# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Lacroix, P.G.' 'Munoz, M.' 'Gaspar, Ana' 'Real, Jose' 'Bonhommeau, Sebastien' 'Rodriguez, Vincent' 'Nakatani, Keitaro' _publ_contact_author_name 'Lacroix, P.G.' _publ_contact_author_email pascal@lcc-toulouse.fr _publ_section_title ; Synthesis, Crystal Structures, and Solid State Quadratic Nonlinear Optical Properties of a Series of Stilbazolium Cations Combined with Gold Cyanide Counter-Ion ; # Attachment '- DEASHAu(CN)2.txt' # #Synthesis, Crystal Structures, and Solid State Quadratic Nonlinear Optical #Properties of a Serie of Stilbazolium Cations Combined with Gold Cyanide #Counter-Ion #Pascal G. Lacroix, M. Carmen Munoz, Ana Belen Gaspar, Jose Antonio Real, #Vincent Rodriguez, Sebastien Bonhommeau, and Keitaro Nakatani # data_DEASAu(CN)2 _database_code_depnum_ccdc_archive 'CCDC 826266' #TrackingRef '- DEASHAu(CN)2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Au N4' _chemical_formula_weight 502.36 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' 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 Cc 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' _cell_length_a 25.7310(16) _cell_length_b 8.0720(7) _cell_length_c 18.4110(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.441(3) _cell_angle_gamma 90.00 _cell_volume 3667.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 8.029 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7463 _exptl_absorpt_correction_T_max 0.8924 _exptl_absorpt_process_details 'Empirical absorption correction:XABS2' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5288 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0849 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 24.37 _reflns_number_total 5285 _reflns_number_gt 3520 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO and SCALEPACK' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0291P)^2^+29.5342P] 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 0.07(4) _refine_ls_number_reflns 5285 _refine_ls_number_parameters 434 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.005 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 0.51150(3) 0.31061(9) 0.49933(4) 0.0732(2) Uani 1 1 d . . . Au2 Au 0.12417(3) 0.91752(8) 0.42590(4) 0.0743(3) Uani 1 1 d D . . N1 N 0.4123(12) 0.291(3) 0.3570(15) 0.094(10) Uani 1 1 d . . . N3 N 0.2160(9) 0.949(3) 0.5767(11) 0.093(9) Uani 1 1 d D . . N4 N 0.0277(9) 0.899(3) 0.2820(15) 0.098(10) Uani 1 1 d D . . N5 N 0.4268(10) 0.631(3) 0.6818(12) 0.088(6) Uani 1 1 d . . . N6 N 0.1517(7) 0.6052(19) 0.1184(11) 0.068(5) Uani 1 1 d . . . N7 N 0.2122(8) 0.900(2) -0.2553(10) 0.066(5) Uani 1 1 d . . . N8 N 0.4787(9) 0.829(2) 0.3098(11) 0.089(6) Uani 1 1 d . . . C1 C 0.4536(13) 0.291(4) 0.4064(18) 0.108(15) Uani 1 1 d . . . C3 C 0.1835(9) 0.926(2) 0.5168(11) 0.058(9) Uani 1 1 d D . . C4 C 0.0686(10) 0.892(5) 0.3330(11) 0.120(16) Uani 1 1 d D . . C5 C 0.3800(13) 0.718(3) 0.6697(17) 0.078(8) Uani 1 1 d . . . H5 H 0.3744 0.7779 0.7100 0.083(8) Uiso 1 1 calc R . . C6 C 0.3413(10) 0.722(3) 0.6039(14) 0.082(7) Uani 1 1 d . . . H6 H 0.3092 0.7795 0.5992 0.083(8) Uiso 1 1 calc R . . C7 C 0.3503(9) 0.638(3) 0.5421(12) 0.062(6) Uani 1 1 d . . . C8 C 0.3965(10) 0.545(2) 0.5548(15) 0.076(6) Uani 1 1 d . . . H8 H 0.4018 0.4820 0.5151 0.083(8) Uiso 1 1 calc R . . C9 C 0.4363(12) 0.540(3) 0.6252(19) 0.083(8) Uani 1 1 d . . . H9 H 0.4678 0.4780 0.6324 0.083(8) Uiso 1 1 calc R . . C10 C 0.3057(11) 0.650(4) 0.4705(16) 0.083(8) Uani 1 1 d . . . H10 H 0.2748 0.7100 0.4702 0.083(8) Uiso 1 1 calc R . . C11 C 0.3085(10) 0.577(2) 0.4066(15) 0.065(7) Uani 1 1 d . . . H11 H 0.3395 0.5150 0.4092 0.083(8) Uiso 1 1 calc R . . C12 C 0.2664(9) 0.586(2) 0.3308(13) 0.064(6) Uani 1 1 d . . . C13 C 0.2164(10) 0.6750(19) 0.3196(14) 0.055(7) Uani 1 1 d . . . H13 H 0.2083 0.7281 0.3598 0.083(8) Uiso 1 1 calc R . . C14 C 0.1817(11) 0.680(2) 0.2495(15) 0.076(8) Uani 1 1 d . . . H14 H 0.1506 0.7434 0.2430 0.083(8) Uiso 1 1 calc R . . C15 C 0.1881(11) 0.597(2) 0.1847(14) 0.067(6) Uani 1 1 d . . . C16 C 0.2370(9) 0.507(2) 0.2000(13) 0.064(5) Uani 1 1 d . . . H16 H 0.2438 0.4468 0.1606 0.083(8) Uiso 1 1 calc R . . C17 C 0.2743(10) 0.502(3) 0.2679(15) 0.066(7) Uani 1 1 d . . . H17 H 0.3060 0.4413 0.2734 0.083(8) Uiso 1 1 calc R . . C18 C 0.1083(10) 0.723(3) 0.0996(17) 0.085(8) Uani 1 1 d . . . H18A H 0.1025 0.7566 0.0473 0.083(8) Uiso 1 1 calc R . . H18B H 0.1196 0.8209 0.1308 0.083(8) Uiso 1 1 calc R . . C19 C 0.0543(10) 0.665(3) 0.109(2) 0.111(11) Uani 1 1 d . . . H19A H 0.0285 0.7534 0.0971 0.083(8) Uiso 1 1 calc R . . H19B H 0.0593 0.6311 0.1609 0.083(8) Uiso 1 1 calc R . . H19C H 0.0412 0.5725 0.0763 0.083(8) Uiso 1 1 calc R . . C20 C 0.1535(8) 0.496(2) 0.0550(10) 0.074(5) Uani 1 1 d . . . H20A H 0.1167 0.4708 0.0252 0.083(8) Uiso 1 1 calc R . . H20B H 0.1707 0.3919 0.0752 0.083(8) Uiso 1 1 calc R . . C21 C 0.1850(14) 0.574(3) 0.0022(14) 0.090(11) Uani 1 1 d . . . H21A H 0.1853 0.4975 -0.0377 0.083(8) Uiso 1 1 calc R . . H21B H 0.2216 0.5974 0.0312 0.083(8) Uiso 1 1 calc R . . H21C H 0.1675 0.6747 -0.0194 0.083(8) Uiso 1 1 calc R . . C22 C 0.2615(15) 0.953(3) -0.2518(16) 0.094(10) Uani 1 1 d . . . H22 H 0.2692 0.9909 -0.2954 0.083(8) Uiso 1 1 calc R . . C23 C 0.3027(11) 0.953(2) -0.1819(17) 0.083(7) Uani 1 1 d . . . H23 H 0.3374 0.9885 -0.1804 0.083(8) Uiso 1 1 calc R . . C24 C 0.2920(10) 0.901(2) -0.1147(17) 0.067(7) Uani 1 1 d . . . C25 C 0.2374(10) 0.848(2) -0.1234(13) 0.069(6) Uani 1 1 d . . . H25 H 0.2263 0.8138 -0.0818 0.083(8) Uiso 1 1 calc R . . C26 C 0.2024(10) 0.849(3) -0.1937(19) 0.073(7) Uani 1 1 d . . . H26 H 0.1678 0.8082 -0.1984 0.083(8) Uiso 1 1 calc R . . C27 C 0.3301(11) 0.906(3) -0.0428(15) 0.065(7) Uani 1 1 d . . . H27 H 0.3632 0.9535 -0.0417 0.083(8) Uiso 1 1 calc R . . C28 C 0.3260(10) 0.853(3) 0.0247(14) 0.064(6) Uani 1 1 d . . . H28 H 0.2917 0.8157 0.0245 0.083(8) Uiso 1 1 calc R . . C29 C 0.3654(9) 0.845(2) 0.0957(14) 0.065(6) Uani 1 1 d . . . C30 C 0.4169(13) 0.904(3) 0.1089(16) 0.084(9) Uani 1 1 d . . . H30 H 0.4266 0.9458 0.0675 0.083(8) Uiso 1 1 calc R . . C31 C 0.4549(10) 0.909(3) 0.1761(16) 0.081(8) Uani 1 1 d . . . H31 H 0.4882 0.9595 0.1810 0.083(8) Uiso 1 1 calc R . . C32 C 0.4433(8) 0.836(2) 0.2385(12) 0.060(5) Uani 1 1 d . . . C33 C 0.3911(10) 0.770(2) 0.2282(12) 0.071(6) Uani 1 1 d . . . H33 H 0.3819 0.7199 0.2684 0.083(8) Uiso 1 1 calc R . . C34 C 0.3542(9) 0.779(2) 0.1585(13) 0.066(6) Uani 1 1 d . . . H34 H 0.3195 0.7389 0.1532 0.083(8) Uiso 1 1 calc R . . C35 C 0.5286(16) 0.962(4) 0.3310(19) 0.132(15) Uani 1 1 d . . . H35A H 0.5205 1.0611 0.3001 0.083(8) Uiso 1 1 calc R . . H35B H 0.5388 0.9922 0.3842 0.083(8) Uiso 1 1 calc R . . C36 C 0.5663(16) 0.868(4) 0.3135(14) 0.147(15) Uani 1 1 d . . . H36A H 0.5996 0.9289 0.3230 0.083(8) Uiso 1 1 calc R . . H36B H 0.5541 0.8379 0.2609 0.083(8) Uiso 1 1 calc R . . H36C H 0.5722 0.7695 0.3440 0.083(8) Uiso 1 1 calc R . . C37 C 0.4743(10) 0.728(3) 0.3728(11) 0.084(6) Uani 1 1 d . . . H37A H 0.5103 0.6982 0.4035 0.083(8) Uiso 1 1 calc R . . H37B H 0.4550 0.6271 0.3536 0.083(8) Uiso 1 1 calc R . . C38 C 0.4457(15) 0.816(3) 0.420(2) 0.120(15) Uani 1 1 d . . . H38A H 0.4432 0.7456 0.4608 0.083(8) Uiso 1 1 calc R . . H38B H 0.4100 0.8455 0.3897 0.083(8) Uiso 1 1 calc R . . H38C H 0.4653 0.9148 0.4402 0.083(8) Uiso 1 1 calc R . . N2 N 0.6050(9) 0.341(3) 0.6507(15) 0.084(8) Uani 1 1 d . . . C2 C 0.5735(13) 0.322(2) 0.5966(15) 0.056(9) 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 Au1 0.0682(5) 0.0754(5) 0.0792(5) 0.0007(4) 0.0259(4) 0.0003(4) Au2 0.0694(5) 0.0773(5) 0.0788(5) 0.0031(5) 0.0250(4) -0.0002(5) N1 0.10(2) 0.115(16) 0.085(19) 0.009(11) 0.053(17) -0.027(13) N3 0.056(16) 0.126(16) 0.10(2) 0.003(13) 0.028(15) 0.011(11) N4 0.10(2) 0.099(17) 0.10(2) -0.001(11) 0.038(17) -0.025(13) N5 0.109(19) 0.062(11) 0.096(16) 0.019(11) 0.034(14) -0.009(12) N6 0.055(12) 0.082(12) 0.065(13) 0.006(9) 0.016(10) 0.015(9) N7 0.044(12) 0.084(13) 0.067(13) 0.008(9) 0.011(10) -0.005(10) N8 0.096(17) 0.100(15) 0.070(15) 0.003(10) 0.025(13) -0.023(11) C1 0.04(2) 0.21(3) 0.07(3) -0.036(18) 0.015(19) 0.020(17) C3 0.07(2) 0.047(11) 0.047(17) 0.004(9) 0.008(15) -0.003(10) C4 0.031(18) 0.23(4) 0.11(3) -0.01(2) 0.033(19) -0.032(19) C5 0.09(2) 0.076(15) 0.083(19) -0.010(13) 0.047(18) -0.001(15) C6 0.067(17) 0.126(17) 0.053(15) 0.000(13) 0.018(13) 0.006(13) C7 0.057(18) 0.073(12) 0.056(14) 0.016(11) 0.018(13) -0.007(12) C8 0.058(17) 0.081(14) 0.102(19) -0.001(12) 0.043(16) -0.010(13) C9 0.054(18) 0.073(15) 0.11(2) 0.010(16) 0.011(17) -0.013(13) C10 0.06(2) 0.12(2) 0.075(19) 0.014(15) 0.022(15) -0.001(14) C11 0.051(16) 0.052(12) 0.10(2) 0.012(11) 0.027(15) 0.001(9) C12 0.050(15) 0.091(16) 0.062(15) 0.023(11) 0.035(13) -0.005(11) C13 0.060(18) 0.038(11) 0.070(18) -0.006(9) 0.021(15) 0.006(9) C14 0.09(2) 0.052(15) 0.074(18) 0.023(12) 0.008(16) 0.007(11) C15 0.10(2) 0.045(12) 0.064(16) 0.011(10) 0.037(15) -0.007(11) C16 0.066(16) 0.059(12) 0.069(14) -0.002(11) 0.020(12) 0.007(11) C17 0.074(18) 0.048(12) 0.097(19) 0.005(12) 0.057(17) 0.016(11) C18 0.068(19) 0.104(15) 0.095(19) 0.000(14) 0.041(15) 0.009(15) C19 0.045(15) 0.13(2) 0.15(3) -0.037(18) 0.021(16) 0.012(14) C20 0.074(15) 0.078(13) 0.068(14) 0.002(11) 0.016(11) 0.000(11) C21 0.15(3) 0.090(19) 0.049(16) -0.024(11) 0.051(19) -0.031(14) C22 0.11(2) 0.11(2) 0.052(15) 0.011(12) 0.001(16) 0.020(17) C23 0.070(18) 0.068(12) 0.13(2) 0.012(13) 0.055(18) -0.002(11) C24 0.033(14) 0.061(13) 0.10(2) -0.003(12) 0.015(14) 0.001(10) C25 0.075(18) 0.071(12) 0.066(15) 0.011(10) 0.031(14) 0.019(11) C26 0.023(13) 0.084(14) 0.12(2) -0.010(14) 0.032(16) -0.001(10) C27 0.07(2) 0.066(15) 0.067(16) -0.009(11) 0.026(15) -0.017(11) C28 0.055(17) 0.086(13) 0.065(16) -0.012(11) 0.038(14) -0.010(11) C29 0.043(15) 0.075(14) 0.071(17) 0.007(11) 0.004(13) -0.006(10) C30 0.08(2) 0.12(2) 0.07(2) -0.012(12) 0.037(19) -0.022(14) C31 0.044(16) 0.12(2) 0.08(2) 0.021(14) 0.030(16) -0.022(12) C32 0.025(12) 0.097(16) 0.059(15) 0.001(10) 0.013(11) -0.007(10) C33 0.094(19) 0.082(13) 0.052(13) -0.001(10) 0.044(13) 0.006(12) C34 0.067(17) 0.063(12) 0.072(16) -0.004(11) 0.029(14) 0.003(10) C35 0.19(4) 0.11(2) 0.075(19) 0.017(16) 0.02(2) 0.08(3) C36 0.23(4) 0.16(3) 0.037(15) 0.017(16) 0.01(2) 0.04(3) C37 0.094(18) 0.096(16) 0.060(13) 0.024(12) 0.017(12) 0.008(13) C38 0.08(3) 0.14(3) 0.16(3) -0.02(2) 0.06(3) -0.007(16) N2 0.050(14) 0.099(14) 0.096(18) -0.024(12) 0.009(13) 0.013(11) C2 0.08(2) 0.044(11) 0.052(18) -0.022(10) 0.026(16) -0.003(11) _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 C1 1.93(3) . ? Au1 C2 2.04(3) . ? Au2 C4 1.905(10) . ? Au2 C3 1.920(10) . ? N1 C1 1.19(3) . ? N3 C3 1.196(10) . ? N4 C4 1.196(10) . ? N5 C9 1.35(3) . ? N5 C5 1.36(3) . ? N6 C15 1.31(3) . ? N6 C18 1.43(3) . ? N6 C20 1.48(2) . ? N7 C26 1.30(3) . ? N7 C22 1.33(4) . ? N8 C32 1.37(2) . ? N8 C37 1.45(3) . ? N8 C35 1.63(4) . ? C5 C6 1.33(3) . ? C5 H5 0.9300 . ? C6 C7 1.40(3) . ? C6 H6 0.9300 . ? C7 C8 1.37(3) . ? C7 C10 1.49(3) . ? C8 C9 1.41(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.34(3) . ? C10 H10 0.9300 . ? C11 C12 1.51(3) . ? C11 H11 0.9300 . ? C12 C17 1.40(3) . ? C12 C13 1.44(3) . ? C13 C14 1.35(3) . ? C13 H13 0.9300 . ? C14 C15 1.42(3) . ? C14 H14 0.9300 . ? C15 C16 1.41(3) . ? C16 C17 1.34(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.52(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.57(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.42(4) . ? C22 H22 0.9300 . ? C23 C24 1.41(3) . ? C23 H23 0.9300 . ? C24 C27 1.41(3) . ? C24 C25 1.43(3) . ? C25 C26 1.35(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.35(3) . ? C27 H27 0.9300 . ? C28 C29 1.41(3) . ? C28 H28 0.9300 . ? C29 C30 1.37(3) . ? C29 C34 1.37(3) . ? C30 C31 1.34(3) . ? C30 H30 0.9300 . ? C31 C32 1.40(3) . ? C31 H31 0.9300 . ? C32 C33 1.41(3) . ? C33 C34 1.37(3) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.34(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.47(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N2 C2 1.10(3) . ? 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 C1 Au1 C2 177.6(11) . . ? C4 Au2 C3 174.6(15) . . ? C9 N5 C5 120(2) . . ? C15 N6 C18 124.0(19) . . ? C15 N6 C20 122.1(17) . . ? C18 N6 C20 113.9(19) . . ? C26 N7 C22 119(2) . . ? C32 N8 C37 127(2) . . ? C32 N8 C35 117.8(19) . . ? C37 N8 C35 114(2) . . ? N1 C1 Au1 168(3) . . ? N3 C3 Au2 170(3) . . ? N4 C4 Au2 166(3) . . ? C6 C5 N5 124(2) . . ? C6 C5 H5 117.9 . . ? N5 C5 H5 117.9 . . ? C5 C6 C7 118(2) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 118(2) . . ? C8 C7 C10 127(2) . . ? C6 C7 C10 115(2) . . ? C7 C8 C9 123(2) . . ? C7 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? N5 C9 C8 117(3) . . ? N5 C9 H9 121.5 . . ? C8 C9 H9 121.5 . . ? C11 C10 C7 122(2) . . ? C11 C10 H10 119.0 . . ? C7 C10 H10 119.0 . . ? C10 C11 C12 126(2) . . ? C10 C11 H11 116.9 . . ? C12 C11 H11 116.9 . . ? C17 C12 C13 117(2) . . ? C17 C12 C11 121(2) . . ? C13 C12 C11 122(2) . . ? C14 C13 C12 118(2) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 126(2) . . ? C13 C14 H14 116.9 . . ? C15 C14 H14 116.9 . . ? N6 C15 C16 125(2) . . ? N6 C15 C14 122(2) . . ? C16 C15 C14 113(2) . . ? C17 C16 C15 124(2) . . ? C17 C16 H16 117.9 . . ? C15 C16 H16 117.9 . . ? C16 C17 C12 121(2) . . ? C16 C17 H17 119.3 . . ? C12 C17 H17 119.3 . . ? N6 C18 C19 116(2) . . ? N6 C18 H18A 108.3 . . ? C19 C18 H18A 108.3 . . ? N6 C18 H18B 108.3 . . ? C19 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N6 C20 C21 112.8(16) . . ? N6 C20 H20A 109.0 . . ? C21 C20 H20A 109.1 . . ? N6 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N7 C22 C23 120(3) . . ? N7 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 121(3) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C27 C24 C23 124(2) . . ? C27 C24 C25 121(2) . . ? C23 C24 C25 115(2) . . ? C26 C25 C24 118(2) . . ? C26 C25 H25 121.0 . . ? C24 C25 H25 121.0 . . ? N7 C26 C25 127(2) . . ? N7 C26 H26 116.6 . . ? C25 C26 H26 116.6 . . ? C28 C27 C24 130(2) . . ? C28 C27 H27 115.0 . . ? C24 C27 H27 115.0 . . ? C27 C28 C29 130(2) . . ? C27 C28 H28 114.9 . . ? C29 C28 H28 114.9 . . ? C30 C29 C34 114(2) . . ? C30 C29 C28 124(2) . . ? C34 C29 C28 122(2) . . ? C31 C30 C29 126(2) . . ? C31 C30 H30 116.9 . . ? C29 C30 H30 116.9 . . ? C30 C31 C32 119(2) . . ? C30 C31 H31 120.7 . . ? C32 C31 H31 120.7 . . ? N8 C32 C31 124.5(19) . . ? N8 C32 C33 117.6(19) . . ? C31 C32 C33 118(2) . . ? C34 C33 C32 119.1(19) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C33 C34 C29 124(2) . . ? C33 C34 H34 118.0 . . ? C29 C34 H34 118.1 . . ? C36 C35 N8 98(3) . . ? C36 C35 H35A 112.1 . . ? N8 C35 H35A 112.1 . . ? C36 C35 H35B 112.1 . . ? N8 C35 H35B 112.1 . . ? H35A C35 H35B 109.8 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N8 C37 C38 112(2) . . ? N8 C37 H37A 109.3 . . ? C38 C37 H37A 109.3 . . ? N8 C37 H37B 109.3 . . ? C38 C37 H37B 109.3 . . ? H37A C37 H37B 108.0 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N2 C2 Au1 173(2) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.37 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.744 _refine_diff_density_min -0.771 _refine_diff_density_rms 0.127 # Attachment '- MPSHAu(CN)2.txt' data_MPSHAu(CN)2 _database_code_depnum_ccdc_archive 'CCDC 826267' #TrackingRef '- MPSHAu(CN)2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 Au N4 O' _chemical_formula_weight 544.40 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' 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.6150(3) _cell_length_b 7.6610(3) _cell_length_c 10.2670(6) _cell_angle_alpha 83.806(2) _cell_angle_beta 83.545(2) _cell_angle_gamma 77.497(3) _cell_volume 502.87(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour pink _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 7.331 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8672 _exptl_absorpt_correction_T_max 0.9303 _exptl_absorpt_process_details 'Empirical absorption correction:XABS2' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3270 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3270 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO and SCALEPACK' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0631P)^2^+0.5090P] 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 0.023(17) _refine_ls_number_reflns 3270 _refine_ls_number_parameters 249 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.013 _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 Au Au 0.37694(8) 0.96709(8) 0.26793(8) 0.06187(13) Uani 1 1 d . . . O1 O 0.1583(13) 1.5305(10) 0.9183(8) 0.0637(19) Uani 1 1 d . . . N1 N 1.5616(13) 0.4134(13) 0.4113(10) 0.061(2) Uani 1 1 d . . . N2 N 0.1385(11) 1.1957(11) 0.8336(7) 0.0474(15) Uani 1 1 d . . . N3 N -0.050(3) 1.209(3) 0.354(3) 0.083(6) Uani 1 1 d . . . N4 N 0.807(5) 0.735(6) 0.172(4) 0.140(13) Uani 1 1 d . . . C1 C 1.531(2) 0.474(2) 0.5315(14) 0.072(3) Uani 1 1 d . . . H1 H 1.6374 0.4460 0.5867 0.086(10) Uiso 1 1 calc R . . C2 C 1.3439(17) 0.5750(18) 0.5727(12) 0.068(3) Uani 1 1 d . . . H2 H 1.3232 0.6147 0.6566 0.086(10) Uiso 1 1 calc R . . C3 C 1.1816(14) 0.6205(14) 0.4897(10) 0.052(2) Uani 1 1 d . . . C4 C 1.2275(17) 0.5577(17) 0.3650(12) 0.067(3) Uani 1 1 d . . . H4 H 1.1281 0.5878 0.3047 0.086(10) Uiso 1 1 calc R . . C5 C 1.4135(18) 0.4544(19) 0.3309(13) 0.071(3) Uani 1 1 d . . . H5 H 1.4383 0.4106 0.2483 0.086(10) Uiso 1 1 calc R . . C6 C 0.9755(15) 0.7294(14) 0.5264(11) 0.052(2) Uani 1 1 d . . . H6 H 0.8841 0.7659 0.4615 0.086(10) Uiso 1 1 calc R . . C7 C 0.9124(13) 0.7786(12) 0.6467(9) 0.0486(18) Uani 1 1 d . . . H7 H 1.0070 0.7415 0.7097 0.086(10) Uiso 1 1 calc R . . C8 C 0.7123(13) 0.8835(12) 0.6901(9) 0.0465(17) Uani 1 1 d . . . C9 C 0.6637(13) 0.9151(11) 0.8257(9) 0.0441(16) Uani 1 1 d . . . H9 H 0.7615 0.8630 0.8843 0.086(10) Uiso 1 1 calc R . . C10 C 0.4813(14) 1.0175(12) 0.8733(9) 0.0482(18) Uani 1 1 d . . . H10 H 0.4594 1.0359 0.9623 0.086(10) Uiso 1 1 calc R . . C11 C 0.3242(13) 1.0965(10) 0.7890(8) 0.0424(16) Uani 1 1 d . . . C12 C 0.3681(15) 1.0679(13) 0.6534(10) 0.053(2) Uani 1 1 d . . . H12 H 0.2703 1.1194 0.5945 0.086(10) Uiso 1 1 calc R . . C13 C 0.5568(15) 0.9632(14) 0.6086(9) 0.053(2) Uani 1 1 d . . . H13 H 0.5806 0.9453 0.5195 0.086(10) Uiso 1 1 calc R . . C14 C 0.0816(13) 1.2381(11) 0.9716(8) 0.0421(16) Uani 1 1 d . . . C15 C -0.1534(15) 1.2910(16) 0.9799(12) 0.058(2) Uani 1 1 d . . . H15A H -0.2149 1.1870 1.0057 0.086(10) Uiso 1 1 calc R . . H15B H -0.2048 1.3789 1.0435 0.086(10) Uiso 1 1 calc R . . C16 C -0.2048(15) 1.3699(15) 0.8433(12) 0.059(2) Uani 1 1 d . . . H16A H -0.2074 1.4977 0.8334 0.086(10) Uiso 1 1 calc R . . H16B H -0.3390 1.3508 0.8257 0.086(10) Uiso 1 1 calc R . . C17 C -0.0324(13) 1.2713(12) 0.7512(9) 0.0471(18) Uani 1 1 d . . . H17A H -0.0781 1.1768 0.7140 0.086(10) Uiso 1 1 calc R . . H17B H 0.0107 1.3532 0.6800 0.086(10) Uiso 1 1 calc R . . C18 C 0.1919(19) 1.3754(15) 1.0090(10) 0.050(2) Uani 1 1 d . . . H18A H 0.1398 1.4080 1.0971 0.086(10) Uiso 1 1 calc R . . H18B H 0.3397 1.3250 1.0086 0.086(10) Uiso 1 1 calc R . . C19 C 0.247(2) 1.6661(18) 0.9543(17) 0.083(4) Uani 1 1 d . . . H19A H 0.2206 1.7691 0.8917 0.086(10) Uiso 1 1 calc R . . H19B H 0.3947 1.6235 0.9558 0.086(10) Uiso 1 1 calc R . . H19C H 0.1877 1.6989 1.0402 0.086(10) Uiso 1 1 calc R . . C20 C 0.099(3) 1.114(3) 0.3270(19) 0.081(7) Uani 1 1 d . . . C21 C 0.644(4) 0.818(3) 0.2143(19) 0.085(8) Uani 1 1 d . . . H14 H 0.148(12) 1.123(10) 1.042(8) 0.022(16) 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 0.05501(17) 0.0691(2) 0.05065(17) -0.00193(12) -0.00356(11) 0.00865(12) O1 0.086(5) 0.058(4) 0.053(4) 0.004(3) -0.014(4) -0.028(4) N1 0.049(4) 0.063(5) 0.063(5) -0.003(4) -0.006(4) 0.003(4) N2 0.043(3) 0.056(4) 0.041(4) -0.008(3) -0.009(3) -0.001(3) N3 0.048(8) 0.076(9) 0.101(13) 0.000(8) 0.012(7) 0.030(6) N4 0.096(18) 0.21(3) 0.102(18) -0.044(18) -0.006(14) 0.016(18) C1 0.069(7) 0.081(10) 0.056(7) -0.008(7) -0.014(5) 0.012(7) C2 0.059(6) 0.089(8) 0.052(5) -0.018(5) -0.011(4) 0.002(5) C3 0.045(4) 0.058(5) 0.052(5) -0.007(4) 0.002(4) -0.008(4) C4 0.057(5) 0.078(7) 0.058(6) -0.011(5) -0.005(4) 0.003(5) C5 0.058(6) 0.095(9) 0.058(6) -0.021(6) -0.002(5) -0.003(6) C6 0.044(4) 0.049(5) 0.060(6) -0.008(4) -0.009(4) 0.002(4) C7 0.043(4) 0.051(5) 0.049(5) -0.013(4) 0.001(3) -0.002(3) C8 0.046(4) 0.042(4) 0.049(5) -0.012(3) 0.001(3) -0.001(3) C9 0.043(4) 0.044(4) 0.045(4) -0.009(3) -0.006(3) -0.005(3) C10 0.046(4) 0.050(5) 0.049(5) -0.002(4) -0.013(3) -0.007(4) C11 0.047(4) 0.034(4) 0.046(4) 0.000(3) -0.009(3) -0.006(3) C12 0.051(4) 0.051(5) 0.050(5) -0.001(4) -0.011(4) 0.003(4) C13 0.051(4) 0.063(6) 0.040(4) -0.009(4) -0.001(4) 0.001(4) C14 0.045(4) 0.044(4) 0.036(4) -0.006(3) -0.004(3) -0.003(3) C15 0.046(5) 0.061(6) 0.067(6) -0.006(5) 0.009(4) -0.016(5) C16 0.044(4) 0.062(6) 0.068(6) -0.002(5) -0.009(4) -0.003(4) C17 0.040(4) 0.050(5) 0.048(4) 0.001(3) -0.009(3) -0.003(3) C18 0.060(6) 0.046(6) 0.043(4) -0.012(4) -0.004(4) -0.005(5) C19 0.095(9) 0.064(7) 0.104(11) 0.001(7) -0.023(8) -0.044(7) C20 0.059(9) 0.080(11) 0.071(12) 0.000(8) 0.025(8) 0.043(8) C21 0.095(14) 0.117(16) 0.053(10) 0.031(10) -0.037(9) -0.047(12) _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 C20 2.004(14) . ? Au C21 1.94(3) . ? O1 C18 1.422(13) . ? O1 C19 1.400(14) . ? N1 C1 1.343(18) . ? N1 C5 1.316(15) . ? N2 C11 1.357(12) . ? N2 C14 1.477(11) . ? N2 C17 1.468(11) . ? N3 C20 1.12(2) . ? N4 C21 1.18(4) . ? C1 C2 1.358(19) . ? C1 H1 0.9300 . ? C2 C3 1.407(15) . ? C2 H2 0.9300 . ? C3 C4 1.395(15) . ? C3 C6 1.468(13) . ? C4 C5 1.343(17) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.326(14) . ? C6 H6 0.9300 . ? C7 C8 1.442(12) . ? C7 H7 0.9300 . ? C8 C13 1.394(13) . ? C8 C9 1.428(12) . ? C9 C10 1.360(13) . ? C9 H9 0.9300 . ? C10 C11 1.418(12) . ? C10 H10 0.9300 . ? C11 C12 1.421(13) . ? C12 C13 1.389(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.506(14) . ? C14 C15 1.514(13) . ? C14 H14 1.12(8) . ? C15 C16 1.511(16) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.518(14) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C21 Au C20 178.2(11) . . ? C19 O1 C18 111.6(9) . . ? C5 N1 C1 120.6(11) . . ? C11 N2 C14 124.2(7) . . ? C11 N2 C17 124.2(8) . . ? C17 N2 C14 111.6(7) . . ? N1 C1 C2 120.3(12) . . ? N1 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C2 C3 120.6(11) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 115.8(10) . . ? C4 C3 C6 120.1(9) . . ? C2 C3 C6 124.2(10) . . ? C5 C4 C3 120.9(11) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N1 C5 C4 121.7(12) . . ? N1 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C7 C6 C3 123.7(9) . . ? C7 C6 H6 118.1 . . ? C3 C6 H6 118.1 . . ? C6 C7 C8 126.8(9) . . ? C6 C7 H7 116.6 . . ? C8 C7 H7 116.6 . . ? C13 C8 C9 115.1(8) . . ? C13 C8 C7 125.1(9) . . ? C9 C8 C7 119.8(8) . . ? C10 C9 C8 123.3(8) . . ? C10 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? C9 C10 C11 120.9(9) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? N2 C11 C10 122.5(8) . . ? N2 C11 C12 120.3(8) . . ? C10 C11 C12 117.2(8) . . ? C13 C12 C11 120.1(8) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 123.5(9) . . ? C12 C13 H13 118.3 . . ? C8 C13 H13 118.3 . . ? N2 C14 C18 112.5(7) . . ? N2 C14 C15 103.2(7) . . ? C18 C14 C15 115.9(9) . . ? N2 C14 H14 111(4) . . ? C18 C14 H14 98(4) . . ? C15 C14 H14 116(4) . . ? C16 C15 C14 105.3(8) . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15B 110.7 . . ? C14 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? C15 C16 C17 105.1(8) . . ? C15 C16 H16A 110.7 . . ? C17 C16 H16A 110.7 . . ? C15 C16 H16B 110.7 . . ? C17 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? N2 C17 C16 105.0(8) . . ? N2 C17 H17A 110.7 . . ? C16 C17 H17A 110.7 . . ? N2 C17 H17B 110.7 . . ? C16 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? O1 C18 C14 109.8(8) . . ? O1 C18 H18A 109.7 . . ? C14 C18 H18A 109.7 . . ? O1 C18 H18B 109.7 . . ? C14 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 Au 174(2) . . ? N4 C21 Au 175(2) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.631 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.111