# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Nick Hadjiliadis' _publ_contact_author_email NHADJIS@UOI.GR _publ_section_title ; Synthesis, structural characterization and in vitro cytotoxicity of new Au(III) and Au(I) complexes with thioamides.Oxidation and desulfuration of thioamides by Au(III) ions. ; loop_ _publ_author_name 'Nick Hadjiliadis' 'A. V. Dolganov' 'Sotiris Hadjikakou' 'Michael B. Hursthouse' ; N.Kourkoumelis ; 'K. N. Kouroulis' 'Maciej Kubicki' 'Louise Male' 'A. K. Metsios' 'E. R. Milaeva' ; S.Skoulika ; 'V. Y. Tyurin' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 732324' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzothiazolium tetrachloroaurate(III) ; _chemical_name_common 'Benzothiazolium tetrachloroaurate(iii)' _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 N S, Au Cl4' _chemical_formula_sum 'C7 H6 Au Cl4 N S' _chemical_formula_weight 474.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3524(4) _cell_length_b 7.7452(2) _cell_length_c 19.3505(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2300.92(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19111 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour 'Pale brown' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 13.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5319 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27049 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2623 _reflns_number_gt 2225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SIR92 (Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON/PLUTON (Spek, A. L., 1998)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0255P)^2^+5.4614P] 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 2623 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.0706(3) 0.1480(6) 0.6184(2) 0.0159(11) Uani 1 1 d . . . H1 H 0.0913 0.1150 0.6627 0.019 Uiso 1 1 calc R . . C2 C 0.0443(3) 0.2080(6) 0.4976(2) 0.0129(10) Uani 1 1 d . . . C3 C 0.0395(3) 0.2306(6) 0.4251(2) 0.0147(11) Uani 1 1 d . . . H3 H 0.0852 0.1945 0.3954 0.018 Uiso 1 1 calc R . . C4 C -0.0350(4) 0.3080(6) 0.3999(3) 0.0193(12) Uani 1 1 d . . . H4 H -0.0412 0.3226 0.3514 0.023 Uiso 1 1 calc R . . C5 C -0.1022(3) 0.3659(6) 0.4436(3) 0.0187(11) Uani 1 1 d . . . H5 H -0.1521 0.4197 0.4241 0.022 Uiso 1 1 calc R . . C6 C -0.0969(3) 0.3458(6) 0.5143(3) 0.0156(10) Uani 1 1 d . . . H6 H -0.1416 0.3865 0.5441 0.019 Uiso 1 1 calc R . . C7 C -0.0233(3) 0.2632(6) 0.5400(2) 0.0133(10) Uani 1 1 d . . . N1 N -0.0046(3) 0.2242(5) 0.60900(19) 0.0150(9) Uani 1 1 d . . . H1A H -0.0403 0.2487 0.6432 0.018 Uiso 1 1 calc R . . S1 S 0.12752(9) 0.11343(16) 0.54529(6) 0.0162(3) Uani 1 1 d . . . Au1 Au 0.762841(12) 0.97059(2) 0.723121(8) 0.01032(8) Uani 1 1 d . . . Cl1 Cl 0.78010(9) 1.08082(16) 0.61426(6) 0.0183(3) Uani 1 1 d . . . Cl2 Cl 0.61488(8) 0.97963(16) 0.71007(6) 0.0171(3) Uani 1 1 d . . . Cl3 Cl 0.74370(8) 0.85957(16) 0.83128(6) 0.0169(3) Uani 1 1 d . . . Cl4 Cl 0.91020(8) 0.96550(16) 0.73800(6) 0.0174(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(3) 0.018(3) 0.010(2) 0.0023(19) 0.001(2) -0.003(2) C2 0.017(3) 0.007(2) 0.015(2) -0.0002(17) 0.000(2) -0.0038(19) C3 0.020(3) 0.015(3) 0.009(2) -0.0024(18) 0.005(2) -0.006(2) C4 0.029(3) 0.018(3) 0.011(2) 0.0042(19) -0.001(2) -0.005(2) C5 0.014(3) 0.015(3) 0.026(3) 0.006(2) -0.007(2) 0.000(2) C6 0.016(3) 0.007(2) 0.024(3) 0.0004(19) 0.002(2) -0.0041(19) C7 0.016(3) 0.011(2) 0.012(2) -0.0021(17) 0.000(2) -0.0021(19) N1 0.017(2) 0.021(2) 0.007(2) -0.0010(15) 0.0054(17) -0.0025(18) S1 0.0129(7) 0.0204(7) 0.0153(6) -0.0007(5) -0.0016(5) 0.0022(5) Au1 0.00987(12) 0.01106(12) 0.01002(12) -0.00122(7) -0.00030(7) -0.00058(6) Cl1 0.0193(7) 0.0239(7) 0.0116(6) 0.0036(5) 0.0000(5) -0.0028(5) Cl2 0.0111(7) 0.0227(6) 0.0175(6) -0.0036(5) -0.0016(5) 0.0013(5) Cl3 0.0181(7) 0.0191(7) 0.0134(6) 0.0027(5) 0.0002(5) 0.0004(4) Cl4 0.0116(7) 0.0255(7) 0.0152(5) -0.0022(5) -0.0013(5) -0.0011(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 C1 N1 1.308(7) . ? C1 S1 1.684(5) . ? C1 H1 0.9500 . ? C2 C7 1.391(7) . ? C2 C3 1.415(7) . ? C2 S1 1.738(5) . ? C3 C4 1.381(7) . ? C3 H3 0.9500 . ? C4 C5 1.408(7) . ? C4 H4 0.9500 . ? C5 C6 1.379(7) . ? C5 H5 0.9500 . ? C6 C7 1.390(7) . ? C6 H6 0.9500 . ? C7 N1 1.398(6) . ? N1 H1A 0.8800 . ? Au1 Cl4 2.2808(13) . ? Au1 Cl3 2.2816(12) . ? Au1 Cl2 2.2867(13) . ? Au1 Cl1 2.2884(12) . ? 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 N1 C1 S1 114.4(4) . . ? N1 C1 H1 122.8 . . ? S1 C1 H1 122.8 . . ? C7 C2 C3 120.5(5) . . ? C7 C2 S1 111.4(3) . . ? C3 C2 S1 128.1(4) . . ? C4 C3 C2 116.6(5) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? C3 C4 C5 122.2(5) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C4 121.1(5) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 117.1(5) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C6 C7 C2 122.4(4) . . ? C6 C7 N1 127.5(5) . . ? C2 C7 N1 110.1(4) . . ? C1 N1 C7 114.3(4) . . ? C1 N1 H1A 122.9 . . ? C7 N1 H1A 122.9 . . ? C1 S1 C2 89.8(2) . . ? Cl4 Au1 Cl3 90.31(4) . . ? Cl4 Au1 Cl2 178.81(4) . . ? Cl3 Au1 Cl2 89.14(4) . . ? Cl4 Au1 Cl1 90.45(5) . . ? Cl3 Au1 Cl1 179.20(5) . . ? Cl2 Au1 Cl1 90.11(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl2 0.88 2.49 3.257(4) 146.5 7_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.305 _refine_diff_density_min -1.822 _refine_diff_density_rms 0.208 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 732325' _audit_creation_method SHELXL-97 _publ_section_comment ; Each formula unit of this structure contains, in total five water molecules, one of which is disordered, and one disordered molecule of [H3O]+. There are also four chloride ions. The presence of the [H3O]+ molecule means that the charge in the formula unit is balanced. It was only possible to locate hydrogen atoms for one of the water moieties, O2. For all other water molecules and the [H3O]+ molecule it was impossible to locate the hydrogen atoms because of the use of X-ray radiation, the presence of the very heavy gold atom and the low occupancies of the species at these positions. For this reason it is not possible to assign which of atoms O4 and O5 belongs to a water molecule and which belongs to the acid, as the assignment of either atom as the acid would give the correct charge balance. It is highly probable that the O3, O4 and O5 moieties are involved in hydrogen bonding, but this is impossible to confirm due to the fact that the hydrogen atoms in these moieties could not be located. ; # start Validation Reply Form _vrf_PLAT430_2 ; PROBLEM: Short Inter D...A Contact O4 .. O4' .. 2.06 Ang. RESPONSE: It was not possible to locte the hydrogen atoms belonging to these species in the electron density. ; _vrf_PLAT431_2 ; PROBLEM: Short Inter HL..A Contact Cl4 .. O4' .. 2.91 Ang. RESPONSE: It was not possible to locte the hydrogen atoms belonging to these oxygen atoms in the electron density. ; # end Validation Reply Form _chemical_name_systematic ; 5-Ethoxy-benzimidazolium oxonium dichloride tetrachloroaurate(III) pentahydrate ; _chemical_name_common ;5-Ethoxy-benzimidazolium oxonium dichloride tetrachloroaurate(iii) pentahydrate ; _chemical_melting_point ? _chemical_formula_moiety '4(C9 H10 N2 O), AU CL4, 4CL, 5(O H2), 0 H3' _chemical_formula_sum 'C36 H53 Au Cl8 N8 O10' _chemical_formula_weight 1238.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.0808(5) _cell_length_b 25.1431(7) _cell_length_c 4.87740(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.500(2) _cell_angle_gamma 90.00 _cell_volume 2705.26(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3097 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 3.168 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7424 _exptl_absorpt_correction_T_max 0.9109 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 16733 reflections reduced R(int) from 0.1044 to 0.0516 Ratio of minimum to maximum apparent transmission: 0.824694 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15931 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3171 _reflns_number_gt 3106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 for Windows (Farrugia, L.J., 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0429P)^2^+29.0597P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3171 _refine_ls_number_parameters 175 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6079(2) 0.1207(2) 0.9634(9) 0.0272(10) Uani 1 1 d . . . H1 H 0.5855 0.1046 1.1034 0.033 Uiso 1 1 calc R . . C2 C 0.6747(2) 0.1330(2) 0.6469(9) 0.0274(10) Uani 1 1 d . . . C3 C 0.6393(2) 0.1784(2) 0.6629(9) 0.0282(10) Uani 1 1 d . . . C4 C 0.6499(2) 0.2227(2) 0.4984(11) 0.0323(11) Uani 1 1 d . . . H4 H 0.6259 0.2540 0.5066 0.039 Uiso 1 1 calc R . . C5 C 0.6973(2) 0.2185(2) 0.3229(10) 0.0334(12) Uani 1 1 d . . . H5 H 0.7058 0.2475 0.2063 0.040 Uiso 1 1 calc R . . C6 C 0.7331(2) 0.1724(2) 0.3120(10) 0.0307(11) Uani 1 1 d . . . C7 C 0.7228(2) 0.1280(2) 0.4715(10) 0.0296(10) Uani 1 1 d . . . H7 H 0.7465 0.0966 0.4623 0.036 Uiso 1 1 calc R . . C8 C 0.8177(3) 0.1302(2) 0.1014(11) 0.0385(12) Uani 1 1 d . . . H8A H 0.7939 0.0999 0.0251 0.046 Uiso 1 1 calc R . . H8B H 0.8364 0.1196 0.2812 0.046 Uiso 1 1 calc R . . C9 C 0.8653(3) 0.1458(3) -0.0891(14) 0.0501(16) Uani 1 1 d . . . H9A H 0.8461 0.1585 -0.2620 0.075 Uiso 1 1 calc R . . H9B H 0.8909 0.1150 -0.1253 0.075 Uiso 1 1 calc R . . H9C H 0.8903 0.1742 -0.0058 0.075 Uiso 1 1 calc R . . N1 N 0.65347(18) 0.09758(18) 0.8385(8) 0.0281(9) Uani 1 1 d . . . N2 N 0.59817(18) 0.16904(17) 0.8646(8) 0.0274(9) Uani 1 1 d . . . H2 H 0.5704 0.1914 0.9176 0.033 Uiso 1 1 calc R . . O1 O 0.77931(18) 0.17561(16) 0.1328(8) 0.0375(9) Uani 1 1 d . . . Au1 Au 0.5000 0.0000 0.5000 0.02145(12) Uani 1 4 d S . . Cl1 Cl 0.59459(8) 0.0000 0.3303(4) 0.0339(4) Uani 1 2 d S . . Cl2 Cl 0.5000 0.09054(6) 0.5000 0.0266(3) Uani 1 2 d S . . Cl3 Cl 0.5000 0.24899(9) 0.0000 0.0477(5) Uani 1 2 d S . . Cl4 Cl 0.79842(12) 0.0000 0.4671(5) 0.0567(6) Uani 1 2 d S . . O2 O 0.7166(3) 0.0000 0.9394(10) 0.0307(11) Uani 1 2 d SD . . H2A H 0.739(3) 0.0000 1.082(10) 0.046 Uiso 1 2 d SD . . H2B H 0.6805(11) 0.0000 0.975(15) 0.046 Uiso 1 2 d SD . . O3 O 0.4821(5) 0.3205(5) 0.493(4) 0.083(4) Uani 0.50 1 d P . . O4 O 0.5737(11) 0.5000 0.289(8) 0.073(6) Uani 0.25 2 d SPU A 1 O4' O 0.5776(11) 0.5000 0.712(8) 0.073(6) Uani 0.25 2 d SPU B 2 O5 O 0.4963(19) 0.5790(9) 0.451(4) 0.027(6) Uani 0.125 1 d PU C 1 O5' O 0.5061(18) 0.5750(12) 0.656(5) 0.027(6) Uani 0.125 1 d PU D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(2) 0.033(3) 0.021(2) -0.0022(19) 0.0027(17) -0.005(2) C2 0.030(2) 0.034(3) 0.018(2) -0.0014(19) -0.0006(17) -0.010(2) C3 0.027(2) 0.036(3) 0.021(2) -0.002(2) -0.0003(18) -0.010(2) C4 0.036(3) 0.029(3) 0.032(3) 0.000(2) 0.000(2) -0.006(2) C5 0.040(3) 0.036(3) 0.024(2) 0.002(2) 0.002(2) -0.019(2) C6 0.028(2) 0.040(3) 0.024(2) -0.005(2) 0.0006(19) -0.012(2) C7 0.027(2) 0.038(3) 0.024(2) -0.007(2) 0.0002(18) -0.007(2) C8 0.040(3) 0.047(3) 0.029(3) -0.006(2) 0.000(2) -0.002(3) C9 0.038(3) 0.065(4) 0.049(3) -0.018(3) 0.014(3) -0.005(3) N1 0.026(2) 0.038(2) 0.0204(18) -0.0002(17) 0.0003(15) -0.0061(17) N2 0.027(2) 0.031(2) 0.0252(19) -0.0007(17) 0.0013(16) -0.0023(16) O1 0.042(2) 0.041(2) 0.0305(18) -0.0027(16) 0.0115(16) -0.0090(17) Au1 0.02104(18) 0.02319(19) 0.02024(18) 0.000 0.00237(12) 0.000 Cl1 0.0272(8) 0.0284(9) 0.0472(10) 0.000 0.0155(7) 0.000 Cl2 0.0263(8) 0.0228(8) 0.0308(8) 0.000 0.0042(6) 0.000 Cl3 0.0421(11) 0.0422(11) 0.0597(13) 0.000 0.0106(9) 0.000 Cl4 0.0611(14) 0.0587(14) 0.0515(13) 0.000 0.0151(11) 0.000 O2 0.043(3) 0.026(2) 0.024(2) 0.000 0.008(2) 0.000 O3 0.077(11) 0.103(9) 0.071(7) -0.022(8) 0.032(11) -0.016(6) O4 0.017(7) 0.090(13) 0.112(14) 0.000 0.013(9) 0.000 O4' 0.017(7) 0.090(13) 0.112(14) 0.000 0.013(9) 0.000 O5 0.049(10) 0.021(7) 0.012(14) -0.003(6) 0.009(14) -0.008(11) O5' 0.049(10) 0.021(7) 0.012(14) -0.003(6) 0.009(14) -0.008(11) _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 C1 N2 1.322(7) . ? C1 N1 1.333(6) . ? C1 H1 0.9500 . ? C2 N1 1.388(6) . ? C2 C3 1.388(8) . ? C2 C7 1.397(7) . ? C3 N2 1.389(6) . ? C3 C4 1.398(7) . ? C4 C5 1.385(7) . ? C4 H4 0.9500 . ? C5 C6 1.404(8) . ? C5 H5 0.9500 . ? C6 O1 1.375(6) . ? C6 C7 1.385(8) . ? C7 H7 0.9500 . ? C8 O1 1.433(7) . ? C8 C9 1.485(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.8800 . ? Au1 Cl2 2.2765(16) 5_656 ? Au1 Cl2 2.2765(16) . ? Au1 Cl1 2.2799(16) 5_656 ? Au1 Cl1 2.2799(16) . ? O2 H2A 0.84(2) . ? O2 H2B 0.83(2) . ? 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 N2 C1 N1 110.4(4) . . ? N2 C1 H1 124.8 . . ? N1 C1 H1 124.8 . . ? N1 C2 C3 106.4(4) . . ? N1 C2 C7 130.0(5) . . ? C3 C2 C7 123.5(5) . . ? C2 C3 N2 106.7(4) . . ? C2 C3 C4 121.0(5) . . ? N2 C3 C4 132.3(5) . . ? C5 C4 C3 116.2(5) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? C4 C5 C6 122.0(5) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? O1 C6 C7 123.3(5) . . ? O1 C6 C5 114.3(5) . . ? C7 C6 C5 122.4(5) . . ? C6 C7 C2 114.8(5) . . ? C6 C7 H7 122.6 . . ? C2 C7 H7 122.6 . . ? O1 C8 C9 107.2(5) . . ? O1 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 N1 C2 108.2(4) . . ? C1 N2 C3 108.3(4) . . ? C1 N2 H2 125.8 . . ? C3 N2 H2 125.8 . . ? C6 O1 C8 118.7(4) . . ? Cl2 Au1 Cl2 180.0 5_656 . ? Cl2 Au1 Cl1 90.0 5_656 5_656 ? Cl2 Au1 Cl1 90.0 . 5_656 ? Cl2 Au1 Cl1 90.0 5_656 . ? Cl2 Au1 Cl1 90.0 . . ? Cl1 Au1 Cl1 180.00(3) 5_656 . ? H2A O2 H2B 111(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Cl3 0.88 2.17 3.050(5) 173.6 1_556 O2 H2A Cl4 0.84(2) 2.24(2) 3.079(6) 179(7) 1_556 O2 H2B Cl1 0.83(2) 2.62(4) 3.368(5) 151(7) 1_556 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.075 _refine_diff_density_min -0.989 _refine_diff_density_rms 0.153 # Attachment '7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 732368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 Au Cl N P S2' _chemical_formula_weight 659.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Au Au -2.0133 8.8022 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8981(4) _cell_length_b 11.0221(4) _cell_length_c 14.1845(6) _cell_angle_alpha 89.145(3) _cell_angle_beta 76.610(4) _cell_angle_gamma 83.837(4) _cell_volume 1345.45(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5921 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 5.793 _exptl_absorpt_correction_T_min 0.20319 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4CCD diffractometer' _diffrn_measurement_method \w-scan _diffrn_reflns_number 9926 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4736 _reflns_number_gt 3939 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_cell_refinement ; CrysAlis RED Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_data_reduction ; CrysAlis RED Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens, 1989)' _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^)+(0.1500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4736 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.2069 _refine_ls_wR_factor_gt 0.1957 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.002 _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 1.23938(4) 0.44657(3) 0.86467(3) 0.0475(2) Uani 1 1 d . . . P1 P 1.1285(3) 0.2764(2) 0.9200(2) 0.0395(6) Uani 1 1 d . . . C111 C 1.1189(11) 0.2514(9) 1.0491(8) 0.044(2) Uani 1 1 d . . . C112 C 0.9976(13) 0.1998(11) 1.1083(8) 0.055(3) Uani 1 1 d . . . H112 H 0.9151 0.1810 1.0832 0.066 Uiso 1 1 calc R . . C113 C 0.9958(15) 0.1763(14) 1.2007(10) 0.069(3) Uani 1 1 d . . . H113 H 0.9155 0.1387 1.2400 0.083 Uiso 1 1 calc R . . C114 C 1.121(2) 0.2107(15) 1.2376(10) 0.084(5) Uani 1 1 d . . . H114 H 1.1203 0.1955 1.3023 0.101 Uiso 1 1 calc R . . C115 C 1.2384(18) 0.2636(15) 1.1835(11) 0.066(4) Uani 1 1 d . . . H115 H 1.3187 0.2848 1.2097 0.080 Uiso 1 1 calc R . . C116 C 1.2384(15) 0.2866(11) 1.0857(10) 0.059(3) Uani 1 1 d . . . H116 H 1.3179 0.3250 1.0463 0.071 Uiso 1 1 calc R . . C121 C 1.2453(11) 0.1455(9) 0.8576(8) 0.045(2) Uani 1 1 d . . . C122 C 1.2842(15) 0.1429(13) 0.7598(10) 0.069(3) Uani 1 1 d . . . H122 H 1.2525 0.2103 0.7263 0.083 Uiso 1 1 calc R . . C123 C 1.3702(17) 0.0424(16) 0.7074(11) 0.079(4) Uani 1 1 d . . . H123 H 1.3900 0.0409 0.6400 0.095 Uiso 1 1 calc R . . C124 C 1.4257(16) -0.0553(12) 0.7570(13) 0.076(4) Uani 1 1 d . . . H124 H 1.4899 -0.1201 0.7229 0.091 Uiso 1 1 calc R . . C125 C 1.3855(15) -0.0566(11) 0.8581(11) 0.071(4) Uani 1 1 d . . . H125 H 1.4185 -0.1236 0.8916 0.085 Uiso 1 1 calc R . . C126 C 1.2970(13) 0.0418(10) 0.9071(9) 0.054(3) Uani 1 1 d . . . H126 H 1.2699 0.0410 0.9745 0.065 Uiso 1 1 calc R . . C131 C 0.9350(10) 0.2651(9) 0.9004(7) 0.039(2) Uani 1 1 d . . . C132 C 0.8352(13) 0.3742(11) 0.9086(9) 0.056(3) Uani 1 1 d . . . H132 H 0.8676 0.4476 0.9233 0.067 Uiso 1 1 calc R . . C133 C 0.6866(15) 0.3694(16) 0.8942(10) 0.076(4) Uani 1 1 d . . . H133 H 0.6206 0.4411 0.8955 0.091 Uiso 1 1 calc R . . C134 C 0.6364(13) 0.2598(15) 0.8780(9) 0.066(3) Uani 1 1 d . . . H134 H 0.5344 0.2567 0.8731 0.079 Uiso 1 1 calc R . . C135 C 0.7353(17) 0.1564(16) 0.8694(11) 0.076(4) Uani 1 1 d . . . H135 H 0.7047 0.0823 0.8545 0.091 Uiso 1 1 calc R . . C136 C 0.8849(14) 0.1634(12) 0.8833(10) 0.064(3) Uani 1 1 d . . . H136 H 0.9514 0.0918 0.8802 0.077 Uiso 1 1 calc R . . S21 S 1.5061(4) 0.4154(3) 0.6570(3) 0.0686(8) Uani 1 1 d . . . C22 C 1.4948(15) 0.5660(11) 0.7026(10) 0.062(3) Uani 1 1 d . . . S22 S 1.3673(4) 0.6136(3) 0.8110(3) 0.0589(8) Uani 1 1 d . . . N23 N 1.5871(13) 0.6353(10) 0.6516(7) 0.063(3) Uani 1 1 d . . . C23A C 1.6751(13) 0.5724(12) 0.5693(8) 0.058(3) Uani 1 1 d . . . C24 C 1.7873(16) 0.6248(18) 0.4987(11) 0.083(5) Uani 1 1 d . . . H24 H 1.8076 0.7051 0.5039 0.099 Uiso 1 1 calc R . . C25 C 1.8681(19) 0.549(2) 0.4191(11) 0.092(6) Uani 1 1 d . . . Cl25 Cl 2.0097(5) 0.6076(6) 0.3309(3) 0.121(2) Uani 1 1 d . . . C26 C 1.8385(19) 0.4303(18) 0.4105(10) 0.083(5) Uani 1 1 d . . . H26 H 1.8935 0.3831 0.3573 0.099 Uiso 1 1 calc R . . C27 C 1.728(2) 0.3815(17) 0.4799(12) 0.084(5) Uani 1 1 d . . . H27 H 1.7072 0.3011 0.4755 0.101 Uiso 1 1 calc R . . C27A C 1.6497(16) 0.4555(13) 0.5562(9) 0.067(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0426(3) 0.0367(3) 0.0624(4) -0.0018(2) -0.0095(2) -0.00627(18) P1 0.0347(12) 0.0340(13) 0.0501(15) -0.0050(11) -0.0101(10) -0.0030(10) C111 0.038(5) 0.041(5) 0.056(6) -0.010(5) -0.019(4) -0.006(4) C112 0.044(6) 0.065(7) 0.060(7) -0.002(6) -0.016(5) -0.013(5) C113 0.057(7) 0.087(10) 0.067(8) 0.002(7) -0.017(6) -0.016(7) C114 0.113(12) 0.091(11) 0.045(7) -0.009(7) -0.031(8) 0.029(9) C115 0.068(8) 0.073(9) 0.060(8) -0.013(7) -0.029(7) 0.009(7) C116 0.062(7) 0.046(6) 0.076(8) -0.011(6) -0.031(6) 0.004(5) C121 0.035(5) 0.039(5) 0.060(7) -0.012(5) -0.010(4) -0.007(4) C122 0.062(7) 0.065(8) 0.078(9) -0.007(7) -0.017(6) 0.009(6) C123 0.077(9) 0.094(11) 0.065(9) -0.023(8) -0.010(7) -0.007(8) C124 0.057(7) 0.050(7) 0.111(12) -0.028(8) -0.004(7) 0.005(6) C125 0.069(8) 0.044(6) 0.087(10) -0.004(7) -0.003(6) 0.015(6) C126 0.052(6) 0.046(6) 0.065(7) 0.005(5) -0.015(5) -0.007(5) C131 0.038(5) 0.040(5) 0.035(5) -0.009(4) -0.004(3) 0.002(4) C132 0.049(6) 0.052(6) 0.066(7) -0.011(6) -0.017(5) 0.006(5) C133 0.052(7) 0.095(11) 0.083(9) -0.003(8) -0.031(6) 0.011(7) C134 0.036(5) 0.104(11) 0.057(7) -0.004(7) -0.011(5) -0.002(6) C135 0.064(8) 0.092(11) 0.080(10) 0.009(8) -0.025(7) -0.029(8) C136 0.050(6) 0.060(7) 0.094(9) 0.005(7) -0.034(6) -0.015(6) S21 0.083(2) 0.0514(17) 0.072(2) -0.0061(16) -0.0178(16) -0.0080(16) C22 0.064(7) 0.052(7) 0.077(8) -0.002(6) -0.024(6) -0.014(6) S22 0.0614(17) 0.0385(15) 0.0694(19) -0.0089(14) 0.0042(13) -0.0134(13) N23 0.077(7) 0.063(6) 0.053(6) 0.001(5) -0.016(5) -0.027(5) C23A 0.048(6) 0.075(8) 0.052(7) -0.008(6) -0.015(5) -0.006(6) C24 0.059(8) 0.126(14) 0.072(9) 0.011(9) -0.030(7) -0.024(8) C25 0.078(10) 0.146(18) 0.054(9) 0.016(10) -0.023(7) 0.001(11) Cl25 0.089(3) 0.194(6) 0.067(2) 0.020(3) 0.0018(19) 0.001(3) C26 0.082(10) 0.105(13) 0.049(8) -0.012(8) -0.006(7) 0.023(9) C27 0.097(12) 0.076(10) 0.076(10) -0.016(8) -0.022(9) 0.015(9) C27A 0.074(8) 0.072(9) 0.062(8) -0.013(7) -0.030(6) 0.002(7) _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 2.259(3) . ? Au1 S22 2.296(3) . ? P1 C111 1.831(11) . ? P1 C121 1.799(11) . ? P1 C131 1.824(10) . ? C111 C112 1.375(15) . ? C111 C116 1.380(15) . ? C112 C113 1.330(17) . ? C112 H112 0.9300 . ? C113 C114 1.42(2) . ? C113 H113 0.9300 . ? C114 C115 1.33(2) . ? C114 H114 0.9300 . ? C115 C116 1.407(19) . ? C115 H115 0.9300 . ? C116 H116 0.9300 . ? C121 C126 1.422(15) . ? C121 C122 1.350(17) . ? C122 C123 1.39(2) . ? C122 H122 0.9300 . ? C123 C124 1.39(2) . ? C123 H123 0.9300 . ? C124 C125 1.39(2) . ? C124 H124 0.9300 . ? C125 C126 1.366(17) . ? C125 H125 0.9300 . ? C126 H126 0.9300 . ? C131 C136 1.295(15) . ? C131 C132 1.405(15) . ? C132 C133 1.390(17) . ? C132 H132 0.9300 . ? C133 C134 1.37(2) . ? C133 H133 0.9300 . ? C134 C135 1.35(2) . ? C134 H134 0.9300 . ? C135 C136 1.401(18) . ? C135 H135 0.9300 . ? C136 H136 0.9300 . ? S21 C27A 1.769(15) . ? S21 C22 1.775(13) . ? C22 N23 1.275(16) . ? C22 S22 1.736(14) . ? N23 C23A 1.393(16) . ? C23A C24 1.406(19) . ? C23A C27A 1.354(19) . ? C24 C25 1.42(3) . ? C24 H24 0.9300 . ? C25 C26 1.37(3) . ? C25 Cl25 1.732(18) . ? C26 C27 1.37(2) . ? C26 H26 0.9300 . ? C27 C27A 1.37(2) . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 S22 176.11(9) . . ? C111 P1 C121 106.0(5) . . ? C111 P1 C131 107.5(4) . . ? C121 P1 C131 104.4(4) . . ? C111 P1 Au1 112.7(3) . . ? C121 P1 Au1 109.1(3) . . ? C131 P1 Au1 116.4(3) . . ? C112 C111 C116 120.6(11) . . ? C112 C111 P1 121.9(8) . . ? C116 C111 P1 117.5(9) . . ? C111 C112 C113 121.3(11) . . ? C111 C112 H112 119.3 . . ? C113 C112 H112 119.3 . . ? C114 C113 C112 117.8(13) . . ? C114 C113 H113 121.1 . . ? C112 C113 H113 121.1 . . ? C113 C114 C115 122.8(13) . . ? C113 C114 H114 118.6 . . ? C115 C114 H114 118.6 . . ? C114 C115 C116 118.4(13) . . ? C114 C115 H115 120.8 . . ? C116 C115 H115 120.8 . . ? C111 C116 C115 119.0(13) . . ? C111 C116 H116 120.5 . . ? C115 C116 H116 120.5 . . ? C126 C121 C122 117.7(10) . . ? C126 C121 P1 122.7(9) . . ? C122 C121 P1 119.6(9) . . ? C121 C122 C123 122.2(13) . . ? C121 C122 H122 118.9 . . ? C123 C122 H122 118.9 . . ? C124 C123 C122 119.1(14) . . ? C124 C123 H123 120.5 . . ? C122 C123 H123 120.5 . . ? C125 C124 C123 120.1(12) . . ? C125 C124 H124 119.9 . . ? C123 C124 H124 119.9 . . ? C124 C125 C126 119.1(12) . . ? C124 C125 H125 120.5 . . ? C126 C125 H125 120.5 . . ? C125 C126 C121 121.6(12) . . ? C125 C126 H126 119.2 . . ? C121 C126 H126 119.2 . . ? C136 C131 C132 119.6(10) . . ? C136 C131 P1 123.9(8) . . ? C132 C131 P1 116.5(8) . . ? C133 C132 C131 118.2(12) . . ? C133 C132 H132 120.9 . . ? C131 C132 H132 120.9 . . ? C134 C133 C132 120.6(13) . . ? C134 C133 H133 119.7 . . ? C132 C133 H133 119.7 . . ? C133 C134 C135 119.9(12) . . ? C133 C134 H134 120.1 . . ? C135 C134 H134 120.1 . . ? C136 C135 C134 118.5(15) . . ? C136 C135 H135 120.8 . . ? C134 C135 H135 120.8 . . ? C131 C136 C135 123.1(13) . . ? C131 C136 H136 118.5 . . ? C135 C136 H136 118.5 . . ? C27A S21 C22 88.2(6) . . ? N23 C22 S22 122.7(10) . . ? N23 C22 S21 115.8(11) . . ? S22 C22 S21 121.5(7) . . ? C22 S22 Au1 104.8(4) . . ? C22 N23 C23A 109.8(11) . . ? N23 C23A C24 123.2(14) . . ? N23 C23A C27A 118.3(12) . . ? C24 C23A C27A 118.4(14) . . ? C25 C24 C23A 116.6(17) . . ? C25 C24 H24 121.7 . . ? C23A C24 H24 121.7 . . ? C26 C25 C24 122.2(16) . . ? C26 C25 Cl25 119.2(15) . . ? C24 C25 Cl25 118.5(17) . . ? C27 C26 C25 120.2(15) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C27A 117.4(18) . . ? C26 C27 H27 121.3 . . ? C27A C27 H27 121.3 . . ? C27 C27A C23A 125.2(16) . . ? C27 C27A S21 127.0(13) . . ? C23A C27A S21 107.8(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.006 _refine_diff_density_min -3.069 _refine_diff_density_rms 0.259 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 732369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H19 Au N P S2' _chemical_formula_sum 'C25 H19 Au N P S2' _chemical_formula_weight 625.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 12.7430(9) _cell_length_b 12.9378(7) _cell_length_c 13.6063(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.993(5) _cell_angle_gamma 90.00 _cell_volume 2231.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13335 _cell_measurement_theta_min 3 _cell_measurement_theta_max 24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 6.866 _exptl_absorpt_correction_T_min 0.46271 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4CCD diffractometer' _diffrn_measurement_method \w-scan _diffrn_reflns_number 27267 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.11 _reflns_number_total 5080 _reflns_number_gt 3819 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_cell_refinement ; CrysAlis RED Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_data_reduction ; CrysAlis RED Version 1.171.32.5 (Oxford Diffraction, 2007) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens, 1989)' _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^)+(0.0219P)^2^+4.6887P] 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 5080 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.002 _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 0.808920(15) -0.107875(15) -0.076490(12) 0.04644(7) Uani 1 1 d . . . P1 P 0.79031(9) -0.03589(9) 0.07170(8) 0.0398(2) Uani 1 1 d . . . C111 C 0.6572(3) -0.0427(3) 0.1065(3) 0.0411(9) Uani 1 1 d . . . C112 C 0.6203(4) 0.0249(4) 0.1734(4) 0.0546(12) Uani 1 1 d . . . H112 H 0.6645 0.0765 0.2018 0.066 Uiso 1 1 calc R . . C113 C 0.5177(4) 0.0166(4) 0.1990(4) 0.0608(13) Uani 1 1 d . . . H113 H 0.4936 0.0632 0.2435 0.073 Uiso 1 1 calc R . . C114 C 0.4523(4) -0.0593(4) 0.1592(4) 0.0558(12) Uani 1 1 d . . . H114 H 0.3843 -0.0655 0.1775 0.067 Uiso 1 1 calc R . . C115 C 0.4875(4) -0.1261(4) 0.0924(4) 0.0627(14) Uani 1 1 d . . . H115 H 0.4428 -0.1774 0.0644 0.075 Uiso 1 1 calc R . . C116 C 0.5887(4) -0.1181(4) 0.0658(4) 0.0500(11) Uani 1 1 d . . . H116 H 0.6114 -0.1641 0.0199 0.060 Uiso 1 1 calc R . . C121 C 0.8755(3) -0.0963(3) 0.1713(3) 0.0409(9) Uani 1 1 d . . . C122 C 0.9808(4) -0.1092(4) 0.1588(4) 0.0572(12) Uani 1 1 d . . . H122 H 1.0065 -0.0860 0.1012 0.069 Uiso 1 1 calc R . . C123 C 1.0487(4) -0.1569(5) 0.2319(4) 0.0689(15) Uani 1 1 d . . . H123 H 1.1198 -0.1649 0.2238 0.083 Uiso 1 1 calc R . . C124 C 1.0098(5) -0.1916(4) 0.3156(4) 0.0682(15) Uani 1 1 d . . . H124 H 1.0547 -0.2243 0.3642 0.082 Uiso 1 1 calc R . . C125 C 0.9050(5) -0.1790(5) 0.3290(4) 0.0698(15) Uani 1 1 d . . . H125 H 0.8793 -0.2027 0.3864 0.084 Uiso 1 1 calc R . . C126 C 0.8384(4) -0.1309(4) 0.2566(4) 0.0562(13) Uani 1 1 d . . . H126 H 0.7676 -0.1218 0.2657 0.067 Uiso 1 1 calc R . . C131 C 0.8254(3) 0.1001(3) 0.0766(3) 0.0404(9) Uani 1 1 d . . . C132 C 0.8083(4) 0.1586(4) -0.0089(4) 0.0518(11) Uani 1 1 d . . . H132 H 0.7809 0.1275 -0.0676 0.062 Uiso 1 1 calc R . . C133 C 0.8315(4) 0.2621(4) -0.0075(4) 0.0633(14) Uani 1 1 d . . . H133 H 0.8201 0.3007 -0.0653 0.076 Uiso 1 1 calc R . . C134 C 0.8715(4) 0.3088(4) 0.0789(5) 0.0667(15) Uani 1 1 d . . . H134 H 0.8855 0.3793 0.0799 0.080 Uiso 1 1 calc R . . C135 C 0.8908(4) 0.2521(4) 0.1630(4) 0.0633(14) Uani 1 1 d . . . H135 H 0.9189 0.2838 0.2212 0.076 Uiso 1 1 calc R . . C136 C 0.8687(4) 0.1482(4) 0.1621(4) 0.0539(12) Uani 1 1 d . . . H136 H 0.8831 0.1098 0.2196 0.065 Uiso 1 1 calc R . . S21 S 0.89191(11) -0.07382(13) -0.40373(11) 0.0676(4) Uani 1 1 d . . . C22 C 0.8086(4) -0.0873(4) -0.3100(3) 0.0516(12) Uani 1 1 d . . . S22 S 0.83861(13) -0.18477(12) -0.22313(9) 0.0668(4) Uani 1 1 d . . . N23 N 0.7256(3) -0.0285(3) -0.3174(3) 0.0554(10) Uani 1 1 d . . . C23A C 0.7230(4) 0.0313(4) -0.4035(3) 0.0502(11) Uani 1 1 d . . . C24 C 0.6413(5) 0.0980(4) -0.4350(4) 0.0689(15) Uani 1 1 d . . . H24 H 0.5852 0.1081 -0.3974 0.083 Uiso 1 1 calc R . . C25 C 0.6452(6) 0.1489(5) -0.5228(5) 0.0798(18) Uani 1 1 d . . . H25 H 0.5900 0.1923 -0.5460 0.096 Uiso 1 1 calc R . . C26 C 0.7290(7) 0.1369(5) -0.5769(5) 0.083(2) Uani 1 1 d . . . H26 H 0.7306 0.1741 -0.6352 0.100 Uiso 1 1 calc R . . C27 C 0.8109(5) 0.0711(5) -0.5472(4) 0.0721(16) Uani 1 1 d . . . H27 H 0.8673 0.0628 -0.5847 0.087 Uiso 1 1 calc R . . C27A C 0.8065(4) 0.0177(4) -0.4600(3) 0.0524(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.05375(11) 0.05168(11) 0.03413(9) -0.00417(8) 0.00569(7) 0.00313(9) P1 0.0439(6) 0.0430(6) 0.0331(5) -0.0016(5) 0.0065(5) -0.0031(5) C111 0.044(2) 0.044(2) 0.035(2) 0.0027(19) 0.0015(18) -0.0024(19) C112 0.054(3) 0.054(3) 0.058(3) -0.014(2) 0.014(2) -0.009(2) C113 0.063(3) 0.061(3) 0.062(3) -0.006(3) 0.022(3) 0.010(3) C114 0.044(3) 0.071(3) 0.052(3) 0.009(3) 0.005(2) -0.005(2) C115 0.049(3) 0.077(4) 0.061(3) 0.002(3) -0.004(2) -0.016(3) C116 0.054(3) 0.049(3) 0.047(3) -0.006(2) 0.003(2) -0.001(2) C121 0.047(2) 0.040(2) 0.035(2) -0.0059(19) 0.0038(18) -0.0065(19) C122 0.051(3) 0.073(3) 0.049(3) 0.009(3) 0.011(2) 0.001(3) C123 0.061(3) 0.079(4) 0.065(3) 0.006(3) -0.001(3) 0.016(3) C124 0.091(4) 0.058(3) 0.052(3) 0.009(3) -0.011(3) 0.008(3) C125 0.092(4) 0.074(4) 0.045(3) 0.010(3) 0.013(3) -0.003(3) C126 0.058(3) 0.068(3) 0.044(3) 0.006(2) 0.011(2) -0.002(2) C131 0.040(2) 0.041(2) 0.042(2) 0.001(2) 0.0096(18) 0.0002(18) C132 0.048(3) 0.055(3) 0.052(3) 0.004(2) 0.006(2) -0.001(2) C133 0.068(3) 0.051(3) 0.071(4) 0.024(3) 0.009(3) 0.008(3) C134 0.050(3) 0.046(3) 0.105(5) 0.000(3) 0.013(3) -0.002(2) C135 0.061(3) 0.054(3) 0.074(4) -0.013(3) -0.001(3) -0.002(3) C136 0.061(3) 0.054(3) 0.045(3) -0.004(2) 0.002(2) -0.011(2) S21 0.0535(7) 0.0886(10) 0.0629(8) -0.0043(8) 0.0164(6) 0.0079(7) C22 0.054(3) 0.062(3) 0.039(2) -0.013(2) 0.004(2) 0.008(2) S22 0.0939(10) 0.0656(8) 0.0407(6) -0.0074(6) 0.0060(7) 0.0287(8) N23 0.060(2) 0.058(3) 0.049(2) -0.003(2) 0.0132(19) 0.012(2) C23A 0.063(3) 0.046(3) 0.042(2) -0.009(2) 0.007(2) 0.000(2) C24 0.073(4) 0.064(4) 0.070(4) -0.002(3) 0.006(3) 0.023(3) C25 0.098(5) 0.066(4) 0.072(4) -0.001(3) -0.011(4) 0.013(3) C26 0.138(6) 0.054(3) 0.056(3) 0.004(3) 0.003(4) -0.012(4) C27 0.092(4) 0.066(4) 0.060(3) 0.002(3) 0.018(3) -0.008(3) C27A 0.062(3) 0.052(3) 0.044(3) -0.006(2) 0.007(2) -0.006(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 Au1 P1 2.2559(11) . ? Au1 S22 2.2960(13) . ? P1 C111 1.811(4) . ? P1 C131 1.815(4) . ? P1 C121 1.822(4) . ? C111 C112 1.379(6) . ? C111 C116 1.386(6) . ? C112 C113 1.392(7) . ? C112 H112 0.9300 . ? C113 C114 1.363(7) . ? C113 H113 0.9300 . ? C114 C115 1.364(7) . ? C114 H114 0.9300 . ? C115 C116 1.380(7) . ? C115 H115 0.9300 . ? C116 H116 0.9300 . ? C121 C126 1.373(6) . ? C121 C122 1.380(6) . ? C122 C123 1.393(7) . ? C122 H122 0.9300 . ? C123 C124 1.364(8) . ? C123 H123 0.9300 . ? C124 C125 1.377(8) . ? C124 H124 0.9300 . ? C125 C126 1.379(7) . ? C125 H125 0.9300 . ? C126 H126 0.9300 . ? C131 C136 1.383(6) . ? C131 C132 1.386(6) . ? C132 C133 1.371(7) . ? C132 H132 0.9300 . ? C133 C134 1.372(8) . ? C133 H133 0.9300 . ? C134 C135 1.359(8) . ? C134 H134 0.9300 . ? C135 C136 1.373(7) . ? C135 H135 0.9300 . ? C136 H136 0.9300 . ? S21 C27A 1.731(5) . ? S21 C22 1.751(5) . ? C22 N23 1.298(6) . ? C22 S22 1.743(5) . ? N23 C23A 1.402(6) . ? C23A C27A 1.387(7) . ? C23A C24 1.386(7) . ? C24 C25 1.369(9) . ? C24 H24 0.9300 . ? C25 C26 1.368(10) . ? C25 H25 0.9300 . ? C26 C27 1.374(9) . ? C26 H26 0.9300 . ? C27 C27A 1.379(7) . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 S22 176.25(5) . . ? C111 P1 C131 105.8(2) . . ? C111 P1 C121 106.6(2) . . ? C131 P1 C121 105.3(2) . . ? C111 P1 Au1 113.75(14) . . ? C131 P1 Au1 112.59(14) . . ? C121 P1 Au1 112.19(14) . . ? C112 C111 C116 117.8(4) . . ? C112 C111 P1 122.3(3) . . ? C116 C111 P1 119.8(3) . . ? C111 C112 C113 120.6(5) . . ? C111 C112 H112 119.7 . . ? C113 C112 H112 119.7 . . ? C114 C113 C112 120.5(5) . . ? C114 C113 H113 119.7 . . ? C112 C113 H113 119.7 . . ? C115 C114 C113 119.4(5) . . ? C115 C114 H114 120.3 . . ? C113 C114 H114 120.3 . . ? C114 C115 C116 120.6(5) . . ? C114 C115 H115 119.7 . . ? C116 C115 H115 119.7 . . ? C115 C116 C111 121.0(5) . . ? C115 C116 H116 119.5 . . ? C111 C116 H116 119.5 . . ? C126 C121 C122 119.4(4) . . ? C126 C121 P1 122.5(4) . . ? C122 C121 P1 118.1(3) . . ? C121 C122 C123 120.3(5) . . ? C121 C122 H122 119.8 . . ? C123 C122 H122 119.8 . . ? C124 C123 C122 119.3(5) . . ? C124 C123 H123 120.3 . . ? C122 C123 H123 120.3 . . ? C123 C124 C125 120.9(5) . . ? C123 C124 H124 119.6 . . ? C125 C124 H124 119.6 . . ? C124 C125 C126 119.5(5) . . ? C124 C125 H125 120.3 . . ? C126 C125 H125 120.3 . . ? C121 C126 C125 120.6(5) . . ? C121 C126 H126 119.7 . . ? C125 C126 H126 119.7 . . ? C136 C131 C132 118.3(4) . . ? C136 C131 P1 122.9(4) . . ? C132 C131 P1 118.9(3) . . ? C133 C132 C131 120.5(5) . . ? C133 C132 H132 119.8 . . ? C131 C132 H132 119.8 . . ? C132 C133 C134 120.2(5) . . ? C132 C133 H133 119.9 . . ? C134 C133 H133 119.9 . . ? C135 C134 C133 120.1(5) . . ? C135 C134 H134 119.9 . . ? C133 C134 H134 119.9 . . ? C134 C135 C136 120.1(5) . . ? C134 C135 H135 119.9 . . ? C136 C135 H135 119.9 . . ? C135 C136 C131 120.8(5) . . ? C135 C136 H136 119.6 . . ? C131 C136 H136 119.6 . . ? C27A S21 C22 89.4(2) . . ? N23 C22 S22 126.6(4) . . ? N23 C22 S21 115.9(4) . . ? S22 C22 S21 117.3(3) . . ? C22 S22 Au1 103.40(16) . . ? C22 N23 C23A 109.6(4) . . ? C27A C23A C24 120.2(5) . . ? C27A C23A N23 116.1(4) . . ? C24 C23A N23 123.6(5) . . ? C25 C24 C23A 118.3(6) . . ? C25 C24 H24 120.8 . . ? C23A C24 H24 120.8 . . ? C24 C25 C26 121.1(6) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C25 C26 C27 121.6(6) . . ? C25 C26 H26 119.2 . . ? C27 C26 H26 119.2 . . ? C26 C27 C27A 117.8(6) . . ? C26 C27 H27 121.1 . . ? C27A C27 H27 121.1 . . ? C27 C27A C23A 121.0(5) . . ? C27 C27A S21 130.0(4) . . ? C23A C27A S21 109.0(4) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.443 _refine_diff_density_min -1.084 _refine_diff_density_rms 0.106 # Attachment '4.CIF' data_hatzi26a _database_code_depnum_ccdc_archive 'CCDC 733449' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Au Cl P' _chemical_formula_weight 494.69 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.1850(10) _cell_length_b 12.3820(10) _cell_length_c 13.1070(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1652.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 52 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 16.7 _exptl_crystal_description prismatic _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 9.148 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.394 _exptl_absorpt_correction_T_max 0.792 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type P4 _diffrn_measurement_method scintillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1999 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1922 _reflns_number_gt 1810 _reflns_threshold_expression >2sigma(I) _computing_data_collection XSCANS _computing_cell_refinement XSCANS _computing_data_reduction XSCANS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+0.7376P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(13) _refine_ls_number_reflns 1922 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0585 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.16285(3) 0.06947(2) 0.759392(19) 0.04554(10) Uani 1 d . . . P1 P -0.03868(18) 0.12566(15) 0.71981(14) 0.0427(4) Uani 1 d . . . Cl1 Cl 0.36932(19) 0.01250(19) 0.80005(16) 0.0630(5) Uani 1 d . . . C1 C -0.1538(7) 0.0154(6) 0.7023(5) 0.0465(16) Uani 1 d . . . C2 C -0.1680(9) -0.0558(6) 0.7835(6) 0.0570(18) Uani 1 d . . . H2 H -0.1186 -0.0460 0.8424 0.068 Uiso 1 calc R . . C3 C 0.2551(8) 0.3586(7) 0.7229(8) 0.066(2) Uani 1 d . . . H3 H 0.2663 0.3119 0.6680 0.079 Uiso 1 calc R . . C4 C 0.3248(9) 0.3439(7) 0.8113(8) 0.069(2) Uani 1 d . . . H4 H 0.3822 0.2858 0.8165 0.082 Uiso 1 calc R . . C5 C -0.3115(10) -0.0880(8) 0.6092(8) 0.070(3) Uani 1 d . . . H5 H -0.3612 -0.0987 0.5505 0.084 Uiso 1 calc R . . C6 C -0.2231(8) -0.0009(7) 0.6139(6) 0.055(2) Uani 1 d . . . H6 H -0.2119 0.0448 0.5583 0.066 Uiso 1 calc R . . C7 C -0.0403(7) 0.2041(6) 0.6030(6) 0.0430(16) Uani 1 d . . . C8 C -0.1070(8) 0.3040(7) 0.5968(7) 0.055(2) Uani 1 d . . . H8 H -0.1541 0.3301 0.6524 0.066 Uiso 1 calc R . . C9 C -0.1013(10) 0.3603(8) 0.5101(7) 0.068(3) Uani 1 d . . . H9 H -0.1484 0.4244 0.5052 0.081 Uiso 1 calc R . . C10 C 0.4713(9) 0.1731(7) 0.5719(7) 0.062(2) Uani 1 d . . . H10 H 0.4748 0.1313 0.6308 0.075 Uiso 1 calc R . . C11 C 0.4613(10) -0.2315(8) 0.9336(7) 0.065(2) Uani 1 d . . . H11 H 0.4118 -0.2073 0.8785 0.078 Uiso 1 calc R . . C12 C 0.0318(9) 0.1721(6) 0.5219(6) 0.056(2) Uani 1 d . . . H12 H 0.0785 0.1077 0.5261 0.067 Uiso 1 calc R . . C13 C -0.1142(7) 0.2092(7) 0.8169(6) 0.0468(18) Uani 1 d . . . C14 C -0.2513(8) 0.2136(8) 0.8278(7) 0.061(2) Uani 1 d . . . H14 H -0.3049 0.1709 0.7869 0.074 Uiso 1 calc R . . C15 C 0.3058(10) -0.2187(10) 0.6008(8) 0.076(3) Uani 1 d . . . H15 H 0.3966 -0.2141 0.5944 0.091 Uiso 1 calc R . . C16 C 0.2732(13) 0.1584(9) 1.0394(8) 0.081(4) Uani 1 d . . . H16 H 0.2348 0.1161 0.9889 0.097 Uiso 1 calc R . . C17 C 0.4073(12) 0.1577(8) 1.0494(8) 0.069(3) Uani 1 d . . . H17 H 0.4588 0.1120 1.0098 0.083 Uiso 1 calc R . . C18 C -0.0357(10) 0.2728(8) 0.8798(6) 0.059(2) Uani 1 d . . . H18 H 0.0552 0.2689 0.8744 0.071 Uiso 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 Au1 0.04557(15) 0.04577(15) 0.04527(14) 0.00295(13) -0.00112(13) 0.00460(13) P1 0.0427(9) 0.0431(9) 0.0423(9) -0.0012(8) 0.0002(8) 0.0030(8) Cl1 0.0512(10) 0.0732(13) 0.0646(12) 0.0120(11) -0.0056(9) 0.0147(10) C1 0.045(4) 0.047(4) 0.048(4) 0.001(3) -0.001(4) 0.007(4) C2 0.061(5) 0.053(4) 0.057(4) 0.001(4) -0.001(4) 0.006(5) C3 0.056(5) 0.055(5) 0.087(7) -0.018(5) 0.012(5) 0.008(4) C4 0.047(5) 0.056(5) 0.103(7) 0.004(5) 0.003(6) 0.009(5) C5 0.060(6) 0.068(6) 0.082(6) -0.015(5) -0.019(5) -0.003(5) C6 0.059(5) 0.047(4) 0.060(5) -0.004(4) 0.002(4) -0.005(4) C7 0.044(4) 0.038(4) 0.047(4) 0.004(3) 0.000(3) 0.003(4) C8 0.058(5) 0.050(5) 0.057(5) 0.005(4) 0.003(4) 0.016(4) C9 0.073(6) 0.056(6) 0.074(6) 0.012(5) -0.009(5) 0.001(5) C10 0.066(5) 0.066(6) 0.055(5) 0.015(4) 0.010(4) 0.004(5) C11 0.072(6) 0.070(6) 0.053(5) -0.006(5) -0.012(5) 0.007(5) C12 0.065(5) 0.049(4) 0.052(4) 0.006(4) 0.014(4) 0.012(5) C13 0.053(4) 0.052(4) 0.035(4) -0.001(4) 0.005(3) 0.007(4) C14 0.057(5) 0.076(6) 0.052(5) -0.004(5) 0.000(4) 0.020(5) C15 0.067(6) 0.100(8) 0.062(5) 0.010(6) 0.010(5) -0.032(6) C16 0.116(9) 0.079(7) 0.048(5) -0.003(5) -0.023(6) -0.044(7) C17 0.102(9) 0.048(5) 0.057(5) -0.011(4) -0.011(5) 0.005(6) C18 0.069(6) 0.061(5) 0.048(5) -0.001(4) 0.008(4) -0.003(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 2.2285(18) . ? Au1 Cl1 2.2812(19) . ? P1 C13 1.811(8) . ? P1 C7 1.814(7) . ? P1 C1 1.815(8) . ? C1 C6 1.371(11) . ? C1 C2 1.389(10) . ? C2 C3 1.384(11) 3_546 ? C2 H2 0.9300 . ? C3 C4 1.371(13) . ? C3 C2 1.384(11) 3_556 ? C3 H3 0.9300 . ? C4 C5 1.348(13) 3_556 ? C4 H4 0.9300 . ? C5 C4 1.348(13) 3_546 ? C5 C6 1.406(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.351(11) . ? C7 C8 1.413(11) . ? C8 C9 1.335(12) . ? C8 H8 0.9300 . ? C9 C10 1.369(14) 4_456 ? C9 H9 0.9300 . ? C10 C11 1.368(12) 3_656 ? C10 C9 1.369(14) 4_556 ? C10 H10 0.9300 . ? C11 C10 1.368(12) 3_646 ? C11 C12 1.374(12) 2 ? C11 H11 0.9300 . ? C12 C11 1.374(12) 2_554 ? C12 H12 0.9300 . ? C13 C18 1.393(12) . ? C13 C14 1.404(11) . ? C14 C15 1.373(12) 3_556 ? C14 H14 0.9300 . ? C15 C16 1.361(16) 2_554 ? C15 C14 1.373(12) 3_546 ? C15 H15 0.9300 . ? C16 C15 1.361(16) 2 ? C16 C17 1.372(14) . ? C16 H16 0.9300 . ? C17 C18 1.393(13) 4_557 ? C17 H17 0.9300 . ? C18 C17 1.393(13) 4_457 ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 Cl1 179.82(8) . . ? C13 P1 C7 106.5(4) . . ? C13 P1 C1 104.1(3) . . ? C7 P1 C1 106.9(3) . . ? C13 P1 Au1 114.0(3) . . ? C7 P1 Au1 111.9(3) . . ? C1 P1 Au1 112.9(2) . . ? C6 C1 C2 120.0(7) . . ? C6 C1 P1 123.4(6) . . ? C2 C1 P1 116.6(6) . . ? C3 C2 C1 120.4(8) 3_546 . ? C3 C2 H2 119.8 3_546 . ? C1 C2 H2 119.8 . . ? C4 C3 C2 119.0(8) . 3_556 ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 3_556 . ? C5 C4 C3 121.2(8) 3_556 . ? C5 C4 H4 119.4 3_556 . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.7(9) 3_546 . ? C4 C5 H5 119.7 3_546 . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.6(8) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C12 C7 C8 118.2(7) . . ? C12 C7 P1 120.1(6) . . ? C8 C7 P1 121.4(6) . . ? C9 C8 C7 119.0(8) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 122.3(9) . 4_456 ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 4_456 . ? C11 C10 C9 119.4(8) 3_656 4_556 ? C11 C10 H10 120.3 3_656 . ? C9 C10 H10 120.3 4_556 . ? C10 C11 C12 118.7(8) 3_646 2 ? C10 C11 H11 120.6 3_646 . ? C12 C11 H11 120.6 2 . ? C7 C12 C11 122.3(8) . 2_554 ? C7 C12 H12 118.9 . . ? C11 C12 H12 118.9 2_554 . ? C18 C13 C14 119.2(8) . . ? C18 C13 P1 119.7(6) . . ? C14 C13 P1 121.1(7) . . ? C15 C14 C13 119.7(10) 3_556 . ? C15 C14 H14 120.1 3_556 . ? C13 C14 H14 120.1 . . ? C16 C15 C14 119.9(10) 2_554 3_546 ? C16 C15 H15 120.1 2_554 . ? C14 C15 H15 120.1 3_546 . ? C15 C16 C17 122.4(11) 2 . ? C15 C16 H16 118.8 2 . ? C17 C16 H16 118.8 . . ? C16 C17 C18 118.3(11) . 4_557 ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 4_557 . ? C13 C18 C17 120.3(9) . 4_457 ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 4_457 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl1 Au1 P1 C13 -48(20) . . . . ? Cl1 Au1 P1 C7 72(20) . . . . ? Cl1 Au1 P1 C1 -167(32) . . . . ? C13 P1 C1 C6 113.6(7) . . . . ? C7 P1 C1 C6 1.2(8) . . . . ? Au1 P1 C1 C6 -122.3(6) . . . . ? C13 P1 C1 C2 -67.7(7) . . . . ? C7 P1 C1 C2 179.8(6) . . . . ? Au1 P1 C1 C2 56.4(6) . . . . ? C6 C1 C2 C3 -2.2(12) . . . 3_546 ? P1 C1 C2 C3 179.1(6) . . . 3_546 ? C2 C3 C4 C5 -1.2(14) 3_556 . . 3_556 ? C2 C1 C6 C5 2.4(12) . . . . ? P1 C1 C6 C5 -179.0(7) . . . . ? C4 C5 C6 C1 -2.0(14) 3_546 . . . ? C13 P1 C7 C12 167.1(7) . . . . ? C1 P1 C7 C12 -82.1(8) . . . . ? Au1 P1 C7 C12 42.0(8) . . . . ? C13 P1 C7 C8 -7.4(8) . . . . ? C1 P1 C7 C8 103.4(7) . . . . ? Au1 P1 C7 C8 -132.5(6) . . . . ? C12 C7 C8 C9 3.1(13) . . . . ? P1 C7 C8 C9 177.7(7) . . . . ? C7 C8 C9 C10 -2.8(14) . . . 4_456 ? C8 C7 C12 C11 -2.2(14) . . . 2_554 ? P1 C7 C12 C11 -176.8(8) . . . 2_554 ? C7 P1 C13 C18 -94.2(7) . . . . ? C1 P1 C13 C18 153.0(7) . . . . ? Au1 P1 C13 C18 29.6(8) . . . . ? C7 P1 C13 C14 83.7(8) . . . . ? C1 P1 C13 C14 -29.1(9) . . . . ? Au1 P1 C13 C14 -152.5(7) . . . . ? C18 C13 C14 C15 0.7(15) . . . 3_556 ? P1 C13 C14 C15 -177.2(7) . . . 3_556 ? C15 C16 C17 C18 -4.6(19) 2 . . 4_557 ? C14 C13 C18 C17 -1.8(14) . . . 4_457 ? P1 C13 C18 C17 176.2(7) . . . 4_457 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.439 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.093 # Attachment '3.CIF' data_hatzi40a _database_code_depnum_ccdc_archive 'CCDC 733450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N O5 S' _chemical_formula_weight 203.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7620(10) _cell_length_b 7.8400(10) _cell_length_c 8.7970(10) _cell_angle_alpha 63.610(10) _cell_angle_beta 85.350(10) _cell_angle_gamma 65.390(10) _cell_volume 376.71(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 24.27 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 3.826 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type P4 _diffrn_measurement_method scintillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1670 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.66 _diffrn_reflns_theta_max 68.93 _reflns_number_total 1358 _reflns_number_gt 1084 _reflns_threshold_expression >2sigma(I) _computing_data_collection XSCANS _computing_cell_refinement XSCANS _computing_data_reduction XSCANS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.2259P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1358 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.23352(13) 0.07686(13) 0.18521(11) 0.0241(3) Uani 1 d . . . O1 O 0.1634(4) 0.0678(4) 0.3470(4) 0.0332(7) Uani 1 d . . . O2 O 0.3812(5) 0.1753(4) 0.1221(4) 0.0390(7) Uani 1 d . . . O3 O 0.0557(5) 0.1433(4) 0.0628(4) 0.0450(9) Uani 1 d . . . O4 O 0.6397(4) -0.1685(5) 0.4742(4) 0.0375(7) Uani 1 d . . . O5 O 0.9282(5) -0.2694(7) 0.3425(5) 0.0566(10) Uani 1 d . . . C1 C 0.3989(5) -0.1925(5) 0.2255(4) 0.0189(7) Uani 1 d . . . N2 N 0.3006(4) -0.2726(4) 0.1662(4) 0.0214(6) Uani 1 d . . . H2 H 0.1669 -0.1951 0.1186 0.026 Uiso 1 calc R . . C3 C 0.3979(6) -0.4653(6) 0.1766(5) 0.0273(8) Uani 1 d . . . H3 H 0.3211 -0.5132 0.1345 0.033 Uiso 1 calc R . . C4 C 0.6117(6) -0.5920(6) 0.2497(5) 0.0327(9) Uani 1 d . . . H4 H 0.6818 -0.7270 0.2587 0.039 Uiso 1 calc R . . C5 C 0.7215(6) -0.5144(6) 0.3103(5) 0.0320(9) Uani 1 d . . . H5 H 0.8677 -0.5971 0.3577 0.038 Uiso 1 calc R . . C6 C 0.6158(5) -0.3159(5) 0.3009(4) 0.0213(7) Uani 1 d . . . C7 C 0.7453(5) -0.2439(6) 0.3722(5) 0.0258(8) Uani 1 d . . . H1 H 0.724(10) -0.144(10) 0.523(9) 0.080 Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0247(5) 0.0213(5) 0.0275(5) -0.0145(4) -0.0060(3) -0.0055(3) O1 0.0244(12) 0.0434(16) 0.0406(18) -0.0307(14) 0.0052(11) -0.0096(11) O2 0.0539(17) 0.0356(15) 0.0421(18) -0.0193(13) 0.0073(14) -0.0302(14) O3 0.0425(16) 0.0307(15) 0.052(2) -0.0223(14) -0.0266(14) 0.0023(12) O4 0.0303(14) 0.0582(19) 0.0448(18) -0.0403(16) 0.0044(12) -0.0188(13) O5 0.0356(16) 0.107(3) 0.072(3) -0.066(2) 0.0246(16) -0.0448(18) C1 0.0202(15) 0.0254(17) 0.0164(17) -0.0130(14) 0.0040(12) -0.0108(13) N2 0.0199(13) 0.0248(14) 0.0235(16) -0.0148(12) -0.0003(11) -0.0084(11) C3 0.0339(18) 0.0301(19) 0.029(2) -0.0196(16) 0.0045(15) -0.0174(16) C4 0.037(2) 0.0257(18) 0.035(2) -0.0185(16) 0.0010(16) -0.0076(16) C5 0.0249(18) 0.0316(19) 0.034(2) -0.0179(16) -0.0056(15) -0.0020(15) C6 0.0226(15) 0.0299(18) 0.0149(17) -0.0125(13) 0.0029(12) -0.0118(14) C7 0.0216(16) 0.0350(19) 0.0235(19) -0.0151(15) 0.0010(13) -0.0121(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.437(3) . ? S1 O2 1.439(3) . ? S1 O1 1.444(3) . ? S1 C1 1.808(3) . ? O4 C7 1.296(4) . ? O4 H1 0.86(7) . ? O5 C7 1.194(4) . ? C1 N2 1.343(4) . ? C1 C6 1.390(4) . ? N2 C3 1.335(4) . ? N2 H2 0.8600 . ? C3 C4 1.370(5) . ? C3 H3 0.9300 . ? C4 C5 1.391(5) . ? C4 H4 0.9300 . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.515(5) . ? 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 O3 S1 O2 115.8(2) . . ? O3 S1 O1 112.69(18) . . ? O2 S1 O1 114.40(16) . . ? O3 S1 C1 102.60(15) . . ? O2 S1 C1 103.50(16) . . ? O1 S1 C1 106.09(16) . . ? C7 O4 H1 110(4) . . ? N2 C1 C6 118.4(3) . . ? N2 C1 S1 114.7(2) . . ? C6 C1 S1 126.8(3) . . ? C3 N2 C1 124.0(3) . . ? C3 N2 H2 118.0 . . ? C1 N2 H2 118.0 . . ? N2 C3 C4 119.5(3) . . ? N2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.8(3) . . ? C5 C6 C7 117.7(3) . . ? C1 C6 C7 123.5(3) . . ? O5 C7 O4 126.2(3) . . ? O5 C7 C6 121.6(3) . . ? O4 C7 C6 112.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 C1 N2 -12.9(3) . . . . ? O2 S1 C1 N2 -133.7(3) . . . . ? O1 S1 C1 N2 105.5(3) . . . . ? O3 S1 C1 C6 163.1(3) . . . . ? O2 S1 C1 C6 42.3(4) . . . . ? O1 S1 C1 C6 -78.5(3) . . . . ? C6 C1 N2 C3 0.7(5) . . . . ? S1 C1 N2 C3 177.1(3) . . . . ? C1 N2 C3 C4 -0.8(6) . . . . ? N2 C3 C4 C5 -0.4(6) . . . . ? C3 C4 C5 C6 1.6(6) . . . . ? C4 C5 C6 C1 -1.7(6) . . . . ? C4 C5 C6 C7 179.0(4) . . . . ? N2 C1 C6 C5 0.6(5) . . . . ? S1 C1 C6 C5 -175.4(3) . . . . ? N2 C1 C6 C7 179.8(3) . . . . ? S1 C1 C6 C7 3.9(5) . . . . ? C5 C6 C7 O5 45.0(6) . . . . ? C1 C6 C7 O5 -134.2(4) . . . . ? C5 C6 C7 O4 -130.6(4) . . . . ? C1 C6 C7 O4 50.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 68.93 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.710 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.107 # Attachment '5.cif' data_56pph3 _database_code_depnum_ccdc_archive 'CCDC 733451' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 Au N P S2' _chemical_formula_weight 577.43 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' S S 0.1246 0.1234 '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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8350(10) _cell_length_b 10.9260(10) _cell_length_c 11.426(2) _cell_angle_alpha 87.140(10) _cell_angle_beta 87.720(10) _cell_angle_gamma 75.210(10) _cell_volume 1064.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 1.9465 _cell_measurement_theta_max 12.507 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 7.185 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.194 _exptl_absorpt_correction_T_max 0.663 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type P4 _diffrn_measurement_method scintilation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4546 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3750 _reflns_number_gt 3470 _reflns_threshold_expression >2sigma(I) _computing_data_collection XSCANS _computing_cell_refinement XSCANS _computing_data_reduction XSCANS _computing_structure_solution 'SHELXL-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+1.5745P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3750 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C1 C 0.6652(7) -0.0788(6) 0.2409(6) 0.0497(14) Uani 1 1 d . . . C2 C 0.8218(9) -0.1383(8) 0.2603(8) 0.068(2) Uani 1 1 d . . . H2 H 0.8876 -0.0925 0.2878 0.081 Uiso 1 1 calc R . . C3 C 0.8794(9) -0.2650(8) 0.2389(8) 0.076(2) Uani 1 1 d . . . H3 H 0.9838 -0.3048 0.2526 0.091 Uiso 1 1 calc R . . C4 C 0.7838(11) -0.3321(8) 0.1975(9) 0.084(3) Uani 1 1 d . . . H4 H 0.8241 -0.4166 0.1796 0.101 Uiso 1 1 calc R . . C5 C 0.6286(11) -0.2755(9) 0.1824(10) 0.086(3) Uani 1 1 d . . . H5 H 0.5626 -0.3230 0.1584 0.103 Uiso 1 1 calc R . . C6 C 0.5694(9) -0.1497(8) 0.2021(8) 0.070(2) Uani 1 1 d . . . H6 H 0.4643 -0.1116 0.1894 0.084 Uiso 1 1 calc R . . C7 C 0.3839(7) 0.1260(6) 0.2589(6) 0.0501(14) Uani 1 1 d . . . C8 C 0.3100(9) 0.1613(9) 0.1525(8) 0.073(2) Uani 1 1 d . . . H8 H 0.3678 0.1660 0.0834 0.087 Uiso 1 1 calc R . . C9 C 0.1444(10) 0.1898(11) 0.1524(10) 0.089(3) Uani 1 1 d . . . H9 H 0.0921 0.2155 0.0828 0.107 Uiso 1 1 calc R . . C10 C 0.0603(10) 0.1795(9) 0.2552(10) 0.084(3) Uani 1 1 d . . . H10 H -0.0482 0.1956 0.2541 0.101 Uiso 1 1 calc R . . C11 C 0.1359(9) 0.1457(8) 0.3591(9) 0.073(2) Uani 1 1 d . . . H11 H 0.0787 0.1414 0.4286 0.087 Uiso 1 1 calc R . . C12 C 0.2972(8) 0.1182(6) 0.3599(7) 0.0602(17) Uani 1 1 d . . . H12 H 0.3481 0.0938 0.4302 0.072 Uiso 1 1 calc R . . C13 C 0.6598(8) 0.1714(7) 0.1386(6) 0.0525(15) Uani 1 1 d . . . C14 C 0.7340(9) 0.1089(8) 0.0441(7) 0.0668(18) Uani 1 1 d . . . H14 H 0.7537 0.0211 0.0434 0.080 Uiso 1 1 calc R . . C15 C 0.7805(11) 0.1761(11) -0.0514(7) 0.082(3) Uani 1 1 d . . . H15 H 0.8310 0.1335 -0.1161 0.098 Uiso 1 1 calc R . . C16 C 0.7514(11) 0.3061(11) -0.0497(8) 0.086(3) Uani 1 1 d . . . H16 H 0.7822 0.3517 -0.1131 0.103 Uiso 1 1 calc R . . C17 C 0.6773(12) 0.3672(10) 0.0457(9) 0.083(3) Uani 1 1 d . . . H17 H 0.6557 0.4551 0.0460 0.100 Uiso 1 1 calc R . . C18 C 0.6336(10) 0.3012(7) 0.1418(7) 0.0671(19) Uani 1 1 d . . . H18 H 0.5871 0.3436 0.2078 0.081 Uiso 1 1 calc R . . Au1 Au 0.68043(3) 0.14513(2) 0.433749(19) 0.04792(12) Uani 1 1 d . . . S1 S 0.7707(3) 0.19767(17) 0.60494(16) 0.0613(4) Uani 1 1 d . . . S2 S 0.7406(4) 0.4318(2) 0.44295(19) 0.0923(8) Uani 1 1 d . . . P1 P 0.59515(18) 0.08862(16) 0.26611(15) 0.0463(3) Uani 1 1 d . . . N1 N 0.7579(10) 0.4291(6) 0.6689(6) 0.0746(19) Uani 1 1 d . . . C19 C 0.7535(8) 0.3599(6) 0.5840(6) 0.0495(14) Uani 1 1 d . . . C21 C 0.7583(15) 0.5577(8) 0.6302(9) 0.092(3) Uani 1 1 d . . . H21A H 0.8603 0.5714 0.6434 0.110 Uiso 1 1 calc R . . H21B H 0.6814 0.6168 0.6766 0.110 Uiso 1 1 calc R . . C20 C 0.7220(16) 0.5834(8) 0.5040(9) 0.097(3) Uani 1 1 d . . . H20A H 0.7949 0.6262 0.4650 0.117 Uiso 1 1 calc R . . H20B H 0.6165 0.6365 0.4951 0.117 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 C1 0.036(3) 0.053(4) 0.055(3) -0.012(3) 0.001(3) -0.001(3) C2 0.046(4) 0.069(5) 0.083(5) 0.000(4) -0.008(4) -0.004(3) C3 0.047(4) 0.071(5) 0.095(6) -0.001(4) -0.001(4) 0.009(4) C4 0.082(6) 0.058(5) 0.099(7) -0.006(4) -0.010(5) 0.009(4) C5 0.071(5) 0.065(5) 0.118(8) -0.025(5) -0.020(5) -0.005(4) C6 0.050(4) 0.059(4) 0.098(6) -0.019(4) -0.013(4) -0.003(3) C7 0.036(3) 0.044(3) 0.070(4) -0.012(3) 0.006(3) -0.008(2) C8 0.046(4) 0.089(6) 0.076(5) -0.023(4) -0.009(3) -0.001(4) C9 0.047(4) 0.113(7) 0.101(7) -0.036(6) -0.024(4) 0.002(4) C10 0.043(4) 0.079(6) 0.128(8) -0.026(5) 0.011(5) -0.011(4) C11 0.044(4) 0.066(5) 0.104(6) 0.002(4) 0.021(4) -0.012(3) C12 0.052(4) 0.045(4) 0.081(5) 0.004(3) 0.011(3) -0.010(3) C13 0.044(3) 0.070(4) 0.043(3) 0.002(3) -0.004(3) -0.015(3) C14 0.063(4) 0.075(5) 0.063(4) -0.005(4) 0.002(3) -0.019(4) C15 0.072(5) 0.125(8) 0.049(4) 0.003(4) 0.012(4) -0.031(5) C16 0.079(6) 0.113(8) 0.067(5) 0.028(5) -0.005(4) -0.030(5) C17 0.085(6) 0.076(6) 0.087(6) 0.024(5) -0.009(5) -0.023(5) C18 0.072(5) 0.061(4) 0.065(4) 0.006(3) -0.004(4) -0.014(4) Au1 0.04641(17) 0.05099(17) 0.04737(16) -0.00189(10) -0.00112(10) -0.01425(11) S1 0.0830(13) 0.0505(9) 0.0528(9) 0.0042(7) -0.0159(8) -0.0201(9) S2 0.161(3) 0.0593(12) 0.0563(11) 0.0054(9) -0.0008(13) -0.0298(14) P1 0.0362(8) 0.0522(9) 0.0498(8) -0.0057(7) 0.0016(6) -0.0098(7) N1 0.106(6) 0.052(3) 0.062(4) -0.003(3) -0.008(4) -0.013(3) C19 0.044(3) 0.050(3) 0.051(3) -0.003(3) 0.000(3) -0.007(3) C21 0.133(9) 0.051(5) 0.090(6) -0.006(4) 0.016(6) -0.025(5) C20 0.148(10) 0.051(5) 0.089(6) 0.010(4) -0.008(6) -0.020(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 C1 C6 1.382(10) . ? C1 C2 1.392(9) . ? C1 P1 1.809(7) . ? C2 C3 1.379(12) . ? C2 H2 0.9300 . ? C3 C4 1.363(13) . ? C3 H3 0.9300 . ? C4 C5 1.367(13) . ? C4 H4 0.9300 . ? C5 C6 1.367(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.371(10) . ? C7 C8 1.393(11) . ? C7 P1 1.810(6) . ? C8 C9 1.416(11) . ? C8 H8 0.9300 . ? C9 C10 1.379(15) . ? C9 H9 0.9300 . ? C10 C11 1.374(14) . ? C10 H10 0.9300 . ? C11 C12 1.379(10) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.361(10) . ? C13 C18 1.379(10) . ? C13 P1 1.826(7) . ? C14 C15 1.392(11) . ? C14 H14 0.9300 . ? C15 C16 1.379(14) . ? C15 H15 0.9300 . ? C16 C17 1.361(14) . ? C16 H16 0.9300 . ? C17 C18 1.381(12) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? Au1 P1 2.2557(17) . ? Au1 S1 2.2937(18) . ? S1 C19 1.745(7) . ? S2 C19 1.752(7) . ? S2 C20 1.796(10) . ? N1 C19 1.267(9) . ? N1 C21 1.452(11) . ? C21 C20 1.487(14) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 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 C6 C1 C2 118.8(7) . . ? C6 C1 P1 122.5(5) . . ? C2 C1 P1 118.7(6) . . ? C3 C2 C1 120.0(8) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.2(7) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.0(8) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.6(9) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.3(7) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C12 C7 C8 120.3(6) . . ? C12 C7 P1 118.9(6) . . ? C8 C7 P1 120.8(5) . . ? C7 C8 C9 118.2(9) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 120.2(9) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.4(8) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.7(8) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 121.2(8) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C18 120.4(7) . . ? C14 C13 P1 122.1(6) . . ? C18 C13 P1 117.5(5) . . ? C13 C14 C15 120.1(8) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 119.7(9) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 119.5(8) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 121.2(9) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C13 C18 C17 119.1(8) . . ? C13 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? P1 Au1 S1 178.62(6) . . ? C19 S1 Au1 103.2(2) . . ? C19 S2 C20 90.3(4) . . ? C7 P1 C1 106.3(3) . . ? C7 P1 C13 105.3(3) . . ? C1 P1 C13 106.3(3) . . ? C7 P1 Au1 113.6(2) . . ? C1 P1 Au1 113.3(2) . . ? C13 P1 Au1 111.3(2) . . ? C19 N1 C21 112.3(7) . . ? N1 C19 S1 121.6(6) . . ? N1 C19 S2 117.3(6) . . ? S1 C19 S2 121.0(4) . . ? N1 C21 C20 112.2(8) . . ? N1 C21 H21A 109.2 . . ? C20 C21 H21A 109.2 . . ? N1 C21 H21B 109.2 . . ? C20 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C21 C20 S2 106.1(6) . . ? C21 C20 H20A 110.5 . . ? S2 C20 H20A 110.5 . . ? C21 C20 H20B 110.5 . . ? S2 C20 H20B 110.5 . . ? H20A C20 H20B 108.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.2(13) . . . . ? P1 C1 C2 C3 -178.3(7) . . . . ? C1 C2 C3 C4 0.6(14) . . . . ? C2 C3 C4 C5 -3.0(16) . . . . ? C3 C4 C5 C6 3.6(17) . . . . ? C4 C5 C6 C1 -1.8(16) . . . . ? C2 C1 C6 C5 -0.6(14) . . . . ? P1 C1 C6 C5 178.8(8) . . . . ? C12 C7 C8 C9 0.7(12) . . . . ? P1 C7 C8 C9 -179.8(7) . . . . ? C7 C8 C9 C10 -1.5(14) . . . . ? C8 C9 C10 C11 2.2(15) . . . . ? C9 C10 C11 C12 -2.0(14) . . . . ? C8 C7 C12 C11 -0.5(11) . . . . ? P1 C7 C12 C11 179.9(6) . . . . ? C10 C11 C12 C7 1.2(12) . . . . ? C18 C13 C14 C15 -1.7(12) . . . . ? P1 C13 C14 C15 179.7(6) . . . . ? C13 C14 C15 C16 0.2(13) . . . . ? C14 C15 C16 C17 0.0(14) . . . . ? C15 C16 C17 C18 1.4(15) . . . . ? C14 C13 C18 C17 2.9(12) . . . . ? P1 C13 C18 C17 -178.4(7) . . . . ? C16 C17 C18 C13 -2.8(14) . . . . ? P1 Au1 S1 C19 155(2) . . . . ? C12 C7 P1 C1 91.0(6) . . . . ? C8 C7 P1 C1 -88.6(7) . . . . ? C12 C7 P1 C13 -156.4(5) . . . . ? C8 C7 P1 C13 24.0(7) . . . . ? C12 C7 P1 Au1 -34.4(6) . . . . ? C8 C7 P1 Au1 146.1(6) . . . . ? C6 C1 P1 C7 10.9(8) . . . . ? C2 C1 P1 C7 -169.7(6) . . . . ? C6 C1 P1 C13 -101.0(7) . . . . ? C2 C1 P1 C13 78.4(7) . . . . ? C6 C1 P1 Au1 136.4(6) . . . . ? C2 C1 P1 Au1 -44.1(7) . . . . ? C14 C13 P1 C7 -107.8(6) . . . . ? C18 C13 P1 C7 73.5(6) . . . . ? C14 C13 P1 C1 4.8(7) . . . . ? C18 C13 P1 C1 -173.9(5) . . . . ? C14 C13 P1 Au1 128.6(6) . . . . ? C18 C13 P1 Au1 -50.1(6) . . . . ? S1 Au1 P1 C7 125(3) . . . . ? S1 Au1 P1 C1 4(3) . . . . ? S1 Au1 P1 C13 -116(3) . . . . ? C21 N1 C19 S1 173.8(7) . . . . ? C21 N1 C19 S2 -2.6(11) . . . . ? Au1 S1 C19 N1 163.5(6) . . . . ? Au1 S1 C19 S2 -20.2(5) . . . . ? C20 S2 C19 N1 -5.1(8) . . . . ? C20 S2 C19 S1 178.4(6) . . . . ? C19 N1 C21 C20 11.2(14) . . . . ? N1 C21 C20 S2 -14.1(13) . . . . ? C19 S2 C20 C21 10.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.429 _refine_diff_density_min -1.753 _refine_diff_density_rms 0.144