Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'Chang Tong Yang' 'Daming Fan' 'Peng Foo Lee' 'John D. Ranford' 'Jagadese J. Vittal' _publ_contact_author_name 'Dr Chang Tong Yang' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive Singapore 117543 SINGAPORE ; _publ_contact_author_email CHMYCT@NUS.EDU.SG _publ_section_title ; Synthesis, Characterization, and Biologaical Activities of 2-Phenylpyridine Gold(III) Complexes with Thiolate Ligands ; data_jdr48 _database_code_CSD 214284 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Au Cl N2 O4.50 S' _chemical_formula_weight 547.76 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' Au Au -2.0133 8.8022 '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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.4444(1) _cell_length_b 10.1827(1) _cell_length_c 13.5174(1) _cell_angle_alpha 90.00 _cell_angle_beta 116.695(1) _cell_angle_gamma 90.00 _cell_volume 1653.288(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 29.46 _exptl_crystal_description 'thin plates' _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 9.210 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.2552 _exptl_absorpt_correction_T_max 0.4552 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10751 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 29.46 _reflns_number_total 6919 _reflns_number_gt 6344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _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^)+(0.0089P)^2^+0.0000P] 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 mixed _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 0.017(7) _refine_ls_number_reflns 6919 _refine_ls_number_parameters 442 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 Au1 Au 0.53108(2) 0.52391(2) 0.28002(2) 0.02430(7) Uani 1 1 d . . . S1 S 0.5277(2) 0.7442(2) 0.2556(2) 0.0401(5) Uani 1 1 d . . . O1 O 0.6047(4) 0.5451(5) 0.0357(5) 0.0406(14) Uani 1 1 d . . . O2 O 0.5862(4) 0.7639(5) 0.0284(5) 0.0385(14) Uani 1 1 d . . . H2O H 0.6528 0.7651 0.0449 0.046 Uiso 1 1 calc R . . N1 N 0.5474(5) 0.3241(6) 0.3185(6) 0.0291(14) Uani 1 1 d . . . N2 N 0.4477(5) 0.5116(7) 0.1032(5) 0.0253(13) Uani 1 1 d . . . H2A H 0.4807 0.4494 0.0809 0.030 Uiso 1 1 calc R . . H2B H 0.3767 0.4868 0.0817 0.030 Uiso 1 1 calc R . . C1 C 0.6003(6) 0.5351(11) 0.4459(7) 0.0334(18) Uani 1 1 d . . . C2 C 0.6266(7) 0.6482(9) 0.5111(8) 0.038(2) Uani 1 1 d . . . H2 H 0.6150 0.7306 0.4781 0.046 Uiso 1 1 calc R . . C3 C 0.6700(8) 0.6374(11) 0.6256(8) 0.047(2) Uani 1 1 d . . . H3 H 0.6875 0.7129 0.6688 0.056 Uiso 1 1 calc R . . C4 C 0.6876(7) 0.5150(13) 0.6757(8) 0.051(3) Uani 1 1 d . . . H4 H 0.7163 0.5094 0.7523 0.061 Uiso 1 1 calc R . . C5 C 0.6633(7) 0.4033(10) 0.6145(8) 0.041(2) Uani 1 1 d . . . H5 H 0.6744 0.3215 0.6484 0.049 Uiso 1 1 calc R . . C6 C 0.6210(7) 0.4135(9) 0.4990(8) 0.035(2) Uani 1 1 d . . . C7 C 0.5956(6) 0.2945(7) 0.4260(7) 0.0284(16) Uani 1 1 d . . . C8 C 0.6175(7) 0.1670(9) 0.4614(9) 0.043(2) Uani 1 1 d . . . H8 H 0.6505 0.1480 0.5367 0.051 Uiso 1 1 calc R . . C9 C 0.5910(7) 0.0684(8) 0.3865(9) 0.048(2) Uani 1 1 d . . . H9 H 0.6048 -0.0185 0.4099 0.057 Uiso 1 1 calc R . . C10 C 0.5438(8) 0.0978(9) 0.2764(9) 0.055(3) Uani 1 1 d . . . H10 H 0.5271 0.0313 0.2241 0.066 Uiso 1 1 calc R . . C11 C 0.5213(9) 0.2267(8) 0.2435(9) 0.046(2) Uani 1 1 d . . . H11 H 0.4875 0.2469 0.1684 0.055 Uiso 1 1 calc R . . C12 C 0.4296(6) 0.7506(8) 0.1102(7) 0.036(2) Uani 1 1 d . . . H12A H 0.3542 0.7471 0.1023 0.043 Uiso 1 1 calc R . . H12B H 0.4384 0.8328 0.0787 0.043 Uiso 1 1 calc R . . C13 C 0.4484(6) 0.6368(8) 0.0487(7) 0.0292(16) Uani 1 1 d . . . H13 H 0.3868 0.6352 -0.0263 0.035 Uiso 1 1 calc R . . C14 C 0.5574(6) 0.6478(7) 0.0390(6) 0.0263(15) Uani 1 1 d . . . Au2 Au -0.07389(2) 0.46218(3) -0.37486(3) 0.02541(7) Uani 1 1 d . . . S2 S -0.04776(19) 0.2518(2) -0.31500(19) 0.0370(5) Uani 1 1 d . . . O3 O 0.2093(5) 0.4771(7) -0.1445(7) 0.062(2) Uani 1 1 d . . . O4 O 0.2139(5) 0.2821(5) -0.0722(5) 0.0426(14) Uani 1 1 d . . . H4O H 0.2007 0.2267 -0.1205 0.051 Uiso 1 1 calc R . . N3 N -0.1037(5) 0.6505(6) -0.4446(6) 0.0304(15) Uani 1 1 d . . . N4 N -0.0063(5) 0.5209(8) -0.2060(6) 0.0354(15) Uani 1 1 d . . . H3A H 0.0438 0.5852 -0.1933 0.042 Uiso 1 1 calc R . . H3B H -0.0611 0.5529 -0.1920 0.042 Uiso 1 1 calc R . . C15 C -0.1337(6) 0.4112(8) -0.5359(7) 0.0255(17) Uani 1 1 d . . . C16 C -0.1487(7) 0.2862(9) -0.5778(7) 0.0311(18) Uani 1 1 d . . . H16 H -0.1334 0.2144 -0.5307 0.037 Uiso 1 1 calc R . . C17 C -0.1866(7) 0.2670(9) -0.6909(8) 0.041(2) Uani 1 1 d . . . H17 H -0.1952 0.1822 -0.7191 0.049 Uiso 1 1 calc R . . C18 C -0.2117(8) 0.3728(11) -0.7614(8) 0.051(2) Uani 1 1 d . . . H18 H -0.2382 0.3598 -0.8371 0.061 Uiso 1 1 calc R . . C19 C -0.1972(7) 0.4974(9) -0.7192(7) 0.043(2) Uani 1 1 d . . . H19 H -0.2130 0.5690 -0.7666 0.051 Uiso 1 1 calc R . . C20 C -0.1588(6) 0.5186(10) -0.6050(6) 0.0300(16) Uani 1 1 d . . . C21 C -0.1472(7) 0.6490(9) -0.5565(8) 0.0314(19) Uani 1 1 d . . . C22 C -0.1763(8) 0.7673(9) -0.6147(9) 0.044(2) Uani 1 1 d . . . H22 H -0.2049 0.7688 -0.6914 0.052 Uiso 1 1 calc R . . C23 C -0.1612(8) 0.8836(9) -0.5545(10) 0.050(3) Uani 1 1 d . . . H23 H -0.1785 0.9637 -0.5916 0.060 Uiso 1 1 calc R . . C24 C -0.1219(7) 0.8815(9) -0.4429(9) 0.049(2) Uani 1 1 d . . . H24 H -0.1134 0.9589 -0.4034 0.059 Uiso 1 1 calc R . . C25 C -0.0945(7) 0.7614(9) -0.3888(9) 0.040(2) Uani 1 1 d . . . H25 H -0.0694 0.7583 -0.3125 0.047 Uiso 1 1 calc R . . C26 C -0.0235(7) 0.2854(9) -0.1727(7) 0.038(2) Uani 1 1 d . . . H26A H -0.0942 0.3005 -0.1713 0.046 Uiso 1 1 calc R . . H26B H 0.0118 0.2100 -0.1263 0.046 Uiso 1 1 calc R . . C27 C 0.0501(6) 0.4049(8) -0.1279(7) 0.0294(16) Uani 1 1 d . . . H27 H 0.0555 0.4257 -0.0548 0.035 Uiso 1 1 calc R . . C28 C 0.1674(6) 0.3906(7) -0.1168(7) 0.0305(16) Uani 1 1 d . . . Cl1 Cl 0.22293(17) 0.49277(18) 0.2068(2) 0.0416(5) Uani 1 1 d D . . O5 O 0.2862(7) 0.4788(10) 0.3249(6) 0.103(3) Uani 1 1 d D . . O6 O 0.2397(7) 0.6183(7) 0.1737(9) 0.113(4) Uani 1 1 d D . . O7 O 0.2644(5) 0.3938(7) 0.1595(7) 0.067(2) Uani 1 1 d D . . O8 O 0.1092(5) 0.4706(8) 0.1753(7) 0.084(3) Uani 1 1 d D . . Cl2 Cl -0.1088(5) 0.6731(6) -1.0973(5) 0.0700(15) Uani 0.50 1 d P . . Cl3 Cl -0.1074(6) 0.2460(7) 0.0411(7) 0.092(2) Uani 0.50 1 d P . . O9 O -0.2145(7) 0.4864(6) -1.0134(8) 0.067(2) Uani 1 1 d D . . H1S H -0.149(6) 0.445(13) -0.996(12) 0.12(4) Uiso 1 1 d D . . H2S H -0.195(11) 0.564(7) -1.031(12) 0.12(4) Uiso 1 1 d 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 Au1 0.02940(15) 0.01821(11) 0.02578(16) -0.00071(13) 0.01283(12) -0.00140(12) S1 0.0560(14) 0.0196(10) 0.0401(13) -0.0027(9) 0.0176(12) -0.0033(9) O1 0.048(3) 0.028(3) 0.054(4) -0.005(3) 0.030(3) -0.002(2) O2 0.032(3) 0.032(3) 0.050(4) 0.010(3) 0.016(3) -0.006(2) N1 0.039(4) 0.018(3) 0.026(4) -0.001(3) 0.011(3) -0.006(2) N2 0.031(3) 0.023(3) 0.027(3) 0.001(3) 0.017(3) -0.006(2) C1 0.027(4) 0.049(5) 0.030(4) -0.003(5) 0.017(3) -0.005(4) C2 0.040(5) 0.030(4) 0.042(6) -0.007(4) 0.016(4) -0.007(4) C3 0.049(5) 0.045(5) 0.043(6) -0.022(5) 0.017(5) -0.005(4) C4 0.037(5) 0.074(7) 0.031(5) -0.011(6) 0.007(4) -0.005(5) C5 0.032(4) 0.055(6) 0.032(5) 0.005(4) 0.011(4) 0.004(4) C6 0.036(5) 0.041(5) 0.034(5) -0.009(4) 0.020(4) -0.008(4) C7 0.028(4) 0.028(4) 0.029(5) 0.006(3) 0.013(3) 0.003(3) C8 0.044(5) 0.037(5) 0.046(6) 0.010(4) 0.019(5) 0.006(4) C9 0.057(5) 0.019(4) 0.066(7) 0.011(4) 0.027(5) 0.003(3) C10 0.085(7) 0.024(4) 0.060(7) 0.000(4) 0.036(6) -0.006(4) C11 0.074(7) 0.017(4) 0.043(6) -0.007(4) 0.023(5) -0.003(4) C12 0.034(4) 0.022(4) 0.048(6) 0.008(4) 0.014(4) 0.002(3) C13 0.026(4) 0.029(4) 0.022(4) 0.003(3) 0.001(3) 0.000(3) C14 0.030(4) 0.029(4) 0.017(4) 0.002(3) 0.008(3) -0.002(3) Au2 0.02668(14) 0.02657(13) 0.02283(15) -0.00065(13) 0.01098(12) 0.00090(12) S2 0.0509(13) 0.0284(10) 0.0280(11) -0.0007(8) 0.0145(10) -0.0037(8) O3 0.039(3) 0.046(4) 0.097(6) 0.023(4) 0.029(4) 0.002(3) O4 0.047(3) 0.035(3) 0.044(4) 0.006(3) 0.018(3) 0.007(3) N3 0.034(3) 0.025(3) 0.033(4) 0.002(3) 0.015(3) 0.003(3) N4 0.042(4) 0.027(3) 0.030(4) -0.001(4) 0.009(3) 0.008(4) C15 0.016(3) 0.034(4) 0.024(4) -0.003(3) 0.008(3) 0.001(3) C16 0.033(4) 0.037(5) 0.025(4) 0.000(4) 0.016(4) 0.007(3) C17 0.048(5) 0.034(4) 0.035(5) -0.006(4) 0.015(4) -0.002(4) C18 0.051(6) 0.069(7) 0.026(5) -0.008(4) 0.012(5) -0.006(5) C19 0.057(5) 0.045(6) 0.025(4) 0.007(3) 0.017(4) 0.008(4) C20 0.024(3) 0.045(4) 0.019(4) -0.002(4) 0.008(3) 0.001(4) C21 0.027(4) 0.031(4) 0.037(5) 0.012(4) 0.015(4) 0.012(3) C22 0.046(5) 0.038(5) 0.049(6) 0.015(4) 0.023(5) 0.008(4) C23 0.056(6) 0.031(4) 0.071(8) 0.018(5) 0.036(6) 0.008(4) C24 0.052(5) 0.032(5) 0.071(8) 0.006(5) 0.035(6) 0.009(4) C25 0.038(5) 0.034(5) 0.049(6) -0.012(4) 0.022(4) -0.002(4) C26 0.037(5) 0.052(5) 0.023(4) 0.006(4) 0.011(4) 0.000(4) C27 0.032(4) 0.031(4) 0.020(4) 0.002(3) 0.007(3) 0.002(3) C28 0.036(4) 0.027(4) 0.029(4) -0.002(3) 0.015(4) 0.002(3) Cl1 0.0452(11) 0.0350(12) 0.0498(14) -0.0037(8) 0.0259(11) -0.0052(8) O5 0.133(8) 0.108(8) 0.056(6) -0.028(6) 0.031(6) -0.014(7) O6 0.082(6) 0.051(5) 0.219(13) 0.061(7) 0.081(8) 0.010(4) O7 0.058(4) 0.064(5) 0.086(6) -0.034(4) 0.039(5) -0.008(4) O8 0.046(4) 0.077(5) 0.142(8) -0.023(6) 0.055(5) -0.016(4) Cl2 0.085(4) 0.064(4) 0.063(4) -0.006(3) 0.035(3) 0.001(3) Cl3 0.086(4) 0.083(5) 0.111(6) 0.010(4) 0.048(5) 0.014(4) O9 0.078(5) 0.036(4) 0.104(7) 0.002(4) 0.057(5) 0.001(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 Au1 C1 2.008(9) . ? Au1 N1 2.087(6) . ? Au1 N2 2.139(6) . ? Au1 S1 2.265(2) . ? S1 C12 1.810(9) . ? O1 C14 1.236(9) . ? O2 C14 1.271(9) . ? N1 C7 1.333(11) . ? N1 C11 1.348(11) . ? N2 C13 1.475(10) . ? C1 C6 1.395(13) . ? C1 C2 1.396(13) . ? C2 C3 1.391(13) . ? C3 C4 1.388(15) . ? C4 C5 1.357(14) . ? C5 C6 1.406(13) . ? C6 C7 1.501(12) . ? C7 C8 1.369(11) . ? C8 C9 1.354(14) . ? C9 C10 1.363(14) . ? C10 C11 1.376(13) . ? C12 C13 1.513(11) . ? C13 C14 1.532(10) . ? Au2 C15 2.020(8) . ? Au2 N3 2.094(7) . ? Au2 N4 2.128(7) . ? Au2 S2 2.261(2) . ? S2 C26 1.833(9) . ? O3 C28 1.193(9) . ? O4 C28 1.279(9) . ? N3 C25 1.333(11) . ? N3 C21 1.354(11) . ? N4 C27 1.538(10) . ? C15 C16 1.370(11) . ? C15 C20 1.379(12) . ? C16 C17 1.392(12) . ? C17 C18 1.376(14) . ? C18 C19 1.369(14) . ? C19 C20 1.406(11) . ? C20 C21 1.459(12) . ? C21 C22 1.395(12) . ? C22 C23 1.400(14) . ? C23 C24 1.356(15) . ? C24 C25 1.386(13) . ? C26 C27 1.513(11) . ? C27 C28 1.523(10) . ? Cl1 O6 1.406(7) . ? Cl1 O8 1.409(6) . ? Cl1 O7 1.434(6) . ? Cl1 O5 1.439(7) . ? 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 C1 Au1 N1 80.4(4) . . ? C1 Au1 N2 176.5(3) . . ? N1 Au1 N2 99.5(3) . . ? C1 Au1 S1 94.3(3) . . ? N1 Au1 S1 174.2(2) . . ? N2 Au1 S1 85.93(19) . . ? C12 S1 Au1 98.7(3) . . ? C7 N1 C11 119.2(7) . . ? C7 N1 Au1 115.9(5) . . ? C11 N1 Au1 124.6(6) . . ? C13 N2 Au1 112.9(5) . . ? C6 C1 C2 118.2(7) . . ? C6 C1 Au1 114.2(7) . . ? C2 C1 Au1 127.7(8) . . ? C3 C2 C1 119.9(9) . . ? C4 C3 C2 120.6(9) . . ? C5 C4 C3 120.9(8) . . ? C4 C5 C6 118.8(9) . . ? C1 C6 C5 121.6(8) . . ? C1 C6 C7 116.4(8) . . ? C5 C6 C7 122.0(9) . . ? N1 C7 C8 121.2(8) . . ? N1 C7 C6 112.9(7) . . ? C8 C7 C6 125.9(9) . . ? C9 C8 C7 119.9(9) . . ? C8 C9 C10 119.4(8) . . ? C9 C10 C11 119.3(10) . . ? N1 C11 C10 120.9(10) . . ? C13 C12 S1 110.4(5) . . ? N2 C13 C12 110.3(6) . . ? N2 C13 C14 109.1(6) . . ? C12 C13 C14 113.2(6) . . ? O1 C14 O2 126.5(7) . . ? O1 C14 C13 117.9(6) . . ? O2 C14 C13 115.4(7) . . ? C15 Au2 N3 81.2(3) . . ? C15 Au2 N4 177.8(3) . . ? N3 Au2 N4 97.4(3) . . ? C15 Au2 S2 93.7(2) . . ? N3 Au2 S2 174.9(2) . . ? N4 Au2 S2 87.7(2) . . ? C26 S2 Au2 97.1(3) . . ? C25 N3 C21 121.7(8) . . ? C25 N3 Au2 124.8(6) . . ? C21 N3 Au2 113.1(6) . . ? C27 N4 Au2 111.3(5) . . ? C16 C15 C20 120.7(8) . . ? C16 C15 Au2 126.7(7) . . ? C20 C15 Au2 112.6(6) . . ? C15 C16 C17 119.9(9) . . ? C18 C17 C16 120.4(9) . . ? C19 C18 C17 119.5(9) . . ? C18 C19 C20 120.9(9) . . ? C15 C20 C19 118.7(8) . . ? C15 C20 C21 118.2(7) . . ? C19 C20 C21 123.1(8) . . ? N3 C21 C22 119.4(9) . . ? N3 C21 C20 114.7(7) . . ? C22 C21 C20 125.9(9) . . ? C21 C22 C23 118.2(10) . . ? C24 C23 C22 121.0(9) . . ? C23 C24 C25 118.6(10) . . ? N3 C25 C24 120.9(10) . . ? C27 C26 S2 110.3(6) . . ? C26 C27 C28 115.2(7) . . ? C26 C27 N4 108.1(6) . . ? C28 C27 N4 108.1(6) . . ? O3 C28 O4 125.9(7) . . ? O3 C28 C27 120.9(7) . . ? O4 C28 C27 113.2(7) . . ? O6 Cl1 O8 110.9(5) . . ? O6 Cl1 O7 110.3(5) . . ? O8 Cl1 O7 109.8(4) . . ? O6 Cl1 O5 110.1(6) . . ? O8 Cl1 O5 109.9(5) . . ? O7 Cl1 O5 105.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Au1 S1 C12 -163.5(3) . . . . ? N1 Au1 S1 C12 172.3(19) . . . . ? N2 Au1 S1 C12 13.1(3) . . . . ? C1 Au1 N1 C7 -2.1(6) . . . . ? N2 Au1 N1 C7 -178.6(5) . . . . ? S1 Au1 N1 C7 22(2) . . . . ? C1 Au1 N1 C11 -176.5(8) . . . . ? N2 Au1 N1 C11 7.1(8) . . . . ? S1 Au1 N1 C11 -151.9(16) . . . . ? C1 Au1 N2 C13 107(7) . . . . ? N1 Au1 N2 C13 -165.5(5) . . . . ? S1 Au1 N2 C13 12.4(5) . . . . ? N1 Au1 C1 C6 -1.0(6) . . . . ? N2 Au1 C1 C6 87(7) . . . . ? S1 Au1 C1 C6 -178.6(6) . . . . ? N1 Au1 C1 C2 -179.4(7) . . . . ? N2 Au1 C1 C2 -91(7) . . . . ? S1 Au1 C1 C2 3.0(7) . . . . ? C6 C1 C2 C3 -1.2(12) . . . . ? Au1 C1 C2 C3 177.1(6) . . . . ? C1 C2 C3 C4 0.0(14) . . . . ? C2 C3 C4 C5 0.3(14) . . . . ? C3 C4 C5 C6 0.7(13) . . . . ? C2 C1 C6 C5 2.2(12) . . . . ? Au1 C1 C6 C5 -176.3(6) . . . . ? C2 C1 C6 C7 -177.7(7) . . . . ? Au1 C1 C6 C7 3.7(9) . . . . ? C4 C5 C6 C1 -2.0(13) . . . . ? C4 C5 C6 C7 178.0(8) . . . . ? C11 N1 C7 C8 -1.0(12) . . . . ? Au1 N1 C7 C8 -175.7(6) . . . . ? C11 N1 C7 C6 179.2(8) . . . . ? Au1 N1 C7 C6 4.5(8) . . . . ? C1 C6 C7 N1 -5.5(10) . . . . ? C5 C6 C7 N1 174.6(8) . . . . ? C1 C6 C7 C8 174.7(8) . . . . ? C5 C6 C7 C8 -5.2(13) . . . . ? N1 C7 C8 C9 0.7(13) . . . . ? C6 C7 C8 C9 -179.5(8) . . . . ? C7 C8 C9 C10 0.8(14) . . . . ? C8 C9 C10 C11 -1.8(15) . . . . ? C7 N1 C11 C10 -0.1(14) . . . . ? Au1 N1 C11 C10 174.1(7) . . . . ? C9 C10 C11 N1 1.5(16) . . . . ? Au1 S1 C12 C13 -38.2(6) . . . . ? Au1 N2 C13 C12 -40.1(7) . . . . ? Au1 N2 C13 C14 84.8(6) . . . . ? S1 C12 C13 N2 53.0(7) . . . . ? S1 C12 C13 C14 -69.6(7) . . . . ? N2 C13 C14 O1 26.4(9) . . . . ? C12 C13 C14 O1 149.6(7) . . . . ? N2 C13 C14 O2 -157.7(7) . . . . ? C12 C13 C14 O2 -34.6(9) . . . . ? C15 Au2 S2 C26 -167.7(3) . . . . ? N3 Au2 S2 C26 -167(2) . . . . ? N4 Au2 S2 C26 14.0(3) . . . . ? C15 Au2 N3 C25 173.1(7) . . . . ? N4 Au2 N3 C25 -8.7(7) . . . . ? S2 Au2 N3 C25 171.9(17) . . . . ? C15 Au2 N3 C21 0.9(6) . . . . ? N4 Au2 N3 C21 179.1(5) . . . . ? S2 Au2 N3 C21 0(2) . . . . ? C15 Au2 N4 C27 -115(8) . . . . ? N3 Au2 N4 C27 -167.1(5) . . . . ? S2 Au2 N4 C27 12.9(5) . . . . ? N3 Au2 C15 C16 -179.0(7) . . . . ? N4 Au2 C15 C16 129(8) . . . . ? S2 Au2 C15 C16 0.9(7) . . . . ? N3 Au2 C15 C20 1.8(5) . . . . ? N4 Au2 C15 C20 -51(8) . . . . ? S2 Au2 C15 C20 -178.3(5) . . . . ? C20 C15 C16 C17 1.8(12) . . . . ? Au2 C15 C16 C17 -177.4(6) . . . . ? C15 C16 C17 C18 -1.4(13) . . . . ? C16 C17 C18 C19 1.0(15) . . . . ? C17 C18 C19 C20 -1.0(15) . . . . ? C16 C15 C20 C19 -1.7(12) . . . . ? Au2 C15 C20 C19 177.5(6) . . . . ? C16 C15 C20 C21 176.6(7) . . . . ? Au2 C15 C20 C21 -4.2(9) . . . . ? C18 C19 C20 C15 1.3(13) . . . . ? C18 C19 C20 C21 -176.9(8) . . . . ? C25 N3 C21 C22 4.5(12) . . . . ? Au2 N3 C21 C22 177.0(6) . . . . ? C25 N3 C21 C20 -175.7(7) . . . . ? Au2 N3 C21 C20 -3.2(8) . . . . ? C15 C20 C21 N3 5.0(10) . . . . ? C19 C20 C21 N3 -176.8(7) . . . . ? C15 C20 C21 C22 -175.2(8) . . . . ? C19 C20 C21 C22 3.0(13) . . . . ? N3 C21 C22 C23 -1.4(12) . . . . ? C20 C21 C22 C23 178.9(8) . . . . ? C21 C22 C23 C24 -1.5(14) . . . . ? C22 C23 C24 C25 1.3(14) . . . . ? C21 N3 C25 C24 -4.8(12) . . . . ? Au2 N3 C25 C24 -176.3(6) . . . . ? C23 C24 C25 N3 1.8(13) . . . . ? Au2 S2 C26 C27 -41.9(6) . . . . ? S2 C26 C27 C28 -63.8(8) . . . . ? S2 C26 C27 N4 57.1(7) . . . . ? Au2 N4 C27 C26 -42.3(7) . . . . ? Au2 N4 C27 C28 82.9(6) . . . . ? C26 C27 C28 O3 136.8(9) . . . . ? N4 C27 C28 O3 15.9(11) . . . . ? C26 C27 C28 O4 -45.8(10) . . . . ? N4 C27 C28 O4 -166.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 29.46 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 1.068 _refine_diff_density_min -2.130 _refine_diff_density_rms 0.195 data_jdr20 _database_code_CSD 214285 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H15 Au N O3.50 S' _chemical_formula_weight 530.34 _chemical_melting_point ? _chemical_compound_source 'see text' 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.013(4) _cell_length_b 20.133(4) _cell_length_c 13.332(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3492.7(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 29.32 _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.017 _exptl_crystal_density_method ? _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 8.562 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.2917 _exptl_absorpt_correction_T_max 0.5413 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens SMART CCD System' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20261 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 29.32 _reflns_number_total 4431 _reflns_number_observed 3281 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _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^)+(0.0359P)^2^+16.5456P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4431 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.251 _refine_ls_restrained_S_all 1.251 _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 Au1 Au 0.39226(2) 0.924371(13) 0.12395(2) 0.03141(11) Uani 1 1 d . . . N1 N 0.3596(5) 1.0251(3) 0.1288(5) 0.0347(13) Uani 1 1 d . . . C1 C 0.2649(7) 1.0496(5) 0.1301(6) 0.046(2) Uani 1 1 d . . . H1 H 0.2089 1.0209 0.1286 0.055 Uiso 1 1 calc R . . C2 C 0.2491(8) 1.1177(5) 0.1338(7) 0.056(2) Uani 1 1 d . . . H2 H 0.1828 1.1348 0.1351 0.068 Uiso 1 1 calc R . . C3 C 0.3330(9) 1.1597(5) 0.1354(7) 0.057(2) Uani 1 1 d . . . H3 H 0.3238 1.2055 0.1377 0.069 Uiso 1 1 calc R . . C4 C 0.4313(8) 1.1329(4) 0.1337(6) 0.049(2) Uani 1 1 d . . . H4 H 0.4884 1.1606 0.1354 0.059 Uiso 1 1 calc R . . C5 C 0.4441(6) 1.0642(4) 0.1294(6) 0.0358(17) Uani 1 1 d . . . C6 C 0.5415(6) 1.0289(4) 0.1264(6) 0.0344(15) Uani 1 1 d . . . C7 C 0.6372(7) 1.0604(4) 0.1261(6) 0.0415(18) Uani 1 1 d . . . H7 H 0.6408 1.1065 0.1282 0.050 Uiso 1 1 calc R . . C8 C 0.7270(7) 1.0231(5) 0.1226(6) 0.049(2) Uani 1 1 d . . . H8 H 0.7905 1.0443 0.1214 0.059 Uiso 1 1 calc R . . C9 C 0.7221(7) 0.9550(5) 0.1207(7) 0.047(2) Uani 1 1 d . . . H9 H 0.7824 0.9302 0.1205 0.056 Uiso 1 1 calc R . . C10 C 0.6272(7) 0.9228(4) 0.1191(6) 0.0414(18) Uani 1 1 d . . . H10 H 0.6249 0.8767 0.1158 0.050 Uiso 1 1 calc R . . C11 C 0.5363(6) 0.9587(4) 0.1224(6) 0.0311(15) Uani 1 1 d . . . S1 S 0.43393(18) 0.81468(10) 0.11633(18) 0.0444(5) Uani 1 1 d . . . C12 C 0.3481(6) 0.7891(3) 0.0198(6) 0.0348(17) Uani 1 1 d . . . C13 C 0.3888(7) 0.7451(4) -0.0511(7) 0.046(2) Uani 1 1 d . . . H13 H 0.4559 0.7300 -0.0443 0.055 Uiso 1 1 calc R . . C14 C 0.3297(9) 0.7242(5) -0.1310(8) 0.062(3) Uani 1 1 d . . . H14 H 0.3574 0.6946 -0.1772 0.075 Uiso 1 1 calc R . . C15 C 0.2309(9) 0.7460(5) -0.1434(7) 0.056(3) Uani 1 1 d . . . H15 H 0.1925 0.7334 -0.1990 0.067 Uiso 1 1 calc R . . C16 C 0.1891(7) 0.7881(4) -0.0699(7) 0.048(2) Uani 1 1 d . . . H16 H 0.1211 0.8018 -0.0758 0.058 Uiso 1 1 calc R . . C17 C 0.2465(6) 0.8096(4) 0.0107(6) 0.0362(17) Uani 1 1 d . . . C18 C 0.1911(6) 0.8527(4) 0.0844(6) 0.0384(18) Uani 1 1 d . . . O1 O 0.2390(4) 0.9000(3) 0.1323(5) 0.0485(15) Uani 1 1 d . . . O2 O 0.0993(5) 0.8419(4) 0.1009(6) 0.0612(19) Uani 1 1 d . . . O1S O 0.0000 0.919(2) 0.2500 0.094(13) Uiso 0.50 2 d SP . . O2S O -0.033(3) 0.9204(18) 0.224(2) 0.052(7) Uiso 0.25 1 d P . . O3S O -0.007(3) 0.9238(19) -0.069(3) 0.070(11) Uiso 0.25 1 d P . . O4S O -0.029(3) 0.942(2) -0.014(3) 0.063(11) Uiso 0.25 1 d P . . O5S O -0.003(5) 0.942(3) -0.038(5) 0.089(19) Uiso 0.25 1 d P . . O6S O 0.0000 1.057(3) 0.2500 0.066(19) Uiso 0.25 2 d SP . . O7S O -0.010(3) 1.055(3) 0.215(4) 0.032(10) Uiso 0.13 1 d P . . 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 Au1 0.03598(17) 0.03011(16) 0.02816(15) -0.00276(12) 0.00132(13) -0.00250(12) N1 0.043(4) 0.032(3) 0.028(3) 0.003(3) 0.005(3) 0.006(3) C1 0.045(5) 0.047(5) 0.046(5) -0.007(4) 0.005(4) 0.007(4) C2 0.064(6) 0.050(5) 0.056(5) -0.011(5) -0.013(5) 0.019(5) C3 0.078(7) 0.032(4) 0.062(6) 0.001(4) -0.013(6) 0.013(5) C4 0.073(6) 0.033(4) 0.041(5) 0.010(4) -0.001(5) 0.001(4) C5 0.044(5) 0.036(4) 0.027(3) -0.004(3) 0.011(4) -0.003(3) C6 0.043(4) 0.039(4) 0.022(3) -0.001(3) 0.004(4) -0.005(3) C7 0.051(5) 0.038(4) 0.036(4) 0.001(4) 0.003(4) -0.012(3) C8 0.041(5) 0.068(6) 0.040(4) 0.004(5) -0.002(4) -0.012(4) C9 0.034(4) 0.060(6) 0.046(5) 0.001(5) -0.001(4) 0.003(4) C10 0.048(5) 0.045(5) 0.031(4) -0.003(4) -0.003(4) 0.000(4) C11 0.033(4) 0.038(4) 0.023(3) 0.003(3) 0.003(3) -0.004(3) S1 0.0485(12) 0.0325(10) 0.0522(12) 0.0013(10) -0.0054(11) 0.0012(9) C12 0.044(5) 0.019(3) 0.042(4) 0.000(3) 0.005(4) -0.005(3) C13 0.061(6) 0.020(4) 0.056(5) -0.003(3) 0.012(4) -0.007(4) C14 0.089(8) 0.038(5) 0.060(6) -0.022(5) 0.018(6) -0.018(5) C15 0.078(7) 0.050(6) 0.040(5) -0.010(4) 0.001(5) -0.021(5) C16 0.051(6) 0.044(5) 0.050(5) -0.001(4) 0.002(4) -0.010(4) C17 0.043(5) 0.028(4) 0.038(4) 0.004(3) 0.006(3) -0.011(3) C18 0.038(5) 0.035(4) 0.042(4) 0.005(3) 0.002(3) -0.001(3) O1 0.038(3) 0.051(3) 0.057(4) -0.022(3) 0.007(3) -0.005(3) O2 0.044(4) 0.062(4) 0.078(5) -0.024(4) 0.013(3) -0.017(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 Au1 C11 1.998(7) . ? Au1 O1 2.057(6) . ? Au1 N1 2.074(6) . ? Au1 S1 2.276(2) . ? N1 C1 1.327(11) . ? N1 C5 1.351(10) . ? C1 C2 1.387(13) . ? C2 C3 1.382(15) . ? C3 C4 1.388(15) . ? C4 C5 1.394(11) . ? C5 C6 1.454(11) . ? C6 C7 1.398(11) . ? C6 C11 1.416(11) . ? C7 C8 1.390(13) . ? C8 C9 1.372(13) . ? C9 C10 1.394(12) . ? C10 C11 1.387(11) . ? S1 C12 1.780(8) . ? C12 C17 1.391(11) . ? C12 C13 1.398(11) . ? C13 C14 1.380(14) . ? C14 C15 1.368(15) . ? C15 C16 1.405(13) . ? C16 C17 1.378(11) . ? C17 C18 1.495(11) . ? C18 O2 1.234(10) . ? C18 O1 1.305(10) . ? O1S O2S 0.55(4) 3 ? O1S O2S 0.55(4) . ? O2S O2S 1.11(8) 3 ? O3S O5S 0.56(7) . ? O3S O4S 0.87(6) . ? O6S O7S 0.49(6) 3 ? O7S O7S 0.98(12) 3 ? 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 C11 Au1 O1 173.1(3) . . ? C11 Au1 N1 81.6(3) . . ? O1 Au1 N1 91.9(3) . . ? C11 Au1 S1 96.4(2) . . ? O1 Au1 S1 90.11(18) . . ? N1 Au1 S1 177.88(19) . . ? C1 N1 C5 122.7(7) . . ? C1 N1 Au1 123.6(6) . . ? C5 N1 Au1 113.8(5) . . ? N1 C1 C2 120.3(9) . . ? C3 C2 C1 119.3(9) . . ? C2 C3 C4 119.2(8) . . ? C3 C4 C5 119.8(9) . . ? N1 C5 C4 118.7(8) . . ? N1 C5 C6 115.1(7) . . ? C4 C5 C6 126.2(8) . . ? C7 C6 C11 119.7(7) . . ? C7 C6 C5 123.7(7) . . ? C11 C6 C5 116.6(7) . . ? C8 C7 C6 120.2(8) . . ? C9 C8 C7 120.1(8) . . ? C8 C9 C10 120.4(8) . . ? C11 C10 C9 120.8(8) . . ? C10 C11 C6 118.7(7) . . ? C10 C11 Au1 128.4(6) . . ? C6 C11 Au1 112.9(5) . . ? C12 S1 Au1 99.4(3) . . ? C17 C12 C13 119.2(8) . . ? C17 C12 S1 125.0(6) . . ? C13 C12 S1 115.7(7) . . ? C14 C13 C12 120.3(9) . . ? C15 C14 C13 121.2(9) . . ? C14 C15 C16 118.3(9) . . ? C17 C16 C15 121.5(9) . . ? C16 C17 C12 119.4(8) . . ? C16 C17 C18 115.7(8) . . ? C12 C17 C18 124.9(7) . . ? O2 C18 O1 120.2(8) . . ? O2 C18 C17 118.8(8) . . ? O1 C18 C17 121.0(7) . . ? C18 O1 Au1 127.6(5) . . ? O2S O1S O2S 175(10) 3 . ? O1S O2S O2S 2(7) . 3 ? O5S O3S O4S 29(8) . . ? 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 C11 Au1 N1 C1 178.8(7) . . . . ? O1 Au1 N1 C1 -3.4(7) . . . . ? S1 Au1 N1 C1 159(5) . . . . ? C11 Au1 N1 C5 -0.4(5) . . . . ? O1 Au1 N1 C5 177.3(5) . . . . ? S1 Au1 N1 C5 -20(5) . . . . ? C5 N1 C1 C2 -1.0(13) . . . . ? Au1 N1 C1 C2 179.8(6) . . . . ? N1 C1 C2 C3 0.4(14) . . . . ? C1 C2 C3 C4 -0.2(14) . . . . ? C2 C3 C4 C5 0.6(14) . . . . ? C1 N1 C5 C4 1.5(12) . . . . ? Au1 N1 C5 C4 -179.3(6) . . . . ? C1 N1 C5 C6 -179.2(7) . . . . ? Au1 N1 C5 C6 0.0(8) . . . . ? C3 C4 C5 N1 -1.2(12) . . . . ? C3 C4 C5 C6 179.6(8) . . . . ? N1 C5 C6 C7 179.8(7) . . . . ? C4 C5 C6 C7 -1.0(13) . . . . ? N1 C5 C6 C11 0.6(10) . . . . ? C4 C5 C6 C11 179.8(7) . . . . ? C11 C6 C7 C8 -0.5(12) . . . . ? C5 C6 C7 C8 -179.6(8) . . . . ? C6 C7 C8 C9 -0.9(13) . . . . ? C7 C8 C9 C10 2.1(13) . . . . ? C8 C9 C10 C11 -2.0(13) . . . . ? C9 C10 C11 C6 0.6(11) . . . . ? C9 C10 C11 Au1 -178.6(6) . . . . ? C7 C6 C11 C10 0.6(11) . . . . ? C5 C6 C11 C10 179.8(7) . . . . ? C7 C6 C11 Au1 179.9(6) . . . . ? C5 C6 C11 Au1 -0.9(8) . . . . ? O1 Au1 C11 C10 160(2) . . . . ? N1 Au1 C11 C10 179.9(8) . . . . ? S1 Au1 C11 C10 -0.8(7) . . . . ? O1 Au1 C11 C6 -19(3) . . . . ? N1 Au1 C11 C6 0.7(5) . . . . ? S1 Au1 C11 C6 180.0(5) . . . . ? C11 Au1 S1 C12 -132.6(3) . . . . ? O1 Au1 S1 C12 49.7(3) . . . . ? N1 Au1 S1 C12 -113(5) . . . . ? Au1 S1 C12 C17 -41.6(7) . . . . ? Au1 S1 C12 C13 138.2(5) . . . . ? C17 C12 C13 C14 2.1(12) . . . . ? S1 C12 C13 C14 -177.7(7) . . . . ? C12 C13 C14 C15 0.6(14) . . . . ? C13 C14 C15 C16 -3.0(14) . . . . ? C14 C15 C16 C17 2.8(14) . . . . ? C15 C16 C17 C12 -0.1(12) . . . . ? C15 C16 C17 C18 -178.4(8) . . . . ? C13 C12 C17 C16 -2.3(11) . . . . ? S1 C12 C17 C16 177.5(6) . . . . ? C13 C12 C17 C18 175.8(7) . . . . ? S1 C12 C17 C18 -4.4(11) . . . . ? C16 C17 C18 O2 34.8(11) . . . . ? C12 C17 C18 O2 -143.4(8) . . . . ? C16 C17 C18 O1 -146.7(8) . . . . ? C12 C17 C18 O1 35.1(12) . . . . ? O2 C18 O1 Au1 176.4(6) . . . . ? C17 C18 O1 Au1 -2.1(11) . . . . ? C11 Au1 O1 C18 160(2) . . . . ? N1 Au1 O1 C18 140.6(7) . . . . ? S1 Au1 O1 C18 -38.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 29.32 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 2.545 _refine_diff_density_min -1.317 _refine_diff_density_rms 0.181 data_9982 _database_code_CSD 214286 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 Au N3 S2' _chemical_formula_weight 467.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Au Au -2.0133 8.8022 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.745(1) _cell_length_b 5.7751(3) _cell_length_c 9.2660(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.948(1) _cell_angle_gamma 90.00 _cell_volume 1361.5(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4682 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 29.49 _exptl_crystal_description 'rectangular rod, cut' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 11.098 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.3370 _exptl_absorpt_correction_T_max 0.6652 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _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 6286 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 29.49 _reflns_number_total 3302 _reflns_number_gt 2741 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, 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^)+(0.0204P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00051(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.082(16) _refine_ls_number_reflns 3302 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 Au1 Au 0.371779(11) 0.35509(12) 0.32603(3) 0.04152(12) Uani 1 1 d . . . S1 S 0.32641(14) 0.3283(11) 0.0711(3) 0.0729(11) Uani 1 1 d . . . S2 S 0.46816(14) 1.0257(6) 0.2588(6) 0.0904(12) Uani 1 1 d . . . N1 N 0.4038(2) 0.350(3) 0.5592(7) 0.0431(16) Uani 1 1 d . . . N2 N 0.3329(6) 0.757(2) -0.0573(12) 0.107(5) Uani 1 1 d . . . N3 N 0.4157(4) 0.6341(15) 0.3014(11) 0.063(2) Uani 1 1 d . . . C1 C 0.3320(3) 0.0823(14) 0.3701(11) 0.040(2) Uani 1 1 d . . . C2 C 0.2963(4) -0.0571(16) 0.2689(13) 0.050(2) Uani 1 1 d . . . H2 H 0.2862 -0.0242 0.1657 0.060 Uiso 1 1 calc R . . C3 C 0.2753(4) -0.2473(18) 0.3213(13) 0.052(3) Uani 1 1 d . . . H3 H 0.2511 -0.3414 0.2525 0.062 Uiso 1 1 calc R . . C4 C 0.2894(4) -0.2981(15) 0.4717(13) 0.052(3) Uani 1 1 d . . . H4 H 0.2746 -0.4258 0.5043 0.062 Uiso 1 1 calc R . . C5 C 0.3261(3) -0.160(3) 0.5789(9) 0.048(2) Uani 1 1 d . . . H5 H 0.3364 -0.1960 0.6817 0.057 Uiso 1 1 calc R . . C6 C 0.3466(3) 0.0329(14) 0.5244(10) 0.0368(19) Uani 1 1 d . . . C7 C 0.3838(4) 0.1860(16) 0.6273(11) 0.042(2) Uani 1 1 d . . . C8 C 0.3980(4) 0.1846(19) 0.7842(11) 0.052(2) Uani 1 1 d . . . H8 H 0.3843 0.0715 0.8328 0.063 Uiso 1 1 calc R . . C9 C 0.4317(4) 0.346(4) 0.8687(12) 0.069(3) Uani 1 1 d . . . H9 H 0.4415 0.3422 0.9741 0.083 Uiso 1 1 calc R . . C10 C 0.4516(4) 0.519(2) 0.7942(13) 0.059(3) Uani 1 1 d . . . H10 H 0.4743 0.6332 0.8486 0.071 Uiso 1 1 calc R . . C11 C 0.4366(4) 0.5140(19) 0.6394(14) 0.059(3) Uani 1 1 d . . . H11 H 0.4492 0.6267 0.5879 0.070 Uiso 1 1 calc R . . C12 C 0.3330(5) 0.5828(19) 0.0020(11) 0.062(3) Uani 1 1 d . . . C13 C 0.4361(4) 0.7983(19) 0.2794(14) 0.063(4) 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 Au1 0.04465(18) 0.04364(16) 0.03893(17) 0.0074(3) 0.01678(13) 0.0005(3) S1 0.099(2) 0.073(3) 0.0418(13) 0.0095(19) 0.0137(13) -0.014(2) S2 0.070(2) 0.0587(17) 0.151(4) 0.029(2) 0.047(2) -0.0021(15) N1 0.040(4) 0.046(3) 0.041(3) 0.004(7) 0.009(3) 0.021(7) N2 0.169(13) 0.104(9) 0.044(6) 0.012(5) 0.028(7) -0.015(8) N3 0.059(6) 0.054(5) 0.077(7) 0.014(5) 0.023(5) -0.008(4) C1 0.034(5) 0.032(4) 0.056(6) 0.005(4) 0.018(4) 0.008(3) C2 0.053(6) 0.053(5) 0.048(6) 0.002(4) 0.021(5) -0.002(4) C3 0.041(6) 0.058(5) 0.052(7) -0.004(5) 0.009(5) -0.005(4) C4 0.054(6) 0.035(4) 0.075(8) 0.010(4) 0.032(6) -0.001(4) C5 0.046(4) 0.059(6) 0.040(4) 0.015(7) 0.014(4) -0.021(7) C6 0.032(5) 0.040(4) 0.041(5) 0.006(4) 0.015(4) 0.006(4) C7 0.039(5) 0.047(5) 0.041(5) 0.001(4) 0.013(4) 0.002(4) C8 0.052(6) 0.066(6) 0.037(5) 0.013(5) 0.010(5) -0.001(5) C9 0.064(6) 0.090(7) 0.048(5) 0.025(11) 0.010(5) 0.016(12) C10 0.048(6) 0.068(6) 0.055(7) -0.001(5) 0.004(5) -0.014(5) C11 0.049(6) 0.055(6) 0.065(7) 0.014(5) 0.010(5) -0.003(5) C12 0.097(9) 0.063(6) 0.032(5) 0.010(5) 0.032(6) -0.004(6) C13 0.044(5) 0.077(13) 0.071(7) 0.014(6) 0.021(5) 0.019(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.012(8) . ? Au1 N3 2.048(9) . ? Au1 N1 2.064(6) . ? Au1 S1 2.304(3) . ? S1 C12 1.634(12) . ? S2 C13 1.612(12) . ? N1 C7 1.336(16) . ? N1 C11 1.350(17) . ? N2 C12 1.146(14) . ? N3 C13 1.142(13) . ? C1 C2 1.374(14) . ? C1 C6 1.391(13) . ? C2 C3 1.388(12) . ? C3 C4 1.358(15) . ? C4 C5 1.408(15) . ? C5 C6 1.404(15) . ? C6 C7 1.448(12) . ? C7 C8 1.384(13) . ? C8 C9 1.37(2) . ? C9 C10 1.41(2) . ? C10 C11 1.365(16) . ? 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 C1 Au1 N3 174.9(4) . . ? C1 Au1 N1 81.4(5) . . ? N3 Au1 N1 93.5(5) . . ? C1 Au1 S1 90.6(3) . . ? N3 Au1 S1 94.4(3) . . ? N1 Au1 S1 171.6(4) . . ? C12 S1 Au1 104.8(5) . . ? C7 N1 C11 121.6(8) . . ? C7 N1 Au1 114.1(8) . . ? C11 N1 Au1 123.7(10) . . ? C13 N3 Au1 173.7(9) . . ? C2 C1 C6 119.8(8) . . ? C2 C1 Au1 128.4(8) . . ? C6 C1 Au1 111.8(6) . . ? C1 C2 C3 119.8(10) . . ? C4 C3 C2 121.0(10) . . ? C3 C4 C5 121.0(9) . . ? C6 C5 C4 117.4(8) . . ? C1 C6 C5 121.0(8) . . ? C1 C6 C7 118.0(8) . . ? C5 C6 C7 120.9(8) . . ? N1 C7 C8 118.7(9) . . ? N1 C7 C6 114.5(8) . . ? C8 C7 C6 126.8(9) . . ? C9 C8 C7 121.2(10) . . ? C8 C9 C10 119.1(9) . . ? C11 C10 C9 117.7(11) . . ? N1 C11 C10 121.7(10) . . ? N2 C12 S1 173.1(14) . . ? N3 C13 S2 175.9(12) . . ? 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 C1 Au1 S1 C12 160.0(5) . . . . ? N3 Au1 S1 C12 -20.0(6) . . . . ? N1 Au1 S1 C12 142(3) . . . . ? C1 Au1 N1 C7 -1.9(7) . . . . ? N3 Au1 N1 C7 178.3(8) . . . . ? S1 Au1 N1 C7 16(4) . . . . ? C1 Au1 N1 C11 -173.3(9) . . . . ? N3 Au1 N1 C11 6.9(9) . . . . ? S1 Au1 N1 C11 -155(3) . . . . ? C1 Au1 N3 C13 -134(8) . . . . ? N1 Au1 N3 C13 -131(9) . . . . ? S1 Au1 N3 C13 46(9) . . . . ? N3 Au1 C1 C2 -175(4) . . . . ? N1 Au1 C1 C2 -177.7(9) . . . . ? S1 Au1 C1 C2 4.8(8) . . . . ? N3 Au1 C1 C6 1(4) . . . . ? N1 Au1 C1 C6 -1.1(6) . . . . ? S1 Au1 C1 C6 -178.5(6) . . . . ? C6 C1 C2 C3 -0.5(13) . . . . ? Au1 C1 C2 C3 175.9(7) . . . . ? C1 C2 C3 C4 0.1(14) . . . . ? C2 C3 C4 C5 -0.5(16) . . . . ? C3 C4 C5 C6 1.2(17) . . . . ? C2 C1 C6 C5 1.2(14) . . . . ? Au1 C1 C6 C5 -175.8(8) . . . . ? C2 C1 C6 C7 -179.2(8) . . . . ? Au1 C1 C6 C7 3.9(9) . . . . ? C4 C5 C6 C1 -1.5(16) . . . . ? C4 C5 C6 C7 178.9(9) . . . . ? C11 N1 C7 C8 -0.9(15) . . . . ? Au1 N1 C7 C8 -172.5(7) . . . . ? C11 N1 C7 C6 176.0(9) . . . . ? Au1 N1 C7 C6 4.4(11) . . . . ? C1 C6 C7 N1 -5.6(12) . . . . ? C5 C6 C7 N1 174.0(10) . . . . ? C1 C6 C7 C8 171.0(9) . . . . ? C5 C6 C7 C8 -9.3(15) . . . . ? N1 C7 C8 C9 -0.1(16) . . . . ? C6 C7 C8 C9 -176.6(11) . . . . ? C7 C8 C9 C10 1(2) . . . . ? C8 C9 C10 C11 -1(2) . . . . ? C7 N1 C11 C10 1.0(17) . . . . ? Au1 N1 C11 C10 171.8(8) . . . . ? C9 C10 C11 N1 0.0(18) . . . . ? Au1 S1 C12 N2 -153(10) . . . . ? Au1 N3 C13 S2 161(10) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 29.49 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 1.275 _refine_diff_density_min -1.220 _refine_diff_density_rms 0.159