#------------------------------------------------------------------------------ #$Date: 2021-10-05 03:28:18 +0300 (Tue, 05 Oct 2021) $ #$Revision: 269554 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060997.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_7060997 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_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03824A _journal_year 2021 _chemical_formula_sum 'C20 H24 Cl0.35 I0.65 Ir N2' _chemical_formula_weight 579.50 _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-2016/6 _audit_update_record ; 2021-09-02 deposited with the CCDC. 2021-09-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.717(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.6569(8) _cell_length_b 8.7972(5) _cell_length_c 16.3348(10) _cell_measurement_reflns_used 9920 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 56.97 _cell_measurement_theta_min 2.89 _cell_volume 1914.4(2) _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-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0495 _diffrn_reflns_av_unetI/netI 0.0282 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 26774 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 56.980 _diffrn_reflns_theta_min 4.829 _exptl_absorpt_coefficient_mu 14.925 _exptl_absorpt_correction_T_max 0.370 _exptl_absorpt_correction_T_min 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.011 _exptl_crystal_description block _exptl_crystal_F_000 1102 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.867 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.101 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 3894 _refine_ls_number_restraints 45 _refine_ls_restrained_S_all 1.137 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0255 _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^)+(0.0235P)^2^+2.7157P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.0611 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3503 _reflns_number_total 3894 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03824a2.cif _cod_data_source_block ga_210507b_c _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060997 _shelx_shelxl_version_number 2016/6 _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 0.247 _shelx_estimated_absorpt_t_max 0.587 _shelx_res_file ; TITL ga_210507b_a.res in P2(1)/c ga_210507b_a.res created by SHELXL-2016/6 at 13:30:13 on 01-Sep-2021 CELL 1.34138 13.6569 8.7972 16.3348 90.000 102.717 90.000 ZERR 4.000 0.0008 0.0005 0.0010 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H Cl Ir N I UNIT 80 96 1.4 4 8 2.6 L.S. 7 ACTA BOND $H CONF FMAP 2 PLAN 5 SIZE 0.04 0.11 0.13 DFIX 2.38 0.05 Ir1 Cl1 DFIX 2.70 0.05 Ir1 I1 DFIX 0.32 0.05 I1 Cl1 SIMU 0.02 0.05 2.0 Cl1 I1 ISOR 0.02 C20 Cl1 ISOR 0.007 C16 C17 C18 C19 TEMP -100.160 WGHT 0.023500 2.715700 FVAR 0.31834 IR1 4 0.228050 0.687183 0.370176 11.00000 0.02928 0.02750 = 0.02863 -0.00165 0.00576 0.00014 CL1 3 0.204127 0.487206 0.464152 10.35000 0.08387 0.03018 = 0.08269 0.02310 0.00976 -0.00250 I1 6 0.192700 0.449377 0.461598 10.65000 0.03825 0.03310 = 0.04388 0.00969 0.01042 0.00087 N1 5 0.440295 0.623889 0.398766 11.00000 0.03114 0.04825 = 0.05521 0.02183 0.01135 0.00351 N2 5 0.424826 0.758694 0.504912 11.00000 0.05033 0.04318 = 0.04904 0.00982 -0.00903 -0.01205 C1 1 0.298073 0.542447 0.303102 11.00000 0.05653 0.02836 = 0.03625 0.00486 0.01341 0.00833 C2 1 0.254968 0.448616 0.235258 11.00000 0.08656 0.03874 = 0.03738 0.00100 0.01315 0.01203 AFIX 43 H2 2 0.183954 0.445468 0.217164 11.00000 -1.20000 AFIX 0 C3 1 0.312953 0.360273 0.193793 11.00000 0.13955 0.04512 = 0.04619 0.00138 0.03453 0.02598 AFIX 43 H3 2 0.281680 0.298467 0.147739 11.00000 -1.20000 AFIX 0 C4 1 0.415788 0.362493 0.219579 11.00000 0.14932 0.06098 = 0.06207 0.01967 0.06054 0.05760 AFIX 43 H4 2 0.455141 0.302605 0.190599 11.00000 -1.20000 AFIX 0 C5 1 0.462777 0.450072 0.286728 11.00000 0.08377 0.06892 = 0.08145 0.03546 0.05656 0.03763 AFIX 43 H5 2 0.533841 0.451557 0.304577 11.00000 -1.20000 AFIX 0 C6 1 0.402731 0.535990 0.327361 11.00000 0.05660 0.03992 = 0.04525 0.01695 0.02680 0.01815 C7 1 0.371050 0.697020 0.432573 11.00000 0.04002 0.03052 = 0.03756 0.00810 0.00633 -0.00391 C8 1 0.525410 0.724684 0.515679 11.00000 0.04635 0.05859 = 0.07183 0.02396 -0.01389 -0.01699 AFIX 43 H8 2 0.577511 0.755535 0.561335 11.00000 -1.20000 AFIX 0 C9 1 0.536220 0.640606 0.450335 11.00000 0.02854 0.07274 = 0.09066 0.04793 0.00388 -0.00197 AFIX 43 H9 2 0.597116 0.599961 0.440644 11.00000 -1.20000 AFIX 0 C10 1 0.382734 0.844706 0.564490 11.00000 0.09888 0.05335 = 0.04540 -0.00812 -0.01392 0.00212 AFIX 137 H10A 2 0.385749 0.953476 0.552323 11.00000 -1.50000 H10B 2 0.421289 0.824350 0.621490 11.00000 -1.50000 H10C 2 0.312676 0.814509 0.559981 11.00000 -1.50000 AFIX 0 C11 1 0.167358 0.838639 0.267796 11.00000 0.06438 0.05332 = 0.03643 0.01227 0.01116 0.02723 C12 1 0.086264 0.749231 0.280200 11.00000 0.04666 0.03844 = 0.08321 -0.01294 -0.02795 0.00714 C13 1 0.072845 0.782578 0.362359 11.00000 0.04078 0.05746 = 0.11138 0.03578 0.03483 0.02182 C14 1 0.142991 0.892678 0.398434 11.00000 0.06891 0.05076 = 0.03813 -0.00317 0.00720 0.03037 C15 1 0.201243 0.926685 0.340192 11.00000 0.04200 0.03169 = 0.05871 0.00719 -0.00902 0.00207 C16 1 0.203881 0.849435 0.186215 11.00000 0.13070 0.11454 = 0.05826 0.02389 0.04160 0.06067 AFIX 137 H16A 2 0.202758 0.748220 0.160965 11.00000 -1.50000 H16B 2 0.272572 0.889271 0.198021 11.00000 -1.50000 H16C 2 0.159779 0.917749 0.147242 11.00000 -1.50000 AFIX 0 C17 1 0.017325 0.652645 0.217065 11.00000 0.10073 0.07910 = 0.14647 -0.03434 -0.06348 0.01048 AFIX 137 H17A 2 -0.004538 0.564798 0.245338 11.00000 -1.50000 H17B 2 0.052793 0.617370 0.174586 11.00000 -1.50000 H17C 2 -0.041375 0.712588 0.189971 11.00000 -1.50000 AFIX 0 C18 1 -0.006866 0.718652 0.402756 11.00000 0.07551 0.10483 = 0.19039 0.05771 0.07503 0.02481 AFIX 137 H18A 2 -0.066823 0.783005 0.389034 11.00000 -1.50000 H18B 2 0.018076 0.715785 0.463767 11.00000 -1.50000 H18C 2 -0.023895 0.615429 0.381843 11.00000 -1.50000 AFIX 0 C19 1 0.142092 0.977575 0.479193 11.00000 0.15648 0.11484 = 0.06461 -0.01432 0.01878 0.08699 AFIX 137 H19A 2 0.208455 1.021943 0.501367 11.00000 -1.50000 H19B 2 0.125509 0.906892 0.520496 11.00000 -1.50000 H19C 2 0.091733 1.058687 0.467842 11.00000 -1.50000 AFIX 0 C20 1 0.282063 1.046135 0.351547 11.00000 0.07207 0.04999 = 0.13709 0.02271 -0.01103 -0.01273 AFIX 137 H20A 2 0.254937 1.138909 0.321786 11.00000 -1.50000 H20B 2 0.338261 1.008782 0.328814 11.00000 -1.50000 H20C 2 0.305597 1.068465 0.411434 11.00000 -1.50000 AFIX 0 HKLF 4 REM ga_210507b_a.res in P2(1)/c REM R1 = 0.0255 for 3503 Fo > 4sig(Fo) and 0.0305 for all 3894 data REM 232 parameters refined using 45 restraints END WGHT 0.0234 2.7033 REM Highest difference peak 0.867, deepest hole -0.500, 1-sigma level 0.101 Q1 1 0.2800 0.6824 0.4254 11.00000 0.05 0.87 Q2 1 0.1797 0.6850 0.3162 11.00000 0.05 0.83 Q3 1 0.2716 0.6116 0.3505 11.00000 0.05 0.75 Q4 1 -0.0228 0.6344 0.3164 11.00000 0.05 0.74 Q5 1 0.1804 0.6243 0.3865 11.00000 0.05 0.73 ; _shelx_res_checksum 54964 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 0.22805(2) 0.68718(2) 0.37018(2) 0.02857(7) Uani 1 1 d D . . . . Cl1 Cl 0.2041(10) 0.4872(11) 0.4642(9) 0.067(3) Uani 0.35 1 d D U P . . I1 I 0.19270(10) 0.44938(16) 0.46160(9) 0.0382(2) Uani 0.65 1 d D U P . . N1 N 0.4403(3) 0.6239(5) 0.3988(3) 0.0446(10) Uani 1 1 d . . . . . N2 N 0.4248(3) 0.7587(5) 0.5049(3) 0.0506(11) Uani 1 1 d . . . . . C1 C 0.2981(4) 0.5424(5) 0.3031(3) 0.0399(10) Uani 1 1 d . . . . . C2 C 0.2550(5) 0.4486(6) 0.2353(3) 0.0543(14) Uani 1 1 d . . . . . H2 H 0.183954 0.445468 0.217164 0.065 Uiso 1 1 calc R U . . . C3 C 0.3130(7) 0.3603(7) 0.1938(4) 0.075(2) Uani 1 1 d . . . . . H3 H 0.281680 0.298467 0.147739 0.090 Uiso 1 1 calc R U . . . C4 C 0.4158(7) 0.3625(8) 0.2196(4) 0.085(3) Uani 1 1 d . . . . . H4 H 0.455141 0.302605 0.190599 0.102 Uiso 1 1 calc R U . . . C5 C 0.4628(5) 0.4501(7) 0.2867(4) 0.072(2) Uani 1 1 d . . . . . H5 H 0.533841 0.451557 0.304577 0.087 Uiso 1 1 calc R U . . . C6 C 0.4027(4) 0.5360(5) 0.3274(3) 0.0449(11) Uani 1 1 d . . . . . C7 C 0.3711(3) 0.6970(5) 0.4326(3) 0.0364(10) Uani 1 1 d . . . . . C8 C 0.5254(4) 0.7247(7) 0.5157(4) 0.0631(17) Uani 1 1 d . . . . . H8 H 0.577511 0.755535 0.561335 0.076 Uiso 1 1 calc R U . . . C9 C 0.5362(4) 0.6406(7) 0.4503(4) 0.0654(18) Uani 1 1 d . . . . . H9 H 0.597116 0.599961 0.440644 0.078 Uiso 1 1 calc R U . . . C10 C 0.3827(5) 0.8447(7) 0.5645(3) 0.0705(18) Uani 1 1 d . . . . . H10A H 0.385749 0.953476 0.552323 0.106 Uiso 1 1 calc R U . . . H10B H 0.421289 0.824350 0.621490 0.106 Uiso 1 1 calc R U . . . H10C H 0.312676 0.814509 0.559981 0.106 Uiso 1 1 calc R U . . . C11 C 0.1674(4) 0.8386(6) 0.2678(3) 0.0514(13) Uani 1 1 d . . . . . C12 C 0.0863(4) 0.7492(6) 0.2802(4) 0.0626(17) Uani 1 1 d . . . . . C13 C 0.0728(4) 0.7826(7) 0.3624(5) 0.0671(19) Uani 1 1 d . . . . . C14 C 0.1430(4) 0.8927(6) 0.3984(3) 0.0533(14) Uani 1 1 d . . . . . C15 C 0.2012(4) 0.9267(5) 0.3402(3) 0.0472(12) Uani 1 1 d . . . . . C16 C 0.2039(7) 0.8494(9) 0.1862(4) 0.098(3) Uani 1 1 d . U . . . H16A H 0.202758 0.748220 0.160965 0.147 Uiso 1 1 calc R U . . . H16B H 0.272572 0.889271 0.198021 0.147 Uiso 1 1 calc R U . . . H16C H 0.159779 0.917749 0.147242 0.147 Uiso 1 1 calc R U . . . C17 C 0.0173(6) 0.6526(9) 0.2171(6) 0.123(4) Uani 1 1 d . U . . . H17A H -0.004538 0.564798 0.245338 0.184 Uiso 1 1 calc R U . . . H17B H 0.052793 0.617370 0.174586 0.184 Uiso 1 1 calc R U . . . H17C H -0.041375 0.712588 0.189971 0.184 Uiso 1 1 calc R U . . . C18 C -0.0069(6) 0.7187(10) 0.4028(7) 0.117(3) Uani 1 1 d . U . . . H18A H -0.066823 0.783005 0.389034 0.175 Uiso 1 1 calc R U . . . H18B H 0.018076 0.715785 0.463767 0.175 Uiso 1 1 calc R U . . . H18C H -0.023895 0.615429 0.381843 0.175 Uiso 1 1 calc R U . . . C19 C 0.1421(7) 0.9776(10) 0.4792(4) 0.113(3) Uani 1 1 d . U . . . H19A H 0.208455 1.021943 0.501367 0.169 Uiso 1 1 calc R U . . . H19B H 0.125509 0.906892 0.520496 0.169 Uiso 1 1 calc R U . . . H19C H 0.091733 1.058687 0.467842 0.169 Uiso 1 1 calc R U . . . C20 C 0.2821(5) 1.0461(7) 0.3515(5) 0.092(3) Uani 1 1 d . U . . . H20A H 0.254937 1.138909 0.321786 0.137 Uiso 1 1 calc R U . . . H20B H 0.338261 1.008782 0.328814 0.137 Uiso 1 1 calc R U . . . H20C H 0.305597 1.068465 0.411434 0.137 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 0.02928(10) 0.02750(11) 0.02863(10) -0.00165(7) 0.00576(7) 0.00014(7) Cl1 0.084(6) 0.030(5) 0.083(5) 0.023(3) 0.010(4) -0.002(3) I1 0.0383(3) 0.0331(6) 0.0439(4) 0.0097(4) 0.0104(2) 0.0009(4) N1 0.0311(19) 0.048(2) 0.055(2) 0.022(2) 0.0113(17) 0.0035(17) N2 0.050(2) 0.043(2) 0.049(2) 0.0098(19) -0.009(2) -0.0120(19) C1 0.057(3) 0.028(2) 0.036(2) 0.0049(18) 0.013(2) 0.0083(19) C2 0.087(4) 0.039(3) 0.037(3) 0.001(2) 0.013(3) 0.012(3) C3 0.140(7) 0.045(3) 0.046(3) 0.001(3) 0.035(4) 0.026(4) C4 0.149(7) 0.061(4) 0.062(4) 0.020(3) 0.061(5) 0.058(5) C5 0.084(4) 0.069(4) 0.081(4) 0.035(4) 0.057(4) 0.038(3) C6 0.057(3) 0.040(3) 0.045(3) 0.017(2) 0.027(2) 0.018(2) C7 0.040(2) 0.031(2) 0.038(2) 0.0081(18) 0.0063(18) -0.0039(18) C8 0.046(3) 0.059(4) 0.072(4) 0.024(3) -0.014(3) -0.017(3) C9 0.029(2) 0.073(4) 0.091(5) 0.048(4) 0.004(3) -0.002(2) C10 0.099(5) 0.053(3) 0.045(3) -0.008(3) -0.014(3) 0.002(3) C11 0.064(3) 0.053(3) 0.036(2) 0.012(2) 0.011(2) 0.027(3) C12 0.047(3) 0.038(3) 0.083(4) -0.013(3) -0.028(3) 0.007(2) C13 0.041(3) 0.057(4) 0.111(5) 0.036(4) 0.035(3) 0.022(3) C14 0.069(3) 0.051(3) 0.038(3) -0.003(2) 0.007(2) 0.030(3) C15 0.042(2) 0.032(2) 0.059(3) 0.007(2) -0.009(2) 0.002(2) C16 0.131(6) 0.115(6) 0.058(4) 0.024(4) 0.042(4) 0.061(5) C17 0.101(6) 0.079(5) 0.146(7) -0.034(5) -0.063(5) 0.010(4) C18 0.076(5) 0.105(6) 0.190(9) 0.058(6) 0.075(5) 0.025(4) C19 0.156(7) 0.115(6) 0.065(4) -0.014(4) 0.019(4) 0.087(5) C20 0.072(4) 0.050(4) 0.137(7) 0.023(4) -0.011(4) -0.013(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' I I 0.0030 5.4350 '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 77.33(19) . . ? C7 Ir1 C11 122.4(2) . . ? C1 Ir1 C11 96.56(18) . . ? C7 Ir1 C15 99.80(17) . . ? C1 Ir1 C15 123.8(2) . . ? C11 Ir1 C15 37.82(19) . . ? C7 Ir1 C12 159.7(2) . . ? C1 Ir1 C12 103.9(2) . . ? C11 Ir1 C12 37.5(2) . . ? C15 Ir1 C12 62.30(18) . . ? C7 Ir1 C14 110.6(2) . . ? C1 Ir1 C14 158.67(18) . . ? C11 Ir1 C14 62.30(18) . . ? C15 Ir1 C14 36.8(2) . . ? C12 Ir1 C14 61.7(2) . . ? C7 Ir1 C13 144.5(2) . . ? C1 Ir1 C13 138.1(3) . . ? C11 Ir1 C13 62.0(2) . . ? C15 Ir1 C13 61.2(2) . . ? C12 Ir1 C13 37.0(2) . . ? C14 Ir1 C13 36.1(2) . . ? C7 Ir1 Cl1 87.8(3) . . ? C1 Ir1 Cl1 91.8(3) . . ? C11 Ir1 Cl1 149.8(4) . . ? C15 Ir1 Cl1 144.4(3) . . ? C12 Ir1 Cl1 112.4(4) . . ? C14 Ir1 Cl1 107.9(4) . . ? C13 Ir1 Cl1 92.9(4) . . ? C7 Ir1 I1 91.45(12) . . ? C1 Ir1 I1 88.59(13) . . ? C11 Ir1 I1 146.14(17) . . ? C15 Ir1 I1 147.22(15) . . ? C12 Ir1 I1 108.83(18) . . ? C14 Ir1 I1 110.42(16) . . ? C13 Ir1 I1 92.28(15) . . ? Cl1 Ir1 I1 5.6(3) . . ? C7 N1 C6 116.1(4) . . ? C7 N1 C9 110.4(5) . . ? C6 N1 C9 133.0(5) . . ? C7 N2 C8 110.9(5) . . ? C7 N2 C10 125.1(4) . . ? C8 N2 C10 124.0(5) . . ? C6 C1 C2 115.2(5) . . ? C6 C1 Ir1 116.2(3) . . ? C2 C1 Ir1 128.6(4) . . ? C3 C2 C1 122.0(6) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C4 C3 C2 119.8(6) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.1(6) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 117.7(6) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C5 C6 C1 124.2(6) . . ? C5 C6 N1 123.6(5) . . ? C1 C6 N1 112.2(4) . . ? N1 C7 N2 104.6(4) . . ? N1 C7 Ir1 117.6(3) . . ? N2 C7 Ir1 137.9(4) . . ? C9 C8 N2 107.5(5) . . ? C9 C8 H8 126.2 . . ? N2 C8 H8 126.2 . . ? C8 C9 N1 106.6(5) . . ? C8 C9 H9 126.7 . . ? N1 C9 H9 126.7 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C11 C12 108.1(5) . . ? C15 C11 C16 126.2(6) . . ? C12 C11 C16 125.4(6) . . ? C15 C11 Ir1 71.8(3) . . ? C12 C11 Ir1 74.0(3) . . ? C16 C11 Ir1 124.9(4) . . ? C11 C12 C13 106.8(5) . . ? C11 C12 C17 127.8(7) . . ? C13 C12 C17 125.0(7) . . ? C11 C12 Ir1 68.6(3) . . ? C13 C12 Ir1 72.7(3) . . ? C17 C12 Ir1 129.7(4) . . ? C14 C13 C12 108.8(5) . . ? C14 C13 C18 124.8(7) . . ? C12 C13 C18 126.4(7) . . ? C14 C13 Ir1 71.7(3) . . ? C12 C13 Ir1 70.3(3) . . ? C18 C13 Ir1 126.8(4) . . ? C13 C14 C15 107.5(5) . . ? C13 C14 C19 124.8(7) . . ? C15 C14 C19 126.8(6) . . ? C13 C14 Ir1 72.2(3) . . ? C15 C14 Ir1 68.7(3) . . ? C19 C14 Ir1 132.6(4) . . ? C14 C15 C11 108.9(5) . . ? C14 C15 C20 125.2(6) . . ? C11 C15 C20 125.8(6) . . ? C14 C15 Ir1 74.5(3) . . ? C11 C15 Ir1 70.3(3) . . ? C20 C15 Ir1 124.4(4) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 . . ? 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 1.996(4) . ? Ir1 C1 2.049(4) . ? Ir1 C11 2.156(5) . ? Ir1 C15 2.176(5) . ? Ir1 C12 2.226(5) . ? Ir1 C14 2.251(5) . ? Ir1 C13 2.257(5) . ? Ir1 Cl1 2.404(11) . ? Ir1 I1 2.6753(14) . ? N1 C7 1.358(6) . ? N1 C6 1.399(7) . ? N1 C9 1.401(6) . ? N2 C7 1.359(6) . ? N2 C8 1.379(7) . ? N2 C10 1.448(8) . ? C1 C6 1.398(7) . ? C1 C2 1.403(7) . ? C2 C3 1.388(8) . ? C2 H2 0.9500 . ? C3 C4 1.375(11) . ? C3 H3 0.9500 . ? C4 C5 1.378(10) . ? C4 H4 0.9500 . ? C5 C6 1.387(7) . ? C5 H5 0.9500 . ? C8 C9 1.333(9) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C15 1.404(7) . ? C11 C12 1.409(8) . ? C11 C16 1.525(8) . ? C12 C13 1.424(9) . ? C12 C17 1.498(8) . ? C13 C14 1.398(9) . ? C13 C18 1.501(9) . ? C14 C15 1.400(8) . ? C14 C19 1.518(8) . ? C15 C20 1.506(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 . ? 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 -2.2(7) . . . . ? Ir1 C1 C2 C3 177.5(4) . . . . ? C1 C2 C3 C4 0.5(8) . . . . ? C2 C3 C4 C5 0.6(9) . . . . ? C3 C4 C5 C6 0.0(9) . . . . ? C4 C5 C6 C1 -1.8(8) . . . . ? C4 C5 C6 N1 176.7(5) . . . . ? C2 C1 C6 C5 2.9(7) . . . . ? Ir1 C1 C6 C5 -176.8(4) . . . . ? C2 C1 C6 N1 -175.9(4) . . . . ? Ir1 C1 C6 N1 4.4(5) . . . . ? C7 N1 C6 C5 -177.8(4) . . . . ? C9 N1 C6 C5 -6.3(8) . . . . ? C7 N1 C6 C1 0.9(6) . . . . ? C9 N1 C6 C1 172.4(5) . . . . ? C6 N1 C7 N2 173.4(4) . . . . ? C9 N1 C7 N2 0.1(5) . . . . ? C6 N1 C7 Ir1 -6.1(5) . . . . ? C9 N1 C7 Ir1 -179.5(3) . . . . ? C8 N2 C7 N1 0.1(5) . . . . ? C10 N2 C7 N1 -178.1(5) . . . . ? C8 N2 C7 Ir1 179.5(4) . . . . ? C10 N2 C7 Ir1 1.3(8) . . . . ? C7 N2 C8 C9 -0.2(6) . . . . ? C10 N2 C8 C9 178.0(5) . . . . ? N2 C8 C9 N1 0.2(6) . . . . ? C7 N1 C9 C8 -0.2(6) . . . . ? C6 N1 C9 C8 -172.0(5) . . . . ? C15 C11 C12 C13 -1.1(5) . . . . ? C16 C11 C12 C13 -175.2(5) . . . . ? Ir1 C11 C12 C13 63.1(4) . . . . ? C15 C11 C12 C17 171.4(6) . . . . ? C16 C11 C12 C17 -2.6(9) . . . . ? Ir1 C11 C12 C17 -124.4(6) . . . . ? C15 C11 C12 Ir1 -64.2(3) . . . . ? C16 C11 C12 Ir1 121.7(5) . . . . ? C11 C12 C13 C14 1.3(6) . . . . ? C17 C12 C13 C14 -171.5(5) . . . . ? Ir1 C12 C13 C14 61.7(4) . . . . ? C11 C12 C13 C18 177.8(5) . . . . ? C17 C12 C13 C18 5.0(9) . . . . ? Ir1 C12 C13 C18 -121.7(6) . . . . ? C11 C12 C13 Ir1 -60.4(3) . . . . ? C17 C12 C13 Ir1 126.8(6) . . . . ? C12 C13 C14 C15 -1.0(6) . . . . ? C18 C13 C14 C15 -177.6(5) . . . . ? Ir1 C13 C14 C15 59.9(3) . . . . ? C12 C13 C14 C19 169.2(5) . . . . ? C18 C13 C14 C19 -7.4(9) . . . . ? Ir1 C13 C14 C19 -129.9(5) . . . . ? C12 C13 C14 Ir1 -60.8(4) . . . . ? C18 C13 C14 Ir1 122.6(6) . . . . ? C13 C14 C15 C11 0.3(5) . . . . ? C19 C14 C15 C11 -169.7(5) . . . . ? Ir1 C14 C15 C11 62.4(3) . . . . ? C13 C14 C15 C20 176.4(5) . . . . ? C19 C14 C15 C20 6.4(8) . . . . ? Ir1 C14 C15 C20 -121.5(5) . . . . ? C13 C14 C15 Ir1 -62.1(3) . . . . ? C19 C14 C15 Ir1 127.9(5) . . . . ? C12 C11 C15 C14 0.6(5) . . . . ? C16 C11 C15 C14 174.5(5) . . . . ? Ir1 C11 C15 C14 -65.0(3) . . . . ? C12 C11 C15 C20 -175.5(5) . . . . ? C16 C11 C15 C20 -1.6(8) . . . . ? Ir1 C11 C15 C20 118.9(5) . . . . ? C12 C11 C15 Ir1 65.6(3) . . . . ? C16 C11 C15 Ir1 -120.4(5) . . . . ?