Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email abram@chemie.fu-berlin.de _publ_contact_author_name 'Prof Ulrich Abram' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_address ; Institute of Chemistry Freie Universitaet Berlin Fabeckstrasse 34-36 Berlin D-14195 GERMANY ; _publ_contact_author_phone '0049 (0)30 838 54002' _publ_contact_author_fax '0049 (0)30 838 52676' #============================================================================ # 2. TITLE AND AUTHOR LIST _publ_section_title ; Stable Gold(III) Complexes with Thiosemicarbazone Derivatives ; loop_ _publ_author_name _publ_author_address I.Garcia ; Free University of Berlin Institute of Chemistry Fabeckstrasse 34-36 D-14195 Berlin Germany ; A.Hagenbach ; Free University of Berlin Institute of Chemistry Fabeckstrasse 34-36 D-14195 Berlin Germany ; U.Abram ; Free University of Berlin Institute of Chemistry Fabeckstrasse 34-36 D-14195 Berlin Germany ; data_audite _database_code_depnum_ccdc_archive 'CCDC 221997' _chemical_name_common Bromo(2,3-diphenyltetrazole-5-thione)-gold(i) _audit_creation_method SHELXL-97 _chemical_name_systematic Bromo(2,3-diphenyltetrazole-5-thione)-gold(I) _chemical_melting_point ? _chemical_formula_moiety [AuBr(C13H10N4S)] _chemical_formula_sum 'C13 H10 Au Br N4 S' _chemical_formula_weight 531.19 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.724(1) _cell_length_b 12.061(2) _cell_length_c 12.8757(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.49(1) _cell_angle_gamma 90.00 _cell_volume 1468.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max .2 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 12.875 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.572237 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '10 sec/frame' _diffrn_standards_decay_% 0 _diffrn_reflns_number 11593 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2506 _reflns_number_gt 1974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction SAINT _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material WINGX _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^)+(0.0400P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2506 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 0.14654(3) 0.47574(3) 0.10677(2) 0.02387(11) Uani 1 1 d . . . S1 S 0.2813(2) 0.59088(18) 0.03167(16) 0.0309(5) Uani 1 1 d . . . C1 C 0.4352(7) 0.5988(6) 0.1272(6) 0.0208(16) Uani 1 1 d . . . N2 N 0.5502(6) 0.6540(5) 0.1105(4) 0.0223(14) Uani 1 1 d . . . N3 N 0.6478(6) 0.6405(5) 0.2004(5) 0.0205(14) Uani 1 1 d . . . N4 N 0.5963(6) 0.5812(5) 0.2685(5) 0.0204(14) Uani 1 1 d . . . N5 N 0.4632(6) 0.5527(5) 0.2263(5) 0.0236(15) Uani 1 1 d . . . Br1 Br 0.01520(8) 0.34858(8) 0.18828(7) 0.0362(2) Uani 1 1 d . . . C6 C 0.7892(7) 0.6881(6) 0.2195(6) 0.0236(17) Uani 1 1 d . . . C7 C 0.8448(8) 0.7414(6) 0.3137(6) 0.0258(18) Uani 1 1 d . . . H7 H 0.7945 0.7467 0.3667 0.031 Uiso 1 1 calc R . . C8 C 0.9773(8) 0.7870(6) 0.3274(6) 0.0273(18) Uani 1 1 d . . . H8 H 1.0174 0.8237 0.3907 0.033 Uiso 1 1 calc R . . C9 C 1.0517(8) 0.7791(6) 0.2488(7) 0.035(2) Uani 1 1 d . . . H9 H 1.1430 0.8074 0.2603 0.042 Uiso 1 1 calc R . . C10 C 0.9886(8) 0.7278(6) 0.1510(7) 0.0316(19) Uani 1 1 d . . . H10 H 1.0359 0.7257 0.0960 0.038 Uiso 1 1 calc R . . C11 C 0.8555(8) 0.6805(7) 0.1373(6) 0.0308(19) Uani 1 1 d . . . H11 H 0.8128 0.6446 0.0740 0.037 Uiso 1 1 calc R . . C12 C 0.6742(7) 0.5398(6) 0.3713(6) 0.0222(17) Uani 1 1 d . . . C13 C 0.6340(9) 0.5751(8) 0.4613(6) 0.037(2) Uani 1 1 d . . . H13 H 0.5596 0.6247 0.4566 0.044 Uiso 1 1 calc R . . C14 C 0.7072(9) 0.5347(8) 0.5586(7) 0.044(2) Uani 1 1 d . . . H14 H 0.6838 0.5588 0.6210 0.053 Uiso 1 1 calc R . . C15 C 0.8132(10) 0.4601(7) 0.5642(7) 0.041(2) Uani 1 1 d . . . H15 H 0.8600 0.4320 0.6302 0.049 Uiso 1 1 calc R . . C16 C 0.8527(9) 0.4252(7) 0.4727(7) 0.036(2) Uani 1 1 d . . . H16 H 0.9266 0.3750 0.4779 0.043 Uiso 1 1 calc R . . C17 C 0.7816(9) 0.4653(7) 0.3727(7) 0.034(2) Uani 1 1 d . . . H17 H 0.8058 0.4426 0.3103 0.041 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 0.02088(16) 0.02558(18) 0.02367(17) -0.00048(15) 0.00220(11) -0.00157(13) S1 0.0254(10) 0.0370(13) 0.0269(11) 0.0063(10) -0.0006(8) -0.0056(9) C1 0.026(4) 0.019(4) 0.020(4) -0.002(3) 0.010(3) -0.004(3) N2 0.030(4) 0.023(4) 0.013(3) 0.003(3) 0.003(3) -0.001(3) N3 0.022(3) 0.021(4) 0.017(3) 0.003(3) 0.002(3) -0.003(3) N4 0.014(3) 0.030(4) 0.018(3) 0.000(3) 0.005(2) -0.002(3) N5 0.023(3) 0.023(4) 0.024(4) -0.003(3) 0.006(3) -0.004(3) Br1 0.0299(4) 0.0401(5) 0.0375(5) 0.0053(4) 0.0053(4) -0.0092(4) C6 0.017(4) 0.024(4) 0.029(4) 0.001(4) 0.003(3) -0.007(3) C7 0.025(4) 0.025(5) 0.026(4) 0.005(4) 0.002(3) -0.003(3) C8 0.030(4) 0.020(4) 0.030(4) 0.001(4) 0.005(3) -0.006(3) C9 0.030(5) 0.021(5) 0.053(6) 0.015(4) 0.007(4) 0.001(3) C10 0.039(5) 0.021(5) 0.039(5) 0.006(4) 0.016(4) -0.002(4) C11 0.036(5) 0.028(5) 0.029(5) -0.002(4) 0.009(4) -0.003(4) C12 0.024(4) 0.022(5) 0.017(4) 0.007(3) -0.003(3) -0.003(3) C13 0.041(5) 0.044(6) 0.026(5) -0.002(4) 0.008(4) 0.014(4) C14 0.043(5) 0.071(7) 0.016(4) 0.012(4) 0.003(4) 0.011(5) C15 0.061(6) 0.032(6) 0.028(5) 0.010(4) 0.007(4) -0.006(4) C16 0.035(5) 0.027(5) 0.042(5) 0.006(4) -0.001(4) 0.012(4) C17 0.036(5) 0.034(5) 0.030(5) -0.003(4) 0.004(4) -0.004(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 S1 2.274(2) . ? Au1 Br1 2.3896(9) . ? S1 C1 1.704(7) . ? C1 N5 1.360(9) . ? C1 N2 1.361(9) . ? N2 N3 1.325(8) . ? N3 N4 1.317(8) . ? N3 C6 1.457(9) . ? N4 N5 1.327(8) . ? N4 C12 1.451(9) . ? C6 C11 1.365(10) . ? C6 C7 1.368(10) . ? C7 C8 1.374(10) . ? C8 C9 1.378(11) . ? C9 C10 1.409(11) . ? C10 C11 1.388(11) . ? C12 C13 1.374(10) . ? C12 C17 1.375(11) . ? C13 C14 1.378(11) . ? C14 C15 1.358(12) . ? C15 C16 1.386(12) . ? C16 C17 1.398(11) . ? 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 Br1 177.05(6) . . ? C1 S1 Au1 102.9(3) . . ? N5 C1 N2 110.9(6) . . ? N5 C1 S1 127.2(5) . . ? N2 C1 S1 121.9(5) . . ? N3 N2 C1 104.4(6) . . ? N4 N3 N2 110.0(5) . . ? N4 N3 C6 126.3(6) . . ? N2 N3 C6 123.6(6) . . ? N3 N4 N5 110.7(5) . . ? N3 N4 C12 126.5(6) . . ? N5 N4 C12 122.4(6) . . ? N4 N5 C1 103.9(6) . . ? C11 C6 C7 124.0(7) . . ? C11 C6 N3 116.2(7) . . ? C7 C6 N3 119.8(7) . . ? C6 C7 C8 117.8(7) . . ? C7 C8 C9 121.0(8) . . ? C8 C9 C10 119.5(7) . . ? C11 C10 C9 119.5(8) . . ? C6 C11 C10 118.0(8) . . ? C13 C12 C17 123.8(7) . . ? C13 C12 N4 118.1(7) . . ? C17 C12 N4 118.1(7) . . ? C12 C13 C14 118.0(8) . . ? C15 C14 C13 120.4(8) . . ? C14 C15 C16 120.9(8) . . ? C15 C16 C17 120.1(8) . . ? C12 C17 C16 116.7(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.130 _refine_diff_density_min -1.264 _refine_diff_density_rms 0.163 data_ig4mauda _database_code_depnum_ccdc_archive 'CCDC 221998' _chemical_name_common ; ((2-dimethylammoniummethyl-phenyl) 2-pyridineformamide -N(4) - methylthiosemicarbazonatogold(iii)) dichloride x 3H2O ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(2-dimethylammoniummethyl-phenyl) 2-pyridineformamide -N(4) -methylthiosemicarbazonatogold(III)] dichloride x 3H2O ; _chemical_melting_point ? _chemical_formula_moiety [Au(Hdamp-C1)(Am4Me)]Cl2.3H2O _chemical_formula_sum 'C17 H23 Au Cl2 N6 O3 S' _chemical_formula_weight 659.34 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' Cl Cl 0.1484 0.1585 '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' _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 9.967(10) _cell_length_b 10.818(6) _cell_length_c 12.923(4) _cell_angle_alpha 83.14(3) _cell_angle_beta 74.27(3) _cell_angle_gamma 63.34(5) _cell_volume 1198.6(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.23 _cell_measurement_theta_max 14.39 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max .5 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 6.476 _exptl_absorpt_correction_type 'Psi scan' _exptl_absorpt_correction_T_min 0.6204 _exptl_absorpt_correction_T_max 0.9084 _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 CAD4 _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 3 _diffrn_reflns_number 6066 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 26.94 _reflns_number_total 5188 _reflns_number_gt 4511 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement SET4 _computing_data_reduction HELENA _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material WINGX _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^)+(0.0741P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5188 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au Au 0.38720(2) 0.05869(2) 0.218660(16) 0.02710(9) Uani 1 1 d . . . N1 N 0.2981(6) 0.2139(5) 0.1130(4) 0.0286(10) Uani 1 1 d . . . C1 C 0.2732(8) 0.3450(7) 0.1156(5) 0.0372(14) Uani 1 1 d . . . H1 H 0.2940 0.3747 0.1715 0.045 Uiso 1 1 calc R . . C2 C 0.2175(8) 0.4381(7) 0.0377(6) 0.0428(15) Uani 1 1 d . . . H2 H 0.1990 0.5298 0.0417 0.051 Uiso 1 1 calc R . . C3 C 0.1897(8) 0.3938(7) -0.0458(5) 0.0410(15) Uani 1 1 d . . . H3 H 0.1541 0.4548 -0.0999 0.049 Uiso 1 1 calc R . . C4 C 0.2151(7) 0.2573(7) -0.0489(5) 0.0357(13) Uani 1 1 d . . . H4 H 0.1958 0.2261 -0.1048 0.043 Uiso 1 1 calc R . . C5 C 0.2688(7) 0.1687(6) 0.0310(5) 0.0287(12) Uani 1 1 d . . . C6 C 0.3003(6) 0.0219(6) 0.0354(5) 0.0284(11) Uani 1 1 d . . . N5 N 0.2701(7) -0.0324(6) -0.0367(4) 0.0398(12) Uani 1 1 d . . . H5A H 0.2926 -0.1192 -0.0345 0.048 Uiso 1 1 calc R . . H5B H 0.2279 0.0190 -0.0858 0.048 Uiso 1 1 calc R . . N2 N 0.3638(6) -0.0479(5) 0.1124(4) 0.0307(10) Uani 1 1 d . . . N3 N 0.3971(6) -0.1859(5) 0.1255(4) 0.0320(11) Uani 1 1 d . . . C7 C 0.4511(7) -0.2367(6) 0.2095(5) 0.0334(13) Uani 1 1 d . . . S S 0.4833(2) -0.14648(17) 0.30108(13) 0.0400(4) Uani 1 1 d . . . N4 N 0.4885(7) -0.3708(6) 0.2356(5) 0.0445(14) Uani 1 1 d . . . H41 H 0.5290 -0.4049 0.2894 0.053 Uiso 1 1 calc R . . C8 C 0.4619(11) -0.4586(8) 0.1749(8) 0.057(2) Uani 1 1 d . . . H8A H 0.4962 -0.5500 0.2049 0.085 Uiso 1 1 calc R . . H8B H 0.5185 -0.4627 0.1013 0.085 Uiso 1 1 calc R . . H8C H 0.3534 -0.4211 0.1783 0.085 Uiso 1 1 calc R . . C11 C 0.4082(7) 0.1714(6) 0.3240(5) 0.0292(12) Uani 1 1 d . . . C12 C 0.5544(7) 0.1644(7) 0.3138(5) 0.0366(14) Uani 1 1 d . . . H12 H 0.6395 0.1025 0.2651 0.044 Uiso 1 1 calc R . . C13 C 0.5748(8) 0.2477(8) 0.3748(6) 0.0429(16) Uani 1 1 d . . . H13 H 0.6725 0.2436 0.3659 0.052 Uiso 1 1 calc R . . C14 C 0.4511(8) 0.3364(7) 0.4487(6) 0.0413(15) Uani 1 1 d . . . H14 H 0.4646 0.3913 0.4913 0.050 Uiso 1 1 calc R . . C15 C 0.3055(8) 0.3437(7) 0.4595(5) 0.0363(14) Uani 1 1 d . . . H15 H 0.2213 0.4052 0.5090 0.044 Uiso 1 1 calc R . . C16 C 0.2826(7) 0.2608(6) 0.3978(5) 0.0294(12) Uani 1 1 d . . . C17 C 0.1226(7) 0.2729(7) 0.4159(5) 0.0321(12) Uani 1 1 d . . . H17A H 0.1197 0.2243 0.3587 0.039 Uiso 1 1 calc R . . H17B H 0.0514 0.3696 0.4121 0.039 Uiso 1 1 calc R . . N6 N 0.0696(6) 0.2155(6) 0.5220(4) 0.0353(11) Uani 1 1 d . . . H6 H 0.0693 0.2649 0.5743 0.042 Uiso 1 1 calc R . . C18 C 0.1760(11) 0.0707(9) 0.5341(7) 0.060(2) Uani 1 1 d . . . H18A H 0.1398 0.0377 0.6033 0.090 Uiso 1 1 calc R . . H18B H 0.2774 0.0636 0.5282 0.090 Uiso 1 1 calc R . . H18C H 0.1807 0.0160 0.4788 0.090 Uiso 1 1 calc R . . C19 C -0.0929(9) 0.2356(10) 0.5364(7) 0.056(2) Uani 1 1 d . . . H19A H -0.1583 0.3317 0.5277 0.085 Uiso 1 1 calc R . . H19B H -0.1291 0.2061 0.6071 0.085 Uiso 1 1 calc R . . H19C H -0.0957 0.1819 0.4837 0.085 Uiso 1 1 calc R . . Cl1 Cl 0.0101(2) 0.3835(2) 0.71696(14) 0.0495(4) Uani 1 1 d . . . Cl2 Cl -0.0137(2) 0.1292(2) 0.24805(15) 0.0508(4) Uani 1 1 d . . . O1 O 0.7721(7) -0.5410(6) 0.3157(5) 0.0570(14) Uani 1 1 d . . . O2 O 0.1767(8) -0.2505(6) -0.0485(5) 0.0662(16) Uani 1 1 d . . . O3 O 0.0306(7) 0.1165(6) -0.1505(5) 0.0563(14) 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 Au 0.03028(13) 0.02936(13) 0.02327(12) -0.00298(8) -0.00762(8) -0.01305(9) N1 0.032(2) 0.028(2) 0.027(2) -0.0046(19) -0.007(2) -0.013(2) C1 0.045(4) 0.036(3) 0.034(3) -0.005(3) -0.010(3) -0.020(3) C2 0.050(4) 0.036(4) 0.041(4) -0.001(3) -0.007(3) -0.019(3) C3 0.044(4) 0.042(4) 0.031(3) 0.008(3) -0.007(3) -0.017(3) C4 0.038(3) 0.041(3) 0.028(3) 0.000(2) -0.012(3) -0.015(3) C5 0.029(3) 0.033(3) 0.025(3) -0.002(2) -0.004(2) -0.015(2) C6 0.026(3) 0.035(3) 0.027(3) -0.006(2) -0.005(2) -0.014(2) N5 0.051(3) 0.040(3) 0.037(3) -0.003(2) -0.019(3) -0.022(3) N2 0.033(3) 0.027(2) 0.034(3) -0.007(2) -0.006(2) -0.014(2) N3 0.037(3) 0.022(2) 0.038(3) -0.002(2) -0.012(2) -0.011(2) C7 0.029(3) 0.032(3) 0.036(3) -0.002(2) -0.005(2) -0.012(2) S 0.0521(10) 0.0349(8) 0.0341(8) 0.0019(6) -0.0201(7) -0.0149(7) N4 0.059(4) 0.029(3) 0.052(4) 0.005(2) -0.026(3) -0.019(3) C8 0.070(5) 0.036(4) 0.071(5) -0.002(4) -0.020(4) -0.027(4) C11 0.034(3) 0.036(3) 0.024(3) 0.001(2) -0.011(2) -0.019(3) C12 0.033(3) 0.043(4) 0.034(3) -0.005(3) -0.008(3) -0.016(3) C13 0.041(4) 0.059(4) 0.042(4) 0.004(3) -0.016(3) -0.030(3) C14 0.050(4) 0.045(4) 0.043(4) -0.007(3) -0.014(3) -0.030(3) C15 0.039(3) 0.040(3) 0.034(3) -0.009(3) -0.003(3) -0.021(3) C16 0.034(3) 0.032(3) 0.026(3) -0.003(2) -0.008(2) -0.016(2) C17 0.034(3) 0.040(3) 0.024(3) 0.000(2) -0.005(2) -0.018(3) N6 0.040(3) 0.039(3) 0.031(3) -0.005(2) -0.003(2) -0.022(2) C18 0.065(5) 0.051(5) 0.056(5) 0.015(4) -0.004(4) -0.028(4) C19 0.048(4) 0.083(6) 0.049(4) -0.006(4) -0.001(3) -0.043(4) Cl1 0.0669(12) 0.0490(10) 0.0364(8) -0.0060(7) -0.0079(8) -0.0298(9) Cl2 0.0442(9) 0.0634(11) 0.0495(10) -0.0172(8) 0.0020(8) -0.0310(9) O1 0.060(3) 0.049(3) 0.070(4) 0.001(3) -0.029(3) -0.024(3) O2 0.082(4) 0.049(3) 0.075(4) 0.000(3) -0.019(3) -0.034(3) O3 0.079(4) 0.057(3) 0.055(3) 0.009(3) -0.039(3) -0.038(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au N2 2.016(5) . ? Au C11 2.040(6) . ? Au N1 2.061(5) . ? Au S 2.249(2) . ? N1 C1 1.328(8) . ? N1 C5 1.366(7) . ? C1 C2 1.377(10) . ? C2 C3 1.368(10) . ? C3 C4 1.385(10) . ? C4 C5 1.369(9) . ? C5 C6 1.472(8) . ? C6 N2 1.301(8) . ? C6 N5 1.321(7) . ? N2 N3 1.375(7) . ? N3 C7 1.297(8) . ? C7 N4 1.350(8) . ? C7 S 1.794(6) . ? N4 C8 1.451(9) . ? C11 C16 1.378(8) . ? C11 C12 1.396(8) . ? C12 C13 1.377(9) . ? C13 C14 1.368(10) . ? C14 C15 1.387(9) . ? C15 C16 1.395(8) . ? C16 C17 1.494(8) . ? C17 N6 1.498(8) . ? N6 C18 1.464(10) . ? N6 C19 1.495(9) . ? 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 Au C11 178.4(2) . . ? N2 Au N1 79.5(2) . . ? C11 Au N1 99.0(2) . . ? N2 Au S 84.89(16) . . ? C11 Au S 96.67(18) . . ? N1 Au S 164.33(14) . . ? C1 N1 C5 119.8(5) . . ? C1 N1 Au 127.4(4) . . ? C5 N1 Au 112.8(4) . . ? N1 C1 C2 121.7(6) . . ? C3 C2 C1 119.2(6) . . ? C2 C3 C4 119.4(6) . . ? C5 C4 C3 119.4(6) . . ? C4 C5 N1 120.5(6) . . ? C4 C5 C6 124.0(5) . . ? N1 C5 C6 115.6(5) . . ? N2 C6 N5 124.2(6) . . ? N2 C6 C5 114.6(5) . . ? N5 C6 C5 121.2(5) . . ? C6 N2 N3 120.0(5) . . ? C6 N2 Au 117.3(4) . . ? N3 N2 Au 122.4(4) . . ? C7 N3 N2 111.6(5) . . ? N3 C7 N4 119.8(6) . . ? N3 C7 S 126.9(5) . . ? N4 C7 S 113.4(5) . . ? C7 S Au 94.1(2) . . ? C7 N4 C8 121.5(6) . . ? C16 C11 C12 119.6(5) . . ? C16 C11 Au 122.5(4) . . ? C12 C11 Au 117.7(5) . . ? C13 C12 C11 121.0(6) . . ? C14 C13 C12 119.9(6) . . ? C13 C14 C15 119.5(6) . . ? C14 C15 C16 121.4(6) . . ? C11 C16 C15 118.6(5) . . ? C11 C16 C17 123.3(5) . . ? C15 C16 C17 118.1(5) . . ? C16 C17 N6 113.0(5) . . ? C18 N6 C19 112.4(6) . . ? C18 N6 C17 111.6(5) . . ? C19 N6 C17 110.1(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 N5 H5A O2 0.86 2.24 2.931(8) 136.8 . N5 H5B O3 0.86 2.12 2.888(8) 148.4 . N4 H41 O1 0.86 2.30 2.986(9) 137.1 . N6 H6 Cl1 0.91 2.16 3.053(6) 165.1 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.94 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.717 _refine_diff_density_min -3.050 _refine_diff_density_rms 0.200 data_audmdm _database_code_depnum_ccdc_archive 'CCDC 221999' _chemical_name_common ; (((2-Dimethylammoniummethyl)phenyl)(2-pyridineformamide (N3- dimethyl)thiosemicarbazonatogold(iii))) dichloride x H2O (Au(Hdamp- C)(dmpytsc))Cl2 x H2O ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; [{(2-Dimethylammoniummethyl)phenyl}{2-pyridineformamide (N3-dimethyl)thiosemicarbazonatogold(III)}] dichloride x H2O [Au(Hdamp-C)(dmpytsc)]Cl2 x H2O ; _chemical_melting_point ? _chemical_formula_moiety '[Au(Hdamp-C)(dmpytsc)]Cl2 x H2O' _chemical_formula_sum 'C18 H27 Au Cl2 N6 O S' _chemical_formula_weight 643.38 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' Au Au -2.0133 8.8022 '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' _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 11.181(2) _cell_length_b 11.348(2) _cell_length_c 11.926(2) _cell_angle_alpha 65.74(1) _cell_angle_beta 64.32(1) _cell_angle_gamma 63.94(1) _cell_volume 1178.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.13 _cell_measurement_theta_max 13.64 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 6.577 _exptl_absorpt_correction_type DELABS _exptl_absorpt_correction_T_min 0.313 _exptl_absorpt_correction_T_max 0.748 _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 CAD4 _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4486 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 26.96 _reflns_number_total 3964 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 _computing_cell_refinement SET4 _computing_data_reduction WINGX _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material WINGX _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^)+(0.0412P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3964 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 Au Au 0.35563(2) 0.07009(2) 0.18174(2) 0.03225(10) Uani 1 1 d . . . Cl1 Cl 0.99493(18) 0.31056(17) 0.74919(18) 0.0500(4) Uani 1 1 d . . . S S 0.43461(17) -0.15291(16) 0.27643(17) 0.0415(4) Uani 1 1 d . . . N6 N 0.0425(5) 0.2199(5) 0.5196(5) 0.0400(13) Uani 1 1 d . . . H6 H 0.0517 0.2356 0.5840 0.048 Uiso 1 1 calc R . . C10 C 0.3929(6) 0.1286(6) 0.2985(6) 0.0359(15) Uani 1 1 d . . . N2 N 0.3215(5) 0.0112(4) 0.0644(5) 0.0330(12) Uani 1 1 d . . . C16 C 0.3031(6) 0.1355(6) 0.4247(6) 0.0352(15) Uani 1 1 d . . . C4 C 0.1793(7) 0.3603(6) -0.1079(7) 0.0458(17) Uani 1 1 d . . . H4 H 0.1518 0.3521 -0.1669 0.055 Uiso 1 1 calc R . . C8 C 0.4721(9) -0.4381(7) 0.3147(8) 0.067(2) Uani 1 1 d . . . H8A H 0.4939 -0.5295 0.3136 0.100 Uiso 1 1 calc R . . H8B H 0.3957 -0.4203 0.3908 0.100 Uiso 1 1 calc R . . H8C H 0.5526 -0.4278 0.3151 0.100 Uiso 1 1 calc R . . C12 C 0.5523(7) 0.1951(6) 0.3280(7) 0.0485(19) Uani 1 1 d . . . H12 H 0.6344 0.2166 0.2956 0.058 Uiso 1 1 calc R . . N5 N 0.2032(5) 0.0838(5) -0.0823(6) 0.0425(14) Uani 1 1 d . . . H5A H 0.2151 0.0020 -0.0779 0.051 Uiso 1 1 calc R . . H5B H 0.1585 0.1520 -0.1320 0.051 Uiso 1 1 calc R . . N4 N 0.4330(6) -0.3433(5) 0.2015(6) 0.0464(15) Uani 1 1 d . . . C18 C 0.0293(8) 0.3495(7) 0.4132(7) 0.057(2) Uani 1 1 d . . . H18A H 0.1132 0.3732 0.3800 0.085 Uiso 1 1 calc R . . H18B H -0.0492 0.4211 0.4461 0.085 Uiso 1 1 calc R . . H18C H 0.0154 0.3374 0.3451 0.085 Uiso 1 1 calc R . . N1 N 0.2747(5) 0.2576(5) 0.0652(5) 0.0364(13) Uani 1 1 d . . . C5 C 0.2335(6) 0.2475(6) -0.0215(6) 0.0346(16) Uani 1 1 d . . . C19 C -0.0872(6) 0.1819(7) 0.5738(7) 0.0512(19) Uani 1 1 d . . . H19A H -0.1664 0.2559 0.6018 0.077 Uiso 1 1 calc R . . H19B H -0.0799 0.1023 0.6461 0.077 Uiso 1 1 calc R . . H19C H -0.0990 0.1628 0.5086 0.077 Uiso 1 1 calc R . . N3 N 0.3471(5) -0.1271(5) 0.0817(5) 0.0370(13) Uani 1 1 d . . . C13 C 0.4643(7) 0.2007(7) 0.4517(7) 0.0478(18) Uani 1 1 d . . . H13 H 0.4883 0.2247 0.5031 0.057 Uiso 1 1 calc R . . C7 C 0.3985(6) -0.2060(6) 0.1749(6) 0.0350(15) Uani 1 1 d . . . C2 C 0.2056(7) 0.4972(7) -0.0204(8) 0.054(2) Uani 1 1 d . . . H2 H 0.1959 0.5820 -0.0184 0.065 Uiso 1 1 calc R . . C15 C 0.3424(7) 0.1713(7) 0.4988(7) 0.0508(19) Uani 1 1 d . . . H15 H 0.2845 0.1753 0.5823 0.061 Uiso 1 1 calc R . . C17 C 0.1688(6) 0.1047(6) 0.4788(7) 0.0439(17) Uani 1 1 d . . . H17A H 0.1735 0.0252 0.5529 0.053 Uiso 1 1 calc R . . H17B H 0.1582 0.0823 0.4141 0.053 Uiso 1 1 calc R . . C3 C 0.1653(7) 0.4880(6) -0.1076(8) 0.051(2) Uani 1 1 d . . . H3 H 0.1288 0.5661 -0.1666 0.061 Uiso 1 1 calc R . . C1 C 0.2615(6) 0.3798(6) 0.0659(7) 0.0435(17) Uani 1 1 d . . . H1 H 0.2901 0.3865 0.1250 0.052 Uiso 1 1 calc R . . C11 C 0.5177(6) 0.1576(6) 0.2537(7) 0.0440(18) Uani 1 1 d . . . H11 H 0.5785 0.1513 0.1716 0.053 Uiso 1 1 calc R . . C9 C 0.3976(8) -0.3958(7) 0.1309(8) 0.057(2) Uani 1 1 d . . . H9A H 0.4284 -0.4936 0.1588 0.085 Uiso 1 1 calc R . . H9B H 0.4431 -0.3659 0.0399 0.085 Uiso 1 1 calc R . . H9C H 0.2981 -0.3624 0.1474 0.085 Uiso 1 1 calc R . . C6 C 0.2534(6) 0.1047(6) -0.0128(6) 0.0344(15) Uani 1 1 d . . . Cl2 Cl 0.96463(19) 0.16870(17) 0.24722(18) 0.0558(5) Uani 1 1 d . . . O1 O 0.8396(5) 0.1600(5) 0.0551(5) 0.0563(13) Uani 1 1 d . . . H111 H 0.8692 0.1741 0.1215 0.050 Uiso 1 1 d . . . H112 H 0.8783 0.1998 -0.0232 0.050 Uiso 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 Au 0.03226(12) 0.03310(12) 0.03228(15) -0.00978(9) -0.00981(9) -0.01049(8) Cl1 0.0584(10) 0.0522(9) 0.0429(10) -0.0116(8) -0.0237(8) -0.0138(8) S 0.0473(9) 0.0381(8) 0.0410(10) -0.0082(7) -0.0201(8) -0.0112(7) N6 0.045(3) 0.040(3) 0.034(3) -0.008(2) -0.014(2) -0.014(2) C10 0.041(3) 0.036(3) 0.035(4) -0.013(3) -0.012(3) -0.012(3) N2 0.035(2) 0.031(2) 0.033(3) -0.010(2) -0.010(2) -0.010(2) C16 0.048(4) 0.041(3) 0.031(4) -0.013(3) -0.016(3) -0.019(3) C4 0.051(4) 0.042(3) 0.049(4) -0.010(3) -0.022(3) -0.015(3) C8 0.081(6) 0.047(4) 0.069(6) -0.011(4) -0.033(5) -0.014(4) C12 0.048(4) 0.048(4) 0.058(5) -0.015(4) -0.019(4) -0.019(3) N5 0.047(3) 0.042(3) 0.048(4) -0.015(3) -0.022(3) -0.012(2) N4 0.057(3) 0.030(3) 0.052(4) -0.009(3) -0.025(3) -0.008(2) C18 0.064(5) 0.049(4) 0.053(5) 0.002(3) -0.025(4) -0.023(3) N1 0.036(3) 0.037(3) 0.038(3) -0.014(2) -0.008(2) -0.013(2) C5 0.029(3) 0.035(3) 0.036(4) -0.009(3) -0.010(3) -0.009(2) C19 0.041(4) 0.050(4) 0.055(5) -0.011(3) -0.008(3) -0.018(3) N3 0.043(3) 0.032(2) 0.039(3) -0.011(2) -0.017(3) -0.009(2) C13 0.061(4) 0.056(4) 0.044(5) -0.012(3) -0.032(4) -0.019(3) C7 0.032(3) 0.037(3) 0.036(4) -0.015(3) -0.007(3) -0.010(2) C2 0.056(4) 0.039(4) 0.068(5) -0.018(4) -0.018(4) -0.013(3) C15 0.059(4) 0.058(4) 0.033(4) -0.013(3) -0.007(3) -0.023(3) C17 0.044(3) 0.045(3) 0.041(4) -0.018(3) -0.008(3) -0.011(3) C3 0.059(4) 0.033(3) 0.059(5) 0.000(3) -0.036(4) -0.006(3) C1 0.050(4) 0.035(3) 0.055(5) -0.016(3) -0.022(3) -0.012(3) C11 0.033(3) 0.047(3) 0.054(5) -0.024(3) -0.007(3) -0.012(3) C9 0.061(4) 0.043(4) 0.073(6) -0.021(4) -0.024(4) -0.014(3) C6 0.031(3) 0.039(3) 0.033(4) -0.012(3) -0.007(3) -0.011(2) Cl2 0.0662(11) 0.0495(9) 0.0495(11) -0.0047(8) -0.0205(9) -0.0220(8) O1 0.063(3) 0.066(3) 0.052(3) -0.013(3) -0.016(3) -0.035(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au N2 2.001(5) . ? Au C10 2.015(7) . ? Au N1 2.061(5) . ? Au S 2.2386(16) . ? S C7 1.797(7) . ? N6 C19 1.488(8) . ? N6 C18 1.494(8) . ? N6 C17 1.499(7) . ? C10 C11 1.398(8) . ? C10 C16 1.413(8) . ? N2 C6 1.284(8) . ? N2 N3 1.406(6) . ? C16 C15 1.389(9) . ? C16 C17 1.493(8) . ? C4 C5 1.358(9) . ? C4 C3 1.389(9) . ? C8 N4 1.440(9) . ? C12 C11 1.365(10) . ? C12 C13 1.383(10) . ? N5 C6 1.318(8) . ? N4 C7 1.360(7) . ? N4 C9 1.459(9) . ? N1 C1 1.332(7) . ? N1 C5 1.360(8) . ? C5 C6 1.500(8) . ? N3 C7 1.284(8) . ? C13 C15 1.367(9) . ? C2 C3 1.353(10) . ? C2 C1 1.387(10) . ? 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 Au C10 179.2(2) . . ? N2 Au N1 80.0(2) . . ? C10 Au N1 100.2(2) . . ? N2 Au S 85.38(14) . . ? C10 Au S 94.43(17) . . ? N1 Au S 165.39(16) . . ? C7 S Au 94.7(2) . . ? C19 N6 C18 110.5(5) . . ? C19 N6 C17 110.8(5) . . ? C18 N6 C17 112.9(5) . . ? C11 C10 C16 118.7(6) . . ? C11 C10 Au 117.8(5) . . ? C16 C10 Au 123.5(5) . . ? C6 N2 N3 120.4(5) . . ? C6 N2 Au 117.2(4) . . ? N3 N2 Au 121.4(4) . . ? C15 C16 C10 118.6(6) . . ? C15 C16 C17 120.0(6) . . ? C10 C16 C17 121.4(6) . . ? C5 C4 C3 119.6(7) . . ? C11 C12 C13 119.6(7) . . ? C7 N4 C8 123.3(6) . . ? C7 N4 C9 118.4(6) . . ? C8 N4 C9 116.7(6) . . ? C1 N1 C5 119.8(6) . . ? C1 N1 Au 127.8(5) . . ? C5 N1 Au 112.4(4) . . ? C4 C5 N1 121.0(6) . . ? C4 C5 C6 124.2(7) . . ? N1 C5 C6 114.8(5) . . ? C7 N3 N2 112.4(5) . . ? C15 C13 C12 120.4(7) . . ? N3 C7 N4 119.6(6) . . ? N3 C7 S 126.0(5) . . ? N4 C7 S 114.4(5) . . ? C3 C2 C1 119.9(6) . . ? C13 C15 C16 121.4(6) . . ? C16 C17 N6 113.7(5) . . ? C2 C3 C4 119.1(6) . . ? N1 C1 C2 120.7(7) . . ? C12 C11 C10 121.4(6) . . ? N2 C6 N5 125.5(6) . . ? N2 C6 C5 114.6(6) . . ? N5 C6 C5 119.9(6) . . ? 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 O1 H111 Cl2 1.068(5) 2.155(2) 3.209(5) 168.8(3) . N5 H5A O1 0.86 2.06 2.878(7) 157.5 2_655 N5 H5B Cl1 0.86 2.42 3.260(6) 165.8 1_454 N6 H6 Cl1 0.91 2.20 3.067(6) 159.7 1_455 O1 H112 Cl1 0.859(5) 2.4933(18) 3.353(5) 178.8(4) 1_554 _diffrn_measured_fraction_theta_max 0.772 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.772 _refine_diff_density_max 0.782 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.137 data_auhm4dh _database_code_depnum_ccdc_archive 'CCDC 222000' _chemical_name_common ;Chloro(2-pyridineformamide thiosemicarbazonato)gold(iii) chloride ; _audit_creation_method SHELXL-97 _chemical_name_systematic 'Chloro(2-pyridineformamide thiosemicarbazonato)gold(III) chloride' _chemical_melting_point ? _chemical_formula_moiety [AuCl(hm4dh)]Cl _chemical_formula_sum 'C9 H16 Au Cl2 N5 O2 S' _chemical_formula_weight 526.19 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' Au Au -2.0133 8.8022 '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' _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 36.752(6) _cell_length_b 12.413(2) _cell_length_c 13.958(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.70(1) _cell_angle_gamma 90.00 _cell_volume 6367.2(17) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4000 _exptl_absorpt_coefficient_mu 9.716 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.5654 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Bruker areal 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_% 1 _diffrn_reflns_number 39108 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 30.56 _reflns_number_total 9721 _reflns_number_gt 8385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker CCD' _computing_cell_refinement 'Bruker CCD' _computing_data_reduction SAINT _computing_structure_solution SHELXS-98 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material WINGX _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^)+(0.0240P)^2^+20.9728P] 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 model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9721 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0207 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.006 _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 0.497419(3) -0.182707(9) 0.122554(8) 0.02026(3) Uani 1 1 d . . . Cl1 Cl 0.51056(2) -0.36153(6) 0.10896(7) 0.03593(19) Uani 1 1 d . . . N1 N 0.54746(6) -0.1207(2) 0.08496(18) 0.0218(5) Uani 1 1 d . . . C1 C 0.57699(9) -0.1761(3) 0.0585(3) 0.0287(7) Uani 1 1 d . . . H1 H 0.5760 -0.2525 0.0555 0.034 Uiso 1 1 calc R . . C2 C 0.60875(9) -0.1236(3) 0.0357(3) 0.0322(7) Uani 1 1 d . . . H2 H 0.6296 -0.1634 0.0170 0.039 Uiso 1 1 calc R . . C3 C 0.60999(8) -0.0140(3) 0.0402(2) 0.0298(7) Uani 1 1 d . . . H3 H 0.6320 0.0227 0.0260 0.036 Uiso 1 1 calc R . . C4 C 0.57936(8) 0.0444(2) 0.0653(2) 0.0242(6) Uani 1 1 d . . . H4 H 0.5799 0.1209 0.0668 0.029 Uiso 1 1 calc R . . C5 C 0.54812(7) -0.0113(2) 0.0880(2) 0.0198(5) Uani 1 1 d . . . C6 C 0.51337(8) 0.0405(2) 0.1161(2) 0.0198(5) Uani 1 1 d . . . N5 N 0.50950(7) 0.1454(2) 0.1194(2) 0.0250(5) Uani 1 1 d . . . H5A H 0.4883 0.1736 0.1342 0.030 Uiso 1 1 calc R . . H5B H 0.5281 0.1876 0.1067 0.030 Uiso 1 1 calc R . . N2 N 0.48664(6) -0.02766(19) 0.13430(17) 0.0193(5) Uani 1 1 d . . . N3 N 0.45314(6) 0.0108(2) 0.16297(18) 0.0216(5) Uani 1 1 d . . . C7 C 0.42964(7) -0.0657(2) 0.1783(2) 0.0209(5) Uani 1 1 d . . . S1 S 0.43895(2) -0.20646(6) 0.16562(6) 0.02587(15) Uani 1 1 d . . . N4 N 0.39587(7) -0.0424(2) 0.2071(2) 0.0277(6) Uani 1 1 d . . . H4A H 0.3894 0.0251 0.2158 0.033 Uiso 1 1 calc R . . H4B H 0.3802 -0.0946 0.2173 0.033 Uiso 1 1 calc R . . Au2 Au 0.706450(3) -0.152092(9) 0.398992(8) 0.01857(3) Uani 1 1 d . . . Cl2 Cl 0.652328(19) -0.22149(6) 0.45071(6) 0.02906(16) Uani 1 1 d . . . N11 N 0.73442(6) -0.2963(2) 0.38672(18) 0.0205(5) Uani 1 1 d . . . C11 C 0.72133(9) -0.3952(2) 0.4020(2) 0.0260(6) Uani 1 1 d . . . H11 H 0.6969 -0.4039 0.4221 0.031 Uiso 1 1 calc R . . C12 C 0.74293(9) -0.4848(3) 0.3889(2) 0.0291(7) Uani 1 1 d . . . H12 H 0.7336 -0.5549 0.4007 0.035 Uiso 1 1 calc R . . C13 C 0.77807(9) -0.4715(2) 0.3588(2) 0.0278(6) Uani 1 1 d . . . H13 H 0.7931 -0.5327 0.3490 0.033 Uiso 1 1 calc R . . C14 C 0.79167(8) -0.3686(2) 0.3423(2) 0.0240(6) Uani 1 1 d . . . H14 H 0.8160 -0.3586 0.3216 0.029 Uiso 1 1 calc R . . C15 C 0.76910(8) -0.2814(2) 0.3568(2) 0.0202(5) Uani 1 1 d . . . C16 C 0.77992(8) -0.1680(2) 0.3432(2) 0.0204(5) Uani 1 1 d . . . N15 N 0.81284(7) -0.1405(2) 0.3157(2) 0.0299(6) Uani 1 1 d . . . H15A H 0.8186 -0.0721 0.3096 0.036 Uiso 1 1 calc R . . H15B H 0.8291 -0.1906 0.3034 0.036 Uiso 1 1 calc R . . N12 N 0.75437(6) -0.09604(19) 0.36267(18) 0.0195(5) Uani 1 1 d . . . N13 N 0.76264(7) 0.01252(19) 0.35944(19) 0.0225(5) Uani 1 1 d . . . C17 C 0.73486(8) 0.0735(2) 0.3796(2) 0.0220(6) Uani 1 1 d . . . S2 S 0.690115(19) 0.02367(6) 0.40317(6) 0.02476(15) Uani 1 1 d . . . N14 N 0.73792(8) 0.1805(2) 0.3810(2) 0.0302(6) Uani 1 1 d . . . H14A H 0.7589 0.2111 0.3683 0.036 Uiso 1 1 calc R . . H14B H 0.7189 0.2206 0.3947 0.036 Uiso 1 1 calc R . . Cl3 Cl 0.68127(2) -0.21808(6) 0.18742(6) 0.03357(17) Uani 1 1 d . . . Cl4 Cl 0.87869(2) -0.28595(7) 0.24430(7) 0.03316(17) Uani 1 1 d . . . O20 O 0.44957(7) 0.2768(2) 0.1341(2) 0.0439(7) Uani 1 1 d . . . H20 H 0.4299 0.2630 0.1616 0.066 Uiso 1 1 calc R . . C21 C 0.45904(13) 0.3857(3) 0.1504(4) 0.0524(11) Uani 1 1 d . . . H21A H 0.4592 0.4003 0.2194 0.079 Uiso 1 1 calc R . . H21B H 0.4412 0.4326 0.1184 0.079 Uiso 1 1 calc R . . H21C H 0.4833 0.3997 0.1246 0.079 Uiso 1 1 calc R . . O30 O 0.56567(8) 0.3033(2) 0.1075(2) 0.0435(7) Uani 1 1 d . . . H30 H 0.5840 0.2830 0.1390 0.065 Uiso 1 1 calc R . . C31 C 0.57465(12) 0.3942(3) 0.0525(3) 0.0460(9) Uani 1 1 d . . . H31A H 0.5727 0.4591 0.0921 0.069 Uiso 1 1 calc R . . H31B H 0.5579 0.3998 -0.0023 0.069 Uiso 1 1 calc R . . H31C H 0.5996 0.3871 0.0295 0.069 Uiso 1 1 calc R . . O40 O 0.68321(9) 0.3094(3) 0.4726(3) 0.0625(9) Uani 1 1 d . . . H40 H 0.6801 0.2721 0.5221 0.094 Uiso 1 1 calc R . . C41 C 0.65649(11) 0.3869(3) 0.4664(3) 0.0462(10) Uani 1 1 d . . . H41A H 0.6330 0.3548 0.4823 0.069 Uiso 1 1 calc R . . H41B H 0.6554 0.4156 0.4011 0.069 Uiso 1 1 calc R . . H41C H 0.6621 0.4453 0.5115 0.069 Uiso 1 1 calc R . . O50 O 0.84230(7) 0.0531(2) 0.2571(2) 0.0476(7) Uani 1 1 d . . . H50 H 0.8346 0.1138 0.2739 0.071 Uiso 1 1 calc R . . C51 C 0.87965(10) 0.0592(4) 0.2402(3) 0.0480(10) Uani 1 1 d . . . H51A H 0.8916 0.0989 0.2925 0.072 Uiso 1 1 calc R . . H51B H 0.8837 0.0968 0.1795 0.072 Uiso 1 1 calc R . . H51C H 0.8898 -0.0136 0.2367 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.01916(5) 0.01695(5) 0.02469(6) -0.00081(4) 0.00109(4) 0.00076(4) Cl1 0.0354(4) 0.0172(3) 0.0554(5) -0.0033(3) 0.0074(4) 0.0021(3) N1 0.0191(11) 0.0217(12) 0.0248(13) 0.0000(10) 0.0018(9) 0.0021(9) C1 0.0236(14) 0.0251(15) 0.0375(18) -0.0018(13) 0.0041(13) 0.0064(12) C2 0.0222(14) 0.0332(18) 0.0413(19) 0.0006(14) 0.0086(13) 0.0068(13) C3 0.0220(14) 0.0344(17) 0.0332(17) 0.0022(14) 0.0065(12) 0.0006(12) C4 0.0248(14) 0.0219(14) 0.0261(15) 0.0014(11) 0.0046(11) 0.0000(11) C5 0.0182(12) 0.0223(14) 0.0190(13) 0.0004(10) 0.0020(10) 0.0012(10) C6 0.0206(12) 0.0217(14) 0.0172(13) 0.0000(10) 0.0006(10) 0.0014(10) N5 0.0209(12) 0.0182(12) 0.0359(15) 0.0000(10) 0.0056(10) 0.0010(9) N2 0.0175(10) 0.0189(11) 0.0214(12) -0.0011(9) 0.0013(9) 0.0005(9) N3 0.0177(10) 0.0214(12) 0.0259(13) -0.0015(10) 0.0023(9) 0.0014(9) C7 0.0189(12) 0.0227(14) 0.0211(14) -0.0018(11) -0.0007(10) 0.0004(10) S1 0.0208(3) 0.0212(4) 0.0356(4) -0.0016(3) 0.0030(3) -0.0027(3) N4 0.0176(11) 0.0278(14) 0.0378(15) -0.0067(11) 0.0058(10) -0.0013(10) Au2 0.01591(5) 0.01799(5) 0.02183(5) 0.00083(4) 0.00121(4) 0.00089(3) Cl2 0.0192(3) 0.0274(4) 0.0408(4) 0.0018(3) 0.0072(3) -0.0018(3) N11 0.0201(11) 0.0189(12) 0.0226(12) 0.0012(9) -0.0007(9) 0.0001(9) C11 0.0264(14) 0.0192(14) 0.0324(16) -0.0001(12) -0.0037(12) -0.0022(11) C12 0.0368(17) 0.0181(14) 0.0325(17) -0.0009(12) -0.0030(13) -0.0010(12) C13 0.0351(16) 0.0173(14) 0.0311(17) -0.0044(12) -0.0008(13) 0.0045(12) C14 0.0238(13) 0.0241(15) 0.0243(15) -0.0014(11) 0.0014(11) 0.0043(11) C15 0.0222(13) 0.0191(13) 0.0193(13) -0.0010(10) 0.0005(10) 0.0012(10) C16 0.0198(12) 0.0177(13) 0.0235(14) -0.0011(10) 0.0004(10) 0.0024(10) N15 0.0202(12) 0.0201(13) 0.0497(17) 0.0031(12) 0.0106(11) 0.0037(10) N12 0.0183(11) 0.0159(11) 0.0245(12) 0.0000(9) 0.0034(9) 0.0005(8) N13 0.0219(11) 0.0150(11) 0.0306(13) -0.0005(10) 0.0037(10) 0.0000(9) C17 0.0235(13) 0.0196(14) 0.0229(14) -0.0002(11) 0.0027(11) 0.0004(10) S2 0.0199(3) 0.0204(3) 0.0342(4) 0.0016(3) 0.0061(3) 0.0043(3) N14 0.0291(13) 0.0173(12) 0.0444(17) -0.0008(11) 0.0067(12) 0.0024(10) Cl3 0.0444(4) 0.0215(4) 0.0347(4) 0.0032(3) -0.0049(3) -0.0076(3) Cl4 0.0218(3) 0.0289(4) 0.0489(5) -0.0064(3) 0.0079(3) 0.0030(3) O20 0.0334(13) 0.0308(13) 0.0681(19) 0.0015(13) 0.0215(13) 0.0029(11) C21 0.059(3) 0.033(2) 0.066(3) 0.001(2) 0.022(2) 0.0047(19) O30 0.0413(15) 0.0340(14) 0.0548(18) 0.0095(12) -0.0104(13) -0.0096(12) C31 0.054(2) 0.032(2) 0.053(2) 0.0010(18) 0.0023(19) -0.0072(17) O40 0.0509(18) 0.052(2) 0.085(3) 0.0066(17) 0.0231(18) 0.0165(15) C41 0.040(2) 0.038(2) 0.061(3) 0.0092(19) 0.0069(19) 0.0040(17) O50 0.0391(14) 0.0203(12) 0.084(2) -0.0046(13) 0.0235(14) -0.0019(10) C51 0.0333(19) 0.046(2) 0.065(3) 0.007(2) 0.0053(18) -0.0028(17) _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 N2 1.972(2) . ? Au1 N1 2.067(2) . ? Au1 S1 2.2579(8) . ? Au1 Cl1 2.2801(9) . ? N1 C1 1.340(4) . ? N1 C5 1.359(4) . ? C1 C2 1.378(5) . ? C2 C3 1.363(5) . ? C3 C4 1.387(4) . ? C4 C5 1.381(4) . ? C5 C6 1.487(4) . ? C6 N5 1.311(4) . ? C6 N2 1.323(4) . ? N2 N3 1.384(3) . ? N3 C7 1.304(4) . ? C7 N4 1.341(4) . ? C7 S1 1.789(3) . ? Au2 N12 1.966(2) . ? Au2 N11 2.073(2) . ? Au2 S2 2.2637(8) . ? Au2 Cl2 2.2923(8) . ? N11 C11 1.336(4) . ? N11 C15 1.359(4) . ? C11 C12 1.380(4) . ? C12 C13 1.373(5) . ? C13 C14 1.392(4) . ? C14 C15 1.380(4) . ? C15 C16 1.476(4) . ? C16 N15 1.319(4) . ? C16 N12 1.326(4) . ? N12 N13 1.382(3) . ? N13 C17 1.304(4) . ? C17 N14 1.334(4) . ? C17 S2 1.791(3) . ? O20 C21 1.413(5) . ? O30 C31 1.406(5) . ? O40 C41 1.377(5) . ? O50 C51 1.398(4) . ? 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 Au1 N1 80.69(10) . . ? N2 Au1 S1 84.98(7) . . ? N1 Au1 S1 165.65(7) . . ? N2 Au1 Cl1 179.36(7) . . ? N1 Au1 Cl1 98.70(7) . . ? S1 Au1 Cl1 95.64(3) . . ? C1 N1 C5 120.5(3) . . ? C1 N1 Au1 127.2(2) . . ? C5 N1 Au1 112.31(18) . . ? N1 C1 C2 120.8(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C4 120.4(3) . . ? C5 C4 C3 118.4(3) . . ? N1 C5 C4 120.5(3) . . ? N1 C5 C6 115.2(2) . . ? C4 C5 C6 124.3(3) . . ? N5 C6 N2 123.2(3) . . ? N5 C6 C5 122.2(3) . . ? N2 C6 C5 114.6(3) . . ? C6 N2 N3 120.0(2) . . ? C6 N2 Au1 117.22(19) . . ? N3 N2 Au1 122.76(18) . . ? C7 N3 N2 112.9(2) . . ? N3 C7 N4 120.6(3) . . ? N3 C7 S1 124.6(2) . . ? N4 C7 S1 114.8(2) . . ? C7 S1 Au1 94.74(10) . . ? N12 Au2 N11 80.66(10) . . ? N12 Au2 S2 84.51(7) . . ? N11 Au2 S2 165.16(7) . . ? N12 Au2 Cl2 176.16(8) . . ? N11 Au2 Cl2 97.73(7) . . ? S2 Au2 Cl2 97.04(3) . . ? C11 N11 C15 121.0(3) . . ? C11 N11 Au2 126.9(2) . . ? C15 N11 Au2 112.05(19) . . ? N11 C11 C12 120.7(3) . . ? C13 C12 C11 119.2(3) . . ? C12 C13 C14 120.1(3) . . ? C15 C14 C13 118.5(3) . . ? N11 C15 C14 120.4(3) . . ? N11 C15 C16 115.1(2) . . ? C14 C15 C16 124.5(3) . . ? N15 C16 N12 122.7(3) . . ? N15 C16 C15 122.2(3) . . ? N12 C16 C15 115.1(2) . . ? C16 N12 N13 119.6(2) . . ? C16 N12 Au2 116.94(19) . . ? N13 N12 Au2 123.46(18) . . ? C17 N13 N12 112.7(2) . . ? N13 C17 N14 121.0(3) . . ? N13 C17 S2 124.2(2) . . ? N14 C17 S2 114.7(2) . . ? C17 S2 Au2 94.78(10) . . ? 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 N5 H5A O20 0.88 1.92 2.751(4) 157.7 . N5 H5B O30 0.88 1.99 2.853(4) 165.3 . N15 H15A O50 0.88 1.93 2.764(4) 157.5 . N14 H14B O40 0.88 2.04 2.880(4) 159.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.726 _refine_diff_density_min -1.255 _refine_diff_density_rms 0.133 data_auhexim _database_code_depnum_ccdc_archive 'CCDC 222001' _chemical_name_common ; Chloro(2-pyridineformamide(N-3- hexamethylene)thiosemicarbazonato)gold(iii) chloride ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Chloro{2-pyridineformamide(N-3-hexamethylene)thiosemicarbazonato}gold(III) chloride ; _chemical_melting_point ? _chemical_formula_moiety '[Au(Amhexim)Cl]Cl * MeOH' _chemical_formula_sum 'C14 H22 Au Cl2 N5 O S' _chemical_formula_weight 576.29 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' 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.594(2) _cell_length_b 9.266(1) _cell_length_c 17.738(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.91(1) _cell_angle_gamma 90.00 _cell_volume 1871.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2.8 _cell_measurement_theta_min 30.4 _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 8.272 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.5147 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'BRUKER CCD' _diffrn_measurement_method 'Omega and Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7513 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4592 _reflns_number_gt 3731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER CCD' _computing_cell_refinement 'BRUKER CCD' _computing_data_reduction SAINT _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material WINGX _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^)+(0.1192P)^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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4592 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au Au 0.42905(3) 0.38425(3) 0.085558(14) 0.02486(14) Uani 1 1 d . . . Cl1 Cl 0.4186(2) 0.1376(2) 0.07933(12) 0.0356(5) Uani 1 1 d . . . N1 N 0.5678(6) 0.4060(6) 0.1775(4) 0.0215(13) Uani 1 1 d . . . C1 C 0.6237(8) 0.3009(8) 0.2213(4) 0.0299(17) Uani 1 1 d . . . H1 H 0.6004 0.2036 0.2106 0.036 Uiso 1 1 calc R . . C2 C 0.7157(8) 0.3306(8) 0.2826(4) 0.0307(17) Uani 1 1 d . . . H2 H 0.7551 0.2556 0.3137 0.037 Uiso 1 1 calc R . . C3 C 0.7467(8) 0.4732(8) 0.2958(4) 0.035(2) Uani 1 1 d . . . H3 H 0.8104 0.4968 0.3361 0.042 Uiso 1 1 calc R . . C4 C 0.6868(8) 0.5833(8) 0.2517(4) 0.0288(18) Uani 1 1 d . . . H4 H 0.7077 0.6814 0.2621 0.035 Uiso 1 1 calc R . . C5 C 0.5966(7) 0.5467(7) 0.1928(4) 0.0226(15) Uani 1 1 d . . . C6 C 0.5271(7) 0.6523(7) 0.1402(4) 0.0230(15) Uani 1 1 d . . . N5 N 0.5469(7) 0.7924(7) 0.1445(4) 0.0367(18) Uani 1 1 d . . . H5A H 0.5039 0.8510 0.1116 0.044 Uiso 1 1 calc R . . H5B H 0.6032 0.8272 0.1802 0.044 Uiso 1 1 calc R . . N2 N 0.4444(6) 0.5947(7) 0.0882(3) 0.0248(15) Uani 1 1 d . . . N3 N 0.3755(6) 0.6830(7) 0.0343(4) 0.0325(16) Uani 1 1 d . . . C7 C 0.3020(8) 0.6144(8) -0.0167(4) 0.0296(19) Uani 1 1 d . . . S S 0.28329(19) 0.4207(2) -0.01673(11) 0.0310(5) Uani 1 1 d . . . N4 N 0.2344(6) 0.6867(7) -0.0746(3) 0.0323(15) Uani 1 1 d . . . C8 C 0.1317(9) 0.6210(8) -0.1246(4) 0.038(2) Uani 1 1 d . . . H8A H 0.1509 0.5198 -0.1352 0.045 Uiso 1 1 calc R . . H8B H 0.1165 0.6732 -0.1742 0.045 Uiso 1 1 calc R . . C9 C 0.0216(9) 0.6223(9) -0.0917(5) 0.041(2) Uani 1 1 d . . . H9A H 0.0309 0.5530 -0.0485 0.050 Uiso 1 1 calc R . . H9B H -0.0444 0.5883 -0.1315 0.050 Uiso 1 1 calc R . . C10 C -0.0103(9) 0.7705(11) -0.0628(5) 0.043(2) Uani 1 1 d . . . H10A H -0.0887 0.7640 -0.0486 0.052 Uiso 1 1 calc R . . H10B H -0.0158 0.8410 -0.1053 0.052 Uiso 1 1 calc R . . C11 C 0.0786(8) 0.8278(10) 0.0071(5) 0.037(2) Uani 1 1 d . . . H11A H 0.0361 0.8905 0.0379 0.045 Uiso 1 1 calc R . . H11B H 0.1102 0.7448 0.0397 0.045 Uiso 1 1 calc R . . C12 C 0.1815(8) 0.9128(9) -0.0131(5) 0.038(2) Uani 1 1 d . . . H12A H 0.1530 1.0096 -0.0317 0.046 Uiso 1 1 calc R . . H12B H 0.2412 0.9266 0.0343 0.046 Uiso 1 1 calc R . . C13 C 0.2402(8) 0.8425(9) -0.0734(5) 0.037(2) Uani 1 1 d . . . H13A H 0.2027 0.8794 -0.1246 0.044 Uiso 1 1 calc R . . H13B H 0.3237 0.8720 -0.0642 0.044 Uiso 1 1 calc R . . O20 O -0.0465(7) 0.5778(8) -0.2954(4) 0.0513(18) Uani 1 1 d . . . H20 H -0.1048 0.5492 -0.2777 0.077 Uiso 1 1 calc R . . Cl2 Cl 0.72046(19) 0.95892(19) 0.27474(11) 0.0357(5) Uani 1 1 d . . . C21 C -0.0593(11) 0.7283(12) -0.3135(6) 0.057(3) Uani 1 1 d . . . H21A H -0.0425 0.7849 -0.2660 0.085 Uiso 1 1 calc R . . H21B H -0.1400 0.7474 -0.3400 0.085 Uiso 1 1 calc R . . H21C H -0.0044 0.7555 -0.3467 0.085 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au 0.0298(3) 0.02229(15) 0.02052(16) 0.00037(8) -0.00019(13) -0.00159(10) Cl1 0.0428(15) 0.0227(8) 0.0396(11) -0.0008(6) 0.0033(10) -0.0049(7) N1 0.011(3) 0.031(3) 0.023(3) 0.000(2) 0.006(2) -0.001(2) C1 0.038(5) 0.026(3) 0.024(3) 0.003(2) 0.002(3) -0.001(3) C2 0.034(5) 0.026(3) 0.030(3) 0.004(3) 0.000(3) 0.005(3) C3 0.049(5) 0.026(3) 0.023(3) -0.001(3) -0.010(3) 0.001(3) C4 0.040(5) 0.023(3) 0.020(3) -0.001(2) -0.002(3) -0.001(3) C5 0.024(4) 0.026(3) 0.017(3) 0.004(2) 0.004(3) 0.002(3) C6 0.025(4) 0.024(3) 0.019(3) 0.004(2) 0.003(3) 0.005(3) N5 0.051(5) 0.022(3) 0.028(3) 0.001(2) -0.015(3) -0.002(3) N2 0.025(4) 0.031(3) 0.018(3) 0.000(2) 0.004(3) -0.003(2) N3 0.042(4) 0.026(3) 0.025(3) 0.004(2) -0.004(3) 0.005(3) C7 0.033(5) 0.033(4) 0.021(3) 0.004(2) 0.003(3) 0.001(3) S 0.0313(12) 0.0339(9) 0.0242(8) -0.0022(7) -0.0039(8) -0.0010(8) N4 0.038(4) 0.034(3) 0.021(3) 0.003(2) -0.003(3) 0.003(3) C8 0.049(6) 0.040(4) 0.017(3) -0.001(3) -0.011(4) 0.003(3) C9 0.033(6) 0.051(5) 0.035(4) 0.001(3) -0.006(4) -0.007(4) C10 0.033(5) 0.060(6) 0.032(4) -0.002(4) -0.001(4) 0.003(4) C11 0.030(5) 0.050(5) 0.033(4) -0.006(3) 0.008(4) 0.007(4) C12 0.034(5) 0.039(4) 0.039(4) -0.007(3) 0.002(4) 0.006(4) C13 0.037(5) 0.036(4) 0.033(4) 0.006(3) -0.004(4) 0.007(4) O20 0.043(5) 0.062(4) 0.047(4) -0.007(3) 0.002(3) 0.008(3) Cl2 0.0452(13) 0.0237(8) 0.0330(9) -0.0021(6) -0.0055(8) -0.0001(7) C21 0.057(7) 0.062(7) 0.048(6) 0.010(5) 0.003(5) 0.008(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au N2 1.958(7) . ? Au N1 2.073(6) . ? Au S 2.2587(18) . ? Au Cl1 2.290(2) . ? N1 C1 1.335(9) . ? N1 C5 1.360(9) . ? C1 C2 1.398(10) . ? C2 C3 1.378(11) . ? C3 C4 1.388(10) . ? C4 C5 1.374(10) . ? C5 C6 1.480(9) . ? C6 N2 1.313(9) . ? C6 N5 1.317(9) . ? N2 N3 1.389(8) . ? N3 C7 1.288(10) . ? C7 N4 1.346(9) . ? C7 S 1.808(7) . ? N4 C13 1.446(11) . ? N4 C8 1.474(10) . ? C8 C9 1.500(17) . ? C9 C10 1.535(13) . ? C10 C11 1.548(11) . ? C11 C12 1.528(14) . ? C12 C13 1.519(13) . ? O20 C21 1.432(13) . ? 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 Au N1 80.3(2) . . ? N2 Au S 85.44(19) . . ? N1 Au S 165.66(18) . . ? N2 Au Cl1 177.2(2) . . ? N1 Au Cl1 99.28(17) . . ? S Au Cl1 94.93(7) . . ? C1 N1 C5 120.7(6) . . ? C1 N1 Au 127.3(5) . . ? C5 N1 Au 112.0(4) . . ? N1 C1 C2 121.5(7) . . ? C3 C2 C1 117.2(7) . . ? C2 C3 C4 121.4(7) . . ? C5 C4 C3 118.4(7) . . ? N1 C5 C4 120.7(6) . . ? N1 C5 C6 115.1(6) . . ? C4 C5 C6 124.2(6) . . ? N2 C6 N5 122.5(6) . . ? N2 C6 C5 114.4(6) . . ? N5 C6 C5 123.2(6) . . ? C6 N2 N3 119.5(6) . . ? C6 N2 Au 118.2(5) . . ? N3 N2 Au 122.2(5) . . ? C7 N3 N2 114.2(6) . . ? N3 C7 N4 120.2(7) . . ? N3 C7 S 123.6(6) . . ? N4 C7 S 116.2(6) . . ? C7 S Au 94.4(3) . . ? C7 N4 C13 117.8(6) . . ? C7 N4 C8 122.7(7) . . ? C13 N4 C8 116.8(6) . . ? N4 C8 C9 114.3(7) . . ? C8 C9 C10 114.4(8) . . ? C9 C10 C11 114.1(8) . . ? C12 C11 C10 114.8(8) . . ? C13 C12 C11 114.7(7) . . ? N4 C13 C12 114.4(8) . . ? 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 N5 H5B Cl2 0.88 2.30 3.164(6) 167.2 . N5 H5A Cl1 0.88 2.85 3.624(7) 147.1 1_565 O20 H20 Cl2 0.84 2.39 3.199(8) 163.4 4_475 _diffrn_measured_fraction_theta_max 0.802 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.802 _refine_diff_density_max 5.019 _refine_diff_density_min -5.773 _refine_diff_density_rms 0.371 #----END