#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:44:43 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297249 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573645.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_1573645 _journal_paper_doi 10.1039/D4DT03036B _chemical_formula_moiety 'C15 H22 Au O P' _chemical_formula_sum 'C15 H22 Au O P' _chemical_formula_weight 446.26 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-05-24 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2024-07-24 deposited with the CCDC. 2025-01-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.5789(3) _cell_length_b 9.75229(9) _cell_length_c 16.0089(5) _cell_measurement_reflns_used 4040 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.6660 _cell_measurement_theta_min 1.8590 _cell_volume 2588.35(10) _computing_cell_refinement 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment 'Diamond Anvil Cell filled with Daphne-7575' _diffrn_ambient_pressure 3300000 _diffrn_ambient_temperature 293(2) _diffrn_crystal_treatment 'pressurized rapidly in Daphne-7575 as a hydrostatic medium' _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 13.3333 _diffrn_measured_fraction_theta_full 0.622 _diffrn_measured_fraction_theta_max 0.405 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -39.00 39.00 0.50 1.00 -- 0.00 0.00 0.00 156 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'esperanto-CrysAlisPro-abstract goniometer imported esperanto images' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'Diamond Anvil Cell, effective opening angle 38 deg.' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0121328290 _diffrn_orient_matrix_UB_12 0.0038577742 _diffrn_orient_matrix_UB_13 -0.0221935258 _diffrn_orient_matrix_UB_21 0.0010265596 _diffrn_orient_matrix_UB_22 -0.0416611305 _diffrn_orient_matrix_UB_23 -0.0032799743 _diffrn_orient_matrix_UB_31 -0.0215196770 _diffrn_orient_matrix_UB_32 -0.0041430559 _diffrn_orient_matrix_UB_33 0.0123599203 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.410 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_unetI/netI 0.0372 _diffrn_reflns_Laue_measured_fraction_full 0.622 _diffrn_reflns_Laue_measured_fraction_max 0.405 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8771 _diffrn_reflns_point_group_measured_fraction_full 0.622 _diffrn_reflns_point_group_measured_fraction_max 0.405 _diffrn_reflns_theta_full 14.241 _diffrn_reflns_theta_max 21.699 _diffrn_reflns_theta_min 1.578 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 2.792 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79465 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 2.290 _exptl_crystal_description needle _exptl_crystal_F_000 1712 _exptl_crystal_preparation 'Mounted in a Diamond-Anvil Cell using Daphne-7575 as pressure medium.,Luminescent' _exptl_crystal_pressure_history 'Pressurized to 3.30 GPa and left to stabilize over ? hours.' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-pentane/dichloromethane' _exptl_crystal_size_max 0.0025 _exptl_crystal_size_mid 0.002 _exptl_crystal_size_min 0.0015 _refine_diff_density_max 0.731 _refine_diff_density_min -0.860 _refine_diff_density_rms 0.113 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 3220 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0234 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0213P)^2^+0.8571P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.0645 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2818 _reflns_number_total 3220 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b3.cif _cod_data_source_block 0019_3p30GPa _cod_database_code 1573645 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H22 O P Au' _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. ; _diffrn_orient_matrix_axis[1] matrixX _diffrn_orient_matrix_axis[2] matrixY _diffrn_orient_matrix_axis[3] matrixZ _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B) 2.b Aromatic/amide H refined with riding coordinates: C8(H8), C7(H7), C4(H4), C5(H5) 2.c Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C) ; _shelx_res_file ; TITL 0019_3p30GPa in Pbca #61 0019_3p30GPa.res created by SHELXL-2018/3 at 13:04:31 on 24-May-2023 CELL 0.41 16.5789 9.752287 16.008866 90 90 90 ZERR 8 0.000307 0.000092 0.000534 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H O P Au DISP Au -0.4672 3.5799 8847.0811 DISP C -0.0001 0.0005 5.0796 DISP H 0 0 0.5971 DISP O 0.0016 0.0018 9.9389 DISP P 0.0342 0.0304 85.9578 UNIT 120 176 8 8 8 L.S. 40 0 0 PLAN 1 CONF BOND MORE -1 BOND $H fmap 2 53 acta OMIT 21 8 8 OMIT 16 9 16 OMIT 21 1 4 REM REM REM WGHT 0.021300 0.857100 FVAR 1.46117 AU1 5 0.384232 0.878447 0.345225 11.00000 0.02743 0.02159 = 0.02213 0.00481 -0.00056 -0.00130 P1 4 0.377401 1.072836 0.267869 11.00000 0.02387 0.01787 = 0.02082 0.00141 0.00019 0.00033 O1 3 0.335884 0.057033 0.557494 11.00000 0.03812 0.02360 = 0.04543 0.01045 0.00073 -0.00260 C6 1 0.353525 0.179665 0.520312 11.00000 0.02831 0.02111 = 0.02002 0.00173 -0.00058 -0.00089 C3 1 0.376578 0.438649 0.450482 11.00000 0.02980 0.02122 = 0.01694 0.00354 -0.00070 -0.00108 C10 1 0.390262 1.030044 0.158520 11.00000 0.02991 0.02352 = 0.02436 0.00087 0.00127 -0.00162 AFIX 23 H10A 2 0.360131 1.095202 0.125022 11.00000 -1.20000 H10B 2 0.446809 1.039445 0.144052 11.00000 -1.20000 AFIX 0 C8 1 0.442156 0.357977 0.474744 11.00000 0.02240 0.02403 = 0.02570 0.00210 0.00176 0.00040 AFIX 43 H8 2 0.494325 0.390974 0.467547 11.00000 -1.20000 AFIX 0 C2 1 0.387739 0.575141 0.419111 11.00000 0.02474 0.02565 = 0.02956 0.00311 0.00083 0.00140 C12 1 0.281563 1.162270 0.271806 11.00000 0.02566 0.02593 = 0.04031 -0.00649 0.00045 0.00187 AFIX 23 H12A 2 0.269920 1.188693 0.328962 11.00000 -1.20000 H12B 2 0.284628 1.244997 0.238317 11.00000 -1.20000 AFIX 0 C7 1 0.430338 0.229428 0.509388 11.00000 0.02638 0.02281 = 0.02989 0.00228 -0.00050 0.00231 AFIX 43 H7 2 0.474476 0.176680 0.525290 11.00000 -1.20000 AFIX 0 C15 1 0.438161 1.336571 0.247893 11.00000 0.03130 0.02362 = 0.04292 0.00637 -0.00075 -0.00404 AFIX 137 H15A 2 0.423670 1.323947 0.190346 11.00000 -1.50000 H15B 2 0.485057 1.394029 0.251380 11.00000 -1.50000 H15C 2 0.394242 1.379171 0.277115 11.00000 -1.50000 AFIX 0 C14 1 0.456347 1.198455 0.287129 11.00000 0.02960 0.02493 = 0.02177 -0.00234 -0.00538 -0.00229 AFIX 23 H14A 2 0.462879 1.210131 0.346920 11.00000 -1.20000 H14B 2 0.506884 1.164092 0.264904 11.00000 -1.20000 AFIX 0 C4 1 0.298912 0.385889 0.460930 11.00000 0.02159 0.02795 = 0.03052 0.00460 -0.00358 0.00026 AFIX 43 H4 2 0.254664 0.438096 0.444696 11.00000 -1.20000 AFIX 0 C1 1 0.390988 0.693570 0.396804 11.00000 0.02804 0.02730 = 0.02493 0.00663 -0.00141 -0.00051 C13 1 0.215216 1.072232 0.239506 11.00000 0.02634 0.03877 = 0.04750 -0.01231 -0.00183 -0.00061 AFIX 137 H13A 2 0.224168 1.053314 0.181392 11.00000 -1.50000 H13B 2 0.164366 1.118020 0.246200 11.00000 -1.50000 H13C 2 0.214636 0.987718 0.270246 11.00000 -1.50000 AFIX 0 C5 1 0.286815 0.257829 0.494879 11.00000 0.02233 0.02903 = 0.03141 0.00468 -0.00194 -0.00413 AFIX 43 H5 2 0.234835 0.223371 0.500915 11.00000 -1.20000 AFIX 0 C9 1 0.400396 -0.038966 0.562925 11.00000 0.05111 0.02075 = 0.04338 -0.00001 0.00081 0.00553 AFIX 137 H9A 2 0.426752 -0.045807 0.509693 11.00000 -1.50000 H9B 2 0.379485 -0.127109 0.578543 11.00000 -1.50000 H9C 2 0.438441 -0.008698 0.604202 11.00000 -1.50000 AFIX 0 C11 1 0.362488 0.884824 0.136297 11.00000 0.03311 0.02447 = 0.03309 -0.00531 -0.00241 -0.00100 AFIX 137 H11A 2 0.376038 0.865400 0.079209 11.00000 -1.50000 H11B 2 0.305147 0.878052 0.143552 11.00000 -1.50000 H11C 2 0.388865 0.819966 0.172197 11.00000 -1.50000 AFIX 0 HKLF 4 REM 0019_3p30GPa in Pbca #61 REM wR2 = 0.0645, GooF = S = 1.101, Restrained GooF = 1.101 for all data REM R1 = 0.0234 for 2818 Fo > 4sig(Fo) and 0.0264 for all 3220 data REM 167 parameters refined using 0 restraints END WGHT 0.0213 0.8571 REM Highest difference peak 0.731, deepest hole -0.860, 1-sigma level 0.113 Q1 1 0.3553 0.7851 0.3438 11.00000 0.05 0.72 ; _shelx_res_checksum 94204 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.541 _oxdiff_exptl_absorpt_empirical_full_min 0.782 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 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 0.38423(2) 0.87845(2) 0.34522(2) 0.02372(6) Uani 1 1 d . . . . . P1 P 0.37740(4) 1.07284(5) 0.26787(6) 0.02085(17) Uani 1 1 d . . . . . O1 O 0.33588(13) 0.05703(17) 0.5575(2) 0.0357(7) Uani 1 1 d . . . . . C6 C 0.35353(16) 0.1797(2) 0.5203(2) 0.0232(6) Uani 1 1 d . . . . . C3 C 0.37658(15) 0.4386(2) 0.4505(2) 0.0227(7) Uani 1 1 d . . . . . C10 C 0.39026(16) 1.0300(3) 0.1585(2) 0.0259(8) Uani 1 1 d . . . . . H10A H 0.360131 1.095202 0.125022 0.031 Uiso 1 1 calc R U . . . H10B H 0.446809 1.039445 0.144052 0.031 Uiso 1 1 calc R U . . . C8 C 0.44216(16) 0.3580(2) 0.4747(2) 0.0240(7) Uani 1 1 d . . . . . H8 H 0.494325 0.390974 0.467547 0.029 Uiso 1 1 calc R U . . . C2 C 0.38774(15) 0.5751(3) 0.4191(3) 0.0267(7) Uani 1 1 d . . . . . C12 C 0.28156(16) 1.1623(2) 0.2718(3) 0.0306(8) Uani 1 1 d . . . . . H12A H 0.269920 1.188693 0.328962 0.037 Uiso 1 1 calc R U . . . H12B H 0.284628 1.244997 0.238317 0.037 Uiso 1 1 calc R U . . . C7 C 0.43034(16) 0.2294(2) 0.5094(2) 0.0264(7) Uani 1 1 d . . . . . H7 H 0.474476 0.176680 0.525290 0.032 Uiso 1 1 calc R U . . . C15 C 0.43816(17) 1.3366(2) 0.2479(3) 0.0326(9) Uani 1 1 d . . . . . H15A H 0.423670 1.323947 0.190346 0.049 Uiso 1 1 calc R U . . . H15B H 0.485057 1.394029 0.251380 0.049 Uiso 1 1 calc R U . . . H15C H 0.394242 1.379171 0.277115 0.049 Uiso 1 1 calc R U . . . C14 C 0.45635(16) 1.1985(2) 0.2871(2) 0.0254(7) Uani 1 1 d . . . . . H14A H 0.462879 1.210131 0.346920 0.031 Uiso 1 1 calc R U . . . H14B H 0.506884 1.164092 0.264904 0.031 Uiso 1 1 calc R U . . . C4 C 0.29891(17) 0.3859(2) 0.4609(3) 0.0267(8) Uani 1 1 d . . . . . H4 H 0.254664 0.438096 0.444696 0.032 Uiso 1 1 calc R U . . . C1 C 0.39099(15) 0.6936(2) 0.3968(3) 0.0268(7) Uani 1 1 d . . . . . C13 C 0.21522(18) 1.0722(3) 0.2395(3) 0.0375(10) Uani 1 1 d . . . . . H13A H 0.224168 1.053314 0.181392 0.056 Uiso 1 1 calc R U . . . H13B H 0.164366 1.118020 0.246200 0.056 Uiso 1 1 calc R U . . . H13C H 0.214636 0.987718 0.270246 0.056 Uiso 1 1 calc R U . . . C5 C 0.28682(17) 0.2578(2) 0.4949(2) 0.0276(7) Uani 1 1 d . . . . . H5 H 0.234835 0.223371 0.500915 0.033 Uiso 1 1 calc R U . . . C9 C 0.4004(2) -0.0390(3) 0.5629(3) 0.0384(10) Uani 1 1 d . . . . . H9A H 0.426752 -0.045807 0.509693 0.058 Uiso 1 1 calc R U . . . H9B H 0.379485 -0.127109 0.578543 0.058 Uiso 1 1 calc R U . . . H9C H 0.438441 -0.008698 0.604202 0.058 Uiso 1 1 calc R U . . . C11 C 0.3625(2) 0.8848(2) 0.1363(3) 0.0302(8) Uani 1 1 d . . . . . H11A H 0.376038 0.865400 0.079209 0.045 Uiso 1 1 calc R U . . . H11B H 0.305147 0.878052 0.143552 0.045 Uiso 1 1 calc R U . . . H11C H 0.388865 0.819966 0.172197 0.045 Uiso 1 1 calc R U . . . 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 0.02743(9) 0.02159(6) 0.02213(15) 0.00481(3) -0.00056(3) -0.00130(2) P1 0.0239(3) 0.0179(2) 0.0208(6) 0.0014(2) 0.0002(2) 0.00033(15) O1 0.0381(13) 0.0236(7) 0.045(3) 0.0105(9) 0.0007(10) -0.0026(6) C6 0.0283(13) 0.0211(8) 0.020(2) 0.0017(9) -0.0006(9) -0.0009(7) C3 0.0298(14) 0.0212(9) 0.017(2) 0.0035(9) -0.0007(9) -0.0011(6) C10 0.0299(16) 0.0235(10) 0.024(3) 0.0009(10) 0.0013(9) -0.0016(7) C8 0.0224(13) 0.0240(8) 0.026(3) 0.0021(10) 0.0018(9) 0.0004(6) C2 0.0247(14) 0.0257(11) 0.030(3) 0.0031(11) 0.0008(9) 0.0014(7) C12 0.0257(14) 0.0259(9) 0.040(3) -0.0065(11) 0.0004(11) 0.0019(7) C7 0.0264(14) 0.0228(9) 0.030(3) 0.0023(10) -0.0005(10) 0.0023(7) C15 0.0313(15) 0.0236(9) 0.043(3) 0.0064(12) -0.0007(11) -0.0040(8) C14 0.0296(13) 0.0249(9) 0.022(3) -0.0023(10) -0.0054(10) -0.0023(7) C4 0.0216(15) 0.0280(10) 0.031(3) 0.0046(10) -0.0036(10) 0.0003(6) C1 0.0280(14) 0.0273(11) 0.025(3) 0.0066(11) -0.0014(10) -0.0005(7) C13 0.0263(15) 0.0388(12) 0.048(4) -0.0123(14) -0.0018(12) -0.0006(9) C5 0.0223(13) 0.0290(9) 0.031(3) 0.0047(10) -0.0019(10) -0.0041(7) C9 0.051(2) 0.0207(10) 0.043(4) 0.0000(12) 0.0008(15) 0.0055(9) C11 0.0331(18) 0.0245(11) 0.033(3) -0.0053(10) -0.0024(15) -0.0010(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0001 0.0005 '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' O O 0.0016 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.0342 0.0304 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -0.4672 3.5799 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _axis.id _axis.type _axis.equipment _axis.parity _axis.depends_on _axis.zero _axis.vector[1] _axis.vector[2] _axis.vector[3] source . source . . . 1.00000000 0.00000000 0.00000000 omega rotation goniometer -1 . -0.00106000 0.00000000 0.00000000 1.00000000 kappa rotation goniometer -1 omega 0.00000000 -0.76604444 0.00000000 0.64278761 phi rotation goniometer -1 kappa . 0.00000000 0.00000000 1.00000000 theta rotation goniometer -1 . 0.00200000 0.00000000 0.00000000 1.00000000 matrixX general general . phi . 1.00000000 0.00000000 0.00000000 matrixY general general . phi . 0.00000000 1.00000000 0.00000000 matrixZ general general . phi . 0.00000000 0.00000000 1.00000000 dacX translation general . phi . 0.00000000 1.00000000 0.00000000 dacY translation general . phi . -1.00000000 0.00000000 0.00000000 dacZ translation general . phi . 0.00000000 0.00000000 1.00000000 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Au1 P1 171.46(12) . . ? C10 P1 Au1 109.22(9) . . ? C10 P1 C12 104.32(16) . . ? C10 P1 C14 103.54(15) . . ? C12 P1 Au1 115.27(11) . . ? C12 P1 C14 107.49(11) . . ? C14 P1 Au1 115.76(11) . . ? C6 O1 C9 116.2(2) . . ? O1 C6 C7 124.2(2) . . ? O1 C6 C5 115.6(2) . . ? C7 C6 C5 120.1(2) . . ? C8 C3 C2 121.3(2) . . ? C4 C3 C8 118.5(2) . . ? C4 C3 C2 120.2(2) . . ? P1 C10 H10A 108.8 . . ? P1 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C11 C10 P1 113.7(3) . . ? C11 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C3 C8 H8 119.6 . . ? C7 C8 C3 120.7(2) . . ? C7 C8 H8 119.6 . . ? C1 C2 C3 174.0(3) . . ? P1 C12 H12A 109.6 . . ? P1 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C13 C12 P1 110.43(18) . . ? C13 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? P1 C14 H14A 109.1 . . ? P1 C14 H14B 109.1 . . ? C15 C14 P1 112.6(2) . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C3 C4 H4 119.5 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C2 C1 Au1 170.6(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C5 H5 120.3 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.3 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2672(7) . ? Au1 C1 1.986(3) . ? P1 C10 1.812(4) . ? P1 C12 1.814(3) . ? P1 C14 1.819(2) . ? O1 C6 1.368(3) . ? O1 C9 1.424(3) . ? C6 C7 1.374(4) . ? C6 C5 1.404(4) . ? C3 C8 1.397(4) . ? C3 C2 1.435(4) . ? C3 C4 1.397(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.531(3) . ? C8 H8 0.9300 . ? C8 C7 1.385(3) . ? C2 C1 1.210(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.499(4) . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 C14 1.516(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C4 H4 0.9300 . ? C4 C5 1.377(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C5 H5 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 P1 C10 C11 27.9(2) . . . . ? Au1 P1 C12 C13 -60.8(3) . . . . ? Au1 P1 C14 C15 -167.5(2) . . . . ? O1 C6 C7 C8 -176.8(3) . . . . ? O1 C6 C5 C4 176.6(3) . . . . ? C3 C8 C7 C6 0.0(6) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C10 P1 C12 C13 59.0(3) . . . . ? C10 P1 C14 C15 73.0(3) . . . . ? C8 C3 C4 C5 0.5(6) . . . . ? C2 C3 C8 C7 176.3(4) . . . . ? C2 C3 C4 C5 -176.7(4) . . . . ? C12 P1 C10 C11 -95.8(2) . . . . ? C12 P1 C14 C15 -37.0(3) . . . . ? C7 C6 C5 C4 -1.6(5) . . . . ? C14 P1 C10 C11 151.8(2) . . . . ? C14 P1 C12 C13 168.5(3) . . . . ? C4 C3 C8 C7 -0.9(6) . . . . ? C5 C6 C7 C8 1.3(5) . . . . ? C9 O1 C6 C7 -18.4(5) . . . . ? C9 O1 C6 C5 163.5(3) . . . . ?