#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:45:50 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573666.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_1573666 _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 2024-02-08 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _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 16.215(3) _cell_length_b 11.0942(12) _cell_length_c 17.732(4) _cell_measurement_reflns_used 1269 _cell_measurement_temperature 295.40(16) _cell_measurement_theta_max 24.6000 _cell_measurement_theta_min 2.4440 _cell_volume 3189.9(10) _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 320000 _diffrn_ambient_temperature 295.40(16) _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 0.703 _diffrn_measured_fraction_theta_max 0.688 _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 6.00 42.00 1.00 90.00 -- 22.04 -39.00-167.00 36 2 \w 10.00 36.00 1.00 90.00 -- 22.04 -81.00-151.00 26 3 \w -27.00 10.00 1.00 90.00 -- 22.04 39.00 167.00 37 4 \w 10.00 35.00 1.00 90.00 -- 22.04 -77.00 30.00 25 5 \w -18.00 22.00 1.00 90.00 -- 22.04 -53.00-162.00 40 6 \w -41.00 -6.00 1.00 90.00 -- 22.04 114.00 -45.00 35 7 \w -56.00 -31.00 1.00 90.00 -- -22.19 150.00 -64.00 25 8 \w -58.00 -25.00 1.00 90.00 -- -22.19 135.00 123.00 33 9 \w -107.00 -81.00 1.00 90.00 -- -22.19-160.00-120.00 26 ; _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 -0.0205790101 _diffrn_orient_matrix_UB_12 -0.0027264149 _diffrn_orient_matrix_UB_13 0.0252727070 _diffrn_orient_matrix_UB_21 -0.0037463354 _diffrn_orient_matrix_UB_22 0.0500986059 _diffrn_orient_matrix_UB_23 -0.0005056057 _diffrn_orient_matrix_UB_31 -0.0274023848 _diffrn_orient_matrix_UB_32 -0.0048782065 _diffrn_orient_matrix_UB_33 -0.0189292525 _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 0.0837 _diffrn_reflns_av_unetI/netI 0.1092 _diffrn_reflns_Laue_measured_fraction_full 0.703 _diffrn_reflns_Laue_measured_fraction_max 0.688 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8296 _diffrn_reflns_point_group_measured_fraction_full 0.703 _diffrn_reflns_point_group_measured_fraction_max 0.688 _diffrn_reflns_theta_full 19.665 _diffrn_reflns_theta_max 20.514 _diffrn_reflns_theta_min 1.975 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Ag) X-ray Source' _exptl_absorpt_coefficient_mu 5.034 _exptl_absorpt_correction_T_max 0.64452 _exptl_absorpt_correction_T_min 0.63711 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Spherical absorption correction using equivalent radius and absorption coefficient. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.858 _exptl_crystal_description sphere _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 0.32 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 _exptl_crystal_size_rad 0.400 _refine_diff_density_max 0.623 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.088 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 2239 _refine_ls_number_restraints 228 _refine_ls_restrained_S_all 0.884 _refine_ls_R_factor_all 0.1764 _refine_ls_R_factor_gt 0.0525 _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^)+(0.0161P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0953 _reflns_Friedel_coverage 0.000 _reflns_number_gt 807 _reflns_number_total 2239 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b2.cif _cod_data_source_block appr4_0p32GPa _cod_database_code 1573666 _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 O1A \\sim O1 \\sim C9A \\sim C9: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A C3 \\sim C3A \\sim C4A \\sim C4 \\sim C5A \\sim C5 \\sim C6A \\sim C6 \\sim C7A \\sim C7 \\sim C8A \\sim C8: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C8 \\sim C7 \\sim C4 \\sim C13 \\sim C3 \\sim C11 \\sim C5 \\sim C10 \\sim C1: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C2 \\sim O1: 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 C13 \\sim C12 \\sim C15 \\sim C14 \\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(H15A)=Sof(H15B)=Sof(H15C)=Sof(C9A)= Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(O1A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)= Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=1-FVAR(1) Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)= Sof(H8)=Sof(O1)=Sof(H14A)=Sof(H14B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)= Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C10(H10A,H10B), C14(H14C,H14D), C14(H14A,H14B) 4.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C7(H7), C8(H8), C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A) 4.c Fitted hexagon refined as free rotating group: C3(C4,C5,C6,C7,C8), C3A(C4A,C5A,C6A,C7A,C8A) 4.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C15A(H15A,H15B,H15C), C9(H9A,H9B, H9C), C9A(H9AA,H9AB,H9AC), C15(H15D,H15E,H15F) ; _shelx_res_file ; TITL appr4_0p32GPa_b.res in Pbca appr4_0p32GPa.res created by SHELXL-2018/3 at 15:30:02 on 08-Feb-2024 REM Old TITL appr4_0p32GPa in Pbca #61 REM SHELXT solution in Pbca: R1 0.221, Rweak 0.011, Alpha 0.078 REM 0.305 for 170 systematic absences, Orientation as input REM Formula found by SHELXT: C10 O P Au CELL 0.56087 16.215 11.0942 17.7324 90 90 90 ZERR 8 0.0027 0.0012 0.0043 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 0.01 0.02 1.7 O1A O1 C9A C9 SIMU 0.04 0.08 1.7 C3 C3A C4A C4 C5A C5 C6A C6 C7A C7 C8A C8 SIMU 0.04 0.08 1.7 C8 C7 C4 C13 C3 C11 C5 C10 C1 SIMU 0.04 0.08 1.7 C2 O1 SIMU C11 C10 P1 C13 C12 C15 C14 C15A L.S. 10 PLAN 6 TEMP 22 CONF BOND LIST 6 MORE -1 BOND $H fmap 2 acta SHEL 100 0.8 REM REM REM WGHT 0.016100 FVAR 0.20817 0.65371 AU1 5 0.387743 0.753163 0.326154 11.00000 0.08605 0.08418 = 0.09800 0.00771 0.01022 0.00035 P1 4 0.401241 0.929851 0.261680 11.00000 0.12155 0.08378 = 0.09771 0.00762 0.02178 0.00011 PART 1 AFIX 66 C3 1 0.383018 0.380673 0.449442 21.00000 0.05715 0.08174 = 0.08724 -0.00704 -0.02960 -0.01632 C4 1 0.322304 0.298037 0.429713 21.00000 0.06604 0.09684 = 0.10639 -0.00417 -0.05430 0.00194 AFIX 43 H4 2 0.279261 0.321241 0.398238 21.00000 -1.20000 AFIX 65 C5 1 0.325922 0.180718 0.457027 21.00000 0.07767 0.08688 = 0.10865 0.00219 -0.03010 -0.00424 AFIX 43 H5 2 0.285300 0.125429 0.443826 21.00000 -1.20000 AFIX 65 C6 1 0.390255 0.146035 0.504070 21.00000 0.09060 0.09177 = 0.11293 0.01018 -0.01193 0.00894 C7 1 0.450969 0.228670 0.523799 21.00000 0.06873 0.11027 = 0.11503 0.01785 -0.03093 0.00326 AFIX 43 H7 2 0.494012 0.205464 0.555274 21.00000 -1.20000 AFIX 65 C8 1 0.447352 0.345989 0.496486 21.00000 0.07732 0.09382 = 0.10913 0.00773 -0.02911 -0.02322 AFIX 43 H8 2 0.487974 0.401278 0.509687 21.00000 -1.20000 AFIX 0 PART 0 C12 1 0.309256 1.022694 0.269205 11.00000 0.16002 0.13836 = 0.09406 0.03717 0.02137 0.05667 AFIX 23 H12A 2 0.263069 0.978899 0.247809 11.00000 -1.20000 H12B 2 0.297406 1.036177 0.322156 11.00000 -1.20000 AFIX 0 PART 1 O1 3 0.398760 0.032727 0.529829 21.00000 0.18023 0.10393 = 0.12165 0.03152 -0.03619 -0.03926 PART 0 C2 1 0.377261 0.501696 0.410660 11.00000 0.07415 0.08049 = 0.06676 -0.01316 0.00702 -0.00505 C1 1 0.381438 0.599002 0.382723 11.00000 0.10974 0.07002 = 0.09482 -0.01506 0.02062 -0.00303 C10 1 0.423485 0.909969 0.162636 11.00000 0.18530 0.09153 = 0.10115 0.00162 0.01577 0.01023 AFIX 23 H10A 2 0.432879 0.988498 0.140172 11.00000 -1.20000 H10B 2 0.474061 0.863948 0.157693 11.00000 -1.20000 AFIX 0 C13 1 0.316269 1.147214 0.228946 11.00000 0.24155 0.13858 = 0.13606 0.05097 0.06235 0.05938 AFIX 137 H13A 2 0.321437 1.135046 0.175555 11.00000 -1.50000 H13B 2 0.363948 1.189236 0.247355 11.00000 -1.50000 H13C 2 0.267742 1.194028 0.239141 11.00000 -1.50000 AFIX 0 C11 1 0.355890 0.846536 0.118979 11.00000 0.32678 0.15944 = 0.09837 0.00404 -0.02148 -0.08773 AFIX 137 H11A 2 0.377867 0.816290 0.072406 11.00000 -1.50000 H11B 2 0.312159 0.902409 0.108497 11.00000 -1.50000 H11C 2 0.334817 0.780719 0.148373 11.00000 -1.50000 AFIX 0 C14 1 0.487864 1.020064 0.295853 11.00000 0.16456 0.11679 = 0.15386 0.01656 0.02370 -0.03799 PART 2 AFIX 23 H14C 2 0.538636 0.975088 0.289139 -21.00000 -1.20000 H14D 2 0.491839 1.093292 0.266186 -21.00000 -1.20000 AFIX 23 PART 1 H14A 2 0.492685 1.093157 0.266160 21.00000 -1.20000 H14B 2 0.478670 1.042688 0.348018 21.00000 -1.20000 AFIX 0 PART 2 C15A 1 0.477714 1.054285 0.382138 -21.00000 0.22281 0.21805 = 0.23664 -0.04457 -0.00478 -0.02153 AFIX 137 H15A 2 0.446729 1.127706 0.386386 -21.00000 -1.50000 H15B 2 0.531165 1.065186 0.404397 -21.00000 -1.50000 H15C 2 0.449101 0.990688 0.407891 -21.00000 -1.50000 AFIX 0 PART 1 C9 1 0.344593 -0.054704 0.507529 21.00000 0.18388 0.10465 = 0.12548 0.03594 -0.00699 -0.04526 AFIX 137 H9A 2 0.360876 -0.085378 0.459146 21.00000 -1.50000 H9B 2 0.290174 -0.021074 0.504062 21.00000 -1.50000 H9C 2 0.344688 -0.119061 0.543720 21.00000 -1.50000 AFIX 0 PART 2 C9A 1 0.291042 -0.032438 0.544978 -21.00000 0.18508 0.10015 = 0.12341 0.04582 -0.02531 -0.04292 AFIX 137 H9AA 2 0.292734 -0.033241 0.490864 -21.00000 -1.50000 H9AB 2 0.235361 -0.019501 0.561501 -21.00000 -1.50000 H9AC 2 0.310518 -0.108299 0.563982 -21.00000 -1.50000 AFIX 0 O1A 3 0.346848 0.070607 0.575034 -21.00000 0.17879 0.10326 = 0.12003 0.03651 -0.03746 -0.04175 AFIX 66 C3A 1 0.363946 0.382930 0.441201 -21.00000 0.06190 0.08202 = 0.08771 -0.01361 -0.02654 -0.01720 C4A 1 0.301085 0.303171 0.422484 -21.00000 0.08839 0.09085 = 0.10812 -0.01099 -0.02574 -0.00779 AFIX 43 H4A 2 0.265590 0.320878 0.382806 -21.00000 -1.20000 AFIX 65 C5A 1 0.291276 0.196946 0.463071 -21.00000 0.08868 0.09587 = 0.10952 0.00344 -0.01785 0.00867 AFIX 43 H5A 2 0.249218 0.143582 0.450548 -21.00000 -1.20000 AFIX 65 C6A 1 0.344329 0.170479 0.522374 -21.00000 0.08698 0.06388 = 0.12210 0.02262 -0.02407 0.00877 C7A 1 0.407190 0.250237 0.541092 -21.00000 0.06665 0.09798 = 0.10900 0.02177 -0.02736 -0.00733 AFIX 43 H7A 2 0.442685 0.232528 0.580770 -21.00000 -1.20000 AFIX 65 C8A 1 0.417000 0.356462 0.500506 -21.00000 0.05758 0.09177 = 0.10306 -0.00392 -0.02657 -0.02883 AFIX 43 H8A 2 0.459058 0.409826 0.513029 -21.00000 -1.20000 AFIX 0 PART 1 C15 1 0.569220 0.944228 0.289198 21.00000 0.10702 0.21643 = 0.11200 0.04290 0.00948 -0.05191 AFIX 137 H15D 2 0.587151 0.920453 0.338603 21.00000 -1.50000 H15E 2 0.611290 0.992119 0.265677 21.00000 -1.50000 H15F 2 0.558995 0.873715 0.259243 21.00000 -1.50000 AFIX 0 HKLF 4 REM appr4_0p32GPa_b.res in Pbca REM wR2 = 0.0953, GooF = S = 0.923, Restrained GooF = 0.884 for all data REM R1 = 0.0525 for 807 Fo > 4sig(Fo) and 0.1764 for all 2239 data REM 227 parameters refined using 228 restraints END WGHT 0.0161 0.0000 REM Highest difference peak 0.623, deepest hole -0.409, 1-sigma level 0.088 Q1 1 0.3297 0.7492 0.1885 11.00000 0.05 0.62 Q2 1 0.3402 0.6988 0.2822 11.00000 0.05 0.53 Q3 1 0.3636 0.7204 0.2548 11.00000 0.05 0.50 Q4 1 0.3196 0.7449 0.3612 11.00000 0.05 0.49 Q5 1 0.3384 0.8003 0.2866 11.00000 0.05 0.47 Q6 1 0.5748 0.2437 0.5764 11.00000 0.05 0.41 ; _shelx_res_checksum 55680 _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 1.874 _oxdiff_exptl_absorpt_empirical_full_min 0.525 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 0.38774(3) 0.75316(5) 0.32615(4) 0.0894(3) Uani 1 1 d . . . . . P1 P 0.4012(3) 0.9299(3) 0.2617(3) 0.1010(18) Uani 1 1 d . U . . . C3 C 0.383(2) 0.381(3) 0.449(2) 0.075(8) Uani 0.654(18) 1 d G U P A 1 C4 C 0.3223(19) 0.298(3) 0.430(2) 0.090(8) Uani 0.654(18) 1 d G U P A 1 H4 H 0.279261 0.321241 0.398238 0.108 Uiso 0.654(18) 1 calc R U P A 1 C5 C 0.3259(15) 0.181(3) 0.4570(16) 0.091(9) Uani 0.654(18) 1 d G U P A 1 H5 H 0.285300 0.125429 0.443826 0.109 Uiso 0.654(18) 1 calc R U P A 1 C6 C 0.3903(15) 0.146(2) 0.5041(14) 0.098(9) Uani 0.654(18) 1 d G U P A 1 C7 C 0.4510(14) 0.229(2) 0.5238(14) 0.098(9) Uani 0.654(18) 1 d G U P A 1 H7 H 0.494012 0.205464 0.555274 0.118 Uiso 0.654(18) 1 calc R U P A 1 C8 C 0.4474(16) 0.346(2) 0.496(2) 0.093(9) Uani 0.654(18) 1 d G U P A 1 H8 H 0.487974 0.401278 0.509687 0.112 Uiso 0.654(18) 1 calc R U P A 1 C12 C 0.3093(10) 1.0227(12) 0.2692(12) 0.131(7) Uani 1 1 d . U . . . H12A H 0.263069 0.978899 0.247809 0.157 Uiso 1 1 calc R U . . . H12B H 0.297406 1.036177 0.322156 0.157 Uiso 1 1 calc R U . . . O1 O 0.3988(18) 0.0327(18) 0.5298(18) 0.135(8) Uani 0.654(18) 1 d . U P A 1 C2 C 0.3773(8) 0.5017(12) 0.4107(9) 0.074(5) Uani 1 1 d . . . . . C1 C 0.3814(9) 0.5990(11) 0.3827(10) 0.092(6) Uani 1 1 d . . . . . C10 C 0.4235(11) 0.9100(13) 0.1626(12) 0.126(7) Uani 1 1 d . U . . . H10A H 0.432879 0.988498 0.140172 0.151 Uiso 1 1 calc R U . . . H10B H 0.474061 0.863948 0.157693 0.151 Uiso 1 1 calc R U . . . C13 C 0.3163(11) 1.1472(13) 0.2289(12) 0.172(9) Uani 1 1 d . U . . . H13A H 0.321437 1.135046 0.175555 0.258 Uiso 1 1 calc R U . . . H13B H 0.363948 1.189236 0.247355 0.258 Uiso 1 1 calc R U . . . H13C H 0.267742 1.194028 0.239141 0.258 Uiso 1 1 calc R U . . . C11 C 0.3559(14) 0.8465(16) 0.1190(14) 0.195(11) Uani 1 1 d . U . . . H11A H 0.377867 0.816290 0.072406 0.292 Uiso 1 1 calc R U . . . H11B H 0.312159 0.902409 0.108497 0.292 Uiso 1 1 calc R U . . . H11C H 0.334817 0.780719 0.148373 0.292 Uiso 1 1 calc R U . . . C14 C 0.4879(14) 1.0201(16) 0.2959(14) 0.145(9) Uani 1 1 d . U . . . H14C H 0.538636 0.975088 0.289139 0.174 Uiso 0.346(18) 1 calc R U P A 2 H14D H 0.491839 1.093292 0.266186 0.174 Uiso 0.346(18) 1 calc R U P A 2 H14A H 0.492685 1.093157 0.266160 0.174 Uiso 0.654(18) 1 calc R U P A 1 H14B H 0.478670 1.042688 0.348018 0.174 Uiso 0.654(18) 1 calc R U P A 1 C15A C 0.478(4) 1.054(6) 0.382(5) 0.23(3) Uani 0.346(18) 1 d . U P A 2 H15A H 0.446729 1.127706 0.386386 0.339 Uiso 0.346(18) 1 calc R U P A 2 H15B H 0.531165 1.065186 0.404397 0.339 Uiso 0.346(18) 1 calc R U P A 2 H15C H 0.449101 0.990688 0.407891 0.339 Uiso 0.346(18) 1 calc R U P A 2 C9 C 0.345(2) -0.055(3) 0.508(2) 0.138(10) Uani 0.654(18) 1 d . U P A 1 H9A H 0.360876 -0.085378 0.459146 0.207 Uiso 0.654(18) 1 calc R U P A 1 H9B H 0.290174 -0.021074 0.504062 0.207 Uiso 0.654(18) 1 calc R U P A 1 H9C H 0.344688 -0.119061 0.543720 0.207 Uiso 0.654(18) 1 calc R U P A 1 C9A C 0.291(4) -0.032(5) 0.545(4) 0.136(11) Uani 0.346(18) 1 d . U P A 2 H9AA H 0.292734 -0.033241 0.490864 0.204 Uiso 0.346(18) 1 calc R U P A 2 H9AB H 0.235361 -0.019501 0.561501 0.204 Uiso 0.346(18) 1 calc R U P A 2 H9AC H 0.310518 -0.108299 0.563982 0.204 Uiso 0.346(18) 1 calc R U P A 2 O1A O 0.347(3) 0.071(4) 0.575(3) 0.134(9) Uani 0.346(18) 1 d . U P A 2 C3A C 0.364(4) 0.383(6) 0.441(4) 0.077(11) Uani 0.346(18) 1 d G U P A 2 C4A C 0.301(4) 0.303(6) 0.422(4) 0.096(11) Uani 0.346(18) 1 d G U P A 2 H4A H 0.265590 0.320878 0.382806 0.115 Uiso 0.346(18) 1 calc R U P A 2 C5A C 0.291(3) 0.197(5) 0.463(3) 0.098(13) Uani 0.346(18) 1 d G U P A 2 H5A H 0.249218 0.143582 0.450548 0.118 Uiso 0.346(18) 1 calc R U P A 2 C6A C 0.344(3) 0.170(4) 0.522(3) 0.091(12) Uani 0.346(18) 1 d G U P A 2 C7A C 0.407(2) 0.250(5) 0.541(3) 0.091(11) Uani 0.346(18) 1 d G U P A 2 H7A H 0.442685 0.232528 0.580770 0.109 Uiso 0.346(18) 1 calc R U P A 2 C8A C 0.417(3) 0.356(5) 0.501(4) 0.084(11) Uani 0.346(18) 1 d G U P A 2 H8A H 0.459058 0.409826 0.513029 0.101 Uiso 0.346(18) 1 calc R U P A 2 C15 C 0.5692(17) 0.944(3) 0.2892(17) 0.145(14) Uani 0.654(18) 1 d . U P A 1 H15D H 0.587151 0.920453 0.338603 0.218 Uiso 0.654(18) 1 calc R U P A 1 H15E H 0.611290 0.992119 0.265677 0.218 Uiso 0.654(18) 1 calc R U P A 1 H15F H 0.558995 0.873715 0.259243 0.218 Uiso 0.654(18) 1 calc R U P A 1 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 0.0861(5) 0.0842(4) 0.0980(8) 0.0077(5) 0.0102(3) 0.0004(4) P1 0.122(5) 0.084(2) 0.098(7) 0.008(3) 0.022(3) 0.000(3) C3 0.06(2) 0.082(12) 0.087(18) -0.007(12) -0.030(15) -0.016(13) C4 0.07(2) 0.097(13) 0.106(18) -0.004(13) -0.054(14) 0.002(13) C5 0.08(2) 0.087(13) 0.11(2) 0.002(14) -0.030(16) -0.004(16) C6 0.09(2) 0.092(16) 0.11(2) 0.010(15) -0.012(18) 0.009(17) C7 0.07(2) 0.110(15) 0.12(2) 0.018(15) -0.031(15) 0.003(17) C8 0.08(2) 0.094(14) 0.11(2) 0.008(14) -0.029(16) -0.023(15) C12 0.160(17) 0.138(12) 0.09(2) 0.037(13) 0.021(12) 0.057(11) O1 0.18(3) 0.104(14) 0.12(3) 0.032(15) -0.036(14) -0.039(14) C2 0.074(13) 0.080(9) 0.067(19) -0.013(10) 0.007(8) -0.005(9) C1 0.110(15) 0.070(9) 0.09(2) -0.015(10) 0.021(10) -0.003(9) C10 0.19(2) 0.092(10) 0.10(2) 0.002(12) 0.016(13) 0.010(11) C13 0.24(3) 0.139(13) 0.14(3) 0.051(15) 0.062(16) 0.059(14) C11 0.33(3) 0.159(16) 0.10(3) 0.004(17) -0.021(19) -0.088(18) C14 0.16(2) 0.117(13) 0.15(3) 0.017(15) 0.024(17) -0.038(13) C15A 0.22(6) 0.22(5) 0.24(8) -0.04(6) 0.00(6) -0.02(5) C9 0.18(3) 0.105(16) 0.13(3) 0.036(17) -0.007(17) -0.045(18) C9A 0.19(3) 0.100(18) 0.12(3) 0.05(2) -0.025(19) -0.04(2) O1A 0.18(3) 0.103(15) 0.12(3) 0.037(16) -0.037(15) -0.042(16) C3A 0.06(3) 0.082(18) 0.09(2) -0.014(18) -0.03(2) -0.017(18) C4A 0.09(3) 0.091(17) 0.11(2) -0.011(17) -0.026(19) -0.008(19) C5A 0.09(3) 0.096(19) 0.11(2) 0.003(19) -0.02(2) 0.01(2) C6A 0.09(3) 0.064(18) 0.12(2) 0.023(19) -0.02(2) 0.01(2) C7A 0.07(3) 0.098(18) 0.11(2) 0.022(18) -0.027(19) -0.01(2) C8A 0.06(2) 0.092(17) 0.10(2) -0.004(17) -0.027(19) -0.029(19) C15 0.11(3) 0.22(3) 0.11(4) 0.04(2) 0.009(18) -0.05(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(5) . . ? C12 P1 Au1 111.8(6) . . ? C12 P1 C14 107.2(10) . . ? C10 P1 Au1 113.7(5) . . ? C10 P1 C12 107.7(9) . . ? C10 P1 C14 103.6(10) . . ? C14 P1 Au1 112.2(7) . . ? C4 C3 C8 120.0 . . ? C4 C3 C2 115.3(19) . . ? C8 C3 C2 124.4(18) . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.0 . . ? O1 C6 C5 123(2) . . ? O1 C6 C7 117(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 H8 120.0 . . ? C7 C8 C3 120.0 . . ? C7 C8 H8 120.0 . . ? P1 C12 H12A 108.7 . . ? P1 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C13 C12 P1 114.1(11) . . ? C13 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C6 O1 C9 120(3) . . ? C1 C2 C3 173(2) . . ? C1 C2 C3A 174(3) . . ? C2 C1 Au1 174.3(16) . . ? P1 C10 H10A 108.7 . . ? P1 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C10 P1 114.1(17) . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? 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 . . ? 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 H14C 109.3 . . ? P1 C14 H14D 109.3 . . ? P1 C14 H14A 109.9 . . ? P1 C14 H14B 109.9 . . ? H14C C14 H14D 107.9 . . ? H14A C14 H14B 108.3 . . ? C15A C14 P1 112(3) . . ? C15A C14 H14C 109.3 . . ? C15A C14 H14D 109.3 . . ? C15 C14 P1 109.1(16) . . ? C15 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? C14 C15A H15A 109.5 . . ? C14 C15A H15B 109.5 . . ? C14 C15A H15C 109.5 . . ? H15A C15A H15B 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? 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 . . ? 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 109(4) . . ? C4A C3A C2 127(4) . . ? C4A C3A C8A 120.0 . . ? C8A C3A C2 113(4) . . ? C3A C4A H4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C5A C4A H4A 120.0 . . ? C4A C5A H5A 120.0 . . ? C4A C5A C6A 120.0 . . ? C6A C5A H5A 120.0 . . ? C5A C6A O1A 132(4) . . ? C7A C6A O1A 108(4) . . ? C7A C6A C5A 120.0 . . ? C6A C7A H7A 120.0 . . ? C6A C7A C8A 120.0 . . ? C8A C7A H7A 120.0 . . ? C3A C8A H8A 120.0 . . ? C7A C8A C3A 120.0 . . ? C7A C8A H8A 120.0 . . ? C14 C15 H15D 109.5 . . ? C14 C15 H15E 109.5 . . ? C14 C15 H15F 109.5 . . ? H15D C15 H15E 109.5 . . ? H15D C15 H15F 109.5 . . ? H15E C15 H15F 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 2.280(4) . ? Au1 C1 1.985(15) . ? P1 C12 1.818(14) . ? P1 C10 1.81(2) . ? P1 C14 1.828(19) . ? C3 C4 1.3900 . ? C3 C8 1.3900 . ? C3 C2 1.51(3) . ? C4 H4 0.9300 . ? C4 C5 1.3900 . ? C5 H5 0.9300 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C6 O1 1.34(3) . ? C7 H7 0.9300 . ? C7 C8 1.3900 . ? C8 H8 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.559(17) . ? O1 C9 1.37(3) . ? C2 C1 1.190(16) . ? C2 C3A 1.44(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.52(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 H14C 0.9700 . ? C14 H14D 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15A 1.59(8) . ? C14 C15 1.57(3) . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9A H9AA 0.9600 . ? C9A H9AB 0.9600 . ? C9A H9AC 0.9600 . ? C9A O1A 1.55(6) . ? O1A C6A 1.45(6) . ? C3A C4A 1.3900 . ? C3A C8A 1.3900 . ? C4A H4A 0.9300 . ? C4A C5A 1.3900 . ? C5A H5A 0.9300 . ? C5A C6A 1.3900 . ? C6A C7A 1.3900 . ? C7A H7A 0.9300 . ? C7A C8A 1.3900 . ? C8A H8A 0.9300 . ? C15 H15D 0.9600 . ? C15 H15E 0.9600 . ? C15 H15F 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 C12 C13 177.6(13) . . . . ? Au1 P1 C10 C11 63.2(14) . . . . ? Au1 P1 C14 C15A -60(3) . . . . ? Au1 P1 C14 C15 57.8(17) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C3 C8 C7 0.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C4 C5 C6 O1 -177(3) . . . . ? C5 C6 C7 C8 0.0 . . . . ? C5 C6 O1 C9 3(4) . . . . ? C6 C7 C8 C3 0.0 . . . . ? C7 C6 O1 C9 -175(2) . . . . ? C8 C3 C4 C5 0.0 . . . . ? C12 P1 C10 C11 -61.3(14) . . . . ? C12 P1 C14 C15A 63(4) . . . . ? C12 P1 C14 C15 -179.1(15) . . . . ? O1 C6 C7 C8 177(2) . . . . ? C2 C3 C4 C5 174(3) . . . . ? C2 C3 C8 C7 -174(4) . . . . ? C2 C3A C4A C5A -173(7) . . . . ? C2 C3A C8A C7A 174(6) . . . . ? C10 P1 C12 C13 -56.8(17) . . . . ? C10 P1 C14 C15A 177(3) . . . . ? C10 P1 C14 C15 -65.3(17) . . . . ? C14 P1 C12 C13 54.2(19) . . . . ? C14 P1 C10 C11 -174.7(13) . . . . ? C9A O1A C6A C5A 15(6) . . . . ? C9A O1A C6A C7A -167(3) . . . . ? O1A C6A C7A C8A -178(4) . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C4A C3A C8A C7A 0.0 . . . . ? C4A C5A C6A O1A 178(5) . . . . ? C4A C5A C6A C7A 0.0 . . . . ? C5A C6A C7A C8A 0.0 . . . . ? C6A C7A C8A C3A 0.0 . . . . ? C8A C3A C4A C5A 0.0 . . . . ?