# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_111201_s6_lm #TrackingRef '111201_s6_lm Ir3ph.cif' _audit_creation_date 2011-12-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C43 H31 Ir N2 O2 S2' _chemical_formula_sum 'C43 H31 Ir N2 O2 S2' _chemical_formula_weight 864.02 _chemical_melting_point ? _chemical_oxdiff_formula C20H20N2O2S2Ir1 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' 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' 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 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.3091(3) _cell_length_b 12.6428(2) _cell_length_c 18.5370(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.9796(16) _cell_angle_gamma 90.00 _cell_volume 4034.48(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6904 _cell_measurement_temperature 130.0 _cell_measurement_theta_max 29.2044 _cell_measurement_theta_min 2.8811 _exptl_absorpt_coefficient_mu 3.448 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0475 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 17296 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.89 _diffrn_ambient_temperature 130.0 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -50.00 45.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -77.0000 -180.0000 95 #__ type_ start__ end____ width___ exp.time_ 2 omega 2.00 90.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 38.0000 120.0000 88 #__ type_ start__ end____ width___ exp.time_ 3 omega 22.00 67.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -112.0000 -41.0000 45 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0014241000 _diffrn_orient_matrix_UB_12 0.0110139000 _diffrn_orient_matrix_UB_13 0.0376298000 _diffrn_orient_matrix_UB_21 0.0410841000 _diffrn_orient_matrix_UB_22 -0.0041039000 _diffrn_orient_matrix_UB_23 0.0032059000 _diffrn_orient_matrix_UB_31 0.0027745000 _diffrn_orient_matrix_UB_32 0.0548634000 _diffrn_orient_matrix_UB_33 -0.0073241000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6861 _reflns_number_total 8188 _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.120 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.104 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 453 _refine_ls_number_reflns 8188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0312 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0244P)^2^+2.1308P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.0673 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.412666(8) 0.768329(11) 0.237362(7) 0.01947(5) Uani 1 1 d . . . S1 S 0.48229(7) 0.46525(8) 0.13770(5) 0.0317(2) Uani 1 1 d . . . S2 S 0.32827(6) 0.98851(7) 0.40118(5) 0.0251(2) Uani 1 1 d . . . O1 O 0.34783(15) 0.86910(19) 0.16083(13) 0.0253(6) Uani 1 1 d . . . O2 O 0.51709(14) 0.82039(19) 0.19567(13) 0.0244(6) Uani 1 1 d . . . N1 N 0.41840(18) 0.6415(2) 0.16866(16) 0.0226(7) Uani 1 1 d . . . N2 N 0.40534(17) 0.8848(2) 0.31321(15) 0.0178(6) Uani 1 1 d . . . C1 C 0.4154(2) 0.5221(3) 0.0720(2) 0.0303(9) Uani 1 1 d . . . C2 C 0.3896(3) 0.4852(3) 0.0037(2) 0.0389(11) Uani 1 1 d . . . H2 H 0.4104 0.4240 -0.0143 0.047 Uiso 1 1 calc R . . C3 C 0.3329(3) 0.5407(3) -0.0372(2) 0.0421(12) Uani 1 1 d . . . H3 H 0.3146 0.5163 -0.0832 0.050 Uiso 1 1 calc R . . C4 C 0.3023(3) 0.6329(3) -0.0108(2) 0.0361(11) Uani 1 1 d . . . H4 H 0.2634 0.6689 -0.0392 0.043 Uiso 1 1 calc R . . C5 C 0.3286(3) 0.6717(3) 0.0564(2) 0.0319(10) Uani 1 1 d . . . H5 H 0.3081 0.7337 0.0736 0.038 Uiso 1 1 calc R . . C6 C 0.3864(2) 0.6165(3) 0.0982(2) 0.0272(9) Uani 1 1 d . . . C7 C 0.4679(2) 0.5687(3) 0.19538(19) 0.0246(8) Uani 1 1 d . . . C8 C 0.5008(2) 0.5775(3) 0.26943(19) 0.0218(8) Uani 1 1 d . . . C9 C 0.5481(2) 0.5012(3) 0.3052(2) 0.0242(8) Uani 1 1 d . . . H9 H 0.5614 0.4412 0.2802 0.029 Uiso 1 1 calc R . . C10 C 0.5758(2) 0.5136(3) 0.37758(19) 0.0251(9) Uani 1 1 d . . . C11 C 0.5528(2) 0.6054(3) 0.4130(2) 0.0298(9) Uani 1 1 d . . . H11 H 0.5704 0.6159 0.4616 0.036 Uiso 1 1 calc R . . C12 C 0.5045(2) 0.6807(3) 0.3772(2) 0.0277(9) Uani 1 1 d . . . H12 H 0.4904 0.7398 0.4027 0.033 Uiso 1 1 calc R . . C13 C 0.4764(2) 0.6704(3) 0.30396(19) 0.0213(8) Uani 1 1 d . . . C14 C 0.6246(2) 0.4307(3) 0.4166(2) 0.0261(9) Uani 1 1 d . . . C15 C 0.6735(2) 0.3682(3) 0.3798(2) 0.0295(9) Uani 1 1 d . . . H15 H 0.6772 0.3808 0.3308 0.035 Uiso 1 1 calc R . . C16 C 0.7170(2) 0.2875(3) 0.4146(2) 0.0313(9) Uani 1 1 d . . . H16 H 0.7486 0.2453 0.3889 0.038 Uiso 1 1 calc R . . C17 C 0.7130(2) 0.2700(3) 0.4877(2) 0.0287(9) Uani 1 1 d . . . H17 H 0.7423 0.2164 0.5115 0.034 Uiso 1 1 calc R . . C18 C 0.6654(2) 0.3324(3) 0.5253(2) 0.0295(9) Uani 1 1 d . . . H18 H 0.6630 0.3208 0.5745 0.035 Uiso 1 1 calc R . . C19 C 0.6214(2) 0.4117(3) 0.4903(2) 0.0265(9) Uani 1 1 d . . . H19 H 0.5893 0.4529 0.5161 0.032 Uiso 1 1 calc R . . C20 C 0.4243(2) 1.0248(3) 0.3944(2) 0.0250(9) Uani 1 1 d . . . C21 C 0.4666(3) 1.1053(4) 0.4313(2) 0.0418(12) Uani 1 1 d . . . H21 H 0.4437 1.1495 0.4631 0.050 Uiso 1 1 calc R . . C22 C 0.5427(3) 1.1174(4) 0.4195(2) 0.0413(12) Uani 1 1 d . . . H22 H 0.5720 1.1706 0.4437 0.050 Uiso 1 1 calc R . . C23 C 0.5773(2) 1.0513(3) 0.3715(2) 0.0369(11) Uani 1 1 d . . . H23 H 0.6293 1.0608 0.3648 0.044 Uiso 1 1 calc R . . C24 C 0.5349(2) 0.9715(3) 0.3338(2) 0.0281(9) Uani 1 1 d . . . H24 H 0.5580 0.9273 0.3022 0.034 Uiso 1 1 calc R . . C25 C 0.4576(2) 0.9599(3) 0.34474(19) 0.0226(8) Uani 1 1 d . . . C26 C 0.3369(2) 0.8898(3) 0.33830(19) 0.0181(8) Uani 1 1 d . . . C27 C 0.2810(2) 0.8087(3) 0.31651(18) 0.0193(8) Uani 1 1 d . . . C28 C 0.3112(2) 0.7308(3) 0.27178(18) 0.0199(8) Uani 1 1 d . . . C29 C 0.2625(2) 0.6433(3) 0.2544(2) 0.0255(9) Uani 1 1 d . . . H29 H 0.2801 0.5884 0.2270 0.031 Uiso 1 1 calc R . . C30 C 0.1894(2) 0.6370(3) 0.27694(19) 0.0261(9) Uani 1 1 d . . . H30 H 0.1586 0.5785 0.2636 0.031 Uiso 1 1 calc R . . C31 C 0.1599(2) 0.7158(3) 0.31921(19) 0.0217(8) Uani 1 1 d . . . C32 C 0.2071(2) 0.8018(3) 0.33935(19) 0.0216(8) Uani 1 1 d . . . H32 H 0.1892 0.8549 0.3681 0.026 Uiso 1 1 calc R . . C33 C 0.0806(2) 0.7091(3) 0.3423(2) 0.0231(8) Uani 1 1 d . . . C34 C 0.0165(2) 0.6898(3) 0.2917(2) 0.0285(9) Uani 1 1 d . . . H34 H 0.0237 0.6783 0.2433 0.034 Uiso 1 1 calc R . . C35 C -0.0576(3) 0.6876(3) 0.3134(3) 0.0375(10) Uani 1 1 d . . . H35 H -0.0997 0.6754 0.2790 0.045 Uiso 1 1 calc R . . C36 C -0.0703(2) 0.7033(3) 0.3847(2) 0.0359(10) Uani 1 1 d . . . H36 H -0.1204 0.7019 0.3985 0.043 Uiso 1 1 calc R . . C37 C -0.0070(2) 0.7210(3) 0.4355(2) 0.0305(9) Uani 1 1 d . . . H37 H -0.0145 0.7313 0.4840 0.037 Uiso 1 1 calc R . . C38 C 0.0669(2) 0.7234(3) 0.4145(2) 0.0249(8) Uani 1 1 d . . . H38 H 0.1087 0.7349 0.4492 0.030 Uiso 1 1 calc R . . C39 C 0.3184(2) 0.9815(3) 0.0617(2) 0.0328(10) Uani 1 1 d . . . H39A H 0.2904 0.9317 0.0298 0.049 Uiso 1 1 calc R . . H39B H 0.3443 1.0316 0.0337 0.049 Uiso 1 1 calc R . . H39C H 0.2827 1.0181 0.0892 0.049 Uiso 1 1 calc R . . C40 C 0.3773(2) 0.9238(3) 0.1124(2) 0.0239(8) Uani 1 1 d . . . C41 C 0.4556(2) 0.9337(3) 0.1036(2) 0.0304(9) Uani 1 1 d . . . H41 H 0.4676 0.9784 0.0665 0.037 Uiso 1 1 calc R . . C42 C 0.5192(2) 0.8848(3) 0.1437(2) 0.0256(9) Uani 1 1 d . . . C43 C 0.5991(3) 0.9080(4) 0.1232(2) 0.0410(11) Uani 1 1 d . . . H43A H 0.6326 0.9267 0.1659 0.061 Uiso 1 1 calc R . . H43B H 0.5966 0.9658 0.0894 0.061 Uiso 1 1 calc R . . H43C H 0.6192 0.8465 0.1013 0.061 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 0.01959(8) 0.01867(8) 0.02079(8) 0.00177(6) 0.00514(6) -0.00275(6) S1 0.0402(7) 0.0270(5) 0.0287(5) -0.0046(4) 0.0078(5) 0.0003(5) S2 0.0210(5) 0.0231(5) 0.0316(5) -0.0046(4) 0.0052(4) -0.0033(4) O1 0.0270(16) 0.0241(14) 0.0249(14) 0.0015(11) 0.0038(11) 0.0006(12) O2 0.0214(15) 0.0243(14) 0.0292(14) 0.0033(11) 0.0098(11) 0.0005(11) N1 0.0256(18) 0.0226(17) 0.0210(16) 0.0026(13) 0.0090(13) -0.0051(14) N2 0.0137(16) 0.0175(15) 0.0221(16) 0.0040(12) 0.0023(12) -0.0019(12) C1 0.038(3) 0.031(2) 0.024(2) -0.0002(17) 0.0088(18) -0.0088(19) C2 0.062(3) 0.030(2) 0.027(2) -0.0049(18) 0.014(2) -0.008(2) C3 0.064(3) 0.041(3) 0.021(2) -0.0054(19) 0.003(2) -0.011(2) C4 0.050(3) 0.033(2) 0.023(2) 0.0062(18) -0.002(2) -0.011(2) C5 0.044(3) 0.028(2) 0.025(2) 0.0050(16) 0.0045(18) -0.0047(19) C6 0.036(2) 0.022(2) 0.024(2) 0.0026(16) 0.0058(17) -0.0085(18) C7 0.028(2) 0.024(2) 0.023(2) 0.0020(16) 0.0121(16) -0.0088(17) C8 0.019(2) 0.022(2) 0.025(2) 0.0008(15) 0.0077(15) -0.0041(16) C9 0.022(2) 0.024(2) 0.028(2) 0.0015(16) 0.0127(16) -0.0014(16) C10 0.027(2) 0.027(2) 0.023(2) 0.0065(16) 0.0093(16) 0.0012(17) C11 0.040(3) 0.033(2) 0.0175(19) 0.0026(16) 0.0086(17) 0.0075(19) C12 0.031(2) 0.026(2) 0.028(2) -0.0022(16) 0.0127(17) 0.0052(18) C13 0.021(2) 0.021(2) 0.0237(19) 0.0010(15) 0.0093(15) -0.0028(15) C14 0.023(2) 0.025(2) 0.031(2) 0.0063(16) 0.0053(17) -0.0003(17) C15 0.027(2) 0.039(2) 0.024(2) 0.0054(17) 0.0080(17) 0.0037(19) C16 0.021(2) 0.033(2) 0.042(2) 0.0007(18) 0.0075(18) -0.0019(18) C17 0.019(2) 0.027(2) 0.038(2) 0.0054(18) -0.0067(17) -0.0054(17) C18 0.030(2) 0.029(2) 0.028(2) 0.0035(17) -0.0033(18) -0.0088(18) C19 0.025(2) 0.028(2) 0.027(2) 0.0000(16) 0.0059(17) -0.0043(17) C20 0.023(2) 0.025(2) 0.028(2) -0.0009(16) 0.0024(16) -0.0061(17) C21 0.041(3) 0.041(3) 0.042(3) -0.010(2) -0.003(2) -0.015(2) C22 0.040(3) 0.047(3) 0.035(3) -0.011(2) -0.004(2) -0.026(2) C23 0.017(2) 0.047(3) 0.045(3) 0.007(2) -0.0056(19) -0.013(2) C24 0.023(2) 0.030(2) 0.031(2) 0.0041(17) 0.0021(17) -0.0028(17) C25 0.020(2) 0.023(2) 0.024(2) 0.0033(15) -0.0015(16) -0.0037(16) C26 0.0182(19) 0.0157(17) 0.0200(18) 0.0022(14) 0.0001(15) 0.0004(15) C27 0.021(2) 0.0188(18) 0.0176(18) 0.0042(14) -0.0006(15) 0.0006(16) C28 0.0203(19) 0.0228(18) 0.0169(18) -0.0006(14) 0.0041(14) -0.0020(16) C29 0.026(2) 0.024(2) 0.026(2) -0.0050(16) 0.0024(17) -0.0087(17) C30 0.031(2) 0.026(2) 0.021(2) -0.0036(16) 0.0033(17) -0.0154(17) C31 0.022(2) 0.021(2) 0.0208(19) 0.0054(15) -0.0005(15) -0.0044(16) C32 0.021(2) 0.0214(19) 0.0216(19) 0.0054(15) -0.0011(15) 0.0013(16) C33 0.022(2) 0.019(2) 0.028(2) 0.0048(15) 0.0012(16) -0.0043(15) C34 0.022(2) 0.029(2) 0.034(2) -0.0014(17) 0.0025(17) -0.0050(18) C35 0.024(2) 0.037(2) 0.051(3) -0.006(2) 0.000(2) -0.009(2) C36 0.021(2) 0.031(2) 0.058(3) 0.001(2) 0.016(2) -0.0031(18) C37 0.033(2) 0.026(2) 0.035(2) 0.0020(17) 0.0141(19) -0.0034(18) C38 0.024(2) 0.025(2) 0.027(2) 0.0054(16) 0.0033(16) -0.0042(17) C39 0.037(3) 0.028(2) 0.032(2) 0.0092(17) -0.0010(19) -0.0007(19) C40 0.033(2) 0.0155(18) 0.024(2) 0.0000(15) 0.0037(17) -0.0021(16) C41 0.035(3) 0.028(2) 0.028(2) 0.0091(17) 0.0080(18) 0.0003(19) C42 0.030(2) 0.0183(19) 0.031(2) 0.0017(16) 0.0150(17) 0.0019(17) C43 0.033(3) 0.044(3) 0.049(3) 0.014(2) 0.020(2) -0.001(2) _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 O1 2.136(2) . ? Ir1 O2 2.142(3) . ? Ir1 N1 2.057(3) . ? Ir1 N2 2.049(3) . ? Ir1 C13 1.998(4) . ? Ir1 C28 1.988(4) . ? S1 C1 1.745(4) . ? S1 C7 1.723(4) . ? S2 C20 1.741(4) . ? S2 C26 1.724(4) . ? O1 C40 1.280(4) . ? O2 C42 1.265(4) . ? N1 C6 1.401(5) . ? N1 C7 1.318(5) . ? N2 C25 1.397(4) . ? N2 C26 1.318(5) . ? C1 C2 1.380(5) . ? C1 C6 1.401(5) . ? C2 H2 0.9300 . ? C2 C3 1.369(6) . ? C3 H3 0.9300 . ? C3 C4 1.391(6) . ? C4 H4 0.9300 . ? C4 C5 1.373(5) . ? C5 H5 0.9300 . ? C5 C6 1.388(5) . ? C7 C8 1.435(5) . ? C8 C9 1.387(5) . ? C8 C13 1.423(5) . ? C9 H9 0.9300 . ? C9 C10 1.386(5) . ? C10 C11 1.412(5) . ? C10 C14 1.485(5) . ? C11 H11 0.9300 . ? C11 C12 1.388(5) . ? C12 H12 0.9300 . ? C12 C13 1.400(5) . ? C14 C15 1.389(5) . ? C14 C19 1.392(5) . ? C15 H15 0.9300 . ? C15 C16 1.388(5) . ? C16 H16 0.9300 . ? C16 C17 1.381(6) . ? C17 H17 0.9300 . ? C17 C18 1.380(6) . ? C18 H18 0.9300 . ? C18 C19 1.381(5) . ? C19 H19 0.9300 . ? C20 C21 1.392(5) . ? C20 C25 1.401(5) . ? C21 H21 0.9300 . ? C21 C22 1.366(6) . ? C22 H22 0.9300 . ? C22 C23 1.400(6) . ? C23 H23 0.9300 . ? C23 C24 1.391(5) . ? C24 H24 0.9300 . ? C24 C25 1.382(5) . ? C26 C27 1.439(5) . ? C27 C28 1.421(5) . ? C27 C32 1.392(5) . ? C28 C29 1.408(5) . ? C29 H29 0.9300 . ? C29 C30 1.375(5) . ? C30 H30 0.9300 . ? C30 C31 1.396(5) . ? C31 C32 1.387(5) . ? C31 C33 1.483(5) . ? C32 H32 0.9300 . ? C33 C34 1.398(5) . ? C33 C38 1.394(5) . ? C34 H34 0.9300 . ? C34 C35 1.384(6) . ? C35 H35 0.9300 . ? C35 C36 1.376(6) . ? C36 H36 0.9300 . ? C36 C37 1.387(6) . ? C37 H37 0.9300 . ? C37 C38 1.375(5) . ? C38 H38 0.9300 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C39 C40 1.503(5) . ? C40 C41 1.388(5) . ? C41 H41 0.9300 . ? C41 C42 1.405(5) . ? C42 C43 1.500(5) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ir1 O2 88.96(10) . . ? N1 Ir1 O1 96.31(11) . . ? N1 Ir1 O2 85.37(11) . . ? N2 Ir1 O1 87.79(10) . . ? N2 Ir1 O2 98.15(10) . . ? N2 Ir1 N1 174.67(11) . . ? C13 Ir1 O1 176.52(12) . . ? C13 Ir1 O2 88.89(12) . . ? C13 Ir1 N1 80.80(13) . . ? C13 Ir1 N2 95.22(13) . . ? C28 Ir1 O1 86.27(12) . . ? C28 Ir1 O2 175.03(12) . . ? C28 Ir1 N1 96.53(13) . . ? C28 Ir1 N2 80.29(13) . . ? C28 Ir1 C13 95.94(14) . . ? C7 S1 C1 89.56(19) . . ? C26 S2 C20 89.49(18) . . ? C40 O1 Ir1 124.6(3) . . ? C42 O2 Ir1 124.4(2) . . ? C6 N1 Ir1 135.5(3) . . ? C7 N1 Ir1 112.5(2) . . ? C7 N1 C6 111.8(3) . . ? C25 N2 Ir1 133.8(3) . . ? C26 N2 Ir1 113.5(2) . . ? C26 N2 C25 112.7(3) . . ? C2 C1 S1 129.0(3) . . ? C2 C1 C6 120.8(4) . . ? C6 C1 S1 110.2(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 C1 118.7(4) . . ? C3 C2 H2 120.6 . . ? C2 C3 H3 119.6 . . ? C2 C3 C4 120.8(4) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 119.4 . . ? C5 C4 C3 121.2(4) . . ? C5 C4 H4 119.4 . . ? C4 C5 H5 120.7 . . ? C4 C5 C6 118.5(4) . . ? C6 C5 H5 120.7 . . ? N1 C6 C1 113.2(3) . . ? C5 C6 N1 126.8(4) . . ? C5 C6 C1 119.9(4) . . ? N1 C7 S1 115.3(3) . . ? N1 C7 C8 118.9(3) . . ? C8 C7 S1 125.7(3) . . ? C9 C8 C7 124.0(3) . . ? C9 C8 C13 123.1(3) . . ? C13 C8 C7 112.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 C8 120.8(4) . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 117.1(3) . . ? C9 C10 C14 121.0(3) . . ? C11 C10 C14 121.8(3) . . ? C10 C11 H11 119.1 . . ? C12 C11 C10 121.8(4) . . ? C12 C11 H11 119.1 . . ? C11 C12 H12 119.0 . . ? C11 C12 C13 122.0(4) . . ? C13 C12 H12 119.0 . . ? C8 C13 Ir1 113.8(3) . . ? C12 C13 Ir1 130.9(3) . . ? C12 C13 C8 115.1(3) . . ? C15 C14 C10 120.4(3) . . ? C15 C14 C19 118.2(4) . . ? C19 C14 C10 121.4(4) . . ? C14 C15 H15 119.4 . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C15 C16 H16 120.2 . . ? C17 C16 C15 119.6(4) . . ? C17 C16 H16 120.2 . . ? C16 C17 H17 120.1 . . ? C18 C17 C16 119.8(4) . . ? C18 C17 H17 120.1 . . ? C17 C18 H18 119.8 . . ? C17 C18 C19 120.5(4) . . ? C19 C18 H18 119.8 . . ? C14 C19 H19 119.7 . . ? C18 C19 C14 120.7(4) . . ? C18 C19 H19 119.7 . . ? C21 C20 S2 127.9(3) . . ? C21 C20 C25 121.3(4) . . ? C25 C20 S2 110.8(3) . . ? C20 C21 H21 121.0 . . ? C22 C21 C20 118.0(4) . . ? C22 C21 H21 121.0 . . ? C21 C22 H22 119.4 . . ? C21 C22 C23 121.2(4) . . ? C23 C22 H22 119.4 . . ? C22 C23 H23 119.6 . . ? C24 C23 C22 120.9(4) . . ? C24 C23 H23 119.6 . . ? C23 C24 H24 120.9 . . ? C25 C24 C23 118.1(4) . . ? C25 C24 H24 120.9 . . ? N2 C25 C20 112.3(3) . . ? C24 C25 N2 127.3(4) . . ? C24 C25 C20 120.3(3) . . ? N2 C26 S2 114.7(3) . . ? N2 C26 C27 118.0(3) . . ? C27 C26 S2 127.0(3) . . ? C28 C27 C26 112.4(3) . . ? C32 C27 C26 124.9(3) . . ? C32 C27 C28 122.6(3) . . ? C27 C28 Ir1 114.4(3) . . ? C29 C28 Ir1 130.0(3) . . ? C29 C28 C27 115.5(3) . . ? C28 C29 H29 119.2 . . ? C30 C29 C28 121.6(4) . . ? C30 C29 H29 119.2 . . ? C29 C30 H30 119.0 . . ? C29 C30 C31 122.0(3) . . ? C31 C30 H30 119.0 . . ? C30 C31 C33 121.6(3) . . ? C32 C31 C30 118.2(4) . . ? C32 C31 C33 120.2(3) . . ? C27 C32 H32 120.0 . . ? C31 C32 C27 120.0(4) . . ? C31 C32 H32 120.0 . . ? C34 C33 C31 120.7(3) . . ? C38 C33 C31 121.7(3) . . ? C38 C33 C34 117.6(4) . . ? C33 C34 H34 119.9 . . ? C35 C34 C33 120.3(4) . . ? C35 C34 H34 119.9 . . ? C34 C35 H35 119.3 . . ? C36 C35 C34 121.4(4) . . ? C36 C35 H35 119.3 . . ? C35 C36 H36 120.6 . . ? C35 C36 C37 118.8(4) . . ? C37 C36 H36 120.6 . . ? C36 C37 H37 119.9 . . ? C38 C37 C36 120.2(4) . . ? C38 C37 H37 119.9 . . ? C33 C38 H38 119.1 . . ? C37 C38 C33 121.7(4) . . ? C37 C38 H38 119.1 . . ? H39A C39 H39B 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C40 C39 H39A 109.5 . . ? C40 C39 H39B 109.5 . . ? C40 C39 H39C 109.5 . . ? O1 C40 C39 114.0(4) . . ? O1 C40 C41 126.6(3) . . ? C41 C40 C39 119.4(3) . . ? C40 C41 H41 115.9 . . ? C40 C41 C42 128.2(4) . . ? C42 C41 H41 115.9 . . ? O2 C42 C41 127.1(4) . . ? O2 C42 C43 114.8(3) . . ? C41 C42 C43 118.1(3) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43B 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 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 Ir1 O1 C40 C39 175.5(2) . . . . ? Ir1 O1 C40 C41 -4.6(5) . . . . ? Ir1 O2 C42 C41 -0.3(5) . . . . ? Ir1 O2 C42 C43 -179.0(3) . . . . ? Ir1 N1 C6 C1 173.4(3) . . . . ? Ir1 N1 C6 C5 -10.2(6) . . . . ? Ir1 N1 C7 S1 -174.58(17) . . . . ? Ir1 N1 C7 C8 9.4(4) . . . . ? Ir1 N2 C25 C20 179.1(2) . . . . ? Ir1 N2 C25 C24 -3.7(6) . . . . ? Ir1 N2 C26 S2 -178.96(15) . . . . ? Ir1 N2 C26 C27 6.7(4) . . . . ? Ir1 C28 C29 C30 -171.9(3) . . . . ? S1 C1 C2 C3 176.2(3) . . . . ? S1 C1 C6 N1 0.7(4) . . . . ? S1 C1 C6 C5 -176.0(3) . . . . ? S1 C7 C8 C9 -1.4(6) . . . . ? S1 C7 C8 C13 -178.2(3) . . . . ? S2 C20 C21 C22 177.6(3) . . . . ? S2 C20 C25 N2 0.8(4) . . . . ? S2 C20 C25 C24 -176.6(3) . . . . ? S2 C26 C27 C28 -171.1(3) . . . . ? S2 C26 C27 C32 5.2(5) . . . . ? O1 Ir1 O2 C42 -1.6(3) . . . . ? O1 Ir1 N1 C6 -6.2(4) . . . . ? O1 Ir1 N1 C7 168.5(2) . . . . ? O1 Ir1 N2 C25 -103.7(3) . . . . ? O1 Ir1 N2 C26 76.9(2) . . . . ? O1 Ir1 C13 C8 -25(2) . . . . ? O1 Ir1 C13 C12 150.5(18) . . . . ? O1 Ir1 C28 C27 -77.4(3) . . . . ? O1 Ir1 C28 C29 97.3(3) . . . . ? O1 C40 C41 C42 1.8(7) . . . . ? O2 Ir1 O1 C40 3.9(3) . . . . ? O2 Ir1 N1 C6 -94.7(4) . . . . ? O2 Ir1 N1 C7 80.1(3) . . . . ? O2 Ir1 N2 C25 -15.1(3) . . . . ? O2 Ir1 N2 C26 165.5(2) . . . . ? O2 Ir1 C13 C8 -77.3(3) . . . . ? O2 Ir1 C13 C12 98.6(4) . . . . ? O2 Ir1 C28 C27 -61.1(14) . . . . ? O2 Ir1 C28 C29 113.6(13) . . . . ? N1 Ir1 O1 C40 -81.4(3) . . . . ? N1 Ir1 O2 C42 94.8(3) . . . . ? N1 Ir1 N2 C25 116.0(12) . . . . ? N1 Ir1 N2 C26 -63.4(13) . . . . ? N1 Ir1 C13 C8 8.2(3) . . . . ? N1 Ir1 C13 C12 -175.9(4) . . . . ? N1 Ir1 C28 C27 -173.3(3) . . . . ? N1 Ir1 C28 C29 1.4(4) . . . . ? N1 C7 C8 C9 174.2(3) . . . . ? N1 C7 C8 C13 -2.6(5) . . . . ? N2 Ir1 O1 C40 102.1(3) . . . . ? N2 Ir1 O2 C42 -89.2(3) . . . . ? N2 Ir1 N1 C6 133.8(11) . . . . ? N2 Ir1 N1 C7 -51.5(13) . . . . ? N2 Ir1 C13 C8 -175.3(3) . . . . ? N2 Ir1 C13 C12 0.6(4) . . . . ? N2 Ir1 C28 C27 11.0(2) . . . . ? N2 Ir1 C28 C29 -174.3(4) . . . . ? N2 C26 C27 C28 2.4(4) . . . . ? N2 C26 C27 C32 178.7(3) . . . . ? C1 S1 C7 N1 -0.9(3) . . . . ? C1 S1 C7 C8 174.8(3) . . . . ? C1 C2 C3 C4 0.7(7) . . . . ? C2 C1 C6 N1 179.5(4) . . . . ? C2 C1 C6 C5 2.8(6) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C4 C5 C6 N1 -177.5(4) . . . . ? C4 C5 C6 C1 -1.4(6) . . . . ? C6 N1 C7 S1 1.5(4) . . . . ? C6 N1 C7 C8 -174.6(3) . . . . ? C6 C1 C2 C3 -2.4(6) . . . . ? C7 S1 C1 C2 -178.6(4) . . . . ? C7 S1 C1 C6 0.1(3) . . . . ? C7 N1 C6 C1 -1.3(5) . . . . ? C7 N1 C6 C5 175.1(4) . . . . ? C7 C8 C9 C10 -177.9(4) . . . . ? C7 C8 C13 Ir1 -5.8(4) . . . . ? C7 C8 C13 C12 177.6(3) . . . . ? C8 C9 C10 C11 1.0(6) . . . . ? C8 C9 C10 C14 178.2(3) . . . . ? C9 C8 C13 Ir1 177.4(3) . . . . ? C9 C8 C13 C12 0.8(5) . . . . ? C9 C10 C11 C12 0.0(6) . . . . ? C9 C10 C14 C15 31.1(6) . . . . ? C9 C10 C14 C19 -147.4(4) . . . . ? C10 C11 C12 C13 -0.6(6) . . . . ? C10 C14 C15 C16 -177.2(4) . . . . ? C10 C14 C19 C18 178.1(3) . . . . ? C11 C10 C14 C15 -151.8(4) . . . . ? C11 C10 C14 C19 29.7(6) . . . . ? C11 C12 C13 Ir1 -175.6(3) . . . . ? C11 C12 C13 C8 0.2(6) . . . . ? C13 Ir1 O1 C40 -48(2) . . . . ? C13 Ir1 O2 C42 175.7(3) . . . . ? C13 Ir1 N1 C6 175.7(4) . . . . ? C13 Ir1 N1 C7 -9.6(3) . . . . ? C13 Ir1 N2 C25 74.5(3) . . . . ? C13 Ir1 N2 C26 -104.9(2) . . . . ? C13 Ir1 C28 C27 105.3(3) . . . . ? C13 Ir1 C28 C29 -80.0(3) . . . . ? C13 C8 C9 C10 -1.4(6) . . . . ? C14 C10 C11 C12 -177.2(4) . . . . ? C14 C15 C16 C17 -1.4(6) . . . . ? C15 C14 C19 C18 -0.4(6) . . . . ? C15 C16 C17 C18 0.5(6) . . . . ? C16 C17 C18 C19 0.4(6) . . . . ? C17 C18 C19 C14 -0.4(6) . . . . ? C19 C14 C15 C16 1.4(6) . . . . ? C20 S2 C26 N2 -0.9(3) . . . . ? C20 S2 C26 C27 172.8(3) . . . . ? C20 C21 C22 C23 0.2(7) . . . . ? C21 C20 C25 N2 -179.5(3) . . . . ? C21 C20 C25 C24 3.1(6) . . . . ? C21 C22 C23 C24 0.6(7) . . . . ? C22 C23 C24 C25 0.4(6) . . . . ? C23 C24 C25 N2 -179.2(3) . . . . ? C23 C24 C25 C20 -2.2(5) . . . . ? C25 N2 C26 S2 1.5(4) . . . . ? C25 N2 C26 C27 -172.8(3) . . . . ? C25 C20 C21 C22 -2.0(6) . . . . ? C26 S2 C20 C21 -179.7(4) . . . . ? C26 S2 C20 C25 0.0(3) . . . . ? C26 N2 C25 C20 -1.4(4) . . . . ? C26 N2 C25 C24 175.7(3) . . . . ? C26 C27 C28 Ir1 -10.6(4) . . . . ? C26 C27 C28 C29 173.8(3) . . . . ? C26 C27 C32 C31 -175.2(3) . . . . ? C27 C28 C29 C30 2.7(5) . . . . ? C28 Ir1 O1 C40 -177.5(3) . . . . ? C28 Ir1 O2 C42 -17.9(15) . . . . ? C28 Ir1 N1 C6 80.7(4) . . . . ? C28 Ir1 N1 C7 -104.6(3) . . . . ? C28 Ir1 N2 C25 169.7(3) . . . . ? C28 Ir1 N2 C26 -9.7(2) . . . . ? C28 Ir1 C13 C8 103.9(3) . . . . ? C28 Ir1 C13 C12 -80.2(4) . . . . ? C28 C27 C32 C31 0.8(5) . . . . ? C28 C29 C30 C31 -1.1(6) . . . . ? C29 C30 C31 C32 -0.8(5) . . . . ? C29 C30 C31 C33 179.0(3) . . . . ? C30 C31 C32 C27 1.0(5) . . . . ? C30 C31 C33 C34 -51.2(5) . . . . ? C30 C31 C33 C38 129.8(4) . . . . ? C31 C33 C34 C35 -177.6(4) . . . . ? C31 C33 C38 C37 177.6(3) . . . . ? C32 C27 C28 Ir1 172.9(3) . . . . ? C32 C27 C28 C29 -2.6(5) . . . . ? C32 C31 C33 C34 128.7(4) . . . . ? C32 C31 C33 C38 -50.3(5) . . . . ? C33 C31 C32 C27 -178.9(3) . . . . ? C33 C34 C35 C36 -0.7(6) . . . . ? C34 C33 C38 C37 -1.4(5) . . . . ? C34 C35 C36 C37 -0.3(6) . . . . ? C35 C36 C37 C38 0.4(6) . . . . ? C36 C37 C38 C33 0.5(6) . . . . ? C38 C33 C34 C35 1.5(6) . . . . ? C39 C40 C41 C42 -178.3(4) . . . . ? C40 C41 C42 O2 1.0(7) . . . . ? C40 C41 C42 C43 179.7(4) . . . . ? _platon_squeeze_details ; ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.131 -0.141 0.131 72 24 ' ' 2 0.250 0.026 0.750 247 76 ' ' 3 0.750 -0.036 0.250 247 77 ' ' 4 0.869 0.141 0.869 72 24 ' ' 5 0.369 0.359 0.369 72 24 ' ' 6 0.631 0.641 0.631 72 24 ' ' _database_code_depnum_ccdc_archive 'CCDC 857631' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_twin_twin1_hklf4 #TrackingRef 'twin_twin1_hklf4 Irbt.cif' _audit_creation_date 2011-12-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H23 Ir N2 O2 S2, C6 H6' _chemical_formula_sum 'C37 H28 Ir N2 O2 S2' _chemical_formula_weight 788.93 _chemical_melting_point ? _chemical_oxdiff_formula C20H20N2O2S2Ir1 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' 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' 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 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 14.8264(7) _cell_length_b 15.4413(5) _cell_length_c 13.7415(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.573(4) _cell_angle_gamma 90.00 _cell_volume 3125.3(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5224 _cell_measurement_temperature 130.00(10) _cell_measurement_theta_max 26.3151 _cell_measurement_theta_min 2.7523 _exptl_absorpt_coefficient_mu 4.443 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73458 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1556 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_unetI/netI 0.0648 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8700 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.98 _diffrn_ambient_temperature 130.00(10) _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.742 _diffrn_measured_fraction_theta_max 0.742 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -26.00 5.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -65.0000 130.0000 31 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 87.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 77.0000 120.0000 89 #__ type_ start__ end____ width___ exp.time_ 3 omega -47.00 49.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -77.0000 0.0000 96 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0298578000 _diffrn_orient_matrix_UB_12 0.0326995000 _diffrn_orient_matrix_UB_13 -0.0208012000 _diffrn_orient_matrix_UB_21 0.0315750000 _diffrn_orient_matrix_UB_22 0.0109034000 _diffrn_orient_matrix_UB_23 -0.0331011000 _diffrn_orient_matrix_UB_31 -0.0206920000 _diffrn_orient_matrix_UB_32 -0.0303987000 _diffrn_orient_matrix_UB_33 -0.0342091000 loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.7198 3642 9600 2 0.2802 3603 9600 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3144 _reflns_number_total 4094 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.988 _refine_diff_density_min -1.049 _refine_diff_density_rms 0.127 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 399 _refine_ls_number_reflns 4094 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0350 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.0845 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.285835(18) 0.008402(14) 0.733156(18) 0.01746(10) Uani 1 1 d . . . S1 S 0.19470(17) -0.12713(13) 0.45082(14) 0.0378(5) Uani 1 1 d . . . S2 S 0.21019(14) 0.14178(11) 1.00168(13) 0.0261(4) Uani 1 1 d . . . O1 O 0.3876(3) 0.0722(3) 0.6584(3) 0.0218(11) Uani 1 1 d . . . O2 O 0.3942(3) -0.0517(3) 0.8261(3) 0.0211(11) Uani 1 1 d . . . N1 N 0.2721(4) -0.0781(3) 0.6184(4) 0.0205(13) Uani 1 1 d . . . N2 N 0.2774(4) 0.0946(3) 0.8451(4) 0.0202(13) Uani 1 1 d . . . C1 C 0.2765(6) -0.1933(5) 0.5108(5) 0.034(2) Uani 1 1 d . . . C1A C 0.3116(5) -0.1575(4) 0.6008(5) 0.0211(16) Uani 1 1 d . . . C1B C 0.2109(6) -0.0548(4) 0.5456(5) 0.0267(18) Uani 1 1 d . . . C1C C 0.5419(5) -0.0841(5) 0.8989(5) 0.035(2) Uani 1 1 d . . . H1CA H 0.5392 -0.0565 0.9611 0.052 Uiso 1 1 calc R . . H1CB H 0.6025 -0.0798 0.8811 0.052 Uiso 1 1 calc R . . H1CC H 0.5255 -0.1440 0.9034 0.052 Uiso 1 1 calc R . . C1D C 0.5284(5) 0.1085(5) 0.6101(6) 0.041(2) Uani 1 1 d . . . H1DA H 0.5267 0.0781 0.5490 0.062 Uiso 1 1 calc R . . H1DB H 0.5900 0.1116 0.6404 0.062 Uiso 1 1 calc R . . H1DC H 0.5050 0.1660 0.5985 0.062 Uiso 1 1 calc R . . C2 C 0.5160(6) 0.0109(4) 0.7532(5) 0.0269(17) Uani 1 1 d . . . H2 H 0.5791 0.0116 0.7586 0.032 Uiso 1 1 calc R . . C3 C 0.3749(5) -0.2021(4) 0.6624(6) 0.0296(18) Uani 1 1 d . . . H3 H 0.3968 -0.1799 0.7235 0.035 Uiso 1 1 calc R . . C4 C 0.3765(6) 0.3122(5) 0.8307(6) 0.036(2) Uani 1 1 d . . . H4 H 0.4106 0.3457 0.7921 0.043 Uiso 1 1 calc R . . C5 C 0.4049(6) -0.2807(5) 0.6311(7) 0.042(2) Uani 1 1 d . . . H5 H 0.4492 -0.3107 0.6711 0.051 Uiso 1 1 calc R . . C6 C 0.3076(7) -0.2741(6) 0.4818(7) 0.044(2) Uani 1 1 d . . . H6 H 0.2847 -0.2981 0.4220 0.052 Uiso 1 1 calc R . . C7 C 0.3711(6) -0.3164(5) 0.5420(7) 0.041(2) Uani 1 1 d . . . H7 H 0.3924 -0.3699 0.5234 0.049 Uiso 1 1 calc R . . C8 C 0.1619(5) 0.0247(4) 0.5556(6) 0.0303(18) Uani 1 1 d . . . C9 C 0.1871(5) 0.0673(4) 0.6475(5) 0.0236(18) Uani 1 1 d . . . C10 C 0.1445(5) 0.1457(4) 0.6597(5) 0.0281(18) Uani 1 1 d . . . H10 H 0.1586 0.1761 0.7179 0.034 Uiso 1 1 calc R . . C11 C 0.0811(6) 0.1808(5) 0.5875(6) 0.038(2) Uani 1 1 d . . . H11 H 0.0545 0.2341 0.5977 0.045 Uiso 1 1 calc R . . C12 C 0.0576(5) 0.1362(5) 0.5001(6) 0.039(2) Uani 1 1 d . . . H12 H 0.0154 0.1595 0.4520 0.046 Uiso 1 1 calc R . . C13 C 0.0973(6) 0.0576(5) 0.4855(6) 0.036(2) Uani 1 1 d . . . H13 H 0.0805 0.0266 0.4283 0.043 Uiso 1 1 calc R . . C14 C 0.2773(5) 0.2142(4) 0.9455(5) 0.0241(17) Uani 1 1 d . . . C15 C 0.3064(5) 0.1789(4) 0.8623(5) 0.0220(16) Uani 1 1 d . . . C16 C 0.3547(6) 0.2272(5) 0.8029(6) 0.0279(18) Uani 1 1 d . . . H16 H 0.3725 0.2041 0.7456 0.034 Uiso 1 1 calc R . . C17 C 0.4769(5) -0.0401(4) 0.8223(5) 0.0239(16) Uani 1 1 d . . . C18 C 0.3482(5) 0.3479(4) 0.9152(6) 0.0324(19) Uani 1 1 d . . . H18 H 0.3638 0.4047 0.9323 0.039 Uiso 1 1 calc R . . C19 C 0.2976(5) 0.3003(4) 0.9735(5) 0.0274(18) Uani 1 1 d . . . H19 H 0.2775 0.3240 1.0294 0.033 Uiso 1 1 calc R . . C20 C 0.2247(5) 0.0678(4) 0.9112(5) 0.0186(16) Uani 1 1 d . . . C21 C 0.1802(5) -0.0146(4) 0.8950(4) 0.0182(14) Uani 1 1 d . . . C22 C 0.1958(5) -0.0531(4) 0.8050(5) 0.0206(16) Uani 1 1 d . . . C23 C 0.1498(5) -0.1297(4) 0.7804(5) 0.0229(16) Uani 1 1 d . . . H23 H 0.1571 -0.1564 0.7212 0.028 Uiso 1 1 calc R . . C24 C 0.0930(5) -0.1673(4) 0.8422(5) 0.0290(18) Uani 1 1 d . . . H24 H 0.0636 -0.2191 0.8242 0.035 Uiso 1 1 calc R . . C25 C 0.0798(6) -0.1283(4) 0.9308(6) 0.032(2) Uani 1 1 d . . . H25 H 0.0424 -0.1541 0.9723 0.038 Uiso 1 1 calc R . . C26 C 0.1226(5) -0.0509(4) 0.9564(5) 0.0219(16) Uani 1 1 d . . . H26 H 0.1128 -0.0233 1.0145 0.026 Uiso 1 1 calc R . . C27 C 0.2033(6) 0.0054(6) 1.2217(6) 0.044(2) Uani 1 1 d . . . H27 H 0.2490 0.0469 1.2301 0.053 Uiso 1 1 calc R . . C28 C 0.2250(6) -0.0743(6) 1.1995(6) 0.046(2) Uani 1 1 d . . . H28 H 0.2849 -0.0883 1.1922 0.055 Uiso 1 1 calc R . . C29 C 0.1582(7) -0.1368(5) 1.1871(6) 0.041(2) Uani 1 1 d . . . H29 H 0.1731 -0.1934 1.1720 0.049 Uiso 1 1 calc R . . C30 C 0.0697(7) -0.1158(6) 1.1971(6) 0.050(3) Uani 1 1 d . . . H30 H 0.0242 -0.1574 1.1874 0.060 Uiso 1 1 calc R . . C31 C 0.0492(6) -0.0320(7) 1.2217(6) 0.051(2) Uani 1 1 d . . . H31 H -0.0099 -0.0166 1.2307 0.061 Uiso 1 1 calc R . . C32 C 0.1184(8) 0.0290(6) 1.2326(6) 0.047(3) Uani 1 1 d . . . H32 H 0.1057 0.0861 1.2475 0.057 Uiso 1 1 calc R . . C48 C 0.4711(5) 0.0609(4) 0.6770(5) 0.0253(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02086(16) 0.01784(15) 0.01440(14) 0.00062(10) 0.00510(10) 0.00052(12) S1 0.0512(15) 0.0417(11) 0.0197(10) -0.0060(8) 0.0005(10) -0.0064(11) S2 0.0353(12) 0.0248(9) 0.0200(9) -0.0055(7) 0.0105(8) -0.0051(8) O1 0.019(3) 0.024(2) 0.024(3) 0.0037(19) 0.006(2) 0.000(2) O2 0.023(3) 0.018(2) 0.023(3) 0.0030(18) 0.008(2) 0.000(2) N1 0.019(3) 0.023(3) 0.020(3) 0.001(2) 0.006(3) -0.004(3) N2 0.022(4) 0.020(3) 0.018(3) -0.001(2) -0.001(3) -0.001(3) C1 0.037(5) 0.038(4) 0.030(4) -0.012(3) 0.020(4) -0.014(4) C1A 0.019(4) 0.019(3) 0.027(4) -0.003(3) 0.013(3) -0.007(3) C1B 0.036(5) 0.031(4) 0.014(4) -0.003(3) 0.009(3) 0.009(4) C1C 0.033(5) 0.039(4) 0.034(5) 0.011(3) 0.008(4) 0.007(4) C1D 0.028(5) 0.063(5) 0.034(5) 0.013(4) 0.007(4) -0.005(4) C2 0.026(4) 0.023(4) 0.034(4) 0.002(3) 0.009(3) -0.003(3) C3 0.027(5) 0.027(4) 0.035(5) -0.010(3) 0.003(4) 0.001(4) C4 0.043(6) 0.026(4) 0.043(5) -0.002(3) 0.027(4) -0.007(4) C5 0.034(6) 0.034(4) 0.060(6) -0.010(4) 0.010(5) 0.014(4) C6 0.057(7) 0.035(4) 0.043(6) -0.017(4) 0.027(5) -0.023(5) C7 0.038(6) 0.031(4) 0.059(6) -0.021(4) 0.024(5) 0.001(4) C8 0.031(5) 0.023(4) 0.039(5) 0.008(3) 0.012(4) -0.004(3) C9 0.031(5) 0.018(3) 0.026(4) 0.007(3) 0.020(4) -0.004(3) C10 0.031(5) 0.034(4) 0.021(4) 0.003(3) 0.009(3) 0.013(4) C11 0.038(5) 0.039(4) 0.039(5) 0.021(4) 0.020(4) 0.018(4) C12 0.025(5) 0.055(5) 0.034(5) 0.021(4) -0.001(4) 0.004(4) C13 0.033(5) 0.043(5) 0.031(5) 0.008(4) -0.002(4) -0.004(4) C14 0.025(5) 0.021(4) 0.026(4) -0.006(3) 0.004(3) 0.003(3) C15 0.021(4) 0.021(3) 0.023(4) 0.001(3) -0.001(3) 0.002(3) C16 0.037(5) 0.023(3) 0.026(4) -0.002(3) 0.014(4) -0.006(4) C17 0.028(5) 0.019(3) 0.024(4) -0.005(3) 0.003(3) 0.006(3) C18 0.039(5) 0.014(3) 0.045(5) -0.010(3) 0.007(4) -0.007(3) C19 0.029(5) 0.027(4) 0.028(4) -0.011(3) 0.008(4) -0.002(3) C20 0.018(4) 0.025(4) 0.012(3) 0.003(3) -0.001(3) 0.001(3) C21 0.024(4) 0.019(3) 0.011(3) 0.005(3) -0.002(3) -0.002(3) C22 0.014(4) 0.029(4) 0.018(4) -0.001(3) -0.002(3) 0.013(3) C23 0.025(4) 0.027(4) 0.016(4) -0.006(3) 0.003(3) -0.002(3) C24 0.041(5) 0.022(4) 0.024(4) 0.002(3) 0.006(4) -0.015(3) C25 0.048(6) 0.021(4) 0.030(5) 0.003(3) 0.021(4) -0.006(4) C26 0.025(4) 0.023(4) 0.019(4) -0.006(3) 0.008(3) -0.008(3) C27 0.038(6) 0.064(6) 0.027(4) 0.008(4) -0.008(4) -0.015(5) C28 0.035(6) 0.068(6) 0.034(5) 0.007(4) 0.005(4) 0.014(5) C29 0.063(7) 0.035(5) 0.025(5) 0.014(3) 0.007(4) 0.006(5) C30 0.064(7) 0.059(6) 0.024(5) 0.021(4) -0.004(5) -0.031(6) C31 0.027(5) 0.101(7) 0.026(4) 0.010(5) 0.006(4) 0.015(5) C32 0.071(8) 0.046(5) 0.023(4) 0.009(4) -0.003(5) 0.013(5) C48 0.032(5) 0.027(4) 0.019(4) 0.002(3) 0.013(4) 0.000(4) _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 O1 2.158(4) . ? Ir1 O2 2.145(5) . ? Ir1 N1 2.059(5) . ? Ir1 N2 2.050(5) . ? Ir1 C9 1.991(8) . ? Ir1 C22 1.990(7) . ? S1 C1 1.721(9) . ? S1 C1B 1.712(7) . ? S2 C14 1.735(8) . ? S2 C20 1.720(7) . ? O1 C48 1.248(8) . ? O2 C17 1.247(8) . ? N1 C1A 1.392(8) . ? N1 C1B 1.321(9) . ? N2 C15 1.383(8) . ? N2 C20 1.329(8) . ? C1 C1A 1.399(10) . ? C1 C6 1.404(12) . ? C1A C3 1.374(10) . ? C1B C8 1.442(10) . ? C1C H1CA 0.9600 . ? C1C H1CB 0.9600 . ? C1C H1CC 0.9600 . ? C1C C17 1.506(9) . ? C1D H1DA 0.9600 . ? C1D H1DB 0.9600 . ? C1D H1DC 0.9600 . ? C1D C48 1.512(9) . ? C2 H2 0.9300 . ? C2 C17 1.408(10) . ? C2 C48 1.406(9) . ? C3 H3 0.9300 . ? C3 C5 1.378(10) . ? C4 H4 0.9300 . ? C4 C16 1.394(9) . ? C4 C18 1.394(10) . ? C5 H5 0.9300 . ? C5 C7 1.384(11) . ? C6 H6 0.9300 . ? C6 C7 1.349(13) . ? C7 H7 0.9300 . ? C8 C9 1.434(10) . ? C8 C13 1.375(10) . ? C9 C10 1.385(9) . ? C10 H10 0.9300 . ? C10 C11 1.396(10) . ? C11 H11 0.9300 . ? C11 C12 1.393(11) . ? C12 H12 0.9300 . ? C12 C13 1.373(11) . ? C13 H13 0.9300 . ? C14 C15 1.379(9) . ? C14 C19 1.408(10) . ? C15 C16 1.368(10) . ? C16 H16 0.9300 . ? C18 H18 0.9300 . ? C18 C19 1.372(10) . ? C19 H19 0.9300 . ? C20 C21 1.440(8) . ? C21 C22 1.415(9) . ? C21 C26 1.385(9) . ? C22 C23 1.388(9) . ? C23 H23 0.9300 . ? C23 C24 1.390(9) . ? C24 H24 0.9300 . ? C24 C25 1.392(9) . ? C25 H25 0.9300 . ? C25 C26 1.380(9) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C27 C28 1.315(11) . ? C27 C32 1.335(13) . ? C28 H28 0.9300 . ? C28 C29 1.380(12) . ? C29 H29 0.9300 . ? C29 C30 1.374(13) . ? C30 H30 0.9300 . ? C30 C31 1.380(13) . ? C31 H31 0.9300 . ? C31 C32 1.388(14) . ? C32 H32 0.9300 . ? 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 O2 Ir1 O1 87.95(17) . . ? N1 Ir1 O1 86.85(19) . . ? N1 Ir1 O2 100.19(19) . . ? N2 Ir1 O1 99.61(19) . . ? N2 Ir1 O2 86.57(19) . . ? N2 Ir1 N1 170.9(2) . . ? C9 Ir1 O1 91.0(2) . . ? C9 Ir1 O2 178.4(2) . . ? C9 Ir1 N1 80.9(3) . . ? C9 Ir1 N2 92.5(2) . . ? C22 Ir1 O1 177.8(2) . . ? C22 Ir1 O2 89.9(2) . . ? C22 Ir1 N1 93.3(2) . . ? C22 Ir1 N2 80.5(2) . . ? C22 Ir1 C9 91.2(3) . . ? C1B S1 C1 89.6(4) . . ? C20 S2 C14 88.9(3) . . ? C48 O1 Ir1 124.8(4) . . ? C17 O2 Ir1 125.9(4) . . ? C1A N1 Ir1 134.2(5) . . ? C1B N1 Ir1 113.7(4) . . ? C1B N1 C1A 112.0(6) . . ? C15 N2 Ir1 134.0(5) . . ? C20 N2 Ir1 113.7(4) . . ? C20 N2 C15 111.9(6) . . ? C1A C1 S1 111.1(5) . . ? C1A C1 C6 120.0(8) . . ? C6 C1 S1 128.9(7) . . ? N1 C1A C1 112.3(7) . . ? C3 C1A N1 127.3(6) . . ? C3 C1A C1 120.4(7) . . ? N1 C1B S1 115.0(5) . . ? N1 C1B C8 118.0(6) . . ? C8 C1B S1 126.8(6) . . ? H1CA C1C H1CB 109.5 . . ? H1CA C1C H1CC 109.5 . . ? H1CB C1C H1CC 109.5 . . ? C17 C1C H1CA 109.5 . . ? C17 C1C H1CB 109.5 . . ? C17 C1C H1CC 109.5 . . ? H1DA C1D H1DB 109.5 . . ? H1DA C1D H1DC 109.5 . . ? H1DB C1D H1DC 109.5 . . ? C48 C1D H1DA 109.5 . . ? C48 C1D H1DB 109.5 . . ? C48 C1D H1DC 109.5 . . ? C17 C2 H2 116.1 . . ? C48 C2 H2 116.1 . . ? C48 C2 C17 127.8(8) . . ? C1A C3 H3 121.0 . . ? C1A C3 C5 118.1(7) . . ? C5 C3 H3 121.0 . . ? C16 C4 H4 119.4 . . ? C18 C4 H4 119.4 . . ? C18 C4 C16 121.2(7) . . ? C3 C5 H5 119.0 . . ? C3 C5 C7 122.0(8) . . ? C7 C5 H5 119.0 . . ? C1 C6 H6 120.5 . . ? C7 C6 C1 119.1(8) . . ? C7 C6 H6 120.5 . . ? C5 C7 H7 119.8 . . ? C6 C7 C5 120.4(8) . . ? C6 C7 H7 119.8 . . ? C9 C8 C1B 113.0(7) . . ? C13 C8 C1B 124.5(7) . . ? C13 C8 C9 122.5(7) . . ? C8 C9 Ir1 114.3(5) . . ? C10 C9 Ir1 130.0(6) . . ? C10 C9 C8 115.5(7) . . ? C9 C10 H10 118.9 . . ? C9 C10 C11 122.2(7) . . ? C11 C10 H10 118.9 . . ? C10 C11 H11 119.9 . . ? C12 C11 C10 120.2(7) . . ? C12 C11 H11 119.9 . . ? C11 C12 H12 120.2 . . ? C13 C12 C11 119.6(8) . . ? C13 C12 H12 120.2 . . ? C8 C13 H13 120.0 . . ? C12 C13 C8 120.0(8) . . ? C12 C13 H13 120.0 . . ? C15 C14 S2 111.4(5) . . ? C15 C14 C19 121.5(7) . . ? C19 C14 S2 127.1(5) . . ? C14 C15 N2 113.1(6) . . ? C16 C15 N2 125.8(6) . . ? C16 C15 C14 121.0(6) . . ? C4 C16 H16 121.0 . . ? C15 C16 C4 118.1(7) . . ? C15 C16 H16 121.0 . . ? O2 C17 C1C 117.4(6) . . ? O2 C17 C2 126.2(7) . . ? C2 C17 C1C 116.4(7) . . ? C4 C18 H18 119.6 . . ? C19 C18 C4 120.8(6) . . ? C19 C18 H18 119.6 . . ? C14 C19 H19 121.3 . . ? C18 C19 C14 117.4(6) . . ? C18 C19 H19 121.3 . . ? N2 C20 S2 114.8(5) . . ? N2 C20 C21 117.7(6) . . ? C21 C20 S2 127.2(5) . . ? C22 C21 C20 112.8(6) . . ? C26 C21 C20 124.6(6) . . ? C26 C21 C22 122.5(6) . . ? C21 C22 Ir1 114.8(5) . . ? C23 C22 Ir1 128.7(5) . . ? C23 C22 C21 116.4(6) . . ? C22 C23 H23 119.2 . . ? C22 C23 C24 121.6(6) . . ? C24 C23 H23 119.2 . . ? C23 C24 H24 119.7 . . ? C23 C24 C25 120.6(6) . . ? C25 C24 H24 119.7 . . ? C24 C25 H25 120.3 . . ? C26 C25 C24 119.5(7) . . ? C26 C25 H25 120.3 . . ? C21 C26 H26 120.3 . . ? C25 C26 C21 119.5(6) . . ? C25 C26 H26 120.3 . . ? C28 C27 H27 118.7 . . ? C28 C27 C32 122.6(9) . . ? C32 C27 H27 118.7 . . ? C27 C28 H28 120.3 . . ? C27 C28 C29 119.5(9) . . ? C29 C28 H28 120.3 . . ? C28 C29 H29 119.9 . . ? C30 C29 C28 120.1(8) . . ? C30 C29 H29 119.9 . . ? C29 C30 H30 120.5 . . ? C29 C30 C31 119.1(9) . . ? C31 C30 H30 120.5 . . ? C30 C31 H31 120.6 . . ? C30 C31 C32 118.8(9) . . ? C32 C31 H31 120.6 . . ? C27 C32 C31 119.9(9) . . ? C27 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? O1 C48 C1D 114.9(6) . . ? O1 C48 C2 127.1(7) . . ? C2 C48 C1D 117.9(7) . . ? _database_code_depnum_ccdc_archive 'CCDC 857633' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110315_S2_LM _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C43 H31 Ir N2 O2 S2, 2(C6 H6)' _chemical_formula_sum 'C55 H43 Ir N2 O2 S2' _chemical_formula_weight 1020.23 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' 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' 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_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_angle_alpha 85.0404(15) _cell_angle_beta 70.7698(16) _cell_angle_gamma 68.6685(16) _cell_formula_units_Z 2 _cell_length_a 12.4036(2) _cell_length_b 12.4491(2) _cell_length_c 16.4077(3) _cell_measurement_reflns_used 9372 _cell_measurement_temperature 150.1 _cell_measurement_theta_max 29.2496 _cell_measurement_theta_min 2.8844 _cell_volume 2226.73(7) _exptl_absorpt_coefficient_mu 3.137 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.94212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 1024 _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_special_details ? _diffrn_ambient_temperature 150.1 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -44.00 48.40 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 77.0000 -30.0000 154 #__ type_ start__ end____ width___ exp.time_ 2 omega -23.00 5.20 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -91.0000 118.0000 47 #__ type_ start__ end____ width___ exp.time_ 3 omega -84.00 10.20 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -77.0000 -150.0000 157 #__ type_ start__ end____ width___ exp.time_ 4 omega 38.00 85.40 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 38.0000 60.0000 79 #__ type_ start__ end____ width___ exp.time_ 5 omega -3.00 78.00 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 38.0000 150.0000 135 #__ type_ start__ end____ width___ exp.time_ 6 omega -42.00 39.00 0.6000 15.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 38.0000 -180.0000 135 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0320236 _diffrn_orient_matrix_UB_12 0.0132408 _diffrn_orient_matrix_UB_13 -0.0417577 _diffrn_orient_matrix_UB_21 -0.0553465 _diffrn_orient_matrix_UB_22 0.0414586 _diffrn_orient_matrix_UB_23 -0.0033737 _diffrn_orient_matrix_UB_31 0.0106197 _diffrn_orient_matrix_UB_32 0.0430393 _diffrn_orient_matrix_UB_33 0.0185569 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetl/netI 0.0575 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 18767 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.89 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8001 _reflns_number_total 9108 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 1.153 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.109 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0356 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 580 _refine_ls_number_reflns 9108 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.0745 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.7052P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. DFIX The bond distance between O1 and C39 was fixed to be 1.3(0.01) DFIX The bond distance between O2 and C41 was fixed to be 1.55(0.01) EADP C37A C37B EADP C38A C38B EADP C36A C36B EADP C33A C33B EADP C34B C34A EADP C35B C35A ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.000457(14) 0.298820(14) 0.265335(10) 0.02359(6) Uani 1 1 d . . . S1 S -0.10000(11) 0.60267(10) 0.10057(8) 0.0359(3) Uani 1 1 d . . . S2 S 0.18397(11) -0.07093(10) 0.31833(8) 0.0367(3) Uani 1 1 d . . . O1 O -0.1823(2) 0.3812(2) 0.36132(19) 0.0244(6) Uani 1 1 d D . . O2 O 0.0736(3) 0.3239(3) 0.3622(2) 0.0405(9) Uani 1 1 d D . . N1 N -0.0207(3) 0.4546(3) 0.2070(2) 0.0261(8) Uani 1 1 d . . . N2 N 0.0341(3) 0.1343(3) 0.3074(2) 0.0262(8) Uani 1 1 d . . . C1 C -0.0267(4) 0.6395(4) 0.1618(3) 0.0317(10) Uani 1 1 d . . . C2 C -0.0056(4) 0.7418(4) 0.1617(3) 0.0373(11) Uani 1 1 d . . . H2 H -0.0332 0.8032 0.1263 0.045 Uiso 1 1 calc R . . C3 C 0.0564(5) 0.7507(4) 0.2146(3) 0.0429(13) Uani 1 1 d . . . H3 H 0.0715 0.8199 0.2163 0.051 Uiso 1 1 calc R . . C4 C 0.0980(5) 0.6597(5) 0.2661(3) 0.0461(13) Uani 1 1 d . . . H4 H 0.1418 0.6683 0.3014 0.055 Uiso 1 1 calc R . . C5 C 0.0774(4) 0.5580(4) 0.2671(3) 0.0371(11) Uani 1 1 d . . . H5 H 0.1065 0.4964 0.3019 0.045 Uiso 1 1 calc R . . C6 C 0.0118(4) 0.5494(4) 0.2149(3) 0.0292(10) Uani 1 1 d . . . C7 C -0.0781(4) 0.4712(4) 0.1490(3) 0.0282(10) Uani 1 1 d . . . C8 C -0.1098(4) 0.3777(3) 0.1303(3) 0.0260(9) Uani 1 1 d . . . C9 C -0.0762(3) 0.2802(3) 0.1798(3) 0.0232(9) Uani 1 1 d . . . C10 C -0.1048(4) 0.1856(3) 0.1657(3) 0.0260(10) Uani 1 1 d . . . H10 H -0.0851 0.1188 0.1985 0.031 Uiso 1 1 calc R . . C11 C -0.1614(4) 0.1876(3) 0.1048(3) 0.0275(10) Uani 1 1 d . . . C12 C -0.1904(4) 0.2846(4) 0.0558(3) 0.0314(10) Uani 1 1 d . . . H12 H -0.2268 0.2847 0.0131 0.038 Uiso 1 1 calc R . . C13 C -0.1667(4) 0.3799(4) 0.0687(3) 0.0310(10) Uani 1 1 d . . . H13 H -0.1885 0.4468 0.0363 0.037 Uiso 1 1 calc R . . C14 C -0.1917(4) 0.0859(4) 0.0920(3) 0.0303(10) Uani 1 1 d . . . C15 C -0.2536(4) 0.0358(4) 0.1606(3) 0.0347(11) Uani 1 1 d . . . H15 H -0.2753 0.0650 0.2176 0.042 Uiso 1 1 calc R . . C16 C -0.2850(4) -0.0566(4) 0.1481(3) 0.0392(12) Uani 1 1 d . . . H16 H -0.3289 -0.0893 0.1958 0.047 Uiso 1 1 calc R . . C17 C -0.2510(5) -0.1002(4) 0.0646(3) 0.0428(13) Uani 1 1 d . . . H17 H -0.2717 -0.1632 0.0550 0.051 Uiso 1 1 calc R . . C18 C -0.1879(5) -0.0528(4) -0.0033(4) 0.0504(15) Uani 1 1 d . . . H18 H -0.1645 -0.0841 -0.0600 0.060 Uiso 1 1 calc R . . C19 C -0.1573(5) 0.0390(4) 0.0078(3) 0.0451(13) Uani 1 1 d . . . H19 H -0.1133 0.0709 -0.0406 0.054 Uiso 1 1 calc R . . C20 C 0.0308(4) -0.0350(4) 0.3820(3) 0.0317(11) Uani 1 1 d . . . C21 C -0.0228(5) -0.1011(4) 0.4405(3) 0.0393(12) Uani 1 1 d . . . H21 H 0.0244 -0.1765 0.4522 0.047 Uiso 1 1 calc R . . C22 C -0.1474(5) -0.0549(4) 0.4820(3) 0.0444(13) Uani 1 1 d . . . H22 H -0.1867 -0.0982 0.5236 0.053 Uiso 1 1 calc R . . C23 C -0.2159(4) 0.0553(4) 0.4631(3) 0.0400(12) Uani 1 1 d . . . H23 H -0.3018 0.0848 0.4908 0.048 Uiso 1 1 calc R . . C24 C -0.1620(4) 0.1218(4) 0.4053(3) 0.0335(11) Uani 1 1 d . . . H24 H -0.2098 0.1964 0.3929 0.040 Uiso 1 1 calc R . . C25 C -0.0360(4) 0.0778(4) 0.3654(3) 0.0260(9) Uani 1 1 d . . . C26 C 0.1506(4) 0.0659(4) 0.2758(3) 0.0285(10) Uani 1 1 d . . . C27 C 0.2316(4) 0.1100(4) 0.2110(3) 0.0326(11) Uani 1 1 d . A . C28 C 0.1729(4) 0.2236(4) 0.1886(3) 0.0288(10) Uani 1 1 d . . . C29 C 0.2441(4) 0.2710(4) 0.1226(3) 0.0336(11) Uani 1 1 d . A . H29 H 0.2071 0.3469 0.1059 0.040 Uiso 1 1 calc R . . C30 C 0.3681(4) 0.2109(5) 0.0799(3) 0.0470(14) Uani 1 1 d . . . C31 C 0.4228(4) 0.0987(5) 0.1050(3) 0.0543(17) Uani 1 1 d . A . H31 H 0.5069 0.0569 0.0767 0.065 Uiso 1 1 calc R . . C32 C 0.3563(4) 0.0490(5) 0.1695(3) 0.0470(14) Uani 1 1 d . . . H32 H 0.3944 -0.0267 0.1862 0.056 Uiso 1 1 calc R A . C33A C 0.4441(11) 0.2400(9) 0.0023(7) 0.0253(17) Uani 0.506(4) 1 d P A 2 C33B C 0.4381(11) 0.2890(9) 0.0181(8) 0.0253(17) Uani 0.494(4) 1 d P A 1 C34A C 0.5724(10) 0.2055(12) -0.0198(8) 0.036(2) Uani 0.494(4) 1 d P A 2 H34 H 0.6131 0.1512 0.0145 0.044 Uiso 0.494(4) 1 calc PR A 2 C34B C 0.5365(10) 0.2270(12) -0.0492(8) 0.036(2) Uani 0.506(4) 1 d P A 1 H34A H 0.5563 0.1461 -0.0540 0.044 Uiso 0.506(4) 1 calc PR A 1 C35A C 0.6392(16) 0.249(2) -0.0893(12) 0.039(3) Uani 0.494(4) 1 d P A 2 H35 H 0.7249 0.2263 -0.1015 0.047 Uiso 0.494(4) 1 calc PR A 2 C35B C 0.6080(15) 0.2781(19) -0.1105(12) 0.039(3) Uani 0.506(4) 1 d P A 1 H35A H 0.6730 0.2337 -0.1582 0.047 Uiso 0.506(4) 1 calc PR A 1 C36A C 0.5810(10) 0.3257(10) -0.1428(7) 0.0413(19) Uani 0.506(4) 1 d P A 2 H36 H 0.6279 0.3531 -0.1925 0.050 Uiso 0.506(4) 1 calc PR A 2 C36B C 0.5827(9) 0.3975(9) -0.1011(6) 0.0413(19) Uani 0.494(4) 1 d P A 1 H36A H 0.6313 0.4340 -0.1421 0.050 Uiso 0.494(4) 1 calc PR A 1 C37A C 0.4571(8) 0.3612(8) -0.1234(6) 0.0395(17) Uani 0.506(4) 1 d P A 2 H37 H 0.4173 0.4145 -0.1586 0.047 Uiso 0.506(4) 1 calc PR A 2 C37B C 0.4864(9) 0.4612(8) -0.0315(6) 0.0395(17) Uani 0.494(4) 1 d P . 1 H37A H 0.4295 0.5196 -0.0584 0.047 Uiso 0.494(4) 1 calc PR A 1 C38A C 0.3897(8) 0.3186(7) -0.0512(6) 0.0318(15) Uani 0.506(4) 1 d P A 2 H38 H 0.3036 0.3440 -0.0381 0.038 Uiso 0.506(4) 1 calc PR A 2 C38B C 0.4141(8) 0.4071(8) 0.0265(6) 0.0318(15) Uani 0.494(4) 1 d P A 1 H38A H 0.3466 0.4515 0.0729 0.038 Uiso 0.494(4) 1 calc PR A 1 C39 C -0.1967(5) 0.3979(4) 0.4364(3) 0.0464(14) Uani 1 1 d D . . C40 C -0.1126(5) 0.3849(4) 0.4761(4) 0.0486(14) Uani 1 1 d . . . H40 H -0.1431 0.4009 0.5366 0.058 Uiso 1 1 calc R . . C41 C 0.0151(4) 0.3503(4) 0.4370(4) 0.0386(12) Uani 1 1 d D . . C42 C -0.3301(5) 0.4419(5) 0.4930(4) 0.0634(17) Uani 1 1 d . . . H42B H -0.3749 0.5129 0.4698 0.095 Uiso 1 1 calc R . . H42C H -0.3353 0.4577 0.5519 0.095 Uiso 1 1 calc R . . H42A H -0.3659 0.3833 0.4938 0.095 Uiso 1 1 calc R . . C43 C 0.0927(5) 0.3540(5) 0.4930(4) 0.0582(16) Uani 1 1 d . . . H43A H 0.1549 0.2775 0.4916 0.087 Uiso 1 1 calc R . . H43C H 0.0396 0.3767 0.5527 0.087 Uiso 1 1 calc R . . H43B H 0.1327 0.4102 0.4703 0.087 Uiso 1 1 calc R . . C44 C 0.3926(7) 0.2687(7) 0.3054(7) 0.096(3) Uani 1 1 d . . . H44 H 0.3285 0.2479 0.3003 0.115 Uiso 1 1 calc R . . C45 C 0.4468(8) 0.3257(7) 0.2434(5) 0.089(2) Uani 1 1 d . . . H45 H 0.4213 0.3445 0.1937 0.107 Uiso 1 1 calc R . . C46 C 0.5378(6) 0.3579(6) 0.2491(5) 0.0714(19) Uani 1 1 d . . . H46 H 0.5754 0.3988 0.2041 0.086 Uiso 1 1 calc R . . C47 C 0.5739(5) 0.3306(5) 0.3197(5) 0.068(2) Uani 1 1 d . . . H47 H 0.6379 0.3520 0.3242 0.082 Uiso 1 1 calc R . . C48 C 0.5197(6) 0.2728(6) 0.3845(5) 0.069(2) Uani 1 1 d . . . H48 H 0.5439 0.2551 0.4348 0.083 Uiso 1 1 calc R . . C49 C 0.4292(6) 0.2406(5) 0.3759(5) 0.079(2) Uani 1 1 d . . . H49 H 0.3921 0.1981 0.4197 0.095 Uiso 1 1 calc R . . C50 C 0.5130(6) 0.7844(7) 0.3356(4) 0.0715(19) Uani 1 1 d . . . H50 H 0.4480 0.7746 0.3225 0.086 Uiso 1 1 calc R . . C51 C 0.5036(6) 0.8901(7) 0.3564(4) 0.072(2) Uani 1 1 d . . . H51 H 0.4327 0.9548 0.3572 0.086 Uiso 1 1 calc R . . C52 C 0.5964(7) 0.9045(6) 0.3765(4) 0.074(2) Uani 1 1 d . . . H52 H 0.5887 0.9789 0.3929 0.089 Uiso 1 1 calc R . . C53 C 0.7001(6) 0.8120(7) 0.3730(4) 0.0730(19) Uani 1 1 d . . . H53 H 0.7654 0.8227 0.3852 0.088 Uiso 1 1 calc R . . C54 C 0.7100(5) 0.7030(6) 0.3519(4) 0.0667(19) Uani 1 1 d . . . H54 H 0.7811 0.6381 0.3505 0.080 Uiso 1 1 calc R . . C55 C 0.6162(7) 0.6900(6) 0.3332(4) 0.0728(19) Uani 1 1 d . . . H55 H 0.6219 0.6156 0.3183 0.087 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 0.01906(9) 0.03259(10) 0.02042(9) -0.00086(6) -0.00875(6) -0.00810(7) S1 0.0452(7) 0.0350(6) 0.0429(7) 0.0092(5) -0.0266(6) -0.0224(6) S2 0.0324(6) 0.0388(7) 0.0319(6) 0.0006(5) -0.0144(5) -0.0008(5) O1 0.0253(15) 0.0288(16) 0.0302(17) 0.0077(12) -0.0199(13) -0.0136(13) O2 0.044(2) 0.0357(19) 0.064(3) 0.0087(17) -0.045(2) -0.0161(16) N1 0.0221(17) 0.031(2) 0.0256(19) -0.0010(15) -0.0085(15) -0.0091(16) N2 0.0221(18) 0.034(2) 0.0238(19) -0.0019(15) -0.0112(15) -0.0078(16) C1 0.032(2) 0.038(3) 0.029(2) 0.000(2) -0.013(2) -0.015(2) C2 0.041(3) 0.043(3) 0.034(3) 0.002(2) -0.009(2) -0.025(2) C3 0.055(3) 0.051(3) 0.034(3) 0.002(2) -0.006(2) -0.040(3) C4 0.060(3) 0.069(4) 0.032(3) 0.006(2) -0.018(3) -0.046(3) C5 0.043(3) 0.058(3) 0.025(2) 0.006(2) -0.015(2) -0.032(3) C6 0.030(2) 0.042(3) 0.021(2) -0.0021(19) -0.0063(19) -0.019(2) C7 0.025(2) 0.033(2) 0.028(2) 0.0013(19) -0.0107(19) -0.010(2) C8 0.024(2) 0.027(2) 0.028(2) -0.0008(18) -0.0108(19) -0.0073(19) C9 0.0149(19) 0.030(2) 0.022(2) -0.0046(17) -0.0058(17) -0.0039(18) C10 0.025(2) 0.027(2) 0.023(2) -0.0026(17) -0.0091(18) -0.0047(19) C11 0.029(2) 0.027(2) 0.027(2) -0.0045(18) -0.0114(19) -0.0060(19) C12 0.038(3) 0.037(3) 0.029(2) 0.0023(19) -0.021(2) -0.014(2) C13 0.037(2) 0.033(2) 0.034(3) 0.0064(19) -0.024(2) -0.014(2) C14 0.036(2) 0.027(2) 0.031(2) 0.0000(19) -0.017(2) -0.008(2) C15 0.043(3) 0.034(3) 0.029(2) -0.003(2) -0.018(2) -0.011(2) C16 0.047(3) 0.035(3) 0.041(3) 0.010(2) -0.021(2) -0.017(2) C17 0.061(3) 0.022(2) 0.055(3) -0.002(2) -0.035(3) -0.010(2) C18 0.082(4) 0.037(3) 0.040(3) -0.009(2) -0.029(3) -0.019(3) C19 0.072(4) 0.043(3) 0.028(3) 0.000(2) -0.021(3) -0.025(3) C20 0.033(2) 0.035(3) 0.029(2) -0.005(2) -0.016(2) -0.008(2) C21 0.049(3) 0.033(3) 0.036(3) 0.003(2) -0.017(2) -0.012(2) C22 0.053(3) 0.046(3) 0.042(3) 0.003(2) -0.011(3) -0.030(3) C23 0.034(3) 0.041(3) 0.045(3) -0.001(2) -0.008(2) -0.018(2) C24 0.025(2) 0.037(3) 0.038(3) -0.001(2) -0.010(2) -0.011(2) C25 0.030(2) 0.031(2) 0.023(2) -0.0020(18) -0.0134(19) -0.011(2) C26 0.025(2) 0.036(2) 0.023(2) -0.0011(18) -0.0136(19) -0.003(2) C27 0.022(2) 0.046(3) 0.025(2) -0.002(2) -0.0123(19) -0.001(2) C28 0.024(2) 0.046(3) 0.020(2) -0.0022(19) -0.0116(18) -0.011(2) C29 0.024(2) 0.055(3) 0.021(2) 0.004(2) -0.0110(19) -0.011(2) C30 0.022(2) 0.088(4) 0.029(3) 0.009(3) -0.012(2) -0.015(3) C31 0.019(2) 0.096(5) 0.030(3) 0.010(3) -0.009(2) 0.000(3) C32 0.026(2) 0.066(4) 0.031(3) 0.005(2) -0.012(2) 0.005(3) C33A 0.021(3) 0.024(6) 0.031(4) -0.003(4) -0.011(3) -0.005(5) C33B 0.021(3) 0.024(6) 0.031(4) -0.003(4) -0.011(3) -0.005(5) C34A 0.023(5) 0.038(5) 0.042(7) -0.012(4) -0.005(3) -0.006(4) C34B 0.023(5) 0.038(5) 0.042(7) -0.012(4) -0.005(3) -0.006(4) C35A 0.024(8) 0.064(11) 0.028(9) -0.013(6) -0.002(4) -0.017(8) C35B 0.024(8) 0.064(11) 0.028(9) -0.013(6) -0.002(4) -0.017(8) C36A 0.037(4) 0.054(5) 0.029(4) 0.010(3) -0.005(3) -0.020(4) C36B 0.037(4) 0.054(5) 0.029(4) 0.010(3) -0.005(3) -0.020(4) C37A 0.036(4) 0.042(4) 0.040(4) 0.007(3) -0.012(3) -0.014(3) C37B 0.036(4) 0.042(4) 0.040(4) 0.007(3) -0.012(3) -0.014(3) C38A 0.026(3) 0.037(4) 0.031(3) 0.003(3) -0.007(3) -0.013(3) C38B 0.026(3) 0.037(4) 0.031(3) 0.003(3) -0.007(3) -0.013(3) C39 0.041(3) 0.032(3) 0.060(4) -0.002(2) -0.006(3) -0.014(2) C40 0.042(3) 0.042(3) 0.068(4) 0.006(3) -0.027(3) -0.014(3) C41 0.035(3) 0.026(2) 0.066(4) 0.021(2) -0.031(3) -0.016(2) C42 0.042(3) 0.065(4) 0.064(4) -0.014(3) 0.003(3) -0.011(3) C43 0.069(4) 0.063(4) 0.054(4) -0.002(3) -0.030(3) -0.026(3) C44 0.084(6) 0.100(6) 0.148(9) 0.026(6) -0.069(6) -0.058(5) C45 0.107(6) 0.098(6) 0.081(6) 0.012(5) -0.065(5) -0.029(5) C46 0.067(4) 0.070(4) 0.065(5) 0.005(4) 0.000(4) -0.029(4) C47 0.036(3) 0.063(4) 0.104(6) -0.027(4) -0.024(4) -0.008(3) C48 0.067(4) 0.065(4) 0.067(5) -0.002(3) -0.039(4) 0.004(4) C49 0.061(4) 0.060(4) 0.103(6) 0.024(4) -0.007(4) -0.028(4) C50 0.046(4) 0.101(6) 0.078(5) 0.028(4) -0.031(3) -0.034(4) C51 0.048(4) 0.083(5) 0.059(4) 0.017(4) -0.007(3) -0.007(4) C52 0.100(6) 0.074(5) 0.045(4) 0.008(3) -0.026(4) -0.024(4) C53 0.070(5) 0.112(6) 0.054(4) 0.025(4) -0.036(4) -0.043(5) C54 0.042(3) 0.087(5) 0.048(4) 0.014(3) -0.010(3) -0.003(4) C55 0.086(5) 0.068(4) 0.064(5) 0.005(3) -0.028(4) -0.024(4) _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. asd sdf DFIX The bond distance between O1 and C39 was fixed to be 1.3(0.01) DFIX The bond distance between O2 and C41 was fixed to be 1.55(0.01) EADP C37A C37B EADP C38A C38B EADP C36A C36B EADP C33A C33B EADP C34B C34A EADP C35B C35A ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 O1 2.215(3) . ? Ir1 O2 2.165(3) . ? Ir1 N1 2.054(4) . ? Ir1 N2 2.042(4) . ? Ir1 C9 2.006(4) . ? Ir1 C28 2.002(4) . ? S1 C1 1.741(5) . ? S1 C7 1.726(5) . ? S2 C20 1.748(5) . ? S2 C26 1.741(5) . ? O1 C39 1.209(5) . ? O2 C41 1.204(5) . ? N1 C6 1.407(5) . ? N1 C7 1.327(5) . ? N2 C25 1.392(6) . ? N2 C26 1.330(5) . ? C1 C2 1.390(6) . ? C1 C6 1.400(6) . ? C2 H2 0.9500 . ? C2 C3 1.369(7) . ? C3 H3 0.9500 . ? C3 C4 1.400(7) . ? C4 H4 0.9500 . ? C4 C5 1.378(7) . ? C5 H5 0.9500 . ? C5 C6 1.394(6) . ? C7 C8 1.442(6) . ? C8 C9 1.412(6) . ? C8 C13 1.403(6) . ? C9 C10 1.404(6) . ? C10 H10 0.9500 . ? C10 C11 1.392(6) . ? C11 C12 1.394(6) . ? C11 C14 1.494(6) . ? C12 H12 0.9500 . ? C12 C13 1.370(6) . ? C13 H13 0.9500 . ? C14 C15 1.379(6) . ? C14 C19 1.414(6) . ? C15 H15 0.9500 . ? C15 C16 1.391(6) . ? C16 H16 0.9500 . ? C16 C17 1.389(6) . ? C17 H17 0.9500 . ? C17 C18 1.360(8) . ? C18 H18 0.9500 . ? C18 C19 1.372(7) . ? C19 H19 0.9500 . ? C20 C21 1.373(7) . ? C20 C25 1.403(6) . ? C21 H21 0.9500 . ? C21 C22 1.383(7) . ? C22 H22 0.9500 . ? C22 C23 1.397(7) . ? C23 H23 0.9500 . ? C23 C24 1.371(7) . ? C24 H24 0.9500 . ? C24 C25 1.392(6) . ? C26 C27 1.428(6) . ? C27 C28 1.415(6) . ? C27 C32 1.405(6) . ? C28 C29 1.393(6) . ? C29 H29 0.9500 . ? C29 C30 1.400(6) . ? C30 C31 1.406(7) . ? C30 C33A 1.421(13) . ? C30 C33B 1.609(13) . ? C31 H31 0.9500 . ? C31 C32 1.366(8) . ? C32 H32 0.9500 . ? C33A C34A 1.413(16) . ? C33A C38A 1.394(15) . ? C33B C34B 1.371(16) . ? C33B C38B 1.400(13) . ? C34A H34 0.9500 . ? C34A C35A 1.37(2) . ? C34B H34A 0.9500 . ? C34B C35B 1.38(2) . ? C35A H35 0.9500 . ? C35A C36A 1.408(17) . ? C35B H35A 0.9500 . ? C35B C36B 1.41(3) . ? C36A H36 0.9500 . ? C36A C37A 1.366(14) . ? C36B H36A 0.9500 . ? C36B C37B 1.388(12) . ? C37A H37 0.9500 . ? C37A C38A 1.394(13) . ? C37B C37B 1.659(19) 2_665 ? C37B H37A 1.0000 . ? C37B C38B 1.388(13) . ? C38A H38 0.9500 . ? C38B H38A 0.9500 . ? C39 C40 1.359(7) . ? C39 C42 1.522(7) . ? C40 H40 0.9500 . ? C40 C41 1.410(7) . ? C41 C43 1.548(7) . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C42 H42A 0.9800 . ? C43 H43A 0.9800 . ? C43 H43C 0.9800 . ? C43 H43B 0.9800 . ? C44 H44 0.9500 . ? C44 C45 1.328(11) . ? C44 C49 1.351(10) . ? C45 H45 0.9500 . ? C45 C46 1.360(10) . ? C46 H46 0.9500 . ? C46 C47 1.349(9) . ? C47 H47 0.9500 . ? C47 C48 1.360(10) . ? C48 H48 0.9500 . ? C48 C49 1.372(9) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C50 C51 1.342(9) . ? C50 C55 1.379(8) . ? C51 H51 0.9500 . ? C51 C52 1.369(9) . ? C52 H52 0.9500 . ? C52 C53 1.367(9) . ? C53 H53 0.9500 . ? C53 C54 1.382(9) . ? C54 H54 0.9500 . ? C54 C55 1.362(9) . ? C55 H55 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C39 C40 129.7(5) . . ? O1 C39 C42 113.8(5) . . ? O2 Ir1 O1 86.21(12) . . ? O2 C41 C40 128.0(5) . . ? O2 C41 C43 113.7(4) . . ? N1 Ir1 O1 88.25(11) . . ? N1 Ir1 O2 99.40(13) . . ? N1 C7 S1 114.9(3) . . ? N1 C7 C8 117.7(4) . . ? N2 Ir1 O1 98.04(12) . . ? N2 Ir1 O2 85.20(12) . . ? N2 Ir1 N1 172.47(13) . . ? N2 C25 C20 114.4(4) . . ? N2 C25 C24 126.5(4) . . ? N2 C26 S2 114.2(3) . . ? N2 C26 C27 117.9(4) . . ? C1 C2 H2 121.3 . . ? C1 C6 N1 112.9(4) . . ? C2 C1 S1 127.7(4) . . ? C2 C1 C6 121.6(4) . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.2(4) . . ? C3 C2 C1 117.4(5) . . ? C3 C2 H2 121.3 . . ? C3 C4 H4 119.0 . . ? C4 C3 H3 119.4 . . ? C4 C5 H5 121.5 . . ? C4 C5 C6 117.1(5) . . ? C5 C4 C3 122.0(5) . . ? C5 C4 H4 119.0 . . ? C5 C6 N1 126.5(4) . . ? C5 C6 C1 120.6(4) . . ? C6 N1 Ir1 134.2(3) . . ? C6 C1 S1 110.7(3) . . ? C6 C5 H5 121.5 . . ? C7 S1 C1 89.7(2) . . ? C7 N1 Ir1 113.9(3) . . ? C7 N1 C6 111.8(4) . . ? C8 C7 S1 127.3(3) . . ? C8 C9 Ir1 114.8(3) . . ? C8 C13 H13 120.4 . . ? C9 Ir1 O1 90.75(13) . . ? C9 Ir1 O2 176.96(14) . . ? C9 Ir1 N1 80.23(16) . . ? C9 Ir1 N2 95.48(15) . . ? C9 C8 C7 113.1(4) . . ? C9 C10 H10 119.2 . . ? C10 C9 Ir1 128.6(3) . . ? C10 C9 C8 116.5(4) . . ? C10 C11 C12 120.1(4) . . ? C10 C11 C14 120.2(4) . . ? C11 C10 C9 121.5(4) . . ? C11 C10 H10 119.2 . . ? C11 C12 H12 119.8 . . ? C12 C11 C14 119.8(4) . . ? C12 C13 C8 119.3(4) . . ? C12 C13 H13 120.4 . . ? C13 C8 C7 124.8(4) . . ? C13 C8 C9 122.1(4) . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.8 . . ? C14 C15 H15 119.3 . . ? C14 C15 C16 121.5(4) . . ? C14 C19 H19 120.3 . . ? C15 C14 C11 121.7(4) . . ? C15 C14 C19 118.4(4) . . ? C15 C16 H16 120.5 . . ? C16 C15 H15 119.3 . . ? C16 C17 H17 119.9 . . ? C17 C16 C15 118.9(5) . . ? C17 C16 H16 120.5 . . ? C17 C18 H18 119.1 . . ? C17 C18 C19 121.7(5) . . ? C18 C17 C16 120.1(5) . . ? C18 C17 H17 119.9 . . ? C18 C19 C14 119.4(5) . . ? C18 C19 H19 120.3 . . ? C19 C14 C11 119.9(4) . . ? C19 C18 H18 119.1 . . ? C20 C21 H21 121.0 . . ? C20 C21 C22 118.1(5) . . ? C21 C20 S2 128.4(4) . . ? C21 C20 C25 122.2(4) . . ? C21 C22 H22 119.9 . . ? C21 C22 C23 120.3(5) . . ? C22 C21 H21 121.0 . . ? C22 C23 H23 119.2 . . ? C23 C22 H22 119.9 . . ? C23 C24 H24 120.7 . . ? C23 C24 C25 118.7(4) . . ? C24 C23 C22 121.6(5) . . ? C24 C23 H23 119.2 . . ? C24 C25 C20 119.1(4) . . ? C25 N2 Ir1 134.6(3) . . ? C25 C20 S2 109.4(4) . . ? C25 C24 H24 120.7 . . ? C26 S2 C20 90.1(2) . . ? C26 N2 Ir1 113.5(3) . . ? C26 N2 C25 111.8(4) . . ? C27 C26 S2 127.9(3) . . ? C27 C28 Ir1 114.0(3) . . ? C27 C32 H32 120.1 . . ? C28 Ir1 O1 173.95(13) . . ? C28 Ir1 O2 87.85(15) . . ? C28 Ir1 N1 93.83(16) . . ? C28 Ir1 N2 80.32(16) . . ? C28 Ir1 C9 95.19(15) . . ? C28 C27 C26 113.1(4) . . ? C28 C29 H29 118.7 . . ? C28 C29 C30 122.5(5) . . ? C29 C28 Ir1 128.9(3) . . ? C29 C28 C27 116.8(4) . . ? C29 C30 C31 118.6(5) . . ? C29 C30 C33A 127.7(6) . . ? C29 C30 C33B 114.1(6) . . ? C30 C29 H29 118.7 . . ? C30 C31 H31 119.6 . . ? C31 C30 C33A 112.7(6) . . ? C31 C30 C33B 126.3(6) . . ? C31 C32 C27 119.8(5) . . ? C31 C32 H32 120.1 . . ? C32 C27 C26 125.4(4) . . ? C32 C27 C28 121.4(5) . . ? C32 C31 C30 120.8(4) . . ? C32 C31 H31 119.6 . . ? C33A C30 C33B 23.9(4) . . ? C33A C34A H34 119.2 . . ? C33A C38A H38 118.8 . . ? C33B C34B H34A 118.8 . . ? C33B C34B C35B 122.4(14) . . ? C33B C38B H38A 119.2 . . ? C34A C33A C30 124.0(11) . . ? C34A C35A H35 120.0 . . ? C34A C35A C36A 120.0(15) . . ? C34B C33B C30 113.2(9) . . ? C34B C33B C38B 117.9(11) . . ? C34B C35B H35A 120.5 . . ? C34B C35B C36B 118.9(16) . . ? C35A C34A C33A 121.6(12) . . ? C35A C34A H34 119.2 . . ? C35A C36A H36 120.0 . . ? C35B C34B H34A 118.8 . . ? C35B C36B H36A 120.2 . . ? C36A C35A H35 120.0 . . ? C36A C37A H37 120.3 . . ? C36A C37A C38A 119.4(10) . . ? C36B C35B H35A 120.5 . . ? C36B C37B C37B 118.7(10) . 2_665 ? C36B C37B H37A 104.4 . . ? C37A C36A C35A 120.0(13) . . ? C37A C36A H36 120.0 . . ? C37A C38A C33A 122.4(9) . . ? C37A C38A H38 118.8 . . ? C37B C36B C35B 119.7(12) . . ? C37B C36B H36A 120.2 . . ? C37B C37B H37A 104.4 2_665 . ? C37B C38B C33B 121.7(9) . . ? C37B C38B H38A 119.2 . . ? C38A C33A C30 118.9(9) . . ? C38A C33A C34A 116.6(11) . . ? C38A C37A H37 120.3 . . ? C38B C33B C30 128.8(9) . . ? C38B C37B C36B 119.4(9) . . ? C38B C37B C37B 103.8(10) . 2_665 ? C38B C37B H37A 104.4 . . ? C39 O1 Ir1 122.7(3) . . ? C39 C40 H40 116.5 . . ? C39 C40 C41 127.0(5) . . ? C39 C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? C39 C42 H42A 109.5 . . ? C40 C39 C42 116.5(5) . . ? C40 C41 C43 118.1(5) . . ? C41 O2 Ir1 124.8(3) . . ? C41 C40 H40 116.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43C 109.5 . . ? C41 C43 H43B 109.5 . . ? H42B C42 H42C 109.5 . . ? H42B C42 H42A 109.5 . . ? H42C C42 H42A 109.5 . . ? H43A C43 H43C 109.5 . . ? H43A C43 H43B 109.5 . . ? H43C C43 H43B 109.5 . . ? C44 C45 H45 119.1 . . ? C44 C45 C46 121.7(7) . . ? C44 C49 C48 120.5(7) . . ? C44 C49 H49 119.7 . . ? C45 C44 H44 120.3 . . ? C45 C44 C49 119.5(7) . . ? C45 C46 H46 120.6 . . ? C46 C45 H45 119.1 . . ? C46 C47 H47 119.6 . . ? C46 C47 C48 120.7(6) . . ? C47 C46 C45 118.9(7) . . ? C47 C46 H46 120.6 . . ? C47 C48 H48 120.7 . . ? C47 C48 C49 118.6(7) . . ? C48 C47 H47 119.6 . . ? C48 C49 H49 119.7 . . ? C49 C44 H44 120.3 . . ? C49 C48 H48 120.7 . . ? C50 C51 H51 120.0 . . ? C50 C51 C52 119.9(6) . . ? C50 C55 H55 119.9 . . ? C51 C50 H50 119.7 . . ? C51 C50 C55 120.6(7) . . ? C51 C52 H52 119.9 . . ? C52 C51 H51 120.0 . . ? C52 C53 H53 120.0 . . ? C52 C53 C54 120.1(7) . . ? C53 C52 C51 120.2(7) . . ? C53 C52 H52 119.9 . . ? C53 C54 H54 120.5 . . ? C54 C53 H53 120.0 . . ? C54 C55 C50 120.3(6) . . ? C54 C55 H55 119.9 . . ? C55 C50 H50 119.7 . . ? C55 C54 C53 119.0(6) . . ? C55 C54 H54 120.5 . . ? _database_code_depnum_ccdc_archive 'CCDC 818631'