#------------------------------------------------------------------------------ #$Date: 2020-10-06 13:11:15 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257764 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557797.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_1557797 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_page_last 7837 _journal_paper_doi 10.1039/D0NJ00465K _journal_volume 44 _journal_year 2020 _chemical_formula_moiety 'C35 H21 F Ir N3 O' _chemical_formula_sum 'C35 H21 F Ir N3 O' _chemical_formula_weight 710.77 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary heavy _audit_creation_date 2019-09-21 _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 101.136(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 21.5039(6) _cell_length_b 16.6692(5) _cell_length_c 14.8357(4) _cell_measurement_reflns_used 3169 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.7120 _cell_measurement_theta_min 3.6520 _cell_volume 5217.8(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 0.997 _diffrn_measured_fraction_theta_max 0.877 _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 60.50 0.90 25.00 -- 18.63 -99.00 150.00 45 2 \w -89.00 10.00 0.90 25.00 -- -18.94 -77.00-120.00 110 3 \w -27.00 0.00 0.90 25.00 -- -18.94 -57.00 0.00 30 4 \w -45.00 46.80 0.90 25.00 -- -18.94 77.00 0.00 102 5 \w -85.00 9.50 0.90 25.00 -- -18.94 -19.00 60.00 105 ; _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 -0.0129973000 _diffrn_orient_matrix_UB_12 -0.0362622000 _diffrn_orient_matrix_UB_13 0.0132539000 _diffrn_orient_matrix_UB_21 0.0307169000 _diffrn_orient_matrix_UB_22 -0.0128805000 _diffrn_orient_matrix_UB_23 0.0215485000 _diffrn_orient_matrix_UB_31 -0.0041660000 _diffrn_orient_matrix_UB_32 0.0181744000 _diffrn_orient_matrix_UB_33 0.0416450000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_unetI/netI 0.0925 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.877 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 18790 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.877 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.290 _diffrn_reflns_theta_min 3.362 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 5.161 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77928 _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 yellow _exptl_crystal_density_diffrn 1.810 _exptl_crystal_description block _exptl_crystal_F_000 2768 _refine_diff_density_max 1.259 _refine_diff_density_min -0.961 _refine_diff_density_rms 0.145 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 6270 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.999 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0448 _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^)+(0.0104P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.0624 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3953 _reflns_number_total 6270 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj00465k2.cif _cod_data_source_block 64 _cod_depositor_comments ;Adding full bibliography for 1557795--1557798.cif. Adding full bibliography for 1557795--1557798.cif. ; _cod_database_code 1557797 _shelxl_version_number 2014-3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.71 _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), C0AA(H0AA), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31) ; _shelx_res_file ; TITL 64 in Cc #9 New: C2/c CELL 0.71073 21.5039 16.6692 14.8357 90 101.136 90 ZERR 8 0.0006 0.0005 0.0004 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C 2.310 20.844 1.02 10.208 1.589 0.569 0.865 51.651 0.216 0.003 0.002 = 11.5 0.68 12.01 SFAC H F SFAC Ir 27.305 1.593 16.73 8.866 15.612 0.418 5.834 45.001 11.472 -1.444 = 7.989 33100 1.32 192.22 SFAC N 12.213 0.006 3.132 9.893 2.013 28.998 1.166 0.583 -11.529 0.006 = 0.003 19.6 0.68 14.01 SFAC O 3.049 13.277 2.287 5.701 1.546 0.324 0.867 32.909 0.251 0.011 0.006 = 32.5 0.68 16 UNIT 280 168 8 8 24 8 L.S. 5 PLAN 20 fmap 2 acta REM REM REM WGHT 0.010400 FVAR 0.41524 IR1 4 0.162529 0.410765 0.162723 11.00000 0.03527 0.03696 = 0.03365 -0.00237 0.00883 0.00025 F1 3 -0.003887 0.078285 0.140666 11.00000 0.06604 0.05712 = 0.11257 0.00408 0.01897 -0.02163 O1 6 0.074577 0.380752 0.073743 11.00000 0.03758 0.04567 = 0.03886 0.00316 0.00396 -0.00223 N1 5 0.146993 0.291829 0.205627 11.00000 0.03419 0.03787 = 0.03962 -0.00027 0.01411 0.00131 N2 5 0.216045 0.374046 0.070541 11.00000 0.03539 0.03841 = 0.03815 -0.00734 0.00937 -0.00308 C3 1 0.249059 0.426135 0.241341 11.00000 0.04808 0.02912 = 0.03266 -0.00286 0.01000 -0.00261 C4 1 0.166893 0.524473 0.121380 11.00000 0.03725 0.04119 = 0.03438 0.00335 0.00710 -0.00302 N5 5 0.113461 0.464474 0.252736 11.00000 0.03155 0.04837 = 0.03671 -0.00398 0.00653 0.00316 C1 1 0.054457 0.309177 0.088887 11.00000 0.03344 0.04418 = 0.03383 -0.00704 0.00976 0.00269 C2 1 -0.001397 0.275616 0.040513 11.00000 0.04012 0.06203 = 0.05499 0.00396 -0.00259 -0.00574 AFIX 43 H2 2 -0.026573 0.305616 -0.005412 11.00000 -1.20000 AFIX 0 C0AA 1 -0.020729 0.198829 0.058603 11.00000 0.03879 0.07006 = 0.07510 0.00014 0.00130 -0.01575 AFIX 43 H0AA 2 -0.058173 0.178112 0.024625 11.00000 -1.20000 AFIX 0 C1AA 1 0.014341 0.154414 0.124836 11.00000 0.04878 0.04477 = 0.07573 -0.00597 0.01758 -0.01362 C5 1 0.071314 0.181504 0.177972 11.00000 0.04739 0.04231 = 0.05241 -0.00448 0.02446 0.00121 C6 1 0.110933 0.138308 0.248231 11.00000 0.06185 0.02863 = 0.07163 0.00927 0.02518 0.00182 AFIX 43 H6 2 0.099142 0.087615 0.265035 11.00000 -1.20000 AFIX 0 C7 1 0.166466 0.171469 0.291100 11.00000 0.06076 0.04862 = 0.05643 0.01380 0.00513 0.00956 AFIX 43 H7 2 0.193701 0.142342 0.335580 11.00000 -1.20000 AFIX 0 C8 1 0.182892 0.248475 0.269055 11.00000 0.04469 0.04954 = 0.04385 0.00313 -0.00281 0.00366 AFIX 43 H8 2 0.220776 0.270213 0.300401 11.00000 -1.20000 AFIX 0 C9 1 0.090443 0.259476 0.159904 11.00000 0.03188 0.04388 = 0.04034 -0.00110 0.01761 0.00185 C10 1 0.194560 0.349439 -0.015365 11.00000 0.04474 0.04505 = 0.03594 -0.00499 0.00510 -0.00263 AFIX 43 H10 2 0.151373 0.340754 -0.035334 11.00000 -1.20000 AFIX 0 C11 1 0.235710 0.336597 -0.075424 11.00000 0.06865 0.05747 = 0.04097 -0.00320 0.00980 0.00745 AFIX 43 H11 2 0.219794 0.321299 -0.135752 11.00000 -1.20000 AFIX 0 C12 1 0.298913 0.346263 -0.046488 11.00000 0.06815 0.06403 = 0.05223 -0.00055 0.04061 0.01444 AFIX 43 H12 2 0.326243 0.337649 -0.087057 11.00000 -1.20000 AFIX 0 C13 1 0.323157 0.369003 0.043581 11.00000 0.04289 0.04046 = 0.06157 0.00179 0.02087 0.00345 C14 1 0.388181 0.380326 0.083106 11.00000 0.04141 0.06726 = 0.08252 0.00367 0.03053 0.00427 AFIX 43 H14 2 0.418648 0.371125 0.047529 11.00000 -1.20000 AFIX 0 C15 1 0.406766 0.404198 0.171362 11.00000 0.03118 0.05656 = 0.08783 0.00788 0.00720 -0.00799 AFIX 43 H15 2 0.449703 0.412234 0.194303 11.00000 -1.20000 AFIX 0 C16 1 0.362993 0.417361 0.230003 11.00000 0.04308 0.03597 = 0.05922 0.00393 0.00166 -0.00452 C17 1 0.378789 0.440115 0.323250 11.00000 0.04775 0.05095 = 0.07132 0.00310 -0.01136 -0.00669 AFIX 43 H17 2 0.421108 0.445407 0.351594 11.00000 -1.20000 AFIX 0 C18 1 0.332495 0.454299 0.371706 11.00000 0.07095 0.05190 = 0.05168 -0.00988 -0.01117 -0.00516 AFIX 43 H18 2 0.343965 0.468165 0.433405 11.00000 -1.20000 AFIX 0 C19 1 0.268001 0.448784 0.332031 11.00000 0.06393 0.04763 = 0.04518 -0.00111 0.01166 0.00109 AFIX 43 H19 2 0.237673 0.460482 0.367089 11.00000 -1.20000 AFIX 0 C20 1 0.297874 0.410279 0.193160 11.00000 0.03292 0.02457 = 0.04242 -0.00069 0.00569 -0.00131 C21 1 0.280173 0.383088 0.100730 11.00000 0.03145 0.03451 = 0.04278 0.00050 0.00854 0.00222 C22 1 0.192755 0.560411 0.052421 11.00000 0.05185 0.04664 = 0.03702 0.00295 0.01330 -0.00179 AFIX 43 H22 2 0.212716 0.528132 0.015484 11.00000 -1.20000 AFIX 0 C23 1 0.189934 0.643708 0.036275 11.00000 0.05780 0.04985 = 0.06010 0.02565 0.00360 -0.00938 AFIX 43 H23 2 0.207218 0.664648 -0.011535 11.00000 -1.20000 AFIX 0 C24 1 0.162418 0.694286 0.089217 11.00000 0.04683 0.04116 = 0.07954 0.00785 -0.01474 -0.00586 AFIX 43 H24 2 0.161463 0.749247 0.078263 11.00000 -1.20000 AFIX 0 C25 1 0.135456 0.662312 0.160695 11.00000 0.04076 0.03569 = 0.05339 -0.00199 -0.00677 0.00286 C26 1 0.104474 0.710276 0.217767 11.00000 0.06077 0.04115 = 0.08737 -0.00938 -0.00024 0.00612 AFIX 43 H26 2 0.102669 0.765575 0.209349 11.00000 -1.20000 AFIX 0 C27 1 0.077789 0.677421 0.283515 11.00000 0.05179 0.05549 = 0.08355 -0.03486 0.00308 0.00880 AFIX 43 H27 2 0.057935 0.710830 0.319470 11.00000 -1.20000 AFIX 0 C28 1 0.078700 0.592850 0.300468 11.00000 0.03266 0.05056 = 0.04794 -0.01232 -0.00125 0.00212 C29 1 0.050202 0.552972 0.365345 11.00000 0.04597 0.07742 = 0.04987 -0.02881 0.00624 0.00777 AFIX 43 H29 2 0.029512 0.582129 0.404168 11.00000 -1.20000 AFIX 0 C30 1 0.052932 0.471930 0.371218 11.00000 0.04955 0.07665 = 0.04797 -0.00646 0.02096 -0.00853 AFIX 43 H30 2 0.033159 0.445305 0.413052 11.00000 -1.20000 AFIX 0 C31 1 0.085534 0.428098 0.314313 11.00000 0.04792 0.04662 = 0.04756 0.00166 0.01461 0.00434 AFIX 43 H31 2 0.087701 0.372535 0.319668 11.00000 -1.20000 AFIX 0 C32 1 0.109645 0.545960 0.244775 11.00000 0.03601 0.03904 = 0.04396 -0.01477 -0.00077 0.00261 C33 1 0.138092 0.578602 0.174442 11.00000 0.03707 0.03828 = 0.03985 -0.00127 -0.00122 0.00451 HKLF 4 1 -1 0 0 0 1 0 0 0 -1 REM 64 in Cc #9 New: C2/c REM R1 = 0.0448 for 3953 Fo > 4sig(Fo) and 0.0966 for all 6270 data REM 370 parameters refined using 0 restraints END WGHT 0.0104 0.0000 REM Highest difference peak 1.259, deepest hole -0.961, 1-sigma level 0.145 Q1 1 0.4916 0.4110 -0.0085 11.00000 0.05 1.26 Q2 1 0.1611 0.7740 0.1612 11.00000 0.05 1.07 Q3 1 0.1841 0.4772 0.1658 11.00000 0.05 0.67 Q4 1 0.1676 0.2501 0.2079 11.00000 0.05 0.66 Q5 1 0.1494 0.3531 0.2187 11.00000 0.05 0.64 Q6 1 0.1901 0.3686 0.2171 11.00000 0.05 0.63 Q7 1 0.1560 0.4072 0.0818 11.00000 0.05 0.62 Q8 1 0.1085 0.3991 0.1724 11.00000 0.05 0.61 Q9 1 0.2026 0.5743 0.1566 11.00000 0.05 0.58 Q10 1 0.2061 0.3772 0.1203 11.00000 0.05 0.57 Q11 1 0.1328 0.2732 0.2321 11.00000 0.05 0.57 Q12 1 0.1623 0.4069 0.2384 11.00000 0.05 0.57 Q13 1 0.1715 0.3483 0.0998 11.00000 0.05 0.57 Q14 1 0.1215 0.4413 0.2219 11.00000 0.05 0.56 Q15 1 0.3681 0.4521 0.2596 11.00000 0.05 0.55 Q16 1 0.1686 0.5760 0.2184 11.00000 0.05 0.53 Q17 1 0.1432 0.4614 0.1073 11.00000 0.05 0.53 Q18 1 0.1897 0.4241 0.2465 11.00000 0.05 0.52 Q19 1 0.2423 0.5089 0.0713 11.00000 0.05 0.50 Q20 1 0.2182 0.5619 0.2382 11.00000 0.05 0.50 ; _shelx_res_checksum 5122 _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 1.211 _oxdiff_exptl_absorpt_empirical_full_min 0.859 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.16253(2) 0.41077(2) 0.16272(2) 0.03500(7) Uani 1 1 d . . . . . F1 F -0.00389(16) 0.0783(2) 0.1407(2) 0.0783(12) Uani 1 1 d . . . . . O1 O 0.07458(16) 0.3808(2) 0.0737(2) 0.0412(10) Uani 1 1 d . . . . . N1 N 0.1470(2) 0.2918(3) 0.2056(3) 0.0363(12) Uani 1 1 d . . . . . N2 N 0.2160(2) 0.3740(3) 0.0705(3) 0.0370(12) Uani 1 1 d . . . . . C3 C 0.2491(2) 0.4261(3) 0.2413(3) 0.0363(14) Uani 1 1 d . . . . . C4 C 0.1669(2) 0.5245(3) 0.1214(3) 0.0376(14) Uani 1 1 d . . . . . N5 N 0.11346(19) 0.4645(3) 0.2527(3) 0.0389(12) Uani 1 1 d . . . . . C1 C 0.0545(3) 0.3092(4) 0.0889(3) 0.0367(14) Uani 1 1 d . . . . . C2 C -0.0014(3) 0.2756(4) 0.0405(4) 0.0540(18) Uani 1 1 d . . . . . H2 H -0.0266 0.3056 -0.0054 0.065 Uiso 1 1 calc R . . . . C0AA C -0.0207(3) 0.1988(4) 0.0586(4) 0.063(2) Uani 1 1 d . . . . . H0AA H -0.0582 0.1781 0.0246 0.075 Uiso 1 1 calc R . . . . C1AA C 0.0143(3) 0.1544(4) 0.1248(5) 0.0557(18) Uani 1 1 d . . . . . C5 C 0.0713(3) 0.1815(4) 0.1780(4) 0.0454(16) Uani 1 1 d . . . . . C6 C 0.1109(3) 0.1383(4) 0.2482(4) 0.0524(17) Uani 1 1 d . . . . . H6 H 0.0991 0.0876 0.2650 0.063 Uiso 1 1 calc R . . . . C7 C 0.1665(3) 0.1715(4) 0.2911(4) 0.0561(18) Uani 1 1 d . . . . . H7 H 0.1937 0.1423 0.3356 0.067 Uiso 1 1 calc R . . . . C8 C 0.1829(3) 0.2485(4) 0.2691(3) 0.0475(17) Uani 1 1 d . . . . . H8 H 0.2208 0.2702 0.3004 0.057 Uiso 1 1 calc R . . . . C9 C 0.0904(2) 0.2595(4) 0.1599(3) 0.0373(14) Uani 1 1 d . . . . . C10 C 0.1946(3) 0.3494(3) -0.0154(3) 0.0423(15) Uani 1 1 d . . . . . H10 H 0.1514 0.3408 -0.0353 0.051 Uiso 1 1 calc R . . . . C11 C 0.2357(3) 0.3366(4) -0.0754(4) 0.0558(18) Uani 1 1 d . . . . . H11 H 0.2198 0.3213 -0.1358 0.067 Uiso 1 1 calc R . . . . C12 C 0.2989(3) 0.3463(4) -0.0465(4) 0.0576(19) Uani 1 1 d . . . . . H12 H 0.3262 0.3376 -0.0871 0.069 Uiso 1 1 calc R . . . . C13 C 0.3232(3) 0.3690(4) 0.0436(4) 0.0469(16) Uani 1 1 d . . . . . C14 C 0.3882(3) 0.3803(4) 0.0831(5) 0.061(2) Uani 1 1 d . . . . . H14 H 0.4186 0.3711 0.0475 0.073 Uiso 1 1 calc R . . . . C15 C 0.4068(3) 0.4042(4) 0.1714(5) 0.0591(18) Uani 1 1 d . . . . . H15 H 0.4497 0.4122 0.1943 0.071 Uiso 1 1 calc R . . . . C16 C 0.3630(3) 0.4174(4) 0.2300(4) 0.0472(15) Uani 1 1 d . . . . . C17 C 0.3788(3) 0.4401(4) 0.3232(4) 0.0597(19) Uani 1 1 d . . . . . H17 H 0.4211 0.4454 0.3516 0.072 Uiso 1 1 calc R . . . . C18 C 0.3325(3) 0.4543(4) 0.3717(4) 0.061(2) Uani 1 1 d . . . . . H18 H 0.3440 0.4682 0.4334 0.074 Uiso 1 1 calc R . . . . C19 C 0.2680(3) 0.4488(3) 0.3320(4) 0.0521(17) Uani 1 1 d . . . . . H19 H 0.2377 0.4605 0.3671 0.063 Uiso 1 1 calc R . . . . C20 C 0.2979(2) 0.4103(3) 0.1932(3) 0.0335(12) Uani 1 1 d . . . . . C21 C 0.2802(2) 0.3831(3) 0.1007(4) 0.0361(14) Uani 1 1 d . . . . . C22 C 0.1928(3) 0.5604(4) 0.0524(3) 0.0445(16) Uani 1 1 d . . . . . H22 H 0.2127 0.5281 0.0155 0.053 Uiso 1 1 calc R . . . . C23 C 0.1899(3) 0.6437(4) 0.0363(4) 0.0570(19) Uani 1 1 d . . . . . H23 H 0.2072 0.6646 -0.0115 0.068 Uiso 1 1 calc R . . . . C24 C 0.1624(3) 0.6943(4) 0.0892(4) 0.0595(19) Uani 1 1 d . . . . . H24 H 0.1615 0.7492 0.0783 0.071 Uiso 1 1 calc R . . . . C25 C 0.1355(3) 0.6623(4) 0.1607(4) 0.0454(16) Uani 1 1 d . . . . . C26 C 0.1045(3) 0.7103(4) 0.2178(5) 0.065(2) Uani 1 1 d . . . . . H26 H 0.1027 0.7656 0.2093 0.078 Uiso 1 1 calc R . . . . C27 C 0.0778(3) 0.6774(4) 0.2835(5) 0.065(2) Uani 1 1 d . . . . . H27 H 0.0579 0.7108 0.3195 0.078 Uiso 1 1 calc R . . . . C28 C 0.0787(2) 0.5928(4) 0.3005(4) 0.0449(15) Uani 1 1 d . . . . . C29 C 0.0502(3) 0.5530(5) 0.3653(4) 0.058(2) Uani 1 1 d . . . . . H29 H 0.0295 0.5821 0.4042 0.070 Uiso 1 1 calc R . . . . C30 C 0.0529(3) 0.4719(5) 0.3712(4) 0.0565(19) Uani 1 1 d . . . . . H30 H 0.0332 0.4453 0.4131 0.068 Uiso 1 1 calc R . . . . C31 C 0.0855(2) 0.4281(4) 0.3143(4) 0.0466(16) Uani 1 1 d . . . . . H31 H 0.0877 0.3725 0.3197 0.056 Uiso 1 1 calc R . . . . C32 C 0.1096(3) 0.5460(4) 0.2448(4) 0.0408(15) Uani 1 1 d . . . . . C33 C 0.1381(2) 0.5786(4) 0.1744(3) 0.0396(14) 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 0.03527(12) 0.03696(14) 0.03365(11) -0.00237(13) 0.00883(9) 0.00025(14) F1 0.066(2) 0.057(3) 0.113(3) 0.004(2) 0.019(2) -0.022(2) O1 0.038(2) 0.046(3) 0.039(2) 0.0032(19) 0.0040(18) -0.002(2) N1 0.034(3) 0.038(3) 0.040(3) 0.000(2) 0.014(2) 0.001(2) N2 0.035(3) 0.038(3) 0.038(3) -0.007(2) 0.009(2) -0.003(2) C3 0.048(3) 0.029(4) 0.033(3) -0.003(3) 0.010(3) -0.003(3) C4 0.037(3) 0.041(4) 0.034(3) 0.003(3) 0.007(3) -0.003(3) N5 0.032(3) 0.048(4) 0.037(3) -0.004(2) 0.007(2) 0.003(3) C1 0.033(3) 0.044(4) 0.034(3) -0.007(3) 0.010(3) 0.003(3) C2 0.040(4) 0.062(5) 0.055(4) 0.004(4) -0.003(3) -0.006(4) C0AA 0.039(4) 0.070(6) 0.075(5) 0.000(4) 0.001(4) -0.016(4) C1AA 0.049(4) 0.045(5) 0.076(5) -0.006(4) 0.018(4) -0.014(4) C5 0.047(4) 0.042(4) 0.052(4) -0.004(3) 0.024(3) 0.001(3) C6 0.062(4) 0.029(4) 0.072(4) 0.009(3) 0.025(4) 0.002(4) C7 0.061(5) 0.049(5) 0.056(4) 0.014(4) 0.005(4) 0.010(4) C8 0.045(4) 0.050(5) 0.044(3) 0.003(3) -0.003(3) 0.004(3) C9 0.032(3) 0.044(4) 0.040(3) -0.001(3) 0.018(3) 0.002(3) C10 0.045(4) 0.045(4) 0.036(3) -0.005(3) 0.005(3) -0.003(3) C11 0.069(5) 0.057(5) 0.041(4) -0.003(3) 0.010(4) 0.007(4) C12 0.068(5) 0.064(5) 0.052(4) -0.001(4) 0.041(4) 0.014(4) C13 0.043(4) 0.040(4) 0.062(4) 0.002(3) 0.021(3) 0.003(3) C14 0.041(4) 0.067(6) 0.083(5) 0.004(4) 0.031(4) 0.004(4) C15 0.031(3) 0.057(5) 0.088(5) 0.008(4) 0.007(4) -0.008(4) C16 0.043(4) 0.036(4) 0.059(4) 0.004(3) 0.002(3) -0.005(3) C17 0.048(4) 0.051(5) 0.071(5) 0.003(4) -0.011(4) -0.007(4) C18 0.071(5) 0.052(5) 0.052(4) -0.010(3) -0.011(4) -0.005(4) C19 0.064(5) 0.048(5) 0.045(4) -0.001(3) 0.012(4) 0.001(4) C20 0.033(3) 0.025(3) 0.042(3) -0.001(3) 0.006(3) -0.001(3) C21 0.031(3) 0.035(4) 0.043(3) 0.001(3) 0.009(3) 0.002(3) C22 0.052(4) 0.047(4) 0.037(3) 0.003(3) 0.013(3) -0.002(3) C23 0.058(5) 0.050(5) 0.060(4) 0.026(4) 0.004(4) -0.009(4) C24 0.047(4) 0.041(5) 0.080(5) 0.008(4) -0.015(4) -0.006(4) C25 0.041(4) 0.036(4) 0.053(4) -0.002(3) -0.007(3) 0.003(3) C26 0.061(5) 0.041(5) 0.087(5) -0.009(4) 0.000(4) 0.006(4) C27 0.052(4) 0.055(6) 0.084(5) -0.035(4) 0.003(4) 0.009(4) C28 0.033(3) 0.051(4) 0.048(3) -0.012(4) -0.001(3) 0.002(4) C29 0.046(4) 0.077(6) 0.050(4) -0.029(4) 0.006(3) 0.008(4) C30 0.050(4) 0.077(6) 0.048(4) -0.006(4) 0.021(3) -0.009(4) C31 0.048(4) 0.047(5) 0.048(3) 0.002(3) 0.015(3) 0.004(3) C32 0.036(3) 0.039(4) 0.044(3) -0.015(3) -0.001(3) 0.003(3) C33 0.037(3) 0.038(4) 0.040(3) -0.001(3) -0.001(3) 0.005(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 -1.4440 7.9890 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 78.24(15) . . ? N2 Ir1 O1 93.54(15) . . ? N2 Ir1 N1 93.57(16) . . ? N2 Ir1 N5 171.55(19) . . ? C3 Ir1 O1 172.99(18) . . ? C3 Ir1 N1 97.25(19) . . ? C3 Ir1 N2 81.31(18) . . ? C3 Ir1 N5 95.80(18) . . ? C4 Ir1 O1 96.91(17) . . ? C4 Ir1 N1 173.69(18) . . ? C4 Ir1 N2 90.7(2) . . ? C4 Ir1 C3 87.9(2) . . ? C4 Ir1 N5 81.2(2) . . ? N5 Ir1 O1 89.95(14) . . ? N5 Ir1 N1 94.66(18) . . ? C1 O1 Ir1 112.9(3) . . ? C8 N1 Ir1 128.5(4) . . ? C8 N1 C9 118.5(5) . . ? C9 N1 Ir1 113.0(4) . . ? C10 N2 Ir1 126.6(4) . . ? C10 N2 C21 119.1(5) . . ? C21 N2 Ir1 114.1(3) . . ? C19 C3 Ir1 131.7(4) . . ? C19 C3 C20 116.0(5) . . ? C20 C3 Ir1 112.3(3) . . ? C22 C4 Ir1 133.1(5) . . ? C22 C4 C33 114.5(5) . . ? C33 C4 Ir1 112.4(4) . . ? C31 N5 Ir1 127.0(4) . . ? C31 N5 C32 119.0(5) . . ? C32 N5 Ir1 114.0(4) . . ? O1 C1 C2 124.1(5) . . ? O1 C1 C9 120.2(5) . . ? C2 C1 C9 115.7(6) . . ? C0AA C2 C1 122.1(6) . . ? C1AA C0AA C2 120.3(6) . . ? F1 C1AA C5 117.0(6) . . ? C0AA C1AA F1 120.1(6) . . ? C0AA C1AA C5 122.9(7) . . ? C1AA C5 C6 126.2(6) . . ? C1AA C5 C9 116.6(6) . . ? C9 C5 C6 117.1(6) . . ? C7 C6 C5 119.3(6) . . ? C6 C7 C8 120.5(6) . . ? N1 C8 C7 122.5(6) . . ? N1 C9 C1 115.6(5) . . ? N1 C9 C5 122.0(5) . . ? C5 C9 C1 122.4(5) . . ? N2 C10 C11 121.0(5) . . ? C12 C11 C10 120.2(5) . . ? C11 C12 C13 120.3(6) . . ? C12 C13 C14 126.1(6) . . ? C21 C13 C12 117.5(5) . . ? C21 C13 C14 116.3(5) . . ? C15 C14 C13 121.5(6) . . ? C14 C15 C16 122.2(6) . . ? C17 C16 C15 125.5(6) . . ? C20 C16 C15 118.6(5) . . ? C20 C16 C17 115.9(5) . . ? C18 C17 C16 120.3(6) . . ? C17 C18 C19 122.3(6) . . ? C3 C19 C18 120.6(6) . . ? C3 C20 C16 124.9(5) . . ? C3 C20 C21 117.6(4) . . ? C16 C20 C21 117.5(5) . . ? N2 C21 C13 121.8(5) . . ? N2 C21 C20 114.4(5) . . ? C13 C21 C20 123.7(5) . . ? C4 C22 C23 122.7(6) . . ? C24 C23 C22 121.4(6) . . ? C23 C24 C25 119.2(6) . . ? C24 C25 C26 123.0(7) . . ? C24 C25 C33 118.2(6) . . ? C33 C25 C26 118.8(6) . . ? C27 C26 C25 121.3(7) . . ? C26 C27 C28 122.5(7) . . ? C29 C28 C27 126.4(7) . . ? C32 C28 C27 116.1(6) . . ? C32 C28 C29 117.5(7) . . ? C30 C29 C28 119.8(6) . . ? C29 C30 C31 120.1(6) . . ? N5 C31 C30 121.3(6) . . ? N5 C32 C28 122.3(6) . . ? N5 C32 C33 114.8(5) . . ? C28 C32 C33 123.0(6) . . ? C25 C33 C4 124.0(6) . . ? C25 C33 C32 118.4(6) . . ? C32 C33 C4 117.5(6) . . ? 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 2.146(3) . ? Ir1 N1 2.128(4) . ? Ir1 N2 2.044(4) . ? Ir1 C3 2.012(5) . ? Ir1 C4 2.000(6) . ? Ir1 N5 2.060(4) . ? F1 C1AA 1.362(7) . ? O1 C1 1.303(6) . ? N1 C8 1.313(6) . ? N1 C9 1.382(6) . ? N2 C10 1.334(5) . ? N2 C21 1.373(6) . ? C3 C19 1.381(6) . ? C3 C20 1.404(6) . ? C4 C22 1.391(7) . ? C4 C33 1.416(7) . ? N5 C31 1.332(6) . ? N5 C32 1.365(6) . ? C1 C2 1.392(7) . ? C1 C9 1.442(7) . ? C2 C0AA 1.388(8) . ? C0AA C1AA 1.340(8) . ? C1AA C5 1.398(7) . ? C5 C6 1.410(7) . ? C5 C9 1.405(7) . ? C6 C7 1.357(7) . ? C7 C8 1.387(7) . ? C10 C11 1.388(7) . ? C11 C12 1.354(7) . ? C12 C13 1.390(7) . ? C13 C14 1.421(7) . ? C13 C21 1.390(7) . ? C14 C15 1.353(7) . ? C15 C16 1.417(7) . ? C16 C17 1.411(7) . ? C16 C20 1.406(6) . ? C17 C18 1.357(8) . ? C18 C19 1.401(7) . ? C20 C21 1.424(6) . ? C22 C23 1.408(7) . ? C23 C24 1.363(8) . ? C24 C25 1.408(7) . ? C25 C26 1.421(8) . ? C25 C33 1.410(7) . ? C26 C27 1.340(8) . ? C27 C28 1.431(8) . ? C28 C29 1.404(8) . ? C28 C32 1.396(7) . ? C29 C30 1.354(8) . ? C30 C31 1.402(7) . ? C32 C33 1.416(7) . ?