# Electronic Supplementary Material (ESI) for ChemComm. # This journal is © The Royal Society of Chemistry 2015 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_l0473a _database_code_depnum_ccdc_archive 'CCDC 1410768' _audit_update_record ; 2015-07-06 deposited with the CCDC. 2015-08-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H39 Cl2 Ir N O2 P S' _chemical_formula_sum 'C32 H39 Cl2 Ir N O2 P S' _chemical_formula_weight 795.77 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.16597(16) _cell_length_b 10.5116(3) _cell_length_c 15.5310(3) _cell_angle_alpha 76.518(1) _cell_angle_beta 78.361(1) _cell_angle_gamma 80.796(1) _cell_volume 1569.58(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 21217 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 4.571 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.1472 _exptl_absorpt_correction_T_max 0.6906 _exptl_absorpt_process_details SADABS-2012/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22217 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7214 _reflns_number_gt 7109 _reflns_threshold_expression I>2\s(I) _computing_data_collection Apex2 _computing_cell_refinement Eval15 _computing_data_reduction 'Eval15, SADABS-2012/1' _computing_structure_solution 'SHELXT (Sheldrick, 2012)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0135P)^2^+0.9434P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7214 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0120 _refine_ls_R_factor_gt 0.0117 _refine_ls_wR_factor_ref 0.0298 _refine_ls_wR_factor_gt 0.0297 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.697964(5) 0.321929(5) 0.268537(3) 0.01074(2) Uani 1 1 d . . . Cl1 Cl 0.89913(4) 0.17774(4) 0.29720(3) 0.02174(8) Uani 1 1 d . . . Cl2 Cl 0.57973(4) 0.18597(4) 0.39856(2) 0.02032(7) Uani 1 1 d . . . S1 S 0.66795(4) -0.11112(4) 0.22070(3) 0.01702(7) Uani 1 1 d . . . P1 P 0.66179(4) 0.18526(4) 0.18308(2) 0.01170(7) Uani 1 1 d . . . O1 O 0.68460(12) -0.10014(13) 0.12538(8) 0.0257(3) Uani 1 1 d . . . O2 O 0.74977(12) -0.21214(12) 0.27277(9) 0.0261(3) Uani 1 1 d . . . N1 N 0.70042(13) 0.02738(13) 0.23763(9) 0.0148(2) Uani 1 1 d . . . H1N H 0.726(2) 0.020(2) 0.2845(16) 0.031(6) Uiso 1 1 d . . . C1 C 0.49603(16) -0.12513(15) 0.26606(11) 0.0174(3) Uani 1 1 d . . . C2 C 0.40743(17) -0.12821(16) 0.20951(11) 0.0212(3) Uani 1 1 d . . . H2 H 0.4393 -0.1252 0.1473 0.025 Uiso 1 1 calc R . . C3 C 0.27152(17) -0.13576(17) 0.24523(11) 0.0227(3) Uani 1 1 d . . . H3 H 0.2104 -0.1376 0.2067 0.027 Uiso 1 1 calc R . . C4 C 0.22296(16) -0.14072(16) 0.33626(11) 0.0205(3) Uani 1 1 d . . . C5 C 0.31463(17) -0.13843(17) 0.39178(11) 0.0216(3) Uani 1 1 d . . . H5 H 0.2831 -0.1423 0.4541 0.026 Uiso 1 1 calc R . . C6 C 0.45082(16) -0.13059(17) 0.35751(11) 0.0202(3) Uani 1 1 d . . . H6 H 0.5122 -0.1290 0.3958 0.024 Uiso 1 1 calc R . . C7 C 0.07444(17) -0.14671(18) 0.37372(13) 0.0264(4) Uani 1 1 d . . . H7A H 0.0271 -0.1500 0.3246 0.032 Uiso 1 1 calc R . . H7B H 0.0368 -0.0648 0.3955 0.032 Uiso 1 1 calc R . . C8 C 0.04529(19) -0.2642(2) 0.45029(14) 0.0318(4) Uani 1 1 d . . . H8A H 0.0863 -0.2574 0.5014 0.038 Uiso 1 1 calc R . . H8B H 0.0886 -0.3461 0.4302 0.038 Uiso 1 1 calc R . . C9 C -0.1058(2) -0.2738(2) 0.48234(15) 0.0374(5) Uani 1 1 d . . . H9A H -0.1464 -0.2821 0.4314 0.045 Uiso 1 1 calc R . . H9B H -0.1175 -0.3547 0.5295 0.045 Uiso 1 1 calc R . . C10 C -0.1811(2) -0.1568(3) 0.51945(18) 0.0531(6) Uani 1 1 d . . . H10A H -0.1371 -0.1434 0.5667 0.080 Uiso 1 1 calc R . . H10B H -0.2748 -0.1732 0.5446 0.080 Uiso 1 1 calc R . . H10C H -0.1803 -0.0779 0.4711 0.080 Uiso 1 1 calc R . . C11 C 0.49158(15) 0.19570(15) 0.16096(10) 0.0149(3) Uani 1 1 d . . . C12 C 0.46236(16) 0.16725(17) 0.08380(11) 0.0201(3) Uani 1 1 d . . . H12 H 0.5338 0.1401 0.0397 0.024 Uiso 1 1 calc R . . C13 C 0.32879(18) 0.17855(19) 0.07139(12) 0.0257(4) Uani 1 1 d . . . H13 H 0.3095 0.1618 0.0180 0.031 Uiso 1 1 calc R . . C14 C 0.22407(17) 0.21412(19) 0.13680(12) 0.0272(4) Uani 1 1 d . . . H14 H 0.1330 0.2226 0.1279 0.033 Uiso 1 1 calc R . . C15 C 0.25184(16) 0.23737(19) 0.21511(12) 0.0253(4) Uani 1 1 d . . . H15 H 0.1797 0.2584 0.2609 0.030 Uiso 1 1 calc R . . C16 C 0.38482(16) 0.22996(17) 0.22692(11) 0.0193(3) Uani 1 1 d . . . H16 H 0.4034 0.2483 0.2801 0.023 Uiso 1 1 calc R . . C17 C 0.77290(15) 0.19981(15) 0.07490(10) 0.0149(3) Uani 1 1 d . . . C18 C 0.73516(16) 0.28276(17) -0.00274(11) 0.0197(3) Uani 1 1 d . . . H18 H 0.6464 0.3285 -0.0006 0.024 Uiso 1 1 calc R . . C19 C 0.82643(18) 0.29898(18) -0.08324(11) 0.0244(3) Uani 1 1 d . . . H19 H 0.7995 0.3546 -0.1359 0.029 Uiso 1 1 calc R . . C20 C 0.95677(18) 0.23394(18) -0.08658(11) 0.0247(4) Uani 1 1 d . . . H20 H 1.0186 0.2435 -0.1418 0.030 Uiso 1 1 calc R . . C21 C 0.99632(16) 0.15518(17) -0.00932(12) 0.0227(3) Uani 1 1 d . . . H21 H 1.0864 0.1128 -0.0113 0.027 Uiso 1 1 calc R . . C22 C 0.90531(15) 0.13742(16) 0.07119(11) 0.0182(3) Uani 1 1 d . . . H22 H 0.9333 0.0827 0.1238 0.022 Uiso 1 1 calc R . . C23 C 0.76526(16) 0.49941(15) 0.17941(10) 0.0174(3) Uani 1 1 d . . . C24 C 0.61935(16) 0.50888(15) 0.19135(11) 0.0177(3) Uani 1 1 d . . . C25 C 0.56611(16) 0.50156(15) 0.28483(11) 0.0168(3) Uani 1 1 d . . . C26 C 0.67899(15) 0.49518(15) 0.33074(10) 0.0161(3) Uani 1 1 d . . . C27 C 0.79934(16) 0.49600(14) 0.26611(10) 0.0162(3) Uani 1 1 d . . . C28 C 0.86094(19) 0.51192(18) 0.09139(11) 0.0260(4) Uani 1 1 d . . . H28A H 0.8283 0.4697 0.0511 0.039 Uiso 1 1 calc R . . H28B H 0.9510 0.4689 0.1016 0.039 Uiso 1 1 calc R . . H28C H 0.8660 0.6053 0.0640 0.039 Uiso 1 1 calc R . . C29 C 0.53708(19) 0.53739(17) 0.11799(12) 0.0251(4) Uani 1 1 d . . . H29A H 0.4608 0.4850 0.1366 0.038 Uiso 1 1 calc R . . H29B H 0.5936 0.5145 0.0634 0.038 Uiso 1 1 calc R . . H29C H 0.5029 0.6313 0.1059 0.038 Uiso 1 1 calc R . . C30 C 0.42002(16) 0.51238(18) 0.32775(12) 0.0240(3) Uani 1 1 d . . . H30A H 0.3925 0.5998 0.3420 0.036 Uiso 1 1 calc R . . H30B H 0.4072 0.4448 0.3831 0.036 Uiso 1 1 calc R . . H30C H 0.3648 0.4996 0.2862 0.036 Uiso 1 1 calc R . . C31 C 0.66696(17) 0.49448(17) 0.42813(11) 0.0219(3) Uani 1 1 d . . . H31A H 0.7569 0.4739 0.4451 0.033 Uiso 1 1 calc R . . H31B H 0.6094 0.4277 0.4637 0.033 Uiso 1 1 calc R . . H31C H 0.6266 0.5814 0.4396 0.033 Uiso 1 1 calc R . . C32 C 0.93797(16) 0.49284(17) 0.28505(12) 0.0218(3) Uani 1 1 d . . . H32A H 0.9504 0.5802 0.2922 0.033 Uiso 1 1 calc R . . H32B H 1.0051 0.4683 0.2350 0.033 Uiso 1 1 calc R . . H32C H 0.9496 0.4280 0.3404 0.033 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 0.01019(3) 0.01064(3) 0.01102(3) -0.00159(2) -0.00177(2) -0.00116(2) Cl1 0.01535(16) 0.01786(18) 0.0339(2) -0.00599(16) -0.01107(15) 0.00218(13) Cl2 0.02402(18) 0.02298(19) 0.01287(16) -0.00010(14) -0.00023(13) -0.00868(15) S1 0.01696(17) 0.01367(17) 0.02041(18) -0.00665(14) 0.00151(14) -0.00316(13) P1 0.01012(16) 0.01262(17) 0.01205(16) -0.00255(13) -0.00123(13) -0.00135(13) O1 0.0261(6) 0.0315(7) 0.0222(6) -0.0146(5) 0.0055(5) -0.0097(5) O2 0.0231(6) 0.0131(6) 0.0387(7) -0.0031(5) -0.0028(5) 0.0008(5) N1 0.0170(6) 0.0120(6) 0.0157(6) -0.0019(5) -0.0043(5) -0.0023(5) C1 0.0177(7) 0.0139(7) 0.0204(7) -0.0044(6) 0.0003(6) -0.0048(6) C2 0.0257(8) 0.0208(8) 0.0180(7) -0.0047(6) -0.0013(6) -0.0081(6) C3 0.0233(8) 0.0228(8) 0.0234(8) -0.0015(7) -0.0077(6) -0.0073(6) C4 0.0182(7) 0.0167(8) 0.0244(8) -0.0002(6) -0.0031(6) -0.0024(6) C5 0.0210(8) 0.0247(8) 0.0174(7) -0.0036(6) -0.0001(6) -0.0026(6) C6 0.0199(8) 0.0223(8) 0.0192(8) -0.0052(6) -0.0035(6) -0.0039(6) C7 0.0181(8) 0.0269(9) 0.0298(9) 0.0013(7) -0.0032(7) -0.0015(7) C8 0.0230(9) 0.0274(10) 0.0393(11) 0.0044(8) -0.0039(8) -0.0052(7) C9 0.0271(10) 0.0423(12) 0.0400(11) 0.0030(9) -0.0035(8) -0.0155(9) C10 0.0336(12) 0.0708(18) 0.0465(14) -0.0102(13) 0.0119(10) -0.0078(11) C11 0.0121(6) 0.0161(7) 0.0165(7) -0.0015(6) -0.0034(5) -0.0030(5) C12 0.0184(7) 0.0253(8) 0.0177(7) -0.0048(6) -0.0025(6) -0.0060(6) C13 0.0246(8) 0.0351(10) 0.0213(8) -0.0044(7) -0.0098(7) -0.0096(7) C14 0.0159(8) 0.0359(10) 0.0309(9) -0.0032(8) -0.0092(7) -0.0053(7) C15 0.0130(7) 0.0349(10) 0.0276(9) -0.0084(7) -0.0015(6) -0.0015(7) C16 0.0151(7) 0.0244(8) 0.0195(7) -0.0066(6) -0.0023(6) -0.0030(6) C17 0.0151(7) 0.0165(7) 0.0143(7) -0.0058(6) 0.0006(5) -0.0053(6) C18 0.0189(7) 0.0233(8) 0.0170(7) -0.0036(6) -0.0022(6) -0.0045(6) C19 0.0297(9) 0.0286(9) 0.0149(7) -0.0028(7) -0.0006(6) -0.0098(7) C20 0.0255(8) 0.0294(9) 0.0196(8) -0.0099(7) 0.0083(6) -0.0129(7) C21 0.0165(7) 0.0232(8) 0.0292(9) -0.0117(7) 0.0044(6) -0.0060(6) C22 0.0157(7) 0.0179(8) 0.0216(8) -0.0059(6) -0.0013(6) -0.0035(6) C23 0.0223(8) 0.0116(7) 0.0178(7) -0.0010(6) -0.0028(6) -0.0040(6) C24 0.0229(8) 0.0111(7) 0.0183(7) -0.0001(6) -0.0062(6) -0.0010(6) C25 0.0187(7) 0.0112(7) 0.0202(7) -0.0030(6) -0.0050(6) 0.0007(5) C26 0.0185(7) 0.0118(7) 0.0186(7) -0.0045(6) -0.0039(6) -0.0009(5) C27 0.0202(7) 0.0090(7) 0.0195(7) -0.0022(6) -0.0031(6) -0.0038(5) C28 0.0317(9) 0.0267(9) 0.0193(8) -0.0027(7) 0.0023(7) -0.0142(7) C29 0.0329(9) 0.0190(8) 0.0242(8) -0.0011(7) -0.0138(7) 0.0012(7) C30 0.0169(7) 0.0244(9) 0.0308(9) -0.0109(7) -0.0032(6) 0.0036(6) C31 0.0248(8) 0.0236(8) 0.0189(8) -0.0088(6) -0.0033(6) -0.0020(6) C32 0.0186(8) 0.0209(8) 0.0268(8) -0.0050(7) -0.0036(6) -0.0057(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C23 2.1649(15) . ? Ir1 C25 2.1685(15) . ? Ir1 C24 2.1734(15) . ? Ir1 C26 2.2181(15) . ? Ir1 C27 2.2287(15) . ? Ir1 P1 2.2838(4) . ? Ir1 Cl1 2.3956(4) . ? Ir1 Cl2 2.4061(4) . ? S1 O1 1.4351(12) . ? S1 O2 1.4358(13) . ? S1 N1 1.6325(13) . ? S1 C1 1.7635(16) . ? P1 N1 1.7019(13) . ? P1 C11 1.8127(15) . ? P1 C17 1.8143(15) . ? N1 H1N 0.81(2) . ? C1 C2 1.388(2) . ? C1 C6 1.392(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 C5 1.398(2) . ? C4 C7 1.510(2) . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.522(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.528(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.511(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.397(2) . ? C11 C16 1.398(2) . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.396(2) . ? C17 C18 1.397(2) . ? C18 C19 1.391(2) . ? C18 H18 0.9500 . ? C19 C20 1.387(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.391(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.447(2) . ? C23 C27 1.448(2) . ? C23 C28 1.501(2) . ? C24 C25 1.432(2) . ? C24 C29 1.494(2) . ? C25 C26 1.454(2) . ? C25 C30 1.498(2) . ? C26 C27 1.417(2) . ? C26 C31 1.491(2) . ? C27 C32 1.490(2) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 C23 Ir1 C25 65.16(6) . . ? C23 Ir1 C24 38.98(6) . . ? C25 Ir1 C24 38.52(6) . . ? C23 Ir1 C26 64.20(6) . . ? C25 Ir1 C26 38.68(5) . . ? C24 Ir1 C26 64.10(6) . . ? C23 Ir1 C27 38.45(6) . . ? C25 Ir1 C27 63.76(6) . . ? C24 Ir1 C27 63.84(6) . . ? C26 Ir1 C27 37.17(6) . . ? C23 Ir1 P1 108.34(4) . . ? C25 Ir1 P1 122.87(4) . . ? C24 Ir1 P1 98.97(4) . . ? C26 Ir1 P1 161.27(4) . . ? C27 Ir1 P1 144.21(4) . . ? C23 Ir1 Cl1 105.97(4) . . ? C25 Ir1 Cl1 149.09(4) . . ? C24 Ir1 Cl1 144.69(4) . . ? C26 Ir1 Cl1 110.41(4) . . ? C27 Ir1 Cl1 90.57(4) . . ? P1 Ir1 Cl1 87.981(13) . . ? C23 Ir1 Cl2 158.45(4) . . ? C25 Ir1 Cl2 94.79(4) . . ? C24 Ir1 Cl2 127.37(4) . . ? C26 Ir1 Cl2 95.41(4) . . ? C27 Ir1 Cl2 126.83(4) . . ? P1 Ir1 Cl2 88.821(13) . . ? Cl1 Ir1 Cl2 87.075(14) . . ? O1 S1 O2 119.83(8) . . ? O1 S1 N1 107.51(7) . . ? O2 S1 N1 105.18(7) . . ? O1 S1 C1 107.86(8) . . ? O2 S1 C1 108.88(7) . . ? N1 S1 C1 106.89(7) . . ? N1 P1 C11 106.09(7) . . ? N1 P1 C17 104.71(7) . . ? C11 P1 C17 106.43(7) . . ? N1 P1 Ir1 107.74(5) . . ? C11 P1 Ir1 117.26(5) . . ? C17 P1 Ir1 113.68(5) . . ? S1 N1 P1 130.29(9) . . ? S1 N1 H1N 113.5(16) . . ? P1 N1 H1N 115.1(16) . . ? C2 C1 C6 121.05(15) . . ? C2 C1 S1 119.29(12) . . ? C6 C1 S1 119.65(12) . . ? C1 C2 C3 119.01(15) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.36(15) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 118.41(15) . . ? C3 C4 C7 120.67(15) . . ? C5 C4 C7 120.92(15) . . ? C6 C5 C4 121.22(15) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 118.95(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C4 C7 C8 114.03(15) . . ? C4 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C4 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 113.03(16) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 113.55(18) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.06(14) . . ? C12 C11 P1 123.63(12) . . ? C16 C11 P1 117.28(11) . . ? C13 C12 C11 120.19(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.10(16) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.10(15) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.16(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.31(15) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 C17 C18 118.85(14) . . ? C22 C17 P1 118.71(12) . . ? C18 C17 P1 122.05(12) . . ? C19 C18 C17 120.56(15) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.01(16) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.77(15) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.55(16) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C17 120.20(15) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? C24 C23 C27 107.04(13) . . ? C24 C23 C28 126.08(15) . . ? C27 C23 C28 126.27(14) . . ? C24 C23 Ir1 70.83(9) . . ? C27 C23 Ir1 73.16(8) . . ? C28 C23 Ir1 128.22(11) . . ? C25 C24 C23 108.26(13) . . ? C25 C24 C29 125.38(15) . . ? C23 C24 C29 125.99(15) . . ? C25 C24 Ir1 70.56(9) . . ? C23 C24 Ir1 70.19(9) . . ? C29 C24 Ir1 130.34(11) . . ? C24 C25 C26 107.73(13) . . ? C24 C25 C30 126.95(14) . . ? C26 C25 C30 125.05(14) . . ? C24 C25 Ir1 70.93(9) . . ? C26 C25 Ir1 72.50(8) . . ? C30 C25 Ir1 126.78(11) . . ? C27 C26 C25 108.01(13) . . ? C27 C26 C31 126.83(14) . . ? C25 C26 C31 125.10(14) . . ? C27 C26 Ir1 71.82(9) . . ? C25 C26 Ir1 68.81(8) . . ? C31 C26 Ir1 127.08(11) . . ? C26 C27 C23 108.80(13) . . ? C26 C27 C32 125.28(14) . . ? C23 C27 C32 125.92(14) . . ? C26 C27 Ir1 71.01(8) . . ? C23 C27 Ir1 68.39(8) . . ? C32 C27 Ir1 126.25(11) . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C23 Ir1 P1 N1 147.21(7) . . . . ? C25 Ir1 P1 N1 -141.02(7) . . . . ? C24 Ir1 P1 N1 -173.76(6) . . . . ? C26 Ir1 P1 N1 -149.55(13) . . . . ? C27 Ir1 P1 N1 129.22(8) . . . . ? Cl1 Ir1 P1 N1 41.04(5) . . . . ? Cl2 Ir1 P1 N1 -46.07(5) . . . . ? C23 Ir1 P1 C11 -93.32(7) . . . . ? C25 Ir1 P1 C11 -21.54(8) . . . . ? C24 Ir1 P1 C11 -54.28(7) . . . . ? C26 Ir1 P1 C11 -30.08(14) . . . . ? C27 Ir1 P1 C11 -111.31(9) . . . . ? Cl1 Ir1 P1 C11 160.52(6) . . . . ? Cl2 Ir1 P1 C11 73.41(6) . . . . ? C23 Ir1 P1 C17 31.66(7) . . . . ? C25 Ir1 P1 C17 103.44(8) . . . . ? C24 Ir1 P1 C17 70.69(7) . . . . ? C26 Ir1 P1 C17 94.90(14) . . . . ? C27 Ir1 P1 C17 13.67(9) . . . . ? Cl1 Ir1 P1 C17 -74.51(6) . . . . ? Cl2 Ir1 P1 C17 -161.62(6) . . . . ? O1 S1 N1 P1 38.76(13) . . . . ? O2 S1 N1 P1 167.52(10) . . . . ? C1 S1 N1 P1 -76.83(12) . . . . ? C11 P1 N1 S1 40.31(12) . . . . ? C17 P1 N1 S1 -72.03(11) . . . . ? Ir1 P1 N1 S1 166.65(9) . . . . ? O1 S1 C1 C2 2.08(16) . . . . ? O2 S1 C1 C2 -129.41(14) . . . . ? N1 S1 C1 C2 117.44(13) . . . . ? O1 S1 C1 C6 -176.79(13) . . . . ? O2 S1 C1 C6 51.71(15) . . . . ? N1 S1 C1 C6 -61.44(15) . . . . ? C6 C1 C2 C3 0.5(2) . . . . ? S1 C1 C2 C3 -178.32(13) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C2 C3 C4 C7 179.01(16) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C7 C4 C5 C6 -178.85(16) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? S1 C1 C6 C5 178.47(13) . . . . ? C3 C4 C7 C8 123.85(19) . . . . ? C5 C4 C7 C8 -56.9(2) . . . . ? C4 C7 C8 C9 -175.71(17) . . . . ? C7 C8 C9 C10 -61.8(3) . . . . ? N1 P1 C11 C12 -88.55(15) . . . . ? C17 P1 C11 C12 22.58(16) . . . . ? Ir1 P1 C11 C12 151.10(12) . . . . ? N1 P1 C11 C16 89.22(13) . . . . ? C17 P1 C11 C16 -159.65(12) . . . . ? Ir1 P1 C11 C16 -31.13(14) . . . . ? C16 C11 C12 C13 2.7(2) . . . . ? P1 C11 C12 C13 -179.53(13) . . . . ? C11 C12 C13 C14 -2.0(3) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C13 C14 C15 C16 2.4(3) . . . . ? C14 C15 C16 C11 -1.7(3) . . . . ? C12 C11 C16 C15 -0.9(2) . . . . ? P1 C11 C16 C15 -178.80(13) . . . . ? N1 P1 C17 C22 -38.49(14) . . . . ? C11 P1 C17 C22 -150.59(12) . . . . ? Ir1 P1 C17 C22 78.83(13) . . . . ? N1 P1 C17 C18 148.69(13) . . . . ? C11 P1 C17 C18 36.60(15) . . . . ? Ir1 P1 C17 C18 -93.99(13) . . . . ? C22 C17 C18 C19 2.4(2) . . . . ? P1 C17 C18 C19 175.24(13) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C18 C19 C20 C21 -1.3(3) . . . . ? C19 C20 C21 C22 1.9(3) . . . . ? C20 C21 C22 C17 -0.4(2) . . . . ? C18 C17 C22 C21 -1.8(2) . . . . ? P1 C17 C22 C21 -174.84(12) . . . . ? C25 Ir1 C23 C24 -37.00(9) . . . . ? C26 Ir1 C23 C24 -79.98(9) . . . . ? C27 Ir1 C23 C24 -115.43(13) . . . . ? P1 Ir1 C23 C24 81.46(9) . . . . ? Cl1 Ir1 C23 C24 174.68(8) . . . . ? Cl2 Ir1 C23 C24 -59.84(16) . . . . ? C25 Ir1 C23 C27 78.42(9) . . . . ? C24 Ir1 C23 C27 115.43(13) . . . . ? C26 Ir1 C23 C27 35.45(9) . . . . ? P1 Ir1 C23 C27 -163.12(8) . . . . ? Cl1 Ir1 C23 C27 -69.89(9) . . . . ? Cl2 Ir1 C23 C27 55.59(16) . . . . ? C25 Ir1 C23 C28 -158.33(16) . . . . ? C24 Ir1 C23 C28 -121.32(18) . . . . ? C26 Ir1 C23 C28 158.70(16) . . . . ? C27 Ir1 C23 C28 123.25(18) . . . . ? P1 Ir1 C23 C28 -39.86(15) . . . . ? Cl1 Ir1 C23 C28 53.36(15) . . . . ? Cl2 Ir1 C23 C28 178.84(10) . . . . ? C27 C23 C24 C25 -4.13(17) . . . . ? C28 C23 C24 C25 -175.57(15) . . . . ? Ir1 C23 C24 C25 60.57(11) . . . . ? C27 C23 C24 C29 169.23(15) . . . . ? C28 C23 C24 C29 -2.2(3) . . . . ? Ir1 C23 C24 C29 -126.07(16) . . . . ? C27 C23 C24 Ir1 -64.70(10) . . . . ? C28 C23 C24 Ir1 123.86(16) . . . . ? C23 Ir1 C24 C25 -118.71(13) . . . . ? C26 Ir1 C24 C25 -38.43(9) . . . . ? C27 Ir1 C24 C25 -79.98(10) . . . . ? P1 Ir1 C24 C25 133.15(8) . . . . ? Cl1 Ir1 C24 C25 -127.58(8) . . . . ? Cl2 Ir1 C24 C25 37.74(10) . . . . ? C25 Ir1 C24 C23 118.71(13) . . . . ? C26 Ir1 C24 C23 80.28(9) . . . . ? C27 Ir1 C24 C23 38.73(9) . . . . ? P1 Ir1 C24 C23 -108.14(8) . . . . ? Cl1 Ir1 C24 C23 -8.87(13) . . . . ? Cl2 Ir1 C24 C23 156.45(7) . . . . ? C23 Ir1 C24 C29 120.90(19) . . . . ? C25 Ir1 C24 C29 -120.39(19) . . . . ? C26 Ir1 C24 C29 -158.82(17) . . . . ? C27 Ir1 C24 C29 159.64(17) . . . . ? P1 Ir1 C24 C29 12.77(16) . . . . ? Cl1 Ir1 C24 C29 112.04(15) . . . . ? Cl2 Ir1 C24 C29 -82.65(16) . . . . ? C23 C24 C25 C26 3.27(17) . . . . ? C29 C24 C25 C26 -170.14(15) . . . . ? Ir1 C24 C25 C26 63.61(10) . . . . ? C23 C24 C25 C30 177.48(15) . . . . ? C29 C24 C25 C30 4.1(3) . . . . ? Ir1 C24 C25 C30 -122.18(16) . . . . ? C23 C24 C25 Ir1 -60.34(11) . . . . ? C29 C24 C25 Ir1 126.25(16) . . . . ? C23 Ir1 C25 C24 37.44(9) . . . . ? C26 Ir1 C25 C24 116.54(13) . . . . ? C27 Ir1 C25 C24 80.22(10) . . . . ? P1 Ir1 C25 C24 -59.09(10) . . . . ? Cl1 Ir1 C25 C24 116.91(10) . . . . ? Cl2 Ir1 C25 C24 -150.78(8) . . . . ? C23 Ir1 C25 C26 -79.10(9) . . . . ? C24 Ir1 C25 C26 -116.54(13) . . . . ? C27 Ir1 C25 C26 -36.32(9) . . . . ? P1 Ir1 C25 C26 -175.63(7) . . . . ? Cl1 Ir1 C25 C26 0.37(14) . . . . ? Cl2 Ir1 C25 C26 92.68(8) . . . . ? C23 Ir1 C25 C30 159.83(16) . . . . ? C24 Ir1 C25 C30 122.39(18) . . . . ? C26 Ir1 C25 C30 -121.07(18) . . . . ? C27 Ir1 C25 C30 -157.39(16) . . . . ? P1 Ir1 C25 C30 63.30(15) . . . . ? Cl1 Ir1 C25 C30 -120.70(13) . . . . ? Cl2 Ir1 C25 C30 -28.39(14) . . . . ? C24 C25 C26 C27 -1.13(17) . . . . ? C30 C25 C26 C27 -175.47(15) . . . . ? Ir1 C25 C26 C27 61.45(11) . . . . ? C24 C25 C26 C31 176.23(15) . . . . ? C30 C25 C26 C31 1.9(2) . . . . ? Ir1 C25 C26 C31 -121.19(15) . . . . ? C24 C25 C26 Ir1 -62.58(10) . . . . ? C30 C25 C26 Ir1 123.07(16) . . . . ? C23 Ir1 C26 C27 -36.65(9) . . . . ? C25 Ir1 C26 C27 -118.44(13) . . . . ? C24 Ir1 C26 C27 -80.17(10) . . . . ? P1 Ir1 C26 C27 -106.93(14) . . . . ? Cl1 Ir1 C26 C27 61.76(9) . . . . ? Cl2 Ir1 C26 C27 150.64(8) . . . . ? C23 Ir1 C26 C25 81.79(10) . . . . ? C24 Ir1 C26 C25 38.27(9) . . . . ? C27 Ir1 C26 C25 118.44(13) . . . . ? P1 Ir1 C26 C25 11.51(18) . . . . ? Cl1 Ir1 C26 C25 -179.80(8) . . . . ? Cl2 Ir1 C26 C25 -90.91(8) . . . . ? C23 Ir1 C26 C31 -159.52(15) . . . . ? C25 Ir1 C26 C31 118.69(17) . . . . ? C24 Ir1 C26 C31 156.96(15) . . . . ? C27 Ir1 C26 C31 -122.87(17) . . . . ? P1 Ir1 C26 C31 130.20(13) . . . . ? Cl1 Ir1 C26 C31 -61.11(14) . . . . ? Cl2 Ir1 C26 C31 27.78(14) . . . . ? C25 C26 C27 C23 -1.46(17) . . . . ? C31 C26 C27 C23 -178.76(15) . . . . ? Ir1 C26 C27 C23 58.09(10) . . . . ? C25 C26 C27 C32 178.95(14) . . . . ? C31 C26 C27 C32 1.6(3) . . . . ? Ir1 C26 C27 C32 -121.50(15) . . . . ? C25 C26 C27 Ir1 -59.55(10) . . . . ? C31 C26 C27 Ir1 123.15(16) . . . . ? C24 C23 C27 C26 3.45(17) . . . . ? C28 C23 C27 C26 174.87(15) . . . . ? Ir1 C23 C27 C26 -59.70(11) . . . . ? C24 C23 C27 C32 -176.96(14) . . . . ? C28 C23 C27 C32 -5.5(3) . . . . ? Ir1 C23 C27 C32 119.89(15) . . . . ? C24 C23 C27 Ir1 63.15(10) . . . . ? C28 C23 C27 Ir1 -125.43(16) . . . . ? C23 Ir1 C27 C26 120.19(13) . . . . ? C25 Ir1 C27 C26 37.79(9) . . . . ? C24 Ir1 C27 C26 80.92(10) . . . . ? P1 Ir1 C27 C26 148.32(7) . . . . ? Cl1 Ir1 C27 C26 -124.34(8) . . . . ? Cl2 Ir1 C27 C26 -37.57(10) . . . . ? C25 Ir1 C27 C23 -82.40(10) . . . . ? C24 Ir1 C27 C23 -39.27(9) . . . . ? C26 Ir1 C27 C23 -120.19(13) . . . . ? P1 Ir1 C27 C23 28.13(12) . . . . ? Cl1 Ir1 C27 C23 115.47(9) . . . . ? Cl2 Ir1 C27 C23 -157.76(7) . . . . ? C23 Ir1 C27 C32 -119.47(17) . . . . ? C25 Ir1 C27 C32 158.12(16) . . . . ? C24 Ir1 C27 C32 -158.74(16) . . . . ? C26 Ir1 C27 C32 120.33(17) . . . . ? P1 Ir1 C27 C32 -91.35(14) . . . . ? Cl1 Ir1 C27 C32 -4.01(13) . . . . ? Cl2 Ir1 C27 C32 82.77(14) . . . . ? 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 N1 H1N Cl1 0.81(2) 2.67(2) 3.1451(13) 119.8(19) . N1 H1N Cl2 0.81(2) 2.82(2) 3.2529(14) 115.9(19) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.805 _refine_diff_density_min -0.681 _refine_diff_density_rms 0.058 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_l0548a _database_code_depnum_ccdc_archive 'CCDC 1410769' _audit_update_record ; 2015-07-06 deposited with the CCDC. 2015-08-24 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H38 Cl Ir N O2 P S' _chemical_formula_sum 'C32 H38 Cl Ir N O2 P S' _chemical_formula_weight 759.31 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _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. ; 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' _cell_length_a 14.3385(17) _cell_length_b 14.6511(17) _cell_length_c 15.2223(18) _cell_angle_alpha 90 _cell_angle_beta 107.9132(17) _cell_angle_gamma 90 _cell_volume 3042.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9935 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_F_000 1512 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_absorpt_coefficient_mu 4.627 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2755 _exptl_absorpt_correction_T_max 0.4305 _exptl_absorpt_process_details SADABS-2012/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed tube' _diffrn_measurement_device_type 'Bruker Kappa ApexII' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 45334 _diffrn_reflns_av_unetI/netI 0.0079 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.707 _diffrn_reflns_theta_max 27.561 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 7021 _reflns_number_gt 6806 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection Apex2 _computing_cell_refinement 'SAINT V8.27B' _computing_data_reduction 'SAINT V8.27B, SADABS-2012/1' _computing_structure_solution 'coordinates from Rh complex' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0129P)^2^+2.1251P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 7021 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0126 _refine_ls_R_factor_gt 0.0118 _refine_ls_wR_factor_ref 0.0296 _refine_ls_wR_factor_gt 0.0293 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 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 0.28058(2) 0.27146(2) 0.70745(2) 0.01257(2) Uani 1 1 d . . . . . Cl1 Cl 0.12173(3) 0.22578(2) 0.61028(3) 0.02066(7) Uani 1 1 d . . . . . S1 S 0.37325(3) 0.13203(2) 0.59496(2) 0.01623(7) Uani 1 1 d . . . . . P1 P 0.32049(3) 0.31152(2) 0.57760(2) 0.01381(7) Uani 1 1 d . . . . . O1 O 0.33005(8) 0.14051(7) 0.67338(7) 0.0193(2) Uani 1 1 d . . . . . O2 O 0.47548(8) 0.10636(8) 0.62628(8) 0.0237(2) Uani 1 1 d . . . . . N1 N 0.35004(10) 0.21745(8) 0.53230(9) 0.0185(2) Uani 1 1 d . . . . . C1 C 0.31062(11) 0.03832(10) 0.52896(10) 0.0179(3) Uani 1 1 d . . . . . C2 C 0.20948(12) 0.03192(11) 0.50703(11) 0.0253(3) Uani 1 1 d . . . . . H2 H 0.1726 0.0803 0.5217 0.030 Uiso 1 1 calc R U . . . C3 C 0.16295(13) -0.04641(12) 0.46330(12) 0.0288(4) Uani 1 1 d . . . . . H3 H 0.0937 -0.0512 0.4482 0.035 Uiso 1 1 calc R U . . . C4 C 0.21550(13) -0.11807(11) 0.44110(11) 0.0247(3) Uani 1 1 d . . . . . C5 C 0.31633(13) -0.10799(11) 0.46048(12) 0.0254(3) Uani 1 1 d . . . . . H5 H 0.3529 -0.1548 0.4430 0.030 Uiso 1 1 calc R U . . . C6 C 0.36435(12) -0.03071(11) 0.50494(11) 0.0221(3) Uani 1 1 d . . . . . H6 H 0.4334 -0.0252 0.5188 0.027 Uiso 1 1 calc R U . . . C7 C 0.16598(14) -0.20658(12) 0.40162(12) 0.0293(4) Uani 1 1 d . . . . . H7A H 0.0972 -0.2044 0.4024 0.035 Uiso 1 1 calc R U . . . H7B H 0.1990 -0.2571 0.4427 0.035 Uiso 1 1 calc R U . . . C8 C 0.16574(14) -0.22862(11) 0.30368(12) 0.0254(3) Uani 1 1 d . . . . . H8A H 0.1261 -0.1826 0.2605 0.030 Uiso 1 1 calc R U . . . H8B H 0.2336 -0.2258 0.3004 0.030 Uiso 1 1 calc R U . . . C9 C 0.12352(13) -0.32331(12) 0.27501(12) 0.0279(4) Uani 1 1 d . . . . . H9A H 0.1645 -0.3687 0.3181 0.034 Uiso 1 1 calc R U . . . H9B H 0.0570 -0.3260 0.2815 0.034 Uiso 1 1 calc R U . . . C10 C 0.11719(17) -0.35049(15) 0.17687(13) 0.0414(5) Uani 1 1 d . . . . . H10A H 0.0759 -0.3067 0.1334 0.062 Uiso 1 1 calc R U . . . H10B H 0.0886 -0.4116 0.1638 0.062 Uiso 1 1 calc R U . . . H10C H 0.1831 -0.3507 0.1702 0.062 Uiso 1 1 calc R U . . . C11 C 0.22743(10) 0.36515(9) 0.48341(10) 0.0155(3) Uani 1 1 d . . . . . C12 C 0.16329(12) 0.42897(10) 0.50056(11) 0.0209(3) Uani 1 1 d . . . . . H12 H 0.1665 0.4432 0.5623 0.025 Uiso 1 1 calc R U . . . C13 C 0.09460(12) 0.47183(11) 0.42733(11) 0.0230(3) Uani 1 1 d . . . . . H13 H 0.0516 0.5162 0.4391 0.028 Uiso 1 1 calc R U . . . C14 C 0.08866(11) 0.44989(10) 0.33717(11) 0.0212(3) Uani 1 1 d . . . . . H14 H 0.0413 0.4790 0.2873 0.025 Uiso 1 1 calc R U . . . C15 C 0.15166(12) 0.38564(11) 0.31974(10) 0.0222(3) Uani 1 1 d . . . . . H15 H 0.1471 0.3703 0.2579 0.027 Uiso 1 1 calc R U . . . C16 C 0.22159(11) 0.34359(10) 0.39265(10) 0.0191(3) Uani 1 1 d . . . . . H16 H 0.2654 0.3002 0.3807 0.023 Uiso 1 1 calc R U . . . C17 C 0.42592(11) 0.38660(10) 0.59789(10) 0.0187(3) Uani 1 1 d . . . . . C18 C 0.41811(12) 0.48040(11) 0.58136(11) 0.0236(3) Uani 1 1 d . . . . . H18 H 0.3557 0.5070 0.5528 0.028 Uiso 1 1 calc R U . . . C19 C 0.50144(14) 0.53519(12) 0.60652(13) 0.0320(4) Uani 1 1 d . . . . . H19 H 0.4956 0.5991 0.5954 0.038 Uiso 1 1 calc R U . . . C20 C 0.59233(14) 0.49713(15) 0.64745(14) 0.0384(4) Uani 1 1 d . . . . . H20 H 0.6489 0.5349 0.6655 0.046 Uiso 1 1 calc R U . . . C21 C 0.60113(14) 0.40412(15) 0.66223(15) 0.0407(5) Uani 1 1 d . . . . . H21 H 0.6640 0.3779 0.6894 0.049 Uiso 1 1 calc R U . . . C22 C 0.51859(13) 0.34853(13) 0.63763(13) 0.0307(4) Uani 1 1 d . . . . . H22 H 0.5252 0.2846 0.6479 0.037 Uiso 1 1 calc R U . . . C23 C 0.23298(12) 0.27428(9) 0.83358(10) 0.0177(3) Uani 1 1 d . . . . . C24 C 0.22623(11) 0.36349(10) 0.78942(9) 0.0166(3) Uani 1 1 d . . . . . C25 C 0.32360(11) 0.39148(10) 0.79430(10) 0.0173(3) Uani 1 1 d . . . . . C26 C 0.38952(11) 0.31738(10) 0.83329(10) 0.0188(3) Uani 1 1 d . . . . . C27 C 0.33185(12) 0.24664(10) 0.85920(10) 0.0191(3) Uani 1 1 d . . . . . C28 C 0.14785(13) 0.22322(11) 0.84677(12) 0.0254(3) Uani 1 1 d . . . . . H28A H 0.1694 0.1624 0.8717 0.038 Uiso 1 1 calc R U . . . H28B H 0.0965 0.2172 0.7873 0.038 Uiso 1 1 calc R U . . . H28C H 0.1220 0.2566 0.8900 0.038 Uiso 1 1 calc R U . . . C29 C 0.13478(12) 0.41904(10) 0.75576(11) 0.0218(3) Uani 1 1 d . . . . . H29A H 0.1507 0.4793 0.7364 0.033 Uiso 1 1 calc R U . . . H29B H 0.1054 0.4261 0.8056 0.033 Uiso 1 1 calc R U . . . H29C H 0.0883 0.3882 0.7032 0.033 Uiso 1 1 calc R U . . . C30 C 0.35205(13) 0.48474(11) 0.77198(11) 0.0249(3) Uani 1 1 d . . . . . H30A H 0.3561 0.5259 0.8237 0.037 Uiso 1 1 calc R U . . . H30B H 0.3027 0.5076 0.7164 0.037 Uiso 1 1 calc R U . . . H30C H 0.4159 0.4819 0.7612 0.037 Uiso 1 1 calc R U . . . C31 C 0.49879(12) 0.31813(14) 0.85957(12) 0.0310(4) Uani 1 1 d . . . . . H31A H 0.5198 0.3646 0.8233 0.047 Uiso 1 1 calc R U . . . H31B H 0.5221 0.2581 0.8472 0.047 Uiso 1 1 calc R U . . . H31C H 0.5262 0.3322 0.9254 0.047 Uiso 1 1 calc R U . . . C32 C 0.37453(14) 0.15870(11) 0.90356(11) 0.0288(4) Uani 1 1 d . . . . . H32A H 0.3225 0.1210 0.9142 0.043 Uiso 1 1 calc R U . . . H32B H 0.4245 0.1714 0.9627 0.043 Uiso 1 1 calc R U . . . H32C H 0.4045 0.1261 0.8629 0.043 Uiso 1 1 calc R U . . . 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 0.01470(3) 0.01167(3) 0.01029(3) -0.00028(2) 0.00231(2) 0.00057(2) Cl1 0.01772(17) 0.02272(17) 0.01894(17) -0.00345(13) 0.00181(13) -0.00304(13) S1 0.01976(17) 0.01451(15) 0.01246(15) -0.00077(12) 0.00208(13) 0.00323(13) P1 0.01548(17) 0.01319(15) 0.01174(16) 0.00039(13) 0.00268(13) 0.00059(13) O1 0.0308(6) 0.0134(5) 0.0142(5) 0.0006(4) 0.0074(4) 0.0044(4) O2 0.0202(5) 0.0238(5) 0.0222(5) -0.0026(4) -0.0005(4) 0.0055(4) N1 0.0259(7) 0.0158(6) 0.0136(6) 0.0010(4) 0.0061(5) 0.0039(5) C1 0.0239(7) 0.0151(6) 0.0133(6) -0.0010(5) 0.0035(5) 0.0002(6) C2 0.0245(8) 0.0248(8) 0.0240(8) -0.0059(6) 0.0037(6) 0.0046(6) C3 0.0233(8) 0.0327(9) 0.0284(8) -0.0078(7) 0.0052(7) -0.0012(7) C4 0.0340(9) 0.0227(7) 0.0197(7) -0.0042(6) 0.0114(7) -0.0051(7) C5 0.0322(9) 0.0188(7) 0.0291(8) -0.0057(6) 0.0153(7) 0.0002(6) C6 0.0242(8) 0.0200(7) 0.0244(8) -0.0033(6) 0.0106(6) 0.0000(6) C7 0.0379(10) 0.0256(8) 0.0278(9) -0.0066(7) 0.0151(7) -0.0104(7) C8 0.0329(9) 0.0215(8) 0.0214(8) -0.0017(6) 0.0081(7) -0.0068(6) C9 0.0316(9) 0.0269(8) 0.0266(8) -0.0066(7) 0.0109(7) -0.0111(7) C10 0.0535(13) 0.0422(11) 0.0292(10) -0.0132(8) 0.0137(9) -0.0205(10) C11 0.0167(7) 0.0140(6) 0.0143(6) 0.0019(5) 0.0024(5) -0.0014(5) C12 0.0243(8) 0.0202(7) 0.0168(7) -0.0007(6) 0.0043(6) 0.0032(6) C13 0.0232(8) 0.0196(7) 0.0237(8) -0.0005(6) 0.0036(6) 0.0048(6) C14 0.0195(7) 0.0201(7) 0.0193(7) 0.0041(6) -0.0009(6) 0.0010(6) C15 0.0231(8) 0.0272(8) 0.0141(7) 0.0004(6) 0.0024(6) 0.0000(6) C16 0.0185(7) 0.0218(7) 0.0167(7) 0.0001(6) 0.0048(6) 0.0020(6) C17 0.0195(7) 0.0217(7) 0.0153(7) -0.0015(6) 0.0061(6) -0.0037(6) C18 0.0269(8) 0.0219(7) 0.0253(8) -0.0025(6) 0.0130(7) -0.0032(6) C19 0.0392(10) 0.0263(8) 0.0376(10) -0.0083(7) 0.0222(8) -0.0123(7) C20 0.0296(10) 0.0456(11) 0.0426(11) -0.0108(9) 0.0149(8) -0.0199(8) C21 0.0186(8) 0.0509(12) 0.0480(12) 0.0013(10) 0.0038(8) -0.0058(8) C22 0.0218(8) 0.0311(9) 0.0362(10) 0.0045(7) 0.0047(7) -0.0015(7) C23 0.0245(8) 0.0161(7) 0.0131(7) -0.0013(5) 0.0065(6) 0.0001(6) C24 0.0212(7) 0.0152(7) 0.0132(6) -0.0024(5) 0.0049(6) 0.0016(5) C25 0.0222(7) 0.0163(6) 0.0123(6) -0.0042(5) 0.0036(5) -0.0020(6) C26 0.0207(7) 0.0217(7) 0.0117(6) -0.0032(5) 0.0017(5) 0.0008(6) C27 0.0270(8) 0.0183(7) 0.0108(6) -0.0010(5) 0.0038(6) 0.0029(6) C28 0.0318(9) 0.0234(8) 0.0254(8) 0.0001(6) 0.0152(7) -0.0050(6) C29 0.0224(8) 0.0189(7) 0.0241(8) -0.0004(6) 0.0072(6) 0.0048(6) C30 0.0345(9) 0.0185(7) 0.0230(8) -0.0045(6) 0.0109(7) -0.0075(6) C31 0.0198(8) 0.0448(10) 0.0234(8) -0.0048(7) -0.0009(6) -0.0003(7) C32 0.0412(10) 0.0233(8) 0.0192(8) 0.0039(6) 0.0054(7) 0.0118(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C24 2.1402(14) . ? Ir1 O1 2.1630(10) . ? Ir1 C25 2.1722(14) . ? Ir1 C26 2.1728(14) . ? Ir1 C23 2.2271(15) . ? Ir1 C27 2.2280(15) . ? Ir1 P1 2.2968(4) . ? Ir1 Cl1 2.3981(4) . ? S1 O2 1.4448(11) . ? S1 O1 1.5098(11) . ? S1 N1 1.5464(13) . ? S1 C1 1.7736(15) . ? P1 N1 1.6535(13) . ? P1 C11 1.8102(14) . ? P1 C17 1.8175(15) . ? C1 C6 1.387(2) . ? C1 C2 1.388(2) . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.393(2) . ? C3 H3 0.9500 . ? C4 C5 1.392(2) . ? C4 C7 1.512(2) . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.524(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.523(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.522(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.391(2) . ? C11 C16 1.394(2) . ? C12 C13 1.390(2) . ? C12 H12 0.9500 . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.390(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.395(2) . ? C17 C22 1.396(2) . ? C18 C19 1.392(2) . ? C18 H18 0.9500 . ? C19 C20 1.378(3) . ? C19 H19 0.9500 . ? C20 C21 1.381(3) . ? C20 H20 0.9500 . ? C21 C22 1.390(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C27 1.409(2) . ? C23 C24 1.459(2) . ? C23 C28 1.497(2) . ? C24 C25 1.435(2) . ? C24 C29 1.494(2) . ? C25 C26 1.442(2) . ? C25 C30 1.495(2) . ? C26 C27 1.454(2) . ? C26 C31 1.493(2) . ? C27 C32 1.495(2) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? 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 C24 Ir1 O1 154.64(5) . . ? C24 Ir1 C25 38.86(6) . . ? O1 Ir1 C25 144.21(5) . . ? C24 Ir1 C26 65.35(6) . . ? O1 Ir1 C26 106.63(5) . . ? C25 Ir1 C26 38.76(5) . . ? C24 Ir1 C23 38.98(5) . . ? O1 Ir1 C23 115.67(5) . . ? C25 Ir1 C23 64.23(5) . . ? C26 Ir1 C23 64.03(6) . . ? C24 Ir1 C27 64.00(5) . . ? O1 Ir1 C27 94.35(5) . . ? C25 Ir1 C27 63.88(5) . . ? C26 Ir1 C27 38.56(6) . . ? C23 Ir1 C27 36.88(6) . . ? C24 Ir1 P1 124.93(4) . . ? O1 Ir1 P1 80.41(3) . . ? C25 Ir1 P1 102.57(4) . . ? C26 Ir1 P1 112.19(4) . . ? C23 Ir1 P1 163.90(4) . . ? C27 Ir1 P1 147.56(4) . . ? C24 Ir1 Cl1 95.07(4) . . ? O1 Ir1 Cl1 85.63(3) . . ? C25 Ir1 Cl1 129.74(4) . . ? C26 Ir1 Cl1 156.78(4) . . ? C23 Ir1 Cl1 92.99(4) . . ? C27 Ir1 Cl1 122.81(4) . . ? P1 Ir1 Cl1 88.926(15) . . ? O2 S1 O1 112.45(7) . . ? O2 S1 N1 114.72(7) . . ? O1 S1 N1 110.99(6) . . ? O2 S1 C1 105.72(7) . . ? O1 S1 C1 104.61(7) . . ? N1 S1 C1 107.56(7) . . ? N1 P1 C11 104.63(7) . . ? N1 P1 C17 105.60(7) . . ? C11 P1 C17 104.12(7) . . ? N1 P1 Ir1 108.03(5) . . ? C11 P1 Ir1 118.33(5) . . ? C17 P1 Ir1 115.01(5) . . ? S1 O1 Ir1 120.47(6) . . ? S1 N1 P1 116.84(8) . . ? C6 C1 C2 120.76(14) . . ? C6 C1 S1 119.23(12) . . ? C2 C1 S1 119.88(12) . . ? C1 C2 C3 118.89(15) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 121.51(16) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 118.22(15) . . ? C5 C4 C7 120.38(15) . . ? C3 C4 C7 121.33(16) . . ? C6 C5 C4 121.13(15) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 119.40(15) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C4 C7 C8 115.47(14) . . ? C4 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C4 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C7 110.75(13) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 114.73(15) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.77(13) . . ? C12 C11 P1 120.78(11) . . ? C16 C11 P1 119.43(11) . . ? C13 C12 C11 119.96(14) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.12(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.13(14) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.06(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 119.96(14) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C18 C17 C22 118.98(15) . . ? C18 C17 P1 123.30(12) . . ? C22 C17 P1 117.58(12) . . ? C19 C18 C17 120.26(16) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.24(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.97(17) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 120.45(18) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.06(17) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C27 C23 C24 107.66(13) . . ? C27 C23 C28 127.71(14) . . ? C24 C23 C28 124.62(14) . . ? C27 C23 Ir1 71.59(9) . . ? C24 C23 Ir1 67.29(8) . . ? C28 C23 Ir1 125.81(11) . . ? C25 C24 C23 107.85(13) . . ? C25 C24 C29 126.84(13) . . ? C23 C24 C29 124.95(14) . . ? C25 C24 Ir1 71.77(8) . . ? C23 C24 Ir1 73.73(8) . . ? C29 C24 Ir1 125.59(10) . . ? C24 C25 C26 108.08(13) . . ? C24 C25 C30 125.35(14) . . ? C26 C25 C30 126.28(14) . . ? C24 C25 Ir1 69.36(8) . . ? C26 C25 Ir1 70.64(8) . . ? C30 C25 Ir1 130.39(10) . . ? C25 C26 C27 107.03(13) . . ? C25 C26 C31 127.28(15) . . ? C27 C26 C31 124.75(15) . . ? C25 C26 Ir1 70.60(8) . . ? C27 C26 Ir1 72.77(8) . . ? C31 C26 Ir1 130.47(11) . . ? C23 C27 C26 109.13(13) . . ? C23 C27 C32 127.57(15) . . ? C26 C27 C32 123.28(15) . . ? C23 C27 Ir1 71.53(8) . . ? C26 C27 Ir1 68.67(8) . . ? C32 C27 Ir1 124.58(11) . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 O2 S1 O1 Ir1 114.66(8) . . . . ? N1 S1 O1 Ir1 -15.38(10) . . . . ? C1 S1 O1 Ir1 -131.10(7) . . . . ? O2 S1 N1 P1 -108.31(9) . . . . ? O1 S1 N1 P1 20.51(11) . . . . ? C1 S1 N1 P1 134.39(9) . . . . ? C11 P1 N1 S1 -143.29(9) . . . . ? C17 P1 N1 S1 107.17(9) . . . . ? Ir1 P1 N1 S1 -16.37(10) . . . . ? O2 S1 C1 C6 -11.00(14) . . . . ? O1 S1 C1 C6 -129.90(12) . . . . ? N1 S1 C1 C6 112.02(13) . . . . ? O2 S1 C1 C2 164.93(13) . . . . ? O1 S1 C1 C2 46.03(14) . . . . ? N1 S1 C1 C2 -72.06(14) . . . . ? C6 C1 C2 C3 2.2(2) . . . . ? S1 C1 C2 C3 -173.66(13) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -2.6(3) . . . . ? C2 C3 C4 C7 174.28(16) . . . . ? C3 C4 C5 C6 3.2(3) . . . . ? C7 C4 C5 C6 -173.69(16) . . . . ? C2 C1 C6 C5 -1.6(2) . . . . ? S1 C1 C6 C5 174.29(12) . . . . ? C4 C5 C6 C1 -1.2(2) . . . . ? C5 C4 C7 C8 -67.5(2) . . . . ? C3 C4 C7 C8 115.70(19) . . . . ? C4 C7 C8 C9 174.19(16) . . . . ? C7 C8 C9 C10 178.17(17) . . . . ? N1 P1 C11 C12 159.40(12) . . . . ? C17 P1 C11 C12 -89.98(13) . . . . ? Ir1 P1 C11 C12 39.13(14) . . . . ? N1 P1 C11 C16 -22.05(14) . . . . ? C17 P1 C11 C16 88.58(13) . . . . ? Ir1 P1 C11 C16 -142.32(10) . . . . ? C16 C11 C12 C13 -0.8(2) . . . . ? P1 C11 C12 C13 177.70(12) . . . . ? C11 C12 C13 C14 1.2(2) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C14 C15 C16 C11 0.9(2) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? P1 C11 C16 C15 -178.76(12) . . . . ? N1 P1 C17 C18 139.78(13) . . . . ? C11 P1 C17 C18 29.87(15) . . . . ? Ir1 P1 C17 C18 -101.22(13) . . . . ? N1 P1 C17 C22 -44.51(14) . . . . ? C11 P1 C17 C22 -154.43(13) . . . . ? Ir1 P1 C17 C22 74.49(14) . . . . ? C22 C17 C18 C19 -1.7(2) . . . . ? P1 C17 C18 C19 173.95(12) . . . . ? C17 C18 C19 C20 0.4(3) . . . . ? C18 C19 C20 C21 1.1(3) . . . . ? C19 C20 C21 C22 -1.2(3) . . . . ? C20 C21 C22 C17 -0.2(3) . . . . ? C18 C17 C22 C21 1.6(3) . . . . ? P1 C17 C22 C21 -174.31(15) . . . . ? C27 C23 C24 C25 -3.64(16) . . . . ? C28 C23 C24 C25 177.06(14) . . . . ? Ir1 C23 C24 C25 -64.14(9) . . . . ? C27 C23 C24 C29 -177.11(13) . . . . ? C28 C23 C24 C29 3.6(2) . . . . ? Ir1 C23 C24 C29 122.39(14) . . . . ? C27 C23 C24 Ir1 60.50(10) . . . . ? C28 C23 C24 Ir1 -118.81(14) . . . . ? C23 C24 C25 C26 5.13(15) . . . . ? C29 C24 C25 C26 178.45(13) . . . . ? Ir1 C24 C25 C26 -60.29(10) . . . . ? C23 C24 C25 C30 -169.01(13) . . . . ? C29 C24 C25 C30 4.3(2) . . . . ? Ir1 C24 C25 C30 125.57(14) . . . . ? C23 C24 C25 Ir1 65.42(10) . . . . ? C29 C24 C25 Ir1 -121.26(14) . . . . ? C24 C25 C26 C27 -4.64(16) . . . . ? C30 C25 C26 C27 169.43(14) . . . . ? Ir1 C25 C26 C27 -64.13(10) . . . . ? C24 C25 C26 C31 -173.88(14) . . . . ? C30 C25 C26 C31 0.2(2) . . . . ? Ir1 C25 C26 C31 126.63(15) . . . . ? C24 C25 C26 Ir1 59.49(10) . . . . ? C30 C25 C26 Ir1 -126.44(15) . . . . ? C24 C23 C27 C26 0.75(16) . . . . ? C28 C23 C27 C26 -179.97(14) . . . . ? Ir1 C23 C27 C26 58.54(10) . . . . ? C24 C23 C27 C32 -177.66(14) . . . . ? C28 C23 C27 C32 1.6(3) . . . . ? Ir1 C23 C27 C32 -119.86(16) . . . . ? C24 C23 C27 Ir1 -57.80(10) . . . . ? C28 C23 C27 Ir1 121.48(16) . . . . ? C25 C26 C27 C23 2.40(16) . . . . ? C31 C26 C27 C23 171.98(14) . . . . ? Ir1 C26 C27 C23 -60.30(10) . . . . ? C25 C26 C27 C32 -179.12(13) . . . . ? C31 C26 C27 C32 -9.5(2) . . . . ? Ir1 C26 C27 C32 118.19(14) . . . . ? C25 C26 C27 Ir1 62.69(9) . . . . ? C31 C26 C27 Ir1 -127.73(15) . . . . ? _refine_diff_density_max 0.916 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.055 _shelxl_version_number 2013-3 _shelx_res_file ; TITL l0548a CELL 0.71073 14.3385 14.6511 15.2223 90.0000 107.9132 90.0000 ZERR 4 0.0017 0.0017 0.0018 0.0000 0.0017 0.0000 LATT 1 SYMM 0.5-x, y+0.5, 0.5-z SFAC C H Cl IR N O P S UNIT 128 152 4 4 4 8 4 4 TEMP -123 L.S. 15 FMAP 2 PLAN -20 ACTA BOND $H CONF WGHT 0.012900 2.125100 FVAR 0.27891 IR1 4 0.280583 0.271457 0.707453 11.00000 0.01470 0.01167 = 0.01029 -0.00028 0.00231 0.00057 CL1 3 0.121733 0.225781 0.610283 11.00000 0.01772 0.02272 = 0.01894 -0.00345 0.00181 -0.00304 S1 8 0.373251 0.132031 0.594956 11.00000 0.01976 0.01451 = 0.01246 -0.00077 0.00208 0.00323 P1 7 0.320491 0.311522 0.577598 11.00000 0.01548 0.01319 = 0.01174 0.00039 0.00268 0.00059 O1 6 0.330047 0.140515 0.673383 11.00000 0.03079 0.01341 = 0.01419 0.00057 0.00742 0.00437 O2 6 0.475475 0.106356 0.626277 11.00000 0.02022 0.02385 = 0.02215 -0.00258 -0.00050 0.00551 N1 5 0.350045 0.217452 0.532304 11.00000 0.02594 0.01581 = 0.01362 0.00103 0.00611 0.00391 C1 1 0.310623 0.038325 0.528959 11.00000 0.02393 0.01510 = 0.01328 -0.00096 0.00349 0.00023 C2 1 0.209476 0.031918 0.507032 11.00000 0.02454 0.02476 = 0.02403 -0.00586 0.00373 0.00459 AFIX 43 H2 2 0.172648 0.080261 0.521668 11.00000 -1.20000 AFIX 0 C3 1 0.162947 -0.046410 0.463297 11.00000 0.02332 0.03265 = 0.02845 -0.00785 0.00520 -0.00123 AFIX 43 H3 2 0.093726 -0.051189 0.448195 11.00000 -1.20000 AFIX 0 C4 1 0.215502 -0.118068 0.441104 11.00000 0.03404 0.02267 = 0.01969 -0.00419 0.01144 -0.00506 C5 1 0.316330 -0.107990 0.460479 11.00000 0.03221 0.01876 = 0.02913 -0.00567 0.01532 0.00024 AFIX 43 H5 2 0.352928 -0.154794 0.442983 11.00000 -1.20000 AFIX 0 C6 1 0.364353 -0.030709 0.504938 11.00000 0.02416 0.01998 = 0.02440 -0.00326 0.01060 0.00005 AFIX 43 H6 2 0.433387 -0.025166 0.518780 11.00000 -1.20000 AFIX 0 C7 1 0.165978 -0.206584 0.401621 11.00000 0.03792 0.02562 = 0.02776 -0.00665 0.01513 -0.01037 AFIX 23 H7A 2 0.097229 -0.204448 0.402407 11.00000 -1.20000 H7B 2 0.198954 -0.257108 0.442662 11.00000 -1.20000 AFIX 0 C8 1 0.165739 -0.228617 0.303682 11.00000 0.03290 0.02154 = 0.02142 -0.00175 0.00806 -0.00681 AFIX 23 H8A 2 0.126111 -0.182600 0.260476 11.00000 -1.20000 H8B 2 0.233575 -0.225795 0.300408 11.00000 -1.20000 AFIX 0 C9 1 0.123523 -0.323310 0.275009 11.00000 0.03156 0.02690 = 0.02664 -0.00663 0.01088 -0.01108 AFIX 23 H9A 2 0.164539 -0.368654 0.318095 11.00000 -1.20000 H9B 2 0.056950 -0.326036 0.281461 11.00000 -1.20000 AFIX 0 C10 1 0.117194 -0.350495 0.176872 11.00000 0.05353 0.04220 = 0.02921 -0.01317 0.01366 -0.02048 AFIX 137 H10A 2 0.075890 -0.306675 0.133354 11.00000 -1.50000 H10B 2 0.088565 -0.411640 0.163804 11.00000 -1.50000 H10C 2 0.183050 -0.350677 0.170249 11.00000 -1.50000 AFIX 0 C11 1 0.227427 0.365147 0.483410 11.00000 0.01675 0.01398 = 0.01429 0.00193 0.00240 -0.00144 C12 1 0.163291 0.428971 0.500564 11.00000 0.02432 0.02015 = 0.01684 -0.00065 0.00426 0.00322 AFIX 43 H12 2 0.166451 0.443243 0.562292 11.00000 -1.20000 AFIX 0 C13 1 0.094599 0.471830 0.427331 11.00000 0.02321 0.01963 = 0.02373 -0.00045 0.00358 0.00475 AFIX 43 H13 2 0.051635 0.516238 0.439073 11.00000 -1.20000 AFIX 0 C14 1 0.088662 0.449891 0.337174 11.00000 0.01955 0.02007 = 0.01929 0.00413 -0.00093 0.00099 AFIX 43 H14 2 0.041309 0.478964 0.287254 11.00000 -1.20000 AFIX 0 C15 1 0.151659 0.385645 0.319740 11.00000 0.02306 0.02715 = 0.01413 0.00038 0.00235 0.00004 AFIX 43 H15 2 0.147058 0.370325 0.257906 11.00000 -1.20000 AFIX 0 C16 1 0.221589 0.343587 0.392651 11.00000 0.01852 0.02176 = 0.01671 0.00010 0.00479 0.00200 AFIX 43 H16 2 0.265376 0.300182 0.380653 11.00000 -1.20000 AFIX 0 C17 1 0.425916 0.386603 0.597893 11.00000 0.01953 0.02175 = 0.01534 -0.00152 0.00605 -0.00369 C18 1 0.418108 0.480402 0.581364 11.00000 0.02689 0.02195 = 0.02530 -0.00248 0.01305 -0.00318 AFIX 43 H18 2 0.355669 0.506970 0.552830 11.00000 -1.20000 AFIX 0 C19 1 0.501444 0.535194 0.606519 11.00000 0.03917 0.02631 = 0.03760 -0.00834 0.02219 -0.01233 AFIX 43 H19 2 0.495629 0.599064 0.595420 11.00000 -1.20000 AFIX 0 C20 1 0.592327 0.497135 0.647453 11.00000 0.02962 0.04562 = 0.04258 -0.01077 0.01490 -0.01987 AFIX 43 H20 2 0.648917 0.534875 0.665504 11.00000 -1.20000 AFIX 0 C21 1 0.601133 0.404116 0.662233 11.00000 0.01864 0.05092 = 0.04803 0.00133 0.00378 -0.00580 AFIX 43 H21 2 0.664045 0.377929 0.689404 11.00000 -1.20000 AFIX 0 C22 1 0.518590 0.348534 0.637632 11.00000 0.02178 0.03106 = 0.03624 0.00447 0.00467 -0.00153 AFIX 43 H22 2 0.525249 0.284570 0.647873 11.00000 -1.20000 AFIX 0 C23 1 0.232976 0.274276 0.833579 11.00000 0.02451 0.01609 = 0.01307 -0.00127 0.00653 0.00012 C24 1 0.226227 0.363490 0.789417 11.00000 0.02118 0.01523 = 0.01324 -0.00239 0.00487 0.00157 C25 1 0.323602 0.391477 0.794299 11.00000 0.02221 0.01627 = 0.01227 -0.00418 0.00359 -0.00204 C26 1 0.389517 0.317379 0.833289 11.00000 0.02071 0.02169 = 0.01167 -0.00323 0.00168 0.00077 C27 1 0.331852 0.246636 0.859199 11.00000 0.02698 0.01826 = 0.01079 -0.00105 0.00378 0.00293 C28 1 0.147853 0.223216 0.846766 11.00000 0.03182 0.02344 = 0.02536 0.00007 0.01520 -0.00498 AFIX 137 H28A 2 0.169384 0.162424 0.871680 11.00000 -1.50000 H28B 2 0.096478 0.217174 0.787266 11.00000 -1.50000 H28C 2 0.121965 0.256618 0.889988 11.00000 -1.50000 AFIX 0 C29 1 0.134775 0.419043 0.755755 11.00000 0.02244 0.01893 = 0.02407 -0.00037 0.00721 0.00479 AFIX 137 H29A 2 0.150679 0.479324 0.736379 11.00000 -1.50000 H29B 2 0.105357 0.426089 0.805571 11.00000 -1.50000 H29C 2 0.088290 0.388162 0.703231 11.00000 -1.50000 AFIX 0 C30 1 0.352046 0.484742 0.771977 11.00000 0.03454 0.01851 = 0.02296 -0.00446 0.01094 -0.00750 AFIX 137 H30A 2 0.356140 0.525943 0.823746 11.00000 -1.50000 H30B 2 0.302715 0.507560 0.716363 11.00000 -1.50000 H30C 2 0.415931 0.481872 0.761185 11.00000 -1.50000 AFIX 0 C31 1 0.498790 0.318129 0.859568 11.00000 0.01977 0.04484 = 0.02336 -0.00485 -0.00088 -0.00027 AFIX 137 H31A 2 0.519809 0.364592 0.823350 11.00000 -1.50000 H31B 2 0.522071 0.258064 0.847152 11.00000 -1.50000 H31C 2 0.526209 0.332223 0.925449 11.00000 -1.50000 AFIX 0 C32 1 0.374531 0.158702 0.903558 11.00000 0.04119 0.02327 = 0.01916 0.00393 0.00537 0.01175 AFIX 137 H32A 2 0.322550 0.121033 0.914181 11.00000 -1.50000 H32B 2 0.424478 0.171374 0.962659 11.00000 -1.50000 H32C 2 0.404534 0.126070 0.862904 11.00000 -1.50000 AFIX 0 HKLF 4 REM l0548a REM R1 = 0.0118 for 6806 Fo > 4sig(Fo) and 0.0126 for all 7021 data REM 358 parameters refined using 0 restraints END WGHT 0.0127 2.1542 REM Highest difference peak 0.916, deepest hole -0.355, 1-sigma level 0.055 Q1 1 0.2391 0.2732 0.7407 11.00000 0.05 0.92 Q2 1 0.3190 0.2716 0.6690 11.00000 0.05 0.76 Q3 1 0.3383 0.1368 0.6309 11.00000 0.05 0.38 Q4 1 0.2719 0.3429 0.5298 11.00000 0.05 0.34 Q5 1 0.3399 0.0788 0.5591 11.00000 0.05 0.33 Q6 1 0.1218 0.4142 0.3329 11.00000 0.05 0.32 Q7 1 0.2795 0.2613 0.8654 11.00000 0.05 0.32 Q8 1 0.1943 0.3758 0.3620 11.00000 0.05 0.32 Q9 1 0.2735 0.3788 0.7959 11.00000 0.05 0.31 Q10 1 0.3283 0.2537 0.5552 11.00000 0.05 0.31 Q11 1 0.3590 0.1840 0.5665 11.00000 0.05 0.31 Q12 1 0.3654 0.2761 0.8500 11.00000 0.05 0.31 Q13 1 0.2002 0.2544 0.8397 11.00000 0.05 0.30 Q14 1 0.3599 0.3594 0.8238 11.00000 0.05 0.30 Q15 1 0.3796 0.3528 0.5934 11.00000 0.05 0.30 Q16 1 0.2052 0.4102 0.4858 11.00000 0.05 0.30 Q17 1 0.2226 0.3598 0.4365 11.00000 0.05 0.30 Q18 1 0.2359 0.3212 0.8282 11.00000 0.05 0.29 Q19 1 0.2251 0.3174 0.8031 11.00000 0.05 0.28 Q20 1 0.1441 -0.2749 0.2886 11.00000 0.05 0.28 ; _shelx_res_checksum 16031 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_I _database_code_depnum_ccdc_archive 'CCDC 1412995' _audit_update_record ; 2015-07-15 deposited with the CCDC. 2015-08-24 downloaded from the CCDC. ; _chemical_name_systematic ? _chemical_name_common SO834E _chemical_formula_moiety ? _chemical_formula_sum 'C40 H44 Cl Ir N O2 P S' _chemical_formula_iupac ? _chemical_formula_weight 861.44 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' 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' _cell_length_a 22.7439(8) _cell_length_b 18.8669(7) _cell_length_c 17.5730(6) _cell_angle_alpha 90 _cell_angle_beta 106.1060(15) _cell_angle_gamma 90 _cell_volume 7244.7(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 150.(2) _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 3.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.30 _exptl_absorpt_correction_T_max 0.70 _exptl_special_details ; ; _diffrn_ambient_temperature 150.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 40820 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.0255 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _refine_special_details ; ; _reflns_number_total 6384 _reflns_number_gt 5662 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.0707 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_number_reflns 6384 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.124 _refine_diff_density_min -1.142 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir1 0.23486(2) 0.48786(2) 0.76545(2) 0.01701(7) Uani d . . . 1 . . P P1 0.33364(4) 0.47973(4) 0.76985(5) 0.01592(17) Uani d . . . 1 . . Cl Cl1 0.20780(4) 0.54232(5) 0.63644(4) 0.02942(19) Uani d . . . 1 . . N N1 0.34194(11) 0.56719(14) 0.79786(15) 0.0185(5) Uani d . . . 1 . . C C1 0.27993(14) 0.58268(16) 0.80311(17) 0.0179(6) Uani d . . . 1 . . C C2 0.26610(15) 0.64616(18) 0.82735(19) 0.0245(7) Uani d . . . 1 . . H H2 0.2988 0.6788 0.8453 0.029 Uiso calc U . R 1 . . C C3 0.20506(16) 0.66993(17) 0.8288(2) 0.0287(8) Uani d . . . 1 . . C C4 0.19746(19) 0.7076(2) 0.8935(3) 0.0399(9) Uani d . . . 1 . . H H4 0.2321 0.7172 0.9369 0.048 Uiso calc U . R 1 . . C C5 0.1402(2) 0.7314(2) 0.8959(3) 0.0514(12) Uani d . . . 1 . . H H5 0.136 0.7563 0.9411 0.062 Uiso calc U . R 1 . . C C6 0.0895(2) 0.7191(2) 0.8331(3) 0.0474(11) Uani d . . . 1 . . H H6 0.0503 0.7353 0.8347 0.057 Uiso calc U . R 1 . . C C7 0.09609(19) 0.6830(2) 0.7677(3) 0.0424(10) Uani d . . . 1 . . H H7 0.0613 0.6747 0.7241 0.051 Uiso calc U . R 1 . . C C8 0.15317(16) 0.6585(2) 0.7649(2) 0.0312(8) Uani d . . . 1 . . H H8 0.157 0.6338 0.7194 0.037 Uiso calc U . R 1 . . S S1 0.40348(4) 0.61810(4) 0.81698(4) 0.02040(16) Uani d . . . 1 . . O O1 0.40664(11) 0.66031(13) 0.88600(13) 0.0282(5) Uani d . . . 1 . . O O2 0.45370(10) 0.57207(13) 0.81842(14) 0.0289(5) Uani d . . . 1 . . C C9 0.39282(14) 0.67699(17) 0.73648(18) 0.0204(6) Uani d . . . 1 . . C C10 0.42138(18) 0.7417(2) 0.7512(2) 0.0326(8) Uani d . . . 1 . . H H10 0.4427 0.7545 0.8039 0.039 Uiso calc U . R 1 . . C C11 0.41921(19) 0.7882(2) 0.6897(2) 0.0361(9) Uani d . . . 1 . . H H11 0.4387 0.833 0.7008 0.043 Uiso calc U . R 1 . . C C12 0.38902(14) 0.77048(18) 0.61208(19) 0.0223(7) Uani d . . . 1 . . C C13 0.35915(18) 0.7058(2) 0.5994(2) 0.0353(9) Uani d . . . 1 . . H H13 0.3369 0.6933 0.5469 0.042 Uiso calc U . R 1 . . C C14 0.36048(19) 0.6588(2) 0.6602(2) 0.0355(9) Uani d . . . 1 . . H H14 0.3395 0.6148 0.6497 0.043 Uiso calc U . R 1 . . C C15 0.38884(15) 0.81975(19) 0.54413(19) 0.0269(7) Uani d . . . 1 . . H H15A 0.3644 0.8623 0.548 0.032 Uiso calc U . R 1 . . H H15B 0.3685 0.7956 0.4937 0.032 Uiso calc U . R 1 . . C C16 0.45256(15) 0.84321(18) 0.54202(19) 0.0244(7) Uani d . . . 1 . . H H16A 0.4709 0.8727 0.5892 0.029 Uiso calc U . R 1 . . H H16B 0.4787 0.8008 0.5448 0.029 Uiso calc U . R 1 . . C C17 0.45192(16) 0.8852(2) 0.4678(2) 0.0290(8) Uani d . . . 1 . . H H17A 0.4316 0.8566 0.4206 0.035 Uiso calc U . R 1 . . H H17B 0.4275 0.9288 0.4665 0.035 Uiso calc U . R 1 . . C C18 0.51539(17) 0.9056(2) 0.4634(2) 0.0407(10) Uani d . . . 1 . . H H18A 0.5344 0.9374 0.5074 0.061 Uiso calc U . R 1 . . H H18B 0.5123 0.9297 0.413 0.061 Uiso calc U . R 1 . . H H18C 0.5404 0.8628 0.4668 0.061 Uiso calc U . R 1 . . C C19 0.22047(14) 0.42346(17) 0.86155(19) 0.0215(7) Uani d . . . 1 . . C C20 0.21477(15) 0.37683(18) 0.7942(2) 0.0267(7) Uani d . . . 1 . . C C21 0.16548(15) 0.40179(19) 0.7318(2) 0.0293(8) Uani d . . . 1 . . C C22 0.13707(14) 0.4609(2) 0.7617(2) 0.0273(7) Uani d . . . 1 . . C C23 0.17000(15) 0.47253(18) 0.8423(2) 0.0238(7) Uani d . . . 1 . . C C24 0.26203(15) 0.4120(2) 0.9435(2) 0.0307(8) Uani d . . . 1 . . H H24A 0.2722 0.4579 0.9701 0.046 Uiso calc U . R 1 . . H H24B 0.2996 0.3886 0.94 0.046 Uiso calc U . R 1 . . H H24C 0.2413 0.3822 0.9738 0.046 Uiso calc U . R 1 . . C C25 0.25225(18) 0.31179(19) 0.7929(3) 0.0376(9) Uani d . . . 1 . . H H25A 0.2307 0.2701 0.8049 0.056 Uiso calc U . R 1 . . H H25B 0.292 0.3163 0.8326 0.056 Uiso calc U . R 1 . . H H25C 0.2586 0.3064 0.7403 0.056 Uiso calc U . R 1 . . C C26 0.1439(2) 0.3710(3) 0.6494(2) 0.0499(11) Uani d . . . 1 . . H H26A 0.1421 0.4086 0.6103 0.075 Uiso calc U . R 1 . . H H26B 0.1031 0.3504 0.6414 0.075 Uiso calc U . R 1 . . H H26C 0.1725 0.3341 0.643 0.075 Uiso calc U . R 1 . . C C27 0.0798(2) 0.4964(2) 0.7150(3) 0.0472(11) Uani d . . . 1 . . H H27A 0.0459 0.4623 0.7039 0.071 Uiso calc U . R 1 . . H H27B 0.0854 0.514 0.665 0.071 Uiso calc U . R 1 . . H H27C 0.0704 0.5362 0.7455 0.071 Uiso calc U . R 1 . . C C28 0.1542(2) 0.5227(2) 0.8993(3) 0.0376(10) Uani d . . . 1 . . H H28A 0.1277 0.5603 0.8699 0.056 Uiso calc U . R 1 . . H H28B 0.1918 0.5437 0.9332 0.056 Uiso calc U . R 1 . . H H28C 0.1328 0.4971 0.9321 0.056 Uiso calc U . R 1 . . C C29 0.38542(13) 0.42895(17) 0.84758(17) 0.0188(6) Uani d . . . 1 . . C C30 0.40363(15) 0.36100(18) 0.8322(2) 0.0232(7) Uani d . . . 1 . . H H30 0.3911 0.3424 0.7799 0.028 Uiso calc U . R 1 . . C C31 0.44013(16) 0.32062(19) 0.8936(2) 0.0311(8) Uani d . . . 1 . . H H31 0.4524 0.2743 0.8833 0.037 Uiso calc U . R 1 . . C C32 0.45880(16) 0.34794(19) 0.9702(2) 0.0300(8) Uani d . . . 1 . . H H32 0.4838 0.3203 1.0119 0.036 Uiso calc U . R 1 . . C C33 0.44102(15) 0.41509(18) 0.98568(19) 0.0259(7) Uani d . . . 1 . . H H33 0.4542 0.4338 1.0378 0.031 Uiso calc U . R 1 . . C C34 0.40387(14) 0.45527(18) 0.92498(18) 0.0219(7) Uani d . . . 1 . . H H34 0.3909 0.501 0.9361 0.026 Uiso calc U . R 1 . . C C35 0.35805(15) 0.45790(18) 0.68329(18) 0.0221(7) Uani d . . . 1 . . C C36 0.31465(16) 0.43029(18) 0.61707(19) 0.0259(7) Uani d . . . 1 . . H H36 0.2727 0.4278 0.6161 0.031 Uiso calc U . R 1 . . C C37 0.33359(18) 0.4066(2) 0.5529(2) 0.0334(8) Uani d . . . 1 . . H H37 0.3043 0.3883 0.5075 0.04 Uiso calc U . R 1 . . C C38 0.39414(18) 0.40928(19) 0.5544(2) 0.0333(8) Uani d . . . 1 . . H H38 0.4067 0.3917 0.5107 0.04 Uiso calc U . R 1 . . C C39 0.43721(18) 0.4374(2) 0.6191(2) 0.0346(8) Uani d . . . 1 . . H H39 0.479 0.4396 0.6196 0.042 Uiso calc U . R 1 . . C C40 0.41911(15) 0.4624(2) 0.6833(2) 0.0294(7) Uani d . . . 1 . . H H40 0.4484 0.4826 0.7273 0.035 Uiso calc U . R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ir1 0.01493(9) 0.02024(10) 0.01556(9) 0.00163(4) 0.00371(6) 0.00283(4) P1 0.0172(4) 0.0182(4) 0.0130(4) 0.0018(3) 0.0052(3) 0.0019(3) Cl1 0.0288(4) 0.0392(5) 0.0194(4) 0.0088(4) 0.0053(3) 0.0100(3) N1 0.0146(12) 0.0196(13) 0.0218(13) -0.0004(10) 0.0059(10) 0.0034(11) C1 0.0193(15) 0.0191(15) 0.0163(14) 0.0006(12) 0.0067(12) 0.0084(12) C2 0.0234(17) 0.0216(17) 0.0298(17) 0.0041(13) 0.0095(14) 0.0066(14) C3 0.0347(19) 0.0161(16) 0.0407(19) 0.0051(14) 0.0192(16) 0.0061(15) C4 0.041(2) 0.028(2) 0.056(2) 0.0033(17) 0.0202(19) -0.0056(18) C5 0.059(3) 0.030(2) 0.081(3) 0.002(2) 0.047(3) -0.012(2) C6 0.039(2) 0.032(2) 0.082(3) 0.0156(18) 0.034(2) 0.012(2) C7 0.034(2) 0.040(2) 0.057(3) 0.0127(18) 0.0190(19) 0.019(2) C8 0.0299(19) 0.0301(19) 0.0370(19) 0.0127(15) 0.0150(16) 0.0104(16) S1 0.0193(4) 0.0215(4) 0.0193(4) -0.0016(3) 0.0035(3) 0.0026(3) O1 0.0340(13) 0.0307(13) 0.0191(11) -0.0063(10) 0.0057(10) -0.0007(10) O2 0.0192(11) 0.0288(13) 0.0373(13) 0.0018(10) 0.0057(10) 0.0066(11) C9 0.0204(15) 0.0206(16) 0.0208(15) 0.0014(13) 0.0069(12) 0.0026(13) C10 0.045(2) 0.031(2) 0.0196(16) -0.0132(17) 0.0051(15) -0.0032(14) C11 0.051(2) 0.028(2) 0.0290(19) -0.0166(17) 0.0102(17) -0.0015(15) C12 0.0214(16) 0.0231(17) 0.0240(16) 0.0033(13) 0.0090(13) 0.0024(13) C13 0.047(2) 0.031(2) 0.0217(17) -0.0145(17) -0.0009(15) 0.0030(15) C14 0.050(2) 0.0243(19) 0.0254(17) -0.0119(17) -0.0005(16) 0.0001(15) C15 0.0230(17) 0.0297(18) 0.0267(17) 0.0014(14) 0.0046(14) 0.0077(14) C16 0.0246(17) 0.0252(17) 0.0229(16) 0.0004(14) 0.0059(13) 0.0034(13) C17 0.0264(18) 0.035(2) 0.0258(17) -0.0003(15) 0.0071(14) 0.0082(15) C18 0.030(2) 0.055(3) 0.037(2) 0.0015(18) 0.0101(16) 0.0204(19) C19 0.0166(15) 0.0255(17) 0.0237(15) 0.0002(13) 0.0079(12) 0.0113(13) C20 0.0257(17) 0.0258(18) 0.0322(17) -0.0041(14) 0.0141(14) 0.0010(14) C21 0.0226(17) 0.0317(19) 0.0316(18) -0.0098(14) 0.0043(14) -0.0024(15) C22 0.0128(15) 0.039(2) 0.0292(17) 0.0003(15) 0.0044(13) 0.0149(16) C23 0.0229(17) 0.0274(18) 0.0233(16) 0.0014(14) 0.0099(14) 0.0155(14) C24 0.0253(17) 0.038(2) 0.0273(17) -0.0012(15) 0.0052(14) 0.0161(15) C25 0.036(2) 0.0216(19) 0.061(2) -0.0050(16) 0.0225(19) -0.0027(18) C26 0.045(2) 0.063(3) 0.038(2) -0.022(2) 0.0063(19) -0.010(2) C27 0.022(2) 0.060(3) 0.057(3) 0.0047(18) 0.005(2) 0.021(2) C28 0.046(2) 0.035(2) 0.042(2) 0.0127(17) 0.028(2) 0.0124(17) C29 0.0176(15) 0.0216(16) 0.0169(14) 0.0000(12) 0.0043(12) 0.0029(12) C30 0.0219(16) 0.0225(17) 0.0249(16) -0.0003(13) 0.0061(13) 0.0013(13) C31 0.0319(19) 0.0197(17) 0.041(2) 0.0050(14) 0.0083(16) 0.0050(15) C32 0.0248(17) 0.032(2) 0.0288(17) 0.0016(15) 0.0009(14) 0.0142(15) C33 0.0256(17) 0.0301(19) 0.0198(15) -0.0014(14) 0.0024(13) 0.0040(14) C34 0.0224(16) 0.0219(17) 0.0225(15) 0.0003(13) 0.0082(13) 0.0006(13) C35 0.0278(17) 0.0212(16) 0.0173(14) 0.0057(14) 0.0061(13) 0.0031(13) C36 0.0301(18) 0.0254(18) 0.0221(16) 0.0022(14) 0.0068(14) -0.0030(14) C37 0.046(2) 0.033(2) 0.0186(16) 0.0052(17) 0.0042(15) -0.0028(14) C38 0.055(2) 0.0270(18) 0.0257(17) 0.0099(17) 0.0248(17) 0.0063(15) C39 0.037(2) 0.041(2) 0.0343(19) 0.0032(17) 0.0223(16) 0.0007(17) C40 0.0232(17) 0.041(2) 0.0264(17) -0.0014(16) 0.0105(14) -0.0045(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ir1 C1 . 2.077(3) ? Ir1 C19 . 2.178(3) ? Ir1 C21 . 2.227(3) ? Ir1 C20 . 2.232(3) ? Ir1 P1 . 2.2317(8) ? Ir1 C22 . 2.265(3) ? Ir1 C23 . 2.278(3) ? Ir1 Cl1 . 2.4083(8) ? P1 N1 . 1.717(3) ? P1 C35 . 1.806(3) ? P1 C29 . 1.811(3) ? N1 C1 . 1.468(4) ? N1 S1 . 1.653(3) ? C1 C2 . 1.338(5) ? C2 C3 . 1.466(5) ? C2 H2 . 0.95 ? C3 C4 . 1.393(5) ? C3 C8 . 1.401(5) ? C4 C5 . 1.389(6) ? C4 H4 . 0.95 ? C5 C6 . 1.378(7) ? C5 H5 . 0.95 ? C6 C7 . 1.379(6) ? C6 H6 . 0.95 ? C7 C8 . 1.392(5) ? C7 H7 . 0.95 ? C8 H8 . 0.95 ? S1 O2 . 1.429(2) ? S1 O1 . 1.436(2) ? S1 C9 . 1.762(3) ? C9 C10 . 1.373(5) ? C9 C14 . 1.382(5) ? C10 C11 . 1.382(5) ? C10 H10 . 0.95 ? C11 C12 . 1.387(5) ? C11 H11 . 0.95 ? C12 C13 . 1.384(5) ? C12 C15 . 1.512(4) ? C13 C14 . 1.383(5) ? C13 H13 . 0.95 ? C14 H14 . 0.95 ? C15 C16 . 1.526(5) ? C15 H15A . 0.99 ? C15 H15B . 0.99 ? C16 C17 . 1.523(4) ? C16 H16A . 0.99 ? C16 H16B . 0.99 ? C17 C18 . 1.517(5) ? C17 H17A . 0.99 ? C17 H17B . 0.99 ? C18 H18A . 0.98 ? C18 H18B . 0.98 ? C18 H18C . 0.98 ? C19 C23 . 1.440(5) ? C19 C20 . 1.452(5) ? C19 C24 . 1.503(4) ? C20 C21 . 1.413(5) ? C20 C25 . 1.498(5) ? C21 C22 . 1.457(5) ? C21 C26 . 1.511(5) ? C22 C23 . 1.424(5) ? C22 C27 . 1.493(5) ? C23 C28 . 1.493(5) ? C24 H24A . 0.98 ? C24 H24B . 0.98 ? C24 H24C . 0.98 ? C25 H25A . 0.98 ? C25 H25B . 0.98 ? C25 H25C . 0.98 ? C26 H26A . 0.98 ? C26 H26B . 0.98 ? C26 H26C . 0.98 ? C27 H27A . 0.98 ? C27 H27B . 0.98 ? C27 H27C . 0.98 ? C28 H28A . 0.98 ? C28 H28B . 0.98 ? C28 H28C . 0.98 ? C29 C30 . 1.397(5) ? C29 C34 . 1.399(4) ? C30 C31 . 1.392(5) ? C30 H30 . 0.95 ? C31 C32 . 1.394(5) ? C31 H31 . 0.95 ? C32 C33 . 1.379(5) ? C32 H32 . 0.95 ? C33 C34 . 1.388(5) ? C33 H33 . 0.95 ? C34 H34 . 0.95 ? C35 C40 . 1.391(5) ? C35 C36 . 1.401(5) ? C36 C37 . 1.388(5) ? C36 H36 . 0.95 ? C37 C38 . 1.371(5) ? C37 H37 . 0.95 ? C38 C39 . 1.385(6) ? C38 H38 . 0.95 ? C39 C40 . 1.386(5) ? C39 H39 . 0.95 ? C40 H40 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 Ir1 C19 . . 113.62(12) ? C1 Ir1 C21 . . 164.48(13) ? C19 Ir1 C21 . . 63.32(13) ? C1 Ir1 C20 . . 148.27(12) ? C19 Ir1 C20 . . 38.42(13) ? C21 Ir1 C20 . . 36.96(13) ? C1 Ir1 P1 . . 69.21(9) ? C19 Ir1 P1 . . 107.53(8) ? C21 Ir1 P1 . . 126.27(10) ? C20 Ir1 P1 . . 101.24(9) ? C1 Ir1 C22 . . 126.66(13) ? C19 Ir1 C22 . . 62.59(12) ? C21 Ir1 C22 . . 37.84(14) ? C20 Ir1 C22 . . 62.25(13) ? P1 Ir1 C22 . . 163.06(11) ? C1 Ir1 C23 . . 105.31(12) ? C19 Ir1 C23 . . 37.63(12) ? C21 Ir1 C23 . . 62.41(13) ? C20 Ir1 C23 . . 62.60(12) ? P1 Ir1 C23 . . 141.45(8) ? C22 Ir1 C23 . . 36.54(12) ? C1 Ir1 Cl1 . . 84.67(8) ? C19 Ir1 Cl1 . . 156.05(9) ? C21 Ir1 Cl1 . . 94.83(9) ? C20 Ir1 Cl1 . . 126.76(9) ? P1 Ir1 Cl1 . . 93.09(3) ? C22 Ir1 Cl1 . . 94.35(9) ? C23 Ir1 Cl1 . . 125.01(8) ? N1 P1 C35 . . 115.19(14) ? N1 P1 C29 . . 107.18(14) ? C35 P1 C29 . . 103.13(14) ? N1 P1 Ir1 . . 88.48(9) ? C35 P1 Ir1 . . 121.90(11) ? C29 P1 Ir1 . . 120.02(10) ? C1 N1 S1 . . 130.2(2) ? C1 N1 P1 . . 100.26(19) ? S1 N1 P1 . . 129.49(16) ? C2 C1 N1 . . 120.9(3) ? C2 C1 Ir1 . . 137.2(2) ? N1 C1 Ir1 . . 101.91(19) ? C1 C2 C3 . . 125.9(3) ? C1 C2 H2 . . 117.0 ? C3 C2 H2 . . 117.0 ? C4 C3 C8 . . 117.7(3) ? C4 C3 C2 . . 120.2(3) ? C8 C3 C2 . . 122.1(3) ? C5 C4 C3 . . 121.3(4) ? C5 C4 H4 . . 119.3 ? C3 C4 H4 . . 119.3 ? C6 C5 C4 . . 120.3(4) ? C6 C5 H5 . . 119.8 ? C4 C5 H5 . . 119.8 ? C5 C6 C7 . . 119.4(4) ? C5 C6 H6 . . 120.3 ? C7 C6 H6 . . 120.3 ? C6 C7 C8 . . 120.8(4) ? C6 C7 H7 . . 119.6 ? C8 C7 H7 . . 119.6 ? C7 C8 C3 . . 120.5(4) ? C7 C8 H8 . . 119.7 ? C3 C8 H8 . . 119.7 ? O2 S1 O1 . . 118.00(15) ? O2 S1 N1 . . 106.14(14) ? O1 S1 N1 . . 109.58(14) ? O2 S1 C9 . . 109.18(15) ? O1 S1 C9 . . 106.97(15) ? N1 S1 C9 . . 106.44(14) ? C10 C9 C14 . . 120.0(3) ? C10 C9 S1 . . 117.2(2) ? C14 C9 S1 . . 122.7(3) ? C9 C10 C11 . . 120.3(3) ? C9 C10 H10 . . 119.8 ? C11 C10 H10 . . 119.8 ? C10 C11 C12 . . 121.1(3) ? C10 C11 H11 . . 119.5 ? C12 C11 H11 . . 119.5 ? C13 C12 C11 . . 117.2(3) ? C13 C12 C15 . . 121.4(3) ? C11 C12 C15 . . 121.4(3) ? C14 C13 C12 . . 122.4(3) ? C14 C13 H13 . . 118.8 ? C12 C13 H13 . . 118.8 ? C9 C14 C13 . . 118.8(3) ? C9 C14 H14 . . 120.6 ? C13 C14 H14 . . 120.6 ? C12 C15 C16 . . 113.8(3) ? C12 C15 H15A . . 108.8 ? C16 C15 H15A . . 108.8 ? C12 C15 H15B . . 108.8 ? C16 C15 H15B . . 108.8 ? H15A C15 H15B . . 107.7 ? C17 C16 C15 . . 112.9(3) ? C17 C16 H16A . . 109.0 ? C15 C16 H16A . . 109.0 ? C17 C16 H16B . . 109.0 ? C15 C16 H16B . . 109.0 ? H16A C16 H16B . . 107.8 ? C18 C17 C16 . . 113.2(3) ? C18 C17 H17A . . 108.9 ? C16 C17 H17A . . 108.9 ? C18 C17 H17B . . 108.9 ? C16 C17 H17B . . 108.9 ? H17A C17 H17B . . 107.8 ? C17 C18 H18A . . 109.5 ? C17 C18 H18B . . 109.5 ? H18A C18 H18B . . 109.5 ? C17 C18 H18C . . 109.5 ? H18A C18 H18C . . 109.5 ? H18B C18 H18C . . 109.5 ? C23 C19 C20 . . 108.2(3) ? C23 C19 C24 . . 124.5(3) ? C20 C19 C24 . . 125.8(3) ? C23 C19 Ir1 . . 74.96(18) ? C20 C19 Ir1 . . 72.80(18) ? C24 C19 Ir1 . . 129.3(2) ? C21 C20 C19 . . 107.6(3) ? C21 C20 C25 . . 126.4(3) ? C19 C20 C25 . . 125.9(3) ? C21 C20 Ir1 . . 71.3(2) ? C19 C20 Ir1 . . 68.78(18) ? C25 C20 Ir1 . . 127.8(2) ? C20 C21 C22 . . 108.2(3) ? C20 C21 C26 . . 126.3(4) ? C22 C21 C26 . . 125.5(3) ? C20 C21 Ir1 . . 71.70(19) ? C22 C21 Ir1 . . 72.49(19) ? C26 C21 Ir1 . . 123.5(3) ? C23 C22 C21 . . 108.2(3) ? C23 C22 C27 . . 127.9(4) ? C21 C22 C27 . . 123.6(4) ? C23 C22 Ir1 . . 72.23(18) ? C21 C22 Ir1 . . 69.68(18) ? C27 C22 Ir1 . . 128.0(3) ? C22 C23 C19 . . 107.4(3) ? C22 C23 C28 . . 127.4(3) ? C19 C23 C28 . . 125.1(3) ? C22 C23 Ir1 . . 71.23(18) ? C19 C23 Ir1 . . 67.41(17) ? C28 C23 Ir1 . . 129.3(3) ? C19 C24 H24A . . 109.5 ? C19 C24 H24B . . 109.5 ? H24A C24 H24B . . 109.5 ? C19 C24 H24C . . 109.5 ? H24A C24 H24C . . 109.5 ? H24B C24 H24C . . 109.5 ? C20 C25 H25A . . 109.5 ? C20 C25 H25B . . 109.5 ? H25A C25 H25B . . 109.5 ? C20 C25 H25C . . 109.5 ? H25A C25 H25C . . 109.5 ? H25B C25 H25C . . 109.5 ? C21 C26 H26A . . 109.5 ? C21 C26 H26B . . 109.5 ? H26A C26 H26B . . 109.5 ? C21 C26 H26C . . 109.5 ? H26A C26 H26C . . 109.5 ? H26B C26 H26C . . 109.5 ? C22 C27 H27A . . 109.5 ? C22 C27 H27B . . 109.5 ? H27A C27 H27B . . 109.5 ? C22 C27 H27C . . 109.5 ? H27A C27 H27C . . 109.5 ? H27B C27 H27C . . 109.5 ? C23 C28 H28A . . 109.5 ? C23 C28 H28B . . 109.5 ? H28A C28 H28B . . 109.5 ? C23 C28 H28C . . 109.5 ? H28A C28 H28C . . 109.5 ? H28B C28 H28C . . 109.5 ? C30 C29 C34 . . 119.3(3) ? C30 C29 P1 . . 120.4(2) ? C34 C29 P1 . . 120.2(2) ? C31 C30 C29 . . 119.8(3) ? C31 C30 H30 . . 120.1 ? C29 C30 H30 . . 120.1 ? C30 C31 C32 . . 120.2(3) ? C30 C31 H31 . . 119.9 ? C32 C31 H31 . . 119.9 ? C33 C32 C31 . . 120.2(3) ? C33 C32 H32 . . 119.9 ? C31 C32 H32 . . 119.9 ? C32 C33 C34 . . 120.0(3) ? C32 C33 H33 . . 120.0 ? C34 C33 H33 . . 120.0 ? C33 C34 C29 . . 120.5(3) ? C33 C34 H34 . . 119.7 ? C29 C34 H34 . . 119.7 ? C40 C35 C36 . . 119.7(3) ? C40 C35 P1 . . 121.8(2) ? C36 C35 P1 . . 118.3(3) ? C37 C36 C35 . . 119.3(3) ? C37 C36 H36 . . 120.4 ? C35 C36 H36 . . 120.4 ? C38 C37 C36 . . 120.6(3) ? C38 C37 H37 . . 119.7 ? C36 C37 H37 . . 119.7 ? C37 C38 C39 . . 120.5(3) ? C37 C38 H38 . . 119.7 ? C39 C38 H38 . . 119.7 ? C38 C39 C40 . . 119.8(3) ? C38 C39 H39 . . 120.1 ? C40 C39 H39 . . 120.1 ? C39 C40 C35 . . 120.1(3) ? C39 C40 H40 . . 120.0 ? C35 C40 H40 . . 120.0 ? _shelx_res_file ; SO834E_0m_a.res created by SHELXL-2014/7 TITL SO834E_0m in C2/c CELL 0.71073 22.7439 18.8669 17.5730 90.000 106.106 90.000 ZERR 8.00 0.00080 0.00070 0.00060 0.0000 0.0015 0.0000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H N O P S Cl Ir UNIT 320 352 8 16 8 8 8 8 L.S. 10 ACTA BOND BOND $H FMAP 2 PLAN 10 OMIT -2 50 SIZE 0.100 0.100 0.400 TEMP -123.150 WGHT 0.050000 FVAR 0.12975 IR1 8 0.234860 0.487861 0.765448 11.00000 0.01493 0.02024 = 0.01556 0.00283 0.00371 0.00163 P1 5 0.333637 0.479731 0.769848 11.00000 0.01716 0.01820 = 0.01299 0.00188 0.00518 0.00175 CL1 7 0.207797 0.542323 0.636442 11.00000 0.02883 0.03916 = 0.01944 0.01002 0.00529 0.00882 N1 3 0.341937 0.567194 0.797859 11.00000 0.01462 0.01962 = 0.02176 0.00342 0.00594 -0.00041 C1 1 0.279930 0.582679 0.803108 11.00000 0.01927 0.01915 = 0.01628 0.00841 0.00667 0.00062 C2 1 0.266101 0.646163 0.827352 11.00000 0.02336 0.02162 = 0.02984 0.00659 0.00945 0.00414 AFIX 43 H2 2 0.298820 0.678816 0.845284 11.00000 -1.20000 AFIX 0 C3 1 0.205064 0.669925 0.828768 11.00000 0.03466 0.01610 = 0.04072 0.00612 0.01916 0.00512 C4 1 0.197458 0.707606 0.893534 11.00000 0.04060 0.02780 = 0.05553 -0.00559 0.02016 0.00334 AFIX 43 H4 2 0.232115 0.717207 0.936948 11.00000 -1.20000 AFIX 0 C5 1 0.140222 0.731419 0.895907 11.00000 0.05919 0.03018 = 0.08123 -0.01231 0.04650 0.00176 AFIX 43 H5 2 0.136030 0.756330 0.941092 11.00000 -1.20000 AFIX 0 C6 1 0.089488 0.719103 0.833069 11.00000 0.03862 0.03235 = 0.08167 0.01231 0.03395 0.01564 AFIX 43 H6 2 0.050328 0.735340 0.834745 11.00000 -1.20000 AFIX 0 C7 1 0.096088 0.682972 0.767696 11.00000 0.03421 0.03971 = 0.05699 0.01922 0.01902 0.01274 AFIX 43 H7 2 0.061269 0.674730 0.724054 11.00000 -1.20000 AFIX 0 C8 1 0.153167 0.658456 0.764941 11.00000 0.02985 0.03008 = 0.03703 0.01042 0.01497 0.01273 AFIX 43 H8 2 0.156979 0.633755 0.719440 11.00000 -1.20000 AFIX 0 S1 6 0.403479 0.618098 0.816983 11.00000 0.01927 0.02153 = 0.01930 0.00257 0.00353 -0.00159 O1 4 0.406643 0.660313 0.886002 11.00000 0.03402 0.03065 = 0.01906 -0.00065 0.00574 -0.00630 O2 4 0.453698 0.572070 0.818422 11.00000 0.01918 0.02885 = 0.03733 0.00658 0.00574 0.00180 C9 1 0.392820 0.676985 0.736484 11.00000 0.02044 0.02064 = 0.02082 0.00260 0.00686 0.00137 C10 1 0.421383 0.741681 0.751194 11.00000 0.04475 0.03107 = 0.01963 -0.00316 0.00514 -0.01316 AFIX 43 H10 2 0.442734 0.754537 0.803884 11.00000 -1.20000 AFIX 0 C11 1 0.419214 0.788186 0.689696 11.00000 0.05073 0.02810 = 0.02900 -0.00155 0.01018 -0.01656 AFIX 43 H11 2 0.438728 0.833022 0.700772 11.00000 -1.20000 AFIX 0 C12 1 0.389017 0.770475 0.612080 11.00000 0.02136 0.02315 = 0.02399 0.00242 0.00904 0.00326 C13 1 0.359152 0.705834 0.599389 11.00000 0.04679 0.03114 = 0.02174 0.00301 -0.00088 -0.01449 AFIX 43 H13 2 0.336905 0.693294 0.546949 11.00000 -1.20000 AFIX 0 C14 1 0.360485 0.658804 0.660201 11.00000 0.05009 0.02431 = 0.02541 0.00012 -0.00047 -0.01187 AFIX 43 H14 2 0.339534 0.614770 0.649706 11.00000 -1.20000 AFIX 0 C15 1 0.388839 0.819750 0.544127 11.00000 0.02299 0.02966 = 0.02672 0.00771 0.00460 0.00141 AFIX 23 H15A 2 0.364371 0.862305 0.548019 11.00000 -1.20000 H15B 2 0.368523 0.795587 0.493674 11.00000 -1.20000 AFIX 0 C16 1 0.452558 0.843208 0.542023 11.00000 0.02460 0.02522 = 0.02286 0.00338 0.00586 0.00041 AFIX 23 H16A 2 0.470924 0.872729 0.589209 11.00000 -1.20000 H16B 2 0.478694 0.800793 0.544785 11.00000 -1.20000 AFIX 0 C17 1 0.451919 0.885230 0.467829 11.00000 0.02636 0.03488 = 0.02583 0.00817 0.00711 -0.00028 AFIX 23 H17A 2 0.431599 0.856617 0.420637 11.00000 -1.20000 H17B 2 0.427459 0.928849 0.466510 11.00000 -1.20000 AFIX 0 C18 1 0.515387 0.905612 0.463362 11.00000 0.03002 0.05542 = 0.03700 0.02038 0.01009 0.00146 AFIX 137 H18A 2 0.534446 0.937423 0.507379 11.00000 -1.50000 H18B 2 0.512286 0.929745 0.413016 11.00000 -1.50000 H18C 2 0.540436 0.862838 0.466803 11.00000 -1.50000 AFIX 0 C19 1 0.220465 0.423459 0.861546 11.00000 0.01659 0.02554 = 0.02365 0.01125 0.00795 0.00019 C20 1 0.214769 0.376828 0.794166 11.00000 0.02574 0.02576 = 0.03218 0.00100 0.01410 -0.00410 C21 1 0.165478 0.401794 0.731829 11.00000 0.02257 0.03171 = 0.03162 -0.00238 0.00431 -0.00978 C22 1 0.137071 0.460860 0.761655 11.00000 0.01276 0.03893 = 0.02918 0.01494 0.00435 0.00025 C23 1 0.170001 0.472530 0.842284 11.00000 0.02292 0.02736 = 0.02325 0.01549 0.00989 0.00144 C24 1 0.262034 0.412049 0.943478 11.00000 0.02528 0.03832 = 0.02726 0.01607 0.00522 -0.00125 AFIX 137 H24A 2 0.272224 0.457896 0.970084 11.00000 -1.50000 H24B 2 0.299648 0.388584 0.940021 11.00000 -1.50000 H24C 2 0.241339 0.382225 0.973765 11.00000 -1.50000 AFIX 0 C25 1 0.252253 0.311795 0.792872 11.00000 0.03623 0.02161 = 0.06057 -0.00271 0.02253 -0.00501 AFIX 137 H25A 2 0.230715 0.270117 0.804902 11.00000 -1.50000 H25B 2 0.291953 0.316337 0.832607 11.00000 -1.50000 H25C 2 0.258614 0.306380 0.740260 11.00000 -1.50000 AFIX 0 C26 1 0.143883 0.371012 0.649369 11.00000 0.04498 0.06337 = 0.03809 -0.00979 0.00632 -0.02204 AFIX 137 H26A 2 0.142095 0.408585 0.610284 11.00000 -1.50000 H26B 2 0.103077 0.350369 0.641363 11.00000 -1.50000 H26C 2 0.172474 0.334120 0.642981 11.00000 -1.50000 AFIX 0 C27 1 0.079752 0.496387 0.715023 11.00000 0.02155 0.05954 = 0.05691 0.02112 0.00476 0.00474 AFIX 137 H27A 2 0.045900 0.462328 0.703889 11.00000 -1.50000 H27B 2 0.085352 0.513974 0.665024 11.00000 -1.50000 H27C 2 0.070368 0.536186 0.745537 11.00000 -1.50000 AFIX 0 C28 1 0.154217 0.522743 0.899264 11.00000 0.04583 0.03451 = 0.04210 0.01244 0.02830 0.01266 AFIX 137 H28A 2 0.127706 0.560337 0.869891 11.00000 -1.50000 H28B 2 0.191799 0.543738 0.933206 11.00000 -1.50000 H28C 2 0.132785 0.497118 0.932101 11.00000 -1.50000 AFIX 0 C29 1 0.385416 0.428953 0.847582 11.00000 0.01760 0.02160 = 0.01691 0.00288 0.00429 0.00002 C30 1 0.403633 0.360996 0.832181 11.00000 0.02194 0.02252 = 0.02490 0.00126 0.00612 -0.00030 AFIX 43 H30 2 0.391146 0.342382 0.779927 11.00000 -1.20000 AFIX 0 C31 1 0.440135 0.320624 0.893612 11.00000 0.03189 0.01970 = 0.04071 0.00495 0.00835 0.00504 AFIX 43 H31 2 0.452364 0.274295 0.883266 11.00000 -1.20000 AFIX 0 C32 1 0.458798 0.347943 0.970239 11.00000 0.02484 0.03249 = 0.02884 0.01416 0.00085 0.00159 AFIX 43 H32 2 0.483823 0.320255 1.011944 11.00000 -1.20000 AFIX 0 C33 1 0.441025 0.415086 0.985684 11.00000 0.02555 0.03006 = 0.01983 0.00397 0.00238 -0.00142 AFIX 43 H33 2 0.454210 0.433817 1.037845 11.00000 -1.20000 AFIX 0 C34 1 0.403868 0.455274 0.924984 11.00000 0.02243 0.02191 = 0.02254 0.00061 0.00816 0.00031 AFIX 43 H34 2 0.390867 0.501017 0.936104 11.00000 -1.20000 AFIX 0 C35 1 0.358050 0.457900 0.683294 11.00000 0.02783 0.02118 = 0.01726 0.00313 0.00614 0.00565 C36 1 0.314651 0.430292 0.617069 11.00000 0.03007 0.02538 = 0.02207 -0.00301 0.00676 0.00220 AFIX 43 H36 2 0.272726 0.427838 0.616084 11.00000 -1.20000 AFIX 0 C37 1 0.333595 0.406556 0.552888 11.00000 0.04585 0.03292 = 0.01859 -0.00277 0.00420 0.00518 AFIX 43 H37 2 0.304346 0.388269 0.507540 11.00000 -1.20000 AFIX 0 C38 1 0.394139 0.409279 0.554389 11.00000 0.05532 0.02698 = 0.02567 0.00633 0.02476 0.00993 AFIX 43 H38 2 0.406650 0.391711 0.510665 11.00000 -1.20000 AFIX 0 C39 1 0.437206 0.437433 0.619132 11.00000 0.03653 0.04060 = 0.03431 0.00065 0.02230 0.00325 AFIX 43 H39 2 0.479025 0.439634 0.619554 11.00000 -1.20000 AFIX 0 C40 1 0.419107 0.462380 0.683293 11.00000 0.02324 0.04057 = 0.02641 -0.00453 0.01048 -0.00144 AFIX 43 H40 2 0.448426 0.482570 0.727339 11.00000 -1.20000 AFIX 0 HKLF 4 REM SO834E_0m in C2/c REM R1 = 0.0226 for 5662 Fo > 4sig(Fo) and 0.0292 for all 6384 data REM 430 parameters refined using 0 restraints END WGHT 0.0297 21.7200 REM Highest difference peak 1.124, deepest hole -1.142, 1-sigma level 0.091 Q1 1 0.2337 0.5368 0.7669 11.00000 0.05 1.12 Q2 1 0.2919 0.4900 0.6997 11.00000 0.05 0.97 Q3 1 0.2779 0.4895 0.8006 11.00000 0.05 0.90 Q4 1 0.1907 0.4877 0.7280 11.00000 0.05 0.53 Q5 1 0.2553 0.4618 0.7195 11.00000 0.05 0.50 Q6 1 0.2008 0.4360 0.6396 11.00000 0.05 0.49 Q7 1 0.2669 0.5407 0.9017 11.00000 0.05 0.45 Q8 1 0.2322 0.4886 0.6557 11.00000 0.05 0.45 Q9 1 0.2053 0.5091 0.8074 11.00000 0.05 0.44 Q10 1 0.1801 0.4023 0.7004 11.00000 0.05 0.43 ; _shelx_res_checksum 95116