#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:45:50 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573657.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_1573657 _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 dual _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 16.527(3) _cell_length_b 11.2886(14) _cell_length_c 17.901(13) _cell_measurement_reflns_used 1039 _cell_measurement_temperature 295.1(4) _cell_measurement_theta_max 22.9480 _cell_measurement_theta_min 1.9440 _cell_volume 3340(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 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment 'Diamond Anvil Cell filled with silicone oil' _diffrn_ambient_pressure 160000 _diffrn_ambient_temperature 295.1(4) _diffrn_crystal_treatment 'pressurized rapidly in silicone oil as a hydrostatic medium' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0128 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.484 _diffrn_measured_fraction_theta_max 0.468 _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 -4.00 21.00 1.00 80.00 -- 22.04 53.00 -17.00 25 2 \w 1.00 26.00 1.00 80.00 -- -22.19 -39.00-167.00 25 3 \w -45.00 4.00 1.00 80.00 -- -22.19 67.00 -23.00 49 4 \w -34.00 12.00 1.00 80.00 -- -22.19 19.00-180.00 46 5 \w -1.00 43.00 1.00 80.00 -- -22.19 -26.00 8.00 44 6 \w -19.00 15.00 1.00 80.00 -- -22.19 26.00 -8.00 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, Eos' _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 -0.0040619000 _diffrn_orient_matrix_UB_12 0.0038847000 _diffrn_orient_matrix_UB_13 0.0308869000 _diffrn_orient_matrix_UB_21 -0.0267055000 _diffrn_orient_matrix_UB_22 0.0296468000 _diffrn_orient_matrix_UB_23 -0.0045164000 _diffrn_orient_matrix_UB_31 -0.0204574000 _diffrn_orient_matrix_UB_32 -0.0395192000 _diffrn_orient_matrix_UB_33 -0.0002217000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ag K\a' _diffrn_radiation_wavelength 0.56087 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_unetI/netI 0.0811 _diffrn_reflns_Laue_measured_fraction_full 0.484 _diffrn_reflns_Laue_measured_fraction_max 0.468 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7576 _diffrn_reflns_point_group_measured_fraction_full 0.484 _diffrn_reflns_point_group_measured_fraction_max 0.468 _diffrn_reflns_theta_full 19.665 _diffrn_reflns_theta_max 20.518 _diffrn_reflns_theta_min 1.944 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Ag) X-ray Source' _exptl_absorpt_coefficient_mu 4.808 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84228 _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 orange _exptl_crystal_density_diffrn 1.775 _exptl_crystal_description needle _exptl_crystal_F_000 1712 _exptl_crystal_preparation 'Mounted in a Diamond-Anvil Cell using silicone oil as pressure medium.,Luminescent' _exptl_crystal_pressure_history 'Pressurized to 0.16 GPa and left to stabilize over ? hours.' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-pentane/dichloromethane' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.424 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 1596 _refine_ls_number_restraints 252 _refine_ls_restrained_S_all 0.892 _refine_ls_R_factor_all 0.1751 _refine_ls_R_factor_gt 0.0440 _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^)+(0.0277P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1075 _reflns_Friedel_coverage 0.000 _reflns_number_gt 531 _reflns_number_total 1596 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b2.cif _cod_data_source_block appr4_0p16GPa _cod_original_cell_volume 3340(2) _cod_database_code 1573657 _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, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints C9A \\sim C9 \\sim O1A \\sim O1 \\sim C6A \\sim C6 \\sim C5A \\sim C5 \\sim C4A \\sim C4 \\sim C3A \\sim C3 \\sim C8A \\sim C8 \\sim C7A \\sim C7: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C11 \\sim C10 \\sim P1 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C15A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A 3. Others Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C9A)= Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(O1A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)= Sof(H8A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=1-FVAR(1) Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)= Sof(H5)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(O1)=Sof(H14A)=Sof(H14B)= Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C10(H10A,H10B), C14(H14A,H14B), C14(H14C,H14D) 4.b Me refined with riding coordinates: C11(H11A,H11B,H11C), C9A(H9AA,H9AB,H9AC) 4.c Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C4(H4), C5(H5), C7A(H7A), C8A(H8A), C4A(H4A), C5A(H5A) 4.d Fitted hexagon refined as free rotating group: C6(C7,C8,C3,C4,C5), C6A(C7A,C8A,C3A,C4A,C5A) 4.e Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F) ; _shelx_res_file ; TITL appr4_0p16GPa_a.res in Pbca appr4_0p16GPa.res created by SHELXL-2018/3 at 17:18:30 on 15-May-2023 REM Old TITL appr4_0p16GPa_b.res in Pbca REM SHELXT solution in Pbca: R1 0.223, Rweak 0.036, Alpha 0.052 REM 0.349 for 154 systematic absences, Orientation as input REM Formula found by SHELXT: C15 O P Au CELL 0.56087 16.5272 11.2886 17.9007 90 90 90 ZERR 8 0.0025 0.0014 0.0128 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O P Au DISP Au -0.657 6.026 19723.5 DISP C 0.0013 0.0009 7.4 DISP H 0 0 0.7 DISP O 0.0058 0.0036 18.2 DISP P 0.0671 0.0586 203.6 UNIT 120 176 8 8 8 SIMU 0.04 0.08 1.7 C9A C9 O1A O1 C6A C6 C5A C5 C4A C4 C3A C3 C8A C8 C7A C7 SIMU C11 C10 P1 C12 C13 C14 C15 C15A L.S. 10 PLAN 8 TEMP 22 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta SHEL 100 0.8 REM REM REM WGHT 0.027700 FVAR 0.13725 0.58117 AU1 5 0.388030 0.748670 0.326273 11.00000 0.11485 0.09747 = 0.11525 0.01042 0.01595 -0.00150 P1 4 0.400755 0.920948 0.259802 11.00000 0.14892 0.09837 = 0.19909 0.01988 0.03312 -0.00334 PART 1 AFIX 66 C6 1 0.383491 0.157502 0.497106 21.00000 0.15600 0.10360 = 0.08521 0.02074 0.00183 -0.03597 C7 1 0.443859 0.236318 0.518382 21.00000 0.12988 0.11393 = 0.08473 0.00788 -0.00611 -0.02034 AFIX 43 H7 2 0.484808 0.211676 0.550449 21.00000 -1.20000 AFIX 65 C8 1 0.443024 0.351964 0.491730 21.00000 0.12736 0.10562 = 0.08057 0.01003 0.00488 -0.03030 AFIX 43 H8 2 0.483414 0.404696 0.505966 21.00000 -1.20000 AFIX 65 C3 1 0.381821 0.388795 0.443803 21.00000 0.11123 0.09527 = 0.07441 0.01044 0.00713 -0.02364 C4 1 0.321452 0.309980 0.422526 21.00000 0.10539 0.09266 = 0.07556 0.01503 -0.00642 -0.03138 AFIX 43 H4 2 0.280504 0.334624 0.390460 21.00000 -1.20000 AFIX 65 C5 1 0.322286 0.194334 0.449177 21.00000 0.12527 0.11336 = 0.07890 0.00191 -0.00999 -0.04680 AFIX 43 H5 2 0.281896 0.141601 0.434942 21.00000 -1.20000 AFIX 0 C9 1 0.344765 -0.038783 0.507608 21.00000 0.19520 0.13465 = 0.12001 0.03241 0.02919 -0.06164 AFIX 137 H9A 2 0.313026 -0.009369 0.466702 21.00000 -1.50000 H9B 2 0.309523 -0.063516 0.547282 21.00000 -1.50000 H9C 2 0.376544 -0.104979 0.491096 21.00000 -1.50000 AFIX 0 PART 0 C1 1 0.380202 0.599719 0.379058 11.00000 0.12951 0.10113 = 0.06989 -0.06619 0.02161 -0.02727 C2 1 0.375953 0.501759 0.410986 11.00000 0.10914 0.09934 = 0.13496 -0.03910 0.02253 -0.00271 PART 1 O1 3 0.394428 0.047995 0.532637 21.00000 0.20154 0.12012 = 0.10233 0.04261 -0.00804 -0.05680 PART 0 C13 1 0.321950 1.134279 0.228033 11.00000 0.33485 0.16633 = 0.22527 0.01188 0.06665 0.07597 AFIX 137 H13A 2 0.304364 1.130443 0.176978 11.00000 -1.50000 H13B 2 0.377985 1.156524 0.229693 11.00000 -1.50000 H13C 2 0.290269 1.192020 0.254388 11.00000 -1.50000 AFIX 0 C12 1 0.311104 1.012231 0.264959 11.00000 0.19242 0.13242 = 0.23444 0.05711 0.05410 0.05998 AFIX 23 H12A 2 0.266707 0.971136 0.240783 11.00000 -1.20000 H12B 2 0.296686 1.023418 0.317010 11.00000 -1.20000 AFIX 0 C10 1 0.428505 0.899349 0.164812 11.00000 0.22030 0.18100 = 0.20238 0.06271 0.06150 -0.01563 AFIX 23 H10A 2 0.440832 0.975011 0.141788 11.00000 -1.20000 H10B 2 0.476371 0.849831 0.161958 11.00000 -1.20000 AFIX 0 C11 1 0.356537 0.838375 0.122412 11.00000 0.38341 0.17745 = 0.19266 0.08447 -0.03238 -0.06744 AFIX 33 H11A 2 0.371176 0.826478 0.071060 11.00000 -1.50000 H11B 2 0.344930 0.763276 0.145180 11.00000 -1.50000 H11C 2 0.309496 0.888085 0.125070 11.00000 -1.50000 AFIX 0 C14 1 0.490028 1.008704 0.291286 11.00000 0.17266 0.16717 = 0.23043 0.02150 0.04033 -0.04868 PART 1 AFIX 23 H14A 2 0.494196 1.080150 0.261428 21.00000 -1.20000 H14B 2 0.482520 1.032045 0.342974 21.00000 -1.20000 AFIX 23 PART 2 H14C 2 0.538733 0.961557 0.285787 -21.00000 -1.20000 H14D 2 0.495565 1.078702 0.260275 -21.00000 -1.20000 AFIX 0 PART 1 C15 1 0.568029 0.937620 0.284130 21.00000 0.11404 0.24972 = 0.24141 0.00680 0.08782 -0.05635 AFIX 137 H15A 2 0.555270 0.856705 0.272572 21.00000 -1.50000 H15B 2 0.597292 0.940901 0.330409 21.00000 -1.50000 H15C 2 0.600662 0.970474 0.244899 21.00000 -1.50000 AFIX 0 PART 2 C15A 1 0.479672 1.047981 0.377948 -21.00000 0.25171 0.23380 = 0.25409 -0.01073 0.04367 -0.04021 AFIX 137 H15D 2 0.423363 1.046948 0.391094 -21.00000 -1.50000 H15E 2 0.500809 1.126476 0.384650 -21.00000 -1.50000 H15F 2 0.508717 0.993759 0.409376 -21.00000 -1.50000 AFIX 0 C9A 1 0.293264 -0.022486 0.536685 -21.00000 0.19475 0.17917 = 0.11278 0.09103 0.01286 -0.09495 AFIX 33 H9AA 2 0.293545 -0.091912 0.567656 -21.00000 -1.50000 H9AB 2 0.238819 0.006016 0.531562 -21.00000 -1.50000 H9AC 2 0.314531 -0.041856 0.488298 -21.00000 -1.50000 AFIX 0 O1A 3 0.345931 0.074048 0.572773 -21.00000 0.15020 0.13130 = 0.09913 0.04669 0.00894 -0.06689 AFIX 66 C6A 1 0.354134 0.173668 0.541174 -21.00000 0.15079 0.11838 = 0.08984 0.02653 0.00289 -0.04083 C7A 1 0.413238 0.257458 0.557290 -21.00000 0.13615 0.10895 = 0.08406 0.01641 -0.00546 -0.03091 AFIX 43 H7A 2 0.448898 0.245011 0.596706 -21.00000 -1.20000 AFIX 65 C8A 1 0.419045 0.359851 0.514496 -21.00000 0.12735 0.09560 = 0.08032 0.00126 0.00305 -0.02660 AFIX 43 H8A 2 0.458590 0.415912 0.525279 -21.00000 -1.20000 AFIX 65 C3A 1 0.365748 0.378454 0.455584 -21.00000 0.10853 0.09803 = 0.07654 0.00123 0.00292 -0.02212 C4A 1 0.306644 0.294665 0.439467 -21.00000 0.11104 0.10117 = 0.07390 0.00284 -0.00037 -0.02229 AFIX 43 H4A 2 0.270984 0.307113 0.400052 -21.00000 -1.20000 AFIX 65 C5A 1 0.300836 0.192272 0.482261 -21.00000 0.14414 0.11320 = 0.08111 0.01341 -0.01160 -0.03258 AFIX 43 H5A 2 0.261291 0.136211 0.471478 -21.00000 -1.20000 AFIX 0 HKLF 4 REM appr4_0p16GPa_a.res in Pbca REM wR2 = 0.1075, GooF = S = 0.954, Restrained GooF = 0.892 for all data REM R1 = 0.0440 for 531 Fo > 4sig(Fo) and 0.1751 for all 1596 data REM 225 parameters refined using 252 restraints END WGHT 0.0277 0.0000 REM Highest difference peak 0.424, deepest hole -0.303, 1-sigma level 0.061 Q1 1 0.3291 0.7523 0.1742 11.00000 0.05 0.42 Q2 1 0.3295 0.7015 0.3218 11.00000 0.05 0.38 Q3 1 0.3563 0.7201 0.2430 11.00000 0.05 0.37 Q4 1 0.3332 0.8025 0.3182 11.00000 0.05 0.36 Q5 1 0.3551 0.7517 0.4053 11.00000 0.05 0.35 Q6 1 0.4055 0.7635 0.3270 11.00000 0.05 0.26 Q7 1 0.3818 0.7516 0.0250 11.00000 0.05 0.21 Q8 1 0.4206 0.7517 0.2899 11.00000 0.05 0.19 ; _shelx_res_checksum 9065 _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 1.130 _oxdiff_exptl_absorpt_empirical_full_min 0.884 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 0.38803(4) 0.74867(6) 0.32627(7) 0.1092(8) Uani 1 1 d . . . . . P1 P 0.4008(4) 0.9209(5) 0.2598(9) 0.149(7) Uani 1 1 d . U . . . C6 C 0.383(3) 0.158(3) 0.497(4) 0.115(15) Uani 0.58(3) 1 d G U P A 1 C7 C 0.444(2) 0.236(3) 0.518(4) 0.110(15) Uani 0.58(3) 1 d G U P A 1 H7 H 0.484808 0.211676 0.550449 0.131 Uiso 0.58(3) 1 calc R U P A 1 C8 C 0.443(3) 0.352(3) 0.492(4) 0.105(15) Uani 0.58(3) 1 d G U P A 1 H8 H 0.483414 0.404696 0.505966 0.125 Uiso 0.58(3) 1 calc R U P A 1 C3 C 0.382(3) 0.389(4) 0.444(5) 0.094(15) Uani 0.58(3) 1 d G U P A 1 C4 C 0.321(3) 0.310(4) 0.423(4) 0.091(16) Uani 0.58(3) 1 d G U P A 1 H4 H 0.280504 0.334624 0.390460 0.109 Uiso 0.58(3) 1 calc R U P A 1 C5 C 0.322(3) 0.194(4) 0.449(4) 0.106(17) Uani 0.58(3) 1 d G U P A 1 H5 H 0.281896 0.141601 0.434942 0.127 Uiso 0.58(3) 1 calc R U P A 1 C9 C 0.345(3) -0.039(5) 0.508(5) 0.15(3) Uani 0.58(3) 1 d . U P A 1 H9A H 0.313026 -0.009369 0.466702 0.225 Uiso 0.58(3) 1 calc R U P A 1 H9B H 0.309523 -0.063516 0.547282 0.225 Uiso 0.58(3) 1 calc R U P A 1 H9C H 0.376544 -0.104979 0.491096 0.225 Uiso 0.58(3) 1 calc R U P A 1 C1 C 0.3802(10) 0.5997(15) 0.3791(19) 0.100(18) Uani 1 1 d . . . . . C2 C 0.3760(10) 0.5018(18) 0.4110(18) 0.11(2) Uani 1 1 d . . . . . O1 O 0.394(2) 0.048(3) 0.533(3) 0.141(16) Uani 0.58(3) 1 d . U P A 1 C13 C 0.3220(16) 1.1343(18) 0.228(3) 0.24(2) Uani 1 1 d . U . . . H13A H 0.304364 1.130443 0.176978 0.363 Uiso 1 1 calc R U . . . H13B H 0.377985 1.156524 0.229693 0.363 Uiso 1 1 calc R U . . . H13C H 0.290269 1.192020 0.254388 0.363 Uiso 1 1 calc R U . . . C12 C 0.3111(11) 1.0122(16) 0.265(2) 0.186(13) Uani 1 1 d . U . . . H12A H 0.266707 0.971136 0.240783 0.224 Uiso 1 1 calc R U . . . H12B H 0.296686 1.023418 0.317010 0.224 Uiso 1 1 calc R U . . . C10 C 0.4285(19) 0.899(2) 0.165(3) 0.201(16) Uani 1 1 d . U . . . H10A H 0.440832 0.975011 0.141788 0.241 Uiso 1 1 calc R U . . . H10B H 0.476371 0.849831 0.161958 0.241 Uiso 1 1 calc R U . . . C11 C 0.3565(19) 0.838(2) 0.122(3) 0.25(3) Uani 1 1 d . U . . . H11A H 0.371176 0.826478 0.071060 0.377 Uiso 1 1 calc R U . . . H11B H 0.344930 0.763276 0.145180 0.377 Uiso 1 1 calc R U . . . H11C H 0.309496 0.888085 0.125070 0.377 Uiso 1 1 calc R U . . . C14 C 0.4900(18) 1.009(2) 0.291(3) 0.190(15) Uani 1 1 d . U . . . H14A H 0.494196 1.080150 0.261428 0.228 Uiso 0.58(3) 1 calc R U P A 1 H14B H 0.482520 1.032045 0.342974 0.228 Uiso 0.58(3) 1 calc R U P A 1 H14C H 0.538733 0.961557 0.285787 0.228 Uiso 0.42(3) 1 calc R U P A 2 H14D H 0.495565 1.078702 0.260275 0.228 Uiso 0.42(3) 1 calc R U P A 2 C15 C 0.568(2) 0.938(4) 0.284(5) 0.20(3) Uani 0.58(3) 1 d . U P A 1 H15A H 0.555270 0.856705 0.272572 0.303 Uiso 0.58(3) 1 calc R U P A 1 H15B H 0.597292 0.940901 0.330409 0.303 Uiso 0.58(3) 1 calc R U P A 1 H15C H 0.600662 0.970474 0.244899 0.303 Uiso 0.58(3) 1 calc R U P A 1 C15A C 0.480(5) 1.048(7) 0.378(8) 0.25(4) Uani 0.42(3) 1 d . U P A 2 H15D H 0.423363 1.046948 0.391094 0.370 Uiso 0.42(3) 1 calc R U P A 2 H15E H 0.500809 1.126476 0.384650 0.370 Uiso 0.42(3) 1 calc R U P A 2 H15F H 0.508717 0.993759 0.409376 0.370 Uiso 0.42(3) 1 calc R U P A 2 C9A C 0.293(4) -0.022(7) 0.537(7) 0.16(3) Uani 0.42(3) 1 d . U P A 2 H9AA H 0.293545 -0.091912 0.567656 0.243 Uiso 0.42(3) 1 calc R U P A 2 H9AB H 0.238819 0.006016 0.531562 0.243 Uiso 0.42(3) 1 calc R U P A 2 H9AC H 0.314531 -0.041856 0.488298 0.243 Uiso 0.42(3) 1 calc R U P A 2 O1A O 0.346(3) 0.074(4) 0.573(5) 0.127(17) Uani 0.42(3) 1 d . U P A 2 C6A C 0.354(3) 0.174(4) 0.541(5) 0.120(16) Uani 0.42(3) 1 d G U P A 2 C7A C 0.413(3) 0.257(5) 0.557(6) 0.110(16) Uani 0.42(3) 1 d G U P A 2 H7A H 0.448898 0.245011 0.596706 0.132 Uiso 0.42(3) 1 calc R U P A 2 C8A C 0.419(4) 0.360(5) 0.514(6) 0.101(16) Uani 0.42(3) 1 d G U P A 2 H8A H 0.458590 0.415912 0.525279 0.121 Uiso 0.42(3) 1 calc R U P A 2 C3A C 0.366(5) 0.378(6) 0.456(6) 0.094(16) Uani 0.42(3) 1 d G U P A 2 C4A C 0.307(5) 0.295(7) 0.439(6) 0.095(17) Uani 0.42(3) 1 d G U P A 2 H4A H 0.270984 0.307113 0.400052 0.114 Uiso 0.42(3) 1 calc R U P A 2 C5A C 0.301(4) 0.192(5) 0.482(6) 0.113(17) Uani 0.42(3) 1 d G U P A 2 H5A H 0.261291 0.136211 0.471478 0.135 Uiso 0.42(3) 1 calc R U P A 2 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 0.1148(6) 0.0975(6) 0.115(3) 0.0104(8) 0.0159(5) -0.0015(5) P1 0.149(5) 0.098(4) 0.20(3) 0.020(6) 0.033(7) -0.003(4) C6 0.16(2) 0.104(16) 0.09(5) 0.02(2) 0.00(2) -0.036(17) C7 0.13(2) 0.114(17) 0.08(5) 0.01(2) -0.01(2) -0.020(18) C8 0.13(3) 0.106(15) 0.08(5) 0.010(18) 0.00(2) -0.030(17) C3 0.11(2) 0.095(16) 0.07(5) 0.010(18) 0.01(2) -0.024(15) C4 0.11(2) 0.093(17) 0.08(5) 0.02(2) -0.01(2) -0.031(17) C5 0.13(2) 0.113(16) 0.08(5) 0.00(2) -0.01(2) -0.047(18) C9 0.20(5) 0.13(3) 0.12(8) 0.03(3) 0.03(5) -0.06(3) C1 0.130(16) 0.101(15) 0.07(7) -0.066(17) 0.022(16) -0.027(12) C2 0.109(16) 0.099(14) 0.13(7) -0.039(17) 0.023(15) -0.003(12) O1 0.20(3) 0.120(17) 0.10(5) 0.04(2) -0.01(2) -0.057(18) C13 0.33(3) 0.17(2) 0.23(8) 0.01(3) 0.07(3) 0.08(2) C12 0.192(17) 0.132(15) 0.23(4) 0.06(2) 0.05(2) 0.060(14) C10 0.22(2) 0.18(2) 0.20(5) 0.06(3) 0.06(3) -0.016(17) C11 0.38(4) 0.18(2) 0.19(8) 0.08(3) -0.03(4) -0.07(2) C14 0.17(2) 0.17(2) 0.23(5) 0.02(3) 0.04(3) -0.049(16) C15 0.11(3) 0.25(4) 0.24(9) 0.01(4) 0.09(4) -0.06(3) C15A 0.25(6) 0.23(6) 0.25(10) -0.01(7) 0.04(8) -0.04(5) C9A 0.19(6) 0.18(4) 0.11(8) 0.09(4) 0.01(5) -0.09(5) O1A 0.15(3) 0.13(2) 0.10(5) 0.05(3) 0.01(3) -0.07(2) C6A 0.15(3) 0.118(18) 0.09(5) 0.03(2) 0.00(2) -0.041(19) C7A 0.14(3) 0.109(19) 0.08(5) 0.02(2) -0.01(2) -0.03(2) C8A 0.13(3) 0.096(17) 0.08(5) 0.00(2) 0.00(2) -0.027(18) C3A 0.11(3) 0.098(18) 0.08(5) 0.00(2) 0.00(2) -0.022(18) C4A 0.11(3) 0.101(19) 0.07(5) 0.00(2) 0.00(2) -0.022(19) C5A 0.14(3) 0.113(19) 0.08(5) 0.01(2) -0.01(3) -0.03(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0013 0.0009 '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 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.0671 0.0586 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -0.6570 6.0260 '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 . . . 0.99999993 0.00000000 0.00037559 omega rotation goniometer -1 . 0.36226000 0.00000000 0.00000000 1.00000000 kappa rotation goniometer -1 omega -0.01457000 -0.76608180 0.00000000 0.64274309 phi rotation goniometer -1 kappa . 0.00014120 0.00000000 0.99999999 theta rotation goniometer -1 . 0.42200000 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 177.4(8) . . ? C12 P1 Au1 112.5(9) . . ? C12 P1 C14 109.3(14) . . ? C10 P1 Au1 113.8(9) . . ? C10 P1 C12 110(2) . . ? C10 P1 C14 99.1(18) . . ? C14 P1 Au1 111.5(14) . . ? C7 C6 C5 120.0 . . ? C7 C6 O1 110(3) . . ? C5 C6 O1 130(3) . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 H8 120.0 . . ? C3 C8 C7 120.0 . . ? C3 C8 H8 120.0 . . ? C8 C3 C2 125(3) . . ? C4 C3 C8 120.0 . . ? C4 C3 C2 115(4) . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? C2 C1 Au1 178(2) . . ? C1 C2 C3 172(3) . . ? C1 C2 C3A 176(4) . . ? C9 O1 C6 114(5) . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? P1 C12 H12A 108.9 . . ? P1 C12 H12B 108.9 . . ? C13 C12 P1 113.2(16) . . ? C13 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? P1 C10 H10A 109.9 . . ? P1 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C11 C10 P1 109(3) . . ? C11 C10 H10A 109.9 . . ? C11 C10 H10B 109.9 . . ? 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 . . ? P1 C14 H14A 109.4 . . ? P1 C14 H14B 109.4 . . ? P1 C14 H14C 109.5 . . ? P1 C14 H14D 109.5 . . ? H14A C14 H14B 108.0 . . ? H14C C14 H14D 108.1 . . ? C15 C14 P1 111(3) . . ? C15 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C15A C14 P1 111(4) . . ? C15A C14 H14C 109.5 . . ? C15A C14 H14D 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C15A H15D 109.5 . . ? C14 C15A H15E 109.5 . . ? C14 C15A H15F 109.5 . . ? H15D C15A H15E 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? H9AA C9A H9AB 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? O1A C9A H9AA 109.5 . . ? O1A C9A H9AB 109.5 . . ? O1A C9A H9AC 109.5 . . ? C6A O1A C9A 120(6) . . ? O1A C6A C7A 126(5) . . ? O1A C6A C5A 114(5) . . ? C7A C6A C5A 120.0 . . ? C6A C7A H7A 120.0 . . ? C6A C7A C8A 120.0 . . ? C8A C7A H7A 120.0 . . ? C7A C8A H8A 120.0 . . ? C3A C8A C7A 120.0 . . ? C3A C8A H8A 120.0 . . ? C8A C3A C2 116(5) . . ? C8A C3A C4A 120.0 . . ? C4A C3A C2 124(5) . . ? C3A C4A H4A 120.0 . . ? C3A C4A C5A 120.0 . . ? C5A C4A H4A 120.0 . . ? C6A C5A H5A 120.0 . . ? C4A C5A C6A 120.0 . . ? C4A C5A H5A 120.0 . . ? 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 2.290(9) . ? Au1 C1 1.93(3) . ? P1 C12 1.807(17) . ? P1 C10 1.78(6) . ? P1 C14 1.86(3) . ? C6 C7 1.3900 . ? C6 C5 1.3900 . ? C6 O1 1.40(5) . ? C7 H7 0.9300 . ? C7 C8 1.3900 . ? C8 H8 0.9300 . ? C8 C3 1.3900 . ? C3 C4 1.3900 . ? C3 C2 1.41(5) . ? C4 H4 0.9300 . ? C4 C5 1.3900 . ? C5 H5 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9 O1 1.35(6) . ? C1 C2 1.25(3) . ? C2 C3A 1.61(7) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13 C12 1.54(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.57(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C14 H14D 0.9700 . ? C14 C15 1.52(4) . ? C14 C15A 1.62(14) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15A H15D 0.9600 . ? C15A H15E 0.9600 . ? C15A H15F 0.9600 . ? C9A H9AA 0.9600 . ? C9A H9AB 0.9600 . ? C9A H9AC 0.9600 . ? C9A O1A 1.54(10) . ? O1A C6A 1.27(6) . ? C6A C7A 1.3900 . ? C6A C5A 1.3900 . ? C7A H7A 0.9300 . ? C7A C8A 1.3900 . ? C8A H8A 0.9300 . ? C8A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A H4A 0.9300 . ? C4A C5A 1.3900 . ? C5A H5A 0.9300 . ? 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 C12 C13 174(2) . . . . ? Au1 P1 C10 C11 68(3) . . . . ? Au1 P1 C14 C15 58(4) . . . . ? Au1 P1 C14 C15A -62(5) . . . . ? C6 C7 C8 C3 0.0 . . . . ? C7 C6 C5 C4 0.0 . . . . ? C7 C6 O1 C9 -172(4) . . . . ? C7 C8 C3 C4 0.0 . . . . ? C7 C8 C3 C2 -178(6) . . . . ? C8 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C5 C6 O1 C9 11(6) . . . . ? C2 C3 C4 C5 178(5) . . . . ? C2 C3A C4A C5A -178(6) . . . . ? O1 C6 C7 C8 -178(4) . . . . ? O1 C6 C5 C4 177(4) . . . . ? C12 P1 C10 C11 -59(2) . . . . ? C12 P1 C14 C15 -177(4) . . . . ? C12 P1 C14 C15A 63(5) . . . . ? C10 P1 C12 C13 -59(3) . . . . ? C10 P1 C14 C15 -62(4) . . . . ? C10 P1 C14 C15A 177(5) . . . . ? C14 P1 C12 C13 49(3) . . . . ? C14 P1 C10 C11 -173(2) . . . . ? C9A O1A C6A C7A -164(5) . . . . ? C9A O1A C6A C5A 12(7) . . . . ? O1A C6A C7A C8A 175(5) . . . . ? O1A C6A C5A C4A -176(4) . . . . ? C6A C7A C8A C3A 0.0 . . . . ? C7A C6A C5A C4A 0.0 . . . . ? C7A C8A C3A C2 178(6) . . . . ? C7A C8A C3A C4A 0.0 . . . . ? C8A C3A C4A C5A 0.0 . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C5A C6A C7A C8A 0.0 . . . . ?