#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:44:43 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297249 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573644.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_1573644 _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 2023-05-31 _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_temperature 293(2) _cell_volume 2591.80(14) _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 3300000 _diffrn_ambient_temperature 293(2) _diffrn_crystal_treatment 'pressurized rapidly in Daphne-7575 as a hydrostatic medium' _diffrn_measured_fraction_theta_full 0.930 _diffrn_measured_fraction_theta_max 0.675 _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 0.0540 _diffrn_reflns_av_unetI/netI 0.0577 _diffrn_reflns_Laue_measured_fraction_full 0.930 _diffrn_reflns_Laue_measured_fraction_max 0.675 _diffrn_reflns_limit_h_max 22 _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 -24 _diffrn_reflns_number 28104 _diffrn_reflns_point_group_measured_fraction_full 0.930 _diffrn_reflns_point_group_measured_fraction_max 0.675 _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 21.765 _diffrn_reflns_theta_min 1.579 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 2.788 _exptl_crystal_colour 'clear violet' _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' _refine_diff_density_max 3.071 _refine_diff_density_min -1.499 _refine_diff_density_rms 0.232 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 5415 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.191 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0406 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.3387P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.1039 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4553 _reflns_number_total 5415 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b3.cif _cod_data_source_block p5m1_3p30GPa _cod_original_cell_volume 2591.80(13) _cod_database_code 1573644 _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 1.932 _exptl_sortav_scale_factor_min 0.396 _diffrn_reflns_number_extinctions 1084 _diffrn_reflns_number_rejects 5 _diffrn_reflns_rejects_percent 0.019 _diffrn_reflns_number_accepted 27015 _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 p5m1_3p30GPa in Pbca #61 p5m1_3p30GPa.res created by SHELXL-2018/3 at 13:46:49 on 31-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 13 3 1 OMIT 11 2 1 OMIT 20 0 6 OMIT 14 2 2 REM REM REM WGHT 0.042500 0.338700 FVAR 0.97078 AU1 5 0.384328 0.878397 0.345130 11.00000 0.03000 0.02345 = 0.02770 0.00515 -0.00056 -0.00148 P1 4 0.377310 1.072859 0.267849 11.00000 0.02618 0.01953 = 0.02501 0.00135 0.00024 0.00015 O1 3 0.335981 0.056822 0.557143 11.00000 0.04061 0.02498 = 0.04859 0.01054 0.00148 -0.00352 C6 1 0.353253 0.179480 0.519884 11.00000 0.03130 0.02322 = 0.02516 0.00162 0.00116 -0.00176 C3 1 0.376324 0.438950 0.449900 11.00000 0.03131 0.02388 = 0.02468 0.00289 -0.00034 -0.00071 C10 1 0.390622 1.030018 0.158397 11.00000 0.03223 0.02631 = 0.02394 0.00050 0.00159 -0.00086 AFIX 23 H10A 2 0.360826 1.095686 0.124985 11.00000 -1.20000 H10B 2 0.447238 1.039538 0.144369 11.00000 -1.20000 AFIX 0 C8 1 0.442269 0.358152 0.474683 11.00000 0.02412 0.02555 = 0.02817 0.00032 0.00356 0.00050 AFIX 43 H8 2 0.494405 0.391343 0.467714 11.00000 -1.20000 AFIX 0 C2 1 0.387446 0.575287 0.419017 11.00000 0.02985 0.02871 = 0.02677 0.00204 -0.00063 0.00019 C12 1 0.281640 1.162565 0.272105 11.00000 0.02948 0.02812 = 0.04540 -0.00642 0.00104 0.00198 AFIX 23 H12A 2 0.270062 1.188683 0.329258 11.00000 -1.20000 H12B 2 0.284708 1.245486 0.238813 11.00000 -1.20000 AFIX 0 C7 1 0.430427 0.229393 0.509439 11.00000 0.02682 0.02566 = 0.03255 0.00131 0.00234 0.00212 AFIX 43 H7 2 0.474481 0.176769 0.525685 11.00000 -1.20000 AFIX 0 C15 1 0.437937 1.336646 0.248050 11.00000 0.03393 0.02589 = 0.04794 0.00598 -0.00151 -0.00413 AFIX 137 H15A 2 0.417117 1.322909 0.192794 11.00000 -1.50000 H15B 2 0.486383 1.390327 0.245208 11.00000 -1.50000 H15C 2 0.398581 1.383978 0.281215 11.00000 -1.50000 AFIX 0 C14 1 0.456446 1.198942 0.287392 11.00000 0.03123 0.02562 = 0.03323 -0.00172 -0.00477 -0.00170 AFIX 23 H14A 2 0.462841 1.210745 0.347117 11.00000 -1.20000 H14B 2 0.507040 1.164745 0.265281 11.00000 -1.20000 AFIX 0 C4 1 0.298857 0.385590 0.460889 11.00000 0.02681 0.02795 = 0.03642 0.00522 -0.00469 -0.00057 AFIX 43 H4 2 0.254457 0.437536 0.444847 11.00000 -1.20000 AFIX 0 C1 1 0.391244 0.693450 0.396859 11.00000 0.03286 0.02920 = 0.02874 0.00560 -0.00012 -0.00278 C13 1 0.215112 1.072313 0.239600 11.00000 0.02665 0.04136 = 0.06220 -0.01608 0.00031 -0.00132 AFIX 137 H13A 2 0.225993 1.048483 0.182588 11.00000 -1.50000 H13B 2 0.164738 1.120520 0.242824 11.00000 -1.50000 H13C 2 0.212152 0.990343 0.272644 11.00000 -1.50000 AFIX 0 C5 1 0.287022 0.257718 0.494978 11.00000 0.02524 0.02959 = 0.04023 0.00635 -0.00269 -0.00528 AFIX 43 H5 2 0.235054 0.223490 0.501413 11.00000 -1.20000 AFIX 0 C9 1 0.400064 -0.038630 0.562631 11.00000 0.05402 0.02341 = 0.04322 0.00054 0.00001 0.00529 AFIX 137 H9A 2 0.426313 -0.045819 0.509430 11.00000 -1.50000 H9B 2 0.379169 -0.126688 0.578471 11.00000 -1.50000 H9C 2 0.438173 -0.008123 0.603715 11.00000 -1.50000 AFIX 0 C11 1 0.363043 0.885044 0.134671 11.00000 0.04280 0.02753 = 0.03000 -0.00585 0.00199 -0.00216 AFIX 137 H11A 2 0.377729 0.866483 0.077848 11.00000 -1.50000 H11B 2 0.305578 0.878443 0.140609 11.00000 -1.50000 H11C 2 0.388558 0.819448 0.170702 11.00000 -1.50000 AFIX 0 HKLF 4 REM p5m1_3p30GPa in Pbca #61 REM wR2 = 0.1039, GooF = S = 1.191, Restrained GooF = 1.191 for all data REM R1 = 0.0406 for 4553 Fo > 4sig(Fo) and 0.0566 for all 5415 data REM 167 parameters refined using 0 restraints END WGHT 0.0425 0.3388 REM Highest difference peak 3.071, deepest hole -1.499, 1-sigma level 0.232 Q1 1 0.4108 0.8410 0.3443 11.00000 0.05 3.07 ; _shelx_res_checksum 65407 _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 0.38433(2) 0.87840(2) 0.34513(2) 0.02705(6) Uani 1 1 d . . . . . P1 P 0.37731(5) 1.07286(7) 0.26785(6) 0.02358(16) Uani 1 1 d . . . . . O1 O 0.33598(17) 0.0568(2) 0.5571(2) 0.0381(6) Uani 1 1 d . . . . . C6 C 0.3533(2) 0.1795(3) 0.5199(2) 0.0266(6) Uani 1 1 d . . . . . C3 C 0.37632(19) 0.4389(3) 0.4499(2) 0.0266(6) Uani 1 1 d . . . . . C10 C 0.3906(2) 1.0300(3) 0.1584(2) 0.0275(7) Uani 1 1 d . . . . . H10A H 0.360826 1.095686 0.124985 0.033 Uiso 1 1 calc R U . . . H10B H 0.447238 1.039538 0.144369 0.033 Uiso 1 1 calc R U . . . C8 C 0.44227(19) 0.3582(3) 0.4747(2) 0.0259(6) Uani 1 1 d . . . . . H8 H 0.494405 0.391343 0.467714 0.031 Uiso 1 1 calc R U . . . C2 C 0.38745(19) 0.5753(3) 0.4190(3) 0.0284(6) Uani 1 1 d . . . . . C12 C 0.2816(2) 1.1626(3) 0.2721(3) 0.0343(7) Uani 1 1 d . . . . . H12A H 0.270062 1.188683 0.329258 0.041 Uiso 1 1 calc R U . . . H12B H 0.284708 1.245486 0.238813 0.041 Uiso 1 1 calc R U . . . C7 C 0.4304(2) 0.2294(3) 0.5094(2) 0.0283(6) Uani 1 1 d . . . . . H7 H 0.474481 0.176769 0.525685 0.034 Uiso 1 1 calc R U . . . C15 C 0.4379(2) 1.3366(3) 0.2481(3) 0.0359(8) Uani 1 1 d . . . . . H15A H 0.417117 1.322909 0.192794 0.054 Uiso 1 1 calc R U . . . H15B H 0.486383 1.390327 0.245208 0.054 Uiso 1 1 calc R U . . . H15C H 0.398581 1.383978 0.281215 0.054 Uiso 1 1 calc R U . . . C14 C 0.4564(2) 1.1989(3) 0.2874(2) 0.0300(6) Uani 1 1 d . . . . . H14A H 0.462841 1.210745 0.347117 0.036 Uiso 1 1 calc R U . . . H14B H 0.507040 1.164745 0.265281 0.036 Uiso 1 1 calc R U . . . C4 C 0.2989(2) 0.3856(3) 0.4609(3) 0.0304(7) Uani 1 1 d . . . . . H4 H 0.254457 0.437536 0.444847 0.036 Uiso 1 1 calc R U . . . C1 C 0.39124(19) 0.6934(3) 0.3969(3) 0.0303(7) Uani 1 1 d . . . . . C13 C 0.2151(2) 1.0723(4) 0.2396(3) 0.0434(10) Uani 1 1 d . . . . . H13A H 0.225993 1.048483 0.182588 0.065 Uiso 1 1 calc R U . . . H13B H 0.164738 1.120520 0.242824 0.065 Uiso 1 1 calc R U . . . H13C H 0.212152 0.990343 0.272644 0.065 Uiso 1 1 calc R U . . . C5 C 0.2870(2) 0.2577(3) 0.4950(3) 0.0317(7) Uani 1 1 d . . . . . H5 H 0.235054 0.223490 0.501413 0.038 Uiso 1 1 calc R U . . . C9 C 0.4001(3) -0.0386(3) 0.5626(3) 0.0402(9) Uani 1 1 d . . . . . H9A H 0.426313 -0.045819 0.509430 0.060 Uiso 1 1 calc R U . . . H9B H 0.379169 -0.126688 0.578471 0.060 Uiso 1 1 calc R U . . . H9C H 0.438173 -0.008123 0.603715 0.060 Uiso 1 1 calc R U . . . C11 C 0.3630(3) 0.8850(3) 0.1347(3) 0.0334(7) Uani 1 1 d . . . . . H11A H 0.377729 0.866483 0.077848 0.050 Uiso 1 1 calc R U . . . H11B H 0.305578 0.878443 0.140609 0.050 Uiso 1 1 calc R U . . . H11C H 0.388558 0.819448 0.170702 0.050 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 0.03000(10) 0.02345(8) 0.02770(11) 0.00515(3) -0.00056(4) -0.00148(3) P1 0.0262(4) 0.0195(3) 0.0250(5) 0.0013(2) 0.0002(3) 0.0001(2) O1 0.0406(15) 0.0250(9) 0.049(2) 0.0105(10) 0.0015(11) -0.0035(8) C6 0.0313(15) 0.0232(11) 0.0252(18) 0.0016(10) 0.0012(11) -0.0018(9) C3 0.0313(16) 0.0239(11) 0.0247(19) 0.0029(10) -0.0003(10) -0.0007(8) C10 0.0322(17) 0.0263(13) 0.024(2) 0.0005(10) 0.0016(10) -0.0009(9) C8 0.0241(14) 0.0256(10) 0.0282(19) 0.0003(10) 0.0036(10) 0.0005(8) C2 0.0299(16) 0.0287(14) 0.027(2) 0.0020(12) -0.0006(10) 0.0002(9) C12 0.0295(16) 0.0281(11) 0.045(2) -0.0064(13) 0.0010(13) 0.0020(10) C7 0.0268(15) 0.0257(11) 0.033(2) 0.0013(11) 0.0023(11) 0.0021(9) C15 0.0339(19) 0.0259(11) 0.048(3) 0.0060(13) -0.0015(13) -0.0041(10) C14 0.0312(15) 0.0256(11) 0.033(2) -0.0017(11) -0.0048(12) -0.0017(9) C4 0.0268(17) 0.0279(12) 0.036(2) 0.0052(11) -0.0047(12) -0.0006(8) C1 0.0329(16) 0.0292(13) 0.029(2) 0.0056(12) -0.0001(12) -0.0028(9) C13 0.0267(18) 0.0414(15) 0.062(3) -0.0161(17) 0.0003(15) -0.0013(12) C5 0.0252(15) 0.0296(11) 0.040(2) 0.0063(12) -0.0027(12) -0.0053(9) C9 0.054(2) 0.0234(13) 0.043(3) 0.0005(13) 0.0000(16) 0.0053(12) C11 0.043(2) 0.0275(14) 0.030(2) -0.0058(11) 0.0020(16) -0.0022(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_ _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 171.54(12) . . ? C10 P1 Au1 109.21(11) . . ? C10 P1 C14 103.48(17) . . ? C12 P1 Au1 115.32(13) . . ? C12 P1 C10 104.69(18) . . ? C12 P1 C14 107.34(14) . . ? C14 P1 Au1 115.62(12) . . ? C6 O1 C9 116.4(3) . . ? O1 C6 C7 123.8(3) . . ? O1 C6 C5 116.0(3) . . ? C7 C6 C5 120.2(3) . . ? C8 C3 C2 121.2(3) . . ? C4 C3 C8 118.1(3) . . ? C4 C3 C2 120.5(3) . . ? P1 C10 H10A 108.6 . . ? P1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C11 C10 P1 114.5(3) . . ? C11 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C3 C8 H8 119.6 . . ? C7 C8 C3 120.7(3) . . ? C7 C8 H8 119.6 . . ? C1 C2 C3 174.5(4) . . ? P1 C12 H12A 109.6 . . ? P1 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C13 C12 P1 110.3(2) . . ? C13 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? 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 112.3(2) . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C3 C4 H4 119.4 . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4 119.4 . . ? C2 C1 Au1 170.2(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 120.1 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? 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 2.2677(8) . ? Au1 C1 1.988(3) . ? P1 C10 1.817(4) . ? P1 C12 1.813(3) . ? P1 C14 1.825(3) . ? O1 C6 1.367(4) . ? O1 C9 1.415(5) . ? C6 C7 1.380(4) . ? C6 C5 1.396(5) . ? C3 C8 1.405(4) . ? C3 C2 1.430(4) . ? C3 C4 1.397(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.533(5) . ? C8 H8 0.9300 . ? C8 C7 1.387(4) . ? C2 C1 1.207(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.504(5) . ? C7 H7 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15 C14 1.515(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C4 H4 0.9300 . ? C4 C5 1.375(4) . ? 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(3) . . . . ? Au1 P1 C12 C13 -61.0(4) . . . . ? Au1 P1 C14 C15 -167.6(2) . . . . ? O1 C6 C7 C8 -176.8(4) . . . . ? O1 C6 C5 C4 176.7(4) . . . . ? C3 C8 C7 C6 0.1(5) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C10 P1 C12 C13 59.0(4) . . . . ? C10 P1 C14 C15 73.1(3) . . . . ? C8 C3 C4 C5 0.0(6) . . . . ? C2 C3 C8 C7 175.9(4) . . . . ? C2 C3 C4 C5 -176.2(4) . . . . ? C12 P1 C10 C11 -95.7(3) . . . . ? C12 P1 C14 C15 -37.3(3) . . . . ? C7 C6 C5 C4 -0.8(5) . . . . ? C14 P1 C10 C11 152.0(3) . . . . ? C14 P1 C12 C13 168.5(3) . . . . ? C4 C3 C8 C7 -0.3(5) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? C9 O1 C6 C7 -18.8(5) . . . . ? C9 O1 C6 C5 163.8(4) . . . . ?