#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:44:43 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297249 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573647.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_1573647 _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 16.5856(7) _cell_length_b 9.7494(2) _cell_length_c 16.0285(4) _cell_measurement_reflns_used 2247 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.1500 _cell_measurement_theta_min 2.0000 _cell_volume 2591.80(14) _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 0.811 _diffrn_measured_fraction_theta_max 0.538 _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 0.0194813214 _diffrn_orient_matrix_UB_12 0.0222172895 _diffrn_orient_matrix_UB_13 0.0080008084 _diffrn_orient_matrix_UB_21 0.0150934351 _diffrn_orient_matrix_UB_22 -0.0309045049 _diffrn_orient_matrix_UB_23 -0.0075977804 _diffrn_orient_matrix_UB_31 0.0018041760 _diffrn_orient_matrix_UB_32 0.0178945170 _diffrn_orient_matrix_UB_33 -0.0230860909 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.410 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_unetI/netI 0.0763 _diffrn_reflns_Laue_measured_fraction_full 0.811 _diffrn_reflns_Laue_measured_fraction_max 0.538 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 8880 _diffrn_reflns_point_group_measured_fraction_full 0.811 _diffrn_reflns_point_group_measured_fraction_max 0.538 _diffrn_reflns_theta_full 14.241 _diffrn_reflns_theta_max 21.575 _diffrn_reflns_theta_min 1.999 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 2.788 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81649 _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 2.287 _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 0.002 _exptl_crystal_size_mid 0.0015 _exptl_crystal_size_min 0.001 _refine_diff_density_max 1.177 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.168 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 4215 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.826 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0363 _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^)+(0.0277P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.0862 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2674 _reflns_number_total 4215 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b3.cif _cod_data_source_block 0017_3p30GPa _cod_original_cell_volume 2591.80(13) _cod_database_code 1573647 _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 0017_3p30GPa in Pbca #61 0017_3p30GPa.res created by SHELXL-2018/3 at 13:01:23 on 24-May-2023 CELL 0.41 16.585592 9.749416 16.028461 90 90 90 ZERR 8 0.000671 0.000199 0.000376 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 PLAN 1 CONF BOND MORE -1 BOND $H fmap 2 53 acta OMIT 18 6 1 OMIT 19 6 3 OMIT 3 3 20 OMIT 0 2 21 REM REM REM WGHT 0.027700 FVAR 0.72262 AU1 5 0.384387 0.878320 0.345167 11.00000 0.03519 0.02349 = 0.02849 0.00528 -0.00060 -0.00170 P1 4 0.377270 1.072786 0.267967 11.00000 0.03166 0.01905 = 0.02626 0.00104 0.00035 -0.00031 O1 3 0.335503 0.057226 0.557534 11.00000 0.04723 0.02361 = 0.04931 0.01224 0.00481 -0.00076 C6 1 0.353655 0.179305 0.519890 11.00000 0.03692 0.01998 = 0.02879 0.00322 0.00200 -0.00083 C3 1 0.375835 0.438627 0.450475 11.00000 0.02728 0.02389 = 0.03007 0.00211 -0.00361 0.00048 C10 1 0.390383 1.029945 0.158098 11.00000 0.04075 0.02247 = 0.02571 -0.00272 0.00362 -0.00042 AFIX 23 H10A 2 0.360009 1.094863 0.124702 11.00000 -1.20000 H10B 2 0.446868 1.040158 0.143694 11.00000 -1.20000 AFIX 0 C8 1 0.442417 0.357898 0.474437 11.00000 0.02632 0.02169 = 0.03191 0.00037 0.00615 0.00100 AFIX 43 H8 2 0.494538 0.390823 0.466903 11.00000 -1.20000 AFIX 0 C2 1 0.388068 0.575482 0.419203 11.00000 0.03653 0.02991 = 0.03350 -0.00015 0.00050 0.00153 C12 1 0.282059 1.161837 0.272219 11.00000 0.03581 0.02896 = 0.04780 -0.00584 -0.00403 0.00046 AFIX 23 H12A 2 0.270561 1.188121 0.329361 11.00000 -1.20000 H12B 2 0.285061 1.244671 0.238841 11.00000 -1.20000 AFIX 0 C7 1 0.430201 0.229519 0.509207 11.00000 0.03917 0.02162 = 0.03303 -0.00053 -0.00229 0.00649 AFIX 43 H7 2 0.474273 0.176930 0.525446 11.00000 -1.20000 AFIX 0 C15 1 0.437538 1.337063 0.248696 11.00000 0.03844 0.02499 = 0.04936 0.00402 -0.00224 -0.00391 AFIX 137 H15A 2 0.418037 1.323792 0.192885 11.00000 -1.50000 H15B 2 0.485690 1.391658 0.247303 11.00000 -1.50000 H15C 2 0.397158 1.383175 0.281172 11.00000 -1.50000 AFIX 0 C14 1 0.455979 1.199608 0.287571 11.00000 0.02735 0.02493 = 0.03688 -0.00227 -0.00669 -0.00235 AFIX 23 H14A 2 0.462347 1.211165 0.347317 11.00000 -1.20000 H14B 2 0.506656 1.165787 0.265451 11.00000 -1.20000 AFIX 0 C4 1 0.298634 0.385493 0.460691 11.00000 0.03098 0.02955 = 0.03484 0.00308 -0.00832 0.00136 AFIX 43 H4 2 0.254356 0.437051 0.443844 11.00000 -1.20000 AFIX 0 C1 1 0.390937 0.693043 0.397633 11.00000 0.03642 0.03153 = 0.03320 0.00622 -0.00350 -0.00345 C13 1 0.215284 1.071334 0.239848 11.00000 0.02727 0.04155 = 0.06527 -0.01514 -0.00169 0.00143 AFIX 137 H13A 2 0.225846 1.047922 0.182708 11.00000 -1.50000 H13B 2 0.164870 1.119333 0.243521 11.00000 -1.50000 H13C 2 0.212629 0.989135 0.272710 11.00000 -1.50000 AFIX 0 C5 1 0.286619 0.257585 0.495399 11.00000 0.03677 0.03384 = 0.03691 0.00241 -0.00041 -0.00443 AFIX 43 H5 2 0.234683 0.223574 0.502497 11.00000 -1.20000 AFIX 0 C9 1 0.400456 -0.039101 0.562599 11.00000 0.05912 0.02034 = 0.04386 0.00130 -0.00113 0.00244 AFIX 137 H9A 2 0.427950 -0.042962 0.509946 11.00000 -1.50000 H9B 2 0.379467 -0.128187 0.575990 11.00000 -1.50000 H9C 2 0.437512 -0.010757 0.605258 11.00000 -1.50000 AFIX 0 C11 1 0.363663 0.886193 0.135751 11.00000 0.03595 0.02615 = 0.03390 -0.00650 -0.00118 -0.00174 AFIX 137 H11A 2 0.377856 0.867027 0.078869 11.00000 -1.50000 H11B 2 0.306297 0.878843 0.142363 11.00000 -1.50000 H11C 2 0.389879 0.821494 0.171842 11.00000 -1.50000 AFIX 0 HKLF 4 REM 0017_3p30GPa in Pbca #61 REM wR2 = 0.0862, GooF = S = 0.826, Restrained GooF = 0.826 for all data REM R1 = 0.0363 for 2674 Fo > 4sig(Fo) and 0.0638 for all 4215 data REM 167 parameters refined using 0 restraints END WGHT 0.0099 0.0000 REM Highest difference peak 1.177, deepest hole -1.120, 1-sigma level 0.168 Q1 1 0.3892 0.8340 0.3000 11.00000 0.05 1.18 ; _shelx_res_checksum 22481 _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 1.611 _oxdiff_exptl_absorpt_empirical_full_min 0.778 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 0.38439(2) 0.87832(2) 0.34517(2) 0.02906(7) Uani 1 1 d . . . . . P1 P 0.37727(8) 1.07279(11) 0.26797(7) 0.0257(3) Uani 1 1 d . . . . . O1 O 0.3355(3) 0.0572(3) 0.5575(2) 0.0400(10) Uani 1 1 d . . . . . C6 C 0.3537(3) 0.1793(4) 0.5199(3) 0.0286(10) Uani 1 1 d . . . . . C3 C 0.3758(3) 0.4386(4) 0.4505(3) 0.0271(10) Uani 1 1 d . . . . . C10 C 0.3904(3) 1.0299(5) 0.1581(2) 0.0296(11) Uani 1 1 d . . . . . H10A H 0.360009 1.094863 0.124702 0.036 Uiso 1 1 calc R U . . . H10B H 0.446868 1.040158 0.143694 0.036 Uiso 1 1 calc R U . . . C8 C 0.4424(3) 0.3579(4) 0.4744(3) 0.0266(9) Uani 1 1 d . . . . . H8 H 0.494538 0.390823 0.466903 0.032 Uiso 1 1 calc R U . . . C2 C 0.3881(3) 0.5755(5) 0.4192(3) 0.0333(11) Uani 1 1 d . . . . . C12 C 0.2821(4) 1.1618(5) 0.2722(3) 0.0375(12) Uani 1 1 d . . . . . H12A H 0.270561 1.188121 0.329361 0.045 Uiso 1 1 calc R U . . . H12B H 0.285061 1.244671 0.238841 0.045 Uiso 1 1 calc R U . . . C7 C 0.4302(3) 0.2295(4) 0.5092(3) 0.0313(11) Uani 1 1 d . . . . . H7 H 0.474273 0.176930 0.525446 0.038 Uiso 1 1 calc R U . . . C15 C 0.4375(4) 1.3371(4) 0.2487(3) 0.0376(12) Uani 1 1 d . . . . . H15A H 0.418037 1.323792 0.192885 0.056 Uiso 1 1 calc R U . . . H15B H 0.485690 1.391658 0.247303 0.056 Uiso 1 1 calc R U . . . H15C H 0.397158 1.383175 0.281172 0.056 Uiso 1 1 calc R U . . . C14 C 0.4560(3) 1.1996(4) 0.2876(3) 0.0297(10) Uani 1 1 d . . . . . H14A H 0.462347 1.211165 0.347317 0.036 Uiso 1 1 calc R U . . . H14B H 0.506656 1.165787 0.265451 0.036 Uiso 1 1 calc R U . . . C4 C 0.2986(3) 0.3855(4) 0.4607(3) 0.0318(10) Uani 1 1 d . . . . . H4 H 0.254356 0.437051 0.443844 0.038 Uiso 1 1 calc R U . . . C1 C 0.3909(3) 0.6930(5) 0.3976(3) 0.0337(11) Uani 1 1 d . . . . . C13 C 0.2153(4) 1.0713(5) 0.2398(4) 0.0447(14) Uani 1 1 d . . . . . H13A H 0.225846 1.047922 0.182708 0.067 Uiso 1 1 calc R U . . . H13B H 0.164870 1.119333 0.243521 0.067 Uiso 1 1 calc R U . . . H13C H 0.212629 0.989135 0.272710 0.067 Uiso 1 1 calc R U . . . C5 C 0.2866(3) 0.2576(5) 0.4954(3) 0.0358(12) Uani 1 1 d . . . . . H5 H 0.234683 0.223574 0.502497 0.043 Uiso 1 1 calc R U . . . C9 C 0.4005(4) -0.0391(5) 0.5626(3) 0.0411(15) Uani 1 1 d . . . . . H9A H 0.427950 -0.042962 0.509946 0.062 Uiso 1 1 calc R U . . . H9B H 0.379467 -0.128187 0.575990 0.062 Uiso 1 1 calc R U . . . H9C H 0.437512 -0.010757 0.605258 0.062 Uiso 1 1 calc R U . . . C11 C 0.3637(4) 0.8862(4) 0.1358(3) 0.0320(11) Uani 1 1 d . . . . . H11A H 0.377856 0.867027 0.078869 0.048 Uiso 1 1 calc R U . . . H11B H 0.306297 0.878843 0.142363 0.048 Uiso 1 1 calc R U . . . H11C H 0.389879 0.821494 0.171842 0.048 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 0.03519(15) 0.02349(9) 0.02849(9) 0.00528(6) -0.00060(7) -0.00170(7) P1 0.0317(9) 0.0190(5) 0.0263(5) 0.0010(4) 0.0003(4) -0.0003(4) O1 0.047(3) 0.0236(17) 0.049(2) 0.0122(14) 0.0048(17) -0.0008(14) C6 0.037(4) 0.0200(19) 0.029(2) 0.0032(15) 0.0020(18) -0.0008(17) C3 0.027(3) 0.024(2) 0.030(2) 0.0021(15) -0.0036(17) 0.0005(16) C10 0.041(4) 0.022(2) 0.026(2) -0.0027(15) 0.0036(18) -0.0004(16) C8 0.026(3) 0.022(2) 0.032(2) 0.0004(15) 0.0062(17) 0.0010(15) C2 0.037(4) 0.030(2) 0.034(2) -0.0002(18) 0.000(2) 0.0015(19) C12 0.036(4) 0.029(2) 0.048(3) -0.0058(19) -0.004(2) 0.0005(18) C7 0.039(4) 0.022(2) 0.033(2) -0.0005(16) -0.0023(19) 0.0065(17) C15 0.038(4) 0.025(2) 0.049(3) 0.004(2) -0.002(2) -0.0039(18) C14 0.027(4) 0.025(2) 0.037(2) -0.0023(17) -0.0067(18) -0.0023(16) C4 0.031(4) 0.030(2) 0.035(2) 0.0031(17) -0.0083(19) 0.0014(18) C1 0.036(4) 0.032(2) 0.033(2) 0.0062(17) -0.004(2) -0.0034(19) C13 0.027(5) 0.042(3) 0.065(4) -0.015(3) -0.002(3) 0.001(2) C5 0.037(4) 0.034(3) 0.037(2) 0.0024(18) 0.000(2) -0.004(2) C9 0.059(5) 0.020(2) 0.044(3) 0.0013(19) -0.001(2) 0.0024(19) C11 0.036(4) 0.026(2) 0.034(2) -0.0065(17) -0.0012(18) -0.0017(17) 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 171.84(15) . . ? C10 P1 Au1 109.24(15) . . ? C10 P1 C14 103.7(2) . . ? C12 P1 Au1 115.31(18) . . ? C12 P1 C10 104.6(2) . . ? C12 P1 C14 107.1(2) . . ? C14 P1 Au1 115.80(15) . . ? C6 O1 C9 115.5(4) . . ? O1 C6 C7 124.7(4) . . ? O1 C6 C5 115.0(5) . . ? C7 C6 C5 120.3(4) . . ? C8 C3 C2 120.1(5) . . ? C4 C3 C8 118.8(4) . . ? C4 C3 C2 121.1(4) . . ? P1 C10 H10A 108.8 . . ? P1 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C11 C10 P1 114.0(3) . . ? C11 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C3 C8 H8 120.0 . . ? C7 C8 C3 120.0(5) . . ? C7 C8 H8 120.0 . . ? C1 C2 C3 173.1(6) . . ? P1 C12 H12A 109.6 . . ? P1 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C13 C12 P1 110.4(4) . . ? C13 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C6 C7 C8 120.5(5) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? 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 112.7(4) . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C3 C4 H4 119.4 . . ? C5 C4 C3 121.1(5) . . ? C5 C4 H4 119.4 . . ? C2 C1 Au1 170.2(4) . . ? 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 119.3(5) . . ? 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 2.2671(11) . ? Au1 C1 1.995(5) . ? P1 C10 1.823(4) . ? P1 C12 1.803(6) . ? P1 C14 1.825(5) . ? O1 C6 1.368(5) . ? O1 C9 1.431(6) . ? C6 C7 1.371(7) . ? C6 C5 1.405(7) . ? C3 C8 1.409(7) . ? C3 C2 1.440(6) . ? C3 C4 1.391(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.513(6) . ? C8 H8 0.9300 . ? C8 C7 1.385(6) . ? C2 C1 1.198(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.508(8) . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 C14 1.509(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C4 H4 0.9300 . ? C4 C5 1.380(6) . ? 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 27.7(4) . . . . ? Au1 P1 C12 C13 -60.9(4) . . . . ? Au1 P1 C14 C15 -167.4(3) . . . . ? O1 C6 C7 C8 -176.4(4) . . . . ? O1 C6 C5 C4 176.8(4) . . . . ? C3 C8 C7 C6 0.6(6) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? C10 P1 C12 C13 59.1(4) . . . . ? C10 P1 C14 C15 73.0(4) . . . . ? C8 C3 C4 C5 1.5(7) . . . . ? C2 C3 C8 C7 176.1(4) . . . . ? C2 C3 C4 C5 -176.0(4) . . . . ? C12 P1 C10 C11 -96.3(4) . . . . ? C12 P1 C14 C15 -37.2(4) . . . . ? C7 C6 C5 C4 -0.1(7) . . . . ? C14 P1 C10 C11 151.7(4) . . . . ? C14 P1 C12 C13 168.6(4) . . . . ? C4 C3 C8 C7 -1.5(6) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C9 O1 C6 C7 -19.3(6) . . . . ? C9 O1 C6 C5 164.0(4) . . . . ?