# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Coetzee, Jacorien' 'Cronje, Stephanie' 'Dobrzanska, Liliana' 'Raubenheimer, Helgard' 'Nell, Margo' 'Joone, Gisela' 'Hoppe, Heinrich' _publ_contact_author_name 'Cronje, Stephanie' _publ_contact_author_email scron@sun.ac.za _publ_section_title ; Novel N-heterocyclic ylideneamine gold(I) complexes: synthesis, characterisation and screening for antitumour and antimalarial activity ; # Attachment '- Revised Ylideneamine gold(I).CIF' data_I _database_code_depnum_ccdc_archive 'CCDC 801423' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common work _chemical_formula_moiety 'C9 H11 N3, 3(H2 O)' _chemical_formula_sum 'C9 H17 N3 O3' _chemical_melting_point '59-60 ^o^C' _exptl_crystal_description block _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 215.26 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.348(3) _cell_length_b 12.090(4) _cell_length_c 8.619(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.098(5) _cell_angle_gamma 90.00 _cell_volume 1170.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1740 _cell_measurement_theta_min 2.475 _cell_measurement_theta_max 26.1485 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9793 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6351 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2400 _reflns_number_gt 2069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The H atoms of the water molecules were located in a difference Fourier map and their geometrical positions were refined with restraints on the distances and angles.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^)+(0.0542P)^2^+0.6984P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2400 _refine_ls_number_parameters 166 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.113 _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 O1 O 0.99355(14) 0.77428(13) 0.09541(16) 0.0300(4) Uani 1 1 d D . . N1 N 0.66456(15) 0.64818(14) 0.02249(19) 0.0252(4) Uani 1 1 d . . . C1 C 0.75336(18) 0.57993(16) 0.0927(2) 0.0210(4) Uani 1 1 d . . . O2 O 1.11900(14) 0.67105(14) 0.35876(17) 0.0321(4) Uani 1 1 d D . . N2 N 0.70431(14) 0.51920(13) 0.20222(18) 0.0205(4) Uani 1 1 d . . . C2 C 0.58496(18) 0.54693(16) 0.1981(2) 0.0222(4) Uani 1 1 d . . . O3 O 0.91249(15) 0.95440(13) 0.24383(19) 0.0362(4) Uani 1 1 d D . . N3 N 0.86018(16) 0.57882(15) 0.0562(2) 0.0261(4) Uani 1 1 d . . . C3 C 0.49960(19) 0.50911(19) 0.2845(2) 0.0290(5) Uani 1 1 d . . . H3 H 0.5169 0.4531 0.3617 0.035 Uiso 1 1 calc R . . C4 C 0.3867(2) 0.5568(2) 0.2535(3) 0.0370(6) Uani 1 1 d . . . H4 H 0.3259 0.5331 0.3112 0.044 Uiso 1 1 calc R . . C5 C 0.3617(2) 0.6378(2) 0.1406(3) 0.0378(6) Uani 1 1 d . . . H5 H 0.2839 0.6682 0.1220 0.045 Uiso 1 1 calc R . . C6 C 0.4476(2) 0.67591(19) 0.0534(3) 0.0331(5) Uani 1 1 d . . . H6 H 0.4302 0.7318 -0.0239 0.040 Uiso 1 1 calc R . . C7 C 0.55988(19) 0.62871(17) 0.0842(2) 0.0245(5) Uani 1 1 d . . . C8 C 0.6797(2) 0.7268(2) -0.1003(3) 0.0396(6) Uani 1 1 d . . . H8C H 0.6017 0.7549 -0.1469 0.059 Uiso 1 1 calc R . . H8B H 0.7183 0.6902 -0.1812 0.059 Uiso 1 1 calc R . . H8A H 0.7293 0.7885 -0.0556 0.059 Uiso 1 1 calc R . . C9 C 0.76843(19) 0.43521(18) 0.3005(3) 0.0299(5) Uani 1 1 d . . . H9A H 0.7805 0.3701 0.2368 0.045 Uiso 1 1 calc R . . H9B H 0.7223 0.4142 0.3838 0.045 Uiso 1 1 calc R . . H9C H 0.8459 0.4646 0.3472 0.045 Uiso 1 1 calc R . . H10 H 0.908(2) 0.525(2) 0.114(3) 0.040(7) Uiso 1 1 d . . . H11 H 0.944(2) 0.7123(18) 0.065(3) 0.055(8) Uiso 1 1 d D . . H12 H 1.035(3) 0.796(3) 0.007(3) 0.091(12) Uiso 1 1 d D . . H13 H 1.082(2) 0.712(2) 0.272(3) 0.051(8) Uiso 1 1 d D . . H14 H 1.111(3) 0.5932(17) 0.331(4) 0.088(12) Uiso 1 1 d D . . H15 H 0.888(3) 0.935(2) 0.339(2) 0.069(10) Uiso 1 1 d D . . H16 H 0.934(3) 0.887(2) 0.192(3) 0.094(12) Uiso 1 1 d 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 O1 0.0418(9) 0.0267(8) 0.0230(7) -0.0018(6) 0.0094(7) -0.0073(7) N1 0.0334(10) 0.0213(9) 0.0196(8) 0.0034(7) -0.0009(7) 0.0022(7) C1 0.0285(11) 0.0173(9) 0.0161(9) 0.0003(8) -0.0008(8) 0.0000(8) O2 0.0385(9) 0.0320(9) 0.0260(8) 0.0008(7) 0.0046(7) 0.0032(7) N2 0.0232(9) 0.0195(8) 0.0180(8) 0.0014(7) 0.0000(6) 0.0004(7) C2 0.0251(10) 0.0202(10) 0.0199(9) -0.0073(8) -0.0020(8) 0.0020(8) O3 0.0475(10) 0.0298(9) 0.0355(9) -0.0006(7) 0.0202(8) 0.0011(8) N3 0.0280(10) 0.0239(9) 0.0264(9) 0.0051(8) 0.0037(7) -0.0015(8) C3 0.0285(11) 0.0308(11) 0.0280(11) -0.0052(9) 0.0053(9) -0.0018(9) C4 0.0281(12) 0.0424(14) 0.0412(13) -0.0188(11) 0.0080(10) -0.0033(10) C5 0.0265(12) 0.0399(14) 0.0444(13) -0.0223(12) -0.0043(10) 0.0071(10) C6 0.0364(13) 0.0270(11) 0.0314(11) -0.0099(9) -0.0105(9) 0.0098(10) C7 0.0300(11) 0.0215(10) 0.0197(9) -0.0089(8) -0.0036(8) 0.0018(9) C8 0.0503(15) 0.0333(13) 0.0340(12) 0.0152(10) 0.0013(11) 0.0061(11) C9 0.0296(12) 0.0301(11) 0.0299(11) 0.0133(9) 0.0042(9) 0.0050(9) _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 O1 H11 0.951(17) . ? O1 H12 0.982(17) . ? N1 C1 1.375(3) . ? N1 C7 1.388(3) . ? N1 C8 1.451(3) . ? C1 N3 1.295(3) . ? C1 N2 1.374(2) . ? O2 H13 0.944(17) . ? O2 H14 0.971(18) . ? N2 C2 1.391(3) . ? N2 C9 1.451(3) . ? C2 C3 1.380(3) . ? C2 C7 1.394(3) . ? O3 H15 0.937(16) . ? O3 H16 0.974(17) . ? N3 H10 0.94(3) . ? C3 C4 1.396(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 H11 O1 H12 109(2) . . ? C1 N1 C7 110.06(16) . . ? C1 N1 C8 124.04(18) . . ? C7 N1 C8 125.88(18) . . ? N3 C1 N2 130.20(18) . . ? N3 C1 N1 123.52(18) . . ? N2 C1 N1 106.29(17) . . ? H13 O2 H14 107(3) . . ? C1 N2 C2 109.94(16) . . ? C1 N2 C9 123.82(17) . . ? C2 N2 C9 126.17(17) . . ? C3 C2 N2 131.40(19) . . ? C3 C2 C7 121.72(19) . . ? N2 C2 C7 106.87(17) . . ? H15 O3 H16 108.7(18) . . ? C1 N3 H10 111.3(15) . . ? C2 C3 C4 117.1(2) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 117.1(2) . . ? C7 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? C6 C7 N1 132.0(2) . . ? C6 C7 C2 121.2(2) . . ? N1 C7 C2 106.82(17) . . ? N1 C8 H8C 109.5 . . ? N1 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? N1 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 N3 178.79(18) . . . . ? C8 N1 C1 N3 0.0(3) . . . . ? C7 N1 C1 N2 -1.5(2) . . . . ? C8 N1 C1 N2 179.65(19) . . . . ? N3 C1 N2 C2 -178.8(2) . . . . ? N1 C1 N2 C2 1.5(2) . . . . ? N3 C1 N2 C9 -1.6(3) . . . . ? N1 C1 N2 C9 178.72(17) . . . . ? C1 N2 C2 C3 -179.9(2) . . . . ? C9 N2 C2 C3 3.0(3) . . . . ? C1 N2 C2 C7 -1.0(2) . . . . ? C9 N2 C2 C7 -178.09(18) . . . . ? N2 C2 C3 C4 178.43(19) . . . . ? C7 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 N1 -178.6(2) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C1 N1 C7 C6 179.5(2) . . . . ? C8 N1 C7 C6 -1.7(3) . . . . ? C1 N1 C7 C2 0.9(2) . . . . ? C8 N1 C7 C2 179.74(19) . . . . ? C3 C2 C7 C6 0.3(3) . . . . ? N2 C2 C7 C6 -178.75(17) . . . . ? C3 C2 C7 N1 179.04(18) . . . . ? N2 C2 C7 N1 0.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.275 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.050 #===END data_II _database_code_depnum_ccdc_archive 'CCDC 801424' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point '46-48 ^o^C' _chemical_formula_moiety 'C5 H8 N2 S' _chemical_formula_sum 'C5 H8 N2 S' _chemical_formula_weight 128.19 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' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9494(14) _cell_length_b 13.498(3) _cell_length_c 14.301(3) _cell_angle_alpha 108.286(3) _cell_angle_beta 101.346(3) _cell_angle_gamma 91.652(3) _cell_volume 1242.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1620 _cell_measurement_theta_min 2.5515 _cell_measurement_theta_max 25.652 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8874 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6852 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0968 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.69 _reflns_number_total 4625 _reflns_number_gt 3101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0265P)^2^] 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 4625 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.880 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.28681(11) -0.12126(6) 1.05834(6) 0.01761(19) Uani 1 1 d . . . N1 N 0.2697(3) 0.05823(17) 1.03296(17) 0.0147(5) Uani 1 1 d . . . C1 C 0.3141(4) 0.0180(2) 1.1108(2) 0.0150(7) Uani 1 1 d . . . S2 S 0.17573(11) 0.29950(6) 0.83201(6) 0.0205(2) Uani 1 1 d . . . N2 N 0.3658(4) 0.07499(18) 1.20362(18) 0.0179(6) Uani 1 1 d . . . H8 H 0.3852 0.0395 1.2368 0.022 Uiso 1 1 calc R . . C2 C 0.2151(4) -0.0160(2) 0.9362(2) 0.0164(7) Uani 1 1 d . . . S3 S 0.90125(11) 0.70773(6) 0.68916(6) 0.01976(19) Uani 1 1 d . . . N3 N 0.0479(3) 0.47984(18) 0.87299(18) 0.0177(6) Uani 1 1 d . . . C3 C 0.2173(4) -0.1143(2) 0.9369(2) 0.0180(7) Uani 1 1 d . . . H1 H 0.1846 -0.1740 0.8777 0.022 Uiso 1 1 calc R . . S4 S 0.32297(11) 0.18618(6) 0.56989(6) 0.02025(19) Uani 1 1 d . . . N4 N -0.2060(3) 0.34876(19) 0.8381(2) 0.0229(6) Uani 1 1 d . . . H16 H -0.2234 0.2885 0.8177 0.028 Uiso 1 1 calc R . . C4 C 0.2796(4) 0.1714(2) 1.0561(2) 0.0188(7) Uani 1 1 d . . . H2 H 0.1854 0.1999 1.0981 0.028 Uiso 1 1 calc R . . H4 H 0.2469 0.1881 0.9933 0.028 Uiso 1 1 calc R . . H3 H 0.4133 0.2025 1.0926 0.028 Uiso 1 1 calc R . . N5 N 0.6854(3) 0.53424(18) 0.63639(18) 0.0192(6) Uani 1 1 d . . . C5 C 0.1631(4) 0.0174(2) 0.8451(2) 0.0196(7) Uani 1 1 d . . . H7 H 0.1242 -0.0447 0.7848 0.029 Uiso 1 1 calc R . . H6 H 0.2775 0.0575 0.8395 0.029 Uiso 1 1 calc R . . H5 H 0.0532 0.0612 0.8512 0.029 Uiso 1 1 calc R . . N6 N 0.5072(3) 0.67740(18) 0.69110(19) 0.0199(6) Uani 1 1 d . . . H24 H 0.5256 0.7375 0.7146 0.024 Uiso 1 1 calc R . . C6 C -0.0250(4) 0.3771(2) 0.8469(2) 0.0170(7) Uani 1 1 d . . . N7 N 0.6608(3) 0.11630(18) 0.58032(18) 0.0160(6) Uani 1 1 d . . . C7 C 0.2498(4) 0.4975(2) 0.8787(2) 0.0176(7) Uani 1 1 d . . . N8 N 0.5358(4) 0.1230(2) 0.72179(19) 0.0226(6) Uani 1 1 d . . . H32 H 0.4438 0.1392 0.7432 0.027 Uiso 1 1 calc R . . C8 C 0.3401(4) 0.4103(2) 0.8592(2) 0.0213(7) Uani 1 1 d . . . H9 H 0.4770 0.4083 0.8599 0.026 Uiso 1 1 calc R . . C9 C -0.0869(4) 0.5618(2) 0.8912(2) 0.0250(8) Uani 1 1 d . . . H12 H -0.1741 0.5582 0.8271 0.037 Uiso 1 1 calc R . . H11 H -0.0107 0.6306 0.9211 0.037 Uiso 1 1 calc R . . H10 H -0.1663 0.5513 0.9374 0.037 Uiso 1 1 calc R . . C10 C 0.3425(4) 0.6061(2) 0.9054(2) 0.0260(8) Uani 1 1 d . . . H15 H 0.4834 0.6044 0.9054 0.039 Uiso 1 1 calc R . . H14 H 0.3257 0.6476 0.9725 0.039 Uiso 1 1 calc R . . H13 H 0.2795 0.6379 0.8557 0.039 Uiso 1 1 calc R . . C11 C 0.6668(4) 0.6400(2) 0.6735(2) 0.0164(7) Uani 1 1 d . . . C12 C 0.8735(4) 0.5066(2) 0.6240(2) 0.0197(7) Uani 1 1 d . . . C13 C 1.0052(4) 0.5896(2) 0.6480(2) 0.0208(7) Uani 1 1 d . . . H17 H 1.1393 0.5849 0.6434 0.025 Uiso 1 1 calc R . . C14 C 0.5161(4) 0.4594(2) 0.6190(2) 0.0286(8) Uani 1 1 d . . . H18 H 0.4063 0.4723 0.5710 0.043 Uiso 1 1 calc R . . H19 H 0.4765 0.4676 0.6829 0.043 Uiso 1 1 calc R . . H20 H 0.5517 0.3879 0.5913 0.043 Uiso 1 1 calc R . . C15 C 0.9092(5) 0.3940(2) 0.5871(2) 0.0279(8) Uani 1 1 d . . . H23 H 1.0465 0.3886 0.5804 0.042 Uiso 1 1 calc R . . H22 H 0.8210 0.3594 0.5213 0.042 Uiso 1 1 calc R . . H21 H 0.8837 0.3600 0.6354 0.042 Uiso 1 1 calc R . . C16 C 0.5181(4) 0.1376(2) 0.6365(2) 0.0167(7) Uani 1 1 d . . . C17 C 0.6184(4) 0.1361(2) 0.4889(2) 0.0177(7) Uani 1 1 d . . . C18 C 0.4442(4) 0.1732(2) 0.4712(2) 0.0200(7) Uani 1 1 d . . . H25 H 0.3923 0.1904 0.4122 0.024 Uiso 1 1 calc R . . C19 C 0.8431(4) 0.0785(2) 0.6205(2) 0.0235(7) Uani 1 1 d . . . H26 H 0.9226 0.1357 0.6769 0.035 Uiso 1 1 calc R . . H28 H 0.9175 0.0539 0.5674 0.035 Uiso 1 1 calc R . . H27 H 0.8115 0.0206 0.6442 0.035 Uiso 1 1 calc R . . C20 C 0.7629(4) 0.1171(2) 0.4215(2) 0.0216(7) Uani 1 1 d . . . H31 H 0.7116 0.1381 0.3624 0.032 Uiso 1 1 calc R . . H30 H 0.7829 0.0424 0.3996 0.032 Uiso 1 1 calc R . . H29 H 0.8889 0.1583 0.4585 0.032 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 S1 0.0204(4) 0.0140(4) 0.0186(4) 0.0048(3) 0.0055(3) 0.0024(3) N1 0.0171(13) 0.0128(13) 0.0152(14) 0.0043(11) 0.0058(11) 0.0031(10) C1 0.0105(15) 0.0156(16) 0.0212(17) 0.0055(13) 0.0090(13) 0.0028(12) S2 0.0203(4) 0.0153(4) 0.0273(5) 0.0065(4) 0.0083(4) 0.0053(3) N2 0.0230(15) 0.0171(13) 0.0163(14) 0.0079(11) 0.0058(12) 0.0050(11) C2 0.0105(15) 0.0176(16) 0.0209(17) 0.0034(14) 0.0076(13) 0.0027(12) S3 0.0181(4) 0.0180(4) 0.0233(5) 0.0074(4) 0.0041(3) 0.0006(3) N3 0.0184(14) 0.0151(13) 0.0209(15) 0.0059(11) 0.0064(11) 0.0071(10) C3 0.0170(16) 0.0205(17) 0.0132(16) 0.0009(13) 0.0033(13) 0.0013(13) S4 0.0169(4) 0.0239(4) 0.0243(5) 0.0119(4) 0.0074(3) 0.0053(3) N4 0.0191(15) 0.0206(14) 0.0297(17) 0.0078(14) 0.0075(12) -0.0002(11) C4 0.0243(18) 0.0156(16) 0.0188(18) 0.0075(14) 0.0064(14) 0.0054(13) N5 0.0191(14) 0.0161(14) 0.0229(15) 0.0062(12) 0.0059(11) -0.0002(11) C5 0.0168(16) 0.0231(17) 0.0197(18) 0.0061(14) 0.0068(13) 0.0036(13) N6 0.0201(14) 0.0174(14) 0.0223(15) 0.0059(13) 0.0054(12) 0.0035(11) C6 0.0188(17) 0.0181(16) 0.0167(17) 0.0081(14) 0.0052(13) 0.0051(13) N7 0.0137(13) 0.0184(14) 0.0182(14) 0.0082(11) 0.0045(11) 0.0043(10) C7 0.0181(16) 0.0194(17) 0.0176(17) 0.0066(14) 0.0082(13) 0.0025(13) N8 0.0267(16) 0.0224(15) 0.0222(16) 0.0095(12) 0.0091(12) 0.0041(12) C8 0.0147(16) 0.0212(17) 0.0286(19) 0.0082(15) 0.0062(14) 0.0010(13) C9 0.0253(19) 0.0216(17) 0.031(2) 0.0097(15) 0.0087(15) 0.0103(14) C10 0.0230(18) 0.0236(18) 0.031(2) 0.0099(16) 0.0041(15) 0.0028(14) C11 0.0181(16) 0.0173(16) 0.0144(16) 0.0078(13) 0.0010(13) -0.0020(13) C12 0.0243(18) 0.0207(17) 0.0160(17) 0.0066(14) 0.0069(14) 0.0089(14) C13 0.0215(17) 0.0229(17) 0.0214(18) 0.0098(14) 0.0070(14) 0.0094(14) C14 0.0282(19) 0.0190(17) 0.036(2) 0.0055(16) 0.0066(16) -0.0031(14) C15 0.034(2) 0.0232(18) 0.030(2) 0.0074(16) 0.0144(16) 0.0121(15) C16 0.0176(16) 0.0135(16) 0.0197(18) 0.0057(13) 0.0053(13) 0.0002(13) C17 0.0191(17) 0.0145(16) 0.0157(17) 0.0017(13) 0.0013(13) -0.0024(13) C18 0.0180(17) 0.0272(18) 0.0168(17) 0.0106(14) 0.0027(13) 0.0039(14) C19 0.0205(17) 0.0235(17) 0.0277(19) 0.0096(15) 0.0053(14) 0.0079(13) C20 0.0205(17) 0.0232(18) 0.0222(18) 0.0073(15) 0.0072(14) 0.0023(14) _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 S1 C3 1.742(3) . ? S1 C1 1.781(3) . ? N1 C1 1.372(4) . ? N1 C2 1.401(3) . ? N1 C4 1.455(3) . ? C1 N2 1.280(3) . ? S2 C8 1.748(3) . ? S2 C6 1.775(3) . ? N2 H8 0.7700 . ? C2 C3 1.329(4) . ? C2 C5 1.491(4) . ? S3 C13 1.748(3) . ? S3 C11 1.784(3) . ? N3 C6 1.371(4) . ? N3 C7 1.398(4) . ? N3 C9 1.464(3) . ? C3 H1 0.9500 . ? S4 C18 1.747(3) . ? S4 C16 1.764(3) . ? N4 C6 1.274(3) . ? N4 H16 0.7700 . ? C4 H2 0.9800 . ? C4 H4 0.9800 . ? C4 H3 0.9800 . ? N5 C11 1.378(3) . ? N5 C12 1.399(4) . ? N5 C14 1.458(4) . ? C5 H7 0.9800 . ? C5 H6 0.9800 . ? C5 H5 0.9800 . ? N6 C11 1.269(3) . ? N6 H24 0.7700 . ? N7 C16 1.377(4) . ? N7 C17 1.393(4) . ? N7 C19 1.460(3) . ? C7 C8 1.328(4) . ? C7 C10 1.485(4) . ? N8 C16 1.278(4) . ? N8 H32 0.7700 . ? C8 H9 0.9500 . ? C9 H12 0.9800 . ? C9 H11 0.9800 . ? C9 H10 0.9800 . ? C10 H15 0.9800 . ? C10 H14 0.9800 . ? C10 H13 0.9800 . ? C12 C13 1.336(4) . ? C12 C15 1.491(4) . ? C13 H17 0.9500 . ? C14 H18 0.9800 . ? C14 H19 0.9800 . ? C14 H20 0.9800 . ? C15 H23 0.9800 . ? C15 H22 0.9800 . ? C15 H21 0.9800 . ? C17 C18 1.332(4) . ? C17 C20 1.498(4) . ? C18 H25 0.9500 . ? C19 H26 0.9800 . ? C19 H28 0.9800 . ? C19 H27 0.9800 . ? C20 H31 0.9800 . ? C20 H30 0.9800 . ? C20 H29 0.9800 . ? 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 C3 S1 C1 90.96(14) . . ? C1 N1 C2 115.5(2) . . ? C1 N1 C4 118.9(2) . . ? C2 N1 C4 125.6(2) . . ? N2 C1 N1 123.5(3) . . ? N2 C1 S1 128.5(2) . . ? N1 C1 S1 108.0(2) . . ? C8 S2 C6 91.64(14) . . ? C1 N2 H8 109.5 . . ? C3 C2 N1 113.0(3) . . ? C3 C2 C5 126.1(3) . . ? N1 C2 C5 120.9(3) . . ? C13 S3 C11 91.48(14) . . ? C6 N3 C7 115.9(2) . . ? C6 N3 C9 119.1(2) . . ? C7 N3 C9 124.9(2) . . ? C2 C3 S1 112.4(2) . . ? C2 C3 H1 123.8 . . ? S1 C3 H1 123.8 . . ? C18 S4 C16 91.57(14) . . ? C6 N4 H16 109.5 . . ? N1 C4 H2 109.5 . . ? N1 C4 H4 109.5 . . ? H2 C4 H4 109.5 . . ? N1 C4 H3 109.5 . . ? H2 C4 H3 109.5 . . ? H4 C4 H3 109.5 . . ? C11 N5 C12 116.2(2) . . ? C11 N5 C14 119.3(2) . . ? C12 N5 C14 124.5(2) . . ? C2 C5 H7 109.5 . . ? C2 C5 H6 109.5 . . ? H7 C5 H6 109.5 . . ? C2 C5 H5 109.5 . . ? H7 C5 H5 109.5 . . ? H6 C5 H5 109.5 . . ? C11 N6 H24 109.5 . . ? N4 C6 N3 123.1(3) . . ? N4 C6 S2 129.4(2) . . ? N3 C6 S2 107.5(2) . . ? C16 N7 C17 115.6(2) . . ? C16 N7 C19 119.1(2) . . ? C17 N7 C19 125.3(2) . . ? C8 C7 N3 113.4(3) . . ? C8 C7 C10 126.6(3) . . ? N3 C7 C10 120.0(2) . . ? C16 N8 H32 109.5 . . ? C7 C8 S2 111.5(2) . . ? C7 C8 H9 124.2 . . ? S2 C8 H9 124.2 . . ? N3 C9 H12 109.5 . . ? N3 C9 H11 109.5 . . ? H12 C9 H11 109.5 . . ? N3 C9 H10 109.5 . . ? H12 C9 H10 109.5 . . ? H11 C9 H10 109.5 . . ? C7 C10 H15 109.5 . . ? C7 C10 H14 109.5 . . ? H15 C10 H14 109.5 . . ? C7 C10 H13 109.5 . . ? H15 C10 H13 109.5 . . ? H14 C10 H13 109.5 . . ? N6 C11 N5 123.7(3) . . ? N6 C11 S3 128.9(2) . . ? N5 C11 S3 107.3(2) . . ? C13 C12 N5 113.0(3) . . ? C13 C12 C15 127.0(3) . . ? N5 C12 C15 120.0(3) . . ? C12 C13 S3 111.9(2) . . ? C12 C13 H17 124.0 . . ? S3 C13 H17 124.0 . . ? N5 C14 H18 109.5 . . ? N5 C14 H19 109.5 . . ? H18 C14 H19 109.5 . . ? N5 C14 H20 109.5 . . ? H18 C14 H20 109.5 . . ? H19 C14 H20 109.5 . . ? C12 C15 H23 109.5 . . ? C12 C15 H22 109.5 . . ? H23 C15 H22 109.5 . . ? C12 C15 H21 109.5 . . ? H23 C15 H21 109.5 . . ? H22 C15 H21 109.5 . . ? N8 C16 N7 122.8(3) . . ? N8 C16 S4 129.3(2) . . ? N7 C16 S4 107.9(2) . . ? C18 C17 N7 113.3(3) . . ? C18 C17 C20 126.0(3) . . ? N7 C17 C20 120.6(2) . . ? C17 C18 S4 111.6(2) . . ? C17 C18 H25 124.2 . . ? S4 C18 H25 124.2 . . ? N7 C19 H26 109.5 . . ? N7 C19 H28 109.5 . . ? H26 C19 H28 109.5 . . ? N7 C19 H27 109.5 . . ? H26 C19 H27 109.5 . . ? H28 C19 H27 109.5 . . ? C17 C20 H31 109.5 . . ? C17 C20 H30 109.5 . . ? H31 C20 H30 109.5 . . ? C17 C20 H29 109.5 . . ? H31 C20 H29 109.5 . . ? H30 C20 H29 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 -179.7(3) . . . . ? C4 N1 C1 N2 -0.6(4) . . . . ? C2 N1 C1 S1 0.4(3) . . . . ? C4 N1 C1 S1 179.59(19) . . . . ? C3 S1 C1 N2 179.9(3) . . . . ? C3 S1 C1 N1 -0.2(2) . . . . ? C1 N1 C2 C3 -0.4(3) . . . . ? C4 N1 C2 C3 -179.5(3) . . . . ? C1 N1 C2 C5 180.0(2) . . . . ? C4 N1 C2 C5 0.9(4) . . . . ? N1 C2 C3 S1 0.2(3) . . . . ? C5 C2 C3 S1 179.8(2) . . . . ? C1 S1 C3 C2 0.0(2) . . . . ? C7 N3 C6 N4 -179.6(3) . . . . ? C9 N3 C6 N4 -0.5(4) . . . . ? C7 N3 C6 S2 1.5(3) . . . . ? C9 N3 C6 S2 -179.4(2) . . . . ? C8 S2 C6 N4 180.0(3) . . . . ? C8 S2 C6 N3 -1.2(2) . . . . ? C6 N3 C7 C8 -1.1(4) . . . . ? C9 N3 C7 C8 179.8(3) . . . . ? C6 N3 C7 C10 179.4(3) . . . . ? C9 N3 C7 C10 0.3(4) . . . . ? N3 C7 C8 S2 0.1(3) . . . . ? C10 C7 C8 S2 179.6(2) . . . . ? C6 S2 C8 C7 0.7(2) . . . . ? C12 N5 C11 N6 -178.3(3) . . . . ? C14 N5 C11 N6 -2.2(4) . . . . ? C12 N5 C11 S3 2.1(3) . . . . ? C14 N5 C11 S3 178.2(2) . . . . ? C13 S3 C11 N6 179.0(3) . . . . ? C13 S3 C11 N5 -1.4(2) . . . . ? C11 N5 C12 C13 -1.8(4) . . . . ? C14 N5 C12 C13 -177.8(3) . . . . ? C11 N5 C12 C15 178.2(3) . . . . ? C14 N5 C12 C15 2.2(4) . . . . ? N5 C12 C13 S3 0.6(3) . . . . ? C15 C12 C13 S3 -179.4(3) . . . . ? C11 S3 C13 C12 0.4(2) . . . . ? C17 N7 C16 N8 179.7(3) . . . . ? C19 N7 C16 N8 -2.0(4) . . . . ? C17 N7 C16 S4 -0.6(3) . . . . ? C19 N7 C16 S4 177.72(19) . . . . ? C18 S4 C16 N8 -179.7(3) . . . . ? C18 S4 C16 N7 0.7(2) . . . . ? C16 N7 C17 C18 0.1(4) . . . . ? C19 N7 C17 C18 -178.0(3) . . . . ? C16 N7 C17 C20 179.4(2) . . . . ? C19 N7 C17 C20 1.2(4) . . . . ? N7 C17 C18 S4 0.4(3) . . . . ? C20 C17 C18 S4 -178.8(2) . . . . ? C16 S4 C18 C17 -0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.433 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.067 #===END data_1 _database_code_depnum_ccdc_archive 'CCDC 801425' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point "94-100 ^o^C'(decompose)" _chemical_formula_moiety 'C15 H11 Au F5 N3' _chemical_formula_sum 'C15 H11 Au F5 N3' _chemical_formula_weight 525.23 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6840(19) _cell_length_b 13.5223(18) _cell_length_c 16.365(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.753(2) _cell_angle_gamma 90.00 _cell_volume 2883.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4716 _cell_measurement_theta_min 2.171 _cell_measurement_theta_max 26.3915 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 10.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2218 _exptl_absorpt_correction_T_max 0.5336 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15450 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.47 _reflns_number_total 5763 _reflns_number_gt 4788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0251P)^2^+4.0000P] 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 5763 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.14158(2) -0.07820(2) 0.020480(17) 0.01234(9) Uani 1 1 d . . . Au2 Au 0.38974(2) 0.03437(2) 0.069232(17) 0.01259(9) Uani 1 1 d . . . N11 N 0.1225(4) 0.1801(4) 0.0484(3) 0.0111(12) Uani 1 1 d . . . N12 N 0.1594(4) 0.1758(4) 0.1897(4) 0.0134(13) Uani 1 1 d . . . N13 N 0.1511(5) 0.0217(4) 0.1161(4) 0.0136(13) Uani 1 1 d . . . H11 H 0.1615 -0.0060 0.1667 0.016 Uiso 1 1 calc R . . N21 N 0.3566(4) -0.1315(4) -0.1040(3) 0.0113(13) Uani 1 1 d . . . N22 N 0.4041(4) -0.2658(4) -0.0247(3) 0.0124(13) Uani 1 1 d . . . N23 N 0.4108(4) -0.1133(4) 0.0483(4) 0.0134(13) Uani 1 1 d . . . H22 H 0.4371 -0.1478 0.0955 0.016 Uiso 1 1 calc R . . C111 C 0.1258(5) -0.1812(5) -0.0710(4) 0.0127(15) Uani 1 1 d . . . F112 F 0.0663(3) -0.0610(3) -0.1821(3) 0.0209(10) Uani 1 1 d . . . C112 C 0.0891(5) -0.1572(5) -0.1575(4) 0.0136(15) Uani 1 1 d . . . F113 F 0.0407(3) -0.1979(3) -0.3055(3) 0.0254(10) Uani 1 1 d . . . C113 C 0.0760(6) -0.2253(5) -0.2221(4) 0.0157(16) Uani 1 1 d . . . F114 F 0.0787(3) -0.3919(3) -0.2651(3) 0.0242(10) Uani 1 1 d . . . C114 C 0.0955(5) -0.3231(5) -0.2020(4) 0.0164(16) Uani 1 1 d . . . F115 F 0.1524(4) -0.4475(3) -0.0981(3) 0.0258(11) Uani 1 1 d . . . C115 C 0.1315(6) -0.3518(5) -0.1171(5) 0.0184(17) Uani 1 1 d . . . F116 F 0.1817(3) -0.3127(3) 0.0277(2) 0.0233(10) Uani 1 1 d . . . C116 C 0.1448(5) -0.2796(5) -0.0548(4) 0.0130(15) Uani 1 1 d . . . C121 C 0.3806(5) 0.1787(5) 0.0963(4) 0.0112(15) Uani 1 1 d . . . F122 F 0.3393(3) 0.2277(3) -0.0501(2) 0.0205(10) Uani 1 1 d . . . C122 C 0.3604(5) 0.2517(5) 0.0348(4) 0.0140(15) Uani 1 1 d . . . F123 F 0.3389(4) 0.4197(3) -0.0115(3) 0.0267(11) Uani 1 1 d . . . C123 C 0.3573(6) 0.3515(5) 0.0524(5) 0.0168(16) Uani 1 1 d . . . F124 F 0.3790(3) 0.4787(3) 0.1548(3) 0.0245(10) Uani 1 1 d . . . C124 C 0.3778(6) 0.3821(5) 0.1357(5) 0.0199(17) Uani 1 1 d . . . F125 F 0.4162(3) 0.3407(3) 0.2821(3) 0.0227(10) Uani 1 1 d . . . C125 C 0.3976(6) 0.3115(5) 0.1992(4) 0.0152(16) Uani 1 1 d . . . F126 F 0.4199(3) 0.1479(3) 0.2458(2) 0.0218(10) Uani 1 1 d . . . C126 C 0.3980(6) 0.2120(5) 0.1792(4) 0.0151(16) Uani 1 1 d . . . C211 C 0.1449(5) 0.1179(5) 0.1180(4) 0.0109(14) Uani 1 1 d . . . C212 C 0.1455(6) 0.2745(5) 0.1653(5) 0.0165(16) Uani 1 1 d . . . C213 C 0.1514(5) 0.3598(5) 0.2132(5) 0.0157(16) Uani 1 1 d . . . H1 H 0.1676 0.3580 0.2739 0.019 Uiso 1 1 calc R . . C214 C 0.1322(6) 0.4484(5) 0.1677(5) 0.0198(17) Uani 1 1 d . . . H2 H 0.1333 0.5085 0.1980 0.024 Uiso 1 1 calc R . . C215 C 0.1116(6) 0.4514(5) 0.0791(5) 0.0175(17) Uani 1 1 d . . . H3 H 0.1023 0.5136 0.0508 0.021 Uiso 1 1 calc R . . C216 C 0.1043(5) 0.3663(5) 0.0315(5) 0.0143(15) Uani 1 1 d . . . H4 H 0.0876 0.3685 -0.0293 0.017 Uiso 1 1 calc R . . C217 C 0.1222(5) 0.2773(5) 0.0754(4) 0.0139(15) Uani 1 1 d . . . C218 C 0.1049(6) 0.1502(5) -0.0410(4) 0.0150(16) Uani 1 1 d . . . H6 H 0.1653 0.1150 -0.0462 0.023 Uiso 1 1 calc R . . H5 H 0.0926 0.2091 -0.0777 0.023 Uiso 1 1 calc R . . H7 H 0.0449 0.1066 -0.0590 0.023 Uiso 1 1 calc R . . C219 C 0.1869(6) 0.1366(5) 0.2766(4) 0.0169(16) Uani 1 1 d . . . H10 H 0.2064 0.1911 0.3178 0.025 Uiso 1 1 calc R . . H8 H 0.2447 0.0908 0.2856 0.025 Uiso 1 1 calc R . . H9 H 0.1279 0.1015 0.2848 0.025 Uiso 1 1 calc R . . C221 C 0.3923(5) -0.1646(5) -0.0216(4) 0.0128(15) Uani 1 1 d . . . C222 C 0.3767(5) -0.2963(5) -0.1103(4) 0.0157(16) Uani 1 1 d . . . C223 C 0.3774(5) -0.3877(6) -0.1471(4) 0.0146(16) Uani 1 1 d . . . H12 H 0.3979 -0.4453 -0.1129 0.018 Uiso 1 1 calc R . . C224 C 0.3466(6) -0.3924(6) -0.2370(5) 0.0204(17) Uani 1 1 d . . . H13 H 0.3471 -0.4541 -0.2646 0.024 Uiso 1 1 calc R . . C225 C 0.3157(5) -0.3081(6) -0.2859(4) 0.0173(16) Uani 1 1 d . . . H14 H 0.2945 -0.3134 -0.3466 0.021 Uiso 1 1 calc R . . C226 C 0.3148(5) -0.2153(5) -0.2484(4) 0.0160(16) Uani 1 1 d . . . H15 H 0.2927 -0.1580 -0.2825 0.019 Uiso 1 1 calc R . . C227 C 0.3473(5) -0.2102(5) -0.1597(5) 0.0143(16) Uani 1 1 d . . . C228 C 0.3334(6) -0.0286(5) -0.1304(4) 0.0171(16) Uani 1 1 d . . . H20 H 0.3354 -0.0202 -0.1894 0.026 Uiso 1 1 calc R . . H19 H 0.3844 0.0149 -0.0921 0.026 Uiso 1 1 calc R . . H21 H 0.2649 -0.0115 -0.1276 0.026 Uiso 1 1 calc R . . C229 C 0.4357(6) -0.3297(6) 0.0501(4) 0.0200(17) Uani 1 1 d . . . H17 H 0.4293 -0.3990 0.0317 0.030 Uiso 1 1 calc R . . H18 H 0.3919 -0.3176 0.0866 0.030 Uiso 1 1 calc R . . H16 H 0.5073 -0.3156 0.0826 0.030 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 0.01537(16) 0.00918(15) 0.01242(15) -0.00092(11) 0.00419(11) -0.00039(11) Au2 0.01508(16) 0.01087(15) 0.01180(15) -0.00099(11) 0.00408(11) -0.00045(11) N11 0.018(3) 0.012(3) 0.003(3) 0.003(2) 0.002(2) 0.002(2) N12 0.014(3) 0.014(3) 0.012(3) 0.000(3) 0.003(3) -0.004(2) N13 0.021(4) 0.006(3) 0.016(3) 0.000(3) 0.009(3) -0.001(2) N21 0.018(3) 0.009(3) 0.006(3) 0.001(2) 0.003(2) -0.001(2) N22 0.016(3) 0.008(3) 0.013(3) -0.002(2) 0.004(3) -0.004(2) N23 0.016(3) 0.013(3) 0.008(3) 0.004(3) 0.000(2) -0.001(3) C111 0.019(4) 0.010(4) 0.010(3) -0.005(3) 0.006(3) 0.001(3) F112 0.036(3) 0.011(2) 0.014(2) 0.0075(18) 0.006(2) 0.0060(19) C112 0.012(4) 0.009(3) 0.017(4) 0.004(3) 0.000(3) -0.002(3) F113 0.034(3) 0.025(2) 0.016(2) 0.000(2) 0.006(2) -0.004(2) C113 0.017(4) 0.021(4) 0.010(4) 0.003(3) 0.006(3) 0.002(3) F114 0.032(3) 0.019(2) 0.021(2) -0.011(2) 0.007(2) 0.000(2) C114 0.014(4) 0.019(4) 0.017(4) -0.009(3) 0.006(3) -0.005(3) F115 0.039(3) 0.010(2) 0.028(3) 0.001(2) 0.010(2) 0.005(2) C115 0.024(4) 0.015(4) 0.017(4) -0.004(3) 0.007(3) -0.001(3) F116 0.039(3) 0.011(2) 0.017(2) 0.0052(19) 0.004(2) -0.0017(19) C116 0.012(4) 0.018(4) 0.007(3) 0.007(3) 0.000(3) -0.002(3) C121 0.007(4) 0.010(3) 0.016(4) -0.002(3) 0.002(3) -0.001(3) F122 0.028(3) 0.021(2) 0.011(2) 0.0033(19) 0.0039(18) -0.0021(19) C122 0.015(4) 0.009(4) 0.016(4) 0.001(3) 0.002(3) -0.003(3) F123 0.037(3) 0.018(2) 0.025(2) 0.007(2) 0.010(2) 0.002(2) C123 0.018(4) 0.010(4) 0.020(4) 0.004(3) 0.002(3) 0.004(3) F124 0.034(3) 0.008(2) 0.032(3) -0.008(2) 0.011(2) -0.0033(19) C124 0.018(4) 0.012(4) 0.030(4) -0.004(3) 0.008(4) 0.003(3) F125 0.030(3) 0.020(2) 0.019(2) -0.011(2) 0.008(2) 0.0011(19) C125 0.019(4) 0.012(4) 0.014(4) -0.005(3) 0.004(3) -0.004(3) F126 0.032(3) 0.016(2) 0.016(2) 0.0026(19) 0.005(2) -0.0004(19) C126 0.019(4) 0.011(4) 0.016(4) 0.002(3) 0.006(3) -0.004(3) C211 0.007(3) 0.014(4) 0.011(3) 0.000(3) 0.002(3) 0.005(3) C212 0.020(4) 0.009(4) 0.020(4) 0.004(3) 0.006(3) -0.008(3) C213 0.013(4) 0.015(4) 0.020(4) -0.007(3) 0.005(3) 0.000(3) C214 0.020(4) 0.014(4) 0.027(4) -0.001(3) 0.008(3) -0.003(3) C215 0.022(4) 0.008(4) 0.024(4) 0.006(3) 0.010(3) -0.003(3) C216 0.020(4) 0.005(3) 0.018(4) 0.004(3) 0.006(3) 0.003(3) C217 0.007(4) 0.012(4) 0.020(4) 0.001(3) 0.001(3) 0.000(3) C218 0.025(4) 0.009(4) 0.011(3) 0.000(3) 0.005(3) -0.003(3) C219 0.026(4) 0.017(4) 0.009(4) 0.004(3) 0.006(3) 0.002(3) C221 0.012(4) 0.011(3) 0.015(4) -0.003(3) 0.004(3) -0.002(3) C222 0.010(4) 0.022(4) 0.014(4) -0.003(3) 0.002(3) -0.001(3) C223 0.008(4) 0.023(4) 0.015(4) 0.002(3) 0.007(3) -0.002(3) C224 0.021(4) 0.021(4) 0.022(4) -0.005(3) 0.011(3) -0.004(3) C225 0.012(4) 0.029(4) 0.008(3) -0.005(3) -0.001(3) -0.002(3) C226 0.012(4) 0.021(4) 0.012(4) 0.002(3) -0.001(3) -0.002(3) C227 0.003(3) 0.017(4) 0.022(4) -0.003(3) 0.003(3) -0.001(3) C228 0.019(4) 0.014(4) 0.013(4) 0.000(3) -0.003(3) 0.004(3) C229 0.030(5) 0.022(4) 0.012(4) 0.008(3) 0.012(3) 0.003(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 C111 2.009(7) . ? Au1 N13 2.041(5) . ? Au2 C121 2.014(7) . ? Au2 N23 2.061(6) . ? N11 C211 1.373(8) . ? N11 C217 1.387(9) . ? N11 C218 1.466(8) . ? N12 C211 1.374(8) . ? N12 C212 1.389(9) . ? N12 C219 1.456(8) . ? N13 C211 1.305(8) . ? N13 H11 0.8800 . ? N21 C221 1.362(8) . ? N21 C227 1.382(9) . ? N21 C228 1.463(8) . ? N22 C221 1.381(9) . ? N22 C222 1.398(8) . ? N22 C229 1.452(8) . ? N23 C221 1.295(8) . ? N23 H22 0.8800 . ? C111 C116 1.366(10) . ? C111 C112 1.388(9) . ? F112 C112 1.369(8) . ? C112 C113 1.372(10) . ? F113 C113 1.353(8) . ? C113 C114 1.370(10) . ? F114 C114 1.356(8) . ? C114 C115 1.381(10) . ? F115 C115 1.342(8) . ? C115 C116 1.382(10) . ? F116 C116 1.365(7) . ? C121 C122 1.377(9) . ? C121 C126 1.379(9) . ? F122 C122 1.369(8) . ? C122 C123 1.383(10) . ? F123 C123 1.360(8) . ? C123 C124 1.370(10) . ? F124 C124 1.342(8) . ? C124 C125 1.376(10) . ? F125 C125 1.361(8) . ? C125 C126 1.386(9) . ? F126 C126 1.353(8) . ? C212 C213 1.383(9) . ? C212 C217 1.407(10) . ? C213 C214 1.393(10) . ? C213 H1 0.9500 . ? C214 C215 1.391(10) . ? C214 H2 0.9500 . ? C215 C216 1.377(10) . ? C215 H3 0.9500 . ? C216 C217 1.385(9) . ? C216 H4 0.9500 . ? C218 H6 0.9800 . ? C218 H5 0.9800 . ? C218 H7 0.9800 . ? C219 H10 0.9800 . ? C219 H8 0.9800 . ? C219 H9 0.9800 . ? C222 C223 1.375(10) . ? C222 C227 1.405(10) . ? C223 C224 1.403(10) . ? C223 H12 0.9500 . ? C224 C225 1.382(10) . ? C224 H13 0.9500 . ? C225 C226 1.398(10) . ? C225 H14 0.9500 . ? C226 C227 1.385(9) . ? C226 H15 0.9500 . ? C228 H20 0.9800 . ? C228 H19 0.9800 . ? C228 H21 0.9800 . ? C229 H17 0.9800 . ? C229 H18 0.9800 . ? C229 H16 0.9800 . ? 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 C111 Au1 N13 176.4(2) . . ? C121 Au2 N23 175.4(2) . . ? C211 N11 C217 109.7(5) . . ? C211 N11 C218 125.9(6) . . ? C217 N11 C218 124.3(6) . . ? C211 N12 C212 109.3(6) . . ? C211 N12 C219 123.6(6) . . ? C212 N12 C219 127.1(6) . . ? C211 N13 Au1 133.5(5) . . ? C211 N13 H11 113.2 . . ? Au1 N13 H11 113.2 . . ? C221 N21 C227 109.4(5) . . ? C221 N21 C228 125.9(6) . . ? C227 N21 C228 124.7(5) . . ? C221 N22 C222 109.3(6) . . ? C221 N22 C229 124.5(6) . . ? C222 N22 C229 126.1(6) . . ? C221 N23 Au2 131.8(5) . . ? C221 N23 H22 114.1 . . ? Au2 N23 H22 114.1 . . ? C116 C111 C112 114.5(6) . . ? C116 C111 Au1 124.0(5) . . ? C112 C111 Au1 121.4(5) . . ? F112 C112 C113 116.5(6) . . ? F112 C112 C111 120.1(6) . . ? C113 C112 C111 123.4(6) . . ? F113 C113 C114 119.3(6) . . ? F113 C113 C112 121.1(6) . . ? C114 C113 C112 119.5(6) . . ? F114 C114 C113 120.3(6) . . ? F114 C114 C115 119.9(6) . . ? C113 C114 C115 119.7(7) . . ? F115 C115 C114 119.3(6) . . ? F115 C115 C116 122.6(6) . . ? C114 C115 C116 118.1(7) . . ? F116 C116 C111 120.2(6) . . ? F116 C116 C115 115.1(6) . . ? C111 C116 C115 124.7(6) . . ? C122 C121 C126 114.9(6) . . ? C122 C121 Au2 123.1(5) . . ? C126 C121 Au2 122.0(5) . . ? F122 C122 C121 120.3(6) . . ? F122 C122 C123 115.6(6) . . ? C121 C122 C123 124.0(7) . . ? F123 C123 C124 119.6(6) . . ? F123 C123 C122 120.8(6) . . ? C124 C123 C122 119.5(7) . . ? F124 C124 C123 120.7(7) . . ? F124 C124 C125 120.9(7) . . ? C123 C124 C125 118.4(7) . . ? F125 C125 C124 119.1(6) . . ? F125 C125 C126 120.3(6) . . ? C124 C125 C126 120.6(6) . . ? F126 C126 C121 120.8(6) . . ? F126 C126 C125 116.6(6) . . ? C121 C126 C125 122.6(7) . . ? N13 C211 N11 126.2(6) . . ? N13 C211 N12 126.5(6) . . ? N11 C211 N12 107.3(6) . . ? C213 C212 N12 131.2(7) . . ? C213 C212 C217 121.7(7) . . ? N12 C212 C217 107.1(6) . . ? C212 C213 C214 116.5(7) . . ? C212 C213 H1 121.8 . . ? C214 C213 H1 121.8 . . ? C215 C214 C213 121.8(7) . . ? C215 C214 H2 119.1 . . ? C213 C214 H2 119.1 . . ? C216 C215 C214 121.5(7) . . ? C216 C215 H3 119.3 . . ? C214 C215 H3 119.3 . . ? C215 C216 C217 117.5(6) . . ? C215 C216 H4 121.2 . . ? C217 C216 H4 121.2 . . ? C216 C217 N11 132.5(6) . . ? C216 C217 C212 120.9(7) . . ? N11 C217 C212 106.6(6) . . ? N11 C218 H6 109.5 . . ? N11 C218 H5 109.5 . . ? H6 C218 H5 109.5 . . ? N11 C218 H7 109.5 . . ? H6 C218 H7 109.5 . . ? H5 C218 H7 109.5 . . ? N12 C219 H10 109.5 . . ? N12 C219 H8 109.5 . . ? H10 C219 H8 109.5 . . ? N12 C219 H9 109.5 . . ? H10 C219 H9 109.5 . . ? H8 C219 H9 109.5 . . ? N23 C221 N21 127.7(6) . . ? N23 C221 N22 124.8(6) . . ? N21 C221 N22 107.5(6) . . ? C223 C222 N22 131.9(7) . . ? C223 C222 C227 122.2(6) . . ? N22 C222 C227 105.9(6) . . ? C222 C223 C224 117.3(7) . . ? C222 C223 H12 121.3 . . ? C224 C223 H12 121.3 . . ? C225 C224 C223 120.7(7) . . ? C225 C224 H13 119.6 . . ? C223 C224 H13 119.6 . . ? C224 C225 C226 121.9(6) . . ? C224 C225 H14 119.1 . . ? C226 C225 H14 119.1 . . ? C227 C226 C225 117.5(7) . . ? C227 C226 H15 121.2 . . ? C225 C226 H15 121.2 . . ? C226 C227 N21 131.8(7) . . ? C226 C227 C222 120.3(7) . . ? N21 C227 C222 107.9(6) . . ? N21 C228 H20 109.5 . . ? N21 C228 H19 109.5 . . ? H20 C228 H19 109.5 . . ? N21 C228 H21 109.5 . . ? H20 C228 H21 109.5 . . ? H19 C228 H21 109.5 . . ? N22 C229 H17 109.5 . . ? N22 C229 H18 109.5 . . ? H17 C229 H18 109.5 . . ? N22 C229 H16 109.5 . . ? H17 C229 H16 109.5 . . ? H18 C229 H16 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C116 C111 C112 F112 179.4(6) . . . . ? Au1 C111 C112 F112 2.5(9) . . . . ? C116 C111 C112 C113 -2.3(11) . . . . ? Au1 C111 C112 C113 -179.3(6) . . . . ? F112 C112 C113 F113 -1.2(10) . . . . ? C111 C112 C113 F113 -179.5(6) . . . . ? F112 C112 C113 C114 -178.8(6) . . . . ? C111 C112 C113 C114 2.9(11) . . . . ? F113 C113 C114 F114 -0.6(10) . . . . ? C112 C113 C114 F114 177.1(6) . . . . ? F113 C113 C114 C115 -179.9(7) . . . . ? C112 C113 C114 C115 -2.2(11) . . . . ? F114 C114 C115 F115 2.1(11) . . . . ? C113 C114 C115 F115 -178.6(6) . . . . ? F114 C114 C115 C116 -178.1(6) . . . . ? C113 C114 C115 C116 1.2(11) . . . . ? C112 C111 C116 F116 179.6(6) . . . . ? Au1 C111 C116 F116 -3.5(10) . . . . ? C112 C111 C116 C115 1.2(11) . . . . ? Au1 C111 C116 C115 178.1(6) . . . . ? F115 C115 C116 F116 0.6(10) . . . . ? C114 C115 C116 F116 -179.2(6) . . . . ? F115 C115 C116 C111 179.1(7) . . . . ? C114 C115 C116 C111 -0.7(11) . . . . ? C126 C121 C122 F122 -178.4(6) . . . . ? Au2 C121 C122 F122 4.0(9) . . . . ? C126 C121 C122 C123 0.0(10) . . . . ? Au2 C121 C122 C123 -177.7(6) . . . . ? F122 C122 C123 F123 -2.9(10) . . . . ? C121 C122 C123 F123 178.7(6) . . . . ? F122 C122 C123 C124 -179.8(6) . . . . ? C121 C122 C123 C124 1.8(11) . . . . ? F123 C123 C124 F124 0.6(11) . . . . ? C122 C123 C124 F124 177.5(6) . . . . ? F123 C123 C124 C125 -179.0(6) . . . . ? C122 C123 C124 C125 -2.1(11) . . . . ? F124 C124 C125 F125 1.6(11) . . . . ? C123 C124 C125 F125 -178.8(7) . . . . ? F124 C124 C125 C126 -178.9(6) . . . . ? C123 C124 C125 C126 0.8(11) . . . . ? C122 C121 C126 F126 -179.2(6) . . . . ? Au2 C121 C126 F126 -1.5(9) . . . . ? C122 C121 C126 C125 -1.4(10) . . . . ? Au2 C121 C126 C125 176.3(5) . . . . ? F125 C125 C126 F126 -1.5(10) . . . . ? C124 C125 C126 F126 179.0(6) . . . . ? F125 C125 C126 C121 -179.4(6) . . . . ? C124 C125 C126 C121 1.1(11) . . . . ? Au1 N13 C211 N11 4.5(11) . . . . ? Au1 N13 C211 N12 -175.7(5) . . . . ? C217 N11 C211 N13 179.6(7) . . . . ? C218 N11 C211 N13 -2.4(11) . . . . ? C217 N11 C211 N12 -0.3(7) . . . . ? C218 N11 C211 N12 177.7(6) . . . . ? C212 N12 C211 N13 -179.5(7) . . . . ? C219 N12 C211 N13 1.5(11) . . . . ? C212 N12 C211 N11 0.3(7) . . . . ? C219 N12 C211 N11 -178.6(6) . . . . ? C211 N12 C212 C213 179.8(7) . . . . ? C219 N12 C212 C213 -1.3(12) . . . . ? C211 N12 C212 C217 -0.3(8) . . . . ? C219 N12 C212 C217 178.6(6) . . . . ? N12 C212 C213 C214 -179.7(7) . . . . ? C217 C212 C213 C214 0.4(10) . . . . ? C212 C213 C214 C215 -2.0(11) . . . . ? C213 C214 C215 C216 3.1(12) . . . . ? C214 C215 C216 C217 -2.4(11) . . . . ? C215 C216 C217 N11 -179.1(7) . . . . ? C215 C216 C217 C212 0.9(10) . . . . ? C211 N11 C217 C216 -180.0(7) . . . . ? C218 N11 C217 C216 2.0(12) . . . . ? C211 N11 C217 C212 0.1(8) . . . . ? C218 N11 C217 C212 -178.0(6) . . . . ? C213 C212 C217 C216 0.1(11) . . . . ? N12 C212 C217 C216 -179.8(6) . . . . ? C213 C212 C217 N11 -179.9(6) . . . . ? N12 C212 C217 N11 0.1(8) . . . . ? Au2 N23 C221 N21 3.5(11) . . . . ? Au2 N23 C221 N22 -175.1(5) . . . . ? C227 N21 C221 N23 -179.9(7) . . . . ? C228 N21 C221 N23 1.3(12) . . . . ? C227 N21 C221 N22 -1.1(8) . . . . ? C228 N21 C221 N22 -179.9(6) . . . . ? C222 N22 C221 N23 179.7(6) . . . . ? C229 N22 C221 N23 2.1(11) . . . . ? C222 N22 C221 N21 0.9(8) . . . . ? C229 N22 C221 N21 -176.7(6) . . . . ? C221 N22 C222 C223 178.2(7) . . . . ? C229 N22 C222 C223 -4.4(12) . . . . ? C221 N22 C222 C227 -0.3(8) . . . . ? C229 N22 C222 C227 177.2(6) . . . . ? N22 C222 C223 C224 -178.6(7) . . . . ? C227 C222 C223 C224 -0.4(10) . . . . ? C222 C223 C224 C225 -0.9(11) . . . . ? C223 C224 C225 C226 0.7(11) . . . . ? C224 C225 C226 C227 0.7(10) . . . . ? C225 C226 C227 N21 179.2(7) . . . . ? C225 C226 C227 C222 -1.9(10) . . . . ? C221 N21 C227 C226 180.0(7) . . . . ? C228 N21 C227 C226 -1.2(12) . . . . ? C221 N21 C227 C222 0.9(8) . . . . ? C228 N21 C227 C222 179.8(6) . . . . ? C223 C222 C227 C226 1.8(11) . . . . ? N22 C222 C227 C226 -179.6(6) . . . . ? C223 C222 C227 N21 -179.0(6) . . . . ? N22 C222 C227 N21 -0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.035 _refine_diff_density_min -1.230 _refine_diff_density_rms 0.235 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 801426' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point '128-132 ^o^C' _chemical_formula_moiety 'C14 H8 Au F5 N2 S, C4 H8 O' _chemical_formula_sum 'C18 H16 Au F5 N2 O S' _chemical_formula_weight 600.35 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' F F 0.0171 0.0103 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.309(2) _cell_length_b 9.355(2) _cell_length_c 11.773(3) _cell_angle_alpha 99.080(3) _cell_angle_beta 112.817(3) _cell_angle_gamma 96.171(3) _cell_volume 917.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5740 _cell_measurement_theta_min 2.2425 _cell_measurement_theta_max 25.769 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 8.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4396 _exptl_absorpt_correction_T_max 0.5258 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9785 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3994 _reflns_number_gt 3618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0443P)^2^+1.7566P] 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 3994 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.04904(2) 0.72257(2) 0.550178(17) 0.01506(8) Uani 1 1 d . . . S1 S -0.12590(15) 0.50530(15) 0.69047(12) 0.0176(3) Uani 1 1 d . . . O1 O 0.4994(5) 0.6803(4) 0.7687(4) 0.0238(9) Uani 1 1 d . . . N1 N 0.1502(5) 0.4900(5) 0.8513(4) 0.0182(9) Uani 1 1 d . . . C1 C 0.4792(7) 0.6185(6) 0.6414(6) 0.0251(12) Uani 1 1 d . . . H16 H 0.3686 0.5663 0.5900 0.030 Uiso 1 1 calc R . . H15 H 0.5511 0.5475 0.6428 0.030 Uiso 1 1 calc R . . N2 N 0.1518(6) 0.6362(5) 0.7044(4) 0.0202(10) Uani 1 1 d . . . H8 H 0.2558 0.6591 0.7437 0.024 Uiso 1 1 calc R . . C2 C 0.5183(8) 0.7456(7) 0.5856(6) 0.0316(14) Uani 1 1 d . . . H14 H 0.6258 0.7512 0.5869 0.038 Uiso 1 1 calc R . . H13 H 0.4402 0.7352 0.4976 0.038 Uiso 1 1 calc R . . C3 C 0.5093(7) 0.8801(6) 0.6718(5) 0.0254(13) Uani 1 1 d . . . H11 H 0.5796 0.9691 0.6744 0.030 Uiso 1 1 calc R . . H12 H 0.3994 0.8985 0.6447 0.030 Uiso 1 1 calc R . . C4 C 0.5658(7) 0.8367(6) 0.7980(5) 0.0241(12) Uani 1 1 d . . . H9 H 0.6831 0.8538 0.8390 0.029 Uiso 1 1 calc R . . H10 H 0.5268 0.8937 0.8548 0.029 Uiso 1 1 calc R . . C111 C -0.0463(7) 0.8171(5) 0.4029(5) 0.0167(11) Uani 1 1 d . . . F112 F 0.2077(4) 0.9391(4) 0.4320(3) 0.0229(7) Uani 1 1 d . . . C112 C 0.0456(6) 0.9099(6) 0.3677(5) 0.0166(11) Uani 1 1 d . . . F113 F 0.0843(4) 1.0740(4) 0.2415(3) 0.0220(7) Uani 1 1 d . . . C113 C -0.0130(6) 0.9812(6) 0.2694(5) 0.0156(10) Uani 1 1 d . . . F114 F -0.2362(4) 1.0243(4) 0.1024(3) 0.0252(7) Uani 1 1 d . . . C114 C -0.1720(7) 0.9578(6) 0.1997(5) 0.0207(12) Uani 1 1 d . . . F115 F -0.4306(4) 0.8368(4) 0.1586(3) 0.0259(7) Uani 1 1 d . . . C115 C -0.2718(6) 0.8632(6) 0.2292(5) 0.0187(11) Uani 1 1 d . . . F116 F -0.3113(4) 0.7052(4) 0.3526(3) 0.0248(7) Uani 1 1 d . . . C116 C -0.2076(6) 0.7960(6) 0.3277(5) 0.0167(11) Uani 1 1 d . . . C211 C 0.0805(6) 0.5514(6) 0.7509(5) 0.0142(10) Uani 1 1 d . . . C212 C -0.1126(6) 0.3923(6) 0.7994(5) 0.0164(10) Uani 1 1 d . . . C213 C -0.2369(6) 0.3058(6) 0.8094(5) 0.0185(11) Uani 1 1 d . . . H1 H -0.3444 0.3024 0.7548 0.022 Uiso 1 1 calc R . . C214 C -0.1966(7) 0.2247(6) 0.9027(5) 0.0225(12) Uani 1 1 d . . . H2 H -0.2782 0.1633 0.9114 0.027 Uiso 1 1 calc R . . C215 C -0.0390(7) 0.2311(6) 0.9840(5) 0.0180(11) Uani 1 1 d . . . H3 H -0.0153 0.1746 1.0472 0.022 Uiso 1 1 calc R . . C216 C 0.0844(6) 0.3194(6) 0.9738(5) 0.0175(11) Uani 1 1 d . . . H4 H 0.1916 0.3252 1.0301 0.021 Uiso 1 1 calc R . . C217 C 0.0459(6) 0.3982(5) 0.8794(5) 0.0153(10) Uani 1 1 d . . . C218 C 0.3180(6) 0.5149(6) 0.9192(5) 0.0167(11) Uani 1 1 d . . . H6 H 0.3662 0.4794 0.8620 0.025 Uiso 1 1 calc R . . H7 H 0.3450 0.4619 0.9879 0.025 Uiso 1 1 calc R . . H5 H 0.3584 0.6206 0.9543 0.025 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 0.01561(12) 0.01528(11) 0.01465(11) 0.00443(7) 0.00634(8) 0.00221(7) S1 0.0122(6) 0.0224(7) 0.0165(6) 0.0061(5) 0.0038(5) 0.0018(5) O1 0.018(2) 0.026(2) 0.023(2) 0.0050(17) 0.0052(16) -0.0028(16) N1 0.017(2) 0.019(2) 0.017(2) 0.0045(18) 0.0060(18) 0.0020(18) C1 0.023(3) 0.022(3) 0.032(3) 0.000(2) 0.015(3) 0.004(2) N2 0.017(2) 0.021(2) 0.023(2) 0.0073(19) 0.0073(19) 0.0038(18) C2 0.037(4) 0.035(3) 0.024(3) 0.004(3) 0.017(3) -0.002(3) C3 0.024(3) 0.025(3) 0.021(3) 0.006(2) 0.003(2) -0.001(2) C4 0.017(3) 0.022(3) 0.026(3) 0.003(2) 0.003(2) -0.003(2) C111 0.032(3) 0.007(2) 0.014(2) -0.0004(19) 0.014(2) 0.008(2) F112 0.0152(16) 0.0302(18) 0.0213(16) 0.0093(14) 0.0048(13) 0.0011(13) C112 0.012(2) 0.019(3) 0.013(2) -0.003(2) 0.001(2) 0.002(2) F113 0.0182(16) 0.0251(17) 0.0222(16) 0.0090(13) 0.0078(13) -0.0022(13) C113 0.020(3) 0.015(2) 0.016(2) 0.002(2) 0.012(2) 0.002(2) F114 0.0235(18) 0.0293(18) 0.0190(16) 0.0118(14) 0.0024(14) 0.0046(14) C114 0.030(3) 0.018(3) 0.011(2) 0.005(2) 0.004(2) 0.007(2) F115 0.0102(15) 0.0302(18) 0.0284(18) 0.0072(15) -0.0005(13) -0.0003(13) C115 0.011(2) 0.019(3) 0.021(3) -0.002(2) 0.005(2) -0.002(2) F116 0.0191(17) 0.0258(17) 0.0317(18) 0.0118(14) 0.0121(14) -0.0013(13) C116 0.010(2) 0.015(2) 0.018(3) -0.002(2) 0.005(2) -0.0096(19) C211 0.012(2) 0.016(2) 0.019(3) 0.002(2) 0.011(2) 0.0054(19) C212 0.020(3) 0.014(2) 0.013(2) 0.001(2) 0.005(2) 0.003(2) C213 0.014(3) 0.022(3) 0.014(2) -0.001(2) 0.002(2) 0.003(2) C214 0.029(3) 0.017(3) 0.022(3) 0.003(2) 0.013(2) -0.002(2) C215 0.024(3) 0.017(3) 0.016(2) 0.007(2) 0.009(2) 0.003(2) C216 0.015(3) 0.018(3) 0.017(3) 0.001(2) 0.006(2) 0.002(2) C217 0.014(3) 0.011(2) 0.018(3) -0.003(2) 0.008(2) -0.0044(19) C218 0.016(3) 0.022(3) 0.014(2) 0.009(2) 0.006(2) 0.003(2) _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 C111 2.009(5) . ? Au1 N2 2.037(5) . ? S1 C211 1.746(5) . ? S1 C212 1.763(5) . ? O1 C1 1.450(7) . ? O1 C4 1.457(7) . ? N1 C211 1.359(7) . ? N1 C217 1.396(7) . ? N1 C218 1.425(7) . ? C1 C2 1.522(8) . ? C1 H16 0.9900 . ? C1 H15 0.9900 . ? N2 C211 1.294(7) . ? N2 H8 0.8800 . ? C2 C3 1.519(9) . ? C2 H14 0.9900 . ? C2 H13 0.9900 . ? C3 C4 1.510(8) . ? C3 H11 0.9900 . ? C3 H12 0.9900 . ? C4 H9 0.9900 . ? C4 H10 0.9900 . ? C111 C112 1.373(8) . ? C111 C116 1.388(8) . ? F112 C112 1.372(6) . ? C112 C113 1.384(7) . ? F113 C113 1.354(6) . ? C113 C114 1.358(8) . ? F114 C114 1.352(6) . ? C114 C115 1.392(8) . ? F115 C115 1.357(6) . ? C115 C116 1.368(8) . ? F116 C116 1.364(6) . ? C212 C213 1.394(8) . ? C212 C217 1.399(7) . ? C213 C214 1.389(8) . ? C213 H1 0.9500 . ? C214 C215 1.395(8) . ? C214 H2 0.9500 . ? C215 C216 1.397(7) . ? C215 H3 0.9500 . ? C216 C217 1.384(7) . ? C216 H4 0.9500 . ? C218 H6 0.9800 . ? C218 H7 0.9800 . ? C218 H5 0.9800 . ? 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 C111 Au1 N2 177.29(19) . . ? C211 S1 C212 91.0(3) . . ? C1 O1 C4 107.9(4) . . ? C211 N1 C217 115.1(4) . . ? C211 N1 C218 121.7(4) . . ? C217 N1 C218 123.2(4) . . ? O1 C1 C2 107.5(5) . . ? O1 C1 H16 110.2 . . ? C2 C1 H16 110.2 . . ? O1 C1 H15 110.2 . . ? C2 C1 H15 110.2 . . ? H16 C1 H15 108.5 . . ? C211 N2 Au1 127.0(4) . . ? C211 N2 H8 116.5 . . ? Au1 N2 H8 116.5 . . ? C3 C2 C1 103.4(5) . . ? C3 C2 H14 111.1 . . ? C1 C2 H14 111.1 . . ? C3 C2 H13 111.1 . . ? C1 C2 H13 111.1 . . ? H14 C2 H13 109.1 . . ? C4 C3 C2 102.3(5) . . ? C4 C3 H11 111.3 . . ? C2 C3 H11 111.3 . . ? C4 C3 H12 111.3 . . ? C2 C3 H12 111.3 . . ? H11 C3 H12 109.2 . . ? O1 C4 C3 104.8(4) . . ? O1 C4 H9 110.8 . . ? C3 C4 H9 110.8 . . ? O1 C4 H10 110.8 . . ? C3 C4 H10 110.8 . . ? H9 C4 H10 108.9 . . ? C112 C111 C116 113.8(5) . . ? C112 C111 Au1 121.9(4) . . ? C116 C111 Au1 124.3(4) . . ? F112 C112 C111 120.5(5) . . ? F112 C112 C113 114.9(5) . . ? C111 C112 C113 124.6(5) . . ? F113 C113 C114 119.3(5) . . ? F113 C113 C112 121.6(5) . . ? C114 C113 C112 119.1(5) . . ? F114 C114 C113 121.8(5) . . ? F114 C114 C115 119.0(5) . . ? C113 C114 C115 119.2(5) . . ? F115 C115 C116 121.0(5) . . ? F115 C115 C114 119.7(5) . . ? C116 C115 C114 119.3(5) . . ? F116 C116 C115 116.7(4) . . ? F116 C116 C111 119.4(5) . . ? C115 C116 C111 123.9(5) . . ? N2 C211 N1 126.6(5) . . ? N2 C211 S1 122.3(4) . . ? N1 C211 S1 111.1(4) . . ? C213 C212 C217 122.0(5) . . ? C213 C212 S1 127.5(4) . . ? C217 C212 S1 110.5(4) . . ? C214 C213 C212 117.0(5) . . ? C214 C213 H1 121.5 . . ? C212 C213 H1 121.5 . . ? C213 C214 C215 121.6(5) . . ? C213 C214 H2 119.2 . . ? C215 C214 H2 119.2 . . ? C214 C215 C216 120.9(5) . . ? C214 C215 H3 119.6 . . ? C216 C215 H3 119.6 . . ? C217 C216 C215 118.1(5) . . ? C217 C216 H4 121.0 . . ? C215 C216 H4 121.0 . . ? C216 C217 N1 127.3(5) . . ? C216 C217 C212 120.5(5) . . ? N1 C217 C212 112.2(5) . . ? N1 C218 H6 109.5 . . ? N1 C218 H7 109.5 . . ? H6 C218 H7 109.5 . . ? N1 C218 H5 109.5 . . ? H6 C218 H5 109.5 . . ? H7 C218 H5 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C2 -6.2(6) . . . . ? O1 C1 C2 C3 -17.3(6) . . . . ? C1 C2 C3 C4 33.1(6) . . . . ? C1 O1 C4 C3 27.7(6) . . . . ? C2 C3 C4 O1 -37.7(6) . . . . ? C116 C111 C112 F112 -178.8(4) . . . . ? Au1 C111 C112 F112 1.0(7) . . . . ? C116 C111 C112 C113 1.8(8) . . . . ? Au1 C111 C112 C113 -178.3(4) . . . . ? F112 C112 C113 F113 -0.9(7) . . . . ? C111 C112 C113 F113 178.4(5) . . . . ? F112 C112 C113 C114 179.4(5) . . . . ? C111 C112 C113 C114 -1.2(8) . . . . ? F113 C113 C114 F114 0.4(8) . . . . ? C112 C113 C114 F114 -180.0(5) . . . . ? F113 C113 C114 C115 -179.5(5) . . . . ? C112 C113 C114 C115 0.2(8) . . . . ? F114 C114 C115 F115 1.4(8) . . . . ? C113 C114 C115 F115 -178.7(5) . . . . ? F114 C114 C115 C116 -179.8(5) . . . . ? C113 C114 C115 C116 0.1(8) . . . . ? F115 C115 C116 F116 -1.6(7) . . . . ? C114 C115 C116 F116 179.6(5) . . . . ? F115 C115 C116 C111 179.4(5) . . . . ? C114 C115 C116 C111 0.7(8) . . . . ? C112 C111 C116 F116 179.5(5) . . . . ? Au1 C111 C116 F116 -0.3(7) . . . . ? C112 C111 C116 C115 -1.5(8) . . . . ? Au1 C111 C116 C115 178.6(4) . . . . ? Au1 N2 C211 N1 177.5(4) . . . . ? Au1 N2 C211 S1 -4.2(7) . . . . ? C217 N1 C211 N2 -177.8(5) . . . . ? C218 N1 C211 N2 0.2(8) . . . . ? C217 N1 C211 S1 3.8(6) . . . . ? C218 N1 C211 S1 -178.2(4) . . . . ? C212 S1 C211 N2 178.2(5) . . . . ? C212 S1 C211 N1 -3.3(4) . . . . ? C211 S1 C212 C213 -177.4(5) . . . . ? C211 S1 C212 C217 2.1(4) . . . . ? C217 C212 C213 C214 -0.1(8) . . . . ? S1 C212 C213 C214 179.4(4) . . . . ? C212 C213 C214 C215 0.9(8) . . . . ? C213 C214 C215 C216 -0.3(8) . . . . ? C214 C215 C216 C217 -1.1(8) . . . . ? C215 C216 C217 N1 -178.6(5) . . . . ? C215 C216 C217 C212 1.9(8) . . . . ? C211 N1 C217 C216 178.4(5) . . . . ? C218 N1 C217 C216 0.4(8) . . . . ? C211 N1 C217 C212 -2.2(6) . . . . ? C218 N1 C217 C212 179.9(5) . . . . ? C213 C212 C217 C216 -1.3(8) . . . . ? S1 C212 C217 C216 179.1(4) . . . . ? C213 C212 C217 N1 179.1(5) . . . . ? S1 C212 C217 N1 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 3.632 _refine_diff_density_min -1.243 _refine_diff_density_rms 0.212 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 801427' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point '100-106 ^o^C' _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Au F5 N2 O S' _chemical_formula_weight 550.30 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' F F 0.0171 0.0103 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7762(14) _cell_length_b 17.691(4) _cell_length_c 15.393(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.25(3) _cell_angle_gamma 90.00 _cell_volume 1682.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3190 _cell_measurement_theta_min 2.3025 _cell_measurement_theta_max 25.635 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 8.922 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.7756 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9242 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.72 _reflns_number_total 3191 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0337P)^2^] 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 3191 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.11109(3) 0.720413(10) 0.716473(13) 0.01600(8) Uani 1 1 d . . . S1 S 0.2226(2) 0.87754(7) 0.85484(9) 0.0182(3) Uani 1 1 d . . . O1 O 0.4634(7) 0.5805(2) 0.9368(3) 0.0308(10) Uani 1 1 d . . . N1 N 0.3984(7) 0.7978(2) 1.0056(3) 0.0148(9) Uani 1 1 d . . . C1 C 0.6307(12) 0.4874(4) 0.8795(5) 0.0477(19) Uani 1 1 d . . . H3 H 0.6349 0.4347 0.8998 0.072 Uiso 1 1 calc R . . H2 H 0.7639 0.5131 0.9215 0.072 Uiso 1 1 calc R . . H1 H 0.6181 0.4889 0.8138 0.072 Uiso 1 1 calc R . . N2 N 0.2596(7) 0.7274(2) 0.8607(3) 0.0184(10) Uani 1 1 d . . . H14 H 0.3008 0.6848 0.8926 0.022 Uiso 1 1 calc R . . C2 C 0.4382(10) 0.5266(3) 0.8849(4) 0.0289(14) Uani 1 1 d . . . C3 C 0.2205(12) 0.4966(4) 0.8248(5) 0.054(2) Uani 1 1 d . . . H4 H 0.1102 0.5280 0.8330 0.081 Uiso 1 1 calc R . . H6 H 0.2086 0.4446 0.8439 0.081 Uiso 1 1 calc R . . H5 H 0.1987 0.4974 0.7578 0.081 Uiso 1 1 calc R . . C11 C -0.0339(8) 0.7112(3) 0.5744(3) 0.0145(11) Uani 1 1 d . . . F12 F -0.0481(5) 0.57839(15) 0.58294(19) 0.0216(7) Uani 1 1 d . . . C12 C -0.0925(8) 0.6428(3) 0.5295(4) 0.0157(11) Uani 1 1 d . . . F13 F -0.2455(5) 0.56381(17) 0.3928(2) 0.0264(7) Uani 1 1 d . . . C13 C -0.1938(8) 0.6331(3) 0.4325(3) 0.0188(11) Uani 1 1 d . . . F14 F -0.3406(5) 0.68806(18) 0.2794(2) 0.0292(7) Uani 1 1 d . . . C14 C -0.2425(9) 0.6957(3) 0.3748(4) 0.0217(12) Uani 1 1 d . . . F15 F -0.2318(5) 0.82815(18) 0.3585(2) 0.0312(8) Uani 1 1 d . . . C15 C -0.1881(9) 0.7664(3) 0.4147(4) 0.0217(12) Uani 1 1 d . . . F16 F -0.0340(5) 0.84391(16) 0.5484(2) 0.0265(7) Uani 1 1 d . . . C16 C -0.0855(8) 0.7727(3) 0.5129(4) 0.0175(11) Uani 1 1 d . . . C21 C 0.2986(8) 0.7893(3) 0.9095(4) 0.0173(11) Uani 1 1 d . . . C22 C 0.3246(8) 0.9221(3) 0.9657(4) 0.0201(11) Uani 1 1 d . . . H7 H 0.3186 0.9751 0.9742 0.024 Uiso 1 1 calc R . . C23 C 0.4122(8) 0.8730(3) 1.0372(4) 0.0182(11) Uani 1 1 d . . . C24 C 0.4729(9) 0.7327(3) 1.0698(4) 0.0198(12) Uani 1 1 d . . . H10 H 0.3566 0.7158 1.0874 0.030 Uiso 1 1 calc R . . H8 H 0.5992 0.7472 1.1273 0.030 Uiso 1 1 calc R . . H9 H 0.5127 0.6915 1.0375 0.030 Uiso 1 1 calc R . . C25 C 0.5172(9) 0.8904(3) 1.1412(3) 0.0232(12) Uani 1 1 d . . . H11 H 0.5189 0.9452 1.1506 0.035 Uiso 1 1 calc R . . H13 H 0.6660 0.8712 1.1679 0.035 Uiso 1 1 calc R . . H12 H 0.4356 0.8661 1.1734 0.035 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 0.01550(12) 0.01662(11) 0.01358(11) -0.00116(8) 0.00364(8) -0.00027(9) S1 0.0199(7) 0.0160(6) 0.0160(7) 0.0026(5) 0.0047(6) 0.0013(5) O1 0.043(3) 0.017(2) 0.028(2) 0.0016(16) 0.010(2) 0.0078(18) N1 0.020(2) 0.012(2) 0.013(2) 0.0009(16) 0.0069(19) -0.0005(17) C1 0.067(5) 0.034(4) 0.048(4) 0.008(3) 0.030(4) 0.013(4) N2 0.021(2) 0.016(2) 0.013(2) 0.0002(17) 0.0020(19) 0.0016(19) C2 0.045(4) 0.020(3) 0.024(3) 0.007(2) 0.016(3) 0.002(3) C3 0.053(5) 0.056(5) 0.043(4) -0.014(4) 0.009(4) -0.013(4) C11 0.013(3) 0.021(3) 0.012(2) 0.0018(19) 0.008(2) 0.001(2) F12 0.0272(18) 0.0167(15) 0.0180(15) 0.0028(12) 0.0063(14) 0.0006(13) C12 0.012(3) 0.013(3) 0.023(3) 0.002(2) 0.007(2) 0.001(2) F13 0.0309(19) 0.0248(17) 0.0208(16) -0.0087(13) 0.0079(14) -0.0032(14) C13 0.020(3) 0.020(3) 0.014(3) -0.004(2) 0.005(2) 0.001(2) F14 0.0304(19) 0.0426(19) 0.0104(15) 0.0000(14) 0.0041(14) 0.0022(16) C14 0.020(3) 0.030(3) 0.011(3) 0.001(2) 0.002(2) 0.008(2) F15 0.040(2) 0.0310(19) 0.0234(17) 0.0106(14) 0.0138(16) 0.0098(16) C15 0.021(3) 0.021(3) 0.025(3) 0.009(2) 0.012(2) 0.004(2) F16 0.0287(18) 0.0156(16) 0.0324(18) -0.0006(13) 0.0098(15) 0.0019(13) C16 0.018(3) 0.016(3) 0.021(3) -0.001(2) 0.010(2) 0.002(2) C21 0.011(3) 0.022(3) 0.017(3) 0.001(2) 0.004(2) 0.000(2) C22 0.017(3) 0.019(3) 0.022(3) -0.003(2) 0.006(2) -0.002(2) C23 0.017(3) 0.019(3) 0.021(3) -0.004(2) 0.010(2) -0.003(2) C24 0.025(3) 0.017(3) 0.013(3) 0.001(2) 0.003(2) 0.000(2) C25 0.027(3) 0.028(3) 0.015(3) -0.004(2) 0.009(2) -0.004(2) _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 C11 2.002(5) . ? Au1 N2 2.031(4) . ? S1 C22 1.744(5) . ? S1 C21 1.748(5) . ? O1 C2 1.211(6) . ? N1 C21 1.359(6) . ? N1 C23 1.406(6) . ? N1 C24 1.466(6) . ? C1 C2 1.509(9) . ? C1 H3 0.9800 . ? C1 H2 0.9800 . ? C1 H1 0.9800 . ? N2 C21 1.292(6) . ? N2 H14 0.8800 . ? C2 C3 1.481(9) . ? C3 H4 0.9800 . ? C3 H6 0.9800 . ? C3 H5 0.9800 . ? C11 C12 1.370(7) . ? C11 C16 1.390(7) . ? F12 C12 1.364(5) . ? C12 C13 1.374(7) . ? F13 C13 1.350(6) . ? C13 C14 1.372(7) . ? F14 C14 1.347(6) . ? C14 C15 1.376(8) . ? F15 C15 1.349(6) . ? C15 C16 1.385(8) . ? F16 C16 1.360(5) . ? C22 C23 1.334(7) . ? C22 H7 0.9500 . ? C23 C25 1.493(7) . ? C24 H10 0.9800 . ? C24 H8 0.9800 . ? C24 H9 0.9800 . ? C25 H11 0.9800 . ? C25 H13 0.9800 . ? C25 H12 0.9800 . ? 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 C11 Au1 N2 178.78(17) . . ? C22 S1 C21 90.7(2) . . ? C21 N1 C23 114.5(4) . . ? C21 N1 C24 121.7(4) . . ? C23 N1 C24 123.7(4) . . ? C2 C1 H3 109.5 . . ? C2 C1 H2 109.5 . . ? H3 C1 H2 109.5 . . ? C2 C1 H1 109.5 . . ? H3 C1 H1 109.5 . . ? H2 C1 H1 109.5 . . ? C21 N2 Au1 125.3(3) . . ? C21 N2 H14 117.3 . . ? Au1 N2 H14 117.3 . . ? O1 C2 C3 121.9(6) . . ? O1 C2 C1 120.5(6) . . ? C3 C2 C1 117.6(6) . . ? C2 C3 H4 109.5 . . ? C2 C3 H6 109.5 . . ? H4 C3 H6 109.5 . . ? C2 C3 H5 109.5 . . ? H4 C3 H5 109.5 . . ? H6 C3 H5 109.5 . . ? C12 C11 C16 114.1(5) . . ? C12 C11 Au1 122.3(4) . . ? C16 C11 Au1 123.6(4) . . ? F12 C12 C11 119.1(4) . . ? F12 C12 C13 116.1(4) . . ? C11 C12 C13 124.8(5) . . ? F13 C13 C14 119.4(4) . . ? F13 C13 C12 121.7(4) . . ? C14 C13 C12 118.9(5) . . ? F14 C14 C13 120.3(5) . . ? F14 C14 C15 120.0(5) . . ? C13 C14 C15 119.7(5) . . ? F15 C15 C14 120.1(5) . . ? F15 C15 C16 121.0(5) . . ? C14 C15 C16 118.9(5) . . ? F16 C16 C15 116.4(4) . . ? F16 C16 C11 120.0(5) . . ? C15 C16 C11 123.6(5) . . ? N2 C21 N1 128.2(5) . . ? N2 C21 S1 121.8(4) . . ? N1 C21 S1 109.9(4) . . ? C23 C22 S1 112.1(4) . . ? C23 C22 H7 123.9 . . ? S1 C22 H7 123.9 . . ? C22 C23 N1 112.7(4) . . ? C22 C23 C25 127.3(5) . . ? N1 C23 C25 120.0(4) . . ? N1 C24 H10 109.5 . . ? N1 C24 H8 109.5 . . ? H10 C24 H8 109.5 . . ? N1 C24 H9 109.5 . . ? H10 C24 H9 109.5 . . ? H8 C24 H9 109.5 . . ? C23 C25 H11 109.5 . . ? C23 C25 H13 109.5 . . ? H11 C25 H13 109.5 . . ? C23 C25 H12 109.5 . . ? H11 C25 H12 109.5 . . ? H13 C25 H12 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 F12 179.5(4) . . . . ? Au1 C11 C12 F12 -0.9(7) . . . . ? C16 C11 C12 C13 -0.1(8) . . . . ? Au1 C11 C12 C13 179.4(4) . . . . ? F12 C12 C13 F13 -0.2(7) . . . . ? C11 C12 C13 F13 179.4(5) . . . . ? F12 C12 C13 C14 -179.9(5) . . . . ? C11 C12 C13 C14 -0.3(8) . . . . ? F13 C13 C14 F14 -0.1(8) . . . . ? C12 C13 C14 F14 179.6(5) . . . . ? F13 C13 C14 C15 -179.2(5) . . . . ? C12 C13 C14 C15 0.5(8) . . . . ? F14 C14 C15 F15 -0.3(8) . . . . ? C13 C14 C15 F15 178.8(5) . . . . ? F14 C14 C15 C16 -179.4(5) . . . . ? C13 C14 C15 C16 -0.3(8) . . . . ? F15 C15 C16 F16 0.4(7) . . . . ? C14 C15 C16 F16 179.5(5) . . . . ? F15 C15 C16 C11 -179.2(5) . . . . ? C14 C15 C16 C11 -0.1(8) . . . . ? C12 C11 C16 F16 -179.3(4) . . . . ? Au1 C11 C16 F16 1.2(7) . . . . ? C12 C11 C16 C15 0.3(8) . . . . ? Au1 C11 C16 C15 -179.2(4) . . . . ? Au1 N2 C21 N1 -179.4(4) . . . . ? Au1 N2 C21 S1 0.7(7) . . . . ? C23 N1 C21 N2 -178.7(5) . . . . ? C24 N1 C21 N2 -2.0(8) . . . . ? C23 N1 C21 S1 1.2(5) . . . . ? C24 N1 C21 S1 177.9(4) . . . . ? C22 S1 C21 N2 178.6(5) . . . . ? C22 S1 C21 N1 -1.3(4) . . . . ? C21 S1 C22 C23 1.1(4) . . . . ? S1 C22 C23 N1 -0.6(6) . . . . ? S1 C22 C23 C25 179.2(4) . . . . ? C21 N1 C23 C22 -0.4(7) . . . . ? C24 N1 C23 C22 -177.0(5) . . . . ? C21 N1 C23 C25 179.7(5) . . . . ? C24 N1 C23 C25 3.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.72 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.386 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.156 #===END data_4b _database_code_depnum_ccdc_archive 'CCDC 801428' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point '126-128 ^o^C' _chemical_formula_moiety 'C27 H26 Au N3 P, N O3' _chemical_formula_sum 'C27 H26 Au N4 O3 P' _chemical_formula_weight 682.45 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' Au Au -2.0133 8.8022 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3222(16) _cell_length_b 15.499(3) _cell_length_c 17.446(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.825(3) _cell_angle_gamma 90.00 _cell_volume 2502.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6944 _cell_measurement_theta_min 2.625 _cell_measurement_theta_max 26.376 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 5.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4674 _exptl_absorpt_correction_T_max 0.7542 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13604 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4946 _reflns_number_gt 4219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0298P)^2^+0.4369P] 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 4946 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.280305(14) 0.371680(8) 0.026725(7) 0.01627(6) Uani 1 1 d . . . P1 P 0.32583(10) 0.24356(6) 0.08260(5) 0.01455(19) Uani 1 1 d . . . O1 O 0.1872(3) 0.69901(18) 0.12406(15) 0.0313(7) Uani 1 1 d . . . N1 N 0.2101(3) 0.56946(19) -0.14719(16) 0.0166(7) Uani 1 1 d . . . O2 O 0.0586(3) 0.61523(17) 0.04363(16) 0.0279(7) Uani 1 1 d . . . N2 N 0.3991(3) 0.48297(19) -0.12896(17) 0.0169(7) Uani 1 1 d . . . O3 O 0.1715(3) 0.56285(18) 0.14927(16) 0.0291(7) Uani 1 1 d . . . N3 N 0.2376(3) 0.4842(2) -0.03238(16) 0.0178(7) Uani 1 1 d . . . H11 H 0.1827 0.5209 -0.0108 0.021 Uiso 1 1 calc R . . N4 N 0.1390(3) 0.6259(2) 0.10572(19) 0.0206(7) Uani 1 1 d . . . C111 C 0.2454(4) 0.1579(2) 0.02088(19) 0.0154(8) Uani 1 1 d . . . C112 C 0.1066(4) 0.1704(2) -0.0156(2) 0.0186(8) Uani 1 1 d . . . H112 H 0.0581 0.2234 -0.0095 0.022 Uiso 1 1 calc R . . C113 C 0.0381(4) 0.1053(3) -0.0614(2) 0.0227(9) Uani 1 1 d . . . H113 H -0.0573 0.1137 -0.0860 0.027 Uiso 1 1 calc R . . C114 C 0.1087(4) 0.0290(3) -0.0707(2) 0.0241(9) Uani 1 1 d . . . H114 H 0.0618 -0.0151 -0.1022 0.029 Uiso 1 1 calc R . . C115 C 0.2478(4) 0.0157(3) -0.0348(2) 0.0254(9) Uani 1 1 d . . . H115 H 0.2959 -0.0372 -0.0418 0.030 Uiso 1 1 calc R . . C116 C 0.3167(4) 0.0800(2) 0.0116(2) 0.0207(8) Uani 1 1 d . . . H116 H 0.4117 0.0710 0.0367 0.025 Uiso 1 1 calc R . . C121 C 0.2569(4) 0.2265(2) 0.1743(2) 0.0158(8) Uani 1 1 d . . . C122 C 0.2006(4) 0.1476(2) 0.1940(2) 0.0188(8) Uani 1 1 d . . . H122 H 0.1986 0.1002 0.1594 0.023 Uiso 1 1 calc R . . C123 C 0.1471(4) 0.1384(2) 0.2646(2) 0.0201(8) Uani 1 1 d . . . H123 H 0.1057 0.0851 0.2776 0.024 Uiso 1 1 calc R . . C124 C 0.1539(4) 0.2063(3) 0.3160(2) 0.0243(9) Uani 1 1 d . . . H124 H 0.1179 0.1996 0.3644 0.029 Uiso 1 1 calc R . . C125 C 0.2129(4) 0.2841(3) 0.2974(2) 0.0279(10) Uani 1 1 d . . . H125 H 0.2196 0.3302 0.3335 0.034 Uiso 1 1 calc R . . C126 C 0.2627(4) 0.2952(2) 0.2261(2) 0.0211(8) Uani 1 1 d . . . H126 H 0.3004 0.3494 0.2127 0.025 Uiso 1 1 calc R . . C131 C 0.5174(4) 0.2208(2) 0.0988(2) 0.0153(8) Uani 1 1 d . . . C132 C 0.5853(4) 0.1909(2) 0.1689(2) 0.0187(8) Uani 1 1 d . . . H132 H 0.5307 0.1801 0.2105 0.022 Uiso 1 1 calc R . . C133 C 0.7340(4) 0.1767(2) 0.1780(2) 0.0202(8) Uani 1 1 d . . . H133 H 0.7807 0.1563 0.2260 0.024 Uiso 1 1 calc R . . C134 C 0.8139(4) 0.1920(2) 0.1177(2) 0.0204(8) Uani 1 1 d . . . H134 H 0.9153 0.1825 0.1242 0.024 Uiso 1 1 calc R . . C135 C 0.7457(4) 0.2213(2) 0.0474(2) 0.0200(8) Uani 1 1 d . . . H135 H 0.8005 0.2314 0.0058 0.024 Uiso 1 1 calc R . . C136 C 0.5986(4) 0.2358(2) 0.0379(2) 0.0175(8) Uani 1 1 d . . . H136 H 0.5525 0.2560 -0.0103 0.021 Uiso 1 1 calc R . . C211 C 0.2796(4) 0.5099(2) -0.0976(2) 0.0178(8) Uani 1 1 d . . . C212 C 0.4051(4) 0.5240(2) -0.1995(2) 0.0178(8) Uani 1 1 d . . . C213 C 0.5017(4) 0.5164(2) -0.2531(2) 0.0224(9) Uani 1 1 d . . . H7 H 0.5830 0.4792 -0.2451 0.027 Uiso 1 1 calc R . . C214 C 0.4737(4) 0.5660(2) -0.3194(2) 0.0236(9) Uani 1 1 d . . . H8 H 0.5367 0.5620 -0.3582 0.028 Uiso 1 1 calc R . . C215 C 0.3563(5) 0.6214(2) -0.3306(2) 0.0252(9) Uani 1 1 d . . . H9 H 0.3419 0.6549 -0.3765 0.030 Uiso 1 1 calc R . . C216 C 0.2590(4) 0.6292(2) -0.2765(2) 0.0223(9) Uani 1 1 d . . . H10 H 0.1788 0.6674 -0.2840 0.027 Uiso 1 1 calc R . . C217 C 0.2850(4) 0.5785(2) -0.2112(2) 0.0176(8) Uani 1 1 d . . . C218 C 0.0654(4) 0.6020(2) -0.1404(2) 0.0215(8) Uani 1 1 d . . . H1 H -0.0023 0.5535 -0.1414 0.032 Uiso 1 1 calc R . . H3 H 0.0353 0.6409 -0.1836 0.032 Uiso 1 1 calc R . . H2 H 0.0659 0.6334 -0.0916 0.032 Uiso 1 1 calc R . . C219 C 0.4982(4) 0.4148(3) -0.0987(2) 0.0244(9) Uani 1 1 d . . . H4 H 0.5295 0.4254 -0.0439 0.037 Uiso 1 1 calc R . . H6 H 0.5826 0.4144 -0.1273 0.037 Uiso 1 1 calc R . . H5 H 0.4490 0.3589 -0.1047 0.037 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 0.01652(9) 0.01539(9) 0.01715(9) 0.00248(5) 0.00306(6) 0.00117(6) P1 0.0137(5) 0.0155(5) 0.0148(5) 0.0013(4) 0.0030(4) 0.0007(4) O1 0.0449(19) 0.0244(16) 0.0252(15) -0.0037(12) 0.0060(14) -0.0104(14) N1 0.0162(16) 0.0151(16) 0.0183(16) -0.0003(12) 0.0015(13) -0.0011(13) O2 0.0219(15) 0.0347(17) 0.0258(16) -0.0081(12) -0.0026(13) 0.0033(12) N2 0.0157(16) 0.0152(16) 0.0197(16) 0.0038(12) 0.0014(13) 0.0022(12) O3 0.0281(16) 0.0275(16) 0.0318(16) 0.0094(13) 0.0046(13) -0.0002(13) N3 0.0165(17) 0.0147(17) 0.0229(17) 0.0025(12) 0.0053(14) 0.0024(12) N4 0.0178(17) 0.0235(19) 0.0223(18) -0.0041(14) 0.0092(15) 0.0020(14) C111 0.0143(18) 0.019(2) 0.0129(18) 0.0037(14) 0.0032(15) -0.0033(15) C112 0.018(2) 0.020(2) 0.0179(19) 0.0045(15) 0.0046(16) 0.0004(16) C113 0.0129(19) 0.033(2) 0.021(2) 0.0056(17) -0.0002(16) -0.0041(17) C114 0.026(2) 0.026(2) 0.022(2) -0.0016(16) 0.0055(17) -0.0127(18) C115 0.025(2) 0.018(2) 0.034(2) -0.0038(17) 0.0060(19) 0.0012(17) C116 0.020(2) 0.019(2) 0.023(2) 0.0014(16) 0.0031(17) 0.0006(16) C121 0.0108(18) 0.020(2) 0.0167(19) 0.0022(14) 0.0014(15) 0.0031(14) C122 0.017(2) 0.021(2) 0.0182(19) 0.0031(15) 0.0012(16) 0.0013(15) C123 0.0135(19) 0.022(2) 0.024(2) 0.0058(16) -0.0001(16) 0.0025(15) C124 0.022(2) 0.033(2) 0.019(2) 0.0039(17) 0.0060(17) 0.0040(18) C125 0.033(2) 0.030(2) 0.023(2) -0.0080(17) 0.0118(19) -0.0058(19) C126 0.021(2) 0.020(2) 0.023(2) 0.0008(16) 0.0051(17) -0.0026(16) C131 0.0146(19) 0.0153(19) 0.0159(18) -0.0021(14) 0.0013(15) 0.0007(14) C132 0.017(2) 0.020(2) 0.0184(19) 0.0003(15) 0.0020(16) -0.0006(16) C133 0.022(2) 0.020(2) 0.0185(19) 0.0002(15) -0.0003(16) 0.0012(16) C134 0.0143(19) 0.016(2) 0.030(2) -0.0054(16) -0.0008(16) 0.0021(15) C135 0.018(2) 0.019(2) 0.023(2) 0.0009(15) 0.0071(17) -0.0011(16) C136 0.0137(19) 0.021(2) 0.0174(19) 0.0041(15) -0.0003(15) 0.0009(15) C211 0.019(2) 0.0135(19) 0.020(2) -0.0032(15) 0.0012(16) -0.0015(15) C212 0.020(2) 0.0153(19) 0.0171(19) 0.0009(14) -0.0022(15) -0.0039(15) C213 0.021(2) 0.019(2) 0.027(2) -0.0011(16) 0.0057(17) -0.0017(16) C214 0.026(2) 0.025(2) 0.021(2) -0.0029(16) 0.0086(17) -0.0057(17) C215 0.035(2) 0.024(2) 0.016(2) 0.0023(16) 0.0001(18) -0.0069(18) C216 0.027(2) 0.017(2) 0.022(2) 0.0003(15) -0.0007(17) -0.0025(16) C217 0.022(2) 0.0146(19) 0.0162(19) -0.0034(15) 0.0030(16) -0.0060(16) C218 0.019(2) 0.017(2) 0.028(2) 0.0013(16) 0.0022(17) 0.0029(16) C219 0.022(2) 0.025(2) 0.027(2) 0.0089(17) 0.0047(17) 0.0054(17) _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 N3 2.040(3) . ? Au1 P1 2.2305(10) . ? P1 C131 1.809(4) . ? P1 C121 1.812(4) . ? P1 C111 1.814(4) . ? O1 N4 1.246(4) . ? N1 C211 1.373(5) . ? N1 C217 1.393(4) . ? N1 C218 1.458(4) . ? O2 N4 1.253(4) . ? N2 C211 1.364(4) . ? N2 C212 1.392(4) . ? N2 C219 1.460(4) . ? O3 N4 1.253(4) . ? N3 C211 1.309(4) . ? N3 H11 0.8800 . ? C111 C112 1.387(5) . ? C111 C116 1.396(6) . ? C112 C113 1.393(5) . ? C112 H112 0.9500 . ? C113 C114 1.373(5) . ? C113 H113 0.9500 . ? C114 C115 1.387(5) . ? C114 H114 0.9500 . ? C115 C116 1.392(5) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C122 1.391(5) . ? C121 C126 1.394(5) . ? C122 C123 1.390(5) . ? C122 H122 0.9500 . ? C123 C124 1.380(5) . ? C123 H123 0.9500 . ? C124 C125 1.379(5) . ? C124 H124 0.9500 . ? C125 C126 1.389(5) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C131 C132 1.389(5) . ? C131 C136 1.395(5) . ? C132 C133 1.394(5) . ? C132 H132 0.9500 . ? C133 C134 1.380(5) . ? C133 H133 0.9500 . ? C134 C135 1.388(5) . ? C134 H134 0.9500 . ? C135 C136 1.380(5) . ? C135 H135 0.9500 . ? C136 H136 0.9500 . ? C212 C213 1.379(5) . ? C212 C217 1.397(5) . ? C213 C214 1.388(5) . ? C213 H7 0.9500 . ? C214 C215 1.386(6) . ? C214 H8 0.9500 . ? C215 C216 1.390(6) . ? C215 H9 0.9500 . ? C216 C217 1.382(5) . ? C216 H10 0.9500 . ? C218 H1 0.9800 . ? C218 H3 0.9800 . ? C218 H2 0.9800 . ? C219 H4 0.9800 . ? C219 H6 0.9800 . ? C219 H5 0.9800 . ? 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 N3 Au1 P1 175.60(8) . . ? C131 P1 C121 106.30(16) . . ? C131 P1 C111 106.30(16) . . ? C121 P1 C111 104.62(16) . . ? C131 P1 Au1 112.00(12) . . ? C121 P1 Au1 116.51(12) . . ? C111 P1 Au1 110.39(12) . . ? C211 N1 C217 109.2(3) . . ? C211 N1 C218 123.6(3) . . ? C217 N1 C218 126.0(3) . . ? C211 N2 C212 109.6(3) . . ? C211 N2 C219 126.1(3) . . ? C212 N2 C219 124.0(3) . . ? C211 N3 Au1 129.7(3) . . ? C211 N3 H11 115.1 . . ? Au1 N3 H11 115.1 . . ? O1 N4 O3 120.0(3) . . ? O1 N4 O2 120.2(3) . . ? O3 N4 O2 119.9(3) . . ? C112 C111 C116 119.9(4) . . ? C112 C111 P1 117.9(3) . . ? C116 C111 P1 122.2(3) . . ? C111 C112 C113 120.1(4) . . ? C111 C112 H112 120.0 . . ? C113 C112 H112 120.0 . . ? C114 C113 C112 119.9(4) . . ? C114 C113 H113 120.0 . . ? C112 C113 H113 120.0 . . ? C113 C114 C115 120.6(4) . . ? C113 C114 H114 119.7 . . ? C115 C114 H114 119.7 . . ? C114 C115 C116 119.9(4) . . ? C114 C115 H115 120.0 . . ? C116 C115 H115 120.0 . . ? C115 C116 C111 119.5(4) . . ? C115 C116 H116 120.2 . . ? C111 C116 H116 120.2 . . ? C122 C121 C126 119.8(3) . . ? C122 C121 P1 122.1(3) . . ? C126 C121 P1 118.1(3) . . ? C123 C122 C121 119.7(4) . . ? C123 C122 H122 120.1 . . ? C121 C122 H122 120.1 . . ? C124 C123 C122 120.2(4) . . ? C124 C123 H123 119.9 . . ? C122 C123 H123 119.9 . . ? C125 C124 C123 120.2(4) . . ? C125 C124 H124 119.9 . . ? C123 C124 H124 119.9 . . ? C124 C125 C126 120.3(4) . . ? C124 C125 H125 119.9 . . ? C126 C125 H125 119.9 . . ? C125 C126 C121 119.7(3) . . ? C125 C126 H126 120.2 . . ? C121 C126 H126 120.2 . . ? C132 C131 C136 119.6(3) . . ? C132 C131 P1 122.8(3) . . ? C136 C131 P1 117.6(3) . . ? C131 C132 C133 119.7(3) . . ? C131 C132 H132 120.1 . . ? C133 C132 H132 120.1 . . ? C134 C133 C132 120.4(4) . . ? C134 C133 H133 119.8 . . ? C132 C133 H133 119.8 . . ? C133 C134 C135 119.8(4) . . ? C133 C134 H134 120.1 . . ? C135 C134 H134 120.1 . . ? C136 C135 C134 120.3(4) . . ? C136 C135 H135 119.9 . . ? C134 C135 H135 119.9 . . ? C135 C136 C131 120.1(3) . . ? C135 C136 H136 119.9 . . ? C131 C136 H136 119.9 . . ? N3 C211 N2 126.7(3) . . ? N3 C211 N1 125.8(3) . . ? N2 C211 N1 107.5(3) . . ? C213 C212 N2 131.2(3) . . ? C213 C212 C217 121.9(3) . . ? N2 C212 C217 106.8(3) . . ? C212 C213 C214 116.4(4) . . ? C212 C213 H7 121.8 . . ? C214 C213 H7 121.8 . . ? C215 C214 C213 121.8(4) . . ? C215 C214 H8 119.1 . . ? C213 C214 H8 119.1 . . ? C214 C215 C216 121.8(4) . . ? C214 C215 H9 119.1 . . ? C216 C215 H9 119.1 . . ? C217 C216 C215 116.4(4) . . ? C217 C216 H10 121.8 . . ? C215 C216 H10 121.8 . . ? C216 C217 N1 131.5(4) . . ? C216 C217 C212 121.6(3) . . ? N1 C217 C212 107.0(3) . . ? N1 C218 H1 109.5 . . ? N1 C218 H3 109.5 . . ? H1 C218 H3 109.5 . . ? N1 C218 H2 109.5 . . ? H1 C218 H2 109.5 . . ? H3 C218 H2 109.5 . . ? N2 C219 H4 109.5 . . ? N2 C219 H6 109.5 . . ? H4 C219 H6 109.5 . . ? N2 C219 H5 109.5 . . ? H4 C219 H5 109.5 . . ? H6 C219 H5 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C131 P1 C111 C112 -164.6(3) . . . . ? C121 P1 C111 C112 83.2(3) . . . . ? Au1 P1 C111 C112 -42.9(3) . . . . ? C131 P1 C111 C116 17.6(3) . . . . ? C121 P1 C111 C116 -94.6(3) . . . . ? Au1 P1 C111 C116 139.3(3) . . . . ? C116 C111 C112 C113 0.2(5) . . . . ? P1 C111 C112 C113 -177.6(3) . . . . ? C111 C112 C113 C114 -0.5(5) . . . . ? C112 C113 C114 C115 0.3(6) . . . . ? C113 C114 C115 C116 0.3(6) . . . . ? C114 C115 C116 C111 -0.6(6) . . . . ? C112 C111 C116 C115 0.4(5) . . . . ? P1 C111 C116 C115 178.1(3) . . . . ? C131 P1 C121 C122 -92.5(3) . . . . ? C111 P1 C121 C122 19.7(3) . . . . ? Au1 P1 C121 C122 141.9(3) . . . . ? C131 P1 C121 C126 86.9(3) . . . . ? C111 P1 C121 C126 -160.9(3) . . . . ? Au1 P1 C121 C126 -38.7(3) . . . . ? C126 C121 C122 C123 1.5(5) . . . . ? P1 C121 C122 C123 -179.0(3) . . . . ? C121 C122 C123 C124 -2.0(6) . . . . ? C122 C123 C124 C125 0.5(6) . . . . ? C123 C124 C125 C126 1.6(6) . . . . ? C124 C125 C126 C121 -2.0(6) . . . . ? C122 C121 C126 C125 0.5(6) . . . . ? P1 C121 C126 C125 -179.0(3) . . . . ? C121 P1 C131 C132 3.9(3) . . . . ? C111 P1 C131 C132 -107.2(3) . . . . ? Au1 P1 C131 C132 132.1(3) . . . . ? C121 P1 C131 C136 -175.2(3) . . . . ? C111 P1 C131 C136 73.8(3) . . . . ? Au1 P1 C131 C136 -46.9(3) . . . . ? C136 C131 C132 C133 0.5(5) . . . . ? P1 C131 C132 C133 -178.4(3) . . . . ? C131 C132 C133 C134 -0.2(5) . . . . ? C132 C133 C134 C135 -0.3(6) . . . . ? C133 C134 C135 C136 0.5(6) . . . . ? C134 C135 C136 C131 -0.2(6) . . . . ? C132 C131 C136 C135 -0.4(5) . . . . ? P1 C131 C136 C135 178.7(3) . . . . ? Au1 N3 C211 N2 -24.4(5) . . . . ? Au1 N3 C211 N1 155.5(3) . . . . ? C212 N2 C211 N3 178.8(3) . . . . ? C219 N2 C211 N3 5.1(6) . . . . ? C212 N2 C211 N1 -1.1(4) . . . . ? C219 N2 C211 N1 -174.8(3) . . . . ? C217 N1 C211 N3 -178.6(3) . . . . ? C218 N1 C211 N3 -10.9(6) . . . . ? C217 N1 C211 N2 1.4(4) . . . . ? C218 N1 C211 N2 169.1(3) . . . . ? C211 N2 C212 C213 -177.9(4) . . . . ? C219 N2 C212 C213 -4.1(6) . . . . ? C211 N2 C212 C217 0.4(4) . . . . ? C219 N2 C212 C217 174.3(3) . . . . ? N2 C212 C213 C214 178.4(4) . . . . ? C217 C212 C213 C214 0.2(5) . . . . ? C212 C213 C214 C215 1.0(6) . . . . ? C213 C214 C215 C216 -1.0(6) . . . . ? C214 C215 C216 C217 -0.4(6) . . . . ? C215 C216 C217 N1 -179.1(4) . . . . ? C215 C216 C217 C212 1.7(5) . . . . ? C211 N1 C217 C216 179.6(4) . . . . ? C218 N1 C217 C216 12.3(6) . . . . ? C211 N1 C217 C212 -1.1(4) . . . . ? C218 N1 C217 C212 -168.5(3) . . . . ? C213 C212 C217 C216 -1.7(6) . . . . ? N2 C212 C217 C216 179.8(3) . . . . ? C213 C212 C217 N1 179.0(3) . . . . ? N2 C212 C217 N1 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.515 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.128 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 801429' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Au N2 P S, N O3' _chemical_formula_sum 'C26 H23 Au N3 O3 P S' _chemical_formula_weight 685.48 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' 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' P P 0.1023 0.0942 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1497(7) _cell_length_b 9.4618(11) _cell_length_c 17.9130(16) _cell_angle_alpha 86.292(2) _cell_angle_beta 80.051(2) _cell_angle_gamma 64.497(2) _cell_volume 1227.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2313 _cell_measurement_theta_min 2.309 _cell_measurement_theta_max 22.802 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.854 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 6.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.603 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details 'SADABS, Blessing, Acta Cryst. A51(1995) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11163 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.71 _reflns_number_total 4614 _reflns_number_gt 3935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 2002)' _computing_cell_refinement 'SAINT (Bruker 2003)' _computing_data_reduction 'SAINT (Bruker 2002)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0402P)^2^] 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 4614 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.21036(4) 0.80859(3) 0.320667(16) 0.01858(10) Uani 1 1 d . . . S1 S 0.3127(3) 0.5136(2) 0.44904(11) 0.0273(5) Uani 1 1 d . . . P1 P 0.3517(2) 0.8010(2) 0.20207(10) 0.0168(4) Uani 1 1 d . . . O1 O -0.2414(8) 1.0970(6) 0.4434(3) 0.0364(14) Uani 1 1 d . . . N1 N 0.0278(9) 0.6873(7) 0.5448(3) 0.0258(15) Uani 1 1 d . . . H1 H -0.2320 0.7853 0.5948 0.053 Uiso 1 1 calc R . . O2 O -0.4493(8) 1.1999(7) 0.3705(3) 0.0482(17) Uani 1 1 d . . . N2 N 0.0826(8) 0.8094(7) 0.4284(3) 0.0236(14) Uani 1 1 d . . . H2 H -0.1668 0.9035 0.5446 0.053 Uiso 1 1 calc R . . O3 O -0.1642(8) 1.0652(6) 0.3223(3) 0.0441(16) Uani 1 1 d . . . H3 H -0.1028 0.8491 0.6253 0.053 Uiso 1 1 calc R . . N4 N -0.2873(10) 1.1232(7) 0.3786(4) 0.0311(17) Uani 1 1 d . . . H4 H 0.4642 0.2067 0.5324 0.039 Uiso 1 1 calc R . . H5 H 0.3441 0.1387 0.6484 0.044 Uiso 1 1 calc R . . H6 H 0.0918 0.3199 0.7247 0.041 Uiso 1 1 calc R . . H7 H -0.0683 0.5737 0.6812 0.037 Uiso 1 1 calc R . . H8 H -0.0089 0.8986 0.4454 0.028 Uiso 1 1 calc R . . C111 C 0.2217(10) 0.7885(8) 0.1323(4) 0.0183(16) Uani 1 1 d . . . C112 C 0.0322(10) 0.8867(9) 0.1425(4) 0.0236(17) Uani 1 1 d . . . H112 H -0.0264 0.9481 0.1874 0.028 Uiso 1 1 calc R . . C113 C -0.0690(10) 0.8934(8) 0.0864(4) 0.0244(18) Uani 1 1 d . . . H113 H -0.1966 0.9617 0.0924 0.029 Uiso 1 1 calc R . . C114 C 0.0144(11) 0.8016(9) 0.0220(4) 0.0265(18) Uani 1 1 d . . . H114 H -0.0564 0.8067 -0.0159 0.032 Uiso 1 1 calc R . . C115 C 0.1997(10) 0.7024(8) 0.0120(4) 0.0240(17) Uani 1 1 d . . . H115 H 0.2556 0.6390 -0.0324 0.029 Uiso 1 1 calc R . . C116 C 0.3046(10) 0.6948(8) 0.0667(4) 0.0191(16) Uani 1 1 d . . . H116 H 0.4322 0.6264 0.0598 0.023 Uiso 1 1 calc R . . C121 C 0.3895(9) 0.9749(7) 0.1734(4) 0.0151(15) Uani 1 1 d . . . C122 C 0.4239(9) 1.0534(8) 0.2273(4) 0.0221(17) Uani 1 1 d . . . H122 H 0.4308 1.0149 0.2775 0.026 Uiso 1 1 calc R . . C123 C 0.4483(10) 1.1887(9) 0.2075(4) 0.0273(18) Uani 1 1 d . . . H123 H 0.4735 1.2416 0.2442 0.033 Uiso 1 1 calc R . . C124 C 0.4363(10) 1.2455(8) 0.1356(4) 0.0268(18) Uani 1 1 d . . . H124 H 0.4519 1.3385 0.1228 0.032 Uiso 1 1 calc R . . C125 C 0.4017(10) 1.1690(8) 0.0812(4) 0.0234(17) Uani 1 1 d . . . H125 H 0.3945 1.2083 0.0312 0.028 Uiso 1 1 calc R . . C126 C 0.3777(9) 1.0340(8) 0.1008(4) 0.0187(16) Uani 1 1 d . . . H126 H 0.3529 0.9814 0.0638 0.022 Uiso 1 1 calc R . . C131 C 0.5762(9) 0.6351(8) 0.1853(4) 0.0183(16) Uani 1 1 d . . . C132 C 0.6009(10) 0.4983(8) 0.2266(4) 0.0185(16) Uani 1 1 d . . . H132 H 0.5011 0.4943 0.2616 0.022 Uiso 1 1 calc R . . C133 C 0.7700(10) 0.3690(8) 0.2169(4) 0.0218(17) Uani 1 1 d . . . H133 H 0.7858 0.2755 0.2439 0.026 Uiso 1 1 calc R . . C134 C 0.9156(11) 0.3774(9) 0.1673(4) 0.0250(18) Uani 1 1 d . . . H134 H 1.0325 0.2898 0.1611 0.030 Uiso 1 1 calc R . . C135 C 0.8925(10) 0.5127(8) 0.1267(4) 0.0258(18) Uani 1 1 d . . . H135 H 0.9933 0.5175 0.0927 0.031 Uiso 1 1 calc R . . C136 C 0.7230(10) 0.6405(8) 0.1355(4) 0.0200(16) Uani 1 1 d . . . H136 H 0.7073 0.7327 0.1072 0.024 Uiso 1 1 calc R . . C211 C 0.1202(10) 0.6939(9) 0.4748(4) 0.0233(17) Uani 1 1 d . . . C212 C 0.2596(11) 0.4323(9) 0.5356(4) 0.0249(18) Uani 1 1 d . . . C213 C 0.3552(11) 0.2803(10) 0.5617(5) 0.032(2) Uani 1 1 d . . . C214 C 0.2854(12) 0.2425(10) 0.6307(5) 0.037(2) Uani 1 1 d . . . C215 C 0.1326(12) 0.3496(10) 0.6759(4) 0.034(2) Uani 1 1 d . . . C216 C 0.0384(12) 0.5002(10) 0.6507(4) 0.0305(19) Uani 1 1 d . . . C217 C 0.1037(10) 0.5411(8) 0.5795(4) 0.0223(17) Uani 1 1 d . . . C218 C -0.1307(12) 0.8163(9) 0.5801(4) 0.035(2) 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 0.01846(16) 0.01992(16) 0.01618(16) -0.00048(10) -0.00035(11) -0.00788(12) S1 0.0251(11) 0.0302(11) 0.0227(10) 0.0022(8) -0.0031(8) -0.0087(9) P1 0.0162(10) 0.0178(9) 0.0156(10) 0.0001(7) -0.0005(8) -0.0072(8) O1 0.041(4) 0.041(4) 0.025(3) 0.001(3) -0.006(3) -0.015(3) N1 0.026(4) 0.030(4) 0.024(4) 0.003(3) -0.005(3) -0.014(3) O2 0.026(3) 0.054(4) 0.043(4) -0.001(3) -0.012(3) 0.006(3) N2 0.022(3) 0.025(3) 0.019(3) -0.004(3) 0.005(3) -0.007(3) O3 0.042(4) 0.030(3) 0.036(4) 0.008(3) 0.007(3) 0.001(3) N4 0.034(4) 0.013(3) 0.039(4) -0.003(3) 0.003(4) -0.005(3) C111 0.023(4) 0.014(3) 0.019(4) 0.003(3) -0.005(3) -0.008(3) C112 0.027(4) 0.029(4) 0.020(4) 0.001(3) -0.005(3) -0.017(4) C113 0.021(4) 0.018(4) 0.039(5) 0.005(3) -0.007(4) -0.012(3) C114 0.030(5) 0.035(5) 0.022(4) 0.005(3) -0.008(4) -0.020(4) C115 0.022(4) 0.023(4) 0.031(4) -0.003(3) -0.002(3) -0.012(3) C116 0.015(4) 0.017(4) 0.027(4) 0.003(3) 0.003(3) -0.011(3) C121 0.013(4) 0.015(3) 0.017(4) -0.002(3) 0.006(3) -0.008(3) C122 0.019(4) 0.021(4) 0.024(4) 0.000(3) -0.002(3) -0.006(3) C123 0.028(5) 0.028(4) 0.034(5) -0.005(4) -0.004(4) -0.020(4) C124 0.022(4) 0.016(4) 0.038(5) 0.005(3) 0.002(4) -0.007(3) C125 0.023(4) 0.025(4) 0.020(4) -0.003(3) 0.001(3) -0.009(3) C126 0.019(4) 0.016(4) 0.023(4) -0.004(3) 0.000(3) -0.009(3) C131 0.014(4) 0.022(4) 0.018(4) -0.003(3) -0.003(3) -0.006(3) C132 0.023(4) 0.020(4) 0.023(4) 0.001(3) -0.006(3) -0.018(3) C133 0.025(4) 0.017(4) 0.023(4) 0.002(3) -0.001(3) -0.010(3) C134 0.027(4) 0.024(4) 0.022(4) -0.010(3) -0.005(3) -0.007(3) C135 0.019(4) 0.028(4) 0.025(4) -0.003(3) 0.001(3) -0.006(3) C136 0.028(4) 0.016(4) 0.016(4) 0.006(3) -0.007(3) -0.009(3) C211 0.024(4) 0.029(4) 0.023(4) -0.002(3) -0.007(3) -0.016(4) C212 0.028(4) 0.040(5) 0.016(4) 0.007(3) -0.008(3) -0.022(4) C213 0.028(5) 0.038(5) 0.033(5) 0.002(4) -0.010(4) -0.013(4) C214 0.047(6) 0.035(5) 0.036(5) 0.010(4) -0.016(4) -0.024(5) C215 0.056(6) 0.053(6) 0.014(4) 0.014(4) -0.019(4) -0.040(5) C216 0.038(5) 0.042(5) 0.022(4) 0.001(4) -0.010(4) -0.025(4) C217 0.023(4) 0.028(4) 0.026(4) 0.000(3) -0.006(3) -0.019(4) C218 0.046(6) 0.039(5) 0.021(4) 0.000(4) 0.006(4) -0.022(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 N2 2.028(6) . ? Au1 P1 2.2245(18) . ? S1 C212 1.755(7) . ? S1 C211 1.770(8) . ? P1 C111 1.812(7) . ? P1 C131 1.816(7) . ? P1 C121 1.827(7) . ? O1 N4 1.257(8) . ? N1 C211 1.359(9) . ? N1 C217 1.403(9) . ? N1 C218 1.421(9) . ? O2 N4 1.232(8) . ? N2 C211 1.289(9) . ? N2 H8 0.8800 . ? N4 O3 1.255(8) . ? C111 C116 1.402(9) . ? C111 C112 1.404(10) . ? C112 H112 0.9500 . ? C113 C114 1.377(10) . ? C113 C112 1.388(10) . ? C113 H113 0.9500 . ? C114 C115 1.379(10) . ? C114 H114 0.9500 . ? C115 C116 1.387(10) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C126 1.385(9) . ? C121 C122 1.388(9) . ? C122 C123 1.393(10) . ? C122 H122 0.9500 . ? C123 H123 0.9500 . ? C124 C123 1.367(10) . ? C124 H124 0.9500 . ? C125 C124 1.383(10) . ? C125 H125 0.9500 . ? C126 C125 1.388(10) . ? C126 H126 0.9500 . ? C131 C136 1.381(10) . ? C132 C133 1.385(9) . ? C132 C131 1.403(9) . ? C132 H132 0.9500 . ? C133 C134 1.382(10) . ? C133 H133 0.9500 . ? C134 H134 0.9500 . ? C135 C134 1.387(10) . ? C135 H135 0.9500 . ? C136 C135 1.381(9) . ? C136 H136 0.9500 . ? C212 C217 1.388(10) . ? C212 C213 1.403(11) . ? C213 C214 1.362(11) . ? C213 H4 0.9500 . ? C214 H5 0.9500 . ? C215 C214 1.380(12) . ? C215 H6 0.9500 . ? C216 C215 1.385(11) . ? C216 H7 0.9500 . ? C217 C216 1.391(10) . ? C218 H3 0.9800 . ? C218 H1 0.9800 . ? C218 H2 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Au1 P1 178.43(18) . . ? C212 S1 C211 90.4(4) . . ? C111 P1 C131 107.0(3) . . ? C111 P1 C121 103.0(3) . . ? C131 P1 C121 106.4(3) . . ? C111 P1 Au1 113.1(2) . . ? C131 P1 Au1 111.9(2) . . ? C121 P1 Au1 114.6(2) . . ? O2 N4 O1 121.2(7) . . ? O3 N4 O1 118.1(7) . . ? C211 N1 C217 113.8(6) . . ? C211 N1 C218 123.4(6) . . ? C217 N1 C218 122.8(6) . . ? C211 N2 Au1 127.3(5) . . ? C211 N2 H8 116.3 . . ? Au1 N2 H8 116.3 . . ? O2 N4 O3 120.6(7) . . ? C116 C111 C112 119.5(6) . . ? C116 C111 P1 122.8(5) . . ? C112 C111 P1 117.6(5) . . ? C113 C112 C111 119.5(7) . . ? C113 C112 H112 120.3 . . ? C111 C112 H112 120.3 . . ? C114 C113 C112 120.5(7) . . ? C114 C113 H113 119.8 . . ? C112 C113 H113 119.8 . . ? C113 C114 C115 120.6(7) . . ? C113 C114 H114 119.7 . . ? C115 C114 H114 119.7 . . ? C114 C115 C116 120.2(7) . . ? C114 C115 H115 119.9 . . ? C116 C115 H115 119.9 . . ? C115 C116 C111 119.8(7) . . ? C115 C116 H116 120.1 . . ? C111 C116 H116 120.1 . . ? C126 C121 C122 119.2(6) . . ? C126 C121 P1 122.1(5) . . ? C122 C121 P1 118.6(5) . . ? C121 C122 C123 119.8(7) . . ? C121 C122 H122 120.1 . . ? C123 C122 H122 120.1 . . ? C124 C123 C122 120.3(7) . . ? C124 C123 H123 119.8 . . ? C122 C123 H123 119.8 . . ? C123 C124 C125 120.6(7) . . ? C123 C124 H124 119.7 . . ? C125 C124 H124 119.7 . . ? C124 C125 C126 119.2(7) . . ? C124 C125 H125 120.4 . . ? C126 C125 H125 120.4 . . ? C121 C126 C125 120.9(6) . . ? C121 C126 H126 119.6 . . ? C125 C126 H126 119.6 . . ? C136 C131 C132 119.3(6) . . ? C136 C131 P1 122.7(5) . . ? C132 C131 P1 118.0(5) . . ? C133 C132 C131 120.4(7) . . ? C133 C132 H132 119.8 . . ? C131 C132 H132 119.8 . . ? C134 C133 C132 119.3(7) . . ? C134 C133 H133 120.3 . . ? C132 C133 H133 120.3 . . ? C133 C134 C135 120.5(7) . . ? C133 C134 H134 119.7 . . ? C135 C134 H134 119.7 . . ? C136 C135 C134 120.0(7) . . ? C136 C135 H135 120.0 . . ? C134 C135 H135 120.0 . . ? C135 C136 C131 120.4(7) . . ? C135 C136 H136 119.8 . . ? C131 C136 H136 119.8 . . ? N2 C211 N1 128.6(7) . . ? N2 C211 S1 120.0(6) . . ? N1 C211 S1 111.5(5) . . ? C217 C212 C213 121.2(7) . . ? C217 C212 S1 111.0(6) . . ? C213 C212 S1 127.8(6) . . ? C214 C213 C212 117.3(8) . . ? C214 C213 H4 121.4 . . ? C212 C213 H4 121.4 . . ? C213 C214 C215 122.4(8) . . ? C213 C214 H5 118.8 . . ? C215 C214 H5 118.8 . . ? C214 C215 C216 120.5(8) . . ? C214 C215 H6 119.8 . . ? C216 C215 H6 119.8 . . ? C215 C216 C217 118.4(8) . . ? C215 C216 H7 120.8 . . ? C217 C216 H7 120.8 . . ? C212 C217 C216 120.2(7) . . ? C212 C217 N1 113.3(7) . . ? C216 C217 N1 126.5(7) . . ? N1 C218 H3 109.5 . . ? N1 C218 H1 109.5 . . ? H3 C218 H1 109.5 . . ? N1 C218 H2 109.5 . . ? H3 C218 H2 109.5 . . ? H1 C218 H2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C131 P1 C111 C116 -16.7(7) . . . . ? C121 P1 C111 C116 95.3(6) . . . . ? Au1 P1 C111 C116 -140.4(5) . . . . ? C131 P1 C111 C112 168.3(6) . . . . ? C121 P1 C111 C112 -79.8(6) . . . . ? Au1 P1 C111 C112 44.5(6) . . . . ? C112 C113 C114 C115 -0.3(11) . . . . ? C114 C113 C112 C111 1.6(11) . . . . ? C116 C111 C112 C113 -2.1(11) . . . . ? P1 C111 C112 C113 173.1(5) . . . . ? C111 P1 C121 C126 -20.7(6) . . . . ? C131 P1 C121 C126 91.8(6) . . . . ? Au1 P1 C121 C126 -143.9(5) . . . . ? C111 P1 C121 C122 156.8(5) . . . . ? C131 P1 C121 C122 -90.8(6) . . . . ? Au1 P1 C121 C122 33.5(6) . . . . ? C113 C114 C115 C116 -0.5(11) . . . . ? C122 C121 C126 C125 0.7(10) . . . . ? P1 C121 C126 C125 178.1(5) . . . . ? C121 C126 C125 C124 -0.5(11) . . . . ? C114 C115 C116 C111 0.0(11) . . . . ? C112 C111 C116 C115 1.3(10) . . . . ? P1 C111 C116 C115 -173.7(5) . . . . ? C126 C121 C122 C123 -0.8(10) . . . . ? P1 C121 C122 C123 -178.3(5) . . . . ? C126 C125 C124 C123 0.5(11) . . . . ? C125 C124 C123 C122 -0.7(11) . . . . ? C121 C122 C123 C124 0.8(11) . . . . ? C133 C132 C131 C136 -1.0(10) . . . . ? C133 C132 C131 P1 -179.1(5) . . . . ? C111 P1 C131 C136 88.3(6) . . . . ? C121 P1 C131 C136 -21.3(7) . . . . ? Au1 P1 C131 C136 -147.2(5) . . . . ? C111 P1 C131 C132 -93.7(6) . . . . ? C121 P1 C131 C132 156.7(5) . . . . ? Au1 P1 C131 C132 30.8(6) . . . . ? C132 C131 C136 C135 -0.1(10) . . . . ? P1 C131 C136 C135 177.9(5) . . . . ? C131 C132 C133 C134 1.6(10) . . . . ? C131 C136 C135 C134 0.6(11) . . . . ? C132 C133 C134 C135 -1.1(11) . . . . ? C136 C135 C134 C133 0.0(11) . . . . ? Au1 N2 C211 N1 -174.0(5) . . . . ? Au1 N2 C211 S1 5.0(9) . . . . ? C217 N1 C211 N2 178.4(7) . . . . ? C218 N1 C211 N2 -1.9(12) . . . . ? C217 N1 C211 S1 -0.7(8) . . . . ? C218 N1 C211 S1 179.0(6) . . . . ? C212 S1 C211 N2 -178.6(6) . . . . ? C212 S1 C211 N1 0.5(6) . . . . ? C211 S1 C212 C217 -0.2(6) . . . . ? C211 S1 C212 C213 -179.5(7) . . . . ? C213 C212 C217 C216 -0.5(11) . . . . ? S1 C212 C217 C216 -179.9(6) . . . . ? C213 C212 C217 N1 179.2(7) . . . . ? S1 C212 C217 N1 -0.1(8) . . . . ? C211 N1 C217 C212 0.5(9) . . . . ? C218 N1 C217 C212 -179.2(7) . . . . ? C211 N1 C217 C216 -179.7(7) . . . . ? C218 N1 C217 C216 0.5(11) . . . . ? C212 C217 C216 C215 0.1(11) . . . . ? N1 C217 C216 C215 -179.6(7) . . . . ? C217 C212 C213 C214 2.1(11) . . . . ? S1 C212 C213 C214 -178.8(6) . . . . ? C217 C216 C215 C214 -1.3(11) . . . . ? C212 C213 C214 C215 -3.3(12) . . . . ? C216 C215 C214 C213 2.9(13) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.71 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.418 _refine_diff_density_min -0.897 _refine_diff_density_rms 0.196 #===END data_6b _database_code_depnum_ccdc_archive 'CCDC 801430' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety '3(C23 H23 Au N2 P S), 3(C F3 O3 S), H2 O' _chemical_formula_sum 'C72 H71 Au3 F9 N6 O10 P3 S6' _chemical_formula_weight 2227.52 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' 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' 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 trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.318(5) _cell_length_b 35.318(5) _cell_length_c 11.178(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 12075(3) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4792 _cell_measurement_theta_min 2.256 _cell_measurement_theta_max 24.276 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6504 _exptl_absorpt_coefficient_mu 5.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4999 _exptl_absorpt_correction_T_max 0.7620 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22365 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.76 _reflns_number_total 5126 _reflns_number_gt 4067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The water H atoms were located in a difference Fourier map and refined with restraints on the distances and angles as well as fixed Uiso values equal to 1.2 times Ueq of the parent O atom. The disordered CF3SO3- counterion was modelled in two orientations (58:42). The bond lengths S2-O1, S2-O2, S2-O3, S2A-O1A, S2A-O2A, S2A-O3A, C1-F1, C1-F2, C1-F3, C1A-F2A were restrained to chemically reasonably values. 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^)+(0.0398P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5126 _refine_ls_number_parameters 409 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.019 _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 0.550508(7) 0.600422(7) 0.566490(18) 0.02250(8) Uani 1 1 d . . . S1 S 0.51168(6) 0.61499(6) 0.30350(14) 0.0456(4) Uani 1 1 d . . . P1 P 0.58720(4) 0.56473(4) 0.58962(12) 0.0205(3) Uani 1 1 d . . . F1 F 0.4288(4) 0.6788(8) 0.9574(17) 0.061(5) Uani 0.425(7) 1 d PD A 1 F1A F 0.4031(2) 0.6392(2) 0.7563(6) 0.0450(19) Uani 0.575(7) 1 d PD A 2 O1 O 0.4525(9) 0.6079(9) 0.934(2) 0.055(7) Uani 0.425(7) 1 d PD A 1 O1A O 0.4379(4) 0.6026(6) 0.9384(19) 0.039(5) Uani 0.575(7) 1 d PD A 2 N1 N 0.47666(15) 0.65320(14) 0.4102(4) 0.0268(11) Uani 1 1 d . . . C1 C 0.4644(4) 0.6855(5) 0.8989(10) 0.040(4) Uani 0.425(7) 1 d PD A 1 C1A C 0.4329(3) 0.6645(3) 0.8369(8) 0.028(2) Uani 0.575(7) 1 d PD A 2 S2 S 0.4602(2) 0.6366(2) 0.8357(6) 0.0363(16) Uani 0.425(7) 1 d PD A 1 S2A S 0.46846(15) 0.64255(16) 0.8811(4) 0.0268(10) Uani 0.575(7) 1 d PD A 2 F2 F 0.4966(3) 0.7048(4) 0.9766(9) 0.064(3) Uani 0.425(7) 1 d PD A 1 F2A F 0.4123(4) 0.6668(6) 0.9323(11) 0.051(3) Uani 0.575(7) 1 d PD A 2 O2 O 0.4238(3) 0.6223(4) 0.7559(8) 0.048(3) Uani 0.425(7) 1 d PD A 1 O2A O 0.4991(2) 0.6749(2) 0.9601(6) 0.041(2) Uani 0.575(7) 1 d PD A 2 N2 N 0.51757(14) 0.63314(14) 0.5366(4) 0.0240(10) Uani 1 1 d . . . H8 H 0.5136 0.6465 0.5976 0.029 Uiso 1 1 calc R . . F3 F 0.4695(16) 0.7130(13) 0.811(3) 0.092(13) Uani 0.425(7) 1 d PD A 1 F3A F 0.4575(11) 0.7045(9) 0.794(3) 0.069(6) Uani 0.575(7) 1 d P A 2 O3 O 0.5009(4) 0.6533(8) 0.7735(19) 0.044(6) Uani 0.425(7) 1 d PD A 1 O3A O 0.4862(5) 0.6383(6) 0.7700(12) 0.040(3) Uani 0.575(7) 1 d PD A 2 O4 O 0.3333 0.6667 0.7970(6) 0.059(2) Uani 1 3 d SD . . H4A H 0.355(3) 0.661(4) 0.756(2) 0.070 Uiso 0.333 1 d PD . . H4B H 0.307(2) 0.650(6) 0.758(14) 0.070 Uiso 0.333 1 d PD . . C111 C 0.58307(15) 0.53304(16) 0.4571(4) 0.0193(11) Uani 1 1 d . . . C112 C 0.59362(17) 0.55466(18) 0.3469(5) 0.0258(12) Uani 1 1 d . . . H112 H 0.6018 0.5847 0.3427 0.031 Uiso 1 1 calc R . . C113 C 0.59211(17) 0.53192(19) 0.2430(5) 0.0275(13) Uani 1 1 d . . . H113 H 0.6001 0.5466 0.1682 0.033 Uiso 1 1 calc R . . C114 C 0.57902(17) 0.48829(19) 0.2493(5) 0.0278(13) Uani 1 1 d . . . H114 H 0.5775 0.4727 0.1785 0.033 Uiso 1 1 calc R . . C115 C 0.56805(18) 0.46696(19) 0.3576(5) 0.0311(13) Uani 1 1 d . . . H115 H 0.5591 0.4367 0.3609 0.037 Uiso 1 1 calc R . . C116 C 0.56993(17) 0.48905(17) 0.4622(5) 0.0254(12) Uani 1 1 d . . . H116 H 0.5623 0.4741 0.5366 0.030 Uiso 1 1 calc R . . C121 C 0.56953(16) 0.52747(16) 0.7153(4) 0.0191(11) Uani 1 1 d . . . C122 C 0.52664(16) 0.50968(16) 0.7558(4) 0.0197(11) Uani 1 1 d . . . H122 H 0.5071 0.5166 0.7162 0.024 Uiso 1 1 calc R . . C123 C 0.51231(17) 0.48171(17) 0.8543(5) 0.0232(12) Uani 1 1 d . . . H123 H 0.4831 0.4698 0.8818 0.028 Uiso 1 1 calc R . . C124 C 0.54047(18) 0.47135(17) 0.9117(5) 0.0274(13) Uani 1 1 d . . . H124 H 0.5308 0.4525 0.9793 0.033 Uiso 1 1 calc R . . C125 C 0.58294(18) 0.48845(18) 0.8707(5) 0.0284(13) Uani 1 1 d . . . H125 H 0.6022 0.4809 0.9097 0.034 Uiso 1 1 calc R . . C126 C 0.59756(18) 0.51634(18) 0.7736(5) 0.0264(13) Uani 1 1 d . . . H126 H 0.6268 0.5280 0.7463 0.032 Uiso 1 1 calc R . . C131 C 0.64538(16) 0.60195(17) 0.6075(4) 0.0219(12) Uani 1 1 d . . . C132 C 0.65952(18) 0.64155(18) 0.6667(5) 0.0284(13) Uani 1 1 d . . . H132 H 0.6387 0.6484 0.6986 0.034 Uiso 1 1 calc R . . C133 C 0.70333(18) 0.67071(19) 0.6790(5) 0.0320(14) Uani 1 1 d . . . H133 H 0.7128 0.6975 0.7201 0.038 Uiso 1 1 calc R . . C134 C 0.73394(17) 0.66105(19) 0.6312(5) 0.0306(14) Uani 1 1 d . . . H134 H 0.7643 0.6814 0.6386 0.037 Uiso 1 1 calc R . . C135 C 0.71991(18) 0.62160(19) 0.5727(5) 0.0285(13) Uani 1 1 d . . . H135 H 0.7408 0.6150 0.5403 0.034 Uiso 1 1 calc R . . C136 C 0.67580(17) 0.59174(18) 0.5611(5) 0.0260(12) Uani 1 1 d . . . H136 H 0.6664 0.5646 0.5220 0.031 Uiso 1 1 calc R . . C211 C 0.50216(18) 0.63556(16) 0.4336(5) 0.0258(13) Uani 1 1 d . . . C212 C 0.4807(2) 0.6314(2) 0.2214(5) 0.0466(18) Uani 1 1 d . . . H212 H 0.4756 0.6268 0.1378 0.056 Uiso 1 1 calc R . . C213 C 0.4650(2) 0.65106(18) 0.2892(5) 0.0361(15) Uani 1 1 d . . . C214 C 0.4378(2) 0.6703(2) 0.2495(6) 0.0506(19) Uani 1 1 d . . . H21D H 0.4316 0.6649 0.1638 0.076 Uiso 1 1 calc R . . H21E H 0.4538 0.7019 0.2644 0.076 Uiso 1 1 calc R . . H21F H 0.4103 0.6568 0.2942 0.076 Uiso 1 1 calc R . . C215 C 0.46291(19) 0.6717(2) 0.5053(5) 0.0334(14) Uani 1 1 d . . . H21A H 0.4494 0.6503 0.5698 0.050 Uiso 1 1 calc R . . H21B H 0.4417 0.6794 0.4737 0.050 Uiso 1 1 calc R . . H21C H 0.4884 0.6981 0.5366 0.050 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 0.02192(12) 0.02023(12) 0.02600(13) 0.00122(9) -0.00051(9) 0.01101(10) S1 0.0756(13) 0.0480(10) 0.0276(9) -0.0038(8) -0.0009(8) 0.0417(10) P1 0.0181(7) 0.0201(7) 0.0226(7) 0.0015(6) 0.0005(6) 0.0090(6) F1 0.058(10) 0.053(11) 0.067(11) -0.008(7) 0.013(9) 0.025(10) F1A 0.048(4) 0.061(5) 0.038(4) 0.000(3) -0.009(3) 0.036(4) O1 0.11(2) 0.066(15) 0.031(9) 0.011(10) 0.008(13) 0.078(13) O1A 0.041(7) 0.051(7) 0.035(7) -0.002(5) -0.005(5) 0.030(6) N1 0.033(3) 0.020(2) 0.028(3) 0.001(2) -0.007(2) 0.014(2) C1 0.057(11) 0.053(10) 0.017(8) 0.007(7) 0.013(8) 0.032(9) C1A 0.040(6) 0.033(6) 0.017(5) 0.001(5) -0.002(5) 0.023(5) S2 0.048(4) 0.026(3) 0.035(4) -0.005(3) -0.010(3) 0.018(3) S2A 0.026(2) 0.030(2) 0.023(3) -0.0056(19) -0.0033(17) 0.0128(16) F2 0.064(7) 0.065(7) 0.053(6) -0.029(6) -0.014(5) 0.025(6) F2A 0.061(7) 0.070(11) 0.040(5) -0.006(5) 0.006(6) 0.047(8) O2 0.038(6) 0.055(7) 0.030(6) 0.001(5) -0.007(5) 0.008(6) O2A 0.036(4) 0.055(6) 0.024(4) -0.014(4) -0.006(3) 0.016(4) N2 0.030(3) 0.024(2) 0.023(3) -0.0031(19) -0.004(2) 0.017(2) F3 0.13(3) 0.054(14) 0.11(2) 0.041(17) 0.07(2) 0.062(18) F3A 0.103(14) 0.061(12) 0.066(8) 0.018(7) -0.002(8) 0.059(11) O3 0.054(13) 0.063(17) 0.040(9) -0.002(8) -0.005(7) 0.048(12) O3A 0.052(8) 0.058(11) 0.021(6) -0.002(5) 0.013(6) 0.036(8) O4 0.081(4) 0.081(4) 0.013(4) 0.000 0.000 0.041(2) C111 0.013(3) 0.020(3) 0.020(3) 0.000(2) 0.000(2) 0.005(2) C112 0.023(3) 0.029(3) 0.028(3) 0.008(2) 0.004(2) 0.015(3) C113 0.023(3) 0.039(3) 0.019(3) 0.005(2) 0.000(2) 0.014(3) C114 0.019(3) 0.037(3) 0.027(3) -0.006(3) -0.003(2) 0.014(3) C115 0.030(3) 0.025(3) 0.032(3) -0.001(3) -0.004(3) 0.010(3) C116 0.024(3) 0.023(3) 0.026(3) 0.003(2) 0.001(2) 0.009(2) C121 0.022(3) 0.020(3) 0.017(3) -0.003(2) 0.000(2) 0.012(2) C122 0.014(3) 0.022(3) 0.022(3) 0.000(2) -0.004(2) 0.008(2) C123 0.017(3) 0.024(3) 0.024(3) 0.001(2) 0.005(2) 0.007(2) C124 0.036(3) 0.025(3) 0.020(3) 0.004(2) 0.003(2) 0.015(3) C125 0.032(3) 0.032(3) 0.026(3) 0.003(3) -0.005(2) 0.019(3) C126 0.024(3) 0.034(3) 0.023(3) 0.004(2) 0.008(2) 0.017(3) C131 0.019(3) 0.026(3) 0.017(3) 0.003(2) 0.000(2) 0.008(2) C132 0.023(3) 0.032(3) 0.029(3) -0.002(3) 0.004(2) 0.012(3) C133 0.030(3) 0.030(3) 0.030(3) -0.010(3) -0.006(3) 0.010(3) C134 0.016(3) 0.037(3) 0.026(3) 0.006(3) 0.001(2) 0.004(3) C135 0.027(3) 0.042(4) 0.024(3) 0.002(3) 0.000(2) 0.023(3) C136 0.027(3) 0.026(3) 0.023(3) 0.004(2) 0.004(2) 0.012(3) C211 0.029(3) 0.014(3) 0.028(3) 0.004(2) 0.002(2) 0.006(2) C212 0.080(5) 0.036(4) 0.023(3) -0.001(3) -0.009(3) 0.028(4) C213 0.046(4) 0.022(3) 0.031(3) 0.007(3) -0.008(3) 0.010(3) C214 0.056(5) 0.045(4) 0.047(4) 0.007(3) -0.019(4) 0.023(4) C215 0.031(3) 0.042(4) 0.034(3) -0.002(3) -0.005(3) 0.022(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 N2 2.036(4) . ? Au1 P1 2.2291(14) . ? S1 C211 1.732(6) . ? S1 C212 1.736(7) . ? P1 C121 1.809(5) . ? P1 C131 1.813(5) . ? P1 C111 1.817(5) . ? F1 C1 1.327(5) . ? F1A C1A 1.334(11) . ? O1 S2 1.429(5) . ? O1A S2A 1.429(5) . ? N1 C211 1.353(7) . ? N1 C213 1.405(7) . ? N1 C215 1.454(7) . ? C1 F2 1.318(5) . ? C1 F3 1.330(5) . ? C1 S2 1.804(16) . ? C1A F2A 1.316(5) . ? C1A F3A 1.33(2) . ? C1A S2A 1.842(11) . ? S2 O3 1.431(5) . ? S2 O2 1.434(5) . ? S2A O2A 1.421(5) . ? S2A O3A 1.432(5) . ? N2 C211 1.294(7) . ? N2 H8 0.8800 . ? O4 H4A 0.990(2) . ? O4 H4B 0.92(4) . ? C111 C116 1.383(7) . ? C111 C112 1.398(7) . ? C112 C113 1.398(7) . ? C112 H112 0.9500 . ? C113 C114 1.371(8) . ? C113 H113 0.9500 . ? C114 C115 1.375(8) . ? C114 H114 0.9500 . ? C115 C116 1.388(7) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C122 1.394(7) . ? C121 C126 1.396(7) . ? C122 C123 1.394(7) . ? C122 H122 0.9500 . ? C123 C124 1.378(7) . ? C123 H123 0.9500 . ? C124 C125 1.385(8) . ? C124 H124 0.9500 . ? C125 C126 1.381(7) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C131 C136 1.393(7) . ? C131 C132 1.395(7) . ? C132 C133 1.371(7) . ? C132 H132 0.9500 . ? C133 C134 1.393(8) . ? C133 H133 0.9500 . ? C134 C135 1.387(8) . ? C134 H134 0.9500 . ? C135 C136 1.383(7) . ? C135 H135 0.9500 . ? C136 H136 0.9500 . ? C212 C213 1.323(9) . ? C212 H212 0.9500 . ? C213 C214 1.494(8) . ? C214 H21D 0.9800 . ? C214 H21E 0.9800 . ? C214 H21F 0.9800 . ? C215 H21A 0.9800 . ? C215 H21B 0.9800 . ? C215 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Au1 P1 177.19(13) . . ? C211 S1 C212 91.0(3) . . ? C121 P1 C131 107.2(2) . . ? C121 P1 C111 107.0(2) . . ? C131 P1 C111 104.4(2) . . ? C121 P1 Au1 114.50(16) . . ? C131 P1 Au1 111.78(18) . . ? C111 P1 Au1 111.30(17) . . ? C211 N1 C213 114.0(5) . . ? C211 N1 C215 121.0(5) . . ? C213 N1 C215 125.0(5) . . ? F2 C1 F1 105.3(12) . . ? F2 C1 F3 110(2) . . ? F1 C1 F3 106(3) . . ? F2 C1 S2 112.9(10) . . ? F1 C1 S2 113.8(14) . . ? F3 C1 S2 109(2) . . ? F2A C1A F3A 109(2) . . ? F2A C1A F1A 108.2(9) . . ? F3A C1A F1A 110.1(14) . . ? F2A C1A S2A 108.9(10) . . ? F3A C1A S2A 109.0(15) . . ? F1A C1A S2A 112.2(7) . . ? O1 S2 O3 117.6(18) . . ? O1 S2 O2 114.2(13) . . ? O3 S2 O2 112.5(12) . . ? O1 S2 C1 105.8(16) . . ? O3 S2 C1 102.3(11) . . ? O2 S2 C1 102.1(7) . . ? O2A S2A O1A 114.2(10) . . ? O2A S2A O3A 115.2(8) . . ? O1A S2A O3A 116.1(15) . . ? O2A S2A C1A 103.6(6) . . ? O1A S2A C1A 101.4(9) . . ? O3A S2A C1A 103.7(11) . . ? C211 N2 Au1 124.2(4) . . ? C211 N2 H8 117.9 . . ? Au1 N2 H8 117.9 . . ? H4A O4 H4B 107(6) . . ? C116 C111 C112 119.8(5) . . ? C116 C111 P1 122.5(4) . . ? C112 C111 P1 117.7(4) . . ? C113 C112 C111 119.7(5) . . ? C113 C112 H112 120.2 . . ? C111 C112 H112 120.2 . . ? C114 C113 C112 119.8(5) . . ? C114 C113 H113 120.1 . . ? C112 C113 H113 120.1 . . ? C113 C114 C115 120.3(5) . . ? C113 C114 H114 119.8 . . ? C115 C114 H114 119.8 . . ? C114 C115 C116 120.8(5) . . ? C114 C115 H115 119.6 . . ? C116 C115 H115 119.6 . . ? C111 C116 C115 119.5(5) . . ? C111 C116 H116 120.3 . . ? C115 C116 H116 120.3 . . ? C122 C121 C126 119.0(5) . . ? C122 C121 P1 118.8(4) . . ? C126 C121 P1 122.1(4) . . ? C121 C122 C123 120.2(5) . . ? C121 C122 H122 119.9 . . ? C123 C122 H122 119.9 . . ? C124 C123 C122 120.1(5) . . ? C124 C123 H123 120.0 . . ? C122 C123 H123 120.0 . . ? C123 C124 C125 119.9(5) . . ? C123 C124 H124 120.1 . . ? C125 C124 H124 120.1 . . ? C126 C125 C124 120.6(5) . . ? C126 C125 H125 119.7 . . ? C124 C125 H125 119.7 . . ? C125 C126 C121 120.2(5) . . ? C125 C126 H126 119.9 . . ? C121 C126 H126 119.9 . . ? C136 C131 C132 120.0(5) . . ? C136 C131 P1 120.8(4) . . ? C132 C131 P1 119.1(4) . . ? C133 C132 C131 120.3(5) . . ? C133 C132 H132 119.8 . . ? C131 C132 H132 119.8 . . ? C132 C133 C134 120.0(5) . . ? C132 C133 H133 120.0 . . ? C134 C133 H133 120.0 . . ? C135 C134 C133 119.7(5) . . ? C135 C134 H134 120.1 . . ? C133 C134 H134 120.1 . . ? C136 C135 C134 120.7(5) . . ? C136 C135 H135 119.7 . . ? C134 C135 H135 119.7 . . ? C135 C136 C131 119.2(5) . . ? C135 C136 H136 120.4 . . ? C131 C136 H136 120.4 . . ? N2 C211 N1 127.0(5) . . ? N2 C211 S1 122.9(4) . . ? N1 C211 S1 110.1(4) . . ? C213 C212 S1 111.8(5) . . ? C213 C212 H212 124.1 . . ? S1 C212 H212 124.1 . . ? C212 C213 N1 113.0(5) . . ? C212 C213 C214 127.0(6) . . ? N1 C213 C214 120.0(6) . . ? C213 C214 H21D 109.5 . . ? C213 C214 H21E 109.5 . . ? H21D C214 H21E 109.5 . . ? C213 C214 H21F 109.5 . . ? H21D C214 H21F 109.5 . . ? H21E C214 H21F 109.5 . . ? N1 C215 H21A 109.5 . . ? N1 C215 H21B 109.5 . . ? H21A C215 H21B 109.5 . . ? N1 C215 H21C 109.5 . . ? H21A C215 H21C 109.5 . . ? H21B C215 H21C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F2 C1 S2 O1 60.3(16) . . . . ? F1 C1 S2 O1 -59.6(18) . . . . ? F3 C1 S2 O1 -177(3) . . . . ? F2 C1 S2 O3 -63.3(15) . . . . ? F1 C1 S2 O3 176.8(18) . . . . ? F3 C1 S2 O3 59(3) . . . . ? F2 C1 S2 O2 -179.9(10) . . . . ? F1 C1 S2 O2 60.2(15) . . . . ? F3 C1 S2 O2 -57(2) . . . . ? F2A C1A S2A O2A -63.8(10) . . . . ? F3A C1A S2A O2A 54.3(17) . . . . ? F1A C1A S2A O2A 176.5(7) . . . . ? F2A C1A S2A O1A 54.8(14) . . . . ? F3A C1A S2A O1A 173(2) . . . . ? F1A C1A S2A O1A -64.9(13) . . . . ? F2A C1A S2A O3A 175.5(11) . . . . ? F3A C1A S2A O3A -66.3(18) . . . . ? F1A C1A S2A O3A 55.8(10) . . . . ? C121 P1 C111 C116 -2.0(5) . . . . ? C131 P1 C111 C116 111.4(4) . . . . ? Au1 P1 C111 C116 -127.8(4) . . . . ? C121 P1 C111 C112 177.8(4) . . . . ? C131 P1 C111 C112 -68.8(4) . . . . ? Au1 P1 C111 C112 52.0(4) . . . . ? C116 C111 C112 C113 -2.0(7) . . . . ? P1 C111 C112 C113 178.2(4) . . . . ? C111 C112 C113 C114 2.0(8) . . . . ? C112 C113 C114 C115 -1.1(8) . . . . ? C113 C114 C115 C116 0.1(8) . . . . ? C112 C111 C116 C115 1.0(8) . . . . ? P1 C111 C116 C115 -179.2(4) . . . . ? C114 C115 C116 C111 -0.1(8) . . . . ? C131 P1 C121 C122 150.8(4) . . . . ? C111 P1 C121 C122 -97.7(4) . . . . ? Au1 P1 C121 C122 26.2(5) . . . . ? C131 P1 C121 C126 -28.6(5) . . . . ? C111 P1 C121 C126 83.0(5) . . . . ? Au1 P1 C121 C126 -153.2(4) . . . . ? C126 C121 C122 C123 1.0(7) . . . . ? P1 C121 C122 C123 -178.4(4) . . . . ? C121 C122 C123 C124 -0.3(8) . . . . ? C122 C123 C124 C125 -0.6(8) . . . . ? C123 C124 C125 C126 0.9(8) . . . . ? C124 C125 C126 C121 -0.3(8) . . . . ? C122 C121 C126 C125 -0.7(8) . . . . ? P1 C121 C126 C125 178.7(4) . . . . ? C121 P1 C131 C136 88.6(4) . . . . ? C111 P1 C131 C136 -24.8(5) . . . . ? Au1 P1 C131 C136 -145.2(4) . . . . ? C121 P1 C131 C132 -92.6(5) . . . . ? C111 P1 C131 C132 154.1(4) . . . . ? Au1 P1 C131 C132 33.7(5) . . . . ? C136 C131 C132 C133 0.4(8) . . . . ? P1 C131 C132 C133 -178.5(4) . . . . ? C131 C132 C133 C134 0.7(9) . . . . ? C132 C133 C134 C135 -0.9(8) . . . . ? C133 C134 C135 C136 0.2(8) . . . . ? C134 C135 C136 C131 0.9(8) . . . . ? C132 C131 C136 C135 -1.1(8) . . . . ? P1 C131 C136 C135 177.7(4) . . . . ? Au1 N2 C211 N1 173.4(4) . . . . ? Au1 N2 C211 S1 -5.7(7) . . . . ? C213 N1 C211 N2 180.0(5) . . . . ? C215 N1 C211 N2 -0.9(8) . . . . ? C213 N1 C211 S1 -0.8(6) . . . . ? C215 N1 C211 S1 178.4(4) . . . . ? C212 S1 C211 N2 179.5(5) . . . . ? C212 S1 C211 N1 0.2(4) . . . . ? C211 S1 C212 C213 0.4(5) . . . . ? S1 C212 C213 N1 -0.9(7) . . . . ? S1 C212 C213 C214 178.6(5) . . . . ? C211 N1 C213 C212 1.1(7) . . . . ? C215 N1 C213 C212 -178.0(5) . . . . ? C211 N1 C213 C214 -178.4(5) . . . . ? C215 N1 C213 C214 2.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.690 _refine_diff_density_min -1.095 _refine_diff_density_rms 0.140 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 801431' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point '127-132 ^o^C' _chemical_formula_moiety '2(C20 H31 Au N5), C H2 Cl2, 2(N O3)' _chemical_formula_sum 'C41 H64 Au2 Cl2 N12 O6' _chemical_formula_weight 1285.88 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' Cl Cl 0.1484 0.1585 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1086(14) _cell_length_b 10.9681(16) _cell_length_c 12.2928(18) _cell_angle_alpha 86.931(2) _cell_angle_beta 85.686(2) _cell_angle_gamma 82.015(2) _cell_volume 1211.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9551 _cell_measurement_theta_min 2.263 _cell_measurement_theta_max 26.384 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 6.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6702 _exptl_absorpt_correction_T_max 0.7464 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12702 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4929 _reflns_number_gt 4814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0325P)^2^+1.4742P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4929 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.185594(15) 0.248786(12) 0.844242(10) 0.01400(6) Uani 1 1 d . . . Cl1 Cl 0.0800(8) 0.6203(8) 0.4818(7) 0.0451(15) Uani 0.50 1 d P A -1 O1 O 0.4119(4) 0.6940(3) 0.7330(3) 0.0304(7) Uani 1 1 d . . . N1 N 0.5436(4) 0.2186(3) 0.5876(3) 0.0178(7) Uani 1 1 d . . . C1 C 0.0897(11) 0.4729(8) 0.5272(9) 0.034(2) Uani 0.50 1 d P A -1 H1A H 0.1184 0.4673 0.6036 0.040 Uiso 0.50 1 calc PR A -1 H1B H 0.1701 0.4237 0.4832 0.040 Uiso 0.50 1 calc PR A -1 Cl2 Cl -0.0686(11) 0.4075(9) 0.5233(9) 0.070(3) Uani 0.50 1 d P A -1 O2 O 0.3062(3) 0.5370(3) 0.6956(2) 0.0215(6) Uani 1 1 d . . . N2 N 0.4664(4) 0.0623(3) 0.6861(3) 0.0172(7) Uani 1 1 d . . . O3 O 0.5149(4) 0.5080(3) 0.7729(3) 0.0437(9) Uani 1 1 d . . . N3 N 0.3396(4) 0.2649(3) 0.7182(3) 0.0193(7) Uani 1 1 d . . . N4 N 0.0415(4) 0.2907(3) 1.0699(3) 0.0153(6) Uani 1 1 d . . . N5 N -0.1076(3) 0.2166(3) 0.9690(3) 0.0156(6) Uani 1 1 d . . . N6 N 0.4123(4) 0.5797(3) 0.7343(3) 0.0217(7) Uani 1 1 d . . . H11 H 0.349(6) 0.338(5) 0.703(4) 0.030(14) Uiso 1 1 d . . . C111 C 0.4410(4) 0.1883(3) 0.6684(3) 0.0157(7) Uani 1 1 d . . . C112 C 0.5864(4) 0.0139(4) 0.6167(3) 0.0176(8) Uani 1 1 d . . . C113 C 0.6535(5) -0.1057(4) 0.6041(3) 0.0215(8) Uani 1 1 d . . . H1 H 0.6194 -0.1728 0.6460 0.026 Uiso 1 1 calc R . . C114 C 0.7743(5) -0.1234(4) 0.5266(4) 0.0265(9) Uani 1 1 d . . . H2 H 0.8232 -0.2044 0.5149 0.032 Uiso 1 1 calc R . . C115 C 0.8240(5) -0.0240(4) 0.4661(4) 0.0268(9) Uani 1 1 d . . . H3 H 0.9075 -0.0390 0.4151 0.032 Uiso 1 1 calc R . . C116 C 0.7549(5) 0.0966(4) 0.4783(3) 0.0228(9) Uani 1 1 d . . . H4 H 0.7881 0.1638 0.4360 0.027 Uiso 1 1 calc R . . C117 C 0.6354(4) 0.1134(4) 0.5552(3) 0.0168(8) Uani 1 1 d . . . C118 C 0.5451(5) 0.3435(4) 0.5407(3) 0.0251(9) Uani 1 1 d . . . H7 H 0.4462 0.3759 0.5174 0.038 Uiso 1 1 calc R . . H6 H 0.6177 0.3422 0.4777 0.038 Uiso 1 1 calc R . . H5 H 0.5724 0.3962 0.5957 0.038 Uiso 1 1 calc R . . C119 C 0.3831(5) -0.0096(4) 0.7650(3) 0.0201(8) Uani 1 1 d . . . H10 H 0.3974 0.0136 0.8390 0.030 Uiso 1 1 calc R . . H9 H 0.4185 -0.0975 0.7575 0.030 Uiso 1 1 calc R . . H8 H 0.2773 0.0067 0.7518 0.030 Uiso 1 1 calc R . . C211 C 0.0315(4) 0.2496(3) 0.9683(3) 0.0150(7) Uani 1 1 d . . . C212 C -0.0909(4) 0.2853(4) 1.1313(3) 0.0176(8) Uani 1 1 d . . . H12 H -0.1127 0.3098 1.2044 0.021 Uiso 1 1 calc R . . C213 C -0.1836(5) 0.2393(4) 1.0694(3) 0.0189(8) Uani 1 1 d . . . H13 H -0.2824 0.2250 1.0904 0.023 Uiso 1 1 calc R . . C214 C -0.1713(4) 0.1655(4) 0.8745(3) 0.0181(8) Uani 1 1 d . . . C215 C -0.1766(5) 0.2605(4) 0.7785(3) 0.0246(9) Uani 1 1 d . . . H25 H -0.2409 0.3358 0.8000 0.037 Uiso 1 1 calc R . . H26 H -0.2163 0.2267 0.7164 0.037 Uiso 1 1 calc R . . H24 H -0.0761 0.2797 0.7577 0.037 Uiso 1 1 calc R . . C216 C -0.0753(5) 0.0449(4) 0.8439(4) 0.0233(9) Uani 1 1 d . . . H30 H 0.0273 0.0602 0.8254 0.035 Uiso 1 1 calc R . . H31 H -0.1141 0.0122 0.7808 0.035 Uiso 1 1 calc R . . H32 H -0.0775 -0.0151 0.9058 0.035 Uiso 1 1 calc R . . C217 C -0.3292(5) 0.1394(5) 0.9085(4) 0.0285(10) Uani 1 1 d . . . H27 H -0.3267 0.0785 0.9700 0.043 Uiso 1 1 calc R . . H28 H -0.3716 0.1070 0.8469 0.043 Uiso 1 1 calc R . . H29 H -0.3906 0.2158 0.9306 0.043 Uiso 1 1 calc R . . C218 C 0.1754(4) 0.3369(4) 1.1098(3) 0.0169(8) Uani 1 1 d . . . C219 C 0.3066(4) 0.2330(4) 1.1058(3) 0.0200(8) Uani 1 1 d . . . H14 H 0.2798 0.1616 1.1504 0.030 Uiso 1 1 calc R . . H17 H 0.3929 0.2615 1.1344 0.030 Uiso 1 1 calc R . . H15 H 0.3311 0.2095 1.0301 0.030 Uiso 1 1 calc R . . C220 C 0.2126(5) 0.4496(4) 1.0393(3) 0.0205(8) Uani 1 1 d . . . H19 H 0.2363 0.4262 0.9635 0.031 Uiso 1 1 calc R . . H20 H 0.2983 0.4802 1.0667 0.031 Uiso 1 1 calc R . . H18 H 0.1269 0.5144 1.0425 0.031 Uiso 1 1 calc R . . C221 C 0.1394(5) 0.3754(4) 1.2279(3) 0.0243(9) Uani 1 1 d . . . H22 H 0.0562 0.4424 1.2304 0.036 Uiso 1 1 calc R . . H23 H 0.2267 0.4036 1.2552 0.036 Uiso 1 1 calc R . . H21 H 0.1124 0.3048 1.2735 0.036 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 0.01495(9) 0.01355(9) 0.01357(8) -0.00065(5) 0.00078(5) -0.00307(6) Cl1 0.026(2) 0.052(3) 0.058(3) 0.006(3) -0.0103(16) -0.006(2) O1 0.0419(19) 0.0197(15) 0.0313(17) -0.0077(13) 0.0065(14) -0.0118(14) N1 0.0225(17) 0.0163(16) 0.0146(16) -0.0020(13) 0.0044(13) -0.0055(13) C1 0.033(5) 0.019(4) 0.052(6) -0.002(4) -0.018(4) -0.004(4) Cl2 0.054(3) 0.088(6) 0.079(4) -0.040(3) 0.016(2) -0.042(3) O2 0.0199(14) 0.0212(15) 0.0246(15) -0.0042(12) -0.0022(12) -0.0056(12) N2 0.0188(17) 0.0145(16) 0.0183(16) 0.0012(13) -0.0007(13) -0.0029(13) O3 0.034(2) 0.035(2) 0.063(3) -0.0098(18) -0.0226(18) 0.0052(16) N3 0.0275(19) 0.0131(17) 0.0174(17) -0.0005(13) 0.0045(14) -0.0065(14) N4 0.0152(16) 0.0155(16) 0.0148(15) -0.0002(12) -0.0004(12) -0.0007(12) N5 0.0124(15) 0.0157(16) 0.0187(16) -0.0009(13) -0.0023(12) -0.0006(12) N6 0.0246(19) 0.0218(18) 0.0188(17) -0.0042(14) 0.0035(14) -0.0050(15) C111 0.0188(19) 0.0159(18) 0.0133(17) 0.0004(14) -0.0025(14) -0.0057(15) C112 0.0159(19) 0.021(2) 0.0171(18) -0.0022(15) -0.0046(15) -0.0035(15) C113 0.023(2) 0.020(2) 0.021(2) -0.0025(16) -0.0057(16) 0.0026(16) C114 0.028(2) 0.027(2) 0.023(2) -0.0059(18) -0.0056(18) 0.0065(18) C115 0.020(2) 0.037(3) 0.023(2) -0.0113(19) 0.0008(17) -0.0002(19) C116 0.022(2) 0.028(2) 0.020(2) -0.0052(17) -0.0014(16) -0.0062(17) C117 0.0162(19) 0.0208(19) 0.0146(18) -0.0053(15) -0.0032(14) -0.0039(15) C118 0.034(2) 0.019(2) 0.021(2) 0.0025(16) 0.0078(18) -0.0058(18) C119 0.022(2) 0.0156(19) 0.022(2) 0.0013(16) 0.0032(16) -0.0050(16) C211 0.0131(18) 0.0108(17) 0.0200(19) 0.0024(14) -0.0002(15) 0.0012(14) C212 0.019(2) 0.0175(19) 0.0148(18) 0.0017(15) 0.0016(15) -0.0009(15) C213 0.020(2) 0.0169(19) 0.0190(19) 0.0009(15) 0.0043(15) -0.0025(15) C214 0.0156(19) 0.0191(19) 0.0207(19) -0.0026(16) -0.0027(15) -0.0049(15) C215 0.030(2) 0.023(2) 0.022(2) 0.0022(17) -0.0112(18) -0.0043(18) C216 0.024(2) 0.022(2) 0.026(2) -0.0046(17) -0.0030(17) -0.0085(17) C217 0.016(2) 0.041(3) 0.030(2) -0.008(2) -0.0004(17) -0.0093(19) C218 0.0159(19) 0.0179(19) 0.0182(19) -0.0012(15) -0.0035(15) -0.0049(15) C219 0.019(2) 0.021(2) 0.020(2) 0.0003(16) -0.0028(16) -0.0023(16) C220 0.026(2) 0.0158(19) 0.021(2) 0.0015(16) -0.0053(16) -0.0069(16) C221 0.028(2) 0.025(2) 0.020(2) -0.0032(17) -0.0043(17) -0.0046(18) _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 C211 1.993(4) . ? Au1 N3 2.028(3) . ? Cl1 C1 1.675(11) . ? O1 N6 1.252(4) . ? N1 C111 1.373(5) . ? N1 C117 1.386(5) . ? N1 C118 1.458(5) . ? C1 Cl2 1.702(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? O2 N6 1.265(4) . ? N2 C111 1.378(5) . ? N2 C112 1.397(5) . ? N2 C119 1.452(5) . ? O3 N6 1.241(5) . ? N3 C111 1.299(5) . ? N3 H11 0.82(5) . ? N4 C211 1.363(5) . ? N4 C212 1.381(5) . ? N4 C218 1.508(5) . ? N5 C211 1.364(5) . ? N5 C213 1.386(5) . ? N5 C214 1.503(5) . ? C112 C113 1.379(6) . ? C112 C117 1.400(6) . ? C113 C114 1.400(6) . ? C113 H1 0.9500 . ? C114 C115 1.394(7) . ? C114 H2 0.9500 . ? C115 C116 1.395(6) . ? C115 H3 0.9500 . ? C116 C117 1.386(6) . ? C116 H4 0.9500 . ? C118 H7 0.9800 . ? C118 H6 0.9800 . ? C118 H5 0.9800 . ? C119 H10 0.9800 . ? C119 H9 0.9800 . ? C119 H8 0.9800 . ? C212 C213 1.343(6) . ? C212 H12 0.9500 . ? C213 H13 0.9500 . ? C214 C217 1.529(5) . ? C214 C216 1.530(6) . ? C214 C215 1.530(6) . ? C215 H25 0.9800 . ? C215 H26 0.9800 . ? C215 H24 0.9800 . ? C216 H30 0.9800 . ? C216 H31 0.9800 . ? C216 H32 0.9800 . ? C217 H27 0.9800 . ? C217 H28 0.9800 . ? C217 H29 0.9800 . ? C218 C219 1.532(5) . ? C218 C221 1.532(6) . ? C218 C220 1.534(5) . ? C219 H14 0.9800 . ? C219 H17 0.9800 . ? C219 H15 0.9800 . ? C220 H19 0.9800 . ? C220 H20 0.9800 . ? C220 H18 0.9800 . ? C221 H22 0.9800 . ? C221 H23 0.9800 . ? C221 H21 0.9800 . ? 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 C211 Au1 N3 174.81(14) . . ? C111 N1 C117 109.8(3) . . ? C111 N1 C118 123.2(3) . . ? C117 N1 C118 126.9(3) . . ? Cl1 C1 Cl2 115.8(7) . . ? Cl1 C1 H1A 108.3 . . ? Cl2 C1 H1A 108.3 . . ? Cl1 C1 H1B 108.3 . . ? Cl2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C111 N2 C112 109.2(3) . . ? C111 N2 C119 125.7(3) . . ? C112 N2 C119 125.0(3) . . ? C111 N3 Au1 134.5(3) . . ? C111 N3 H11 113(4) . . ? Au1 N3 H11 111(4) . . ? C211 N4 C212 109.7(3) . . ? C211 N4 C218 125.7(3) . . ? C212 N4 C218 124.6(3) . . ? C211 N5 C213 109.9(3) . . ? C211 N5 C214 125.4(3) . . ? C213 N5 C214 124.6(3) . . ? O3 N6 O1 121.1(4) . . ? O3 N6 O2 119.6(4) . . ? O1 N6 O2 119.3(4) . . ? N3 C111 N1 126.0(4) . . ? N3 C111 N2 127.0(3) . . ? N1 C111 N2 107.0(3) . . ? C113 C112 N2 131.0(4) . . ? C113 C112 C117 122.1(4) . . ? N2 C112 C117 106.9(3) . . ? C112 C113 C114 116.8(4) . . ? C112 C113 H1 121.6 . . ? C114 C113 H1 121.6 . . ? C115 C114 C113 121.0(4) . . ? C115 C114 H2 119.5 . . ? C113 C114 H2 119.5 . . ? C114 C115 C116 122.0(4) . . ? C114 C115 H3 119.0 . . ? C116 C115 H3 119.0 . . ? C117 C116 C115 116.6(4) . . ? C117 C116 H4 121.7 . . ? C115 C116 H4 121.7 . . ? N1 C117 C116 131.5(4) . . ? N1 C117 C112 107.0(3) . . ? C116 C117 C112 121.4(4) . . ? N1 C118 H7 109.5 . . ? N1 C118 H6 109.5 . . ? H7 C118 H6 109.5 . . ? N1 C118 H5 109.5 . . ? H7 C118 H5 109.5 . . ? H6 C118 H5 109.5 . . ? N2 C119 H10 109.5 . . ? N2 C119 H9 109.5 . . ? H10 C119 H9 109.5 . . ? N2 C119 H8 109.5 . . ? H10 C119 H8 109.5 . . ? H9 C119 H8 109.5 . . ? N4 C211 N5 105.5(3) . . ? N4 C211 Au1 126.3(3) . . ? N5 C211 Au1 128.1(3) . . ? C213 C212 N4 107.8(3) . . ? C213 C212 H12 126.1 . . ? N4 C212 H12 126.1 . . ? C212 C213 N5 107.0(3) . . ? C212 C213 H13 126.5 . . ? N5 C213 H13 126.5 . . ? N5 C214 C217 109.2(3) . . ? N5 C214 C216 108.9(3) . . ? C217 C214 C216 109.0(3) . . ? N5 C214 C215 109.3(3) . . ? C217 C214 C215 109.0(3) . . ? C216 C214 C215 111.4(3) . . ? C214 C215 H25 109.5 . . ? C214 C215 H26 109.5 . . ? H25 C215 H26 109.5 . . ? C214 C215 H24 109.5 . . ? H25 C215 H24 109.5 . . ? H26 C215 H24 109.5 . . ? C214 C216 H30 109.5 . . ? C214 C216 H31 109.5 . . ? H30 C216 H31 109.5 . . ? C214 C216 H32 109.5 . . ? H30 C216 H32 109.5 . . ? H31 C216 H32 109.5 . . ? C214 C217 H27 109.5 . . ? C214 C217 H28 109.5 . . ? H27 C217 H28 109.5 . . ? C214 C217 H29 109.5 . . ? H27 C217 H29 109.5 . . ? H28 C217 H29 109.5 . . ? N4 C218 C219 109.1(3) . . ? N4 C218 C221 108.8(3) . . ? C219 C218 C221 109.4(3) . . ? N4 C218 C220 110.0(3) . . ? C219 C218 C220 110.9(3) . . ? C221 C218 C220 108.6(3) . . ? C218 C219 H14 109.5 . . ? C218 C219 H17 109.5 . . ? H14 C219 H17 109.5 . . ? C218 C219 H15 109.5 . . ? H14 C219 H15 109.5 . . ? H17 C219 H15 109.5 . . ? C218 C220 H19 109.5 . . ? C218 C220 H20 109.5 . . ? H19 C220 H20 109.5 . . ? C218 C220 H18 109.5 . . ? H19 C220 H18 109.5 . . ? H20 C220 H18 109.5 . . ? C218 C221 H22 109.5 . . ? C218 C221 H23 109.5 . . ? H22 C221 H23 109.5 . . ? C218 C221 H21 109.5 . . ? H22 C221 H21 109.5 . . ? H23 C221 H21 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Au1 N3 C111 N1 -175.2(3) . . . . ? Au1 N3 C111 N2 4.8(7) . . . . ? C117 N1 C111 N3 179.0(4) . . . . ? C118 N1 C111 N3 -4.5(6) . . . . ? C117 N1 C111 N2 -1.0(4) . . . . ? C118 N1 C111 N2 175.5(4) . . . . ? C112 N2 C111 N3 -179.5(4) . . . . ? C119 N2 C111 N3 0.0(6) . . . . ? C112 N2 C111 N1 0.5(4) . . . . ? C119 N2 C111 N1 180.0(3) . . . . ? C111 N2 C112 C113 179.8(4) . . . . ? C119 N2 C112 C113 0.3(7) . . . . ? C111 N2 C112 C117 0.1(4) . . . . ? C119 N2 C112 C117 -179.3(3) . . . . ? N2 C112 C113 C114 -179.5(4) . . . . ? C117 C112 C113 C114 0.1(6) . . . . ? C112 C113 C114 C115 0.5(6) . . . . ? C113 C114 C115 C116 -1.2(7) . . . . ? C114 C115 C116 C117 1.2(6) . . . . ? C111 N1 C117 C116 -179.3(4) . . . . ? C118 N1 C117 C116 4.4(7) . . . . ? C111 N1 C117 C112 1.1(4) . . . . ? C118 N1 C117 C112 -175.2(4) . . . . ? C115 C116 C117 N1 179.9(4) . . . . ? C115 C116 C117 C112 -0.5(6) . . . . ? C113 C112 C117 N1 179.5(4) . . . . ? N2 C112 C117 N1 -0.8(4) . . . . ? C113 C112 C117 C116 -0.1(6) . . . . ? N2 C112 C117 C116 179.6(3) . . . . ? C212 N4 C211 N5 -1.2(4) . . . . ? C218 N4 C211 N5 179.6(3) . . . . ? C212 N4 C211 Au1 175.5(3) . . . . ? C218 N4 C211 Au1 -3.8(5) . . . . ? C213 N5 C211 N4 1.1(4) . . . . ? C214 N5 C211 N4 180.0(3) . . . . ? C213 N5 C211 Au1 -175.5(3) . . . . ? C214 N5 C211 Au1 3.4(5) . . . . ? C211 N4 C212 C213 0.9(4) . . . . ? C218 N4 C212 C213 -179.8(3) . . . . ? N4 C212 C213 N5 -0.2(4) . . . . ? C211 N5 C213 C212 -0.5(4) . . . . ? C214 N5 C213 C212 -179.4(3) . . . . ? C211 N5 C214 C217 179.5(4) . . . . ? C213 N5 C214 C217 -1.8(5) . . . . ? C211 N5 C214 C216 60.5(5) . . . . ? C213 N5 C214 C216 -120.7(4) . . . . ? C211 N5 C214 C215 -61.4(5) . . . . ? C213 N5 C214 C215 117.4(4) . . . . ? C211 N4 C218 C219 -61.3(5) . . . . ? C212 N4 C218 C219 119.5(4) . . . . ? C211 N4 C218 C221 179.3(3) . . . . ? C212 N4 C218 C221 0.2(5) . . . . ? C211 N4 C218 C220 60.5(5) . . . . ? C212 N4 C218 C220 -118.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.294 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.134 #===END data_III _database_code_depnum_ccdc_archive 'CCDC 801432' #TrackingRef '- Revised Ylideneamine gold(I).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common work _chemical_melting_point ? _chemical_formula_moiety '2(C16 H14 N3 S2), 2(C F3 O3 S), C H2 Cl2' _chemical_formula_sum 'C35 H30 Cl2 F6 N6 O6 S6' _chemical_formula_weight 1007.91 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.381(2) _cell_length_b 13.755(2) _cell_length_c 20.620(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.291(3) _cell_angle_gamma 90.00 _cell_volume 4036.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1634 _cell_measurement_theta_min 2.619 _cell_measurement_theta_max 24.288 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 0.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8925 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20878 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.52 _reflns_number_total 7476 _reflns_number_gt 4536 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1998)' _computing_molecular_graphics 'X-Seed (Barbour, 2003)' _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^)+(0.0842P)^2^+1.0250P] 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 7476 _refine_ls_number_parameters 554 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.1917 _refine_ls_wR_factor_gt 0.1656 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Cl1 Cl 0.00147(10) 0.55588(12) 0.18560(7) 0.0418(4) Uani 1 1 d . . . S1 S -0.17256(8) 0.39312(9) 0.48416(6) 0.0219(3) Uani 1 1 d . . . F1 F 0.4183(2) 0.6829(3) 0.27297(17) 0.0614(11) Uani 1 1 d . . . O1 O 0.2486(3) 0.6245(3) 0.38748(17) 0.0340(9) Uani 1 1 d . . . N1 N -0.1960(3) 0.3961(3) 0.35827(19) 0.0237(9) Uani 1 1 d . . . C1 C -0.1272(4) 0.3875(3) 0.4099(2) 0.0225(11) Uani 1 1 d . . . Cl2 Cl 0.00132(10) 0.59809(13) 0.32257(7) 0.0509(5) Uani 1 1 d . . . S2 S 0.03702(9) 0.37238(9) 0.53056(6) 0.0220(3) Uani 1 1 d . . . F2 F 0.4451(2) 0.6699(3) 0.37698(17) 0.0523(9) Uani 1 1 d . . . O2 O 0.3193(3) 0.5123(3) 0.3182(2) 0.0503(11) Uani 1 1 d . . . N2 N -0.0393(3) 0.3773(3) 0.39886(19) 0.0219(9) Uani 1 1 d . . . C2 C -0.2865(4) 0.4064(3) 0.4429(2) 0.0246(12) Uani 1 1 d . . . S3 S 0.27931(9) 0.60699(10) 0.32520(6) 0.0267(3) Uani 1 1 d . . . F3 F 0.3532(2) 0.7819(2) 0.33242(16) 0.0419(8) Uani 1 1 d . . . O3 O 0.2162(2) 0.6411(3) 0.26954(17) 0.0381(10) Uani 1 1 d . . . N3 N 0.1221(3) 0.3642(3) 0.42942(19) 0.0220(9) Uani 1 1 d . . . C3 C -0.3701(4) 0.4155(4) 0.4692(3) 0.0307(13) Uani 1 1 d . . . H3 H -0.3706 0.4141 0.5152 0.037 Uiso 1 1 calc R . . S4 S -0.03332(9) 0.12522(9) 0.46437(6) 0.0223(3) Uani 1 1 d . . . F4 F 0.3602(2) 0.2254(3) 0.81795(18) 0.0577(10) Uani 1 1 d . . . O4 O 0.2415(3) 0.3551(3) 0.88415(17) 0.0369(10) Uani 1 1 d . . . N4 N -0.1181(3) 0.1440(3) 0.56498(19) 0.0210(9) Uani 1 1 d . . . C4 C -0.4521(4) 0.4266(4) 0.4259(3) 0.0318(13) Uani 1 1 d . . . H4 H -0.5099 0.4337 0.4428 0.038 Uiso 1 1 calc R . . S5 S 0.17461(8) 0.10680(9) 0.51089(6) 0.0216(3) Uani 1 1 d . . . F5 F 0.4429(2) 0.3289(3) 0.87900(18) 0.0645(12) Uani 1 1 d . . . O5 O 0.3125(3) 0.4906(3) 0.83561(19) 0.0398(10) Uani 1 1 d . . . N5 N 0.0424(3) 0.1285(3) 0.59654(19) 0.0213(9) Uani 1 1 d . . . C5 C -0.4527(4) 0.4277(4) 0.3582(3) 0.0325(13) Uani 1 1 d . . . H5 H -0.5104 0.4353 0.3299 0.039 Uiso 1 1 calc R . . S6 S 0.27751(9) 0.39307(10) 0.82807(6) 0.0241(3) Uani 1 1 d . . . F6 F 0.4252(3) 0.3458(4) 0.7761(2) 0.0833(15) Uani 1 1 d . . . O6 O 0.2221(3) 0.3709(3) 0.76626(17) 0.0360(9) Uani 1 1 d . . . N6 N 0.2003(3) 0.1111(3) 0.63682(19) 0.0211(9) Uani 1 1 d . . . C6 C -0.3688(4) 0.4176(4) 0.3317(3) 0.0289(13) Uani 1 1 d . . . H6 H -0.3682 0.4188 0.2857 0.035 Uiso 1 1 calc R . . C7 C -0.2875(4) 0.4059(3) 0.3751(2) 0.0232(11) Uani 1 1 d . . . C8 C -0.1796(4) 0.3887(4) 0.2899(2) 0.0297(12) Uani 1 1 d . . . H8A H -0.1120 0.3922 0.2880 0.045 Uiso 1 1 calc R . . H8B H -0.2115 0.4424 0.2645 0.045 Uiso 1 1 calc R . . H8C H -0.2043 0.3266 0.2715 0.045 Uiso 1 1 calc R . . C9 C 0.0341(3) 0.3722(3) 0.4455(2) 0.0216(11) Uani 1 1 d . . . C10 C 0.1596(3) 0.3606(3) 0.5429(2) 0.0212(11) Uani 1 1 d . . . C11 C 0.2196(4) 0.3540(3) 0.6018(3) 0.0256(12) Uani 1 1 d . . . H11 H 0.1965 0.3570 0.6426 0.031 Uiso 1 1 calc R . . C12 C 0.3148(4) 0.3429(4) 0.5986(3) 0.0290(12) Uani 1 1 d . . . H12 H 0.3580 0.3388 0.6380 0.035 Uiso 1 1 calc R . . C13 C 0.3477(4) 0.3376(4) 0.5386(3) 0.0311(13) Uani 1 1 d . . . H13 H 0.4130 0.3279 0.5381 0.037 Uiso 1 1 calc R . . C14 C 0.2895(3) 0.3459(4) 0.4803(3) 0.0261(12) Uani 1 1 d . . . H14 H 0.3135 0.3445 0.4397 0.031 Uiso 1 1 calc R . . C15 C 0.1932(4) 0.3565(3) 0.4824(2) 0.0218(11) Uani 1 1 d . . . C16 C 0.1411(4) 0.3635(4) 0.3613(2) 0.0303(13) Uani 1 1 d . . . H16A H 0.0830 0.3777 0.3318 0.046 Uiso 1 1 calc R . . H16B H 0.1646 0.2993 0.3509 0.046 Uiso 1 1 calc R . . H16C H 0.1884 0.4129 0.3558 0.046 Uiso 1 1 calc R . . C17 C 0.3793(4) 0.6898(4) 0.3272(2) 0.0304(13) Uani 1 1 d . . . C18 C -0.0036(4) 0.6473(4) 0.2437(2) 0.0311(13) Uani 1 1 d . . . H18A H -0.0627 0.6844 0.2326 0.037 Uiso 1 1 calc R . . H18B H 0.0495 0.6927 0.2428 0.037 Uiso 1 1 calc R . . C19 C -0.0307(3) 0.1328(3) 0.5495(2) 0.0188(11) Uani 1 1 d . . . C20 C -0.1551(4) 0.1391(3) 0.4517(2) 0.0227(12) Uani 1 1 d . . . C21 C -0.2156(4) 0.1426(3) 0.3925(2) 0.0262(12) Uani 1 1 d . . . H21 H -0.1924 0.1363 0.3519 0.031 Uiso 1 1 calc R . . C22 C -0.3107(4) 0.1554(4) 0.3949(3) 0.0290(12) Uani 1 1 d . . . H22 H -0.3535 0.1580 0.3553 0.035 Uiso 1 1 calc R . . C23 C -0.3440(4) 0.1644(4) 0.4546(2) 0.0283(12) Uani 1 1 d . . . H23 H -0.4094 0.1738 0.4548 0.034 Uiso 1 1 calc R . . C24 C -0.2848(3) 0.1601(4) 0.5139(2) 0.0257(12) Uani 1 1 d . . . H24 H -0.3083 0.1653 0.5544 0.031 Uiso 1 1 calc R . . C25 C -0.1893(3) 0.1477(3) 0.5114(2) 0.0243(12) Uani 1 1 d . . . C26 C -0.1369(3) 0.1547(4) 0.6325(2) 0.0254(12) Uani 1 1 d . . . H26A H -0.0788 0.1438 0.6628 0.038 Uiso 1 1 calc R . . H26B H -0.1843 0.1071 0.6411 0.038 Uiso 1 1 calc R . . H26C H -0.1602 0.2205 0.6388 0.038 Uiso 1 1 calc R . . C27 C 0.1309(3) 0.1163(3) 0.5855(2) 0.0222(11) Uani 1 1 d . . . C28 C 0.2887(3) 0.0944(3) 0.5522(2) 0.0221(11) Uani 1 1 d . . . C29 C 0.3720(4) 0.0819(3) 0.5253(3) 0.0253(12) Uani 1 1 d . . . H29 H 0.3715 0.0790 0.4792 0.030 Uiso 1 1 calc R . . C30 C 0.4547(4) 0.0740(4) 0.5681(3) 0.0304(13) Uani 1 1 d . . . H30 H 0.5122 0.0673 0.5510 0.036 Uiso 1 1 calc R . . C31 C 0.4560(4) 0.0756(4) 0.6361(3) 0.0328(13) Uani 1 1 d . . . H31 H 0.5140 0.0683 0.6643 0.039 Uiso 1 1 calc R . . C32 C 0.3735(3) 0.0877(3) 0.6629(2) 0.0249(12) Uani 1 1 d . . . H32 H 0.3740 0.0893 0.7090 0.030 Uiso 1 1 calc R . . C33 C 0.2902(3) 0.0974(3) 0.6199(2) 0.0230(11) Uani 1 1 d . . . C34 C 0.1848(4) 0.1242(4) 0.7052(2) 0.0297(12) Uani 1 1 d . . . H34A H 0.1172 0.1245 0.7074 0.045 Uiso 1 1 calc R . . H34B H 0.2124 0.1860 0.7219 0.045 Uiso 1 1 calc R . . H34C H 0.2145 0.0706 0.7320 0.045 Uiso 1 1 calc R . . C35 C 0.3821(4) 0.3198(5) 0.8248(3) 0.0415(15) 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 Cl1 0.0307(8) 0.0672(11) 0.0285(8) -0.0139(7) 0.0075(6) -0.0076(7) S1 0.0206(7) 0.0263(7) 0.0197(7) -0.0001(5) 0.0058(5) -0.0009(5) F1 0.035(2) 0.102(3) 0.053(2) -0.021(2) 0.0296(18) -0.018(2) O1 0.031(2) 0.046(2) 0.026(2) 0.0031(17) 0.0077(17) -0.0031(17) N1 0.024(2) 0.030(3) 0.017(2) -0.0007(18) 0.0030(19) -0.0009(19) C1 0.027(3) 0.019(3) 0.024(3) 0.001(2) 0.011(2) -0.001(2) Cl2 0.0293(9) 0.1014(14) 0.0230(8) 0.0024(8) 0.0072(6) 0.0025(8) S2 0.0226(7) 0.0254(7) 0.0181(7) 0.0000(5) 0.0028(5) -0.0005(5) F2 0.0284(19) 0.060(2) 0.062(2) 0.0103(19) -0.0161(17) -0.0082(17) O2 0.031(2) 0.037(3) 0.081(3) -0.017(2) 0.004(2) -0.0019(18) N2 0.022(2) 0.022(2) 0.021(2) 0.0014(17) 0.0018(19) -0.0017(17) C2 0.023(3) 0.021(3) 0.029(3) -0.002(2) 0.000(2) -0.003(2) S3 0.0189(7) 0.0338(8) 0.0276(7) -0.0070(6) 0.0038(6) -0.0018(6) F3 0.0336(19) 0.035(2) 0.059(2) 0.0001(16) 0.0137(16) -0.0042(14) O3 0.023(2) 0.067(3) 0.022(2) -0.0013(18) -0.0034(16) -0.0064(18) N3 0.024(2) 0.024(2) 0.017(2) -0.0002(17) 0.0025(19) 0.0012(17) C3 0.027(3) 0.033(3) 0.034(3) 0.002(2) 0.011(3) 0.001(2) S4 0.0221(7) 0.0260(7) 0.0195(7) -0.0002(5) 0.0050(5) -0.0007(5) F4 0.043(2) 0.050(2) 0.074(3) -0.024(2) -0.0135(19) 0.0174(18) O4 0.036(2) 0.048(3) 0.029(2) 0.0029(17) 0.0117(18) 0.0009(18) N4 0.021(2) 0.023(2) 0.019(2) -0.0001(17) 0.0040(19) 0.0005(17) C4 0.025(3) 0.035(4) 0.037(3) -0.004(2) 0.008(3) -0.003(2) S5 0.0192(7) 0.0267(7) 0.0198(7) 0.0001(5) 0.0057(5) 0.0001(5) F5 0.032(2) 0.082(3) 0.068(3) -0.033(2) -0.0304(18) 0.023(2) O5 0.034(2) 0.032(2) 0.052(3) -0.0019(18) 0.0006(19) -0.0035(17) N5 0.020(2) 0.025(2) 0.021(2) 0.0010(17) 0.0060(19) 0.0020(17) C5 0.025(3) 0.037(4) 0.033(3) 0.000(2) -0.001(3) -0.002(2) S6 0.0179(7) 0.0310(8) 0.0237(7) -0.0001(6) 0.0044(5) 0.0010(6) F6 0.040(2) 0.143(4) 0.075(3) -0.009(3) 0.039(2) 0.012(2) O6 0.030(2) 0.048(3) 0.028(2) -0.0022(17) -0.0008(17) 0.0059(18) N6 0.018(2) 0.024(2) 0.021(2) -0.0029(18) 0.0033(18) -0.0033(18) C6 0.030(3) 0.029(3) 0.025(3) -0.002(2) -0.004(2) -0.002(2) C7 0.024(3) 0.021(3) 0.025(3) -0.003(2) 0.003(2) -0.002(2) C8 0.027(3) 0.042(3) 0.021(3) -0.001(2) 0.006(2) 0.001(2) C9 0.023(3) 0.019(3) 0.024(3) 0.003(2) 0.006(2) -0.001(2) C10 0.017(3) 0.020(3) 0.025(3) 0.000(2) 0.000(2) -0.0005(19) C11 0.033(3) 0.019(3) 0.026(3) -0.002(2) 0.006(2) -0.001(2) C12 0.033(3) 0.025(3) 0.029(3) 0.002(2) 0.002(2) -0.002(2) C13 0.026(3) 0.025(3) 0.042(3) 0.003(3) 0.006(3) 0.001(2) C14 0.022(3) 0.029(3) 0.028(3) -0.003(2) 0.005(2) -0.003(2) C15 0.025(3) 0.015(3) 0.023(3) -0.0026(19) -0.003(2) -0.001(2) C16 0.029(3) 0.042(4) 0.020(3) -0.002(2) 0.006(2) 0.005(2) C17 0.025(3) 0.042(4) 0.022(3) -0.005(2) -0.002(2) 0.002(3) C18 0.031(3) 0.030(3) 0.034(3) -0.001(2) 0.012(3) 0.000(2) C19 0.027(3) 0.012(3) 0.019(3) -0.0021(18) 0.007(2) -0.0026(19) C20 0.028(3) 0.015(3) 0.026(3) 0.003(2) 0.009(2) 0.002(2) C21 0.030(3) 0.025(3) 0.023(3) 0.000(2) 0.003(2) -0.004(2) C22 0.027(3) 0.031(3) 0.025(3) 0.001(2) -0.006(2) 0.002(2) C23 0.023(3) 0.025(3) 0.035(3) 0.003(2) 0.000(2) 0.007(2) C24 0.024(3) 0.026(3) 0.028(3) -0.001(2) 0.005(2) -0.002(2) C25 0.023(3) 0.022(3) 0.027(3) 0.000(2) 0.002(2) 0.000(2) C26 0.023(3) 0.035(3) 0.019(3) 0.001(2) 0.006(2) 0.002(2) C27 0.026(3) 0.020(3) 0.022(3) -0.002(2) 0.008(2) -0.003(2) C28 0.018(3) 0.022(3) 0.027(3) 0.003(2) 0.007(2) -0.001(2) C29 0.030(3) 0.019(3) 0.029(3) 0.001(2) 0.011(3) 0.000(2) C30 0.019(3) 0.036(4) 0.039(3) -0.005(2) 0.014(3) -0.001(2) C31 0.020(3) 0.036(4) 0.040(3) -0.005(3) -0.003(3) -0.002(2) C32 0.023(3) 0.027(3) 0.024(3) 0.005(2) 0.000(2) -0.001(2) C33 0.021(3) 0.021(3) 0.028(3) 0.002(2) 0.007(2) 0.000(2) C34 0.025(3) 0.040(3) 0.024(3) -0.002(2) 0.004(2) 0.002(2) C35 0.018(3) 0.059(4) 0.048(4) -0.015(3) 0.006(3) 0.008(3) _geom_special_details ; To improve the refinement stability, restraints were placed on the displacement parameters of the atoms C1C2C3O1 of one acetone molecule. A restraint on the bond length C2-C3 was also applied. 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 Cl1 C18 1.745(5) . ? S1 C2 1.743(5) . ? S1 C1 1.749(5) . ? F1 C17 1.324(6) . ? O1 S3 1.437(3) . ? N1 C1 1.350(6) . ? N1 C7 1.414(6) . ? N1 C8 1.465(6) . ? C1 N2 1.324(6) . ? Cl2 C18 1.753(5) . ? S2 C9 1.749(5) . ? S2 C10 1.752(5) . ? F2 C17 1.321(6) . ? O2 S3 1.439(4) . ? N2 C9 1.324(6) . ? C2 C3 1.393(7) . ? C2 C7 1.398(7) . ? S3 O3 1.436(4) . ? S3 C17 1.830(6) . ? F3 C17 1.330(6) . ? N3 C9 1.358(6) . ? N3 C15 1.389(6) . ? N3 C16 1.469(6) . ? C3 C4 1.381(7) . ? C3 H3 0.9500 . ? S4 C20 1.743(5) . ? S4 C19 1.753(5) . ? F4 C35 1.338(7) . ? O4 S6 1.432(4) . ? N4 C19 1.350(6) . ? N4 C25 1.395(6) . ? N4 C26 1.464(5) . ? C4 C5 1.395(7) . ? C4 H4 0.9500 . ? S5 C28 1.745(5) . ? S5 C27 1.748(5) . ? F5 C35 1.322(6) . ? O5 S6 1.433(4) . ? N5 C19 1.325(6) . ? N5 C27 1.335(6) . ? C5 C6 1.402(7) . ? C5 H5 0.9500 . ? S6 O6 1.435(4) . ? S6 C35 1.820(6) . ? F6 C35 1.304(7) . ? N6 C27 1.348(6) . ? N6 C33 1.399(6) . ? N6 C34 1.471(6) . ? C6 C7 1.376(7) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.388(7) . ? C10 C15 1.401(7) . ? C11 C12 1.388(7) . ? C11 H11 0.9500 . ? C12 C13 1.389(7) . ? C12 H12 0.9500 . ? C13 C14 1.369(7) . ? C13 H13 0.9500 . ? C14 C15 1.399(7) . ? C14 H14 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C21 1.393(7) . ? C20 C25 1.395(6) . ? C21 C22 1.387(7) . ? C21 H21 0.9500 . ? C22 C23 1.389(7) . ? C22 H22 0.9500 . ? C23 C24 1.387(7) . ? C23 H23 0.9500 . ? C24 C25 1.392(7) . ? C24 H24 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C28 C33 1.395(6) . ? C28 C29 1.401(6) . ? C29 C30 1.380(7) . ? C29 H29 0.9500 . ? C30 C31 1.400(7) . ? C30 H30 0.9500 . ? C31 C32 1.389(7) . ? C31 H31 0.9500 . ? C32 C33 1.391(7) . ? C32 H32 0.9500 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 C2 S1 C1 91.2(2) . . ? C1 N1 C7 114.6(4) . . ? C1 N1 C8 123.5(4) . . ? C7 N1 C8 121.8(4) . . ? N2 C1 N1 118.8(4) . . ? N2 C1 S1 129.9(4) . . ? N1 C1 S1 111.3(3) . . ? C9 S2 C10 91.3(2) . . ? C1 N2 C9 124.2(4) . . ? C3 C2 C7 120.3(5) . . ? C3 C2 S1 128.6(4) . . ? C7 C2 S1 111.2(4) . . ? O3 S3 O1 114.8(2) . . ? O3 S3 O2 115.6(2) . . ? O1 S3 O2 114.8(2) . . ? O3 S3 C17 102.6(2) . . ? O1 S3 C17 102.6(2) . . ? O2 S3 C17 104.0(2) . . ? C9 N3 C15 114.8(4) . . ? C9 N3 C16 122.8(4) . . ? C15 N3 C16 122.4(4) . . ? C4 C3 C2 117.7(5) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C20 S4 C19 91.1(2) . . ? C19 N4 C25 114.7(4) . . ? C19 N4 C26 122.9(4) . . ? C25 N4 C26 122.3(4) . . ? C3 C4 C5 121.9(5) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C28 S5 C27 90.6(2) . . ? C19 N5 C27 123.7(4) . . ? C4 C5 C6 120.6(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? O4 S6 O5 114.6(2) . . ? O4 S6 O6 114.9(2) . . ? O5 S6 O6 115.9(2) . . ? O4 S6 C35 103.0(3) . . ? O5 S6 C35 104.1(3) . . ? O6 S6 C35 101.9(3) . . ? C27 N6 C33 114.7(4) . . ? C27 N6 C34 123.3(4) . . ? C33 N6 C34 121.9(4) . . ? C7 C6 C5 117.1(5) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C6 C7 C2 122.4(5) . . ? C6 C7 N1 125.8(5) . . ? C2 C7 N1 111.7(4) . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 N3 120.1(4) . . ? N2 C9 S2 129.0(4) . . ? N3 C9 S2 110.9(4) . . ? C11 C10 C15 121.7(5) . . ? C11 C10 S2 128.2(4) . . ? C15 C10 S2 110.1(4) . . ? C12 C11 C10 117.3(5) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C11 C12 C13 120.8(5) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 122.4(5) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 117.6(5) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? N3 C15 C14 127.0(4) . . ? N3 C15 C10 112.9(4) . . ? C14 C15 C10 120.1(5) . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? F2 C17 F1 107.4(4) . . ? F2 C17 F3 108.2(4) . . ? F1 C17 F3 107.2(4) . . ? F2 C17 S3 111.2(4) . . ? F1 C17 S3 111.4(4) . . ? F3 C17 S3 111.4(4) . . ? Cl1 C18 Cl2 111.0(3) . . ? Cl1 C18 H18A 109.4 . . ? Cl2 C18 H18A 109.4 . . ? Cl1 C18 H18B 109.4 . . ? Cl2 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? N5 C19 N4 119.9(4) . . ? N5 C19 S4 129.1(4) . . ? N4 C19 S4 111.0(4) . . ? C21 C20 C25 121.0(5) . . ? C21 C20 S4 128.5(4) . . ? C25 C20 S4 110.6(4) . . ? C22 C21 C20 117.9(5) . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 122.0(5) . . ? C24 C23 H23 119.0 . . ? C22 C23 H23 119.0 . . ? C23 C24 C25 117.2(5) . . ? C23 C24 H24 121.4 . . ? C25 C24 H24 121.4 . . ? C24 C25 C20 121.2(5) . . ? C24 C25 N4 126.2(4) . . ? C20 C25 N4 112.6(4) . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 N6 119.3(4) . . ? N5 C27 S5 129.2(4) . . ? N6 C27 S5 111.5(3) . . ? C33 C28 C29 120.7(5) . . ? C33 C28 S5 111.3(3) . . ? C29 C28 S5 128.0(4) . . ? C30 C29 C28 117.6(5) . . ? C30 C29 H29 121.2 . . ? C28 C29 H29 121.2 . . ? C29 C30 C31 121.7(4) . . ? C29 C30 H30 119.1 . . ? C31 C30 H30 119.1 . . ? C32 C31 C30 120.8(5) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 117.7(5) . . ? C31 C32 H32 121.2 . . ? C33 C32 H32 121.2 . . ? C32 C33 C28 121.5(4) . . ? C32 C33 N6 126.6(4) . . ? C28 C33 N6 111.9(4) . . ? N6 C34 H34A 109.5 . . ? N6 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N6 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? F6 C35 F5 107.2(5) . . ? F6 C35 F4 108.4(5) . . ? F5 C35 F4 107.4(5) . . ? F6 C35 S6 111.3(5) . . ? F5 C35 S6 111.5(4) . . ? F4 C35 S6 111.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 N2 179.5(4) . . . . ? C8 N1 C1 N2 4.0(7) . . . . ? C7 N1 C1 S1 -1.0(5) . . . . ? C8 N1 C1 S1 -176.6(4) . . . . ? C2 S1 C1 N2 179.8(5) . . . . ? C2 S1 C1 N1 0.5(4) . . . . ? N1 C1 N2 C9 177.1(4) . . . . ? S1 C1 N2 C9 -2.2(7) . . . . ? C1 S1 C2 C3 179.4(5) . . . . ? C1 S1 C2 C7 0.1(4) . . . . ? C7 C2 C3 C4 -1.7(7) . . . . ? S1 C2 C3 C4 179.1(4) . . . . ? C2 C3 C4 C5 0.7(8) . . . . ? C3 C4 C5 C6 -0.1(8) . . . . ? C4 C5 C6 C7 0.6(8) . . . . ? C5 C6 C7 C2 -1.6(7) . . . . ? C5 C6 C7 N1 -179.0(5) . . . . ? C3 C2 C7 C6 2.2(7) . . . . ? S1 C2 C7 C6 -178.4(4) . . . . ? C3 C2 C7 N1 179.9(4) . . . . ? S1 C2 C7 N1 -0.7(5) . . . . ? C1 N1 C7 C6 178.7(5) . . . . ? C8 N1 C7 C6 -5.6(7) . . . . ? C1 N1 C7 C2 1.1(6) . . . . ? C8 N1 C7 C2 176.8(4) . . . . ? C1 N2 C9 N3 -178.3(4) . . . . ? C1 N2 C9 S2 2.7(7) . . . . ? C15 N3 C9 N2 -178.2(4) . . . . ? C16 N3 C9 N2 1.7(7) . . . . ? C15 N3 C9 S2 1.0(5) . . . . ? C16 N3 C9 S2 -179.1(3) . . . . ? C10 S2 C9 N2 178.7(5) . . . . ? C10 S2 C9 N3 -0.4(4) . . . . ? C9 S2 C10 C11 -179.2(5) . . . . ? C9 S2 C10 C15 -0.3(4) . . . . ? C15 C10 C11 C12 -0.2(7) . . . . ? S2 C10 C11 C12 178.6(4) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C11 C12 C13 C14 2.0(8) . . . . ? C12 C13 C14 C15 -2.3(8) . . . . ? C9 N3 C15 C14 178.9(5) . . . . ? C16 N3 C15 C14 -1.1(7) . . . . ? C9 N3 C15 C10 -1.2(6) . . . . ? C16 N3 C15 C10 178.9(4) . . . . ? C13 C14 C15 N3 -178.6(5) . . . . ? C13 C14 C15 C10 1.4(7) . . . . ? C11 C10 C15 N3 179.8(4) . . . . ? S2 C10 C15 N3 0.9(5) . . . . ? C11 C10 C15 C14 -0.2(7) . . . . ? S2 C10 C15 C14 -179.2(4) . . . . ? O3 S3 C17 F2 178.9(4) . . . . ? O1 S3 C17 F2 59.6(4) . . . . ? O2 S3 C17 F2 -60.3(4) . . . . ? O3 S3 C17 F1 -61.4(4) . . . . ? O1 S3 C17 F1 179.3(4) . . . . ? O2 S3 C17 F1 59.4(4) . . . . ? O3 S3 C17 F3 58.2(4) . . . . ? O1 S3 C17 F3 -61.2(4) . . . . ? O2 S3 C17 F3 179.0(4) . . . . ? C27 N5 C19 N4 179.1(4) . . . . ? C27 N5 C19 S4 -0.5(7) . . . . ? C25 N4 C19 N5 179.9(4) . . . . ? C26 N4 C19 N5 1.9(7) . . . . ? C25 N4 C19 S4 -0.5(5) . . . . ? C26 N4 C19 S4 -178.5(3) . . . . ? C20 S4 C19 N5 -179.7(4) . . . . ? C20 S4 C19 N4 0.7(3) . . . . ? C19 S4 C20 C21 179.0(5) . . . . ? C19 S4 C20 C25 -0.7(4) . . . . ? C25 C20 C21 C22 0.4(7) . . . . ? S4 C20 C21 C22 -179.3(4) . . . . ? C20 C21 C22 C23 0.0(7) . . . . ? C21 C22 C23 C24 -0.7(8) . . . . ? C22 C23 C24 C25 1.0(8) . . . . ? C23 C24 C25 C20 -0.6(7) . . . . ? C23 C24 C25 N4 178.3(5) . . . . ? C21 C20 C25 C24 0.0(7) . . . . ? S4 C20 C25 C24 179.7(4) . . . . ? C21 C20 C25 N4 -179.1(4) . . . . ? S4 C20 C25 N4 0.6(5) . . . . ? C19 N4 C25 C24 -179.1(5) . . . . ? C26 N4 C25 C24 -1.1(7) . . . . ? C19 N4 C25 C20 -0.1(6) . . . . ? C26 N4 C25 C20 177.9(4) . . . . ? C19 N5 C27 N6 -178.9(4) . . . . ? C19 N5 C27 S5 2.1(7) . . . . ? C33 N6 C27 N5 179.5(4) . . . . ? C34 N6 C27 N5 -3.8(7) . . . . ? C33 N6 C27 S5 -1.3(5) . . . . ? C34 N6 C27 S5 175.4(3) . . . . ? C28 S5 C27 N5 179.7(5) . . . . ? C28 S5 C27 N6 0.7(4) . . . . ? C27 S5 C28 C33 0.2(4) . . . . ? C27 S5 C28 C29 179.7(5) . . . . ? C33 C28 C29 C30 -0.7(7) . . . . ? S5 C28 C29 C30 179.8(4) . . . . ? C28 C29 C30 C31 1.7(7) . . . . ? C29 C30 C31 C32 -1.6(8) . . . . ? C30 C31 C32 C33 0.5(7) . . . . ? C31 C32 C33 C28 0.5(7) . . . . ? C31 C32 C33 N6 -179.3(5) . . . . ? C29 C28 C33 C32 -0.4(7) . . . . ? S5 C28 C33 C32 179.2(4) . . . . ? C29 C28 C33 N6 179.5(4) . . . . ? S5 C28 C33 N6 -0.9(5) . . . . ? C27 N6 C33 C32 -178.7(5) . . . . ? C34 N6 C33 C32 4.6(7) . . . . ? C27 N6 C33 C28 1.5(6) . . . . ? C34 N6 C33 C28 -175.3(4) . . . . ? O4 S6 C35 F6 -179.2(4) . . . . ? O5 S6 C35 F6 -59.4(5) . . . . ? O6 S6 C35 F6 61.4(5) . . . . ? O4 S6 C35 F5 -59.7(5) . . . . ? O5 S6 C35 F5 60.2(5) . . . . ? O6 S6 C35 F5 -179.0(4) . . . . ? O4 S6 C35 F4 60.0(5) . . . . ? O5 S6 C35 F4 179.8(4) . . . . ? O6 S6 C35 F4 -59.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.701 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.107 #===END