#------------------------------------------------------------------------------ #$Date: 2026-06-30 01:16:59 +0100 (Tue, 30 Jun 2026) $ #$Revision: 306683 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/11/7721183.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_7721183 loop_ _publ_author_name 'Monte, Laura' 'Lentz, Nicolas' 'Albrecht, Martin' _publ_section_title ; Pyridinium amidate (PYA) substituents impact ligand-centered hydride formation and (catalytic) hydride transfer reactivity ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT01322H _journal_year 2026 _chemical_formula_moiety 'C24 H30 Ir N2 O2, F6 P' _chemical_formula_sum 'C24 H30 F6 Ir N2 O2 P' _chemical_formula_weight 715.67 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-04-11T15:12:38-00:00 _audit_update_record ; 2026-05-21 deposited with the CCDC. 2026-06-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.3315(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.16248(11) _cell_length_b 7.96837(9) _cell_length_c 34.6978(5) _cell_measurement_reflns_used 45491 _cell_measurement_temperature 173.00(10) _cell_measurement_theta_max 33.182 _cell_measurement_theta_min 2.262 _cell_volume 2529.01(6) _computing_cell_refinement 'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.144a 64-bit (release 23-01-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 173.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10 _diffrn_detector_type 'HyPix-Arc 100' _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _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 10.00 63.00 0.50 4.50 -- 13.17-114.00 24.00 106 2 \w -63.00 -6.00 0.50 4.50 -- -13.56 114.00 114.00 114 3 \w -35.00 63.00 0.50 4.50 -- -13.56 57.00 -90.00 196 4 \w -19.00 29.00 0.50 4.50 -- -13.56 -99.00 150.00 96 5 \w -25.00 67.00 0.50 4.50 -- -13.56 19.00 30.00 184 6 \w -87.00 -42.00 0.50 4.50 -- -13.56-178.00 0.00 90 7 \w -19.00 29.00 0.50 4.50 -- -13.56 -99.00 60.00 96 8 \w -87.00 -42.00 0.50 4.50 -- -13.56-178.00 90.00 90 9 \w -94.00 7.00 0.50 4.50 -- -13.56 -38.00-180.00 202 10 \w -94.00 7.00 0.50 4.50 -- -13.56 -38.00-180.00 202 11 \w -87.00 -42.00 0.50 4.50 -- -13.56-178.00 150.00 90 12 \w -19.00 29.00 0.50 4.50 -- -13.56 -99.00-120.00 96 13 \w -19.00 29.00 0.50 4.50 -- -13.56 -99.00 -30.00 96 14 \w -94.00 -38.00 0.50 4.50 -- -13.56 -38.00 -60.00 112 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix-Arc 100' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0678434 _diffrn_orient_matrix_UB_12 0.0345405 _diffrn_orient_matrix_UB_13 0.0069767 _diffrn_orient_matrix_UB_21 -0.013506 _diffrn_orient_matrix_UB_22 -0.0273622 _diffrn_orient_matrix_UB_23 0.0189128 _diffrn_orient_matrix_UB_31 0.0350625 _diffrn_orient_matrix_UB_32 -0.0773546 _diffrn_orient_matrix_UB_33 -0.0035788 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0138 _diffrn_reflns_Laue_measured_fraction_full 1 _diffrn_reflns_Laue_measured_fraction_max 1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_number 75638 _diffrn_reflns_point_group_measured_fraction_full 1 _diffrn_reflns_point_group_measured_fraction_max 1 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.507 _diffrn_reflns_theta_min 2.27 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 5.412 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.88 _exptl_crystal_description plate _exptl_crystal_F_000 1400 _exptl_crystal_size_max 0.145 _exptl_crystal_size_mid 0.121 _exptl_crystal_size_min 0.012 _refine_diff_density_max 1.029 _refine_diff_density_min -0.883 _refine_diff_density_rms 0.093 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.274 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 409 _refine_ls_number_reflns 7729 _refine_ls_number_restraints 169 _refine_ls_restrained_S_all 1.302 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0248 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0148P)^2^+3.2127P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.0487 _reflns_Friedel_coverage 0 _reflns_number_gt 7144 _reflns_number_total 7729 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt01322h2.cif _cod_data_source_block 25MA038_pMeO _cod_original_cell_volume 2529.00(5) _cod_database_code 7721183 _shelx_estimated_absorpt_t_min 0.497 _shelx_estimated_absorpt_t_max 0.948 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.141 _oxdiff_exptl_absorpt_empirical_full_min 0.905 _shelx_shelxl_version_number 2019/3 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N2-C13 \\sim N2A-C14A with sigma of 0.002 P1-F4A \\sim P1-F4 \\sim P1-F1A \\sim P1-F1 \\sim P1-F6 \\sim P1-F6A \\sim P1-F2 \\sim P1-F2A with sigma of 0.002 C9-C14 \\sim C9A-C13A with sigma of 0.002 3. Rigid bond restraints C13, N2, C8, C9, C14, C10, C11, C12 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 C13A, C9A, C8, N2A, C14A, C10, C11, C12 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 4. Uiso/Uaniso restraints and constraints Uanis(F1) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005 Uanis(F1A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F6A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005 Uanis(C14) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C9) \\sim Ueq, Uanis(N2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.02 5. Others Sof(H10A)=Sof(H12A)=Sof(N2A)=Sof(C9A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)= Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1) Sof(C9)=Sof(N2)=Sof(H10)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)= Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(H12)=FVAR(1) Sof(F2A)=Sof(F4A)=Sof(F1A)=Sof(F6A)=1-FVAR(2) Sof(F2)=Sof(F4)=Sof(F6)=Sof(F1)=FVAR(2) 6.a Aromatic/amide H refined with riding coordinates: C6(H6), C3(H3), C5(H5), C10(H10), C10(H10A), C12(H12), C12(H12A), C11(H11) 6.b Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C7(H7A,H7B,H7C), C22(H22A,H22B, H22C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C13(H13A,H13B,H13C), C14(H14A, H14B,H14C), C14A(H14D,H14E,H14F), C13A(H13D,H13E,H13F) ; _shelx_res_file ; TITL 25ma038_pmeo_a.res in P2(1)/n 25ma038_pmeo.res created by SHELXL-2019/3 at 15:10:29 on 11-Apr-2025 REM Old TITL 25MA038_pMeO_GC1 in P2(1) REM SHELXT solution in P2(1)/n: R1 0.051, Rweak 0.004, Alpha 0.037 REM 1.565 for 395 systematic absences, Orientation as input REM Formula found by SHELXT: C25 O2 F7 P Ir CELL 0.71073 9.162481 7.968369 34.69775 90 93.3315 90 ZERR 4 0.000109 0.000089 0.000474 0 0.0011 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F Ir N O P UNIT 96 120 24 4 8 8 4 SADI 0.002 N2 C13 N2A C14A ISOR 0.01 0.005 F1 F5 F4 F2 F6 F3 SADI 0.002 P1 F4A P1 F4 P1 F1A P1 F1 P1 F6 P1 F6A P1 F2 P1 F2A SADI 0.002 C9 C14 C9A C13A ISOR 0.01 0.005 F1A F4A F2A F6A DELU 0.001 0.001 C13 N2 C8 C9 C14 C10 C11 C12 ISOR 0.01 0.02 C14 C14A C13 C13A C9A N2 ISOR 0.005 0.02 C9 N2A DELU 0.001 0.001 C13A C9A C8 N2A C14A C10 C11 C12 L.S. 20 0 0 PLAN 20 SIZE 0.01 0.12 0.15 TEMP -100 CONF BOND list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.014800 3.212700 FVAR 0.22473 0.45044 0.43821 IR1 4 0.666055 0.358475 0.432559 11.00000 0.01794 0.02074 = 0.01635 0.00080 0.00045 -0.00188 P1 7 0.027147 0.455851 0.274449 11.00000 0.04480 0.03130 = 0.03832 0.00015 0.00878 0.00081 O1 6 0.540982 0.193242 0.458757 11.00000 0.02387 0.02535 = 0.01734 0.00252 -0.00046 -0.00431 N1 5 0.528006 0.293142 0.389334 11.00000 0.02244 0.02364 = 0.01710 0.00283 -0.00010 -0.00510 O2 6 0.113129 -0.089612 0.361936 11.00000 0.03178 0.03262 = 0.03007 0.00117 -0.00632 -0.01265 F3 3 -0.099203 0.588288 0.282425 11.00000 0.05361 0.04645 = 0.07395 0.00075 0.01762 0.00911 PART 1 F2 3 -0.056466 0.301614 0.292673 31.00000 0.05034 0.03606 = 0.06898 0.00894 -0.00835 -0.00687 PART 0 C1 1 0.433120 0.123150 0.436075 11.00000 0.01983 0.02053 = 0.01991 0.00017 0.00158 0.00065 C2 1 0.422677 0.173790 0.397322 11.00000 0.02049 0.01665 = 0.02032 0.00059 0.00156 -0.00016 F5 3 0.148248 0.321932 0.266082 11.00000 0.07549 0.06177 = 0.09095 0.00315 0.02537 0.02717 C18 1 0.811730 0.557366 0.415342 11.00000 0.02198 0.02560 = 0.02379 0.00301 -0.00028 -0.00566 C19 1 0.742705 0.604721 0.449978 11.00000 0.02121 0.02251 = 0.02694 0.00002 -0.00095 -0.00311 C6 1 0.335938 0.004535 0.448990 11.00000 0.02622 0.02327 = 0.01991 0.00254 0.00318 -0.00203 AFIX 43 H6 2 0.341814 -0.030468 0.475207 11.00000 -1.20000 AFIX 0 C15 1 0.782489 0.484035 0.479974 11.00000 0.01967 0.02620 = 0.01855 -0.00224 -0.00060 -0.00490 PART 1 C9 1 0.604643 0.266102 0.324562 21.00000 0.02751 0.02936 = 0.02056 -0.00580 0.00096 -0.00710 PART 0 C16 1 0.875569 0.362074 0.463998 11.00000 0.01759 0.02690 = 0.02309 0.00130 -0.00094 -0.00209 PART 1 F4 3 -0.038682 0.408922 0.232214 31.00000 0.11295 0.08889 = 0.04454 -0.00589 0.00457 0.01920 PART 0 C17 1 0.892968 0.406694 0.423827 11.00000 0.01853 0.02806 = 0.02336 -0.00118 0.00284 -0.00402 C8 1 0.529745 0.357219 0.351874 11.00000 0.02099 0.02419 = 0.01742 0.00048 -0.00096 -0.00472 C3 1 0.316670 0.106391 0.370878 11.00000 0.02241 0.02103 = 0.02049 0.00040 -0.00077 -0.00028 AFIX 43 H3 2 0.310422 0.140914 0.344628 11.00000 -1.20000 AFIX 0 C5 1 0.230218 -0.062075 0.423080 11.00000 0.02540 0.02183 = 0.02776 0.00299 0.00337 -0.00486 AFIX 43 H5 2 0.163016 -0.142526 0.431766 11.00000 -1.20000 AFIX 0 C4 1 0.221314 -0.012345 0.384365 11.00000 0.02127 0.01938 = 0.02780 -0.00100 -0.00119 -0.00143 C21 1 0.944092 0.214345 0.484401 11.00000 0.02676 0.03110 = 0.03320 0.00673 -0.00282 0.00207 AFIX 137 H21A 2 0.873222 0.162571 0.500844 11.00000 -1.50000 H21B 2 1.029851 0.251185 0.500381 11.00000 -1.50000 H21C 2 0.974177 0.132319 0.465370 11.00000 -1.50000 AFIX 0 C24 1 0.651713 0.758318 0.454907 11.00000 0.03409 0.02778 = 0.04040 -0.00468 -0.00130 0.00316 AFIX 137 H24A 2 0.592534 0.780202 0.430997 11.00000 -1.50000 H24B 2 0.715736 0.854554 0.460831 11.00000 -1.50000 H24C 2 0.587275 0.740797 0.476121 11.00000 -1.50000 AFIX 0 PART 1 N2 5 0.463052 0.498965 0.342020 21.00000 0.02189 0.02796 = 0.02412 0.00502 -0.00230 -0.00332 PART 0 C7 1 0.106588 -0.055558 0.321397 11.00000 0.04456 0.03232 = 0.03177 0.00197 -0.01410 -0.00782 AFIX 137 H7A 2 0.028625 -0.122773 0.308494 11.00000 -1.50000 H7B 2 0.200368 -0.084466 0.310900 11.00000 -1.50000 H7C 2 0.086290 0.063897 0.317021 11.00000 -1.50000 AFIX 0 PART 1 F6 3 0.103413 0.486526 0.316420 31.00000 0.07168 0.07033 = 0.06322 -0.00642 -0.01015 -0.02850 PART 0 C22 1 0.985856 0.313394 0.397057 11.00000 0.02891 0.04438 = 0.03442 -0.00626 0.01058 0.00277 AFIX 137 H22A 2 0.973867 0.192422 0.400864 11.00000 -1.50000 H22B 2 1.088610 0.344032 0.402436 11.00000 -1.50000 H22C 2 0.956026 0.342523 0.370310 11.00000 -1.50000 AFIX 0 PART 1 F1 3 0.126626 0.605300 0.260033 31.00000 0.06092 0.05136 = 0.06281 0.01088 0.01865 -0.01081 PART 0 C23 1 0.807316 0.653183 0.378173 11.00000 0.03484 0.03856 = 0.02999 0.01249 0.00001 -0.00945 AFIX 137 H23A 2 0.820507 0.575564 0.356744 11.00000 -1.50000 H23B 2 0.885860 0.736824 0.379171 11.00000 -1.50000 H23C 2 0.712693 0.709875 0.374275 11.00000 -1.50000 AFIX 0 C20 1 0.734560 0.486782 0.520676 11.00000 0.03146 0.03804 = 0.02244 -0.00447 0.00327 -0.00541 AFIX 137 H20A 2 0.647983 0.558315 0.521982 11.00000 -1.50000 H20B 2 0.813716 0.531330 0.537942 11.00000 -1.50000 H20C 2 0.710737 0.372490 0.528639 11.00000 -1.50000 AFIX 0 C10 1 0.614051 0.343792 0.288562 11.00000 0.03797 0.05263 = 0.01841 -0.00351 0.00405 -0.00985 PART 1 AFIX 43 H10 2 0.672000 0.292815 0.269978 21.00000 -1.20000 AFIX 43 PART 2 H10A 2 0.666107 0.285226 0.269856 -21.00000 -1.20000 AFIX 0 PART 1 C13 1 0.379414 0.590878 0.371025 21.00000 0.02761 0.03898 = 0.03800 0.00225 -0.00075 0.01067 AFIX 137 H13A 2 0.280612 0.614861 0.360076 21.00000 -1.50000 H13B 2 0.429303 0.696495 0.377827 21.00000 -1.50000 H13C 2 0.373391 0.521648 0.394222 21.00000 -1.50000 AFIX 0 C14 1 0.679396 0.104330 0.334795 21.00000 0.04377 0.03931 = 0.04183 -0.00754 0.00610 0.01006 AFIX 137 H14A 2 0.707487 0.102980 0.362480 21.00000 -1.50000 H14B 2 0.766984 0.093084 0.320079 21.00000 -1.50000 H14C 2 0.612791 0.010728 0.328542 21.00000 -1.50000 AFIX 0 PART 0 C12 1 0.462436 0.568089 0.305940 11.00000 0.04245 0.03708 = 0.02861 0.01226 -0.00671 -0.00495 PART 1 AFIX 43 H12 2 0.407957 0.666805 0.299679 21.00000 -1.20000 AFIX 43 PART 2 H12A 2 0.413497 0.669697 0.298969 -21.00000 -1.20000 AFIX 0 PART 0 C11 1 0.542816 0.490371 0.279211 11.00000 0.04488 0.05588 = 0.02011 0.01120 -0.00195 -0.01295 AFIX 43 H11 2 0.549215 0.537874 0.254254 11.00000 -1.20000 AFIX 0 PART 2 N2A 5 0.609051 0.283867 0.324840 -21.00000 0.02626 0.03217 = 0.02016 -0.00414 0.00119 -0.00512 C9A 1 0.449303 0.505381 0.342595 -21.00000 0.02524 0.03336 = 0.02340 0.00522 -0.00443 0.00216 C14A 1 0.682936 0.120913 0.334299 -21.00000 0.04327 0.03267 = 0.03190 -0.01377 0.00137 0.00355 AFIX 137 H14D 2 0.762104 0.139092 0.354080 -21.00000 -1.50000 H14E 2 0.723353 0.074785 0.311003 -21.00000 -1.50000 H14F 2 0.611880 0.041832 0.344026 -21.00000 -1.50000 AFIX 0 C13A 1 0.358133 0.585906 0.371718 -21.00000 0.02999 0.05288 = 0.03468 -0.00099 -0.00599 0.01861 AFIX 137 H13D 2 0.277774 0.510610 0.377552 -21.00000 -1.50000 H13E 2 0.318113 0.691768 0.361337 -21.00000 -1.50000 H13F 2 0.418665 0.608201 0.395381 -21.00000 -1.50000 AFIX 0 F2A 3 -0.055597 0.330838 0.301878 -31.00000 0.05588 0.04614 = 0.03732 0.00949 0.00424 -0.00376 F4A 3 -0.082510 0.394372 0.239714 -31.00000 0.06440 0.07016 = 0.02923 -0.00442 0.00003 0.00802 F1A 3 0.091832 0.582438 0.244083 -31.00000 0.05940 0.06743 = 0.07881 0.02190 0.02524 -0.00395 F6A 3 0.123676 0.528927 0.310345 -31.00000 0.06340 0.06232 = 0.08976 -0.01951 -0.01774 -0.01746 HKLF 4 REM 25ma038_pmeo_a.res in P2(1)/n REM wR2 = 0.0487, GooF = S = 1.274, Restrained GooF = 1.302 for all data REM R1 = 0.0248 for 7144 Fo > 4sig(Fo) and 0.0287 for all 7729 data REM 409 parameters refined using 169 restraints END WGHT 0.0148 3.2129 REM Highest difference peak 1.029, deepest hole -0.883, 1-sigma level 0.093 Q1 1 -0.0003 0.0771 0.3007 11.00000 0.05 1.03 Q2 1 0.7191 0.3037 0.4210 11.00000 0.05 0.73 Q3 1 0.6232 0.4207 0.4226 11.00000 0.05 0.70 Q4 1 0.6451 0.2630 0.4384 11.00000 0.05 0.60 Q5 1 0.6260 0.9546 0.4339 11.00000 0.05 0.57 Q6 1 0.5823 0.3556 0.4387 11.00000 0.05 0.56 Q7 1 0.6535 0.3414 0.4592 11.00000 0.05 0.55 Q8 1 0.1962 0.3691 0.2857 11.00000 0.05 0.53 Q9 1 0.6907 0.4591 0.4230 11.00000 0.05 0.52 Q10 1 0.1727 -0.1369 0.3411 11.00000 0.05 0.51 Q11 1 0.7193 0.8962 0.4359 11.00000 0.05 0.49 Q12 1 0.4342 0.1658 0.4210 11.00000 0.05 0.48 Q13 1 -0.0357 0.6908 0.2976 11.00000 0.05 0.45 Q14 1 0.0443 0.5944 0.2991 11.00000 0.05 0.40 Q15 1 0.2340 0.0819 0.3814 11.00000 0.05 0.40 Q16 1 0.5789 0.3357 0.3408 11.00000 0.05 0.39 Q17 1 0.1064 0.5205 0.2947 11.00000 0.05 0.38 Q18 1 -0.1111 0.5459 0.2580 11.00000 0.05 0.38 Q19 1 0.8660 0.3600 0.4387 11.00000 0.05 0.38 Q20 1 0.8809 0.5017 0.4207 11.00000 0.05 0.37 ; _shelx_res_checksum 5955 loop_ _symmetry_equiv_pos_as_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 0.66606(2) 0.35847(2) 0.43256(2) 0.01837(3) Uani 1 1 d . . . . . P1 P 0.02715(9) 0.45585(10) 0.27445(2) 0.03789(18) Uani 1 1 d D . . . . O1 O 0.54098(19) 0.1932(2) 0.45876(5) 0.0223(3) Uani 1 1 d . . . . . N1 N 0.5280(2) 0.2931(3) 0.38933(6) 0.0211(4) Uani 1 1 d . . . . . O2 O 0.1131(2) -0.0896(3) 0.36194(6) 0.0318(4) Uani 1 1 d . . . . . F3 F -0.0992(2) 0.5883(3) 0.28243(7) 0.0575(6) Uani 1 1 d . U . . . F2 F -0.0565(13) 0.3016(12) 0.2927(4) 0.052(3) Uani 0.44(2) 1 d D U P A 1 C1 C 0.4331(3) 0.1232(3) 0.43607(7) 0.0201(4) Uani 1 1 d . . . . . C2 C 0.4227(3) 0.1738(3) 0.39732(7) 0.0191(4) Uani 1 1 d . . . . . F5 F 0.1482(3) 0.3219(3) 0.26608(9) 0.0753(8) Uani 1 1 d . U . . . C18 C 0.8117(3) 0.5574(3) 0.41534(7) 0.0239(5) Uani 1 1 d . . . . . C19 C 0.7427(3) 0.6047(3) 0.44998(8) 0.0236(5) Uani 1 1 d . . . . . C6 C 0.3359(3) 0.0045(3) 0.44899(7) 0.0231(5) Uani 1 1 d . . . . . H6 H 0.341814 -0.030468 0.475207 0.028 Uiso 1 1 calc R U . . . C15 C 0.7825(3) 0.4840(3) 0.47997(7) 0.0215(5) Uani 1 1 d . . . . . C9 C 0.605(4) 0.266(3) 0.3246(8) 0.0258(17) Uani 0.45(2) 1 d D U P B 1 C16 C 0.8756(3) 0.3621(3) 0.46400(7) 0.0226(5) Uani 1 1 d . . . . . F4 F -0.0387(18) 0.4089(17) 0.2322(2) 0.082(3) Uani 0.44(2) 1 d D U P A 1 C17 C 0.8930(3) 0.4067(3) 0.42383(7) 0.0233(5) Uani 1 1 d . . . . . C8 C 0.5297(3) 0.3572(3) 0.35187(7) 0.0209(4) Uani 1 1 d . U . . . C3 C 0.3167(3) 0.1064(3) 0.37088(7) 0.0214(5) Uani 1 1 d . . . . . H3 H 0.310422 0.140914 0.344628 0.026 Uiso 1 1 calc R U . . . C5 C 0.2302(3) -0.0621(3) 0.42308(7) 0.0249(5) Uani 1 1 d . . . . . H5 H 0.163016 -0.142526 0.431766 0.03 Uiso 1 1 calc R U . . . C4 C 0.2213(3) -0.0123(3) 0.38437(7) 0.0229(5) Uani 1 1 d . . . . . C21 C 0.9441(3) 0.2143(4) 0.48440(8) 0.0305(6) Uani 1 1 d . . . . . H21A H 0.873222 0.162571 0.500844 0.046 Uiso 1 1 calc R U . . . H21B H 1.029851 0.251185 0.500381 0.046 Uiso 1 1 calc R U . . . H21C H 0.974177 0.132319 0.46537 0.046 Uiso 1 1 calc R U . . . C24 C 0.6517(3) 0.7583(4) 0.45491(9) 0.0342(6) Uani 1 1 d . . . . . H24A H 0.592534 0.780202 0.430997 0.051 Uiso 1 1 calc R U . . . H24B H 0.715736 0.854554 0.460831 0.051 Uiso 1 1 calc R U . . . H24C H 0.587275 0.740797 0.476121 0.051 Uiso 1 1 calc R U . . . N2 N 0.463(4) 0.499(3) 0.3420(6) 0.025(2) Uani 0.45(2) 1 d D U P B 1 C7 C 0.1066(4) -0.0556(4) 0.32140(8) 0.0369(7) Uani 1 1 d . . . . . H7A H 0.028625 -0.122773 0.308494 0.055 Uiso 1 1 calc R U . . . H7B H 0.200368 -0.084466 0.3109 0.055 Uiso 1 1 calc R U . . . H7C H 0.08629 0.063897 0.317021 0.055 Uiso 1 1 calc R U . . . F6 F 0.1034(14) 0.4865(17) 0.31642(17) 0.069(3) Uani 0.44(2) 1 d D U P A 1 C22 C 0.9859(3) 0.3134(4) 0.39706(9) 0.0356(6) Uani 1 1 d . . . . . H22A H 0.973867 0.192422 0.400864 0.053 Uiso 1 1 calc R U . . . H22B H 1.08861 0.344032 0.402436 0.053 Uiso 1 1 calc R U . . . H22C H 0.956026 0.342523 0.37031 0.053 Uiso 1 1 calc R U . . . F1 F 0.1266(10) 0.6053(7) 0.2600(4) 0.058(2) Uani 0.44(2) 1 d D U P A 1 C23 C 0.8073(3) 0.6532(4) 0.37817(8) 0.0345(6) Uani 1 1 d . . . . . H23A H 0.820507 0.575564 0.356744 0.052 Uiso 1 1 calc R U . . . H23B H 0.88586 0.736824 0.379171 0.052 Uiso 1 1 calc R U . . . H23C H 0.712693 0.709875 0.374275 0.052 Uiso 1 1 calc R U . . . C20 C 0.7346(3) 0.4868(4) 0.52068(8) 0.0306(6) Uani 1 1 d . . . . . H20A H 0.647983 0.558315 0.521982 0.046 Uiso 1 1 calc R U . . . H20B H 0.813716 0.53133 0.537942 0.046 Uiso 1 1 calc R U . . . H20C H 0.710737 0.37249 0.528639 0.046 Uiso 1 1 calc R U . . . C10 C 0.6141(3) 0.3438(4) 0.28856(8) 0.0362(5) Uani 1 1 d . U . . . H10 H 0.672 0.292815 0.269978 0.043 Uiso 0.45(2) 1 calc R U P B 1 H10A H 0.666107 0.285226 0.269856 0.043 Uiso 0.55(2) 1 calc R U P B 2 C13 C 0.379(3) 0.591(3) 0.3710(6) 0.035(3) Uani 0.45(2) 1 d D U P B 1 H13A H 0.280612 0.614861 0.360076 0.052 Uiso 0.45(2) 1 calc R U P B 1 H13B H 0.429303 0.696495 0.377827 0.052 Uiso 0.45(2) 1 calc R U P B 1 H13C H 0.373391 0.521648 0.394222 0.052 Uiso 0.45(2) 1 calc R U P B 1 C14 C 0.679(3) 0.104(3) 0.3348(8) 0.041(4) Uani 0.45(2) 1 d D U P B 1 H14A H 0.707487 0.10298 0.36248 0.062 Uiso 0.45(2) 1 calc R U P B 1 H14B H 0.766984 0.093084 0.320079 0.062 Uiso 0.45(2) 1 calc R U P B 1 H14C H 0.612791 0.010728 0.328542 0.062 Uiso 0.45(2) 1 calc R U P B 1 C12 C 0.4624(3) 0.5681(4) 0.30594(8) 0.0364(6) Uani 1 1 d . U . . . H12 H 0.407957 0.666805 0.299679 0.044 Uiso 0.45(2) 1 calc R U P B 1 H12A H 0.413497 0.669697 0.298969 0.044 Uiso 0.55(2) 1 calc R U P B 2 C11 C 0.5428(4) 0.4904(5) 0.27921(8) 0.0404(6) Uani 1 1 d . U . . . H11 H 0.549215 0.537874 0.254254 0.049 Uiso 1 1 calc R U . . . N2A N 0.609(3) 0.284(2) 0.3248(5) 0.0262(19) Uani 0.55(2) 1 d D U P B 2 C9A C 0.449(4) 0.505(3) 0.3426(6) 0.028(2) Uani 0.55(2) 1 d D U P B 2 C14A C 0.683(3) 0.121(2) 0.3343(6) 0.036(2) Uani 0.55(2) 1 d D U P B 2 H14D H 0.762104 0.139092 0.35408 0.054 Uiso 0.55(2) 1 calc R U P B 2 H14E H 0.723353 0.074785 0.311003 0.054 Uiso 0.55(2) 1 calc R U P B 2 H14F H 0.61188 0.041832 0.344026 0.054 Uiso 0.55(2) 1 calc R U P B 2 C13A C 0.358(2) 0.586(2) 0.3717(5) 0.039(3) Uani 0.55(2) 1 d D U P B 2 H13D H 0.277774 0.51061 0.377552 0.059 Uiso 0.55(2) 1 calc R U P B 2 H13E H 0.318113 0.691768 0.361337 0.059 Uiso 0.55(2) 1 calc R U P B 2 H13F H 0.418665 0.608201 0.395381 0.059 Uiso 0.55(2) 1 calc R U P B 2 F2A F -0.0556(10) 0.3308(10) 0.3019(2) 0.0464(17) Uani 0.56(2) 1 d D U P A 2 F4A F -0.0825(8) 0.3944(10) 0.23971(18) 0.0547(18) Uani 0.56(2) 1 d D U P A 2 F1A F 0.0918(10) 0.5824(10) 0.2441(3) 0.068(2) Uani 0.56(2) 1 d D U P A 2 F6A F 0.1237(11) 0.5289(13) 0.3103(2) 0.073(2) Uani 0.56(2) 1 d D U P A 2 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 0.01794(4) 0.02074(4) 0.01635(4) 0.00080(4) 0.00045(3) -0.00188(4) P1 0.0448(5) 0.0313(4) 0.0383(4) 0.0001(3) 0.0088(3) 0.0008(3) O1 0.0239(9) 0.0253(8) 0.0173(8) 0.0025(7) -0.0005(6) -0.0043(7) N1 0.0224(10) 0.0236(10) 0.0171(9) 0.0028(8) -0.0001(7) -0.0051(8) O2 0.0318(10) 0.0326(10) 0.0301(10) 0.0012(8) -0.0063(8) -0.0126(8) F3 0.0536(12) 0.0465(11) 0.0739(15) 0.0008(11) 0.0176(11) 0.0091(10) F2 0.050(3) 0.036(3) 0.069(5) 0.009(3) -0.008(3) -0.007(3) C1 0.0198(11) 0.0205(11) 0.0199(10) 0.0002(9) 0.0016(8) 0.0007(9) C2 0.0205(11) 0.0166(11) 0.0203(11) 0.0006(8) 0.0016(8) -0.0002(8) F5 0.0755(17) 0.0618(15) 0.0910(19) 0.0032(13) 0.0254(14) 0.0272(13) C18 0.0220(11) 0.0256(12) 0.0238(12) 0.0030(10) -0.0003(9) -0.0057(10) C19 0.0212(11) 0.0225(12) 0.0269(12) 0.0000(9) -0.0009(9) -0.0031(9) C6 0.0262(12) 0.0233(12) 0.0199(11) 0.0025(9) 0.0032(9) -0.0020(10) C15 0.0197(11) 0.0262(12) 0.0185(11) -0.0022(9) -0.0006(8) -0.0049(9) C9 0.028(4) 0.029(3) 0.021(2) -0.0058(18) 0.001(3) -0.007(3) C16 0.0176(10) 0.0269(12) 0.0231(11) 0.0013(10) -0.0009(8) -0.0021(10) F4 0.113(5) 0.089(5) 0.045(4) -0.006(3) 0.005(3) 0.019(4) C17 0.0185(11) 0.0281(12) 0.0234(11) -0.0012(9) 0.0028(9) -0.0040(9) C8 0.0210(11) 0.0242(10) 0.0174(8) 0.0005(7) -0.0010(7) -0.0047(8) C3 0.0224(11) 0.0210(12) 0.0205(11) 0.0004(8) -0.0008(9) -0.0003(9) C5 0.0254(12) 0.0218(12) 0.0278(12) 0.0030(10) 0.0034(10) -0.0049(10) C4 0.0213(11) 0.0194(11) 0.0278(12) -0.0010(9) -0.0012(9) -0.0014(9) C21 0.0268(13) 0.0311(14) 0.0332(14) 0.0067(11) -0.0028(11) 0.0021(11) C24 0.0341(15) 0.0278(14) 0.0404(16) -0.0047(12) -0.0013(12) 0.0032(11) N2 0.022(6) 0.028(4) 0.024(2) 0.005(2) -0.002(3) -0.003(3) C7 0.0446(17) 0.0323(15) 0.0318(14) 0.0020(12) -0.0141(12) -0.0078(13) F6 0.072(4) 0.070(5) 0.063(4) -0.006(3) -0.010(3) -0.028(3) C22 0.0289(14) 0.0444(17) 0.0344(15) -0.0063(13) 0.0106(12) 0.0028(12) F1 0.061(4) 0.051(3) 0.063(4) 0.011(3) 0.019(3) -0.011(2) C23 0.0348(15) 0.0386(16) 0.0300(14) 0.0125(12) 0.0000(11) -0.0094(13) C20 0.0315(14) 0.0380(15) 0.0224(12) -0.0045(11) 0.0033(10) -0.0054(12) C10 0.0380(15) 0.0526(15) 0.0184(9) -0.0035(10) 0.0041(10) -0.0099(11) C13 0.028(7) 0.039(5) 0.038(3) 0.002(4) -0.001(4) 0.011(4) C14 0.044(10) 0.039(6) 0.042(6) -0.008(4) 0.006(6) 0.010(6) C12 0.0425(16) 0.0371(14) 0.0286(11) 0.0123(9) -0.0067(10) -0.0049(11) C11 0.0449(17) 0.0559(16) 0.0201(10) 0.0112(10) -0.0020(10) -0.0130(12) N2A 0.026(3) 0.032(4) 0.0202(17) -0.004(2) 0.001(2) -0.005(3) C9A 0.025(6) 0.033(4) 0.023(2) 0.005(3) -0.004(3) 0.002(4) C14A 0.043(7) 0.033(4) 0.032(4) -0.014(3) 0.001(5) 0.004(3) C13A 0.030(6) 0.053(5) 0.035(3) -0.001(3) -0.006(3) 0.019(4) F2A 0.056(3) 0.046(3) 0.037(3) 0.009(2) 0.004(2) -0.004(2) F4A 0.064(3) 0.070(3) 0.029(2) -0.004(2) 0.000(2) 0.008(2) F1A 0.059(3) 0.067(3) 0.079(4) 0.022(3) 0.025(3) -0.004(2) F6A 0.063(3) 0.062(4) 0.090(4) -0.020(3) -0.018(3) -0.017(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 1 0.0663 0 -1 -1 0.0578 1 0 1 0.0519 1 -1 0 0.0781 -1 0 1 0.0757 1 1 -1 0.0805 -6 -10 -10 0.038 0 0 -1 0.0112 0 0 1 0.001 -11 5 -11 0.066 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ir1 C18 168.80(8) . . ? O1 Ir1 C19 131.10(9) . . ? O1 Ir1 C15 103.31(8) . . ? O1 Ir1 C16 107.24(8) . . ? O1 Ir1 C17 139.95(9) . . ? N1 Ir1 O1 79.21(8) . . ? N1 Ir1 C18 111.05(9) . . ? N1 Ir1 C19 129.49(9) . . ? N1 Ir1 C15 165.75(9) . . ? N1 Ir1 C16 154.35(9) . . ? N1 Ir1 C17 121.42(9) . . ? C19 Ir1 C18 38.80(10) . . ? C15 Ir1 C18 65.63(9) . . ? C15 Ir1 C19 39.23(9) . . ? C16 Ir1 C18 65.58(10) . . ? C16 Ir1 C19 65.16(10) . . ? C16 Ir1 C15 38.68(10) . . ? C16 Ir1 C17 39.54(9) . . ? C17 Ir1 C18 38.67(10) . . ? C17 Ir1 C19 64.91(10) . . ? C17 Ir1 C15 65.49(9) . . ? F2 P1 F3 94.0(5) . . ? F5 P1 F3 178.39(16) . . ? F5 P1 F2 84.9(5) . . ? F5 P1 F4 84.5(5) . . ? F5 P1 F6 89.8(5) . . ? F5 P1 F1 91.5(3) . . ? F5 P1 F2A 92.9(4) . . ? F5 P1 F4A 94.1(3) . . ? F5 P1 F1A 90.8(3) . . ? F5 P1 F6A 91.5(4) . . ? F4 P1 F3 94.3(5) . . ? F4 P1 F2 91.1(6) . . ? F4 P1 F6 174.2(8) . . ? F4 P1 F1 94.5(5) . . ? F6 P1 F3 91.4(5) . . ? F6 P1 F2 87.2(5) . . ? F6 P1 F1 86.8(5) . . ? F1 P1 F3 89.7(3) . . ? F1 P1 F2 173.0(6) . . ? F2A P1 F3 86.3(4) . . ? F2A P1 F4A 87.6(4) . . ? F4A P1 F3 84.5(3) . . ? F1A P1 F3 89.9(3) . . ? F1A P1 F2A 173.2(5) . . ? F1A P1 F4A 86.4(4) . . ? F6A P1 F3 89.9(4) . . ? F6A P1 F2A 91.3(5) . . ? F6A P1 F4A 174.3(5) . . ? F6A P1 F1A 94.3(4) . . ? C1 O1 Ir1 115.32(14) . . ? C2 N1 Ir1 116.68(15) . . ? C2 N1 C8 118.7(2) . . ? C8 N1 Ir1 124.66(16) . . ? C4 O2 C7 117.4(2) . . ? O1 C1 C2 116.6(2) . . ? O1 C1 C6 123.7(2) . . ? C6 C1 C2 119.7(2) . . ? N1 C2 C1 112.2(2) . . ? N1 C2 C3 126.3(2) . . ? C1 C2 C3 121.5(2) . . ? C19 C18 Ir1 69.88(14) . . ? C19 C18 C23 126.4(2) . . ? C17 C18 Ir1 69.73(14) . . ? C17 C18 C19 107.2(2) . . ? C17 C18 C23 126.3(2) . . ? C23 C18 Ir1 128.39(18) . . ? C18 C19 Ir1 71.32(14) . . ? C18 C19 C15 108.7(2) . . ? C18 C19 C24 125.7(2) . . ? C15 C19 Ir1 70.23(14) . . ? C15 C19 C24 125.4(2) . . ? C24 C19 Ir1 126.95(19) . . ? C1 C6 H6 120.4 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 H6 120.4 . . ? C19 C15 Ir1 70.53(14) . . ? C19 C15 C20 126.2(2) . . ? C16 C15 Ir1 70.58(14) . . ? C16 C15 C19 107.7(2) . . ? C16 C15 C20 126.1(2) . . ? C20 C15 Ir1 124.43(17) . . ? C8 C9 C14 121.4(19) . . ? C10 C9 C8 115.5(12) . . ? C10 C9 C14 122.8(19) . . ? C15 C16 Ir1 70.74(13) . . ? C15 C16 C17 107.9(2) . . ? C15 C16 C21 126.7(2) . . ? C17 C16 Ir1 70.25(13) . . ? C17 C16 C21 125.4(2) . . ? C21 C16 Ir1 124.60(18) . . ? C18 C17 Ir1 71.60(14) . . ? C18 C17 C16 108.5(2) . . ? C18 C17 C22 126.6(2) . . ? C16 C17 Ir1 70.21(13) . . ? C16 C17 C22 124.9(2) . . ? C22 C17 Ir1 126.04(19) . . ? N1 C8 C9 118.1(9) . . ? N1 C8 C9A 118.8(7) . . ? N2 C8 N1 121.6(7) . . ? N2 C8 C9 120.3(10) . . ? N2A C8 N1 121.5(6) . . ? N2A C8 C9A 119.7(8) . . ? C2 C3 H3 121.1 . . ? C4 C3 C2 117.8(2) . . ? C4 C3 H3 121.1 . . ? C6 C5 H5 119.6 . . ? C6 C5 C4 120.9(2) . . ? C4 C5 H5 119.6 . . ? O2 C4 C3 124.3(2) . . ? O2 C4 C5 114.7(2) . . ? C3 C4 C5 121.0(2) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 N2 C13 119.6(15) . . ? C8 N2 C12 124.0(11) . . ? C12 N2 C13 116.4(12) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C10 H10 118.8 . . ? C11 C10 C9 122.4(9) . . ? C11 C10 H10 118.8 . . ? C11 C10 H10A 120.6 . . ? N2A C10 H10A 120.6 . . ? N2A C10 C11 118.8(6) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C12 H12 121.1 . . ? C11 C12 N2 117.7(6) . . ? C11 C12 H12 121.1 . . ? C11 C12 H12A 118.6 . . ? C11 C12 C9A 122.8(6) . . ? C9A C12 H12A 118.6 . . ? C10 C11 H11 120.2 . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11 120.2 . . ? C8 N2A C14A 118.6(13) . . ? C10 N2A C8 122.9(10) . . ? C10 N2A C14A 118.3(13) . . ? C8 C9A C13A 120.5(14) . . ? C12 C9A C8 116.0(10) . . ? C12 C9A C13A 123.4(13) . . ? N2A C14A H14D 109.5 . . ? N2A C14A H14E 109.5 . . ? N2A C14A H14F 109.5 . . ? H14D C14A H14E 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C9A C13A H13D 109.5 . . ? C9A C13A H13E 109.5 . . ? C9A C13A H13F 109.5 . . ? H13D C13A H13E 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? 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 1.9985(17) . ? Ir1 N1 1.975(2) . ? Ir1 C18 2.178(2) . ? Ir1 C19 2.159(2) . ? Ir1 C15 2.154(2) . ? Ir1 C16 2.152(2) . ? Ir1 C17 2.153(2) . ? P1 F3 1.602(2) . ? P1 F2 1.5980(19) . ? P1 F5 1.578(2) . ? P1 F4 1.596(2) . ? P1 F6 1.597(2) . ? P1 F1 1.5976(19) . ? P1 F2A 1.5990(19) . ? P1 F4A 1.6004(19) . ? P1 F1A 1.5973(19) . ? P1 F6A 1.5952(19) . ? O1 C1 1.348(3) . ? N1 C2 1.394(3) . ? N1 C8 1.397(3) . ? O2 C4 1.370(3) . ? O2 C7 1.430(3) . ? C1 C2 1.402(3) . ? C1 C6 1.390(3) . ? C2 C3 1.404(3) . ? C18 C19 1.440(4) . ? C18 C17 1.434(4) . ? C18 C23 1.497(4) . ? C19 C15 1.448(4) . ? C19 C24 1.496(4) . ? C6 H6 0.95 . ? C6 C5 1.388(4) . ? C15 C16 1.426(4) . ? C15 C20 1.503(4) . ? C9 C8 1.40(2) . ? C9 C10 1.40(2) . ? C9 C14 1.493(14) . ? C16 C17 1.456(3) . ? C16 C21 1.493(4) . ? C17 C22 1.494(4) . ? C8 N2 1.320(16) . ? C8 N2A 1.352(17) . ? C8 C9A 1.419(16) . ? C3 H3 0.95 . ? C3 C4 1.387(3) . ? C5 H5 0.95 . ? C5 C4 1.398(4) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? N2 C13 1.492(12) . ? N2 C12 1.367(18) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C10 H10 0.95 . ? C10 H10A 0.95 . ? C10 C11 1.368(5) . ? C10 N2A 1.350(17) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C12 H12 0.95 . ? C12 H12A 0.95 . ? C12 C11 1.366(5) . ? C12 C9A 1.378(19) . ? C11 H11 0.95 . ? N2A C14A 1.492(12) . ? C9A C13A 1.493(14) . ? C14A H14D 0.98 . ? C14A H14E 0.98 . ? C14A H14F 0.98 . ? C13A H13D 0.98 . ? C13A H13E 0.98 . ? C13A H13F 0.98 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ir1 O1 C1 C2 0.3(3) . . . . ? Ir1 O1 C1 C6 179.38(19) . . . . ? Ir1 N1 C2 C1 1.2(3) . . . . ? Ir1 N1 C2 C3 -178.30(19) . . . . ? Ir1 N1 C8 C9 95.1(19) . . . . ? Ir1 N1 C8 N2 -85(2) . . . . ? Ir1 N1 C8 N2A 89.8(14) . . . . ? Ir1 N1 C8 C9A -88(2) . . . . ? Ir1 C18 C19 C15 60.55(17) . . . . ? Ir1 C18 C19 C24 -122.6(3) . . . . ? Ir1 C18 C17 C16 -60.84(17) . . . . ? Ir1 C18 C17 C22 121.7(3) . . . . ? Ir1 C19 C15 C16 61.11(17) . . . . ? Ir1 C19 C15 C20 -119.0(2) . . . . ? Ir1 C15 C16 C17 60.75(17) . . . . ? Ir1 C15 C16 C21 -119.3(3) . . . . ? Ir1 C16 C17 C18 61.72(17) . . . . ? Ir1 C16 C17 C22 -120.8(3) . . . . ? O1 C1 C2 N1 -0.9(3) . . . . ? O1 C1 C2 C3 178.6(2) . . . . ? O1 C1 C6 C5 -178.9(2) . . . . ? N1 C2 C3 C4 179.7(2) . . . . ? N1 C8 N2 C13 -2(4) . . . . ? N1 C8 N2 C12 179(2) . . . . ? N1 C8 N2A C10 -179.3(14) . . . . ? N1 C8 N2A C14A 7(3) . . . . ? N1 C8 C9A C12 176.2(19) . . . . ? N1 C8 C9A C13A -3(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C1 C6 C5 C4 0.5(4) . . . . ? C2 N1 C8 C9 -85(2) . . . . ? C2 N1 C8 N2 95(2) . . . . ? C2 N1 C8 N2A -89.9(14) . . . . ? C2 N1 C8 C9A 92(2) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C2 C3 C4 O2 -179.6(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C18 C19 C15 Ir1 -61.23(17) . . . . ? C18 C19 C15 C16 -0.1(3) . . . . ? C18 C19 C15 C20 179.8(2) . . . . ? C19 C18 C17 Ir1 60.11(17) . . . . ? C19 C18 C17 C16 -0.7(3) . . . . ? C19 C18 C17 C22 -178.2(3) . . . . ? C19 C15 C16 Ir1 -61.08(16) . . . . ? C19 C15 C16 C17 -0.3(3) . . . . ? C19 C15 C16 C21 179.6(2) . . . . ? C6 C1 C2 N1 179.9(2) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? C6 C5 C4 O2 179.2(2) . . . . ? C6 C5 C4 C3 -0.8(4) . . . . ? C15 C16 C17 Ir1 -61.06(17) . . . . ? C15 C16 C17 C18 0.7(3) . . . . ? C15 C16 C17 C22 178.2(2) . . . . ? C9 C8 N2 C13 178(3) . . . . ? C9 C8 N2 C12 -1(5) . . . . ? C9 C10 C11 C12 2(2) . . . . ? C17 C18 C19 Ir1 -60.02(17) . . . . ? C17 C18 C19 C15 0.5(3) . . . . ? C17 C18 C19 C24 177.4(2) . . . . ? C8 N1 C2 C1 -179.1(2) . . . . ? C8 N1 C2 C3 1.4(4) . . . . ? C8 C9 C10 C11 -6(4) . . . . ? C8 N2 C12 C11 -4(4) . . . . ? C21 C16 C17 Ir1 119.0(3) . . . . ? C21 C16 C17 C18 -179.3(2) . . . . ? C21 C16 C17 C22 -1.7(4) . . . . ? C24 C19 C15 Ir1 121.9(3) . . . . ? C24 C19 C15 C16 -177.0(2) . . . . ? C24 C19 C15 C20 2.9(4) . . . . ? N2 C12 C11 C10 3(2) . . . . ? C7 O2 C4 C3 5.5(4) . . . . ? C7 O2 C4 C5 -174.5(2) . . . . ? C23 C18 C19 Ir1 123.5(3) . . . . ? C23 C18 C19 C15 -176.0(2) . . . . ? C23 C18 C19 C24 0.9(4) . . . . ? C23 C18 C17 Ir1 -123.4(3) . . . . ? C23 C18 C17 C16 175.8(2) . . . . ? C23 C18 C17 C22 -1.7(4) . . . . ? C20 C15 C16 Ir1 119.0(2) . . . . ? C20 C15 C16 C17 179.8(2) . . . . ? C20 C15 C16 C21 -0.3(4) . . . . ? C10 C9 C8 N1 -174.4(18) . . . . ? C10 C9 C8 N2 6(4) . . . . ? C13 N2 C12 C11 177(2) . . . . ? C14 C9 C8 N1 1(4) . . . . ? C14 C9 C8 N2 -179(3) . . . . ? C14 C9 C10 C11 179(3) . . . . ? C11 C10 N2A C8 4(3) . . . . ? C11 C10 N2A C14A 178.0(17) . . . . ? C11 C12 C9A C8 3(4) . . . . ? C11 C12 C9A C13A -178(2) . . . . ? N2A C8 C9A C12 -2(4) . . . . ? N2A C8 C9A C13A 178(3) . . . . ? N2A C10 C11 C12 -3.3(14) . . . . ? C9A C8 N2A C10 -1(3) . . . . ? C9A C8 N2A C14A -175(3) . . . . ? C9A C12 C11 C10 0(2) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0001 0.9996 0.9999 0.0415 -0.0084 -0.0809 -0.0001 -0.9996 -0.9999 -0.0415 0.0084 0.0809 0.9995 -0.0001 1.0028 0.0748 0.0055 0.0315 0.9994 -0.9997 0.0029 0.0333 0.0139 0.1124 -1.0001 -0.0001 0.998 -0.0609 0.0324 -0.0386 1.0005 0.9998 -0.9985 0.0954 -0.0598 -0.0387 -5.592 -9.7809 -10.1417 -0.788 0.1513 0.5968 0.0003 0.0001 -1.0004 -0.007 -0.0189 0.0036 -0.0003 -0.0001 1.0004 0.007 0.0189 -0.0036 -10.9927 4.9991 -11.0329 -0.6501 -0.197 -0.7326