# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Rossana Galassi' _publ_contact_author_email rossana.galassi@unicam.it _publ_section_title ; Synthesis and Characterization of Azolate Gold(I) Phosphane Complexes as Thioredoxin-Reductase Inhibiting Antitumor Agents ; _publ_contact_author_address ? _publ_contact_author_phone ? loop_ _publ_author_name R.Galassi A.Burini S.Ricci M.Pellei M.P.Rigobello A.Citta ; A.Dolmella ; V.Gandin C.Marzano #===END data_cam2_w _database_code_depnum_ccdc_archive 'CCDC 847346' #TrackingRef '- Cam23_d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Au N4 O4 P' _chemical_formula_sum 'C21 H16 Au N4 O4 P' _chemical_formula_weight 616.31 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' P P 0.1023 0.0942 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1300(16) _cell_length_b 11.393(2) _cell_length_c 23.339(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.60(3) _cell_angle_gamma 90.00 _cell_volume 2142.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 12.2 _cell_measurement_theta_max 15.1 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 6.980 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.906 _exptl_absorpt_process_details '(North et al., 1968)' _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 'Philips PW1100 dffractometer' _diffrn_measurement_method 'omega-2 theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0(1) _diffrn_reflns_number 4266 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4165 _reflns_number_gt 3856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'FEBO system' _computing_cell_refinement 'FEBO system' _computing_data_reduction 'FEBO system' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX 1.70.00 (Farrugia, 1999)' _computing_publication_material 'SHELXTL NT vers.5.10 (Sheldrick, 1999)' _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^)+(0.0000P)^2^+9.0950P] 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 4165 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.364 _refine_ls_restrained_S_all 1.364 _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 0.06445(3) 0.69382(2) 0.071363(11) 0.04489(11) Uani 1 1 d . . . P P 0.1981(2) 0.54116(14) 0.11492(7) 0.0414(4) Uani 1 1 d . . . N1 N -0.0729(7) 0.8360(5) 0.0374(2) 0.0422(11) Uani 1 1 d . . . N2 N -0.0946(7) 0.8597(5) -0.0192(2) 0.0437(12) Uani 1 1 d . . . N3 N -0.2572(8) 0.9960(6) -0.0819(3) 0.0575(16) Uani 1 1 d . . . N4 N -0.1661(9) 0.9055(6) 0.1252(3) 0.0630(17) Uani 1 1 d . . . O1 O -0.1856(8) 0.9646(6) -0.1214(3) 0.0797(18) Uani 1 1 d . . . O2 O -0.3685(8) 1.0681(6) -0.0856(3) 0.086(2) Uani 1 1 d . . . O3 O -0.2437(9) 0.9818(6) 0.1467(3) 0.0848(19) Uani 1 1 d . . . O4 O -0.0917(11) 0.8271(7) 0.1533(3) 0.096(2) Uani 1 1 d . . . C1 C -0.2036(8) 0.9479(5) -0.0254(3) 0.0414(14) Uani 1 1 d . . . C2 C -0.2547(9) 0.9835(6) 0.0259(3) 0.0506(16) Uani 1 1 d . . . H2 H -0.3291 1.0423 0.0326 0.061 Uiso 1 1 calc R . . C3 C -0.1670(8) 0.9095(6) 0.0639(3) 0.0436(14) Uani 1 1 d . . . C4 C 0.3508(8) 0.5888(5) 0.1738(3) 0.0416(13) Uani 1 1 d . . . C5 C 0.4437(11) 0.6881(6) 0.1666(3) 0.0568(18) Uani 1 1 d . . . H5 H 0.4234 0.7310 0.1325 0.068 Uiso 1 1 calc R . . C6 C 0.5677(11) 0.7243(7) 0.2101(4) 0.065(2) Uani 1 1 d . . . H6 H 0.6324 0.7896 0.2045 0.077 Uiso 1 1 calc R . . C7 C 0.5938(10) 0.6639(8) 0.2608(3) 0.0598(19) Uani 1 1 d . . . H7 H 0.6755 0.6883 0.2900 0.072 Uiso 1 1 calc R . . C8 C 0.4994(10) 0.5671(8) 0.2687(3) 0.064(2) Uani 1 1 d . . . H8 H 0.5169 0.5266 0.3036 0.076 Uiso 1 1 calc R . . C9 C 0.3806(9) 0.5294(7) 0.2262(3) 0.0527(17) Uani 1 1 d . . . H9 H 0.3184 0.4631 0.2322 0.063 Uiso 1 1 calc R . . C10 C 0.0574(7) 0.4463(5) 0.1469(3) 0.0422(14) Uani 1 1 d . . . C11 C -0.0332(11) 0.4941(8) 0.1880(4) 0.071(2) Uani 1 1 d . . . H11 H -0.0234 0.5735 0.1969 0.086 Uiso 1 1 calc R . . C12 C -0.1362(12) 0.4248(10) 0.2151(5) 0.090(3) Uani 1 1 d . . . H12 H -0.1946 0.4568 0.2431 0.108 Uiso 1 1 calc R . . C13 C -0.1536(12) 0.3086(9) 0.2013(5) 0.086(3) Uani 1 1 d . . . H13 H -0.2239 0.2619 0.2199 0.103 Uiso 1 1 calc R . . C14 C -0.0681(11) 0.2596(8) 0.1600(5) 0.083(3) Uani 1 1 d . . . H14 H -0.0821 0.1808 0.1501 0.099 Uiso 1 1 calc R . . C15 C 0.0396(10) 0.3299(6) 0.1333(4) 0.0586(18) Uani 1 1 d . . . H15 H 0.0997 0.2974 0.1060 0.070 Uiso 1 1 calc R . . C16 C 0.3083(9) 0.4485(6) 0.0694(3) 0.0489(15) Uani 1 1 d . . . C17 C 0.4295(10) 0.3715(7) 0.0940(4) 0.0616(19) Uani 1 1 d . . . H17 H 0.4568 0.3681 0.1340 0.074 Uiso 1 1 calc R . . C18 C 0.5092(13) 0.3000(8) 0.0587(4) 0.074(2) Uani 1 1 d . . . H18 H 0.5893 0.2472 0.0750 0.089 Uiso 1 1 calc R . . C19 C 0.4722(12) 0.3057(8) 0.0007(4) 0.071(2) Uani 1 1 d . . . H19 H 0.5272 0.2572 -0.0225 0.085 Uiso 1 1 calc R . . C20 C 0.3545(11) 0.3824(8) -0.0241(3) 0.067(2) Uani 1 1 d . . . H20 H 0.3302 0.3859 -0.0641 0.081 Uiso 1 1 calc R . . C21 C 0.2715(9) 0.4545(7) 0.0100(3) 0.0544(17) Uani 1 1 d . . . H21 H 0.1915 0.5067 -0.0069 0.065 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 0.05015(17) 0.04014(16) 0.04186(15) 0.00471(10) -0.00331(11) 0.00170(10) P 0.0462(9) 0.0365(8) 0.0396(8) 0.0021(6) -0.0014(7) 0.0001(7) N1 0.045(3) 0.035(3) 0.046(3) -0.001(2) 0.002(2) 0.003(2) N2 0.045(3) 0.042(3) 0.042(3) -0.001(2) 0.000(2) -0.004(2) N3 0.053(3) 0.050(3) 0.063(4) 0.004(3) -0.017(3) -0.004(3) N4 0.078(4) 0.061(4) 0.054(4) -0.009(3) 0.022(3) -0.007(3) O1 0.091(4) 0.095(5) 0.049(3) 0.008(3) -0.005(3) 0.012(4) O2 0.084(4) 0.082(4) 0.084(4) 0.022(4) -0.015(3) 0.029(4) O3 0.104(5) 0.085(4) 0.072(4) -0.021(3) 0.039(4) 0.000(4) O4 0.145(7) 0.101(5) 0.047(3) 0.016(3) 0.025(4) 0.029(5) C1 0.040(3) 0.035(3) 0.045(3) 0.003(3) -0.011(3) -0.003(2) C2 0.048(4) 0.039(3) 0.065(4) -0.008(3) 0.011(3) 0.001(3) C3 0.046(3) 0.049(4) 0.035(3) -0.003(3) 0.002(3) -0.006(3) C4 0.051(4) 0.032(3) 0.041(3) -0.002(2) 0.004(3) -0.001(3) C5 0.081(5) 0.044(4) 0.044(4) 0.001(3) 0.007(4) -0.009(3) C6 0.074(5) 0.057(4) 0.063(5) -0.005(4) 0.010(4) -0.023(4) C7 0.061(5) 0.070(5) 0.045(4) -0.011(4) -0.005(3) -0.003(4) C8 0.060(5) 0.081(6) 0.046(4) 0.009(4) -0.009(3) -0.010(4) C9 0.058(4) 0.055(4) 0.042(3) 0.013(3) -0.005(3) -0.009(3) C10 0.033(3) 0.040(3) 0.052(4) 0.002(3) 0.000(3) 0.001(2) C11 0.063(5) 0.058(5) 0.097(7) -0.005(4) 0.028(5) -0.003(4) C12 0.069(6) 0.089(7) 0.122(9) 0.009(6) 0.046(6) -0.001(5) C13 0.058(5) 0.082(7) 0.123(9) 0.024(6) 0.030(6) -0.008(5) C14 0.067(6) 0.047(5) 0.134(9) 0.011(5) 0.011(6) -0.013(4) C15 0.056(4) 0.046(4) 0.075(5) -0.003(4) 0.012(4) -0.005(3) C16 0.051(4) 0.045(4) 0.049(4) -0.005(3) 0.001(3) -0.010(3) C17 0.071(5) 0.052(4) 0.063(5) -0.004(4) 0.013(4) 0.012(4) C18 0.078(6) 0.072(6) 0.075(6) -0.008(4) 0.020(5) 0.021(4) C19 0.071(6) 0.069(5) 0.079(6) -0.027(4) 0.031(5) -0.009(4) C20 0.068(5) 0.088(6) 0.049(4) -0.020(4) 0.020(4) -0.029(5) C21 0.048(4) 0.062(4) 0.053(4) -0.011(3) 0.004(3) -0.017(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 P 2.2244(17) . ? Au N1 2.065(5) . ? P C4 1.808(6) . ? P C10 1.806(7) . ? P C16 1.816(7) . ? N1 N2 1.339(7) . ? N1 C3 1.339(8) . ? N2 C1 1.335(8) . ? N3 O1 1.209(9) . ? N3 O2 1.216(8) . ? N3 C1 1.442(8) . ? N4 O3 1.221(9) . ? N4 O4 1.220(9) . ? N4 C3 1.431(9) . ? C1 C2 1.378(10) . ? C2 H2 0.9300 . ? C2 C3 1.355(10) . ? C4 C5 1.382(9) . ? C4 C9 1.391(9) . ? C5 H5 0.9300 . ? C5 C6 1.396(11) . ? C6 H6 0.9300 . ? C6 C7 1.361(12) . ? C7 H7 0.9300 . ? C7 C8 1.370(11) . ? C8 H8 0.9300 . ? C8 C9 1.360(10) . ? C9 H9 0.9300 . ? C10 C11 1.394(11) . ? C10 C15 1.368(10) . ? C11 H11 0.9300 . ? C11 C12 1.367(12) . ? C12 H12 0.9300 . ? C12 C13 1.365(14) . ? C13 H13 0.9300 . ? C13 C14 1.379(15) . ? C14 H14 0.9300 . ? C14 C15 1.392(12) . ? C15 H15 0.9300 . ? C16 C17 1.385(11) . ? C16 C21 1.381(10) . ? C17 H17 0.9300 . ? C17 C18 1.381(11) . ? C18 H18 0.9300 . ? C18 C19 1.347(14) . ? C19 H19 0.9300 . ? C19 C20 1.366(13) . ? C20 H20 0.9300 . ? C20 C21 1.380(11) . ? C21 H21 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 N1 Au P 174.51(16) . . ? C4 P Au 110.9(2) . . ? C4 P C16 106.1(3) . . ? C10 P Au 111.0(2) . . ? C10 P C4 105.9(3) . . ? C10 P C16 106.4(3) . . ? C16 P Au 115.9(2) . . ? N2 N1 Au 122.1(4) . . ? N2 N1 C3 108.7(5) . . ? C3 N1 Au 128.8(4) . . ? C1 N2 N1 104.9(5) . . ? O1 N3 O2 125.0(7) . . ? O1 N3 C1 118.0(6) . . ? O2 N3 C1 117.0(7) . . ? O3 N4 C3 116.9(7) . . ? O4 N4 O3 123.1(7) . . ? O4 N4 C3 119.9(7) . . ? N2 C1 N3 120.0(6) . . ? N2 C1 C2 113.6(6) . . ? C2 C1 N3 126.4(6) . . ? C1 C2 H2 129.4 . . ? C3 C2 C1 101.1(6) . . ? C3 C2 H2 129.4 . . ? N1 C3 N4 120.9(6) . . ? N1 C3 C2 111.7(6) . . ? C2 C3 N4 127.4(7) . . ? C5 C4 P 119.0(5) . . ? C5 C4 C9 118.1(6) . . ? C9 C4 P 122.9(5) . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.5(7) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 120.1 . . ? C7 C6 C5 119.8(7) . . ? C7 C6 H6 120.1 . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 119.9(7) . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.8(7) . . ? C9 C8 H8 119.6 . . ? C4 C9 H9 119.6 . . ? C8 C9 C4 120.8(7) . . ? C8 C9 H9 119.6 . . ? C11 C10 P 118.2(5) . . ? C15 C10 P 122.5(6) . . ? C15 C10 C11 119.3(7) . . ? C10 C11 H11 119.8 . . ? C12 C11 C10 120.4(9) . . ? C12 C11 H11 119.8 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.0(10) . . ? C13 C12 H12 120.0 . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.8(9) . . ? C14 C13 H13 119.6 . . ? C13 C14 H14 120.5 . . ? C13 C14 C15 119.0(9) . . ? C15 C14 H14 120.5 . . ? C10 C15 C14 120.4(8) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 P 120.3(6) . . ? C21 C16 P 120.0(6) . . ? C21 C16 C17 119.7(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 C16 119.3(8) . . ? C18 C17 H17 120.3 . . ? C17 C18 H18 119.7 . . ? C19 C18 C17 120.7(9) . . ? C19 C18 H18 119.7 . . ? C18 C19 H19 119.8 . . ? C18 C19 C20 120.5(8) . . ? C20 C19 H19 119.8 . . ? C19 C20 H20 119.8 . . ? C19 C20 C21 120.3(8) . . ? C21 C20 H20 119.8 . . ? C16 C21 H21 120.3 . . ? C20 C21 C16 119.4(8) . . ? C20 C21 H21 120.3 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.847 _refine_diff_density_min -1.085 _refine_diff_density_rms 0.138 # Attachment '- Cam23_d.cif' data_camCF3 _database_code_depnum_ccdc_archive 'CCDC 847347' #TrackingRef '- Cam23_d.cif' _audit_creation_date 2011-11-17 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H16 Au F6 N2 P' _chemical_formula_sum 'C23 H16 Au F6 N2 P' _chemical_formula_weight 662.31 _chemical_melting_point ? 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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 14.633(4) _cell_length_b 9.092(2) _cell_length_c 35.389(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.79(3) _cell_angle_gamma 90.00 _cell_volume 4664.8(17) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_temperature 293(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 6.437 _exptl_absorpt_correction_T_min 0.3199 _exptl_absorpt_correction_T_max 0.4160 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 2528 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0443 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 9147 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.94 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.856 _diffrn_measured_fraction_theta_max 0.856 _diffrn_measurement_device_type 'Enraf-Nonius dip1030 image plate diffractometer' _diffrn_measurement_method '\f-scans with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6221 _reflns_number_total 9147 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Denzo (Otwinowski & Minor 1997)' _computing_data_collection 'XPRESS (MacScience, 2002)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_molecular_graphics 'Ortep3 for Windows (Farrugia,1997)' _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.991 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.104 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 593 _refine_ls_number_reflns 9147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0368 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.0979 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.270898(19) 0.47186(2) 0.145654(6) 0.06229(9) Uani 1 1 d . . . Au2 Au 0.804352(18) 0.51107(2) 0.112167(7) 0.06020(8) Uani 1 1 d . . . P1 P 0.25154(12) 0.62791(15) 0.09627(4) 0.0592(4) Uani 1 1 d . . . P2 P 0.90244(12) 0.33223(15) 0.13474(4) 0.0578(4) Uani 1 1 d . . . N1 N 0.2890(4) 0.3232(5) 0.18952(13) 0.0648(13) Uani 1 1 d . . . N2 N 0.7102(4) 0.6750(5) 0.09586(13) 0.0622(13) Uani 1 1 d . . . N3 N 0.2269(4) 0.2155(5) 0.19040(15) 0.0735(15) Uani 1 1 d . . . N4 N 0.7310(4) 0.7887(5) 0.07371(14) 0.0692(14) Uani 1 1 d . . . C1 C 0.3543(5) 0.3123(7) 0.22047(17) 0.0703(17) Uani 1 1 d . . . C2 C 0.3347(5) 0.1935(7) 0.24191(17) 0.0745(18) Uani 1 1 d . . . H2 H 0.3673 0.1583 0.2645 0.089 Uiso 1 1 calc R . . C3 C 0.2558(5) 0.1399(7) 0.22196(19) 0.0726(18) Uani 1 1 d . . . C4 C 0.4291(9) 0.4143(15) 0.2277(3) 0.131(4) Uani 1 1 d . . . C5 C 0.2006(9) 0.0109(10) 0.2316(4) 0.118(4) Uani 1 1 d . . . C6 C 0.1311(4) 0.6699(6) 0.08016(15) 0.0604(15) Uani 1 1 d . . . C7 C 0.0898(5) 0.7960(7) 0.09176(19) 0.0741(19) Uani 1 1 d . . . H7 H 0.1248 0.8643 0.1070 0.089 Uiso 1 1 calc R . . C8 C -0.0022(6) 0.8206(7) 0.0809(2) 0.079(2) Uani 1 1 d . . . H8 H -0.0291 0.9060 0.0888 0.095 Uiso 1 1 calc R . . C9 C -0.0561(5) 0.7205(8) 0.0583(2) 0.085(2) Uani 1 1 d . . . H9 H -0.1188 0.7378 0.0512 0.102 Uiso 1 1 calc R . . C10 C -0.0162(5) 0.5964(8) 0.0466(2) 0.081(2) Uani 1 1 d . . . H10 H -0.0515 0.5296 0.0309 0.097 Uiso 1 1 calc R . . C11 C 0.0765(5) 0.5688(7) 0.05784(19) 0.0729(18) Uani 1 1 d . . . H11 H 0.1026 0.4820 0.0504 0.087 Uiso 1 1 calc R . . C12 C 0.2990(4) 0.5547(5) 0.05531(16) 0.0569(14) Uani 1 1 d . . . C13 C 0.3665(5) 0.4498(6) 0.06126(18) 0.0664(16) Uani 1 1 d . . . H13 H 0.3847 0.4128 0.0856 0.080 Uiso 1 1 calc R . . C14 C 0.4079(5) 0.3984(7) 0.0302(2) 0.080(2) Uani 1 1 d . . . H14 H 0.4551 0.3294 0.0343 0.096 Uiso 1 1 calc R . . C15 C 0.3796(6) 0.4487(7) -0.0059(2) 0.080(2) Uani 1 1 d . . . H15 H 0.4071 0.4133 -0.0263 0.096 Uiso 1 1 calc R . . C16 C 0.3102(6) 0.5522(8) -0.01199(19) 0.088(2) Uani 1 1 d . . . H16 H 0.2911 0.5871 -0.0365 0.105 Uiso 1 1 calc R . . C17 C 0.2694(5) 0.6035(7) 0.01812(17) 0.0756(18) Uani 1 1 d . . . H17 H 0.2217 0.6714 0.0138 0.091 Uiso 1 1 calc R . . C18 C 0.3079(4) 0.8044(6) 0.10680(16) 0.0612(15) Uani 1 1 d . . . C19 C 0.3201(5) 0.9017(6) 0.07777(19) 0.0733(18) Uani 1 1 d . . . H19 H 0.2991 0.8765 0.0526 0.088 Uiso 1 1 calc R . . C20 C 0.3634(6) 1.0373(7) 0.0858(2) 0.083(2) Uani 1 1 d . . . H20 H 0.3712 1.1030 0.0664 0.099 Uiso 1 1 calc R . . C21 C 0.3938(6) 1.0704(8) 0.1229(3) 0.092(2) Uani 1 1 d . . . H21 H 0.4238 1.1593 0.1287 0.110 Uiso 1 1 calc R . . C22 C 0.3814(6) 0.9770(7) 0.1517(2) 0.093(2) Uani 1 1 d . . . H22 H 0.4014 1.0037 0.1769 0.112 Uiso 1 1 calc R . . C23 C 0.3392(5) 0.8428(7) 0.14388(18) 0.080(2) Uani 1 1 d . . . H23 H 0.3320 0.7782 0.1636 0.096 Uiso 1 1 calc R . . C24 C 0.6257(5) 0.6905(7) 0.10592(17) 0.0686(17) Uani 1 1 d . . . C25 C 0.5866(5) 0.8188(7) 0.08965(19) 0.0761(19) Uani 1 1 d . . . H25 H 0.5287 0.8584 0.0914 0.091 Uiso 1 1 calc R . . C26 C 0.6551(5) 0.8726(7) 0.07016(19) 0.0713(18) Uani 1 1 d . . . C27 C 0.5860(6) 0.5873(9) 0.1305(2) 0.082(2) Uani 1 1 d . . . C28 C 0.6557(7) 1.0090(9) 0.0462(3) 0.105(3) Uani 1 1 d . . . C29 C 0.8424(5) 0.1768(6) 0.15194(17) 0.0681(17) Uani 1 1 d . . . C30 C 0.7576(6) 0.1972(10) 0.1633(2) 0.103(3) Uani 1 1 d . . . H30 H 0.7317 0.2907 0.1630 0.124 Uiso 1 1 calc R . . C31 C 0.7104(7) 0.0762(13) 0.1754(3) 0.132(4) Uani 1 1 d . . . H31 H 0.6528 0.0896 0.1833 0.159 Uiso 1 1 calc R . . C32 C 0.7477(10) -0.0613(13) 0.1759(3) 0.136(5) Uani 1 1 d . . . H32 H 0.7152 -0.1415 0.1835 0.163 Uiso 1 1 calc R . . C33 C 0.8319(9) -0.0803(9) 0.1652(2) 0.117(4) Uani 1 1 d . . . H33 H 0.8572 -0.1742 0.1659 0.141 Uiso 1 1 calc R . . C34 C 0.8816(7) 0.0366(7) 0.1533(2) 0.093(3) Uani 1 1 d . . . H34 H 0.9400 0.0219 0.1463 0.112 Uiso 1 1 calc R . . C35 C 0.9824(4) 0.4027(6) 0.17394(16) 0.0578(14) Uani 1 1 d . . . C36 C 1.0031(5) 0.3293(7) 0.20796(18) 0.080(2) Uani 1 1 d . . . H36 H 0.9755 0.2392 0.2116 0.095 Uiso 1 1 calc R . . C37 C 1.0653(6) 0.3898(9) 0.2367(2) 0.099(3) Uani 1 1 d . . . H37 H 1.0800 0.3395 0.2596 0.118 Uiso 1 1 calc R . . C38 C 1.1053(6) 0.5227(9) 0.2318(2) 0.100(3) Uani 1 1 d . . . H38 H 1.1451 0.5646 0.2516 0.121 Uiso 1 1 calc R . . C39 C 1.0866(6) 0.5935(8) 0.1979(2) 0.093(2) Uani 1 1 d . . . H39 H 1.1173 0.6807 0.1940 0.112 Uiso 1 1 calc R . . C40 C 1.0226(6) 0.5381(7) 0.1689(2) 0.083(2) Uani 1 1 d . . . H40 H 1.0069 0.5910 0.1465 0.100 Uiso 1 1 calc R . . C41 C 0.9720(4) 0.2587(6) 0.10049(16) 0.0596(15) Uani 1 1 d . . . C42 C 0.9326(5) 0.2321(6) 0.06338(16) 0.0671(17) Uani 1 1 d . . . H42 H 0.8699 0.2481 0.0562 0.081 Uiso 1 1 calc R . . C43 C 0.9870(6) 0.1813(7) 0.0369(2) 0.083(2) Uani 1 1 d . . . H43 H 0.9603 0.1631 0.0120 0.100 Uiso 1 1 calc R . . C44 C 1.0786(7) 0.1580(7) 0.0469(2) 0.093(2) Uani 1 1 d . . . H44 H 1.1143 0.1255 0.0287 0.112 Uiso 1 1 calc R . . C45 C 1.1192(6) 0.1825(7) 0.0841(2) 0.084(2) Uani 1 1 d . . . H45 H 1.1819 0.1659 0.0910 0.101 Uiso 1 1 calc R . . C46 C 1.0653(5) 0.2322(6) 0.11097(18) 0.0684(17) Uani 1 1 d . . . H46 H 1.0920 0.2477 0.1360 0.082 Uiso 1 1 calc R . . F3 F 0.4788(5) 0.3966(9) 0.26102(19) 0.223(4) Uani 1 1 d . . . F1 F 0.4102(7) 0.5539(8) 0.2235(3) 0.230(5) Uani 1 1 d . . . F2 F 0.4886(6) 0.4027(12) 0.2032(3) 0.218(4) Uani 1 1 d . . . F4 F 0.2481(5) -0.1100(6) 0.2350(3) 0.195(3) Uani 1 1 d . . . F5 F 0.1756(7) 0.0230(9) 0.2648(3) 0.217(4) Uani 1 1 d . . . F6 F 0.1299(6) -0.0180(7) 0.2091(3) 0.225(5) Uani 1 1 d . . . F7 F 0.5794(4) 0.4491(5) 0.11595(15) 0.1110(15) Uani 1 1 d . . . F9 F 0.5020(4) 0.6224(6) 0.13661(16) 0.1289(19) Uani 1 1 d . . . F8 F 0.6380(3) 0.5685(5) 0.16468(12) 0.1070(14) Uani 1 1 d . . . F11 F 0.5758(9) 1.0482(12) 0.0316(4) 0.116(4) Uiso 0.484(12) 1 d P . . F10 F 0.6829(9) 1.1293(11) 0.0682(3) 0.115(4) Uiso 0.484(12) 1 d P . . F12 F 0.7164(10) 1.0113(11) 0.0220(4) 0.119(5) Uiso 0.484(12) 1 d P . . F10A F 0.5908(9) 1.1052(11) 0.0581(3) 0.125(4) Uiso 0.516(12) 1 d P . . F11A F 0.6228(9) 0.9844(10) 0.0102(4) 0.121(4) Uiso 0.516(12) 1 d P . . F12A F 0.7309(10) 1.0764(13) 0.0494(3) 0.128(4) Uiso 0.516(12) 1 d P . . 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 0.0663(2) 0.06384(14) 0.05678(14) 0.00907(9) 0.00849(11) 0.00414(10) Au2 0.05145(18) 0.06835(14) 0.06039(14) 0.00199(9) 0.00613(10) 0.00817(10) P1 0.0630(13) 0.0587(8) 0.0560(9) 0.0050(6) 0.0089(7) 0.0071(7) P2 0.0546(12) 0.0603(8) 0.0574(9) 0.0027(6) 0.0039(7) 0.0021(7) N1 0.060(4) 0.076(3) 0.058(3) 0.006(2) 0.009(3) -0.002(3) N2 0.056(4) 0.068(3) 0.063(3) -0.001(2) 0.009(2) 0.012(2) N3 0.065(4) 0.072(3) 0.080(4) 0.014(2) -0.002(3) -0.009(3) N4 0.061(4) 0.076(3) 0.070(3) 0.007(2) 0.007(3) 0.004(3) C1 0.061(5) 0.081(4) 0.067(4) 0.011(3) 0.002(3) -0.006(3) C2 0.073(6) 0.092(4) 0.058(4) 0.017(3) 0.006(3) 0.003(4) C3 0.073(6) 0.069(4) 0.078(4) 0.015(3) 0.016(4) -0.001(3) C4 0.112(10) 0.186(11) 0.086(7) 0.039(6) -0.023(6) -0.068(8) C5 0.134(11) 0.100(7) 0.119(8) 0.041(5) 0.010(7) -0.021(6) C6 0.067(5) 0.056(3) 0.059(3) 0.010(2) 0.011(3) 0.004(3) C7 0.076(6) 0.066(4) 0.084(5) 0.002(3) 0.020(4) 0.007(3) C8 0.067(6) 0.073(4) 0.103(5) 0.007(3) 0.028(4) 0.021(4) C9 0.058(6) 0.105(5) 0.095(5) 0.038(4) 0.017(4) 0.003(4) C10 0.068(6) 0.080(4) 0.092(5) 0.011(3) 0.001(4) -0.001(4) C11 0.068(6) 0.061(3) 0.089(5) 0.002(3) 0.009(4) 0.010(3) C12 0.058(4) 0.053(3) 0.060(3) 0.002(2) 0.014(3) 0.003(3) C13 0.061(5) 0.061(3) 0.077(4) 0.011(3) 0.011(3) 0.004(3) C14 0.067(6) 0.076(4) 0.103(6) -0.009(3) 0.028(4) 0.010(3) C15 0.090(6) 0.087(4) 0.067(4) -0.019(3) 0.024(4) 0.000(4) C16 0.109(7) 0.100(5) 0.053(4) -0.002(3) 0.007(4) 0.019(5) C17 0.072(5) 0.086(4) 0.067(4) 0.002(3) 0.004(3) 0.017(4) C18 0.057(5) 0.061(3) 0.066(4) -0.002(2) 0.012(3) 0.009(3) C19 0.081(6) 0.063(4) 0.077(4) 0.002(3) 0.013(4) 0.001(3) C20 0.077(6) 0.071(4) 0.102(6) 0.008(3) 0.017(4) 0.005(3) C21 0.077(6) 0.060(4) 0.139(8) -0.011(4) 0.020(5) -0.001(4) C22 0.094(7) 0.086(5) 0.096(6) -0.027(4) 0.000(5) -0.003(4) C23 0.101(7) 0.068(4) 0.072(4) -0.009(3) 0.010(4) 0.002(3) C24 0.060(5) 0.083(4) 0.064(4) -0.004(3) 0.011(3) 0.005(3) C25 0.043(5) 0.091(4) 0.092(5) 0.000(3) 0.002(3) 0.025(3) C26 0.056(5) 0.077(4) 0.079(4) 0.011(3) 0.004(3) 0.010(3) C27 0.053(6) 0.106(5) 0.090(5) 0.004(4) 0.016(4) 0.013(4) C28 0.074(7) 0.113(6) 0.123(8) 0.000(5) -0.001(6) 0.030(5) C29 0.071(6) 0.068(4) 0.063(4) 0.008(3) 0.003(3) -0.007(3) C30 0.083(8) 0.115(6) 0.111(6) 0.041(5) 0.013(5) -0.006(5) C31 0.070(7) 0.180(10) 0.142(9) 0.067(8) 0.000(6) -0.051(7) C32 0.176(14) 0.134(8) 0.087(7) 0.025(6) -0.017(7) -0.093(9) C33 0.204(13) 0.079(5) 0.067(5) 0.004(3) 0.011(6) -0.049(6) C34 0.140(8) 0.072(4) 0.068(4) -0.004(3) 0.016(5) -0.012(4) C35 0.051(4) 0.063(3) 0.059(3) -0.006(2) 0.005(3) 0.002(3) C36 0.091(6) 0.081(4) 0.064(4) -0.006(3) 0.003(4) 0.004(4) C37 0.112(8) 0.112(6) 0.065(5) -0.007(4) -0.012(4) 0.005(5) C38 0.087(7) 0.121(7) 0.085(6) -0.040(5) -0.019(5) 0.012(5) C39 0.086(7) 0.081(5) 0.110(6) -0.021(4) 0.007(5) -0.015(4) C40 0.080(6) 0.077(4) 0.089(5) -0.004(3) -0.005(4) -0.009(4) C41 0.055(5) 0.063(3) 0.059(4) 0.004(2) 0.002(3) 0.008(3) C42 0.073(5) 0.062(3) 0.064(4) 0.001(2) 0.002(3) 0.010(3) C43 0.102(7) 0.081(4) 0.068(4) -0.007(3) 0.016(4) 0.010(4) C44 0.109(8) 0.079(4) 0.100(6) -0.005(4) 0.042(5) 0.014(4) C45 0.072(6) 0.079(4) 0.103(6) -0.006(4) 0.021(4) 0.009(4) C46 0.063(5) 0.065(3) 0.076(4) -0.005(3) 0.008(3) 0.007(3) F3 0.207(8) 0.275(8) 0.153(6) 0.089(6) -0.103(5) -0.146(7) F1 0.286(12) 0.136(5) 0.228(8) 0.048(6) -0.107(8) -0.116(7) F2 0.140(7) 0.301(12) 0.217(9) 0.026(7) 0.038(6) -0.119(7) F4 0.165(7) 0.101(4) 0.325(10) 0.085(5) 0.056(6) 0.007(4) F5 0.267(11) 0.224(8) 0.178(8) 0.033(5) 0.097(7) -0.118(7) F6 0.182(8) 0.167(6) 0.295(11) 0.101(6) -0.080(8) -0.107(5) F7 0.107(4) 0.096(3) 0.131(4) 0.005(3) 0.021(3) -0.016(3) F9 0.076(4) 0.144(4) 0.179(5) 0.044(3) 0.061(3) 0.027(3) F8 0.108(4) 0.139(3) 0.075(3) 0.018(2) 0.018(3) -0.004(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 P1 2.2390(14) . ? Au1 N1 2.048(5) . ? Au2 P2 2.2431(15) . ? Au2 N2 2.058(5) . ? P1 C6 1.817(6) . ? P1 C12 1.816(6) . ? P1 C18 1.820(6) . ? P2 C29 1.812(6) . ? P2 C35 1.807(6) . ? P2 C41 1.813(6) . ? N1 N3 1.340(7) . ? N1 C1 1.356(7) . ? N2 N4 1.356(6) . ? N2 C24 1.340(8) . ? N3 C3 1.331(7) . ? N4 C26 1.339(8) . ? C1 C2 1.372(8) . ? C1 C4 1.431(11) . ? C2 H2 0.9300 . ? C2 C3 1.359(9) . ? C3 C5 1.489(11) . ? C4 F3 1.309(9) . ? C4 F1 1.303(15) . ? C4 F2 1.312(14) . ? C5 F4 1.297(12) . ? C5 F5 1.282(13) . ? C5 F6 1.246(12) . ? C6 C7 1.384(8) . ? C6 C11 1.391(8) . ? C7 H7 0.9300 . ? C7 C8 1.368(9) . ? C8 H8 0.9300 . ? C8 C9 1.386(10) . ? C9 H9 0.9300 . ? C9 C10 1.360(10) . ? C10 H10 0.9300 . ? C10 C11 1.385(9) . ? C11 H11 0.9300 . ? C12 C13 1.369(8) . ? C12 C17 1.401(8) . ? C13 H13 0.9300 . ? C13 C14 1.404(8) . ? C14 H14 0.9300 . ? C14 C15 1.368(9) . ? C15 H15 0.9300 . ? C15 C16 1.380(10) . ? C16 H16 0.9300 . ? C16 C17 1.371(9) . ? C17 H17 0.9300 . ? C18 C19 1.385(8) . ? C18 C23 1.375(8) . ? C19 H19 0.9300 . ? C19 C20 1.398(9) . ? C20 H20 0.9300 . ? C20 C21 1.363(10) . ? C21 H21 0.9300 . ? C21 C22 1.357(11) . ? C22 H22 0.9300 . ? C22 C23 1.379(9) . ? C23 H23 0.9300 . ? C24 C25 1.389(8) . ? C24 C27 1.454(10) . ? C25 H25 0.9300 . ? C25 C26 1.381(9) . ? C26 C28 1.503(11) . ? C27 F7 1.357(9) . ? C27 F9 1.315(8) . ? C27 F8 1.348(8) . ? C28 F11 1.263(14) . ? C28 F10 1.371(14) . ? C28 F12 1.314(15) . ? C28 F10A 1.398(14) . ? C28 F11A 1.318(14) . ? C28 F12A 1.251(14) . ? C29 C30 1.369(10) . ? C29 C34 1.396(9) . ? C30 H30 0.9300 . ? C30 C31 1.397(11) . ? C31 H31 0.9300 . ? C31 C32 1.364(17) . ? C32 H32 0.9300 . ? C32 C33 1.347(15) . ? C33 H33 0.9300 . ? C33 C34 1.386(11) . ? C34 H34 0.9300 . ? C35 C36 1.374(8) . ? C35 C40 1.387(9) . ? C36 H36 0.9300 . ? C36 C37 1.384(9) . ? C37 H37 0.9300 . ? C37 C38 1.363(11) . ? C38 H38 0.9300 . ? C38 C39 1.357(10) . ? C39 H39 0.9300 . ? C39 C40 1.385(10) . ? C40 H40 0.9300 . ? C41 C42 1.382(7) . ? C41 C46 1.387(8) . ? C42 H42 0.9300 . ? C42 C43 1.388(9) . ? C43 H43 0.9300 . ? C43 C44 1.355(10) . ? C44 H44 0.9300 . ? C44 C45 1.389(10) . ? C45 H45 0.9300 . ? C45 C46 1.389(9) . ? C46 H46 0.9300 . ? F11 F10A 1.069(12) . ? F11 F11A 1.234(14) . ? F10 F10A 1.365(13) . ? F10 F12A 1.139(14) . ? F12 F11A 1.399(15) . ? F12 F12A 1.129(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Au1 P1 178.00(14) . . ? N2 Au2 P2 175.13(14) . . ? C6 P1 Au1 113.13(18) . . ? C6 P1 C18 105.8(3) . . ? C12 P1 Au1 111.65(18) . . ? C12 P1 C6 106.6(3) . . ? C12 P1 C18 106.0(3) . . ? C18 P1 Au1 113.2(2) . . ? C29 P2 Au2 111.7(2) . . ? C29 P2 C41 106.2(3) . . ? C35 P2 Au2 109.44(19) . . ? C35 P2 C29 108.1(3) . . ? C35 P2 C41 106.3(3) . . ? C41 P2 Au2 114.79(18) . . ? N3 N1 Au1 118.8(4) . . ? N3 N1 C1 109.5(5) . . ? C1 N1 Au1 131.7(4) . . ? N4 N2 Au2 121.3(4) . . ? C24 N2 Au2 127.5(4) . . ? C24 N2 N4 111.1(5) . . ? C3 N3 N1 104.9(5) . . ? C26 N4 N2 103.9(5) . . ? N1 C1 C2 109.1(6) . . ? N1 C1 C4 122.3(6) . . ? C2 C1 C4 128.6(7) . . ? C1 C2 H2 128.6 . . ? C3 C2 C1 102.8(6) . . ? C3 C2 H2 128.6 . . ? N3 C3 C2 113.7(6) . . ? N3 C3 C5 118.6(7) . . ? C2 C3 C5 127.7(7) . . ? F3 C4 C1 113.5(8) . . ? F3 C4 F2 104.4(12) . . ? F1 C4 C1 117.7(11) . . ? F1 C4 F3 107.7(10) . . ? F1 C4 F2 98.8(9) . . ? F2 C4 C1 113.0(11) . . ? F4 C5 C3 112.8(10) . . ? F5 C5 C3 112.0(9) . . ? F5 C5 F4 101.8(9) . . ? F6 C5 C3 116.7(8) . . ? F6 C5 F4 105.6(10) . . ? F6 C5 F5 106.7(13) . . ? C7 C6 P1 121.7(5) . . ? C7 C6 C11 118.4(6) . . ? C11 C6 P1 119.8(5) . . ? C6 C7 H7 119.8 . . ? C8 C7 C6 120.4(6) . . ? C8 C7 H7 119.8 . . ? C7 C8 H8 119.5 . . ? C7 C8 C9 121.1(6) . . ? C9 C8 H8 119.5 . . ? C8 C9 H9 120.5 . . ? C10 C9 C8 119.1(7) . . ? C10 C9 H9 120.5 . . ? C9 C10 H10 119.8 . . ? C9 C10 C11 120.5(7) . . ? C11 C10 H10 119.8 . . ? C6 C11 H11 119.7 . . ? C10 C11 C6 120.6(6) . . ? C10 C11 H11 119.7 . . ? C13 C12 P1 118.6(4) . . ? C13 C12 C17 119.3(5) . . ? C17 C12 P1 122.1(5) . . ? C12 C13 H13 120.3 . . ? C12 C13 C14 119.4(6) . . ? C14 C13 H13 120.3 . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.8(6) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.8(6) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 119.9(6) . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 119.6 . . ? C16 C17 C12 120.7(6) . . ? C16 C17 H17 119.6 . . ? C19 C18 P1 120.8(5) . . ? C23 C18 P1 120.1(5) . . ? C23 C18 C19 119.1(6) . . ? C18 C19 H19 119.6 . . ? C18 C19 C20 120.9(6) . . ? C20 C19 H19 119.6 . . ? C19 C20 H20 121.0 . . ? C21 C20 C19 118.0(7) . . ? C21 C20 H20 121.0 . . ? C20 C21 H21 119.1 . . ? C22 C21 C20 121.8(7) . . ? C22 C21 H21 119.1 . . ? C21 C22 H22 119.9 . . ? C21 C22 C23 120.3(7) . . ? C23 C22 H22 119.9 . . ? C18 C23 C22 119.9(7) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? N2 C24 C25 108.7(6) . . ? N2 C24 C27 123.3(6) . . ? C25 C24 C27 127.9(7) . . ? C24 C25 H25 128.7 . . ? C26 C25 C24 102.6(6) . . ? C26 C25 H25 128.7 . . ? N4 C26 C25 113.6(6) . . ? N4 C26 C28 117.1(7) . . ? C25 C26 C28 129.4(7) . . ? F7 C27 C24 112.5(6) . . ? F9 C27 C24 113.5(6) . . ? F9 C27 F7 105.5(6) . . ? F9 C27 F8 108.1(7) . . ? F8 C27 C24 113.3(7) . . ? F8 C27 F7 103.1(6) . . ? F11 C28 C26 112.8(10) . . ? F11 C28 F10 100.9(9) . . ? F11 C28 F12 113.6(11) . . ? F11 C28 F10A 47.0(6) . . ? F11 C28 F11A 57.1(8) . . ? F10 C28 C26 111.1(9) . . ? F10 C28 F10A 59.0(7) . . ? F12 C28 C26 115.9(8) . . ? F12 C28 F10 100.8(10) . . ? F12 C28 F10A 137.2(10) . . ? F12 C28 F11A 64.2(8) . . ? F10A C28 C26 106.8(9) . . ? F11A C28 C26 112.1(8) . . ? F11A C28 F10 136.5(9) . . ? F11A C28 F10A 102.9(9) . . ? F12A C28 C26 115.2(9) . . ? F12A C28 F11 130.7(11) . . ? F12A C28 F10 51.3(8) . . ? F12A C28 F12 52.2(8) . . ? F12A C28 F10A 107.0(11) . . ? F12A C28 F11A 111.8(11) . . ? C30 C29 P2 119.5(5) . . ? C30 C29 C34 119.9(7) . . ? C34 C29 P2 120.5(6) . . ? C29 C30 H30 120.3 . . ? C29 C30 C31 119.3(9) . . ? C31 C30 H30 120.3 . . ? C30 C31 H31 119.6 . . ? C32 C31 C30 120.7(11) . . ? C32 C31 H31 119.6 . . ? C31 C32 H32 120.2 . . ? C33 C32 C31 119.6(9) . . ? C33 C32 H32 120.2 . . ? C32 C33 H33 119.2 . . ? C32 C33 C34 121.7(10) . . ? C34 C33 H33 119.2 . . ? C29 C34 H34 120.7 . . ? C33 C34 C29 118.7(10) . . ? C33 C34 H34 120.7 . . ? C36 C35 P2 122.9(5) . . ? C36 C35 C40 119.8(6) . . ? C40 C35 P2 117.3(5) . . ? C35 C36 H36 120.1 . . ? C35 C36 C37 119.7(7) . . ? C37 C36 H36 120.1 . . ? C36 C37 H37 119.7 . . ? C38 C37 C36 120.6(7) . . ? C38 C37 H37 119.7 . . ? C37 C38 H38 120.2 . . ? C39 C38 C37 119.7(7) . . ? C39 C38 H38 120.2 . . ? C38 C39 H39 119.5 . . ? C38 C39 C40 121.1(7) . . ? C40 C39 H39 119.5 . . ? C35 C40 H40 120.5 . . ? C39 C40 C35 119.0(7) . . ? C39 C40 H40 120.5 . . ? C42 C41 P2 120.1(5) . . ? C42 C41 C46 119.5(6) . . ? C46 C41 P2 120.5(4) . . ? C41 C42 H42 120.1 . . ? C41 C42 C43 119.8(7) . . ? C43 C42 H42 120.1 . . ? C42 C43 H43 119.5 . . ? C44 C43 C42 120.9(7) . . ? C44 C43 H43 119.5 . . ? C43 C44 H44 119.9 . . ? C43 C44 C45 120.1(7) . . ? C45 C44 H44 119.9 . . ? C44 C45 H45 120.2 . . ? C44 C45 C46 119.5(7) . . ? C46 C45 H45 120.2 . . ? C41 C46 C45 120.2(6) . . ? C41 C46 H46 119.9 . . ? C45 C46 H46 119.9 . . ? F10A F11 C28 73.1(12) . . ? F10A F11 F11A 134.6(17) . . ? F11A F11 C28 63.7(10) . . ? F10A F10 C28 61.5(8) . . ? F12A F10 C28 58.9(9) . . ? F12A F10 F10A 116.3(14) . . ? C28 F12 F11A 58.0(9) . . ? F12A F12 C28 61.0(10) . . ? F12A F12 F11A 114.2(15) . . ? F11 F10A C28 59.9(10) . . ? F11 F10A F10 112.7(15) . . ? F10 F10A C28 59.5(8) . . ? C28 F11A F12 57.8(9) . . ? F11 F11A C28 59.2(9) . . ? F11 F11A F12 109.8(13) . . ? F10 F12A C28 69.8(11) . . ? F12 F12A C28 66.8(11) . . ? F12 F12A F10 131.7(18) . . ?