#------------------------------------------------------------------------------ #$Date: 2020-04-15 14:37:22 +0300 (Wed, 15 Apr 2020) $ #$Revision: 250763 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557798.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_1557798 _journal_paper_doi 10.1039/D0NJ00465K _chemical_formula_moiety 'C33 H25 F Ir N3 O' _chemical_formula_sum 'C33 H25 F Ir N3 O' _chemical_formula_weight 690.76 _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 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 100.056(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.4836(17) _cell_length_b 16.3026(14) _cell_length_c 15.6214(13) _cell_measurement_reflns_used 9405 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.520 _cell_measurement_theta_min 2.943 _cell_volume 5136.4(7) _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 0.998 _diffrn_measured_fraction_theta_max 0.997 _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 0.0364 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 52961 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.556 _diffrn_reflns_theta_min 2.943 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.239 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1548 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.5634. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.787 _exptl_crystal_description block _exptl_crystal_F_000 2704 _exptl_crystal_size_max 0.333 _exptl_crystal_size_mid 0.264 _exptl_crystal_size_min 0.148 _refine_diff_density_max 0.754 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.098 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 354 _refine_ls_number_reflns 5921 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0210 _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^)+(0.0230P)^2^+8.8322P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.0513 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5028 _reflns_number_total 5921 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj00465k2.cif _cod_data_source_block aaaa _cod_database_code 1557798 _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 0.511 _shelx_estimated_absorpt_t_min 0.274 _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 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33) 2.b Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C21(H21A,H21B,H21C) ; _shelx_res_file ; TITL aaaa in C2/c #15 REM reset to C2/c #15 CELL 0.71073 20.4836 16.3026 15.6214 90 100.056 90 ZERR 8 0.0017 0.0014 0.0013 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H F Ir N O UNIT 264 200 8 8 24 8 L.S. 4 PLAN 20 SIZE 0.148 0.264 0.333 TEMP 0 BOND fmap 2 ACTA REM REM REM WGHT 0.023000 8.832200 FVAR 0.04782 IR1 4 0.169839 0.076949 0.165136 11.00000 0.03173 0.02862 = 0.03203 0.00199 0.00781 0.00225 F1 3 -0.006552 0.417176 0.144346 11.00000 0.07372 0.04568 = 0.11268 0.00641 0.01766 0.02621 O1 6 0.078738 0.108288 0.079061 11.00000 0.04073 0.03794 = 0.04003 -0.00270 0.00107 0.00357 N1 5 0.116421 0.019330 0.246234 11.00000 0.03257 0.03757 = 0.03613 0.00507 0.00780 0.00197 N2 5 0.152263 0.199928 0.204077 11.00000 0.03490 0.03250 = 0.03507 0.00099 0.00956 0.00060 N3 5 0.231488 0.118163 0.085255 11.00000 0.04371 0.03156 = 0.03885 0.00071 0.01622 -0.00128 C1 1 0.087639 0.060234 0.304515 11.00000 0.04798 0.05066 = 0.04881 0.00900 0.01790 0.00974 AFIX 43 H1 2 0.088801 0.117262 0.304684 11.00000 -1.20000 AFIX 0 C2 1 0.056611 0.020588 0.363744 11.00000 0.05797 0.06833 = 0.05217 0.01128 0.02599 0.00928 AFIX 43 H2 2 0.036070 0.050126 0.402524 11.00000 -1.20000 AFIX 0 C3 1 0.056547 -0.062506 0.364506 11.00000 0.05228 0.07954 = 0.04941 0.02230 0.01630 -0.00517 AFIX 43 H3 2 0.036920 -0.090037 0.405583 11.00000 -1.20000 AFIX 0 C4 1 0.085125 -0.107304 0.305336 11.00000 0.04675 0.04925 = 0.05206 0.01514 0.00363 -0.00825 C5 1 0.084707 -0.199249 0.312641 11.00000 0.12801 0.05690 = 0.08338 0.01574 0.03348 -0.02183 AFIX 137 H5A 2 0.069100 -0.214706 0.364838 11.00000 -1.50000 H5B 2 0.128843 -0.219849 0.314544 11.00000 -1.50000 H5C 2 0.055912 -0.221902 0.263205 11.00000 -1.50000 AFIX 0 C6 1 0.114528 -0.064531 0.242848 11.00000 0.02914 0.03922 = 0.04153 0.00826 0.00008 -0.00128 C7 1 0.143977 -0.098439 0.170780 11.00000 0.03168 0.03514 = 0.04760 -0.00027 -0.00374 -0.00272 C8 1 0.142989 -0.180488 0.145240 11.00000 0.04389 0.03375 = 0.06962 0.00246 0.00022 -0.00466 AFIX 43 H8 2 0.123724 -0.219538 0.176392 11.00000 -1.20000 AFIX 0 C9 1 0.170183 -0.204505 0.074438 11.00000 0.05522 0.03986 = 0.07169 -0.01677 -0.00299 0.00171 AFIX 43 H9 2 0.169994 -0.259630 0.059080 11.00000 -1.20000 AFIX 0 C10 1 0.197408 -0.147752 0.026716 11.00000 0.05838 0.05079 = 0.05101 -0.01557 0.00368 0.00874 AFIX 43 H10 2 0.214379 -0.163877 -0.022133 11.00000 -1.20000 AFIX 0 C11 1 0.199588 -0.065820 0.051595 11.00000 0.05329 0.04413 = 0.04310 0.00044 0.01001 0.00672 AFIX 43 H11 2 0.219001 -0.027863 0.019338 11.00000 -1.20000 AFIX 0 C12 1 0.173479 -0.038554 0.123718 11.00000 0.03351 0.03027 = 0.04035 -0.00199 0.00204 0.00576 C13 1 0.257084 0.064536 0.243526 11.00000 0.03580 0.02848 = 0.03976 -0.00002 0.00517 0.00454 C14 1 0.268395 0.045494 0.331940 11.00000 0.04540 0.04719 = 0.04650 0.00726 0.00503 0.00299 AFIX 43 H14 2 0.232949 0.028729 0.357644 11.00000 -1.20000 AFIX 0 C15 1 0.330722 0.050824 0.382397 11.00000 0.05788 0.05481 = 0.05137 0.00468 -0.00817 0.00383 AFIX 43 H15 2 0.336479 0.038110 0.441273 11.00000 -1.20000 AFIX 0 C16 1 0.383972 0.074588 0.346644 11.00000 0.04264 0.05504 = 0.07668 -0.00209 -0.01269 0.00013 AFIX 43 H16 2 0.425618 0.079368 0.381244 11.00000 -1.20000 AFIX 0 C17 1 0.375582 0.091486 0.258730 11.00000 0.03745 0.04604 = 0.08028 -0.00160 0.00879 -0.00048 AFIX 43 H17 2 0.412064 0.106282 0.234109 11.00000 -1.20000 AFIX 0 C18 1 0.313097 0.086649 0.206383 11.00000 0.03403 0.02758 = 0.05560 -0.00069 0.00911 0.00323 C19 1 0.297671 0.109126 0.113854 11.00000 0.03975 0.02689 = 0.05635 -0.00241 0.02020 -0.00078 C20 1 0.341524 0.118183 0.054199 11.00000 0.05725 0.03625 = 0.07586 -0.00017 0.03498 -0.00153 C21 1 0.414372 0.097467 0.074997 11.00000 0.06135 0.07354 = 0.10945 -0.00058 0.04648 0.00564 AFIX 137 H21A 2 0.438012 0.141833 0.106891 11.00000 -1.50000 H21B 2 0.431025 0.089011 0.021920 11.00000 -1.50000 H21C 2 0.420426 0.048376 0.109412 11.00000 -1.50000 AFIX 0 C22 1 0.314682 0.141676 -0.029978 11.00000 0.08802 0.05194 = 0.07186 0.00484 0.05159 -0.00325 AFIX 43 H22 2 0.342773 0.148528 -0.070212 11.00000 -1.20000 AFIX 0 C23 1 0.249137 0.154893 -0.055316 11.00000 0.08866 0.05709 = 0.05039 0.01073 0.03019 0.00049 AFIX 43 H23 2 0.232445 0.172731 -0.111418 11.00000 -1.20000 AFIX 0 C24 1 0.207607 0.141514 0.003255 11.00000 0.06069 0.04539 = 0.04122 0.00605 0.01563 0.00101 AFIX 43 H24 2 0.162179 0.148714 -0.014043 11.00000 -1.20000 AFIX 0 C25 1 0.056613 0.180973 0.094558 11.00000 0.03576 0.03958 = 0.03757 0.00729 0.00646 0.00012 C26 1 -0.002519 0.213591 0.049821 11.00000 0.04100 0.05589 = 0.05325 0.00510 -0.00348 0.00406 AFIX 43 H26 2 -0.028596 0.182300 0.007185 11.00000 -1.20000 AFIX 0 C27 1 -0.023350 0.292158 0.067700 11.00000 0.04241 0.05900 = 0.07030 0.01602 0.00221 0.01401 AFIX 43 H27 2 -0.063068 0.312431 0.036998 11.00000 -1.20000 AFIX 0 C28 1 0.013620 0.339394 0.129342 11.00000 0.05236 0.03875 = 0.07142 0.00914 0.02032 0.01465 C29 1 0.073670 0.312592 0.178099 11.00000 0.04448 0.03441 = 0.04702 0.00612 0.01781 0.00252 C30 1 0.094213 0.232017 0.159774 11.00000 0.03495 0.03125 = 0.03641 0.00636 0.01283 -0.00032 C31 1 0.115770 0.358733 0.240304 11.00000 0.06050 0.03533 = 0.05946 -0.00559 0.01914 0.00214 AFIX 43 H31 2 0.103929 0.411716 0.253506 11.00000 -1.20000 AFIX 0 C32 1 0.173596 0.326284 0.281150 11.00000 0.05800 0.04057 = 0.05739 -0.01380 0.00518 -0.00566 AFIX 43 H32 2 0.202027 0.357103 0.321753 11.00000 -1.20000 AFIX 0 C33 1 0.190414 0.245952 0.261924 11.00000 0.04228 0.04256 = 0.04740 -0.00525 0.00203 -0.00214 AFIX 43 H33 2 0.230072 0.224115 0.291083 11.00000 -1.20000 AFIX 0 HKLF 4 REM aaaa in C2/c #15 REM R1 = 0.0210 for 5028 Fo > 4sig(Fo) and 0.0309 for all 5921 data REM 354 parameters refined using 0 restraints END WGHT 0.0230 8.8322 REM Highest difference peak 0.754, deepest hole -0.780, 1-sigma level 0.098 Q1 1 0.5088 0.0799 -0.0043 11.00000 0.05 0.75 Q2 1 0.1997 0.1013 0.2043 11.00000 0.05 0.73 Q3 1 0.1682 -0.2290 0.1655 11.00000 0.05 0.46 Q4 1 0.1697 0.0743 0.1060 11.00000 0.05 0.43 Q5 1 0.1384 0.3906 0.1611 11.00000 0.05 0.37 Q6 1 0.4329 0.0940 0.2472 11.00000 0.05 0.34 Q7 1 0.0125 0.1049 0.0004 11.00000 0.05 0.32 Q8 1 0.0527 0.1195 0.0431 11.00000 0.05 0.32 Q9 1 0.3121 0.0902 -0.1530 11.00000 0.05 0.31 Q10 1 0.0490 0.0873 0.0373 11.00000 0.05 0.31 Q11 1 0.0860 0.1110 0.0017 11.00000 0.05 0.31 Q12 1 0.0068 0.3269 0.0811 11.00000 0.05 0.30 Q13 1 0.4174 0.1596 0.2540 11.00000 0.05 0.30 Q14 1 0.0049 0.0532 0.4799 11.00000 0.05 0.30 Q15 1 0.3070 0.1188 -0.1528 11.00000 0.05 0.30 Q16 1 0.0234 -0.0410 0.4806 11.00000 0.05 0.29 Q17 1 0.3021 -0.0506 0.2972 11.00000 0.05 0.29 Q18 1 0.0437 0.0195 0.0351 11.00000 0.05 0.29 Q19 1 0.0394 -0.0110 0.4636 11.00000 0.05 0.29 Q20 1 0.0070 -0.0656 0.4394 11.00000 0.05 0.28 ; _shelx_res_checksum 48837 _olex2_submission_special_instructions 'No special instructions were received' 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 0.16984(2) 0.07695(2) 0.16514(2) 0.03052(4) Uani 1 1 d . . . . . F1 F -0.00655(13) 0.41718(12) 0.14435(19) 0.0772(7) Uani 1 1 d . . . . . O1 O 0.07874(10) 0.10829(13) 0.07906(13) 0.0403(5) Uani 1 1 d . . . . . N1 N 0.11642(12) 0.01933(15) 0.24623(15) 0.0352(5) Uani 1 1 d . . . . . N2 N 0.15226(12) 0.19993(14) 0.20408(15) 0.0337(5) Uani 1 1 d . . . . . N3 N 0.23149(12) 0.11816(15) 0.08525(16) 0.0370(5) Uani 1 1 d . . . . . C1 C 0.08764(17) 0.0602(2) 0.3045(2) 0.0480(8) Uani 1 1 d . . . . . H1 H 0.0888 0.1173 0.3047 0.058 Uiso 1 1 calc R . . . . C2 C 0.05661(19) 0.0206(2) 0.3637(2) 0.0575(10) Uani 1 1 d . . . . . H2 H 0.0361 0.0501 0.4025 0.069 Uiso 1 1 calc R . . . . C3 C 0.05655(19) -0.0625(3) 0.3645(2) 0.0595(10) Uani 1 1 d . . . . . H3 H 0.0369 -0.0900 0.4056 0.071 Uiso 1 1 calc R . . . . C4 C 0.08512(17) -0.1073(2) 0.3053(2) 0.0500(8) Uani 1 1 d . . . . . C5 C 0.0847(3) -0.1992(3) 0.3126(3) 0.0876(15) Uani 1 1 d . . . . . H5A H 0.0691 -0.2147 0.3648 0.131 Uiso 1 1 calc GR . . . . H5B H 0.1288 -0.2198 0.3145 0.131 Uiso 1 1 calc GR . . . . H5C H 0.0559 -0.2219 0.2632 0.131 Uiso 1 1 calc GR . . . . C6 C 0.11453(15) -0.06453(18) 0.2428(2) 0.0374(7) Uani 1 1 d . . . . . C7 C 0.14398(15) -0.09844(19) 0.1708(2) 0.0394(7) Uani 1 1 d . . . . . C8 C 0.14299(17) -0.1805(2) 0.1452(2) 0.0502(8) Uani 1 1 d . . . . . H8 H 0.1237 -0.2195 0.1764 0.060 Uiso 1 1 calc R . . . . C9 C 0.17018(18) -0.2045(2) 0.0744(3) 0.0573(10) Uani 1 1 d . . . . . H9 H 0.1700 -0.2596 0.0591 0.069 Uiso 1 1 calc R . . . . C10 C 0.19741(18) -0.1478(2) 0.0267(2) 0.0541(9) Uani 1 1 d . . . . . H10 H 0.2144 -0.1639 -0.0221 0.065 Uiso 1 1 calc R . . . . C11 C 0.19959(18) -0.0658(2) 0.0516(2) 0.0466(8) Uani 1 1 d . . . . . H11 H 0.2190 -0.0279 0.0193 0.056 Uiso 1 1 calc R . . . . C12 C 0.17348(14) -0.03855(18) 0.12372(19) 0.0352(6) Uani 1 1 d . . . . . C13 C 0.25708(15) 0.06454(16) 0.2435(2) 0.0348(6) Uani 1 1 d . . . . . C14 C 0.26839(17) 0.0455(2) 0.3319(2) 0.0467(8) Uani 1 1 d . . . . . H14 H 0.2329 0.0287 0.3576 0.056 Uiso 1 1 calc R . . . . C15 C 0.33072(19) 0.0508(2) 0.3824(3) 0.0568(9) Uani 1 1 d . . . . . H15 H 0.3365 0.0381 0.4413 0.068 Uiso 1 1 calc R . . . . C16 C 0.38397(19) 0.0746(2) 0.3466(3) 0.0609(10) Uani 1 1 d . . . . . H16 H 0.4256 0.0794 0.3812 0.073 Uiso 1 1 calc R . . . . C17 C 0.37558(18) 0.0915(2) 0.2587(3) 0.0548(9) Uani 1 1 d . . . . . H17 H 0.4121 0.1063 0.2341 0.066 Uiso 1 1 calc R . . . . C18 C 0.31310(15) 0.08665(17) 0.2064(2) 0.0389(7) Uani 1 1 d . . . . . C19 C 0.29767(15) 0.10913(18) 0.1139(2) 0.0396(7) Uani 1 1 d . . . . . C20 C 0.34152(18) 0.1182(2) 0.0542(3) 0.0536(9) Uani 1 1 d . . . . . C21 C 0.4144(2) 0.0975(3) 0.0750(3) 0.0777(13) Uani 1 1 d . . . . . H21A H 0.4380 0.1418 0.1069 0.116 Uiso 1 1 calc GR . . . . H21B H 0.4310 0.0890 0.0219 0.116 Uiso 1 1 calc GR . . . . H21C H 0.4204 0.0484 0.1094 0.116 Uiso 1 1 calc GR . . . . C22 C 0.3147(2) 0.1417(2) -0.0300(3) 0.0661(11) Uani 1 1 d . . . . . H22 H 0.3428 0.1485 -0.0702 0.079 Uiso 1 1 calc R . . . . C23 C 0.2491(2) 0.1549(2) -0.0553(3) 0.0632(11) Uani 1 1 d . . . . . H23 H 0.2324 0.1727 -0.1114 0.076 Uiso 1 1 calc R . . . . C24 C 0.20761(19) 0.1415(2) 0.0033(2) 0.0483(8) Uani 1 1 d . . . . . H24 H 0.1622 0.1487 -0.0140 0.058 Uiso 1 1 calc R . . . . C25 C 0.05661(15) 0.18097(19) 0.09456(19) 0.0376(7) Uani 1 1 d . . . . . C26 C -0.00252(17) 0.2136(2) 0.0498(2) 0.0515(8) Uani 1 1 d . . . . . H26 H -0.0286 0.1823 0.0072 0.062 Uiso 1 1 calc R . . . . C27 C -0.02335(18) 0.2922(2) 0.0677(3) 0.0582(10) Uani 1 1 d . . . . . H27 H -0.0631 0.3124 0.0370 0.070 Uiso 1 1 calc R . . . . C28 C 0.01362(18) 0.3394(2) 0.1293(3) 0.0530(9) Uani 1 1 d . . . . . C29 C 0.07367(16) 0.31259(19) 0.1781(2) 0.0408(7) Uani 1 1 d . . . . . C30 C 0.09421(14) 0.23202(18) 0.15977(18) 0.0334(6) Uani 1 1 d . . . . . C31 C 0.11577(18) 0.3587(2) 0.2403(2) 0.0507(8) Uani 1 1 d . . . . . H31 H 0.1039 0.4117 0.2535 0.061 Uiso 1 1 calc R . . . . C32 C 0.17360(19) 0.3263(2) 0.2811(2) 0.0526(9) Uani 1 1 d . . . . . H32 H 0.2020 0.3571 0.3218 0.063 Uiso 1 1 calc R . . . . C33 C 0.19041(16) 0.2460(2) 0.2619(2) 0.0448(7) Uani 1 1 d . . . . . H33 H 0.2301 0.2241 0.2911 0.054 Uiso 1 1 calc R . . . . 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 0.03173(7) 0.02862(6) 0.03203(6) 0.00199(4) 0.00781(4) 0.00225(5) F1 0.0737(16) 0.0457(12) 0.113(2) 0.0064(12) 0.0177(14) 0.0262(11) O1 0.0407(12) 0.0379(11) 0.0400(11) -0.0027(9) 0.0011(9) 0.0036(9) N1 0.0326(13) 0.0376(14) 0.0361(13) 0.0051(10) 0.0078(10) 0.0020(10) N2 0.0349(13) 0.0325(12) 0.0351(13) 0.0010(10) 0.0096(10) 0.0006(10) N3 0.0437(14) 0.0316(13) 0.0388(13) 0.0007(11) 0.0162(11) -0.0013(11) C1 0.0480(19) 0.0507(19) 0.0488(19) 0.0090(15) 0.0179(16) 0.0097(15) C2 0.058(2) 0.068(3) 0.052(2) 0.0113(18) 0.0260(18) 0.0093(19) C3 0.052(2) 0.080(3) 0.049(2) 0.0223(19) 0.0163(17) -0.0052(19) C4 0.0468(19) 0.0492(19) 0.052(2) 0.0151(17) 0.0036(15) -0.0082(16) C5 0.128(4) 0.057(3) 0.083(3) 0.016(2) 0.033(3) -0.022(3) C6 0.0291(15) 0.0392(17) 0.0415(16) 0.0083(13) 0.0001(12) -0.0013(12) C7 0.0317(15) 0.0351(16) 0.0476(18) -0.0003(13) -0.0037(13) -0.0027(13) C8 0.0439(19) 0.0337(17) 0.070(2) 0.0025(16) 0.0002(17) -0.0047(15) C9 0.055(2) 0.0399(19) 0.072(2) -0.0168(18) -0.0030(19) 0.0017(16) C10 0.058(2) 0.051(2) 0.051(2) -0.0156(17) 0.0037(17) 0.0087(17) C11 0.053(2) 0.0441(19) 0.0431(18) 0.0004(14) 0.0100(15) 0.0067(15) C12 0.0335(15) 0.0303(14) 0.0403(16) -0.0020(13) 0.0020(12) 0.0058(12) C13 0.0358(15) 0.0285(15) 0.0398(15) 0.0000(12) 0.0052(12) 0.0045(12) C14 0.0454(19) 0.0472(18) 0.0465(18) 0.0073(15) 0.0050(15) 0.0030(15) C15 0.058(2) 0.055(2) 0.051(2) 0.0047(17) -0.0082(17) 0.0038(18) C16 0.043(2) 0.055(2) 0.077(3) -0.0021(19) -0.0127(19) 0.0001(17) C17 0.0375(18) 0.046(2) 0.080(3) -0.0016(18) 0.0088(18) -0.0005(15) C18 0.0340(16) 0.0276(15) 0.0556(19) -0.0007(13) 0.0091(14) 0.0032(12) C19 0.0398(17) 0.0269(14) 0.0563(19) -0.0024(14) 0.0202(14) -0.0008(13) C20 0.057(2) 0.0363(18) 0.076(2) -0.0002(18) 0.0350(19) -0.0015(16) C21 0.061(3) 0.074(3) 0.109(4) -0.001(3) 0.046(3) 0.006(2) C22 0.088(3) 0.052(2) 0.072(3) 0.005(2) 0.052(2) -0.003(2) C23 0.089(3) 0.057(2) 0.050(2) 0.0107(18) 0.030(2) 0.000(2) C24 0.061(2) 0.0454(19) 0.0412(18) 0.0061(15) 0.0156(16) 0.0010(16) C25 0.0358(16) 0.0396(16) 0.0376(16) 0.0073(13) 0.0065(12) 0.0001(13) C26 0.0410(18) 0.056(2) 0.053(2) 0.0051(17) -0.0035(15) 0.0041(16) C27 0.042(2) 0.059(2) 0.070(2) 0.0160(19) 0.0022(17) 0.0140(17) C28 0.052(2) 0.0387(18) 0.071(2) 0.0091(17) 0.0203(18) 0.0146(16) C29 0.0445(18) 0.0344(16) 0.0470(18) 0.0061(13) 0.0178(14) 0.0025(14) C30 0.0350(15) 0.0312(14) 0.0364(15) 0.0064(12) 0.0128(12) -0.0003(12) C31 0.060(2) 0.0353(17) 0.059(2) -0.0056(15) 0.0191(18) 0.0021(16) C32 0.058(2) 0.0406(18) 0.057(2) -0.0138(16) 0.0052(17) -0.0057(17) C33 0.0423(18) 0.0426(18) 0.0474(18) -0.0052(14) 0.0020(14) -0.0021(14) 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 89.81(9) . . ? N1 Ir1 N2 96.86(9) . . ? N2 Ir1 O1 77.64(9) . . ? N3 Ir1 O1 95.80(9) . . ? N3 Ir1 N1 171.15(9) . . ? N3 Ir1 N2 91.04(9) . . ? C12 Ir1 O1 95.64(10) . . ? C12 Ir1 N1 79.72(11) . . ? C12 Ir1 N2 172.55(10) . . ? C12 Ir1 N3 92.88(11) . . ? C13 Ir1 O1 172.01(9) . . ? C13 Ir1 N1 95.29(11) . . ? C13 Ir1 N2 95.60(10) . . ? C13 Ir1 N3 79.90(11) . . ? C13 Ir1 C12 91.33(11) . . ? C25 O1 Ir1 112.88(18) . . ? C1 N1 Ir1 122.5(2) . . ? C1 N1 C6 120.6(3) . . ? C6 N1 Ir1 116.8(2) . . ? C30 N2 Ir1 112.80(19) . . ? C33 N2 Ir1 128.1(2) . . ? C33 N2 C30 119.1(3) . . ? C19 N3 Ir1 116.9(2) . . ? C24 N3 Ir1 121.0(2) . . ? C24 N3 C19 121.3(3) . . ? N1 C1 C2 122.2(3) . . ? C3 C2 C1 118.6(4) . . ? C2 C3 C4 121.3(3) . . ? C3 C4 C5 117.8(3) . . ? C3 C4 C6 118.7(3) . . ? C6 C4 C5 123.5(4) . . ? N1 C6 C4 118.5(3) . . ? N1 C6 C7 113.0(3) . . ? C4 C6 C7 128.4(3) . . ? C8 C7 C6 126.2(3) . . ? C8 C7 C12 119.8(3) . . ? C12 C7 C6 113.9(3) . . ? C9 C8 C7 120.9(3) . . ? C10 C9 C8 120.4(3) . . ? C9 C10 C11 119.6(3) . . ? C10 C11 C12 122.1(3) . . ? C7 C12 Ir1 115.9(2) . . ? C11 C12 Ir1 126.9(2) . . ? C11 C12 C7 117.1(3) . . ? C14 C13 Ir1 127.4(2) . . ? C14 C13 C18 117.1(3) . . ? C18 C13 Ir1 115.2(2) . . ? C15 C14 C13 121.9(3) . . ? C16 C15 C14 120.6(4) . . ? C15 C16 C17 119.6(3) . . ? C16 C17 C18 120.9(3) . . ? C13 C18 C19 114.5(3) . . ? C17 C18 C13 119.9(3) . . ? C17 C18 C19 125.4(3) . . ? N3 C19 C18 112.4(2) . . ? N3 C19 C20 119.0(3) . . ? C20 C19 C18 128.5(3) . . ? C19 C20 C21 123.7(4) . . ? C22 C20 C19 117.5(3) . . ? C22 C20 C21 118.6(3) . . ? C23 C22 C20 122.1(3) . . ? C22 C23 C24 118.7(4) . . ? N3 C24 C23 121.1(4) . . ? O1 C25 C26 123.5(3) . . ? O1 C25 C30 119.9(3) . . ? C26 C25 C30 116.6(3) . . ? C27 C26 C25 121.3(3) . . ? C28 C27 C26 120.8(3) . . ? F1 C28 C29 117.4(3) . . ? C27 C28 F1 120.0(3) . . ? C27 C28 C29 122.6(3) . . ? C28 C29 C30 116.2(3) . . ? C28 C29 C31 125.9(3) . . ? C31 C29 C30 117.9(3) . . ? N2 C30 C25 116.7(3) . . ? N2 C30 C29 120.8(3) . . ? C29 C30 C25 122.6(3) . . ? C32 C31 C29 120.0(3) . . ? C31 C32 C33 119.5(3) . . ? N2 C33 C32 122.7(3) . . ? 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 2.162(2) . ? Ir1 N1 2.042(2) . ? Ir1 N2 2.144(2) . ? Ir1 N3 2.038(2) . ? Ir1 C12 1.997(3) . ? Ir1 C13 1.992(3) . ? F1 C28 1.367(4) . ? O1 C25 1.306(4) . ? N1 C1 1.345(4) . ? N1 C6 1.368(4) . ? N2 C30 1.371(4) . ? N2 C33 1.320(4) . ? N3 C19 1.359(4) . ? N3 C24 1.344(4) . ? C1 C2 1.372(5) . ? C2 C3 1.355(5) . ? C3 C4 1.385(5) . ? C4 C5 1.503(5) . ? C4 C6 1.417(5) . ? C6 C7 1.474(5) . ? C7 C8 1.395(4) . ? C7 C12 1.419(5) . ? C8 C9 1.379(5) . ? C9 C10 1.367(5) . ? C10 C11 1.390(5) . ? C11 C12 1.401(4) . ? C13 C14 1.395(4) . ? C13 C18 1.420(4) . ? C14 C15 1.381(5) . ? C15 C16 1.365(6) . ? C16 C17 1.382(6) . ? C17 C18 1.396(5) . ? C18 C19 1.471(5) . ? C19 C20 1.410(4) . ? C20 C21 1.509(6) . ? C20 C22 1.388(6) . ? C22 C23 1.349(6) . ? C23 C24 1.371(5) . ? C25 C26 1.394(4) . ? C25 C30 1.432(4) . ? C26 C27 1.394(5) . ? C27 C28 1.356(5) . ? C28 C29 1.399(5) . ? C29 C30 1.424(4) . ? C29 C31 1.400(5) . ? C31 C32 1.351(5) . ? C32 C33 1.400(5) . ?