#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:23:38 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119067.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7119067 loop_ _publ_author_name 'Ming Chen' 'Ning Sun' 'Haoyi Chen' 'Yuanhong Liu' _publ_section_title ; Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles ; _journal_name_full Chem.Commun. _journal_page_first 6324 _journal_volume 52 _journal_year 2016 _chemical_absolute_configuration ad _chemical_formula_sum 'C29 H36 Au F6 N3 O4 S2' _chemical_formula_weight 865.69 _chemical_name_systematic ; ? ; _space_group_crystal_system trigonal _space_group_IT_number 154 _space_group_name_Hall 'P 32 2"' _space_group_name_H-M_alt 'P 32 2 1' _symmetry_space_group_name_Hall 'P 32 2"' _symmetry_space_group_name_H-M 'P 32 2 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2016-02-23 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 11.4418(8) _cell_length_b 11.4418(8) _cell_length_c 23.880(3) _cell_measurement_reflns_used 5319 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 45.740 _cell_measurement_theta_min 4.451 _cell_volume 2707.4(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_unetI/netI 0.0477 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 16240 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.955 _diffrn_reflns_theta_min 2.055 _exptl_absorpt_coefficient_mu 4.257 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.3224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.593 _exptl_crystal_description prismatic _exptl_crystal_F_000 1284 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.969 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.079 _refine_ls_abs_structure_details ; Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.002(6) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3549 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0280 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.0620 _reflns_Friedel_coverage 0.734 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3318 _reflns_number_total 3549 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cc02776h2.cif _cod_data_source_block cd15206 _cod_original_cell_volume 2707.4(5) _cod_database_code 7119067 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.515 _shelx_estimated_absorpt_t_max 0.652 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd15206 in P3(2)21 CELL 0.71073 11.4418 11.4418 23.8803 90.000 90.000 120.000 ZERR 3.00 0.0008 0.0008 0.0025 0.000 0.000 0.000 LATT -1 SYMM -Y, X-Y, 0.66667+Z SYMM -X+Y, -X, 0.33333+Z SYMM Y, X, -Z SYMM X-Y, -Y, 0.33333-Z SYMM -X, -X+Y, 0.66667-Z SFAC C H N O F S Au UNIT 87 108 9 12 18 6 3 OMIT -3.00 52.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 isor 0.006 c11 f1 f2 f3 size 0.18 0.15 0.11 wpdb -1 mpla c3 > c8 mpla n1 c1 c2 htab conf EQIV $1 x+1, y+1, z HTAB C2 O2_$1 WGHT 0.024700 FVAR 0.08179 AU1 7 0.193062 0.193062 0.000000 10.50000 0.02985 0.02985 = 0.04485 0.00230 -0.00230 0.00692 S1 6 0.012446 -0.130287 -0.005631 11.00000 0.05172 0.03774 = 0.08988 0.00286 -0.00567 0.01398 F1 5 0.111767 -0.057518 -0.104257 11.00000 0.22152 0.17719 = 0.12028 -0.00358 0.06631 0.05921 F2 5 -0.101413 -0.166187 -0.102637 11.00000 0.19967 0.24046 = 0.10832 -0.05315 -0.05792 0.13837 F3 5 0.005930 -0.266123 -0.093530 11.00000 0.20166 0.14324 = 0.17501 -0.06685 -0.02829 0.10836 N1 3 0.465694 0.409210 0.038045 11.00000 0.03061 0.03062 = 0.04377 0.00016 -0.00264 0.00966 N2 3 0.009034 0.009034 0.000000 10.50000 0.02977 0.02977 = 0.07392 0.00498 -0.00498 0.00533 O1 4 0.140410 -0.104846 0.011114 11.00000 0.06841 0.07239 = 0.15513 -0.00432 -0.02666 0.04174 O2 4 -0.103951 -0.242425 0.015458 11.00000 0.08197 0.03654 = 0.15535 0.02648 0.00623 0.00556 C1 1 0.366112 0.366112 0.000000 10.50000 0.02063 0.02063 = 0.03838 -0.00229 0.00229 0.00297 C2 1 0.571042 0.536527 0.022956 11.00000 0.03355 0.03657 = 0.05742 -0.01070 -0.00268 0.00324 AFIX 43 H2 2 0.651436 0.587270 0.042407 11.00000 -1.20000 AFIX 0 C3 1 0.463937 0.333278 0.086347 11.00000 0.03283 0.03978 = 0.03799 0.00038 -0.00341 0.01368 C4 1 0.507687 0.238890 0.080128 11.00000 0.04214 0.04304 = 0.05120 -0.00612 -0.00379 0.01814 C5 1 0.506986 0.171216 0.128255 11.00000 0.08597 0.05173 = 0.07072 0.00115 -0.00843 0.04510 AFIX 43 H5 2 0.535827 0.108412 0.126151 11.00000 -1.20000 AFIX 0 C6 1 0.465847 0.193194 0.178224 11.00000 0.11195 0.05932 = 0.05284 0.01015 -0.00551 0.04143 AFIX 43 H6 2 0.468646 0.147182 0.209835 11.00000 -1.20000 AFIX 0 C7 1 0.419997 0.283014 0.182540 11.00000 0.09083 0.07065 = 0.03881 0.00345 0.00488 0.03594 AFIX 43 H7 2 0.389183 0.294839 0.216934 11.00000 -1.20000 AFIX 0 C8 1 0.418695 0.356260 0.136795 11.00000 0.04837 0.05217 = 0.04555 -0.00560 -0.00169 0.02373 C9 1 0.373552 0.461490 0.141553 11.00000 0.07738 0.08167 = 0.05464 -0.00529 0.00690 0.05448 AFIX 13 H9 2 0.363135 0.486683 0.103431 11.00000 -1.20000 AFIX 0 C10 1 0.480273 0.588080 0.170460 11.00000 0.14849 0.10477 = 0.21692 -0.07832 -0.06082 0.09248 AFIX 137 H10A 2 0.448413 0.650982 0.174286 11.00000 -1.50000 H10B 2 0.561497 0.628177 0.148547 11.00000 -1.50000 H10C 2 0.498512 0.565266 0.206856 11.00000 -1.50000 AFIX 0 C11 1 0.240319 0.405637 0.169959 11.00000 0.12377 0.15409 = 0.19372 0.01641 0.05102 0.09226 AFIX 137 H11A 2 0.246207 0.376154 0.206955 11.00000 -1.50000 H11B 2 0.173283 0.330516 0.148864 11.00000 -1.50000 H11C 2 0.215591 0.474241 0.172368 11.00000 -1.50000 AFIX 0 C12 1 0.554475 0.214480 0.024264 11.00000 0.06429 0.06625 = 0.05766 -0.01357 -0.00425 0.03715 AFIX 13 H12 2 0.515674 0.246842 -0.004193 11.00000 -1.20000 AFIX 0 C13 1 0.501822 0.068508 0.011299 11.00000 0.08667 0.08126 = 0.11581 -0.04035 0.01102 0.03128 AFIX 137 H13A 2 0.545352 0.034091 0.035073 11.00000 -1.50000 H13B 2 0.520160 0.059192 -0.027169 11.00000 -1.50000 H13C 2 0.406196 0.018654 0.017679 11.00000 -1.50000 AFIX 0 C14 1 0.706322 0.299954 0.017563 11.00000 0.07939 0.10999 = 0.10658 -0.02803 0.01928 0.03190 AFIX 137 H14A 2 0.733135 0.393590 0.021388 11.00000 -1.50000 H14B 2 0.731922 0.284639 -0.018793 11.00000 -1.50000 H14C 2 0.749999 0.275722 0.045854 11.00000 -1.50000 AFIX 0 C15 1 0.007646 -0.154646 -0.081293 11.00000 0.14375 0.08467 = 0.11016 -0.02658 -0.02044 0.06616 HKLF 4 REM cd15206 in P3(2)21 REM R1 = 0.0280 for 3318 Fo > 4sig(Fo) and 0.0313 for all 3549 data REM 209 parameters refined using 24 restraints END WGHT 0.0248 0.0000 REM Instructions for potential hydrogen bonds HTAB C2 O2_$1 REM Highest difference peak 0.969, deepest hole -0.630, 1-sigma level 0.079 Q1 1 0.1969 0.1999 0.0417 11.00000 0.05 0.97 Q2 1 0.2770 0.2770 0.0000 10.50000 0.05 0.79 Q3 1 0.2788 0.2377 0.0172 11.00000 0.05 0.79 Q4 1 0.1550 0.2394 0.0218 11.00000 0.05 0.65 Q5 1 0.1590 0.1158 0.0204 11.00000 0.05 0.56 Q6 1 0.0057 -0.0611 -0.1095 11.00000 0.05 0.43 Q7 1 0.3865 0.4940 0.2052 11.00000 0.05 0.28 Q8 1 -0.0556 -0.0540 -0.0682 11.00000 0.05 0.26 Q9 1 0.2909 0.4509 0.2153 11.00000 0.05 0.25 Q10 1 -0.0957 -0.2157 -0.1073 11.00000 0.05 0.24 Q11 1 0.4171 0.3212 0.1044 11.00000 0.05 0.24 Q12 1 0.3678 0.2738 0.0430 11.00000 0.05 0.24 Q13 1 0.2024 0.3717 0.1326 11.00000 0.05 0.24 Q14 1 0.4719 0.3882 0.1038 11.00000 0.05 0.23 Q15 1 0.0973 -0.1404 -0.1066 11.00000 0.05 0.23 Q16 1 0.1927 0.1984 0.0856 11.00000 0.05 0.23 Q17 1 -0.1847 -0.2849 -0.0775 11.00000 0.05 0.23 Q18 1 -0.1570 -0.2159 -0.0978 11.00000 0.05 0.22 Q19 1 0.4647 0.1598 0.2551 11.00000 0.05 0.22 Q20 1 0.2627 0.0043 0.2243 11.00000 0.05 0.21 ; _shelx_res_checksum 96771 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'y, x, -z' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.19306(3) 0.19306(3) 0.0000 0.03840(11) Uani 1 2 d S T P . . S1 S 0.01245(19) -0.13029(18) -0.00563(9) 0.0635(5) Uani 1 1 d . . . . . F1 F 0.1118(11) -0.0575(11) -0.1043(3) 0.191(4) Uani 1 1 d . U . . . F2 F -0.1014(10) -0.1662(10) -0.1026(3) 0.170(3) Uani 1 1 d . U . . . F3 F 0.0059(9) -0.2661(9) -0.0935(4) 0.163(3) Uani 1 1 d . U . . . N1 N 0.4657(5) 0.4092(5) 0.0380(2) 0.0375(12) Uani 1 1 d . . . . . N2 N 0.0090(6) 0.0090(6) 0.0000 0.049(2) Uani 1 2 d S T P . . O1 O 0.1404(6) -0.1048(7) 0.0111(3) 0.096(2) Uani 1 1 d . . . . . O2 O -0.1040(7) -0.2424(6) 0.0155(3) 0.102(2) Uani 1 1 d . . . . . C1 C 0.3661(6) 0.3661(6) 0.0000 0.0298(18) Uani 1 2 d S T P . . C2 C 0.5710(8) 0.5365(6) 0.0230(3) 0.0489(16) Uani 1 1 d . . . . . H2 H 0.6514 0.5873 0.0424 0.059 Uiso 1 1 calc R U . . . C3 C 0.4639(5) 0.3333(6) 0.0863(2) 0.0389(11) Uani 1 1 d . . . . . C4 C 0.5077(7) 0.2389(6) 0.0801(3) 0.0469(15) Uani 1 1 d . . . . . C5 C 0.5070(8) 0.1712(7) 0.1283(3) 0.065(2) Uani 1 1 d . . . . . H5 H 0.5358 0.1084 0.1262 0.078 Uiso 1 1 calc R U . . . C6 C 0.4658(10) 0.1932(8) 0.1782(4) 0.075(2) Uani 1 1 d . . . . . H6 H 0.4686 0.1472 0.2098 0.090 Uiso 1 1 calc R U . . . C7 C 0.4200(8) 0.2830(8) 0.1825(3) 0.069(2) Uani 1 1 d . . . . . H7 H 0.3892 0.2948 0.2169 0.082 Uiso 1 1 calc R U . . . C8 C 0.4187(7) 0.3563(7) 0.1368(3) 0.0493(16) Uani 1 1 d . . . . . C9 C 0.3736(9) 0.4615(9) 0.1416(3) 0.065(2) Uani 1 1 d . . . . . H9 H 0.3631 0.4867 0.1034 0.078 Uiso 1 1 calc R U . . . C10 C 0.4803(13) 0.5881(12) 0.1705(6) 0.144(6) Uani 1 1 d . . . . . H10A H 0.4484 0.6510 0.1743 0.216 Uiso 1 1 calc R U . . . H10B H 0.5615 0.6282 0.1485 0.216 Uiso 1 1 calc R U . . . H10C H 0.4985 0.5653 0.2069 0.216 Uiso 1 1 calc R U . . . C11 C 0.2403(14) 0.4056(15) 0.1700(6) 0.147(6) Uani 1 1 d . U . . . H11A H 0.2462 0.3762 0.2070 0.221 Uiso 1 1 calc R U . . . H11B H 0.1733 0.3305 0.1489 0.221 Uiso 1 1 calc R U . . . H11C H 0.2156 0.4742 0.1724 0.221 Uiso 1 1 calc R U . . . C12 C 0.5545(9) 0.2145(9) 0.0243(3) 0.061(2) Uani 1 1 d . . . . . H12 H 0.5157 0.2468 -0.0042 0.073 Uiso 1 1 calc R U . . . C13 C 0.5018(10) 0.0685(10) 0.0113(5) 0.099(4) Uani 1 1 d . . . . . H13A H 0.5454 0.0341 0.0351 0.149 Uiso 1 1 calc R U . . . H13B H 0.5202 0.0592 -0.0272 0.149 Uiso 1 1 calc R U . . . H13C H 0.4062 0.0187 0.0177 0.149 Uiso 1 1 calc R U . . . C14 C 0.7063(10) 0.3000(11) 0.0176(5) 0.106(4) Uani 1 1 d . . . . . H14A H 0.7331 0.3936 0.0214 0.158 Uiso 1 1 calc R U . . . H14B H 0.7319 0.2846 -0.0188 0.158 Uiso 1 1 calc R U . . . H14C H 0.7500 0.2757 0.0459 0.158 Uiso 1 1 calc R U . . . C15 C 0.0076(14) -0.1546(11) -0.0813(5) 0.109(4) 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 0.02985(13) 0.02985(13) 0.04485(18) 0.00230(8) -0.00230(8) 0.00692(16) S1 0.0517(12) 0.0377(8) 0.0899(14) 0.0029(8) -0.0057(9) 0.0140(8) F1 0.222(9) 0.177(7) 0.120(6) -0.004(5) 0.066(6) 0.059(7) F2 0.200(8) 0.240(9) 0.108(5) -0.053(6) -0.058(5) 0.138(7) F3 0.202(9) 0.143(6) 0.175(7) -0.067(5) -0.028(5) 0.108(6) N1 0.031(3) 0.031(2) 0.044(3) 0.000(2) -0.003(2) 0.010(2) N2 0.030(3) 0.030(3) 0.074(6) 0.005(2) -0.005(2) 0.005(3) O1 0.068(4) 0.072(4) 0.155(7) -0.004(4) -0.027(4) 0.042(3) O2 0.082(4) 0.037(3) 0.155(7) 0.026(4) 0.006(4) 0.006(3) C1 0.021(3) 0.021(3) 0.038(5) -0.0023(18) 0.0023(18) 0.003(3) C2 0.034(4) 0.037(3) 0.057(4) -0.011(3) -0.003(3) 0.003(3) C3 0.033(3) 0.040(3) 0.038(3) 0.000(3) -0.003(2) 0.014(3) C4 0.042(4) 0.043(3) 0.051(4) -0.006(3) -0.004(3) 0.018(3) C5 0.086(6) 0.052(4) 0.071(5) 0.001(4) -0.008(4) 0.045(4) C6 0.112(7) 0.059(5) 0.053(5) 0.010(4) -0.006(5) 0.041(5) C7 0.091(6) 0.071(5) 0.039(4) 0.003(4) 0.005(4) 0.036(5) C8 0.048(4) 0.052(4) 0.046(4) -0.006(3) -0.002(3) 0.024(3) C9 0.077(5) 0.082(6) 0.055(4) -0.005(4) 0.007(4) 0.054(5) C10 0.148(11) 0.105(9) 0.217(17) -0.078(11) -0.061(11) 0.092(9) C11 0.124(9) 0.154(11) 0.194(12) 0.016(9) 0.051(8) 0.092(9) C12 0.064(6) 0.066(5) 0.058(4) -0.014(4) -0.004(4) 0.037(5) C13 0.087(7) 0.081(7) 0.116(8) -0.040(7) 0.011(6) 0.031(6) C14 0.079(7) 0.110(9) 0.107(8) -0.028(7) 0.019(6) 0.032(6) C15 0.144(13) 0.085(7) 0.110(9) -0.027(6) -0.020(8) 0.066(9) 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' 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 C1 Au1 N2 180.00(3) . . O1 S1 O2 120.2(5) . . O1 S1 N2 108.0(4) . . O2 S1 N2 113.1(4) . . O1 S1 C15 105.2(6) . . O2 S1 C15 105.9(5) . . N2 S1 C15 102.6(4) . . C1 N1 C2 109.9(5) . . C1 N1 C3 124.6(5) . . C2 N1 C3 125.5(5) . . S1 N2 S1 122.6(5) . 4 S1 N2 Au1 118.7(2) . . S1 N2 Au1 118.7(2) 4 . N1 C1 N1 105.2(6) 4 . N1 C1 Au1 127.4(3) 4 . N1 C1 Au1 127.4(3) . . C2 C2 N1 107.5(4) 4 . C2 C2 H2 126.2 4 . N1 C2 H2 126.2 . . C8 C3 C4 123.2(5) . . C8 C3 N1 118.4(5) . . C4 C3 N1 118.4(5) . . C5 C4 C3 115.9(6) . . C5 C4 C12 122.1(6) . . C3 C4 C12 121.9(6) . . C6 C5 C4 122.3(7) . . C6 C5 H5 118.9 . . C4 C5 H5 118.9 . . C5 C6 C7 120.3(7) . . C5 C6 H6 119.8 . . C7 C6 H6 119.8 . . C6 C7 C8 121.3(7) . . C6 C7 H7 119.4 . . C8 C7 H7 119.4 . . C7 C8 C3 117.0(6) . . C7 C8 C9 121.9(6) . . C3 C8 C9 121.2(6) . . C11 C9 C10 111.4(9) . . C11 C9 C8 111.8(8) . . C10 C9 C8 110.9(7) . . C11 C9 H9 107.5 . . C10 C9 H9 107.5 . . C8 C9 H9 107.5 . . C9 C10 H10A 109.5 . . C9 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . C9 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . C9 C11 H11A 109.5 . . C9 C11 H11B 109.5 . . H11A C11 H11B 109.5 . . C9 C11 H11C 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . C13 C12 C4 113.9(7) . . C13 C12 C14 112.9(7) . . C4 C12 C14 111.7(7) . . C13 C12 H12 105.8 . . C4 C12 H12 105.8 . . C14 C12 H12 105.8 . . C12 C13 H13A 109.5 . . C12 C13 H13B 109.5 . . H13A C13 H13B 109.5 . . C12 C13 H13C 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . C12 C14 H14A 109.5 . . C12 C14 H14B 109.5 . . H14A C14 H14B 109.5 . . C12 C14 H14C 109.5 . . H14A C14 H14C 109.5 . . H14B C14 H14C 109.5 . . F1 C15 F2 110.6(13) . . F1 C15 F3 107.9(12) . . F2 C15 F3 105.7(10) . . F1 C15 S1 110.4(8) . . F2 C15 S1 111.1(9) . . F3 C15 S1 110.9(9) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Au1 C1 1.980(7) . Au1 N2 2.106(7) . S1 O1 1.401(6) . S1 O2 1.402(6) . S1 N2 1.620(4) . S1 C15 1.825(12) . F1 C15 1.277(13) . F2 C15 1.292(13) . F3 C15 1.299(12) . N1 C1 1.343(6) . N1 C2 1.396(8) . N1 C3 1.438(7) . N2 S1 1.620(4) 4 C1 N1 1.343(6) 4 C2 C2 1.292(14) 4 C2 H2 0.9300 . C3 C8 1.387(8) . C3 C4 1.407(8) . C4 C5 1.384(9) . C4 C12 1.515(9) . C5 C6 1.352(11) . C5 H5 0.9300 . C6 C7 1.372(11) . C6 H6 0.9300 . C7 C8 1.381(10) . C7 H7 0.9300 . C8 C9 1.533(9) . C9 C11 1.489(14) . C9 C10 1.516(12) . C9 H9 0.9800 . C10 H10A 0.9600 . C10 H10B 0.9600 . C10 H10C 0.9600 . C11 H11A 0.9600 . C11 H11B 0.9600 . C11 H11C 0.9600 . C12 C13 1.497(12) . C12 C14 1.517(12) . C12 H12 0.9800 . C13 H13A 0.9600 . C13 H13B 0.9600 . C13 H13C 0.9600 . C14 H14A 0.9600 . C14 H14B 0.9600 . C14 H14C 0.9600 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O2 0.93 2.57 3.294(9) 135.3 1_665 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 O1 S1 N2 S1 -158.2(4) . . . 4 O2 S1 N2 S1 -22.7(4) . . . 4 C15 S1 N2 S1 90.9(5) . . . 4 O1 S1 N2 Au1 21.8(4) . . . . O2 S1 N2 Au1 157.3(4) . . . . C15 S1 N2 Au1 -89.1(5) . . . . C2 N1 C1 N1 -0.2(4) . . . 4 C3 N1 C1 N1 -179.0(6) . . . 4 C2 N1 C1 Au1 179.8(4) . . . . C3 N1 C1 Au1 1.0(6) . . . . C1 N1 C2 C2 0.4(10) . . . 4 C3 N1 C2 C2 179.3(7) . . . 4 C1 N1 C3 C8 -94.6(6) . . . . C2 N1 C3 C8 86.7(8) . . . . C1 N1 C3 C4 85.1(6) . . . . C2 N1 C3 C4 -93.5(7) . . . . C8 C3 C4 C5 -1.8(9) . . . . N1 C3 C4 C5 178.5(6) . . . . C8 C3 C4 C12 179.0(6) . . . . N1 C3 C4 C12 -0.7(9) . . . . C3 C4 C5 C6 0.5(11) . . . . C12 C4 C5 C6 179.7(8) . . . . C4 C5 C6 C7 1.4(14) . . . . C5 C6 C7 C8 -2.1(14) . . . . C6 C7 C8 C3 0.9(12) . . . . C6 C7 C8 C9 -177.3(8) . . . . C4 C3 C8 C7 1.1(10) . . . . N1 C3 C8 C7 -179.1(6) . . . . C4 C3 C8 C9 179.3(7) . . . . N1 C3 C8 C9 -1.0(10) . . . . C7 C8 C9 C11 -50.9(12) . . . . C3 C8 C9 C11 131.0(8) . . . . C7 C8 C9 C10 74.1(11) . . . . C3 C8 C9 C10 -104.0(9) . . . . C5 C4 C12 C13 44.2(10) . . . . C3 C4 C12 C13 -136.7(7) . . . . C5 C4 C12 C14 -85.3(9) . . . . C3 C4 C12 C14 93.8(9) . . . . O1 S1 C15 F1 -50.7(11) . . . . O2 S1 C15 F1 -179.0(10) . . . . N2 S1 C15 F1 62.2(11) . . . . O1 S1 C15 F2 -173.8(9) . . . . O2 S1 C15 F2 57.9(10) . . . . N2 S1 C15 F2 -60.9(10) . . . . O1 S1 C15 F3 68.9(10) . . . . O2 S1 C15 F3 -59.4(11) . . . . N2 S1 C15 F3 -178.2(9) . . . .