Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Edward R. T. Tiekink' _publ_contact_author_address ; Department of Chemistry The University of Texas at San Antonio One UTSA Circle San Antonio Texas 78249-0698 UNITED STATES OF AMERICA ; _publ_contact_author_email EDWARD.TIEKINK@UTSA.EDU _publ_section_title ; Electronic and steric control over Au...Au, C-H...O and C-H...pi interactions in the crystal structures of mononuclear triarylphosphinegold(I) carbonimidothioates: R3PAu[SC(OMe)=NR'] for R = Ph, o-tol, m-tol or p-tol, and R' = Ph, o-tol, m-tol, p-tol or C6H4NO2-4 ; loop_ _publ_author_name 'Edward R. T. Tiekink' 'Soo Yei Ho.' 'Fong Sheen Kuan.' 'Primjira P. Tadbuppa' # Attachment 'ptolPh.CIF' data_(p-tol)3PAu(SC(OMe)=NC6H5) _database_code_depnum_ccdc_archive 'CCDC 666589' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H29 Au N O P S' _chemical_formula_sum 'C29 H29 Au N O P S' _chemical_formula_weight 667.53 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 19.0501(10) _cell_length_b 14.5809(8) _cell_length_c 19.5329(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5425.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6380 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 24.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2624 _exptl_absorpt_coefficient_mu 5.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.586 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 43977 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 30.1 _reflns_number_total 7940 _reflns_number_gt 5380 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0365P)^2^] 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 7940 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.063 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.083 _refine_ls_wR_factor_gt 0.072 _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_restrained_S_all 1.00 _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 Au Au -0.058544(7) -0.072585(10) -0.164906(7) 0.03575(5) Uani 1 1 d . . . S1 S -0.13886(5) -0.11644(7) -0.08303(5) 0.0421(2) Uani 1 1 d . . . P1 P 0.00500(5) -0.01943(7) -0.25443(5) 0.0360(2) Uani 1 1 d . . . O1 O -0.16322(16) -0.2716(2) -0.02956(15) 0.0578(8) Uani 1 1 d . . . N1 N -0.04609(19) -0.2536(2) -0.04454(18) 0.0510(9) Uani 1 1 d . . . C1 C -0.1075(2) -0.2214(3) -0.05048(19) 0.0452(9) Uani 1 1 d . . . C2 C 0.0139(2) -0.2022(3) -0.0608(2) 0.0448(9) Uani 1 1 d . . . C3 C 0.0516(2) -0.2218(3) -0.1190(2) 0.0421(9) Uani 1 1 d . . . H3 H 0.0348 -0.2662 -0.1498 0.051 Uiso 1 1 calc R . . C4 C 0.1139(2) -0.1771(3) -0.1327(2) 0.0506(10) Uani 1 1 d . . . H4 H 0.1389 -0.1914 -0.1728 0.061 Uiso 1 1 calc R . . C5 C 0.1396(2) -0.1125(3) -0.0889(3) 0.0609(12) Uani 1 1 d . . . H5 H 0.1827 -0.0835 -0.0979 0.073 Uiso 1 1 calc R . . C6 C 0.1020(3) -0.0907(3) -0.0317(3) 0.0676(15) Uani 1 1 d . . . H6 H 0.1184 -0.0448 -0.0019 0.081 Uiso 1 1 calc R . . C7 C 0.0399(3) -0.1356(4) -0.0173(2) 0.0609(13) Uani 1 1 d . . . H7 H 0.0150 -0.1206 0.0227 0.073 Uiso 1 1 calc R . . C8 C -0.1478(3) -0.3615(3) -0.0026(3) 0.0792(17) Uani 1 1 d . . . H8A H -0.1912 -0.3916 0.0105 0.119 Uiso 1 1 calc R . . H8B H -0.1177 -0.3557 0.0373 0.119 Uiso 1 1 calc R . . H8C H -0.1241 -0.3977 -0.0373 0.119 Uiso 1 1 calc R . . C9 C -0.05236(19) 0.0191(3) -0.32286(18) 0.0371(8) Uani 1 1 d . . . C10 C -0.0302(2) 0.0249(3) -0.39052(19) 0.0434(9) Uani 1 1 d . . . H10 H 0.0152 0.0053 -0.4025 0.052 Uiso 1 1 calc R . . C11 C -0.0744(2) 0.0593(3) -0.4401(2) 0.0499(11) Uani 1 1 d . . . H11 H -0.0583 0.0638 -0.4855 0.060 Uiso 1 1 calc R . . C12 C -0.1419(3) 0.0873(3) -0.4245(2) 0.0530(11) Uani 1 1 d . . . C13 C -0.1638(2) 0.0809(3) -0.3580(2) 0.0504(11) Uani 1 1 d . . . H13 H -0.2096 0.0996 -0.3467 0.061 Uiso 1 1 calc R . . C14 C -0.1205(2) 0.0476(3) -0.3072(2) 0.0443(9) Uani 1 1 d . . . H14 H -0.1368 0.0440 -0.2619 0.053 Uiso 1 1 calc R . . C15 C 0.06210(19) -0.1048(3) -0.29308(19) 0.0373(8) Uani 1 1 d . . . C16 C 0.1331(2) -0.0899(3) -0.3057(2) 0.0431(9) Uani 1 1 d . . . H16 H 0.1530 -0.0322 -0.2967 0.052 Uiso 1 1 calc R . . C17 C 0.1745(2) -0.1598(3) -0.33147(19) 0.0458(9) Uani 1 1 d . . . H17 H 0.2222 -0.1485 -0.3404 0.055 Uiso 1 1 calc R . . C18 C 0.1471(2) -0.2458(3) -0.34437(19) 0.0457(10) Uani 1 1 d . . . C19 C 0.0761(2) -0.2620(3) -0.3321(2) 0.0510(11) Uani 1 1 d . . . H19 H 0.0565 -0.3201 -0.3402 0.061 Uiso 1 1 calc R . . C20 C 0.0344(2) -0.1902(3) -0.3073(2) 0.0482(10) Uani 1 1 d . . . H20 H -0.0138 -0.2005 -0.3002 0.058 Uiso 1 1 calc R . . C21 C 0.06100(18) 0.0765(2) -0.23333(19) 0.0358(8) Uani 1 1 d . . . C22 C 0.0883(2) 0.1358(3) -0.28230(19) 0.0393(8) Uani 1 1 d . . . H22 H 0.0762 0.1277 -0.3286 0.047 Uiso 1 1 calc R . . C23 C 0.13273(19) 0.2063(3) -0.2640(2) 0.0416(9) Uani 1 1 d . . . H23 H 0.1507 0.2452 -0.2981 0.050 Uiso 1 1 calc R . . C24 C 0.15144(19) 0.2208(3) -0.1965(2) 0.0438(9) Uani 1 1 d . . . C25 C 0.1248(2) 0.1604(3) -0.1474(2) 0.0458(10) Uani 1 1 d . . . H25 H 0.1375 0.1677 -0.1012 0.055 Uiso 1 1 calc R . . C26 C 0.0802(2) 0.0903(3) -0.16579(19) 0.0404(9) Uani 1 1 d . . . H26 H 0.0625 0.0510 -0.1318 0.048 Uiso 1 1 calc R . . C27 C -0.1887(3) 0.1282(4) -0.4792(3) 0.0815(17) Uani 1 1 d . . . H27A H -0.1714 0.1105 -0.5241 0.122 Uiso 1 1 calc R . . H27B H -0.1883 0.1945 -0.4754 0.122 Uiso 1 1 calc R . . H27C H -0.2362 0.1057 -0.4734 0.122 Uiso 1 1 calc R . . C28 C 0.1929(2) -0.3226(3) -0.3708(3) 0.0642(13) Uani 1 1 d . . . H28A H 0.2175 -0.3023 -0.4116 0.096 Uiso 1 1 calc R . . H28B H 0.1639 -0.3752 -0.3819 0.096 Uiso 1 1 calc R . . H28C H 0.2267 -0.3396 -0.3359 0.096 Uiso 1 1 calc R . . C29 C 0.1987(3) 0.2997(3) -0.1770(2) 0.0633(13) Uani 1 1 d . . . H29A H 0.2316 0.3114 -0.2138 0.095 Uiso 1 1 calc R . . H29B H 0.2242 0.2843 -0.1356 0.095 Uiso 1 1 calc R . . H29C H 0.1704 0.3540 -0.1690 0.095 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 Au 0.03243(8) 0.04076(9) 0.03405(8) 0.00213(6) 0.00241(6) 0.00011(6) S1 0.0381(5) 0.0454(6) 0.0427(5) 0.0008(4) 0.0096(4) 0.0020(4) P1 0.0302(5) 0.0429(6) 0.0348(5) 0.0032(4) 0.0003(4) 0.0003(4) O1 0.0562(19) 0.0540(19) 0.0631(19) 0.0110(14) 0.0194(16) -0.0055(15) N1 0.052(2) 0.055(2) 0.046(2) 0.0128(16) 0.0111(17) 0.0074(17) C1 0.052(3) 0.051(2) 0.032(2) 0.0015(17) 0.0097(18) 0.000(2) C2 0.045(2) 0.048(2) 0.042(2) 0.0060(18) -0.0043(19) 0.0085(19) C3 0.038(2) 0.045(2) 0.044(2) 0.0006(17) -0.0038(18) 0.0047(17) C4 0.040(2) 0.057(3) 0.055(3) 0.007(2) 0.001(2) 0.007(2) C5 0.041(2) 0.056(3) 0.086(4) 0.009(3) -0.014(3) 0.004(2) C6 0.062(3) 0.062(3) 0.079(4) -0.020(3) -0.028(3) 0.009(3) C7 0.066(3) 0.068(3) 0.048(3) -0.010(2) 0.002(2) 0.018(3) C8 0.090(4) 0.056(3) 0.092(4) 0.028(3) 0.040(3) 0.006(3) C9 0.033(2) 0.040(2) 0.039(2) 0.0018(15) -0.0053(16) -0.0003(15) C10 0.045(2) 0.051(2) 0.035(2) -0.0024(17) -0.0022(18) 0.0019(19) C11 0.064(3) 0.053(3) 0.033(2) -0.0032(17) -0.006(2) 0.002(2) C12 0.066(3) 0.048(3) 0.045(2) -0.0029(18) -0.021(2) 0.004(2) C13 0.038(2) 0.054(3) 0.058(3) -0.001(2) -0.008(2) 0.0078(19) C14 0.036(2) 0.051(2) 0.046(2) 0.0034(18) 0.0029(18) 0.0034(18) C15 0.032(2) 0.045(2) 0.035(2) 0.0035(16) 0.0009(16) 0.0042(16) C16 0.035(2) 0.049(2) 0.045(2) -0.0034(17) 0.0024(18) -0.0044(17) C17 0.0308(19) 0.061(3) 0.046(2) 0.0040(19) 0.0047(18) 0.0032(18) C18 0.043(2) 0.055(3) 0.039(2) -0.0040(17) 0.0052(18) 0.0055(19) C19 0.048(2) 0.045(2) 0.060(3) -0.006(2) 0.008(2) 0.0023(19) C20 0.032(2) 0.057(3) 0.055(3) -0.006(2) 0.0085(19) -0.0066(19) C21 0.0306(18) 0.040(2) 0.0364(19) 0.0032(15) -0.0005(15) 0.0025(16) C22 0.036(2) 0.051(2) 0.0310(19) 0.0045(16) -0.0016(16) 0.0022(18) C23 0.035(2) 0.046(2) 0.044(2) 0.0087(17) 0.0037(17) 0.0005(17) C24 0.0274(19) 0.048(2) 0.056(3) -0.0018(19) -0.0011(18) 0.0011(17) C25 0.035(2) 0.057(3) 0.045(2) -0.0035(18) -0.0044(18) -0.0008(19) C26 0.037(2) 0.048(2) 0.036(2) 0.0082(16) 0.0012(17) -0.0015(16) C27 0.089(4) 0.092(4) 0.063(3) 0.006(3) -0.033(3) 0.025(3) C28 0.055(3) 0.067(3) 0.071(3) -0.011(2) 0.004(3) 0.014(2) C29 0.052(3) 0.069(3) 0.069(3) -0.007(2) -0.004(2) -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 Au P1 2.2635(9) . ? Au S1 2.3039(10) . ? S1 C1 1.762(4) . ? P1 C21 1.806(4) . ? P1 C9 1.815(4) . ? P1 C15 1.818(4) . ? O1 C1 1.352(5) . ? O1 C8 1.444(5) . ? N1 C1 1.266(5) . ? N1 C2 1.403(5) . ? C2 C3 1.375(5) . ? C2 C7 1.383(6) . ? C3 C4 1.379(5) . ? C3 H3 0.9400 . ? C4 C5 1.365(6) . ? C4 H4 0.9400 . ? C5 C6 1.365(7) . ? C5 H5 0.9400 . ? C6 C7 1.380(7) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.390(5) . ? C9 C14 1.396(5) . ? C10 C11 1.378(6) . ? C10 H10 0.9400 . ? C11 C12 1.385(6) . ? C11 H11 0.9400 . ? C12 C13 1.367(6) . ? C12 C27 1.514(6) . ? C13 C14 1.379(6) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.381(6) . ? C15 C16 1.392(5) . ? C16 C17 1.383(5) . ? C16 H16 0.9400 . ? C17 C18 1.381(6) . ? C17 H17 0.9400 . ? C18 C19 1.394(6) . ? C18 C28 1.511(6) . ? C19 C20 1.400(6) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.384(5) . ? C21 C22 1.390(5) . ? C22 C23 1.379(5) . ? C22 H22 0.9400 . ? C23 C24 1.382(5) . ? C23 H23 0.9400 . ? C24 C25 1.397(6) . ? C24 C29 1.510(6) . ? C25 C26 1.376(6) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 170.56(4) . . ? C1 S1 Au 105.45(14) . . ? C21 P1 C9 106.50(17) . . ? C21 P1 C15 105.75(17) . . ? C9 P1 C15 105.45(17) . . ? C21 P1 Au 113.87(13) . . ? C9 P1 Au 110.66(12) . . ? C15 P1 Au 113.97(13) . . ? C1 O1 C8 116.2(4) . . ? C1 N1 C2 122.3(4) . . ? N1 C1 O1 119.9(4) . . ? N1 C1 S1 131.9(3) . . ? O1 C1 S1 108.2(3) . . ? C3 C2 C7 117.8(4) . . ? C3 C2 N1 120.1(4) . . ? C7 C2 N1 121.9(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.9(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.0(5) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 120.4(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 121.0(4) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.2(3) . . ? C10 C9 P1 122.4(3) . . ? C14 C9 P1 119.4(3) . . ? C9 C10 C11 120.3(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 121.4(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 118.2(4) . . ? C11 C12 C27 120.5(4) . . ? C13 C12 C27 121.2(5) . . ? C12 C13 C14 121.7(4) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C9 120.3(4) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C20 C15 C16 118.5(4) . . ? C20 C15 P1 118.2(3) . . ? C16 C15 P1 123.2(3) . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 121.3(4) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C19 119.3(4) . . ? C17 C18 C28 121.1(4) . . ? C19 C18 C28 119.6(4) . . ? C20 C19 C18 118.9(4) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C15 C20 C19 121.8(4) . . ? C15 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C26 C21 C22 117.8(3) . . ? C26 C21 P1 119.1(3) . . ? C22 C21 P1 123.0(3) . . ? C21 C22 C23 121.0(4) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 121.4(4) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 117.7(4) . . ? C23 C24 C29 120.7(4) . . ? C25 C24 C29 121.6(4) . . ? C26 C25 C24 120.8(4) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C21 C26 C25 121.4(4) . . ? C21 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.14 # 0.81 A from Au _refine_diff_density_min -0.46 _refine_diff_density_rms 0.116 # Attachment 'mtolNO2.CIF' data_(m-tol)3PAu(SC(OMe)=NC6H4NO2-4) _database_code_depnum_ccdc_archive 'CCDC 666590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H28 Au N2 O3 P S' _chemical_formula_sum 'C29 H28 Au N2 O3 P S' _chemical_formula_weight 712.53 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5246(6) _cell_length_b 11.8876(7) _cell_length_c 13.2790(8) _cell_angle_alpha 93.580(1) _cell_angle_beta 93.252(1) _cell_angle_gamma 112.034(1) _cell_volume 1385.75(15) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4885 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 29.8 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 5.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.592 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w & \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11669 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.046 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7917 _reflns_number_gt 6791 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHEXLTL (Bruker, 2000)' _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^)+(0.0565P)^2^] 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 7917 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.097 _refine_ls_wR_factor_gt 0.089 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _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 Au Au 0.013591(15) 0.128559(13) 0.230334(11) 0.03715(6) Uani 1 1 d . . . S1 S -0.18057(11) -0.02010(9) 0.12997(8) 0.0389(2) Uani 1 1 d . . . P1 P 0.19859(11) 0.27175(9) 0.33477(7) 0.0336(2) Uani 1 1 d . . . O3 O -0.8722(4) -0.4688(4) -0.1061(4) 0.0766(13) Uani 1 1 d . . . O2 O -0.7135(4) -0.5554(3) -0.0862(4) 0.0683(11) Uani 1 1 d . . . O1 O -0.0619(3) 0.1514(3) 0.0117(2) 0.0426(7) Uani 1 1 d . . . N1 N -0.2629(3) -0.0087(3) -0.0661(3) 0.0358(7) Uani 1 1 d . . . N2 N -0.7416(4) -0.4653(3) -0.0940(3) 0.0446(8) Uani 1 1 d . . . C1 C -0.1725(4) 0.0403(3) 0.0126(3) 0.0325(7) Uani 1 1 d . . . C2 C -0.3792(4) -0.1241(3) -0.0675(3) 0.0307(7) Uani 1 1 d . . . C3 C -0.5295(4) -0.1318(4) -0.0841(3) 0.0383(8) Uani 1 1 d . . . H3 H -0.5489 -0.0604 -0.0893 0.046 Uiso 1 1 calc R . . C4 C -0.6483(4) -0.2428(4) -0.0929(3) 0.0383(8) Uani 1 1 d . . . H4 H -0.7492 -0.2482 -0.1031 0.046 Uiso 1 1 calc R . . C5 C -0.6166(4) -0.3466(3) -0.0863(3) 0.0340(7) Uani 1 1 d . . . C6 C -0.4691(4) -0.3424(4) -0.0716(3) 0.0356(8) Uani 1 1 d . . . H6 H -0.4502 -0.4142 -0.0681 0.043 Uiso 1 1 calc R . . C7 C -0.3508(4) -0.2295(4) -0.0621(3) 0.0343(7) Uani 1 1 d . . . H7 H -0.2501 -0.2244 -0.0519 0.041 Uiso 1 1 calc R . . C8 C -0.0573(6) 0.2076(4) -0.0831(4) 0.0572(13) Uani 1 1 d . . . H8A H 0.0252 0.2870 -0.0766 0.086 Uiso 1 1 calc R . . H8B H -0.1529 0.2170 -0.0984 0.086 Uiso 1 1 calc R . . H8C H -0.0412 0.1563 -0.1373 0.086 Uiso 1 1 calc R . . C9 C 0.2781(4) 0.4139(4) 0.2780(3) 0.0356(8) Uani 1 1 d . . . C10 C 0.4279(4) 0.4970(4) 0.2995(3) 0.0372(8) Uani 1 1 d . . . H10 H 0.4942 0.4783 0.3444 0.045 Uiso 1 1 calc R . . C11 C 0.4806(5) 0.6068(4) 0.2555(3) 0.0387(8) Uani 1 1 d . . . C12 C 0.3814(5) 0.6323(4) 0.1880(3) 0.0438(9) Uani 1 1 d . . . H12 H 0.4156 0.7061 0.1577 0.053 Uiso 1 1 calc R . . C13 C 0.2347(5) 0.5515(5) 0.1650(4) 0.0478(10) Uani 1 1 d . . . H13 H 0.1693 0.5703 0.1195 0.057 Uiso 1 1 calc R . . C14 C 0.1816(5) 0.4403(4) 0.2095(3) 0.0430(9) Uani 1 1 d . . . H14 H 0.0815 0.3843 0.1929 0.052 Uiso 1 1 calc R . . C15 C 0.3513(4) 0.2259(4) 0.3765(3) 0.0348(8) Uani 1 1 d . . . C16 C 0.4493(5) 0.2830(4) 0.4614(3) 0.0447(9) Uani 1 1 d . . . H16 H 0.4399 0.3498 0.4980 0.054 Uiso 1 1 calc R . . C17 C 0.5610(5) 0.2418(5) 0.4923(4) 0.0557(12) Uani 1 1 d . . . H17 H 0.6282 0.2815 0.5495 0.067 Uiso 1 1 calc R . . C18 C 0.5751(6) 0.1439(5) 0.4406(4) 0.0588(13) Uani 1 1 d . . . H18 H 0.6525 0.1180 0.4628 0.071 Uiso 1 1 calc R . . C19 C 0.4760(6) 0.0808(5) 0.3546(4) 0.0538(12) Uani 1 1 d . . . C20 C 0.3656(5) 0.1251(4) 0.3250(3) 0.0424(9) Uani 1 1 d . . . H20 H 0.2978 0.0857 0.2680 0.051 Uiso 1 1 calc R . . C21 C 0.1259(5) 0.3063(4) 0.4521(3) 0.0422(9) Uani 1 1 d . . . C22 C 0.1668(6) 0.4240(5) 0.4981(4) 0.0517(11) Uani 1 1 d . . . H22 H 0.2335 0.4905 0.4677 0.062 Uiso 1 1 calc R . . C23 C 0.1096(6) 0.4436(6) 0.5885(4) 0.0619(14) Uani 1 1 d . . . C24 C 0.0107(6) 0.3479(7) 0.6318(5) 0.0701(17) Uani 1 1 d . . . H24 H -0.0314 0.3617 0.6915 0.084 Uiso 1 1 calc R . . C25 C -0.0276(7) 0.2312(7) 0.5885(4) 0.0682(16) Uani 1 1 d . . . H25 H -0.0920 0.1650 0.6205 0.082 Uiso 1 1 calc R . . C26 C 0.0279(6) 0.2102(5) 0.4979(4) 0.0540(12) Uani 1 1 d . . . H26 H -0.0014 0.1302 0.4677 0.065 Uiso 1 1 calc R . . C27 C 0.6429(5) 0.6990(5) 0.2788(4) 0.0529(11) Uani 1 1 d . . . H27A H 0.6443 0.7626 0.3288 0.079 Uiso 1 1 calc R . . H27B H 0.6812 0.7346 0.2173 0.079 Uiso 1 1 calc R . . H27C H 0.7066 0.6583 0.3052 0.079 Uiso 1 1 calc R . . C28 C 0.4861(9) -0.0285(6) 0.3003(5) 0.083(2) Uani 1 1 d . . . H28A H 0.4177 -0.0520 0.2389 0.124 Uiso 1 1 calc R . . H28B H 0.4576 -0.0950 0.3435 0.124 Uiso 1 1 calc R . . H28C H 0.5895 -0.0100 0.2829 0.124 Uiso 1 1 calc R . . C29 C 0.1552(10) 0.5643(9) 0.6437(6) 0.105(3) Uani 1 1 d . . . H29A H 0.0953 0.5588 0.7012 0.158 Uiso 1 1 calc R . . H29B H 0.1384 0.6204 0.5990 0.158 Uiso 1 1 calc R . . H29C H 0.2621 0.5937 0.6673 0.158 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 Au 0.03457(9) 0.03429(9) 0.03641(9) -0.00334(6) -0.00750(6) 0.00855(6) S1 0.0364(5) 0.0323(5) 0.0377(5) 0.0011(4) -0.0066(4) 0.0032(4) P1 0.0334(4) 0.0330(5) 0.0316(5) -0.0024(4) -0.0065(3) 0.0115(4) O3 0.0284(15) 0.055(2) 0.133(4) 0.025(2) -0.0145(19) 0.0008(15) O2 0.0436(18) 0.0329(17) 0.116(3) 0.0084(19) 0.0012(19) 0.0015(15) O1 0.0309(13) 0.0284(13) 0.0583(18) 0.0074(12) -0.0047(12) 0.0003(11) N1 0.0297(14) 0.0304(16) 0.0389(17) 0.0045(13) -0.0033(12) 0.0026(13) N2 0.0328(16) 0.0336(18) 0.056(2) 0.0062(16) -0.0036(15) 0.0003(14) C1 0.0270(15) 0.0264(16) 0.0414(19) 0.0019(14) -0.0026(13) 0.0081(14) C2 0.0276(15) 0.0297(17) 0.0276(16) 0.0011(13) -0.0004(12) 0.0032(14) C3 0.0357(18) 0.034(2) 0.043(2) 0.0032(16) -0.0047(15) 0.0118(16) C4 0.0253(16) 0.040(2) 0.046(2) 0.0011(17) -0.0002(14) 0.0097(16) C5 0.0270(16) 0.0300(18) 0.0357(18) 0.0007(14) -0.0022(13) 0.0013(14) C6 0.0344(18) 0.0317(18) 0.040(2) 0.0024(15) -0.0001(15) 0.0120(15) C7 0.0261(15) 0.0364(19) 0.0370(19) 0.0013(15) -0.0009(13) 0.0090(15) C8 0.049(2) 0.037(2) 0.077(3) 0.024(2) 0.003(2) 0.004(2) C9 0.0387(18) 0.0353(19) 0.0315(18) -0.0035(15) -0.0063(14) 0.0150(16) C10 0.0345(18) 0.041(2) 0.0347(19) -0.0014(16) -0.0071(14) 0.0150(17) C11 0.0377(18) 0.039(2) 0.0347(19) 0.0024(16) -0.0036(15) 0.0103(17) C12 0.050(2) 0.044(2) 0.040(2) 0.0102(18) 0.0014(18) 0.020(2) C13 0.047(2) 0.051(3) 0.048(2) 0.007(2) -0.0097(18) 0.024(2) C14 0.0359(19) 0.044(2) 0.047(2) 0.0009(18) -0.0097(16) 0.0149(18) C15 0.0347(17) 0.0366(19) 0.0318(18) 0.0045(15) -0.0025(14) 0.0127(16) C16 0.046(2) 0.037(2) 0.046(2) 0.0020(18) -0.0105(18) 0.0114(18) C17 0.046(2) 0.056(3) 0.060(3) 0.012(2) -0.014(2) 0.014(2) C18 0.052(3) 0.071(4) 0.065(3) 0.027(3) 0.004(2) 0.033(3) C19 0.067(3) 0.067(3) 0.045(2) 0.019(2) 0.016(2) 0.042(3) C20 0.055(2) 0.047(2) 0.0298(18) 0.0036(17) 0.0033(16) 0.024(2) C21 0.0359(19) 0.053(3) 0.038(2) -0.0035(18) -0.0073(15) 0.0199(19) C22 0.049(2) 0.055(3) 0.051(3) -0.012(2) -0.0066(19) 0.023(2) C23 0.053(3) 0.084(4) 0.053(3) -0.023(3) -0.009(2) 0.036(3) C24 0.053(3) 0.111(5) 0.055(3) -0.001(3) 0.005(2) 0.042(4) C25 0.061(3) 0.101(5) 0.044(3) 0.018(3) 0.008(2) 0.030(3) C26 0.051(2) 0.067(3) 0.041(2) 0.002(2) 0.0031(19) 0.019(2) C27 0.046(2) 0.046(3) 0.057(3) 0.007(2) -0.007(2) 0.008(2) C28 0.138(6) 0.101(5) 0.057(3) 0.021(3) 0.029(4) 0.094(5) C29 0.105(6) 0.143(8) 0.082(5) -0.015(5) 0.007(4) 0.067(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 Au P1 2.2590(10) . ? Au S1 2.3007(10) . ? S1 C1 1.750(4) . ? P1 C9 1.806(4) . ? P1 C15 1.805(4) . ? P1 C21 1.826(5) . ? O3 N2 1.230(5) . ? O2 N2 1.206(5) . ? O1 C1 1.347(4) . ? O1 C8 1.457(6) . ? N1 C1 1.273(5) . ? N1 C2 1.401(5) . ? N2 C5 1.459(5) . ? C2 C7 1.382(5) . ? C2 C3 1.404(5) . ? C3 C4 1.371(6) . ? C3 H3 0.9400 . ? C4 C5 1.383(6) . ? C4 H4 0.9400 . ? C5 C6 1.388(5) . ? C6 C7 1.384(5) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C14 1.388(5) . ? C9 C10 1.398(5) . ? C10 C11 1.391(6) . ? C10 H10 0.9400 . ? C11 C12 1.393(6) . ? C11 C27 1.522(6) . ? C12 C13 1.369(6) . ? C12 H12 0.9400 . ? C13 C14 1.407(6) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.384(6) . ? C15 C20 1.397(6) . ? C16 C17 1.381(6) . ? C16 H16 0.9400 . ? C17 C18 1.368(8) . ? C17 H17 0.9400 . ? C18 C19 1.413(8) . ? C18 H18 0.9400 . ? C19 C20 1.390(7) . ? C19 C28 1.484(8) . ? C20 H20 0.9400 . ? C21 C22 1.392(7) . ? C21 C26 1.377(7) . ? C22 C23 1.389(7) . ? C22 H22 0.9400 . ? C23 C24 1.360(9) . ? C23 C29 1.467(10) . ? C24 C25 1.373(9) . ? C24 H24 0.9400 . ? C25 C26 1.386(7) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 177.52(3) . . ? C1 S1 Au 103.58(13) . . ? C9 P1 C15 108.80(18) . . ? C9 P1 C21 106.3(2) . . ? C15 P1 C21 104.08(18) . . ? C9 P1 Au 111.80(13) . . ? C15 P1 Au 113.90(14) . . ? C21 P1 Au 111.46(14) . . ? C1 O1 C8 115.3(3) . . ? C1 N1 C2 121.4(3) . . ? O2 N2 O3 122.7(4) . . ? O2 N2 C5 119.1(4) . . ? O3 N2 C5 118.2(4) . . ? N1 C1 O1 120.1(3) . . ? N1 C1 S1 126.1(3) . . ? O1 C1 S1 113.7(3) . . ? C7 C2 N1 122.7(3) . . ? C7 C2 C3 119.6(3) . . ? N1 C2 C3 117.4(3) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 122.4(3) . . ? C4 C5 N2 119.3(3) . . ? C6 C5 N2 118.3(4) . . ? C7 C6 C5 118.2(4) . . ? C7 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C6 C7 C2 120.7(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 119.3(4) . . ? C14 C9 P1 116.7(3) . . ? C10 C9 P1 124.1(3) . . ? C11 C10 C9 121.2(4) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 118.6(4) . . ? C10 C11 C27 121.9(4) . . ? C12 C11 C27 119.5(4) . . ? C11 C12 C13 121.1(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 120.2(4) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 119.6(4) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C20 118.8(4) . . ? C16 C15 P1 122.0(3) . . ? C20 C15 P1 119.1(3) . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.8(5) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 121.6(4) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C20 C19 C18 116.1(5) . . ? C20 C19 C28 121.7(5) . . ? C18 C19 C28 122.2(5) . . ? C19 C20 C15 122.8(4) . . ? C19 C20 H20 118.6 . . ? C15 C20 H20 118.6 . . ? C22 C21 C26 118.8(5) . . ? C22 C21 P1 123.3(4) . . ? C26 C21 P1 117.8(4) . . ? C21 C22 C23 120.3(5) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.1(6) . . ? C24 C23 C29 116.9(6) . . ? C22 C23 C29 122.9(6) . . ? C23 C24 C25 120.0(5) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 120.5(6) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.1(5) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C11 C27 H27A 109.5 . . ? C11 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C11 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C19 C28 H28A 109.5 . . ? C19 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C19 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C23 C29 H29A 109.5 . . ? C23 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C23 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.87 # 0.78 A from Au _refine_diff_density_min -0.77 _refine_diff_density_rms 0.137 # Attachment 'mtolPh.CIF' data_(m-tol)3PAu(SC(OMe)=NC6H5) _database_code_depnum_ccdc_archive 'CCDC 666591' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H29 Au N O P S' _chemical_formula_sum 'C29 H29 Au N O P S' _chemical_formula_weight 667.53 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ' P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8426(10) _cell_length_b 10.4687(12) _cell_length_c 15.2214(19) _cell_angle_alpha 74.347(2) _cell_angle_beta 82.829(3) _cell_angle_gamma 81.799(3) _cell_volume 1337.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 5.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.615 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w & \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11172 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.047 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.4 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7635 _reflns_number_gt 7240 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHEXLTL (Bruker, 2000)' _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^)+(0.0300P)^2^+1.6227P] 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 7635 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.038 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.086 _refine_ls_wR_factor_gt 0.084 _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_restrained_S_all 1.12 _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 Au Au 0.170523(18) 0.035480(15) 0.240302(11) 0.02643(5) Uani 1 1 d . . . S1 S 0.34565(13) 0.18811(12) 0.21158(9) 0.0382(3) Uani 1 1 d . . . P1 P 0.03757(12) -0.14370(10) 0.27398(7) 0.0254(2) Uani 1 1 d . . . O1 O 0.3655(5) 0.4144(4) 0.0999(3) 0.0533(10) Uani 1 1 d . . . N1 N 0.1171(5) 0.3924(4) 0.1515(3) 0.0375(9) Uani 1 1 d . . . C1 C 0.2558(6) 0.3433(4) 0.1525(3) 0.0352(9) Uani 1 1 d . . . C2 C -0.0016(5) 0.3293(4) 0.2076(3) 0.0324(9) Uani 1 1 d . . . C3 C -0.0236(6) 0.3224(6) 0.3006(4) 0.0457(12) Uani 1 1 d . . . H3 H 0.0478 0.3544 0.3279 0.055 Uiso 1 1 calc R . . C4 C -0.1494(7) 0.2692(7) 0.3535(4) 0.0599(17) Uani 1 1 d . . . H4 H -0.1628 0.2656 0.4164 0.072 Uiso 1 1 calc R . . C5 C -0.2545(7) 0.2217(6) 0.3156(5) 0.0609(18) Uani 1 1 d . . . H5 H -0.3393 0.1846 0.3520 0.073 Uiso 1 1 calc R . . C6 C -0.2348(6) 0.2290(6) 0.2241(5) 0.0584(17) Uani 1 1 d . . . H6 H -0.3076 0.1975 0.1976 0.070 Uiso 1 1 calc R . . C7 C -0.1103(6) 0.2814(5) 0.1700(4) 0.0455(12) Uani 1 1 d . . . H7 H -0.0987 0.2849 0.1072 0.055 Uiso 1 1 calc R . . C8 C 0.3122(8) 0.5476(6) 0.0490(5) 0.068(2) Uani 1 1 d . . . H8A H 0.3986 0.5906 0.0137 0.102 Uiso 1 1 calc R . . H8B H 0.2631 0.5990 0.0912 0.102 Uiso 1 1 calc R . . H8C H 0.2390 0.5426 0.0079 0.102 Uiso 1 1 calc R . . C9 C 0.1653(5) -0.2952(4) 0.3121(3) 0.0285(8) Uani 1 1 d . . . C10 C 0.1315(6) -0.3957(5) 0.3902(4) 0.0441(12) Uani 1 1 d . . . H10 H 0.0381 -0.3884 0.4264 0.053 Uiso 1 1 calc R . . C11 C 0.2391(7) -0.5072(5) 0.4135(4) 0.0539(15) Uani 1 1 d . . . H11 H 0.2177 -0.5753 0.4664 0.065 Uiso 1 1 calc R . . C12 C 0.3766(7) -0.5204(5) 0.3606(4) 0.0495(13) Uani 1 1 d . . . H12 H 0.4468 -0.5972 0.3777 0.059 Uiso 1 1 calc R . . C13 C 0.4115(6) -0.4215(5) 0.2829(4) 0.0447(12) Uani 1 1 d . . . C14 C 0.3051(5) -0.3085(5) 0.2589(3) 0.0359(10) Uani 1 1 d . . . H14 H 0.3277 -0.2403 0.2063 0.043 Uiso 1 1 calc R . . C15 C -0.0507(5) -0.1663(4) 0.1790(3) 0.0266(8) Uani 1 1 d . . . C16 C -0.0450(5) -0.2884(5) 0.1591(3) 0.0332(9) Uani 1 1 d . . . H16 H 0.0072 -0.3650 0.1956 0.040 Uiso 1 1 calc R . . C17 C -0.1162(6) -0.2977(5) 0.0855(4) 0.0435(11) Uani 1 1 d . . . H17 H -0.1102 -0.3804 0.0714 0.052 Uiso 1 1 calc R . . C18 C -0.1961(6) -0.1861(6) 0.0325(3) 0.0424(11) Uani 1 1 d . . . H18 H -0.2454 -0.1940 -0.0167 0.051 Uiso 1 1 calc R . . C19 C -0.2043(6) -0.0618(5) 0.0513(3) 0.0369(10) Uani 1 1 d . . . C20 C -0.1277(5) -0.0532(4) 0.1231(3) 0.0330(9) Uani 1 1 d . . . H20 H -0.1273 0.0306 0.1345 0.040 Uiso 1 1 calc R . . C21 C -0.1147(5) -0.1431(4) 0.3655(3) 0.0262(8) Uani 1 1 d . . . C22 C -0.0789(5) -0.1177(4) 0.4456(3) 0.0310(8) Uani 1 1 d . . . H22 H 0.0214 -0.1025 0.4509 0.037 Uiso 1 1 calc R . . C23 C -0.1915(5) -0.1151(5) 0.5174(3) 0.0340(9) Uani 1 1 d . . . H23 H -0.1671 -0.1001 0.5719 0.041 Uiso 1 1 calc R . . C24 C -0.3397(5) -0.1344(4) 0.5087(3) 0.0332(9) Uani 1 1 d . . . H24 H -0.4159 -0.1301 0.5571 0.040 Uiso 1 1 calc R . . C25 C -0.3783(5) -0.1600(4) 0.4300(3) 0.0313(9) Uani 1 1 d . . . C26 C -0.2641(5) -0.1650(4) 0.3587(3) 0.0288(8) Uani 1 1 d . . . H26 H -0.2882 -0.1833 0.3052 0.035 Uiso 1 1 calc R . . C27 C 0.5624(7) -0.4322(7) 0.2262(5) 0.068(2) Uani 1 1 d . . . H27A H 0.6454 -0.4355 0.2630 0.101 Uiso 1 1 calc R . . H27B H 0.5653 -0.3552 0.1738 0.101 Uiso 1 1 calc R . . H27C H 0.5738 -0.5129 0.2051 0.101 Uiso 1 1 calc R . . C28 C -0.2922(7) 0.0607(6) -0.0057(4) 0.0514(14) Uani 1 1 d . . . H28A H -0.3735 0.0962 0.0331 0.077 Uiso 1 1 calc R . . H28B H -0.3363 0.0367 -0.0534 0.077 Uiso 1 1 calc R . . H28C H -0.2231 0.1277 -0.0333 0.077 Uiso 1 1 calc R . . C29 C -0.5395(6) -0.1831(6) 0.4215(4) 0.0482(13) Uani 1 1 d . . . H29A H -0.6082 -0.1560 0.4697 0.072 Uiso 1 1 calc R . . H29B H -0.5429 -0.2772 0.4270 0.072 Uiso 1 1 calc R . . H29C H -0.5711 -0.1311 0.3623 0.072 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 Au 0.02612(8) 0.02286(8) 0.02949(8) -0.00571(5) -0.00176(5) -0.00275(5) S1 0.0265(5) 0.0332(5) 0.0530(7) -0.0042(5) -0.0057(5) -0.0085(4) P1 0.0250(5) 0.0222(4) 0.0283(5) -0.0059(4) -0.0028(4) -0.0017(4) O1 0.048(2) 0.0317(17) 0.069(3) -0.0023(17) 0.0238(19) -0.0127(16) N1 0.036(2) 0.0311(19) 0.041(2) -0.0040(16) 0.0030(16) -0.0027(16) C1 0.038(2) 0.025(2) 0.041(2) -0.0081(17) 0.0070(19) -0.0081(18) C2 0.030(2) 0.0195(18) 0.044(2) -0.0022(16) -0.0079(18) 0.0033(15) C3 0.034(3) 0.057(3) 0.042(3) -0.003(2) -0.007(2) -0.008(2) C4 0.042(3) 0.070(4) 0.047(3) 0.007(3) 0.005(2) 0.007(3) C5 0.031(3) 0.041(3) 0.100(5) -0.009(3) 0.017(3) -0.005(2) C6 0.028(3) 0.051(3) 0.108(6) -0.041(4) 0.002(3) -0.007(2) C7 0.037(3) 0.044(3) 0.061(3) -0.025(3) -0.008(2) 0.000(2) C8 0.069(4) 0.032(3) 0.083(5) 0.005(3) 0.029(4) -0.009(3) C9 0.028(2) 0.0207(17) 0.037(2) -0.0067(15) -0.0051(16) -0.0028(15) C10 0.043(3) 0.027(2) 0.051(3) 0.001(2) 0.005(2) 0.002(2) C11 0.055(3) 0.027(2) 0.062(4) 0.010(2) 0.006(3) 0.002(2) C12 0.046(3) 0.028(2) 0.067(4) -0.004(2) -0.005(3) 0.004(2) C13 0.040(3) 0.035(2) 0.058(3) -0.016(2) -0.001(2) 0.005(2) C14 0.033(2) 0.030(2) 0.041(2) -0.0052(18) 0.0026(18) -0.0038(18) C15 0.0265(19) 0.0253(18) 0.0257(18) -0.0050(14) 0.0012(14) -0.0013(15) C16 0.034(2) 0.031(2) 0.034(2) -0.0090(17) -0.0006(17) -0.0041(17) C17 0.055(3) 0.038(2) 0.044(3) -0.019(2) -0.001(2) -0.012(2) C18 0.046(3) 0.054(3) 0.032(2) -0.017(2) -0.006(2) -0.007(2) C19 0.038(2) 0.038(2) 0.031(2) -0.0038(18) -0.0044(18) -0.0016(19) C20 0.038(2) 0.029(2) 0.032(2) -0.0102(17) -0.0001(18) -0.0034(18) C21 0.0252(19) 0.0231(17) 0.0286(19) -0.0056(14) -0.0038(15) 0.0021(14) C22 0.028(2) 0.033(2) 0.033(2) -0.0104(17) -0.0037(16) -0.0022(17) C23 0.036(2) 0.037(2) 0.032(2) -0.0130(18) -0.0022(17) -0.0060(19) C24 0.033(2) 0.033(2) 0.033(2) -0.0121(17) 0.0033(17) -0.0025(18) C25 0.033(2) 0.0246(19) 0.038(2) -0.0115(16) -0.0006(17) -0.0039(16) C26 0.027(2) 0.0293(19) 0.032(2) -0.0102(16) -0.0042(16) -0.0037(16) C27 0.039(3) 0.054(4) 0.091(5) -0.005(3) 0.015(3) 0.009(3) C28 0.059(4) 0.053(3) 0.037(3) -0.002(2) -0.013(2) 0.003(3) C29 0.031(2) 0.067(4) 0.050(3) -0.022(3) -0.001(2) -0.009(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 Au P1 2.2635(11) . ? Au S1 2.3026(12) . ? S1 C1 1.761(5) . ? P1 C9 1.812(4) . ? P1 C15 1.809(4) . ? P1 C21 1.813(4) . ? O1 C1 1.351(6) . ? O1 C8 1.445(7) . ? N1 C1 1.261(6) . ? N1 C2 1.392(6) . ? C2 C7 1.390(7) . ? C2 C3 1.388(7) . ? C3 C4 1.381(8) . ? C3 H3 0.9400 . ? C4 C5 1.366(10) . ? C4 H4 0.9400 . ? C5 C6 1.363(10) . ? C5 H5 0.9400 . ? C6 C7 1.376(8) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C14 1.401(6) . ? C9 C10 1.391(6) . ? C10 C11 1.392(7) . ? C10 H10 0.9400 . ? C11 C12 1.383(8) . ? C11 H11 0.9400 . ? C12 C13 1.381(8) . ? C12 H12 0.9400 . ? C13 C14 1.397(7) . ? C13 C27 1.503(8) . ? C14 H14 0.9400 . ? C15 C20 1.401(6) . ? C15 C16 1.384(6) . ? C16 C17 1.383(7) . ? C16 H16 0.9400 . ? C17 C18 1.384(7) . ? C17 H17 0.9400 . ? C18 C19 1.396(7) . ? C18 H18 0.9400 . ? C19 C20 1.385(6) . ? C19 C28 1.511(7) . ? C20 H20 0.9400 . ? C21 C26 1.393(6) . ? C21 C22 1.398(6) . ? C22 C23 1.386(6) . ? C22 H22 0.9400 . ? C23 C24 1.382(6) . ? C23 H23 0.9400 . ? C24 C25 1.386(6) . ? C24 H24 0.9400 . ? C25 C26 1.394(6) . ? C25 C29 1.506(7) . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 169.14(4) . . ? C1 S1 Au 107.62(16) . . ? C9 P1 C15 105.67(19) . . ? C9 P1 C21 106.1(2) . . ? C15 P1 C21 105.98(19) . . ? C9 P1 Au 109.69(14) . . ? C15 P1 Au 114.99(14) . . ? C21 P1 Au 113.71(14) . . ? C1 O1 C8 115.5(4) . . ? C1 N1 C2 123.4(4) . . ? N1 C1 O1 119.8(4) . . ? N1 C1 S1 132.1(4) . . ? O1 C1 S1 108.1(3) . . ? C7 C2 N1 120.3(5) . . ? C7 C2 C3 117.8(5) . . ? N1 C2 C3 121.7(4) . . ? C4 C3 C2 120.7(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.7(6) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.1(6) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.3(6) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 120.4(6) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 119.7(4) . . ? C14 C9 P1 116.8(3) . . ? C10 C9 P1 123.5(4) . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 121.6(5) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 120.4(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 118.6(5) . . ? C12 C13 C27 121.1(5) . . ? C14 C13 C27 120.2(5) . . ? C9 C14 C13 121.1(5) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C20 C15 C16 119.0(4) . . ? C20 C15 P1 117.5(3) . . ? C16 C15 P1 123.5(3) . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.5(5) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 120.7(4) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 118.1(4) . . ? C20 C19 C28 120.7(5) . . ? C18 C19 C28 121.2(5) . . ? C19 C20 C15 121.6(4) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? C26 C21 C22 119.3(4) . . ? C26 C21 P1 123.0(3) . . ? C22 C21 P1 117.6(3) . . ? C23 C22 C21 120.0(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 121.4(4) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 118.6(4) . . ? C24 C25 C29 121.1(4) . . ? C26 C25 C29 120.3(4) . . ? C21 C26 C25 120.9(4) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C13 C27 H27A 109.5 . . ? C13 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C13 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C19 C28 H28A 109.5 . . ? C19 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C19 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.51 # 0.80 A from Au _refine_diff_density_min -0.98 _refine_diff_density_rms 0.139 # Attachment 'otolMe4.CIF' data_(o-tol)3PAu(SC(OMe)=NC6H4Me-4) _database_code_depnum_ccdc_archive 'CCDC 666592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H31 Au N O P S' _chemical_formula_sum 'C30 H31 Au N O P S' _chemical_formula_weight 681.55 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7125(8) _cell_length_b 11.0257(9) _cell_length_c 14.7644(12) _cell_angle_alpha 111.187(2) _cell_angle_beta 103.553(2) _cell_angle_gamma 97.693(2) _cell_volume 1390.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4742 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 5.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.259 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11586 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.6 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7941 _reflns_number_gt 6756 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0683P)^2^] 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 7941 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.051 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.114 _refine_ls_wR_factor_gt 0.106 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 Au Au 0.149262(18) 0.308144(15) 0.301887(12) 0.04039(7) Uani 1 1 d . . . S1 S 0.21909(15) 0.44080(12) 0.22296(10) 0.0471(3) Uani 1 1 d . . . P1 P 0.08119(12) 0.18023(10) 0.38179(8) 0.0330(2) Uani 1 1 d . . . O1 O 0.3349(5) 0.2390(4) 0.1616(3) 0.0630(10) Uani 1 1 d . . . N1 N 0.3449(6) 0.3680(5) 0.0729(4) 0.0590(12) Uani 1 1 d . . . C1 C 0.3061(6) 0.3449(5) 0.1424(4) 0.0485(11) Uani 1 1 d . . . C2 C 0.3077(6) 0.4731(5) 0.0455(4) 0.0499(12) Uani 1 1 d . . . C3 C 0.4090(6) 0.5894(6) 0.0746(4) 0.0528(12) Uani 1 1 d . . . H3 H 0.5022 0.6040 0.1191 0.063 Uiso 1 1 calc R . . C4 C 0.3769(6) 0.6867(5) 0.0395(4) 0.0541(12) Uani 1 1 d . . . H4 H 0.4485 0.7659 0.0604 0.065 Uiso 1 1 calc R . . C5 C 0.2410(6) 0.6683(5) -0.0258(4) 0.0486(11) Uani 1 1 d . . . C5' C 0.2057(9) 0.7721(8) -0.0651(6) 0.0719(17) Uani 1 1 d . . . H5'1 H 0.2629 0.8601 -0.0152 0.108 Uiso 1 1 calc R . . H5'2 H 0.1026 0.7698 -0.0771 0.108 Uiso 1 1 calc R . . H5'3 H 0.2288 0.7533 -0.1286 0.108 Uiso 1 1 calc R . . C6 C 0.1389(6) 0.5514(6) -0.0538(4) 0.0544(13) Uani 1 1 d . . . H6 H 0.0448 0.5375 -0.0971 0.065 Uiso 1 1 calc R . . C7 C 0.1716(6) 0.4536(6) -0.0196(4) 0.0530(12) Uani 1 1 d . . . H7 H 0.1006 0.3738 -0.0410 0.064 Uiso 1 1 calc R . . C8 C 0.4051(11) 0.1558(9) 0.0964(7) 0.093(3) Uani 1 1 d . . . H8A H 0.4205 0.0823 0.1157 0.140 Uiso 1 1 calc R . . H8B H 0.4984 0.2087 0.1036 0.140 Uiso 1 1 calc R . . H8C H 0.3438 0.1204 0.0261 0.140 Uiso 1 1 calc R . . C9 C 0.1478(5) 0.0277(4) 0.3479(4) 0.0415(10) Uani 1 1 d . . . C10 C 0.1243(6) -0.0562(5) 0.2448(4) 0.0538(13) Uani 1 1 d . . . C11 C 0.1828(7) -0.1688(5) 0.2253(5) 0.0628(17) Uani 1 1 d . . . H11 H 0.1660 -0.2282 0.1572 0.075 Uiso 1 1 calc R . . C12 C 0.2635(7) -0.1952(5) 0.3016(6) 0.0666(18) Uani 1 1 d . . . H12 H 0.3039 -0.2702 0.2855 0.080 Uiso 1 1 calc R . . C13 C 0.2864(7) -0.1125(5) 0.4029(5) 0.0600(15) Uani 1 1 d . . . H13 H 0.3409 -0.1315 0.4556 0.072 Uiso 1 1 calc R . . C14 C 0.2275(6) -0.0013(5) 0.4250(4) 0.0458(10) Uani 1 1 d . . . H14 H 0.2419 0.0552 0.4934 0.055 Uiso 1 1 calc R . . C15 C -0.1161(5) 0.1242(4) 0.3538(3) 0.0379(9) Uani 1 1 d . . . C16 C -0.2061(5) 0.2146(5) 0.3587(4) 0.0450(10) Uani 1 1 d . . . C17 C -0.3558(6) 0.1655(6) 0.3322(5) 0.0586(13) Uani 1 1 d . . . H17 H -0.4176 0.2246 0.3349 0.070 Uiso 1 1 calc R . . C18 C -0.4146(7) 0.0306(7) 0.3018(5) 0.0647(16) Uani 1 1 d . . . H18 H -0.5162 -0.0010 0.2837 0.078 Uiso 1 1 calc R . . C19 C -0.3280(7) -0.0569(6) 0.2976(5) 0.0604(14) Uani 1 1 d . . . H19 H -0.3695 -0.1483 0.2771 0.072 Uiso 1 1 calc R . . C20 C -0.1785(6) -0.0112(5) 0.3235(4) 0.0483(11) Uani 1 1 d . . . H20 H -0.1185 -0.0718 0.3208 0.058 Uiso 1 1 calc R . . C21 C 0.1549(5) 0.2677(4) 0.5196(3) 0.0331(8) Uani 1 1 d . . . C22 C 0.3039(5) 0.3337(4) 0.5683(3) 0.0376(8) Uani 1 1 d . . . C23 C 0.3513(6) 0.4035(5) 0.6737(4) 0.0456(10) Uani 1 1 d . . . H23 H 0.4506 0.4463 0.7069 0.055 Uiso 1 1 calc R . . C24 C 0.2558(6) 0.4117(5) 0.7309(4) 0.0487(11) Uani 1 1 d . . . H24 H 0.2901 0.4612 0.8020 0.058 Uiso 1 1 calc R . . C25 C 0.1110(6) 0.3475(5) 0.6837(4) 0.0478(11) Uani 1 1 d . . . H25 H 0.0458 0.3532 0.7223 0.057 Uiso 1 1 calc R . . C26 C 0.0611(5) 0.2743(4) 0.5790(3) 0.0388(9) Uani 1 1 d . . . H26 H -0.0376 0.2283 0.5474 0.047 Uiso 1 1 calc R . . C27 C 0.0357(9) -0.0334(7) 0.1573(5) 0.0725(18) Uani 1 1 d . . . H27A H -0.0608 -0.0286 0.1638 0.109 Uiso 1 1 calc R . . H27B H 0.0270 -0.1069 0.0937 0.109 Uiso 1 1 calc R . . H27C H 0.0834 0.0500 0.1578 0.109 Uiso 1 1 calc R . . C28 C -0.1464(7) 0.3630(5) 0.3948(6) 0.0639(16) Uani 1 1 d . . . H28A H -0.0878 0.4001 0.4659 0.096 Uiso 1 1 calc R . . H28B H -0.2265 0.4062 0.3875 0.096 Uiso 1 1 calc R . . H28C H -0.0863 0.3784 0.3541 0.096 Uiso 1 1 calc R . . C29 C 0.4161(5) 0.3291(6) 0.5114(4) 0.0497(11) Uani 1 1 d . . . H29A H 0.5103 0.3841 0.5591 0.075 Uiso 1 1 calc R . . H29B H 0.3864 0.3630 0.4596 0.075 Uiso 1 1 calc R . . H29C H 0.4233 0.2373 0.4793 0.075 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 Au 0.04302(11) 0.03815(10) 0.04253(11) 0.02221(7) 0.01292(7) 0.00167(7) S1 0.0551(7) 0.0444(6) 0.0521(7) 0.0288(5) 0.0225(5) 0.0078(5) P1 0.0368(5) 0.0268(4) 0.0362(5) 0.0139(4) 0.0134(4) 0.0034(4) O1 0.075(3) 0.057(2) 0.081(3) 0.043(2) 0.037(2) 0.027(2) N1 0.070(3) 0.063(3) 0.067(3) 0.039(2) 0.038(3) 0.025(2) C1 0.047(3) 0.044(2) 0.056(3) 0.023(2) 0.018(2) 0.005(2) C2 0.061(3) 0.054(3) 0.048(3) 0.025(2) 0.032(2) 0.017(2) C3 0.051(3) 0.060(3) 0.047(3) 0.022(2) 0.012(2) 0.013(2) C4 0.057(3) 0.050(3) 0.054(3) 0.020(2) 0.021(2) 0.005(2) C5 0.061(3) 0.056(3) 0.042(2) 0.024(2) 0.027(2) 0.022(2) C5' 0.079(5) 0.077(4) 0.072(4) 0.038(4) 0.027(3) 0.029(4) C6 0.048(3) 0.075(4) 0.048(3) 0.031(3) 0.018(2) 0.019(3) C7 0.045(3) 0.059(3) 0.061(3) 0.029(3) 0.021(2) 0.009(2) C8 0.118(7) 0.096(6) 0.112(6) 0.065(5) 0.060(6) 0.065(5) C9 0.046(2) 0.0292(18) 0.048(2) 0.0102(17) 0.025(2) 0.0048(17) C10 0.058(3) 0.038(2) 0.056(3) 0.007(2) 0.029(2) -0.003(2) C11 0.068(4) 0.036(2) 0.076(4) 0.001(2) 0.046(3) 0.005(2) C12 0.056(3) 0.038(2) 0.108(5) 0.019(3) 0.047(4) 0.011(2) C13 0.061(3) 0.043(2) 0.097(5) 0.038(3) 0.041(3) 0.020(2) C14 0.051(3) 0.038(2) 0.061(3) 0.027(2) 0.027(2) 0.015(2) C15 0.036(2) 0.037(2) 0.040(2) 0.0181(17) 0.0117(17) 0.0021(17) C16 0.041(2) 0.043(2) 0.051(3) 0.023(2) 0.0110(19) 0.0052(19) C17 0.044(3) 0.065(3) 0.074(4) 0.036(3) 0.019(3) 0.016(3) C18 0.039(3) 0.068(4) 0.085(4) 0.037(3) 0.015(3) -0.001(3) C19 0.056(3) 0.048(3) 0.072(4) 0.028(3) 0.016(3) -0.008(2) C20 0.050(3) 0.038(2) 0.053(3) 0.018(2) 0.015(2) 0.001(2) C21 0.039(2) 0.0242(15) 0.0367(19) 0.0124(15) 0.0139(16) 0.0065(15) C22 0.037(2) 0.0350(19) 0.045(2) 0.0194(17) 0.0139(17) 0.0088(17) C23 0.040(2) 0.042(2) 0.051(3) 0.018(2) 0.0079(19) 0.0109(19) C24 0.060(3) 0.045(2) 0.038(2) 0.014(2) 0.014(2) 0.018(2) C25 0.058(3) 0.050(3) 0.044(2) 0.019(2) 0.026(2) 0.020(2) C26 0.040(2) 0.039(2) 0.041(2) 0.0184(18) 0.0155(17) 0.0076(18) C27 0.094(5) 0.060(3) 0.045(3) 0.005(3) 0.024(3) 0.002(3) C28 0.054(3) 0.038(2) 0.100(5) 0.029(3) 0.022(3) 0.012(2) C29 0.035(2) 0.058(3) 0.058(3) 0.024(2) 0.018(2) 0.007(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 Au P1 2.2663(10) . ? Au S1 2.3008(12) . ? S1 C1 1.746(5) . ? P1 C21 1.815(4) . ? P1 C9 1.826(4) . ? P1 C15 1.831(5) . ? O1 C1 1.345(6) . ? O1 C8 1.439(8) . ? N1 C1 1.267(7) . ? N1 C2 1.422(7) . ? C2 C3 1.365(8) . ? C2 C7 1.377(8) . ? C3 C4 1.390(8) . ? C3 H3 0.9400 . ? C4 C5 1.379(8) . ? C4 H4 0.9400 . ? C5 C6 1.377(8) . ? C5 C5' 1.502(8) . ? C5' H5'1 0.9700 . ? C5' H5'2 0.9700 . ? C5' H5'3 0.9700 . ? C6 C7 1.389(8) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C14 1.383(7) . ? C9 C10 1.409(7) . ? C10 C11 1.399(8) . ? C10 C27 1.498(10) . ? C11 C12 1.361(10) . ? C11 H11 0.9400 . ? C12 C13 1.386(10) . ? C12 H12 0.9400 . ? C13 C14 1.387(7) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.394(6) . ? C15 C16 1.405(7) . ? C16 C17 1.389(7) . ? C16 C28 1.507(7) . ? C17 C18 1.382(9) . ? C17 H17 0.9400 . ? C18 C19 1.357(9) . ? C18 H18 0.9400 . ? C19 C20 1.383(8) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.397(6) . ? C21 C22 1.412(6) . ? C22 C23 1.388(7) . ? C22 C29 1.519(6) . ? C23 C24 1.385(7) . ? C23 H23 0.9400 . ? C24 C25 1.372(8) . ? C24 H24 0.9400 . ? C25 C26 1.385(7) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 179.15(4) . . ? C1 S1 Au 103.61(18) . . ? C21 P1 C9 106.0(2) . . ? C21 P1 C15 106.1(2) . . ? C9 P1 C15 105.6(2) . . ? C21 P1 Au 111.83(13) . . ? C9 P1 Au 111.74(15) . . ? C15 P1 Au 114.98(15) . . ? C1 O1 C8 115.6(5) . . ? C1 N1 C2 121.6(5) . . ? N1 C1 O1 119.9(5) . . ? N1 C1 S1 126.6(4) . . ? O1 C1 S1 113.4(4) . . ? C3 C2 C7 118.6(5) . . ? C3 C2 N1 121.1(5) . . ? C7 C2 N1 120.0(5) . . ? C2 C3 C4 121.2(5) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 117.7(5) . . ? C4 C5 C5' 121.1(6) . . ? C6 C5 C5' 121.1(6) . . ? C5 C5' H5'1 109.5 . . ? C5 C5' H5'2 109.5 . . ? H5'1 C5' H5'2 109.5 . . ? C5 C5' H5'3 109.5 . . ? H5'1 C5' H5'3 109.5 . . ? H5'2 C5' H5'3 109.5 . . ? C7 C6 C5 121.5(5) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C2 120.2(5) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 120.4(5) . . ? C14 C9 P1 118.9(3) . . ? C10 C9 P1 120.6(4) . . ? C9 C10 C11 117.1(6) . . ? C9 C10 C27 123.4(5) . . ? C11 C10 C27 119.5(5) . . ? C12 C11 C10 122.1(5) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 120.6(5) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 118.7(6) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C9 C14 C13 121.0(5) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C20 C15 C16 119.5(4) . . ? C20 C15 P1 119.4(4) . . ? C16 C15 P1 121.0(3) . . ? C15 C16 C17 118.6(5) . . ? C15 C16 C28 122.6(5) . . ? C17 C16 C28 118.8(5) . . ? C18 C17 C16 120.6(5) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 121.0(5) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 119.8(5) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 120.4(5) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C26 C21 C22 118.9(4) . . ? C26 C21 P1 119.3(3) . . ? C22 C21 P1 121.8(3) . . ? C23 C22 C21 118.5(4) . . ? C23 C22 C29 118.2(4) . . ? C21 C22 C29 123.2(4) . . ? C22 C23 C24 121.7(5) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C25 C24 C23 119.9(5) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 119.8(4) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C21 121.2(4) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C10 C27 H27A 109.5 . . ? C10 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C10 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C16 C28 H28A 109.5 . . ? C16 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C16 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C22 C29 H29A 109.5 . . ? C22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 2.07 # 0.74 A from Au _refine_diff_density_min -0.96 _refine_diff_density_rms 0.165 # Attachment 'otolNO2.CIF' data_(o-tol)3PAu(SC(OMe)=NC6H4NO2-4).0.5(CHCl3) _database_code_depnum_ccdc_archive 'CCDC 666593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H28 Au N2 O3 P S, 0.5(C H Cl3)' _chemical_formula_sum 'C29.50 H28.50 Au Cl1.50 N2 O3 P S' _chemical_formula_weight 772.21 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7818(5) _cell_length_b 25.6944(17) _cell_length_c 14.9227(10) _cell_angle_alpha 90 _cell_angle_beta 95.948(2) _cell_angle_gamma 90 _cell_volume 2967.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4185 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 23.5 _exptl_crystal_description needle _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1516 _exptl_absorpt_coefficient_mu 5.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.491 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24780 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.070 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.6 _diffrn_reflns_theta_max 30.0 _reflns_number_total 8593 _reflns_number_gt 6134 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The crystal was found to contain solvent chloroform so that the ratio of complex to solvent was 2:1. The solvent molecule was disordered about a centre of inversion. Hydrogen was not included for this group. ; _vrf_PLAT220_o-tol3PAuSCOMe=NC6H4NO2-4.0.5CHCl3 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.72 Ratio RESPONSE: ...Disordered chloroform was modelled in the refinement, see "_refine_special_details " ; _vrf_PLAT222_o-tol3PAuSCOMe=NC6H4NO2-4.0.5CHCl3 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.42 Ratio RESPONSE: ...Disordered chloroform was modelled in the refinement, see "_refine_special_details " ; _vrf_PLAT773_o-tol3PAuSCOMe=NC6H4NO2-4.0.5CHCl3 ; PROBLEM: Suspect C-C Bond in CIF: C30 -C30 .. 1.77 Ang. RESPONSE: ...Disordered chloroform was modelled in the refinement, see "_refine_special_details " ; # end Validation Reply Form _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^)+(0.0541P)^2^+0.576P] 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 8593 _refine_ls_number_parameters 364 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.073 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.120 _refine_ls_wR_factor_gt 0.098 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.05 _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 Au Au -0.22229(2) -0.207563(8) -0.314622(13) 0.03137(8) Uani 1 1 d . . . S1 S -0.02710(19) -0.27498(6) -0.29061(10) 0.0394(3) Uani 1 1 d . . . P1 P -0.39643(16) -0.13637(5) -0.33078(9) 0.0277(3) Uani 1 1 d . . . O1 O -0.1211(7) -0.2785(2) -0.4627(3) 0.0741(18) Uani 1 1 d . . . O2 O 0.7994(7) -0.4070(2) -0.2038(4) 0.0845(19) Uani 1 1 d . . . O3 O 0.6184(8) -0.4611(3) -0.1607(4) 0.0810(18) Uani 1 1 d . . . N1 N 0.1228(8) -0.3237(3) -0.4217(4) 0.067(2) Uani 1 1 d . . . N2 N 0.6532(7) -0.4233(2) -0.2040(4) 0.0506(14) Uani 1 1 d . . . C1 C 0.0008(9) -0.2965(3) -0.3992(4) 0.0504(18) Uani 1 1 d . . . C2 C 0.2514(8) -0.3459(3) -0.3589(4) 0.0476(17) Uani 1 1 d . . . C3 C 0.2131(8) -0.3867(3) -0.3043(4) 0.0510(17) Uani 1 1 d . . . H3 H 0.0978 -0.3970 -0.3019 0.061 Uiso 1 1 calc R . . C4 C 0.3448(8) -0.4123(3) -0.2533(4) 0.0444(14) Uani 1 1 d . . . H4 H 0.3203 -0.4403 -0.2162 0.053 Uiso 1 1 calc R . . C5 C 0.5132(7) -0.3961(2) -0.2574(4) 0.0384(13) Uani 1 1 d . . . C6 C 0.5514(9) -0.3546(3) -0.3082(4) 0.0475(15) Uani 1 1 d . . . H6 H 0.6662 -0.3432 -0.3077 0.057 Uiso 1 1 calc R . . C7 C 0.4217(9) -0.3296(3) -0.3601(4) 0.0506(16) Uani 1 1 d . . . H7 H 0.4476 -0.3014 -0.3966 0.061 Uiso 1 1 calc R . . C8 C -0.1038(16) -0.2958(5) -0.5531(6) 0.137(6) Uani 1 1 d . . . H8A H -0.1961 -0.2811 -0.5940 0.206 Uiso 1 1 calc R . . H8B H -0.1106 -0.3335 -0.5555 0.206 Uiso 1 1 calc R . . H8C H 0.0069 -0.2846 -0.5707 0.206 Uiso 1 1 calc R . . C9 C -0.5748(6) -0.1415(2) -0.4194(3) 0.0300(11) Uani 1 1 d . . . C10 C -0.5491(7) -0.1611(2) -0.5057(4) 0.0317(11) Uani 1 1 d . . . C11 C -0.6944(8) -0.1657(2) -0.5695(4) 0.0401(13) Uani 1 1 d . . . H11 H -0.6799 -0.1782 -0.6275 0.048 Uiso 1 1 calc R . . C12 C -0.8583(8) -0.1522(3) -0.5491(4) 0.0475(16) Uani 1 1 d . . . H12 H -0.9535 -0.1560 -0.5928 0.057 Uiso 1 1 calc R . . C13 C -0.8824(7) -0.1332(3) -0.4645(4) 0.0452(15) Uani 1 1 d . . . H13 H -0.9934 -0.1239 -0.4507 0.054 Uiso 1 1 calc R . . C14 C -0.7403(7) -0.1279(2) -0.4000(4) 0.0384(13) Uani 1 1 d . . . H14 H -0.7566 -0.1151 -0.3425 0.046 Uiso 1 1 calc R . . C15 C -0.2725(6) -0.0792(2) -0.3561(3) 0.0289(11) Uani 1 1 d . . . C16 C -0.1184(6) -0.0662(2) -0.3016(3) 0.0310(11) Uani 1 1 d . . . C17 C -0.0292(7) -0.0219(2) -0.3242(4) 0.0393(13) Uani 1 1 d . . . H17 H 0.0729 -0.0125 -0.2886 0.047 Uiso 1 1 calc R . . C18 C -0.0864(8) 0.0086(2) -0.3972(4) 0.0400(13) Uani 1 1 d . . . H18 H -0.0243 0.0385 -0.4104 0.048 Uiso 1 1 calc R . . C19 C -0.2351(7) -0.0047(2) -0.4512(4) 0.0365(12) Uani 1 1 d . . . H19 H -0.2730 0.0156 -0.5017 0.044 Uiso 1 1 calc R . . C20 C -0.3274(6) -0.0482(2) -0.4303(4) 0.0319(11) Uani 1 1 d . . . H20 H -0.4291 -0.0570 -0.4667 0.038 Uiso 1 1 calc R . . C21 C -0.4942(6) -0.1186(2) -0.2281(3) 0.0341(12) Uani 1 1 d . . . C22 C -0.5704(7) -0.1565(3) -0.1774(4) 0.0408(14) Uani 1 1 d . . . C23 C -0.6314(8) -0.1396(4) -0.0966(4) 0.059(2) Uani 1 1 d . . . H23 H -0.6833 -0.1640 -0.0610 0.071 Uiso 1 1 calc R . . C24 C -0.6184(9) -0.0898(4) -0.0681(5) 0.061(2) Uani 1 1 d . . . H24 H -0.6565 -0.0805 -0.0125 0.073 Uiso 1 1 calc R . . C25 C -0.5503(9) -0.0531(3) -0.1197(5) 0.061(2) Uani 1 1 d . . . H25 H -0.5457 -0.0182 -0.1011 0.074 Uiso 1 1 calc R . . C26 C -0.4885(8) -0.0673(3) -0.1987(4) 0.0461(15) Uani 1 1 d . . . H26 H -0.4411 -0.0417 -0.2339 0.055 Uiso 1 1 calc R . . C27 C -0.3749(8) -0.1747(3) -0.5327(4) 0.0469(15) Uani 1 1 d . . . H27A H -0.2991 -0.1447 -0.5238 0.070 Uiso 1 1 calc R . . H27B H -0.3856 -0.1847 -0.5957 0.070 Uiso 1 1 calc R . . H27C H -0.3269 -0.2034 -0.4961 0.070 Uiso 1 1 calc R . . C28 C -0.0471(8) -0.0978(3) -0.2209(4) 0.0429(14) Uani 1 1 d . . . H28A H 0.0547 -0.0808 -0.1915 0.064 Uiso 1 1 calc R . . H28B H -0.0164 -0.1323 -0.2404 0.064 Uiso 1 1 calc R . . H28C H -0.1339 -0.1007 -0.1790 0.064 Uiso 1 1 calc R . . C29 C -0.5932(10) -0.2115(3) -0.2060(6) 0.061(2) Uani 1 1 d . . . H29A H -0.4810 -0.2281 -0.2050 0.092 Uiso 1 1 calc R . . H29B H -0.6517 -0.2129 -0.2666 0.092 Uiso 1 1 calc R . . H29C H -0.6618 -0.2296 -0.1651 0.092 Uiso 1 1 calc R . . C30 C -0.022(2) -0.4665(7) -0.4931(10) 0.086(6) Uani 0.50 1 d PD . . Cl1 Cl -0.1214(5) -0.50386(14) -0.5775(2) 0.1400(14) Uani 1 1 d D . . Cl2 Cl -0.1795(9) -0.4386(4) -0.4362(6) 0.158(3) Uani 0.50 1 d PD . . 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 Au 0.02800(11) 0.03297(12) 0.03285(12) 0.00098(9) 0.00176(7) 0.00399(9) S1 0.0380(8) 0.0435(8) 0.0356(7) -0.0012(6) -0.0018(6) 0.0128(6) P1 0.0234(6) 0.0316(7) 0.0281(6) 0.0016(5) 0.0029(5) 0.0007(5) O1 0.074(4) 0.097(4) 0.045(3) -0.027(3) -0.022(2) 0.055(3) O2 0.040(3) 0.087(4) 0.119(5) 0.010(4) -0.023(3) 0.011(3) O3 0.082(4) 0.082(4) 0.077(4) 0.028(3) -0.006(3) 0.028(3) N1 0.063(4) 0.094(5) 0.043(3) -0.013(3) -0.006(3) 0.042(4) N2 0.045(3) 0.047(3) 0.057(3) 0.002(3) -0.007(3) 0.016(3) C1 0.043(3) 0.064(5) 0.041(3) -0.013(3) -0.009(3) 0.026(3) C2 0.048(4) 0.058(4) 0.036(3) -0.013(3) -0.004(3) 0.031(3) C3 0.032(3) 0.068(5) 0.052(4) -0.014(4) -0.001(3) 0.007(3) C4 0.043(3) 0.044(4) 0.046(3) -0.001(3) 0.007(3) -0.001(3) C5 0.034(3) 0.040(3) 0.040(3) -0.003(3) -0.004(2) 0.011(2) C6 0.045(4) 0.043(4) 0.053(4) 0.001(3) -0.001(3) 0.004(3) C7 0.054(4) 0.049(4) 0.048(4) 0.011(3) 0.002(3) 0.006(3) C8 0.158(11) 0.193(13) 0.049(5) -0.052(6) -0.048(6) 0.118(10) C9 0.023(2) 0.030(3) 0.036(3) 0.004(2) 0.000(2) -0.002(2) C10 0.031(3) 0.031(3) 0.033(3) 0.005(2) 0.004(2) 0.003(2) C11 0.046(3) 0.034(3) 0.038(3) -0.002(3) -0.004(3) 0.001(3) C12 0.037(3) 0.052(4) 0.050(4) 0.002(3) -0.012(3) -0.005(3) C13 0.024(3) 0.064(4) 0.047(3) -0.003(3) 0.001(2) 0.001(3) C14 0.026(3) 0.050(4) 0.039(3) 0.005(3) 0.003(2) -0.001(2) C15 0.022(2) 0.039(3) 0.027(2) 0.001(2) 0.0079(19) 0.002(2) C16 0.025(2) 0.036(3) 0.032(3) -0.004(2) 0.003(2) 0.002(2) C17 0.032(3) 0.043(3) 0.042(3) -0.001(3) 0.001(2) -0.005(2) C18 0.043(3) 0.029(3) 0.049(3) 0.000(3) 0.012(3) -0.009(2) C19 0.038(3) 0.033(3) 0.039(3) 0.010(2) 0.004(2) -0.001(2) C20 0.024(2) 0.036(3) 0.035(3) -0.001(2) 0.002(2) 0.003(2) C21 0.022(2) 0.052(4) 0.029(3) 0.002(3) 0.0025(19) 0.005(2) C22 0.026(3) 0.058(4) 0.039(3) 0.009(3) 0.004(2) -0.003(3) C23 0.041(4) 0.097(6) 0.041(4) 0.024(4) 0.011(3) 0.000(4) C24 0.049(4) 0.094(6) 0.041(4) -0.011(4) 0.015(3) 0.008(4) C25 0.056(4) 0.077(5) 0.053(4) -0.028(4) 0.014(3) 0.006(4) C26 0.039(3) 0.052(4) 0.049(4) -0.003(3) 0.014(3) 0.002(3) C27 0.042(3) 0.060(4) 0.038(3) -0.002(3) 0.004(3) 0.014(3) C28 0.037(3) 0.048(4) 0.042(3) 0.005(3) -0.006(2) -0.005(3) C29 0.052(4) 0.062(5) 0.071(5) 0.026(4) 0.015(4) -0.013(3) C30 0.082(13) 0.121(16) 0.051(9) -0.013(11) -0.008(8) -0.023(12) Cl1 0.184(4) 0.114(3) 0.111(2) 0.024(2) -0.040(2) -0.032(2) Cl2 0.103(5) 0.206(9) 0.162(6) -0.066(6) 0.008(4) -0.056(5) _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 Au P1 2.2745(13) . ? Au S1 2.3073(14) . ? S1 C1 1.747(7) . ? P1 C15 1.818(5) . ? P1 C9 1.820(5) . ? P1 C21 1.838(5) . ? O1 C1 1.351(7) . ? O1 C8 1.441(9) . ? O2 N2 1.213(8) . ? O3 N2 1.212(8) . ? N1 C1 1.252(8) . ? N1 C2 1.418(8) . ? N2 C5 1.460(7) . ? C2 C3 1.378(10) . ? C2 C7 1.392(9) . ? C3 C4 1.379(8) . ? C3 H3 0.9400 . ? C4 C5 1.382(8) . ? C4 H4 0.9400 . ? C5 C6 1.358(9) . ? C6 C7 1.368(8) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.416(7) . ? C9 C14 1.393(7) . ? C10 C11 1.406(7) . ? C10 C27 1.496(8) . ? C11 C12 1.386(9) . ? C11 H11 0.9400 . ? C12 C13 1.384(9) . ? C12 H12 0.9400 . ? C13 C14 1.395(8) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.394(7) . ? C15 C16 1.417(7) . ? C16 C17 1.394(8) . ? C16 C28 1.509(8) . ? C17 C18 1.378(8) . ? C17 H17 0.9400 . ? C18 C19 1.382(8) . ? C18 H18 0.9400 . ? C19 C20 1.381(8) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C22 1.401(8) . ? C21 C26 1.389(9) . ? C22 C23 1.410(9) . ? C22 C29 1.482(9) . ? C23 C24 1.348(11) . ? C23 H23 0.9400 . ? C24 C25 1.358(11) . ? C24 H24 0.9400 . ? C25 C26 1.369(9) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C30 Cl1 1.705(13) . ? C30 Cl1 1.639(18) 3_544 ? C30 Cl2 1.719(15) . ? C30 C30 1.77(4) 3_544 ? Cl1 C30 1.639(18) 3_544 ? 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 P1 Au S1 174.69(5) . . ? C1 S1 Au 103.7(2) . . ? C15 P1 C9 106.8(2) . . ? C15 P1 C21 104.3(3) . . ? C9 P1 C21 105.8(2) . . ? C15 P1 Au 110.41(17) . . ? C9 P1 Au 114.85(18) . . ? C21 P1 Au 113.89(18) . . ? C1 O1 C8 115.0(5) . . ? C1 N1 C2 123.3(6) . . ? O3 N2 O2 122.5(6) . . ? O3 N2 C5 118.7(6) . . ? O2 N2 C5 118.8(6) . . ? N1 C1 O1 120.0(6) . . ? N1 C1 S1 126.6(5) . . ? O1 C1 S1 113.3(4) . . ? C3 C2 C7 120.1(5) . . ? C3 C2 N1 121.0(7) . . ? C7 C2 N1 118.5(7) . . ? C2 C3 C4 119.7(6) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.0(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.6(6) . . ? C6 C5 N2 119.1(6) . . ? C4 C5 N2 119.3(6) . . ? C5 C6 C7 119.6(6) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C2 C7 C6 119.9(6) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 119.9(5) . . ? C10 C9 P1 121.2(4) . . ? C14 C9 P1 118.9(4) . . ? C9 C10 C11 117.9(5) . . ? C9 C10 C27 123.0(5) . . ? C11 C10 C27 119.0(5) . . ? C12 C11 C10 121.6(6) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C13 C12 C11 120.2(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.4(6) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C9 121.0(6) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C20 C15 C16 119.5(5) . . ? C20 C15 P1 120.1(4) . . ? C16 C15 P1 120.4(4) . . ? C17 C16 C15 117.8(5) . . ? C17 C16 C28 118.8(5) . . ? C15 C16 C28 123.4(5) . . ? C18 C17 C16 121.9(5) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 119.6(5) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C19 C20 C15 121.1(5) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? C22 C21 C26 119.4(5) . . ? C22 C21 P1 120.8(5) . . ? C26 C21 P1 119.7(5) . . ? C23 C22 C21 116.5(6) . . ? C23 C22 C29 120.0(6) . . ? C21 C22 C29 123.5(6) . . ? C24 C23 C22 122.8(7) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C25 C24 C23 120.0(7) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C26 C25 C24 119.8(7) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C21 121.4(7) . . ? C25 C26 H26 119.3 . . ? C21 C26 H26 119.3 . . ? C10 C27 H27A 109.5 . . ? C10 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C10 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C16 C28 H28A 109.5 . . ? C16 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C16 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C22 C29 H29A 109.5 . . ? C22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? Cl1 C30 Cl1 116.0(11) . 3_544 ? Cl1 C30 Cl2 107.8(9) . . ? Cl1 C30 Cl2 110.5(9) 3_544 . ? Cl1 C30 C30 56.2(7) . 3_544 ? Cl1 C30 C30 59.8(10) 3_544 3_544 ? Cl2 C30 C30 128.2(17) . 3_544 ? C30 Cl1 C30 64.0(11) . 3_544 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.34 # 0.80 A from Au _refine_diff_density_min -0.94 _refine_diff_density_rms 0.179 data_Ph3PAu(SC(OMe)=NC6H4Me-2).0.25MeOH _database_code_depnum_ccdc_archive 'CCDC 666594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H25 Au N O P S, 0.25(C H4 O)' _chemical_formula_sum 'C27.25 H26 Au N O1.25 P S' _chemical_formula_weight 647.49 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1340(6) _cell_length_b 13.8225(11) _cell_length_c 13.8274(11) _cell_angle_alpha 117.394(2) _cell_angle_beta 98.515(2) _cell_angle_gamma 101.882(2) _cell_volume 1296.92(17) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4076 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 29.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 633 _exptl_absorpt_coefficient_mu 5.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.324 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10940 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.061 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7427 _reflns_number_gt 6298 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Crystals were found to contain solvent methanol. This was disordered over a centre of inversion so that overall there were two complex molecules per solvent molecule. The O-H atom was not located and hence, the _chemical_formula_sum C27.25 H26 Au N O1.25 P S differs from the actual refined formula. ; _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^)+(0.0686P)^2^] 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 7427 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.053 _refine_ls_R_factor_gt 0.040 _refine_ls_wR_factor_ref 0.126 _refine_ls_wR_factor_gt 0.101 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_restrained_S_all 1.09 _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 Au Au -0.14069(3) -0.031690(17) -0.212367(16) 0.03026(8) Uani 1 1 d . . . S1 S -0.12643(19) -0.19360(14) -0.36450(12) 0.0387(3) Uani 1 1 d . . . P1 P -0.13450(17) 0.13453(12) -0.06348(11) 0.0253(3) Uani 1 1 d . . . O1 O -0.4547(6) -0.2080(5) -0.4209(4) 0.0476(12) Uani 1 1 d . . . N1 N -0.3648(7) -0.3218(5) -0.5691(4) 0.0430(13) Uani 1 1 d . . . C1 C -0.3295(8) -0.2492(6) -0.4651(5) 0.0373(13) Uani 1 1 d . . . C2 C -0.2350(8) -0.3646(6) -0.6168(5) 0.0387(13) Uani 1 1 d . . . C3 C -0.1930(9) -0.4543(6) -0.6095(5) 0.0451(15) Uani 1 1 d . . . C3' C -0.2694(12) -0.5015(7) -0.5464(7) 0.064(2) Uani 1 1 d . . . H3'1 H -0.2320 -0.4435 -0.4665 0.096 Uiso 1 1 calc R . . H3'2 H -0.2314 -0.5669 -0.5567 0.096 Uiso 1 1 calc R . . H3'3 H -0.3959 -0.5259 -0.5738 0.096 Uiso 1 1 calc R . . C4 C -0.0739(10) -0.4976(7) -0.6657(6) 0.056(2) Uani 1 1 d . . . H4 H -0.0438 -0.5582 -0.6622 0.068 Uiso 1 1 calc R . . C5 C 0.0007(10) -0.4547(7) -0.7261(6) 0.0548(19) Uani 1 1 d . . . H5 H 0.0798 -0.4867 -0.7636 0.066 Uiso 1 1 calc R . . C6 C -0.0393(10) -0.3643(8) -0.7324(7) 0.0563(19) Uani 1 1 d . . . H6 H 0.0140 -0.3338 -0.7725 0.068 Uiso 1 1 calc R . . C7 C -0.1587(10) -0.3201(7) -0.6786(6) 0.0473(16) Uani 1 1 d . . . H7 H -0.1891 -0.2600 -0.6833 0.057 Uiso 1 1 calc R . . C8 C -0.6254(9) -0.2480(9) -0.5009(6) 0.071(3) Uani 1 1 d . . . H8A H -0.7048 -0.2138 -0.4606 0.106 Uiso 1 1 calc R . . H8B H -0.6716 -0.3308 -0.5381 0.106 Uiso 1 1 calc R . . H8C H -0.6135 -0.2259 -0.5574 0.106 Uiso 1 1 calc R . . C9 C -0.2342(7) 0.2189(5) -0.1085(4) 0.0277(10) Uani 1 1 d . . . C10 C -0.1810(7) 0.3380(5) -0.0437(5) 0.0331(11) Uani 1 1 d . . . H10 H -0.0940 0.3765 0.0260 0.040 Uiso 1 1 calc R . . C11 C -0.2562(8) 0.3998(6) -0.0819(6) 0.0397(13) Uani 1 1 d . . . H11 H -0.2199 0.4803 -0.0384 0.048 Uiso 1 1 calc R . . C12 C -0.3837(8) 0.3433(6) -0.1833(6) 0.0458(16) Uani 1 1 d . . . H12 H -0.4339 0.3856 -0.2091 0.055 Uiso 1 1 calc R . . C13 C -0.4388(9) 0.2258(7) -0.2476(6) 0.0468(16) Uani 1 1 d . . . H13 H -0.5268 0.1880 -0.3167 0.056 Uiso 1 1 calc R . . C14 C -0.3646(7) 0.1626(5) -0.2104(5) 0.0352(12) Uani 1 1 d . . . H14 H -0.4026 0.0821 -0.2541 0.042 Uiso 1 1 calc R . . C15 C 0.0865(6) 0.2296(5) 0.0171(4) 0.0269(10) Uani 1 1 d . . . C16 C 0.1484(8) 0.2790(6) 0.1327(5) 0.0393(13) Uani 1 1 d . . . H16 H 0.0757 0.2623 0.1735 0.047 Uiso 1 1 calc R . . C17 C 0.3176(9) 0.3535(7) 0.1893(6) 0.055(2) Uani 1 1 d . . . H17 H 0.3586 0.3865 0.2683 0.067 Uiso 1 1 calc R . . C18 C 0.4248(9) 0.3793(6) 0.1325(7) 0.055(2) Uani 1 1 d . . . H18 H 0.5390 0.4303 0.1719 0.066 Uiso 1 1 calc R . . C19 C 0.3652(8) 0.3304(6) 0.0171(7) 0.0489(16) Uani 1 1 d . . . H19 H 0.4394 0.3479 -0.0226 0.059 Uiso 1 1 calc R . . C20 C 0.1966(8) 0.2555(6) -0.0418(6) 0.0400(13) Uani 1 1 d . . . H20 H 0.1568 0.2223 -0.1209 0.048 Uiso 1 1 calc R . . C21 C -0.2367(6) 0.1186(4) 0.0379(4) 0.0263(10) Uani 1 1 d . . . C22 C -0.2944(8) 0.2049(5) 0.1122(5) 0.0371(12) Uani 1 1 d . . . H22 H -0.2853 0.2717 0.1080 0.045 Uiso 1 1 calc R . . C23 C -0.3654(8) 0.1918(6) 0.1925(5) 0.0406(13) Uani 1 1 d . . . H23 H -0.4058 0.2495 0.2419 0.049 Uiso 1 1 calc R . . C24 C -0.3770(8) 0.0949(6) 0.2001(5) 0.0390(13) Uani 1 1 d . . . H24 H -0.4244 0.0865 0.2549 0.047 Uiso 1 1 calc R . . C25 C -0.3182(8) 0.0097(6) 0.1265(6) 0.0388(13) Uani 1 1 d . . . H25 H -0.3250 -0.0561 0.1321 0.047 Uiso 1 1 calc R . . C26 C -0.2497(7) 0.0206(5) 0.0449(5) 0.0309(11) Uani 1 1 d . . . H26 H -0.2121 -0.0382 -0.0055 0.037 Uiso 1 1 calc R . . C27 C -0.851(4) 0.021(2) -0.386(3) 0.059(9) Uani 0.25 1 d P . . H27A H -0.7370 0.0105 -0.3758 0.088 Uiso 0.25 1 calc PR . . H27B H -0.9297 -0.0266 -0.3675 0.088 Uiso 0.25 1 calc PR . . H27C H -0.8403 0.1010 -0.3368 0.088 Uiso 0.25 1 calc PR . . O2 O -0.914(3) -0.008(2) -0.492(2) 0.091(11) Uani 0.25 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 Au 0.03535(12) 0.02696(12) 0.02019(11) 0.00574(8) 0.00561(8) 0.01062(8) S1 0.0388(7) 0.0376(8) 0.0229(6) 0.0023(6) 0.0020(5) 0.0167(6) P1 0.0299(6) 0.0225(6) 0.0203(6) 0.0085(5) 0.0045(5) 0.0093(5) O1 0.037(2) 0.067(3) 0.026(2) 0.012(2) 0.0080(17) 0.021(2) N1 0.037(3) 0.057(4) 0.024(2) 0.010(2) 0.0066(19) 0.019(2) C1 0.041(3) 0.047(4) 0.025(3) 0.017(3) 0.008(2) 0.018(3) C2 0.033(3) 0.045(4) 0.019(2) 0.003(2) 0.002(2) 0.013(2) C3 0.046(3) 0.038(3) 0.029(3) 0.005(3) -0.006(3) 0.009(3) C3' 0.080(6) 0.054(5) 0.043(4) 0.017(4) 0.008(4) 0.016(4) C4 0.056(4) 0.042(4) 0.043(4) 0.002(3) -0.002(3) 0.022(3) C5 0.051(4) 0.055(5) 0.039(4) 0.008(3) 0.008(3) 0.023(3) C6 0.057(4) 0.069(5) 0.045(4) 0.026(4) 0.021(3) 0.027(4) C7 0.057(4) 0.051(4) 0.035(3) 0.020(3) 0.013(3) 0.024(3) C8 0.040(4) 0.123(8) 0.037(4) 0.027(5) 0.011(3) 0.034(4) C9 0.029(2) 0.030(3) 0.027(2) 0.017(2) 0.0063(19) 0.011(2) C10 0.028(2) 0.032(3) 0.034(3) 0.013(2) 0.005(2) 0.010(2) C11 0.038(3) 0.035(3) 0.055(4) 0.027(3) 0.015(3) 0.014(2) C12 0.037(3) 0.055(4) 0.060(4) 0.040(4) 0.014(3) 0.018(3) C13 0.044(3) 0.058(4) 0.041(4) 0.031(3) 0.000(3) 0.015(3) C14 0.038(3) 0.033(3) 0.032(3) 0.018(2) 0.001(2) 0.008(2) C15 0.027(2) 0.025(3) 0.027(2) 0.011(2) 0.0048(19) 0.0129(19) C16 0.037(3) 0.045(4) 0.027(3) 0.013(3) 0.001(2) 0.016(3) C17 0.041(3) 0.055(5) 0.040(4) 0.003(3) -0.008(3) 0.020(3) C18 0.030(3) 0.038(4) 0.065(5) 0.007(3) -0.006(3) 0.010(3) C19 0.034(3) 0.043(4) 0.069(5) 0.028(4) 0.016(3) 0.011(3) C20 0.034(3) 0.043(4) 0.042(3) 0.020(3) 0.010(2) 0.013(3) C21 0.029(2) 0.023(2) 0.024(2) 0.010(2) 0.0048(18) 0.0076(19) C22 0.048(3) 0.028(3) 0.039(3) 0.016(3) 0.017(3) 0.019(3) C23 0.047(3) 0.036(3) 0.038(3) 0.014(3) 0.021(3) 0.017(3) C24 0.041(3) 0.043(4) 0.033(3) 0.020(3) 0.014(2) 0.010(3) C25 0.043(3) 0.035(3) 0.049(4) 0.027(3) 0.019(3) 0.013(3) C26 0.032(2) 0.030(3) 0.028(3) 0.012(2) 0.008(2) 0.012(2) C27 0.051(15) 0.036(15) 0.066(19) 0.034(15) -0.012(13) -0.031(12) O2 0.089(17) 0.057(15) 0.079(18) 0.040(14) -0.021(15) -0.052(15) _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 Au P1 2.2558(13) . ? Au S1 2.3009(15) . ? S1 C1 1.751(6) . ? P1 C21 1.805(5) . ? P1 C15 1.813(5) . ? P1 C9 1.820(5) . ? O1 C1 1.356(7) . ? O1 C8 1.457(8) . ? N1 C1 1.261(8) . ? N1 C2 1.416(8) . ? C2 C7 1.406(10) . ? C2 C3 1.394(10) . ? C3 C4 1.391(10) . ? C3 C3' 1.446(11) . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C3' H3'3 0.9700 . ? C4 C5 1.369(12) . ? C4 H4 0.9400 . ? C5 C6 1.391(11) . ? C5 H5 0.9400 . ? C6 C7 1.383(10) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.391(8) . ? C9 C14 1.388(7) . ? C10 C11 1.385(8) . ? C10 H10 0.9400 . ? C11 C12 1.370(10) . ? C11 H11 0.9400 . ? C12 C13 1.372(10) . ? C12 H12 0.9400 . ? C13 C14 1.389(8) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.374(8) . ? C15 C20 1.395(8) . ? C16 C17 1.387(9) . ? C16 H16 0.9400 . ? C17 C18 1.355(12) . ? C17 H17 0.9400 . ? C18 C19 1.372(11) . ? C18 H18 0.9400 . ? C19 C20 1.387(9) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C22 1.395(7) . ? C21 C26 1.386(8) . ? C22 C23 1.389(8) . ? C22 H22 0.9400 . ? C23 C24 1.378(9) . ? C23 H23 0.9400 . ? C24 C25 1.387(9) . ? C24 H24 0.9400 . ? C25 C26 1.383(8) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 O2 1.31(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? O2 O2 1.46(6) 2_354 ? 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 P1 Au S1 175.51(5) . . ? C1 S1 Au 105.0(2) . . ? C21 P1 C15 105.7(2) . . ? C21 P1 C9 108.0(2) . . ? C15 P1 C9 103.2(2) . . ? C21 P1 Au 114.72(18) . . ? C15 P1 Au 112.44(17) . . ? C9 P1 Au 111.94(18) . . ? C1 O1 C8 116.3(5) . . ? C1 N1 C2 121.1(5) . . ? N1 C1 O1 120.4(5) . . ? N1 C1 S1 126.0(5) . . ? O1 C1 S1 113.5(4) . . ? C7 C2 C3 120.8(6) . . ? C7 C2 N1 118.3(6) . . ? C3 C2 N1 120.7(6) . . ? C2 C3 C4 117.4(7) . . ? C2 C3 C3' 121.9(7) . . ? C4 C3 C3' 120.7(7) . . ? C3 C3' H3'1 109.5 . . ? C3 C3' H3'2 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? C3 C3' H3'3 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? C5 C4 C3 122.1(7) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 120.7(7) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 118.8(8) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 120.2(7) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 119.6(5) . . ? C10 C9 P1 121.5(4) . . ? C14 C9 P1 119.0(4) . . ? C9 C10 C11 120.0(5) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 119.9(6) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.8(6) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.0(6) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 119.7(6) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C16 C15 C20 119.0(5) . . ? C16 C15 P1 123.3(4) . . ? C20 C15 P1 117.7(4) . . ? C15 C16 C17 120.2(6) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 121.1(7) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.4(6) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 120.8(7) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C15 119.6(6) . . ? C19 C20 H20 120.2 . . ? C15 C20 H20 120.2 . . ? C22 C21 C26 119.8(5) . . ? C22 C21 P1 121.3(4) . . ? C26 C21 P1 118.8(4) . . ? C21 C22 C23 119.7(5) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 120.5(6) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.5(6) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 120.8(6) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 119.7(5) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C27 O2 O2 110(4) . 2_354 ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.79 # 0.83 A from Au _refine_diff_density_min -2.19 # 0.83 A from Au _refine_diff_density_rms 0.325 # Attachment 'PhMe3.CIF' data_Ph3PAu(SC(OMe)=NC6H4Me-3) _database_code_depnum_ccdc_archive 'CCDC 666595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H25 Au N O P S' _chemical_formula_sum 'C27 H25 Au N O P S' _chemical_formula_weight 639.48 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4994(7) _cell_length_b 10.7694(7) _cell_length_c 12.7755(8) _cell_angle_alpha 93.047(1) _cell_angle_beta 114.068(1) _cell_angle_gamma 107.663(1) _cell_volume 1230.54(14) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4562 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 29.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 6.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.622 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10423 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_av_sigmaI/netI 0.039 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7004 _reflns_number_gt 6255 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0411P)^2^+1.0834P] 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 7004 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.045 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_ref 0.089 _refine_ls_wR_factor_gt 0.086 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 Au Au 0.13142(2) 0.107162(16) 0.250111(13) 0.03864(7) Uani 1 1 d . . . S1 S 0.1940(2) -0.02962(13) 0.37899(11) 0.0638(4) Uani 1 1 d . . . P1 P 0.07582(12) 0.25436(10) 0.13718(8) 0.02903(19) Uani 1 1 d . . . O1 O 0.2821(4) 0.2047(3) 0.5064(3) 0.0506(8) Uani 1 1 d . . . N1 N 0.2796(5) 0.0409(4) 0.6112(3) 0.0438(9) Uani 1 1 d . . . C1 C 0.2557(5) 0.0747(5) 0.5137(4) 0.0410(10) Uani 1 1 d . . . C2 C 0.2452(5) -0.0956(5) 0.6190(3) 0.0379(9) Uani 1 1 d . . . C3 C 0.3609(5) -0.1425(5) 0.6739(3) 0.0380(9) Uani 1 1 d . . . H3 H 0.4604 -0.0847 0.7017 0.046 Uiso 1 1 calc R . . C4 C 0.3313(5) -0.2734(5) 0.6883(4) 0.0397(9) Uani 1 1 d . . . C4' C 0.4600(7) -0.3202(6) 0.7503(5) 0.0553(13) Uani 1 1 d . . . H4'1 H 0.4745 -0.3239 0.8299 0.083 Uiso 1 1 calc R . . H4'2 H 0.5502 -0.2586 0.7516 0.083 Uiso 1 1 calc R . . H4'3 H 0.4378 -0.4081 0.7090 0.083 Uiso 1 1 calc R . . C5 C 0.1847(6) -0.3581(5) 0.6468(4) 0.0465(11) Uani 1 1 d . . . H5 H 0.1633 -0.4474 0.6548 0.056 Uiso 1 1 calc R . . C6 C 0.0697(6) -0.3113(6) 0.5935(4) 0.0482(11) Uani 1 1 d . . . H6 H -0.0296 -0.3691 0.5663 0.058 Uiso 1 1 calc R . . C7 C 0.0986(5) -0.1815(6) 0.5796(4) 0.0470(11) Uani 1 1 d . . . H7 H 0.0194 -0.1508 0.5435 0.056 Uiso 1 1 calc R . . C8 C 0.3229(7) 0.2945(5) 0.6109(4) 0.0579(14) Uani 1 1 d . . . H8A H 0.3386 0.3841 0.5962 0.087 Uiso 1 1 calc R . . H8B H 0.4142 0.2922 0.6726 0.087 Uiso 1 1 calc R . . H8C H 0.2436 0.2682 0.6348 0.087 Uiso 1 1 calc R . . C9 C 0.1343(4) 0.4121(4) 0.2326(3) 0.0297(7) Uani 1 1 d . . . C10 C 0.0486(5) 0.4925(4) 0.2103(4) 0.0343(8) Uani 1 1 d . . . H10 H -0.0428 0.4663 0.1424 0.041 Uiso 1 1 calc R . . C11 C 0.0967(6) 0.6108(4) 0.2871(4) 0.0404(10) Uani 1 1 d . . . H11 H 0.0372 0.6638 0.2723 0.048 Uiso 1 1 calc R . . C12 C 0.2320(6) 0.6505(4) 0.3855(4) 0.0441(11) Uani 1 1 d . . . H12 H 0.2658 0.7315 0.4373 0.053 Uiso 1 1 calc R . . C13 C 0.3174(6) 0.5720(5) 0.4078(4) 0.0499(12) Uani 1 1 d . . . H13 H 0.4099 0.5998 0.4748 0.060 Uiso 1 1 calc R . . C14 C 0.2692(5) 0.4525(5) 0.3330(4) 0.0403(10) Uani 1 1 d . . . H14 H 0.3278 0.3986 0.3500 0.048 Uiso 1 1 calc R . . C15 C -0.1203(4) 0.2136(4) 0.0393(3) 0.0302(8) Uani 1 1 d . . . C16 C -0.1718(5) 0.2140(5) -0.0797(4) 0.0388(9) Uani 1 1 d . . . H16 H -0.1043 0.2344 -0.1124 0.047 Uiso 1 1 calc R . . C17 C -0.3219(5) 0.1845(5) -0.1496(4) 0.0451(11) Uani 1 1 d . . . H17 H -0.3563 0.1839 -0.2301 0.054 Uiso 1 1 calc R . . C18 C -0.4214(5) 0.1561(5) -0.1030(4) 0.0443(10) Uani 1 1 d . . . H18 H -0.5233 0.1376 -0.1512 0.053 Uiso 1 1 calc R . . C19 C -0.3722(5) 0.1545(5) 0.0150(4) 0.0456(11) Uani 1 1 d . . . H19 H -0.4409 0.1347 0.0467 0.055 Uiso 1 1 calc R . . C20 C -0.2227(5) 0.1818(5) 0.0864(4) 0.0391(9) Uani 1 1 d . . . H20 H -0.1898 0.1791 0.1662 0.047 Uiso 1 1 calc R . . C21 C 0.1697(4) 0.2891(4) 0.0447(3) 0.0324(8) Uani 1 1 d . . . C22 C 0.2339(5) 0.4180(5) 0.0342(4) 0.0398(9) Uani 1 1 d . . . H22 H 0.2306 0.4898 0.0769 0.048 Uiso 1 1 calc R . . C23 C 0.3027(6) 0.4414(6) -0.0387(5) 0.0511(12) Uani 1 1 d . . . H23 H 0.3481 0.5291 -0.0440 0.061 Uiso 1 1 calc R . . C24 C 0.3043(6) 0.3358(7) -0.1036(5) 0.0600(15) Uani 1 1 d . . . H24 H 0.3499 0.3517 -0.1538 0.072 Uiso 1 1 calc R . . C25 C 0.2394(6) 0.2070(7) -0.0950(5) 0.0614(16) Uani 1 1 d . . . H25 H 0.2396 0.1352 -0.1400 0.074 Uiso 1 1 calc R . . C26 C 0.1739(5) 0.1839(5) -0.0199(4) 0.0460(11) Uani 1 1 d . . . H26 H 0.1320 0.0963 -0.0126 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 Au 0.05587(12) 0.03093(9) 0.02666(8) 0.00737(6) 0.01327(7) 0.01919(7) S1 0.1221(13) 0.0400(6) 0.0304(5) 0.0114(5) 0.0237(7) 0.0442(8) P1 0.0326(5) 0.0282(5) 0.0233(4) 0.0047(4) 0.0097(4) 0.0108(4) O1 0.077(2) 0.0360(17) 0.0353(16) 0.0070(14) 0.0175(16) 0.0262(17) N1 0.051(2) 0.044(2) 0.0275(16) 0.0074(15) 0.0098(16) 0.0165(18) C1 0.052(3) 0.038(2) 0.0288(18) 0.0034(17) 0.0104(18) 0.022(2) C2 0.043(2) 0.041(2) 0.0256(17) 0.0057(16) 0.0119(17) 0.0135(19) C3 0.039(2) 0.043(2) 0.0264(18) 0.0049(16) 0.0117(17) 0.0106(18) C4 0.047(3) 0.045(2) 0.0269(18) 0.0064(17) 0.0165(18) 0.017(2) C4' 0.061(3) 0.056(3) 0.052(3) 0.012(2) 0.021(3) 0.031(3) C5 0.058(3) 0.043(2) 0.037(2) 0.0101(19) 0.025(2) 0.010(2) C6 0.042(3) 0.060(3) 0.037(2) 0.010(2) 0.021(2) 0.007(2) C7 0.038(2) 0.066(3) 0.033(2) 0.010(2) 0.0115(19) 0.020(2) C8 0.078(4) 0.042(3) 0.037(2) -0.003(2) 0.014(3) 0.020(3) C9 0.034(2) 0.0296(18) 0.0275(17) 0.0067(14) 0.0151(15) 0.0114(15) C10 0.036(2) 0.0318(19) 0.0350(19) 0.0110(16) 0.0142(17) 0.0143(17) C11 0.058(3) 0.032(2) 0.047(2) 0.0161(18) 0.031(2) 0.024(2) C12 0.067(3) 0.032(2) 0.034(2) 0.0036(17) 0.025(2) 0.015(2) C13 0.055(3) 0.045(3) 0.033(2) -0.0021(19) 0.007(2) 0.014(2) C14 0.042(2) 0.042(2) 0.035(2) 0.0020(18) 0.0119(18) 0.0206(19) C15 0.0298(19) 0.0300(18) 0.0267(17) 0.0046(14) 0.0104(15) 0.0083(15) C16 0.036(2) 0.051(3) 0.0278(18) 0.0114(18) 0.0152(17) 0.0126(19) C17 0.038(2) 0.058(3) 0.032(2) 0.009(2) 0.0122(18) 0.013(2) C18 0.034(2) 0.051(3) 0.038(2) 0.002(2) 0.0100(18) 0.012(2) C19 0.038(2) 0.049(3) 0.042(2) -0.003(2) 0.020(2) 0.004(2) C20 0.045(2) 0.042(2) 0.0303(19) 0.0060(17) 0.0204(18) 0.0107(19) C21 0.0271(19) 0.042(2) 0.0247(16) 0.0037(15) 0.0079(14) 0.0139(16) C22 0.038(2) 0.047(2) 0.038(2) 0.0108(19) 0.0175(18) 0.020(2) C23 0.045(3) 0.066(3) 0.047(3) 0.021(2) 0.026(2) 0.018(2) C24 0.047(3) 0.091(5) 0.044(3) 0.004(3) 0.027(2) 0.020(3) C25 0.044(3) 0.082(4) 0.051(3) -0.018(3) 0.022(2) 0.017(3) C26 0.041(2) 0.048(3) 0.043(2) -0.005(2) 0.016(2) 0.013(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 Au P1 2.2479(10) . ? Au S1 2.2968(12) . ? S1 C1 1.757(4) . ? P1 C21 1.811(4) . ? P1 C9 1.812(4) . ? P1 C15 1.814(4) . ? O1 C1 1.359(5) . ? O1 C8 1.430(6) . ? N1 C1 1.263(5) . ? N1 C2 1.423(6) . ? C2 C7 1.390(7) . ? C2 C3 1.392(6) . ? C3 C4 1.388(6) . ? C3 H3 0.9400 . ? C4 C5 1.383(7) . ? C4 C4' 1.514(7) . ? C4' H4'1 0.9700 . ? C4' H4'2 0.9700 . ? C4' H4'3 0.9700 . ? C5 C6 1.382(7) . ? C5 H5 0.9400 . ? C6 C7 1.375(7) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C14 1.387(6) . ? C9 C10 1.390(5) . ? C10 C11 1.383(6) . ? C10 H10 0.9400 . ? C11 C12 1.378(7) . ? C11 H11 0.9400 . ? C12 C13 1.370(7) . ? C12 H12 0.9400 . ? C13 C14 1.380(6) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.391(5) . ? C15 C20 1.399(6) . ? C16 C17 1.379(6) . ? C16 H16 0.9400 . ? C17 C18 1.368(7) . ? C17 H17 0.9400 . ? C18 C19 1.383(7) . ? C18 H18 0.9400 . ? C19 C20 1.381(7) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.388(6) . ? C21 C22 1.388(6) . ? C22 C23 1.384(6) . ? C22 H22 0.9400 . ? C23 C24 1.380(8) . ? C23 H23 0.9400 . ? C24 C25 1.380(9) . ? C24 H24 0.9400 . ? C25 C26 1.383(7) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? 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 P1 Au S1 175.12(4) . . ? C1 S1 Au 101.58(15) . . ? C21 P1 C9 105.74(19) . . ? C21 P1 C15 104.91(17) . . ? C9 P1 C15 106.12(18) . . ? C21 P1 Au 115.31(14) . . ? C9 P1 Au 108.00(13) . . ? C15 P1 Au 115.97(13) . . ? C1 O1 C8 116.1(4) . . ? C1 N1 C2 120.5(4) . . ? N1 C1 O1 120.0(4) . . ? N1 C1 S1 127.0(4) . . ? O1 C1 S1 112.9(3) . . ? C7 C2 C3 119.1(4) . . ? C7 C2 N1 121.4(4) . . ? C3 C2 N1 119.4(4) . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.3(4) . . ? C5 C4 C4' 121.3(5) . . ? C3 C4 C4' 119.3(5) . . ? C4 C4' H4'1 109.5 . . ? C4 C4' H4'2 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? C4 C4' H4'3 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? C4 C5 C6 119.9(5) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 120.9(5) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C2 C7 C6 119.9(5) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 118.9(4) . . ? C14 C9 P1 118.3(3) . . ? C10 C9 P1 122.7(3) . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.7(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.7(5) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 120.0(4) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C20 119.2(4) . . ? C16 C15 P1 122.5(3) . . ? C20 C15 P1 118.3(3) . . ? C15 C16 C17 120.0(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.1(4) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C20 120.3(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 119.8(4) . . ? C19 C20 H20 120.1 . . ? C15 C20 H20 120.1 . . ? C26 C21 C22 119.1(4) . . ? C26 C21 P1 119.2(4) . . ? C22 C21 P1 121.6(3) . . ? C23 C22 C21 120.4(5) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 119.8(5) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.3(5) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 119.8(5) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 120.5(5) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.7 . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 2.44 # 0.84 A from Au _refine_diff_density_min -0.70 _refine_diff_density_rms 0.124 # Attachment 'PhPh.CIF' data_Ph3PAu(SC(OMe)=NC6H5).0.5CHCl3 _database_code_depnum_ccdc_archive 'CCDC 666596' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Au N O P S, 0.5(C H Cl3)' _chemical_formula_sum 'C26.50 H23.50 Au Cl1.50 N O P S' _chemical_formula_weight 685.13 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1461(4) _cell_length_b 13.6666(6) _cell_length_c 13.6850(6) _cell_angle_alpha 116.509(1) _cell_angle_beta 99.132(1) _cell_angle_gamma 101.974(1) _cell_volume 1277.56(10) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5384 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 29.9 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 666 _exptl_absorpt_coefficient_mu 6.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.190 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12754 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 30.0 _reflns_number_total 7360 _reflns_number_gt 6664 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The crystals were found to be a hemi-chloroform solvate. This was modelled as disordered over a centre of inversion. Component atoms were refined isotropically. ; _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^)+(0.0708P)^2^+1.7853P] 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 7360 _refine_ls_number_parameters 300 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.052 _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.120 _refine_ls_wR_factor_gt 0.117 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 Au Au 0.14897(2) 0.041371(15) 0.216506(16) 0.03643(8) Uani 1 1 d . . . S1 S 0.14248(19) 0.21149(12) 0.36246(12) 0.0438(3) Uani 1 1 d . . . P1 P 0.13490(16) -0.13037(11) 0.07169(11) 0.0326(2) Uani 1 1 d . . . O1 O 0.4768(5) 0.2341(4) 0.4157(4) 0.0523(10) Uani 1 1 d . . . N1 N 0.3902(7) 0.3478(5) 0.5652(4) 0.0459(11) Uani 1 1 d . . . C1 C 0.3515(7) 0.2724(5) 0.4604(5) 0.0415(11) Uani 1 1 d . . . C2 C 0.2581(8) 0.3876(5) 0.6123(5) 0.0451(12) Uani 1 1 d . . . C3 C 0.1909(8) 0.3485(6) 0.6794(6) 0.0508(14) Uani 1 1 d . . . H3 H 0.2284 0.2927 0.6905 0.061 Uiso 1 1 calc R . . C4 C 0.0679(9) 0.3911(7) 0.7307(7) 0.0617(17) Uani 1 1 d . . . H4 H 0.0208 0.3630 0.7750 0.074 Uiso 1 1 calc R . . C5 C 0.0153(10) 0.4743(7) 0.7165(6) 0.0632(19) Uani 1 1 d . . . H5 H -0.0670 0.5036 0.7517 0.076 Uiso 1 1 calc R . . C6 C 0.0828(10) 0.5144(6) 0.6510(7) 0.0650(19) Uani 1 1 d . . . H6 H 0.0461 0.5710 0.6411 0.078 Uiso 1 1 calc R . . C7 C 0.2051(10) 0.4718(6) 0.5991(6) 0.0584(16) Uani 1 1 d . . . H7 H 0.2518 0.5003 0.5549 0.070 Uiso 1 1 calc R . . C8 C 0.6532(9) 0.2865(8) 0.4934(6) 0.0638(19) Uani 1 1 d . . . H8A H 0.6827 0.3697 0.5311 0.096 Uiso 1 1 calc R . . H8B H 0.7357 0.2627 0.4509 0.096 Uiso 1 1 calc R . . H8C H 0.6589 0.2620 0.5501 0.096 Uiso 1 1 calc R . . C9 C 0.2322(6) -0.2154(4) 0.1187(5) 0.0357(10) Uani 1 1 d . . . C10 C 0.1806(7) -0.3358(5) 0.0525(5) 0.0388(10) Uani 1 1 d . . . H10 H 0.0992 -0.3735 -0.0201 0.047 Uiso 1 1 calc R . . C11 C 0.2490(8) -0.3994(5) 0.0936(6) 0.0444(12) Uani 1 1 d . . . H11 H 0.2139 -0.4800 0.0486 0.053 Uiso 1 1 calc R . . C12 C 0.3685(8) -0.3449(6) 0.2003(6) 0.0466(13) Uani 1 1 d . . . H12 H 0.4134 -0.3884 0.2283 0.056 Uiso 1 1 calc R . . C13 C 0.4213(8) -0.2269(6) 0.2651(6) 0.0515(14) Uani 1 1 d . . . H13 H 0.5036 -0.1896 0.3373 0.062 Uiso 1 1 calc R . . C14 C 0.3538(8) -0.1621(5) 0.2245(5) 0.0444(12) Uani 1 1 d . . . H14 H 0.3912 -0.0813 0.2695 0.053 Uiso 1 1 calc R . . C15 C 0.2321(6) -0.1185(4) -0.0342(4) 0.0335(9) Uani 1 1 d . . . C16 C 0.2861(8) -0.2050(5) -0.1090(5) 0.0429(12) Uani 1 1 d . . . H16 H 0.2733 -0.2731 -0.1053 0.052 Uiso 1 1 calc R . . C17 C 0.3586(8) -0.1922(5) -0.1891(5) 0.0465(12) Uani 1 1 d . . . H17 H 0.3979 -0.2505 -0.2380 0.056 Uiso 1 1 calc R . . C18 C 0.3731(8) -0.0940(5) -0.1973(6) 0.0454(12) Uani 1 1 d . . . H18 H 0.4199 -0.0864 -0.2529 0.054 Uiso 1 1 calc R . . C19 C 0.3191(8) -0.0065(5) -0.1241(5) 0.0440(12) Uani 1 1 d . . . H19 H 0.3291 0.0603 -0.1300 0.053 Uiso 1 1 calc R . . C20 C 0.2498(7) -0.0183(5) -0.0416(5) 0.0398(11) Uani 1 1 d . . . H20 H 0.2149 0.0415 0.0093 0.048 Uiso 1 1 calc R . . C21 C -0.0889(6) -0.2259(4) -0.0057(5) 0.0345(9) Uani 1 1 d . . . C22 C -0.1926(7) -0.2513(5) 0.0571(5) 0.0435(12) Uani 1 1 d . . . H22 H -0.1469 -0.2187 0.1363 0.052 Uiso 1 1 calc R . . C23 C -0.3645(8) -0.3254(6) 0.0018(7) 0.0540(15) Uani 1 1 d . . . H23 H -0.4357 -0.3414 0.0440 0.065 Uiso 1 1 calc R . . C24 C -0.4299(8) -0.3752(6) -0.1149(7) 0.0549(16) Uani 1 1 d . . . H24 H -0.5443 -0.4270 -0.1524 0.066 Uiso 1 1 calc R . . C25 C -0.3283(8) -0.3490(6) -0.1758(6) 0.0516(14) Uani 1 1 d . . . H25 H -0.3749 -0.3812 -0.2549 0.062 Uiso 1 1 calc R . . C26 C -0.1572(7) -0.2755(5) -0.1223(5) 0.0416(11) Uani 1 1 d . . . H26 H -0.0878 -0.2595 -0.1653 0.050 Uiso 1 1 calc R . . C27 C 0.008(2) 1.0409(15) 0.4812(12) 0.081(5) Uiso 0.50 1 d PD . . H27 H 0.0676 1.1167 0.4922 0.097 Uiso 0.50 1 d PD . . Cl1 Cl -0.1747(8) 0.9644(6) 0.3642(5) 0.1029(16) Uiso 0.50 1 d PD . . Cl2 Cl 0.1567(11) 0.9568(8) 0.4457(8) 0.136(3) Uiso 0.50 1 d PD . . Cl3 Cl -0.0374(16) 1.0629(11) 0.6064(9) 0.181(4) Uiso 0.50 1 d PD . . 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 Au 0.04144(12) 0.03284(11) 0.03089(11) 0.01174(8) 0.01183(8) 0.01225(8) S1 0.0458(7) 0.0402(7) 0.0334(6) 0.0087(5) 0.0085(5) 0.0154(6) P1 0.0351(6) 0.0314(6) 0.0315(6) 0.0145(5) 0.0105(5) 0.0126(5) O1 0.042(2) 0.070(3) 0.038(2) 0.020(2) 0.0160(17) 0.016(2) N1 0.046(2) 0.050(3) 0.031(2) 0.013(2) 0.0094(19) 0.014(2) C1 0.043(3) 0.046(3) 0.034(3) 0.021(2) 0.011(2) 0.010(2) C2 0.043(3) 0.041(3) 0.032(3) 0.007(2) 0.003(2) 0.009(2) C3 0.047(3) 0.049(3) 0.051(3) 0.018(3) 0.017(3) 0.016(3) C4 0.054(4) 0.070(4) 0.060(4) 0.027(4) 0.023(3) 0.025(3) C5 0.058(4) 0.059(4) 0.049(4) 0.006(3) 0.014(3) 0.024(3) C6 0.070(4) 0.046(3) 0.058(4) 0.011(3) 0.003(3) 0.028(3) C7 0.073(4) 0.050(3) 0.043(3) 0.018(3) 0.010(3) 0.019(3) C8 0.044(3) 0.091(6) 0.044(3) 0.026(4) 0.012(3) 0.016(3) C9 0.035(2) 0.040(2) 0.037(3) 0.022(2) 0.0116(19) 0.0144(19) C10 0.036(2) 0.037(2) 0.045(3) 0.021(2) 0.012(2) 0.014(2) C11 0.045(3) 0.044(3) 0.057(4) 0.030(3) 0.023(3) 0.020(2) C12 0.045(3) 0.059(3) 0.056(4) 0.040(3) 0.018(3) 0.024(3) C13 0.045(3) 0.063(4) 0.045(3) 0.029(3) 0.004(2) 0.014(3) C14 0.047(3) 0.043(3) 0.039(3) 0.020(2) 0.008(2) 0.011(2) C15 0.034(2) 0.034(2) 0.033(2) 0.0157(19) 0.0117(18) 0.0126(18) C16 0.057(3) 0.036(2) 0.043(3) 0.021(2) 0.020(3) 0.020(2) C17 0.054(3) 0.042(3) 0.048(3) 0.021(3) 0.023(3) 0.021(2) C18 0.045(3) 0.048(3) 0.047(3) 0.025(3) 0.020(2) 0.013(2) C19 0.052(3) 0.042(3) 0.049(3) 0.028(3) 0.021(3) 0.018(2) C20 0.042(3) 0.038(2) 0.045(3) 0.020(2) 0.019(2) 0.017(2) C21 0.034(2) 0.036(2) 0.039(3) 0.018(2) 0.0144(19) 0.0174(19) C22 0.040(3) 0.046(3) 0.044(3) 0.021(2) 0.017(2) 0.013(2) C23 0.041(3) 0.055(3) 0.071(4) 0.032(3) 0.024(3) 0.018(3) C24 0.037(3) 0.044(3) 0.067(4) 0.015(3) 0.009(3) 0.012(2) C25 0.047(3) 0.051(3) 0.043(3) 0.014(3) 0.002(2) 0.018(3) C26 0.044(3) 0.047(3) 0.033(3) 0.017(2) 0.010(2) 0.020(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 Au P1 2.2613(12) . ? Au S1 2.3101(13) . ? S1 C1 1.755(6) . ? P1 C15 1.810(5) . ? P1 C9 1.811(5) . ? P1 C21 1.821(5) . ? O1 C1 1.351(7) . ? O1 C8 1.455(8) . ? N1 C1 1.273(7) . ? N1 C2 1.421(7) . ? C2 C7 1.382(9) . ? C2 C3 1.380(9) . ? C3 C4 1.392(9) . ? C3 H3 0.9400 . ? C4 C5 1.373(11) . ? C4 H4 0.9400 . ? C5 C6 1.370(12) . ? C5 H5 0.9400 . ? C6 C7 1.390(10) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.402(7) . ? C9 C14 1.383(8) . ? C10 C11 1.385(8) . ? C10 H10 0.9400 . ? C11 C12 1.383(9) . ? C11 H11 0.9400 . ? C12 C13 1.374(9) . ? C12 H12 0.9400 . ? C13 C14 1.393(9) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.384(7) . ? C15 C20 1.397(7) . ? C16 C17 1.384(8) . ? C16 H16 0.9400 . ? C17 C18 1.379(8) . ? C17 H17 0.9400 . ? C18 C19 1.383(8) . ? C18 H18 0.9400 . ? C19 C20 1.396(8) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.383(8) . ? C21 C22 1.395(7) . ? C22 C23 1.397(9) . ? C22 H22 0.9400 . ? C23 C24 1.380(11) . ? C23 H23 0.9400 . ? C24 C25 1.368(10) . ? C24 H24 0.9400 . ? C25 C26 1.387(9) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 Cl3 1.488(19) 2_576 ? C27 C27 1.41(3) 2_576 ? C27 Cl3 1.719(15) . ? C27 Cl1 1.727(15) . ? C27 Cl2 1.797(18) 2_576 ? C27 Cl2 1.810(14) . ? C27 H27 0.980 . ? Cl1 Cl3 1.862(13) 2_576 ? Cl2 Cl3 1.013(13) 2_576 ? Cl2 C27 1.797(18) 2_576 ? Cl3 Cl2 1.013(13) 2_576 ? Cl3 C27 1.488(19) 2_576 ? Cl3 Cl1 1.862(13) 2_576 ? 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 P1 Au S1 175.96(5) . . ? C1 S1 Au 105.0(2) . . ? C15 P1 C9 108.2(2) . . ? C15 P1 C21 105.8(2) . . ? C9 P1 C21 102.0(2) . . ? C15 P1 Au 113.59(16) . . ? C9 P1 Au 113.40(18) . . ? C21 P1 Au 112.82(15) . . ? C1 O1 C8 115.8(5) . . ? C1 N1 C2 120.1(5) . . ? N1 C1 O1 120.2(5) . . ? N1 C1 S1 125.4(5) . . ? O1 C1 S1 114.4(4) . . ? C7 C2 C3 119.2(6) . . ? C7 C2 N1 120.8(6) . . ? C3 C2 N1 119.8(6) . . ? C2 C3 C4 120.4(7) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 120.0(7) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.9(7) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.4(7) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C2 C7 C6 120.1(7) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.6(5) . . ? C10 C9 P1 121.4(4) . . ? C14 C9 P1 119.9(4) . . ? C11 C10 C9 120.3(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 120.4(6) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.6(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.5(6) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 120.6(6) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C16 C15 C20 119.1(5) . . ? C16 C15 P1 122.8(4) . . ? C20 C15 P1 118.1(4) . . ? C15 C16 C17 120.6(5) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.5(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 119.5(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C15 C20 C19 120.2(5) . . ? C15 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C26 C21 C22 119.5(5) . . ? C26 C21 P1 123.2(4) . . ? C22 C21 P1 117.3(4) . . ? C23 C22 C21 119.7(6) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 120.0(6) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0(6) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.8(6) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C21 C26 C25 120.0(6) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? Cl3 C27 C27 72.6(13) 2_576 2_576 ? Cl3 C27 Cl3 128.3(12) 2_576 . ? C27 C27 Cl3 55.7(10) 2_576 . ? Cl3 C27 Cl1 70.3(8) 2_576 . ? C27 C27 Cl1 97.0(15) 2_576 . ? Cl3 C27 Cl1 113.1(10) . . ? Cl3 C27 Cl2 126.8(13) 2_576 2_576 ? C27 C27 Cl2 67.4(11) 2_576 2_576 ? Cl1 C27 Cl2 81.2(8) . 2_576 ? C27 C27 Cl2 66.4(11) 2_576 . ? Cl3 C27 Cl2 112.8(10) . . ? Cl1 C27 Cl2 104.3(9) . . ? Cl2 C27 Cl2 133.8(10) 2_576 . ? Cl3 C27 H27 119(10) 2_576 . ? C27 C27 H27 150(10) 2_576 . ? Cl3 C27 H27 107(10) . . ? Cl1 C27 H27 113(10) . . ? Cl2 C27 H27 113(10) 2_576 . ? Cl2 C27 H27 107(10) . . ? Cl3 Cl1 C27 48.8(6) 2_576 . ? Cl3 Cl2 C27 69.1(9) 2_576 2_576 ? Cl3 Cl2 C27 55.3(10) 2_576 . ? C27 Cl2 C27 46.2(10) 2_576 . ? Cl2 Cl3 C27 90.7(11) 2_576 2_576 ? Cl2 Cl3 Cl1 151.5(12) 2_576 2_576 ? C27 Cl3 Cl1 60.9(7) 2_576 2_576 ? Cl2 Cl3 C27 77.5(10) 2_576 . ? C27 Cl3 C27 51.7(12) 2_576 . ? Cl1 Cl3 C27 82.4(7) 2_576 . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.0 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 2.41 # 0.76 A from Au _refine_diff_density_min -1.65 # 0.62 A from Cl3 _refine_diff_density_rms 0.177 # Attachment 'ptolMe2.CIF' data_(p-tol)3PAu(SC(OMe)=NC6H4Me-2) _database_code_depnum_ccdc_archive 'CCDC 666597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H31 Au N O P S' _chemical_formula_sum 'C30 H31 Au N O P S' _chemical_formula_weight 681.55 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 18.8010(9) _cell_length_b 14.4703(8) _cell_length_c 20.7380(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5641.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6918 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2688 _exptl_absorpt_coefficient_mu 5.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.474 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 45534 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 30.1 _reflns_number_total 8262 _reflns_number_gt 5795 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0381P)^2^] 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 8262 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.060 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.083 _refine_ls_wR_factor_gt 0.074 _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_restrained_S_all 1.00 _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 Au Au -0.057268(7) -0.075464(10) -0.175606(6) 0.03410(5) Uani 1 1 d . . . S1 S -0.13546(5) -0.10755(7) -0.09295(5) 0.0387(2) Uani 1 1 d . . . P1 P 0.00620(5) -0.02927(7) -0.26268(4) 0.0346(2) Uani 1 1 d . . . O1 O -0.16437(15) -0.2591(2) -0.03662(14) 0.0538(7) Uani 1 1 d . . . N1 N -0.04509(17) -0.2485(2) -0.05392(15) 0.0413(8) Uani 1 1 d . . . C1 C -0.1064(2) -0.2133(3) -0.05958(17) 0.0394(8) Uani 1 1 d . . . C2 C 0.0171(2) -0.2007(3) -0.07149(16) 0.0372(8) Uani 1 1 d . . . C3 C 0.04765(19) -0.1372(3) -0.02827(17) 0.0388(8) Uani 1 1 d . . . C3' C 0.0106(2) -0.1145(3) 0.03426(18) 0.0508(10) Uani 1 1 d . . . H3'1 H 0.0389 -0.0703 0.0584 0.076 Uiso 1 1 calc R . . H3'2 H 0.0049 -0.1705 0.0595 0.076 Uiso 1 1 calc R . . H3'3 H -0.0358 -0.0882 0.0252 0.076 Uiso 1 1 calc R . . C4 C 0.1122(2) -0.0971(3) -0.0443(2) 0.0454(10) Uani 1 1 d . . . H4 H 0.1330 -0.0542 -0.0160 0.054 Uiso 1 1 calc R . . C5 C 0.1468(2) -0.1192(3) -0.1017(2) 0.0471(10) Uani 1 1 d . . . H5 H 0.1908 -0.0918 -0.1117 0.056 Uiso 1 1 calc R . . C6 C 0.1165(2) -0.1808(3) -0.1433(2) 0.0493(10) Uani 1 1 d . . . H6 H 0.1394 -0.1950 -0.1824 0.059 Uiso 1 1 calc R . . C7 C 0.0519(2) -0.2228(3) -0.12832(18) 0.0437(9) Uani 1 1 d . . . H7 H 0.0319 -0.2661 -0.1568 0.052 Uiso 1 1 calc R . . C8 C -0.1510(3) -0.3448(3) -0.0032(2) 0.0723(15) Uani 1 1 d . . . H8A H -0.1957 -0.3711 0.0111 0.109 Uiso 1 1 calc R . . H8B H -0.1208 -0.3332 0.0339 0.109 Uiso 1 1 calc R . . H8C H -0.1274 -0.3877 -0.0321 0.109 Uiso 1 1 calc R . . C9 C -0.0509(2) 0.0100(3) -0.32755(17) 0.0378(8) Uani 1 1 d . . . C10 C -0.0284(2) 0.0137(3) -0.39131(18) 0.0483(10) Uani 1 1 d . . . H10 H 0.0169 -0.0085 -0.4025 0.058 Uiso 1 1 calc R . . C11 C -0.0723(3) 0.0499(3) -0.4384(2) 0.0589(12) Uani 1 1 d . . . H11 H -0.0558 0.0528 -0.4812 0.071 Uiso 1 1 calc R . . C12 C -0.1401(3) 0.0821(3) -0.4245(2) 0.0560(12) Uani 1 1 d . . . C13 C -0.1624(2) 0.0764(3) -0.3611(2) 0.0527(11) Uani 1 1 d . . . H13 H -0.2083 0.0970 -0.3503 0.063 Uiso 1 1 calc R . . C14 C -0.1191(2) 0.0411(3) -0.3133(2) 0.0458(9) Uani 1 1 d . . . H14 H -0.1359 0.0381 -0.2707 0.055 Uiso 1 1 calc R . . C15 C 0.06311(19) -0.1177(3) -0.29686(17) 0.0357(8) Uani 1 1 d . . . C16 C 0.1319(2) -0.1022(3) -0.31785(18) 0.0429(9) Uani 1 1 d . . . H16 H 0.1509 -0.0422 -0.3157 0.051 Uiso 1 1 calc R . . C17 C 0.1731(2) -0.1728(3) -0.34172(19) 0.0448(9) Uani 1 1 d . . . H17 H 0.2190 -0.1598 -0.3572 0.054 Uiso 1 1 calc R . . C18 C 0.1481(2) -0.2627(3) -0.34339(18) 0.0425(9) Uani 1 1 d . . . C19 C 0.0791(2) -0.2788(3) -0.32225(16) 0.0403(8) Uani 1 1 d . . . H19 H 0.0606 -0.3391 -0.3235 0.048 Uiso 1 1 calc R . . C20 C 0.0368(2) -0.2069(3) -0.29915(18) 0.0400(9) Uani 1 1 d . . . H20 H -0.0098 -0.2191 -0.2851 0.048 Uiso 1 1 calc R . . C21 C 0.06472(18) 0.0672(2) -0.24405(18) 0.0351(8) Uani 1 1 d . . . C22 C 0.0896(2) 0.1278(3) -0.29094(17) 0.0382(8) Uani 1 1 d . . . H22 H 0.0762 0.1199 -0.3343 0.046 Uiso 1 1 calc R . . C23 C 0.1339(2) 0.1996(3) -0.27380(19) 0.0411(9) Uani 1 1 d . . . H23 H 0.1512 0.2395 -0.3060 0.049 Uiso 1 1 calc R . . C24 C 0.15380(19) 0.2144(3) -0.2100(2) 0.0422(9) Uani 1 1 d . . . C25 C 0.1288(2) 0.1526(3) -0.16456(19) 0.0444(9) Uani 1 1 d . . . H25 H 0.1423 0.1603 -0.1212 0.053 Uiso 1 1 calc R . . C26 C 0.0852(2) 0.0805(3) -0.18046(17) 0.0391(8) Uani 1 1 d . . . H26 H 0.0690 0.0400 -0.1482 0.047 Uiso 1 1 calc R . . C27 C -0.1864(3) 0.1254(5) -0.4757(2) 0.0904(19) Uani 1 1 d . . . H27A H -0.2361 0.1139 -0.4658 0.136 Uiso 1 1 calc R . . H27B H -0.1751 0.0986 -0.5174 0.136 Uiso 1 1 calc R . . H27C H -0.1779 0.1915 -0.4770 0.136 Uiso 1 1 calc R . . C28 C 0.1935(2) -0.3401(3) -0.3682(2) 0.0627(13) Uani 1 1 d . . . H28A H 0.2204 -0.3189 -0.4053 0.094 Uiso 1 1 calc R . . H28B H 0.1634 -0.3915 -0.3807 0.094 Uiso 1 1 calc R . . H28C H 0.2260 -0.3599 -0.3346 0.094 Uiso 1 1 calc R . . C29 C 0.1985(3) 0.2972(3) -0.1914(2) 0.0641(13) Uani 1 1 d . . . H29A H 0.2335 0.3089 -0.2248 0.096 Uiso 1 1 calc R . . H29B H 0.2226 0.2848 -0.1510 0.096 Uiso 1 1 calc R . . H29C H 0.1681 0.3509 -0.1866 0.096 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 Au 0.03041(8) 0.03890(8) 0.03299(8) 0.00022(6) 0.00364(6) -0.00224(6) S1 0.0313(5) 0.0453(5) 0.0394(5) 0.0010(4) 0.0063(4) 0.0002(4) P1 0.0290(5) 0.0414(5) 0.0333(4) 0.0017(4) 0.0023(4) -0.0016(4) O1 0.0459(17) 0.0529(17) 0.0627(18) 0.0124(15) 0.0085(15) -0.0119(13) N1 0.043(2) 0.0438(19) 0.0375(16) 0.0011(14) 0.0049(14) -0.0027(14) C1 0.044(2) 0.043(2) 0.0314(18) -0.0004(16) 0.0039(16) -0.0061(17) C2 0.036(2) 0.041(2) 0.0344(18) 0.0034(15) -0.0028(16) 0.0086(16) C3 0.036(2) 0.047(2) 0.0336(18) 0.0011(17) -0.0002(16) 0.0104(16) C3' 0.047(3) 0.068(3) 0.038(2) -0.005(2) -0.0003(19) -0.001(2) C4 0.038(2) 0.050(2) 0.049(2) -0.0062(18) -0.0103(18) 0.0026(17) C5 0.031(2) 0.059(3) 0.051(2) 0.003(2) 0.0017(18) 0.0037(19) C6 0.040(2) 0.064(3) 0.044(2) -0.001(2) 0.0068(19) 0.010(2) C7 0.041(2) 0.051(2) 0.039(2) -0.0079(18) -0.0018(17) 0.0078(18) C8 0.079(4) 0.063(3) 0.075(3) 0.028(3) 0.010(3) -0.010(3) C9 0.034(2) 0.041(2) 0.0389(19) 0.0013(16) -0.0050(16) -0.0012(15) C10 0.044(2) 0.061(3) 0.040(2) -0.004(2) -0.0005(18) 0.004(2) C11 0.071(3) 0.070(3) 0.035(2) -0.003(2) -0.010(2) 0.005(2) C12 0.058(3) 0.059(3) 0.052(3) -0.004(2) -0.020(2) 0.006(2) C13 0.038(2) 0.056(3) 0.064(3) 0.000(2) -0.009(2) 0.0105(19) C14 0.039(2) 0.052(2) 0.047(2) -0.0005(19) 0.0003(18) 0.0007(19) C15 0.032(2) 0.044(2) 0.0303(17) 0.0005(16) 0.0001(15) -0.0044(16) C16 0.036(2) 0.043(2) 0.049(2) 0.0048(18) 0.0057(18) -0.0048(17) C17 0.030(2) 0.057(3) 0.047(2) -0.0003(19) 0.0080(17) -0.0024(18) C18 0.037(2) 0.048(2) 0.043(2) -0.0057(18) -0.0001(17) 0.0006(17) C19 0.042(2) 0.041(2) 0.0384(19) -0.0061(17) 0.0011(17) -0.0076(17) C20 0.0322(19) 0.051(2) 0.0364(18) -0.0037(17) 0.0051(16) -0.0064(17) C21 0.032(2) 0.0378(19) 0.0357(18) -0.0014(15) 0.0008(15) 0.0002(15) C22 0.037(2) 0.042(2) 0.0352(19) 0.0025(16) 0.0012(16) 0.0015(17) C23 0.034(2) 0.040(2) 0.049(2) 0.0098(17) 0.0070(17) 0.0038(16) C24 0.0254(19) 0.040(2) 0.061(3) -0.0030(19) 0.0009(18) 0.0001(15) C25 0.033(2) 0.053(2) 0.047(2) -0.0050(18) -0.0050(17) -0.0005(18) C26 0.035(2) 0.048(2) 0.0346(19) 0.0031(17) 0.0021(16) 0.0004(17) C27 0.091(5) 0.113(5) 0.067(3) 0.009(3) -0.036(3) 0.025(4) C28 0.052(3) 0.060(3) 0.076(3) -0.012(2) 0.010(2) 0.006(2) C29 0.048(3) 0.057(3) 0.087(3) -0.003(3) -0.008(2) -0.014(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 Au P1 2.2653(9) . ? Au S1 2.3055(9) . ? S1 C1 1.766(4) . ? P1 C15 1.813(4) . ? P1 C9 1.812(4) . ? P1 C21 1.818(4) . ? O1 C1 1.362(4) . ? O1 C8 1.443(5) . ? N1 C1 1.265(5) . ? N1 C2 1.406(5) . ? C2 C7 1.385(5) . ? C2 C3 1.406(5) . ? C3 C4 1.385(5) . ? C3 C3' 1.508(5) . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C3' H3'3 0.9700 . ? C4 C5 1.393(6) . ? C4 H4 0.9400 . ? C5 C6 1.366(6) . ? C5 H5 0.9400 . ? C6 C7 1.393(5) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.389(5) . ? C9 C14 1.391(5) . ? C10 C11 1.382(6) . ? C10 H10 0.9400 . ? C11 C12 1.388(6) . ? C11 H11 0.9400 . ? C12 C13 1.381(6) . ? C12 C27 1.511(6) . ? C13 C14 1.381(6) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.383(5) . ? C15 C16 1.384(5) . ? C16 C17 1.374(6) . ? C16 H16 0.9400 . ? C17 C18 1.383(6) . ? C17 H17 0.9400 . ? C18 C19 1.390(5) . ? C18 C28 1.498(6) . ? C19 C20 1.394(6) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.387(5) . ? C21 C22 1.391(5) . ? C22 C23 1.379(5) . ? C22 H22 0.9400 . ? C23 C24 1.390(5) . ? C23 H23 0.9400 . ? C24 C25 1.382(6) . ? C24 C29 1.513(6) . ? C25 C26 1.367(6) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 171.13(4) . . ? C1 S1 Au 105.57(13) . . ? C15 P1 C9 106.31(17) . . ? C15 P1 C21 105.54(17) . . ? C9 P1 C21 105.96(17) . . ? C15 P1 Au 114.47(13) . . ? C9 P1 Au 111.87(13) . . ? C21 P1 Au 112.07(12) . . ? C1 O1 C8 116.5(3) . . ? C1 N1 C2 122.3(3) . . ? N1 C1 O1 120.0(3) . . ? N1 C1 S1 131.9(3) . . ? O1 C1 S1 108.1(3) . . ? C7 C2 N1 120.0(3) . . ? C7 C2 C3 120.0(4) . . ? N1 C2 C3 119.7(3) . . ? C4 C3 C2 118.6(3) . . ? C4 C3 C3' 121.3(4) . . ? C2 C3 C3' 120.1(4) . . ? C3 C3' H3'1 109.5 . . ? C3 C3' H3'2 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? C3 C3' H3'3 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.6(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.5(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.1(4) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.0(4) . . ? C10 C9 P1 122.6(3) . . ? C14 C9 P1 119.4(3) . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.9(4) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 117.2(4) . . ? C13 C12 C27 121.3(5) . . ? C11 C12 C27 121.4(5) . . ? C12 C13 C14 121.7(4) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C13 C14 C9 120.8(4) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C20 C15 C16 118.4(4) . . ? C20 C15 P1 117.5(3) . . ? C16 C15 P1 124.1(3) . . ? C17 C16 C15 121.2(4) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C18 C17 C16 121.2(4) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 117.8(4) . . ? C17 C18 C28 121.2(4) . . ? C19 C18 C28 121.0(4) . . ? C20 C19 C18 121.1(4) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C15 120.3(4) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C26 C21 C22 118.9(3) . . ? C26 C21 P1 118.5(3) . . ? C22 C21 P1 122.6(3) . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 121.6(4) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C23 C24 C25 117.3(4) . . ? C23 C24 C29 120.9(4) . . ? C25 C24 C29 121.8(4) . . ? C26 C25 C24 122.2(4) . . ? C26 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? C21 C26 C25 120.1(4) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.36 # 0.91 A from Au _refine_diff_density_min -0.52 _refine_diff_density_rms 0.143 # Attachment 'ptolMe3.CIF' data_(p-tol)3PAu(SC(OMe)=NC6H4Me-3) _database_code_depnum_ccdc_archive 'CCDC 666598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H31 Au N O P S' _chemical_formula_sum 'C30 H31 Au N O P S' _chemical_formula_weight 681.55 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5910(13) _cell_length_b 27.184(3) _cell_length_c 10.6679(13) _cell_angle_alpha 90 _cell_angle_beta 113.479(3) _cell_angle_gamma 90 _cell_volume 2817.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5633 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 5.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.485 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23359 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.044 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 30.1 _reflns_number_total 8204 _reflns_number_gt 6123 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0421P)^2^] 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 8204 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.053 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.087 _refine_ls_wR_factor_gt 0.080 _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_restrained_S_all 1.00 _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 Au Au -0.184939(15) -0.125884(5) -0.061101(14) 0.04176(6) Uani 1 1 d . . . S1 S -0.22346(13) -0.07762(4) 0.09612(12) 0.0590(3) Uani 1 1 d . . . P1 P -0.15845(10) -0.18055(3) -0.20815(9) 0.03745(19) Uani 1 1 d . . . O1 O -0.1683(3) -0.01306(11) -0.0524(3) 0.0632(9) Uani 1 1 d . . . N1 N -0.2441(4) 0.02147(12) 0.0981(4) 0.0594(9) Uani 1 1 d . . . C1 C -0.2135(4) -0.01642(14) 0.0488(4) 0.0509(10) Uani 1 1 d . . . C2 C -0.2937(5) 0.01830(15) 0.2024(5) 0.0615(12) Uani 1 1 d . . . C3 C -0.2159(6) -0.00105(17) 0.3292(6) 0.0723(14) Uani 1 1 d . . . H3 H -0.1297 -0.0151 0.3453 0.087 Uiso 1 1 calc R . . C4 C -0.2629(8) -0.0001(2) 0.4342(6) 0.090(2) Uani 1 1 d . . . C4' C -0.1771(10) -0.0226(3) 0.5722(7) 0.137(3) Uani 1 1 d . . . H4'1 H -0.1287 -0.0512 0.5596 0.205 Uiso 1 1 calc R . . H4'2 H -0.2369 -0.0324 0.6171 0.205 Uiso 1 1 calc R . . H4'3 H -0.1110 0.0014 0.6283 0.205 Uiso 1 1 calc R . . C5 C -0.3923(9) 0.0209(3) 0.4053(9) 0.110(3) Uani 1 1 d . . . H5 H -0.4261 0.0223 0.4744 0.132 Uiso 1 1 calc R . . C6 C -0.4710(7) 0.0396(2) 0.2782(9) 0.102(2) Uani 1 1 d . . . H6 H -0.5583 0.0530 0.2602 0.122 Uiso 1 1 calc R . . C7 C -0.4213(6) 0.03845(18) 0.1796(7) 0.0826(17) Uani 1 1 d . . . H7 H -0.4747 0.0517 0.0932 0.099 Uiso 1 1 calc R . . C8 C -0.1556(7) 0.03657(17) -0.0967(6) 0.0851(17) Uani 1 1 d . . . H8A H -0.1210 0.0352 -0.1682 0.128 Uiso 1 1 calc R . . H8B H -0.0922 0.0552 -0.0199 0.128 Uiso 1 1 calc R . . H8C H -0.2451 0.0524 -0.1316 0.128 Uiso 1 1 calc R . . C9 C -0.2559(4) -0.16285(12) -0.3837(4) 0.0384(7) Uani 1 1 d . . . C10 C -0.1964(4) -0.15584(15) -0.4769(4) 0.0473(9) Uani 1 1 d . . . H10 H -0.1023 -0.1626 -0.4514 0.057 Uiso 1 1 calc R . . C11 C -0.2748(4) -0.13897(16) -0.6076(4) 0.0514(9) Uani 1 1 d . . . H11 H -0.2330 -0.1343 -0.6696 0.062 Uiso 1 1 calc R . . C12 C -0.4126(4) -0.12888(13) -0.6481(4) 0.0491(9) Uani 1 1 d . . . C13 C -0.4707(4) -0.13577(17) -0.5551(5) 0.0603(12) Uani 1 1 d . . . H13 H -0.5651 -0.1294 -0.5813 0.072 Uiso 1 1 calc R . . C14 C -0.3942(4) -0.15172(17) -0.4251(4) 0.0572(11) Uani 1 1 d . . . H14 H -0.4363 -0.1552 -0.3628 0.069 Uiso 1 1 calc R . . C15 C -0.2233(4) -0.24033(13) -0.1867(4) 0.0396(8) Uani 1 1 d . . . C16 C -0.2906(4) -0.27233(14) -0.2929(4) 0.0490(9) Uani 1 1 d . . . H16 H -0.3015 -0.2640 -0.3822 0.059 Uiso 1 1 calc R . . C17 C -0.3421(4) -0.31656(14) -0.2692(4) 0.0496(9) Uani 1 1 d . . . H17 H -0.3866 -0.3380 -0.3427 0.060 Uiso 1 1 calc R . . C18 C -0.3292(4) -0.32982(14) -0.1390(4) 0.0463(9) Uani 1 1 d . . . C19 C -0.2617(4) -0.29792(14) -0.0328(4) 0.0497(9) Uani 1 1 d . . . H19 H -0.2514 -0.3064 0.0562 0.060 Uiso 1 1 calc R . . C20 C -0.2087(4) -0.25372(15) -0.0543(4) 0.0451(9) Uani 1 1 d . . . H20 H -0.1629 -0.2326 0.0197 0.054 Uiso 1 1 calc R . . C21 C 0.0171(4) -0.18865(12) -0.1898(3) 0.0376(7) Uani 1 1 d . . . C22 C 0.1038(4) -0.14733(15) -0.1563(4) 0.0491(9) Uani 1 1 d . . . H22 H 0.0693 -0.1167 -0.1441 0.059 Uiso 1 1 calc R . . C23 C 0.2380(4) -0.15117(17) -0.1410(4) 0.0556(10) Uani 1 1 d . . . H23 H 0.2941 -0.1230 -0.1189 0.067 Uiso 1 1 calc R . . C24 C 0.2929(4) -0.19584(17) -0.1576(4) 0.0525(10) Uani 1 1 d . . . C25 C 0.2064(5) -0.23594(17) -0.1933(5) 0.0594(11) Uani 1 1 d . . . H25 H 0.2407 -0.2664 -0.2076 0.071 Uiso 1 1 calc R . . C26 C 0.0710(4) -0.23285(14) -0.2088(4) 0.0508(9) Uani 1 1 d . . . H26 H 0.0150 -0.2611 -0.2325 0.061 Uiso 1 1 calc R . . C27 C -0.4992(5) -0.1109(2) -0.7911(5) 0.0759(15) Uani 1 1 d . . . H27A H -0.4920 -0.0754 -0.7944 0.114 Uiso 1 1 calc R . . H27B H -0.5946 -0.1200 -0.8152 0.114 Uiso 1 1 calc R . . H27C H -0.4666 -0.1258 -0.8553 0.114 Uiso 1 1 calc R . . C28 C -0.3836(6) -0.37827(14) -0.1129(6) 0.0693(14) Uani 1 1 d . . . H28A H -0.3094 -0.4021 -0.0811 0.104 Uiso 1 1 calc R . . H28B H -0.4556 -0.3900 -0.1968 0.104 Uiso 1 1 calc R . . H28C H -0.4207 -0.3739 -0.0438 0.104 Uiso 1 1 calc R . . C29 C 0.4421(5) -0.2006(2) -0.1358(6) 0.0811(16) Uani 1 1 d . . . H29A H 0.4773 -0.1686 -0.1464 0.122 Uiso 1 1 calc R . . H29B H 0.4501 -0.2232 -0.2024 0.122 Uiso 1 1 calc R . . H29C H 0.4949 -0.2129 -0.0444 0.122 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 Au 0.04916(9) 0.03713(8) 0.04324(9) -0.00229(6) 0.02291(6) 0.00174(6) S1 0.0914(9) 0.0412(5) 0.0642(7) -0.0046(5) 0.0518(6) 0.0014(5) P1 0.0422(5) 0.0363(4) 0.0344(5) -0.0004(4) 0.0159(4) 0.0007(4) O1 0.091(2) 0.0466(16) 0.074(2) -0.0046(14) 0.0559(19) -0.0034(14) N1 0.069(2) 0.0437(18) 0.079(3) -0.0102(18) 0.045(2) -0.0040(16) C1 0.057(2) 0.044(2) 0.063(3) -0.0065(19) 0.035(2) -0.0059(17) C2 0.078(3) 0.042(2) 0.083(4) -0.020(2) 0.052(3) -0.013(2) C3 0.098(4) 0.054(3) 0.083(4) -0.028(3) 0.055(3) -0.019(3) C4 0.147(6) 0.069(3) 0.079(4) -0.039(3) 0.071(4) -0.053(4) C4' 0.237(10) 0.107(5) 0.091(5) -0.044(4) 0.091(6) -0.074(6) C5 0.153(7) 0.093(5) 0.146(6) -0.065(5) 0.124(6) -0.065(5) C6 0.102(5) 0.091(4) 0.151(7) -0.043(5) 0.092(5) -0.026(4) C7 0.092(4) 0.052(3) 0.134(5) -0.025(3) 0.078(4) -0.014(3) C8 0.133(5) 0.053(3) 0.106(4) 0.003(3) 0.086(4) -0.001(3) C9 0.0427(19) 0.0337(17) 0.0367(18) 0.0024(14) 0.0136(15) -0.0006(14) C10 0.0382(19) 0.061(2) 0.044(2) 0.0061(18) 0.0172(16) 0.0046(17) C11 0.050(2) 0.062(2) 0.044(2) 0.0107(19) 0.0217(18) -0.0009(18) C12 0.045(2) 0.050(2) 0.045(2) 0.0081(17) 0.0097(17) -0.0082(16) C13 0.035(2) 0.081(3) 0.058(3) 0.019(2) 0.0111(18) 0.0054(19) C14 0.045(2) 0.082(3) 0.050(2) 0.018(2) 0.0250(19) 0.005(2) C15 0.0384(18) 0.0414(18) 0.040(2) 0.0001(15) 0.0167(15) 0.0008(14) C16 0.059(2) 0.049(2) 0.035(2) -0.0017(17) 0.0155(18) -0.0038(18) C17 0.051(2) 0.046(2) 0.044(2) -0.0064(17) 0.0112(17) -0.0092(17) C18 0.041(2) 0.0425(19) 0.057(2) 0.0030(17) 0.0208(17) 0.0011(15) C19 0.062(2) 0.050(2) 0.043(2) 0.0061(17) 0.0276(19) 0.0043(18) C20 0.053(2) 0.045(2) 0.035(2) -0.0037(15) 0.0156(17) -0.0026(16) C21 0.0410(19) 0.0407(18) 0.0297(17) 0.0007(14) 0.0126(14) 0.0004(14) C22 0.046(2) 0.048(2) 0.053(2) -0.0108(18) 0.0202(18) -0.0072(17) C23 0.047(2) 0.063(3) 0.053(3) -0.005(2) 0.0161(19) -0.011(2) C24 0.043(2) 0.069(3) 0.044(2) 0.0066(19) 0.0160(17) 0.0056(19) C25 0.061(3) 0.054(2) 0.070(3) 0.006(2) 0.034(2) 0.014(2) C26 0.056(2) 0.0391(19) 0.065(3) 0.0002(19) 0.032(2) 0.0005(17) C27 0.060(3) 0.095(3) 0.053(3) 0.033(3) 0.001(2) -0.008(3) C28 0.071(3) 0.046(2) 0.095(4) 0.009(2) 0.037(3) -0.010(2) C29 0.049(3) 0.118(4) 0.083(4) 0.005(3) 0.032(3) 0.013(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 Au P1 2.2580(9) . ? Au S1 2.2904(10) . ? S1 C1 1.754(4) . ? P1 C21 1.804(4) . ? P1 C15 1.814(4) . ? P1 C9 1.807(4) . ? O1 C1 1.347(5) . ? O1 C8 1.453(5) . ? N1 C1 1.257(5) . ? N1 C2 1.410(6) . ? C2 C3 1.377(7) . ? C2 C7 1.388(7) . ? C3 C4 1.396(7) . ? C3 H3 0.9400 . ? C4 C5 1.401(10) . ? C4 C4' 1.517(9) . ? C4' H4'1 0.9700 . ? C4' H4'2 0.9700 . ? C4' H4'3 0.9700 . ? C5 C6 1.374(10) . ? C5 H5 0.9400 . ? C6 C7 1.351(8) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.386(5) . ? C9 C14 1.385(5) . ? C10 C11 1.386(5) . ? C10 H10 0.9400 . ? C11 C12 1.375(6) . ? C11 H11 0.9400 . ? C12 C13 1.373(6) . ? C12 C27 1.514(6) . ? C13 C14 1.369(6) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C16 1.380(5) . ? C15 C20 1.406(5) . ? C16 C17 1.384(5) . ? C16 H16 0.9400 . ? C17 C18 1.389(6) . ? C17 H17 0.9400 . ? C18 C19 1.379(5) . ? C18 C28 1.507(5) . ? C19 C20 1.383(5) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.379(5) . ? C21 C22 1.404(5) . ? C22 C23 1.369(5) . ? C22 H22 0.9400 . ? C23 C24 1.388(6) . ? C23 H23 0.9400 . ? C24 C25 1.377(6) . ? C24 C29 1.508(6) . ? C25 C26 1.379(6) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 173.41(4) . . ? C1 S1 Au 106.48(14) . . ? C21 P1 C15 107.61(16) . . ? C21 P1 C9 106.43(16) . . ? C15 P1 C9 106.30(16) . . ? C21 P1 Au 114.40(11) . . ? C15 P1 Au 110.13(12) . . ? C9 P1 Au 111.55(12) . . ? C1 O1 C8 115.6(3) . . ? C1 N1 C2 121.3(4) . . ? N1 C1 O1 120.9(4) . . ? N1 C1 S1 127.0(3) . . ? O1 C1 S1 112.1(3) . . ? C3 C2 N1 122.2(4) . . ? C3 C2 C7 118.9(5) . . ? N1 C2 C7 118.7(5) . . ? C2 C3 C4 121.0(6) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 117.5(6) . . ? C3 C4 C4' 120.3(7) . . ? C5 C4 C4' 122.2(6) . . ? C4 C4' H4'1 109.5 . . ? C4 C4' H4'2 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? C4 C4' H4'3 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? C6 C5 C4 121.6(6) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 119.2(7) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 121.8(7) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 117.8(3) . . ? C10 C9 P1 123.1(3) . . ? C14 C9 P1 118.9(3) . . ? C9 C10 C11 120.4(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 121.2(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 118.1(4) . . ? C11 C12 C27 121.5(4) . . ? C13 C12 C27 120.4(4) . . ? C14 C13 C12 121.4(4) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 121.1(4) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C16 C15 C20 118.4(3) . . ? C16 C15 P1 124.0(3) . . ? C20 C15 P1 117.6(3) . . ? C15 C16 C17 120.6(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 121.3(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 118.1(4) . . ? C19 C18 C28 120.6(4) . . ? C17 C18 C28 121.3(4) . . ? C20 C19 C18 121.5(4) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C15 120.1(3) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C26 C21 C22 117.9(4) . . ? C26 C21 P1 124.0(3) . . ? C22 C21 P1 118.1(3) . . ? C23 C22 C21 120.8(4) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 121.3(4) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 117.5(4) . . ? C23 C24 C29 121.4(4) . . ? C25 C24 C29 121.1(4) . . ? C26 C25 C24 122.0(4) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C25 C26 C21 120.4(4) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.31 # 0.79 A from Au _refine_diff_density_min -0.37 _refine_diff_density_rms 0.105 # Attachment 'ptolMe4.CIF' data_(p-tol)3PAu(SC(OMe)=NC6H4Me-4) _database_code_depnum_ccdc_archive 'CCDC 666599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H31 Au N O P S' _chemical_formula_sum 'C30 H31 Au N O P S' _chemical_formula_weight 681.55 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7389(6) _cell_length_b 15.5653(11) _cell_length_c 18.5362(13) _cell_angle_alpha 90 _cell_angle_beta 100.931(2) _cell_angle_gamma 90 _cell_volume 2758.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3364 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 22.4 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 5.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.302 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 22894 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.071 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_theta_max 30.1 _reflns_number_total 8037 _reflns_number_gt 5806 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0513P)^2^] 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 8037 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.078 _refine_ls_R_factor_gt 0.050 _refine_ls_wR_factor_ref 0.121 _refine_ls_wR_factor_gt 0.103 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 Au Au 0.12515(2) 0.075106(14) 0.356412(12) 0.03437(8) Uani 1 1 d . . . S1 S 0.27051(16) 0.13644(10) 0.45588(8) 0.0396(3) Uani 1 1 d . . . P1 P 0.01420(16) 0.01180(10) 0.25146(8) 0.0333(3) Uani 1 1 d . . . O1 O 0.2905(4) 0.2906(3) 0.5015(3) 0.0473(11) Uani 1 1 d . . . N1 N 0.0643(5) 0.2580(3) 0.4582(3) 0.0394(11) Uani 1 1 d . . . C1 C 0.1902(6) 0.2345(4) 0.4710(3) 0.0367(13) Uani 1 1 d . . . C2 C -0.0499(6) 0.2013(4) 0.4339(3) 0.0378(13) Uani 1 1 d . . . C3 C -0.1358(6) 0.2162(4) 0.3667(3) 0.0433(14) Uani 1 1 d . . . H3 H -0.1146 0.2602 0.3360 0.052 Uiso 1 1 calc R . . C4 C -0.2538(7) 0.1656(5) 0.3451(4) 0.0486(16) Uani 1 1 d . . . H4 H -0.3116 0.1759 0.2992 0.058 Uiso 1 1 calc R . . C5 C -0.2884(7) 0.1012(4) 0.3885(4) 0.0501(17) Uani 1 1 d . . . C6 C -0.1988(8) 0.0860(5) 0.4549(4) 0.0550(19) Uani 1 1 d . . . H6 H -0.2187 0.0415 0.4856 0.066 Uiso 1 1 calc R . . C7 C -0.0817(7) 0.1353(5) 0.4762(4) 0.0492(16) Uani 1 1 d . . . H7 H -0.0218 0.1233 0.5211 0.059 Uiso 1 1 calc R . . C5' C -0.4195(8) 0.0483(5) 0.3654(5) 0.069(2) Uani 1 1 d . . . H5'1 H -0.4998 0.0808 0.3740 0.103 Uiso 1 1 calc R . . H5'2 H -0.4119 -0.0044 0.3937 0.103 Uiso 1 1 calc R . . H5'3 H -0.4309 0.0346 0.3135 0.103 Uiso 1 1 calc R . . C8 C 0.2428(8) 0.3724(5) 0.5216(4) 0.061(2) Uani 1 1 d . . . H8A H 0.3225 0.4075 0.5428 0.092 Uiso 1 1 calc R . . H8B H 0.1829 0.3645 0.5573 0.092 Uiso 1 1 calc R . . H8C H 0.1905 0.4006 0.4783 0.092 Uiso 1 1 calc R . . C9 C 0.1389(6) -0.0259(4) 0.1977(3) 0.0347(12) Uani 1 1 d . . . C10 C 0.1062(7) -0.0356(4) 0.1213(3) 0.0399(14) Uani 1 1 d . . . H10 H 0.0181 -0.0182 0.0954 0.048 Uiso 1 1 calc R . . C11 C 0.2020(7) -0.0705(4) 0.0837(4) 0.0454(15) Uani 1 1 d . . . H11 H 0.1776 -0.0786 0.0327 0.055 Uiso 1 1 calc R . . C12 C 0.3349(8) -0.0939(5) 0.1208(4) 0.0492(17) Uani 1 1 d . . . C13 C 0.3677(7) -0.0825(4) 0.1960(4) 0.0513(18) Uani 1 1 d . . . H13 H 0.4571 -0.0977 0.2217 0.062 Uiso 1 1 calc R . . C14 C 0.2715(7) -0.0493(5) 0.2336(4) 0.0462(15) Uani 1 1 d . . . H14 H 0.2960 -0.0422 0.2848 0.055 Uiso 1 1 calc R . . C15 C -0.1004(6) 0.0865(4) 0.1935(3) 0.0340(12) Uani 1 1 d . . . C16 C -0.2414(6) 0.0705(4) 0.1684(4) 0.0418(14) Uani 1 1 d . . . H16 H -0.2792 0.0168 0.1770 0.050 Uiso 1 1 calc R . . C17 C -0.3265(6) 0.1329(4) 0.1308(4) 0.0453(15) Uani 1 1 d . . . H17 H -0.4214 0.1203 0.1131 0.054 Uiso 1 1 calc R . . C18 C -0.2759(7) 0.2142(4) 0.1182(4) 0.0483(16) Uani 1 1 d . . . C19 C -0.1346(7) 0.2279(5) 0.1414(4) 0.062(2) Uani 1 1 d . . . H19 H -0.0955 0.2809 0.1317 0.074 Uiso 1 1 calc R . . C20 C -0.0497(7) 0.1651(4) 0.1786(4) 0.0533(18) Uani 1 1 d . . . H20 H 0.0461 0.1766 0.1943 0.064 Uiso 1 1 calc R . . C21 C -0.0945(6) -0.0800(3) 0.2619(3) 0.0316(11) Uani 1 1 d . . . C22 C -0.1361(6) -0.1380(4) 0.2053(3) 0.0378(13) Uani 1 1 d . . . H22 H -0.1020 -0.1326 0.1613 0.045 Uiso 1 1 calc R . . C23 C -0.2273(6) -0.2038(4) 0.2130(3) 0.0405(14) Uani 1 1 d . . . H23 H -0.2552 -0.2427 0.1742 0.049 Uiso 1 1 calc R . . C24 C -0.2780(6) -0.2132(4) 0.2775(3) 0.0400(14) Uani 1 1 d . . . C25 C -0.2365(7) -0.1558(4) 0.3334(4) 0.0452(15) Uani 1 1 d . . . H25 H -0.2699 -0.1620 0.3775 0.054 Uiso 1 1 calc R . . C26 C -0.1469(7) -0.0891(4) 0.3263(3) 0.0407(14) Uani 1 1 d . . . H26 H -0.1212 -0.0498 0.3650 0.049 Uiso 1 1 calc R . . C27 C 0.4408(9) -0.1307(7) 0.0792(5) 0.084(3) Uani 1 1 d . . . H27A H 0.5315 -0.1049 0.0972 0.126 Uiso 1 1 calc R . . H27B H 0.4118 -0.1184 0.0273 0.126 Uiso 1 1 calc R . . H27C H 0.4469 -0.1924 0.0865 0.126 Uiso 1 1 calc R . . C28 C -0.3709(8) 0.2839(5) 0.0809(5) 0.065(2) Uani 1 1 d . . . H28A H -0.3980 0.3212 0.1177 0.097 Uiso 1 1 calc R . . H28B H -0.4537 0.2582 0.0515 0.097 Uiso 1 1 calc R . . H28C H -0.3221 0.3173 0.0494 0.097 Uiso 1 1 calc R . . C29 C -0.3767(8) -0.2863(5) 0.2853(5) 0.062(2) Uani 1 1 d . . . H29A H -0.3522 -0.3105 0.3342 0.093 Uiso 1 1 calc R . . H29B H -0.3694 -0.3302 0.2491 0.093 Uiso 1 1 calc R . . H29C H -0.4719 -0.2648 0.2774 0.093 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 Au 0.03471(13) 0.03390(12) 0.03269(12) -0.00469(10) 0.00179(9) 0.00045(10) S1 0.0387(8) 0.0388(8) 0.0372(8) -0.0062(6) -0.0029(6) 0.0049(7) P1 0.0319(7) 0.0338(7) 0.0327(7) -0.0042(6) 0.0021(6) 0.0003(6) O1 0.042(2) 0.037(2) 0.059(3) -0.013(2) -0.002(2) -0.003(2) N1 0.037(3) 0.039(3) 0.040(3) -0.008(2) 0.000(2) 0.000(2) C1 0.039(3) 0.035(3) 0.035(3) -0.001(2) 0.004(2) 0.004(3) C2 0.037(3) 0.038(3) 0.039(3) -0.003(3) 0.008(3) 0.006(3) C3 0.041(3) 0.046(4) 0.041(3) 0.002(3) 0.002(3) 0.004(3) C4 0.036(3) 0.057(4) 0.049(4) 0.000(3) -0.003(3) 0.008(3) C5 0.034(3) 0.046(4) 0.071(5) -0.011(3) 0.012(3) 0.005(3) C6 0.058(5) 0.055(4) 0.057(4) 0.010(3) 0.024(4) -0.001(3) C7 0.050(4) 0.057(4) 0.039(3) 0.008(3) 0.002(3) 0.005(3) C5' 0.034(4) 0.060(5) 0.112(8) -0.018(5) 0.011(4) 0.003(3) C8 0.059(4) 0.045(4) 0.072(5) -0.020(4) -0.008(4) 0.005(4) C9 0.034(3) 0.035(3) 0.035(3) 0.002(2) 0.005(2) 0.000(2) C10 0.041(3) 0.037(3) 0.040(3) 0.003(3) 0.005(3) 0.002(3) C11 0.052(4) 0.049(4) 0.037(3) -0.004(3) 0.013(3) -0.010(3) C12 0.048(4) 0.051(4) 0.050(4) -0.006(3) 0.014(3) 0.003(3) C13 0.032(3) 0.057(4) 0.065(5) -0.005(4) 0.009(3) 0.013(3) C14 0.042(4) 0.057(4) 0.038(3) -0.006(3) 0.001(3) 0.008(3) C15 0.030(3) 0.035(3) 0.036(3) 0.000(2) 0.004(2) 0.001(2) C16 0.036(3) 0.040(3) 0.048(4) 0.002(3) 0.007(3) -0.005(3) C17 0.032(3) 0.051(4) 0.053(4) 0.003(3) 0.006(3) 0.000(3) C18 0.045(4) 0.048(4) 0.049(4) 0.003(3) 0.001(3) 0.003(3) C19 0.054(4) 0.049(4) 0.074(5) 0.016(4) -0.009(4) -0.017(4) C20 0.036(4) 0.051(4) 0.067(5) 0.010(4) -0.003(3) -0.011(3) C21 0.029(3) 0.035(3) 0.031(3) -0.002(2) 0.008(2) 0.003(2) C22 0.042(3) 0.040(3) 0.035(3) -0.007(3) 0.016(3) -0.005(3) C23 0.043(3) 0.036(3) 0.042(3) -0.003(3) 0.006(3) 0.002(3) C24 0.033(3) 0.042(3) 0.042(3) 0.003(3) 0.003(3) -0.001(3) C25 0.041(4) 0.057(4) 0.039(3) 0.003(3) 0.010(3) 0.004(3) C26 0.046(4) 0.042(3) 0.035(3) -0.006(3) 0.009(3) 0.000(3) C27 0.070(6) 0.121(8) 0.067(6) -0.010(6) 0.028(5) 0.031(6) C28 0.054(4) 0.048(4) 0.084(6) 0.013(4) -0.009(4) 0.007(4) C29 0.050(4) 0.063(5) 0.073(5) 0.000(4) 0.014(4) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au P1 2.2641(15) . ? Au S1 2.3076(15) . ? S1 C1 1.762(6) . ? P1 C21 1.810(6) . ? P1 C9 1.810(6) . ? P1 C15 1.815(6) . ? O1 C1 1.352(7) . ? O1 C8 1.429(8) . ? N1 C1 1.258(7) . ? N1 C2 1.425(8) . ? C2 C7 1.364(9) . ? C2 C3 1.382(8) . ? C3 C4 1.387(9) . ? C3 H3 0.9400 . ? C4 C5 1.368(10) . ? C4 H4 0.9400 . ? C5 C6 1.387(11) . ? C5 C5' 1.511(10) . ? C6 C7 1.368(10) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C5' H5'1 0.9700 . ? C5' H5'2 0.9700 . ? C5' H5'3 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.399(8) . ? C9 C14 1.384(8) . ? C10 C11 1.377(9) . ? C10 H10 0.9400 . ? C11 C12 1.394(10) . ? C11 H11 0.9400 . ? C12 C13 1.381(10) . ? C12 C27 1.512(10) . ? C13 C14 1.370(9) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.367(8) . ? C15 C16 1.386(8) . ? C16 C17 1.377(9) . ? C16 H16 0.9400 . ? C17 C18 1.394(9) . ? C17 H17 0.9400 . ? C18 C19 1.378(9) . ? C18 C28 1.506(9) . ? C19 C20 1.378(10) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C22 1.386(8) . ? C21 C26 1.392(8) . ? C22 C23 1.381(8) . ? C22 H22 0.9400 . ? C23 C24 1.385(8) . ? C23 H23 0.9400 . ? C24 C25 1.369(9) . ? C24 C29 1.514(9) . ? C25 C26 1.378(9) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? 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 P1 Au S1 170.80(5) . . ? C1 S1 Au 105.2(2) . . ? C21 P1 C9 105.7(3) . . ? C21 P1 C15 105.2(3) . . ? C9 P1 C15 106.5(3) . . ? C21 P1 Au 116.43(19) . . ? C9 P1 Au 110.72(19) . . ? C15 P1 Au 111.67(19) . . ? C1 O1 C8 116.1(5) . . ? C1 N1 C2 123.6(5) . . ? N1 C1 O1 119.5(5) . . ? N1 C1 S1 132.0(5) . . ? O1 C1 S1 108.6(4) . . ? C7 C2 C3 118.7(6) . . ? C7 C2 N1 122.3(6) . . ? C3 C2 N1 119.0(6) . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 121.9(7) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C4 C5 C6 117.6(6) . . ? C4 C5 C5' 121.4(7) . . ? C6 C5 C5' 121.0(7) . . ? C7 C6 C5 120.7(7) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 121.6(6) . . ? C6 C7 H7 119.2 . . ? C2 C7 H7 119.2 . . ? C5 C5' H5'1 109.5 . . ? C5 C5' H5'2 109.5 . . ? H5'1 C5' H5'2 109.5 . . ? C5 C5' H5'3 109.5 . . ? H5'1 C5' H5'3 109.5 . . ? H5'2 C5' H5'3 109.5 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.1(6) . . ? C10 C9 P1 123.0(4) . . ? C14 C9 P1 118.8(5) . . ? C11 C10 C9 120.5(6) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.6(6) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 118.7(6) . . ? C13 C12 C27 120.9(7) . . ? C11 C12 C27 120.4(7) . . ? C14 C13 C12 120.8(7) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 121.3(6) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? C20 C15 C16 117.7(6) . . ? C20 C15 P1 119.2(5) . . ? C16 C15 P1 122.9(4) . . ? C15 C16 C17 120.5(6) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 121.8(6) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C19 C18 C17 116.9(6) . . ? C19 C18 C28 121.5(7) . . ? C17 C18 C28 121.6(6) . . ? C18 C19 C20 121.1(7) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C15 C20 C19 122.1(6) . . ? C15 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C22 C21 C26 118.7(5) . . ? C22 C21 P1 121.8(4) . . ? C26 C21 P1 119.3(4) . . ? C21 C22 C23 120.4(5) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.6(6) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 118.8(6) . . ? C25 C24 C29 121.4(6) . . ? C23 C24 C29 119.8(6) . . ? C24 C25 C26 121.4(6) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C25 C26 C21 120.1(6) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.75 # 0.88 A from Au _refine_diff_density_min -0.91 _refine_diff_density_rms 0.195 # Attachment 'ptolNO2.CIF' data_(p-tol)3PAu(SC(OMe)=NC6H4NO2-4).0.125H2O _database_code_depnum_ccdc_archive 'CCDC 666600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H28 Au N2 O3 P S, 0.125(H2 O)' _chemical_formula_sum 'C29 H28.25 Au N2 O3.125 P S' _chemical_formula_weight 714.78 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7469(6) _cell_length_b 13.9711(8) _cell_length_c 22.0578(13) _cell_angle_alpha 73.618(1) _cell_angle_beta 82.218(1) _cell_angle_gamma 83.664(1) _cell_volume 2847.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4574 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 25.8 _exptl_crystal_description plate _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1405 _exptl_absorpt_coefficient_mu 5.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24193 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.087 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.0 _diffrn_reflns_theta_max 30.1 _reflns_number_total 16333 _reflns_number_gt 10311 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Two independent gold-containing molecules comprise the asymmetric unit. In addition, a disordered water molecule of solvation was modelled in the refinement so that for each gold-containing molecule, there is 1/8 of a water molecule. This gives rise to a molecular formula "C29 H28 Au N2 O3 P S, 0.125(H2 O)" or "C29 H28.5 Au1 N2 O3.125 P1 S1. As the water-bound H atoms were not located, their is a discrepancy between the actual and ideal formulae. ; _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^)+(0.0631P)^2^] 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 16333 _refine_ls_number_parameters 677 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.088 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.130 _refine_ls_wR_factor_gt 0.102 _refine_ls_goodness_of_fit_ref 0.94 _refine_ls_restrained_S_all 0.94 _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 0.25632(2) 0.391975(17) 0.225242(11) 0.03389(7) Uani 1 1 d . . . Au2 Au 0.05030(3) 0.504226(18) 0.305461(12) 0.03881(8) Uani 1 1 d . . . S1 S 0.36921(19) 0.33431(12) 0.31655(8) 0.0417(4) Uani 1 1 d . . . S1A S 0.18959(17) 0.62856(12) 0.24487(9) 0.0411(4) Uani 1 1 d . . . P1 P 0.14921(17) 0.43479(12) 0.13549(8) 0.0336(3) Uani 1 1 d . . . P1A P -0.09321(19) 0.39094(13) 0.36839(8) 0.0405(4) Uani 1 1 d . . . O1 O 0.3833(6) 0.1864(4) 0.2657(2) 0.0534(13) Uani 1 1 d . . . O2 O 0.4246(11) 0.1529(6) 0.6499(3) 0.109(3) Uani 1 1 d . . . O3 O 0.6405(10) 0.1280(6) 0.6269(3) 0.109(3) Uani 1 1 d . . . O1A O -0.0638(5) 0.7094(3) 0.2301(2) 0.0436(11) Uani 1 1 d . . . O2A O 0.6741(6) 0.9952(5) 0.1535(3) 0.0690(16) Uani 1 1 d . . . O3A O 0.6682(7) 0.9913(7) 0.0580(3) 0.112(3) Uani 1 1 d . . . N1 N 0.4424(6) 0.1352(4) 0.3663(3) 0.0485(15) Uani 1 1 d . . . N2 N 0.5224(13) 0.1407(6) 0.6134(4) 0.086(3) Uani 1 1 d . . . N1A N 0.1019(6) 0.8145(4) 0.1811(3) 0.0464(14) Uani 1 1 d . . . N2A N 0.6204(7) 0.9737(5) 0.1128(3) 0.0562(17) Uani 1 1 d . . . C1 C 0.4002(7) 0.2059(5) 0.3211(3) 0.0420(15) Uani 1 1 d . . . C2 C 0.4627(8) 0.1454(5) 0.4258(3) 0.0494(18) Uani 1 1 d . . . C3 C 0.5881(8) 0.1060(5) 0.4497(4) 0.0534(19) Uani 1 1 d . . . H3 H 0.6596 0.0797 0.4245 0.064 Uiso 1 1 calc R . . C4 C 0.6066(10) 0.1059(6) 0.5106(4) 0.064(3) Uani 1 1 d . . . H4 H 0.6923 0.0806 0.5261 0.077 Uiso 1 1 calc R . . C5 C 0.5038(11) 0.1416(6) 0.5490(4) 0.061(2) Uani 1 1 d . . . C6 C 0.3823(12) 0.1795(7) 0.5263(4) 0.075(3) Uani 1 1 d . . . H6 H 0.3106 0.2040 0.5522 0.091 Uiso 1 1 calc R . . C7 C 0.3622(10) 0.1825(6) 0.4640(4) 0.064(2) Uani 1 1 d . . . H7 H 0.2776 0.2108 0.4483 0.077 Uiso 1 1 calc R . . C8 C 0.4145(10) 0.0842(6) 0.2629(4) 0.067(3) Uani 1 1 d . . . H8A H 0.3995 0.0791 0.2214 0.101 Uiso 1 1 calc R . . H8B H 0.3543 0.0411 0.2954 0.101 Uiso 1 1 calc R . . H8C H 0.5106 0.0637 0.2701 0.101 Uiso 1 1 calc R . . C9 C 0.1116(6) 0.3243(4) 0.1144(3) 0.0316(12) Uani 1 1 d . . . C10 C 0.0063(7) 0.3290(5) 0.0758(3) 0.0426(15) Uani 1 1 d . . . H10 H -0.0459 0.3899 0.0610 0.051 Uiso 1 1 calc R . . C11 C -0.0211(7) 0.2473(5) 0.0595(3) 0.0417(15) Uani 1 1 d . . . H11 H -0.0929 0.2526 0.0340 0.050 Uiso 1 1 calc R . . C12 C 0.0543(7) 0.1551(5) 0.0796(4) 0.0439(16) Uani 1 1 d . . . C13 C 0.1581(7) 0.1507(6) 0.1171(4) 0.054(2) Uani 1 1 d . . . H13 H 0.2109 0.0898 0.1315 0.064 Uiso 1 1 calc R . . C14 C 0.1867(7) 0.2353(5) 0.1344(3) 0.0433(16) Uani 1 1 d . . . H14 H 0.2583 0.2304 0.1599 0.052 Uiso 1 1 calc R . . C15 C -0.0195(6) 0.5033(5) 0.1412(3) 0.0338(13) Uani 1 1 d . . . C16 C -0.0557(7) 0.5951(5) 0.1041(3) 0.0407(15) Uani 1 1 d . . . H16 H 0.0109 0.6291 0.0729 0.049 Uiso 1 1 calc R . . C17 C -0.1896(7) 0.6407(5) 0.1110(4) 0.0481(18) Uani 1 1 d . . . H17 H -0.2118 0.7049 0.0849 0.058 Uiso 1 1 calc R . . C18 C -0.2898(7) 0.5915(6) 0.1563(4) 0.0480(18) Uani 1 1 d . . . C19 C -0.2533(8) 0.5000(6) 0.1933(4) 0.0492(17) Uani 1 1 d . . . H19 H -0.3198 0.4660 0.2246 0.059 Uiso 1 1 calc R . . C20 C -0.1199(7) 0.4543(6) 0.1865(3) 0.0440(16) Uani 1 1 d . . . H20 H -0.0979 0.3900 0.2126 0.053 Uiso 1 1 calc R . . C21 C 0.2479(6) 0.5114(5) 0.0666(3) 0.0325(13) Uani 1 1 d . . . C22 C 0.2739(6) 0.4892(5) 0.0082(3) 0.0384(14) Uani 1 1 d . . . H22 H 0.2432 0.4298 0.0045 0.046 Uiso 1 1 calc R . . C23 C 0.3418(7) 0.5501(6) -0.0431(3) 0.0456(17) Uani 1 1 d . . . H23 H 0.3615 0.5309 -0.0811 0.055 Uiso 1 1 calc R . . C24 C 0.3832(7) 0.6420(6) -0.0405(3) 0.0443(16) Uani 1 1 d . . . C25 C 0.3591(7) 0.6648(5) 0.0178(4) 0.0491(18) Uani 1 1 d . . . H25 H 0.3868 0.7252 0.0213 0.059 Uiso 1 1 calc R . . C26 C 0.2942(7) 0.5986(5) 0.0710(3) 0.0420(15) Uani 1 1 d . . . H26 H 0.2819 0.6136 0.1104 0.050 Uiso 1 1 calc R . . C27 C 0.0226(8) 0.0640(6) 0.0608(4) 0.058(2) Uani 1 1 d . . . H27A H 0.0872 0.0559 0.0247 0.087 Uiso 1 1 calc R . . H27B H -0.0715 0.0730 0.0493 0.087 Uiso 1 1 calc R . . H27C H 0.0319 0.0049 0.0963 0.087 Uiso 1 1 calc R . . C28 C -0.4361(8) 0.6379(7) 0.1648(5) 0.068(3) Uani 1 1 d . . . H28A H -0.4428 0.7052 0.1367 0.103 Uiso 1 1 calc R . . H28B H -0.4592 0.6404 0.2085 0.103 Uiso 1 1 calc R . . H28C H -0.5003 0.5979 0.1546 0.103 Uiso 1 1 calc R . . C29 C 0.4477(9) 0.7137(7) -0.0979(4) 0.067(2) Uani 1 1 d . . . H29A H 0.3808 0.7695 -0.1127 0.101 Uiso 1 1 calc R . . H29B H 0.4760 0.6802 -0.1311 0.101 Uiso 1 1 calc R . . H29C H 0.5283 0.7381 -0.0874 0.101 Uiso 1 1 calc R . . C1A C 0.0711(6) 0.7293(5) 0.2149(3) 0.0361(14) Uani 1 1 d . . . C2A C 0.2362(7) 0.8425(5) 0.1668(4) 0.0425(16) Uani 1 1 d . . . C3A C 0.2944(7) 0.8706(5) 0.1033(3) 0.0445(16) Uani 1 1 d . . . H3A H 0.2455 0.8611 0.0717 0.053 Uiso 1 1 calc R . . C4A C 0.4198(7) 0.9113(6) 0.0856(4) 0.0494(17) Uani 1 1 d . . . H4A H 0.4565 0.9300 0.0426 0.059 Uiso 1 1 calc R . . C5A C 0.4911(7) 0.9244(5) 0.1322(4) 0.0456(16) Uani 1 1 d . . . C6A C 0.4406(7) 0.8944(5) 0.1955(3) 0.0425(15) Uani 1 1 d . . . H6A H 0.4924 0.9014 0.2267 0.051 Uiso 1 1 calc R . . C7A C 0.3130(7) 0.8538(5) 0.2128(3) 0.0434(16) Uani 1 1 d . . . H7A H 0.2780 0.8337 0.2560 0.052 Uiso 1 1 calc R . . C8A C -0.1643(7) 0.7901(6) 0.2086(4) 0.0533(19) Uani 1 1 d . . . H8A1 H -0.2569 0.7673 0.2222 0.080 Uiso 1 1 calc R . . H8A2 H -0.1509 0.8134 0.1626 0.080 Uiso 1 1 calc R . . H8A3 H -0.1534 0.8444 0.2265 0.080 Uiso 1 1 calc R . . C9A C -0.2665(7) 0.4484(6) 0.3814(3) 0.0460(17) Uani 1 1 d . . . C10A C -0.3700(8) 0.3990(6) 0.4258(4) 0.054(2) Uani 1 1 d . . . H10A H -0.3507 0.3329 0.4500 0.065 Uiso 1 1 calc R . . C11A C -0.4992(8) 0.4462(7) 0.4343(4) 0.057(2) Uani 1 1 d . . . H11A H -0.5677 0.4117 0.4641 0.068 Uiso 1 1 calc R . . C12A C -0.5312(8) 0.5454(6) 0.3993(4) 0.0529(19) Uani 1 1 d . . . C13A C -0.4301(8) 0.5947(6) 0.3564(4) 0.061(2) Uani 1 1 d . . . H13A H -0.4499 0.6614 0.3334 0.073 Uiso 1 1 calc R . . C14A C -0.2996(8) 0.5488(5) 0.3463(4) 0.0503(18) Uani 1 1 d . . . H14A H -0.2323 0.5840 0.3161 0.060 Uiso 1 1 calc R . . C15A C -0.0411(8) 0.3360(5) 0.4467(3) 0.0461(17) Uani 1 1 d . . . C16A C -0.0810(10) 0.2428(8) 0.4839(4) 0.077(3) Uani 1 1 d . . . H16A H -0.1297 0.2045 0.4664 0.092 Uiso 1 1 calc R . . C17A C -0.0498(11) 0.2046(8) 0.5473(4) 0.084(3) Uani 1 1 d . . . H17A H -0.0793 0.1425 0.5724 0.100 Uiso 1 1 calc R . . C18A C 0.0253(10) 0.2608(9) 0.5715(4) 0.074(3) Uani 1 1 d . . . C19A C 0.0698(11) 0.3520(7) 0.5336(5) 0.072(3) Uani 1 1 d . . . H19A H 0.1234 0.3891 0.5498 0.086 Uiso 1 1 calc R . . C20A C 0.0363(9) 0.3871(6) 0.4738(4) 0.060(2) Uani 1 1 d . . . H20A H 0.0668 0.4492 0.4492 0.072 Uiso 1 1 calc R . . C21A C -0.1107(7) 0.2874(5) 0.3370(3) 0.0422(15) Uani 1 1 d . . . C22A C -0.2348(7) 0.2726(5) 0.3159(3) 0.0446(16) Uani 1 1 d . . . H22A H -0.3165 0.3130 0.3217 0.054 Uiso 1 1 calc R . . C23A C -0.2334(9) 0.1971(6) 0.2865(4) 0.0536(19) Uani 1 1 d . . . H23A H -0.3161 0.1885 0.2718 0.064 Uiso 1 1 calc R . . C24A C -0.1193(9) 0.1342(6) 0.2775(4) 0.055(2) Uani 1 1 d . . . C25A C 0.0021(9) 0.1478(6) 0.3000(4) 0.061(2) Uani 1 1 d . . . H25A H 0.0818 0.1045 0.2962 0.073 Uiso 1 1 calc R . . C26A C 0.0065(8) 0.2239(6) 0.3278(4) 0.0516(18) Uani 1 1 d . . . H26A H 0.0906 0.2334 0.3409 0.062 Uiso 1 1 calc R . . C27A C -0.6729(8) 0.5963(7) 0.4091(4) 0.065(2) Uani 1 1 d . . . H27D H -0.7375 0.5721 0.3880 0.097 Uiso 1 1 calc R . . H27E H -0.6692 0.6680 0.3914 0.097 Uiso 1 1 calc R . . H27F H -0.7038 0.5817 0.4542 0.097 Uiso 1 1 calc R . . C28A C 0.0535(13) 0.2158(10) 0.6411(4) 0.109(4) Uani 1 1 d . . . H28D H 0.0126 0.2610 0.6660 0.164 Uiso 1 1 calc R . . H28E H 0.1529 0.2060 0.6435 0.164 Uiso 1 1 calc R . . H28F H 0.0129 0.1520 0.6577 0.164 Uiso 1 1 calc R . . C29A C -0.1217(11) 0.0551(6) 0.2439(5) 0.078(3) Uani 1 1 d . . . H29D H -0.1951 0.0117 0.2649 0.117 Uiso 1 1 calc R . . H29E H -0.0330 0.0159 0.2449 0.117 Uiso 1 1 calc R . . H29F H -0.1385 0.0864 0.2001 0.117 Uiso 1 1 calc R . . O7 O 0.913(3) 0.005(2) 0.4543(13) 0.081(7) Uiso 0.25 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 0.04117(14) 0.03307(13) 0.02944(13) -0.00939(10) -0.01130(10) 0.00016(10) Au2 0.04692(15) 0.03358(14) 0.03782(15) -0.01123(11) 0.00002(11) -0.01272(11) S1 0.0567(10) 0.0364(9) 0.0366(9) -0.0107(7) -0.0226(8) 0.0000(7) S1A 0.0417(9) 0.0328(8) 0.0463(10) -0.0083(7) 0.0019(7) -0.0070(7) P1 0.0392(8) 0.0338(8) 0.0288(8) -0.0096(7) -0.0098(7) 0.0027(6) P1A 0.0506(10) 0.0400(9) 0.0336(9) -0.0104(8) -0.0017(8) -0.0180(8) O1 0.084(4) 0.039(3) 0.045(3) -0.018(2) -0.034(3) 0.014(2) O2 0.187(9) 0.094(6) 0.040(4) -0.010(4) -0.016(5) -0.006(6) O3 0.160(7) 0.107(6) 0.063(5) 0.014(4) -0.054(5) -0.075(5) O1A 0.042(2) 0.048(3) 0.043(3) -0.012(2) -0.007(2) -0.009(2) O2A 0.065(4) 0.077(4) 0.071(4) -0.018(3) -0.016(3) -0.023(3) O3A 0.081(5) 0.201(9) 0.050(4) -0.006(5) 0.000(4) -0.073(5) N1 0.061(4) 0.044(3) 0.042(3) -0.005(3) -0.023(3) -0.001(3) N2 0.155(9) 0.063(5) 0.044(5) 0.006(4) -0.041(6) -0.041(6) N1A 0.053(3) 0.036(3) 0.047(4) -0.002(3) -0.011(3) -0.009(3) N2A 0.049(4) 0.066(4) 0.049(4) -0.003(3) -0.007(3) -0.014(3) C1 0.047(4) 0.046(4) 0.036(4) -0.012(3) -0.013(3) -0.004(3) C2 0.070(5) 0.039(4) 0.037(4) 0.002(3) -0.018(4) -0.011(3) C3 0.067(5) 0.043(4) 0.048(4) 0.006(3) -0.025(4) -0.019(3) C4 0.078(6) 0.055(5) 0.055(5) 0.019(4) -0.037(5) -0.038(4) C5 0.093(7) 0.043(4) 0.042(4) 0.008(4) -0.020(5) -0.026(4) C6 0.115(8) 0.061(6) 0.044(5) -0.006(4) -0.008(5) -0.004(5) C7 0.082(6) 0.064(5) 0.043(5) -0.002(4) -0.021(4) -0.005(5) C8 0.105(7) 0.044(4) 0.064(6) -0.022(4) -0.045(5) 0.014(4) C9 0.037(3) 0.029(3) 0.029(3) -0.007(2) -0.011(3) 0.003(2) C10 0.049(4) 0.036(3) 0.042(4) -0.009(3) -0.013(3) 0.004(3) C11 0.047(4) 0.044(4) 0.038(4) -0.013(3) -0.014(3) -0.003(3) C12 0.043(4) 0.044(4) 0.051(4) -0.022(3) -0.006(3) -0.001(3) C13 0.049(4) 0.047(4) 0.076(6) -0.031(4) -0.028(4) 0.012(3) C14 0.042(4) 0.044(4) 0.049(4) -0.018(3) -0.021(3) 0.004(3) C15 0.041(3) 0.037(3) 0.026(3) -0.010(3) -0.011(3) 0.003(3) C16 0.050(4) 0.032(3) 0.040(4) -0.008(3) -0.016(3) 0.002(3) C17 0.051(4) 0.044(4) 0.054(5) -0.017(4) -0.028(4) 0.013(3) C18 0.045(4) 0.054(4) 0.056(5) -0.030(4) -0.018(4) 0.005(3) C19 0.051(4) 0.054(4) 0.040(4) -0.011(3) -0.004(3) 0.001(3) C20 0.040(4) 0.051(4) 0.037(4) -0.007(3) -0.008(3) 0.007(3) C21 0.034(3) 0.038(3) 0.028(3) -0.010(3) -0.011(2) 0.001(2) C22 0.040(3) 0.044(4) 0.033(3) -0.014(3) -0.008(3) 0.001(3) C23 0.044(4) 0.062(5) 0.030(4) -0.015(3) -0.005(3) 0.004(3) C24 0.034(3) 0.060(5) 0.036(4) -0.009(3) -0.001(3) -0.002(3) C25 0.047(4) 0.043(4) 0.061(5) -0.018(4) -0.009(4) -0.008(3) C26 0.046(4) 0.052(4) 0.034(3) -0.022(3) -0.005(3) -0.002(3) C27 0.063(5) 0.046(4) 0.073(6) -0.021(4) -0.021(4) -0.007(4) C28 0.045(4) 0.083(6) 0.090(7) -0.044(6) -0.026(5) 0.019(4) C29 0.068(5) 0.069(6) 0.052(5) -0.002(4) 0.010(4) -0.009(4) C1A 0.040(3) 0.040(4) 0.030(3) -0.012(3) -0.002(3) -0.009(3) C2A 0.046(4) 0.025(3) 0.054(4) -0.006(3) -0.006(3) -0.003(3) C3A 0.057(4) 0.043(4) 0.039(4) -0.015(3) -0.016(3) -0.002(3) C4A 0.051(4) 0.059(5) 0.036(4) -0.008(3) -0.003(3) -0.006(3) C5A 0.048(4) 0.040(4) 0.049(4) -0.008(3) -0.012(3) -0.007(3) C6A 0.050(4) 0.037(4) 0.042(4) -0.010(3) -0.013(3) -0.004(3) C7A 0.056(4) 0.038(4) 0.035(4) -0.007(3) -0.001(3) -0.013(3) C8A 0.049(4) 0.049(4) 0.063(5) -0.012(4) -0.019(4) 0.001(3) C9A 0.053(4) 0.057(4) 0.036(4) -0.019(3) -0.004(3) -0.022(3) C10A 0.063(5) 0.051(4) 0.050(4) -0.017(4) 0.014(4) -0.025(4) C11A 0.058(5) 0.076(6) 0.043(4) -0.026(4) 0.011(4) -0.029(4) C12A 0.051(4) 0.070(5) 0.048(4) -0.034(4) 0.003(4) -0.013(4) C13A 0.058(5) 0.056(5) 0.067(6) -0.014(4) -0.006(4) -0.004(4) C14A 0.051(4) 0.045(4) 0.050(4) -0.002(3) -0.001(3) -0.012(3) C15A 0.057(4) 0.050(4) 0.035(4) -0.011(3) -0.007(3) -0.016(3) C16A 0.091(7) 0.098(7) 0.043(5) -0.002(5) -0.014(5) -0.055(6) C17A 0.098(7) 0.098(8) 0.047(5) 0.007(5) -0.012(5) -0.039(6) C18A 0.068(6) 0.122(9) 0.038(5) -0.034(5) -0.013(4) 0.010(6) C19A 0.099(7) 0.067(6) 0.063(6) -0.029(5) -0.036(5) 0.001(5) C20A 0.087(6) 0.052(5) 0.052(5) -0.024(4) -0.019(4) -0.011(4) C21A 0.055(4) 0.039(4) 0.035(4) -0.008(3) -0.006(3) -0.018(3) C22A 0.050(4) 0.046(4) 0.041(4) -0.011(3) -0.009(3) -0.013(3) C23A 0.067(5) 0.059(5) 0.043(4) -0.019(4) -0.009(4) -0.026(4) C24A 0.068(5) 0.053(5) 0.052(5) -0.022(4) 0.005(4) -0.028(4) C25A 0.065(5) 0.057(5) 0.066(6) -0.029(4) 0.002(4) -0.011(4) C26A 0.046(4) 0.058(5) 0.055(5) -0.017(4) -0.010(4) -0.013(3) C27A 0.058(5) 0.073(6) 0.068(6) -0.024(5) -0.010(4) -0.008(4) C28A 0.129(10) 0.160(12) 0.037(5) -0.026(7) -0.021(6) 0.009(9) C29A 0.115(8) 0.062(6) 0.076(6) -0.045(5) 0.001(6) -0.028(5) _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 P1 2.2629(16) . ? Au1 S1 2.3250(16) . ? Au1 Au2 3.0872(4) . ? Au2 P1A 2.2609(17) . ? Au2 S1A 2.3165(16) . ? S1 C1 1.763(7) . ? S1A C1A 1.754(7) . ? P1 C15 1.817(6) . ? P1 C9 1.819(6) . ? P1 C21 1.815(6) . ? P1A C9A 1.810(8) . ? P1A C15A 1.798(7) . ? P1A C21A 1.804(7) . ? O1 C1 1.360(8) . ? O1 C8 1.443(8) . ? O2 N2 1.192(12) . ? O3 N2 1.210(12) . ? O1A C1A 1.352(7) . ? O1A C8A 1.427(8) . ? O2A N2A 1.217(8) . ? O3A N2A 1.203(9) . ? N1 C1 1.266(8) . ? N1 C2 1.401(9) . ? N2 C5 1.453(11) . ? N1A C1A 1.257(8) . ? N1A C2A 1.378(8) . ? N2A C5A 1.457(9) . ? C2 C7 1.360(12) . ? C2 C3 1.392(10) . ? C3 C4 1.379(11) . ? C3 H3 0.9400 . ? C4 C5 1.367(13) . ? C4 H4 0.9400 . ? C5 C6 1.344(13) . ? C6 C7 1.402(11) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C14 1.362(8) . ? C9 C10 1.405(8) . ? C10 C11 1.352(9) . ? C10 H10 0.9400 . ? C11 C12 1.397(9) . ? C11 H11 0.9400 . ? C12 C13 1.377(9) . ? C12 C27 1.519(9) . ? C13 C14 1.406(9) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.386(9) . ? C15 C16 1.351(9) . ? C16 C17 1.396(9) . ? C16 H16 0.9400 . ? C17 C18 1.386(11) . ? C17 H17 0.9400 . ? C18 C19 1.348(10) . ? C18 C28 1.510(10) . ? C19 C20 1.393(9) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C26 1.378(9) . ? C21 C22 1.391(8) . ? C22 C23 1.350(10) . ? C22 H22 0.9400 . ? C23 C24 1.406(10) . ? C23 H23 0.9400 . ? C24 C25 1.395(10) . ? C24 C29 1.487(10) . ? C25 C26 1.397(10) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C2A C3A 1.401(10) . ? C2A C7A 1.392(9) . ? C3A C4A 1.367(10) . ? C3A H3A 0.9400 . ? C4A C5A 1.380(10) . ? C4A H4A 0.9400 . ? C5A C6A 1.377(10) . ? C6A C7A 1.385(9) . ? C6A H6A 0.9400 . ? C7A H7A 0.9400 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C8A H8A3 0.9700 . ? C9A C10A 1.399(9) . ? C9A C14A 1.424(10) . ? C10A C11A 1.371(11) . ? C10A H10A 0.9400 . ? C11A C12A 1.407(11) . ? C11A H11A 0.9400 . ? C12A C13A 1.368(11) . ? C12A C27A 1.500(11) . ? C13A C14A 1.379(11) . ? C13A H13A 0.9400 . ? C14A H14A 0.9400 . ? C15A C16A 1.394(11) . ? C15A C20A 1.384(9) . ? C16A C17A 1.411(12) . ? C16A H16A 0.9400 . ? C17A C18A 1.380(13) . ? C17A H17A 0.9400 . ? C18A C19A 1.390(14) . ? C18A C28A 1.536(12) . ? C19A C20A 1.343(11) . ? C19A H19A 0.9400 . ? C20A H20A 0.9400 . ? C21A C26A 1.395(10) . ? C21A C22A 1.409(9) . ? C22A C23A 1.384(10) . ? C22A H22A 0.9400 . ? C23A C24A 1.368(11) . ? C23A H23A 0.9400 . ? C24A C25A 1.395(11) . ? C24A C29A 1.498(10) . ? C25A C26A 1.375(10) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? C27A H27D 0.9700 . ? C27A H27E 0.9700 . ? C27A H27F 0.9700 . ? C28A H28D 0.9700 . ? C28A H28E 0.9700 . ? C28A H28F 0.9700 . ? C29A H29D 0.9700 . ? C29A H29E 0.9700 . ? C29A H29F 0.9700 . ? 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 P1 Au1 S1 175.16(6) . . ? P1 Au1 Au2 98.82(4) . . ? S1 Au1 Au2 84.69(5) . . ? P1A Au2 S1A 175.84(6) . . ? P1A Au2 Au1 106.68(5) . . ? S1A Au2 Au1 77.46(4) . . ? C1 S1 Au1 101.1(2) . . ? C1A S1A Au2 104.0(2) . . ? C15 P1 C9 103.6(3) . . ? C15 P1 C21 105.1(3) . . ? C9 P1 C21 107.0(3) . . ? C15 P1 Au1 114.9(2) . . ? C9 P1 Au1 111.1(2) . . ? C21 P1 Au1 114.28(19) . . ? C9A P1A C15A 104.9(3) . . ? C9A P1A C21A 106.7(3) . . ? C15A P1A C21A 105.8(3) . . ? C9A P1A Au2 111.1(2) . . ? C15A P1A Au2 113.6(2) . . ? C21A P1A Au2 114.1(2) . . ? C1 O1 C8 116.6(6) . . ? C1A O1A C8A 116.6(5) . . ? C1 N1 C2 124.6(6) . . ? O3 N2 O2 123.0(9) . . ? O2 N2 C5 120.4(10) . . ? O3 N2 C5 116.6(11) . . ? C1A N1A C2A 123.1(6) . . ? O3A N2A O2A 123.4(7) . . ? O3A N2A C5A 118.8(7) . . ? O2A N2A C5A 117.7(7) . . ? N1 C1 O1 119.1(6) . . ? N1 C1 S1 128.7(5) . . ? O1 C1 S1 112.1(5) . . ? C7 C2 C3 118.1(7) . . ? C7 C2 N1 123.7(7) . . ? C3 C2 N1 117.9(8) . . ? C4 C3 C2 119.5(9) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.8(8) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.0(8) . . ? C4 C5 N2 122.0(9) . . ? C6 C5 N2 119.0(10) . . ? C7 C6 C5 120.2(10) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C2 C7 C6 121.3(9) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 118.1(6) . . ? C14 C9 P1 121.0(4) . . ? C10 C9 P1 120.9(5) . . ? C11 C10 C9 121.1(6) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 121.8(6) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 117.1(6) . . ? C13 C12 C27 121.7(6) . . ? C11 C12 C27 121.2(6) . . ? C12 C13 C14 121.3(7) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 120.6(6) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C20 C15 C16 118.1(6) . . ? C20 C15 P1 116.1(5) . . ? C16 C15 P1 125.8(5) . . ? C17 C16 C15 121.6(7) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 120.2(7) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 118.0(7) . . ? C17 C18 C28 121.8(7) . . ? C19 C18 C28 120.2(8) . . ? C18 C19 C20 121.9(7) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C15 C20 C19 120.2(7) . . ? C15 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C26 C21 C22 117.9(6) . . ? C26 C21 P1 118.6(5) . . ? C22 C21 P1 123.4(5) . . ? C23 C22 C21 122.1(6) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C24 C23 C22 120.8(6) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C25 C24 C23 117.7(6) . . ? C25 C24 C29 120.8(7) . . ? C23 C24 C29 121.6(7) . . ? C24 C25 C26 120.4(7) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.9(6) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C12 C27 H27A 109.5 . . ? C12 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C12 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N1A C1A O1A 119.7(6) . . ? N1A C1A S1A 125.8(5) . . ? O1A C1A S1A 114.6(5) . . ? N1A C2A C3A 119.7(6) . . ? N1A C2A C7A 122.2(7) . . ? C3A C2A C7A 117.8(6) . . ? C2A C3A C4A 122.2(6) . . ? C2A C3A H3A 118.9 . . ? C4A C3A H3A 118.9 . . ? C5A C4A C3A 118.5(7) . . ? C5A C4A H4A 120.8 . . ? C3A C4A H4A 120.8 . . ? C6A C5A C4A 121.3(7) . . ? C6A C5A N2A 120.3(6) . . ? C4A C5A N2A 118.3(7) . . ? C5A C6A C7A 119.7(6) . . ? C5A C6A H6A 120.2 . . ? C7A C6A H6A 120.2 . . ? C2A C7A C6A 120.4(6) . . ? C2A C7A H7A 119.8 . . ? C6A C7A H7A 119.8 . . ? O1A C8A H8A1 109.5 . . ? O1A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? O1A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C10A C9A C14A 117.8(7) . . ? C10A C9A P1A 122.8(6) . . ? C14A C9A P1A 119.3(5) . . ? C11A C10A C9A 120.6(8) . . ? C11A C10A H10A 119.7 . . ? C9A C10A H10A 119.7 . . ? C10A C11A C12A 121.2(7) . . ? C10A C11A H11A 119.4 . . ? C12A C11A H11A 119.4 . . ? C11A C12A C13A 118.6(7) . . ? C11A C12A C27A 120.7(7) . . ? C13A C12A C27A 120.6(8) . . ? C12A C13A C14A 121.4(8) . . ? C12A C13A H13A 119.3 . . ? C14A C13A H13A 119.3 . . ? C9A C14A C13A 120.3(7) . . ? C9A C14A H14A 119.9 . . ? C13A C14A H14A 119.9 . . ? C16A C15A C20A 116.9(7) . . ? C16A C15A P1A 122.1(5) . . ? C20A C15A P1A 120.9(6) . . ? C15A C16A C17A 121.5(8) . . ? C15A C16A H16A 119.3 . . ? C17A C16A H16A 119.3 . . ? C18A C17A C16A 118.3(9) . . ? C18A C17A H17A 120.9 . . ? C16A C17A H17A 120.9 . . ? C17A C18A C19A 120.3(8) . . ? C17A C18A C28A 115.6(11) . . ? C19A C18A C28A 124.1(10) . . ? C20A C19A C18A 120.0(8) . . ? C20A C19A H19A 120.0 . . ? C18A C19A H19A 120.0 . . ? C19A C20A C15A 123.0(8) . . ? C19A C20A H20A 118.5 . . ? C15A C20A H20A 118.5 . . ? C26A C21A C22A 118.0(6) . . ? C26A C21A P1A 118.9(5) . . ? C22A C21A P1A 122.8(6) . . ? C23A C22A C21A 118.4(7) . . ? C23A C22A H22A 120.8 . . ? C21A C22A H22A 120.8 . . ? C22A C23A C24A 124.1(7) . . ? C22A C23A H23A 117.9 . . ? C24A C23A H23A 117.9 . . ? C23A C24A C25A 117.0(7) . . ? C23A C24A C29A 122.3(7) . . ? C25A C24A C29A 120.7(8) . . ? C26A C25A C24A 120.7(8) . . ? C26A C25A H25A 119.6 . . ? C24A C25A H25A 119.6 . . ? C25A C26A C21A 121.7(7) . . ? C25A C26A H26A 119.1 . . ? C21A C26A H26A 119.1 . . ? C12A C27A H27D 109.5 . . ? C12A C27A H27E 109.5 . . ? H27D C27A H27E 109.5 . . ? C12A C27A H27F 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? C18A C28A H28D 109.5 . . ? C18A C28A H28E 109.5 . . ? H28D C28A H28E 109.5 . . ? C18A C28A H28F 109.5 . . ? H28D C28A H28F 109.5 . . ? H28E C28A H28F 109.5 . . ? C24A C29A H29D 109.5 . . ? C24A C29A H29E 109.5 . . ? H29D C29A H29E 109.5 . . ? C24A C29A H29F 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.59 # 0.81 A from Au1 _refine_diff_density_min -1.12 # 1.36 A from Au2 _refine_diff_density_rms 0.239 # Attachment 'PhMe4.CIF' data_Ph3PAu(SC(OMe)=NC6H4Me-4) _database_code_depnum_ccdc_archive 'CCDC 666601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H25 Au N O P S' _chemical_formula_sum 'C27 H25 Au N O P S' _chemical_formula_weight 639.48 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1522(5) _cell_length_b 17.7973(11) _cell_length_c 15.3855(9) _cell_angle_alpha 90 _cell_angle_beta 102.508(1) _cell_angle_gamma 90 _cell_volume 2446.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 6.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.502 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(SADABS, Bruker, 2000 & Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20583 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.057 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 30.1 _reflns_number_total 7153 _reflns_number_gt 5490 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'PATTY in DIRDIF92 (Beurskens et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0244P)^2^+3.0528P] 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 7153 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.056 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.085 _refine_ls_wR_factor_gt 0.080 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _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 Au Au 0.147706(19) 0.206025(10) 0.426951(10) 0.03177(6) Uani 1 1 d . . . S1 S 0.19797(16) 0.08212(7) 0.40246(8) 0.0416(3) Uani 1 1 d . . . P1 P 0.08689(12) 0.32388(6) 0.45719(7) 0.0275(2) Uani 1 1 d . . . O1 O 0.2532(3) 0.10595(19) 0.57267(19) 0.0354(7) Uani 1 1 d . . . N1 N 0.2672(4) -0.0173(2) 0.5388(2) 0.0362(9) Uani 1 1 d . . . C1 C 0.2417(5) 0.0490(3) 0.5129(3) 0.0305(9) Uani 1 1 d . . . C2 C 0.2539(5) -0.0778(3) 0.4774(3) 0.0323(9) Uani 1 1 d . . . C3 C 0.3839(5) -0.1146(3) 0.4688(4) 0.0440(12) Uani 1 1 d . . . H3 H 0.4777 -0.0983 0.5011 0.053 Uiso 1 1 calc R . . C4 C 0.3734(6) -0.1754(3) 0.4121(4) 0.0496(13) Uani 1 1 d . . . H4 H 0.4618 -0.1997 0.4060 0.060 Uiso 1 1 calc R . . C5 C 0.2392(7) -0.2017(3) 0.3643(4) 0.0481(13) Uani 1 1 d . . . C5' C 0.2294(9) -0.2692(4) 0.3031(5) 0.073(2) Uani 1 1 d . . . H5'1 H 0.2313 -0.2524 0.2434 0.109 Uiso 1 1 calc R . . H5'2 H 0.1368 -0.2960 0.3022 0.109 Uiso 1 1 calc R . . H5'3 H 0.3137 -0.3023 0.3246 0.109 Uiso 1 1 calc R . . C6 C 0.1106(6) -0.1642(3) 0.3755(4) 0.0459(12) Uani 1 1 d . . . H6 H 0.0164 -0.1813 0.3445 0.055 Uiso 1 1 calc R . . C7 C 0.1183(5) -0.1037(3) 0.4303(3) 0.0401(11) Uani 1 1 d . . . H7 H 0.0298 -0.0792 0.4359 0.048 Uiso 1 1 calc R . . C8 C 0.2887(6) 0.0844(3) 0.6650(3) 0.0505(14) Uani 1 1 d . . . H8A H 0.2956 0.1289 0.7020 0.076 Uiso 1 1 calc R . . H8B H 0.3837 0.0579 0.6780 0.076 Uiso 1 1 calc R . . H8C H 0.2107 0.0517 0.6772 0.076 Uiso 1 1 calc R . . C9 C 0.1387(5) 0.3429(3) 0.5760(3) 0.0313(9) Uani 1 1 d . . . C10 C 0.0532(5) 0.3858(3) 0.6199(3) 0.0364(10) Uani 1 1 d . . . H10 H -0.0392 0.4047 0.5886 0.044 Uiso 1 1 calc R . . C11 C 0.1010(6) 0.4017(3) 0.7094(3) 0.0437(12) Uani 1 1 d . . . H11 H 0.0407 0.4308 0.7387 0.052 Uiso 1 1 calc R . . C12 C 0.2346(7) 0.3753(3) 0.7553(3) 0.0536(14) Uani 1 1 d . . . H12 H 0.2677 0.3867 0.8161 0.064 Uiso 1 1 calc R . . C13 C 0.3213(8) 0.3319(5) 0.7123(4) 0.072(2) Uani 1 1 d . . . H13 H 0.4136 0.3131 0.7440 0.087 Uiso 1 1 calc R . . C14 C 0.2737(7) 0.3160(4) 0.6233(4) 0.0623(18) Uani 1 1 d . . . H14 H 0.3338 0.2865 0.5945 0.075 Uiso 1 1 calc R . . C15 C -0.1126(5) 0.3404(2) 0.4223(3) 0.0288(9) Uani 1 1 d . . . C16 C -0.1701(5) 0.4100(3) 0.3900(3) 0.0314(9) Uani 1 1 d . . . H16 H -0.1053 0.4503 0.3864 0.038 Uiso 1 1 calc R . . C17 C -0.3238(5) 0.4192(3) 0.3632(3) 0.0370(10) Uani 1 1 d . . . H17 H -0.3629 0.4662 0.3420 0.044 Uiso 1 1 calc R . . C18 C -0.4194(5) 0.3605(3) 0.3673(3) 0.0416(12) Uani 1 1 d . . . H18 H -0.5233 0.3672 0.3482 0.050 Uiso 1 1 calc R . . C19 C -0.3627(6) 0.2917(3) 0.3995(4) 0.0506(14) Uani 1 1 d . . . H19 H -0.4279 0.2515 0.4027 0.061 Uiso 1 1 calc R . . C20 C -0.2089(6) 0.2820(3) 0.4273(3) 0.0423(12) Uani 1 1 d . . . H20 H -0.1704 0.2352 0.4495 0.051 Uiso 1 1 calc R . . C21 C 0.1748(4) 0.3982(2) 0.4061(3) 0.0264(8) Uani 1 1 d . . . C22 C 0.2573(5) 0.4551(3) 0.4544(3) 0.0363(10) Uani 1 1 d . . . H22 H 0.2709 0.4554 0.5167 0.044 Uiso 1 1 calc R . . C23 C 0.3201(5) 0.5116(3) 0.4128(3) 0.0409(11) Uani 1 1 d . . . H23 H 0.3758 0.5499 0.4468 0.049 Uiso 1 1 calc R . . C24 C 0.3009(5) 0.5117(3) 0.3212(3) 0.0381(10) Uani 1 1 d . . . H24 H 0.3427 0.5502 0.2926 0.046 Uiso 1 1 calc R . . C25 C 0.2197(5) 0.4546(3) 0.2720(3) 0.0368(10) Uani 1 1 d . . . H25 H 0.2071 0.4541 0.2097 0.044 Uiso 1 1 calc R . . C26 C 0.1567(5) 0.3980(3) 0.3139(3) 0.0330(9) Uani 1 1 d . . . H26 H 0.1017 0.3594 0.2800 0.040 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 Au 0.04141(10) 0.02730(9) 0.02520(9) 0.00015(7) 0.00413(6) 0.00948(8) S1 0.0683(8) 0.0299(6) 0.0264(5) 0.0012(4) 0.0095(5) 0.0153(6) P1 0.0321(5) 0.0260(5) 0.0234(5) 0.0009(4) 0.0034(4) 0.0069(4) O1 0.0393(17) 0.0388(19) 0.0267(15) -0.0003(13) 0.0040(12) 0.0019(14) N1 0.042(2) 0.035(2) 0.033(2) 0.0049(16) 0.0101(16) 0.0003(17) C1 0.030(2) 0.033(2) 0.028(2) 0.0055(17) 0.0057(17) 0.0060(18) C2 0.035(2) 0.026(2) 0.037(2) 0.0082(18) 0.0112(18) 0.0045(18) C3 0.036(2) 0.040(3) 0.058(3) 0.015(2) 0.014(2) 0.003(2) C4 0.052(3) 0.042(3) 0.064(4) 0.010(3) 0.032(3) 0.013(3) C5 0.066(3) 0.030(3) 0.056(3) 0.008(2) 0.030(3) -0.008(3) C5' 0.097(5) 0.046(4) 0.088(5) -0.014(3) 0.048(4) -0.008(4) C6 0.049(3) 0.038(3) 0.052(3) 0.006(2) 0.014(2) -0.002(2) C7 0.035(3) 0.040(3) 0.049(3) 0.005(2) 0.016(2) 0.004(2) C8 0.064(3) 0.059(4) 0.024(2) 0.001(2) 0.000(2) 0.001(3) C9 0.038(2) 0.030(2) 0.024(2) 0.0029(17) 0.0033(17) 0.0056(19) C10 0.039(2) 0.035(3) 0.034(2) -0.0049(19) 0.0054(19) 0.001(2) C11 0.062(3) 0.039(3) 0.033(2) -0.006(2) 0.015(2) 0.003(2) C12 0.071(4) 0.055(4) 0.029(2) -0.002(2) -0.002(2) 0.003(3) C13 0.074(4) 0.097(6) 0.033(3) -0.006(3) -0.017(3) 0.031(4) C14 0.062(4) 0.085(5) 0.034(3) -0.008(3) -0.004(2) 0.043(3) C15 0.037(2) 0.028(2) 0.0215(19) -0.0030(16) 0.0042(16) 0.0047(18) C16 0.036(2) 0.029(2) 0.028(2) 0.0031(17) 0.0031(17) 0.0048(18) C17 0.042(3) 0.038(3) 0.032(2) 0.0028(19) 0.0085(19) 0.017(2) C18 0.032(2) 0.051(3) 0.038(3) -0.002(2) -0.0017(19) 0.008(2) C19 0.038(3) 0.056(4) 0.054(3) 0.009(3) 0.003(2) -0.016(3) C20 0.044(3) 0.036(3) 0.045(3) 0.012(2) 0.004(2) 0.007(2) C21 0.028(2) 0.024(2) 0.028(2) -0.0005(16) 0.0069(15) 0.0064(16) C22 0.042(3) 0.037(3) 0.029(2) -0.0026(19) 0.0064(19) 0.003(2) C23 0.041(3) 0.038(3) 0.045(3) -0.011(2) 0.012(2) -0.009(2) C24 0.040(3) 0.034(3) 0.043(3) 0.002(2) 0.015(2) 0.003(2) C25 0.044(3) 0.039(3) 0.029(2) 0.0041(19) 0.0123(19) 0.004(2) C26 0.038(2) 0.031(2) 0.028(2) -0.0012(17) 0.0024(17) 0.0061(19) _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 Au P1 2.2446(11) . ? Au S1 2.3003(12) . ? S1 C1 1.760(4) . ? P1 C15 1.813(4) . ? P1 C21 1.814(4) . ? P1 C9 1.818(4) . ? O1 C1 1.357(5) . ? O1 C8 1.439(5) . ? N1 C1 1.251(6) . ? N1 C2 1.420(6) . ? C2 C7 1.375(6) . ? C2 C3 1.389(6) . ? C3 C4 1.380(8) . ? C3 H3 0.9400 . ? C4 C5 1.370(8) . ? C4 H4 0.9400 . ? C5 C6 1.396(8) . ? C5 C5' 1.517(8) . ? C5' H5'1 0.9700 . ? C5' H5'2 0.9700 . ? C5' H5'3 0.9700 . ? C6 C7 1.361(7) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.372(6) . ? C9 C14 1.376(6) . ? C10 C11 1.381(6) . ? C10 H10 0.9400 . ? C11 C12 1.357(7) . ? C11 H11 0.9400 . ? C12 C13 1.375(9) . ? C12 H12 0.9400 . ? C13 C14 1.374(7) . ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C15 C20 1.376(7) . ? C15 C16 1.394(6) . ? C16 C17 1.387(6) . ? C16 H16 0.9400 . ? C17 C18 1.373(7) . ? C17 H17 0.9400 . ? C18 C19 1.379(7) . ? C18 H18 0.9400 . ? C19 C20 1.391(7) . ? C19 H19 0.9400 . ? C20 H20 0.9400 . ? C21 C22 1.380(6) . ? C21 C26 1.391(6) . ? C22 C23 1.382(7) . ? C22 H22 0.9400 . ? C23 C24 1.382(6) . ? C23 H23 0.9400 . ? C24 C25 1.384(7) . ? C24 H24 0.9400 . ? C25 C26 1.388(6) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? 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 P1 Au S1 175.68(4) . . ? C1 S1 Au 100.05(16) . . ? C15 P1 C21 105.43(19) . . ? C15 P1 C9 107.10(19) . . ? C21 P1 C9 104.9(2) . . ? C15 P1 Au 111.71(15) . . ? C21 P1 Au 116.00(14) . . ? C9 P1 Au 111.10(15) . . ? C1 O1 C8 115.9(4) . . ? C1 N1 C2 121.3(4) . . ? N1 C1 O1 120.4(4) . . ? N1 C1 S1 127.7(4) . . ? O1 C1 S1 111.9(3) . . ? C7 C2 C3 119.0(5) . . ? C7 C2 N1 122.9(4) . . ? C3 C2 N1 118.0(4) . . ? C2 C3 C4 119.1(5) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 122.6(5) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C4 C5 C6 116.9(5) . . ? C4 C5 C5' 122.0(5) . . ? C6 C5 C5' 121.1(6) . . ? C5 C5' H5'1 109.5 . . ? C5 C5' H5'2 109.5 . . ? H5'1 C5' H5'2 109.5 . . ? C5 C5' H5'3 109.5 . . ? H5'1 C5' H5'3 109.5 . . ? H5'2 C5' H5'3 109.5 . . ? C5 C6 C7 121.5(5) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C2 C7 C6 120.8(5) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.4(4) . . ? C10 C9 P1 123.1(3) . . ? C14 C9 P1 118.4(4) . . ? C9 C10 C11 120.9(4) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 120.2(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.5(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.2(5) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.7(5) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C20 C15 C16 119.6(4) . . ? C20 C15 P1 118.5(3) . . ? C16 C15 P1 121.9(4) . . ? C15 C16 C17 119.4(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 120.8(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.8(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 119.9(5) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C15 C20 C19 120.4(5) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C26 118.8(4) . . ? C22 C21 P1 122.9(3) . . ? C26 C21 P1 118.3(3) . . ? C21 C22 C23 121.2(4) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 119.5(5) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.4(4) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.1(4) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.1 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.23 # 0.82 A from Au _refine_diff_density_min -0.52 _refine_diff_density_rms 0.136