#------------------------------------------------------------------------------ #$Date: 2021-10-20 02:16:43 +0300 (Wed, 20 Oct 2021) $ #$Revision: 270037 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/85/7708580.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_7708580 loop_ _publ_author_name 'Yang, Yan' 'Wang, Cheng-Ming' 'Pan, Feng-Hua' 'Qin, Qi-Pin' 'Xie, Qiu-Ji' 'Chen, Qing' 'Liang, Hong' _publ_section_title ; Synthesis and biological evaluation of mixed-ligands cyclometalated iridium(III)-quinoline complexes ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D1DT02416G _journal_year 2021 _chemical_formula_moiety 'C39 H24 Br2 Ir N3 O' _chemical_formula_sum 'C39 H24 Br2 Ir N3 O' _chemical_formula_weight 902.63 _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_Hall '-I 4ad' _space_group_name_H-M_alt 'I 41/a :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2020-02-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-07-10 deposited with the CCDC. 2021-10-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 18.1807(5) _cell_length_b 18.1807(5) _cell_length_c 36.8214(13) _cell_measurement_reflns_used 6025 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.2700 _cell_measurement_theta_min 3.6870 _cell_volume 12170.9(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0233 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.931 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 21.00 61.00 1.00 10.00 -- 18.63 -99.00-120.00 40 2 \w -85.00 -59.00 1.00 10.00 -- -18.94 178.00-120.00 26 3 \w -82.00 9.00 1.00 10.00 -- -18.94 -77.00 -30.00 91 4 \w -26.00 0.00 1.00 10.00 -- -18.94 -57.00 90.00 26 5 \w -46.00 50.00 1.00 10.00 -- -18.94 77.00 90.00 96 6 \w -87.00 7.00 1.00 10.00 -- -18.94 -19.00 150.00 94 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0221501000 _diffrn_orient_matrix_UB_12 0.0320167000 _diffrn_orient_matrix_UB_13 0.0008502000 _diffrn_orient_matrix_UB_21 -0.0316185000 _diffrn_orient_matrix_UB_22 -0.0213792000 _diffrn_orient_matrix_UB_23 -0.0040015000 _diffrn_orient_matrix_UB_31 -0.0057047000 _diffrn_orient_matrix_UB_32 -0.0059865000 _diffrn_orient_matrix_UB_33 0.0188425000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_unetI/netI 0.0806 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.931 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_number 46769 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.931 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.184 _diffrn_reflns_theta_min 3.357 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 7.054 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68457 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour BROWN _exptl_crystal_density_diffrn 1.970 _exptl_crystal_description BLOCK _exptl_crystal_F_000 6944 _refine_diff_density_max 2.793 _refine_diff_density_min -1.473 _refine_diff_density_rms 0.178 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 415 _refine_ls_number_reflns 7659 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0530 _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^)+(0.0545P)^2^+118.3956P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1182 _refine_ls_wR_factor_ref 0.1397 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4827 _reflns_number_total 7659 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1dt02416g2.cif _cod_data_source_block 15 _cod_original_cell_volume 12170.8(8) _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 7708580 _shelxl_version_number 2014-3 _chemical_oxdiff_formula 'C1 H1 O1 N1' _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 99.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C36(H36) ; _shelx_res_file ; TITL 15 in I41/a #88 REM reset to I41/a #88 CELL 0.71073 18.18065 18.18065 36.8214 90 90 90 ZERR 16 0.00049 0.00049 0.00134 0 0 0 LATT 2 SYMM 0.75-Y,0.25+X,0.25+Z SYMM -X,0.5-Y,+Z SYMM 0.25+Y,0.25-X,0.25+Z SFAC C H Br Ir N O UNIT 624 384 32 16 48 16 L.S. 10 PLAN 20 fmap 2 53 ACTA REM REM REM WGHT 0.054500 118.395599 FVAR 0.35930 IR1 4 0.763286 0.543499 0.020703 11.00000 0.02857 0.02922 = 0.03193 0.00089 -0.00130 0.00570 BR1 3 0.925674 0.316977 -0.014427 11.00000 0.05192 0.05775 = 0.08563 -0.00249 -0.00198 0.02065 BR2 3 0.709872 0.283005 -0.122568 11.00000 0.10380 0.05612 = 0.05514 -0.01637 -0.00649 0.00327 O1 6 0.824593 0.444213 0.008497 11.00000 0.03892 0.03596 = 0.04761 -0.00577 -0.00314 0.00872 N1 5 0.708741 0.502708 -0.026558 11.00000 0.02719 0.04458 = 0.03656 0.00659 -0.00923 -0.00156 N2 5 0.807820 0.620318 -0.015430 11.00000 0.03390 0.02870 = 0.03432 0.00214 -0.00237 0.00146 N3 5 0.718671 0.475506 0.061317 11.00000 0.03633 0.02537 = 0.03844 0.00045 0.00440 0.00174 C1 1 0.871686 0.612260 -0.036185 11.00000 0.04068 0.03807 = 0.02482 0.00047 0.00035 0.00098 C2 1 0.918179 0.551902 -0.030699 11.00000 0.04758 0.04153 = 0.04429 0.00614 0.00336 0.00974 AFIX 43 H2 2 0.906073 0.516693 -0.013379 11.00000 -1.20000 AFIX 0 C3 1 0.981870 0.544182 -0.050781 11.00000 0.05815 0.06461 = 0.07064 -0.00196 0.01313 0.02238 AFIX 43 H3 2 1.013282 0.504795 -0.046404 11.00000 -1.20000 AFIX 0 C4 1 0.999328 0.596316 -0.078063 11.00000 0.05598 0.08568 = 0.06547 -0.00173 0.03077 0.00751 AFIX 43 H4 2 1.040992 0.590089 -0.092390 11.00000 -1.20000 AFIX 0 C5 1 0.955305 0.654805 -0.083102 11.00000 0.07822 0.05165 = 0.05573 0.00615 0.03382 -0.00397 AFIX 43 H5 2 0.967878 0.689428 -0.100628 11.00000 -1.20000 AFIX 0 C6 1 0.890145 0.665335 -0.062464 11.00000 0.05150 0.04465 = 0.03358 0.00282 0.00504 -0.00539 C7 1 0.845482 0.727453 -0.066608 11.00000 0.06905 0.04206 = 0.04125 0.01616 0.00051 -0.00102 AFIX 43 H7 2 0.856765 0.762536 -0.084125 11.00000 -1.20000 AFIX 0 C8 1 0.786245 0.736299 -0.045218 11.00000 0.04866 0.03449 = 0.05259 0.01206 0.00355 0.00979 AFIX 43 H8 2 0.757261 0.778221 -0.047376 11.00000 -1.20000 AFIX 0 C9 1 0.768139 0.681501 -0.019372 11.00000 0.03749 0.03175 = 0.03777 0.00061 -0.00326 0.00578 C10 1 0.705555 0.688109 0.005258 11.00000 0.04213 0.03089 = 0.03698 -0.00113 -0.00554 0.00330 C11 1 0.696188 0.629224 0.029361 11.00000 0.02845 0.03627 = 0.04034 -0.00637 -0.00247 0.00307 C12 1 0.638354 0.632728 0.053670 11.00000 0.04565 0.03657 = 0.04845 0.00237 0.00541 0.00512 AFIX 43 H12 2 0.630943 0.594057 0.069793 11.00000 -1.20000 AFIX 0 C13 1 0.590928 0.692870 0.054562 11.00000 0.04400 0.05665 = 0.06179 -0.00092 0.01091 0.02008 AFIX 43 H13 2 0.552651 0.694020 0.071307 11.00000 -1.20000 AFIX 0 C14 1 0.600317 0.750624 0.030829 11.00000 0.04688 0.04272 = 0.08876 0.00165 0.00364 0.02204 AFIX 43 H14 2 0.568532 0.790687 0.031400 11.00000 -1.20000 AFIX 0 C15 1 0.657786 0.748351 0.006036 11.00000 0.05010 0.03606 = 0.05986 0.00516 -0.00672 0.01009 AFIX 43 H15 2 0.664543 0.787071 -0.010128 11.00000 -1.20000 AFIX 0 C16 1 0.828898 0.568674 0.062495 11.00000 0.03407 0.03181 = 0.04247 -0.00460 -0.00213 0.01069 C17 1 0.884397 0.623086 0.063455 11.00000 0.03729 0.03995 = 0.05251 -0.00718 -0.00760 0.00397 AFIX 43 H17 2 0.891198 0.653941 0.043592 11.00000 -1.20000 AFIX 0 C18 1 0.928590 0.630671 0.093746 11.00000 0.03822 0.05757 = 0.06000 -0.01009 -0.01028 -0.00644 AFIX 43 H18 2 0.963559 0.667992 0.094238 11.00000 -1.20000 AFIX 0 C19 1 0.922321 0.584661 0.123133 11.00000 0.05661 0.07383 = 0.03573 -0.00564 -0.01216 0.00383 AFIX 43 H19 2 0.953449 0.589889 0.143009 11.00000 -1.20000 AFIX 0 C20 1 0.868511 0.529898 0.122736 11.00000 0.04957 0.05858 = 0.03246 0.00356 -0.00325 0.00833 AFIX 43 H20 2 0.863412 0.497999 0.142319 11.00000 -1.20000 AFIX 0 C21 1 0.822521 0.523647 0.092605 11.00000 0.03916 0.03838 = 0.03165 0.00257 -0.00509 0.00710 C22 1 0.761994 0.470496 0.091178 11.00000 0.03930 0.03699 = 0.02941 0.00592 0.00590 0.00378 C23 1 0.746250 0.418292 0.118376 11.00000 0.05085 0.04946 = 0.04155 0.00650 -0.00153 0.00716 AFIX 43 H23 2 0.778342 0.413148 0.137879 11.00000 -1.20000 AFIX 0 C24 1 0.686682 0.376346 0.116768 11.00000 0.06184 0.03886 = 0.06288 0.00926 0.00353 0.00105 AFIX 43 H24 2 0.677371 0.342438 0.135112 11.00000 -1.20000 AFIX 0 C25 1 0.637433 0.382887 0.087417 11.00000 0.05000 0.03031 = 0.05800 0.00456 0.00641 0.00104 C26 1 0.570928 0.342795 0.084532 11.00000 0.05534 0.03808 = 0.08001 0.01354 0.01023 -0.00605 AFIX 43 H26 2 0.559475 0.308119 0.102218 11.00000 -1.20000 AFIX 0 C27 1 0.523815 0.353642 0.056791 11.00000 0.03932 0.04217 = 0.11393 0.00206 0.00661 -0.00151 AFIX 43 H27 2 0.480675 0.326299 0.055399 11.00000 -1.20000 AFIX 0 C28 1 0.539966 0.406716 0.029721 11.00000 0.04084 0.05229 = 0.07013 -0.00089 -0.00612 -0.00390 AFIX 43 H28 2 0.507675 0.414137 0.010479 11.00000 -1.20000 AFIX 0 C29 1 0.602320 0.446250 0.032071 11.00000 0.03868 0.04565 = 0.05437 0.00437 0.00955 -0.00407 AFIX 43 H29 2 0.611404 0.482230 0.014687 11.00000 -1.20000 AFIX 0 C30 1 0.654391 0.435193 0.059884 11.00000 0.03901 0.02917 = 0.03745 -0.00113 0.00835 0.00445 C31 1 0.654979 0.530696 -0.045401 11.00000 0.04394 0.03946 = 0.06626 -0.00234 0.00319 0.00785 AFIX 43 H31 2 0.637923 0.576717 -0.038283 11.00000 -1.20000 AFIX 0 C32 1 0.616552 0.494620 -0.078643 11.00000 0.07607 0.05504 = 0.04616 0.01639 0.00716 0.04825 AFIX 43 H32 2 0.574971 0.513988 -0.089821 11.00000 -1.20000 AFIX 0 C33 1 0.647932 0.436116 -0.088839 11.00000 0.06836 0.06133 = 0.03308 -0.00412 -0.00768 -0.02064 AFIX 43 H33 2 0.629799 0.414134 -0.109815 11.00000 -1.20000 AFIX 0 C34 1 0.708940 0.399928 -0.071312 11.00000 0.04444 0.05104 = 0.04019 0.00922 0.00147 -0.00618 C35 1 0.746721 0.335541 -0.082160 11.00000 0.06791 0.03141 = 0.03932 -0.00501 0.00672 -0.00626 C36 1 0.807618 0.311453 -0.065402 11.00000 0.06485 0.04046 = 0.06001 0.00230 0.01446 0.00712 AFIX 43 H36 2 0.831382 0.269698 -0.074074 11.00000 -1.20000 AFIX 0 C37 1 0.835714 0.347825 -0.035345 11.00000 0.04178 0.03264 = 0.04924 -0.00218 0.00068 0.00179 C38 1 0.800992 0.409862 -0.020320 11.00000 0.04218 0.02674 = 0.04626 -0.00621 0.00881 0.00002 C39 1 0.737918 0.437610 -0.039636 11.00000 0.04543 0.03596 = 0.03658 0.00066 0.00479 0.00113 HKLF 4 REM 15 in I41/a #88 REM R1 = 0.0530 for 4827 Fo > 4sig(Fo) and 0.1073 for all 7659 data REM 415 parameters refined using 0 restraints END WGHT 0.0544 118.3339 REM Highest difference peak 2.793, deepest hole -1.473, 1-sigma level 0.178 Q1 1 0.7980 0.2455 -0.0997 11.00000 0.05 2.79 Q2 1 0.5853 0.4594 -0.0773 11.00000 0.05 1.10 Q3 1 0.5939 0.4672 -0.0847 11.00000 0.05 0.97 Q4 1 0.6334 0.4970 -0.0736 11.00000 0.05 0.80 Q5 1 0.8696 0.4123 0.0138 11.00000 0.05 0.74 Q6 1 0.6040 0.5217 -0.0799 11.00000 0.05 0.71 Q7 1 0.7199 0.5360 0.0231 11.00000 0.05 0.67 Q8 1 0.6451 0.4999 -0.0826 11.00000 0.05 0.65 Q9 1 0.9151 0.3661 0.0027 11.00000 0.05 0.63 Q10 1 0.6141 0.4765 -0.0990 11.00000 0.05 0.63 Q11 1 0.7748 0.5187 0.0203 11.00000 0.05 0.61 Q12 1 0.8672 0.3116 -0.0242 11.00000 0.05 0.60 Q13 1 0.7384 0.4570 -0.0586 11.00000 0.05 0.60 Q14 1 0.8858 0.4140 0.0170 11.00000 0.05 0.59 Q15 1 0.7320 0.6930 -0.0123 11.00000 0.05 0.57 Q16 1 0.8953 0.4054 0.0233 11.00000 0.05 0.57 Q17 1 0.7512 0.5347 0.0279 11.00000 0.05 0.56 Q18 1 0.6456 0.4809 0.0182 11.00000 0.05 0.56 Q19 1 0.5378 0.3209 0.0619 11.00000 0.05 0.55 Q20 1 0.8212 0.5630 0.0058 11.00000 0.05 0.54 ; _shelx_res_checksum 58491 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.333 _oxdiff_exptl_absorpt_empirical_full_min 0.676 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' 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 0.76329(2) 0.54350(2) 0.02070(2) 0.02991(11) Uani 1 1 d . . . . . Br1 Br 0.92567(6) 0.31698(6) -0.01443(3) 0.0651(3) Uani 1 1 d . . . . . Br2 Br 0.70987(8) 0.28300(6) -0.12257(3) 0.0717(4) Uani 1 1 d . . . . . O1 O 0.8246(3) 0.4442(3) 0.00850(16) 0.0408(14) Uani 1 1 d . . . . . N1 N 0.7087(4) 0.5027(4) -0.02656(18) 0.0361(16) Uani 1 1 d . . . . . N2 N 0.8078(4) 0.6203(4) -0.01543(17) 0.0323(15) Uani 1 1 d . . . . . N3 N 0.7187(4) 0.4755(4) 0.06132(18) 0.0334(15) Uani 1 1 d . . . . . C1 C 0.8717(5) 0.6123(5) -0.0362(2) 0.0345(19) Uani 1 1 d . . . . . C2 C 0.9182(5) 0.5519(5) -0.0307(2) 0.044(2) Uani 1 1 d . . . . . H2 H 0.9061 0.5167 -0.0134 0.053 Uiso 1 1 calc R . . . . C3 C 0.9819(6) 0.5442(6) -0.0508(3) 0.064(3) Uani 1 1 d . . . . . H3 H 1.0133 0.5048 -0.0464 0.077 Uiso 1 1 calc R . . . . C4 C 0.9993(6) 0.5963(7) -0.0781(3) 0.069(3) Uani 1 1 d . . . . . H4 H 1.0410 0.5901 -0.0924 0.083 Uiso 1 1 calc R . . . . C5 C 0.9553(6) 0.6548(6) -0.0831(3) 0.062(3) Uani 1 1 d . . . . . H5 H 0.9679 0.6894 -0.1006 0.074 Uiso 1 1 calc R . . . . C6 C 0.8901(5) 0.6653(5) -0.0625(2) 0.043(2) Uani 1 1 d . . . . . C7 C 0.8455(6) 0.7275(5) -0.0666(2) 0.051(2) Uani 1 1 d . . . . . H7 H 0.8568 0.7625 -0.0841 0.061 Uiso 1 1 calc R . . . . C8 C 0.7862(5) 0.7363(5) -0.0452(2) 0.045(2) Uani 1 1 d . . . . . H8 H 0.7573 0.7782 -0.0474 0.054 Uiso 1 1 calc R . . . . C9 C 0.7681(5) 0.6815(5) -0.0194(2) 0.0357(19) Uani 1 1 d . . . . . C10 C 0.7056(5) 0.6881(5) 0.0053(2) 0.0367(19) Uani 1 1 d . . . . . C11 C 0.6962(4) 0.6292(5) 0.0294(2) 0.0350(19) Uani 1 1 d . . . . . C12 C 0.6384(5) 0.6327(5) 0.0537(2) 0.044(2) Uani 1 1 d . . . . . H12 H 0.6309 0.5941 0.0698 0.052 Uiso 1 1 calc R . . . . C13 C 0.5909(5) 0.6929(6) 0.0546(3) 0.054(3) Uani 1 1 d . . . . . H13 H 0.5527 0.6940 0.0713 0.065 Uiso 1 1 calc R . . . . C14 C 0.6003(6) 0.7506(6) 0.0308(3) 0.059(3) Uani 1 1 d . . . . . H14 H 0.5685 0.7907 0.0314 0.071 Uiso 1 1 calc R . . . . C15 C 0.6578(5) 0.7484(5) 0.0060(3) 0.049(2) Uani 1 1 d . . . . . H15 H 0.6645 0.7871 -0.0101 0.058 Uiso 1 1 calc R . . . . C16 C 0.8289(5) 0.5687(4) 0.0625(2) 0.0361(19) Uani 1 1 d . . . . . C17 C 0.8844(5) 0.6231(5) 0.0635(3) 0.043(2) Uani 1 1 d . . . . . H17 H 0.8912 0.6539 0.0436 0.052 Uiso 1 1 calc R . . . . C18 C 0.9286(5) 0.6307(6) 0.0937(3) 0.052(3) Uani 1 1 d . . . . . H18 H 0.9636 0.6680 0.0942 0.062 Uiso 1 1 calc R . . . . C19 C 0.9223(6) 0.5847(6) 0.1231(3) 0.055(3) Uani 1 1 d . . . . . H19 H 0.9534 0.5899 0.1430 0.066 Uiso 1 1 calc R . . . . C20 C 0.8685(5) 0.5299(6) 0.1227(2) 0.047(2) Uani 1 1 d . . . . . H20 H 0.8634 0.4980 0.1423 0.056 Uiso 1 1 calc R . . . . C21 C 0.8225(5) 0.5236(5) 0.0926(2) 0.0364(19) Uani 1 1 d . . . . . C22 C 0.7620(5) 0.4705(5) 0.0912(2) 0.0352(19) Uani 1 1 d . . . . . C23 C 0.7462(5) 0.4183(5) 0.1184(2) 0.047(2) Uani 1 1 d . . . . . H23 H 0.7783 0.4131 0.1379 0.057 Uiso 1 1 calc R . . . . C24 C 0.6867(6) 0.3763(5) 0.1168(3) 0.055(3) Uani 1 1 d . . . . . H24 H 0.6774 0.3424 0.1351 0.065 Uiso 1 1 calc R . . . . C25 C 0.6374(5) 0.3829(5) 0.0874(3) 0.046(2) Uani 1 1 d . . . . . C26 C 0.5709(6) 0.3428(5) 0.0845(3) 0.058(3) Uani 1 1 d . . . . . H26 H 0.5595 0.3081 0.1022 0.069 Uiso 1 1 calc R . . . . C27 C 0.5238(6) 0.3536(6) 0.0568(4) 0.065(3) Uani 1 1 d . . . . . H27 H 0.4807 0.3263 0.0554 0.078 Uiso 1 1 calc R . . . . C28 C 0.5400(5) 0.4067(6) 0.0297(3) 0.054(3) Uani 1 1 d . . . . . H28 H 0.5077 0.4141 0.0105 0.065 Uiso 1 1 calc R . . . . C29 C 0.6023(5) 0.4462(5) 0.0321(3) 0.046(2) Uani 1 1 d . . . . . H29 H 0.6114 0.4822 0.0147 0.055 Uiso 1 1 calc R . . . . C30 C 0.6544(5) 0.4352(4) 0.0599(2) 0.0352(19) Uani 1 1 d . . . . . C31 C 0.6550(5) 0.5307(5) -0.0454(3) 0.050(2) Uani 1 1 d . . . . . H31 H 0.6379 0.5767 -0.0383 0.060 Uiso 1 1 calc R . . . . C32 C 0.6166(6) 0.4946(6) -0.0786(3) 0.059(3) Uani 1 1 d . . . . . H32 H 0.5750 0.5140 -0.0898 0.071 Uiso 1 1 calc R . . . . C33 C 0.6479(6) 0.4361(6) -0.0888(2) 0.054(3) Uani 1 1 d . . . . . H33 H 0.6298 0.4141 -0.1098 0.065 Uiso 1 1 calc R . . . . C34 C 0.7089(5) 0.3999(5) -0.0713(2) 0.045(2) Uani 1 1 d . . . . . C35 C 0.7467(6) 0.3355(5) -0.0822(2) 0.046(2) Uani 1 1 d . . . . . C36 C 0.8076(6) 0.3115(6) -0.0654(3) 0.055(3) Uani 1 1 d . . . . . H36 H 0.8314 0.2697 -0.0741 0.066 Uiso 1 1 calc R . . . . C37 C 0.8357(5) 0.3478(5) -0.0353(2) 0.041(2) Uani 1 1 d . . . . . C38 C 0.8010(5) 0.4099(4) -0.0203(2) 0.038(2) Uani 1 1 d . . . . . C39 C 0.7379(5) 0.4376(5) -0.0396(2) 0.039(2) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02857(18) 0.02922(18) 0.03193(17) 0.00089(13) -0.00130(13) 0.00570(13) Br1 0.0519(6) 0.0578(7) 0.0856(8) -0.0025(6) -0.0020(6) 0.0206(5) Br2 0.1038(10) 0.0561(7) 0.0551(6) -0.0164(5) -0.0065(6) 0.0033(7) O1 0.039(3) 0.036(3) 0.048(3) -0.006(3) -0.003(3) 0.009(3) N1 0.027(4) 0.045(4) 0.037(4) 0.007(3) -0.009(3) -0.002(3) N2 0.034(4) 0.029(4) 0.034(4) 0.002(3) -0.002(3) 0.001(3) N3 0.036(4) 0.025(4) 0.038(4) 0.000(3) 0.004(3) 0.002(3) C1 0.041(5) 0.038(5) 0.025(4) 0.000(3) 0.000(3) 0.001(4) C2 0.048(6) 0.042(5) 0.044(5) 0.006(4) 0.003(4) 0.010(4) C3 0.058(7) 0.065(7) 0.071(7) -0.002(6) 0.013(6) 0.022(6) C4 0.056(7) 0.086(9) 0.065(7) -0.002(6) 0.031(6) 0.008(6) C5 0.078(8) 0.052(6) 0.056(6) 0.006(5) 0.034(6) -0.004(6) C6 0.051(6) 0.045(5) 0.034(4) 0.003(4) 0.005(4) -0.005(5) C7 0.069(7) 0.042(5) 0.041(5) 0.016(4) 0.001(5) -0.001(5) C8 0.049(6) 0.034(5) 0.053(6) 0.012(4) 0.004(5) 0.010(4) C9 0.037(5) 0.032(4) 0.038(4) 0.001(4) -0.003(4) 0.006(4) C10 0.042(5) 0.031(4) 0.037(4) -0.001(4) -0.006(4) 0.003(4) C11 0.028(4) 0.036(5) 0.040(5) -0.006(4) -0.002(4) 0.003(4) C12 0.046(5) 0.037(5) 0.048(5) 0.002(4) 0.005(4) 0.005(4) C13 0.044(6) 0.057(6) 0.062(6) -0.001(5) 0.011(5) 0.020(5) C14 0.047(6) 0.043(6) 0.089(8) 0.002(6) 0.004(6) 0.022(5) C15 0.050(6) 0.036(5) 0.060(6) 0.005(4) -0.007(5) 0.010(4) C16 0.034(5) 0.032(4) 0.042(5) -0.005(4) -0.002(4) 0.011(4) C17 0.037(5) 0.040(5) 0.053(6) -0.007(4) -0.008(4) 0.004(4) C18 0.038(5) 0.058(6) 0.060(6) -0.010(5) -0.010(5) -0.006(5) C19 0.057(7) 0.074(7) 0.036(5) -0.006(5) -0.012(5) 0.004(6) C20 0.050(6) 0.059(6) 0.032(5) 0.004(4) -0.003(4) 0.008(5) C21 0.039(5) 0.038(5) 0.032(4) 0.003(4) -0.005(4) 0.007(4) C22 0.039(5) 0.037(5) 0.029(4) 0.006(4) 0.006(4) 0.004(4) C23 0.051(6) 0.049(6) 0.042(5) 0.007(4) -0.002(4) 0.007(5) C24 0.062(7) 0.039(5) 0.063(6) 0.009(5) 0.004(5) 0.001(5) C25 0.050(6) 0.030(5) 0.058(6) 0.005(4) 0.006(5) 0.001(4) C26 0.055(6) 0.038(6) 0.080(7) 0.014(5) 0.010(6) -0.006(5) C27 0.039(6) 0.042(6) 0.114(10) 0.002(6) 0.007(6) -0.002(5) C28 0.041(6) 0.052(6) 0.070(7) -0.001(5) -0.006(5) -0.004(5) C29 0.039(5) 0.046(6) 0.054(6) 0.004(4) 0.010(4) -0.004(4) C30 0.039(5) 0.029(4) 0.037(4) -0.001(4) 0.008(4) 0.004(4) C31 0.044(6) 0.039(5) 0.066(6) -0.002(5) 0.003(5) 0.008(5) C32 0.076(8) 0.055(6) 0.046(5) 0.016(5) 0.007(5) 0.048(6) C33 0.068(7) 0.061(7) 0.033(5) -0.004(5) -0.008(5) -0.021(6) C34 0.044(5) 0.051(6) 0.040(5) 0.009(4) 0.001(4) -0.006(5) C35 0.068(7) 0.031(5) 0.039(5) -0.005(4) 0.007(5) -0.006(5) C36 0.065(7) 0.040(6) 0.060(6) 0.002(5) 0.014(5) 0.007(5) C37 0.042(5) 0.033(5) 0.049(5) -0.002(4) 0.001(4) 0.002(4) C38 0.042(5) 0.027(4) 0.046(5) -0.006(4) 0.009(4) 0.000(4) C39 0.045(5) 0.036(5) 0.037(5) 0.001(4) 0.005(4) 0.001(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 N1 Ir1 O1 77.3(2) . . ? N2 Ir1 O1 103.0(2) . . ? N2 Ir1 N1 83.9(3) . . ? N2 Ir1 N3 173.7(3) . . ? N3 Ir1 O1 81.7(2) . . ? N3 Ir1 N1 101.3(3) . . ? C11 Ir1 O1 173.1(3) . . ? C11 Ir1 N1 96.7(3) . . ? C11 Ir1 N2 79.5(3) . . ? C11 Ir1 N3 96.3(3) . . ? C16 Ir1 O1 92.5(3) . . ? C16 Ir1 N1 169.5(3) . . ? C16 Ir1 N2 96.1(3) . . ? C16 Ir1 N3 79.5(3) . . ? C16 Ir1 C11 93.6(3) . . ? C38 O1 Ir1 113.5(5) . . ? C31 N1 Ir1 130.3(7) . . ? C31 N1 C39 115.9(8) . . ? C39 N1 Ir1 113.7(5) . . ? C1 N2 Ir1 126.8(5) . . ? C9 N2 Ir1 114.6(5) . . ? C9 N2 C1 118.5(7) . . ? C22 N3 Ir1 113.1(5) . . ? C22 N3 C30 119.2(7) . . ? C30 N3 Ir1 127.7(5) . . ? N2 C1 C2 120.3(7) . . ? N2 C1 C6 120.1(8) . . ? C2 C1 C6 119.5(8) . . ? C3 C2 C1 120.6(9) . . ? C2 C3 C4 120.0(10) . . ? C5 C4 C3 119.6(9) . . ? C4 C5 C6 122.0(9) . . ? C1 C6 C5 118.3(9) . . ? C7 C6 C1 119.3(8) . . ? C7 C6 C5 122.3(9) . . ? C8 C7 C6 119.8(8) . . ? C7 C8 C9 119.7(8) . . ? N2 C9 C8 122.3(8) . . ? N2 C9 C10 115.0(7) . . ? C8 C9 C10 122.7(8) . . ? C11 C10 C9 115.2(7) . . ? C15 C10 C9 124.1(8) . . ? C15 C10 C11 120.7(8) . . ? C10 C11 Ir1 114.8(6) . . ? C12 C11 Ir1 127.0(7) . . ? C12 C11 C10 117.9(8) . . ? C11 C12 C13 121.5(9) . . ? C14 C13 C12 120.5(9) . . ? C13 C14 C15 119.2(9) . . ? C14 C15 C10 120.3(9) . . ? C17 C16 Ir1 127.2(7) . . ? C21 C16 Ir1 115.6(6) . . ? C21 C16 C17 117.0(8) . . ? C18 C17 C16 120.3(9) . . ? C19 C18 C17 121.8(9) . . ? C18 C19 C20 119.0(9) . . ? C21 C20 C19 119.1(9) . . ? C16 C21 C20 122.7(9) . . ? C16 C21 C22 115.1(7) . . ? C20 C21 C22 122.2(8) . . ? N3 C22 C21 114.9(7) . . ? N3 C22 C23 120.2(8) . . ? C23 C22 C21 124.8(8) . . ? C24 C23 C22 121.4(9) . . ? C23 C24 C25 120.3(9) . . ? C24 C25 C26 123.8(9) . . ? C24 C25 C30 117.7(9) . . ? C26 C25 C30 118.4(9) . . ? C27 C26 C25 121.6(10) . . ? C26 C27 C28 120.1(10) . . ? C29 C28 C27 119.5(10) . . ? C28 C29 C30 122.5(9) . . ? N3 C30 C25 120.7(8) . . ? N3 C30 C29 121.4(8) . . ? C29 C30 C25 117.9(8) . . ? N1 C31 C32 126.3(8) . . ? C33 C32 C31 112.7(9) . . ? C32 C33 C34 126.7(9) . . ? C33 C34 C39 115.0(9) . . ? C35 C34 C33 128.6(9) . . ? C35 C34 C39 116.2(8) . . ? C34 C35 Br2 117.9(8) . . ? C36 C35 Br2 119.3(7) . . ? C36 C35 C34 122.8(9) . . ? C35 C36 C37 121.0(9) . . ? C36 C37 Br1 120.1(7) . . ? C36 C37 C38 122.1(9) . . ? C38 C37 Br1 117.7(7) . . ? O1 C38 C37 123.8(8) . . ? O1 C38 C39 119.7(7) . . ? C37 C38 C39 116.4(8) . . ? N1 C39 C34 123.0(8) . . ? N1 C39 C38 115.7(7) . . ? C38 C39 C34 121.4(8) . . ? 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 O1 2.169(6) . ? Ir1 N1 2.136(7) . ? Ir1 N2 2.092(6) . ? Ir1 N3 2.103(7) . ? Ir1 C11 2.005(8) . ? Ir1 C16 2.000(8) . ? Br1 C37 1.893(9) . ? Br2 C35 1.891(9) . ? O1 C38 1.304(10) . ? N1 C31 1.302(11) . ? N1 C39 1.383(11) . ? N2 C1 1.398(10) . ? N2 C9 1.334(10) . ? N3 C22 1.356(11) . ? N3 C30 1.380(10) . ? C1 C2 1.400(12) . ? C1 C6 1.407(11) . ? C2 C3 1.381(13) . ? C3 C4 1.417(15) . ? C4 C5 1.344(15) . ? C5 C6 1.420(13) . ? C6 C7 1.399(13) . ? C7 C8 1.344(13) . ? C8 C9 1.417(12) . ? C9 C10 1.460(12) . ? C10 C11 1.401(12) . ? C10 C15 1.398(12) . ? C11 C12 1.382(12) . ? C12 C13 1.393(12) . ? C13 C14 1.377(14) . ? C14 C15 1.388(14) . ? C16 C17 1.414(12) . ? C16 C21 1.383(11) . ? C17 C18 1.382(12) . ? C18 C19 1.372(14) . ? C19 C20 1.396(14) . ? C20 C21 1.394(12) . ? C21 C22 1.465(12) . ? C22 C23 1.409(12) . ? C23 C24 1.326(13) . ? C24 C25 1.408(13) . ? C25 C26 1.416(13) . ? C25 C30 1.424(12) . ? C26 C27 1.348(15) . ? C27 C28 1.418(15) . ? C28 C29 1.345(13) . ? C29 C30 1.409(12) . ? C31 C32 1.554(14) . ? C32 C33 1.264(13) . ? C33 C34 1.442(13) . ? C34 C35 1.415(13) . ? C34 C39 1.452(12) . ? C35 C36 1.341(14) . ? C36 C37 1.387(13) . ? C37 C38 1.406(11) . ? C38 C39 1.441(12) . ?