# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_ib49 _database_code_depnum_ccdc_archive 'CCDC 877474' #TrackingRef 'complex.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C39 H30 Ir N4 O2 S), 2(F6 P), C H Cl3, 3(H2 O)' _chemical_formula_sum 'C79 H67 Cl3 F12 Ir2 N8 O7 P2 S2' _chemical_formula_weight 2085.29 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9914(11) _cell_length_b 26.259(3) _cell_length_c 32.326(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9329.9(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5470 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 47.39 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4088 _exptl_absorpt_coefficient_mu 3.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3712 _exptl_absorpt_correction_T_max 0.9698 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 94268 _diffrn_reflns_av_R_equivalents 0.1093 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.50 _reflns_number_total 17367 _reflns_number_gt 16161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0499P)^2^+14.3084P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(6) _refine_ls_number_reflns 17367 _refine_ls_number_parameters 1092 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.013 _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 Ir1A Ir 0.46229(2) 0.961383(10) -0.101632(7) 0.03154(7) Uani 1 1 d . . . N1A N 0.3417(5) 0.9018(2) -0.12013(16) 0.0330(12) Uani 1 1 d . . . N2A N 0.3961(5) 0.9292(2) -0.04148(16) 0.0342(12) Uani 1 1 d . . . C1A C 0.3104(6) 0.8914(3) -0.1596(2) 0.0377(16) Uani 1 1 d . . . H1AA H 0.3545 0.9075 -0.1813 0.045 Uiso 1 1 calc R . . C2A C 0.2186(6) 0.8591(3) -0.1699(2) 0.0387(16) Uani 1 1 d . . . H2AA H 0.2002 0.8523 -0.1981 0.046 Uiso 1 1 calc R . . C3A C 0.1530(7) 0.8362(3) -0.1388(2) 0.0446(17) Uani 1 1 d . . . H3AA H 0.0859 0.8148 -0.1452 0.054 Uiso 1 1 calc R . . C4A C 0.1865(6) 0.8450(3) -0.0980(2) 0.0394(16) Uani 1 1 d . . . H4AA H 0.1436 0.8290 -0.0761 0.047 Uiso 1 1 calc R . . C5A C 0.2826(6) 0.8769(3) -0.0898(2) 0.0319(14) Uani 1 1 d . . . C6A C 0.3283(6) 0.8867(3) -0.0477(2) 0.0313(14) Uani 1 1 d . . . C7A C 0.3026(6) 0.8532(3) -0.0164(2) 0.0364(15) Uani 1 1 d . . . H7AA H 0.2577 0.8229 -0.0215 0.044 Uiso 1 1 calc R . . C8A C 0.3446(6) 0.8650(3) 0.0233(2) 0.0358(15) Uani 1 1 d . . . C9A C 0.4082(6) 0.9088(3) 0.0304(2) 0.0372(14) Uani 1 1 d . . . H9AA H 0.4351 0.9171 0.0575 0.045 Uiso 1 1 calc R . . C10A C 0.4329(5) 0.9410(3) -0.00280(18) 0.0339(14) Uani 1 1 d . . . C11A C 0.4921(6) 0.9907(3) 0.0072(2) 0.0392(16) Uani 1 1 d . . . C12A C 0.4199(7) 1.0326(3) 0.0129(3) 0.054(2) Uani 1 1 d . . . H12A H 0.3351 1.0307 0.0075 0.064 Uiso 1 1 calc R . . C13A C 0.4711(9) 1.0785(4) 0.0268(3) 0.066(2) Uani 1 1 d . . . H13A H 0.4221 1.1078 0.0311 0.079 Uiso 1 1 calc R . . C14A C 0.5937(10) 1.0796(4) 0.0338(3) 0.070(3) Uani 1 1 d . . . H14A H 0.6299 1.1105 0.0428 0.084 Uiso 1 1 calc R . . C15A C 0.6677(8) 1.0369(4) 0.0282(3) 0.062(2) Uani 1 1 d . . . H15A H 0.7525 1.0383 0.0338 0.075 Uiso 1 1 calc R . . C16A C 0.6148(7) 0.9932(3) 0.0144(2) 0.0463(18) Uani 1 1 d . . . H16A H 0.6637 0.9639 0.0098 0.056 Uiso 1 1 calc R . . S1A S 0.31415(17) 0.82261(7) 0.06493(5) 0.0393(4) Uani 1 1 d . . . O1A O 0.3647(5) 0.7735(2) 0.05571(15) 0.0485(13) Uani 1 1 d . . . O2A O 0.3547(5) 0.8483(2) 0.10198(15) 0.0484(12) Uani 1 1 d . . . C17A C 0.1552(7) 0.8177(4) 0.0649(3) 0.055(2) Uani 1 1 d . . . H17A H 0.1279 0.8033 0.0386 0.082 Uiso 1 1 calc R . . H17B H 0.1194 0.8516 0.0686 0.082 Uiso 1 1 calc R . . H17C H 0.1293 0.7955 0.0877 0.082 Uiso 1 1 calc R . . C18A C 0.5858(6) 1.0151(3) -0.08550(19) 0.0365(15) Uani 1 1 d . . . C19A C 0.5672(7) 1.0666(3) -0.0811(2) 0.0443(17) Uani 1 1 d . . . H19A H 0.4873 1.0799 -0.0839 0.053 Uiso 1 1 calc R . . C20A C 0.6631(7) 1.0995(3) -0.0726(2) 0.0502(19) Uani 1 1 d . . . H20A H 0.6483 1.1349 -0.0695 0.060 Uiso 1 1 calc R . . C21A C 0.7802(8) 1.0807(3) -0.0686(3) 0.055(2) Uani 1 1 d . . . H21A H 0.8459 1.1031 -0.0631 0.066 Uiso 1 1 calc R . . C22A C 0.8007(7) 1.0290(3) -0.0727(2) 0.0485(19) Uani 1 1 d . . . H22A H 0.8807 1.0158 -0.0697 0.058 Uiso 1 1 calc R . . C23A C 0.7047(6) 0.9963(3) -0.0812(2) 0.0394(16) Uani 1 1 d . . . C24A C 0.7187(6) 0.9421(3) -0.0865(2) 0.0371(15) Uani 1 1 d . . . C25A C 0.8266(6) 0.9137(4) -0.0823(2) 0.050(2) Uani 1 1 d . . . H25A H 0.9002 0.9306 -0.0753 0.060 Uiso 1 1 calc R . . C26A C 0.8269(7) 0.8624(4) -0.0882(3) 0.053(2) Uani 1 1 d . . . H26A H 0.9001 0.8435 -0.0855 0.064 Uiso 1 1 calc R . . C27A C 0.7200(7) 0.8385(3) -0.0981(3) 0.0504(19) Uani 1 1 d . . . H27A H 0.7188 0.8028 -0.1031 0.061 Uiso 1 1 calc R . . C28A C 0.6165(6) 0.8659(3) -0.1008(2) 0.0431(17) Uani 1 1 d . . . H28A H 0.5425 0.8487 -0.1067 0.052 Uiso 1 1 calc R . . N3A N 0.6140(4) 0.9172(2) -0.09525(16) 0.0332(12) Uani 1 1 d . . . C29A C 0.5000(6) 0.9815(3) -0.1600(2) 0.0372(15) Uani 1 1 d . . . C30A C 0.5929(6) 0.9626(3) -0.1849(2) 0.0447(17) Uani 1 1 d . . . H30A H 0.6512 0.9399 -0.1735 0.054 Uiso 1 1 calc R . . C31A C 0.6013(7) 0.9769(4) -0.2266(2) 0.054(2) Uani 1 1 d . . . H31A H 0.6642 0.9631 -0.2434 0.065 Uiso 1 1 calc R . . C32A C 0.5186(8) 1.0108(3) -0.2434(2) 0.054(2) Uani 1 1 d . . . H32A H 0.5251 1.0206 -0.2716 0.065 Uiso 1 1 calc R . . C33A C 0.4270(7) 1.0304(3) -0.2191(2) 0.0501(19) Uani 1 1 d . . . H33A H 0.3697 1.0534 -0.2306 0.060 Uiso 1 1 calc R . . C34A C 0.4180(6) 1.0164(3) -0.1776(2) 0.0390(15) Uani 1 1 d . . . C35A C 0.3208(6) 1.0334(3) -0.1500(2) 0.0399(16) Uani 1 1 d . . . C36A C 0.2310(7) 1.0697(3) -0.1593(3) 0.0496(19) Uani 1 1 d . . . H36A H 0.2320 1.0866 -0.1853 0.060 Uiso 1 1 calc R . . C37A C 0.1434(7) 1.0808(3) -0.1316(3) 0.054(2) Uani 1 1 d . . . H37A H 0.0814 1.1046 -0.1383 0.065 Uiso 1 1 calc R . . C38A C 0.1443(7) 1.0573(3) -0.0931(3) 0.0482(18) Uani 1 1 d . . . H38A H 0.0831 1.0648 -0.0733 0.058 Uiso 1 1 calc R . . C39A C 0.2348(6) 1.0230(3) -0.0840(2) 0.0401(16) Uani 1 1 d . . . H39A H 0.2355 1.0071 -0.0576 0.048 Uiso 1 1 calc R . . N4A N 0.3233(5) 1.0112(2) -0.11169(17) 0.0370(13) Uani 1 1 d . . . Ir1B Ir 0.54888(2) 0.910115(10) 0.212293(7) 0.03381(7) Uani 1 1 d . . . N1B N 0.6643(5) 0.9611(2) 0.17888(17) 0.0370(12) Uani 1 1 d . . . N2B N 0.6164(5) 0.8624(2) 0.15986(16) 0.0333(12) Uani 1 1 d . . . C1B C 0.6929(7) 1.0082(3) 0.1909(2) 0.0446(17) Uani 1 1 d . . . H1BA H 0.6555 1.0214 0.2151 0.054 Uiso 1 1 calc R . . C2B C 0.7733(8) 1.0383(3) 0.1700(2) 0.055(2) Uani 1 1 d . . . H2BA H 0.7905 1.0719 0.1792 0.066 Uiso 1 1 calc R . . C3B C 0.8294(9) 1.0188(4) 0.1350(3) 0.063(2) Uani 1 1 d . . . H3BA H 0.8876 1.0385 0.1203 0.075 Uiso 1 1 calc R . . C4B C 0.8000(8) 0.9711(3) 0.1220(3) 0.052(2) Uani 1 1 d . . . H4BA H 0.8368 0.9575 0.0978 0.062 Uiso 1 1 calc R . . C5B C 0.7173(7) 0.9425(3) 0.1437(2) 0.0431(18) Uani 1 1 d . . . C6B C 0.6783(6) 0.8903(3) 0.1317(2) 0.0339(14) Uani 1 1 d . . . C7B C 0.7024(6) 0.8728(3) 0.0920(2) 0.0384(16) Uani 1 1 d . . . H7BA H 0.7440 0.8937 0.0726 0.046 Uiso 1 1 calc R . . C8B C 0.6651(6) 0.8252(3) 0.0815(2) 0.0385(16) Uani 1 1 d . . . C9B C 0.6042(7) 0.7957(3) 0.1105(2) 0.0413(16) Uani 1 1 d . . . H9BA H 0.5768 0.7625 0.1034 0.050 Uiso 1 1 calc R . . C10B C 0.5833(6) 0.8145(3) 0.1501(2) 0.0341(14) Uani 1 1 d . . . C11B C 0.5257(7) 0.7794(3) 0.1809(2) 0.0385(15) Uani 1 1 d . . . C12B C 0.5947(8) 0.7601(3) 0.2132(2) 0.0468(17) Uani 1 1 d . . . H12B H 0.6750 0.7722 0.2179 0.056 Uiso 1 1 calc R . . C13B C 0.5451(9) 0.7228(3) 0.2386(2) 0.0526(18) Uani 1 1 d . . . H13B H 0.5918 0.7092 0.2608 0.063 Uiso 1 1 calc R . . C14B C 0.4303(8) 0.7059(4) 0.2319(2) 0.059(2) Uani 1 1 d . . . H14B H 0.3968 0.6807 0.2497 0.071 Uiso 1 1 calc R . . C15B C 0.3618(8) 0.7247(4) 0.2000(3) 0.059(2) Uani 1 1 d . . . H15B H 0.2818 0.7121 0.1955 0.070 Uiso 1 1 calc R . . C16B C 0.4093(7) 0.7618(3) 0.1744(2) 0.0496(19) Uani 1 1 d . . . H16B H 0.3617 0.7752 0.1524 0.059 Uiso 1 1 calc R . . S1B S 0.69031(17) 0.80211(7) 0.03034(5) 0.0405(4) Uani 1 1 d . . . O1B O 0.6423(6) 0.8396(2) 0.00281(16) 0.0565(15) Uani 1 1 d . . . O2B O 0.6454(5) 0.7510(2) 0.02866(15) 0.0450(12) Uani 1 1 d . . . C17B C 0.8498(7) 0.8015(4) 0.0262(2) 0.055(2) Uani 1 1 d . . . H17D H 0.8731 0.7887 -0.0011 0.083 Uiso 1 1 calc R . . H17E H 0.8838 0.7792 0.0476 0.083 Uiso 1 1 calc R . . H17F H 0.8812 0.8361 0.0299 0.083 Uiso 1 1 calc R . . C18B C 0.4296(6) 0.8641(3) 0.2432(2) 0.0409(16) Uani 1 1 d . . . C19B C 0.4483(8) 0.8363(3) 0.2780(2) 0.0529(19) Uani 1 1 d . . . H19B H 0.5274 0.8347 0.2897 0.063 Uiso 1 1 calc R . . C20B C 0.3524(9) 0.8100(3) 0.2967(3) 0.065(3) Uani 1 1 d . . . H20B H 0.3669 0.7906 0.3210 0.078 Uiso 1 1 calc R . . C21B C 0.2382(8) 0.8120(4) 0.2803(4) 0.070(3) Uani 1 1 d . . . H21B H 0.1742 0.7932 0.2928 0.084 Uiso 1 1 calc R . . C22B C 0.2145(8) 0.8414(4) 0.2452(3) 0.067(3) Uani 1 1 d . . . H22B H 0.1351 0.8432 0.2337 0.081 Uiso 1 1 calc R . . C23B C 0.3104(7) 0.8676(3) 0.2279(3) 0.050(2) Uani 1 1 d . . . C24B C 0.2929(7) 0.8994(4) 0.1918(2) 0.052(2) Uani 1 1 d . . . C25B C 0.1825(7) 0.9101(5) 0.1711(3) 0.072(3) Uani 1 1 d . . . H25B H 0.1103 0.8935 0.1801 0.086 Uiso 1 1 calc R . . C26B C 0.1761(10) 0.9427(5) 0.1394(4) 0.083(4) Uani 1 1 d . . . H26B H 0.1004 0.9497 0.1264 0.099 Uiso 1 1 calc R . . C27B C 0.2811(10) 0.9658(5) 0.1258(3) 0.075(3) Uani 1 1 d . . . H27B H 0.2793 0.9880 0.1026 0.090 Uiso 1 1 calc R . . C28B C 0.3883(8) 0.9567(4) 0.1461(2) 0.057(2) Uani 1 1 d . . . H28B H 0.4598 0.9740 0.1374 0.068 Uiso 1 1 calc R . . N3B N 0.3953(6) 0.9236(3) 0.17829(18) 0.0445(15) Uani 1 1 d . . . C29B C 0.5071(6) 0.9611(3) 0.2556(2) 0.0389(15) Uani 1 1 d . . . C30B C 0.4128(7) 0.9973(3) 0.2542(2) 0.049(2) Uani 1 1 d . . . H30B H 0.3572 0.9970 0.2317 0.059 Uiso 1 1 calc R . . C31B C 0.4001(7) 1.0333(4) 0.2850(3) 0.055(2) Uani 1 1 d . . . H31B H 0.3350 1.0570 0.2838 0.065 Uiso 1 1 calc R . . C32B C 0.4816(7) 1.0352(4) 0.3181(2) 0.057(2) Uani 1 1 d . . . H32B H 0.4738 1.0609 0.3386 0.068 Uiso 1 1 calc R . . C33B C 0.5747(7) 0.9991(3) 0.3210(2) 0.0479(19) Uani 1 1 d . . . H33B H 0.6288 0.9992 0.3439 0.058 Uiso 1 1 calc R . . C34B C 0.5867(6) 0.9629(3) 0.2894(2) 0.0391(15) Uani 1 1 d . . . C35B C 0.6842(6) 0.9259(3) 0.2882(2) 0.0358(15) Uani 1 1 d . . . C36B C 0.7712(6) 0.9178(3) 0.3189(2) 0.0435(17) Uani 1 1 d . . . H36B H 0.7683 0.9371 0.3438 0.052 Uiso 1 1 calc R . . C37B C 0.8614(7) 0.8820(3) 0.3133(2) 0.0498(19) Uani 1 1 d . . . H37B H 0.9182 0.8755 0.3348 0.060 Uiso 1 1 calc R . . C38B C 0.8688(6) 0.8558(3) 0.2765(2) 0.0441(17) Uani 1 1 d . . . H38B H 0.9325 0.8320 0.2716 0.053 Uiso 1 1 calc R . . C39B C 0.7812(6) 0.8649(3) 0.2469(2) 0.0398(16) Uani 1 1 d . . . H39B H 0.7858 0.8468 0.2215 0.048 Uiso 1 1 calc R . . N4B N 0.6895(5) 0.8981(2) 0.25229(16) 0.0348(13) Uani 1 1 d . . . P1 P 0.02589(19) 0.95966(11) 0.02079(7) 0.0597(6) Uani 1 1 d . . . F10 F 0.1606(5) 0.9589(4) 0.0333(2) 0.111(3) Uani 1 1 d . . . F11 F -0.0033(7) 0.9183(3) 0.0549(2) 0.109(2) Uani 1 1 d . . . F12 F -0.0015(6) 1.0013(2) 0.0551(2) 0.0884(19) Uani 1 1 d . . . F13 F 0.0468(9) 1.0004(4) -0.0125(2) 0.147(4) Uani 1 1 d . . . F14 F 0.0535(6) 0.9161(4) -0.0122(2) 0.123(3) Uani 1 1 d . . . F15 F -0.1132(5) 0.9554(4) 0.0094(2) 0.118(3) Uani 1 1 d . . . P2 P -0.0339(2) 0.76314(9) 0.16011(7) 0.0499(5) Uani 1 1 d . . . F20 F -0.0537(7) 0.8201(2) 0.1451(2) 0.101(2) Uani 1 1 d . . . F21 F -0.1754(6) 0.7562(3) 0.1634(3) 0.113(3) Uani 1 1 d . . . F22 F -0.0323(7) 0.7797(3) 0.20730(17) 0.0963(19) Uani 1 1 d . . . F23 F 0.1066(5) 0.7706(3) 0.15701(17) 0.0777(17) Uani 1 1 d . . . F24 F -0.0402(7) 0.7445(2) 0.11328(15) 0.0813(16) Uani 1 1 d . . . F25 F -0.0129(7) 0.7057(2) 0.17362(18) 0.0863(19) Uani 1 1 d . . . Cl1 Cl 0.8874(6) 0.6140(2) 0.27282(16) 0.0825(15) Uani 0.50 1 d P A 1 Cl2 Cl 1.1048(7) 0.6717(3) 0.2807(4) 0.139(4) Uani 0.50 1 d P A 1 Cl3 Cl 0.8717(9) 0.7158(3) 0.2987(2) 0.117(3) Uani 0.50 1 d P A 1 C100 C 0.952(2) 0.6743(7) 0.2688(5) 0.065(5) Uani 0.50 1 d P A 1 H10A H 0.9442 0.6856 0.2394 0.079 Uiso 0.50 1 calc PR A 1 Cl4 Cl 0.9204(8) 1.1404(4) 0.0461(5) 0.181(5) Uani 0.50 1 d P . . Cl5 Cl 1.1301(17) 1.1123(6) 0.0945(5) 0.238(7) Uani 0.50 1 d P . . Cl6 Cl 1.1473(13) 1.1395(5) 0.0085(5) 0.202(6) Uani 0.50 1 d P . . C200 C 1.060(3) 1.1142(8) 0.0466(10) 0.115(11) Uani 0.50 1 d P . . H30C H 1.0476 1.0778 0.0386 0.138 Uiso 0.50 1 calc PR . . O100 O 0.8425(15) 1.2150(6) -0.1346(5) 0.191(6) Uani 1 1 d . . . O101 O 0.525(6) 1.1497(18) 0.1451(10) 0.28(2) Uani 0.50 1 d PU B 1 O102 O 0.516(3) 1.2361(10) -0.1124(8) 0.227(14) Uani 0.50 1 d PDU C 1 O103 O 0.320(2) 1.1754(8) -0.0782(12) 0.25(2) Uani 0.50 1 d PD D 2 O104 O 0.405(5) 1.1151(16) 0.1508(18) 0.31(2) Uani 0.50 1 d PU E 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1A 0.02378(11) 0.04382(14) 0.02702(11) 0.00519(10) -0.00069(10) -0.00309(11) N1A 0.023(2) 0.046(3) 0.030(3) 0.007(2) -0.003(2) 0.003(2) N2A 0.024(2) 0.051(3) 0.027(3) 0.004(2) 0.000(2) -0.003(2) C1A 0.038(4) 0.046(4) 0.029(3) 0.002(3) -0.007(3) -0.005(3) C2A 0.044(4) 0.044(4) 0.028(3) 0.002(3) -0.010(3) 0.007(3) C3A 0.045(4) 0.040(4) 0.049(4) 0.009(3) -0.014(3) -0.010(3) C4A 0.033(3) 0.051(4) 0.035(4) 0.008(3) -0.004(3) -0.008(3) C5A 0.025(3) 0.042(4) 0.029(3) 0.004(3) 0.001(3) 0.006(3) C6A 0.024(3) 0.033(3) 0.037(3) 0.005(3) -0.001(3) -0.006(3) C7A 0.032(3) 0.041(4) 0.036(4) 0.004(3) -0.002(3) -0.003(3) C8A 0.030(3) 0.047(4) 0.030(3) 0.006(3) 0.001(3) 0.004(3) C9A 0.033(3) 0.046(4) 0.032(3) 0.001(3) -0.001(3) 0.001(3) C10A 0.025(3) 0.052(4) 0.025(3) 0.000(3) 0.001(2) 0.003(3) C11A 0.040(4) 0.046(4) 0.032(3) 0.002(3) 0.002(3) -0.011(3) C12A 0.048(4) 0.056(5) 0.057(5) 0.001(4) 0.000(4) 0.002(4) C13A 0.067(6) 0.060(5) 0.071(6) -0.014(4) 0.006(5) 0.000(5) C14A 0.078(6) 0.071(7) 0.060(5) -0.017(5) -0.001(5) -0.030(5) C15A 0.051(5) 0.079(6) 0.057(5) 0.002(5) -0.010(4) -0.026(5) C16A 0.043(4) 0.053(5) 0.043(4) 0.000(4) 0.001(3) -0.006(4) S1A 0.0431(9) 0.0470(10) 0.0278(8) 0.0045(7) 0.0010(7) -0.0011(8) O1A 0.062(3) 0.049(3) 0.035(2) 0.004(2) 0.000(2) 0.003(3) O2A 0.068(3) 0.052(3) 0.025(2) 0.001(2) -0.003(2) 0.004(3) C17A 0.039(4) 0.072(6) 0.054(5) 0.015(4) 0.009(4) -0.007(4) C18A 0.029(3) 0.056(4) 0.024(3) 0.012(3) 0.000(3) -0.010(3) C19A 0.043(4) 0.046(4) 0.044(4) 0.004(3) 0.005(3) -0.007(3) C20A 0.057(5) 0.049(5) 0.044(4) 0.005(3) 0.001(4) -0.016(4) C21A 0.048(4) 0.065(6) 0.051(5) 0.004(4) -0.001(4) -0.031(4) C22A 0.036(4) 0.067(6) 0.043(4) 0.006(4) 0.000(3) -0.007(4) C23A 0.035(3) 0.054(5) 0.029(3) 0.006(3) 0.003(3) -0.005(3) C24A 0.030(3) 0.054(4) 0.028(3) 0.001(3) 0.001(3) 0.000(3) C25A 0.022(3) 0.083(6) 0.044(4) 0.001(4) -0.004(3) -0.003(4) C26A 0.037(4) 0.069(6) 0.054(5) 0.002(4) -0.001(4) 0.009(4) C27A 0.047(4) 0.051(5) 0.053(5) 0.003(4) 0.006(4) 0.009(4) C28A 0.037(3) 0.065(5) 0.028(3) 0.007(3) -0.001(3) -0.003(3) N3A 0.026(2) 0.044(3) 0.030(3) 0.001(2) 0.002(2) -0.007(2) C29A 0.031(3) 0.038(4) 0.043(4) 0.008(3) -0.005(3) -0.004(3) C30A 0.034(3) 0.062(5) 0.039(4) 0.002(4) 0.005(3) 0.005(4) C31A 0.043(4) 0.083(6) 0.035(4) 0.002(4) 0.010(3) 0.000(4) C32A 0.067(5) 0.068(5) 0.028(3) 0.011(3) 0.002(4) -0.012(4) C33A 0.051(4) 0.065(5) 0.035(4) 0.017(3) -0.004(3) 0.002(4) C34A 0.034(3) 0.046(4) 0.037(3) 0.002(3) 0.000(3) -0.005(3) C35A 0.032(3) 0.051(4) 0.037(4) 0.011(3) -0.007(3) -0.001(3) C36A 0.048(4) 0.057(5) 0.044(4) 0.007(4) -0.006(4) 0.000(4) C37A 0.039(4) 0.052(5) 0.071(5) 0.011(4) -0.009(4) 0.013(4) C38A 0.034(4) 0.055(5) 0.056(5) 0.004(4) 0.002(3) 0.010(3) C39A 0.028(3) 0.048(4) 0.044(4) 0.005(3) 0.001(3) -0.009(3) N4A 0.029(3) 0.042(3) 0.040(3) -0.002(3) -0.001(2) -0.005(2) Ir1B 0.02690(12) 0.04761(15) 0.02691(12) -0.00857(10) -0.00081(11) 0.00259(12) N1B 0.036(3) 0.043(3) 0.032(3) -0.003(3) -0.005(2) 0.002(3) N2B 0.031(3) 0.041(3) 0.028(3) -0.005(2) 0.005(2) 0.003(2) C1B 0.056(5) 0.044(4) 0.033(4) -0.004(3) -0.002(3) -0.002(4) C2B 0.070(5) 0.052(5) 0.043(4) -0.007(4) -0.004(4) -0.017(5) C3B 0.064(5) 0.069(6) 0.055(5) -0.003(4) 0.017(4) -0.023(5) C4B 0.062(5) 0.050(5) 0.045(4) -0.008(4) 0.009(4) -0.015(4) C5B 0.039(4) 0.051(5) 0.039(4) -0.003(3) -0.001(3) -0.005(3) C6B 0.029(3) 0.043(4) 0.029(3) -0.004(3) -0.001(3) 0.001(3) C7B 0.040(4) 0.048(4) 0.027(3) -0.001(3) 0.005(3) 0.001(3) C8B 0.035(3) 0.051(4) 0.030(3) -0.010(3) 0.005(3) 0.001(3) C9B 0.041(4) 0.053(4) 0.029(3) -0.001(3) 0.003(3) -0.005(3) C10B 0.032(3) 0.039(4) 0.031(3) -0.007(3) 0.003(3) 0.002(3) C11B 0.042(4) 0.044(4) 0.030(3) -0.004(3) 0.002(3) 0.004(3) C12B 0.057(4) 0.053(4) 0.030(3) -0.002(3) -0.001(3) 0.003(4) C13B 0.059(5) 0.063(5) 0.035(3) 0.003(3) -0.003(4) 0.007(5) C14B 0.066(6) 0.065(5) 0.045(4) 0.019(4) 0.019(4) 0.002(4) C15B 0.041(4) 0.067(6) 0.068(5) 0.022(5) 0.009(4) -0.003(4) C16B 0.044(4) 0.064(5) 0.041(4) 0.012(4) 0.003(3) 0.004(4) S1B 0.0440(9) 0.0512(11) 0.0262(8) -0.0058(7) 0.0036(7) 0.0038(8) O1B 0.070(4) 0.064(4) 0.036(3) 0.004(3) 0.001(3) 0.015(3) O2B 0.050(3) 0.050(3) 0.035(2) -0.010(2) 0.008(2) -0.004(2) C17B 0.050(4) 0.078(6) 0.038(4) -0.011(4) 0.016(4) -0.009(4) C18B 0.031(4) 0.052(4) 0.039(4) -0.016(3) 0.002(3) -0.001(3) C19B 0.049(4) 0.057(5) 0.052(4) -0.015(4) 0.015(4) 0.000(4) C20B 0.080(7) 0.050(5) 0.065(6) -0.013(4) 0.033(5) -0.007(5) C21B 0.048(5) 0.077(7) 0.085(7) -0.027(6) 0.028(5) -0.019(5) C22B 0.038(4) 0.090(7) 0.075(6) -0.036(6) 0.016(4) -0.017(5) C23B 0.037(4) 0.064(5) 0.048(4) -0.023(4) 0.007(3) -0.003(4) C24B 0.038(4) 0.080(6) 0.038(4) -0.032(4) -0.003(3) 0.008(4) C25B 0.031(4) 0.119(9) 0.065(6) -0.048(6) -0.014(4) 0.005(5) C26B 0.056(6) 0.128(10) 0.063(7) -0.042(7) -0.020(5) 0.028(6) C27B 0.076(7) 0.107(8) 0.042(5) -0.016(5) -0.027(5) 0.041(7) C28B 0.061(5) 0.068(6) 0.041(4) -0.018(4) -0.014(4) 0.021(5) N3B 0.042(3) 0.061(4) 0.031(3) -0.011(3) -0.010(3) 0.006(3) C29B 0.029(3) 0.053(4) 0.034(3) 0.001(3) -0.001(3) -0.002(3) C30B 0.039(4) 0.071(5) 0.039(4) -0.016(4) -0.004(3) 0.011(4) C31B 0.044(4) 0.070(5) 0.049(4) -0.017(4) -0.003(4) 0.015(4) C32B 0.056(5) 0.070(5) 0.044(4) -0.026(4) -0.002(4) 0.012(4) C33B 0.044(4) 0.067(5) 0.032(3) -0.019(3) 0.004(3) 0.006(4) C34B 0.040(3) 0.040(4) 0.038(3) -0.010(3) 0.004(3) 0.003(3) C35B 0.033(3) 0.049(4) 0.025(3) -0.008(3) 0.003(3) -0.004(3) C36B 0.042(4) 0.057(5) 0.032(3) -0.005(3) -0.005(3) 0.004(4) C37B 0.044(4) 0.067(5) 0.039(4) -0.008(4) -0.010(3) 0.007(4) C38B 0.028(3) 0.059(5) 0.045(4) -0.006(3) -0.004(3) 0.000(3) C39B 0.036(4) 0.053(4) 0.031(3) -0.003(3) 0.002(3) -0.003(3) N4B 0.028(3) 0.050(4) 0.026(3) -0.009(2) 0.004(2) -0.002(3) P1 0.0393(10) 0.0956(17) 0.0443(10) 0.0081(11) 0.0014(9) 0.0145(13) F10 0.046(3) 0.176(7) 0.111(5) -0.030(5) -0.024(3) 0.014(4) F11 0.131(6) 0.083(4) 0.114(5) 0.017(4) 0.028(5) 0.006(4) F12 0.085(4) 0.086(4) 0.094(4) -0.014(3) 0.026(3) -0.008(3) F13 0.141(7) 0.197(9) 0.102(5) 0.090(6) 0.025(6) 0.022(7) F14 0.071(4) 0.206(8) 0.092(4) -0.070(5) -0.007(4) 0.038(5) F15 0.050(3) 0.195(8) 0.110(5) -0.031(6) -0.002(3) 0.026(5) P2 0.0354(9) 0.0615(12) 0.0528(11) -0.0058(9) 0.0082(10) -0.0050(10) F20 0.103(5) 0.059(3) 0.140(6) 0.008(4) 0.002(5) 0.007(4) F21 0.049(3) 0.157(7) 0.134(6) -0.004(6) 0.016(4) -0.030(4) F22 0.112(5) 0.113(5) 0.064(3) -0.033(3) 0.026(4) -0.015(4) F23 0.042(3) 0.126(5) 0.065(3) 0.006(3) 0.005(2) -0.014(3) F24 0.103(4) 0.093(4) 0.048(3) -0.004(3) -0.009(3) -0.007(4) F25 0.124(6) 0.068(3) 0.066(3) 0.009(3) 0.008(3) -0.009(3) Cl1 0.112(4) 0.074(3) 0.061(3) -0.001(2) -0.006(3) -0.019(3) Cl2 0.081(4) 0.097(5) 0.239(11) 0.065(6) -0.038(6) -0.016(4) Cl3 0.166(7) 0.073(4) 0.113(5) 0.006(4) 0.031(5) 0.032(4) C100 0.094(13) 0.072(11) 0.030(7) 0.013(7) -0.004(9) -0.028(12) Cl4 0.096(6) 0.138(8) 0.310(17) -0.024(9) -0.014(8) -0.019(6) Cl5 0.289(18) 0.203(13) 0.221(15) -0.027(12) -0.092(14) -0.060(13) Cl6 0.218(13) 0.131(8) 0.257(15) 0.003(9) 0.084(12) -0.028(9) C200 0.15(3) 0.047(11) 0.14(2) -0.016(13) 0.04(2) -0.025(16) O100 0.214(16) 0.170(12) 0.190(13) -0.052(11) 0.061(12) -0.016(12) O101 0.43(5) 0.30(4) 0.13(2) -0.02(2) 0.07(3) 0.09(4) O102 0.38(4) 0.169(19) 0.132(17) -0.004(15) 0.00(2) 0.15(2) O103 0.15(2) 0.131(19) 0.47(6) -0.17(3) -0.14(3) 0.095(18) O104 0.30(4) 0.22(3) 0.41(4) -0.11(3) 0.18(3) 0.04(3) _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 Ir1A C29A 2.001(7) . ? Ir1A C18A 2.026(7) . ? Ir1A N4A 2.038(6) . ? Ir1A N3A 2.041(5) . ? Ir1A N1A 2.137(6) . ? Ir1A N2A 2.242(5) . ? N1A C5A 1.345(8) . ? N1A C1A 1.350(8) . ? N2A C10A 1.351(8) . ? N2A C6A 1.357(8) . ? C1A C2A 1.360(10) . ? C1A H1AA 0.9500 . ? C2A C3A 1.373(10) . ? C2A H2AA 0.9500 . ? C3A C4A 1.389(10) . ? C3A H3AA 0.9500 . ? C4A C5A 1.375(9) . ? C4A H4AA 0.9500 . ? C5A C6A 1.472(9) . ? C6A C7A 1.370(9) . ? C7A C8A 1.397(9) . ? C7A H7AA 0.9500 . ? C8A C9A 1.363(10) . ? C8A S1A 1.780(7) . ? C9A C10A 1.394(9) . ? C9A H9AA 0.9500 . ? C10A C11A 1.493(10) . ? C11A C16A 1.370(10) . ? C11A C12A 1.370(11) . ? C12A C13A 1.403(12) . ? C12A H12A 0.9500 . ? C13A C14A 1.367(14) . ? C13A H13A 0.9500 . ? C14A C15A 1.398(15) . ? C14A H14A 0.9500 . ? C15A C16A 1.361(12) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? S1A O1A 1.437(6) . ? S1A O2A 1.445(5) . ? S1A C17A 1.752(8) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A C19A 1.375(10) . ? C18A C23A 1.403(10) . ? C19A C20A 1.390(10) . ? C19A H19A 0.9500 . ? C20A C21A 1.384(12) . ? C20A H20A 0.9500 . ? C21A C22A 1.382(12) . ? C21A H21A 0.9500 . ? C22A C23A 1.388(10) . ? C22A H22A 0.9500 . ? C23A C24A 1.443(11) . ? C24A N3A 1.353(8) . ? C24A C25A 1.408(10) . ? C25A C26A 1.359(13) . ? C25A H25A 0.9500 . ? C26A C27A 1.371(12) . ? C26A H26A 0.9500 . ? C27A C28A 1.349(10) . ? C27A H27A 0.9500 . ? C28A N3A 1.359(10) . ? C28A H28A 0.9500 . ? C29A C30A 1.391(10) . ? C29A C34A 1.406(10) . ? C30A C31A 1.402(10) . ? C30A H30A 0.9500 . ? C31A C32A 1.384(12) . ? C31A H31A 0.9500 . ? C32A C33A 1.377(11) . ? C32A H32A 0.9500 . ? C33A C34A 1.395(10) . ? C33A H33A 0.9500 . ? C34A C35A 1.461(10) . ? C35A N4A 1.369(9) . ? C35A C36A 1.405(11) . ? C36A C37A 1.347(12) . ? C36A H36A 0.9500 . ? C37A C38A 1.390(12) . ? C37A H37A 0.9500 . ? C38A C39A 1.373(10) . ? C38A H38A 0.9500 . ? C39A N4A 1.357(9) . ? C39A H39A 0.9500 . ? Ir1B C29B 1.991(7) . ? Ir1B N4B 2.039(5) . ? Ir1B C18B 2.044(7) . ? Ir1B N3B 2.046(6) . ? Ir1B N1B 2.137(6) . ? Ir1B N2B 2.234(5) . ? N1B C1B 1.335(10) . ? N1B C5B 1.368(9) . ? N2B C10B 1.346(9) . ? N2B C6B 1.352(9) . ? C1B C2B 1.365(11) . ? C1B H1BA 0.9500 . ? C2B C3B 1.386(12) . ? C2B H2BA 0.9500 . ? C3B C4B 1.361(12) . ? C3B H3BA 0.9500 . ? C4B C5B 1.372(11) . ? C4B H4BA 0.9500 . ? C5B C6B 1.489(10) . ? C6B C7B 1.388(9) . ? C7B C8B 1.359(10) . ? C7B H7BA 0.9500 . ? C8B C9B 1.390(10) . ? C8B S1B 1.782(7) . ? C9B C10B 1.392(9) . ? C9B H9BA 0.9500 . ? C10B C11B 1.498(10) . ? C11B C16B 1.376(10) . ? C11B C12B 1.386(10) . ? C12B C13B 1.390(11) . ? C12B H12B 0.9500 . ? C13B C14B 1.355(13) . ? C13B H13B 0.9500 . ? C14B C15B 1.369(12) . ? C14B H14B 0.9500 . ? C15B C16B 1.381(11) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? S1B O1B 1.428(6) . ? S1B O2B 1.432(5) . ? S1B C17B 1.758(8) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B C19B 1.355(11) . ? C18B C23B 1.404(10) . ? C19B C20B 1.397(12) . ? C19B H19B 0.9500 . ? C20B C21B 1.364(14) . ? C20B H20B 0.9500 . ? C21B C22B 1.396(15) . ? C21B H21B 0.9500 . ? C22B C23B 1.378(12) . ? C22B H22B 0.9500 . ? C23B C24B 1.446(12) . ? C24B N3B 1.365(11) . ? C24B C25B 1.413(11) . ? C25B C26B 1.340(17) . ? C25B H25B 0.9500 . ? C26B C27B 1.376(17) . ? C26B H26B 0.9500 . ? C27B C28B 1.369(12) . ? C27B H27B 0.9500 . ? C28B N3B 1.358(11) . ? C28B H28B 0.9500 . ? C29B C34B 1.401(9) . ? C29B C30B 1.407(10) . ? C30B C31B 1.381(11) . ? C30B H30B 0.9500 . ? C31B C32B 1.396(11) . ? C31B H31B 0.9500 . ? C32B C33B 1.397(11) . ? C32B H32B 0.9500 . ? C33B C34B 1.402(9) . ? C33B H33B 0.9500 . ? C34B C35B 1.447(10) . ? C35B N4B 1.372(8) . ? C35B C36B 1.396(10) . ? C36B C37B 1.378(11) . ? C36B H36B 0.9500 . ? C37B C38B 1.380(10) . ? C37B H37B 0.9500 . ? C38B C39B 1.377(10) . ? C38B H38B 0.9500 . ? C39B N4B 1.345(9) . ? C39B H39B 0.9500 . ? P1 F13 1.534(7) . ? P1 F10 1.535(6) . ? P1 F15 1.577(6) . ? P1 F11 1.581(7) . ? P1 F12 1.588(6) . ? P1 F14 1.593(7) . ? P2 F23 1.559(5) . ? P2 F21 1.570(6) . ? P2 F25 1.586(6) . ? P2 F22 1.586(6) . ? P2 F20 1.587(6) . ? P2 F24 1.592(5) . ? Cl1 C100 1.741(18) . ? Cl2 C100 1.73(2) . ? Cl3 C100 1.70(2) . ? C100 H10A 1.0000 . ? Cl4 C200 1.68(4) . ? Cl5 C200 1.73(4) . ? Cl6 C200 1.70(3) . ? C200 H30C 1.0000 . ? 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 C29A Ir1A C18A 85.4(3) . . ? C29A Ir1A N4A 80.6(3) . . ? C18A Ir1A N4A 95.5(3) . . ? C29A Ir1A N3A 94.3(2) . . ? C18A Ir1A N3A 79.7(3) . . ? N4A Ir1A N3A 173.4(2) . . ? C29A Ir1A N1A 93.3(2) . . ? C18A Ir1A N1A 176.2(3) . . ? N4A Ir1A N1A 87.7(2) . . ? N3A Ir1A N1A 96.8(2) . . ? C29A Ir1A N2A 169.7(2) . . ? C18A Ir1A N2A 104.9(2) . . ? N4A Ir1A N2A 97.9(2) . . ? N3A Ir1A N2A 87.9(2) . . ? N1A Ir1A N2A 76.4(2) . . ? C5A N1A C1A 118.0(6) . . ? C5A N1A Ir1A 116.8(4) . . ? C1A N1A Ir1A 124.8(5) . . ? C10A N2A C6A 119.4(6) . . ? C10A N2A Ir1A 128.2(4) . . ? C6A N2A Ir1A 111.1(4) . . ? N1A C1A C2A 123.1(6) . . ? N1A C1A H1AA 118.5 . . ? C2A C1A H1AA 118.5 . . ? C1A C2A C3A 118.9(6) . . ? C1A C2A H2AA 120.5 . . ? C3A C2A H2AA 120.5 . . ? C2A C3A C4A 118.9(7) . . ? C2A C3A H3AA 120.6 . . ? C4A C3A H3AA 120.6 . . ? C5A C4A C3A 119.2(7) . . ? C5A C4A H4AA 120.4 . . ? C3A C4A H4AA 120.4 . . ? N1A C5A C4A 121.7(6) . . ? N1A C5A C6A 115.1(6) . . ? C4A C5A C6A 123.2(6) . . ? N2A C6A C7A 122.0(6) . . ? N2A C6A C5A 117.9(6) . . ? C7A C6A C5A 120.1(6) . . ? C6A C7A C8A 117.9(6) . . ? C6A C7A H7AA 121.1 . . ? C8A C7A H7AA 121.1 . . ? C9A C8A C7A 120.8(6) . . ? C9A C8A S1A 119.7(5) . . ? C7A C8A S1A 119.5(5) . . ? C8A C9A C10A 118.7(6) . . ? C8A C9A H9AA 120.6 . . ? C10A C9A H9AA 120.6 . . ? N2A C10A C9A 121.0(6) . . ? N2A C10A C11A 122.1(6) . . ? C9A C10A C11A 116.7(6) . . ? C16A C11A C12A 120.6(8) . . ? C16A C11A C10A 120.5(7) . . ? C12A C11A C10A 118.6(6) . . ? C11A C12A C13A 120.1(8) . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C14A C13A C12A 117.8(9) . . ? C14A C13A H13A 121.1 . . ? C12A C13A H13A 121.1 . . ? C13A C14A C15A 122.3(9) . . ? C13A C14A H14A 118.8 . . ? C15A C14A H14A 118.8 . . ? C16A C15A C14A 118.1(8) . . ? C16A C15A H15A 121.0 . . ? C14A C15A H15A 121.0 . . ? C15A C16A C11A 121.1(9) . . ? C15A C16A H16A 119.4 . . ? C11A C16A H16A 119.4 . . ? O1A S1A O2A 118.2(3) . . ? O1A S1A C17A 108.6(4) . . ? O2A S1A C17A 110.0(4) . . ? O1A S1A C8A 109.4(3) . . ? O2A S1A C8A 106.1(3) . . ? C17A S1A C8A 103.5(4) . . ? S1A C17A H17A 109.5 . . ? S1A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? S1A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C19A C18A C23A 118.2(7) . . ? C19A C18A Ir1A 127.7(5) . . ? C23A C18A Ir1A 113.9(6) . . ? C18A C19A C20A 121.3(7) . . ? C18A C19A H19A 119.4 . . ? C20A C19A H19A 119.4 . . ? C21A C20A C19A 120.1(8) . . ? C21A C20A H20A 119.9 . . ? C19A C20A H20A 119.9 . . ? C22A C21A C20A 119.6(7) . . ? C22A C21A H21A 120.2 . . ? C20A C21A H21A 120.2 . . ? C21A C22A C23A 120.1(7) . . ? C21A C22A H22A 120.0 . . ? C23A C22A H22A 120.0 . . ? C22A C23A C18A 120.7(7) . . ? C22A C23A C24A 123.5(7) . . ? C18A C23A C24A 115.7(7) . . ? N3A C24A C25A 118.8(7) . . ? N3A C24A C23A 114.2(6) . . ? C25A C24A C23A 127.0(7) . . ? C26A C25A C24A 120.9(7) . . ? C26A C25A H25A 119.6 . . ? C24A C25A H25A 119.6 . . ? C25A C26A C27A 119.0(7) . . ? C25A C26A H26A 120.5 . . ? C27A C26A H26A 120.5 . . ? C28A C27A C26A 119.4(8) . . ? C28A C27A H27A 120.3 . . ? C26A C27A H27A 120.3 . . ? C27A C28A N3A 122.6(7) . . ? C27A C28A H28A 118.7 . . ? N3A C28A H28A 118.7 . . ? C24A N3A C28A 119.2(6) . . ? C24A N3A Ir1A 116.2(5) . . ? C28A N3A Ir1A 124.5(4) . . ? C30A C29A C34A 117.9(6) . . ? C30A C29A Ir1A 127.2(5) . . ? C34A C29A Ir1A 114.8(5) . . ? C29A C30A C31A 120.7(7) . . ? C29A C30A H30A 119.6 . . ? C31A C30A H30A 119.6 . . ? C32A C31A C30A 120.3(7) . . ? C32A C31A H31A 119.8 . . ? C30A C31A H31A 119.8 . . ? C33A C32A C31A 119.8(7) . . ? C33A C32A H32A 120.1 . . ? C31A C32A H32A 120.1 . . ? C32A C33A C34A 120.2(7) . . ? C32A C33A H33A 119.9 . . ? C34A C33A H33A 119.9 . . ? C33A C34A C29A 121.0(7) . . ? C33A C34A C35A 123.9(7) . . ? C29A C34A C35A 114.9(6) . . ? N4A C35A C36A 119.7(7) . . ? N4A C35A C34A 114.0(6) . . ? C36A C35A C34A 126.3(7) . . ? C37A C36A C35A 120.5(7) . . ? C37A C36A H36A 119.7 . . ? C35A C36A H36A 119.7 . . ? C36A C37A C38A 119.6(7) . . ? C36A C37A H37A 120.2 . . ? C38A C37A H37A 120.2 . . ? C39A C38A C37A 119.2(7) . . ? C39A C38A H38A 120.4 . . ? C37A C38A H38A 120.4 . . ? N4A C39A C38A 121.9(7) . . ? N4A C39A H39A 119.1 . . ? C38A C39A H39A 119.1 . . ? C39A N4A C35A 119.0(6) . . ? C39A N4A Ir1A 125.4(5) . . ? C35A N4A Ir1A 115.6(5) . . ? C29B Ir1B N4B 80.4(2) . . ? C29B Ir1B C18B 84.6(3) . . ? N4B Ir1B C18B 94.9(3) . . ? C29B Ir1B N3B 94.1(3) . . ? N4B Ir1B N3B 173.1(2) . . ? C18B Ir1B N3B 80.5(3) . . ? C29B Ir1B N1B 94.1(3) . . ? N4B Ir1B N1B 88.1(2) . . ? C18B Ir1B N1B 176.5(3) . . ? N3B Ir1B N1B 96.3(2) . . ? C29B Ir1B N2B 170.7(3) . . ? N4B Ir1B N2B 98.2(2) . . ? C18B Ir1B N2B 104.7(2) . . ? N3B Ir1B N2B 87.9(2) . . ? N1B Ir1B N2B 76.7(2) . . ? C1B N1B C5B 118.1(7) . . ? C1B N1B Ir1B 125.0(5) . . ? C5B N1B Ir1B 116.8(5) . . ? C10B N2B C6B 119.0(5) . . ? C10B N2B Ir1B 127.6(4) . . ? C6B N2B Ir1B 112.0(4) . . ? N1B C1B C2B 123.1(7) . . ? N1B C1B H1BA 118.5 . . ? C2B C1B H1BA 118.5 . . ? C1B C2B C3B 118.5(8) . . ? C1B C2B H2BA 120.7 . . ? C3B C2B H2BA 120.7 . . ? C4B C3B C2B 119.2(8) . . ? C4B C3B H3BA 120.4 . . ? C2B C3B H3BA 120.4 . . ? C3B C4B C5B 120.1(8) . . ? C3B C4B H4BA 119.9 . . ? C5B C4B H4BA 119.9 . . ? N1B C5B C4B 120.9(7) . . ? N1B C5B C6B 115.0(6) . . ? C4B C5B C6B 124.1(7) . . ? N2B C6B C7B 122.6(6) . . ? N2B C6B C5B 117.9(6) . . ? C7B C6B C5B 119.4(7) . . ? C8B C7B C6B 118.6(7) . . ? C8B C7B H7BA 120.7 . . ? C6B C7B H7BA 120.7 . . ? C7B C8B C9B 119.3(6) . . ? C7B C8B S1B 119.9(5) . . ? C9B C8B S1B 120.8(6) . . ? C8B C9B C10B 120.1(7) . . ? C8B C9B H9BA 119.9 . . ? C10B C9B H9BA 119.9 . . ? N2B C10B C9B 120.2(6) . . ? N2B C10B C11B 122.3(6) . . ? C9B C10B C11B 117.5(6) . . ? C16B C11B C12B 120.1(7) . . ? C16B C11B C10B 119.9(7) . . ? C12B C11B C10B 119.6(7) . . ? C11B C12B C13B 119.2(8) . . ? C11B C12B H12B 120.4 . . ? C13B C12B H12B 120.4 . . ? C14B C13B C12B 120.1(8) . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? C13B C14B C15B 121.0(8) . . ? C13B C14B H14B 119.5 . . ? C15B C14B H14B 119.5 . . ? C14B C15B C16B 119.8(8) . . ? C14B C15B H15B 120.1 . . ? C16B C15B H15B 120.1 . . ? C11B C16B C15B 119.8(8) . . ? C11B C16B H16B 120.1 . . ? C15B C16B H16B 120.1 . . ? O1B S1B O2B 119.7(4) . . ? O1B S1B C17B 109.1(4) . . ? O2B S1B C17B 109.4(4) . . ? O1B S1B C8B 106.6(3) . . ? O2B S1B C8B 107.5(3) . . ? C17B S1B C8B 103.2(4) . . ? S1B C17B H17D 109.5 . . ? S1B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? S1B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C19B C18B C23B 118.0(8) . . ? C19B C18B Ir1B 128.8(6) . . ? C23B C18B Ir1B 112.8(6) . . ? C18B C19B C20B 120.7(9) . . ? C18B C19B H19B 119.7 . . ? C20B C19B H19B 119.7 . . ? C21B C20B C19B 120.5(10) . . ? C21B C20B H20B 119.8 . . ? C19B C20B H20B 119.8 . . ? C20B C21B C22B 120.6(9) . . ? C20B C21B H21B 119.7 . . ? C22B C21B H21B 119.7 . . ? C23B C22B C21B 117.6(9) . . ? C23B C22B H22B 121.2 . . ? C21B C22B H22B 121.2 . . ? C22B C23B C18B 122.5(9) . . ? C22B C23B C24B 120.9(8) . . ? C18B C23B C24B 116.5(7) . . ? N3B C24B C25B 117.6(9) . . ? N3B C24B C23B 114.7(7) . . ? C25B C24B C23B 127.6(9) . . ? C26B C25B C24B 122.3(10) . . ? C26B C25B H25B 118.8 . . ? C24B C25B H25B 118.8 . . ? C25B C26B C27B 118.8(9) . . ? C25B C26B H26B 120.6 . . ? C27B C26B H26B 120.6 . . ? C28B C27B C26B 119.5(11) . . ? C28B C27B H27B 120.2 . . ? C26B C27B H27B 120.2 . . ? N3B C28B C27B 121.8(10) . . ? N3B C28B H28B 119.1 . . ? C27B C28B H28B 119.1 . . ? C28B N3B C24B 119.9(7) . . ? C28B N3B Ir1B 124.7(6) . . ? C24B N3B Ir1B 115.3(5) . . ? C34B C29B C30B 117.5(7) . . ? C34B C29B Ir1B 115.3(5) . . ? C30B C29B Ir1B 127.0(5) . . ? C31B C30B C29B 120.9(7) . . ? C31B C30B H30B 119.6 . . ? C29B C30B H30B 119.6 . . ? C30B C31B C32B 120.9(7) . . ? C30B C31B H31B 119.6 . . ? C32B C31B H31B 119.6 . . ? C31B C32B C33B 119.8(7) . . ? C31B C32B H32B 120.1 . . ? C33B C32B H32B 120.1 . . ? C32B C33B C34B 118.6(7) . . ? C32B C33B H33B 120.7 . . ? C34B C33B H33B 120.7 . . ? C29B C34B C33B 122.2(7) . . ? C29B C34B C35B 114.7(6) . . ? C33B C34B C35B 123.0(6) . . ? N4B C35B C36B 119.4(6) . . ? N4B C35B C34B 114.4(6) . . ? C36B C35B C34B 126.2(6) . . ? C37B C36B C35B 120.3(7) . . ? C37B C36B H36B 119.9 . . ? C35B C36B H36B 119.9 . . ? C36B C37B C38B 119.8(7) . . ? C36B C37B H37B 120.1 . . ? C38B C37B H37B 120.1 . . ? C39B C38B C37B 118.1(7) . . ? C39B C38B H38B 120.9 . . ? C37B C38B H38B 120.9 . . ? N4B C39B C38B 123.2(7) . . ? N4B C39B H39B 118.4 . . ? C38B C39B H39B 118.4 . . ? C39B N4B C35B 119.1(6) . . ? C39B N4B Ir1B 125.9(4) . . ? C35B N4B Ir1B 114.9(4) . . ? F13 P1 F10 92.9(5) . . ? F13 P1 F15 91.8(5) . . ? F10 P1 F15 174.9(6) . . ? F13 P1 F11 176.9(5) . . ? F10 P1 F11 90.2(5) . . ? F15 P1 F11 85.2(5) . . ? F13 P1 F12 92.2(5) . . ? F10 P1 F12 90.4(4) . . ? F15 P1 F12 91.6(4) . . ? F11 P1 F12 87.0(4) . . ? F13 P1 F14 90.1(5) . . ? F10 P1 F14 89.1(4) . . ? F15 P1 F14 88.7(4) . . ? F11 P1 F14 90.7(5) . . ? F12 P1 F14 177.6(5) . . ? F23 P2 F21 179.4(5) . . ? F23 P2 F25 89.6(4) . . ? F21 P2 F25 90.9(4) . . ? F23 P2 F22 91.0(4) . . ? F21 P2 F22 88.7(4) . . ? F25 P2 F22 89.7(4) . . ? F23 P2 F20 89.9(4) . . ? F21 P2 F20 89.7(5) . . ? F25 P2 F20 178.1(4) . . ? F22 P2 F20 92.1(4) . . ? F23 P2 F24 91.2(4) . . ? F21 P2 F24 89.2(4) . . ? F25 P2 F24 88.6(3) . . ? F22 P2 F24 177.3(4) . . ? F20 P2 F24 89.6(4) . . ? Cl3 C100 Cl2 113.8(11) . . ? Cl3 C100 Cl1 109.2(11) . . ? Cl2 C100 Cl1 110.1(12) . . ? Cl3 C100 H10A 107.9 . . ? Cl2 C100 H10A 107.9 . . ? Cl1 C100 H10A 107.9 . . ? Cl4 C200 Cl6 110.5(19) . . ? Cl4 C200 Cl5 115.2(19) . . ? Cl6 C200 Cl5 114(2) . . ? Cl4 C200 H30C 105.3 . . ? Cl6 C200 H30C 105.3 . . ? Cl5 C200 H30C 105.3 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.925 _refine_diff_density_min -1.363 _refine_diff_density_rms 0.109 # start Validation Reply Form _vrf_PLAT306_I ; PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O100 RESPONSE: H-atoms could not be located from the difference map ; _vrf_PLAT601_I ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 370 A**3 RESPONSE: No electron density peaks of consquence appear in this void space ; data_ib42 _database_code_depnum_ccdc_archive 'CCDC 877475' #TrackingRef 'ligand1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 N2 S' _chemical_formula_sum 'C17 H14 N2 S' _chemical_formula_weight 278.37 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' 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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.811(4) _cell_length_b 9.938(4) _cell_length_c 14.981(5) _cell_angle_alpha 95.08(3) _cell_angle_beta 95.78(3) _cell_angle_gamma 101.52(3) _cell_volume 1415.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4370 _cell_measurement_theta_min 4.74 _cell_measurement_theta_max 53.31 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8797 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14897 _diffrn_reflns_av_R_equivalents 0.1183 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5026 _reflns_number_gt 3639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0861P)^2^+0.2719P] 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 5026 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1689 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _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 S1A S 0.77102(9) 0.68524(9) -0.06379(6) 0.0808(3) Uani 1 1 d . . . N1A N 0.5234(3) 1.0054(2) 0.14931(15) 0.0685(6) Uani 1 1 d . . . N2A N 0.3325(3) 0.7230(2) -0.01037(14) 0.0645(6) Uani 1 1 d . . . C1A C 0.4967(4) 1.0965(3) 0.2138(2) 0.0746(8) Uani 1 1 d . . . H1AA H 0.5733 1.1642 0.2446 0.090 Uiso 1 1 calc R . . C2A C 0.3669(4) 1.0975(3) 0.2375(2) 0.0795(9) Uani 1 1 d . . . H2AA H 0.3539 1.1637 0.2838 0.095 Uiso 1 1 calc R . . C3A C 0.2556(4) 1.0021(3) 0.1937(2) 0.0811(9) Uani 1 1 d . . . H3AA H 0.1636 1.0004 0.2089 0.097 Uiso 1 1 calc R . . C4A C 0.2795(3) 0.9073(3) 0.1264(2) 0.0734(8) Uani 1 1 d . . . H4AA H 0.2036 0.8405 0.0941 0.088 Uiso 1 1 calc R . . C5A C 0.4131(3) 0.9110(3) 0.10696(17) 0.0609(7) Uani 1 1 d . . . C6A C 0.4443(3) 0.8085(3) 0.03717(17) 0.0616(7) Uani 1 1 d . . . C7A C 0.5810(3) 0.8041(3) 0.02588(17) 0.0651(7) Uani 1 1 d . . . H7AA H 0.6565 0.8677 0.0612 0.078 Uiso 1 1 calc R . . C8A C 0.6062(3) 0.7053(3) -0.03786(18) 0.0655(7) Uani 1 1 d . . . C9A C 0.4907(3) 0.6145(3) -0.08649(18) 0.0672(7) Uani 1 1 d . . . H9AA H 0.5044 0.5433 -0.1291 0.081 Uiso 1 1 calc R . . C10A C 0.3579(3) 0.6270(3) -0.07341(17) 0.0634(7) Uani 1 1 d . . . C11A C 0.2319(3) 0.5342(3) -0.12634(18) 0.0657(7) Uani 1 1 d . . . C12A C 0.1013(3) 0.5244(3) -0.09927(18) 0.0684(7) Uani 1 1 d . . . H12A H 0.0903 0.5805 -0.0469 0.082 Uiso 1 1 calc R . . C13A C -0.0150(3) 0.4348(3) -0.1463(2) 0.0746(8) Uani 1 1 d . . . H13A H -0.1043 0.4294 -0.1258 0.090 Uiso 1 1 calc R . . C14A C -0.0014(4) 0.3532(3) -0.2229(2) 0.0793(8) Uani 1 1 d . . . H14A H -0.0806 0.2905 -0.2551 0.095 Uiso 1 1 calc R . . C15A C 0.1270(4) 0.3636(4) -0.2519(2) 0.0940(11) Uani 1 1 d . . . H15A H 0.1370 0.3085 -0.3050 0.113 Uiso 1 1 calc R . . C16A C 0.2426(4) 0.4534(4) -0.2051(2) 0.0876(10) Uani 1 1 d . . . H16A H 0.3311 0.4602 -0.2269 0.105 Uiso 1 1 calc R . . C17A C 0.8894(4) 0.8197(4) 0.0076(3) 0.0953(11) Uani 1 1 d . . . H17A H 0.8680 0.9090 -0.0044 0.143 Uiso 1 1 calc R . . H17B H 0.9856 0.8183 -0.0042 0.143 Uiso 1 1 calc R . . H17C H 0.8800 0.8060 0.0709 0.143 Uiso 1 1 calc R . . S1B S 0.70906(12) 1.25673(9) 0.45268(7) 0.0958(3) Uani 1 1 d . . . N1B N 1.0360(3) 1.0105(3) 0.67070(17) 0.0801(7) Uani 1 1 d . . . N2B N 0.7532(3) 0.8235(2) 0.50634(15) 0.0671(6) Uani 1 1 d . . . C1B C 1.1245(4) 0.9848(4) 0.7383(2) 0.0868(10) Uani 1 1 d . . . H1BA H 1.1947 1.0599 0.7679 0.104 Uiso 1 1 calc R . . C2B C 1.1201(4) 0.8569(4) 0.7675(2) 0.0906(10) Uani 1 1 d . . . H2BA H 1.1834 0.8448 0.8169 0.109 Uiso 1 1 calc R . . C3B C 1.0223(4) 0.7480(4) 0.7234(2) 0.0926(10) Uani 1 1 d . . . H3BA H 1.0173 0.6578 0.7410 0.111 Uiso 1 1 calc R . . C4B C 0.9308(4) 0.7704(3) 0.6528(2) 0.0809(9) Uani 1 1 d . . . H4BA H 0.8621 0.6957 0.6214 0.097 Uiso 1 1 calc R . . C5B C 0.9397(3) 0.9020(3) 0.62833(18) 0.0673(7) Uani 1 1 d . . . C6B C 0.8379(3) 0.9336(3) 0.55573(17) 0.0663(7) Uani 1 1 d . . . C7B C 0.8323(3) 1.0689(3) 0.54341(19) 0.0710(7) Uani 1 1 d . . . H7BA H 0.8962 1.1434 0.5790 0.085 Uiso 1 1 calc R . . C8B C 0.7330(4) 1.0940(3) 0.47886(19) 0.0720(8) Uani 1 1 d . . . C9B C 0.6429(3) 0.9809(3) 0.42874(19) 0.0722(8) Uani 1 1 d . . . H9BA H 0.5713 0.9945 0.3850 0.087 Uiso 1 1 calc R . . C10B C 0.6573(3) 0.8485(3) 0.44232(18) 0.0659(7) Uani 1 1 d . . . C11B C 0.5652(3) 0.7260(3) 0.38795(18) 0.0661(7) Uani 1 1 d . . . C12B C 0.4781(4) 0.7382(3) 0.3116(2) 0.0859(10) Uani 1 1 d . . . H12B H 0.4807 0.8268 0.2919 0.103 Uiso 1 1 calc R . . C13B C 0.3884(4) 0.6254(3) 0.2640(2) 0.0877(10) Uani 1 1 d . . . H13B H 0.3301 0.6370 0.2119 0.105 Uiso 1 1 calc R . . C14B C 0.3816(4) 0.4964(3) 0.2905(2) 0.0766(8) Uani 1 1 d . . . H14B H 0.3171 0.4188 0.2587 0.092 Uiso 1 1 calc R . . C15B C 0.4703(4) 0.4816(3) 0.3642(2) 0.0902(11) Uani 1 1 d . . . H15B H 0.4691 0.3924 0.3826 0.108 Uiso 1 1 calc R . . C16B C 0.5605(4) 0.5946(3) 0.4115(2) 0.0822(9) Uani 1 1 d . . . H16B H 0.6215 0.5817 0.4620 0.099 Uiso 1 1 calc R . . C17B C 0.8411(5) 1.3734(4) 0.5260(3) 0.1159(14) Uani 1 1 d . . . H17D H 0.8232 1.3649 0.5886 0.174 Uiso 1 1 calc R . . H17E H 0.8409 1.4680 0.5124 0.174 Uiso 1 1 calc R . . H17F H 0.9326 1.3520 0.5176 0.174 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 S1A 0.0777(5) 0.0892(6) 0.0747(5) 0.0006(4) -0.0002(4) 0.0245(4) N1A 0.0812(15) 0.0590(13) 0.0605(13) 0.0027(11) -0.0029(11) 0.0104(11) N2A 0.0765(15) 0.0601(13) 0.0533(12) 0.0030(10) 0.0014(11) 0.0102(11) C1A 0.098(2) 0.0537(15) 0.0642(17) -0.0002(13) -0.0070(16) 0.0082(15) C2A 0.103(3) 0.0598(16) 0.0732(19) -0.0053(14) 0.0042(17) 0.0203(16) C3A 0.085(2) 0.0742(19) 0.082(2) -0.0074(16) 0.0100(17) 0.0173(16) C4A 0.080(2) 0.0678(17) 0.0675(17) -0.0040(14) 0.0028(15) 0.0114(15) C5A 0.0768(18) 0.0533(14) 0.0510(13) 0.0067(11) -0.0011(12) 0.0139(13) C6A 0.0768(18) 0.0542(14) 0.0506(13) 0.0069(11) -0.0013(12) 0.0103(13) C7A 0.0768(18) 0.0611(15) 0.0541(14) 0.0068(12) -0.0025(13) 0.0117(13) C8A 0.0798(18) 0.0649(16) 0.0524(14) 0.0103(12) 0.0006(13) 0.0187(14) C9A 0.0798(19) 0.0636(16) 0.0555(14) 0.0017(12) 0.0022(13) 0.0141(14) C10A 0.0787(19) 0.0587(15) 0.0493(13) 0.0026(12) 0.0013(12) 0.0113(13) C11A 0.0806(19) 0.0612(15) 0.0521(14) 0.0012(12) 0.0022(13) 0.0128(13) C12A 0.082(2) 0.0656(16) 0.0537(14) -0.0031(12) 0.0002(14) 0.0133(14) C13A 0.0780(19) 0.0727(18) 0.0687(17) 0.0017(14) -0.0004(15) 0.0127(15) C14A 0.088(2) 0.0713(18) 0.0688(18) -0.0096(15) -0.0053(16) 0.0090(16) C15A 0.097(3) 0.094(2) 0.078(2) -0.0308(18) 0.0002(19) 0.0116(19) C16A 0.084(2) 0.094(2) 0.0732(19) -0.0266(17) 0.0083(16) 0.0076(17) C17A 0.077(2) 0.099(2) 0.104(3) -0.004(2) -0.0051(19) 0.0180(18) S1B 0.1366(8) 0.0619(5) 0.0887(6) 0.0047(4) 0.0008(6) 0.0281(5) N1B 0.0862(17) 0.0824(17) 0.0643(15) -0.0076(13) -0.0012(13) 0.0117(14) N2B 0.0831(16) 0.0608(13) 0.0543(12) 0.0045(10) 0.0007(11) 0.0127(11) C1B 0.082(2) 0.099(2) 0.0691(19) -0.0134(18) -0.0039(16) 0.0108(18) C2B 0.091(2) 0.111(3) 0.0681(19) 0.0029(19) -0.0081(17) 0.031(2) C3B 0.105(3) 0.089(2) 0.082(2) 0.0102(18) -0.0082(19) 0.025(2) C4B 0.094(2) 0.0742(19) 0.0699(18) 0.0044(15) -0.0046(16) 0.0154(16) C5B 0.0774(18) 0.0688(17) 0.0537(14) -0.0027(13) 0.0079(13) 0.0146(14) C6B 0.0817(19) 0.0626(16) 0.0525(14) 0.0014(12) 0.0080(13) 0.0128(14) C7B 0.086(2) 0.0616(16) 0.0610(16) -0.0036(13) 0.0072(14) 0.0102(14) C8B 0.098(2) 0.0591(15) 0.0606(16) 0.0037(13) 0.0120(15) 0.0197(15) C9B 0.091(2) 0.0652(17) 0.0601(15) 0.0055(13) 0.0016(14) 0.0197(15) C10B 0.0821(18) 0.0618(15) 0.0519(14) 0.0056(12) 0.0061(13) 0.0120(13) C11B 0.0817(19) 0.0622(16) 0.0526(14) 0.0052(12) 0.0040(13) 0.0134(14) C12B 0.105(2) 0.0631(17) 0.082(2) 0.0102(15) -0.0212(18) 0.0154(16) C13B 0.094(2) 0.079(2) 0.080(2) 0.0034(17) -0.0210(18) 0.0123(17) C14B 0.090(2) 0.0671(18) 0.0637(17) -0.0011(14) 0.0020(15) 0.0027(15) C15B 0.139(3) 0.0615(17) 0.0623(17) 0.0052(14) -0.0090(19) 0.0132(19) C16B 0.120(3) 0.0637(17) 0.0557(16) 0.0020(13) -0.0163(16) 0.0167(17) C17B 0.151(4) 0.065(2) 0.124(3) -0.003(2) 0.002(3) 0.018(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 S1A C8A 1.746(3) . ? S1A C17A 1.776(4) . ? N1A C5A 1.343(3) . ? N1A C1A 1.347(4) . ? N2A C6A 1.340(3) . ? N2A C10A 1.359(4) . ? C1A C2A 1.357(5) . ? C1A H1AA 0.9500 . ? C2A C3A 1.361(4) . ? C2A H2AA 0.9500 . ? C3A C4A 1.388(4) . ? C3A H3AA 0.9500 . ? C4A C5A 1.365(4) . ? C4A H4AA 0.9500 . ? C5A C6A 1.492(4) . ? C6A C7A 1.377(4) . ? C7A C8A 1.384(4) . ? C7A H7AA 0.9500 . ? C8A C9A 1.392(4) . ? C9A C10A 1.365(4) . ? C9A H9AA 0.9500 . ? C10A C11A 1.491(4) . ? C11A C12A 1.370(4) . ? C11A C16A 1.392(4) . ? C12A C13A 1.383(4) . ? C12A H12A 0.9500 . ? C13A C14A 1.379(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.360(5) . ? C14A H14A 0.9500 . ? C15A C16A 1.378(5) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? S1B C8B 1.752(3) . ? S1B C17B 1.765(4) . ? N1B C1B 1.342(4) . ? N1B C5B 1.345(4) . ? N2B C6B 1.344(3) . ? N2B C10B 1.350(4) . ? C1B C2B 1.374(5) . ? C1B H1BA 0.9500 . ? C2B C3B 1.364(5) . ? C2B H2BA 0.9500 . ? C3B C4B 1.380(5) . ? C3B H3BA 0.9500 . ? C4B C5B 1.378(4) . ? C4B H4BA 0.9500 . ? C5B C6B 1.498(4) . ? C6B C7B 1.384(4) . ? C7B C8B 1.378(4) . ? C7B H7BA 0.9500 . ? C8B C9B 1.389(4) . ? C9B C10B 1.381(4) . ? C9B H9BA 0.9500 . ? C10B C11B 1.483(4) . ? C11B C16B 1.376(4) . ? C11B C12B 1.386(4) . ? C12B C13B 1.371(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.366(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.372(5) . ? C14B H14B 0.9500 . ? C15B C16B 1.372(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8A S1A C17A 103.93(16) . . ? C5A N1A C1A 116.7(3) . . ? C6A N2A C10A 117.0(3) . . ? N1A C1A C2A 123.9(3) . . ? N1A C1A H1AA 118.1 . . ? C2A C1A H1AA 118.1 . . ? C1A C2A C3A 119.0(3) . . ? C1A C2A H2AA 120.5 . . ? C3A C2A H2AA 120.5 . . ? C2A C3A C4A 118.5(3) . . ? C2A C3A H3AA 120.7 . . ? C4A C3A H3AA 120.7 . . ? C5A C4A C3A 119.4(3) . . ? C5A C4A H4AA 120.3 . . ? C3A C4A H4AA 120.3 . . ? N1A C5A C4A 122.5(3) . . ? N1A C5A C6A 116.2(3) . . ? C4A C5A C6A 121.3(2) . . ? N2A C6A C7A 124.0(3) . . ? N2A C6A C5A 115.7(3) . . ? C7A C6A C5A 120.2(2) . . ? C6A C7A C8A 118.7(3) . . ? C6A C7A H7AA 120.6 . . ? C8A C7A H7AA 120.6 . . ? C7A C8A C9A 117.6(3) . . ? C7A C8A S1A 125.7(2) . . ? C9A C8A S1A 116.7(2) . . ? C10A C9A C8A 120.5(3) . . ? C10A C9A H9AA 119.7 . . ? C8A C9A H9AA 119.7 . . ? N2A C10A C9A 122.0(3) . . ? N2A C10A C11A 116.0(3) . . ? C9A C10A C11A 121.9(3) . . ? C12A C11A C16A 117.3(3) . . ? C12A C11A C10A 121.5(2) . . ? C16A C11A C10A 121.2(3) . . ? C11A C12A C13A 121.7(3) . . ? C11A C12A H12A 119.2 . . ? C13A C12A H12A 119.2 . . ? C14A C13A C12A 120.0(3) . . ? C14A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? C15A C14A C13A 119.2(3) . . ? C15A C14A H14A 120.4 . . ? C13A C14A H14A 120.4 . . ? C14A C15A C16A 120.7(3) . . ? C14A C15A H15A 119.7 . . ? C16A C15A H15A 119.7 . . ? C15A C16A C11A 121.1(3) . . ? C15A C16A H16A 119.4 . . ? C11A C16A H16A 119.4 . . ? S1A C17A H17A 109.5 . . ? S1A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? S1A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C8B S1B C17B 103.77(19) . . ? C1B N1B C5B 116.8(3) . . ? C6B N2B C10B 117.2(2) . . ? N1B C1B C2B 124.2(3) . . ? N1B C1B H1BA 117.9 . . ? C2B C1B H1BA 117.9 . . ? C3B C2B C1B 118.1(3) . . ? C3B C2B H2BA 120.9 . . ? C1B C2B H2BA 120.9 . . ? C2B C3B C4B 119.1(3) . . ? C2B C3B H3BA 120.4 . . ? C4B C3B H3BA 120.4 . . ? C5B C4B C3B 119.6(3) . . ? C5B C4B H4BA 120.2 . . ? C3B C4B H4BA 120.2 . . ? N1B C5B C4B 122.1(3) . . ? N1B C5B C6B 116.1(3) . . ? C4B C5B C6B 121.8(3) . . ? N2B C6B C7B 123.5(3) . . ? N2B C6B C5B 115.7(2) . . ? C7B C6B C5B 120.7(3) . . ? C8B C7B C6B 119.1(3) . . ? C8B C7B H7BA 120.4 . . ? C6B C7B H7BA 120.4 . . ? C7B C8B C9B 117.8(3) . . ? C7B C8B S1B 126.2(2) . . ? C9B C8B S1B 116.0(2) . . ? C10B C9B C8B 120.1(3) . . ? C10B C9B H9BA 119.9 . . ? C8B C9B H9BA 119.9 . . ? N2B C10B C9B 122.2(3) . . ? N2B C10B C11B 116.5(2) . . ? C9B C10B C11B 121.3(3) . . ? C16B C11B C12B 116.7(3) . . ? C16B C11B C10B 121.6(2) . . ? C12B C11B C10B 121.7(3) . . ? C13B C12B C11B 121.5(3) . . ? C13B C12B H12B 119.3 . . ? C11B C12B H12B 119.3 . . ? C14B C13B C12B 120.9(3) . . ? C14B C13B H13B 119.6 . . ? C12B C13B H13B 119.6 . . ? C13B C14B C15B 118.5(3) . . ? C13B C14B H14B 120.8 . . ? C15B C14B H14B 120.8 . . ? C16B C15B C14B 120.6(3) . . ? C16B C15B H15B 119.7 . . ? C14B C15B H15B 119.7 . . ? C15B C16B C11B 121.8(3) . . ? C15B C16B H16B 119.1 . . ? C11B C16B H16B 119.1 . . ? S1B C17B H17D 109.5 . . ? S1B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? S1B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.168 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.048 data_ib63 _database_code_depnum_ccdc_archive 'CCDC 877476' #TrackingRef 'ligand2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 N2 O S' _chemical_formula_sum 'C17 H14 N2 O S' _chemical_formula_weight 294.37 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 -C2yc 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 33.093(6) _cell_length_b 6.1290(7) _cell_length_c 15.202(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.672(15) _cell_angle_gamma 90.00 _cell_volume 2921.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5273 _cell_measurement_theta_min 5.55 _cell_measurement_theta_max 61.81 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8974 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18504 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3011 _reflns_number_gt 2778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0823P)^2^+3.3978P] 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 3011 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.244082(17) 0.34398(11) 0.33188(4) 0.0527(2) Uani 1 1 d . . . O1 O 0.22451(6) 0.1606(4) 0.36536(17) 0.0743(6) Uani 1 1 d . . . N1 N 0.35535(7) -0.2032(3) 0.55358(15) 0.0518(5) Uani 1 1 d . . . N2 N 0.38807(5) 0.2562(3) 0.44384(11) 0.0369(4) Uani 1 1 d . . . C1 C 0.37224(9) -0.3732(4) 0.60788(19) 0.0557(6) Uani 1 1 d . . . H1A H 0.3535 -0.4717 0.6238 0.067 Uiso 1 1 calc R . . C2 C 0.41531(9) -0.4125(4) 0.64183(17) 0.0539(6) Uani 1 1 d . . . H2A H 0.4261 -0.5366 0.6795 0.065 Uiso 1 1 calc R . . C17 C 0.24256(9) 0.5776(5) 0.4013(2) 0.0656(7) Uani 1 1 d . . . H17A H 0.2129 0.6221 0.3898 0.098 Uiso 1 1 calc R . . H17B H 0.2584 0.6976 0.3850 0.098 Uiso 1 1 calc R . . H17C H 0.2556 0.5412 0.4671 0.098 Uiso 1 1 calc R . . C3 C 0.44253(8) -0.2678(4) 0.61995(17) 0.0525(6) Uani 1 1 d . . . H3A H 0.4725 -0.2896 0.6434 0.063 Uiso 1 1 calc R . . C4 C 0.42595(7) -0.0914(4) 0.56384(16) 0.0458(5) Uani 1 1 d . . . H4A H 0.4442 0.0096 0.5478 0.055 Uiso 1 1 calc R . . C5 C 0.38210(7) -0.0645(3) 0.53130(14) 0.0392(4) Uani 1 1 d . . . C6 C 0.36203(7) 0.1188(3) 0.46815(14) 0.0380(4) Uani 1 1 d . . . C7 C 0.31770(7) 0.1403(4) 0.43576(16) 0.0431(5) Uani 1 1 d . . . H7A H 0.2998 0.0430 0.4551 0.052 Uiso 1 1 calc R . . C8 C 0.30093(6) 0.3075(4) 0.37493(15) 0.0419(5) Uani 1 1 d . . . C9 C 0.32711(7) 0.4450(4) 0.34617(15) 0.0456(5) Uani 1 1 d . . . H9A H 0.3155 0.5554 0.3013 0.055 Uiso 1 1 calc R . . C10 C 0.37116(6) 0.4185(3) 0.38438(13) 0.0370(4) Uani 1 1 d . . . C11 C 0.40147(7) 0.5714(3) 0.36192(13) 0.0380(4) Uani 1 1 d . . . C12 C 0.44510(7) 0.5302(4) 0.39307(15) 0.0454(5) Uani 1 1 d . . . H12A H 0.4556 0.4004 0.4268 0.055 Uiso 1 1 calc R . . C13 C 0.47334(8) 0.6774(4) 0.37528(18) 0.0531(6) Uani 1 1 d . . . H13A H 0.5031 0.6480 0.3970 0.064 Uiso 1 1 calc R . . C14 C 0.45858(9) 0.8654(4) 0.32642(18) 0.0538(6) Uani 1 1 d . . . H14A H 0.4780 0.9662 0.3146 0.065 Uiso 1 1 calc R . . C15 C 0.41522(8) 0.9070(4) 0.29455(18) 0.0530(6) Uani 1 1 d . . . H15A H 0.4048 1.0360 0.2601 0.064 Uiso 1 1 calc R . . C16 C 0.38710(7) 0.7619(4) 0.31263(16) 0.0460(5) Uani 1 1 d . . . H16A H 0.3574 0.7927 0.2910 0.055 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 S1 0.0339(3) 0.0624(4) 0.0554(4) -0.0013(3) 0.0054(2) -0.0013(2) O1 0.0516(10) 0.0750(14) 0.0923(15) -0.0036(11) 0.0174(10) -0.0188(10) N1 0.0541(11) 0.0469(11) 0.0575(11) 0.0076(9) 0.0222(9) -0.0032(9) N2 0.0381(8) 0.0366(9) 0.0374(8) 0.0006(7) 0.0141(7) 0.0016(7) C1 0.0686(16) 0.0450(13) 0.0571(14) 0.0075(11) 0.0252(12) -0.0040(11) C2 0.0735(16) 0.0396(12) 0.0482(12) 0.0065(10) 0.0189(12) 0.0080(11) C17 0.0521(14) 0.0615(16) 0.090(2) -0.0061(15) 0.0320(14) 0.0015(12) C3 0.0526(13) 0.0478(13) 0.0531(13) 0.0036(11) 0.0115(11) 0.0089(10) C4 0.0471(12) 0.0407(11) 0.0496(12) 0.0035(9) 0.0155(10) 0.0012(9) C5 0.0447(11) 0.0349(10) 0.0400(10) -0.0007(8) 0.0164(8) 0.0002(8) C6 0.0403(10) 0.0369(10) 0.0374(10) -0.0016(8) 0.0132(8) -0.0012(8) C7 0.0404(11) 0.0421(11) 0.0474(11) 0.0000(9) 0.0147(9) -0.0033(9) C8 0.0342(10) 0.0483(12) 0.0401(10) -0.0040(9) 0.0077(8) -0.0010(8) C9 0.0399(11) 0.0518(13) 0.0423(11) 0.0093(9) 0.0093(9) 0.0028(9) C10 0.0380(10) 0.0397(10) 0.0344(9) 0.0000(8) 0.0131(8) 0.0014(8) C11 0.0419(10) 0.0396(10) 0.0348(9) -0.0005(8) 0.0154(8) 0.0007(8) C12 0.0415(11) 0.0466(12) 0.0470(11) 0.0072(9) 0.0126(9) 0.0016(9) C13 0.0427(12) 0.0569(14) 0.0598(14) 0.0017(11) 0.0165(10) -0.0049(10) C14 0.0571(14) 0.0488(13) 0.0609(14) 0.0007(11) 0.0265(12) -0.0103(11) C15 0.0617(14) 0.0428(12) 0.0597(14) 0.0095(10) 0.0267(12) 0.0033(11) C16 0.0449(11) 0.0446(12) 0.0508(12) 0.0072(10) 0.0188(10) 0.0064(9) _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 1.467(2) . ? S1 C17 1.789(3) . ? S1 C8 1.797(2) . ? N1 C1 1.336(3) . ? N1 C5 1.346(3) . ? N2 C6 1.339(3) . ? N2 C10 1.340(3) . ? C1 C2 1.373(4) . ? C1 H1A 0.9500 . ? C2 C3 1.379(4) . ? C2 H2A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C3 C4 1.378(3) . ? C3 H3A 0.9500 . ? C4 C5 1.385(3) . ? C4 H4A 0.9500 . ? C5 C6 1.489(3) . ? C6 C7 1.396(3) . ? C7 C8 1.373(3) . ? C7 H7A 0.9500 . ? C8 C9 1.376(3) . ? C9 C10 1.395(3) . ? C9 H9A 0.9500 . ? C10 C11 1.490(3) . ? C11 C16 1.386(3) . ? C11 C12 1.391(3) . ? C12 C13 1.386(3) . ? C12 H12A 0.9500 . ? C13 C14 1.373(4) . ? C13 H13A 0.9500 . ? C14 C15 1.383(4) . ? C14 H14A 0.9500 . ? C15 C16 1.377(3) . ? C15 H15A 0.9500 . ? C16 H16A 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 S1 C17 108.04(14) . . ? O1 S1 C8 107.77(12) . . ? C17 S1 C8 96.25(12) . . ? C1 N1 C5 118.0(2) . . ? C6 N2 C10 119.10(17) . . ? N1 C1 C2 123.2(2) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C3 118.4(2) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 118.6(2) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? N1 C5 C4 122.2(2) . . ? N1 C5 C6 116.44(19) . . ? C4 C5 C6 121.35(19) . . ? N2 C6 C7 122.68(19) . . ? N2 C6 C5 117.33(18) . . ? C7 C6 C5 119.99(19) . . ? C8 C7 C6 117.4(2) . . ? C8 C7 H7A 121.3 . . ? C6 C7 H7A 121.3 . . ? C7 C8 C9 120.7(2) . . ? C7 C8 S1 119.24(17) . . ? C9 C8 S1 120.01(17) . . ? C8 C9 C10 118.5(2) . . ? C8 C9 H9A 120.8 . . ? C10 C9 H9A 120.8 . . ? N2 C10 C9 121.49(19) . . ? N2 C10 C11 117.07(18) . . ? C9 C10 C11 121.44(19) . . ? C16 C11 C12 118.4(2) . . ? C16 C11 C10 120.92(19) . . ? C12 C11 C10 120.62(19) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 C11 121.0(2) . . ? C15 C16 H16A 119.5 . . ? C11 C16 H16A 119.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.938 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.048 data_ib57 _database_code_depnum_ccdc_archive 'CCDC 877477' #TrackingRef 'ligand3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 N2 O2 S' _chemical_formula_sum 'C17 H14 N2 O2 S' _chemical_formula_weight 310.37 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 -C2yc 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 32.941(7) _cell_length_b 6.1326(9) _cell_length_c 15.569(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.002(16) _cell_angle_gamma 90.00 _cell_volume 2973.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4993 _cell_measurement_theta_min 6.07 _cell_measurement_theta_max 54.35 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8763 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28003 _diffrn_reflns_av_R_equivalents 0.1010 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3026 _reflns_number_gt 2691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0427P)^2^+1.8925P] 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 3026 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _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 0.244073(11) 0.15713(6) 0.34729(2) 0.03194(13) Uani 1 1 d . . . O1 O 0.22500(4) 0.3310(2) 0.38307(9) 0.0451(3) Uani 1 1 d . . . O2 O 0.22873(3) 0.1201(2) 0.25075(7) 0.0401(3) Uani 1 1 d . . . N1 N 0.35704(5) 0.7066(3) 0.55701(11) 0.0465(4) Uani 1 1 d . . . N2 N 0.38841(4) 0.2487(2) 0.44715(9) 0.0337(3) Uani 1 1 d . . . C1 C 0.37440(7) 0.8739(3) 0.61149(14) 0.0514(5) Uani 1 1 d . . . H1A H 0.3558 0.9730 0.6272 0.062 Uiso 1 1 calc R . . C2 C 0.41810(7) 0.9100(3) 0.64611(13) 0.0512(5) Uani 1 1 d . . . H2A H 0.4293 1.0312 0.6845 0.061 Uiso 1 1 calc R . . C3 C 0.44503(6) 0.7666(3) 0.62375(14) 0.0512(5) Uani 1 1 d . . . H3A H 0.4752 0.7867 0.6471 0.061 Uiso 1 1 calc R . . C4 C 0.42785(6) 0.5923(3) 0.56695(12) 0.0444(4) Uani 1 1 d . . . H4A H 0.4460 0.4919 0.5503 0.053 Uiso 1 1 calc R . . C5 C 0.38363(5) 0.5680(3) 0.53501(10) 0.0353(3) Uani 1 1 d . . . C6 C 0.36286(5) 0.3869(3) 0.47233(10) 0.0336(3) Uani 1 1 d . . . C7 C 0.31824(5) 0.3664(3) 0.44254(10) 0.0344(3) Uani 1 1 d . . . H7A H 0.3007 0.4634 0.4627 0.041 Uiso 1 1 calc R . . C8 C 0.30061(5) 0.2002(3) 0.38282(10) 0.0318(3) Uani 1 1 d . . . C9 C 0.32612(5) 0.0593(3) 0.35356(10) 0.0354(3) Uani 1 1 d . . . H9A H 0.3138 -0.0527 0.3109 0.043 Uiso 1 1 calc R . . C10 C 0.37064(5) 0.0869(3) 0.38877(10) 0.0322(3) Uani 1 1 d . . . C11 C 0.40043(5) -0.0667(3) 0.36519(10) 0.0333(3) Uani 1 1 d . . . C12 C 0.44456(5) -0.0269(3) 0.39514(12) 0.0427(4) Uani 1 1 d . . . H12A H 0.4556 0.1017 0.4287 0.051 Uiso 1 1 calc R . . C13 C 0.47240(6) -0.1745(3) 0.37611(14) 0.0495(4) Uani 1 1 d . . . H13A H 0.5024 -0.1465 0.3973 0.059 Uiso 1 1 calc R . . C14 C 0.45712(6) -0.3608(3) 0.32703(13) 0.0488(4) Uani 1 1 d . . . H14A H 0.4764 -0.4612 0.3143 0.059 Uiso 1 1 calc R . . C15 C 0.41353(6) -0.4002(3) 0.29650(13) 0.0482(4) Uani 1 1 d . . . H15A H 0.4027 -0.5278 0.2620 0.058 Uiso 1 1 calc R . . C16 C 0.38550(5) -0.2552(3) 0.31572(12) 0.0411(4) Uani 1 1 d . . . H16A H 0.3556 -0.2852 0.2947 0.049 Uiso 1 1 calc R . . C17 C 0.23988(6) -0.0877(3) 0.40207(13) 0.0439(4) Uani 1 1 d . . . H17A H 0.2554 -0.0740 0.4673 0.066 Uiso 1 1 calc R . . H17B H 0.2524 -0.2067 0.3769 0.066 Uiso 1 1 calc R . . H17C H 0.2096 -0.1192 0.3926 0.066 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 S1 0.02829(19) 0.0330(2) 0.0343(2) 0.00004(15) 0.00989(14) 0.00247(14) O1 0.0382(6) 0.0429(7) 0.0563(7) -0.0075(6) 0.0181(5) 0.0072(5) O2 0.0373(6) 0.0453(7) 0.0322(6) 0.0010(5) 0.0038(4) 0.0010(5) N1 0.0472(8) 0.0438(8) 0.0502(8) -0.0134(7) 0.0184(7) -0.0024(7) N2 0.0341(6) 0.0331(7) 0.0346(7) -0.0027(5) 0.0119(5) -0.0017(5) C1 0.0593(11) 0.0428(10) 0.0540(11) -0.0138(8) 0.0210(9) -0.0018(9) C2 0.0645(12) 0.0390(10) 0.0464(10) -0.0102(8) 0.0132(8) -0.0118(9) C3 0.0455(9) 0.0453(10) 0.0557(11) -0.0067(9) 0.0065(8) -0.0095(8) C4 0.0409(9) 0.0394(9) 0.0506(10) -0.0060(8) 0.0117(7) -0.0027(7) C5 0.0388(8) 0.0339(8) 0.0328(7) -0.0013(6) 0.0113(6) -0.0023(7) C6 0.0362(8) 0.0325(8) 0.0322(7) -0.0008(6) 0.0113(6) -0.0007(6) C7 0.0351(7) 0.0349(8) 0.0341(8) -0.0015(6) 0.0126(6) 0.0032(6) C8 0.0307(7) 0.0342(8) 0.0302(7) 0.0012(6) 0.0095(6) 0.0013(6) C9 0.0336(7) 0.0359(8) 0.0361(8) -0.0067(6) 0.0103(6) -0.0009(6) C10 0.0325(7) 0.0330(8) 0.0321(7) -0.0008(6) 0.0119(6) -0.0001(6) C11 0.0331(7) 0.0357(8) 0.0325(7) 0.0013(6) 0.0125(6) 0.0021(6) C12 0.0341(8) 0.0459(10) 0.0467(9) -0.0083(8) 0.0112(7) -0.0008(7) C13 0.0324(8) 0.0567(12) 0.0590(11) -0.0009(9) 0.0143(8) 0.0063(8) C14 0.0463(9) 0.0470(11) 0.0570(11) 0.0013(8) 0.0221(8) 0.0142(8) C15 0.0505(10) 0.0385(9) 0.0583(11) -0.0097(8) 0.0216(8) 0.0020(8) C16 0.0360(8) 0.0392(9) 0.0493(9) -0.0071(7) 0.0156(7) -0.0014(7) C17 0.0467(9) 0.0412(9) 0.0494(10) 0.0058(8) 0.0233(8) -0.0017(8) _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 1.4388(12) . ? S1 O2 1.4393(12) . ? S1 C17 1.7542(18) . ? S1 C8 1.7814(15) . ? N1 C1 1.336(2) . ? N1 C5 1.342(2) . ? N2 C6 1.340(2) . ? N2 C10 1.344(2) . ? C1 C2 1.381(3) . ? C1 H1A 0.9500 . ? C2 C3 1.372(3) . ? C2 H2A 0.9500 . ? C3 C4 1.385(3) . ? C3 H3A 0.9500 . ? C4 C5 1.386(2) . ? C4 H4A 0.9500 . ? C5 C6 1.490(2) . ? C6 C7 1.396(2) . ? C7 C8 1.374(2) . ? C7 H7A 0.9500 . ? C8 C9 1.382(2) . ? C9 C10 1.399(2) . ? C9 H9A 0.9500 . ? C10 C11 1.490(2) . ? C11 C16 1.388(2) . ? C11 C12 1.396(2) . ? C12 C13 1.387(2) . ? C12 H12A 0.9500 . ? C13 C14 1.376(3) . ? C13 H13A 0.9500 . ? C14 C15 1.379(3) . ? C14 H14A 0.9500 . ? C15 C16 1.383(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.18(7) . . ? O1 S1 C17 109.43(8) . . ? O2 S1 C17 108.42(8) . . ? O1 S1 C8 108.32(7) . . ? O2 S1 C8 108.89(7) . . ? C17 S1 C8 102.45(8) . . ? C1 N1 C5 117.92(16) . . ? C6 N2 C10 119.22(13) . . ? N1 C1 C2 123.19(18) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C3 C2 C1 118.45(17) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 119.55(18) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 118.37(17) . . ? C3 C4 H4A 120.8 . . ? C5 C4 H4A 120.8 . . ? N1 C5 C4 122.52(16) . . ? N1 C5 C6 116.13(14) . . ? C4 C5 C6 121.34(15) . . ? N2 C6 C7 122.64(14) . . ? N2 C6 C5 117.73(13) . . ? C7 C6 C5 119.63(14) . . ? C8 C7 C6 117.32(14) . . ? C8 C7 H7A 121.3 . . ? C6 C7 H7A 121.3 . . ? C7 C8 C9 121.23(14) . . ? C7 C8 S1 119.24(12) . . ? C9 C8 S1 119.45(12) . . ? C8 C9 C10 117.90(14) . . ? C8 C9 H9A 121.0 . . ? C10 C9 H9A 121.0 . . ? N2 C10 C9 121.63(14) . . ? N2 C10 C11 117.14(13) . . ? C9 C10 C11 121.20(14) . . ? C16 C11 C12 118.26(15) . . ? C16 C11 C10 121.37(14) . . ? C12 C11 C10 120.34(15) . . ? C13 C12 C11 120.22(17) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.85(16) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 119.26(16) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C14 C15 C16 120.41(17) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C15 C16 C11 120.99(16) . . ? C15 C16 H16A 119.5 . . ? C11 C16 H16A 119.5 . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.201 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.045