Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Zijian Guo' 'Jian Ding' 'Liping Lin' 'Qin Liu' 'Chao Tu' 'Qiang Xu' 'Ting Yang' 'Junyong Zhang' 'Xianming Zhang' _publ_contact_author_name 'Prof Zijian Guo' _publ_contact_author_address ; State Key Laboratory of Coordination Chemistry Nanjing University Hankou Road No. 22 Nanjing Jiangsu Province 210093 CHINA ; _publ_contact_author_email ZGUO@NJU.EDU.CN _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Novel Au(III) complexes of Aminoquinoline Derivatives: Crystal Structure, DNA Binding and Cytotoxicity Against Melanoma and Lung Tumor cells ; data_tt _database_code_CSD 210004 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Au Cl2 N3 O' _chemical_formula_weight 482.11 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' 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 Orthohombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.6540(10) _cell_length_b 9.262(2) _cell_length_c 22.169(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1366.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1419 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 24.97 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 11.152 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.146 _exptl_absorpt_correction_T_max 0.188 _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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 7.03 _diffrn_reflns_number 1419 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1419 _reflns_number_gt 1153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_cell_refinement XSCANS _computing_data_reduction 'SHELXTL(Sheldrick, 1997)' _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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^)+(0.2200P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(7) _refine_ls_number_reflns 1419 _refine_ls_number_parameters 167 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.2800 _refine_ls_wR_factor_gt 0.2143 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.009 _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 -0.3455(2) 0.20136(14) 1.11111(7) 0.0370(6) Uani 1 1 d . . . Cl1 Cl -0.382(2) -0.0001(11) 1.0532(6) 0.060(3) Uani 1 1 d . . . Cl2 Cl 0.1414(19) 0.2488(12) 1.0884(5) 0.050(2) Uani 1 1 d . . . O1 O -0.286(8) 0.626(3) 1.1498(18) 0.076(13) Uani 1 1 d . . . N1 N -0.2799(9) 0.107(3) 1.1909(12) 0.031(7) Uani 1 1 d D . . N2 N -0.317(5) 0.380(3) 1.1588(11) 0.029(7) Uani 1 1 d . . . N3 N -0.424(5) 0.344(3) 1.0492(12) 0.027(6) Uani 1 1 d . . . H3B H -0.3943 0.3102 1.0123 0.033 Uiso 1 1 calc R . . H3C H -0.5572 0.3601 1.0510 0.033 Uiso 1 1 calc R . . C1 C -0.261(2) -0.041(4) 1.202(2) 0.050(12) Uani 1 1 d D . . H1A H -0.2741 -0.1076 1.1708 0.060 Uiso 1 1 calc R . . C2 C -0.223(3) -0.084(6) 1.261(2) 0.050(11) Uiso 1 1 d D . . H2A H -0.2103 -0.1823 1.2691 0.060 Uiso 1 1 calc R . . C3 C -0.205(4) 0.000(6) 1.304(3) 0.076(19) Uani 1 1 d D . . H3A H -0.1795 -0.0381 1.3416 0.091 Uiso 1 1 calc R . . C4 C -0.221(3) 0.155(6) 1.299(2) 0.058(13) Uani 1 1 d D . . C5 C -0.203(4) 0.256(7) 1.343(2) 0.08(2) Uani 1 1 d D . . H5A H -0.1776 0.2304 1.3825 0.098 Uiso 1 1 calc R . . C6 C -0.228(4) 0.417(5) 1.323(2) 0.058(14) Uani 1 1 d D . . H6A H -0.2168 0.4892 1.3521 0.070 Uiso 1 1 calc R . . C7 C -0.264(4) 0.454(5) 1.2660(16) 0.055(14) Uani 1 1 d D . . H7A H -0.2782 0.5512 1.2560 0.066 Uiso 1 1 calc R . . C8 C -0.283(3) 0.345(5) 1.2191(16) 0.051(13) Uani 1 1 d D . . C9 C -0.2621(19) 0.210(4) 1.2356(16) 0.037(9) Uani 1 1 d D . . C10 C -0.300(7) 0.505(4) 1.1244(19) 0.046(11) Uani 1 1 d . . . C11 C -0.312(6) 0.485(4) 1.060(2) 0.039(9) Uani 1 1 d . . . H11A H -0.1749 0.4726 1.0447 0.047 Uiso 1 1 calc R . . C12 C -0.408(8) 0.612(6) 1.025(3) 0.071(17) Uani 1 1 d . . . H12A H -0.4063 0.5915 0.9827 0.107 Uiso 1 1 calc R . . H12B H -0.3337 0.6987 1.0329 0.107 Uiso 1 1 calc R . . H12C H -0.5447 0.6246 1.0382 0.107 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 0.0433(9) 0.0265(8) 0.0413(9) -0.0048(6) 0.0052(8) -0.0032(6) Cl1 0.079(9) 0.031(4) 0.069(7) -0.018(5) -0.001(7) 0.002(5) Cl2 0.048(6) 0.053(5) 0.049(5) -0.014(5) -0.014(5) 0.003(5) O1 0.11(3) 0.037(17) 0.08(2) -0.022(17) -0.03(2) -0.01(2) N1 0.047(18) 0.021(13) 0.025(14) 0.015(12) 0.009(13) -0.001(13) N2 0.043(18) 0.028(14) 0.016(13) 0.013(11) -0.012(14) 0.004(13) N3 0.036(16) 0.029(14) 0.016(13) -0.003(11) -0.005(12) -0.007(12) C1 0.07(3) 0.022(18) 0.06(3) 0.003(19) -0.03(3) 0.02(2) C3 0.09(5) 0.07(3) 0.07(3) 0.06(3) 0.00(3) 0.03(3) C4 0.05(3) 0.08(3) 0.05(3) -0.04(2) 0.01(2) -0.01(2) C5 0.12(6) 0.09(4) 0.04(3) -0.02(3) 0.04(3) 0.01(4) C6 0.03(2) 0.06(3) 0.08(4) 0.00(3) -0.03(2) 0.00(2) C7 0.09(4) 0.06(3) 0.008(16) -0.004(17) -0.01(2) 0.00(3) C8 0.07(3) 0.07(3) 0.012(16) -0.009(18) 0.008(18) 0.02(2) C9 0.038(19) 0.05(2) 0.028(18) 0.000(17) 0.026(17) 0.003(19) C10 0.06(3) 0.023(17) 0.05(2) 0.010(17) -0.01(2) -0.008(19) C11 0.03(2) 0.018(16) 0.06(3) -0.008(16) -0.003(19) -0.005(14) C12 0.05(3) 0.07(3) 0.09(4) 0.03(3) -0.01(3) 0.00(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 N2 1.98(3) . ? Au1 N3 1.98(3) . ? Au1 N1 2.02(3) . ? Au1 Cl1 2.278(10) . ? O1 C10 1.26(5) . ? N1 C9 1.38(5) . ? N1 C1 1.39(5) . ? N2 C8 1.40(4) . ? N2 C10 1.39(4) . ? N3 C11 1.52(4) . ? N3 H3B 0.9000 . ? N3 H3C 0.9000 . ? C1 C2 1.40(6) . ? C1 H1A 0.9300 . ? C2 C3 1.23(8) . ? C2 H2A 0.9300 . ? C3 C4 1.44(8) . ? C3 H3A 0.9300 . ? C4 C5 1.36(7) . ? C4 C9 1.51(7) . ? C5 C6 1.56(8) . ? C5 H5A 0.9300 . ? C6 C7 1.33(6) . ? C6 H6A 0.9300 . ? C7 C8 1.45(6) . ? C7 H7A 0.9300 . ? C8 C9 1.31(6) . ? C10 C11 1.44(6) . ? C11 C12 1.55(6) . ? C11 H11A 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 N2 Au1 N3 80.4(10) . . ? N2 Au1 N1 82.8(11) . . ? N3 Au1 N1 162.6(12) . . ? N2 Au1 Cl1 177.9(8) . . ? N3 Au1 Cl1 97.4(9) . . ? N1 Au1 Cl1 99.3(9) . . ? C9 N1 C1 123(3) . . ? C9 N1 Au1 110(2) . . ? C1 N1 Au1 127(3) . . ? C8 N2 C10 135(3) . . ? C8 N2 Au1 109(2) . . ? C10 N2 Au1 114(2) . . ? C11 N3 Au1 110(2) . . ? C11 N3 H3B 109.7 . . ? Au1 N3 H3B 109.7 . . ? C11 N3 H3C 109.7 . . ? Au1 N3 H3C 109.7 . . ? H3B N3 H3C 108.2 . . ? N1 C1 C2 117(4) . . ? N1 C1 H1A 121.3 . . ? C2 C1 H1A 121.3 . . ? C3 C2 C1 124(5) . . ? C3 C2 H2A 118.2 . . ? C1 C2 H2A 118.2 . . ? C2 C3 C4 125(5) . . ? C2 C3 H3A 117.7 . . ? C4 C3 H3A 117.7 . . ? C5 C4 C3 128(6) . . ? C5 C4 C9 117(5) . . ? C3 C4 C9 115(4) . . ? C4 C5 C6 117(5) . . ? C4 C5 H5A 121.7 . . ? C6 C5 H5A 121.7 . . ? C7 C6 C5 122(5) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C8 121(5) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 N2 121(4) . . ? C9 C8 C7 117(4) . . ? N2 C8 C7 122(4) . . ? C8 C9 N1 117(3) . . ? C8 C9 C4 127(4) . . ? N1 C9 C4 116(3) . . ? O1 C10 N2 120(4) . . ? O1 C10 C11 124(4) . . ? N2 C10 C11 116(3) . . ? C10 C11 N3 107(3) . . ? C10 C11 C12 115(4) . . ? N3 C11 C12 112(3) . . ? C10 C11 H11A 107.6 . . ? N3 C11 H11A 107.6 . . ? C12 C11 H11A 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Au1 N1 C9 3.3(10) . . . . ? N3 Au1 N1 C9 -12(3) . . . . ? Cl1 Au1 N1 C9 -176.4(6) . . . . ? N2 Au1 N1 C1 -178.9(12) . . . . ? N3 Au1 N1 C1 166(3) . . . . ? Cl1 Au1 N1 C1 1.4(9) . . . . ? N3 Au1 N2 C8 172(2) . . . . ? N1 Au1 N2 C8 -3.8(18) . . . . ? Cl1 Au1 N2 C8 168(26) . . . . ? N3 Au1 N2 C10 -19(3) . . . . ? N1 Au1 N2 C10 165(3) . . . . ? Cl1 Au1 N2 C10 -23(30) . . . . ? N2 Au1 N3 C11 31(2) . . . . ? N1 Au1 N3 C11 47(5) . . . . ? Cl1 Au1 N3 C11 -149(2) . . . . ? C9 N1 C1 C2 0.00(7) . . . . ? Au1 N1 C1 C2 -177.5(9) . . . . ? N1 C1 C2 C3 0.00(8) . . . . ? C1 C2 C3 C4 0.00(16) . . . . ? C2 C3 C4 C5 180.00(13) . . . . ? C2 C3 C4 C9 0.00(18) . . . . ? C3 C4 C5 C6 180.00(12) . . . . ? C9 C4 C5 C6 0.00(17) . . . . ? C4 C5 C6 C7 -0.01(19) . . . . ? C5 C6 C7 C8 0.01(19) . . . . ? C10 N2 C8 C9 -162(4) . . . . ? Au1 N2 C8 C9 4(3) . . . . ? C10 N2 C8 C7 17(5) . . . . ? Au1 N2 C8 C7 -177.3(7) . . . . ? C6 C7 C8 C9 -0.02(19) . . . . ? C6 C7 C8 N2 -179(2) . . . . ? N2 C8 C9 N1 -1(2) . . . . ? C7 C8 C9 N1 180.00(10) . . . . ? N2 C8 C9 C4 179(2) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C1 N1 C9 C8 -179.99(9) . . . . ? Au1 N1 C9 C8 -2.2(7) . . . . ? C1 N1 C9 C4 0.00(13) . . . . ? Au1 N1 C9 C4 177.8(7) . . . . ? C5 C4 C9 C8 0.0(2) . . . . ? C3 C4 C9 C8 179.99(13) . . . . ? C5 C4 C9 N1 180.00(11) . . . . ? C3 C4 C9 N1 0.00(16) . . . . ? C8 N2 C10 O1 -17(7) . . . . ? Au1 N2 C10 O1 178(4) . . . . ? C8 N2 C10 C11 167(4) . . . . ? Au1 N2 C10 C11 2(5) . . . . ? O1 C10 C11 N3 -153(5) . . . . ? N2 C10 C11 N3 23(5) . . . . ? O1 C10 C11 C12 -28(7) . . . . ? N2 C10 C11 C12 147(4) . . . . ? Au1 N3 C11 C10 -37(4) . . . . ? Au1 N3 C11 C12 -164(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.635 _refine_diff_density_min -2.915 _refine_diff_density_rms 0.517 data_tt_2 _database_code_CSD 210005 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Au Cl2 N3 O' _chemical_formula_weight 468.09 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' 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)/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 6.5239(9) _cell_length_b 19.001(3) _cell_length_c 10.1653(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.855(3) _cell_angle_gamma 90.00 _cell_volume 1260.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7202 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 27.06 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 12.089 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.244 _exptl_absorpt_correction_T_max 0.299 _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 '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 7202 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.06 _reflns_number_total 2735 _reflns_number_gt 1919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0240P)^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 2735 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.827 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.28558(5) 1.087272(16) 0.83570(3) 0.03054(11) Uani 1 1 d . . . Cl1 Cl 0.2949(4) 1.07157(13) 1.0578(2) 0.0490(6) Uani 1 1 d . . . Cl2 Cl 1.1619(3) 0.82756(11) 0.1407(2) 0.0439(5) Uani 1 1 d . . . O1 O 0.2833(10) 1.1899(3) 0.4904(6) 0.0508(17) Uani 1 1 d . . . N1 N 0.2335(9) 0.9861(3) 0.7812(6) 0.0285(15) Uani 1 1 d . . . N2 N 0.2808(9) 1.1043(3) 0.6462(6) 0.0277(15) Uani 1 1 d . . . N3 N 0.3633(10) 1.1903(3) 0.8437(7) 0.0376(17) Uani 1 1 d . . . H3B H 0.2926 1.2118 0.9076 0.045 Uiso 1 1 calc R . . H3C H 0.4979 1.1945 0.8629 0.045 Uiso 1 1 calc R . . C1 C 0.2090(12) 0.9317(4) 0.8542(8) 0.036(2) Uani 1 1 d . . . H1A H 0.2059 0.9373 0.9450 0.044 Uiso 1 1 calc R . . C2 C 0.1869(14) 0.8642(4) 0.8011(10) 0.045(2) Uani 1 1 d . . . H2A H 0.1686 0.8257 0.8562 0.054 Uiso 1 1 calc R . . C3 C 0.1925(12) 0.8552(5) 0.6679(10) 0.045(2) Uani 1 1 d . . . H3A H 0.1780 0.8104 0.6317 0.054 Uiso 1 1 calc R . . C4 C 0.2207(11) 0.9150(4) 0.5839(8) 0.0342(19) Uani 1 1 d . . . C5 C 0.2273(11) 0.9119(5) 0.4467(8) 0.036(2) Uani 1 1 d . . . H5A H 0.2189 0.8686 0.4044 0.044 Uiso 1 1 calc R . . C6 C 0.2457(11) 0.9710(4) 0.3755(9) 0.035(2) Uani 1 1 d . . . H6A H 0.2450 0.9679 0.2842 0.042 Uiso 1 1 calc R . . C7 C 0.2656(11) 1.0358(4) 0.4341(8) 0.0321(19) Uani 1 1 d . . . H7A H 0.2818 1.0758 0.3826 0.039 Uiso 1 1 calc R . . C8 C 0.2614(11) 1.0414(4) 0.5694(8) 0.0267(17) Uani 1 1 d . . . C9 C 0.2386(11) 0.9819(4) 0.6445(7) 0.0293(18) Uani 1 1 d . . . C10 C 0.2934(12) 1.1710(4) 0.6044(9) 0.035(2) Uani 1 1 d . . . C11 C 0.3174(14) 1.2238(4) 0.7168(8) 0.044(2) Uani 1 1 d . . . H11A H 0.4269 1.2563 0.6962 0.052 Uiso 1 1 calc R . . H11B H 0.1918 1.2507 0.7239 0.052 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 0.03093(17) 0.03102(18) 0.02971(17) -0.00045(17) 0.00123(12) 0.00222(15) Cl1 0.0527(14) 0.0647(16) 0.0297(11) 0.0026(11) 0.0004(10) 0.0061(11) Cl2 0.0477(13) 0.0400(13) 0.0439(13) -0.0004(10) -0.0002(11) 0.0010(10) O1 0.084(5) 0.027(3) 0.041(4) 0.010(3) -0.003(4) -0.005(3) N1 0.028(4) 0.018(3) 0.040(4) 0.002(3) 0.001(3) -0.003(3) N2 0.027(3) 0.024(4) 0.033(4) 0.005(3) 0.008(3) 0.004(2) N3 0.042(4) 0.030(4) 0.040(4) -0.004(3) 0.000(3) 0.002(3) C1 0.036(5) 0.040(5) 0.033(5) 0.005(4) -0.006(4) 0.002(4) C2 0.052(6) 0.027(5) 0.056(6) 0.012(5) 0.005(5) 0.003(4) C3 0.037(5) 0.032(5) 0.066(7) -0.003(5) 0.003(5) 0.002(4) C4 0.021(4) 0.032(4) 0.049(5) 0.004(5) 0.002(4) 0.005(4) C5 0.027(4) 0.034(5) 0.048(5) -0.020(5) -0.004(4) 0.003(4) C6 0.026(4) 0.038(5) 0.040(5) -0.002(4) -0.001(4) 0.005(3) C7 0.029(4) 0.035(5) 0.033(5) 0.001(4) 0.006(4) 0.004(3) C8 0.020(4) 0.032(5) 0.028(4) -0.006(4) -0.001(3) 0.000(3) C9 0.021(4) 0.038(5) 0.029(5) -0.002(4) 0.005(3) 0.002(3) C10 0.034(5) 0.020(4) 0.052(6) -0.005(4) 0.004(4) 0.002(3) C11 0.059(6) 0.025(5) 0.047(6) -0.007(4) 0.001(5) -0.002(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 N2 1.953(6) . ? Au1 N3 2.024(6) . ? Au1 N1 2.027(6) . ? Au1 Cl1 2.277(2) . ? O1 C10 1.215(10) . ? N1 C1 1.284(9) . ? N1 C9 1.393(9) . ? N2 C10 1.339(9) . ? N2 C8 1.431(9) . ? N3 C11 1.466(10) . ? N3 H3B 0.9000 . ? N3 H3C 0.9000 . ? C1 C2 1.398(12) . ? C1 H1A 0.9300 . ? C2 C3 1.366(12) . ? C2 H2A 0.9300 . ? C3 C4 1.435(11) . ? C3 H3A 0.9300 . ? C4 C5 1.397(11) . ? C4 C9 1.416(11) . ? C5 C6 1.341(11) . ? C5 H5A 0.9300 . ? C6 C7 1.373(10) . ? C6 H6A 0.9300 . ? C7 C8 1.381(10) . ? C7 H7A 0.9300 . ? C8 C9 1.375(10) . ? C10 C11 1.527(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Au1 N3 83.1(3) . . ? N2 Au1 N1 83.5(3) . . ? N3 Au1 N1 165.7(3) . . ? N2 Au1 Cl1 177.92(19) . . ? N3 Au1 Cl1 94.8(2) . . ? N1 Au1 Cl1 98.6(2) . . ? C1 N1 C9 122.3(7) . . ? C1 N1 Au1 128.8(6) . . ? C9 N1 Au1 108.8(5) . . ? C10 N2 C8 128.5(7) . . ? C10 N2 Au1 118.0(6) . . ? C8 N2 Au1 113.6(5) . . ? C11 N3 Au1 109.7(5) . . ? C11 N3 H3B 109.7 . . ? Au1 N3 H3B 109.7 . . ? C11 N3 H3C 109.7 . . ? Au1 N3 H3C 109.7 . . ? H3B N3 H3C 108.2 . . ? N1 C1 C2 121.9(8) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 119.6(8) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 119.7(8) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C9 117.9(8) . . ? C5 C4 C3 124.5(8) . . ? C9 C4 C3 117.6(8) . . ? C6 C5 C4 120.6(8) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 121.6(8) . . ? C5 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C6 C7 C8 119.9(8) . . ? C6 C7 H7A 120.0 . . ? C8 C7 H7A 120.0 . . ? C7 C8 C9 119.6(7) . . ? C7 C8 N2 127.2(7) . . ? C9 C8 N2 113.2(6) . . ? C8 C9 N1 120.7(7) . . ? C8 C9 C4 120.4(7) . . ? N1 C9 C4 118.9(7) . . ? O1 C10 N2 125.5(8) . . ? O1 C10 C11 121.5(7) . . ? N2 C10 C11 113.0(8) . . ? N3 C11 C10 113.0(7) . . ? N3 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? N3 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Au1 N1 C1 -178.7(7) . . . . ? N3 Au1 N1 C1 160.2(9) . . . . ? Cl1 Au1 N1 C1 1.6(7) . . . . ? N2 Au1 N1 C9 4.6(5) . . . . ? N3 Au1 N1 C9 -16.4(13) . . . . ? Cl1 Au1 N1 C9 -175.1(4) . . . . ? N3 Au1 N2 C10 -10.2(5) . . . . ? N1 Au1 N2 C10 174.9(6) . . . . ? Cl1 Au1 N2 C10 -13(5) . . . . ? N3 Au1 N2 C8 170.4(5) . . . . ? N1 Au1 N2 C8 -4.5(5) . . . . ? Cl1 Au1 N2 C8 168(5) . . . . ? N2 Au1 N3 C11 15.7(5) . . . . ? N1 Au1 N3 C11 36.8(13) . . . . ? Cl1 Au1 N3 C11 -164.4(5) . . . . ? C9 N1 C1 C2 0.4(12) . . . . ? Au1 N1 C1 C2 -175.9(6) . . . . ? N1 C1 C2 C3 0.4(13) . . . . ? C1 C2 C3 C4 0.0(12) . . . . ? C2 C3 C4 C5 -179.5(8) . . . . ? C2 C3 C4 C9 -1.0(11) . . . . ? C9 C4 C5 C6 -1.4(11) . . . . ? C3 C4 C5 C6 177.2(7) . . . . ? C4 C5 C6 C7 2.2(12) . . . . ? C5 C6 C7 C8 -1.7(12) . . . . ? C6 C7 C8 C9 0.4(11) . . . . ? C6 C7 C8 N2 179.7(7) . . . . ? C10 N2 C8 C7 4.8(12) . . . . ? Au1 N2 C8 C7 -175.9(6) . . . . ? C10 N2 C8 C9 -175.9(7) . . . . ? Au1 N2 C8 C9 3.4(7) . . . . ? C7 C8 C9 N1 -179.9(7) . . . . ? N2 C8 C9 N1 0.7(10) . . . . ? C7 C8 C9 C4 0.4(11) . . . . ? N2 C8 C9 C4 -179.0(6) . . . . ? C1 N1 C9 C8 178.8(7) . . . . ? Au1 N1 C9 C8 -4.2(8) . . . . ? C1 N1 C9 C4 -1.4(11) . . . . ? Au1 N1 C9 C4 175.5(5) . . . . ? C5 C4 C9 C8 0.1(10) . . . . ? C3 C4 C9 C8 -178.6(7) . . . . ? C5 C4 C9 N1 -179.7(6) . . . . ? C3 C4 C9 N1 1.7(10) . . . . ? C8 N2 C10 O1 2.7(13) . . . . ? Au1 N2 C10 O1 -176.6(7) . . . . ? C8 N2 C10 C11 -178.8(7) . . . . ? Au1 N2 C10 C11 2.0(9) . . . . ? Au1 N3 C11 C10 -18.8(9) . . . . ? O1 C10 C11 N3 -169.7(8) . . . . ? N2 C10 C11 N3 11.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.711 _refine_diff_density_min -1.138 _refine_diff_density_rms 0.195