# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ag _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Ag F12 N6 P2' _chemical_formula_weight 788.25 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 '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/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 3.8994(4) _cell_length_b 15.6005(15) _cell_length_c 21.254(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.240(2) _cell_angle_gamma 90.00 _cell_volume 1290.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 270 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.028 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 778 _exptl_absorpt_coefficient_mu 1.023 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11831 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_unetI/netI 0.0288 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2285 _reflns_number_gt 1945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.1239P)^2^+16.0692P] 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 2285 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2202 _refine_ls_wR_factor_gt 0.2130 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Ag1 Ag 0.5000 0.5000 0.0000 0.0203(3) Uani 1 2 d S . . P1 P 0.1457(9) 0.0541(2) 0.1231(2) 0.0674(10) Uani 1 1 d . . . N1 N 0.1136(16) 0.6369(4) 0.0769(3) 0.0200(13) Uani 1 1 d . . . N2 N 0.2481(16) 0.5291(4) 0.1341(3) 0.0185(13) Uani 1 1 d . . . C7 C 0.2649(19) 0.5584(5) 0.0747(4) 0.0206(15) Uani 1 1 d . . . N3 N 0.3742(18) 0.3858(4) 0.1131(3) 0.0245(14) Uani 1 1 d . . . C8 C 0.3857(19) 0.4479(5) 0.1554(3) 0.0192(15) Uani 1 1 d . . . C10 C 0.642(2) 0.3605(6) 0.2347(4) 0.0273(18) Uani 1 1 d . . . H10 H 0.7312 0.3521 0.2758 0.033 Uiso 1 1 calc R . . C1 C 0.055(2) 0.6942(5) 0.0275(4) 0.0245(16) Uani 1 1 d . . . H1 H 0.1233 0.6808 -0.0125 0.029 Uiso 1 1 calc R . . C6 C 0.0955(19) 0.5867(5) 0.1734(4) 0.0220(16) Uani 1 1 d . . . H6 H 0.0618 0.5798 0.2161 0.026 Uiso 1 1 calc R . . C5 C 0.0049(19) 0.6555(5) 0.1367(4) 0.0210(16) Uani 1 1 d . . . C9 C 0.512(2) 0.4395(5) 0.2167(4) 0.0255(17) Uani 1 1 d . . . H9 H 0.5099 0.4851 0.2449 0.031 Uiso 1 1 calc R . . C11 C 0.640(2) 0.2949(5) 0.1925(4) 0.0294(18) Uani 1 1 d . . . H11 H 0.7296 0.2415 0.2039 0.035 Uiso 1 1 calc R . . C12 C 0.502(2) 0.3098(5) 0.1324(4) 0.0302(19) Uani 1 1 d . . . H12 H 0.4973 0.2648 0.1037 0.036 Uiso 1 1 calc R . . C2 C -0.101(2) 0.7687(5) 0.0378(4) 0.0304(19) Uani 1 1 d . . . H2 H -0.1384 0.8070 0.0046 0.037 Uiso 1 1 calc R . . C3 C -0.211(2) 0.7910(6) 0.0991(5) 0.033(2) Uani 1 1 d . . . H3 H -0.3155 0.8437 0.1053 0.040 Uiso 1 1 calc R . . C4 C -0.164(2) 0.7356(5) 0.1480(4) 0.0260(17) Uani 1 1 d . . . H4 H -0.2386 0.7490 0.1876 0.031 Uiso 1 1 calc R . . F6 F 0.220(2) 0.1055(4) 0.1832(3) 0.072(2) Uani 1 1 d . . . F1 F -0.123(3) 0.0016(6) 0.1598(6) 0.094(3) Uani 1 1 d . . . F2 F 0.049(4) 0.0041(6) 0.0644(6) 0.108(4) Uani 1 1 d . . . F3 F 0.426(3) -0.0171(6) 0.1383(5) 0.091(3) Uani 1 1 d . . . F4 F 0.415(3) 0.1030(7) 0.0821(5) 0.101(3) Uani 1 1 d . . . F5 F -0.141(3) 0.1231(7) 0.1030(5) 0.099(3) 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 Ag1 0.0251(5) 0.0182(5) 0.0178(5) -0.0031(3) 0.0027(3) 0.0011(3) P1 0.057(2) 0.063(2) 0.083(3) 0.0195(19) 0.0050(17) 0.0028(16) N1 0.020(3) 0.016(3) 0.023(3) -0.004(2) -0.001(2) 0.000(2) N2 0.024(3) 0.016(3) 0.015(3) -0.005(2) 0.002(2) -0.005(3) C7 0.021(4) 0.019(4) 0.022(4) -0.003(3) -0.001(3) -0.003(3) N3 0.032(4) 0.018(3) 0.024(3) 0.002(3) 0.001(3) 0.001(3) C8 0.023(4) 0.013(4) 0.021(4) -0.001(3) 0.004(3) -0.002(3) C10 0.023(4) 0.032(5) 0.026(4) 0.006(3) 0.001(3) -0.003(3) C1 0.026(4) 0.024(4) 0.023(4) 0.000(3) -0.001(3) -0.003(3) C6 0.022(4) 0.024(4) 0.020(4) -0.006(3) 0.007(3) -0.003(3) C5 0.018(3) 0.019(4) 0.026(4) -0.009(3) 0.003(3) -0.004(3) C9 0.029(4) 0.025(4) 0.023(4) -0.001(3) 0.004(3) -0.005(3) C11 0.029(4) 0.017(4) 0.042(5) 0.007(4) 0.004(4) 0.000(3) C12 0.038(5) 0.020(4) 0.033(5) 0.000(3) 0.008(4) -0.001(3) C2 0.034(4) 0.020(4) 0.037(5) 0.000(3) -0.006(4) 0.000(3) C3 0.024(4) 0.027(4) 0.048(5) -0.009(4) -0.002(4) 0.005(3) C4 0.025(4) 0.023(4) 0.029(4) -0.009(3) 0.004(3) -0.003(3) F6 0.127(7) 0.045(4) 0.042(4) 0.006(3) -0.001(4) -0.002(4) F1 0.095(7) 0.094(8) 0.093(7) 0.007(5) 0.018(6) -0.006(5) F2 0.149(11) 0.095(8) 0.086(7) -0.003(5) 0.061(7) 0.028(6) F3 0.110(8) 0.080(6) 0.082(6) 0.010(5) 0.013(6) 0.020(5) F4 0.092(7) 0.104(7) 0.108(7) 0.021(6) 0.017(6) 0.003(6) F5 0.095(7) 0.096(7) 0.107(7) 0.007(6) 0.008(5) 0.017(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 Ag1 C7 2.086(7) . ? Ag1 C7 2.086(7) 3_665 ? P1 F2 1.502(13) . ? P1 F6 1.520(8) . ? P1 F1 1.571(11) . ? P1 F3 1.580(10) . ? P1 F5 1.593(10) . ? P1 F4 1.597(10) . ? N1 C7 1.362(10) . ? N1 C1 1.388(10) . ? N1 C5 1.394(10) . ? N2 C7 1.348(10) . ? N2 C6 1.383(10) . ? N2 C8 1.439(10) . ? N3 C8 1.322(10) . ? N3 C12 1.341(11) . ? C8 C9 1.373(11) . ? C10 C11 1.361(13) . ? C10 C9 1.378(12) . ? C10 H10 0.9300 . ? C1 C2 1.334(12) . ? C1 H1 0.9300 . ? C6 C5 1.361(12) . ? C6 H6 0.9300 . ? C5 C4 1.439(11) . ? C9 H9 0.9300 . ? C11 C12 1.378(13) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C2 C3 1.438(13) . ? C2 H2 0.9300 . ? C3 C4 1.356(13) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? 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 C7 Ag1 C7 180.0(3) . 3_665 ? F2 P1 F6 176.4(7) . . ? F2 P1 F1 89.8(6) . . ? F6 P1 F1 87.7(6) . . ? F2 P1 F3 86.7(6) . . ? F6 P1 F3 95.9(5) . . ? F1 P1 F3 90.3(6) . . ? F2 P1 F5 89.3(6) . . ? F6 P1 F5 88.1(5) . . ? F1 P1 F5 90.4(6) . . ? F3 P1 F5 176.0(6) . . ? F2 P1 F4 86.4(6) . . ? F6 P1 F4 96.2(6) . . ? F1 P1 F4 176.1(7) . . ? F3 P1 F4 88.8(6) . . ? F5 P1 F4 90.2(6) . . ? C7 N1 C1 127.3(7) . . ? C7 N1 C5 111.9(6) . . ? C1 N1 C5 120.7(7) . . ? C7 N2 C6 113.0(7) . . ? C7 N2 C8 123.8(6) . . ? C6 N2 C8 123.2(6) . . ? N2 C7 N1 103.2(6) . . ? N2 C7 Ag1 127.7(6) . . ? N1 C7 Ag1 129.0(6) . . ? C8 N3 C12 116.3(7) . . ? N3 C8 C9 124.9(7) . . ? N3 C8 N2 115.7(7) . . ? C9 C8 N2 119.4(7) . . ? C11 C10 C9 120.1(8) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C2 C1 N1 119.6(8) . . ? C2 C1 H1 120.2 . . ? N1 C1 H1 120.2 . . ? C5 C6 N2 105.9(7) . . ? C5 C6 H6 127.1 . . ? N2 C6 H6 127.1 . . ? C6 C5 N1 106.0(6) . . ? C6 C5 C4 134.1(7) . . ? N1 C5 C4 119.9(7) . . ? C8 C9 C10 117.1(7) . . ? C8 C9 H9 121.4 . . ? C10 C9 H9 121.4 . . ? C10 C11 C12 118.2(8) . . ? C10 C11 H11 120.9 . . ? C12 C11 H11 120.9 . . ? N3 C12 C11 123.5(8) . . ? N3 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? C1 C2 C3 121.5(8) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 120.4(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 118.0(8) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.293 _refine_diff_density_min -1.635 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 910111' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t1aucl3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 Au Cl3 N3' _chemical_formula_weight 498.54 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' 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 7.8238(18) _cell_length_b 9.795(2) _cell_length_c 10.093(2) _cell_angle_alpha 112.116(5) _cell_angle_beta 95.677(5) _cell_angle_gamma 97.329(6) _cell_volume 701.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1720 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 11.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.17 _exptl_absorpt_correction_T_max 0.37 _exptl_absorpt_process_details ;SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.1098 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.4355. The \l/2 correction factor is 0.0015 ; _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 'BRUKER SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6447 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_unetI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2463 _reflns_number_gt 2114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0547P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2463 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 0.79089(5) 0.30497(4) 0.84434(4) 0.03654(17) Uani 1 1 d . . . Cl2 Cl 1.0844(3) 0.3087(3) 0.8894(3) 0.0489(6) Uani 1 1 d . . . Cl1 Cl 0.8333(4) 0.4456(3) 0.7082(3) 0.0602(8) Uani 1 1 d . . . Cl3 Cl 0.4959(4) 0.3009(3) 0.8130(4) 0.0671(8) Uani 1 1 d . . . C6 C 0.7303(13) -0.0235(11) 1.0162(11) 0.045(2) Uani 1 1 d . . . H6 H 0.7325 -0.1201 1.0111 0.054 Uiso 1 1 calc R . . C9 C 0.8729(13) -0.1858(10) 0.7496(11) 0.040(2) Uani 1 1 d . . . H9 H 0.8919 -0.2197 0.8235 0.048 Uiso 1 1 calc R . . C10 C 0.9094(15) -0.2628(12) 0.6120(13) 0.054(3) Uani 1 1 d . . . H10 H 0.9568 -0.3495 0.5923 0.065 Uiso 1 1 calc R . . C11 C 0.8757(16) -0.2114(12) 0.5055(13) 0.059(3) Uani 1 1 d . . . H11 H 0.8969 -0.2628 0.4121 0.070 Uiso 1 1 calc R . . N1 N 0.7031(10) 0.2149(9) 1.0867(8) 0.0381(18) Uani 1 1 d . . . N2 N 0.7676(10) 0.0308(8) 0.9122(8) 0.0356(17) Uani 1 1 d . . . C8 C 0.8075(12) -0.0575(10) 0.7710(10) 0.037(2) Uani 1 1 d . . . C7 C 0.7525(12) 0.1767(10) 0.9573(11) 0.035(2) Uani 1 1 d . . . N3 N 0.7745(12) -0.0036(9) 0.6728(9) 0.048(2) Uani 1 1 d . . . C4 C 0.6357(14) 0.1115(13) 1.2634(11) 0.048(3) Uani 1 1 d . . . H4 H 0.6239 0.0320 1.2929 0.057 Uiso 1 1 calc R . . C5 C 0.6896(13) 0.0921(11) 1.1275(11) 0.043(2) Uani 1 1 d . . . C3 C 0.6023(15) 0.2435(13) 1.3478(13) 0.056(3) Uani 1 1 d . . . H3 H 0.5675 0.2563 1.4366 0.068 Uiso 1 1 calc R . . C12 C 0.8089(16) -0.0805(13) 0.5414(12) 0.057(3) Uani 1 1 d . . . H12 H 0.7869 -0.0441 0.4698 0.068 Uiso 1 1 calc R . . C1 C 0.6697(16) 0.3535(12) 1.1773(13) 0.058(3) Uani 1 1 d . . . H1 H 0.6820 0.4349 1.1505 0.070 Uiso 1 1 calc R . . C2 C 0.6197(16) 0.3658(14) 1.3027(14) 0.066(3) Uani 1 1 d . . . H2 H 0.5953 0.4571 1.3632 0.079 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 0.0400(3) 0.0314(2) 0.0398(3) 0.01575(17) 0.00355(16) 0.00878(16) Cl2 0.0386(14) 0.0549(15) 0.0572(16) 0.0266(13) 0.0070(12) 0.0084(11) Cl1 0.089(2) 0.0486(15) 0.0531(16) 0.0310(13) 0.0091(15) 0.0154(15) Cl3 0.0456(16) 0.0589(17) 0.099(2) 0.0337(17) 0.0017(16) 0.0160(13) C6 0.046(6) 0.040(6) 0.050(6) 0.025(5) -0.008(5) -0.001(5) C9 0.043(6) 0.036(5) 0.044(6) 0.018(4) 0.007(5) 0.011(4) C10 0.049(7) 0.046(6) 0.068(8) 0.019(6) 0.020(6) 0.018(5) C11 0.075(8) 0.050(7) 0.049(7) 0.015(5) 0.024(6) 0.009(6) N1 0.035(4) 0.042(4) 0.038(5) 0.018(4) 0.002(4) 0.006(4) N2 0.039(4) 0.035(4) 0.035(4) 0.018(3) -0.001(3) 0.006(3) C8 0.035(5) 0.034(5) 0.038(5) 0.012(4) 0.001(4) 0.000(4) C7 0.027(5) 0.035(5) 0.045(6) 0.019(4) 0.005(4) 0.009(4) N3 0.061(6) 0.040(5) 0.046(5) 0.021(4) 0.007(4) 0.013(4) C4 0.042(6) 0.065(7) 0.040(6) 0.028(5) 0.004(5) 0.000(5) C5 0.043(6) 0.045(6) 0.040(6) 0.021(5) -0.003(5) 0.001(5) C3 0.056(7) 0.063(8) 0.047(6) 0.018(6) 0.016(6) 0.002(6) C12 0.073(8) 0.054(7) 0.045(6) 0.024(5) 0.007(6) 0.009(6) C1 0.064(8) 0.042(6) 0.063(8) 0.013(5) 0.014(6) 0.008(5) C2 0.057(8) 0.060(8) 0.064(8) 0.003(6) 0.021(6) 0.008(6) _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 C7 2.005(9) . ? Au1 Cl2 2.289(3) . ? Au1 Cl3 2.292(3) . ? Au1 Cl1 2.301(3) . ? C6 C5 1.360(15) . ? C6 N2 1.383(12) . ? C6 H6 0.9300 . ? C9 C8 1.367(13) . ? C9 C10 1.388(14) . ? C9 H9 0.9300 . ? C10 C11 1.365(16) . ? C10 H10 0.9300 . ? C11 C12 1.381(15) . ? C11 H11 0.9300 . ? N1 C7 1.328(12) . ? N1 C1 1.397(13) . ? N1 C5 1.407(12) . ? N2 C7 1.352(12) . ? N2 C8 1.451(12) . ? C8 N3 1.306(12) . ? N3 C12 1.331(13) . ? C4 C3 1.329(15) . ? C4 C5 1.426(14) . ? C4 H4 0.9300 . ? C3 C2 1.430(17) . ? C3 H3 0.9300 . ? C12 H12 0.9300 . ? C1 C2 1.328(16) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? 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 C7 Au1 Cl2 88.7(3) . . ? C7 Au1 Cl3 88.4(3) . . ? Cl2 Au1 Cl3 176.45(10) . . ? C7 Au1 Cl1 178.2(3) . . ? Cl2 Au1 Cl1 91.50(11) . . ? Cl3 Au1 Cl1 91.52(12) . . ? C5 C6 N2 106.5(9) . . ? C5 C6 H6 126.8 . . ? N2 C6 H6 126.8 . . ? C8 C9 C10 116.5(9) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C11 C10 C9 120.0(10) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 117.6(10) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C7 N1 C1 128.5(9) . . ? C7 N1 C5 109.9(8) . . ? C1 N1 C5 121.5(8) . . ? C7 N2 C6 110.3(8) . . ? C7 N2 C8 124.4(7) . . ? C6 N2 C8 125.2(8) . . ? N3 C8 C9 125.6(9) . . ? N3 C8 N2 114.3(8) . . ? C9 C8 N2 120.1(8) . . ? N1 C7 N2 106.8(8) . . ? N1 C7 Au1 127.6(7) . . ? N2 C7 Au1 125.6(7) . . ? C8 N3 C12 116.6(9) . . ? C3 C4 C5 119.9(10) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 N1 106.4(8) . . ? C6 C5 C4 135.5(10) . . ? N1 C5 C4 118.0(9) . . ? C4 C3 C2 120.2(10) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N3 C12 C11 123.6(10) . . ? N3 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? C2 C1 N1 118.1(11) . . ? C2 C1 H1 120.9 . . ? N1 C1 H1 120.9 . . ? C1 C2 C3 122.2(11) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.884 _refine_diff_density_min -2.002 _refine_diff_density_rms 0.238 _database_code_depnum_ccdc_archive 'CCDC 900036'