#------------------------------------------------------------------------------ #$Date: 2021-10-01 03:50:20 +0300 (Fri, 01 Oct 2021) $ #$Revision: 269418 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158327.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_7158327 loop_ _publ_author_name 'Dai, Zengjin' 'Pan, Ying-Min' 'Wang, Shou-Guo' 'Zhang, Xumu' 'Yin, Qin' _publ_section_title ; Direct Reductive Amination of Ketones with Ammonium Salt Catalysed by Cp*Ir(III) Complexes Bearing an Amidato Ligand ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01710A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C27 H32 Cl Ir N O P, 0.323(H2 O)' _chemical_formula_sum 'C27 H32.65 Cl Ir N O1.32 P' _chemical_formula_weight 650.96 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-05-20 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-05-25 deposited with the CCDC. 2021-09-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.8894(7) _cell_length_b 13.1148(7) _cell_length_c 14.7203(8) _cell_measurement_reflns_used 9604 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.27 _cell_measurement_theta_min 4.52 _cell_volume 2488.3(2) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector 'Bruker PHOTON 100 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CMOS area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.0251 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 47540 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.330 _diffrn_reflns_theta_min 4.515 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.1 _diffrn_source_power 0.055 _diffrn_source_type 'Incoatec I\ms' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 12.144 _exptl_absorpt_correction_T_max 0.1665 _exptl_absorpt_correction_T_min 0.0376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1469 before and 0.0858 after correction. The Ratio of minimum to maximum transmission is 0.2258. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.738 _exptl_crystal_description needle _exptl_crystal_F_000 1285 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 1.788 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.110 _refine_ls_abs_structure_details ; Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.024(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4582 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0261 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+1.1084P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0682 _reflns_Friedel_coverage 0.767 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 4569 _reflns_number_total 4582 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01710a2.cif _cod_data_source_block cxy3274 _cod_database_code 7158327 _shelx_shelxl_version_number 2018/3 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Others Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(1) 3.a Free rotating group: O2(H2A,H2B) 3.b Ternary CH refined with riding coordinates: C2(H2) 3.c Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C1(H1A,H1B), C4(H4A,H4B) 3.d Aromatic/amide H refined with riding coordinates: C15(H15), C14(H14), C13(H13), C17(H17), C8(H8), C7(H7), C11(H11), C16(H16), C9(H9), C10(H10) 3.e Idealised Me refined as rotating group: C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B, H23C), C27(H27A,H27B,H27C) ; _shelx_res_file ; TITL cxy3274_a.res in P2(1)2(1)2(1) cxy3274.res created by SHELXL-2018/3 at 16:30:01 on 20-May-2021 CELL 1.54178 12.8894 13.1148 14.7203 90 90 90 ZERR 4 0.0007 0.0007 0.0008 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H Cl Ir N O P UNIT 108 130.58 4 4 4 5.29 4 L.S. 5 PLAN 5 TEMP -173 CONF BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.051000 1.108400 FVAR 0.08946 0.32321 IR1 4 0.267896 0.686546 0.174421 11.00000 0.02952 0.02058 = 0.02003 0.00044 -0.00066 0.00026 CL1 3 0.369903 0.627735 0.046229 11.00000 0.03620 0.02939 = 0.02513 -0.00243 0.00057 0.00056 P1 7 0.124883 0.620547 0.105051 11.00000 0.03150 0.02107 = 0.02282 0.00043 -0.00086 -0.00058 O1 6 0.388308 0.897739 0.096094 11.00000 0.03942 0.03018 = 0.02981 0.00340 -0.00469 -0.00263 N1 5 0.234406 0.806839 0.088520 11.00000 0.03399 0.02241 = 0.02478 0.00280 -0.00380 0.00566 C3 1 0.300555 0.881587 0.065471 11.00000 0.03268 0.02532 = 0.02502 0.00097 0.00188 0.00163 C26 1 0.328716 0.890608 0.303067 11.00000 0.04127 0.02854 = 0.02889 -0.00453 -0.00048 -0.00066 AFIX 137 H26A 2 0.365538 0.918755 0.250496 11.00000 -1.50000 H26B 2 0.367074 0.906889 0.358688 11.00000 -1.50000 H26C 2 0.259075 0.920358 0.306415 11.00000 -1.50000 AFIX 0 C15 1 0.132616 0.285041 0.014370 11.00000 0.06117 0.02454 = 0.02779 -0.00165 0.00734 -0.00377 AFIX 43 H15 2 0.131928 0.214813 -0.001437 11.00000 -1.20000 AFIX 0 C14 1 0.054016 0.347518 -0.014384 11.00000 0.04697 0.03216 = 0.02654 -0.00404 0.00473 -0.01007 AFIX 43 H14 2 0.000420 0.320443 -0.051541 11.00000 -1.20000 AFIX 0 C13 1 0.051425 0.450779 0.010159 11.00000 0.03551 0.02797 = 0.02237 -0.00227 0.00527 -0.00349 AFIX 43 H13 2 -0.003589 0.493544 -0.009660 11.00000 -1.20000 AFIX 0 C18 1 0.402109 0.712345 0.266197 11.00000 0.03843 0.02704 = 0.02066 0.00262 -0.00313 0.00240 C5 1 0.162234 0.882470 -0.044261 11.00000 0.03352 0.03371 = 0.03061 0.00977 -0.00200 -0.00407 AFIX 23 H5A 2 0.184191 0.843346 -0.098468 11.00000 -1.20000 H5B 2 0.101369 0.924866 -0.060264 11.00000 -1.20000 AFIX 0 C24 1 0.200844 0.519900 0.340572 11.00000 0.04932 0.03093 = 0.02771 0.00642 -0.00257 -0.00436 AFIX 137 H24A 2 0.126882 0.537130 0.342116 11.00000 -1.50000 H24B 2 0.224105 0.501415 0.401777 11.00000 -1.50000 H24C 2 0.211859 0.462194 0.299390 11.00000 -1.50000 AFIX 0 C17 1 0.212957 0.426923 0.091999 11.00000 0.03907 0.02865 = 0.02803 0.00103 0.00450 0.00012 AFIX 43 H17 2 0.267682 0.454133 0.127791 11.00000 -1.20000 AFIX 0 C8 1 -0.111102 0.532908 0.275151 11.00000 0.04506 0.03338 = 0.02808 -0.00005 -0.00030 -0.00656 AFIX 43 H8 2 -0.127103 0.474948 0.311237 11.00000 -1.20000 AFIX 0 C6 1 0.003275 0.618916 0.168165 11.00000 0.03393 0.03105 = 0.02208 -0.00526 -0.00212 0.00012 C7 1 -0.022299 0.533258 0.220635 11.00000 0.04005 0.02573 = 0.03060 -0.00305 -0.00257 -0.00226 AFIX 43 H7 2 0.021218 0.474820 0.219108 11.00000 -1.20000 AFIX 0 C20 1 0.229552 0.716119 0.315165 11.00000 0.03439 0.03194 = 0.01840 0.00149 0.00123 -0.00007 C19 1 0.320219 0.776800 0.293252 11.00000 0.03157 0.02977 = 0.02031 -0.00085 -0.00273 -0.00010 C25 1 0.130564 0.753874 0.357324 11.00000 0.04147 0.03309 = 0.03140 -0.00082 0.00218 0.00211 AFIX 137 H25A 2 0.117557 0.824127 0.337705 11.00000 -1.50000 H25B 2 0.136749 0.751822 0.423653 11.00000 -1.50000 H25C 2 0.072832 0.710294 0.338107 11.00000 -1.50000 AFIX 0 C22 1 0.364024 0.608381 0.275779 11.00000 0.04270 0.02554 = 0.01993 -0.00215 -0.00098 -0.00078 C1 1 0.104102 0.703769 0.006934 11.00000 0.03575 0.02510 = 0.02528 0.00186 0.00164 -0.00207 AFIX 23 H1A 2 0.146029 0.680192 -0.045355 11.00000 -1.20000 H1B 2 0.030048 0.703383 -0.010908 11.00000 -1.20000 AFIX 0 C2 1 0.137318 0.811000 0.035377 11.00000 0.03469 0.02419 = 0.02616 0.00395 -0.00175 -0.00072 AFIX 13 H2 2 0.081455 0.842221 0.073436 11.00000 -1.20000 AFIX 0 C23 1 0.429500 0.514083 0.260698 11.00000 0.04792 0.03276 = 0.02653 -0.00209 -0.00464 0.00508 AFIX 137 H23A 2 0.384900 0.453568 0.261272 11.00000 -1.50000 H23B 2 0.481282 0.508556 0.309197 11.00000 -1.50000 H23C 2 0.464713 0.519069 0.201861 11.00000 -1.50000 AFIX 0 C11 1 -0.063133 0.702669 0.170151 11.00000 0.04022 0.02606 = 0.03214 -0.00019 0.00324 -0.00223 AFIX 43 H11 2 -0.047298 0.761126 0.134651 11.00000 -1.20000 AFIX 0 C16 1 0.213529 0.323924 0.066652 11.00000 0.05223 0.03035 = 0.02343 0.00315 0.00691 0.00461 AFIX 43 H16 2 0.268886 0.280792 0.085057 11.00000 -1.20000 AFIX 0 C12 1 0.130616 0.489386 0.063894 11.00000 0.03787 0.02538 = 0.02051 -0.00007 0.00393 -0.00303 C9 1 -0.175656 0.617248 0.276410 11.00000 0.04525 0.03920 = 0.03041 -0.00474 0.00814 0.00004 AFIX 43 H9 2 -0.235903 0.617108 0.313585 11.00000 -1.20000 AFIX 0 C27 1 0.509151 0.743231 0.239795 11.00000 0.03661 0.03552 = 0.02652 0.00113 -0.00198 0.00337 AFIX 137 H27A 2 0.544233 0.685730 0.210401 11.00000 -1.50000 H27B 2 0.547949 0.763468 0.294137 11.00000 -1.50000 H27C 2 0.505696 0.800817 0.197477 11.00000 -1.50000 AFIX 0 C4 1 0.250662 0.948011 -0.008291 11.00000 0.03420 0.02803 = 0.03120 0.00593 -0.00109 0.00003 AFIX 23 H4A 2 0.224105 1.012593 0.017628 11.00000 -1.20000 H4B 2 0.301035 0.963958 -0.057033 11.00000 -1.20000 AFIX 0 C10 1 -0.152821 0.701940 0.223675 11.00000 0.03926 0.03163 = 0.03901 -0.00457 0.00603 0.00219 AFIX 43 H10 2 -0.197905 0.759245 0.223893 11.00000 -1.20000 AFIX 0 C21 1 0.261631 0.610212 0.307537 11.00000 0.04234 0.03005 = 0.01687 0.00068 -0.00185 -0.00174 AFIX 6 O2 6 0.476451 0.406792 0.033128 21.00000 0.07094 0.04022 = 0.06370 -0.01740 -0.02562 0.00632 H2A 2 0.471859 0.346972 0.007876 21.00000 -1.50000 H2B 2 0.538323 0.431379 0.024364 21.00000 -1.50000 AFIX 0 HKLF 4 REM cxy3274_a.res in P2(1)2(1)2(1) REM wR2 = 0.0682, GooF = S = 1.092, Restrained GooF = 1.092 for all data REM R1 = 0.0261 for 4569 Fo > 4sig(Fo) and 0.0262 for all 4582 data REM 307 parameters refined using 0 restraints END WGHT 0.0510 1.1160 REM Highest difference peak 1.788, deepest hole -0.591, 1-sigma level 0.110 Q1 1 0.2680 0.6204 0.1735 11.00000 0.05 1.79 Q2 1 0.2674 0.7557 0.1756 11.00000 0.05 1.78 Q3 1 0.2667 0.6867 0.1162 11.00000 0.05 1.62 Q4 1 0.2704 0.6878 0.2328 11.00000 0.05 1.60 Q5 1 0.1309 0.5550 0.0870 11.00000 0.05 0.55 ; _shelx_res_checksum 99471 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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 0.26790(2) 0.68655(2) 0.17442(2) 0.02338(10) Uani 1 1 d . . . . . Cl1 Cl 0.36990(12) 0.62773(11) 0.04623(9) 0.0302(3) Uani 1 1 d . . . . . P1 P 0.12488(12) 0.62055(11) 0.10505(10) 0.0251(3) Uani 1 1 d . . . . . O1 O 0.3883(4) 0.8977(3) 0.0961(3) 0.0331(10) Uani 1 1 d . . . . . N1 N 0.2344(4) 0.8068(4) 0.0885(3) 0.0271(10) Uani 1 1 d . . . . . C3 C 0.3006(5) 0.8816(5) 0.0655(4) 0.0277(12) Uani 1 1 d . . . . . C26 C 0.3287(6) 0.8906(5) 0.3031(4) 0.0329(14) Uani 1 1 d . . . . . H26A H 0.365538 0.918755 0.250496 0.049 Uiso 1 1 calc R U . . . H26B H 0.367074 0.906889 0.358688 0.049 Uiso 1 1 calc R U . . . H26C H 0.259075 0.920358 0.306415 0.049 Uiso 1 1 calc R U . . . C15 C 0.1326(6) 0.2850(5) 0.0144(4) 0.0378(15) Uani 1 1 d . . . . . H15 H 0.131928 0.214813 -0.001437 0.045 Uiso 1 1 calc R U . . . C14 C 0.0540(6) 0.3475(5) -0.0144(4) 0.0352(14) Uani 1 1 d . . . . . H14 H 0.000420 0.320443 -0.051541 0.042 Uiso 1 1 calc R U . . . C13 C 0.0514(5) 0.4508(5) 0.0102(4) 0.0286(12) Uani 1 1 d . . . . . H13 H -0.003589 0.493544 -0.009660 0.034 Uiso 1 1 calc R U . . . C18 C 0.4021(5) 0.7123(5) 0.2662(4) 0.0287(13) Uani 1 1 d . . . . . C5 C 0.1622(5) 0.8825(5) -0.0443(4) 0.0326(13) Uani 1 1 d . . . . . H5A H 0.184191 0.843346 -0.098468 0.039 Uiso 1 1 calc R U . . . H5B H 0.101369 0.924866 -0.060264 0.039 Uiso 1 1 calc R U . . . C24 C 0.2008(6) 0.5199(5) 0.3406(4) 0.0360(14) Uani 1 1 d . . . . . H24A H 0.126882 0.537130 0.342116 0.054 Uiso 1 1 calc R U . . . H24B H 0.224105 0.501415 0.401777 0.054 Uiso 1 1 calc R U . . . H24C H 0.211859 0.462194 0.299390 0.054 Uiso 1 1 calc R U . . . C17 C 0.2130(5) 0.4269(5) 0.0920(4) 0.0319(13) Uani 1 1 d . . . . . H17 H 0.267682 0.454133 0.127791 0.038 Uiso 1 1 calc R U . . . C8 C -0.1111(6) 0.5329(5) 0.2752(4) 0.0355(14) Uani 1 1 d . . . . . H8 H -0.127103 0.474948 0.311237 0.043 Uiso 1 1 calc R U . . . C6 C 0.0033(5) 0.6189(5) 0.1682(4) 0.0290(12) Uani 1 1 d . . . . . C7 C -0.0223(5) 0.5333(5) 0.2206(4) 0.0321(13) Uani 1 1 d . . . . . H7 H 0.021218 0.474820 0.219108 0.039 Uiso 1 1 calc R U . . . C20 C 0.2296(5) 0.7161(5) 0.3152(4) 0.0282(12) Uani 1 1 d . . . . . C19 C 0.3202(5) 0.7768(5) 0.2933(4) 0.0272(13) Uani 1 1 d . . . . . C25 C 0.1306(6) 0.7539(5) 0.3573(5) 0.0353(14) Uani 1 1 d . . . . . H25A H 0.117557 0.824127 0.337705 0.053 Uiso 1 1 calc R U . . . H25B H 0.136749 0.751822 0.423653 0.053 Uiso 1 1 calc R U . . . H25C H 0.072832 0.710294 0.338107 0.053 Uiso 1 1 calc R U . . . C22 C 0.3640(6) 0.6084(5) 0.2758(4) 0.0294(13) Uani 1 1 d . . . . . C1 C 0.1041(5) 0.7038(4) 0.0069(4) 0.0287(12) Uani 1 1 d . . . . . H1A H 0.146029 0.680192 -0.045355 0.034 Uiso 1 1 calc R U . . . H1B H 0.030048 0.703383 -0.010908 0.034 Uiso 1 1 calc R U . . . C2 C 0.1373(5) 0.8110(5) 0.0354(4) 0.0283(11) Uani 1 1 d . . . . . H2 H 0.081455 0.842221 0.073436 0.034 Uiso 1 1 calc R U . . . C23 C 0.4295(6) 0.5141(5) 0.2607(4) 0.0357(14) Uani 1 1 d . . . . . H23A H 0.384900 0.453568 0.261272 0.054 Uiso 1 1 calc R U . . . H23B H 0.481282 0.508556 0.309197 0.054 Uiso 1 1 calc R U . . . H23C H 0.464713 0.519069 0.201861 0.054 Uiso 1 1 calc R U . . . C11 C -0.0631(5) 0.7027(5) 0.1702(4) 0.0328(13) Uani 1 1 d . . . . . H11 H -0.047298 0.761126 0.134651 0.039 Uiso 1 1 calc R U . . . C16 C 0.2135(6) 0.3239(5) 0.0667(4) 0.0353(14) Uani 1 1 d . . . . . H16 H 0.268886 0.280792 0.085057 0.042 Uiso 1 1 calc R U . . . C12 C 0.1306(5) 0.4894(5) 0.0639(4) 0.0279(12) Uani 1 1 d . . . . . C9 C -0.1757(6) 0.6172(5) 0.2764(5) 0.0383(15) Uani 1 1 d . . . . . H9 H -0.235903 0.617108 0.313585 0.046 Uiso 1 1 calc R U . . . C27 C 0.5092(5) 0.7432(5) 0.2398(4) 0.0329(13) Uani 1 1 d . . . . . H27A H 0.544233 0.685730 0.210401 0.049 Uiso 1 1 calc R U . . . H27B H 0.547949 0.763468 0.294137 0.049 Uiso 1 1 calc R U . . . H27C H 0.505696 0.800817 0.197477 0.049 Uiso 1 1 calc R U . . . C4 C 0.2507(5) 0.9480(5) -0.0083(4) 0.0311(13) Uani 1 1 d . . . . . H4A H 0.224105 1.012593 0.017628 0.037 Uiso 1 1 calc R U . . . H4B H 0.301035 0.963958 -0.057033 0.037 Uiso 1 1 calc R U . . . C10 C -0.1528(6) 0.7019(5) 0.2237(5) 0.0366(14) Uani 1 1 d . . . . . H10 H -0.197905 0.759245 0.223893 0.044 Uiso 1 1 calc R U . . . C21 C 0.2616(6) 0.6102(5) 0.3075(4) 0.0298(12) Uani 1 1 d . . . . . O2 O 0.4765(17) 0.4068(14) 0.0331(14) 0.058(7) Uani 0.32(2) 1 d G . P . . H2A H 0.471859 0.346972 0.007876 0.087 Uiso 0.32(2) 1 d G U P . . H2B H 0.538323 0.431379 0.024364 0.087 Uiso 0.32(2) 1 d G U P . . 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 0.02952(15) 0.02058(14) 0.02003(14) 0.00044(8) -0.00066(8) 0.00026(8) Cl1 0.0362(7) 0.0294(7) 0.0251(7) -0.0024(5) 0.0006(6) 0.0006(6) P1 0.0315(7) 0.0211(7) 0.0228(7) 0.0004(5) -0.0009(6) -0.0006(6) O1 0.039(3) 0.030(2) 0.030(2) 0.0034(18) -0.005(2) -0.0026(19) N1 0.034(2) 0.022(2) 0.025(2) 0.0028(18) -0.004(2) 0.006(2) C3 0.033(3) 0.025(3) 0.025(3) 0.001(2) 0.002(2) 0.002(3) C26 0.041(4) 0.029(3) 0.029(3) -0.005(2) 0.000(3) -0.001(3) C15 0.061(4) 0.025(3) 0.028(3) -0.002(2) 0.007(3) -0.004(3) C14 0.047(4) 0.032(3) 0.027(3) -0.004(2) 0.005(3) -0.010(3) C13 0.036(3) 0.028(3) 0.022(3) -0.002(2) 0.005(2) -0.003(3) C18 0.038(3) 0.027(3) 0.021(3) 0.003(2) -0.003(2) 0.002(2) C5 0.034(3) 0.034(3) 0.031(3) 0.010(3) -0.002(3) -0.004(3) C24 0.049(4) 0.031(3) 0.028(3) 0.006(2) -0.003(3) -0.004(3) C17 0.039(3) 0.029(3) 0.028(3) 0.001(2) 0.004(3) 0.000(3) C8 0.045(4) 0.033(3) 0.028(3) 0.000(2) 0.000(3) -0.007(3) C6 0.034(3) 0.031(3) 0.022(3) -0.005(2) -0.002(3) 0.000(2) C7 0.040(3) 0.026(3) 0.031(3) -0.003(2) -0.003(3) -0.002(3) C20 0.034(3) 0.032(3) 0.018(2) 0.001(2) 0.001(3) 0.000(2) C19 0.032(3) 0.030(3) 0.020(3) -0.001(2) -0.003(2) 0.000(2) C25 0.041(3) 0.033(4) 0.031(3) -0.001(3) 0.002(3) 0.002(3) C22 0.043(3) 0.026(3) 0.020(3) -0.002(2) -0.001(3) -0.001(3) C1 0.036(3) 0.025(3) 0.025(3) 0.002(2) 0.002(2) -0.002(2) C2 0.035(3) 0.024(3) 0.026(3) 0.004(3) -0.002(2) -0.001(3) C23 0.048(4) 0.033(3) 0.027(3) -0.002(2) -0.005(3) 0.005(3) C11 0.040(3) 0.026(3) 0.032(3) 0.000(3) 0.003(3) -0.002(2) C16 0.052(4) 0.030(3) 0.023(3) 0.003(2) 0.007(3) 0.005(3) C12 0.038(3) 0.025(3) 0.021(3) 0.000(2) 0.004(2) -0.003(3) C9 0.045(4) 0.039(4) 0.030(3) -0.005(3) 0.008(3) 0.000(3) C27 0.037(3) 0.036(3) 0.027(3) 0.001(3) -0.002(2) 0.003(3) C4 0.034(3) 0.028(3) 0.031(3) 0.006(2) -0.001(2) 0.000(3) C10 0.039(3) 0.032(3) 0.039(3) -0.005(3) 0.006(3) 0.002(3) C21 0.042(3) 0.030(3) 0.017(2) 0.001(2) -0.002(2) -0.002(3) O2 0.071(13) 0.040(11) 0.064(13) -0.017(8) -0.026(11) 0.006(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 P1 Ir1 Cl1 88.23(5) . . ? N1 Ir1 Cl1 83.11(14) . . ? N1 Ir1 P1 81.19(15) . . ? N1 Ir1 C18 114.7(2) . . ? N1 Ir1 C20 113.6(2) . . ? N1 Ir1 C19 98.0(2) . . ? N1 Ir1 C22 152.9(2) . . ? N1 Ir1 C21 152.1(2) . . ? C18 Ir1 Cl1 95.71(17) . . ? C18 Ir1 P1 163.91(16) . . ? C20 Ir1 Cl1 157.69(17) . . ? C20 Ir1 P1 108.20(17) . . ? C20 Ir1 C18 64.4(2) . . ? C20 Ir1 C19 38.6(2) . . ? C20 Ir1 C22 64.0(2) . . ? C20 Ir1 C21 38.9(2) . . ? C19 Ir1 Cl1 128.21(18) . . ? C19 Ir1 P1 143.38(18) . . ? C19 Ir1 C18 37.0(2) . . ? C22 Ir1 Cl1 94.26(17) . . ? C22 Ir1 P1 125.76(18) . . ? C22 Ir1 C18 38.5(2) . . ? C22 Ir1 C19 62.7(2) . . ? C22 Ir1 C21 37.2(3) . . ? C21 Ir1 Cl1 124.58(18) . . ? C21 Ir1 P1 101.33(18) . . ? C21 Ir1 C18 63.7(2) . . ? C21 Ir1 C19 63.4(2) . . ? C6 P1 Ir1 118.2(2) . . ? C6 P1 C1 106.5(3) . . ? C6 P1 C12 101.1(3) . . ? C1 P1 Ir1 104.2(2) . . ? C12 P1 Ir1 118.3(2) . . ? C12 P1 C1 107.8(3) . . ? C3 N1 Ir1 125.4(4) . . ? C3 N1 C2 112.2(5) . . ? C2 N1 Ir1 121.9(4) . . ? O1 C3 N1 127.9(6) . . ? O1 C3 C4 123.0(6) . . ? N1 C3 C4 109.1(5) . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.4(6) . . ? C16 C15 H15 119.8 . . ? C15 C14 H14 119.5 . . ? C15 C14 C13 121.0(7) . . ? C13 C14 H14 119.5 . . ? C14 C13 H13 120.6 . . ? C12 C13 C14 118.8(6) . . ? C12 C13 H13 120.6 . . ? C19 C18 Ir1 71.3(4) . . ? C19 C18 C22 106.4(6) . . ? C19 C18 C27 127.2(6) . . ? C22 C18 Ir1 69.7(4) . . ? C22 C18 C27 126.3(6) . . ? C27 C18 Ir1 127.2(4) . . ? H5A C5 H5B 109.0 . . ? C2 C5 H5A 111.0 . . ? C2 C5 H5B 111.0 . . ? C4 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C4 C5 C2 103.6(5) . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? C16 C17 H17 120.4 . . ? C16 C17 C12 119.2(6) . . ? C12 C17 H17 120.4 . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C9 C8 C7 119.8(6) . . ? C7 C6 P1 119.5(5) . . ? C11 C6 P1 122.0(5) . . ? C11 C6 C7 118.4(6) . . ? C8 C7 C6 120.7(6) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C19 C20 Ir1 72.6(3) . . ? C19 C20 C25 126.5(6) . . ? C19 C20 C21 106.1(6) . . ? C25 C20 Ir1 130.4(4) . . ? C21 C20 Ir1 71.9(3) . . ? C21 C20 C25 126.0(6) . . ? C26 C19 Ir1 128.9(4) . . ? C18 C19 Ir1 71.6(3) . . ? C18 C19 C26 124.6(6) . . ? C18 C19 C20 109.7(5) . . ? C20 C19 Ir1 68.7(3) . . ? C20 C19 C26 125.6(6) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C22 Ir1 71.8(4) . . ? C18 C22 C23 124.3(6) . . ? C23 C22 Ir1 126.7(4) . . ? C21 C22 Ir1 71.7(4) . . ? C21 C22 C18 109.5(6) . . ? C21 C22 C23 126.0(6) . . ? P1 C1 H1A 110.3 . . ? P1 C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? C2 C1 P1 107.0(4) . . ? C2 C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? N1 C2 C5 104.5(5) . . ? N1 C2 C1 110.4(5) . . ? N1 C2 H2 109.2 . . ? C5 C2 H2 109.2 . . ? C1 C2 C5 114.3(5) . . ? C1 C2 H2 109.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C6 C11 H11 119.5 . . ? C6 C11 C10 120.9(6) . . ? C10 C11 H11 119.5 . . ? C15 C16 C17 119.7(6) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C13 C12 P1 120.2(5) . . ? C13 C12 C17 120.8(6) . . ? C17 C12 P1 118.9(5) . . ? C8 C9 H9 119.8 . . ? C8 C9 C10 120.3(7) . . ? C10 C9 H9 119.8 . . ? C18 C27 H27A 109.5 . . ? C18 C27 H27B 109.5 . . ? C18 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C3 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 C3 103.9(5) . . ? C5 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C11 C10 H10 120.1 . . ? C9 C10 C11 119.7(6) . . ? C9 C10 H10 120.1 . . ? C24 C21 Ir1 131.8(4) . . ? C20 C21 Ir1 69.2(3) . . ? C20 C21 C24 125.5(6) . . ? C22 C21 Ir1 71.1(3) . . ? C22 C21 C24 125.9(6) . . ? C22 C21 C20 108.1(6) . . ? H2A O2 H2B 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 Cl1 2.4258(14) . ? Ir1 P1 2.2781(15) . ? Ir1 N1 2.067(5) . ? Ir1 C18 2.221(6) . ? Ir1 C20 2.165(6) . ? Ir1 C19 2.217(6) . ? Ir1 C22 2.194(6) . ? Ir1 C21 2.202(6) . ? P1 C6 1.822(6) . ? P1 C1 1.830(6) . ? P1 C12 1.825(6) . ? O1 C3 1.236(8) . ? N1 C3 1.343(8) . ? N1 C2 1.477(7) . ? C3 C4 1.533(8) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C26 C19 1.504(9) . ? C15 H15 0.9500 . ? C15 C14 1.370(11) . ? C15 C16 1.393(11) . ? C14 H14 0.9500 . ? C14 C13 1.402(9) . ? C13 H13 0.9500 . ? C13 C12 1.387(9) . ? C18 C19 1.410(9) . ? C18 C22 1.456(9) . ? C18 C27 1.490(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C2 1.535(8) . ? C5 C4 1.523(9) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 C21 1.501(9) . ? C17 H17 0.9500 . ? C17 C16 1.401(9) . ? C17 C12 1.403(9) . ? C8 H8 0.9500 . ? C8 C7 1.398(10) . ? C8 C9 1.384(10) . ? C6 C7 1.403(9) . ? C6 C11 1.393(9) . ? C7 H7 0.9500 . ? C20 C19 1.450(9) . ? C20 C25 1.503(9) . ? C20 C21 1.454(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C22 C23 1.514(9) . ? C22 C21 1.400(10) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.529(8) . ? C2 H2 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C11 H11 0.9500 . ? C11 C10 1.399(10) . ? C16 H16 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.387(10) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C10 H10 0.9500 . ? O2 H2A 0.8702 . ? O2 H2B 0.8698 . ? 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 Ir1 P1 C6 C7 -91.1(5) . . . . ? Ir1 P1 C6 C11 85.2(5) . . . . ? Ir1 P1 C1 C2 -33.8(4) . . . . ? Ir1 P1 C12 C13 -170.9(4) . . . . ? Ir1 P1 C12 C17 12.9(6) . . . . ? Ir1 N1 C3 O1 -6.8(9) . . . . ? Ir1 N1 C3 C4 173.0(4) . . . . ? Ir1 N1 C2 C5 -157.2(4) . . . . ? Ir1 N1 C2 C1 -33.9(6) . . . . ? Ir1 C18 C19 C26 -125.1(6) . . . . ? Ir1 C18 C19 C20 58.3(4) . . . . ? Ir1 C18 C22 C23 122.4(6) . . . . ? Ir1 C18 C22 C21 -62.2(4) . . . . ? Ir1 C20 C19 C26 123.4(6) . . . . ? Ir1 C20 C19 C18 -60.1(4) . . . . ? Ir1 C20 C21 C24 -127.2(6) . . . . ? Ir1 C20 C21 C22 60.8(4) . . . . ? Ir1 C22 C21 C24 128.4(6) . . . . ? Ir1 C22 C21 C20 -59.6(4) . . . . ? P1 C6 C7 C8 175.1(5) . . . . ? P1 C6 C11 C10 -175.9(5) . . . . ? P1 C1 C2 N1 42.1(6) . . . . ? P1 C1 C2 C5 159.5(4) . . . . ? O1 C3 C4 C5 162.9(6) . . . . ? N1 C3 C4 C5 -16.9(7) . . . . ? C3 N1 C2 C5 15.1(7) . . . . ? C3 N1 C2 C1 138.4(5) . . . . ? C15 C14 C13 C12 0.5(9) . . . . ? C14 C15 C16 C17 1.7(10) . . . . ? C14 C13 C12 P1 -175.0(5) . . . . ? C14 C13 C12 C17 1.1(9) . . . . ? C18 C22 C21 Ir1 62.2(4) . . . . ? C18 C22 C21 C24 -169.4(6) . . . . ? C18 C22 C21 C20 2.6(6) . . . . ? C8 C9 C10 C11 -1.1(11) . . . . ? C6 P1 C1 C2 91.8(4) . . . . ? C6 P1 C12 C13 58.4(5) . . . . ? C6 P1 C12 C17 -117.8(5) . . . . ? C6 C11 C10 C9 0.7(10) . . . . ? C7 C8 C9 C10 0.2(10) . . . . ? C7 C6 C11 C10 0.5(9) . . . . ? C19 C18 C22 Ir1 62.4(4) . . . . ? C19 C18 C22 C23 -175.2(6) . . . . ? C19 C18 C22 C21 0.2(7) . . . . ? C19 C20 C21 Ir1 -65.1(4) . . . . ? C19 C20 C21 C24 167.7(6) . . . . ? C19 C20 C21 C22 -4.3(6) . . . . ? C25 C20 C19 Ir1 -127.8(6) . . . . ? C25 C20 C19 C26 -4.5(10) . . . . ? C25 C20 C19 C18 172.1(6) . . . . ? C25 C20 C21 Ir1 127.3(6) . . . . ? C25 C20 C21 C24 0.1(10) . . . . ? C25 C20 C21 C22 -172.0(6) . . . . ? C22 C18 C19 Ir1 -61.3(4) . . . . ? C22 C18 C19 C26 173.6(6) . . . . ? C22 C18 C19 C20 -3.0(7) . . . . ? C1 P1 C6 C7 152.2(5) . . . . ? C1 P1 C6 C11 -31.4(6) . . . . ? C1 P1 C12 C13 -53.1(6) . . . . ? C1 P1 C12 C17 130.7(5) . . . . ? C2 N1 C3 O1 -178.7(6) . . . . ? C2 N1 C3 C4 1.1(7) . . . . ? C2 C5 C4 C3 24.8(6) . . . . ? C23 C22 C21 Ir1 -122.5(6) . . . . ? C23 C22 C21 C24 5.9(10) . . . . ? C23 C22 C21 C20 177.9(6) . . . . ? C11 C6 C7 C8 -1.4(9) . . . . ? C16 C15 C14 C13 -1.9(10) . . . . ? C16 C17 C12 P1 174.9(5) . . . . ? C16 C17 C12 C13 -1.3(9) . . . . ? C12 P1 C6 C7 39.7(5) . . . . ? C12 P1 C6 C11 -144.0(5) . . . . ? C12 P1 C1 C2 -160.3(4) . . . . ? C12 C17 C16 C15 -0.2(9) . . . . ? C9 C8 C7 C6 1.1(10) . . . . ? C27 C18 C19 Ir1 123.0(6) . . . . ? C27 C18 C19 C26 -2.1(10) . . . . ? C27 C18 C19 C20 -178.7(5) . . . . ? C27 C18 C22 Ir1 -121.9(6) . . . . ? C27 C18 C22 C23 0.5(9) . . . . ? C27 C18 C22 C21 176.0(6) . . . . ? C4 C5 C2 N1 -24.5(6) . . . . ? C4 C5 C2 C1 -145.2(5) . . . . ? C21 C20 C19 Ir1 64.6(4) . . . . ? C21 C20 C19 C26 -172.0(6) . . . . ? C21 C20 C19 C18 4.5(7) . . . . ?