#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:44:43 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297249 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573643.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_1573643 _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 _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 16.7395(3) _cell_length_b 9.79915(17) _cell_length_c 16.1723(3) _cell_measurement_temperature 293(2) _cell_volume 2652.79(8) _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)' _diffrn_ambient_environment 'Diamond Anvil Cell filled with Daphne-7575' _diffrn_ambient_pressure 2660000 _diffrn_ambient_temperature 293(2) _diffrn_crystal_treatment 'pressurized rapidly in Daphne-7575 as a hydrostatic medium' _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.717 _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_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.410 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_unetI/netI 0.0673 _diffrn_reflns_Laue_measured_fraction_full 0.955 _diffrn_reflns_Laue_measured_fraction_max 0.717 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 37626 _diffrn_reflns_point_group_measured_fraction_full 0.955 _diffrn_reflns_point_group_measured_fraction_max 0.717 _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; _diffrn_reflns_theta_full 14.241 _diffrn_reflns_theta_max 21.733 _diffrn_reflns_theta_min 1.567 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 2.724 _exptl_crystal_colour 'clear violet' _exptl_crystal_density_diffrn 2.235 _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 2.66 GPa and left to stabilize over ? hours.' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-pentane/dichloromethane' _refine_diff_density_max 1.620 _refine_diff_density_min -2.557 _refine_diff_density_rms 0.204 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 5873 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.255 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0509 _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^)+2.9019P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1082 _refine_ls_wR_factor_ref 0.1135 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5301 _reflns_number_total 5873 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b3.cif _cod_data_source_block p4m1_2p66GPa _cod_original_cell_volume 2652.79(9) _cod_database_code 1573643 _shelx_shelxl_version_number 2018/3 _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. ; _exptl_sortav_scale_factor_max 1.302 _exptl_sortav_scale_factor_min 0.805 _diffrn_reflns_number_extinctions 1689 _diffrn_reflns_number_rejects 52 _diffrn_reflns_rejects_percent 0.145 _diffrn_reflns_number_accepted 35885 _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 p4m1_2p66GPa in Pbca #61 p4m1_2p66GPa.res created by SHELXL-2018/3 at 20:41:11 on 15-May-2023 CELL 0.41 16.739531 9.799148 16.172261 90 90 90 ZERR 8 0.00031 0.000166 0.000334 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 2.901900 FVAR 1.10363 AU1 5 0.384118 0.874778 0.344216 11.00000 0.03401 0.02674 = 0.02911 0.00564 -0.00055 -0.00172 P1 4 0.376803 1.068262 0.267528 11.00000 0.03011 0.02222 = 0.02589 0.00165 0.00039 0.00009 O1 3 0.336101 0.058074 0.555261 11.00000 0.04482 0.02800 = 0.05191 0.01277 0.00277 -0.00258 C6 1 0.354114 0.180698 0.519373 11.00000 0.03596 0.02504 = 0.02844 0.00158 -0.00053 0.00016 C3 1 0.376238 0.438529 0.450365 11.00000 0.03681 0.02462 = 0.02898 0.00135 -0.00262 -0.00105 C10 1 0.390478 1.026510 0.158790 11.00000 0.03992 0.02587 = 0.02804 0.00112 0.00094 -0.00147 AFIX 23 H10A 2 0.360820 1.091892 0.125842 11.00000 -1.20000 H10B 2 0.446578 1.036901 0.145149 11.00000 -1.20000 AFIX 0 C8 1 0.441347 0.358470 0.474883 11.00000 0.03049 0.02851 = 0.03309 -0.00116 0.00171 -0.00065 AFIX 43 H8 2 0.492967 0.391688 0.468035 11.00000 -1.20000 AFIX 0 C2 1 0.387643 0.574616 0.419550 11.00000 0.02884 0.03214 = 0.03389 0.00298 -0.00134 0.00093 C12 1 0.281928 1.156730 0.271786 11.00000 0.03756 0.02859 = 0.04547 -0.00491 0.00114 0.00310 AFIX 23 H12A 2 0.270745 1.183236 0.328404 11.00000 -1.20000 H12B 2 0.284799 1.238996 0.238560 11.00000 -1.20000 AFIX 0 C7 1 0.429871 0.230279 0.509247 11.00000 0.03365 0.02614 = 0.03404 0.00075 -0.00174 0.00320 AFIX 43 H7 2 0.473598 0.178134 0.525374 11.00000 -1.20000 AFIX 0 C15 1 0.437494 1.331445 0.247497 11.00000 0.03581 0.02938 = 0.05982 0.00704 -0.00150 -0.00557 AFIX 137 H15A 2 0.421357 1.317569 0.191158 11.00000 -1.50000 H15B 2 0.485082 1.386076 0.248802 11.00000 -1.50000 H15C 2 0.395637 1.377360 0.277038 11.00000 -1.50000 AFIX 0 C14 1 0.453907 1.194733 0.287708 11.00000 0.03665 0.02835 = 0.03670 -0.00236 -0.00734 -0.00212 AFIX 23 H14A 2 0.458620 1.207634 0.346975 11.00000 -1.20000 H14B 2 0.504647 1.160218 0.267662 11.00000 -1.20000 AFIX 0 C4 1 0.299677 0.385937 0.460679 11.00000 0.03062 0.03196 = 0.03708 0.00615 -0.00699 0.00261 AFIX 43 H4 2 0.255787 0.437648 0.444512 11.00000 -1.20000 AFIX 0 C1 1 0.390970 0.691658 0.397145 11.00000 0.03175 0.03147 = 0.03467 0.00799 -0.00196 0.00130 C13 1 0.215335 1.066947 0.240167 11.00000 0.03451 0.04529 = 0.06131 -0.01403 0.00220 -0.00013 AFIX 137 H13A 2 0.224511 1.045924 0.182973 11.00000 -1.50000 H13B 2 0.165286 1.113878 0.245768 11.00000 -1.50000 H13C 2 0.213853 0.983932 0.271651 11.00000 -1.50000 AFIX 0 C5 1 0.287814 0.257933 0.494605 11.00000 0.02960 0.03462 = 0.03757 0.00374 -0.00040 -0.00630 AFIX 43 H5 2 0.236404 0.223493 0.500912 11.00000 -1.20000 AFIX 0 C9 1 0.400250 -0.036890 0.562345 11.00000 0.05805 0.02618 = 0.04817 0.00590 0.00090 0.00762 AFIX 137 H9A 2 0.424916 -0.049078 0.509267 11.00000 -1.50000 H9B 2 0.380030 -0.122850 0.581654 11.00000 -1.50000 H9C 2 0.439003 -0.002694 0.600886 11.00000 -1.50000 AFIX 0 C11 1 0.364208 0.883654 0.134421 11.00000 0.04089 0.03287 = 0.03170 -0.00277 0.00927 -0.00326 AFIX 137 H11A 2 0.375942 0.868577 0.077038 11.00000 -1.50000 H11B 2 0.307789 0.874301 0.143432 11.00000 -1.50000 H11C 2 0.392295 0.817819 0.167394 11.00000 -1.50000 AFIX 0 HKLF 4 REM p4m1_2p66GPa in Pbca #61 REM wR2 = 0.1135, GooF = S = 1.255, Restrained GooF = 1.255 for all data REM R1 = 0.0509 for 5301 Fo > 4sig(Fo) and 0.0606 for all 5873 data REM 167 parameters refined using 0 restraints END WGHT 0.0000 2.9019 REM Highest difference peak 1.620, deepest hole -2.557, 1-sigma level 0.204 Q1 1 0.3639 0.8285 0.2963 11.00000 0.05 1.62 Q2 1 0.3625 0.9199 0.2965 11.00000 0.05 1.59 ; _shelx_res_checksum 43098 _olex2_submission_special_instructions 'No special instructions were received' 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 0.38412(2) 0.87478(2) 0.34422(2) 0.02996(7) Uani 1 1 d . . . . . P1 P 0.37680(6) 1.06826(9) 0.26753(6) 0.02607(19) Uani 1 1 d . . . . . O1 O 0.3361(2) 0.0581(3) 0.5553(2) 0.0416(7) Uani 1 1 d . . . . . C6 C 0.3541(3) 0.1807(4) 0.5194(2) 0.0298(7) Uani 1 1 d . . . . . C3 C 0.3762(3) 0.4385(4) 0.4504(3) 0.0301(8) Uani 1 1 d . . . . . C10 C 0.3905(3) 1.0265(4) 0.1588(2) 0.0313(9) Uani 1 1 d . . . . . H10A H 0.360820 1.091892 0.125842 0.038 Uiso 1 1 calc R U . . . H10B H 0.446578 1.036901 0.145149 0.038 Uiso 1 1 calc R U . . . C8 C 0.4413(3) 0.3585(3) 0.4749(3) 0.0307(8) Uani 1 1 d . . . . . H8 H 0.492967 0.391688 0.468035 0.037 Uiso 1 1 calc R U . . . C2 C 0.3876(2) 0.5746(4) 0.4196(3) 0.0316(8) Uani 1 1 d . . . . . C12 C 0.2819(3) 1.1567(4) 0.2718(3) 0.0372(9) Uani 1 1 d . . . . . H12A H 0.270745 1.183236 0.328404 0.045 Uiso 1 1 calc R U . . . H12B H 0.284799 1.238996 0.238560 0.045 Uiso 1 1 calc R U . . . C7 C 0.4299(3) 0.2303(3) 0.5092(3) 0.0313(8) Uani 1 1 d . . . . . H7 H 0.473598 0.178134 0.525374 0.038 Uiso 1 1 calc R U . . . C15 C 0.4375(3) 1.3314(4) 0.2475(3) 0.0417(10) Uani 1 1 d . . . . . H15A H 0.421357 1.317569 0.191158 0.063 Uiso 1 1 calc R U . . . H15B H 0.485082 1.386076 0.248802 0.063 Uiso 1 1 calc R U . . . H15C H 0.395637 1.377360 0.277038 0.063 Uiso 1 1 calc R U . . . C14 C 0.4539(3) 1.1947(4) 0.2877(3) 0.0339(8) Uani 1 1 d . . . . . H14A H 0.458620 1.207634 0.346975 0.041 Uiso 1 1 calc R U . . . H14B H 0.504647 1.160218 0.267662 0.041 Uiso 1 1 calc R U . . . C4 C 0.2997(3) 0.3859(4) 0.4607(3) 0.0332(8) Uani 1 1 d . . . . . H4 H 0.255787 0.437648 0.444512 0.040 Uiso 1 1 calc R U . . . C1 C 0.3910(2) 0.6917(4) 0.3971(3) 0.0326(8) Uani 1 1 d . . . . . C13 C 0.2153(3) 1.0669(5) 0.2402(4) 0.0470(11) Uani 1 1 d . . . . . H13A H 0.224511 1.045924 0.182973 0.071 Uiso 1 1 calc R U . . . H13B H 0.165286 1.113878 0.245768 0.071 Uiso 1 1 calc R U . . . H13C H 0.213853 0.983932 0.271651 0.071 Uiso 1 1 calc R U . . . C5 C 0.2878(3) 0.2579(4) 0.4946(3) 0.0339(8) Uani 1 1 d . . . . . H5 H 0.236404 0.223493 0.500912 0.041 Uiso 1 1 calc R U . . . C9 C 0.4002(3) -0.0369(4) 0.5623(3) 0.0441(11) Uani 1 1 d . . . . . H9A H 0.424916 -0.049078 0.509267 0.066 Uiso 1 1 calc R U . . . H9B H 0.380030 -0.122850 0.581654 0.066 Uiso 1 1 calc R U . . . H9C H 0.439003 -0.002694 0.600886 0.066 Uiso 1 1 calc R U . . . C11 C 0.3642(3) 0.8837(4) 0.1344(3) 0.0352(9) Uani 1 1 d . . . . . H11A H 0.375942 0.868577 0.077038 0.053 Uiso 1 1 calc R U . . . H11B H 0.307789 0.874301 0.143432 0.053 Uiso 1 1 calc R U . . . H11C H 0.392295 0.817819 0.167394 0.053 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 0.03401(14) 0.02674(10) 0.02911(11) 0.00564(4) -0.00055(5) -0.00172(4) P1 0.0301(5) 0.0222(4) 0.0259(4) 0.0016(3) 0.0004(3) 0.0001(3) O1 0.045(2) 0.0280(13) 0.052(2) 0.0128(12) 0.0028(14) -0.0026(11) C6 0.036(2) 0.0250(15) 0.0284(18) 0.0016(12) -0.0005(14) 0.0002(12) C3 0.037(2) 0.0246(15) 0.0290(19) 0.0014(13) -0.0026(14) -0.0011(12) C10 0.040(3) 0.0259(18) 0.028(2) 0.0011(12) 0.0009(14) -0.0015(13) C8 0.030(2) 0.0285(15) 0.033(2) -0.0012(13) 0.0017(15) -0.0006(12) C2 0.029(2) 0.0321(18) 0.034(2) 0.0030(15) -0.0013(14) 0.0009(12) C12 0.038(2) 0.0286(16) 0.045(2) -0.0049(15) 0.0011(18) 0.0031(14) C7 0.034(2) 0.0261(15) 0.0340(19) 0.0007(13) -0.0017(15) 0.0032(12) C15 0.036(3) 0.0294(17) 0.060(3) 0.0070(18) -0.0015(19) -0.0056(15) C14 0.037(2) 0.0284(15) 0.037(2) -0.0024(14) -0.0073(16) -0.0021(13) C4 0.031(2) 0.0320(17) 0.037(2) 0.0061(14) -0.0070(16) 0.0026(12) C1 0.032(2) 0.0315(18) 0.035(2) 0.0080(15) -0.0020(15) 0.0013(13) C13 0.035(3) 0.045(2) 0.061(3) -0.014(2) 0.002(2) -0.0001(17) C5 0.030(2) 0.0346(17) 0.038(2) 0.0037(15) -0.0004(15) -0.0063(13) C9 0.058(3) 0.0262(18) 0.048(3) 0.0059(16) 0.001(2) 0.0076(16) C11 0.041(3) 0.0329(19) 0.032(2) -0.0028(15) 0.009(2) -0.0033(14) 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_ _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 172.32(14) . . ? C10 P1 Au1 109.48(14) . . ? C10 P1 C12 104.8(2) . . ? C10 P1 C14 103.7(2) . . ? C12 P1 Au1 115.25(15) . . ? C14 P1 Au1 115.66(14) . . ? C14 P1 C12 106.82(19) . . ? C6 O1 C9 116.2(4) . . ? O1 C6 C7 124.5(4) . . ? O1 C6 C5 114.9(4) . . ? C7 C6 C5 120.5(3) . . ? C8 C3 C2 121.0(4) . . ? C8 C3 C4 118.4(3) . . ? C4 C3 C2 120.5(4) . . ? P1 C10 H10A 108.5 . . ? P1 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C11 C10 P1 114.9(3) . . ? C11 C10 H10A 108.5 . . ? C11 C10 H10B 108.5 . . ? C3 C8 H8 119.6 . . ? C3 C8 C7 120.9(4) . . ? C7 C8 H8 119.6 . . ? C1 C2 C3 174.2(4) . . ? P1 C12 H12A 109.5 . . ? P1 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C13 C12 P1 110.8(3) . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C6 C7 C8 119.9(4) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? 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 108.9 . . ? P1 C14 H14B 108.9 . . ? C15 C14 P1 113.4(3) . . ? C15 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C3 C4 H4 119.5 . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C2 C1 Au1 170.1(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 120.4 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.4 . . ? 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 2.2689(9) . ? Au1 C1 1.991(4) . ? P1 C10 1.820(4) . ? P1 C12 1.811(4) . ? P1 C14 1.819(4) . ? O1 C6 1.368(5) . ? O1 C9 1.426(6) . ? C6 C7 1.368(6) . ? C6 C5 1.402(6) . ? C3 C8 1.400(6) . ? C3 C2 1.436(5) . ? C3 C4 1.391(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.519(6) . ? C8 H8 0.9300 . ? C8 C7 1.387(5) . ? C2 C1 1.204(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.509(6) . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 C14 1.514(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C4 H4 0.9300 . ? C4 C5 1.383(5) . ? 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 28.3(4) . . . . ? Au1 P1 C12 C13 -60.7(4) . . . . ? Au1 P1 C14 C15 -168.9(3) . . . . ? O1 C6 C7 C8 -177.5(4) . . . . ? O1 C6 C5 C4 177.4(4) . . . . ? C3 C8 C7 C6 0.1(6) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C10 P1 C12 C13 59.7(4) . . . . ? C10 P1 C14 C15 71.2(4) . . . . ? C8 C3 C4 C5 0.3(7) . . . . ? C2 C3 C8 C7 176.1(4) . . . . ? C2 C3 C4 C5 -176.4(4) . . . . ? C12 P1 C10 C11 -95.9(4) . . . . ? C12 P1 C14 C15 -39.2(4) . . . . ? C7 C6 C5 C4 -0.8(6) . . . . ? C14 P1 C10 C11 152.3(4) . . . . ? C14 P1 C12 C13 169.3(3) . . . . ? C4 C3 C8 C7 -0.5(6) . . . . ? C5 C6 C7 C8 0.6(6) . . . . ? C9 O1 C6 C7 -16.9(6) . . . . ? C9 O1 C6 C5 164.9(4) . . . . ?