# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Kelly Chibale' _publ_contact_author_email KELLY.CHIBALE@UCT.AC.ZA _publ_section_title ; Gold(I) Derived Thiosemicarbazone Complexes with rare halogen-halogen interaction - Reduction of [Au(damp-C1,N)Cl2]. ; loop_ _publ_author_name 'Kelly Chibale' 'Nikoletta B Bathoria' 'Setshaba Khanye' 'Gregory S. Smith' # Attachment 'HL1_Br.CIF' data_c:\public~2\david\new_cifs\dk65d _database_code_depnum_ccdc_archive 'CCDC 720892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Au Br2 Cl N8 S2' _chemical_formula_weight 858.86 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.846(2) _cell_length_b 10.358(2) _cell_length_c 24.577(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.89(3) _cell_angle_gamma 90.00 _cell_volume 2950.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12752 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 25.33 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 7.952 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details 'SADABS, Sheldrick' _exptl_special_details ; ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12752 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2705 _reflns_number_gt 2313 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001), Platon (Spek, 2003)' _computing_publication_material 'Platon (Spek, 2003)' _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^)+(0.0282P)^2^+4.8281P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00031(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2705 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.0000 0.15149(3) 0.2500 0.03108(12) Uani 1 2 d S . . Br1 Br 0.62417(6) 0.83019(6) 0.53292(3) 0.0638(2) Uani 1 1 d . . . Cl1 Cl 0.0000 0.47264(15) 0.2500 0.0303(4) Uani 1 2 d S . . S1 S 0.18825(10) 0.13275(12) 0.24263(5) 0.0350(3) Uani 1 1 d . . . N1 N 0.3852(3) 0.2180(4) 0.29962(17) 0.0362(10) Uani 1 1 d . . . H1A H 0.4300 0.2670 0.3243 0.043 Uiso 1 1 calc R . . H1B H 0.4157 0.1584 0.2816 0.043 Uiso 1 1 calc R . . C1 C 0.2724(4) 0.2339(4) 0.28972(18) 0.0283(11) Uani 1 1 d . . . N2 N 0.2275(3) 0.3251(3) 0.31759(16) 0.0308(9) Uani 1 1 d . . . H2 H 0.1525 0.3355 0.3136 0.037 Uiso 1 1 calc R . . C2 C 0.2660(4) 0.4790(4) 0.38628(19) 0.0306(11) Uani 1 1 d . . . N3 N 0.3062(3) 0.4030(4) 0.35342(16) 0.0319(9) Uani 1 1 d . . . C3 C 0.1421(4) 0.4903(5) 0.3903(2) 0.0445(14) Uani 1 1 d . . . H3A H 0.1118 0.5741 0.3754 0.067 Uiso 1 1 calc R . . H3B H 0.1357 0.4834 0.4293 0.067 Uiso 1 1 calc R . . H3C H 0.0976 0.4209 0.3687 0.067 Uiso 1 1 calc R . . N4 N 0.6153(5) 0.3334(5) 0.3549(2) 0.0579(14) Uani 1 1 d . . . C4 C 0.3530(4) 0.5612(5) 0.42226(19) 0.0345(12) Uani 1 1 d . . . C5 C 0.4579(4) 0.5882(5) 0.4071(2) 0.0396(13) Uani 1 1 d . . . H5 H 0.4736 0.5524 0.3739 0.047 Uiso 1 1 calc R . . C6 C 0.5394(5) 0.6666(5) 0.4400(2) 0.0457(14) Uani 1 1 d . . . H6 H 0.6105 0.6848 0.4295 0.055 Uiso 1 1 calc R . . C7 C 0.5159(5) 0.7178(5) 0.4882(2) 0.0443(14) Uani 1 1 d . . . C8 C 0.4160(6) 0.6906(6) 0.5046(2) 0.0565(17) Uani 1 1 d . . . H8 H 0.4021 0.7250 0.5384 0.068 Uiso 1 1 calc R . . C9 C 0.3339(6) 0.6124(6) 0.4717(2) 0.0519(16) Uani 1 1 d . . . H9 H 0.2639 0.5937 0.4832 0.062 Uiso 1 1 calc R . . C10 C 0.7068(5) 0.3653(5) 0.3563(2) 0.0384(13) Uani 1 1 d . . . C11 C 0.8250(4) 0.4039(6) 0.3591(2) 0.0458(14) Uani 1 1 d . . . H11A H 0.8738 0.3676 0.3927 0.069 Uiso 1 1 calc R . . H11B H 0.8303 0.4983 0.3604 0.069 Uiso 1 1 calc R . . H11C H 0.8510 0.3719 0.3263 0.069 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 Au1 0.02906(17) 0.02581(17) 0.03593(18) 0.000 0.00101(11) 0.000 Br1 0.0785(5) 0.0509(4) 0.0488(4) -0.0112(3) -0.0173(3) -0.0091(3) Cl1 0.0239(8) 0.0250(9) 0.0423(9) 0.000 0.0076(7) 0.000 S1 0.0290(6) 0.0329(7) 0.0408(7) -0.0103(5) 0.0018(6) 0.0033(5) N1 0.027(2) 0.035(2) 0.044(2) -0.0094(19) 0.0019(19) 0.0034(18) C1 0.031(3) 0.022(3) 0.032(3) 0.0009(19) 0.007(2) 0.002(2) N2 0.026(2) 0.029(2) 0.036(2) -0.0036(17) 0.0035(18) 0.0016(17) C2 0.040(3) 0.024(3) 0.028(2) 0.005(2) 0.006(2) 0.003(2) N3 0.036(2) 0.021(2) 0.036(2) -0.0027(17) 0.0016(19) -0.0004(17) C3 0.042(3) 0.049(4) 0.045(3) -0.011(3) 0.015(3) -0.005(3) N4 0.044(3) 0.067(4) 0.063(3) -0.003(3) 0.010(3) 0.000(3) C4 0.045(3) 0.023(3) 0.032(3) 0.007(2) 0.001(2) 0.004(2) C5 0.038(3) 0.040(3) 0.038(3) -0.011(2) 0.000(2) 0.009(2) C6 0.039(3) 0.039(3) 0.053(3) -0.007(3) -0.004(3) 0.006(2) C7 0.056(3) 0.034(3) 0.036(3) -0.001(2) -0.008(3) 0.000(3) C8 0.088(5) 0.048(4) 0.034(3) -0.013(3) 0.012(3) -0.010(3) C9 0.070(4) 0.047(4) 0.042(3) -0.009(3) 0.020(3) -0.013(3) C10 0.039(3) 0.036(3) 0.038(3) 0.001(2) 0.002(2) 0.002(2) C11 0.042(3) 0.041(3) 0.055(3) -0.001(3) 0.010(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 S1 2.2826(13) . ? Au1 S1 2.2826(13) 2 ? Br1 C7 1.905(5) . ? S1 C1 1.719(5) . ? N1 C1 1.319(6) . ? C1 N2 1.339(6) . ? N2 N3 1.399(5) . ? C2 N3 1.287(6) . ? C2 C4 1.481(7) . ? C2 C3 1.496(7) . ? N4 C10 1.128(7) . ? C4 C9 1.386(7) . ? C4 C5 1.396(7) . ? C5 C6 1.387(7) . ? C6 C7 1.376(8) . ? C7 C8 1.356(9) . ? C8 C9 1.389(8) . ? C10 C11 1.443(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Au1 S1 170.24(6) . 2 ? C1 S1 Au1 109.57(17) . . ? N1 C1 N2 119.2(4) . . ? N1 C1 S1 118.2(4) . . ? N2 C1 S1 122.6(3) . . ? C1 N2 N3 116.5(4) . . ? N3 C2 C4 115.1(5) . . ? N3 C2 C3 125.7(4) . . ? C4 C2 C3 119.2(4) . . ? C2 N3 N2 117.6(4) . . ? C9 C4 C5 118.1(5) . . ? C9 C4 C2 121.6(5) . . ? C5 C4 C2 120.3(5) . . ? C6 C5 C4 120.8(5) . . ? C7 C6 C5 119.2(6) . . ? C8 C7 C6 121.2(5) . . ? C8 C7 Br1 118.8(4) . . ? C6 C7 Br1 120.0(5) . . ? C7 C8 C9 119.8(5) . . ? C4 C9 C8 120.8(6) . . ? N4 C10 C11 178.6(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.115 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.127 _exptl_crystal_recrystallization_method 'slow evaporation of acetonitrile' # Attachment 'HL2_Cl.CIF' data_d: _database_code_depnum_ccdc_archive 'CCDC 720893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Au Cl5 N8 S2' _chemical_formula_weight 838.83 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.776(2) _cell_length_b 10.658(2) _cell_length_c 24.515(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.79(3) _cell_angle_gamma 90.00 _cell_volume 3055.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9300 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.66 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 5.417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.763 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details 'SADABS, Sheldrick' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9300 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2899 _reflns_number_gt 2377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001), Platon (Spek, 2003)' _computing_publication_material 'Platon (Spek, 2003)' _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^)+(0.0290P)^2^+4.3230P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00039(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2889 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.004 _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 0.5000 0.62628(3) 0.2500 0.03158(12) Uani 1 2 d S . . Cl1 Cl 0.5000 0.94239(15) 0.2500 0.0295(4) Uani 1 2 d S . . S1 S 0.30983(10) 0.60699(12) 0.25830(5) 0.0358(3) Uani 1 1 d . . . N1 N 0.1222(3) 0.6843(4) 0.20078(17) 0.0364(10) Uani 1 1 d . . . H1A H 0.0803 0.7319 0.1770 0.044 Uiso 1 1 calc R . . H1B H 0.0904 0.6221 0.2170 0.044 Uiso 1 1 calc R . . C1 C 0.2323(4) 0.7062(4) 0.21208(18) 0.0283(11) Uani 1 1 d . . . Cl2 Cl -0.15645(11) 1.12731(13) 0.08305(6) 0.0474(3) Uani 1 1 d . . . N2 N 0.2807(3) 0.8002(4) 0.18761(15) 0.0291(9) Uani 1 1 d . . . H2 H 0.3546 0.8153 0.1939 0.035 Uiso 1 1 calc R . . C2 C 0.2532(4) 0.9475(4) 0.11872(18) 0.0283(11) Uani 1 1 d . . . Cl3 Cl -0.08445(14) 1.26839(14) -0.02139(6) 0.0542(4) Uani 1 1 d . . . N3 N 0.2087(3) 0.8730(3) 0.15154(15) 0.0262(8) Uani 1 1 d . . . C3 C 0.3783(4) 0.9602(5) 0.1133(2) 0.0370(12) Uani 1 1 d . . . H2A H 0.4038 1.0451 0.1241 0.056 Uiso 1 1 calc R . . H2B H 0.3911 0.9449 0.0751 0.056 Uiso 1 1 calc R . . H2C H 0.4215 0.8989 0.1373 0.056 Uiso 1 1 calc R . . N4 N -0.1020(4) 0.7956(5) 0.1480(2) 0.0542(13) Uani 1 1 d . . . C4 C 0.1700(4) 1.0253(4) 0.08364(18) 0.0292(11) Uani 1 1 d . . . C5 C 0.0591(4) 1.0408(4) 0.09667(19) 0.0306(11) Uani 1 1 d . . . H5 H 0.0371 1.0002 0.1283 0.037 Uiso 1 1 calc R . . C6 C -0.0194(4) 1.1133(4) 0.0650(2) 0.0330(11) Uani 1 1 d . . . C7 C 0.0114(4) 1.1733(5) 0.0190(2) 0.0371(12) Uani 1 1 d . . . C8 C 0.1202(5) 1.1578(5) 0.0045(2) 0.0392(13) Uani 1 1 d . . . H8 H 0.1408 1.1970 -0.0277 0.047 Uiso 1 1 calc R . . C9 C 0.1999(4) 1.0849(5) 0.0369(2) 0.0355(12) Uani 1 1 d . . . H9 H 0.2751 1.0757 0.0270 0.043 Uiso 1 1 calc R . . C10 C -0.1946(5) 0.8275(5) 0.1457(2) 0.0416(13) Uani 1 1 d . . . C11 C -0.3127(4) 0.8690(5) 0.1410(3) 0.0489(14) Uani 1 1 d . . . H11A H -0.3625 0.8024 0.1242 0.073 Uiso 1 1 calc R . . H11B H -0.3217 0.9444 0.1181 0.073 Uiso 1 1 calc R . . H11C H -0.3335 0.8881 0.1777 0.073 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 Au1 0.02598(16) 0.03079(17) 0.03699(17) 0.000 -0.00040(11) 0.000 Cl1 0.0217(8) 0.0293(9) 0.0378(9) 0.000 0.0041(7) 0.000 S1 0.0270(6) 0.0381(7) 0.0415(7) 0.0137(6) 0.0004(5) -0.0019(5) N1 0.024(2) 0.039(2) 0.047(2) 0.012(2) 0.0036(19) -0.0063(19) C1 0.024(2) 0.029(3) 0.031(2) 0.000(2) 0.003(2) 0.000(2) Cl2 0.0368(7) 0.0490(8) 0.0562(8) -0.0022(7) 0.0044(6) 0.0141(7) N2 0.022(2) 0.033(2) 0.032(2) 0.0069(18) 0.0008(17) 0.0010(18) C2 0.030(3) 0.029(3) 0.025(2) -0.003(2) 0.001(2) -0.003(2) Cl3 0.0645(10) 0.0441(8) 0.0488(8) 0.0047(7) -0.0145(7) 0.0156(7) N3 0.0250(19) 0.025(2) 0.0284(19) -0.0003(18) 0.0016(16) -0.0007(18) C3 0.031(3) 0.038(3) 0.042(3) 0.008(2) 0.007(2) -0.004(2) N4 0.034(3) 0.060(3) 0.069(3) 0.013(3) 0.011(2) 0.004(2) C4 0.030(3) 0.027(3) 0.030(2) -0.003(2) 0.001(2) -0.004(2) C5 0.034(3) 0.026(3) 0.032(3) -0.003(2) 0.001(2) -0.001(2) C6 0.032(3) 0.029(3) 0.037(3) -0.006(2) 0.001(2) 0.003(2) C7 0.041(3) 0.031(3) 0.036(3) 0.000(2) -0.009(2) 0.001(2) C8 0.045(3) 0.038(3) 0.034(3) 0.004(2) 0.003(2) -0.004(2) C9 0.034(3) 0.037(3) 0.035(3) 0.004(2) 0.001(2) -0.001(2) C10 0.041(3) 0.042(3) 0.043(3) 0.005(3) 0.009(3) -0.004(3) C11 0.032(3) 0.054(4) 0.063(4) 0.003(3) 0.013(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 S1 2.2819(13) . ? Au1 S1 2.2819(13) 2_655 ? S1 C1 1.730(5) . ? N1 C1 1.314(6) . ? C1 N2 1.330(6) . ? Cl2 C6 1.730(5) . ? N2 N3 1.388(5) . ? C2 N3 1.286(6) . ? C2 C4 1.479(6) . ? C2 C3 1.500(6) . ? Cl3 C7 1.736(5) . ? N4 C10 1.137(7) . ? C4 C5 1.391(6) . ? C4 C9 1.391(7) . ? C5 C6 1.373(7) . ? C6 C7 1.383(7) . ? C7 C8 1.379(7) . ? C8 C9 1.394(7) . ? C10 C11 1.450(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Au1 S1 169.66(7) . 2_655 ? C1 S1 Au1 109.53(16) . . ? N1 C1 N2 120.2(4) . . ? N1 C1 S1 117.5(4) . . ? N2 C1 S1 122.3(3) . . ? C1 N2 N3 116.4(4) . . ? N3 C2 C4 114.8(4) . . ? N3 C2 C3 126.0(4) . . ? C4 C2 C3 119.2(4) . . ? C2 N3 N2 118.7(4) . . ? C5 C4 C9 118.1(4) . . ? C5 C4 C2 120.6(4) . . ? C9 C4 C2 121.4(4) . . ? C6 C5 C4 121.7(5) . . ? C5 C6 C7 119.9(5) . . ? C5 C6 Cl2 119.4(4) . . ? C7 C6 Cl2 120.8(4) . . ? C8 C7 C6 119.7(5) . . ? C8 C7 Cl3 119.0(4) . . ? C6 C7 Cl3 121.3(4) . . ? C7 C8 C9 120.2(5) . . ? C4 C9 C8 120.4(5) . . ? N4 C10 C11 178.4(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.737 _refine_diff_density_min -1.183 _refine_diff_density_rms 0.127 _exptl_crystal_recrystallization_method 'slow evaporation of acetonitrile'