# 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_I _database_code_depnum_ccdc_archive 'CCDC 917254' #TrackingRef 'web_deposit_cif_file_0_EliZysman-Colman_1356643359.X-ray structures for paper.cif' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C32.50 H27 Ir N4 O2.50 S' _chemical_formula_iupac ? _chemical_formula_weight 737.84 _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7490(2) _cell_length_b 16.2451(4) _cell_length_c 21.1497(4) _cell_angle_alpha 104.1510(10) _cell_angle_beta 94.4650(10) _cell_angle_gamma 102.1170(10) _cell_volume 2823.24(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9804 _cell_measurement_theta_min 3.1158 _cell_measurement_theta_max 69.1219 _cell_measurement_temperature 100.(2) _exptl_crystal_description Needle _exptl_crystal_colour 'clear light yellow' _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 10.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.82 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'ImuS micro--focus source with MX optics' _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator none _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 47407 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 69.70 _diffrn_reflns_theta_full 69.70 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measured_fraction_theta_full 0.971 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _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. ; _reflns_number_total 10354 _reflns_number_gt 9518 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_gt 0.1243 _refine_ls_wR_factor_ref 0.1288 _refine_ls_goodness_of_fit_ref 1.266 _refine_ls_restrained_S_all 1.274 _refine_ls_number_reflns 10354 _refine_ls_number_parameters 638 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+25.5535P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.058 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 3.216 _refine_diff_density_min -3.029 _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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -4.7710 6.5667 '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' _computing_data_collection 'Bruker Instrument Service v2011.8.1.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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 _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.7715(8) 0.6801(5) 0.5311(3) 0.0270(15) Uani d . 1 . . C C2 0.8592(9) 0.7052(6) 0.5936(4) 0.0332(17) Uani d . 1 . . H H2 0.8815 0.7647 0.6183 0.04 Uiso calc R 1 . . C C3 0.9148(10) 0.6454(6) 0.6209(4) 0.041(2) Uani d . 1 . . H H3 0.9719 0.6639 0.664 0.049 Uiso calc R 1 . . C C4 0.8865(10) 0.5588(6) 0.5850(5) 0.045(2) Uani d . 1 . . H H4 0.9299 0.5186 0.6023 0.054 Uiso calc R 1 . . C C5 0.7952(10) 0.5311(6) 0.5241(5) 0.0400(19) Uani d . 1 . . H H5 0.7748 0.4716 0.4997 0.048 Uiso calc R 1 . . C C6 0.7328(9) 0.5901(5) 0.4983(4) 0.0296(16) Uani d . 1 . . C C7 0.6226(9) 0.5658(5) 0.4378(4) 0.0284(15) Uani d . 1 . . C C8 0.5498(10) 0.4795(5) 0.4021(4) 0.0357(18) Uani d . 1 . . H H8 0.5751 0.4318 0.4157 0.043 Uiso calc R 1 . . C C9 0.4419(10) 0.4645(5) 0.3473(4) 0.0383(19) Uani d . 1 . . H H9 0.3905 0.4063 0.3234 0.046 Uiso calc R 1 . . C C10 0.4081(9) 0.5342(5) 0.3267(4) 0.0346(17) Uani d . 1 . . H H10 0.3362 0.525 0.2882 0.041 Uiso calc R 1 . . C C11 0.4829(9) 0.6182(5) 0.3644(4) 0.0299(16) Uani d . 1 . . H H11 0.4597 0.6664 0.351 0.036 Uiso calc R 1 . . C C12 0.5392(9) 0.7691(5) 0.5383(3) 0.0258(14) Uani d . 1 . . C C13 0.3891(9) 0.7146(5) 0.5338(4) 0.0317(16) Uani d . 1 . . H H13 0.3546 0.6638 0.4979 0.038 Uiso calc R 1 . . C C14 0.2899(10) 0.7335(6) 0.5808(4) 0.0365(18) Uani d . 1 . . H H14 0.1893 0.6952 0.5768 0.044 Uiso calc R 1 . . C C15 0.3365(10) 0.8081(6) 0.6335(4) 0.0406(19) Uani d . 1 . . H H15 0.2672 0.8213 0.6649 0.049 Uiso calc R 1 . . C C16 0.4837(10) 0.8625(6) 0.6400(4) 0.0375(18) Uani d . 1 . . H H16 0.5162 0.9135 0.6758 0.045 Uiso calc R 1 . . C C17 0.5850(9) 0.8426(5) 0.5939(3) 0.0291(15) Uani d . 1 . . C C18 0.7444(9) 0.8963(5) 0.5973(3) 0.0287(15) Uani d . 1 . . C C19 0.8247(10) 0.9665(5) 0.6495(4) 0.0344(17) Uani d . 1 . . H H19 0.7741 0.9854 0.6867 0.041 Uiso calc R 1 . . C C20 0.9772(11) 1.0086(5) 0.6472(4) 0.040(2) Uani d . 1 . . H H20 1.0325 1.0559 0.6831 0.048 Uiso calc R 1 . . C C21 1.0501(11) 0.9815(6) 0.5922(4) 0.045(2) Uani d . 1 . . H H21 1.1548 1.0104 0.5896 0.054 Uiso calc R 1 . . C C22 0.9665(10) 0.9114(5) 0.5415(4) 0.0367(18) Uani d . 1 . . H H22 1.0153 0.8928 0.5037 0.044 Uiso calc R 1 . . C C23 0.5172(9) 0.8568(5) 0.3949(4) 0.0304(16) Uani d . 1 . . C C24 0.4530(11) 0.8700(5) 0.3383(4) 0.041(2) Uani d . 1 . . H H24 0.3808 0.9066 0.3414 0.05 Uiso calc R 1 . . C C25 0.6734(11) 0.8039(6) 0.2845(4) 0.045(2) Uani d . 1 . . H H25 0.7447 0.7974 0.253 0.054 Uiso calc R 1 . . C C26 0.7157(10) 0.7968(5) 0.3465(4) 0.0334(17) Uani d . 1 . . C C27 0.8627(9) 0.7663(5) 0.3584(4) 0.0321(17) Uani d . 1 . . C C28 0.9721(10) 0.7584(6) 0.3139(4) 0.0389(19) Uani d . 1 . . H H28 0.9572 0.7737 0.2737 0.047 Uiso calc R 1 . . C C29 1.1019(11) 0.7281(6) 0.3293(4) 0.047(2) Uani d . 1 . . H H29 1.1777 0.7224 0.2997 0.056 Uiso calc R 1 . . C C30 1.1216(11) 0.7060(7) 0.3876(4) 0.047(2) Uani d . 1 . . H H30 1.2099 0.6841 0.3983 0.057 Uiso calc R 1 . . C C31 1.0110(10) 0.7161(6) 0.4306(4) 0.0395(19) Uani d . 1 . . H H31 1.0257 0.7023 0.4715 0.047 Uiso calc R 1 . . C C32 0.4508(11) 0.8909(5) 0.4569(4) 0.0380(19) Uani d . 1 . . H H32A 0.3814 0.9284 0.4487 0.057 Uiso calc R 1 . . H H32B 0.5374 0.9248 0.4918 0.057 Uiso calc R 1 . . H H32C 0.3904 0.8417 0.4706 0.057 Uiso calc R 1 . . C C33 1.1190(13) 0.2648(7) 0.1553(5) 0.0649(9) Uani d G 1 . . C C34 1.2653(13) 0.3219(7) 0.1615(5) 0.0649(9) Uani d G 1 . . H H34 1.2772 0.3668 0.1394 0.078 Uiso calc R 1 . . C C35 1.3942(16) 0.3133(8) 0.2000(5) 0.0649(9) Uani d G 1 . . H H35 1.4942 0.3523 0.2042 0.078 Uiso calc R 1 . . C C36 1.3768(16) 0.2477(8) 0.2323(5) 0.0649(9) Uani d G 1 . . H H36 1.4649 0.2418 0.2586 0.078 Uiso calc R 1 . . C C37 1.2305(16) 0.1906(8) 0.2261(5) 0.0649(9) Uani d G 1 . . H H37 1.2185 0.1457 0.2482 0.078 Uiso calc R 1 . . C C38 1.1016(8) 0.1992(5) 0.1876(4) 0.0649(9) Uani d G 1 . . C C39 0.9476(7) 0.1551(4) 0.1755(2) 0.0649(9) Uani d G 1 . . C C40 0.8993(8) 0.0896(4) 0.2078(3) 0.0649(9) Uani d G 1 . . H H40 0.9687 0.0766 0.2388 0.078 Uiso calc R 1 . . C C41 0.7430(8) 0.0460(4) 0.1904(3) 0.0649(9) Uani d R 1 . . H H41 0.7149 0.0037 0.2141 0.078 Uiso d R 1 . . C C42 0.6263(7) 0.0469(4) 0.1514(3) 0.0649(9) Uani d RD 1 . . H H42 0.5245 0.0088 0.1448 0.078 Uiso d R 1 . . C C43 0.6758(8) 0.1212(5) 0.1154(3) 0.0649(9) Uani d RD 1 . . H H43 0.602 0.1319 0.0849 0.078 Uiso d R 1 . . C C44 0.8912(9) 0.3582(5) 0.1787(4) 0.0326(17) Uani d . 1 . . C C45 0.8136(10) 0.3417(7) 0.2310(4) 0.039(2) Uani d . 1 . . H H45 0.771 0.2831 0.2316 0.047 Uiso calc R 1 . . C C46 0.7982(12) 0.4102(8) 0.2820(4) 0.053(3) Uani d . 1 . . H H46 0.7439 0.3978 0.317 0.064 Uiso calc R 1 . . C C47 0.8593(15) 0.4953(8) 0.2829(5) 0.069(4) Uani d . 1 . . H H47 0.8471 0.5415 0.3181 0.082 Uiso calc R 1 . . C C48 0.9390(15) 0.5133(7) 0.2322(5) 0.064(3) Uani d . 1 . . H H48 0.9822 0.5722 0.2325 0.077 Uiso calc R 1 . . C C49 0.9562(11) 0.4449(6) 0.1803(4) 0.042(2) Uani d . 1 . . C C50 1.0384(12) 0.4595(6) 0.1254(5) 0.046(2) Uani d . 1 . . C C51 1.1194(16) 0.5394(7) 0.1172(6) 0.069(3) Uani d . 1 . . H H51 1.122 0.5919 0.1498 0.083 Uiso calc R 1 . . C C52 1.1938(16) 0.5434(8) 0.0640(7) 0.076(4) Uani d . 1 . . H H52 1.2504 0.5981 0.0599 0.091 Uiso calc R 1 . . C C53 1.1875(14) 0.4676(7) 0.0156(6) 0.059(3) Uani d . 1 . . H H53 1.2371 0.4693 -0.0227 0.071 Uiso calc R 1 . . C C54 1.1069(11) 0.3897(6) 0.0245(4) 0.0418(19) Uani d . 1 . . H H54 1.1023 0.3374 -0.0085 0.05 Uiso calc R 1 . . C C55 1.0421(16) 0.1428(7) -0.0223(4) 0.064(3) Uani d . 1 . . C C56 1.074(2) 0.1191(10) -0.0854(5) 0.096(6) Uani d . 1 . . H H56 1.1381 0.0786 -0.0957 0.116 Uiso calc R 1 . . C C57 0.8389(13) 0.1836(6) -0.1152(4) 0.048(2) Uani d . 1 . . H H57 0.7528 0.1859 -0.1445 0.058 Uiso calc R 1 . . C C58 0.8280(11) 0.2009(5) -0.0494(4) 0.0363(18) Uani d . 1 . . C C59 0.6959(12) 0.2372(10) -0.0257(5) 0.0684(14) Uani d . 1 . . C C60 0.5582(12) 0.2336(9) -0.0656(5) 0.0684(14) Uani d . 1 . . H H60 0.5422 0.2017 -0.1106 0.082 Uiso calc R 1 . . C C61 0.4503(12) 0.2734(9) -0.0420(5) 0.0684(14) Uani d . 1 . . H H61 0.3589 0.272 -0.07 0.082 Uiso calc R 1 . . C C62 0.4720(12) 0.3179(9) 0.0251(5) 0.0684(14) Uani d . 1 . . H H62 0.397 0.3479 0.0436 0.082 Uiso calc R 1 . . C C63 0.6083(12) 0.3165(9) 0.0636(5) 0.0684(14) Uani d . 1 . . H H63 0.6238 0.3452 0.1093 0.082 Uiso calc R 1 . . C C64 1.1317(19) 0.1148(9) 0.0294(5) 0.085(5) Uani d . 1 . . H H64A 1.1916 0.0737 0.0081 0.127 Uiso calc R 1 . . H H64B 1.0571 0.0863 0.0542 0.127 Uiso calc R 1 . . H H64C 1.2044 0.1661 0.0595 0.127 Uiso calc R 1 . . C C65 0.593(3) 0.5755(17) 0.1718(10) 0.151(5) Uani d . 1 . . H H65A 0.6404 0.5887 0.2177 0.227 Uiso calc R 1 . . H H65B 0.5287 0.5154 0.1578 0.227 Uiso calc R 1 . . H H65C 0.5259 0.6159 0.1678 0.227 Uiso calc R 1 . . O O5 0.716(2) 0.5853(13) 0.1305(7) 0.151(5) Uani d . 1 . . H H5A 0.7283 0.6342 0.1225 0.227 Uiso calc R 1 . . N N1 0.5853(7) 0.6340(4) 0.4183(3) 0.0235(12) Uani d . 1 . . N N2 0.8185(7) 0.8686(4) 0.5439(3) 0.0267(13) Uani d . 1 . . N N3 0.6401(7) 0.8165(4) 0.4003(3) 0.0282(13) Uani d . 1 . . N N4 0.8833(7) 0.7451(4) 0.4156(3) 0.0304(14) Uani d . 1 . . N N5 0.8279(13) 0.1678(6) 0.1291(4) 0.0649(9) Uani d . 1 . . N N6 1.0341(8) 0.3838(4) 0.0778(3) 0.0347(15) Uani d . 1 . . N N7 0.7170(10) 0.2767(8) 0.0390(4) 0.0684(14) Uani d . 1 . . N N8 0.9319(9) 0.1897(4) -0.0017(3) 0.0383(16) Uani d . 1 . . O O1 0.3832(7) 0.7427(4) 0.2306(3) 0.0406(13) Uani d . 1 . . O O2 0.5118(9) 0.8851(5) 0.2227(3) 0.064(2) Uani d . 1 . . O O3 1.1152(10) 0.2397(8) -0.1532(4) 0.090(3) Uani d . 1 . . O O4 0.9618(14) 0.0946(8) -0.2078(4) 0.108(4) Uani d . 1 . . S S1 0.4963(3) 0.82390(14) 0.26276(9) 0.0416(5) Uani d . 1 . . S S2 1.0037(4) 0.1579(3) -0.14686(11) 0.0765(10) Uani d . 1 . . Ir Ir1 0.70163(3) 0.754844(18) 0.477067(13) 0.02254(10) Uani d . 1 . . Ir Ir2 0.92063(4) 0.27168(2) 0.097161(14) 0.02842(10) Uani d . 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 C1 0.021(4) 0.039(4) 0.026(3) 0.009(3) 0.011(3) 0.013(3) C2 0.021(4) 0.051(5) 0.030(4) 0.006(3) 0.009(3) 0.014(3) C3 0.028(4) 0.069(6) 0.035(4) 0.013(4) 0.009(3) 0.028(4) C4 0.033(4) 0.060(6) 0.059(6) 0.019(4) 0.017(4) 0.039(5) C5 0.031(4) 0.042(5) 0.055(5) 0.012(4) 0.019(4) 0.022(4) C6 0.023(4) 0.035(4) 0.037(4) 0.010(3) 0.016(3) 0.016(3) C7 0.027(4) 0.031(4) 0.032(4) 0.008(3) 0.017(3) 0.011(3) C8 0.039(5) 0.030(4) 0.041(4) 0.010(3) 0.020(4) 0.009(3) C9 0.037(5) 0.024(4) 0.045(5) -0.002(3) 0.019(4) -0.004(3) C10 0.027(4) 0.039(4) 0.029(4) 0.000(3) 0.010(3) -0.002(3) C11 0.024(4) 0.035(4) 0.030(4) 0.008(3) 0.011(3) 0.005(3) C12 0.030(4) 0.030(4) 0.023(3) 0.011(3) 0.006(3) 0.013(3) C13 0.034(4) 0.035(4) 0.030(4) 0.012(3) 0.008(3) 0.012(3) C14 0.028(4) 0.049(5) 0.041(4) 0.012(3) 0.010(3) 0.022(4) C15 0.038(5) 0.061(5) 0.031(4) 0.024(4) 0.016(4) 0.014(4) C16 0.045(5) 0.048(5) 0.024(4) 0.019(4) 0.007(3) 0.010(3) C17 0.035(4) 0.038(4) 0.018(3) 0.013(3) 0.004(3) 0.009(3) C18 0.035(4) 0.031(4) 0.019(3) 0.009(3) 0.001(3) 0.006(3) C19 0.050(5) 0.035(4) 0.018(3) 0.009(4) 0.003(3) 0.007(3) C20 0.054(5) 0.032(4) 0.022(4) -0.004(4) -0.004(4) 0.001(3) C21 0.040(5) 0.047(5) 0.034(4) -0.012(4) 0.005(4) 0.007(4) C22 0.034(4) 0.043(4) 0.022(4) -0.008(3) 0.005(3) 0.003(3) C23 0.036(4) 0.024(3) 0.026(4) 0.000(3) -0.003(3) 0.006(3) C24 0.053(5) 0.036(4) 0.032(4) 0.003(4) -0.001(4) 0.012(3) C25 0.038(5) 0.065(6) 0.023(4) -0.009(4) 0.002(3) 0.014(4) C26 0.036(4) 0.035(4) 0.021(4) -0.010(3) 0.002(3) 0.008(3) C27 0.031(4) 0.034(4) 0.021(3) -0.009(3) 0.005(3) 0.001(3) C28 0.034(5) 0.044(5) 0.025(4) -0.011(4) 0.007(3) -0.001(3) C29 0.034(5) 0.062(6) 0.032(4) -0.003(4) 0.018(4) -0.002(4) C30 0.029(4) 0.070(6) 0.038(5) 0.008(4) 0.013(4) 0.005(4) C31 0.029(4) 0.057(5) 0.027(4) 0.006(4) 0.004(3) 0.004(4) C32 0.056(5) 0.033(4) 0.026(4) 0.019(4) 0.000(4) 0.004(3) C33 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C34 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C35 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C36 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C37 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C38 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C39 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C40 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C41 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C42 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C43 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) C44 0.028(4) 0.051(5) 0.023(4) 0.025(3) 0.001(3) 0.004(3) C45 0.030(4) 0.072(6) 0.020(4) 0.027(4) 0.000(3) 0.007(4) C46 0.050(6) 0.090(8) 0.027(4) 0.049(6) 0.004(4) 0.003(5) C47 0.087(9) 0.088(9) 0.035(5) 0.063(7) 0.008(5) -0.011(5) C48 0.088(8) 0.055(6) 0.048(6) 0.040(6) 0.003(6) -0.007(5) C49 0.051(5) 0.045(5) 0.031(4) 0.029(4) -0.001(4) -0.002(4) C50 0.059(6) 0.037(5) 0.042(5) 0.023(4) -0.001(4) 0.004(4) C51 0.093(9) 0.039(5) 0.068(7) 0.013(5) -0.003(7) 0.005(5) C52 0.083(9) 0.055(7) 0.091(10) -0.001(6) 0.006(7) 0.038(7) C53 0.061(7) 0.063(7) 0.058(6) 0.012(5) 0.011(5) 0.028(5) C54 0.041(5) 0.051(5) 0.038(5) 0.016(4) 0.006(4) 0.014(4) C55 0.113(10) 0.069(7) 0.019(4) 0.058(7) -0.001(5) -0.003(4) C56 0.160(14) 0.131(12) 0.022(5) 0.117(12) 0.003(6) -0.002(6) C57 0.068(6) 0.055(5) 0.020(4) 0.018(5) 0.000(4) 0.005(4) C58 0.051(5) 0.036(4) 0.016(3) 0.003(4) -0.004(3) 0.004(3) C59 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) C60 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) C61 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) C62 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) C63 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) C64 0.155(13) 0.093(9) 0.030(5) 0.100(10) 0.005(6) 0.002(5) C65 0.169(12) 0.233(15) 0.111(8) 0.131(12) 0.059(8) 0.074(9) O5 0.169(12) 0.233(15) 0.111(8) 0.131(12) 0.059(8) 0.074(9) N1 0.018(3) 0.025(3) 0.022(3) -0.002(2) 0.008(2) -0.001(2) N2 0.027(3) 0.029(3) 0.016(3) -0.003(2) -0.001(2) 0.002(2) N3 0.033(3) 0.025(3) 0.017(3) -0.006(2) 0.000(2) 0.002(2) N4 0.027(3) 0.037(3) 0.020(3) -0.001(3) 0.002(2) 0.001(2) N5 0.094(2) 0.071(2) 0.0339(14) 0.0402(18) 0.0126(16) 0.0029(14) N6 0.035(4) 0.039(4) 0.031(3) 0.017(3) 0.002(3) 0.006(3) N7 0.037(2) 0.133(4) 0.0266(18) 0.019(2) -0.0019(15) 0.007(2) N8 0.057(5) 0.033(3) 0.022(3) 0.015(3) 0.002(3) 0.001(3) O1 0.037(3) 0.053(3) 0.026(3) 0.000(3) 0.005(2) 0.008(2) O2 0.078(5) 0.068(5) 0.036(3) -0.013(4) -0.010(3) 0.028(3) O3 0.057(5) 0.167(10) 0.058(5) 0.020(6) 0.025(4) 0.054(6) O4 0.152(10) 0.157(10) 0.024(4) 0.097(8) 0.000(5) -0.004(5) S1 0.0468(12) 0.0484(11) 0.0225(9) -0.0078(9) -0.0044(8) 0.0154(8) S2 0.101(2) 0.124(3) 0.0194(10) 0.073(2) 0.0083(12) 0.0065(13) Ir1 0.02321(16) 0.02590(16) 0.01615(15) 0.00222(11) 0.00334(11) 0.00414(11) Ir2 0.03729(19) 0.03333(18) 0.01462(15) 0.01301(14) 0.00096(12) 0.00324(12) _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 C1 C2 . 1.397(11) ? C1 C6 . 1.411(11) ? C1 Ir1 . 2.009(7) ? C2 C3 . 1.395(12) ? C2 H2 . 0.95 ? C3 C4 . 1.385(14) ? C3 H3 . 0.95 ? C4 C5 . 1.380(13) ? C4 H4 . 0.95 ? C5 C6 . 1.395(11) ? C5 H5 . 0.95 ? C6 C7 . 1.459(11) ? C7 N1 . 1.363(9) ? C7 C8 . 1.405(11) ? C8 C9 . 1.375(13) ? C8 H8 . 0.95 ? C9 C10 . 1.386(12) ? C9 H9 . 0.95 ? C10 C11 . 1.392(11) ? C10 H10 . 0.95 ? C11 N1 . 1.330(10) ? C11 H11 . 0.95 ? C12 C13 . 1.403(11) ? C12 C17 . 1.417(10) ? C12 Ir1 . 2.007(7) ? C13 C14 . 1.390(11) ? C13 H13 . 0.95 ? C14 C15 . 1.393(12) ? C14 H14 . 0.95 ? C15 C16 . 1.376(13) ? C15 H15 . 0.95 ? C16 C17 . 1.393(11) ? C16 H16 . 0.95 ? C17 C18 . 1.467(11) ? C18 N2 . 1.375(9) ? C18 C19 . 1.393(10) ? C19 C20 . 1.375(12) ? C19 H19 . 0.95 ? C20 C21 . 1.392(12) ? C20 H20 . 0.95 ? C21 C22 . 1.383(11) ? C21 H21 . 0.95 ? C22 N2 . 1.346(10) ? C22 H22 . 0.95 ? C23 C24 . 1.364(11) ? C23 N3 . 1.383(10) ? C23 C32 . 1.505(11) ? C24 S1 . 1.699(9) ? C24 H24 . 0.95 ? C25 C26 . 1.372(11) ? C25 S1 . 1.701(10) ? C25 H25 . 0.95 ? C26 N3 . 1.365(10) ? C26 C27 . 1.498(12) ? C27 N4 . 1.346(10) ? C27 C28 . 1.396(11) ? C28 C29 . 1.376(14) ? C28 H28 . 0.95 ? C29 C30 . 1.373(14) ? C29 H29 . 0.95 ? C30 C31 . 1.386(12) ? C30 H30 . 0.95 ? C31 N4 . 1.346(11) ? C31 H31 . 0.95 ? C32 H32A . 0.98 ? C32 H32B . 0.98 ? C32 H32C . 0.98 ? C33 C34 . 1.39 ? C33 C38 . 1.390(13) ? C33 Ir2 . 2.087(11) ? C34 C35 . 1.390(16) ? C34 H34 . 0.95 ? C35 C36 . 1.390(16) ? C35 H35 . 0.95 ? C36 C37 . 1.390(18) ? C36 H36 . 0.95 ? C37 C38 . 1.390(14) ? C37 H37 . 0.95 ? C38 C39 . 1.3577 ? C39 C40 . 1.4107 ? C39 N5 . 1.460(11) ? C40 C41 . 1.3766 ? C40 H40 . 0.95 ? C41 C42 . 1.2656 ? C41 H41 . 0.95 ? C42 C43 . 1.5814 ? C42 H42 . 0.95 ? C43 N5 . 1.356(13) ? C43 H43 . 0.95 ? C44 C45 . 1.393(12) ? C44 C49 . 1.395(13) ? C44 Ir2 . 2.013(7) ? C45 C46 . 1.385(12) ? C45 H45 . 0.95 ? C46 C47 . 1.369(17) ? C46 H46 . 0.95 ? C47 C48 . 1.380(17) ? C47 H47 . 0.95 ? C48 C49 . 1.401(12) ? C48 H48 . 0.95 ? C49 C50 . 1.456(14) ? C50 N6 . 1.377(11) ? C50 C51 . 1.399(15) ? C51 C52 . 1.352(18) ? C51 H51 . 0.95 ? C52 C53 . 1.383(17) ? C52 H52 . 0.95 ? C53 C54 . 1.378(14) ? C53 H53 . 0.95 ? C54 N6 . 1.351(11) ? C54 H54 . 0.95 ? C55 C56 . 1.362(14) ? C55 N8 . 1.383(12) ? C55 C64 . 1.509(13) ? C56 S2 . 1.703(11) ? C56 H56 . 0.95 ? C57 C58 . 1.366(11) ? C57 S2 . 1.723(11) ? C57 H57 . 0.95 ? C58 N8 . 1.377(10) ? C58 C59 . 1.471(14) ? C59 N7 . 1.342(12) ? C59 C60 . 1.398(13) ? C60 C61 . 1.315(16) ? C60 H60 . 0.95 ? C61 C62 . 1.404(14) ? C61 H61 . 0.95 ? C62 C63 . 1.399(14) ? C62 H62 . 0.95 ? C63 N7 . 1.328(14) ? C63 H63 . 0.95 ? C64 H64A . 0.98 ? C64 H64B . 0.98 ? C64 H64C . 0.98 ? C65 O5 . 1.45(2) ? C65 H65A . 0.98 ? C65 H65B . 0.98 ? C65 H65C . 0.98 ? O5 H5A . 0.84 ? N1 Ir1 . 2.050(5) ? N2 Ir1 . 2.040(6) ? N3 Ir1 . 2.193(6) ? N4 Ir1 . 2.137(6) ? N5 Ir2 . 2.008(10) ? N6 Ir2 . 2.035(7) ? N7 Ir2 . 2.112(8) ? N8 Ir2 . 2.209(6) ? O1 S1 . 1.445(6) ? O2 S1 . 1.449(7) ? O3 S2 . 1.516(11) ? O4 S2 . 1.405(9) ? 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 C2 C1 C6 . . 116.9(7) ? C2 C1 Ir1 . . 129.2(6) ? C6 C1 Ir1 . . 113.8(5) ? C3 C2 C1 . . 121.8(8) ? C3 C2 H2 . . 119.1 ? C1 C2 H2 . . 119.1 ? C4 C3 C2 . . 119.8(8) ? C4 C3 H3 . . 120.1 ? C2 C3 H3 . . 120.1 ? C5 C4 C3 . . 119.8(8) ? C5 C4 H4 . . 120.1 ? C3 C4 H4 . . 120.1 ? C4 C5 C6 . . 120.2(8) ? C4 C5 H5 . . 119.9 ? C6 C5 H5 . . 119.9 ? C5 C6 C1 . . 121.0(8) ? C5 C6 C7 . . 124.3(7) ? C1 C6 C7 . . 114.6(6) ? N1 C7 C8 . . 120.1(7) ? N1 C7 C6 . . 115.2(6) ? C8 C7 C6 . . 124.7(7) ? C9 C8 C7 . . 119.5(7) ? C9 C8 H8 . . 120.2 ? C7 C8 H8 . . 120.2 ? C8 C9 C10 . . 120.0(7) ? C8 C9 H9 . . 120.0 ? C10 C9 H9 . . 120.0 ? C9 C10 C11 . . 117.8(8) ? C9 C10 H10 . . 121.1 ? C11 C10 H10 . . 121.1 ? N1 C11 C10 . . 123.1(7) ? N1 C11 H11 . . 118.5 ? C10 C11 H11 . . 118.5 ? C13 C12 C17 . . 116.5(7) ? C13 C12 Ir1 . . 128.3(6) ? C17 C12 Ir1 . . 115.2(5) ? C14 C13 C12 . . 121.4(7) ? C14 C13 H13 . . 119.3 ? C12 C13 H13 . . 119.3 ? C13 C14 C15 . . 120.6(8) ? C13 C14 H14 . . 119.7 ? C15 C14 H14 . . 119.7 ? C16 C15 C14 . . 119.6(8) ? C16 C15 H15 . . 120.2 ? C14 C15 H15 . . 120.2 ? C15 C16 C17 . . 119.9(8) ? C15 C16 H16 . . 120.0 ? C17 C16 H16 . . 120.0 ? C16 C17 C12 . . 121.9(8) ? C16 C17 C18 . . 123.6(7) ? C12 C17 C18 . . 114.5(6) ? N2 C18 C19 . . 119.8(7) ? N2 C18 C17 . . 113.7(6) ? C19 C18 C17 . . 126.4(7) ? C20 C19 C18 . . 120.1(7) ? C20 C19 H19 . . 120.0 ? C18 C19 H19 . . 120.0 ? C19 C20 C21 . . 119.8(7) ? C19 C20 H20 . . 120.1 ? C21 C20 H20 . . 120.1 ? C22 C21 C20 . . 118.3(8) ? C22 C21 H21 . . 120.8 ? C20 C21 H21 . . 120.8 ? N2 C22 C21 . . 122.4(8) ? N2 C22 H22 . . 118.8 ? C21 C22 H22 . . 118.8 ? C24 C23 N3 . . 125.7(8) ? C24 C23 C32 . . 117.1(8) ? N3 C23 C32 . . 117.2(6) ? C23 C24 S1 . . 123.0(7) ? C23 C24 H24 . . 118.5 ? S1 C24 H24 . . 118.5 ? C26 C25 S1 . . 121.5(7) ? C26 C25 H25 . . 119.2 ? S1 C25 H25 . . 119.2 ? N3 C26 C25 . . 127.3(8) ? N3 C26 C27 . . 114.9(6) ? C25 C26 C27 . . 117.8(8) ? N4 C27 C28 . . 120.9(8) ? N4 C27 C26 . . 115.3(7) ? C28 C27 C26 . . 123.8(7) ? C29 C28 C27 . . 118.9(8) ? C29 C28 H28 . . 120.5 ? C27 C28 H28 . . 120.5 ? C30 C29 C28 . . 119.9(8) ? C30 C29 H29 . . 120.1 ? C28 C29 H29 . . 120.1 ? C29 C30 C31 . . 119.2(9) ? C29 C30 H30 . . 120.4 ? C31 C30 H30 . . 120.4 ? N4 C31 C30 . . 121.2(8) ? N4 C31 H31 . . 119.4 ? C30 C31 H31 . . 119.4 ? C23 C32 H32A . . 109.5 ? C23 C32 H32B . . 109.5 ? H32A C32 H32B . . 109.5 ? C23 C32 H32C . . 109.5 ? H32A C32 H32C . . 109.5 ? H32B C32 H32C . . 109.5 ? C34 C33 C38 . . 120.0(10) ? C34 C33 Ir2 . . 122.4(8) ? C38 C33 Ir2 . . 117.6(7) ? C35 C34 C33 . . 120.0(11) ? C35 C34 H34 . . 120.0 ? C33 C34 H34 . . 120.0 ? C34 C35 C36 . . 120.0(13) ? C34 C35 H35 . . 120.0 ? C36 C35 H35 . . 120.0 ? C37 C36 C35 . . 120.0(12) ? C37 C36 H36 . . 120.0 ? C35 C36 H36 . . 120.0 ? C38 C37 C36 . . 120.0(11) ? C38 C37 H37 . . 120.0 ? C36 C37 H37 . . 120.0 ? C39 C38 C37 . . 131.8(7) ? C39 C38 C33 . . 108.2(6) ? C37 C38 C33 . . 120.0(9) ? C38 C39 C40 . . 118.2 ? C38 C39 N5 . . 124.9(5) ? C40 C39 N5 . . 116.8(5) ? C41 C40 C39 . . 114.1 ? C41 C40 H40 . . 122.9 ? C39 C40 H40 . . 122.9 ? C42 C41 C40 . . 137.5 ? C42 C41 H41 . . 111.3 ? C40 C41 H41 . . 111.3 ? C41 C42 C43 . . 109.6 ? C41 C42 H42 . . 125.2 ? C43 C42 H42 . . 125.2 ? N5 C43 C42 . . 117.5(4) ? N5 C43 H43 . . 121.4 ? C42 C43 H43 . . 121.2 ? C45 C44 C49 . . 118.2(8) ? C45 C44 Ir2 . . 128.3(7) ? C49 C44 Ir2 . . 113.5(6) ? C46 C45 C44 . . 120.3(10) ? C46 C45 H45 . . 119.8 ? C44 C45 H45 . . 119.8 ? C47 C46 C45 . . 121.4(10) ? C47 C46 H46 . . 119.3 ? C45 C46 H46 . . 119.3 ? C46 C47 C48 . . 119.3(9) ? C46 C47 H47 . . 120.3 ? C48 C47 H47 . . 120.3 ? C47 C48 C49 . . 120.1(11) ? C47 C48 H48 . . 119.9 ? C49 C48 H48 . . 119.9 ? C44 C49 C48 . . 120.6(10) ? C44 C49 C50 . . 116.6(7) ? C48 C49 C50 . . 122.8(10) ? N6 C50 C51 . . 119.0(10) ? N6 C50 C49 . . 113.5(8) ? C51 C50 C49 . . 127.4(9) ? C52 C51 C50 . . 121.3(11) ? C52 C51 H51 . . 119.4 ? C50 C51 H51 . . 119.4 ? C51 C52 C53 . . 119.9(11) ? C51 C52 H52 . . 120.0 ? C53 C52 H52 . . 120.0 ? C54 C53 C52 . . 117.8(11) ? C54 C53 H53 . . 121.1 ? C52 C53 H53 . . 121.1 ? N6 C54 C53 . . 123.4(9) ? N6 C54 H54 . . 118.3 ? C53 C54 H54 . . 118.3 ? C56 C55 N8 . . 125.2(9) ? C56 C55 C64 . . 118.0(10) ? N8 C55 C64 . . 116.8(8) ? C55 C56 S2 . . 123.6(8) ? C55 C56 H56 . . 118.2 ? S2 C56 H56 . . 118.2 ? C58 C57 S2 . . 122.2(8) ? C58 C57 H57 . . 118.9 ? S2 C57 H57 . . 118.9 ? C57 C58 N8 . . 126.2(9) ? C57 C58 C59 . . 118.1(8) ? N8 C58 C59 . . 115.7(7) ? N7 C59 C60 . . 120.7(10) ? N7 C59 C58 . . 114.6(8) ? C60 C59 C58 . . 124.7(9) ? C61 C60 C59 . . 121.3(10) ? C61 C60 H60 . . 119.3 ? C59 C60 H60 . . 119.3 ? C60 C61 C62 . . 119.1(10) ? C60 C61 H61 . . 120.4 ? C62 C61 H61 . . 120.4 ? C63 C62 C61 . . 117.5(11) ? C63 C62 H62 . . 121.3 ? C61 C62 H62 . . 121.3 ? N7 C63 C62 . . 122.7(9) ? N7 C63 H63 . . 118.6 ? C62 C63 H63 . . 118.6 ? C55 C64 H64A . . 109.5 ? C55 C64 H64B . . 109.5 ? H64A C64 H64B . . 109.5 ? C55 C64 H64C . . 109.5 ? H64A C64 H64C . . 109.5 ? H64B C64 H64C . . 109.5 ? O5 C65 H65A . . 109.5 ? O5 C65 H65B . . 109.5 ? H65A C65 H65B . . 109.5 ? O5 C65 H65C . . 109.5 ? H65A C65 H65C . . 109.5 ? H65B C65 H65C . . 109.5 ? C65 O5 H5A . . 109.5 ? C11 N1 C7 . . 119.5(6) ? C11 N1 Ir1 . . 126.1(5) ? C7 N1 Ir1 . . 114.4(5) ? C22 N2 C18 . . 119.6(6) ? C22 N2 Ir1 . . 123.9(5) ? C18 N2 Ir1 . . 116.2(5) ? C26 N3 C23 . . 117.3(6) ? C26 N3 Ir1 . . 113.3(5) ? C23 N3 Ir1 . . 128.1(5) ? C31 N4 C27 . . 119.9(7) ? C31 N4 Ir1 . . 123.1(5) ? C27 N4 Ir1 . . 117.0(5) ? C43 N5 C39 . . 124.5(8) ? C43 N5 Ir2 . . 126.5(7) ? C39 N5 Ir2 . . 108.7(7) ? C54 N6 C50 . . 118.5(8) ? C54 N6 Ir2 . . 126.2(6) ? C50 N6 Ir2 . . 115.2(6) ? C63 N7 C59 . . 118.5(9) ? C63 N7 Ir2 . . 123.0(6) ? C59 N7 Ir2 . . 118.4(8) ? C58 N8 C55 . . 117.6(7) ? C58 N8 Ir2 . . 112.1(5) ? C55 N8 Ir2 . . 129.4(6) ? O1 S1 O2 . . 112.2(4) ? O1 S1 C24 . . 111.6(4) ? O2 S1 C24 . . 110.9(5) ? O1 S1 C25 . . 110.1(4) ? O2 S1 C25 . . 111.4(5) ? C24 S1 C25 . . 100.0(4) ? O4 S2 O3 . . 110.9(7) ? O4 S2 C56 . . 113.2(6) ? O3 S2 C56 . . 112.6(7) ? O4 S2 C57 . . 111.0(6) ? O3 S2 C57 . . 110.0(5) ? C56 S2 C57 . . 98.5(6) ? C12 Ir1 C1 . . 85.4(3) ? C12 Ir1 N2 . . 80.3(3) ? C1 Ir1 N2 . . 93.3(3) ? C12 Ir1 N1 . . 96.9(3) ? C1 Ir1 N1 . . 80.7(3) ? N2 Ir1 N1 . . 173.6(2) ? C12 Ir1 N4 . . 177.0(3) ? C1 Ir1 N4 . . 94.2(3) ? N2 Ir1 N4 . . 96.8(2) ? N1 Ir1 N4 . . 86.0(2) ? C12 Ir1 N3 . . 104.9(3) ? C1 Ir1 N3 . . 167.5(3) ? N2 Ir1 N3 . . 95.4(2) ? N1 Ir1 N3 . . 90.8(2) ? N4 Ir1 N3 . . 75.9(2) ? N5 Ir2 C44 . . 93.6(3) ? N5 Ir2 N6 . . 171.7(3) ? C44 Ir2 N6 . . 81.1(3) ? N5 Ir2 C33 . . 80.1(4) ? C44 Ir2 C33 . . 84.3(3) ? N6 Ir2 C33 . . 93.0(4) ? N5 Ir2 N7 . . 98.8(4) ? C44 Ir2 N7 . . 95.6(3) ? N6 Ir2 N7 . . 88.1(4) ? C33 Ir2 N7 . . 178.9(4) ? N5 Ir2 N8 . . 92.8(3) ? C44 Ir2 N8 . . 170.0(3) ? N6 Ir2 N8 . . 93.4(3) ? C33 Ir2 N8 . . 104.4(3) ? N7 Ir2 N8 . . 75.8(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . 4.0(11) ? Ir1 C1 C2 C3 . . . . -171.8(6) ? C1 C2 C3 C4 . . . . 1.5(12) ? C2 C3 C4 C5 . . . . -4.0(12) ? C3 C4 C5 C6 . . . . 0.7(12) ? C4 C5 C6 C1 . . . . 5.1(12) ? C4 C5 C6 C7 . . . . -173.6(7) ? C2 C1 C6 C5 . . . . -7.3(10) ? Ir1 C1 C6 C5 . . . . 169.1(6) ? C2 C1 C6 C7 . . . . 171.5(6) ? Ir1 C1 C6 C7 . . . . -12.1(8) ? C5 C6 C7 N1 . . . . -175.1(7) ? C1 C6 C7 N1 . . . . 6.2(9) ? C5 C6 C7 C8 . . . . 8.4(12) ? C1 C6 C7 C8 . . . . -170.4(7) ? N1 C7 C8 C9 . . . . 0.4(11) ? C6 C7 C8 C9 . . . . 176.9(7) ? C7 C8 C9 C10 . . . . 1.4(12) ? C8 C9 C10 C11 . . . . -1.9(11) ? C9 C10 C11 N1 . . . . 0.6(11) ? C17 C12 C13 C14 . . . . 1.6(10) ? Ir1 C12 C13 C14 . . . . 179.7(6) ? C12 C13 C14 C15 . . . . 0.7(12) ? C13 C14 C15 C16 . . . . -1.4(12) ? C14 C15 C16 C17 . . . . -0.1(12) ? C15 C16 C17 C12 . . . . 2.5(12) ? C15 C16 C17 C18 . . . . -179.2(7) ? C13 C12 C17 C16 . . . . -3.2(10) ? Ir1 C12 C17 C16 . . . . 178.4(6) ? C13 C12 C17 C18 . . . . 178.4(6) ? Ir1 C12 C17 C18 . . . . 0.0(8) ? C16 C17 C18 N2 . . . . -174.9(7) ? C12 C17 C18 N2 . . . . 3.5(9) ? C16 C17 C18 C19 . . . . 8.6(12) ? C12 C17 C18 C19 . . . . -173.0(7) ? N2 C18 C19 C20 . . . . 0.6(11) ? C17 C18 C19 C20 . . . . 177.0(7) ? C18 C19 C20 C21 . . . . 0.9(13) ? C19 C20 C21 C22 . . . . -1.0(14) ? C20 C21 C22 N2 . . . . -0.4(14) ? N3 C23 C24 S1 . . . . 10.0(12) ? C32 C23 C24 S1 . . . . -171.4(6) ? S1 C25 C26 N3 . . . . -10.3(12) ? S1 C25 C26 C27 . . . . 171.2(6) ? N3 C26 C27 N4 . . . . 13.1(9) ? C25 C26 C27 N4 . . . . -168.2(7) ? N3 C26 C27 C28 . . . . -167.8(7) ? C25 C26 C27 C28 . . . . 10.9(11) ? N4 C27 C28 C29 . . . . 0.3(11) ? C26 C27 C28 C29 . . . . -178.8(7) ? C27 C28 C29 C30 . . . . 0.2(13) ? C28 C29 C30 C31 . . . . -1.1(14) ? C29 C30 C31 N4 . . . . 1.6(14) ? C38 C33 C34 C35 . . . . 0.0(15) ? Ir2 C33 C34 C35 . . . . -178.8(7) ? C33 C34 C35 C36 . . . . 0.0(15) ? C34 C35 C36 C37 . . . . 0.0(15) ? C35 C36 C37 C38 . . . . 0.0(15) ? C36 C37 C38 C39 . . . . -177.3(7) ? C36 C37 C38 C33 . . . . 0.0(14) ? C34 C33 C38 C39 . . . . 177.9(8) ? Ir2 C33 C38 C39 . . . . -3.2(8) ? C34 C33 C38 C37 . . . . 0.0(14) ? Ir2 C33 C38 C37 . . . . 178.9(7) ? C37 C38 C39 C40 . . . . 2.5(8) ? C33 C38 C39 C40 . . . . -175.0(7) ? C37 C38 C39 N5 . . . . -174.8(10) ? C33 C38 C39 N5 . . . . 7.7(7) ? C38 C39 C40 C41 . . . . -177.5 ? N5 C39 C40 C41 . . . . 0.1(5) ? C39 C40 C41 C42 . . . . 1.6 ? C40 C41 C42 C43 . . . . -2.7 ? C41 C42 C43 N5 . . . . 2.2(6) ? C49 C44 C45 C46 . . . . 1.8(11) ? Ir2 C44 C45 C46 . . . . -176.8(6) ? C44 C45 C46 C47 . . . . -0.6(13) ? C45 C46 C47 C48 . . . . -0.4(15) ? C46 C47 C48 C49 . . . . 0.2(17) ? C45 C44 C49 C48 . . . . -2.0(12) ? Ir2 C44 C49 C48 . . . . 176.8(7) ? C45 C44 C49 C50 . . . . 179.1(7) ? Ir2 C44 C49 C50 . . . . -2.1(9) ? C47 C48 C49 C44 . . . . 1.0(15) ? C47 C48 C49 C50 . . . . 179.8(10) ? C44 C49 C50 N6 . . . . 2.4(11) ? C48 C49 C50 N6 . . . . -176.4(9) ? C44 C49 C50 C51 . . . . -176.7(10) ? C48 C49 C50 C51 . . . . 4.4(16) ? N6 C50 C51 C52 . . . . -0.5(17) ? C49 C50 C51 C52 . . . . 178.6(11) ? C50 C51 C52 C53 . . . . 2.(2) ? C51 C52 C53 C54 . . . . -1.4(19) ? C52 C53 C54 N6 . . . . 0.1(16) ? N8 C55 C56 S2 . . . . 11.(2) ? C64 C55 C56 S2 . . . . -170.5(12) ? S2 C57 C58 N8 . . . . -8.9(14) ? S2 C57 C58 C59 . . . . 169.4(8) ? C57 C58 C59 N7 . . . . -160.7(11) ? N8 C58 C59 N7 . . . . 17.8(15) ? C57 C58 C59 C60 . . . . 18.3(18) ? N8 C58 C59 C60 . . . . -163.2(12) ? N7 C59 C60 C61 . . . . 4.(2) ? C58 C59 C60 C61 . . . . -174.5(13) ? C59 C60 C61 C62 . . . . -2.(2) ? C60 C61 C62 C63 . . . . -1.(2) ? C61 C62 C63 N7 . . . . 1.(2) ? C10 C11 N1 C7 . . . . 1.2(10) ? C10 C11 N1 Ir1 . . . . 179.9(5) ? C8 C7 N1 C11 . . . . -1.8(10) ? C6 C7 N1 C11 . . . . -178.5(6) ? C8 C7 N1 Ir1 . . . . 179.4(5) ? C6 C7 N1 Ir1 . . . . 2.6(7) ? C21 C22 N2 C18 . . . . 2.0(12) ? C21 C22 N2 Ir1 . . . . -170.9(7) ? C19 C18 N2 C22 . . . . -2.1(11) ? C17 C18 N2 C22 . . . . -178.9(7) ? C19 C18 N2 Ir1 . . . . 171.4(5) ? C17 C18 N2 Ir1 . . . . -5.4(8) ? C25 C26 N3 C23 . . . . -7.6(11) ? C27 C26 N3 C23 . . . . 170.9(6) ? C25 C26 N3 Ir1 . . . . 160.6(7) ? C27 C26 N3 Ir1 . . . . -20.9(7) ? C24 C23 N3 C26 . . . . 7.8(11) ? C32 C23 N3 C26 . . . . -170.8(7) ? C24 C23 N3 Ir1 . . . . -158.4(6) ? C32 C23 N3 Ir1 . . . . 23.0(9) ? C30 C31 N4 C27 . . . . -1.1(12) ? C30 C31 N4 Ir1 . . . . 176.2(7) ? C28 C27 N4 C31 . . . . 0.2(11) ? C26 C27 N4 C31 . . . . 179.4(7) ? C28 C27 N4 Ir1 . . . . -177.3(5) ? C26 C27 N4 Ir1 . . . . 1.9(8) ? C42 C43 N5 C39 . . . . -1.2(11) ? C42 C43 N5 Ir2 . . . . -174.6(4) ? C38 C39 N5 C43 . . . . 177.4(6) ? C40 C39 N5 C43 . . . . 0.1(11) ? C38 C39 N5 Ir2 . . . . -8.2(6) ? C40 C39 N5 Ir2 . . . . 174.4(3) ? C53 C54 N6 C50 . . . . 0.9(13) ? C53 C54 N6 Ir2 . . . . -177.2(7) ? C51 C50 N6 C54 . . . . -0.8(13) ? C49 C50 N6 C54 . . . . -180.0(7) ? C51 C50 N6 Ir2 . . . . 177.6(8) ? C49 C50 N6 Ir2 . . . . -1.6(10) ? C62 C63 N7 C59 . . . . 1.(2) ? C62 C63 N7 Ir2 . . . . -178.5(10) ? C60 C59 N7 C63 . . . . -4.(2) ? C58 C59 N7 C63 . . . . 175.4(11) ? C60 C59 N7 Ir2 . . . . 175.7(10) ? C58 C59 N7 Ir2 . . . . -5.2(16) ? C57 C58 N8 C55 . . . . -12.1(14) ? C59 C58 N8 C55 . . . . 169.5(10) ? C57 C58 N8 Ir2 . . . . 157.6(8) ? C59 C58 N8 Ir2 . . . . -20.8(10) ? C56 C55 N8 C58 . . . . 11.5(19) ? C64 C55 N8 C58 . . . . -167.5(11) ? C56 C55 N8 Ir2 . . . . -156.2(12) ? C64 C55 N8 Ir2 . . . . 24.9(17) ? C23 C24 S1 O1 . . . . 94.0(8) ? C23 C24 S1 O2 . . . . -140.0(7) ? C23 C24 S1 C25 . . . . -22.4(8) ? C26 C25 S1 O1 . . . . -95.3(8) ? C26 C25 S1 O2 . . . . 139.5(7) ? C26 C25 S1 C24 . . . . 22.2(9) ? C55 C56 S2 O4 . . . . -142.4(15) ? C55 C56 S2 O3 . . . . 90.9(17) ? C55 C56 S2 C57 . . . . -25.1(17) ? C58 C57 S2 O4 . . . . 143.1(9) ? C58 C57 S2 O3 . . . . -93.8(9) ? C58 C57 S2 C56 . . . . 24.1(10) ? C13 C12 Ir1 C1 . . . . -86.3(7) ? C17 C12 Ir1 C1 . . . . 91.9(5) ? C13 C12 Ir1 N2 . . . . 179.6(7) ? C17 C12 Ir1 N2 . . . . -2.2(5) ? C13 C12 Ir1 N1 . . . . -6.2(7) ? C17 C12 Ir1 N1 . . . . 172.0(5) ? C13 C12 Ir1 N4 . . . . -170.(5) ? C17 C12 Ir1 N4 . . . . 8.(5) ? C13 C12 Ir1 N3 . . . . 86.5(6) ? C17 C12 Ir1 N3 . . . . -95.3(5) ? C2 C1 Ir1 C12 . . . . -76.0(7) ? C6 C1 Ir1 C12 . . . . 108.2(5) ? C2 C1 Ir1 N2 . . . . 4.0(7) ? C6 C1 Ir1 N2 . . . . -171.9(5) ? C2 C1 Ir1 N1 . . . . -173.7(7) ? C6 C1 Ir1 N1 . . . . 10.4(5) ? C2 C1 Ir1 N4 . . . . 101.0(7) ? C6 C1 Ir1 N4 . . . . -74.8(5) ? C2 C1 Ir1 N3 . . . . 138.1(11) ? C6 C1 Ir1 N3 . . . . -37.7(15) ? C22 N2 Ir1 C12 . . . . 177.4(7) ? C18 N2 Ir1 C12 . . . . 4.3(5) ? C22 N2 Ir1 C1 . . . . 92.7(7) ? C18 N2 Ir1 C1 . . . . -80.5(5) ? C22 N2 Ir1 N1 . . . . 113.(2) ? C18 N2 Ir1 N1 . . . . -60.(2) ? C22 N2 Ir1 N4 . . . . -2.0(7) ? C18 N2 Ir1 N4 . . . . -175.1(5) ? C22 N2 Ir1 N3 . . . . -78.4(6) ? C18 N2 Ir1 N3 . . . . 108.5(5) ? C11 N1 Ir1 C12 . . . . 89.9(6) ? C7 N1 Ir1 C12 . . . . -91.3(5) ? C11 N1 Ir1 C1 . . . . 174.1(6) ? C7 N1 Ir1 C1 . . . . -7.1(5) ? C11 N1 Ir1 N2 . . . . 153.(2) ? C7 N1 Ir1 N2 . . . . -28.(2) ? C11 N1 Ir1 N4 . . . . -91.0(6) ? C7 N1 Ir1 N4 . . . . 87.8(5) ? C11 N1 Ir1 N3 . . . . -15.2(6) ? C7 N1 Ir1 N3 . . . . 163.6(5) ? C31 N4 Ir1 C12 . . . . 69.(5) ? C27 N4 Ir1 C12 . . . . -114.(5) ? C31 N4 Ir1 C1 . . . . -14.9(6) ? C27 N4 Ir1 C1 . . . . 162.6(5) ? C31 N4 Ir1 N2 . . . . 79.0(6) ? C27 N4 Ir1 N2 . . . . -103.6(5) ? C31 N4 Ir1 N1 . . . . -95.3(6) ? C27 N4 Ir1 N1 . . . . 82.2(5) ? C31 N4 Ir1 N3 . . . . 172.9(7) ? C27 N4 Ir1 N3 . . . . -9.7(5) ? C26 N3 Ir1 C12 . . . . -166.4(5) ? C23 N3 Ir1 C12 . . . . 0.2(6) ? C26 N3 Ir1 C1 . . . . -21.7(14) ? C23 N3 Ir1 C1 . . . . 144.9(11) ? C26 N3 Ir1 N2 . . . . 112.2(5) ? C23 N3 Ir1 N2 . . . . -81.1(6) ? C26 N3 Ir1 N1 . . . . -69.0(5) ? C23 N3 Ir1 N1 . . . . 97.6(6) ? C26 N3 Ir1 N4 . . . . 16.6(5) ? C23 N3 Ir1 N4 . . . . -176.7(6) ? C43 N5 Ir2 C44 . . . . 94.6(8) ? C39 N5 Ir2 C44 . . . . -79.6(5) ? C43 N5 Ir2 N6 . . . . 143.9(19) ? C39 N5 Ir2 N6 . . . . -30.(3) ? C43 N5 Ir2 C33 . . . . 178.2(8) ? C39 N5 Ir2 C33 . . . . 4.0(5) ? C43 N5 Ir2 N7 . . . . -1.6(8) ? C39 N5 Ir2 N7 . . . . -175.8(5) ? C43 N5 Ir2 N8 . . . . -77.7(8) ? C39 N5 Ir2 N8 . . . . 108.1(5) ? C45 C44 Ir2 N5 . . . . -6.8(7) ? C49 C44 Ir2 N5 . . . . 174.5(6) ? C45 C44 Ir2 N6 . . . . 179.6(7) ? C49 C44 Ir2 N6 . . . . 0.9(6) ? C45 C44 Ir2 C33 . . . . -86.4(7) ? C49 C44 Ir2 C33 . . . . 94.9(6) ? C45 C44 Ir2 N7 . . . . 92.4(7) ? C49 C44 Ir2 N7 . . . . -86.3(6) ? C45 C44 Ir2 N8 . . . . 122.4(17) ? C49 C44 Ir2 N8 . . . . -56.(2) ? C54 N6 Ir2 N5 . . . . 129.(2) ? C50 N6 Ir2 N5 . . . . -50.(2) ? C54 N6 Ir2 C44 . . . . 178.6(7) ? C50 N6 Ir2 C44 . . . . 0.4(6) ? C54 N6 Ir2 C33 . . . . 94.9(7) ? C50 N6 Ir2 C33 . . . . -83.3(6) ? C54 N6 Ir2 N7 . . . . -85.4(7) ? C50 N6 Ir2 N7 . . . . 96.4(6) ? C54 N6 Ir2 N8 . . . . -9.8(7) ? C50 N6 Ir2 N8 . . . . 172.0(6) ? C34 C33 Ir2 N5 . . . . 178.3(9) ? C38 C33 Ir2 N5 . . . . -0.6(7) ? C34 C33 Ir2 C44 . . . . -87.1(9) ? C38 C33 Ir2 C44 . . . . 94.0(7) ? C34 C33 Ir2 N6 . . . . -6.4(9) ? C38 C33 Ir2 N6 . . . . 174.7(7) ? C34 C33 Ir2 N7 . . . . -170.(30) ? C38 C33 Ir2 N7 . . . . 10.(20) ? C34 C33 Ir2 N8 . . . . 87.9(9) ? C38 C33 Ir2 N8 . . . . -90.9(7) ? C63 N7 Ir2 N5 . . . . 84.3(11) ? C59 N7 Ir2 N5 . . . . -95.0(10) ? C63 N7 Ir2 C44 . . . . -10.1(11) ? C59 N7 Ir2 C44 . . . . 170.5(10) ? C63 N7 Ir2 N6 . . . . -91.0(11) ? C59 N7 Ir2 N6 . . . . 89.7(10) ? C63 N7 Ir2 C33 . . . . 80.(20) ? C59 N7 Ir2 C33 . . . . -100.(20) ? C63 N7 Ir2 N8 . . . . 175.0(12) ? C59 N7 Ir2 N8 . . . . -4.3(10) ? C58 N8 Ir2 N5 . . . . 111.9(6) ? C55 N8 Ir2 N5 . . . . -79.9(10) ? C58 N8 Ir2 C44 . . . . -17.(2) ? C55 N8 Ir2 C44 . . . . 150.9(17) ? C58 N8 Ir2 N6 . . . . -73.6(6) ? C55 N8 Ir2 N6 . . . . 94.6(9) ? C58 N8 Ir2 C33 . . . . -167.6(6) ? C55 N8 Ir2 C33 . . . . 0.6(10) ? C58 N8 Ir2 N7 . . . . 13.6(6) ? C55 N8 Ir2 N7 . . . . -178.3(10) ? data_b12029_0m _database_code_depnum_ccdc_archive 'CCDC 917255' #TrackingRef 'web_deposit_cif_file_0_EliZysman-Colman_1356643359.X-ray structures for paper.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2 O2 S' _chemical_formula_sum 'C10 H10 N2 O2 S' _chemical_formula_weight 222.26 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_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 10.3350(4) _cell_length_b 9.6877(4) _cell_length_c 19.7442(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.8170(10) _cell_angle_gamma 90.00 _cell_volume 1911.10(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9899 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9156 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details SADABS _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24310 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.43 _reflns_number_total 2383 _reflns_number_gt 2187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 2383 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.001 _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 S1 S 1.03152(3) 0.13695(3) 0.375441(16) 0.01966(16) Uani 1 1 d . . . C1 C 0.78993(13) 0.49069(13) 0.58162(7) 0.0236(3) Uani 1 1 d . . . H1 H 0.7102 0.5402 0.5807 0.028 Uiso 1 1 calc R . . C2 C 0.88798(14) 0.48347(14) 0.64463(7) 0.0245(3) Uani 1 1 d . . . H2 H 0.8756 0.5280 0.6854 0.029 Uiso 1 1 calc R . . C3 C 1.00415(14) 0.40997(14) 0.64681(7) 0.0245(3) Uani 1 1 d . . . H3 H 1.0728 0.4030 0.6891 0.029 Uiso 1 1 calc R . . C4 C 1.01812(13) 0.34706(14) 0.58625(7) 0.0220(3) Uani 1 1 d . . . H4 H 1.0963 0.2956 0.5861 0.026 Uiso 1 1 calc R . . C5 C 0.91472(13) 0.36073(11) 0.52528(7) 0.0174(3) Uani 1 1 d . . . C6 C 0.92143(12) 0.29844(12) 0.45745(6) 0.0170(3) Uani 1 1 d . . . C7 C 1.02289(12) 0.21493(13) 0.45180(7) 0.0216(3) Uani 1 1 d . . . H7 H 1.0933 0.1987 0.4925 0.026 Uiso 1 1 calc R . . C8 C 0.89778(12) 0.21118(13) 0.31619(7) 0.0195(3) Uani 1 1 d . . . H8 H 0.8866 0.1915 0.2679 0.023 Uiso 1 1 calc R . . C9 C 0.80804(12) 0.29538(12) 0.33395(6) 0.0171(3) Uani 1 1 d . . . C10 C 0.69244(14) 0.35568(13) 0.27968(7) 0.0219(3) Uani 1 1 d . . . H10A H 0.6081 0.3266 0.2894 0.033 Uiso 1 1 calc R . . H10B H 0.6954 0.3231 0.2331 0.033 Uiso 1 1 calc R . . H10C H 0.6984 0.4566 0.2812 0.033 Uiso 1 1 calc R . . N1 N 0.80176(11) 0.43195(11) 0.52246(6) 0.0203(3) Uani 1 1 d . . . N2 N 0.81688(10) 0.33358(11) 0.40158(6) 0.0176(2) Uani 1 1 d . . . H2A H 0.7517 0.3838 0.4099 0.021 Uiso 1 1 calc R . . O1 O 1.15619(10) 0.17360(11) 0.35877(5) 0.0268(2) Uani 1 1 d . . . O2 O 1.01243(11) -0.01125(10) 0.37932(6) 0.0295(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0178(2) 0.0218(2) 0.0201(2) -0.00167(10) 0.00615(15) 0.00408(10) C1 0.0284(7) 0.0225(6) 0.0228(7) 0.0006(5) 0.0120(5) 0.0032(5) C2 0.0371(7) 0.0209(6) 0.0184(6) -0.0012(5) 0.0123(5) -0.0025(5) C3 0.0288(7) 0.0246(7) 0.0180(6) -0.0003(5) 0.0022(5) -0.0028(5) C4 0.0205(7) 0.0245(6) 0.0197(7) -0.0008(5) 0.0026(5) -0.0004(4) C5 0.0186(6) 0.0171(6) 0.0173(6) 0.0007(4) 0.0063(5) -0.0020(4) C6 0.0168(6) 0.0176(5) 0.0163(6) 0.0003(4) 0.0038(5) -0.0017(4) C7 0.0194(6) 0.0268(6) 0.0177(6) -0.0005(5) 0.0032(5) 0.0046(5) C8 0.0169(6) 0.0238(6) 0.0178(6) -0.0033(5) 0.0044(5) 0.0003(4) C9 0.0167(6) 0.0176(5) 0.0170(6) -0.0010(4) 0.0039(5) -0.0020(4) C10 0.0186(6) 0.0271(7) 0.0181(6) -0.0009(5) 0.0012(5) 0.0035(4) N1 0.0209(6) 0.0215(5) 0.0199(6) 0.0003(4) 0.0079(4) 0.0012(4) N2 0.0166(5) 0.0202(5) 0.0160(5) -0.0014(4) 0.0040(4) 0.0035(4) O1 0.0186(5) 0.0364(5) 0.0269(5) -0.0019(4) 0.0089(4) 0.0036(4) O2 0.0357(6) 0.0218(5) 0.0324(6) -0.0009(4) 0.0113(5) 0.0056(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 S1 O1 1.4531(10) . ? S1 O2 1.4538(10) . ? S1 C7 1.7090(13) . ? S1 C8 1.7232(13) . ? C1 N1 1.3327(17) . ? C1 C2 1.3909(19) . ? C1 H1 0.9500 . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.3821(19) . ? C3 H3 0.9500 . ? C4 C5 1.3968(18) . ? C4 H4 0.9500 . ? C5 N1 1.3450(16) . ? C5 C6 1.4866(17) . ? C6 C7 1.3514(16) . ? C6 N2 1.3750(15) . ? C7 H7 0.9500 . ? C8 C9 1.3473(17) . ? C8 H8 0.9500 . ? C9 N2 1.3659(16) . ? C9 C10 1.5041(16) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N2 H2A 0.8800 . ? 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 S1 O2 113.16(6) . . ? O1 S1 C7 109.95(6) . . ? O2 S1 C7 110.59(7) . . ? O1 S1 C8 110.36(6) . . ? O2 S1 C8 110.60(6) . . ? C7 S1 C8 101.58(6) . . ? N1 C1 C2 123.59(12) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 118.72(12) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 118.72(12) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 118.53(13) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 123.30(12) . . ? N1 C5 C6 114.26(11) . . ? C4 C5 C6 122.44(11) . . ? C7 C6 N2 123.31(11) . . ? C7 C6 C5 122.23(11) . . ? N2 C6 C5 114.46(10) . . ? C6 C7 S1 123.65(10) . . ? C6 C7 H7 118.2 . . ? S1 C7 H7 118.2 . . ? C9 C8 S1 124.19(10) . . ? C9 C8 H8 117.9 . . ? S1 C8 H8 117.9 . . ? C8 C9 N2 122.69(11) . . ? C8 C9 C10 121.60(11) . . ? N2 C9 C10 115.70(11) . . ? 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 . . ? C1 N1 C5 117.13(12) . . ? C9 N2 C6 124.03(11) . . ? C9 N2 H2A 118.0 . . ? C6 N2 H2A 118.0 . . ? 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 N1 C1 C2 C3 -0.8(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 N1 -0.1(2) . . . . ? C3 C4 C5 C6 179.15(12) . . . . ? N1 C5 C6 C7 -174.92(11) . . . . ? C4 C5 C6 C7 5.73(19) . . . . ? N1 C5 C6 N2 5.42(16) . . . . ? C4 C5 C6 N2 -173.92(11) . . . . ? N2 C6 C7 S1 -2.56(19) . . . . ? C5 C6 C7 S1 177.82(9) . . . . ? O1 S1 C7 C6 123.77(12) . . . . ? O2 S1 C7 C6 -110.54(12) . . . . ? C8 S1 C7 C6 6.88(13) . . . . ? O1 S1 C8 C9 -123.22(12) . . . . ? O2 S1 C8 C9 110.78(12) . . . . ? C7 S1 C8 C9 -6.63(13) . . . . ? S1 C8 C9 N2 1.92(19) . . . . ? S1 C8 C9 C10 -179.30(9) . . . . ? C2 C1 N1 C5 0.94(19) . . . . ? C4 C5 N1 C1 -0.45(18) . . . . ? C6 C5 N1 C1 -179.80(11) . . . . ? C8 C9 N2 C6 4.50(19) . . . . ? C10 C9 N2 C6 -174.34(11) . . . . ? C7 C6 N2 C9 -4.20(19) . . . . ? C5 C6 N2 C9 175.45(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.492 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.056