#------------------------------------------------------------------------------ #$Date: 2020-10-06 13:11:15 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257764 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557795.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_1557795 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 'C31 H21 F Ir N3 O' _chemical_formula_sum 'C31 H21 F Ir N3 O' _chemical_formula_weight 662.71 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-09-20 _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 92.268(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4485(7) _cell_length_b 9.3218(6) _cell_length_c 23.3115(14) _cell_measurement_reflns_used 9935 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 2.973 _cell_volume 2485.9(3) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _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 273.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_unetI/netI 0.0332 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 38204 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.520 _diffrn_reflns_theta_min 2.930 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.409 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1502 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.5406. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.771 _exptl_crystal_description block _exptl_crystal_F_000 1288 _exptl_crystal_size_max 0.403 _exptl_crystal_size_mid 0.177 _exptl_crystal_size_min 0.089 _refine_diff_density_max 0.803 _refine_diff_density_min -1.413 _refine_diff_density_rms 0.281 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 334 _refine_ls_number_reflns 5704 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.134 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0280 _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^)+(0.0418P)^2^+0.1620P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.0796 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4666 _reflns_number_total 5704 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj00465k2.cif _cod_data_source_block aaa _cod_depositor_comments ;Adding full bibliography for 1557795--1557798.cif. Adding full bibliography for 1557795--1557798.cif. ; _cod_database_code 1557795 _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. ; _shelx_estimated_absorpt_t_max 0.645 _shelx_estimated_absorpt_t_min 0.219 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30) ; _shelx_res_file ; TITL aaa in P21/n #14 REM reset to P21/n #14 CELL 0.71073 11.4485 9.3218 23.3115 90 92.268 90 ZERR 4 0.0007 0.0006 0.0014 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F Ir N O UNIT 124 84 4 4 12 4 L.S. 4 PLAN 20 SIZE 0.089 0.177 0.403 TEMP 0 BOND fmap 2 ACTA REM REM REM WGHT 0.041800 0.162000 FVAR 0.08778 IR1 4 0.271276 0.737453 0.082226 11.00000 0.03127 0.03438 = 0.03851 0.00333 0.00870 0.00589 F1 3 0.119175 1.003969 -0.170384 11.00000 0.07801 0.13878 = 0.05418 0.03416 -0.01402 -0.00485 O1 6 0.376525 0.852141 0.023404 11.00000 0.02788 0.04575 = 0.04218 0.00646 0.00595 0.00153 N1 5 0.245017 0.912930 0.131848 11.00000 0.03169 0.04221 = 0.03373 -0.00042 0.00349 0.00618 N2 5 0.143782 0.806837 0.019104 11.00000 0.02736 0.03338 = 0.03930 -0.00215 0.00623 0.00213 N3 5 0.305336 0.551805 0.039670 11.00000 0.04694 0.03613 = 0.05499 0.00155 0.02420 0.00251 C1 1 0.296359 1.039830 0.124478 11.00000 0.03238 0.04531 = 0.04841 0.00082 0.00632 -0.00165 AFIX 43 H1 2 0.344419 1.051764 0.093591 11.00000 -1.20000 AFIX 0 C2 1 0.280711 1.153061 0.160825 11.00000 0.04312 0.04908 = 0.06204 -0.00692 -0.00239 -0.00533 AFIX 43 H2 2 0.316954 1.240688 0.154643 11.00000 -1.20000 AFIX 0 C3 1 0.209803 1.134225 0.206941 11.00000 0.05096 0.05869 = 0.05192 -0.02031 -0.00293 0.00244 AFIX 43 H3 2 0.199030 1.208861 0.232671 11.00000 -1.20000 AFIX 0 C4 1 0.156005 1.006017 0.214407 11.00000 0.04607 0.06635 = 0.03759 -0.00643 0.00706 0.00847 AFIX 43 H4 2 0.108020 0.993584 0.245292 11.00000 -1.20000 AFIX 0 C5 1 0.171676 0.893706 0.176661 11.00000 0.03421 0.05296 = 0.02833 0.00200 0.00099 0.01105 C6 1 0.118129 0.750994 0.177770 11.00000 0.03780 0.05059 = 0.03771 0.01191 0.00676 0.00598 C7 1 0.032627 0.712385 0.215210 11.00000 0.05342 0.06950 = 0.04577 0.01024 0.02031 0.00658 AFIX 43 H7 2 0.006262 0.778619 0.241581 11.00000 -1.20000 AFIX 0 C8 1 -0.012849 0.577395 0.213409 11.00000 0.06498 0.07496 = 0.07110 0.01891 0.03297 -0.00334 AFIX 43 H8 2 -0.069685 0.551790 0.238929 11.00000 -1.20000 AFIX 0 C9 1 0.024263 0.478342 0.174278 11.00000 0.07883 0.05402 = 0.09445 0.01554 0.03243 -0.01762 AFIX 43 H9 2 -0.007884 0.386721 0.173010 11.00000 -1.20000 AFIX 0 C10 1 0.110031 0.516508 0.136778 11.00000 0.06639 0.04264 = 0.06982 0.00335 0.02444 -0.00412 AFIX 43 H10 2 0.136085 0.448549 0.111023 11.00000 -1.20000 AFIX 0 C11 1 0.158358 0.653820 0.136555 11.00000 0.03807 0.04110 = 0.04035 0.01178 0.00933 0.00572 C12 1 0.409213 0.667226 0.130712 11.00000 0.03255 0.04930 = 0.04811 0.01706 0.01118 0.00772 C13 1 0.467999 0.736674 0.176896 11.00000 0.04472 0.07160 = 0.05463 0.02461 0.00287 0.00233 AFIX 43 H13 2 0.440490 0.824554 0.189568 11.00000 -1.20000 AFIX 0 C14 1 0.566370 0.676434 0.203926 11.00000 0.04911 0.10236 = 0.06575 0.03454 -0.00156 0.00779 AFIX 43 H14 2 0.605203 0.725356 0.233762 11.00000 -1.20000 AFIX 0 C15 1 0.606666 0.545439 0.186972 11.00000 0.04714 0.12571 = 0.08505 0.05275 0.00949 0.02606 AFIX 43 H15 2 0.671115 0.504461 0.206192 11.00000 -1.20000 AFIX 0 C16 1 0.552229 0.473941 0.141565 11.00000 0.06124 0.07252 = 0.08846 0.04044 0.03109 0.03435 AFIX 43 H16 2 0.580452 0.385449 0.129966 11.00000 -1.20000 AFIX 0 C17 1 0.453851 0.535001 0.112759 11.00000 0.04331 0.05396 = 0.06441 0.02473 0.02397 0.01526 C18 1 0.396660 0.472949 0.062462 11.00000 0.05305 0.03631 = 0.07735 0.01868 0.03544 0.01142 C19 1 0.429685 0.349763 0.034258 11.00000 0.06776 0.04204 = 0.10460 0.00384 0.04516 0.01182 AFIX 43 H19 2 0.492704 0.296644 0.049048 11.00000 -1.20000 AFIX 0 C20 1 0.372573 0.304877 -0.014223 11.00000 0.08567 0.03898 = 0.12382 -0.01909 0.06582 -0.00346 AFIX 43 H20 2 0.396806 0.222125 -0.032597 11.00000 -1.20000 AFIX 0 C21 1 0.277921 0.381900 -0.036644 11.00000 0.08183 0.05617 = 0.08371 -0.02570 0.04507 -0.02407 AFIX 43 H21 2 0.236460 0.351416 -0.069529 11.00000 -1.20000 AFIX 0 C22 1 0.247475 0.505490 -0.008370 11.00000 0.06077 0.04572 = 0.06507 -0.00326 0.02470 -0.00092 AFIX 43 H22 2 0.184559 0.559053 -0.022994 11.00000 -1.20000 AFIX 0 C23 1 0.029107 0.785764 0.017982 11.00000 0.03400 0.04697 = 0.04809 -0.00014 0.00784 -0.00108 AFIX 43 H23 2 -0.004357 0.745816 0.049992 11.00000 -1.20000 AFIX 0 C24 1 -0.043360 0.821543 -0.029702 11.00000 0.03159 0.05524 = 0.06746 -0.00165 -0.00229 -0.00233 AFIX 43 H24 2 -0.123474 0.805603 -0.028947 11.00000 -1.20000 AFIX 0 C25 1 0.003173 0.879133 -0.076710 11.00000 0.04211 0.06025 = 0.05283 0.00048 -0.01061 -0.00119 AFIX 43 H25 2 -0.044277 0.900930 -0.108832 11.00000 -1.20000 AFIX 0 C26 1 0.125407 0.906242 -0.076739 11.00000 0.04400 0.04307 = 0.03952 -0.00401 0.00025 0.00252 C27 1 0.192577 0.867947 -0.027564 11.00000 0.03094 0.03064 = 0.03958 -0.00476 0.00459 0.00279 C28 1 0.316530 0.890168 -0.023013 11.00000 0.03225 0.03276 = 0.03854 -0.00179 0.00780 0.00379 C29 1 0.367473 0.954452 -0.070242 11.00000 0.03646 0.04583 = 0.05156 0.00038 0.01164 -0.00056 AFIX 43 H29 2 0.447462 0.972273 -0.068866 11.00000 -1.20000 AFIX 0 C30 1 0.300625 0.992398 -0.119409 11.00000 0.06219 0.06226 = 0.04311 0.01125 0.01201 -0.00193 AFIX 43 H30 2 0.336419 1.034054 -0.150424 11.00000 -1.20000 AFIX 0 C31 1 0.183103 0.968442 -0.121956 11.00000 0.05609 0.06713 = 0.03585 0.00698 -0.00249 -0.00316 HKLF 4 REM aaa in P21/n #14 REM R1 = 0.0280 for 4666 Fo > 4sig(Fo) and 0.0434 for all 5704 data REM 334 parameters refined using 0 restraints END WGHT 0.0418 0.1620 REM Highest difference peak 0.803, deepest hole -1.413, 1-sigma level 0.281 Q1 1 -0.2519 0.7086 -0.0280 11.00000 0.05 0.80 Q2 1 0.1786 0.2456 -0.0506 11.00000 0.05 0.76 Q3 1 0.2006 0.2626 -0.0171 11.00000 0.05 0.73 Q4 1 0.3304 1.2246 0.0711 11.00000 0.05 0.73 Q5 1 0.3391 1.2792 0.1001 11.00000 0.05 0.72 Q6 1 0.2360 0.6892 0.0630 11.00000 0.05 0.72 Q7 1 0.2763 0.2741 0.0631 11.00000 0.05 0.72 Q8 1 0.2963 0.2969 -0.0413 11.00000 0.05 0.72 Q9 1 -0.2425 0.8009 -0.0291 11.00000 0.05 0.70 Q10 1 0.1966 0.2407 -0.0986 11.00000 0.05 0.69 Q11 1 0.2894 0.2550 -0.0577 11.00000 0.05 0.69 Q12 1 0.3255 0.3273 0.0768 11.00000 0.05 0.68 Q13 1 -0.1178 0.7574 0.1832 11.00000 0.05 0.68 Q14 1 0.2252 0.1828 -0.0599 11.00000 0.05 0.68 Q15 1 0.0242 0.7396 0.3009 11.00000 0.05 0.67 Q16 1 0.3009 0.2995 -0.0007 11.00000 0.05 0.67 Q17 1 0.1157 0.2445 -0.1326 11.00000 0.05 0.67 Q18 1 -0.2308 0.7991 -0.0689 11.00000 0.05 0.66 Q19 1 0.3559 0.2423 0.0450 11.00000 0.05 0.66 Q20 1 0.1474 0.2002 -0.0802 11.00000 0.05 0.66 ; _shelx_res_checksum 19825 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.27128(2) 0.73745(2) 0.08223(2) 0.03453(7) Uani 1 1 d . . . . . F1 F 0.1192(3) 1.0040(4) -0.17038(11) 0.0908(10) Uani 1 1 d . . . . . O1 O 0.3765(2) 0.8521(3) 0.02340(10) 0.0385(6) Uani 1 1 d . . . . . N1 N 0.2450(3) 0.9129(3) 0.13185(12) 0.0358(7) Uani 1 1 d . . . . . N2 N 0.1438(3) 0.8068(3) 0.01910(13) 0.0332(7) Uani 1 1 d . . . . . N3 N 0.3053(3) 0.5518(3) 0.03967(14) 0.0454(8) Uani 1 1 d . . . . . C1 C 0.2964(3) 1.0398(4) 0.12448(17) 0.0419(9) Uani 1 1 d . . . . . H1 H 0.3444 1.0518 0.0936 0.050 Uiso 1 1 calc R . . . . C2 C 0.2807(3) 1.1531(5) 0.16082(19) 0.0515(11) Uani 1 1 d . . . . . H2 H 0.3170 1.2407 0.1546 0.062 Uiso 1 1 calc R . . . . C3 C 0.2098(4) 1.1342(5) 0.20694(18) 0.0540(11) Uani 1 1 d . . . . . H3 H 0.1990 1.2089 0.2327 0.065 Uiso 1 1 calc R . . . . C4 C 0.1560(4) 1.0060(5) 0.21441(17) 0.0499(10) Uani 1 1 d . . . . . H4 H 0.1080 0.9936 0.2453 0.060 Uiso 1 1 calc R . . . . C5 C 0.1717(3) 0.8937(4) 0.17666(15) 0.0385(9) Uani 1 1 d . . . . . C6 C 0.1181(4) 0.7510(4) 0.17777(18) 0.0419(10) Uani 1 1 d . . . . . C7 C 0.0326(4) 0.7124(5) 0.2152(2) 0.0557(12) Uani 1 1 d . . . . . H7 H 0.0063 0.7786 0.2416 0.067 Uiso 1 1 calc R . . . . C8 C -0.0128(4) 0.5774(6) 0.2134(2) 0.0695(14) Uani 1 1 d . . . . . H8 H -0.0697 0.5518 0.2389 0.083 Uiso 1 1 calc R . . . . C9 C 0.0243(5) 0.4783(6) 0.1743(2) 0.0750(15) Uani 1 1 d . . . . . H9 H -0.0079 0.3867 0.1730 0.090 Uiso 1 1 calc R . . . . C10 C 0.1100(4) 0.5165(5) 0.1368(2) 0.0590(12) Uani 1 1 d . . . . . H10 H 0.1361 0.4485 0.1110 0.071 Uiso 1 1 calc R . . . . C11 C 0.1584(3) 0.6538(4) 0.13656(16) 0.0396(9) Uani 1 1 d . . . . . C12 C 0.4092(3) 0.6672(4) 0.13071(17) 0.0431(10) Uani 1 1 d . . . . . C13 C 0.4680(4) 0.7367(5) 0.1769(2) 0.0570(14) Uani 1 1 d . . . . . H13 H 0.4405 0.8246 0.1896 0.068 Uiso 1 1 calc R . . . . C14 C 0.5664(4) 0.6764(7) 0.2039(2) 0.0725(15) Uani 1 1 d . . . . . H14 H 0.6052 0.7254 0.2338 0.087 Uiso 1 1 calc R . . . . C15 C 0.6067(5) 0.5454(8) 0.1870(3) 0.086(2) Uani 1 1 d . . . . . H15 H 0.6711 0.5045 0.2062 0.103 Uiso 1 1 calc R . . . . C16 C 0.5522(4) 0.4739(6) 0.1416(2) 0.0733(16) Uani 1 1 d . . . . . H16 H 0.5805 0.3854 0.1300 0.088 Uiso 1 1 calc R . . . . C17 C 0.4539(4) 0.5350(5) 0.1128(2) 0.0533(11) Uani 1 1 d . . . . . C18 C 0.3967(4) 0.4729(4) 0.0625(2) 0.0547(12) Uani 1 1 d . . . . . C19 C 0.4297(5) 0.3498(5) 0.0343(3) 0.0704(15) Uani 1 1 d . . . . . H19 H 0.4927 0.2966 0.0490 0.084 Uiso 1 1 calc R . . . . C20 C 0.3726(6) 0.3049(6) -0.0142(3) 0.0812(19) Uani 1 1 d . . . . . H20 H 0.3968 0.2221 -0.0326 0.097 Uiso 1 1 calc R . . . . C21 C 0.2779(5) 0.3819(5) -0.0366(2) 0.0728(16) Uani 1 1 d . . . . . H21 H 0.2365 0.3514 -0.0695 0.087 Uiso 1 1 calc R . . . . C22 C 0.2475(4) 0.5055(5) -0.0084(2) 0.0566(12) Uani 1 1 d . . . . . H22 H 0.1846 0.5591 -0.0230 0.068 Uiso 1 1 calc R . . . . C23 C 0.0291(4) 0.7858(4) 0.01798(19) 0.0429(9) Uani 1 1 d . . . . . H23 H -0.0044 0.7458 0.0500 0.051 Uiso 1 1 calc R . . . . C24 C -0.0434(4) 0.8215(5) -0.02970(19) 0.0515(11) Uani 1 1 d . . . . . H24 H -0.1235 0.8056 -0.0289 0.062 Uiso 1 1 calc R . . . . C25 C 0.0032(4) 0.8791(5) -0.07671(19) 0.0521(11) Uani 1 1 d . . . . . H25 H -0.0443 0.9009 -0.1088 0.062 Uiso 1 1 calc R . . . . C26 C 0.1254(3) 0.9062(4) -0.07674(16) 0.0422(9) Uani 1 1 d . . . . . C27 C 0.1926(3) 0.8679(4) -0.02756(15) 0.0336(8) Uani 1 1 d . . . . . C28 C 0.3165(3) 0.8902(4) -0.02301(15) 0.0343(8) Uani 1 1 d . . . . . C29 C 0.3675(4) 0.9545(4) -0.07024(17) 0.0444(10) Uani 1 1 d . . . . . H29 H 0.4475 0.9723 -0.0689 0.053 Uiso 1 1 calc R . . . . C30 C 0.3006(4) 0.9924(5) -0.11941(17) 0.0556(11) Uani 1 1 d . . . . . H30 H 0.3364 1.0341 -0.1504 0.067 Uiso 1 1 calc R . . . . C31 C 0.1831(4) 0.9684(5) -0.12196(17) 0.0531(11) 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 0.03127(10) 0.03438(10) 0.03851(10) 0.00333(6) 0.00870(7) 0.00589(6) F1 0.078(2) 0.139(3) 0.0542(17) 0.0342(18) -0.0140(15) -0.005(2) O1 0.0279(13) 0.0457(15) 0.0422(15) 0.0065(12) 0.0059(11) 0.0015(11) N1 0.0317(17) 0.0422(18) 0.0337(16) -0.0004(13) 0.0035(14) 0.0062(14) N2 0.0274(16) 0.0334(15) 0.0393(17) -0.0021(14) 0.0062(13) 0.0021(13) N3 0.047(2) 0.0361(18) 0.055(2) 0.0015(15) 0.0242(17) 0.0025(15) C1 0.032(2) 0.045(2) 0.048(2) 0.0008(18) 0.0063(18) -0.0017(17) C2 0.043(2) 0.049(3) 0.062(3) -0.007(2) -0.002(2) -0.005(2) C3 0.051(3) 0.059(3) 0.052(3) -0.020(2) -0.003(2) 0.002(2) C4 0.046(3) 0.066(3) 0.038(2) -0.006(2) 0.0071(19) 0.008(2) C5 0.034(2) 0.053(2) 0.0283(19) 0.0020(17) 0.0010(16) 0.0110(18) C6 0.038(2) 0.051(3) 0.038(2) 0.0119(16) 0.0068(18) 0.0060(17) C7 0.053(3) 0.069(3) 0.046(3) 0.010(2) 0.020(2) 0.007(2) C8 0.065(3) 0.075(4) 0.071(3) 0.019(3) 0.033(3) -0.003(3) C9 0.079(4) 0.054(3) 0.094(4) 0.016(3) 0.032(3) -0.018(3) C10 0.066(3) 0.043(2) 0.070(3) 0.003(2) 0.024(3) -0.004(2) C11 0.038(2) 0.041(2) 0.040(2) 0.0118(17) 0.0093(17) 0.0057(18) C12 0.033(2) 0.049(2) 0.048(2) 0.0171(19) 0.0112(18) 0.0077(18) C13 0.045(3) 0.072(4) 0.055(3) 0.025(2) 0.003(2) 0.002(2) C14 0.049(3) 0.102(4) 0.066(3) 0.035(3) -0.002(3) 0.008(3) C15 0.047(3) 0.126(6) 0.085(4) 0.053(4) 0.009(3) 0.026(3) C16 0.061(3) 0.073(3) 0.088(4) 0.040(3) 0.031(3) 0.034(3) C17 0.043(3) 0.054(3) 0.064(3) 0.025(2) 0.024(2) 0.015(2) C18 0.053(3) 0.036(2) 0.077(3) 0.019(2) 0.035(2) 0.011(2) C19 0.068(3) 0.042(3) 0.105(4) 0.004(3) 0.045(3) 0.012(2) C20 0.086(4) 0.039(3) 0.124(5) -0.019(3) 0.066(4) -0.003(3) C21 0.082(4) 0.056(3) 0.084(4) -0.026(3) 0.045(3) -0.024(3) C22 0.061(3) 0.046(2) 0.065(3) -0.003(2) 0.025(2) -0.001(2) C23 0.034(2) 0.047(2) 0.048(2) -0.0001(19) 0.0078(19) -0.0011(18) C24 0.032(2) 0.055(3) 0.067(3) -0.002(2) -0.002(2) -0.002(2) C25 0.042(2) 0.060(3) 0.053(3) 0.000(2) -0.011(2) -0.001(2) C26 0.044(2) 0.043(2) 0.040(2) -0.0040(17) 0.0003(18) 0.0025(18) C27 0.0309(19) 0.0306(18) 0.040(2) -0.0048(15) 0.0046(16) 0.0028(15) C28 0.032(2) 0.0328(19) 0.039(2) -0.0018(15) 0.0078(17) 0.0038(15) C29 0.036(2) 0.046(2) 0.052(2) 0.0004(18) 0.0116(19) -0.0006(18) C30 0.062(3) 0.062(3) 0.043(2) 0.011(2) 0.012(2) -0.002(2) C31 0.056(3) 0.067(3) 0.036(2) 0.007(2) -0.002(2) -0.003(2) 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 N1 Ir1 O1 93.56(11) . . ? N1 Ir1 N2 92.06(11) . . ? N1 Ir1 N3 174.17(12) . . ? N2 Ir1 O1 78.12(10) . . ? N3 Ir1 O1 89.37(10) . . ? N3 Ir1 N2 93.47(13) . . ? C11 Ir1 O1 172.11(12) . . ? C11 Ir1 N1 80.78(14) . . ? C11 Ir1 N2 96.50(13) . . ? C11 Ir1 N3 96.77(14) . . ? C11 Ir1 C12 91.72(15) . . ? C12 Ir1 O1 94.18(12) . . ? C12 Ir1 N1 94.16(15) . . ? C12 Ir1 N2 170.40(13) . . ? C12 Ir1 N3 80.59(16) . . ? C28 O1 Ir1 112.0(2) . . ? C1 N1 Ir1 124.3(3) . . ? C1 N1 C5 119.8(3) . . ? C5 N1 Ir1 115.8(3) . . ? C23 N2 Ir1 128.2(3) . . ? C23 N2 C27 118.8(3) . . ? C27 N2 Ir1 112.7(2) . . ? C18 N3 Ir1 115.1(3) . . ? C22 N3 Ir1 125.3(3) . . ? C22 N3 C18 119.5(4) . . ? N1 C1 C2 122.3(4) . . ? C1 C2 C3 118.6(4) . . ? C4 C3 C2 119.6(4) . . ? C3 C4 C5 120.9(4) . . ? N1 C5 C4 118.8(4) . . ? N1 C5 C6 113.5(3) . . ? C4 C5 C6 127.6(4) . . ? C7 C6 C5 123.6(4) . . ? C7 C6 C11 121.4(4) . . ? C11 C6 C5 115.0(4) . . ? C8 C7 C6 120.0(4) . . ? C7 C8 C9 120.8(4) . . ? C8 C9 C10 119.4(5) . . ? C9 C10 C11 121.9(4) . . ? C6 C11 Ir1 114.6(3) . . ? C10 C11 Ir1 128.7(3) . . ? C10 C11 C6 116.5(4) . . ? C13 C12 Ir1 128.4(3) . . ? C17 C12 Ir1 113.9(3) . . ? C17 C12 C13 117.6(4) . . ? C14 C13 C12 121.1(5) . . ? C15 C14 C13 120.4(6) . . ? C14 C15 C16 120.4(5) . . ? C15 C16 C17 120.0(5) . . ? C12 C17 C16 120.4(5) . . ? C12 C17 C18 115.8(4) . . ? C16 C17 C18 123.7(4) . . ? N3 C18 C17 114.6(4) . . ? N3 C18 C19 118.7(5) . . ? C19 C18 C17 126.6(5) . . ? C20 C19 C18 121.5(5) . . ? C19 C20 C21 120.1(5) . . ? C22 C21 C20 117.5(5) . . ? N3 C22 C21 122.6(5) . . ? N2 C23 C24 122.3(4) . . ? C25 C24 C23 119.9(4) . . ? C24 C25 C26 119.4(4) . . ? C27 C26 C25 117.6(4) . . ? C31 C26 C25 124.8(4) . . ? C31 C26 C27 117.6(4) . . ? N2 C27 C26 121.9(3) . . ? N2 C27 C28 115.8(3) . . ? C26 C27 C28 122.2(3) . . ? O1 C28 C27 120.5(3) . . ? O1 C28 C29 123.0(3) . . ? C29 C28 C27 116.4(3) . . ? C30 C29 C28 121.4(4) . . ? C31 C30 C29 120.1(4) . . ? F1 C31 C26 118.3(4) . . ? F1 C31 C30 119.6(4) . . ? C30 C31 C26 122.2(4) . . ? 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(2) . ? Ir1 N1 2.033(3) . ? Ir1 N2 2.132(3) . ? Ir1 N3 2.040(3) . ? Ir1 C11 2.003(4) . ? Ir1 C12 2.015(4) . ? F1 C31 1.362(5) . ? O1 C28 1.307(4) . ? N1 C1 1.335(5) . ? N1 C5 1.378(5) . ? N2 C23 1.327(5) . ? N2 C27 1.367(4) . ? N3 C18 1.368(5) . ? N3 C22 1.349(5) . ? C1 C2 1.370(5) . ? C2 C3 1.384(6) . ? C3 C4 1.359(6) . ? C4 C5 1.384(5) . ? C5 C6 1.465(5) . ? C6 C7 1.385(6) . ? C6 C11 1.411(6) . ? C7 C8 1.362(7) . ? C8 C9 1.377(7) . ? C9 C10 1.387(6) . ? C10 C11 1.395(5) . ? C12 C13 1.405(6) . ? C12 C17 1.404(6) . ? C13 C14 1.387(6) . ? C14 C15 1.369(8) . ? C15 C16 1.379(8) . ? C16 C17 1.408(6) . ? C17 C18 1.441(6) . ? C18 C19 1.383(6) . ? C19 C20 1.350(8) . ? C20 C21 1.385(8) . ? C21 C22 1.379(6) . ? C23 C24 1.401(6) . ? C24 C25 1.349(6) . ? C25 C26 1.422(5) . ? C26 C27 1.401(5) . ? C26 C31 1.392(5) . ? C27 C28 1.434(5) . ? C28 C29 1.401(5) . ? C29 C30 1.398(5) . ? C30 C31 1.363(6) . ?