#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:12:45 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252861 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557796.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_1557796 loop_ _publ_author_name 'Qin, Li-Qin' 'Zou, Bi-Qun' 'Qin, Qi-Pin' 'Wang, Zhen-Feng' 'Yang, Lin' 'Tan, Ming-Xiong' 'Liang, Chun-Jie' 'Liang, Hong' _publ_section_title ; Highly cytotoxic, cyclometalated iridium(iii)-5-fluoro-8-quinolinol complexes as cancer cell mitochondriotropic agents ; _journal_issue 19 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7832 _journal_paper_doi 10.1039/D0NJ00465K _journal_volume 44 _journal_year 2020 _chemical_formula_moiety 'C27 H19 F Ir N5 O, 2(C H4 O)' _chemical_formula_sum 'C29 H27 F Ir N5 O3' _chemical_formula_weight 704.75 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-10-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-27 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.221(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7444(8) _cell_length_b 22.9897(12) _cell_length_c 10.6487(6) _cell_measurement_reflns_used 5857 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.2880 _cell_measurement_theta_min 3.8330 _cell_volume 2614.9(3) _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 0.998 _diffrn_measured_fraction_theta_max 0.874 _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 60.00 1.00 15.00 -- 18.63 -99.00 150.00 39 2 \w -76.00 -51.00 1.00 15.00 -- -18.94 178.00 150.00 25 3 \w -82.00 11.00 1.00 15.00 -- -18.94 -77.00-120.00 93 4 \w -28.00 -2.00 1.00 15.00 -- -18.94 -57.00 0.00 26 5 \w -45.00 50.00 1.00 15.00 -- -18.94 77.00 0.00 95 6 \w -89.00 11.00 1.00 15.00 -- -18.94 -19.00 60.00 100 ; _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 0.0577584000 _diffrn_orient_matrix_UB_12 -0.0000387000 _diffrn_orient_matrix_UB_13 -0.0263696000 _diffrn_orient_matrix_UB_21 -0.0292116000 _diffrn_orient_matrix_UB_22 0.0135920000 _diffrn_orient_matrix_UB_23 -0.0554505000 _diffrn_orient_matrix_UB_31 0.0144070000 _diffrn_orient_matrix_UB_32 0.0276872000 _diffrn_orient_matrix_UB_33 0.0271396000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_unetI/netI 0.0780 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.874 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 20028 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.874 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.196 _diffrn_reflns_theta_min 3.358 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 5.155 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59069 _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 1.790 _exptl_crystal_description block _exptl_crystal_F_000 1384 _refine_diff_density_max 1.496 _refine_diff_density_min -1.625 _refine_diff_density_rms 0.145 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 356 _refine_ls_number_reflns 6202 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.995 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0435 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.0972 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4282 _reflns_number_total 6202 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj00465k2.cif _cod_data_source_block 9 _cod_depositor_comments 'Adding full bibliography for 1557795--1557798.cif.' _cod_original_cell_volume 2614.8(3) _cod_database_code 1557796 _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 99.69 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26) 2.b Idealised Me refined as rotating group: C28(H28A,H28B,H28C), C29(H29A,H29B,H29C) 2.c Idealised tetrahedral OH refined as rotating group: O2(H2A), O3(H3A) ; _shelx_res_file ; TITL 9 in P21/c #14 REM reset to P21/c #14 CELL 0.71073 10.74439 22.9897 10.64868 90 96.2214 90 ZERR 4 0.00082 0.00123 0.00062 0 0.0062 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F Ir N O UNIT 116 108 4 4 20 12 L.S. 10 PLAN 20 BOND fmap 2 ACTA REM REM REM WGHT 0.034900 FVAR 1.66530 IR1 4 0.269818 0.619398 0.887829 11.00000 0.04760 0.02913 = 0.02686 0.00033 0.01081 0.00403 F1 3 0.042923 0.535211 0.315956 11.00000 0.14192 0.06305 = 0.03868 -0.00668 -0.00990 -0.02424 O1 6 0.370779 0.587546 0.734790 11.00000 0.04854 0.04783 = 0.04006 -0.00278 0.01446 0.01125 N1 5 0.339036 0.522356 1.048996 11.00000 0.06174 0.03753 = 0.03768 0.00162 0.01144 0.01467 N2 5 0.251737 0.538102 0.952742 11.00000 0.06436 0.02930 = 0.03535 -0.00162 0.00942 0.01008 N3 5 0.122192 0.609525 0.736820 11.00000 0.05944 0.02903 = 0.03077 0.00340 0.01327 -0.00307 N4 5 0.229051 0.741959 0.919154 11.00000 0.05085 0.02916 = 0.03611 -0.00157 0.01008 0.00099 N5 5 0.291931 0.704913 0.848592 11.00000 0.04180 0.03188 = 0.03119 0.00140 0.01003 0.00111 C1 1 0.163523 0.654955 1.010359 11.00000 0.04381 0.03572 = 0.02729 -0.00333 0.00779 -0.00040 C2 1 0.091508 0.629131 1.095791 11.00000 0.06205 0.03960 = 0.03922 -0.00075 0.01711 -0.00064 AFIX 43 H2 2 0.095463 0.588969 1.105899 11.00000 -1.20000 AFIX 0 C3 1 0.014412 0.660471 1.166257 11.00000 0.07118 0.05651 = 0.03839 0.00372 0.02320 0.00236 AFIX 43 H3 2 -0.033713 0.641379 1.220980 11.00000 -1.20000 AFIX 0 C4 1 0.008899 0.720775 1.155168 11.00000 0.06553 0.05300 = 0.05423 -0.01044 0.02412 0.01013 AFIX 43 H4 2 -0.042724 0.742173 1.202551 11.00000 -1.20000 AFIX 0 C5 1 0.080730 0.748682 1.073180 11.00000 0.06279 0.03523 = 0.05455 -0.00753 0.01961 0.01056 AFIX 43 H5 2 0.078549 0.788952 1.064943 11.00000 -1.20000 AFIX 0 C6 1 0.154956 0.715764 1.004569 11.00000 0.04457 0.03178 = 0.03262 -0.00129 0.01213 0.00084 C7 1 0.258765 0.797262 0.890809 11.00000 0.06851 0.02701 = 0.04786 0.00142 0.01007 -0.00156 AFIX 43 H7 2 0.228535 0.830575 0.926688 11.00000 -1.20000 AFIX 0 C8 1 0.339452 0.796267 0.801958 11.00000 0.08273 0.03671 = 0.04757 0.00162 0.01807 -0.01723 AFIX 43 H8 2 0.375047 0.828052 0.765309 11.00000 -1.20000 AFIX 0 C9 1 0.358136 0.737687 0.776768 11.00000 0.04953 0.05595 = 0.03379 0.00457 0.01919 -0.00012 AFIX 43 H9 2 0.409178 0.723533 0.718534 11.00000 -1.20000 AFIX 0 C10 1 0.172620 0.493656 0.934392 11.00000 0.07736 0.04442 = 0.04114 -0.00330 0.01816 0.00449 AFIX 43 H10 2 0.103836 0.492384 0.873394 11.00000 -1.20000 AFIX 0 C11 1 0.208285 0.448877 1.020790 11.00000 0.10940 0.03740 = 0.04997 -0.00139 0.02709 -0.01055 AFIX 43 H11 2 0.167857 0.413526 1.028934 11.00000 -1.20000 AFIX 0 C12 1 0.314214 0.468012 1.089987 11.00000 0.10416 0.03644 = 0.04830 0.00853 0.02403 0.01059 AFIX 43 H12 2 0.361243 0.447572 1.153907 11.00000 -1.20000 AFIX 0 C13 1 0.431895 0.563788 1.087414 11.00000 0.06788 0.04609 = 0.03430 -0.00085 0.00599 0.01316 C14 1 0.527070 0.553273 1.181806 11.00000 0.06271 0.07832 = 0.04512 0.00539 0.00935 0.02542 AFIX 43 H14 2 0.532449 0.517711 1.223670 11.00000 -1.20000 AFIX 0 C15 1 0.614267 0.596186 1.213393 11.00000 0.05802 0.11269 = 0.04611 -0.00912 -0.00373 0.03489 AFIX 43 H15 2 0.679040 0.589666 1.277116 11.00000 -1.20000 AFIX 0 C16 1 0.605931 0.648435 1.151289 11.00000 0.05390 0.08918 = 0.06082 -0.01621 0.00262 -0.00078 AFIX 43 H16 2 0.665329 0.677154 1.173068 11.00000 -1.20000 AFIX 0 C17 1 0.509654 0.658957 1.056108 11.00000 0.05425 0.06278 = 0.04115 -0.00209 0.00589 0.00560 AFIX 43 H17 2 0.505426 0.694825 1.015483 11.00000 -1.20000 AFIX 0 C18 1 0.418991 0.616849 1.020023 11.00000 0.05429 0.04771 = 0.02759 -0.00552 0.01132 0.01191 C19 1 0.291679 0.573683 0.633455 11.00000 0.07401 0.03146 = 0.03279 0.00191 0.01842 -0.00170 C20 1 0.333043 0.549150 0.525346 11.00000 0.08610 0.05737 = 0.04502 -0.00357 0.03076 0.01207 AFIX 43 H20 2 0.417569 0.540783 0.523970 11.00000 -1.20000 AFIX 0 C21 1 0.248400 0.537012 0.418873 11.00000 0.11462 0.05021 = 0.03096 -0.00799 0.02639 0.00089 AFIX 43 H21 2 0.277759 0.521079 0.347405 11.00000 -1.20000 AFIX 0 C22 1 0.124653 0.548125 0.418506 11.00000 0.09270 0.03917 = 0.03067 -0.00078 0.00996 -0.01260 C23 1 0.076685 0.573556 0.524004 11.00000 0.08119 0.02833 = 0.03529 0.00761 0.00593 -0.01179 C24 1 -0.050612 0.586503 0.529255 11.00000 0.07321 0.04982 = 0.05263 0.00680 -0.01652 -0.01796 AFIX 43 H24 2 -0.109241 0.579251 0.460203 11.00000 -1.20000 AFIX 0 C25 1 -0.086180 0.609646 0.636330 11.00000 0.04315 0.05659 = 0.06859 0.00094 -0.00517 0.00367 AFIX 43 H25 2 -0.170054 0.618425 0.640960 11.00000 -1.20000 AFIX 0 C26 1 0.002612 0.620653 0.741296 11.00000 0.04699 0.04166 = 0.04302 -0.00015 0.01025 0.00417 AFIX 43 H26 2 -0.023800 0.636005 0.814744 11.00000 -1.20000 AFIX 0 C27 1 0.160832 0.585659 0.629622 11.00000 0.07090 0.02469 = 0.02733 0.00080 0.01097 -0.00164 O2 6 0.588281 0.633987 0.685667 11.00000 0.07481 0.15597 = 0.07820 0.03571 0.01003 -0.00767 AFIX 147 H2A 2 0.530354 0.611585 0.693981 11.00000 -1.50000 AFIX 0 C28 1 0.581816 0.652533 0.558170 11.00000 0.09789 0.25132 = 0.09732 0.08186 0.02381 0.02752 AFIX 137 H28A 2 0.613330 0.622368 0.507884 11.00000 -1.50000 H28B 2 0.631378 0.687022 0.553010 11.00000 -1.50000 H28C 2 0.496363 0.660768 0.527274 11.00000 -1.50000 AFIX 0 O3 6 0.769030 0.698253 0.811447 11.00000 0.18409 0.22491 = 0.25831 -0.11430 0.10682 -0.03483 AFIX 147 H3A 2 0.702071 0.681201 0.796155 11.00000 -1.50000 AFIX 0 C29 1 0.756273 0.741596 0.895223 11.00000 0.13026 0.17603 = 0.12965 0.00791 0.04806 0.00550 AFIX 137 H29A 2 0.682951 0.764019 0.867842 11.00000 -1.50000 H29B 2 0.828706 0.766286 0.900367 11.00000 -1.50000 H29C 2 0.748120 0.725208 0.976846 11.00000 -1.50000 AFIX 0 HKLF 4 REM 9 in P21/c #14 REM R1 = 0.0435 for 4282 Fo > 4sig(Fo) and 0.0746 for all 6202 data REM 356 parameters refined using 0 restraints END WGHT 0.0349 0.0000 REM Highest difference peak 1.496, deepest hole -1.625, 1-sigma level 0.145 Q1 1 0.3535 0.6166 0.9367 11.00000 0.05 1.50 Q2 1 -0.2713 0.6429 0.6157 11.00000 0.05 1.13 Q3 1 0.3915 0.6376 0.9034 11.00000 0.05 0.94 Q4 1 0.2718 0.6012 0.7563 11.00000 0.05 0.81 Q5 1 0.1864 0.6022 0.8144 11.00000 0.05 0.79 Q6 1 0.2684 0.6412 0.7677 11.00000 0.05 0.70 Q7 1 0.1337 0.6384 0.8804 11.00000 0.05 0.70 Q8 1 0.1831 0.6386 0.9341 11.00000 0.05 0.66 Q9 1 0.1667 0.6215 0.8648 11.00000 0.05 0.64 Q10 1 0.2913 0.8795 0.8980 11.00000 0.05 0.63 Q11 1 0.3618 0.6205 0.7790 11.00000 0.05 0.62 Q12 1 0.1081 0.6331 0.7774 11.00000 0.05 0.59 Q13 1 0.2708 0.6402 1.0230 11.00000 0.05 0.55 Q14 1 0.3615 0.6013 0.8338 11.00000 0.05 0.55 Q15 1 0.1013 0.5983 0.3003 11.00000 0.05 0.55 Q16 1 0.3993 0.6213 0.6892 11.00000 0.05 0.55 Q17 1 0.4308 0.6074 0.9018 11.00000 0.05 0.54 Q18 1 0.4333 0.6399 0.9921 11.00000 0.05 0.53 Q19 1 0.5042 0.6703 0.8138 11.00000 0.05 0.52 Q20 1 0.3558 0.6112 1.0147 11.00000 0.05 0.52 ; _shelx_res_checksum 88708 _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 1.597 _oxdiff_exptl_absorpt_empirical_full_min 0.554 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.26982(2) 0.61940(2) 0.88783(2) 0.03403(9) Uani 1 1 d . . . . . F1 F 0.0429(5) 0.53521(17) 0.3160(4) 0.0827(16) Uani 1 1 d . . . . . O1 O 0.3708(4) 0.58755(17) 0.7348(4) 0.0448(11) Uani 1 1 d . . . . . N1 N 0.3390(5) 0.5224(2) 1.0490(5) 0.0452(14) Uani 1 1 d . . . . . N2 N 0.2517(5) 0.5381(2) 0.9527(5) 0.0427(14) Uani 1 1 d . . . . . N3 N 0.1222(5) 0.60953(18) 0.7368(5) 0.0391(13) Uani 1 1 d . . . . . N4 N 0.2291(5) 0.74196(19) 0.9192(5) 0.0383(12) Uani 1 1 d . . . . . N5 N 0.2919(5) 0.70491(19) 0.8486(5) 0.0345(12) Uani 1 1 d . . . . . C1 C 0.1635(6) 0.6550(2) 1.0104(5) 0.0353(14) Uani 1 1 d . . . . . C2 C 0.0915(7) 0.6291(3) 1.0958(6) 0.0461(17) Uani 1 1 d . . . . . H2 H 0.0955 0.5890 1.1059 0.055 Uiso 1 1 calc R . . . . C3 C 0.0144(7) 0.6605(3) 1.1663(6) 0.0541(19) Uani 1 1 d . . . . . H3 H -0.0337 0.6414 1.2210 0.065 Uiso 1 1 calc R . . . . C4 C 0.0089(7) 0.7208(3) 1.1552(7) 0.056(2) Uani 1 1 d . . . . . H4 H -0.0427 0.7422 1.2026 0.068 Uiso 1 1 calc R . . . . C5 C 0.0807(7) 0.7487(3) 1.0732(7) 0.0499(18) Uani 1 1 d . . . . . H5 H 0.0785 0.7890 1.0649 0.060 Uiso 1 1 calc R . . . . C6 C 0.1550(6) 0.7158(2) 1.0046(6) 0.0357(14) Uani 1 1 d . . . . . C7 C 0.2588(7) 0.7973(3) 0.8908(6) 0.0475(18) Uani 1 1 d . . . . . H7 H 0.2285 0.8306 0.9267 0.057 Uiso 1 1 calc R . . . . C8 C 0.3395(7) 0.7963(3) 0.8020(7) 0.055(2) Uani 1 1 d . . . . . H8 H 0.3750 0.8281 0.7653 0.066 Uiso 1 1 calc R . . . . C9 C 0.3581(6) 0.7377(3) 0.7768(6) 0.0454(16) Uani 1 1 d . . . . . H9 H 0.4092 0.7235 0.7185 0.054 Uiso 1 1 calc R . . . . C10 C 0.1726(8) 0.4937(3) 0.9344(6) 0.0534(19) Uani 1 1 d . . . . . H10 H 0.1038 0.4924 0.8734 0.064 Uiso 1 1 calc R . . . . C11 C 0.2083(9) 0.4489(3) 1.0208(7) 0.064(2) Uani 1 1 d . . . . . H11 H 0.1679 0.4135 1.0289 0.077 Uiso 1 1 calc R . . . . C12 C 0.3142(9) 0.4680(3) 1.0900(7) 0.062(2) Uani 1 1 d . . . . . H12 H 0.3612 0.4476 1.1539 0.074 Uiso 1 1 calc R . . . . C13 C 0.4319(7) 0.5638(3) 1.0874(6) 0.0494(18) Uani 1 1 d . . . . . C14 C 0.5271(8) 0.5533(3) 1.1818(7) 0.062(2) Uani 1 1 d . . . . . H14 H 0.5324 0.5177 1.2237 0.074 Uiso 1 1 calc R . . . . C15 C 0.6143(8) 0.5962(4) 1.2134(7) 0.073(3) Uani 1 1 d . . . . . H15 H 0.6790 0.5897 1.2771 0.088 Uiso 1 1 calc R . . . . C16 C 0.6059(7) 0.6484(4) 1.1513(8) 0.068(2) Uani 1 1 d . . . . . H16 H 0.6653 0.6772 1.1731 0.082 Uiso 1 1 calc R . . . . C17 C 0.5097(7) 0.6590(3) 1.0561(6) 0.0527(18) Uani 1 1 d . . . . . H17 H 0.5054 0.6948 1.0155 0.063 Uiso 1 1 calc R . . . . C18 C 0.4190(7) 0.6168(3) 1.0200(6) 0.0427(16) Uani 1 1 d . . . . . C19 C 0.2917(7) 0.5737(3) 0.6335(6) 0.0452(17) Uani 1 1 d . . . . . C20 C 0.3330(8) 0.5492(3) 0.5253(7) 0.061(2) Uani 1 1 d . . . . . H20 H 0.4176 0.5408 0.5240 0.073 Uiso 1 1 calc R . . . . C21 C 0.2484(9) 0.5370(3) 0.4189(7) 0.064(2) Uani 1 1 d . . . . . H21 H 0.2778 0.5211 0.3474 0.077 Uiso 1 1 calc R . . . . C22 C 0.1247(9) 0.5481(3) 0.4185(6) 0.054(2) Uani 1 1 d . . . . . C23 C 0.0767(8) 0.5736(2) 0.5240(6) 0.0483(19) Uani 1 1 d . . . . . C24 C -0.0506(8) 0.5865(3) 0.5293(7) 0.060(2) Uani 1 1 d . . . . . H24 H -0.1092 0.5793 0.4602 0.072 Uiso 1 1 calc R . . . . C25 C -0.0862(7) 0.6096(3) 0.6363(8) 0.057(2) Uani 1 1 d . . . . . H25 H -0.1701 0.6184 0.6410 0.068 Uiso 1 1 calc R . . . . C26 C 0.0026(6) 0.6207(2) 0.7413(6) 0.0435(16) Uani 1 1 d . . . . . H26 H -0.0238 0.6360 0.8147 0.052 Uiso 1 1 calc R . . . . C27 C 0.1608(7) 0.5857(2) 0.6296(6) 0.0406(16) Uani 1 1 d . . . . . O2 O 0.5883(6) 0.6340(4) 0.6857(6) 0.103(2) Uani 1 1 d . . . . . H2A H 0.5304 0.6116 0.6940 0.154 Uiso 1 1 calc GR . . . . C28 C 0.5818(10) 0.6525(6) 0.5582(10) 0.148(5) Uani 1 1 d . . . . . H28A H 0.6133 0.6224 0.5079 0.222 Uiso 1 1 calc GR . . . . H28B H 0.6314 0.6870 0.5530 0.222 Uiso 1 1 calc GR . . . . H28C H 0.4964 0.6608 0.5273 0.222 Uiso 1 1 calc GR . . . . O3 O 0.7690(11) 0.6983(6) 0.8114(15) 0.216(6) Uani 1 1 d . . . . . H3A H 0.7021 0.6812 0.7962 0.325 Uiso 1 1 calc GR . . . . C29 C 0.7563(12) 0.7416(6) 0.8952(11) 0.143(5) Uani 1 1 d . . . . . H29A H 0.6830 0.7640 0.8678 0.214 Uiso 1 1 calc GR . . . . H29B H 0.8287 0.7663 0.9004 0.214 Uiso 1 1 calc GR . . . . H29C H 0.7481 0.7252 0.9768 0.214 Uiso 1 1 calc GR . . . . 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 0.04760(16) 0.02913(13) 0.02686(14) 0.00033(10) 0.01081(11) 0.00403(11) F1 0.142(5) 0.063(3) 0.039(3) -0.007(2) -0.010(3) -0.024(3) O1 0.049(3) 0.048(3) 0.040(3) -0.003(2) 0.014(2) 0.011(2) N1 0.062(4) 0.038(3) 0.038(3) 0.002(2) 0.011(3) 0.015(3) N2 0.064(4) 0.029(3) 0.035(3) -0.002(2) 0.009(3) 0.010(3) N3 0.059(4) 0.029(3) 0.031(3) 0.003(2) 0.013(3) -0.003(2) N4 0.051(3) 0.029(3) 0.036(3) -0.002(2) 0.010(3) 0.001(2) N5 0.042(3) 0.032(3) 0.031(3) 0.001(2) 0.010(2) 0.001(2) C1 0.044(4) 0.036(3) 0.027(3) -0.003(3) 0.008(3) 0.000(3) C2 0.062(5) 0.040(4) 0.039(4) -0.001(3) 0.017(3) -0.001(3) C3 0.071(5) 0.057(4) 0.038(4) 0.004(3) 0.023(4) 0.002(4) C4 0.066(5) 0.053(4) 0.054(5) -0.010(4) 0.024(4) 0.010(4) C5 0.063(5) 0.035(3) 0.055(5) -0.008(3) 0.020(4) 0.011(3) C6 0.045(4) 0.032(3) 0.033(4) -0.001(3) 0.012(3) 0.001(3) C7 0.069(5) 0.027(3) 0.048(4) 0.001(3) 0.010(4) -0.002(3) C8 0.083(6) 0.037(4) 0.048(5) 0.002(3) 0.018(4) -0.017(4) C9 0.050(4) 0.056(4) 0.034(4) 0.005(3) 0.019(3) 0.000(3) C10 0.077(6) 0.044(4) 0.041(4) -0.003(3) 0.018(4) 0.004(4) C11 0.109(7) 0.037(4) 0.050(5) -0.001(4) 0.027(5) -0.011(4) C12 0.104(7) 0.036(4) 0.048(5) 0.009(3) 0.024(5) 0.011(4) C13 0.068(5) 0.046(4) 0.034(4) -0.001(3) 0.006(4) 0.013(4) C14 0.063(5) 0.078(5) 0.045(5) 0.005(4) 0.009(4) 0.025(5) C15 0.058(5) 0.113(7) 0.046(5) -0.009(5) -0.004(4) 0.035(5) C16 0.054(5) 0.089(6) 0.061(5) -0.016(5) 0.003(4) -0.001(5) C17 0.054(5) 0.063(4) 0.041(4) -0.002(3) 0.006(4) 0.006(4) C18 0.054(4) 0.048(4) 0.028(3) -0.006(3) 0.011(3) 0.012(3) C19 0.074(5) 0.031(3) 0.033(4) 0.002(3) 0.018(4) -0.002(3) C20 0.086(6) 0.057(4) 0.045(5) -0.004(4) 0.031(4) 0.012(4) C21 0.115(8) 0.050(4) 0.031(4) -0.008(3) 0.026(5) 0.001(5) C22 0.093(6) 0.039(4) 0.031(4) -0.001(3) 0.010(4) -0.013(4) C23 0.081(6) 0.028(3) 0.035(4) 0.008(3) 0.006(4) -0.012(4) C24 0.073(6) 0.050(4) 0.053(5) 0.007(4) -0.017(5) -0.018(4) C25 0.043(4) 0.057(5) 0.069(6) 0.001(4) -0.005(4) 0.004(3) C26 0.047(4) 0.042(3) 0.043(4) 0.000(3) 0.010(3) 0.004(3) C27 0.071(5) 0.025(3) 0.027(3) 0.001(3) 0.011(3) -0.002(3) O2 0.075(5) 0.156(7) 0.078(5) 0.036(4) 0.010(4) -0.008(4) C28 0.098(9) 0.251(14) 0.097(10) 0.082(10) 0.024(7) 0.028(9) O3 0.184(12) 0.225(12) 0.258(14) -0.114(10) 0.107(11) -0.035(9) C29 0.130(12) 0.176(14) 0.130(12) 0.008(9) 0.048(10) 0.006(9) 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' F F 0.0171 0.0103 '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 N2 Ir1 O1 91.10(18) . . ? N2 Ir1 N3 93.91(19) . . ? N2 Ir1 N5 171.8(2) . . ? N2 Ir1 C18 80.3(2) . . ? N3 Ir1 O1 77.96(19) . . ? N5 Ir1 O1 95.32(18) . . ? N5 Ir1 N3 92.39(18) . . ? C1 Ir1 O1 172.26(19) . . ? C1 Ir1 N2 94.2(2) . . ? C1 Ir1 N3 96.0(2) . . ? C1 Ir1 N5 80.0(2) . . ? C1 Ir1 C18 91.3(2) . . ? C18 Ir1 O1 95.2(2) . . ? C18 Ir1 N3 171.0(2) . . ? C18 Ir1 N5 94.0(2) . . ? C19 O1 Ir1 111.0(4) . . ? N2 N1 C13 116.6(5) . . ? C12 N1 N2 110.1(6) . . ? C12 N1 C13 133.3(6) . . ? N1 N2 Ir1 115.0(4) . . ? C10 N2 Ir1 138.4(5) . . ? C10 N2 N1 106.5(5) . . ? C26 N3 Ir1 126.7(4) . . ? C26 N3 C27 119.5(6) . . ? C27 N3 Ir1 113.6(5) . . ? N5 N4 C6 116.0(5) . . ? C7 N4 N5 108.7(5) . . ? C7 N4 C6 135.2(6) . . ? N4 N5 Ir1 114.6(4) . . ? C9 N5 Ir1 138.4(4) . . ? C9 N5 N4 106.9(5) . . ? C2 C1 Ir1 130.6(4) . . ? C2 C1 C6 114.6(6) . . ? C6 C1 Ir1 114.7(4) . . ? C3 C2 C1 122.9(6) . . ? C2 C3 C4 119.8(7) . . ? C5 C4 C3 119.6(6) . . ? C6 C5 C4 118.6(6) . . ? C1 C6 N4 114.6(5) . . ? C5 C6 N4 120.8(5) . . ? C5 C6 C1 124.6(6) . . ? C8 C7 N4 109.0(6) . . ? C7 C8 C9 105.6(6) . . ? N5 C9 C8 109.8(6) . . ? N2 C10 C11 110.0(7) . . ? C12 C11 C10 105.7(6) . . ? N1 C12 C11 107.8(7) . . ? N1 C13 C18 114.1(6) . . ? C14 C13 N1 122.7(6) . . ? C14 C13 C18 123.1(7) . . ? C13 C14 C15 119.0(7) . . ? C16 C15 C14 120.2(7) . . ? C15 C16 C17 120.6(8) . . ? C16 C17 C18 121.5(7) . . ? C13 C18 Ir1 114.0(5) . . ? C17 C18 Ir1 130.5(5) . . ? C17 C18 C13 115.5(6) . . ? O1 C19 C20 122.0(7) . . ? O1 C19 C27 120.9(6) . . ? C20 C19 C27 117.0(7) . . ? C19 C20 C21 120.7(8) . . ? C22 C21 C20 121.0(7) . . ? F1 C22 C23 118.0(8) . . ? C21 C22 F1 120.7(7) . . ? C21 C22 C23 121.3(7) . . ? C24 C23 C22 124.0(7) . . ? C27 C23 C22 117.7(8) . . ? C27 C23 C24 118.3(7) . . ? C25 C24 C23 118.8(7) . . ? C24 C25 C26 120.7(7) . . ? N3 C26 C25 121.0(7) . . ? N3 C27 C19 116.1(6) . . ? N3 C27 C23 121.6(7) . . ? C23 C27 C19 122.4(7) . . ? 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 2.180(4) . ? Ir1 N2 2.009(5) . ? Ir1 N3 2.145(5) . ? Ir1 N5 2.029(4) . ? Ir1 C1 1.999(6) . ? Ir1 C18 2.016(7) . ? F1 C22 1.358(8) . ? O1 C19 1.338(8) . ? N1 N2 1.361(7) . ? N1 C12 1.359(8) . ? N1 C13 1.408(8) . ? N2 C10 1.330(8) . ? N3 C26 1.316(8) . ? N3 C27 1.371(8) . ? N4 N5 1.363(7) . ? N4 C6 1.407(8) . ? N4 C7 1.353(7) . ? N5 C9 1.333(7) . ? C1 C2 1.390(8) . ? C1 C6 1.402(7) . ? C2 C3 1.380(9) . ? C3 C4 1.392(8) . ? C4 C5 1.384(9) . ? C5 C6 1.367(8) . ? C7 C8 1.351(9) . ? C8 C9 1.392(8) . ? C10 C11 1.406(9) . ? C11 C12 1.360(10) . ? C13 C14 1.375(9) . ? C13 C18 1.414(8) . ? C14 C15 1.377(11) . ? C15 C16 1.369(11) . ? C16 C17 1.389(9) . ? C17 C18 1.397(9) . ? C19 C20 1.397(9) . ? C19 C27 1.429(10) . ? C20 C21 1.402(10) . ? C21 C22 1.354(10) . ? C22 C23 1.412(10) . ? C23 C24 1.407(10) . ? C23 C27 1.393(9) . ? C24 C25 1.350(10) . ? C25 C26 1.412(9) . ? O2 C28 1.418(10) . ? O3 C29 1.354(12) . ?