5) . ? Ir1 C13 2.165(5) . ? Ir1 C14 2.207(6) . ? Ir1 C15 2.232(5) . ? Ir1 C16 2.253(5) . ? Ir1 C12 2.263(5) . ? Ir1 Cl1 2.4765(10) . ? N1 C7 1.347(6) . ? N1 C9 1.380(6) . ? N1 C6 1.418(7) . ? N2 C7 1.350(7) . ? N2 C8 1.381(7) . ? N2 C11 1.446(7) . ? N3 C10 1.132(8) . ? C1 C2 1.377(7) . ? C1 C6 1.414(7) . ? C2 C3 1.402(7) . ? C2 H2 0.9500 . ? C3 C4 1.393(8) . ? C3 C10 1.442(8) . ? C4 C5 1.383(8) . ? C4 H4 0.9500 . ? C5 C6 1.375(7) . ? C5 H5 0.9500 . ? C8 C9 1.328(8) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C16 1.395(8) . ? C12 C13 1.451(9) . ? C12 C17 1.501(9) . ? C13 C14 1.457(8) . ? C13 C18 1.485(9) . ? C14 C15 1.425(8) . ? C14 C19 1.496(9) . ? C15 C16 1.450(8) . ? C15 C20 1.494(8) . ? C16 C21 1.494(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C6 C1 C2 C3 -1.6(8) . . . . ? Ir1 C1 C2 C3 -179.5(4) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C1 C2 C3 C10 176.4(5) . . . . ? C2 C3 C4 C5 2.2(8) . . . . ? C10 C3 C4 C5 -174.8(5) . . . . ? C3 C4 C5 C6 -1.7(8) . . . . ? C4 C5 C6 C1 -0.4(8) . . . . ? C4 C5 C6 N1 177.1(5) . . . . ? C2 C1 C6 C5 2.1(8) . . . . ? Ir1 C1 C6 C5 -179.7(4) . . . . ? C2 C1 C6 N1 -175.6(5) . . . . ? Ir1 C1 C6 N1 2.6(6) . . . . ? C7 N1 C6 C5 -178.7(5) . . . . ? C9 N1 C6 C5 -5.0(9) . . . . ? C7 N1 C6 C1 -1.0(6) . . . . ? C9 N1 C6 C1 172.8(5) . . . . ? C9 N1 C7 N2 0.7(6) . . . . ? C6 N1 C7 N2 175.7(4) . . . . ? C9 N1 C7 Ir1 -176.2(3) . . . . ? C6 N1 C7 Ir1 -1.1(6) . . . . ? C8 N2 C7 N1 -0.4(6) . . . . ? C11 N2 C7 N1 -178.9(5) . . . . ? C8 N2 C7 Ir1 175.4(4) . . . . ? C11 N2 C7 Ir1 -3.0(9) . . . . ? C7 N2 C8 C9 0.0(7) . . . . ? C11 N2 C8 C9 178.5(6) . . . . ? N2 C8 C9 N1 0.4(6) . . . . ? C7 N1 C9 C8 -0.7(6) . . . . ? C6 N1 C9 C8 -174.7(5) . . . . ? C16 C12 C13 C14 5.4(6) . . . . ? C17 C12 C13 C14 -166.1(5) . . . . ? Ir1 C12 C13 C14 65.4(3) . . . . ? C16 C12 C13 C18 174.4(6) . . . . ? C17 C12 C13 C18 3.0(9) . . . . ? Ir1 C12 C13 C18 -125.5(6) . . . . ? C16 C12 C13 Ir1 -60.1(4) . . . . ? C17 C12 C13 Ir1 128.5(6) . . . . ? C12 C13 C14 C15 -5.1(6) . . . . ? C18 C13 C14 C15 -174.3(5) . . . . ? Ir1 C13 C14 C15 62.0(4) . . . . ? C12 C13 C14 C19 171.3(5) . . . . ? C18 C13 C14 C19 2.2(9) . . . . ? Ir1 C13 C14 C19 -121.6(5) . . . . ? C12 C13 C14 Ir1 -67.1(4) . . . . ? C18 C13 C14 Ir1 123.8(6) . . . . ? C13 C14 C15 C16 3.0(6) . . . . ? C19 C14 C15 C16 -173.3(5) . . . . ? Ir1 C14 C15 C16 62.9(4) . . . . ? C13 C14 C15 C20 178.0(5) . . . . ? C19 C14 C15 C20 1.6(9) . . . . ? Ir1 C14 C15 C20 -122.1(6) . . . . ? C13 C14 C15 Ir1 -59.9(4) . . . . ? C19 C14 C15 Ir1 123.8(6) . . . . ? C13 C12 C16 C15 -3.6(6) . . . . ? C17 C12 C16 C15 167.8(6) . . . . ? Ir1 C12 C16 C15 -61.0(4) . . . . ? C13 C12 C16 C21 178.2(5) . . . . ? C17 C12 C16 C21 -10.4(10) . . . . ? Ir1 C12 C16 C21 120.8(6) . . . . ? C13 C12 C16 Ir1 57.4(4) . . . . ? C17 C12 C16 Ir1 -131.3(6) . . . . ? C14 C15 C16 C12 0.4(6) . . . . ? C20 C15 C16 C12 -174.6(5) . . . . ? Ir1 C15 C16 C12 62.2(4) . . . . ? C14 C15 C16 C21 178.5(6) . . . . ? C20 C15 C16 C21 3.6(9) . . . . ? Ir1 C15 C16 C21 -119.6(6) . . . . ? C14 C15 C16 Ir1 -61.9(4) . . . . ? C20 C15 C16 Ir1 123.2(6) . . . . ?