#------------------------------------------------------------------------------ #$Date: 2021-10-20 02:16:43 +0300 (Wed, 20 Oct 2021) $ #$Revision: 270037 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/85/7708579.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_7708579 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 Cl I Ir N3 O' _chemical_formula_sum 'C39 H24 Cl I Ir N3 O' _chemical_formula_weight 905.16 _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 18.4197(4) _cell_length_b 18.4197(4) _cell_length_c 36.1009(13) _cell_measurement_reflns_used 5391 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0620 _cell_measurement_theta_min 3.6570 _cell_volume 12248.5(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 0.939 _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 20.00 59.00 1.00 10.00 -- 18.47 -99.00 90.00 39 2 \w -33.00 10.00 1.00 10.00 -- -18.78 -77.00-180.00 43 3 \w -86.00 1.00 1.00 10.00 -- -18.78 -57.00 -90.00 87 4 \w -8.00 43.00 1.00 10.00 -- -18.78 77.00 60.00 51 5 \w -39.00 36.00 1.00 10.00 -- -18.78 57.00-180.00 75 6 \w -35.00 38.00 1.00 10.00 -- -18.78 38.00 60.00 73 ; _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 -0.0327423000 _diffrn_orient_matrix_UB_12 0.0201398000 _diffrn_orient_matrix_UB_13 -0.0011624000 _diffrn_orient_matrix_UB_21 0.0198098000 _diffrn_orient_matrix_UB_22 0.0327557000 _diffrn_orient_matrix_UB_23 0.0023202000 _diffrn_orient_matrix_UB_31 0.0043066000 _diffrn_orient_matrix_UB_32 0.0026220000 _diffrn_orient_matrix_UB_33 -0.0194629000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1090 _diffrn_reflns_av_unetI/netI 0.1123 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.939 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_number 45801 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.939 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.035 _diffrn_reflns_theta_min 3.326 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 5.495 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.62042 _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 1.963 _exptl_crystal_description BLOCK _exptl_crystal_F_000 6944 _refine_diff_density_max 4.070 _refine_diff_density_min -2.368 _refine_diff_density_rms 0.229 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 403 _refine_ls_number_reflns 7679 _refine_ls_number_restraints 1446 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.1426 _refine_ls_R_factor_gt 0.0700 _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^)+(0.0871P)^2^+181.7377P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1678 _refine_ls_wR_factor_ref 0.2063 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4384 _reflns_number_total 7679 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1dt02416g2.cif _cod_data_source_block 14 _cod_original_cell_volume 12248.5(7) _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 7708579 _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. Uiso/Uaniso restraints and constraints All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.02 and sigma for terminal atoms of 0.04 3.a Aromatic/amide H refined with riding coordinates: C37(H37), C38(H38), C39(H39), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C33(H33) 3.b Fitted hexagon refined as free rotating group: C36(C35,N3,C37,C38,C39) ; _shelx_res_file ; TITL 14 in I41/a #88 REM reset to I41/a #88 CELL 0.71073 18.41971 18.41971 36.10095 90 90 90 ZERR 16 0.00041 0.00041 0.00126 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 Cl I Ir N O UNIT 624 384 16 16 16 48 16 SIMU 0.02 0.04 3.8 L.S. 10 PLAN 20 BOND fmap 2 53 ACTA REM REM REM WGHT 0.087100 181.737701 FVAR 0.27276 IR1 5 0.258023 0.458471 0.019937 11.00000 0.03009 0.02992 = 0.03507 -0.00065 -0.00049 -0.00452 I1 4 0.428255 0.681391 -0.016626 11.00000 0.04930 0.05700 = 0.09933 0.00131 0.00114 -0.01565 CL1 3 0.201423 0.712969 -0.121888 11.00000 0.11764 0.05745 = 0.06260 0.01927 -0.01614 -0.01124 O1 7 0.317586 0.556233 0.007080 11.00000 0.03967 0.03908 = 0.05283 0.00423 0.00285 -0.00480 N1 6 0.214149 0.525312 0.061403 11.00000 0.03723 0.03461 = 0.04244 -0.00334 -0.00277 -0.00432 N2 6 0.303413 0.381772 -0.016316 11.00000 0.03775 0.03454 = 0.03802 -0.00138 -0.00257 -0.00236 AFIX 66 C36 1 0.200417 0.599318 -0.072659 11.00000 0.04793 0.05075 = 0.04630 0.00159 0.00230 0.00068 C35 1 0.230334 0.564722 -0.042034 11.00000 0.04289 0.04320 = 0.04514 0.00380 0.00179 -0.00198 N3 6 0.201752 0.499079 -0.029866 11.00000 0.03859 0.03711 = 0.04125 -0.00014 -0.00079 -0.00521 C37 1 0.143255 0.468032 -0.048324 11.00000 0.05302 0.04750 = 0.04945 0.00250 0.00003 -0.00543 AFIX 43 H37 2 0.124132 0.424112 -0.040183 11.00000 -1.20000 AFIX 65 C38 1 0.113337 0.502627 -0.078949 11.00000 0.04963 0.06772 = 0.05068 -0.03375 0.00913 -0.03470 AFIX 43 H38 2 0.074199 0.481854 -0.091298 11.00000 -1.20000 AFIX 65 C39 1 0.141918 0.568270 -0.091117 11.00000 0.07072 0.04920 = 0.04002 0.00303 0.00057 0.02764 AFIX 43 H39 2 0.121901 0.591417 -0.111607 11.00000 -1.20000 AFIX 0 C1 1 0.367113 0.389603 -0.036583 11.00000 0.03998 0.04211 = 0.04027 0.00315 -0.00231 -0.00206 C2 1 0.413937 0.451690 -0.031214 11.00000 0.04397 0.04667 = 0.04686 -0.00037 0.00459 -0.00383 AFIX 43 H2 2 0.401588 0.487448 -0.014153 11.00000 -1.20000 AFIX 0 C3 1 0.476970 0.457555 -0.051530 11.00000 0.04854 0.05677 = 0.05083 0.00319 0.00178 -0.01015 AFIX 43 H3 2 0.507783 0.496823 -0.047652 11.00000 -1.20000 AFIX 0 C4 1 0.495102 0.404930 -0.077980 11.00000 0.05463 0.06954 = 0.05196 0.00075 0.01725 -0.00730 AFIX 43 H4 2 0.537022 0.410578 -0.092046 11.00000 -1.20000 AFIX 0 C5 1 0.453949 0.347985 -0.083180 11.00000 0.05430 0.05546 = 0.05137 -0.00839 0.01430 0.00162 AFIX 43 H5 2 0.467910 0.313849 -0.100773 11.00000 -1.20000 AFIX 0 C6 1 0.387274 0.335918 -0.062566 11.00000 0.04721 0.04853 = 0.04226 0.00099 0.00473 0.00179 C7 1 0.345613 0.275312 -0.066813 11.00000 0.05127 0.04488 = 0.04658 -0.00175 0.00517 0.00316 AFIX 43 H7 2 0.358422 0.240638 -0.084361 11.00000 -1.20000 AFIX 0 C8 1 0.286806 0.265396 -0.046058 11.00000 0.05335 0.03900 = 0.04362 -0.00394 0.00224 -0.00143 AFIX 43 H8 2 0.259958 0.222812 -0.048036 11.00000 -1.20000 AFIX 0 C9 1 0.265155 0.321402 -0.020464 11.00000 0.03713 0.03348 = 0.03699 0.00172 -0.00046 -0.00435 C10 1 0.202332 0.314639 0.004216 11.00000 0.04137 0.03352 = 0.04479 0.00456 -0.00243 -0.00617 C11 1 0.155834 0.254138 0.005083 11.00000 0.04676 0.03944 = 0.05384 -0.00171 -0.00441 -0.00927 AFIX 43 H11 2 0.162527 0.215377 -0.011067 11.00000 -1.20000 AFIX 0 C12 1 0.099658 0.253854 0.030711 11.00000 0.04822 0.04643 = 0.06345 0.00059 -0.00144 -0.01157 AFIX 43 H12 2 0.069457 0.213503 0.032227 11.00000 -1.20000 AFIX 0 C13 1 0.087817 0.310805 0.053503 11.00000 0.04087 0.04524 = 0.05087 0.00221 0.01301 -0.00852 AFIX 43 H13 2 0.048175 0.310645 0.069457 11.00000 -1.20000 AFIX 0 C14 1 0.134500 0.368942 0.053042 11.00000 0.04123 0.04244 = 0.04838 -0.00160 0.00601 -0.00648 AFIX 43 H14 2 0.126620 0.406636 0.069703 11.00000 -1.20000 AFIX 0 C15 1 0.192387 0.374031 0.029084 11.00000 0.03570 0.03550 = 0.04380 -0.00022 -0.00377 -0.00605 C16 1 0.322916 0.432848 0.062211 11.00000 0.03334 0.03878 = 0.04275 0.00082 -0.00070 -0.00508 C17 1 0.375559 0.379485 0.063794 11.00000 0.03974 0.04146 = 0.04936 -0.00129 -0.00575 0.00036 AFIX 43 H17 2 0.380510 0.347495 0.044024 11.00000 -1.20000 AFIX 0 C18 1 0.422404 0.372281 0.094948 11.00000 0.04519 0.05594 = 0.05557 0.00036 -0.00755 0.00112 AFIX 43 H18 2 0.457092 0.335615 0.095578 11.00000 -1.20000 AFIX 0 C19 1 0.415972 0.420208 0.124288 11.00000 0.04485 0.05097 = 0.05425 0.00007 -0.01764 -0.00536 AFIX 43 H19 2 0.447047 0.416464 0.144502 11.00000 -1.20000 AFIX 0 C20 1 0.363269 0.473692 0.123516 11.00000 0.03825 0.04582 = 0.05136 -0.00400 -0.00300 -0.00484 AFIX 43 H20 2 0.358419 0.505311 0.143447 11.00000 -1.20000 AFIX 0 C21 1 0.317918 0.480324 0.093340 11.00000 0.03707 0.03992 = 0.04724 -0.00054 -0.00571 -0.00803 C22 1 0.258044 0.530613 0.091257 11.00000 0.04052 0.04114 = 0.04486 -0.00558 0.00508 -0.00726 C23 1 0.241996 0.584553 0.119406 11.00000 0.05462 0.04638 = 0.04649 -0.00833 -0.00338 -0.00366 AFIX 43 H23 2 0.273313 0.589307 0.139467 11.00000 -1.20000 AFIX 0 C24 1 0.182549 0.628478 0.117420 11.00000 0.04871 0.04588 = 0.05678 -0.00777 0.00537 -0.00311 AFIX 43 H24 2 0.174112 0.664499 0.134950 11.00000 -1.20000 AFIX 0 C25 1 0.135143 0.617085 0.088076 11.00000 0.04122 0.03613 = 0.05545 -0.00715 0.00653 0.00123 C26 1 0.067812 0.659188 0.084893 11.00000 0.05366 0.04371 = 0.06532 -0.00668 0.00806 0.00239 AFIX 43 H26 2 0.057433 0.694727 0.102409 11.00000 -1.20000 AFIX 0 C27 1 0.020688 0.647103 0.056909 11.00000 0.04244 0.04784 = 0.07757 0.00597 0.00506 0.00181 AFIX 43 H27 2 -0.021897 0.674037 0.055273 11.00000 -1.20000 AFIX 0 C28 1 0.036358 0.593209 0.030029 11.00000 0.04475 0.05142 = 0.06381 0.00207 0.00083 -0.00347 AFIX 43 H28 2 0.003084 0.583848 0.011251 11.00000 -1.20000 AFIX 0 C29 1 0.098604 0.555604 0.031384 11.00000 0.04068 0.04483 = 0.05552 -0.00256 0.00703 0.00131 AFIX 43 H29 2 0.108090 0.520931 0.013294 11.00000 -1.20000 AFIX 0 C30 1 0.150586 0.567697 0.060014 11.00000 0.03688 0.03649 = 0.05145 -0.00266 0.00451 -0.00342 C31 1 0.292609 0.591727 -0.023015 11.00000 0.04178 0.04186 = 0.04543 0.00261 0.00532 0.00122 C32 1 0.326909 0.652119 -0.037400 11.00000 0.03781 0.03809 = 0.04985 0.00723 0.00249 -0.00385 C33 1 0.297393 0.688204 -0.068054 11.00000 0.05309 0.04451 = 0.05441 0.00393 0.00974 -0.00549 AFIX 43 H33 2 0.320438 0.729468 -0.077116 11.00000 -1.20000 AFIX 0 C34 1 0.236146 0.664409 -0.084775 11.00000 0.05927 0.04634 = 0.04570 0.00688 0.00244 0.00225 HKLF 4 REM 14 in I41/a #88 REM R1 = 0.0700 for 4384 Fo > 4sig(Fo) and 0.1426 for all 7679 data REM 403 parameters refined using 1446 restraints END WGHT 0.0871 181.7896 REM Highest difference peak 4.070, deepest hole -2.368, 1-sigma level 0.229 Q1 1 0.0915 0.5378 -0.0893 11.00000 0.05 4.07 Q2 1 0.2443 0.5417 0.0212 11.00000 0.05 1.20 Q3 1 0.3136 0.7536 -0.0984 11.00000 0.05 1.19 Q4 1 0.3208 0.5583 0.0188 11.00000 0.05 1.17 Q5 1 0.2022 0.4989 -0.0173 11.00000 0.05 1.12 Q6 1 0.1579 0.5235 0.0193 11.00000 0.05 1.05 Q7 1 0.2404 0.5405 -0.0577 11.00000 0.05 0.92 Q8 1 0.1597 0.4781 -0.0422 11.00000 0.05 0.91 Q9 1 0.3692 0.6791 -0.0287 11.00000 0.05 0.85 Q10 1 0.1235 0.3649 0.0205 11.00000 0.05 0.84 Q11 1 0.4118 0.6152 -0.0193 11.00000 0.05 0.83 Q12 1 0.3909 0.6261 -0.0102 11.00000 0.05 0.82 Q13 1 0.1805 0.4396 -0.0589 11.00000 0.05 0.74 Q14 1 0.0194 0.2033 0.0219 11.00000 0.05 0.73 Q15 1 0.4104 0.6453 0.0140 11.00000 0.05 0.72 Q16 1 0.2953 0.4134 -0.0183 11.00000 0.05 0.72 Q17 1 0.3562 0.6785 -0.0206 11.00000 0.05 0.72 Q18 1 0.3974 0.7139 0.0184 11.00000 0.05 0.67 Q19 1 0.1161 0.1455 0.0199 11.00000 0.05 0.66 Q20 1 0.2175 0.2373 -0.0216 11.00000 0.05 0.66 ; _shelx_res_checksum 43544 _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 1.558 _oxdiff_exptl_absorpt_empirical_full_min 0.639 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 0.25802(2) 0.45847(2) 0.01994(2) 0.03169(16) Uani 1 1 d . U . . . I1 I 0.42826(6) 0.68139(6) -0.01663(3) 0.0685(3) Uani 1 1 d . U . . . Cl1 Cl 0.2014(3) 0.7130(2) -0.12189(11) 0.0792(13) Uani 1 1 d . U . . . O1 O 0.3176(5) 0.5562(5) 0.0071(2) 0.0439(17) Uani 1 1 d . U . . . N1 N 0.2141(5) 0.5253(5) 0.0614(3) 0.0381(18) Uani 1 1 d . U . . . N2 N 0.3034(5) 0.3818(5) -0.0163(2) 0.0368(18) Uani 1 1 d . U . . . C36 C 0.2004(5) 0.5993(4) -0.0727(2) 0.048(2) Uani 1 1 d . U . . . C35 C 0.2303(4) 0.5647(4) -0.0420(2) 0.044(2) Uani 1 1 d G U . . . N3 N 0.2018(4) 0.4991(4) -0.02987(18) 0.0390(18) Uani 1 1 d G U . . . C37 C 0.1433(4) 0.4680(4) -0.0483(2) 0.050(2) Uani 1 1 d G U . . . H37 H 0.1241 0.4241 -0.0402 0.060 Uiso 1 1 calc R . . . . C38 C 0.1133(4) 0.5026(5) -0.0789(2) 0.056(3) Uani 1 1 d G U . . . H38 H 0.0742 0.4819 -0.0913 0.067 Uiso 1 1 calc R . . . . C39 C 0.1419(5) 0.5683(5) -0.09112(18) 0.053(3) Uani 1 1 d G U . . . H39 H 0.1219 0.5914 -0.1116 0.064 Uiso 1 1 calc R . . . . C1 C 0.3671(7) 0.3896(7) -0.0366(3) 0.041(2) Uani 1 1 d . U . . . C2 C 0.4139(7) 0.4517(7) -0.0312(4) 0.046(2) Uani 1 1 d . U . . . H2 H 0.4016 0.4874 -0.0142 0.055 Uiso 1 1 calc R . . . . C3 C 0.4770(8) 0.4576(8) -0.0515(4) 0.052(3) Uani 1 1 d . U . . . H3 H 0.5078 0.4968 -0.0477 0.062 Uiso 1 1 calc R . . . . C4 C 0.4951(8) 0.4049(9) -0.0780(4) 0.059(3) Uani 1 1 d . U . . . H4 H 0.5370 0.4106 -0.0920 0.070 Uiso 1 1 calc R . . . . C5 C 0.4539(8) 0.3480(8) -0.0832(4) 0.054(3) Uani 1 1 d . U . . . H5 H 0.4679 0.3138 -0.1008 0.064 Uiso 1 1 calc R . . . . C6 C 0.3873(7) 0.3359(7) -0.0626(3) 0.046(2) Uani 1 1 d . U . . . C7 C 0.3456(7) 0.2753(7) -0.0668(4) 0.048(2) Uani 1 1 d . U . . . H7 H 0.3584 0.2406 -0.0844 0.057 Uiso 1 1 calc R . . . . C8 C 0.2868(7) 0.2654(7) -0.0461(3) 0.045(2) Uani 1 1 d . U . . . H8 H 0.2600 0.2228 -0.0480 0.054 Uiso 1 1 calc R . . . . C9 C 0.2652(7) 0.3214(6) -0.0205(3) 0.036(2) Uani 1 1 d . U . . . C10 C 0.2023(7) 0.3146(6) 0.0042(3) 0.040(2) Uani 1 1 d . U . . . C11 C 0.1558(7) 0.2541(7) 0.0051(4) 0.047(3) Uani 1 1 d . U . . . H11 H 0.1625 0.2154 -0.0111 0.056 Uiso 1 1 calc R . . . . C12 C 0.0997(8) 0.2539(8) 0.0307(4) 0.053(3) Uani 1 1 d . U . . . H12 H 0.0695 0.2135 0.0322 0.063 Uiso 1 1 calc R . . . . C13 C 0.0878(7) 0.3108(7) 0.0535(4) 0.046(3) Uani 1 1 d . U . . . H13 H 0.0482 0.3106 0.0695 0.055 Uiso 1 1 calc R . . . . C14 C 0.1345(7) 0.3689(7) 0.0530(3) 0.044(2) Uani 1 1 d . U . . . H14 H 0.1266 0.4066 0.0697 0.053 Uiso 1 1 calc R . . . . C15 C 0.1924(7) 0.3740(7) 0.0291(3) 0.038(2) Uani 1 1 d . U . . . C16 C 0.3229(6) 0.4328(6) 0.0622(3) 0.038(2) Uani 1 1 d . U . . . C17 C 0.3756(7) 0.3795(7) 0.0638(3) 0.044(2) Uani 1 1 d . U . . . H17 H 0.3805 0.3475 0.0440 0.052 Uiso 1 1 calc R . . . . C18 C 0.4224(7) 0.3723(8) 0.0949(4) 0.052(3) Uani 1 1 d . U . . . H18 H 0.4571 0.3356 0.0956 0.063 Uiso 1 1 calc R . . . . C19 C 0.4160(7) 0.4202(7) 0.1243(4) 0.050(3) Uani 1 1 d . U . . . H19 H 0.4470 0.4165 0.1445 0.060 Uiso 1 1 calc R . . . . C20 C 0.3633(7) 0.4737(7) 0.1235(4) 0.045(2) Uani 1 1 d . U . . . H20 H 0.3584 0.5053 0.1434 0.054 Uiso 1 1 calc R . . . . C21 C 0.3179(7) 0.4803(7) 0.0933(3) 0.041(2) Uani 1 1 d . U . . . C22 C 0.2580(7) 0.5306(7) 0.0913(4) 0.042(2) Uani 1 1 d . U . . . C23 C 0.2420(8) 0.5846(7) 0.1194(4) 0.049(3) Uani 1 1 d . U . . . H23 H 0.2733 0.5893 0.1395 0.059 Uiso 1 1 calc R . . . . C24 C 0.1825(7) 0.6285(8) 0.1174(4) 0.050(3) Uani 1 1 d . U . . . H24 H 0.1741 0.6645 0.1350 0.061 Uiso 1 1 calc R . . . . C25 C 0.1351(7) 0.6171(7) 0.0881(4) 0.044(2) Uani 1 1 d . U . . . C26 C 0.0678(8) 0.6592(7) 0.0849(4) 0.054(3) Uani 1 1 d . U . . . H26 H 0.0574 0.6947 0.1024 0.065 Uiso 1 1 calc R . . . . C27 C 0.0207(8) 0.6471(8) 0.0569(4) 0.056(3) Uani 1 1 d . U . . . H27 H -0.0219 0.6740 0.0553 0.067 Uiso 1 1 calc R . . . . C28 C 0.0364(8) 0.5932(8) 0.0300(4) 0.053(3) Uani 1 1 d . U . . . H28 H 0.0031 0.5838 0.0113 0.064 Uiso 1 1 calc R . . . . C29 C 0.0986(7) 0.5556(7) 0.0314(4) 0.047(2) Uani 1 1 d . U . . . H29 H 0.1081 0.5209 0.0133 0.056 Uiso 1 1 calc R . . . . C30 C 0.1506(7) 0.5677(7) 0.0600(3) 0.042(2) Uani 1 1 d . U . . . C31 C 0.2926(7) 0.5917(7) -0.0230(3) 0.043(2) Uani 1 1 d . U . . . C32 C 0.3269(7) 0.6521(7) -0.0374(3) 0.042(2) Uani 1 1 d . U . . . C33 C 0.2974(8) 0.6882(7) -0.0681(4) 0.051(3) Uani 1 1 d . U . . . H33 H 0.3204 0.7295 -0.0771 0.061 Uiso 1 1 calc R . . . . C34 C 0.2361(8) 0.6644(7) -0.0848(4) 0.050(3) Uani 1 1 d . 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 0.0301(3) 0.0299(3) 0.0351(3) -0.00065(18) -0.00049(18) -0.00452(19) I1 0.0493(6) 0.0570(6) 0.0993(8) 0.0013(6) 0.0011(5) -0.0157(5) Cl1 0.118(4) 0.057(2) 0.063(2) 0.019(2) -0.016(2) -0.011(2) O1 0.040(4) 0.039(4) 0.053(4) 0.004(3) 0.003(3) -0.005(3) N1 0.037(4) 0.035(4) 0.042(4) -0.003(3) -0.003(3) -0.004(3) N2 0.038(4) 0.035(4) 0.038(4) -0.001(3) -0.003(3) -0.002(3) C36 0.048(5) 0.051(5) 0.046(5) 0.002(5) 0.002(4) 0.001(5) C35 0.043(5) 0.043(5) 0.045(4) 0.004(4) 0.002(4) -0.002(4) N3 0.039(4) 0.037(4) 0.041(4) 0.000(3) -0.001(3) -0.005(3) C37 0.053(5) 0.047(5) 0.049(5) 0.003(4) 0.000(4) -0.005(5) C38 0.050(6) 0.068(6) 0.051(6) -0.034(5) 0.009(5) -0.035(5) C39 0.071(6) 0.049(5) 0.040(5) 0.003(5) 0.001(5) 0.028(5) C1 0.040(4) 0.042(4) 0.040(4) 0.003(4) -0.002(4) -0.002(4) C2 0.044(5) 0.047(5) 0.047(4) 0.000(4) 0.005(4) -0.004(4) C3 0.049(6) 0.057(6) 0.051(6) 0.003(5) 0.002(5) -0.010(5) C4 0.055(6) 0.070(7) 0.052(6) 0.001(6) 0.017(5) -0.007(6) C5 0.054(6) 0.055(6) 0.051(5) -0.008(5) 0.014(5) 0.002(5) C6 0.047(5) 0.049(5) 0.042(5) 0.001(5) 0.005(5) 0.002(5) C7 0.051(5) 0.045(5) 0.047(5) -0.002(5) 0.005(5) 0.003(5) C8 0.053(5) 0.039(5) 0.044(5) -0.004(4) 0.002(5) -0.001(5) C9 0.037(4) 0.033(4) 0.037(4) 0.002(4) 0.000(4) -0.004(4) C10 0.041(4) 0.034(4) 0.045(4) 0.005(4) -0.002(4) -0.006(4) C11 0.047(5) 0.039(5) 0.054(5) -0.002(5) -0.004(5) -0.009(5) C12 0.048(6) 0.046(6) 0.063(6) 0.001(5) -0.001(5) -0.012(5) C13 0.041(6) 0.045(6) 0.051(6) 0.002(5) 0.013(5) -0.009(5) C14 0.041(5) 0.042(5) 0.048(5) -0.002(4) 0.006(4) -0.006(4) C15 0.036(4) 0.036(4) 0.044(4) 0.000(4) -0.004(4) -0.006(4) C16 0.033(4) 0.039(4) 0.043(4) 0.001(4) -0.001(4) -0.005(4) C17 0.040(5) 0.041(5) 0.049(5) -0.001(4) -0.006(4) 0.000(4) C18 0.045(6) 0.056(6) 0.056(6) 0.000(5) -0.008(5) 0.001(6) C19 0.045(6) 0.051(6) 0.054(6) 0.000(5) -0.018(5) -0.005(5) C20 0.038(5) 0.046(5) 0.051(5) -0.004(5) -0.003(5) -0.005(5) C21 0.037(4) 0.040(5) 0.047(5) -0.001(4) -0.006(4) -0.008(4) C22 0.041(4) 0.041(4) 0.045(4) -0.006(4) 0.005(4) -0.007(4) C23 0.055(5) 0.046(5) 0.046(5) -0.008(5) -0.003(5) -0.004(5) C24 0.049(5) 0.046(5) 0.057(5) -0.008(5) 0.005(5) -0.003(5) C25 0.041(5) 0.036(5) 0.055(5) -0.007(5) 0.007(5) 0.001(5) C26 0.054(6) 0.044(5) 0.065(6) -0.007(5) 0.008(5) 0.002(5) C27 0.042(6) 0.048(6) 0.078(7) 0.006(6) 0.005(6) 0.002(5) C28 0.045(6) 0.051(6) 0.064(6) 0.002(5) 0.001(5) -0.003(5) C29 0.041(4) 0.045(5) 0.056(5) -0.003(4) 0.007(4) 0.001(4) C30 0.037(4) 0.036(4) 0.051(4) -0.003(4) 0.005(4) -0.003(4) C31 0.042(5) 0.042(5) 0.045(5) 0.003(4) 0.005(4) 0.001(4) C32 0.038(5) 0.038(5) 0.050(5) 0.007(5) 0.002(5) -0.004(5) C33 0.053(6) 0.045(5) 0.054(6) 0.004(5) 0.010(5) -0.005(5) C34 0.059(6) 0.046(5) 0.046(5) 0.007(5) 0.002(5) 0.002(5) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 O1 Ir1 N3 77.3(3) . . ? N1 Ir1 O1 81.9(4) . . ? N1 Ir1 N3 101.6(3) . . ? N2 Ir1 O1 103.0(3) . . ? N2 Ir1 N1 172.8(4) . . ? N2 Ir1 N3 84.7(3) . . ? C15 Ir1 O1 173.0(4) . . ? C15 Ir1 N1 96.1(4) . . ? C15 Ir1 N2 79.6(4) . . ? C15 Ir1 N3 96.6(4) . . ? C16 Ir1 O1 93.3(4) . . ? C16 Ir1 N1 79.9(4) . . ? C16 Ir1 N2 94.5(4) . . ? C16 Ir1 N3 170.1(4) . . ? C16 Ir1 C15 93.0(5) . . ? C31 O1 Ir1 113.8(7) . . ? C22 N1 Ir1 112.4(8) . . ? C22 N1 C30 119.1(10) . . ? C30 N1 Ir1 128.3(8) . . ? C1 N2 Ir1 126.5(8) . . ? C9 N2 Ir1 115.0(8) . . ? C9 N2 C1 118.5(10) . . ? C35 C36 C39 120.0 . . ? C35 C36 C34 116.3(8) . . ? C39 C36 C34 123.6(8) . . ? C36 C35 N3 120.0 . . ? C36 C35 C31 122.8(7) . . ? N3 C35 C31 117.1(7) . . ? C35 N3 Ir1 112.0(4) . . ? C37 N3 Ir1 128.0(4) . . ? C37 N3 C35 120.0 . . ? C38 C37 N3 120.0 . . ? C37 C38 C39 120.0 . . ? C38 C39 C36 120.0 . . ? N2 C1 C2 121.0(11) . . ? N2 C1 C6 119.9(11) . . ? C6 C1 C2 119.1(12) . . ? C3 C2 C1 119.6(13) . . ? C2 C3 C4 120.6(13) . . ? C5 C4 C3 121.0(13) . . ? C4 C5 C6 122.6(13) . . ? C1 C6 C5 117.1(12) . . ? C7 C6 C1 120.0(12) . . ? C7 C6 C5 122.9(12) . . ? C8 C7 C6 120.5(13) . . ? C7 C8 C9 119.2(12) . . ? N2 C9 C8 121.7(11) . . ? N2 C9 C10 115.0(10) . . ? C8 C9 C10 123.2(11) . . ? C11 C10 C9 124.2(11) . . ? C11 C10 C15 121.0(12) . . ? C15 C10 C9 114.7(11) . . ? C12 C11 C10 118.2(12) . . ? C13 C12 C11 121.6(13) . . ? C12 C13 C14 119.8(12) . . ? C13 C14 C15 123.1(12) . . ? C10 C15 Ir1 114.5(9) . . ? C14 C15 Ir1 128.8(10) . . ? C14 C15 C10 116.3(11) . . ? C17 C16 Ir1 128.3(9) . . ? C17 C16 C21 116.7(11) . . ? C21 C16 Ir1 114.8(9) . . ? C16 C17 C18 121.6(12) . . ? C19 C18 C17 119.6(13) . . ? C20 C19 C18 119.9(12) . . ? C21 C20 C19 120.3(13) . . ? C16 C21 C22 113.7(10) . . ? C20 C21 C16 121.9(12) . . ? C20 C21 C22 124.2(12) . . ? N1 C22 C21 116.9(11) . . ? N1 C22 C23 119.1(12) . . ? C21 C22 C23 124.0(12) . . ? C24 C23 C22 122.2(13) . . ? C23 C24 C25 117.1(12) . . ? C24 C25 C26 120.8(12) . . ? C24 C25 C30 121.7(12) . . ? C30 C25 C26 117.5(12) . . ? C27 C26 C25 121.0(13) . . ? C26 C27 C28 119.8(14) . . ? C29 C28 C27 120.7(14) . . ? C28 C29 C30 121.3(13) . . ? N1 C30 C29 119.8(11) . . ? C25 C30 N1 120.4(11) . . ? C25 C30 C29 119.5(12) . . ? O1 C31 C35 119.5(10) . . ? O1 C31 C32 122.5(11) . . ? C32 C31 C35 117.9(11) . . ? C31 C32 I1 118.9(9) . . ? C31 C32 C33 120.1(12) . . ? C33 C32 I1 120.6(9) . . ? C34 C33 C32 121.5(13) . . ? C36 C34 Cl1 119.8(10) . . ? C33 C34 Cl1 119.0(11) . . ? C33 C34 C36 121.1(12) . . ? 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 2.159(8) . ? Ir1 N1 2.100(10) . ? Ir1 N2 2.099(10) . ? Ir1 N3 2.206(5) . ? Ir1 C15 1.997(12) . ? Ir1 C16 1.995(12) . ? I1 C32 2.083(13) . ? Cl1 C34 1.733(14) . ? O1 C31 1.349(14) . ? N1 C22 1.351(16) . ? N1 C30 1.408(15) . ? N2 C1 1.390(15) . ? N2 C9 1.325(14) . ? C36 C35 1.3900 . ? C36 C39 1.3900 . ? C36 C34 1.436(15) . ? C35 N3 1.3900 . ? C35 C31 1.426(14) . ? N3 C37 1.3900 . ? C37 C38 1.3900 . ? C38 C39 1.3900 . ? C1 C2 1.445(18) . ? C1 C6 1.413(17) . ? C2 C3 1.378(18) . ? C3 C4 1.401(19) . ? C4 C5 1.308(19) . ? C5 C6 1.453(18) . ? C6 C7 1.363(18) . ? C7 C8 1.330(18) . ? C8 C9 1.441(16) . ? C9 C10 1.466(17) . ? C10 C11 1.406(16) . ? C10 C15 1.427(17) . ? C11 C12 1.388(19) . ? C12 C13 1.351(18) . ? C13 C14 1.373(17) . ? C14 C15 1.376(17) . ? C16 C17 1.382(17) . ? C16 C21 1.427(17) . ? C17 C18 1.424(17) . ? C18 C19 1.384(19) . ? C19 C20 1.383(18) . ? C20 C21 1.378(17) . ? C21 C22 1.442(18) . ? C22 C23 1.452(17) . ? C23 C24 1.363(18) . ? C24 C25 1.389(18) . ? C25 C26 1.467(19) . ? C25 C30 1.391(17) . ? C26 C27 1.35(2) . ? C27 C28 1.42(2) . ? C28 C29 1.340(19) . ? C29 C30 1.426(18) . ? C31 C32 1.381(17) . ? C32 C33 1.401(18) . ? C33 C34 1.352(19) . ?