# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Elena Cerrada' _publ_contact_author_email ecerrada@unizar.es loop_ _publ_author_name E.Vergara E.Cerrada A.Casini P.J.Dyson M.Laguna data_compound3c _database_code_depnum_ccdc_archive 'CCDC 790251' #TrackingRef '- compound3c.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 Au N5 P S' _chemical_formula_weight 493.32 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.735(5) _cell_length_b 7.029(5) _cell_length_c 13.608(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 109.139(5) _cell_angle_gamma 90.000(5) _cell_volume 970.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5404 _cell_measurement_theta_min 3.1291 _cell_measurement_theta_max 26.7755 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 7.771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8237 _exptl_absorpt_correction_T_max 1.1076 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15722 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1846 _reflns_number_gt 1491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD' _computing_cell_refinement 'CrysAlis RED' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'WinGX v1.10.01' _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^)+(0.0481P)^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 1846 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 Au1 Au 0.39138(4) 0.2500 -0.02012(3) 0.02246(16) Uani 1 2 d S . . S1 S 0.5420(3) 0.2500 0.1432(2) 0.0703(14) Uani 1 2 d S . . P1 P 0.2663(3) 0.2500 -0.1877(2) 0.0341(8) Uani 1 2 d S . . N1 N 0.5463(9) 0.2500 0.3351(7) 0.031(2) Uani 1 2 d S . . N4 N 0.2632(10) 0.2500 -0.3902(7) 0.053(3) Uani 1 2 d S . . N3 N 0.0830(7) 0.0741(14) -0.3532(5) 0.056(2) Uani 1 1 d . . . C1 C 0.4922(11) 0.2500 0.4106(8) 0.024(2) Uani 1 2 d S . . C2 C 0.3565(12) 0.2500 0.3855(9) 0.040(3) Uani 1 2 d S . . H2 H 0.3179 0.2500 0.4374 0.048 Uiso 1 2 calc SR . . C3 C 0.2793(12) 0.2500 0.2818(9) 0.039(3) Uani 1 2 d S . . N2 N 0.3307(8) 0.2500 0.2062(6) 0.0211(19) Uani 1 2 d S . . C5 C 0.4636(10) 0.2500 0.2377(8) 0.024(2) Uani 1 2 d S . . C6 C 0.5844(11) 0.2500 0.5198(8) 0.034(3) Uani 1 2 d S . . H6A H 0.6178 0.1237 0.5386 0.052 Uiso 0.50 1 calc PR . . H6B H 0.5382 0.2912 0.5657 0.052 Uiso 0.50 1 calc PR . . H6C H 0.6564 0.3350 0.5255 0.052 Uiso 0.50 1 calc PR . . C7 C 0.1307(13) 0.2500 0.2488(13) 0.114(9) Uani 1 2 d S . . H7A H 0.0949 0.2286 0.1752 0.171 Uiso 0.50 1 calc PR . . H7B H 0.1007 0.3707 0.2654 0.171 Uiso 0.50 1 calc PR . . H7C H 0.1020 0.1507 0.2848 0.171 Uiso 0.50 1 calc PR . . C8 C 0.3566(10) 0.2500 -0.2824(8) 0.042(3) Uani 1 2 d S . . H8A H 0.4125 0.3617 -0.2716 0.050 Uiso 0.50 1 calc PR . . H8B H 0.4125 0.1383 -0.2716 0.050 Uiso 0.50 1 calc PR . . C9 C 0.1514(7) 0.0485(15) -0.2413(6) 0.047(3) Uani 1 1 d . . . H9A H 0.2006 -0.0698 -0.2297 0.056 Uiso 1 1 calc R . . H9B H 0.0871 0.0409 -0.2053 0.056 Uiso 1 1 calc R . . C10 C 0.0053(13) 0.2500 -0.3759(10) 0.069(5) Uani 1 2 d S . . H10A H -0.0478 0.2500 -0.4489 0.083 Uiso 1 2 calc SR . . H10B H -0.0545 0.2500 -0.3357 0.083 Uiso 1 2 calc SR . . C11 C 0.1790(8) 0.0784(18) -0.4101(6) 0.059(3) Uani 1 1 d . . . H11A H 0.1313 0.0704 -0.4840 0.071 Uiso 1 1 calc R . . H11B H 0.2351 -0.0330 -0.3909 0.071 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 0.0222(2) 0.0317(3) 0.0147(2) 0.000 0.00783(16) 0.000 S1 0.0179(16) 0.179(5) 0.0149(15) 0.000 0.0071(13) 0.000 P1 0.0156(14) 0.074(2) 0.0139(14) 0.000 0.0062(12) 0.000 N1 0.024(5) 0.050(7) 0.015(5) 0.000 0.002(4) 0.000 N4 0.027(6) 0.119(10) 0.013(5) 0.000 0.008(4) 0.000 N3 0.024(4) 0.115(8) 0.027(4) -0.012(4) 0.005(3) -0.012(4) C1 0.034(6) 0.021(6) 0.020(5) 0.000 0.014(5) 0.000 C2 0.033(7) 0.062(9) 0.031(7) 0.000 0.018(6) 0.000 C3 0.033(7) 0.059(9) 0.033(7) 0.000 0.023(6) 0.000 N2 0.020(5) 0.027(5) 0.017(4) 0.000 0.006(4) 0.000 C5 0.021(6) 0.029(7) 0.026(6) 0.000 0.015(5) 0.000 C6 0.046(8) 0.039(7) 0.024(6) 0.000 0.019(6) 0.000 C7 0.021(8) 0.28(3) 0.043(9) 0.000 0.015(7) 0.000 C8 0.013(6) 0.096(11) 0.019(6) 0.000 0.010(5) 0.000 C9 0.023(4) 0.091(8) 0.030(5) -0.012(5) 0.013(4) -0.013(5) C10 0.021(7) 0.160(17) 0.024(7) 0.000 0.003(6) 0.000 C11 0.029(5) 0.130(10) 0.020(4) -0.017(5) 0.010(4) -0.010(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 P1 2.235(3) . ? Au1 S1 2.279(3) . ? S1 C5 1.753(10) . ? P1 C8 1.849(11) . ? P1 C9 1.862(9) . ? P1 C9 1.862(9) 4_565 ? N1 C5 1.333(13) . ? N1 C1 1.335(13) . ? N4 C11 1.478(12) . ? N4 C11 1.478(12) 4_565 ? N4 C8 1.480(14) . ? N3 C10 1.467(11) . ? N3 C9 1.469(10) . ? N3 C11 1.477(10) . ? C1 C2 1.383(16) . ? C1 C6 1.491(15) . ? C2 C3 1.382(16) . ? C3 N2 1.318(13) . ? C3 C7 1.509(17) . ? N2 C5 1.348(13) . ? C10 N3 1.467(11) 4_565 ? 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 P1 Au1 S1 172.50(11) . . ? C5 S1 Au1 110.9(4) . . ? C8 P1 C9 99.1(3) . . ? C8 P1 C9 99.1(3) . 4_565 ? C9 P1 C9 99.0(6) . 4_565 ? C8 P1 Au1 115.7(4) . . ? C9 P1 Au1 119.9(3) . . ? C9 P1 Au1 119.9(3) 4_565 . ? C5 N1 C1 116.7(9) . . ? C11 N4 C11 109.4(10) . 4_565 ? C11 N4 C8 110.9(6) . . ? C11 N4 C8 110.9(6) 4_565 . ? C10 N3 C9 112.2(9) . . ? C10 N3 C11 108.6(9) . . ? C9 N3 C11 110.4(6) . . ? N1 C1 C2 119.9(10) . . ? N1 C1 C6 116.9(9) . . ? C2 C1 C6 123.2(10) . . ? C3 C2 C1 118.9(11) . . ? N2 C3 C2 122.2(11) . . ? N2 C3 C7 116.1(11) . . ? C2 C3 C7 121.7(11) . . ? C3 N2 C5 115.0(9) . . ? N1 C5 N2 127.3(9) . . ? N1 C5 S1 114.0(8) . . ? N2 C5 S1 118.7(8) . . ? N4 C8 P1 110.5(7) . . ? N3 C9 P1 110.8(7) . . ? N3 C10 N3 114.9(10) 4_565 . ? N3 C11 N4 114.2(8) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.520 _refine_diff_density_min -1.766 _refine_diff_density_rms 0.198 # Attachment '- compound4d.txt' data_compound4d _database_code_depnum_ccdc_archive 'CCDC 790252' #TrackingRef '- compound4d.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Au N4 O4 P S' _chemical_formula_weight 592.36 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' 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' S S 0.1246 0.1234 '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 6.0539(10) _cell_length_b 10.5087(18) _cell_length_c 15.828(3) _cell_angle_alpha 97.007(3) _cell_angle_beta 96.101(3) _cell_angle_gamma 98.188(3) _cell_volume 981.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3051 _cell_measurement_theta_min 2.213 _cell_measurement_theta_max 27.973 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.072 _exptl_crystal_size_mid 0.057 _exptl_crystal_size_min 0.037 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.011 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 7.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.644221 _exptl_absorpt_correction_T_max 0.813199 _exptl_absorpt_process_details ? _exptl_special_details ; (Sheldrick, M. SADABS empirical absorption program, University of Gottingen, 1996) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9236 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.50 _reflns_number_total 3245 _reflns_number_gt 2915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'WinGX v1.10.01' _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^)+(0.0638P)^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 3245 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.74551(6) 0.34077(3) 0.98025(2) 0.01843(15) Uani 1 1 d . . . S1 S 1.0073(4) 0.3865(3) 1.10202(16) 0.0279(6) Uani 1 1 d . . . P1 P 0.5000(4) 0.2859(2) 0.86056(15) 0.0186(5) Uani 1 1 d . . . N1 N 0.3213(13) 0.3720(7) 0.7139(5) 0.0219(18) Uani 1 1 d . . . N2 N 0.0788(13) 0.2169(8) 0.7838(5) 0.0231(18) Uani 1 1 d . . . N3 N 0.3566(12) 0.0952(7) 0.7235(5) 0.0173(17) Uani 1 1 d . . . N4 N 0.6397(13) 0.2690(7) 1.1664(5) 0.0209(18) Uani 1 1 d . . . O1 O 0.9502(11) 0.3554(6) 1.2609(4) 0.0244(15) Uani 1 1 d . . . O2 O 0.1985(12) 0.3669(7) 0.5735(4) 0.0315(17) Uani 1 1 d . . . O3 O 0.6182(10) 0.1271(6) 0.6325(4) 0.0205(14) Uani 1 1 d . . . C1 C 0.8430(16) 0.3298(9) 1.1768(6) 0.020(2) Uani 1 1 d . . . C2 C 0.5977(16) 0.2494(8) 1.2508(6) 0.020(2) Uani 1 1 d . . . C3 C 0.7838(16) 0.3017(8) 1.3075(6) 0.021(2) Uani 1 1 d . . . C4 C 0.7970(19) 0.2998(10) 1.3938(6) 0.030(2) Uani 1 1 d . . . H4 H 0.9274 0.3346 1.4307 0.036 Uiso 1 1 calc R . . C5 C 0.6060(19) 0.2433(9) 1.4231(6) 0.027(2) Uani 1 1 d . . . H5 H 0.6064 0.2400 1.4816 0.033 Uiso 1 1 calc R . . C6 C 0.4123(19) 0.1911(9) 1.3675(6) 0.028(2) Uani 1 1 d . . . H6 H 0.2860 0.1535 1.3894 0.033 Uiso 1 1 calc R . . C7 C 0.4038(19) 0.1940(9) 1.2798(7) 0.029(2) Uani 1 1 d . . . H7 H 0.2740 0.1602 1.2424 0.035 Uiso 1 1 calc R . . C8 C 0.4920(16) 0.4089(9) 0.7871(6) 0.022(2) Uani 1 1 d . . . H8A H 0.4660 0.4892 0.8188 0.026 Uiso 1 1 calc R . . H8B H 0.6378 0.4254 0.7669 0.026 Uiso 1 1 calc R . . C9 C 0.5276(15) 0.1341(8) 0.7964(6) 0.017(2) Uani 1 1 d . . . H9A H 0.6741 0.1432 0.7763 0.020 Uiso 1 1 calc R . . H9B H 0.5211 0.0659 0.8327 0.020 Uiso 1 1 calc R . . C10 C 0.1991(15) 0.2521(11) 0.8701(6) 0.026(2) Uani 1 1 d . . . H10A H 0.1692 0.1815 0.9035 0.032 Uiso 1 1 calc R . . H10B H 0.1503 0.3283 0.8987 0.032 Uiso 1 1 calc R . . C11 C 0.0918(16) 0.3220(10) 0.7312(7) 0.027(2) Uani 1 1 d . . . H11A H 0.0294 0.3932 0.7597 0.033 Uiso 1 1 calc R . . H11B H -0.0016 0.2914 0.6768 0.033 Uiso 1 1 calc R . . C12 C 0.1236(16) 0.0936(10) 0.7413(6) 0.024(2) Uani 1 1 d . . . H12A H 0.0247 0.0702 0.6876 0.028 Uiso 1 1 calc R . . H12B H 0.0874 0.0269 0.7771 0.028 Uiso 1 1 calc R . . C13 C 0.3560(17) 0.3977(8) 0.6335(6) 0.021(2) Uani 1 1 d . . . C14 C 0.5871(17) 0.4575(9) 0.6197(6) 0.025(2) Uani 1 1 d . . . H14A H 0.6880 0.3954 0.6251 0.037 Uiso 1 1 calc R . . H14B H 0.6387 0.5325 0.6619 0.037 Uiso 1 1 calc R . . H14C H 0.5826 0.4828 0.5634 0.037 Uiso 1 1 calc R . . C15 C 0.4204(16) 0.0955(8) 0.6426(6) 0.018(2) Uani 1 1 d . . . C16 C 0.2402(16) 0.0522(9) 0.5669(6) 0.021(2) Uani 1 1 d . . . H16A H 0.1528 0.1204 0.5596 0.031 Uiso 1 1 calc R . . H16B H 0.1440 -0.0239 0.5769 0.031 Uiso 1 1 calc R . . H16C H 0.3092 0.0326 0.5160 0.031 Uiso 1 1 calc R . . O4 O 0.380(3) 0.0822(12) 1.0316(8) 0.137(7) 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 0.0153(2) 0.0256(2) 0.0136(2) 0.00222(14) 0.00107(14) 0.00139(15) S1 0.0193(13) 0.0423(16) 0.0188(13) 0.0030(11) -0.0007(10) -0.0029(11) P1 0.0161(13) 0.0244(13) 0.0151(12) 0.0023(10) 0.0016(10) 0.0037(10) N1 0.012(4) 0.022(4) 0.030(5) 0.001(4) -0.004(3) 0.001(3) N2 0.010(4) 0.036(5) 0.023(5) 0.003(4) 0.002(3) 0.000(4) N3 0.008(4) 0.022(4) 0.020(4) 0.000(3) -0.001(3) 0.000(3) N4 0.016(4) 0.023(4) 0.022(4) 0.000(3) -0.004(3) 0.003(3) O1 0.028(4) 0.027(4) 0.016(4) 0.002(3) -0.003(3) 0.001(3) O2 0.035(4) 0.026(4) 0.028(4) -0.001(3) -0.013(3) 0.004(3) O3 0.015(4) 0.025(4) 0.020(4) 0.004(3) 0.002(3) 0.000(3) C1 0.024(6) 0.020(5) 0.019(5) 0.006(4) 0.005(4) 0.008(4) C2 0.029(6) 0.011(4) 0.018(5) 0.002(4) -0.004(4) 0.006(4) C3 0.025(6) 0.013(5) 0.022(5) 0.001(4) -0.002(4) 0.002(4) C4 0.042(7) 0.028(6) 0.020(5) -0.003(4) -0.001(5) 0.012(5) C5 0.050(7) 0.016(5) 0.018(5) 0.006(4) 0.010(5) 0.010(5) C6 0.043(7) 0.022(5) 0.021(5) 0.008(4) 0.012(5) 0.004(5) C7 0.035(6) 0.024(5) 0.028(6) 0.004(4) 0.009(5) -0.001(5) C8 0.013(5) 0.023(5) 0.024(5) -0.006(4) -0.008(4) 0.002(4) C9 0.013(5) 0.017(5) 0.018(5) 0.003(4) -0.002(4) -0.002(4) C10 0.010(5) 0.042(6) 0.023(6) -0.002(5) 0.002(4) -0.005(4) C11 0.010(5) 0.035(6) 0.036(6) 0.000(5) 0.000(4) 0.009(4) C12 0.012(5) 0.036(6) 0.023(5) 0.007(4) 0.003(4) 0.002(4) C13 0.027(6) 0.010(4) 0.026(6) 0.002(4) 0.000(5) 0.002(4) C14 0.037(6) 0.017(5) 0.020(5) 0.002(4) -0.004(5) 0.009(4) C15 0.017(5) 0.013(4) 0.025(5) 0.005(4) -0.004(4) 0.002(4) C16 0.018(5) 0.020(5) 0.021(5) 0.000(4) -0.003(4) 0.001(4) O4 0.24(2) 0.065(8) 0.073(9) 0.008(6) -0.021(10) -0.047(10) _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 2.241(2) . ? Au1 S1 2.316(3) . ? S1 C1 1.732(10) . ? P1 C9 1.823(9) . ? P1 C10 1.832(10) . ? P1 C8 1.842(10) . ? N1 C13 1.365(12) . ? N1 C8 1.444(12) . ? N1 C11 1.480(12) . ? N2 C10 1.457(12) . ? N2 C11 1.460(13) . ? N2 C12 1.460(12) . ? N3 C15 1.377(12) . ? N3 C9 1.443(11) . ? N3 C12 1.465(12) . ? N4 C1 1.287(12) . ? N4 C2 1.419(12) . ? O1 C1 1.395(11) . ? O1 C3 1.405(12) . ? O2 C13 1.249(12) . ? O3 C15 1.228(11) . ? C2 C3 1.366(13) . ? C2 C7 1.383(14) . ? C3 C4 1.363(13) . ? C4 C5 1.375(15) . ? C5 C6 1.390(15) . ? C6 C7 1.387(14) . ? C13 C14 1.499(14) . ? C15 C16 1.510(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 S1 176.72(9) . . ? C1 S1 Au1 100.0(3) . . ? C9 P1 C10 98.8(5) . . ? C9 P1 C8 107.0(4) . . ? C10 P1 C8 98.7(5) . . ? C9 P1 Au1 114.6(3) . . ? C10 P1 Au1 119.0(3) . . ? C8 P1 Au1 116.2(3) . . ? C13 N1 C8 122.9(8) . . ? C13 N1 C11 119.6(8) . . ? C8 N1 C11 116.9(8) . . ? C10 N2 C11 114.5(8) . . ? C10 N2 C12 112.7(8) . . ? C11 N2 C12 114.7(8) . . ? C15 N3 C9 118.4(7) . . ? C15 N3 C12 123.4(8) . . ? C9 N3 C12 116.0(7) . . ? C1 N4 C2 103.8(8) . . ? C1 O1 C3 102.5(7) . . ? N4 C1 O1 116.1(8) . . ? N4 C1 S1 130.0(7) . . ? O1 C1 S1 113.9(7) . . ? C3 C2 C7 120.3(9) . . ? C3 C2 N4 109.5(8) . . ? C7 C2 N4 130.0(9) . . ? C4 C3 C2 124.0(10) . . ? C4 C3 O1 127.9(9) . . ? C2 C3 O1 108.1(8) . . ? C3 C4 C5 116.0(10) . . ? C4 C5 C6 121.6(9) . . ? C7 C6 C5 121.2(10) . . ? C2 C7 C6 116.8(10) . . ? N1 C8 P1 113.9(6) . . ? N3 C9 P1 113.7(6) . . ? N2 C10 P1 107.7(6) . . ? N2 C11 N1 114.9(8) . . ? N2 C12 N3 114.2(8) . . ? O2 C13 N1 119.5(9) . . ? O2 C13 C14 122.2(9) . . ? N1 C13 C14 118.2(8) . . ? O3 C15 N3 121.0(8) . . ? O3 C15 C16 121.3(9) . . ? N3 C15 C16 117.7(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.957 _refine_diff_density_min -1.289 _refine_diff_density_rms 0.230