#------------------------------------------------------------------------------ #$Date: 2019-03-20 01:17:39 +0200 (Wed, 20 Mar 2019) $ #$Revision: 214196 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/07/1550754.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_1550754 loop_ _publ_author_name 'Tickner, Ben' 'John, Richard O.' 'Roy, Soumya Singha' 'Hart, Sam' 'Whitwood, Adrian Charles' 'Duckett, Simon B.' _publ_section_title ; Using coligands to gain mechanistic insight into iridium complexes hyperpolarized with para-hydrogen ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC00444K _journal_year 2019 _chemical_formula_moiety 'C41 H47 Ir N4 O5, C H2 Cl2' _chemical_formula_sum 'C42 H49 Cl2 Ir N4 O5' _chemical_formula_weight 952.95 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-09-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-01-25 deposited with the CCDC. 2019-03-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.6750(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.08570(10) _cell_length_b 11.99650(10) _cell_length_c 24.9643(2) _cell_measurement_reflns_used 31122 _cell_measurement_temperature 109.95(10) _cell_measurement_theta_max 31.7570 _cell_measurement_theta_min 3.6920 _cell_volume 4180.65(6) _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 109.95(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1450 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.938 _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 -45.00 55.00 1.00 40.00 -- 24.78 -77.00 150.00 100 2 \w 35.00 101.00 1.00 40.00 -- 24.78 178.00-150.00 66 3 \w 4.00 94.00 1.00 40.00 -- 24.78 57.00 -90.00 90 4 \w -101.00 -55.00 1.00 40.00 -- -24.94 178.00-120.00 46 5 \w -101.00 -55.00 1.00 40.00 -- -24.94 178.00 -60.00 46 6 \w 4.00 94.00 1.00 40.00 -- 24.78 57.00 30.00 90 7 \w 35.00 101.00 1.00 40.00 -- 24.78 178.00 0.00 66 8 \w 2.00 55.00 1.00 40.00 -- 24.78 46.00-163.00 53 9 \w 4.00 94.00 1.00 40.00 -- 24.78 57.00 120.00 90 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0060270000 _diffrn_orient_matrix_UB_12 0.0555856000 _diffrn_orient_matrix_UB_13 0.0086056000 _diffrn_orient_matrix_UB_21 -0.0472565000 _diffrn_orient_matrix_UB_22 0.0004225000 _diffrn_orient_matrix_UB_23 -0.0140223000 _diffrn_orient_matrix_UB_31 -0.0177190000 _diffrn_orient_matrix_UB_32 -0.0201126000 _diffrn_orient_matrix_UB_33 0.0234750000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.938 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 63675 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.938 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.788 _diffrn_reflns_theta_min 3.294 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 3.369 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.514 _exptl_crystal_description block _exptl_crystal_F_000 1920 _exptl_crystal_recrystallization_method 'DCM, H2O hexane' _exptl_crystal_size_max 0.151 _exptl_crystal_size_mid 0.139 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.932 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 502 _refine_ls_number_reflns 13379 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0219 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0145P)^2^+3.0501P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0465 _reflns_Friedel_coverage 0.000 _reflns_number_gt 11691 _reflns_number_total 13379 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; sbd1805.res created by SHELXL-2014/7 TITL sbd1805_a.res in P2(1)/n REM Old TITL sbd1805 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.076, Rweak 0.003, Alpha 0.025, Orientation as input REM Formula found by SHELXT: C40 N9 O6 Ir CELL 0.71073 14.0857 11.9965 24.9643 90 97.675 90 ZERR 4 0.0001 0.0001 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl Ir N O UNIT 168 196 8 4 16 20 EQIV $1 1-X,1-Y,1-Z L.S. 50 PLAN 20 SIZE 0.09 0.139 0.151 HTAB N4 O2_$1 list 4 BOND $H CONF fmap 2 53 acta REM REM REM WGHT 0.014500 3.050100 FVAR 0.24299 C1 1 0.300214 0.436435 0.651804 11.00000 0.01532 0.01290 = 0.01278 0.00063 0.00348 -0.00108 C2 1 0.215283 0.522211 0.711524 11.00000 0.02092 0.02981 = 0.02276 -0.00855 0.00992 0.00386 AFIX 43 H2 2 0.200723 0.556634 0.742798 11.00000 -1.20000 AFIX 0 C3 1 0.154504 0.500588 0.666812 11.00000 0.01692 0.02944 = 0.02531 -0.00662 0.00916 0.00461 AFIX 43 H3 2 0.089497 0.517471 0.661127 11.00000 -1.20000 AFIX 0 C4 1 0.390183 0.506688 0.738920 11.00000 0.01761 0.02331 = 0.01148 -0.00496 0.00364 0.00154 C5 1 0.423443 0.430720 0.779330 11.00000 0.02753 0.02376 = 0.01530 -0.00035 0.00724 0.00031 C6 1 0.505529 0.459079 0.814073 11.00000 0.03305 0.03005 = 0.01421 0.00269 -0.00008 0.00565 AFIX 43 H6 2 0.529412 0.408901 0.840933 11.00000 -1.20000 AFIX 0 C7 1 0.553096 0.559548 0.810114 11.00000 0.02527 0.03159 = 0.01852 -0.00733 -0.00165 0.00442 C8 1 0.515269 0.634161 0.770679 11.00000 0.02354 0.02260 = 0.02023 -0.00721 0.00268 -0.00007 AFIX 43 H8 2 0.545777 0.702279 0.767953 11.00000 -1.20000 AFIX 0 C9 1 0.433287 0.610836 0.735012 11.00000 0.02143 0.01938 = 0.01380 -0.00453 0.00366 0.00436 C10 1 0.371691 0.323407 0.787452 11.00000 0.04395 0.03096 = 0.02094 0.00499 0.01028 -0.00754 AFIX 137 H10A 2 0.305789 0.330132 0.771981 11.00000 -1.50000 H10B 2 0.375245 0.308161 0.825418 11.00000 -1.50000 H10C 2 0.401058 0.263542 0.770132 11.00000 -1.50000 AFIX 0 C11 1 0.641453 0.588201 0.848375 11.00000 0.03456 0.04563 = 0.03340 -0.00634 -0.01119 0.00180 AFIX 137 H11A 2 0.696117 0.552708 0.836572 11.00000 -1.50000 H11B 2 0.634099 0.562663 0.884032 11.00000 -1.50000 H11C 2 0.650541 0.667522 0.848943 11.00000 -1.50000 AFIX 0 C12 1 0.391905 0.699073 0.695199 11.00000 0.02982 0.01987 = 0.02821 -0.00126 0.00265 0.00601 AFIX 137 H12A 2 0.357916 0.663774 0.663831 11.00000 -1.50000 H12B 2 0.442859 0.743774 0.684702 11.00000 -1.50000 H12C 2 0.348707 0.745606 0.711825 11.00000 -1.50000 AFIX 0 C13 1 0.162440 0.414713 0.577314 11.00000 0.01112 0.01925 = 0.01758 -0.00171 0.00206 0.00089 C14 1 0.114863 0.312552 0.571898 11.00000 0.01185 0.02024 = 0.02219 -0.00191 0.00487 0.00059 C15 1 0.075028 0.280335 0.520211 11.00000 0.01577 0.02325 = 0.02737 -0.00743 0.00158 -0.00046 AFIX 43 H15 2 0.043806 0.212027 0.515513 11.00000 -1.20000 AFIX 0 C16 1 0.080710 0.347846 0.475253 11.00000 0.01666 0.03558 = 0.01916 -0.00408 -0.00095 0.00682 C17 1 0.123050 0.451085 0.483003 11.00000 0.01870 0.03287 = 0.02163 0.00615 0.00263 0.00556 AFIX 43 H17 2 0.124694 0.497648 0.453356 11.00000 -1.20000 AFIX 0 C18 1 0.163577 0.487984 0.533999 11.00000 0.01350 0.02132 = 0.02345 0.00188 0.00209 0.00340 C19 1 0.103831 0.240835 0.620059 11.00000 0.02243 0.02293 = 0.02678 0.00293 0.00826 -0.00198 AFIX 137 H19A 2 0.165971 0.220149 0.637879 11.00000 -1.50000 H19B 2 0.068358 0.174904 0.608357 11.00000 -1.50000 H19C 2 0.070120 0.281652 0.644698 11.00000 -1.50000 AFIX 0 C20 1 0.039599 0.309413 0.419408 11.00000 0.03138 0.05326 = 0.02463 -0.00956 -0.00475 0.00799 AFIX 137 H20A 2 0.050048 0.230757 0.416198 11.00000 -1.50000 H20B 2 0.070499 0.348443 0.392954 11.00000 -1.50000 H20C 2 -0.027910 0.324581 0.413535 11.00000 -1.50000 AFIX 0 C21 1 0.204565 0.603709 0.540031 11.00000 0.02305 0.02099 = 0.04161 0.00689 0.00582 0.00176 AFIX 137 H21A 2 0.153470 0.657221 0.535079 11.00000 -1.50000 H21B 2 0.246720 0.615664 0.513372 11.00000 -1.50000 H21C 2 0.239679 0.612142 0.575492 11.00000 -1.50000 AFIX 0 C22 1 0.364701 0.180020 0.655887 11.00000 0.01921 0.01658 = 0.01585 0.00218 0.00779 0.00055 C23 1 0.414551 0.416382 0.505100 11.00000 0.01282 0.01413 = 0.01329 -0.00060 0.00183 -0.00279 C24 1 0.485943 0.322137 0.518008 11.00000 0.01399 0.01332 = 0.01404 -0.00107 0.00450 -0.00161 C25 1 0.539333 0.283322 0.473768 11.00000 0.02372 0.02006 = 0.01858 0.00042 0.01043 0.00293 AFIX 137 H25A 2 0.574091 0.344663 0.461152 11.00000 -1.50000 H25B 2 0.494887 0.254735 0.444488 11.00000 -1.50000 H25C 2 0.583390 0.225581 0.487185 11.00000 -1.50000 AFIX 0 C26 1 0.562036 0.196021 0.585230 11.00000 0.01486 0.01411 = 0.01744 -0.00089 0.00138 0.00307 AFIX 23 H26A 2 0.574748 0.196303 0.624387 11.00000 -1.20000 H26B 2 0.622173 0.208555 0.571250 11.00000 -1.20000 AFIX 0 C27 1 0.521294 0.082506 0.565843 11.00000 0.01928 0.01310 = 0.02180 -0.00121 0.00040 0.00152 AFIX 23 H27A 2 0.461990 0.069211 0.580589 11.00000 -1.20000 H27B 2 0.506977 0.082974 0.526743 11.00000 -1.20000 AFIX 0 C28 1 0.591077 -0.010175 0.583105 11.00000 0.02125 0.01091 = 0.02151 -0.00130 0.00018 -0.00074 C29 1 0.591365 -0.059819 0.633379 11.00000 0.03394 0.01899 = 0.02261 0.00011 0.00636 0.00060 AFIX 43 H29 2 0.547111 -0.037309 0.655704 11.00000 -1.20000 AFIX 0 C30 1 0.657055 -0.142641 0.650565 11.00000 0.04249 0.02282 = 0.03397 0.01150 0.00221 0.00100 AFIX 43 H30 2 0.657960 -0.173713 0.684760 11.00000 -1.20000 AFIX 0 C31 1 0.721016 -0.179099 0.617174 11.00000 0.02999 0.01952 = 0.05207 0.01029 0.00076 0.00534 AFIX 43 H31 2 0.764310 -0.235550 0.628551 11.00000 -1.20000 AFIX 0 C32 1 0.720646 -0.131472 0.566660 11.00000 0.02386 0.02457 = 0.04240 -0.00175 0.00862 0.00464 AFIX 43 H32 2 0.763185 -0.156528 0.543846 11.00000 -1.20000 AFIX 0 C33 1 0.656750 -0.046282 0.550063 11.00000 0.02435 0.01994 = 0.02510 0.00183 0.00463 0.00115 AFIX 43 H33 2 0.657940 -0.013078 0.516496 11.00000 -1.20000 AFIX 0 C34 1 0.593520 0.459992 0.663827 11.00000 0.01529 0.01537 = 0.01800 0.00130 -0.00114 -0.00197 AFIX 23 H34A 2 0.623013 0.398526 0.646936 11.00000 -1.20000 H34B 2 0.582954 0.436984 0.699809 11.00000 -1.20000 AFIX 0 C35 1 0.659447 0.561646 0.667418 11.00000 0.01666 0.01684 = 0.01878 -0.00031 -0.00069 -0.00164 AFIX 23 H35A 2 0.659754 0.591005 0.631238 11.00000 -1.20000 H35B 2 0.632319 0.618574 0.688423 11.00000 -1.20000 AFIX 0 C36 1 0.761533 0.542099 0.691991 11.00000 0.01598 0.02121 = 0.01782 0.00473 0.00135 -0.00314 C37 1 0.806584 0.617895 0.729132 11.00000 0.02309 0.03663 = 0.01892 -0.00139 -0.00076 -0.00674 AFIX 43 H37 2 0.771524 0.676762 0.740746 11.00000 -1.20000 AFIX 0 C38 1 0.902909 0.607379 0.749214 11.00000 0.02288 0.06906 = 0.02022 0.00301 -0.00311 -0.01435 AFIX 43 H38 2 0.932203 0.659630 0.773536 11.00000 -1.20000 AFIX 0 C39 1 0.954993 0.519267 0.732997 11.00000 0.01531 0.07560 = 0.03119 0.02428 0.00066 -0.00152 AFIX 43 H39 2 1.019344 0.511224 0.746680 11.00000 -1.20000 AFIX 0 C40 1 0.911284 0.443261 0.696455 11.00000 0.02053 0.04015 = 0.06056 0.01754 0.01551 0.00647 AFIX 43 H40 2 0.946325 0.383667 0.685540 11.00000 -1.20000 AFIX 0 C41 1 0.815395 0.454758 0.675755 11.00000 0.02236 0.02604 = 0.04401 -0.00176 0.00884 -0.00225 AFIX 43 H41 2 0.786964 0.403317 0.650722 11.00000 -1.20000 AFIX 0 IR1 4 0.401539 0.361620 0.614936 11.00000 0.01052 0.01154 = 0.00929 0.00045 0.00260 0.00029 N1 5 0.304688 0.483027 0.702031 11.00000 0.01553 0.02105 = 0.01446 -0.00345 0.00491 0.00132 N2 5 0.206390 0.448308 0.630484 11.00000 0.01491 0.01962 = 0.01594 -0.00408 0.00437 0.00144 N3 5 0.494607 0.286547 0.567033 11.00000 0.01108 0.01147 = 0.01423 -0.00030 0.00334 -0.00084 N4 5 0.500818 0.489328 0.631405 11.00000 0.01418 0.01361 = 0.01246 -0.00073 0.00304 0.00023 H4A 2 0.515793 0.513174 0.600673 11.00000 0.02418 H4B 2 0.475315 0.542346 0.648464 11.00000 0.02480 O1 6 0.368883 0.447260 0.543614 11.00000 0.01318 0.01572 = 0.01187 0.00219 0.00354 0.00181 O2 6 0.405234 0.460083 0.459975 11.00000 0.01838 0.02136 = 0.01292 0.00350 0.00343 0.00027 O3 6 0.430545 0.252520 0.677357 11.00000 0.01923 0.01709 = 0.01182 0.00348 0.00148 0.00039 O4 6 0.322502 0.216524 0.608501 11.00000 0.01563 0.01426 = 0.01430 0.00153 0.00270 -0.00211 O5 6 0.346004 0.092069 0.677162 11.00000 0.03586 0.02010 = 0.02161 0.00766 0.00579 -0.00486 C42 1 0.209694 -0.013861 0.586069 11.00000 0.02620 0.02306 = 0.03761 -0.00528 0.00198 0.00073 AFIX 23 H42A 2 0.190852 -0.009227 0.621983 11.00000 -1.20000 H42B 2 0.236138 0.057723 0.577681 11.00000 -1.20000 AFIX 0 CL1 3 0.298064 -0.117962 0.585223 11.00000 0.04250 0.02620 = 0.04468 -0.00147 0.01071 0.00984 CL2 3 0.108720 -0.042890 0.539089 11.00000 0.05077 0.04286 = 0.10331 -0.01966 -0.03591 -0.00218 HKLF 4 REM sbd1805_a.res in P2(1)/n REM R1 = 0.0219 for 11691 Fo > 4sig(Fo) and 0.0289 for all 13379 data REM 502 parameters refined using 0 restraints END WGHT 0.0145 3.0505 REM Highest difference peak 0.932, deepest hole -0.640, 1-sigma level 0.094 Q1 1 0.3431 0.3624 0.5996 11.00000 0.05 0.93 Q2 1 0.4568 0.3585 0.6254 11.00000 0.05 0.89 Q3 1 0.4057 0.2985 0.6163 11.00000 0.05 0.77 Q4 1 0.3961 0.4394 0.6183 11.00000 0.05 0.68 Q5 1 0.2986 0.1400 0.6601 11.00000 0.05 0.61 Q6 1 0.6254 -0.0975 0.6401 11.00000 0.05 0.50 Q7 1 0.4339 0.3560 0.5798 11.00000 0.05 0.48 Q8 1 0.3547 0.4242 0.6425 11.00000 0.05 0.48 Q9 1 0.7085 0.5525 0.6792 11.00000 0.05 0.47 Q10 1 0.5553 0.0408 0.5784 11.00000 0.05 0.46 Q11 1 0.4038 0.5599 0.7410 11.00000 0.05 0.44 Q12 1 0.4201 0.4787 0.7569 11.00000 0.05 0.44 Q13 1 0.0844 0.4033 0.4810 11.00000 0.05 0.44 Q14 1 0.1198 -0.0936 0.5589 11.00000 0.05 0.43 Q15 1 0.5423 0.1419 0.5721 11.00000 0.05 0.43 Q16 1 0.1778 0.5407 0.5385 11.00000 0.05 0.42 Q17 1 0.3696 0.3209 0.6428 11.00000 0.05 0.42 Q18 1 0.1346 0.3652 0.5788 11.00000 0.05 0.42 Q19 1 0.1610 0.4648 0.5592 11.00000 0.05 0.41 Q20 1 0.1194 0.2840 0.5405 11.00000 0.05 0.40 REM The information below was added by Olex2. REM REM R1 = 0.0219 for 11691 Fo > 4sig(Fo) and 0.0289 for all 65355 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.93, deepest hole -0.64 REM Mean Shift 0, Max Shift 0.008. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0289 REM R1_gt = 0.0219 REM wR_ref = 0.0465 REM GOOF = 1.043 REM Shift_max = 0.008 REM Shift_mean = 0 REM Reflections_all = 65355 REM Reflections_gt = 11691 REM Parameters = n/a REM Hole = -0.64 REM Peak = 0.93 REM Flack = n/a ; _cod_data_source_file c9sc00444k2.cif _cod_data_source_block sbd1805 _cod_database_code 1550754 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'C37 H44 Ir N4 O2' _chemical_oxdiff_usercomment 'Ben Tickner BT 2AP' _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 0.751 _shelx_estimated_absorpt_t_min 0.630 _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 29.51 _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.a Secondary CH2 refined with riding coordinates: C26(H26A,H26B), C27(H27A,H27B), C34(H34A,H34B), C35(H35A,H35B), C42(H42A,H42B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41) 2.c Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B, H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C) ; _olex2_date_sample_data_collection 2018-09-13 _olex2_date_sample_submission 2018-09-04 _olex2_exptl_crystal_mounting_method 'oil on micromount' _olex2_submission_original_sample_id 'BT 2AP' _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 1.125 _oxdiff_exptl_absorpt_empirical_full_min 0.916 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 C1 C 0.30021(12) 0.43643(14) 0.65180(7) 0.0135(3) Uani 1 1 d . C2 C 0.21528(14) 0.52221(18) 0.71152(9) 0.0239(4) Uani 1 1 d . H2 H 0.2007 0.5566 0.7428 0.029 Uiso 1 1 calc R C3 C 0.15450(14) 0.50059(18) 0.66681(8) 0.0233(4) Uani 1 1 d . H3 H 0.0895 0.5175 0.6611 0.028 Uiso 1 1 calc R C4 C 0.39018(13) 0.50669(16) 0.73892(7) 0.0173(4) Uani 1 1 d . C5 C 0.42344(15) 0.43072(17) 0.77933(8) 0.0218(4) Uani 1 1 d . C6 C 0.50553(16) 0.45908(19) 0.81407(8) 0.0261(4) Uani 1 1 d . H6 H 0.5294 0.4089 0.8409 0.031 Uiso 1 1 calc R C7 C 0.55310(15) 0.55955(19) 0.81011(8) 0.0255(4) Uani 1 1 d . C8 C 0.51527(14) 0.63416(17) 0.77068(8) 0.0221(4) Uani 1 1 d . H8 H 0.5458 0.7023 0.7680 0.027 Uiso 1 1 calc R C9 C 0.43329(14) 0.61084(16) 0.73501(8) 0.0181(4) Uani 1 1 d . C10 C 0.37169(18) 0.3234(2) 0.78745(9) 0.0314(5) Uani 1 1 d . H10A H 0.3058 0.3301 0.7720 0.047 Uiso 1 1 calc GR H10B H 0.3752 0.3082 0.8254 0.047 Uiso 1 1 calc GR H10C H 0.4011 0.2635 0.7701 0.047 Uiso 1 1 calc GR C11 C 0.64145(18) 0.5882(2) 0.84837(10) 0.0393(6) Uani 1 1 d . H11A H 0.6961 0.5527 0.8366 0.059 Uiso 1 1 calc GR H11B H 0.6341 0.5627 0.8840 0.059 Uiso 1 1 calc GR H11C H 0.6505 0.6675 0.8489 0.059 Uiso 1 1 calc GR C12 C 0.39190(16) 0.69907(18) 0.69520(9) 0.0261(4) Uani 1 1 d . H12A H 0.3579 0.6638 0.6638 0.039 Uiso 1 1 calc GR H12B H 0.4429 0.7438 0.6847 0.039 Uiso 1 1 calc GR H12C H 0.3487 0.7456 0.7118 0.039 Uiso 1 1 calc GR C13 C 0.16244(12) 0.41471(16) 0.57731(7) 0.0160(3) Uani 1 1 d . C14 C 0.11486(13) 0.31255(16) 0.57190(8) 0.0179(4) Uani 1 1 d . C15 C 0.07503(14) 0.28033(17) 0.52021(8) 0.0222(4) Uani 1 1 d . H15 H 0.0438 0.2120 0.5155 0.027 Uiso 1 1 calc R C16 C 0.08071(14) 0.34785(19) 0.47525(8) 0.0241(4) Uani 1 1 d . C17 C 0.12305(14) 0.45109(19) 0.48300(9) 0.0244(4) Uani 1 1 d . H17 H 0.1247 0.4976 0.4534 0.029 Uiso 1 1 calc R C18 C 0.16358(13) 0.48798(17) 0.53400(8) 0.0195(4) Uani 1 1 d . C19 C 0.10383(15) 0.24083(17) 0.62006(9) 0.0236(4) Uani 1 1 d . H19A H 0.1660 0.2201 0.6379 0.035 Uiso 1 1 calc GR H19B H 0.0684 0.1749 0.6084 0.035 Uiso 1 1 calc GR H19C H 0.0701 0.2817 0.6447 0.035 Uiso 1 1 calc GR C20 C 0.03960(17) 0.3094(2) 0.41941(9) 0.0372(6) Uani 1 1 d . H20A H 0.0500 0.2308 0.4162 0.056 Uiso 1 1 calc GR H20B H 0.0705 0.3484 0.3930 0.056 Uiso 1 1 calc GR H20C H -0.0279 0.3246 0.4135 0.056 Uiso 1 1 calc GR C21 C 0.20457(15) 0.60371(18) 0.54003(10) 0.0284(5) Uani 1 1 d . H21A H 0.1535 0.6572 0.5351 0.043 Uiso 1 1 calc GR H21B H 0.2467 0.6157 0.5134 0.043 Uiso 1 1 calc GR H21C H 0.2397 0.6121 0.5755 0.043 Uiso 1 1 calc GR C22 C 0.36470(13) 0.18002(16) 0.65589(8) 0.0167(4) Uani 1 1 d . C23 C 0.41455(12) 0.41638(15) 0.50510(7) 0.0134(3) Uani 1 1 d . C24 C 0.48594(12) 0.32214(15) 0.51801(7) 0.0135(3) Uani 1 1 d . C25 C 0.53933(14) 0.28332(17) 0.47377(8) 0.0201(4) Uani 1 1 d . H25A H 0.5741 0.3447 0.4612 0.030 Uiso 1 1 calc GR H25B H 0.4949 0.2547 0.4445 0.030 Uiso 1 1 calc GR H25C H 0.5834 0.2256 0.4872 0.030 Uiso 1 1 calc GR C26 C 0.56204(13) 0.19602(15) 0.58523(8) 0.0155(3) Uani 1 1 d . H26A H 0.5747 0.1963 0.6244 0.019 Uiso 1 1 calc R H26B H 0.6222 0.2086 0.5712 0.019 Uiso 1 1 calc R C27 C 0.52129(13) 0.08251(15) 0.56584(8) 0.0183(4) Uani 1 1 d . H27A H 0.4620 0.0692 0.5806 0.022 Uiso 1 1 calc R H27B H 0.5070 0.0830 0.5267 0.022 Uiso 1 1 calc R C28 C 0.59108(14) -0.01018(15) 0.58311(8) 0.0181(4) Uani 1 1 d . C29 C 0.59136(16) -0.05982(17) 0.63338(9) 0.0249(4) Uani 1 1 d . H29 H 0.5471 -0.0373 0.6557 0.030 Uiso 1 1 calc R C30 C 0.65705(18) -0.14264(19) 0.65057(10) 0.0334(5) Uani 1 1 d . H30 H 0.6580 -0.1737 0.6848 0.040 Uiso 1 1 calc R C31 C 0.72102(17) -0.17910(19) 0.61717(11) 0.0343(5) Uani 1 1 d . H31 H 0.7643 -0.2356 0.6286 0.041 Uiso 1 1 calc R C32 C 0.72065(16) -0.13147(18) 0.56666(10) 0.0299(5) Uani 1 1 d . H32 H 0.7632 -0.1565 0.5438 0.036 Uiso 1 1 calc R C33 C 0.65675(15) -0.04628(17) 0.55006(9) 0.0230(4) Uani 1 1 d . H33 H 0.6579 -0.0131 0.5165 0.028 Uiso 1 1 calc R C34 C 0.59352(13) 0.45999(15) 0.66383(8) 0.0165(3) Uani 1 1 d . H34A H 0.6230 0.3985 0.6469 0.020 Uiso 1 1 calc R H34B H 0.5830 0.4370 0.6998 0.020 Uiso 1 1 calc R C35 C 0.65945(13) 0.56165(16) 0.66742(8) 0.0177(4) Uani 1 1 d . H35A H 0.6598 0.5910 0.6312 0.021 Uiso 1 1 calc R H35B H 0.6323 0.6186 0.6884 0.021 Uiso 1 1 calc R C36 C 0.76153(13) 0.54210(16) 0.69199(8) 0.0184(4) Uani 1 1 d . C37 C 0.80658(15) 0.61789(19) 0.72913(8) 0.0265(5) Uani 1 1 d . H37 H 0.7715 0.6768 0.7407 0.032 Uiso 1 1 calc R C38 C 0.90291(16) 0.6074(3) 0.74921(9) 0.0379(6) Uani 1 1 d . H38 H 0.9322 0.6596 0.7735 0.046 Uiso 1 1 calc R C39 C 0.95499(16) 0.5193(3) 0.73300(10) 0.0409(7) Uani 1 1 d . H39 H 1.0193 0.5112 0.7467 0.049 Uiso 1 1 calc R C40 C 0.91128(16) 0.4433(2) 0.69646(12) 0.0395(6) Uani 1 1 d . H40 H 0.9463 0.3837 0.6855 0.047 Uiso 1 1 calc R C41 C 0.81540(15) 0.45476(19) 0.67576(10) 0.0304(5) Uani 1 1 d . H41 H 0.7870 0.4033 0.6507 0.036 Uiso 1 1 calc R Ir1 Ir 0.40154(2) 0.36162(2) 0.61494(2) 0.01033(2) Uani 1 1 d . N1 N 0.30469(11) 0.48303(14) 0.70203(6) 0.0168(3) Uani 1 1 d . N2 N 0.20639(11) 0.44831(13) 0.63048(6) 0.0166(3) Uani 1 1 d . N3 N 0.49461(10) 0.28655(12) 0.56703(6) 0.0121(3) Uani 1 1 d . N4 N 0.50082(11) 0.48933(13) 0.63141(6) 0.0133(3) Uani 1 1 d . H4A H 0.5158(16) 0.5132(19) 0.6007(10) 0.024(6) Uiso 1 1 d . H4B H 0.4753(17) 0.542(2) 0.6485(10) 0.025(6) Uiso 1 1 d . O1 O 0.36888(9) 0.44726(10) 0.54361(5) 0.0134(2) Uani 1 1 d . O2 O 0.40523(9) 0.46008(11) 0.45998(5) 0.0174(3) Uani 1 1 d . O3 O 0.43055(9) 0.25252(11) 0.67736(5) 0.0161(3) Uani 1 1 d . O4 O 0.32250(9) 0.21652(10) 0.60850(5) 0.0147(2) Uani 1 1 d . O5 O 0.34600(11) 0.09207(12) 0.67716(6) 0.0257(3) Uani 1 1 d . C42 C 0.20969(15) -0.01386(19) 0.58607(10) 0.0292(5) Uani 1 1 d . H42A H 0.1909 -0.0092 0.6220 0.035 Uiso 1 1 calc R H42B H 0.2361 0.0577 0.5777 0.035 Uiso 1 1 calc R Cl1 Cl 0.29806(5) -0.11796(5) 0.58522(3) 0.03735(13) Uani 1 1 d . Cl2 Cl 0.10872(6) -0.04289(7) 0.53909(4) 0.0698(3) 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 C1 0.0153(8) 0.0129(8) 0.0128(8) 0.0006(6) 0.0035(6) -0.0011(6) C2 0.0209(9) 0.0298(11) 0.0228(10) -0.0085(9) 0.0099(8) 0.0039(8) C3 0.0169(9) 0.0294(11) 0.0253(10) -0.0066(9) 0.0092(8) 0.0046(8) C4 0.0176(8) 0.0233(10) 0.0115(8) -0.0050(7) 0.0036(7) 0.0015(7) C5 0.0275(10) 0.0238(10) 0.0153(9) -0.0004(8) 0.0072(8) 0.0003(8) C6 0.0330(11) 0.0300(11) 0.0142(9) 0.0027(8) -0.0001(8) 0.0057(9) C7 0.0253(10) 0.0316(12) 0.0185(10) -0.0073(8) -0.0017(8) 0.0044(8) C8 0.0235(9) 0.0226(10) 0.0202(9) -0.0072(8) 0.0027(8) -0.0001(8) C9 0.0214(9) 0.0194(9) 0.0138(8) -0.0045(7) 0.0037(7) 0.0044(7) C10 0.0439(13) 0.0310(12) 0.0209(10) 0.0050(9) 0.0103(10) -0.0075(10) C11 0.0346(13) 0.0456(15) 0.0334(13) -0.0063(12) -0.0112(10) 0.0018(11) C12 0.0298(11) 0.0199(10) 0.0282(11) -0.0013(9) 0.0026(9) 0.0060(8) C13 0.0111(7) 0.0192(9) 0.0176(8) -0.0017(7) 0.0021(6) 0.0009(7) C14 0.0118(8) 0.0202(9) 0.0222(9) -0.0019(8) 0.0049(7) 0.0006(7) C15 0.0158(8) 0.0232(10) 0.0274(10) -0.0074(8) 0.0016(8) -0.0005(7) C16 0.0167(9) 0.0356(12) 0.0192(9) -0.0041(9) -0.0010(7) 0.0068(8) C17 0.0187(9) 0.0329(11) 0.0216(10) 0.0062(9) 0.0026(8) 0.0056(8) C18 0.0135(8) 0.0213(10) 0.0235(10) 0.0019(8) 0.0021(7) 0.0034(7) C19 0.0224(9) 0.0229(10) 0.0268(11) 0.0029(8) 0.0083(8) -0.0020(8) C20 0.0314(12) 0.0533(16) 0.0246(11) -0.0096(11) -0.0048(9) 0.0080(11) C21 0.0231(10) 0.0210(10) 0.0416(13) 0.0069(9) 0.0058(9) 0.0018(8) C22 0.0192(9) 0.0166(9) 0.0158(8) 0.0022(7) 0.0078(7) 0.0006(7) C23 0.0128(7) 0.0141(8) 0.0133(8) -0.0006(7) 0.0018(6) -0.0028(6) C24 0.0140(8) 0.0133(8) 0.0140(8) -0.0011(7) 0.0045(6) -0.0016(6) C25 0.0237(9) 0.0201(10) 0.0186(9) 0.0004(7) 0.0104(8) 0.0029(7) C26 0.0149(8) 0.0141(8) 0.0174(9) -0.0009(7) 0.0014(7) 0.0031(6) C27 0.0193(9) 0.0131(9) 0.0218(9) -0.0012(7) 0.0004(7) 0.0015(7) C28 0.0212(9) 0.0109(8) 0.0215(9) -0.0013(7) 0.0002(7) -0.0007(7) C29 0.0339(11) 0.0190(10) 0.0226(10) 0.0001(8) 0.0064(9) 0.0006(8) C30 0.0425(13) 0.0228(11) 0.0340(13) 0.0115(10) 0.0022(10) 0.0010(10) C31 0.0300(12) 0.0195(10) 0.0521(15) 0.0103(10) 0.0008(11) 0.0053(9) C32 0.0239(10) 0.0246(11) 0.0424(13) -0.0018(10) 0.0086(9) 0.0046(8) C33 0.0243(10) 0.0199(10) 0.0251(10) 0.0018(8) 0.0046(8) 0.0011(8) C34 0.0153(8) 0.0154(9) 0.0180(9) 0.0013(7) -0.0011(7) -0.0020(6) C35 0.0167(8) 0.0168(9) 0.0188(9) -0.0003(7) -0.0007(7) -0.0016(7) C36 0.0160(8) 0.0212(9) 0.0178(9) 0.0047(7) 0.0014(7) -0.0031(7) C37 0.0231(10) 0.0366(13) 0.0189(10) -0.0014(9) -0.0008(8) -0.0067(9) C38 0.0229(11) 0.0691(18) 0.0202(10) 0.0030(11) -0.0031(9) -0.0143(11) C39 0.0153(10) 0.076(2) 0.0312(12) 0.0243(13) 0.0007(9) -0.0015(11) C40 0.0205(10) 0.0402(14) 0.0606(17) 0.0175(13) 0.0155(11) 0.0065(10) C41 0.0224(10) 0.0260(11) 0.0440(14) -0.0018(10) 0.0088(10) -0.0022(8) Ir1 0.01052(3) 0.01154(3) 0.00929(3) 0.00045(2) 0.00260(2) 0.00029(2) N1 0.0155(7) 0.0211(8) 0.0145(7) -0.0034(6) 0.0049(6) 0.0013(6) N2 0.0149(7) 0.0196(8) 0.0159(7) -0.0041(6) 0.0044(6) 0.0014(6) N3 0.0111(6) 0.0115(7) 0.0142(7) -0.0003(6) 0.0033(5) -0.0008(5) N4 0.0142(7) 0.0136(7) 0.0125(7) -0.0007(6) 0.0030(6) 0.0002(6) O1 0.0132(6) 0.0157(6) 0.0119(6) 0.0022(5) 0.0035(5) 0.0018(5) O2 0.0184(6) 0.0214(7) 0.0129(6) 0.0035(5) 0.0034(5) 0.0003(5) O3 0.0192(6) 0.0171(6) 0.0118(6) 0.0035(5) 0.0015(5) 0.0004(5) O4 0.0156(6) 0.0143(6) 0.0143(6) 0.0015(5) 0.0027(5) -0.0021(5) O5 0.0359(8) 0.0201(7) 0.0216(7) 0.0077(6) 0.0058(6) -0.0049(6) C42 0.0262(11) 0.0231(11) 0.0376(13) -0.0053(9) 0.0020(9) 0.0007(8) Cl1 0.0425(3) 0.0262(3) 0.0447(3) -0.0015(2) 0.0107(3) 0.0098(2) Cl2 0.0508(4) 0.0429(4) 0.1033(7) -0.0197(4) -0.0359(5) -0.0022(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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 0 5 0.0574 0 5 -1 0.0674 -3 0 -5 0.0437 -5 0 -4 0.0449 5 0 4 0.0449 -5 -1 4 0.0600 5 1 -4 0.0600 0 -1 5 0.0532 2 1 -5 0.0778 -5 -2 -5 0.0467 -1 0 -5 0.0662 4 1 5 0.0451 -4 -5 -3 0.0482 -1 -2 -5 0.0604 1 0 -5 0.0781 1 2 5 0.0619 -1 -5 -2 0.0646 1 -2 -5 0.0758 3 -5 5 0.0750 5 -4 -1 0.0761 -4 1 -5 0.0532 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 Ir1 130.86(13) N2 C1 Ir1 125.30(13) N2 C1 N1 103.81(14) C3 C2 H2 126.7 C3 C2 N1 106.54(17) N1 C2 H2 126.7 C2 C3 H3 126.3 C2 C3 N2 107.37(17) N2 C3 H3 126.3 C5 C4 C9 121.86(18) C5 C4 N1 120.30(18) C9 C4 N1 117.67(17) C4 C5 C10 122.31(19) C6 C5 C4 117.54(19) C6 C5 C10 120.11(19) C5 C6 H6 118.8 C7 C6 C5 122.4(2) C7 C6 H6 118.8 C6 C7 C11 121.3(2) C8 C7 C6 117.93(19) C8 C7 C11 120.8(2) C7 C8 H8 118.9 C7 C8 C9 122.3(2) C9 C8 H8 118.9 C4 C9 C12 122.53(18) C8 C9 C4 117.83(18) C8 C9 C12 119.60(19) C5 C10 H10A 109.5 C5 C10 H10B 109.5 C5 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C7 C11 H11A 109.5 C7 C11 H11B 109.5 C7 C11 H11C 109.5 H11A C11 H11B 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C9 C12 H12A 109.5 C9 C12 H12B 109.5 C9 C12 H12C 109.5 H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C14 C13 C18 122.25(18) C14 C13 N2 118.39(17) C18 C13 N2 119.23(17) C13 C14 C19 121.67(18) C15 C14 C13 117.58(18) C15 C14 C19 120.72(18) C14 C15 H15 119.1 C14 C15 C16 121.70(19) C16 C15 H15 119.1 C15 C16 C20 120.7(2) C17 C16 C15 118.65(19) C17 C16 C20 120.7(2) C16 C17 H17 119.0 C16 C17 C18 122.01(19) C18 C17 H17 119.0 C13 C18 C17 117.48(19) C13 C18 C21 123.24(19) C17 C18 C21 119.27(19) C14 C19 H19A 109.5 C14 C19 H19B 109.5 C14 C19 H19C 109.5 H19A C19 H19B 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C16 C20 H20A 109.5 C16 C20 H20B 109.5 C16 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C18 C21 H21A 109.5 C18 C21 H21B 109.5 C18 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 O3 C22 Ir1 54.65(8) O4 C22 Ir1 55.79(9) O4 C22 O3 110.42(15) O5 C22 Ir1 178.38(15) O5 C22 O3 124.52(18) O5 C22 O4 125.07(18) O1 C23 C24 116.15(15) O2 C23 C24 119.79(15) O2 C23 O1 124.04(17) C25 C24 C23 117.41(15) N3 C24 C23 115.14(15) N3 C24 C25 127.43(17) C24 C25 H25A 109.5 C24 C25 H25B 109.5 C24 C25 H25C 109.5 H25A C25 H25B 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 H26A C26 H26B 108.0 C27 C26 H26A 109.4 C27 C26 H26B 109.4 N3 C26 H26A 109.4 N3 C26 H26B 109.4 N3 C26 C27 111.04(14) C26 C27 H27A 109.4 C26 C27 H27B 109.4 H27A C27 H27B 108.0 C28 C27 C26 111.28(15) C28 C27 H27A 109.4 C28 C27 H27B 109.4 C29 C28 C27 119.83(18) C33 C28 C27 121.38(18) C33 C28 C29 118.78(18) C28 C29 H29 119.7 C30 C29 C28 120.6(2) C30 C29 H29 119.7 C29 C30 H30 119.9 C31 C30 C29 120.2(2) C31 C30 H30 119.9 C30 C31 H31 120.1 C30 C31 C32 119.8(2) C32 C31 H31 120.1 C31 C32 H32 120.0 C31 C32 C33 120.0(2) C33 C32 H32 120.0 C28 C33 H33 119.7 C32 C33 C28 120.6(2) C32 C33 H33 119.7 H34A C34 H34B 108.3 C35 C34 H34A 109.9 C35 C34 H34B 109.9 N4 C34 H34A 109.9 N4 C34 H34B 109.9 N4 C34 C35 109.05(15) C34 C35 H35A 108.3 C34 C35 H35B 108.3 H35A C35 H35B 107.4 C36 C35 C34 116.09(16) C36 C35 H35A 108.3 C36 C35 H35B 108.3 C37 C36 C35 119.76(18) C41 C36 C35 121.97(19) C41 C36 C37 118.09(19) C36 C37 H37 119.4 C38 C37 C36 121.2(2) C38 C37 H37 119.4 C37 C38 H38 120.1 C39 C38 C37 119.8(2) C39 C38 H38 120.1 C38 C39 H39 120.2 C40 C39 C38 119.6(2) C40 C39 H39 120.2 C39 C40 H40 119.7 C39 C40 C41 120.6(2) C41 C40 H40 119.7 C36 C41 C40 120.7(2) C36 C41 H41 119.7 C40 C41 H41 119.7 C1 Ir1 C22 90.17(6) C1 Ir1 N3 172.39(7) C1 Ir1 N4 94.61(7) C1 Ir1 O1 94.77(6) C1 Ir1 O3 91.08(6) C1 Ir1 O4 90.21(6) N3 Ir1 C22 92.23(6) N4 Ir1 C22 137.33(6) N4 Ir1 N3 88.51(6) O1 Ir1 C22 139.34(6) O1 Ir1 N3 78.74(5) O1 Ir1 N4 82.51(6) O1 Ir1 O4 107.39(5) O3 Ir1 C22 32.25(6) O3 Ir1 N3 94.81(5) O3 Ir1 N4 105.18(6) O3 Ir1 O1 169.97(5) O3 Ir1 O4 64.37(5) O4 Ir1 C22 32.13(6) O4 Ir1 N3 88.00(5) O4 Ir1 N4 168.63(6) C1 N1 C2 111.22(16) C1 N1 C4 126.74(15) C2 N1 C4 121.40(16) C1 N2 C3 111.06(16) C1 N2 C13 127.08(15) C3 N2 C13 121.86(16) C24 N3 C26 120.87(15) C24 N3 Ir1 114.44(12) C26 N3 Ir1 124.62(11) C34 N4 Ir1 116.94(11) C34 N4 H4A 105.0(16) C34 N4 H4B 107.3(16) Ir1 N4 H4A 107.7(16) Ir1 N4 H4B 109.0(16) H4A N4 H4B 111(2) C23 O1 Ir1 115.42(11) C22 O3 Ir1 93.10(11) C22 O4 Ir1 92.08(11) H42A C42 H42B 108.0 Cl1 C42 H42A 109.4 Cl1 C42 H42B 109.4 Cl2 C42 H42A 109.4 Cl2 C42 H42B 109.4 Cl2 C42 Cl1 111.21(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 Ir1 2.0101(17) C1 N1 1.367(2) C1 N2 1.365(2) C2 H2 0.9300 C2 C3 1.338(3) C2 N1 1.394(2) C3 H3 0.9300 C3 N2 1.388(2) C4 C5 1.393(3) C4 C9 1.398(3) C4 N1 1.443(2) C5 C6 1.392(3) C5 C10 1.506(3) C6 H6 0.9300 C6 C7 1.389(3) C7 C8 1.384(3) C7 C11 1.504(3) C8 H8 0.9300 C8 C9 1.389(3) C9 C12 1.514(3) C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C13 C14 1.395(3) C13 C18 1.395(3) C13 N2 1.445(2) C14 C15 1.391(3) C14 C19 1.503(3) C15 H15 0.9300 C15 C16 1.395(3) C16 C17 1.377(3) C16 C20 1.509(3) C17 H17 0.9300 C17 C18 1.396(3) C18 C21 1.503(3) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C22 Ir1 2.4904(19) C22 O3 1.331(2) C22 O4 1.325(2) C22 O5 1.226(2) C23 C24 1.519(3) C23 O1 1.281(2) C23 O2 1.234(2) C24 C25 1.491(2) C24 N3 1.287(2) C25 H25A 0.9600 C25 H25B 0.9600 C25 H25C 0.9600 C26 H26A 0.9700 C26 H26B 0.9700 C26 C27 1.531(3) C26 N3 1.474(2) C27 H27A 0.9700 C27 H27B 0.9700 C27 C28 1.508(3) C28 C29 1.389(3) C28 C33 1.388(3) C29 H29 0.9300 C29 C30 1.386(3) C30 H30 0.9300 C30 C31 1.378(3) C31 H31 0.9300 C31 C32 1.384(3) C32 H32 0.9300 C32 C33 1.388(3) C33 H33 0.9300 C34 H34A 0.9700 C34 H34B 0.9700 C34 C35 1.528(3) C34 N4 1.484(2) C35 H35A 0.9700 C35 H35B 0.9700 C35 C36 1.504(3) C36 C37 1.390(3) C36 C41 1.386(3) C37 H37 0.9300 C37 C38 1.388(3) C38 H38 0.9300 C38 C39 1.378(4) C39 H39 0.9300 C39 C40 1.376(4) C40 H40 0.9300 C40 C41 1.387(3) C41 H41 0.9300 Ir1 N3 2.0925(14) Ir1 N4 2.0780(15) Ir1 O1 2.0539(12) Ir1 O3 2.0343(12) Ir1 O4 2.0609(12) N4 H4A 0.87(2) N4 H4B 0.87(2) C42 H42A 0.9700 C42 H42B 0.9700 C42 Cl1 1.765(2) C42 Cl2 1.753(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O2 0.87(2) 2.02(2) 2.851(2) 159(2) 3_666 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 C2 C3 N2 C1 0.0(2) C2 C3 N2 C13 -179.09(18) C3 C2 N1 C1 -0.4(2) C3 C2 N1 C4 171.12(18) C4 C5 C6 C7 1.0(3) C5 C4 C9 C8 4.3(3) C5 C4 C9 C12 -173.32(18) C5 C4 N1 C1 -95.4(2) C5 C4 N1 C2 94.6(2) C5 C6 C7 C8 1.4(3) C5 C6 C7 C11 179.7(2) C6 C7 C8 C9 -1.1(3) C7 C8 C9 C4 -1.7(3) C7 C8 C9 C12 175.99(18) C9 C4 C5 C6 -4.0(3) C9 C4 C5 C10 173.59(18) C9 C4 N1 C1 89.3(2) C9 C4 N1 C2 -80.8(2) C10 C5 C6 C7 -176.6(2) C11 C7 C8 C9 -179.4(2) C13 C14 C15 C16 -1.0(3) C14 C13 C18 C17 -6.2(3) C14 C13 C18 C21 172.82(17) C14 C13 N2 C1 97.1(2) C14 C13 N2 C3 -84.0(2) C14 C15 C16 C17 -3.1(3) C14 C15 C16 C20 178.09(19) C15 C16 C17 C18 2.6(3) C16 C17 C18 C13 1.9(3) C16 C17 C18 C21 -177.17(18) C18 C13 C14 C15 5.8(3) C18 C13 C14 C19 -172.33(17) C18 C13 N2 C1 -86.9(2) C18 C13 N2 C3 92.0(2) C19 C14 C15 C16 177.12(18) C20 C16 C17 C18 -178.57(19) C23 C24 N3 C26 -179.44(15) C23 C24 N3 Ir1 3.58(19) C24 C23 O1 Ir1 -0.35(19) C25 C24 N3 C26 -1.1(3) C25 C24 N3 Ir1 -178.06(15) C26 C27 C28 C29 87.1(2) C26 C27 C28 C33 -91.8(2) C27 C26 N3 C24 -77.5(2) C27 C26 N3 Ir1 99.18(16) C27 C28 C29 C30 -177.9(2) C27 C28 C33 C32 179.81(19) C28 C29 C30 C31 -2.0(4) C29 C28 C33 C32 0.9(3) C29 C30 C31 C32 1.1(4) C30 C31 C32 C33 0.8(4) C31 C32 C33 C28 -1.8(3) C33 C28 C29 C30 1.0(3) C34 C35 C36 C37 -136.18(19) C34 C35 C36 C41 48.9(3) C35 C34 N4 Ir1 175.18(12) C35 C36 C37 C38 -174.7(2) C35 C36 C41 C40 175.5(2) C36 C37 C38 C39 -1.2(3) C37 C36 C41 C40 0.5(3) C37 C38 C39 C40 0.9(4) C38 C39 C40 C41 0.1(4) C39 C40 C41 C36 -0.8(4) C41 C36 C37 C38 0.5(3) Ir1 C1 N1 C2 -177.83(14) Ir1 C1 N1 C4 11.3(3) Ir1 C1 N2 C3 178.10(14) Ir1 C1 N2 C13 -2.9(3) N1 C1 N2 C3 -0.2(2) N1 C1 N2 C13 178.82(17) N1 C2 C3 N2 0.2(2) N1 C4 C5 C6 -179.14(17) N1 C4 C5 C10 -1.6(3) N1 C4 C9 C8 179.61(16) N1 C4 C9 C12 2.0(3) N2 C1 N1 C2 0.3(2) N2 C1 N1 C4 -170.58(17) N2 C13 C14 C15 -178.45(16) N2 C13 C14 C19 3.5(3) N2 C13 C18 C17 178.03(16) N2 C13 C18 C21 -2.9(3) N3 C26 C27 C28 178.51(15) N4 C34 C35 C36 -171.42(16) O1 C23 C24 C25 179.23(16) O1 C23 C24 N3 -2.2(2) O2 C23 C24 C25 -2.5(3) O2 C23 C24 N3 176.01(16) O2 C23 O1 Ir1 -178.51(14) O3 C22 O4 Ir1 -1.61(14) O4 C22 O3 Ir1 1.64(14) O5 C22 O3 Ir1 -178.31(17) O5 C22 O4 Ir1 178.33(18) 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 -2.0000 0.0000 5.0001 0.0551 0.0244 0.1528 -0.0000 5.0000 -1.0003 0.2693 0.0161 -0.1240 -3.0000 -0.0000 -4.9998 -0.0249 0.2119 -0.0642 -5.0000 -0.0000 -3.9997 -0.0043 0.2924 -0.0053 5.0000 0.0000 3.9997 0.0043 -0.2924 0.0053 -4.9999 -1.0000 4.0003 0.0090 0.1798 0.2026 4.9999 1.0000 -4.0003 -0.0090 -0.1798 -0.2026 0.0000 -1.0000 5.0001 -0.0126 -0.0705 0.1375 1.9999 1.0000 -5.0002 0.0005 -0.0240 -0.1729 -5.0000 -2.0000 -4.9996 -0.1241 0.3055 0.0115 -1.0000 -0.0000 -5.0000 -0.0370 0.1174 -0.0997 4.0000 1.0000 4.9997 0.0745 -0.2587 0.0264 -3.9999 -5.0000 -2.9995 -0.2796 0.2290 0.1010 -1.0000 -2.0000 -4.9998 -0.1482 0.1165 -0.0594 1.0000 -0.0000 -5.0001 -0.0491 0.0229 -0.1351 1.0000 2.0000 4.9998 0.1482 -0.1165 0.0594 -1.0000 -5.0000 -1.9996 -0.2891 0.0732 0.0713 1.0000 -2.0000 -4.9999 -0.1602 0.0220 -0.0949 3.0000 -5.0000 5.0002 -0.2530 -0.2140 0.1648 5.0000 -4.0000 -1.0000 -0.2611 -0.2239 -0.0316 -4.0000 1.0000 -4.9999 0.0367 0.2596 -0.0666