#------------------------------------------------------------------------------ #$Date: 2017-11-02 04:52:44 +0200 (Thu, 02 Nov 2017) $ #$Revision: 202505 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/78/1547866.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_1547866 loop_ _publ_author_name 'Islamova, Regina M. M' 'Dobrynin, Mikhail V.' 'Vlasov, Andrey V.' 'Eremina, Anzhelika A.' 'Kinzhalov, Mikhail A.' 'Kolesnikov, Ilya E.' 'Zolotarev, Andrei' 'Masloborodova, Eleonora A.' 'Luzyanin, Konstantin' _publ_section_title ; Iridium(III)-catalysed cross-linking of polysiloxanes leading to the thermally resistant luminescent silicone rubbers ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/C7CY02013A _journal_year 2017 _chemical_formula_moiety 'C32 H27 Cl Ir N3, C H2 Cl2' _chemical_formula_sum 'C33 H29 Cl3 Ir N3' _chemical_formula_weight 766.14 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2016-06-16 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-09-21 deposited with the CCDC. 2017-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.838(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.0427(6) _cell_length_b 8.6872(3) _cell_length_c 21.3383(6) _cell_measurement_reflns_used 5599 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 75.9090 _cell_measurement_theta_min 4.0490 _cell_volume 2971.73(18) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.3829 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -113.00 -17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -40.3787 -57.0000 -30.0000 96 #__ type_ start__ end____ width___ exp.time_ 2 omega -86.00 -11.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -40.3787 -57.0000 150.0000 75 #__ type_ start__ end____ width___ exp.time_ 3 omega -122.00 -36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -40.3787 -178.0000 0.0000 86 #__ type_ start__ end____ width___ exp.time_ 4 omega 113.00 139.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -69.0000 -35.1379 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 30.00 95.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -95.0000 -150.0000 65 #__ type_ start__ end____ width___ exp.time_ 6 omega 38.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -30.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 40.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 45.00 85.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -30.0000 0.0000 40 #__ type_ start__ end____ width___ exp.time_ 9 omega 54.00 79.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 15.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 10 omega 98.00 171.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 15.0000 90.0000 73 #__ type_ start__ end____ width___ exp.time_ 11 omega 30.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -95.0000 -30.0000 46 #__ type_ start__ end____ width___ exp.time_ 12 omega 79.00 108.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -95.0000 -30.0000 29 #__ type_ start__ end____ width___ exp.time_ 13 omega 52.00 85.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -30.0000 33 #__ type_ start__ end____ width___ exp.time_ 14 omega 112.00 154.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 30.0000 -180.0000 42 #__ type_ start__ end____ width___ exp.time_ 15 omega 98.00 147.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -77.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 16 omega 48.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 -30.0000 90.0000 43 #__ type_ start__ end____ width___ exp.time_ 17 omega 98.00 124.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 30.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega 133.00 163.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 113.0000 30.0000 120.0000 30 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0254020000 _diffrn_orient_matrix_UB_12 0.1438931000 _diffrn_orient_matrix_UB_13 0.0306896000 _diffrn_orient_matrix_UB_21 -0.0309596000 _diffrn_orient_matrix_UB_22 0.0769335000 _diffrn_orient_matrix_UB_23 -0.0691420000 _diffrn_orient_matrix_UB_31 -0.0873849000 _diffrn_orient_matrix_UB_32 -0.0692157000 _diffrn_orient_matrix_UB_33 -0.0130757000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_unetI/netI 0.0570 _diffrn_reflns_Laue_measured_fraction_full 0.974 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 13389 _diffrn_reflns_point_group_measured_fraction_full 0.974 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.995 _diffrn_reflns_theta_min 2.885 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 11.391 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.712 _exptl_crystal_description prism _exptl_crystal_F_000 1504 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 1.194 _refine_diff_density_min -1.076 _refine_diff_density_rms 0.137 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 5467 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0334 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.0839 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4499 _reflns_number_total 5467 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cy02013a2.cif _cod_data_source_block km_859 _cod_original_cell_volume 2971.72(17) _cod_database_code 1547866 _shelxl_version_number 2014/6 _chemical_oxdiff_formula 'C33 H29 Cl3 Ir N3' _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. ; _reflns_odcompleteness_completeness 89.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 80.95 _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 2.a Secondary CH2 refined with riding coordinates: C33(H33A,H33B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C) ; _shelx_res_file ; TITL CF solution in P21/n CELL 1.54184 17.042671 8.687169 21.33834 90 109.8377 90 ZERR 4 0.000554 0.00025 0.000609 0 0.0035 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N Cl Ir UNIT 132 116 12 12 4 L.S. 4 PLAN 25 BOND MORE -1 BOND $H CONF fmap 2 acta OMIT -4 140 REM REM REM WGHT 0.034600 FVAR 2.22943 IR1 5 0.376535 0.080055 0.611106 11.00000 0.00958 0.01388 = 0.01793 -0.00102 0.00192 -0.00156 CL1 4 0.342095 0.221785 0.503480 11.00000 0.01668 0.01984 = 0.01972 0.00035 0.00437 -0.00283 N1 3 0.561958 0.198534 0.648031 11.00000 0.02026 0.02739 = 0.01902 -0.00326 0.00438 -0.00382 N2 3 0.386338 -0.115120 0.560290 11.00000 0.01428 0.01774 = 0.01996 0.00144 0.00384 0.00074 N3 3 0.350795 0.259562 0.663493 11.00000 0.01029 0.01514 = 0.02267 0.00060 0.00202 -0.00094 C1 1 0.494016 0.151028 0.633840 11.00000 0.00505 0.02113 = 0.01880 0.00211 0.00415 -0.00242 C2 1 0.637479 0.275804 0.661844 11.00000 0.01458 0.02313 = 0.01418 -0.00025 0.00227 -0.00569 C3 1 0.639026 0.433892 0.675843 11.00000 0.01770 0.02190 = 0.01780 -0.00078 0.00196 0.00011 C4 1 0.713855 0.511590 0.685820 11.00000 0.02812 0.02110 = 0.01856 -0.00097 0.00402 -0.00423 AFIX 43 H4 2 0.716492 0.616824 0.694288 11.00000 -1.20000 AFIX 0 C5 1 0.784637 0.435856 0.683439 11.00000 0.01613 0.03089 = 0.01841 -0.00105 0.00304 -0.00868 C6 1 0.780228 0.279486 0.670215 11.00000 0.01325 0.02883 = 0.01942 0.00118 0.00307 0.00122 AFIX 43 H6 2 0.827766 0.229020 0.668892 11.00000 -1.20000 AFIX 0 C7 1 0.706758 0.194294 0.658737 11.00000 0.01717 0.02392 = 0.01826 0.00031 0.00055 -0.00393 C8 1 0.701518 0.027897 0.641313 11.00000 0.02242 0.02959 = 0.03033 -0.00929 0.00602 0.00029 AFIX 137 H8A 2 0.671589 0.015621 0.594556 11.00000 -1.50000 H8B 2 0.672830 -0.025991 0.666374 11.00000 -1.50000 H8C 2 0.756755 -0.013315 0.651767 11.00000 -1.50000 AFIX 0 C9 1 0.864818 0.523778 0.695434 11.00000 0.01864 0.03848 = 0.03471 -0.00339 0.00675 -0.00870 AFIX 137 H9A 2 0.905689 0.489548 0.736294 11.00000 -1.50000 H9B 2 0.854718 0.631785 0.698441 11.00000 -1.50000 H9C 2 0.885036 0.505913 0.659196 11.00000 -1.50000 AFIX 0 C10 1 0.562285 0.515540 0.678664 11.00000 0.01742 0.03252 = 0.03475 0.00001 0.00325 0.00129 AFIX 137 H10A 2 0.574659 0.622586 0.688215 11.00000 -1.50000 H10B 2 0.545093 0.470647 0.713032 11.00000 -1.50000 H10C 2 0.518212 0.505403 0.636541 11.00000 -1.50000 AFIX 0 C11 1 0.455436 -0.159216 0.547476 11.00000 0.01411 0.02278 = 0.02375 -0.00074 0.00374 0.00190 AFIX 43 H11 2 0.502845 -0.097834 0.562858 11.00000 -1.20000 AFIX 0 C12 1 0.458665 -0.290605 0.512761 11.00000 0.02405 0.01826 = 0.01965 0.00112 0.01168 0.00491 AFIX 43 H12 2 0.506976 -0.316415 0.504136 11.00000 -1.20000 AFIX 0 C13 1 0.388630 -0.384495 0.490693 11.00000 0.02814 0.01559 = 0.01901 -0.00435 0.00729 0.00203 AFIX 43 H13 2 0.389899 -0.475645 0.468199 11.00000 -1.20000 AFIX 0 C14 1 0.317604 -0.340881 0.502544 11.00000 0.02566 0.02309 = 0.01721 0.00174 0.00469 -0.00307 AFIX 43 H14 2 0.270439 -0.403048 0.487932 11.00000 -1.20000 AFIX 0 C15 1 0.315286 -0.203671 0.536429 11.00000 0.02107 0.00973 = 0.01956 0.00256 0.00427 -0.00315 C16 1 0.242432 -0.140073 0.549307 11.00000 0.02060 0.01743 = 0.01701 0.00427 0.00150 -0.00235 C17 1 0.163835 -0.211130 0.526564 11.00000 0.01815 0.02163 = 0.02508 -0.00006 0.00347 -0.00637 AFIX 43 H17 2 0.156080 -0.303444 0.503175 11.00000 -1.20000 AFIX 0 C18 1 0.098230 -0.141222 0.539612 11.00000 0.01327 0.02851 = 0.02476 0.00283 0.00133 -0.00526 AFIX 43 H18 2 0.045716 -0.186679 0.524674 11.00000 -1.20000 AFIX 0 C19 1 0.109835 -0.004326 0.574662 11.00000 0.00656 0.02811 = 0.02839 0.00714 0.00490 0.00347 AFIX 43 H19 2 0.065336 0.040769 0.583690 11.00000 -1.20000 AFIX 0 C20 1 0.188265 0.066803 0.596644 11.00000 0.01966 0.01673 = 0.01781 0.00138 0.00457 -0.00014 AFIX 43 H20 2 0.194912 0.159881 0.619390 11.00000 -1.20000 AFIX 0 C21 1 0.256438 0.000469 0.585006 11.00000 0.00398 0.02096 = 0.01618 0.00321 0.00150 -0.00550 C22 1 0.320230 0.397210 0.636032 11.00000 0.01573 0.01988 = 0.02029 -0.00301 0.00091 0.00082 AFIX 43 H22 2 0.314358 0.416347 0.591787 11.00000 -1.20000 AFIX 0 C23 1 0.297659 0.509466 0.672358 11.00000 0.02101 0.01463 = 0.02986 0.00090 0.00373 0.00245 AFIX 43 H23 2 0.276996 0.603651 0.653037 11.00000 -1.20000 AFIX 0 C24 1 0.306328 0.479394 0.738263 11.00000 0.02071 0.02377 = 0.02717 -0.00684 0.00809 -0.00339 AFIX 43 H24 2 0.291437 0.553928 0.763443 11.00000 -1.20000 AFIX 0 C25 1 0.336666 0.340658 0.766277 11.00000 0.01759 0.02277 = 0.02346 -0.00269 0.00338 -0.00100 AFIX 43 H25 2 0.341522 0.320149 0.810214 11.00000 -1.20000 AFIX 0 C26 1 0.360441 0.229374 0.728681 11.00000 0.00998 0.01886 = 0.01912 0.00070 -0.00197 -0.00372 C27 1 0.391619 0.075912 0.750586 11.00000 0.01155 0.01783 = 0.02436 0.00237 0.00321 -0.00497 C28 1 0.410413 0.023686 0.816042 11.00000 0.02190 0.02527 = 0.02176 -0.00196 0.00684 -0.00500 AFIX 43 H28 2 0.403982 0.089359 0.848378 11.00000 -1.20000 AFIX 0 C29 1 0.438469 -0.124875 0.832927 11.00000 0.02900 0.02910 = 0.01818 0.00784 0.00000 -0.00411 AFIX 43 H29 2 0.451342 -0.159094 0.876565 11.00000 -1.20000 AFIX 0 C30 1 0.447307 -0.222483 0.784528 11.00000 0.02272 0.01653 = 0.03391 0.00716 -0.00046 0.00481 AFIX 43 H30 2 0.465376 -0.323045 0.795681 11.00000 -1.20000 AFIX 0 C31 1 0.429410 -0.171612 0.719273 11.00000 0.01876 0.01962 = 0.02584 -0.00233 0.00156 -0.00300 AFIX 43 H31 2 0.435493 -0.238622 0.687241 11.00000 -1.20000 AFIX 0 C32 1 0.402671 -0.022369 0.701620 11.00000 0.01619 0.01580 = 0.02231 -0.00067 0.00460 -0.00230 CL2 4 0.105312 0.355995 0.468091 11.00000 0.03133 0.02851 = 0.03608 -0.00175 0.00912 -0.00267 CL3 4 0.054488 0.129709 0.359460 11.00000 0.02370 0.03420 = 0.03290 -0.00215 0.00098 -0.01036 C33 1 0.134303 0.190904 0.433022 11.00000 0.02512 0.03847 = 0.02793 -0.00412 -0.00420 0.01008 AFIX 23 H33A 2 0.147138 0.108102 0.465433 11.00000 -1.20000 H33B 2 0.184350 0.213208 0.422707 11.00000 -1.20000 AFIX 0 HKLF 4 REM CF solution in P21/n REM R1 = 0.0334 for 4499 Fo > 4sig(Fo) and 0.0470 for all 5467 data REM 364 parameters refined using 0 restraints END WGHT 0.0346 0.0000 REM Highest difference peak 1.194, deepest hole -1.076, 1-sigma level 0.137 Q1 1 0.4218 0.0427 0.6023 11.00000 0.05 1.19 Q2 1 0.3271 0.1035 0.6153 11.00000 0.05 1.07 Q3 1 0.3664 0.4212 0.6625 11.00000 0.05 0.96 Q4 1 0.3828 0.2009 0.6148 11.00000 0.05 0.91 Q5 1 0.3540 0.0779 0.6575 11.00000 0.05 0.83 Q6 1 0.3413 0.0048 0.6134 11.00000 0.05 0.76 Q7 1 0.3767 -0.2521 0.6116 11.00000 0.05 0.70 Q8 1 0.3970 -0.0407 0.6229 11.00000 0.05 0.69 Q9 1 0.2585 0.0812 0.6161 11.00000 0.05 0.68 Q10 1 0.2997 0.1861 0.5064 11.00000 0.05 0.64 Q11 1 0.3863 0.0177 0.6628 11.00000 0.05 0.62 Q12 1 0.3065 -0.1158 0.6262 11.00000 0.05 0.57 Q13 1 0.4451 0.2473 0.6621 11.00000 0.05 0.57 Q14 1 0.3618 -0.0616 0.5872 11.00000 0.05 0.51 Q15 1 0.1210 0.4871 0.4673 11.00000 0.05 0.50 Q16 1 0.0992 0.1521 0.3439 11.00000 0.05 0.50 Q17 1 0.4554 0.2844 0.5943 11.00000 0.05 0.49 Q18 1 0.4181 -0.0941 0.6953 11.00000 0.05 0.49 Q19 1 0.4767 -0.1818 0.7106 11.00000 0.05 0.49 Q20 1 0.4504 -0.0774 0.6611 11.00000 0.05 0.48 Q21 1 0.4413 -0.1271 0.5973 11.00000 0.05 0.47 Q22 1 0.1421 0.3965 0.4459 11.00000 0.05 0.46 Q23 1 0.4946 0.0679 0.6167 11.00000 0.05 0.46 Q24 1 0.4408 0.1178 0.6759 11.00000 0.05 0.45 Q25 1 0.3325 0.2595 0.5388 11.00000 0.05 0.45 ; _shelx_res_checksum 11933 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 Ir1 Ir 0.37654(2) 0.08006(3) 0.61111(2) 0.01450(7) Uani 1 1 d . Cl1 Cl 0.34209(7) 0.22178(15) 0.50348(5) 0.0192(3) Uani 1 1 d . N1 N 0.5620(3) 0.1985(6) 0.6480(2) 0.0228(10) Uani 1 1 d . N2 N 0.3863(3) -0.1151(5) 0.56029(19) 0.0178(9) Uani 1 1 d . N3 N 0.3508(2) 0.2596(5) 0.66349(19) 0.0169(9) Uani 1 1 d . C1 C 0.4940(3) 0.1510(6) 0.6338(2) 0.0150(10) Uani 1 1 d . C2 C 0.6375(3) 0.2758(7) 0.6618(2) 0.0180(11) Uani 1 1 d . C3 C 0.6390(3) 0.4339(7) 0.6758(2) 0.0202(11) Uani 1 1 d . C4 C 0.7139(4) 0.5116(7) 0.6858(2) 0.0236(12) Uani 1 1 d . H4 H 0.7165 0.6168 0.6943 0.028 Uiso 1 1 calc R C5 C 0.7846(3) 0.4359(7) 0.6834(2) 0.0225(12) Uani 1 1 d . C6 C 0.7802(3) 0.2795(7) 0.6702(2) 0.0211(12) Uani 1 1 d . H6 H 0.8278 0.2290 0.6689 0.025 Uiso 1 1 calc R C7 C 0.7068(3) 0.1943(7) 0.6587(2) 0.0212(12) Uani 1 1 d . C8 C 0.7015(4) 0.0279(7) 0.6413(3) 0.0282(13) Uani 1 1 d . H8A H 0.6716 0.0156 0.5946 0.042 Uiso 1 1 calc GR H8B H 0.6728 -0.0260 0.6664 0.042 Uiso 1 1 calc GR H8C H 0.7568 -0.0133 0.6518 0.042 Uiso 1 1 calc GR C9 C 0.8648(4) 0.5238(8) 0.6954(3) 0.0312(14) Uani 1 1 d . H9A H 0.9057 0.4895 0.7363 0.047 Uiso 1 1 calc GR H9B H 0.8547 0.6318 0.6984 0.047 Uiso 1 1 calc GR H9C H 0.8850 0.5059 0.6592 0.047 Uiso 1 1 calc GR C10 C 0.5623(3) 0.5155(8) 0.6787(3) 0.0297(14) Uani 1 1 d . H10A H 0.5747 0.6226 0.6882 0.044 Uiso 1 1 calc GR H10B H 0.5451 0.4706 0.7130 0.044 Uiso 1 1 calc GR H10C H 0.5182 0.5054 0.6365 0.044 Uiso 1 1 calc GR C11 C 0.4554(3) -0.1592(7) 0.5475(2) 0.0209(12) Uani 1 1 d . H11 H 0.5028 -0.0978 0.5629 0.025 Uiso 1 1 calc R C12 C 0.4587(3) -0.2906(6) 0.5128(2) 0.0196(11) Uani 1 1 d . H12 H 0.5070 -0.3164 0.5041 0.023 Uiso 1 1 calc R C13 C 0.3886(3) -0.3845(6) 0.4907(2) 0.0211(12) Uani 1 1 d . H13 H 0.3899 -0.4756 0.4682 0.025 Uiso 1 1 calc R C14 C 0.3176(3) -0.3409(7) 0.5025(2) 0.0226(12) Uani 1 1 d . H14 H 0.2704 -0.4030 0.4879 0.027 Uiso 1 1 calc R C15 C 0.3153(3) -0.2037(6) 0.5364(2) 0.0175(11) Uani 1 1 d . C16 C 0.2424(3) -0.1401(6) 0.5493(2) 0.0196(11) Uani 1 1 d . C17 C 0.1638(3) -0.2111(7) 0.5266(2) 0.0226(12) Uani 1 1 d . H17 H 0.1561 -0.3034 0.5032 0.027 Uiso 1 1 calc R C18 C 0.0982(3) -0.1412(7) 0.5396(2) 0.0235(12) Uani 1 1 d . H18 H 0.0457 -0.1867 0.5247 0.028 Uiso 1 1 calc R C19 C 0.1098(3) -0.0043(7) 0.5747(2) 0.0213(12) Uani 1 1 d . H19 H 0.0653 0.0408 0.5837 0.026 Uiso 1 1 calc R C20 C 0.1883(3) 0.0668(6) 0.5966(2) 0.0185(11) Uani 1 1 d . H20 H 0.1949 0.1599 0.6194 0.022 Uiso 1 1 calc R C21 C 0.2564(3) 0.0005(6) 0.5850(2) 0.0142(10) Uani 1 1 d . C22 C 0.3202(3) 0.3972(6) 0.6360(2) 0.0200(11) Uani 1 1 d . H22 H 0.3144 0.4163 0.5918 0.024 Uiso 1 1 calc R C23 C 0.2977(3) 0.5095(7) 0.6724(3) 0.0231(12) Uani 1 1 d . H23 H 0.2770 0.6037 0.6530 0.028 Uiso 1 1 calc R C24 C 0.3063(3) 0.4794(7) 0.7383(3) 0.0239(12) Uani 1 1 d . H24 H 0.2914 0.5539 0.7634 0.029 Uiso 1 1 calc R C25 C 0.3367(3) 0.3407(7) 0.7663(3) 0.0222(12) Uani 1 1 d . H25 H 0.3415 0.3201 0.8102 0.027 Uiso 1 1 calc R C26 C 0.3604(3) 0.2294(6) 0.7287(2) 0.0177(11) Uani 1 1 d . C27 C 0.3916(3) 0.0759(7) 0.7506(2) 0.0186(11) Uani 1 1 d . C28 C 0.4104(3) 0.0237(7) 0.8160(3) 0.0231(12) Uani 1 1 d . H28 H 0.4040 0.0894 0.8484 0.028 Uiso 1 1 calc R C29 C 0.4385(4) -0.1249(7) 0.8329(2) 0.0275(14) Uani 1 1 d . H29 H 0.4513 -0.1591 0.8766 0.033 Uiso 1 1 calc R C30 C 0.4473(3) -0.2225(7) 0.7845(3) 0.0270(13) Uani 1 1 d . H30 H 0.4654 -0.3230 0.7957 0.032 Uiso 1 1 calc R C31 C 0.4294(3) -0.1716(7) 0.7193(3) 0.0229(12) Uani 1 1 d . H31 H 0.4355 -0.2386 0.6872 0.028 Uiso 1 1 calc R C32 C 0.4027(3) -0.0224(6) 0.7016(2) 0.0186(11) Uani 1 1 d . Cl2 Cl 0.10531(9) 0.35599(18) 0.46809(7) 0.0326(3) Uani 1 1 d . Cl3 Cl 0.05449(9) 0.12971(18) 0.35946(7) 0.0325(3) Uani 1 1 d . C33 C 0.1343(4) 0.1909(8) 0.4330(3) 0.0339(15) Uani 1 1 d . H33A H 0.1471 0.1081 0.4654 0.041 Uiso 1 1 calc R H33B H 0.1844 0.2132 0.4227 0.041 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.00958(11) 0.01388(12) 0.01793(11) -0.00102(8) 0.00192(7) -0.00156(9) Cl1 0.0167(6) 0.0198(7) 0.0197(5) 0.0003(4) 0.0044(4) -0.0028(5) N1 0.020(2) 0.027(3) 0.0190(19) -0.0033(18) 0.0044(17) -0.004(2) N2 0.014(2) 0.018(2) 0.0200(19) 0.0014(17) 0.0038(16) 0.0007(18) N3 0.010(2) 0.015(2) 0.0227(19) 0.0006(17) 0.0020(15) -0.0009(18) C1 0.005(2) 0.021(3) 0.019(2) 0.0021(19) 0.0042(17) -0.002(2) C2 0.015(2) 0.023(3) 0.014(2) -0.0002(19) 0.0023(17) -0.006(2) C3 0.018(3) 0.022(3) 0.018(2) -0.001(2) 0.0020(19) 0.000(2) C4 0.028(3) 0.021(3) 0.019(2) -0.001(2) 0.004(2) -0.004(2) C5 0.016(3) 0.031(3) 0.018(2) -0.001(2) 0.0030(19) -0.009(2) C6 0.013(2) 0.029(3) 0.019(2) 0.001(2) 0.0031(18) 0.001(2) C7 0.017(3) 0.024(3) 0.018(2) 0.000(2) 0.0006(19) -0.004(2) C8 0.022(3) 0.030(3) 0.030(3) -0.009(2) 0.006(2) 0.000(3) C9 0.019(3) 0.038(4) 0.035(3) -0.003(3) 0.007(2) -0.009(3) C10 0.017(3) 0.033(4) 0.035(3) 0.000(3) 0.003(2) 0.001(3) C11 0.014(3) 0.023(3) 0.024(2) -0.001(2) 0.0037(19) 0.002(2) C12 0.024(3) 0.018(3) 0.020(2) 0.001(2) 0.012(2) 0.005(2) C13 0.028(3) 0.016(3) 0.019(2) -0.0044(19) 0.007(2) 0.002(2) C14 0.026(3) 0.023(3) 0.017(2) 0.002(2) 0.005(2) -0.003(2) C15 0.021(3) 0.010(3) 0.020(2) 0.0026(19) 0.0043(19) -0.003(2) C16 0.021(3) 0.017(3) 0.017(2) 0.004(2) 0.0015(19) -0.002(2) C17 0.018(3) 0.022(3) 0.025(2) 0.000(2) 0.003(2) -0.006(2) C18 0.013(3) 0.029(3) 0.025(2) 0.003(2) 0.001(2) -0.005(2) C19 0.007(2) 0.028(3) 0.028(3) 0.007(2) 0.005(2) 0.003(2) C20 0.020(3) 0.017(3) 0.018(2) 0.001(2) 0.0046(19) 0.000(2) C21 0.004(2) 0.021(3) 0.016(2) 0.0032(19) 0.0015(16) -0.006(2) C22 0.016(3) 0.020(3) 0.020(2) -0.003(2) 0.0009(19) 0.001(2) C23 0.021(3) 0.015(3) 0.030(3) 0.001(2) 0.004(2) 0.002(2) C24 0.021(3) 0.024(3) 0.027(3) -0.007(2) 0.008(2) -0.003(2) C25 0.018(3) 0.023(3) 0.023(2) -0.003(2) 0.003(2) -0.001(2) C26 0.010(2) 0.019(3) 0.019(2) 0.001(2) -0.0020(17) -0.004(2) C27 0.012(2) 0.018(3) 0.024(2) 0.002(2) 0.0032(18) -0.005(2) C28 0.022(3) 0.025(3) 0.022(2) -0.002(2) 0.007(2) -0.005(2) C29 0.029(3) 0.029(3) 0.018(2) 0.008(2) 0.000(2) -0.004(3) C30 0.023(3) 0.017(3) 0.034(3) 0.007(2) 0.000(2) 0.005(2) C31 0.019(3) 0.020(3) 0.026(2) -0.002(2) 0.002(2) -0.003(2) C32 0.016(3) 0.016(3) 0.022(2) -0.001(2) 0.0046(19) -0.002(2) Cl2 0.0313(8) 0.0285(8) 0.0361(7) -0.0018(6) 0.0091(6) -0.0027(6) Cl3 0.0237(7) 0.0342(8) 0.0329(6) -0.0021(6) 0.0010(5) -0.0104(6) C33 0.025(3) 0.038(4) 0.028(3) -0.004(3) -0.004(2) 0.010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' N N 0.0311 0.0180 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N2 Ir1 Cl1 87.55(12) N2 Ir1 N3 171.17(17) N2 Ir1 C21 80.2(2) N3 Ir1 Cl1 95.71(12) C1 Ir1 Cl1 88.54(14) C1 Ir1 N2 97.4(2) C1 Ir1 N3 90.87(19) C1 Ir1 C21 177.6(2) C1 Ir1 C32 91.5(2) C21 Ir1 Cl1 90.86(13) C21 Ir1 N3 91.49(19) C32 Ir1 Cl1 176.12(16) C32 Ir1 N2 96.29(19) C32 Ir1 N3 80.41(19) C32 Ir1 C21 89.3(2) C1 N1 C2 171.7(6) C11 N2 Ir1 125.1(4) C11 N2 C15 118.9(5) C15 N2 Ir1 116.0(4) C22 N3 Ir1 123.8(3) C22 N3 C26 120.3(5) C26 N3 Ir1 115.7(4) N1 C1 Ir1 177.1(5) N1 C2 C3 117.8(5) N1 C2 C7 118.8(5) C7 C2 C3 123.4(5) C2 C3 C10 121.0(5) C4 C3 C2 117.2(5) C4 C3 C10 121.8(6) C3 C4 H4 119.1 C5 C4 C3 121.7(6) C5 C4 H4 119.1 C4 C5 C9 120.1(6) C6 C5 C4 119.0(5) C6 C5 C9 121.0(5) C5 C6 H6 118.8 C5 C6 C7 122.5(5) C7 C6 H6 118.8 C2 C7 C6 116.3(5) C2 C7 C8 121.6(5) C6 C7 C8 122.0(5) C7 C8 H8A 109.5 C7 C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8B 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C5 C9 H9A 109.5 C5 C9 H9B 109.5 C5 C9 H9C 109.5 H9A C9 H9B 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C3 C10 H10A 109.5 C3 C10 H10B 109.5 C3 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 N2 C11 H11 118.6 N2 C11 C12 122.8(5) C12 C11 H11 118.6 C11 C12 H12 120.5 C11 C12 C13 119.0(5) C13 C12 H12 120.5 C12 C13 H13 120.5 C14 C13 C12 119.1(5) C14 C13 H13 120.5 C13 C14 H14 119.6 C13 C14 C15 120.7(5) C15 C14 H14 119.6 N2 C15 C14 119.4(5) N2 C15 C16 114.4(5) C14 C15 C16 126.2(5) C17 C16 C15 122.6(5) C17 C16 C21 122.2(5) C21 C16 C15 115.2(5) C16 C17 H17 120.7 C18 C17 C16 118.7(5) C18 C17 H17 120.7 C17 C18 H18 119.7 C17 C18 C19 120.7(5) C19 C18 H18 119.7 C18 C19 H19 119.8 C18 C19 C20 120.4(5) C20 C19 H19 119.8 C19 C20 H20 119.4 C21 C20 C19 121.1(5) C21 C20 H20 119.4 C16 C21 Ir1 114.0(4) C20 C21 Ir1 128.9(4) C20 C21 C16 117.0(5) N3 C22 H22 119.3 N3 C22 C23 121.4(5) C23 C22 H22 119.3 C22 C23 H23 120.6 C22 C23 C24 118.8(5) C24 C23 H23 120.6 C23 C24 H24 119.9 C25 C24 C23 120.2(6) C25 C24 H24 119.9 C24 C25 H25 120.1 C24 C25 C26 119.9(5) C26 C25 H25 120.1 N3 C26 C25 119.4(5) N3 C26 C27 114.0(5) C25 C26 C27 126.5(5) C28 C27 C26 123.6(5) C28 C27 C32 120.0(5) C32 C27 C26 116.3(5) C27 C28 H28 119.8 C29 C28 C27 120.4(5) C29 C28 H28 119.8 C28 C29 H29 120.2 C28 C29 C30 119.6(5) C30 C29 H29 120.2 C29 C30 H30 119.7 C29 C30 C31 120.6(5) C31 C30 H30 119.7 C30 C31 H31 119.7 C32 C31 C30 120.7(5) C32 C31 H31 119.7 C27 C32 Ir1 113.4(4) C31 C32 Ir1 127.9(4) C31 C32 C27 118.7(5) Cl2 C33 Cl3 112.2(3) Cl2 C33 H33A 109.2 Cl2 C33 H33B 109.2 Cl3 C33 H33A 109.2 Cl3 C33 H33B 109.2 H33A C33 H33B 107.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Ir1 Cl1 2.4939(11) Ir1 N2 2.050(4) Ir1 N3 2.051(5) Ir1 C1 1.991(5) Ir1 C21 2.050(5) Ir1 C32 2.034(5) N1 C1 1.168(7) N1 C2 1.392(7) N2 C11 1.352(7) N2 C15 1.378(6) N3 C22 1.356(7) N3 C26 1.369(6) C2 C3 1.404(8) C2 C7 1.397(8) C3 C4 1.394(8) C3 C10 1.507(8) C4 H4 0.9300 C4 C5 1.390(8) C5 C6 1.384(8) C5 C9 1.510(7) C6 H6 0.9300 C6 C7 1.403(7) C7 C8 1.488(8) C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11 0.9300 C11 C12 1.372(7) C12 H12 0.9300 C12 C13 1.389(7) C13 H13 0.9300 C13 C14 1.371(8) C14 H14 0.9300 C14 C15 1.402(7) C15 C16 1.468(8) C16 C17 1.403(7) C16 C21 1.416(8) C17 H17 0.9300 C17 C18 1.381(8) C18 H18 0.9300 C18 C19 1.383(8) C19 H19 0.9300 C19 C20 1.401(7) C20 H20 0.9300 C20 C21 1.393(7) C22 H22 0.9300 C22 C23 1.379(7) C23 H23 0.9300 C23 C24 1.388(8) C24 H24 0.9300 C24 C25 1.367(8) C25 H25 0.9300 C25 C26 1.401(8) C26 C27 1.452(8) C27 C28 1.398(7) C27 C32 1.411(7) C28 H28 0.9300 C28 C29 1.381(8) C29 H29 0.9300 C29 C30 1.383(8) C30 H30 0.9300 C30 C31 1.392(7) C31 H31 0.9300 C31 C32 1.383(8) Cl2 C33 1.764(6) Cl3 C33 1.774(5) C33 H33A 0.9700 C33 H33B 0.9700 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 Ir1 N2 C11 C12 -179.5(4) Ir1 N2 C15 C14 -178.5(4) Ir1 N2 C15 C16 2.2(5) Ir1 N3 C22 C23 174.6(4) Ir1 N3 C26 C25 -174.0(4) Ir1 N3 C26 C27 3.0(6) N1 C2 C3 C4 -176.4(4) N1 C2 C3 C10 2.5(7) N1 C2 C7 C6 177.3(4) N1 C2 C7 C8 -0.2(7) N2 C11 C12 C13 -1.2(8) N2 C15 C16 C17 177.6(4) N2 C15 C16 C21 -1.0(6) N3 C22 C23 C24 -0.3(8) N3 C26 C27 C28 176.4(5) N3 C26 C27 C32 -3.7(7) C2 C3 C4 C5 -1.3(7) C3 C2 C7 C6 -0.3(7) C3 C2 C7 C8 -177.7(5) C3 C4 C5 C6 0.6(7) C3 C4 C5 C9 -179.2(5) C4 C5 C6 C7 0.3(7) C5 C6 C7 C2 -0.5(7) C5 C6 C7 C8 177.0(5) C7 C2 C3 C4 1.2(7) C7 C2 C3 C10 -179.9(5) C9 C5 C6 C7 -179.9(5) C10 C3 C4 C5 179.8(5) C11 N2 C15 C14 3.2(7) C11 N2 C15 C16 -176.1(4) C11 C12 C13 C14 1.9(7) C12 C13 C14 C15 0.0(7) C13 C14 C15 N2 -2.6(7) C13 C14 C15 C16 176.7(5) C14 C15 C16 C17 -1.8(8) C14 C15 C16 C21 179.7(5) C15 N2 C11 C12 -1.4(7) C15 C16 C17 C18 -178.5(5) C15 C16 C21 Ir1 -0.7(5) C15 C16 C21 C20 178.3(4) C16 C17 C18 C19 -0.3(8) C17 C16 C21 Ir1 -179.2(4) C17 C16 C21 C20 -0.2(7) C17 C18 C19 C20 1.0(8) C18 C19 C20 C21 -1.3(8) C19 C20 C21 Ir1 179.7(4) C19 C20 C21 C16 0.9(7) C21 C16 C17 C18 0.0(8) C22 N3 C26 C25 1.4(7) C22 N3 C26 C27 178.4(4) C22 C23 C24 C25 -0.1(9) C23 C24 C25 C26 1.1(9) C24 C25 C26 N3 -1.8(8) C24 C25 C26 C27 -178.3(5) C25 C26 C27 C28 -6.9(9) C25 C26 C27 C32 173.0(5) C26 N3 C22 C23 -0.4(8) C26 C27 C28 C29 178.9(5) C26 C27 C32 Ir1 2.6(6) C26 C27 C32 C31 -177.7(5) C27 C28 C29 C30 -0.5(9) C28 C27 C32 Ir1 -177.4(4) C28 C27 C32 C31 2.2(8) C28 C29 C30 C31 1.0(9) C29 C30 C31 C32 0.2(9) C30 C31 C32 Ir1 177.8(4) C30 C31 C32 C27 -1.8(8) C32 C27 C28 C29 -1.1(8)