# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'W Henderson' _publ_contact_author_address ; Department of Chemistry The University of Waikato Private Bag 3105 Hamilton 3240 NEW ZEALAND ; _publ_contact_author_email W.HENDERSON@WAIKATO.AC.NZ _publ_section_title ; Cycloauration of pyridyl sulfonamides ; loop_ _publ_author_name 'W. Henderson' 'Kelly J. Kilpin' 'B. Nicholson' data_kk28 _database_code_depnum_ccdc_archive 'CCDC 676314' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Au Cl2 N2 O2 S' _chemical_formula_sum 'C7 H9 Au Cl2 N2 O2 S' _chemical_formula_weight 453.09 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' 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 7.3424(1) _cell_length_b 9.2813(1) _cell_length_c 17.2700(2) _cell_angle_alpha 99.383(1) _cell_angle_beta 95.785(1) _cell_angle_gamma 102.127(1) _cell_volume 1124.06(2) _cell_formula_units_Z 4 _cell_measurement_temperature 87 _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2 _cell_measurement_theta_max 34 _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 13.728 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1138 _exptl_absorpt_correction_T_max 0.1699 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 87 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10969 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4562 _reflns_number_gt 4360 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0201P)^2^+3.0458P] 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 4562 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0512 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 0.746621(19) 0.058658(15) 0.473083(8) 0.01147(5) Uani 1 1 d . . . Cl11 Cl 0.82444(14) -0.03252(11) 0.58412(6) 0.0173(2) Uani 1 1 d . . . Cl12 Cl 0.63604(14) -0.18110(11) 0.40607(6) 0.01758(19) Uani 1 1 d . . . S1 S 0.68758(14) 0.10293(11) 0.28925(6) 0.01433(19) Uani 1 1 d . . . O11 O 0.7119(4) 0.2333(3) 0.25180(17) 0.0170(6) Uani 1 1 d . . . O12 O 0.8179(4) 0.0089(3) 0.27911(18) 0.0202(6) Uani 1 1 d . . . N11 N 0.8174(5) 0.2778(4) 0.53046(19) 0.0125(6) Uani 1 1 d . . . N12 N 0.6980(5) 0.1640(4) 0.3832(2) 0.0163(7) Uani 1 1 d . . . C11 C 0.9272(5) 0.3314(4) 0.6010(2) 0.0144(8) Uani 1 1 d . . . H11 H 0.9817 0.2669 0.6265 0.017 Uiso 1 1 calc R . . C12 C 0.9594(6) 0.4808(5) 0.6357(2) 0.0172(8) Uani 1 1 d . . . H12 H 1.0348 0.5169 0.6845 0.021 Uiso 1 1 calc R . . C13 C 0.8784(6) 0.5769(5) 0.5972(2) 0.0168(8) Uani 1 1 d . . . H13 H 0.8976 0.6777 0.6204 0.020 Uiso 1 1 calc R . . C14 C 0.7684(6) 0.5214(5) 0.5239(2) 0.0155(8) Uani 1 1 d . . . H14 H 0.7145 0.5849 0.4973 0.019 Uiso 1 1 calc R . . C15 C 0.7396(5) 0.3709(4) 0.4908(2) 0.0131(8) Uani 1 1 d . . . C16 C 0.6251(6) 0.2968(4) 0.4115(2) 0.0156(8) Uani 1 1 d . . . H16A H 0.4930 0.2669 0.4169 0.019 Uiso 1 1 calc R . . H16B H 0.6388 0.3652 0.3745 0.019 Uiso 1 1 calc R . . C17 C 0.4600(6) -0.0076(5) 0.2532(3) 0.0219(9) Uani 1 1 d . . . H17A H 0.4510 -0.0441 0.1973 0.033 Uiso 1 1 calc R . . H17B H 0.3694 0.0519 0.2626 0.033 Uiso 1 1 calc R . . H17C H 0.4355 -0.0911 0.2800 0.033 Uiso 1 1 calc R . . Au2 Au 0.472287(19) 0.378740(16) 0.160574(9) 0.01306(5) Uani 1 1 d . . . Cl22 Cl 0.19360(14) 0.20964(12) 0.15311(7) 0.0223(2) Uani 1 1 d . . . Cl21 Cl 0.41266(15) 0.51478(13) 0.27367(6) 0.0220(2) Uani 1 1 d . . . S2 S 0.42235(14) 0.26262(11) -0.02119(6) 0.01433(19) Uani 1 1 d . . . O21 O 0.5453(4) 0.2823(4) -0.08061(17) 0.0211(6) Uani 1 1 d . . . O22 O 0.2954(4) 0.3601(3) -0.00925(17) 0.0173(6) Uani 1 1 d . . . N21 N 0.7287(4) 0.5166(4) 0.16229(19) 0.0127(7) Uani 1 1 d . . . N22 N 0.5464(5) 0.2649(4) 0.0633(2) 0.0150(7) Uani 1 1 d . . . C21 C 0.7890(6) 0.6577(5) 0.2046(2) 0.0153(8) Uani 1 1 d . . . H21 H 0.7096 0.6997 0.2354 0.018 Uiso 1 1 calc R . . C22 C 0.9675(6) 0.7400(5) 0.2024(2) 0.0169(8) Uani 1 1 d . . . H22 H 1.0082 0.8376 0.2310 0.020 Uiso 1 1 calc R . . C23 C 1.0858(6) 0.6757(5) 0.1571(3) 0.0183(8) Uani 1 1 d . . . H23 H 1.2079 0.7292 0.1566 0.022 Uiso 1 1 calc R . . C24 C 1.0230(5) 0.5330(5) 0.1127(2) 0.0152(8) Uani 1 1 d . . . H24 H 1.1010 0.4897 0.0817 0.018 Uiso 1 1 calc R . . C25 C 0.8396(5) 0.4543(4) 0.1152(2) 0.0122(7) Uani 1 1 d . . . C26 C 0.7552(5) 0.2989(4) 0.0700(3) 0.0159(8) Uani 1 1 d . . . H26A H 0.7924 0.2890 0.0174 0.019 Uiso 1 1 calc R . . H26B H 0.8025 0.2273 0.0968 0.019 Uiso 1 1 calc R . . C27 C 0.2857(6) 0.0770(5) -0.0473(3) 0.0238(10) Uani 1 1 d . . . H27A H 0.2051 0.0656 -0.0964 0.036 Uiso 1 1 calc R . . H27B H 0.2104 0.0557 -0.0064 0.036 Uiso 1 1 calc R . . H27C H 0.3671 0.0086 -0.0534 0.036 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 0.01175(8) 0.01073(8) 0.01225(8) 0.00268(6) 0.00147(6) 0.00299(6) Cl11 0.0196(5) 0.0172(5) 0.0164(5) 0.0070(4) 0.0015(4) 0.0045(4) Cl12 0.0211(5) 0.0126(4) 0.0177(5) 0.0013(4) 0.0008(4) 0.0029(4) S1 0.0155(5) 0.0150(5) 0.0120(5) 0.0018(4) 0.0005(4) 0.0036(4) O11 0.0199(15) 0.0166(14) 0.0141(14) 0.0048(11) 0.0000(11) 0.0028(12) O12 0.0224(15) 0.0230(16) 0.0169(15) 0.0018(12) 0.0039(12) 0.0099(13) N11 0.0131(16) 0.0141(16) 0.0111(16) 0.0028(13) 0.0023(13) 0.0039(13) N12 0.0196(17) 0.0130(16) 0.0159(17) 0.0036(13) -0.0015(14) 0.0044(14) C11 0.0136(18) 0.0153(19) 0.0133(19) 0.0029(15) 0.0028(15) 0.0004(15) C12 0.0147(19) 0.022(2) 0.0128(19) 0.0013(16) 0.0039(15) 0.0011(16) C13 0.0166(19) 0.0137(19) 0.019(2) 0.0000(16) 0.0093(16) 0.0007(16) C14 0.0141(19) 0.017(2) 0.018(2) 0.0047(16) 0.0064(16) 0.0056(16) C15 0.0115(18) 0.0164(19) 0.0144(19) 0.0063(15) 0.0042(15) 0.0058(15) C16 0.0155(19) 0.0135(19) 0.017(2) 0.0018(15) 0.0012(16) 0.0033(16) C17 0.020(2) 0.023(2) 0.018(2) 0.0012(18) -0.0031(17) 0.0007(18) Au2 0.01061(8) 0.01619(9) 0.01314(8) 0.00449(6) 0.00147(6) 0.00351(6) Cl22 0.0130(5) 0.0255(5) 0.0291(6) 0.0117(4) 0.0019(4) 0.0011(4) Cl21 0.0200(5) 0.0307(6) 0.0168(5) 0.0034(4) 0.0075(4) 0.0076(4) S2 0.0140(4) 0.0132(4) 0.0150(5) 0.0013(4) -0.0008(4) 0.0037(4) O21 0.0198(15) 0.0281(17) 0.0150(15) 0.0009(13) 0.0039(12) 0.0062(13) O22 0.0174(14) 0.0190(14) 0.0165(14) 0.0031(12) 0.0006(11) 0.0072(12) N21 0.0112(15) 0.0167(16) 0.0117(16) 0.0053(13) 0.0006(12) 0.0053(13) N22 0.0119(16) 0.0191(17) 0.0121(16) 0.0013(13) -0.0025(13) 0.0031(14) C21 0.018(2) 0.0172(19) 0.0120(19) 0.0046(15) 0.0012(15) 0.0072(16) C22 0.018(2) 0.016(2) 0.015(2) -0.0003(16) -0.0006(16) 0.0054(16) C23 0.0136(19) 0.020(2) 0.020(2) 0.0041(17) 0.0003(16) 0.0012(16) C24 0.0106(18) 0.018(2) 0.017(2) 0.0036(16) -0.0005(15) 0.0044(16) C25 0.0109(18) 0.0135(18) 0.0127(18) 0.0048(15) -0.0012(14) 0.0037(15) C26 0.0103(18) 0.0153(19) 0.020(2) 0.0003(16) -0.0001(15) 0.0023(15) C27 0.024(2) 0.016(2) 0.027(2) 0.0000(18) -0.0081(19) 0.0022(18) _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 N12 2.006(3) . ? Au1 N11 2.046(3) . ? Au1 Cl12 2.2720(10) . ? Au1 Cl11 2.2872(10) . ? S1 O12 1.429(3) . ? S1 O11 1.450(3) . ? S1 N12 1.617(4) . ? S1 C17 1.759(4) . ? N11 C11 1.348(5) . ? N11 C15 1.365(5) . ? N12 C16 1.476(5) . ? C11 C12 1.379(6) . ? C12 C13 1.388(6) . ? C13 C14 1.388(6) . ? C14 C15 1.384(6) . ? C15 C16 1.508(6) . ? Au2 N22 2.021(3) . ? Au2 N21 2.037(3) . ? Au2 Cl22 2.2800(10) . ? Au2 Cl21 2.2807(10) . ? S2 O22 1.436(3) . ? S2 O21 1.442(3) . ? S2 N22 1.635(3) . ? S2 C27 1.763(4) . ? N21 C21 1.351(5) . ? N21 C25 1.355(5) . ? N22 C26 1.488(5) . ? C21 C22 1.379(6) . ? C22 C23 1.388(6) . ? C23 C24 1.376(6) . ? C24 C25 1.399(5) . ? C25 C26 1.494(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 N12 Au1 N11 78.98(13) . . ? N12 Au1 Cl12 98.02(10) . . ? N11 Au1 Cl12 173.78(10) . . ? N12 Au1 Cl11 172.72(10) . . ? N11 Au1 Cl11 94.08(10) . . ? Cl12 Au1 Cl11 89.09(4) . . ? O12 S1 O11 118.02(18) . . ? O12 S1 N12 107.98(18) . . ? O11 S1 N12 106.73(17) . . ? O12 S1 C17 108.1(2) . . ? O11 S1 C17 107.3(2) . . ? N12 S1 C17 108.4(2) . . ? C11 N11 C15 120.8(3) . . ? C11 N11 Au1 125.7(3) . . ? C15 N11 Au1 113.4(3) . . ? C16 N12 S1 120.4(3) . . ? C16 N12 Au1 109.9(3) . . ? S1 N12 Au1 128.3(2) . . ? N11 C11 C12 120.7(4) . . ? C11 C12 C13 119.5(4) . . ? C14 C13 C12 119.4(4) . . ? C15 C14 C13 119.5(4) . . ? N11 C15 C14 120.0(4) . . ? N11 C15 C16 115.1(3) . . ? C14 C15 C16 124.8(4) . . ? N12 C16 C15 106.4(3) . . ? N22 Au2 N21 82.09(13) . . ? N22 Au2 Cl22 93.79(10) . . ? N21 Au2 Cl22 175.49(10) . . ? N22 Au2 Cl21 175.60(10) . . ? N21 Au2 Cl21 93.89(10) . . ? Cl22 Au2 Cl21 90.17(4) . . ? O22 S2 O21 118.68(19) . . ? O22 S2 N22 109.82(18) . . ? O21 S2 N22 109.54(18) . . ? O22 S2 C27 107.5(2) . . ? O21 S2 C27 106.7(2) . . ? N22 S2 C27 103.5(2) . . ? C21 N21 C25 121.0(3) . . ? C21 N21 Au2 125.4(3) . . ? C25 N21 Au2 113.6(3) . . ? C26 N22 S2 119.4(3) . . ? C26 N22 Au2 108.8(2) . . ? S2 N22 Au2 115.97(19) . . ? N21 C21 C22 120.4(4) . . ? C21 C22 C23 119.4(4) . . ? C24 C23 C22 120.2(4) . . ? C23 C24 C25 118.8(4) . . ? N21 C25 C24 120.2(4) . . ? N21 C25 C26 115.9(3) . . ? C24 C25 C26 123.9(4) . . ? N22 C26 C25 111.0(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.230 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.153 # Attachment 'kkqq.txt' data_kkqq _database_code_depnum_ccdc_archive 'CCDC 676315' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Au Cl2 N2 O2 S , C H2 Cl2' _chemical_formula_sum 'C17 H15 Au Cl4 N2 O2 S' _chemical_formula_weight 650.14 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' 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 P2(1)/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 14.1782(6) _cell_length_b 10.6792(5) _cell_length_c 14.4771(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.147(2) _cell_angle_gamma 90.00 _cell_volume 1984.25(15) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7571 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 32.62 _exptl_crystal_description triangular _exptl_crystal_colour clear _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 8.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0597 _exptl_absorpt_correction_T_max 0.2950 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10934 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 32.83 _reflns_number_total 6252 _reflns_number_gt 5476 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0599P)^2^+0.2227P] 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 6252 _refine_ls_number_parameters 245 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.047 _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 0.047929(9) 0.292441(10) 0.209407(9) 0.01530(5) Uani 1 1 d . . . Cl1 Cl -0.06169(7) 0.12696(8) 0.18461(7) 0.02602(17) Uani 1 1 d . . . Cl2 Cl 0.03258(8) 0.33357(10) 0.35581(8) 0.0324(2) Uani 1 1 d . . . S1 S 0.24364(6) 0.47470(7) 0.32730(6) 0.01576(14) Uani 1 1 d . . . O1 O 0.2684(2) 0.3668(2) 0.39224(19) 0.0220(5) Uani 1 1 d . . . O2 O 0.32347(18) 0.5256(2) 0.30159(18) 0.0209(5) Uani 1 1 d . . . N1 N 0.0544(2) 0.2727(2) 0.0731(2) 0.0146(5) Uani 1 1 d . . . N2 N 0.1425(2) 0.4406(3) 0.2198(2) 0.0176(5) Uani 1 1 d . . . C1 C 0.0135(3) 0.1800(3) 0.0062(3) 0.0188(6) Uani 1 1 d . . . H1 H -0.0156 0.1114 0.0240 0.023 Uiso 1 1 calc R . . C2 C 0.0138(3) 0.1841(3) -0.0898(3) 0.0212(6) Uani 1 1 d . . . H2 H -0.0134 0.1175 -0.1348 0.025 Uiso 1 1 calc R . . C3 C 0.0540(3) 0.2857(3) -0.1182(3) 0.0197(7) Uani 1 1 d . . . H3 H 0.0531 0.2889 -0.1828 0.024 Uiso 1 1 calc R . . C4 C 0.0968(2) 0.3859(3) -0.0493(2) 0.0162(6) Uani 1 1 d . . . C5 C 0.1394(2) 0.4961(3) -0.0721(2) 0.0192(6) Uani 1 1 d . . . H5 H 0.1403 0.5061 -0.1355 0.023 Uiso 1 1 calc R . . C6 C 0.1790(3) 0.5868(3) 0.0006(3) 0.0198(6) Uani 1 1 d . . . H6 H 0.2054 0.6594 -0.0150 0.024 Uiso 1 1 calc R . . C7 C 0.1813(2) 0.5747(3) 0.0985(2) 0.0176(6) Uani 1 1 d . . . H7 H 0.2086 0.6389 0.1459 0.021 Uiso 1 1 calc R . . C8 C 0.1430(2) 0.4677(3) 0.1243(2) 0.0144(5) Uani 1 1 d . . . C9 C 0.0975(2) 0.3755(3) 0.0480(2) 0.0138(5) Uani 1 1 d . . . C10 C 0.2016(2) 0.5949(3) 0.3841(2) 0.0162(6) Uani 1 1 d . . . C11 C 0.1767(3) 0.7112(3) 0.3372(3) 0.0200(7) Uani 1 1 d . . . H11 H 0.1819 0.7257 0.2762 0.024 Uiso 1 1 calc R . . C12 C 0.1438(3) 0.8056(3) 0.3826(3) 0.0228(7) Uani 1 1 d . . . H12 H 0.1254 0.8831 0.3506 0.027 Uiso 1 1 calc R . . C13 C 0.1378(3) 0.7864(3) 0.4752(3) 0.0227(7) Uani 1 1 d . . . C14 C 0.1047(3) 0.8888(4) 0.5256(4) 0.0359(9) Uani 1 1 d . . . H14A H 0.0894 0.9629 0.4843 0.054 Uiso 1 1 calc R . . H14B H 0.1599 0.9061 0.5915 0.054 Uiso 1 1 calc R . . H14C H 0.0436 0.8630 0.5334 0.054 Uiso 1 1 calc R . . C15 C 0.1659(3) 0.6685(4) 0.5220(3) 0.0262(7) Uani 1 1 d . . . H15 H 0.1634 0.6544 0.5843 0.031 Uiso 1 1 calc R . . C16 C 0.1971(3) 0.5733(3) 0.4767(3) 0.0235(7) Uani 1 1 d . . . H16 H 0.2149 0.4953 0.5080 0.028 Uiso 1 1 calc R . . Cl21 Cl -0.38842(12) 0.10276(12) 0.15363(10) 0.0502(3) Uani 1 1 d D . . Cl22 Cl -0.34801(13) 0.36748(13) 0.20826(11) 0.0597(4) Uani 1 1 d D . . C21 C -0.3234(6) 0.2387(7) 0.1433(6) 0.076(2) Uani 1 1 d D . . H21A H -0.3464 0.2598 0.0719 0.091 Uiso 1 1 calc R . . H21B H -0.2490 0.2227 0.1720 0.091 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 0.01923(7) 0.01145(7) 0.01922(7) -0.00022(4) 0.01202(5) -0.00180(4) Cl1 0.0300(4) 0.0181(4) 0.0376(5) -0.0025(3) 0.0218(3) -0.0083(3) Cl2 0.0469(5) 0.0338(5) 0.0292(4) -0.0061(4) 0.0284(4) -0.0115(4) S1 0.0191(3) 0.0112(3) 0.0179(3) -0.0019(3) 0.0088(3) 0.0011(3) O1 0.0283(12) 0.0142(11) 0.0219(11) 0.0025(9) 0.0092(9) 0.0065(9) O2 0.0199(10) 0.0188(12) 0.0268(12) -0.0053(9) 0.0126(9) -0.0023(9) N1 0.0154(11) 0.0105(11) 0.0182(12) -0.0011(9) 0.0074(9) -0.0009(9) N2 0.0237(13) 0.0140(12) 0.0198(13) -0.0021(10) 0.0138(10) -0.0054(10) C1 0.0201(14) 0.0118(13) 0.0239(15) -0.0024(12) 0.0088(12) -0.0017(11) C2 0.0235(15) 0.0183(15) 0.0230(16) -0.0091(12) 0.0111(13) -0.0039(12) C3 0.0222(15) 0.0210(17) 0.0185(14) -0.0036(11) 0.0110(12) 0.0004(11) C4 0.0163(12) 0.0151(14) 0.0188(13) -0.0004(11) 0.0089(10) 0.0020(11) C5 0.0232(15) 0.0203(15) 0.0180(14) 0.0026(12) 0.0124(12) 0.0024(12) C6 0.0231(15) 0.0145(14) 0.0253(16) 0.0018(12) 0.0137(12) 0.0002(11) C7 0.0225(14) 0.0115(13) 0.0223(15) 0.0001(11) 0.0130(12) -0.0018(11) C8 0.0174(12) 0.0122(13) 0.0162(13) -0.0008(10) 0.0098(10) -0.0009(10) C9 0.0145(12) 0.0093(12) 0.0185(13) 0.0007(10) 0.0078(10) 0.0006(10) C10 0.0192(13) 0.0126(14) 0.0186(14) -0.0042(10) 0.0099(11) -0.0002(10) C11 0.0222(16) 0.0143(16) 0.0249(16) -0.0013(11) 0.0116(13) 0.0006(11) C12 0.0224(16) 0.0166(16) 0.0325(19) -0.0038(12) 0.0147(14) -0.0001(12) C13 0.0240(16) 0.0185(17) 0.0313(19) -0.0096(13) 0.0173(14) -0.0037(12) C14 0.043(2) 0.025(2) 0.054(3) -0.0171(18) 0.034(2) -0.0040(17) C15 0.0324(18) 0.0288(19) 0.0233(16) -0.0050(14) 0.0176(14) -0.0006(15) C16 0.0309(17) 0.0202(16) 0.0212(15) 0.0002(12) 0.0128(13) 0.0029(13) Cl21 0.0756(9) 0.0402(6) 0.0490(7) 0.0037(5) 0.0401(6) 0.0149(6) Cl22 0.0805(10) 0.0460(7) 0.0433(7) 0.0121(5) 0.0173(6) -0.0213(7) C21 0.062(4) 0.103(5) 0.091(5) 0.040(5) 0.059(4) 0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 N1 2.026(3) . ? Au1 N2 2.038(3) . ? Au1 Cl2 2.2637(9) . ? Au1 Cl1 2.2789(8) . ? S1 O1 1.434(3) . ? S1 O2 1.440(2) . ? S1 N2 1.648(3) . ? S1 C10 1.758(3) . ? N1 C1 1.332(4) . ? N1 C9 1.377(4) . ? N2 C8 1.415(4) . ? C1 C2 1.392(5) . ? C2 C3 1.368(5) . ? C3 C4 1.412(4) . ? C4 C9 1.410(4) . ? C4 C5 1.424(4) . ? C5 C6 1.363(5) . ? C6 C7 1.410(5) . ? C7 C8 1.383(4) . ? C8 C9 1.414(4) . ? C10 C11 1.387(4) . ? C10 C16 1.390(5) . ? C11 C12 1.387(5) . ? C12 C13 1.394(6) . ? C13 C15 1.405(5) . ? C13 C14 1.496(5) . ? C15 C16 1.381(5) . ? Cl21 C21 1.760(7) . ? Cl22 C21 1.782(8) . ? 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 Au1 N2 81.48(11) . . ? N1 Au1 Cl2 174.14(8) . . ? N2 Au1 Cl2 95.88(8) . . ? N1 Au1 Cl1 94.36(8) . . ? N2 Au1 Cl1 175.60(8) . . ? Cl2 Au1 Cl1 88.13(3) . . ? O1 S1 O2 118.21(16) . . ? O1 S1 N2 108.30(15) . . ? O2 S1 N2 107.65(14) . . ? O1 S1 C10 108.53(16) . . ? O2 S1 C10 107.73(15) . . ? N2 S1 C10 105.75(15) . . ? C1 N1 C9 120.4(3) . . ? C1 N1 Au1 126.8(2) . . ? C9 N1 Au1 112.5(2) . . ? C8 N2 S1 121.0(2) . . ? C8 N2 Au1 111.28(19) . . ? S1 N2 Au1 121.51(15) . . ? N1 C1 C2 121.1(3) . . ? C3 C2 C1 120.2(3) . . ? C2 C3 C4 119.9(3) . . ? C9 C4 C3 117.7(3) . . ? C9 C4 C5 118.3(3) . . ? C3 C4 C5 124.1(3) . . ? C6 C5 C4 118.9(3) . . ? C5 C6 C7 122.5(3) . . ? C8 C7 C6 120.2(3) . . ? C7 C8 C9 117.8(3) . . ? C7 C8 N2 126.7(3) . . ? C9 C8 N2 115.5(3) . . ? N1 C9 C4 120.7(3) . . ? N1 C9 C8 117.1(3) . . ? C4 C9 C8 122.2(3) . . ? C11 C10 C16 120.9(3) . . ? C11 C10 S1 119.5(3) . . ? C16 C10 S1 119.6(3) . . ? C10 C11 C12 119.1(4) . . ? C11 C12 C13 121.3(3) . . ? C12 C13 C15 118.3(3) . . ? C12 C13 C14 121.5(4) . . ? C15 C13 C14 120.2(4) . . ? C16 C15 C13 120.9(4) . . ? C15 C16 C10 119.5(3) . . ? Cl21 C21 Cl22 111.4(3) . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 32.83 _diffrn_measured_fraction_theta_full 0.847 _refine_diff_density_max 1.850 _refine_diff_density_min -5.227 _refine_diff_density_rms 0.223