# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Mohammad Omary' 'Alice E Bruce' 'Mitchell Bruce' 'Thomas R Cundari' 'Oussama Elbjeirami' 'M. W. Alexander Gonser' 'Barbara N. Stewart' _publ_contact_author_name 'Mohammad Omary' _publ_contact_author_email OMARY@UNT.EDU _publ_section_title ; Luminescence, Structural, and Bonding Trends upon Varying the Halogen in Isostructural Aurophilic Dimers ; # Attachment 'pTosylCH2NCAuBr_sub_.cif' data_omary4s _database_code_depnum_ccdc_archive 'CCDC 698231' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromo[(p-tosyl)methylisonitrile]gold ; _chemical_name_common ; [(p-tosyl)methyNC]gold bromide ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 Au Br N O2 S' _chemical_formula_sum 'C9 H9 Au Br N O2 S' _chemical_formula_weight 472.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 ' _symmetry_space_group_name_Hall '-C 2yc' 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 28.554(4) _cell_length_b 5.2623(6) _cell_length_c 21.234(3) _cell_angle_alpha 90.00 _cell_angle_beta 129.315(2) _cell_angle_gamma 90.00 _cell_volume 2468.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 3043 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.66 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 15.305 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0638 _exptl_absorpt_correction_T_max 0.6567 _exptl_absorpt_process_details ;SADABS: an empirical absorption program by G. M. Sheldrick using the method described by Blessing, R. H.; Acta Cryst. A51, 1995, 33. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8653 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2180 _reflns_number_gt 1920 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00044(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2180 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.023 _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 Au1 Au 0.032176(11) 0.52306(5) 0.342399(15) 0.05044(14) Uani 1 1 d . . . Br1 Br -0.03841(3) 0.21861(13) 0.31894(4) 0.0671(2) Uani 1 1 d . . . S1 S 0.22606(7) 0.9029(3) 0.39213(9) 0.0425(4) Uani 1 1 d . . . C1 C 0.1908(3) 0.9281(10) 0.2892(3) 0.0382(13) Uani 1 1 d . . . C6 C 0.1480(3) 0.7531(10) 0.2342(3) 0.0456(14) Uani 1 1 d . . . H6 H 0.1377 0.6191 0.2519 0.055 Uiso 1 1 calc R . . C4 C 0.1352(4) 0.9739(13) 0.1254(5) 0.064(2) Uani 1 1 d . . . C2 C 0.2057(3) 1.1350(11) 0.2623(4) 0.0488(15) Uani 1 1 d . . . H2 H 0.2338 1.2563 0.2989 0.059 Uiso 1 1 calc R . . C5 C 0.1205(3) 0.7771(11) 0.1532(4) 0.0568(16) Uani 1 1 d . . . H5 H 0.0914 0.6589 0.1164 0.068 Uiso 1 1 calc R . . C3 C 0.1776(3) 1.1522(13) 0.1810(4) 0.0568(16) Uani 1 1 d . . . H3 H 0.1871 1.2869 0.1626 0.068 Uiso 1 1 calc R . . O1 O 0.22701(19) 0.6400(8) 0.4103(2) 0.0565(11) Uani 1 1 d . . . O2 O 0.2808(2) 1.0483(8) 0.4393(3) 0.0577(12) Uani 1 1 d . . . N1 N 0.1283(2) 0.9073(9) 0.3819(3) 0.0456(12) Uani 1 1 d . . . C8 C 0.1765(3) 1.0659(10) 0.4047(4) 0.0450(14) Uani 1 1 d . . . H8A H 0.1994 1.1165 0.4611 0.054 Uiso 1 1 calc R . . H8B H 0.1606 1.2182 0.3714 0.054 Uiso 1 1 calc R . . C9 C 0.0923(3) 0.7668(12) 0.3669(4) 0.0498(15) Uani 1 1 d . . . C7 C 0.1053(5) 0.9992(16) 0.0360(6) 0.105(4) Uani 1 1 d . . . H7A H 0.1212 0.8722 0.0215 0.158 Uiso 1 1 calc R . . H7B H 0.1134 1.1650 0.0260 0.158 Uiso 1 1 calc R . . H7C H 0.0624 0.9764 0.0038 0.158 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0435(2) 0.0587(2) 0.0472(2) -0.00391(10) 0.02784(16) -0.00741(10) Br1 0.0516(4) 0.0693(4) 0.0740(5) 0.0024(3) 0.0367(4) -0.0117(3) S1 0.0419(9) 0.0410(7) 0.0386(8) 0.0019(6) 0.0226(8) 0.0014(6) C1 0.042(4) 0.041(3) 0.038(3) 0.001(2) 0.028(3) 0.002(2) C6 0.051(4) 0.038(3) 0.050(4) -0.001(3) 0.033(3) -0.003(3) C4 0.074(6) 0.079(5) 0.046(4) 0.009(3) 0.042(4) 0.020(4) C2 0.052(4) 0.041(3) 0.059(4) 0.001(3) 0.038(4) -0.003(3) C5 0.062(4) 0.052(4) 0.048(4) -0.011(3) 0.031(4) -0.003(3) C3 0.061(4) 0.060(4) 0.064(4) 0.015(3) 0.046(4) 0.008(3) O1 0.076(3) 0.038(2) 0.051(3) 0.0090(18) 0.038(2) 0.010(2) O2 0.042(3) 0.066(3) 0.055(3) -0.006(2) 0.026(3) -0.0082(19) N1 0.050(3) 0.047(3) 0.042(3) -0.005(2) 0.030(3) -0.003(2) C8 0.053(4) 0.038(3) 0.048(4) -0.007(2) 0.034(3) -0.009(3) C9 0.052(4) 0.055(4) 0.043(4) -0.003(3) 0.030(3) -0.003(3) C7 0.129(10) 0.136(9) 0.052(6) 0.018(4) 0.057(7) 0.019(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 C9 1.931(7) . ? Au1 Br1 2.3675(7) . ? Au1 Au1 3.1044(7) 2 ? S1 O2 1.431(5) . ? S1 O1 1.432(4) . ? S1 C1 1.738(6) . ? S1 C8 1.813(6) . ? C1 C6 1.378(8) . ? C1 C2 1.413(8) . ? C6 C5 1.369(8) . ? C6 H6 0.9300 . ? C4 C5 1.384(9) . ? C4 C3 1.389(10) . ? C4 C7 1.515(11) . ? C2 C3 1.370(9) . ? C2 H2 0.9300 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? N1 C9 1.136(7) . ? N1 C8 1.408(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 C9 Au1 Br1 177.31(17) . . ? C9 Au1 Au1 93.07(17) . 2 ? Br1 Au1 Au1 89.48(2) . 2 ? O2 S1 O1 120.2(3) . . ? O2 S1 C1 110.1(3) . . ? O1 S1 C1 108.0(3) . . ? O2 S1 C8 104.6(3) . . ? O1 S1 C8 107.5(3) . . ? C1 S1 C8 105.4(3) . . ? C6 C1 C2 120.3(5) . . ? C6 C1 S1 120.7(4) . . ? C2 C1 S1 119.0(4) . . ? C5 C6 C1 119.8(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C5 C4 C3 118.6(7) . . ? C5 C4 C7 121.2(7) . . ? C3 C4 C7 120.2(7) . . ? C3 C2 C1 118.3(6) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C6 C5 C4 121.2(6) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C2 C3 C4 121.7(6) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C9 N1 C8 175.3(7) . . ? N1 C8 S1 110.7(4) . . ? N1 C8 H8A 109.5 . . ? S1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N1 C9 Au1 178.9(7) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.242 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.153 # Attachment 'pTosylCH2NCAuI_sub_.cif' data_omary5newsad _database_code_depnum_ccdc_archive 'CCDC 698232' _audit_creation_method SHELXL-97 _chemical_name_systematic ; iodo[(p-tosyl)methylisonitrile]gold ; _chemical_name_common ; [(p-tosyl)methyNC]gold iodide ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 Au I N O2 S' _chemical_formula_sum 'C9 H9 Au I N O2 S' _chemical_formula_weight 519.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 ' _symmetry_space_group_name_Hall '-C 2yc' 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 29.476(2) _cell_length_b 5.2471(4) _cell_length_c 21.1923(17) _cell_angle_alpha 90.00 _cell_angle_beta 128.417(2) _cell_angle_gamma 90.00 _cell_volume 2568.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3459 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.52 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 14.004 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0516 _exptl_absorpt_correction_T_max 0.6043 _exptl_absorpt_process_details ;SADABS: an empirical absorption program by G. M. Sheldrick using the method described by Blessing, R. H.; Acta Cryst. A51, 1995, 33. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8964 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2260 _reflns_number_gt 2044 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0210P)^2^+5.5568P] 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 2260 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.035722(10) 0.95860(5) 0.343025(14) 0.05433(11) Uani 1 1 d . . . I1 I -0.035645(18) 1.27223(8) 0.32696(3) 0.06564(15) Uani 1 1 d . . . S1 S 0.22590(6) 0.5932(2) 0.39253(8) 0.0425(3) Uani 1 1 d . . . N1 N 0.1317(2) 0.5875(9) 0.3828(3) 0.0471(11) Uani 1 1 d . . . C1 C 0.1927(2) 0.5591(9) 0.2904(3) 0.0390(11) Uani 1 1 d . . . C2 C 0.2078(2) 0.3529(11) 0.2652(3) 0.0482(13) Uani 1 1 d . . . H2 H 0.2347 0.2331 0.3021 0.058 Uiso 1 1 calc R . . O2 O 0.22640(19) 0.8579(7) 0.4094(2) 0.0586(10) Uani 1 1 d . . . O1 O 0.27838(18) 0.4497(8) 0.4396(3) 0.0580(11) Uani 1 1 d . . . C4 C 0.1423(3) 0.5042(12) 0.1293(4) 0.0554(15) Uani 1 1 d . . . C3 C 0.1820(3) 0.3304(12) 0.1848(4) 0.0547(14) Uani 1 1 d . . . H3 H 0.1918 0.1934 0.1676 0.066 Uiso 1 1 calc R . . C6 C 0.1524(2) 0.7338(10) 0.2358(3) 0.0473(13) Uani 1 1 d . . . H6 H 0.1421 0.8698 0.2528 0.057 Uiso 1 1 calc R . . C5 C 0.1272(3) 0.7051(12) 0.1553(4) 0.0572(15) Uani 1 1 d . . . H5 H 0.0997 0.8225 0.1181 0.069 Uiso 1 1 calc R . . C8 C 0.1785(3) 0.4331(10) 0.4068(3) 0.0454(13) Uani 1 1 d . . . H8A H 0.1643 0.2765 0.3757 0.054 Uiso 1 1 calc R . . H8B H 0.2002 0.3888 0.4632 0.054 Uiso 1 1 calc R . . C9 C 0.0959(3) 0.7227(12) 0.3669(3) 0.0496(13) Uani 1 1 d . . . C7 C 0.1150(4) 0.4751(18) 0.0415(5) 0.098(3) Uani 1 1 d . . . H7A H 0.1273 0.6127 0.0254 0.147 Uiso 1 1 calc R . . H7B H 0.0736 0.4782 0.0098 0.147 Uiso 1 1 calc R . . H7C H 0.1268 0.3159 0.0335 0.147 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 0.04540(17) 0.06370(17) 0.05269(16) 0.00518(10) 0.02988(13) 0.00988(10) I1 0.0504(3) 0.0666(3) 0.0769(3) -0.0042(2) 0.0381(2) 0.00799(18) S1 0.0418(8) 0.0404(7) 0.0410(7) -0.0004(5) 0.0236(6) 0.0002(5) N1 0.043(3) 0.055(3) 0.044(3) 0.002(2) 0.027(2) 0.005(2) C1 0.040(3) 0.038(3) 0.040(3) 0.001(2) 0.025(3) -0.002(2) C2 0.043(3) 0.048(3) 0.055(3) 0.000(3) 0.031(3) 0.001(3) O2 0.074(3) 0.040(2) 0.054(2) -0.0111(18) 0.037(2) -0.009(2) O1 0.044(2) 0.067(3) 0.051(2) 0.0031(19) 0.024(2) 0.0072(19) C4 0.058(4) 0.068(4) 0.047(3) -0.005(3) 0.035(3) -0.010(3) C3 0.059(4) 0.057(3) 0.061(4) -0.013(3) 0.044(3) -0.005(3) C6 0.050(3) 0.041(3) 0.051(3) 0.003(2) 0.032(3) 0.001(2) C5 0.055(4) 0.060(4) 0.049(3) 0.011(3) 0.028(3) 0.003(3) C8 0.049(3) 0.047(3) 0.045(3) 0.005(2) 0.031(3) 0.005(2) C9 0.045(3) 0.062(3) 0.041(3) 0.002(3) 0.026(3) 0.004(3) C7 0.112(8) 0.132(7) 0.051(4) -0.007(4) 0.051(5) 0.001(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 C9 1.954(6) . ? Au1 I1 2.5218(5) . ? Au1 Au1 3.1083(5) 2 ? S1 O1 1.427(4) . ? S1 O2 1.432(4) . ? S1 C1 1.744(5) . ? S1 C8 1.809(6) . ? N1 C9 1.136(7) . ? N1 C8 1.396(7) . ? C1 C6 1.372(7) . ? C1 C2 1.396(8) . ? C2 C3 1.373(8) . ? C2 H2 0.9300 . ? C4 C3 1.369(9) . ? C4 C5 1.384(9) . ? C4 C7 1.508(9) . ? C3 H3 0.9300 . ? C6 C5 1.382(8) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 C9 Au1 I1 174.34(16) . . ? C9 Au1 Au1 96.82(16) . 2 ? I1 Au1 Au1 88.737(13) . 2 ? O1 S1 O2 119.9(3) . . ? O1 S1 C1 110.0(3) . . ? O2 S1 C1 108.7(2) . . ? O1 S1 C8 104.6(3) . . ? O2 S1 C8 107.3(3) . . ? C1 S1 C8 105.3(3) . . ? C9 N1 C8 175.9(6) . . ? C6 C1 C2 120.7(5) . . ? C6 C1 S1 120.1(4) . . ? C2 C1 S1 119.2(4) . . ? C3 C2 C1 118.6(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C3 C4 C5 118.7(6) . . ? C3 C4 C7 120.5(6) . . ? C5 C4 C7 120.8(6) . . ? C4 C3 C2 121.8(6) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C1 C6 C5 119.2(5) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C5 C4 121.0(6) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? N1 C8 S1 111.2(4) . . ? N1 C8 H8A 109.4 . . ? S1 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? S1 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 Au1 178.2(5) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.103 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.119