#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:44:43 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297249 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573642.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_1573642 _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 2023-05-15 _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 16.8614(15) _cell_length_b 9.8359(4) _cell_length_c 16.3043(9) _cell_measurement_reflns_used 1692 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.2100 _cell_measurement_theta_min 1.8340 _cell_volume 2704.0(3) _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 2160000 _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 0.823 _diffrn_measured_fraction_theta_max 0.536 _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 39 deg.' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0194154734 _diffrn_orient_matrix_UB_12 -0.0196827703 _diffrn_orient_matrix_UB_13 -0.0094615094 _diffrn_orient_matrix_UB_21 0.0135962643 _diffrn_orient_matrix_UB_22 0.0338631290 _diffrn_orient_matrix_UB_23 0.0040973511 _diffrn_orient_matrix_UB_31 0.0055703933 _diffrn_orient_matrix_UB_32 -0.0142172611 _diffrn_orient_matrix_UB_33 0.0229091662 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.410 _diffrn_reflns_av_R_equivalents 0.1302 _diffrn_reflns_av_unetI/netI 0.2521 _diffrn_reflns_Laue_measured_fraction_full 0.823 _diffrn_reflns_Laue_measured_fraction_max 0.536 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 9095 _diffrn_reflns_point_group_measured_fraction_full 0.823 _diffrn_reflns_point_group_measured_fraction_max 0.536 _diffrn_reflns_theta_full 14.241 _diffrn_reflns_theta_max 21.703 _diffrn_reflns_theta_min 1.559 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 2.672 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.27354 _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 2.192 _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 2.16 GPa and left to stabilize over ? hours.' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-pentane/dichloromethane' _exptl_crystal_size_max 0.002 _exptl_crystal_size_mid 0.0015 _exptl_crystal_size_min 0.001 _refine_diff_density_max 3.142 _refine_diff_density_min -3.500 _refine_diff_density_rms 0.302 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 4454 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.1884 _refine_ls_R_factor_gt 0.1214 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+18.1786P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3105 _refine_ls_wR_factor_ref 0.3593 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2208 _reflns_number_total 4454 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b3.cif _cod_data_source_block 0010_2p16GPa _cod_database_code 1573642 _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 0010_2p16GPa in Pbca #61 0010_2p16GPa.res created by SHELXL-2018/3 at 20:22:30 on 15-May-2023 CELL 0.41 16.861359 9.835949 16.304312 90 90 90 ZERR 8 0.00145 0.000361 0.000913 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 2 CONF BOND MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.000000 18.178600 FVAR 0.79409 AU1 5 0.383349 0.871556 0.343385 11.00000 0.06653 0.02953 = 0.05578 0.00651 0.00010 -0.00109 P1 4 0.376085 1.064772 0.267077 11.00000 0.05643 0.02573 = 0.04773 0.00181 -0.00281 -0.00083 O1 3 0.334502 0.058077 0.554991 11.00000 0.05978 0.04138 = 0.09304 0.01529 -0.01312 -0.00505 C6 1 0.357671 0.179621 0.519228 11.00000 0.03507 0.03148 = 0.06088 -0.00436 0.00409 0.01085 C3 1 0.375649 0.436188 0.451490 11.00000 0.07377 0.03349 = 0.04929 0.00844 -0.00817 -0.00623 C10 1 0.392554 1.023955 0.160657 11.00000 0.09783 0.02454 = 0.07883 0.00864 0.01510 0.01295 AFIX 23 H10A 2 0.359701 1.083010 0.127253 11.00000 -1.20000 H10B 2 0.447471 1.043299 0.147324 11.00000 -1.20000 AFIX 0 C8 1 0.438951 0.359397 0.476104 11.00000 0.06229 0.03210 = 0.04946 0.00971 0.00310 -0.00127 AFIX 43 H8 2 0.489603 0.395442 0.470041 11.00000 -1.20000 AFIX 0 C2 1 0.388316 0.574900 0.421364 11.00000 0.05644 0.05310 = 0.06788 -0.02284 -0.01123 0.02372 C12 1 0.282014 1.152967 0.272014 11.00000 0.10806 0.02813 = 0.08427 -0.00559 0.01891 0.01327 AFIX 23 H12A 2 0.271246 1.179593 0.328205 11.00000 -1.20000 H12B 2 0.284441 1.234697 0.238815 11.00000 -1.20000 AFIX 0 C7 1 0.431368 0.230151 0.509736 11.00000 0.03690 0.02413 = 0.07249 0.00557 -0.00581 -0.00020 AFIX 43 H7 2 0.475745 0.180182 0.525184 11.00000 -1.20000 AFIX 0 C15 1 0.437183 1.326328 0.249653 11.00000 0.09219 0.03960 = 0.08084 -0.00335 -0.00242 -0.01670 AFIX 137 H15A 2 0.430151 1.315149 0.191615 11.00000 -1.50000 H15B 2 0.482352 1.383358 0.259714 11.00000 -1.50000 H15C 2 0.390681 1.367716 0.272690 11.00000 -1.50000 AFIX 0 C14 1 0.450005 1.192635 0.287877 11.00000 0.04596 0.04119 = 0.05554 0.00050 -0.00285 -0.00980 AFIX 23 H14A 2 0.453087 1.205280 0.346793 11.00000 -1.20000 H14B 2 0.501011 1.158284 0.269777 11.00000 -1.20000 AFIX 0 C4 1 0.299660 0.385730 0.460482 11.00000 0.06578 0.03365 = 0.06974 0.00423 -0.01774 0.00792 AFIX 43 H4 2 0.256083 0.437526 0.444790 11.00000 -1.20000 AFIX 0 C1 1 0.392811 0.687188 0.395863 11.00000 0.05023 0.04660 = 0.07312 0.02456 0.00261 -0.00053 C13 1 0.215210 1.060928 0.240819 11.00000 0.02875 0.06073 = 0.09724 -0.02201 0.01608 0.00450 AFIX 137 H13A 2 0.229180 1.025324 0.187934 11.00000 -1.50000 H13B 2 0.167096 1.112597 0.236417 11.00000 -1.50000 H13C 2 0.207493 0.987187 0.278557 11.00000 -1.50000 AFIX 0 C5 1 0.289084 0.254876 0.493714 11.00000 0.03937 0.04419 = 0.07613 -0.00228 0.00187 -0.00021 AFIX 43 H5 2 0.238580 0.217905 0.499029 11.00000 -1.20000 AFIX 0 C9 1 0.397743 -0.031346 0.564726 11.00000 0.05073 0.02813 = 0.09042 0.00048 0.00913 -0.00340 AFIX 137 H9A 2 0.418582 -0.055313 0.511873 11.00000 -1.50000 H9B 2 0.379781 -0.111890 0.592309 11.00000 -1.50000 H9C 2 0.438502 0.011465 0.596713 11.00000 -1.50000 AFIX 0 C11 1 0.375232 0.880512 0.138382 11.00000 0.17017 0.02495 = 0.10194 -0.00892 0.11093 -0.01883 AFIX 137 H11A 2 0.406713 0.854951 0.091807 11.00000 -1.50000 H11B 2 0.320019 0.871520 0.125076 11.00000 -1.50000 H11C 2 0.387774 0.822389 0.183870 11.00000 -1.50000 AFIX 0 HKLF 4 REM 0010_2p16GPa in Pbca #61 REM wR2 = 0.3593, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.1214 for 2208 Fo > 4sig(Fo) and 0.1884 for all 4454 data REM 167 parameters refined using 0 restraints END WGHT 0.0000 18.1254 REM Highest difference peak 3.142, deepest hole -3.500, 1-sigma level 0.302 Q1 1 0.3385 0.8646 0.3795 11.00000 0.05 3.14 Q2 1 0.3784 0.8204 0.2965 11.00000 0.05 3.06 ; _shelx_res_checksum 48955 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 1.961 _oxdiff_exptl_absorpt_empirical_full_min 0.402 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 0.38335(6) 0.87156(6) 0.34338(4) 0.0506(3) Uani 1 1 d . . . . . P1 P 0.3761(3) 1.0648(4) 0.2671(3) 0.0433(11) Uani 1 1 d . . . . . O1 O 0.3345(11) 0.0581(12) 0.5550(10) 0.065(4) Uani 1 1 d . . . . . C6 C 0.3577(12) 0.1796(14) 0.5192(11) 0.042(4) Uani 1 1 d . . . . . C3 C 0.3756(14) 0.4362(15) 0.4515(11) 0.052(5) Uani 1 1 d . . . . . C10 C 0.3926(17) 1.0240(17) 0.1607(13) 0.067(8) Uani 1 1 d . . . . . H10A H 0.359701 1.083010 0.127253 0.080 Uiso 1 1 calc R U . . . H10B H 0.447471 1.043299 0.147324 0.080 Uiso 1 1 calc R U . . . C8 C 0.4390(15) 0.3594(13) 0.4761(11) 0.048(5) Uani 1 1 d . . . . . H8 H 0.489603 0.395442 0.470041 0.058 Uiso 1 1 calc R U . . . C2 C 0.3883(15) 0.575(2) 0.4214(13) 0.059(6) Uani 1 1 d . . . . . C12 C 0.2820(18) 1.1530(15) 0.2720(15) 0.073(8) Uani 1 1 d . . . . . H12A H 0.271246 1.179593 0.328205 0.088 Uiso 1 1 calc R U . . . H12B H 0.284441 1.234697 0.238815 0.088 Uiso 1 1 calc R U . . . C7 C 0.4314(12) 0.2302(13) 0.5097(11) 0.045(4) Uani 1 1 d . . . . . H7 H 0.475745 0.180182 0.525184 0.053 Uiso 1 1 calc R U . . . C15 C 0.4372(18) 1.3263(16) 0.2497(16) 0.071(7) Uani 1 1 d . . . . . H15A H 0.430151 1.315149 0.191615 0.106 Uiso 1 1 calc R U . . . H15B H 0.482352 1.383358 0.259714 0.106 Uiso 1 1 calc R U . . . H15C H 0.390681 1.367716 0.272690 0.106 Uiso 1 1 calc R U . . . C14 C 0.4500(14) 1.1926(15) 0.2879(11) 0.048(4) Uani 1 1 d . . . . . H14A H 0.453087 1.205280 0.346793 0.057 Uiso 1 1 calc R U . . . H14B H 0.501011 1.158284 0.269777 0.057 Uiso 1 1 calc R U . . . C4 C 0.2997(15) 0.3857(14) 0.4605(14) 0.056(6) Uani 1 1 d . . . . . H4 H 0.256083 0.437526 0.444790 0.068 Uiso 1 1 calc R U . . . C1 C 0.3928(14) 0.6872(19) 0.3959(14) 0.057(5) Uani 1 1 d . . . . . C13 C 0.2152(13) 1.0609(18) 0.2408(15) 0.062(6) Uani 1 1 d . . . . . H13A H 0.229180 1.025324 0.187934 0.093 Uiso 1 1 calc R U . . . H13B H 0.167096 1.112597 0.236417 0.093 Uiso 1 1 calc R U . . . H13C H 0.207493 0.987187 0.278557 0.093 Uiso 1 1 calc R U . . . C5 C 0.2891(13) 0.2549(17) 0.4937(12) 0.053(5) Uani 1 1 d . . . . . H5 H 0.238580 0.217905 0.499029 0.064 Uiso 1 1 calc R U . . . C9 C 0.3977(14) -0.0313(16) 0.5647(15) 0.056(6) Uani 1 1 d . . . . . H9A H 0.418582 -0.055313 0.511873 0.085 Uiso 1 1 calc R U . . . H9B H 0.379781 -0.111890 0.592309 0.085 Uiso 1 1 calc R U . . . H9C H 0.438502 0.011465 0.596713 0.085 Uiso 1 1 calc R U . . . C11 C 0.375(2) 0.8805(16) 0.1384(19) 0.099(14) Uani 1 1 d . . . . . H11A H 0.406713 0.854951 0.091807 0.149 Uiso 1 1 calc R U . . . H11B H 0.320019 0.871520 0.125076 0.149 Uiso 1 1 calc R U . . . H11C H 0.387774 0.822389 0.183870 0.149 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 0.0665(7) 0.0295(3) 0.0558(5) 0.00651(19) 0.0001(3) -0.0011(3) P1 0.056(4) 0.0257(15) 0.048(2) 0.0018(13) -0.0028(19) -0.0008(14) O1 0.060(14) 0.041(6) 0.093(10) 0.015(6) -0.013(9) -0.005(6) C6 0.035(13) 0.031(6) 0.061(9) -0.004(6) 0.004(8) 0.011(6) C3 0.074(18) 0.033(7) 0.049(9) 0.008(6) -0.008(8) -0.006(7) C10 0.10(2) 0.025(7) 0.079(14) 0.009(7) 0.015(12) 0.013(8) C8 0.062(15) 0.032(7) 0.049(8) 0.010(5) 0.003(9) -0.001(6) C2 0.056(17) 0.053(10) 0.068(12) -0.023(8) -0.011(10) 0.024(9) C12 0.11(3) 0.028(7) 0.084(15) -0.006(7) 0.019(15) 0.013(8) C7 0.037(13) 0.024(6) 0.072(10) 0.006(6) -0.006(8) 0.000(5) C15 0.09(2) 0.040(8) 0.081(13) -0.003(8) -0.002(14) -0.017(9) C14 0.046(14) 0.041(7) 0.056(9) 0.000(6) -0.003(8) -0.010(7) C4 0.066(18) 0.034(7) 0.070(12) 0.004(7) -0.018(11) 0.008(7) C1 0.050(16) 0.047(9) 0.073(12) 0.025(8) 0.003(10) -0.001(8) C13 0.029(15) 0.061(10) 0.097(15) -0.022(10) 0.016(11) 0.005(7) C5 0.039(15) 0.044(8) 0.076(12) -0.002(7) 0.002(9) 0.000(7) C9 0.051(16) 0.028(7) 0.090(14) 0.000(7) 0.009(11) -0.003(6) C11 0.17(3) 0.025(7) 0.102(17) -0.009(7) 0.11(2) -0.019(10) 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 171.9(7) . . ? C10 P1 Au1 109.4(5) . . ? C10 P1 C12 106.5(12) . . ? C10 P1 C14 103.3(10) . . ? C12 P1 Au1 115.0(8) . . ? C14 P1 Au1 116.3(6) . . ? C14 P1 C12 105.3(10) . . ? C6 O1 C9 112.2(17) . . ? O1 C6 C5 109.9(17) . . ? C7 C6 O1 128.8(16) . . ? C7 C6 C5 121.3(15) . . ? C8 C3 C2 120(2) . . ? C8 C3 C4 119.6(15) . . ? C4 C3 C2 120.3(18) . . ? P1 C10 H10A 108.6 . . ? P1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C11 C10 P1 114.6(15) . . ? C11 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C3 C8 H8 118.4 . . ? C3 C8 C7 123(2) . . ? C7 C8 H8 118.4 . . ? C1 C2 C3 175(2) . . ? P1 C12 H12A 109.6 . . ? P1 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C13 C12 P1 110.3(11) . . ? C13 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C6 C7 C8 117.9(17) . . ? C6 C7 H7 121.1 . . ? C8 C7 H7 121.1 . . ? 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 108.2 . . ? P1 C14 H14B 108.2 . . ? C15 C14 P1 116.2(16) . . ? C15 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C3 C4 H4 120.4 . . ? C3 C4 C5 119.1(18) . . ? C5 C4 H4 120.4 . . ? C2 C1 Au1 171(2) . . ? 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 120.6 . . ? C4 C5 C6 118.8(19) . . ? C4 C5 H5 120.6 . . ? 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 2.275(4) . ? Au1 C1 2.011(17) . ? P1 C10 1.80(2) . ? P1 C12 1.81(3) . ? P1 C14 1.803(18) . ? O1 C6 1.39(2) . ? O1 C9 1.39(3) . ? C6 C7 1.35(3) . ? C6 C5 1.43(3) . ? C3 C8 1.37(3) . ? C3 C2 1.47(3) . ? C3 C4 1.38(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.49(3) . ? C8 H8 0.9300 . ? C8 C7 1.390(19) . ? C2 C1 1.18(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.53(3) . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 C14 1.47(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C4 H4 0.9300 . ? C4 C5 1.41(2) . ? 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 23(3) . . . . ? Au1 P1 C12 C13 -60.4(18) . . . . ? Au1 P1 C14 C15 -169.4(14) . . . . ? O1 C6 C7 C8 -176.1(18) . . . . ? O1 C6 C5 C4 176.0(17) . . . . ? C3 C8 C7 C6 -1(3) . . . . ? C3 C4 C5 C6 2(3) . . . . ? C10 P1 C12 C13 61.0(18) . . . . ? C10 P1 C14 C15 70.8(18) . . . . ? C8 C3 C4 C5 -1(3) . . . . ? C2 C3 C8 C7 176.2(17) . . . . ? C2 C3 C4 C5 -176.6(17) . . . . ? C12 P1 C10 C11 -102(2) . . . . ? C12 P1 C14 C15 -41(2) . . . . ? C7 C6 C5 C4 -2(3) . . . . ? C14 P1 C10 C11 148(2) . . . . ? C14 P1 C12 C13 170.2(15) . . . . ? C4 C3 C8 C7 1(3) . . . . ? C5 C6 C7 C8 2(3) . . . . ? C9 O1 C6 C7 -15(3) . . . . ? C9 O1 C6 C5 167.0(17) . . . . ?