#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:45:50 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573658.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_1573658 _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 2024-02-23 _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 16.1780(6) _cell_length_b 11.1922(3) _cell_length_c 17.8018(8) _cell_measurement_reflns_used 6481 _cell_measurement_temperature 295.3(10) _cell_measurement_theta_max 24.9240 _cell_measurement_theta_min 1.9750 _cell_volume 3223.3(2) _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 260000 _diffrn_ambient_temperature 295.3(10) _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 0.929 _diffrn_measured_fraction_theta_max 0.920 _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 -88.00 5.00 1.00 80.00 -- -25.00 114.00 -45.00 93 2 \w -37.00 29.00 1.00 80.00 -- -25.00 -39.00-167.00 66 3 \w -42.00 -12.00 1.00 80.00 -- -25.00 -26.00 8.00 30 4 \w -26.00 10.00 1.00 80.00 -- -25.00 67.00 -23.00 36 5 \w -14.00 18.00 1.00 80.00 -- -25.00 -97.00 35.00 32 6 \w -14.00 21.00 1.00 80.00 -- -25.00 -97.00-143.00 35 7 \w 2.00 43.00 1.00 80.00 -- -25.00 -26.00 8.00 41 8 \w -97.00 -14.00 1.00 80.00 -- -25.00 135.00 123.00 83 9 \w -64.00 28.00 1.00 80.00 -- -25.00 53.00 162.00 92 10 \w -29.00 37.00 1.00 80.00 -- 25.08 39.00 167.00 66 11 \w -20.00 60.00 1.00 80.00 -- 25.08 -67.00 23.00 80 12 \w -12.00 14.00 1.00 80.00 -- 25.08 97.00 143.00 26 13 \w -28.00 62.00 1.00 80.00 -- 25.08 -39.00-167.00 90 14 \w -54.00 42.00 1.00 80.00 -- 25.08 26.00 -8.00 96 15 \w -16.00 14.00 1.00 80.00 -- 25.08 97.00 -35.00 30 ; _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 52 deg.' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0222458151 _diffrn_orient_matrix_UB_12 -0.0025691497 _diffrn_orient_matrix_UB_13 0.0239993443 _diffrn_orient_matrix_UB_21 0.0178253313 _diffrn_orient_matrix_UB_22 -0.0354045184 _diffrn_orient_matrix_UB_23 -0.0151575332 _diffrn_orient_matrix_UB_31 0.0195593953 _diffrn_orient_matrix_UB_32 0.0351895299 _diffrn_orient_matrix_UB_33 -0.0134932121 _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 0.0791 _diffrn_reflns_av_unetI/netI 0.0381 _diffrn_reflns_Laue_measured_fraction_full 0.929 _diffrn_reflns_Laue_measured_fraction_max 0.920 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 41474 _diffrn_reflns_point_group_measured_fraction_full 0.929 _diffrn_reflns_point_group_measured_fraction_max 0.920 _diffrn_reflns_theta_full 19.665 _diffrn_reflns_theta_max 21.071 _diffrn_reflns_theta_min 1.966 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Ag) X-ray Source' _exptl_absorpt_coefficient_mu 4.982 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.41620 _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 'clear violet' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.839 _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 0.26 GPa and left to stabilize over ? hours.' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-pentane/dichloromethane' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.563 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.083 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 3269 _refine_ls_number_restraints 224 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0328 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0136P)^2^+1.3805P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.0572 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1624 _reflns_number_total 3269 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b2.cif _cod_data_source_block appr2_0p26GPa _cod_database_code 1573658 _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. Restrained distances C3-C5 \\sim C3A-C5A with sigma of 0.04 C7-C3 \\sim C7A-C3A with sigma of 0.04 3. Uiso/Uaniso restraints and constraints C3A \\sim C3 \\sim C8A \\sim C8 \\sim C7A \\sim C7 \\sim C6A \\sim C6 \\sim C5A \\sim C5 \\sim C4A \\sim C4 \\sim O1A \\sim O1 \\sim C9A \\sim C9: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C15A \\sim C14 \\sim C15: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A 4. Others Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C9A)= Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(O1A)=Sof(C6A)=Sof(C5A)=Sof(H5A)=Sof(C7A)= Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=1-FVAR(1) Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)= Sof(C6)=Sof(O1)=Sof(H14A)=Sof(H14B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)= Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C10(H10A,H10B), C14(H14C,H14D), C14(H14A,H14B) 5.b Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C4(H4), C5(H5), C5A(H5A), C7A(H7A), C8A(H8A), C4A(H4A) 5.c 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 appr2_0p26GPa_a.res in Pbca appr2_0p26GPa.res created by SHELXL-2018/3 at 09:29:14 on 23-Feb-2024 REM Old TITL appr2_0p26GPa in Pbca REM SHELXT solution in Pbca: R1 0.171, Rweak 0.006, Alpha 0.041 REM 0.403 for 323 systematic absences, Orientation as input REM Formula found by SHELXT: C10 O3 P Au CELL 0.56087 16.178 11.1922 17.8018 90 90 90 ZERR 8 0.0006 0.0003 0.0008 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 SADI 0.04 C3 C5 C3A C5A SADI 0.04 C7 C3 C7A C3A SIMU 0.04 0.08 1.7 C3A C3 C8A C8 C7A C7 C6A C6 C5A C5 C4A C4 O1A O1 C9A C9 SIMU 0.02 0.04 1.7 C15A C14 C15 L.S. 20 PLAN 7 TEMP 22 CONF BOND LIST 6 MORE -1 BOND $H fmap 2 acta SHEL 100 0.78 OMIT 3 5 1 OMIT 15 0 22 REM REM REM WGHT 0.013600 1.380500 FVAR 0.20431 0.71389 AU1 5 0.388824 0.750917 0.325983 11.00000 0.06226 0.06253 = 0.07529 0.00663 0.00716 -0.00067 P1 4 0.402884 0.926172 0.261971 11.00000 0.07601 0.06357 = 0.07761 0.00811 0.01500 -0.00221 PART 1 C7 1 0.444548 0.231731 0.519808 21.00000 0.09521 0.07965 = 0.07260 0.01771 -0.02683 -0.01544 AFIX 43 H7 2 0.485712 0.209706 0.553543 21.00000 -1.20000 AFIX 0 C8 1 0.445004 0.344159 0.493181 21.00000 0.06738 0.07810 = 0.06399 0.01204 -0.02295 -0.01930 AFIX 43 H8 2 0.487987 0.395746 0.505486 21.00000 -1.20000 AFIX 0 C3 1 0.378904 0.384211 0.445708 21.00000 0.06337 0.06108 = 0.06441 -0.00273 0.00623 -0.01025 C4 1 0.322245 0.300774 0.423330 21.00000 0.06630 0.07856 = 0.06027 0.01180 -0.00459 -0.01084 AFIX 43 H4 2 0.281826 0.321008 0.388427 21.00000 -1.20000 AFIX 0 C5 1 0.325124 0.181398 0.453821 21.00000 0.06057 0.06502 = 0.07585 -0.01072 0.00837 -0.01191 AFIX 43 H5 2 0.284064 0.126590 0.441595 21.00000 -1.20000 AFIX 0 C6 1 0.387724 0.149035 0.500340 21.00000 0.10163 0.06075 = 0.07135 0.01271 -0.02000 -0.01465 PART 0 C12 1 0.313376 1.020535 0.268500 11.00000 0.09040 0.09540 = 0.09889 0.01738 0.01941 0.01784 AFIX 23 H12A 2 0.266586 0.977211 0.248029 11.00000 -1.20000 H12B 2 0.302029 1.034636 0.321265 11.00000 -1.20000 AFIX 0 PART 1 O1 3 0.395036 0.037344 0.531611 21.00000 0.15959 0.07566 = 0.08549 0.02250 -0.03434 -0.02439 PART 0 C2 1 0.377554 0.500618 0.410726 11.00000 0.05419 0.07390 = 0.05921 -0.00607 0.00382 -0.00335 C1 1 0.380689 0.595607 0.380940 11.00000 0.06323 0.06935 = 0.07599 0.00511 0.00304 -0.00286 C10 1 0.424025 0.907139 0.163632 11.00000 0.10953 0.08122 = 0.08896 0.00085 0.02200 -0.00586 AFIX 23 H10A 2 0.432051 0.985242 0.141169 11.00000 -1.20000 H10B 2 0.475308 0.863075 0.158196 11.00000 -1.20000 AFIX 0 C13 1 0.318291 1.141790 0.228953 11.00000 0.16340 0.09143 = 0.15436 0.05018 0.03265 0.04013 AFIX 137 H13A 2 0.333662 1.130188 0.177380 11.00000 -1.50000 H13B 2 0.358910 1.190768 0.253393 11.00000 -1.50000 H13C 2 0.265383 1.180451 0.231288 11.00000 -1.50000 AFIX 0 C11 1 0.356784 0.842272 0.120748 11.00000 0.19645 0.13592 = 0.08810 -0.00635 -0.00335 -0.05729 AFIX 137 H11A 2 0.372315 0.835780 0.068861 11.00000 -1.50000 H11B 2 0.305961 0.886101 0.124699 11.00000 -1.50000 H11C 2 0.349449 0.763815 0.141497 11.00000 -1.50000 AFIX 0 C14 1 0.490394 1.014488 0.296466 11.00000 0.10425 0.08885 = 0.10304 0.00932 0.00961 -0.02566 PART 2 AFIX 23 H14C 2 0.540367 0.967102 0.292105 -21.00000 -1.20000 H14D 2 0.496865 1.084261 0.264684 -21.00000 -1.20000 AFIX 23 PART 1 H14A 2 0.494054 1.087876 0.267673 21.00000 -1.20000 H14B 2 0.480601 1.035840 0.348520 21.00000 -1.20000 AFIX 0 PART 2 C15A 1 0.480619 1.057636 0.382145 -21.00000 0.09655 0.11472 = 0.20152 -0.04163 0.01111 -0.00807 AFIX 137 H15A 2 0.463029 1.139540 0.383131 -21.00000 -1.50000 H15B 2 0.532769 1.050325 0.407462 -21.00000 -1.50000 H15C 2 0.440223 1.008810 0.407006 -21.00000 -1.50000 AFIX 0 PART 1 C9 1 0.339840 -0.052196 0.506962 21.00000 0.21488 0.06056 = 0.09626 0.00434 -0.00561 -0.04657 AFIX 137 H9A 2 0.345030 -0.062004 0.453597 21.00000 -1.50000 H9B 2 0.284221 -0.029226 0.518991 21.00000 -1.50000 H9C 2 0.352747 -0.126227 0.531542 21.00000 -1.50000 AFIX 0 PART 2 C9A 1 0.299961 -0.024302 0.545059 -21.00000 0.17435 0.07497 = 0.09092 0.01109 -0.03347 -0.02051 AFIX 137 H9AA 2 0.332282 -0.066393 0.508383 -21.00000 -1.50000 H9AB 2 0.249199 0.002065 0.522582 -21.00000 -1.50000 H9AC 2 0.287928 -0.076521 0.586419 -21.00000 -1.50000 AFIX 0 O1A 3 0.344844 0.075760 0.571261 -21.00000 0.09854 0.07573 = 0.07930 0.02587 -0.02745 -0.03234 C6A 1 0.345359 0.175174 0.528315 -21.00000 0.07224 0.06525 = 0.07157 0.00782 -0.00218 -0.01856 C5A 1 0.294202 0.200703 0.469146 -21.00000 0.04957 0.06715 = 0.05392 -0.00986 -0.01433 -0.01570 AFIX 43 H5A 2 0.252740 0.148275 0.454216 -21.00000 -1.20000 AFIX 0 C7A 1 0.413337 0.256675 0.548402 -21.00000 0.06743 0.07287 = 0.05290 0.00835 -0.01119 -0.02090 AFIX 43 H7A 2 0.451168 0.240439 0.586389 -21.00000 -1.20000 AFIX 0 C8A 1 0.415618 0.359103 0.505687 -21.00000 0.05169 0.05228 = 0.04827 -0.00564 0.00042 -0.00648 AFIX 43 H8A 2 0.449871 0.420226 0.522524 -21.00000 -1.20000 AFIX 0 C3A 1 0.373800 0.379242 0.442896 -21.00000 0.05421 0.06536 = 0.05959 0.00689 -0.00047 -0.00609 C4A 1 0.305619 0.295390 0.437010 -21.00000 0.04672 0.06414 = 0.06270 -0.00576 -0.00743 -0.02819 AFIX 43 H4A 2 0.264227 0.317380 0.403498 -21.00000 -1.20000 AFIX 0 PART 1 C15 1 0.571739 0.948119 0.290760 21.00000 0.06426 0.16074 = 0.10601 0.03093 0.00204 -0.02924 AFIX 137 H15D 2 0.570585 0.879782 0.323335 21.00000 -1.50000 H15E 2 0.616066 1.000144 0.305439 21.00000 -1.50000 H15F 2 0.580125 0.922363 0.239889 21.00000 -1.50000 AFIX 0 HKLF 4 REM appr2_0p26GPa_a.res in Pbca REM wR2 = 0.0572, GooF = S = 1.026, Restrained GooF = 0.996 for all data REM R1 = 0.0328 for 1624 Fo > 4sig(Fo) and 0.0915 for all 3269 data REM 251 parameters refined using 224 restraints END WGHT 0.0136 1.3803 REM Highest difference peak 0.563, deepest hole -0.476, 1-sigma level 0.083 Q1 1 0.3289 0.7500 0.1740 11.00000 0.05 0.56 Q2 1 0.4298 0.7484 0.3684 11.00000 0.05 0.54 Q3 1 0.4348 0.7537 0.2823 11.00000 0.05 0.50 Q4 1 0.3764 0.6954 0.2938 11.00000 0.05 0.45 Q5 1 0.3937 0.7497 0.0229 11.00000 0.05 0.41 Q6 1 0.3422 0.7572 0.2769 11.00000 0.05 0.38 Q7 1 0.4425 0.8414 0.3404 11.00000 0.05 0.34 ; _shelx_res_checksum 20240 _olex2_date_sample_data_collection 2022-07-11 _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 2.164 _oxdiff_exptl_absorpt_empirical_full_min 0.840 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 0.38882(2) 0.75092(2) 0.32598(2) 0.06669(10) Uani 1 1 d . . . . . P1 P 0.40288(11) 0.92617(13) 0.26197(11) 0.0724(5) Uani 1 1 d . . . . . C7 C 0.4445(9) 0.2317(13) 0.5198(8) 0.082(4) Uani 0.714(9) 1 d D U P A 1 H7 H 0.485712 0.209706 0.553543 0.099 Uiso 0.714(9) 1 calc R U P A 1 C8 C 0.4450(10) 0.3442(19) 0.4932(12) 0.070(5) Uani 0.714(9) 1 d . U P A 1 H8 H 0.487987 0.395746 0.505486 0.084 Uiso 0.714(9) 1 calc R U P A 1 C3 C 0.379(4) 0.384(4) 0.446(4) 0.063(4) Uani 0.714(9) 1 d D U P A 1 C4 C 0.3222(17) 0.301(3) 0.4233(16) 0.068(6) Uani 0.714(9) 1 d . U P A 1 H4 H 0.281826 0.321008 0.388427 0.082 Uiso 0.714(9) 1 calc R U P A 1 C5 C 0.3251(9) 0.1814(16) 0.4538(10) 0.067(4) Uani 0.714(9) 1 d D U P A 1 H5 H 0.284064 0.126590 0.441595 0.081 Uiso 0.714(9) 1 calc R U P A 1 C6 C 0.3877(9) 0.1490(11) 0.5003(8) 0.078(4) Uani 0.714(9) 1 d . U P A 1 C12 C 0.3134(4) 1.0205(5) 0.2685(4) 0.095(2) Uani 1 1 d . . . . . H12A H 0.266586 0.977211 0.248029 0.114 Uiso 1 1 calc R U . . . H12B H 0.302029 1.034636 0.321265 0.114 Uiso 1 1 calc R U . . . O1 O 0.3950(7) 0.0373(7) 0.5316(6) 0.107(3) Uani 0.714(9) 1 d . U P A 1 C2 C 0.3776(3) 0.5006(5) 0.4107(4) 0.0624(17) Uani 1 1 d . . . . . C1 C 0.3807(3) 0.5956(5) 0.3809(4) 0.0695(18) Uani 1 1 d . . . . . C10 C 0.4240(4) 0.9071(5) 0.1636(4) 0.093(2) Uani 1 1 d . . . . . H10A H 0.432051 0.985242 0.141169 0.112 Uiso 1 1 calc R U . . . H10B H 0.475308 0.863075 0.158196 0.112 Uiso 1 1 calc R U . . . C13 C 0.3183(5) 1.1418(5) 0.2290(5) 0.136(3) Uani 1 1 d . . . . . H13A H 0.333662 1.130188 0.177380 0.205 Uiso 1 1 calc R U . . . H13B H 0.358910 1.190768 0.253393 0.205 Uiso 1 1 calc R U . . . H13C H 0.265383 1.180451 0.231288 0.205 Uiso 1 1 calc R U . . . C11 C 0.3568(5) 0.8423(7) 0.1207(5) 0.140(3) Uani 1 1 d . . . . . H11A H 0.372315 0.835780 0.068861 0.210 Uiso 1 1 calc R U . . . H11B H 0.305961 0.886101 0.124699 0.210 Uiso 1 1 calc R U . . . H11C H 0.349449 0.763815 0.141497 0.210 Uiso 1 1 calc R U . . . C14 C 0.4904(5) 1.0145(6) 0.2965(5) 0.099(2) Uani 1 1 d . U . . . H14C H 0.540367 0.967102 0.292105 0.118 Uiso 0.286(9) 1 calc R U P A 2 H14D H 0.496865 1.084261 0.264684 0.118 Uiso 0.286(9) 1 calc R U P A 2 H14A H 0.494054 1.087876 0.267673 0.118 Uiso 0.714(9) 1 calc R U P A 1 H14B H 0.480601 1.035840 0.348520 0.118 Uiso 0.714(9) 1 calc R U P A 1 C15A C 0.4806(16) 1.058(2) 0.3821(19) 0.138(11) Uani 0.286(9) 1 d . U P A 2 H15A H 0.463029 1.139540 0.383131 0.206 Uiso 0.286(9) 1 calc R U P A 2 H15B H 0.532769 1.050325 0.407462 0.206 Uiso 0.286(9) 1 calc R U P A 2 H15C H 0.440223 1.008810 0.407006 0.206 Uiso 0.286(9) 1 calc R U P A 2 C9 C 0.3398(12) -0.0522(13) 0.5070(11) 0.124(6) Uani 0.714(9) 1 d . U P A 1 H9A H 0.345030 -0.062004 0.453597 0.186 Uiso 0.714(9) 1 calc R U P A 1 H9B H 0.284221 -0.029226 0.518991 0.186 Uiso 0.714(9) 1 calc R U P A 1 H9C H 0.352747 -0.126227 0.531542 0.186 Uiso 0.714(9) 1 calc R U P A 1 C9A C 0.300(3) -0.024(3) 0.545(2) 0.113(14) Uani 0.286(9) 1 d . U P A 2 H9AA H 0.332282 -0.066393 0.508383 0.170 Uiso 0.286(9) 1 calc R U P A 2 H9AB H 0.249199 0.002065 0.522582 0.170 Uiso 0.286(9) 1 calc R U P A 2 H9AC H 0.287928 -0.076521 0.586419 0.170 Uiso 0.286(9) 1 calc R U P A 2 O1A O 0.3448(13) 0.0758(16) 0.5713(12) 0.085(6) Uani 0.286(9) 1 d . U P A 2 C6A C 0.345(2) 0.175(3) 0.528(2) 0.070(7) Uani 0.286(9) 1 d . U P A 2 C5A C 0.294(2) 0.201(4) 0.469(2) 0.057(8) Uani 0.286(9) 1 d D U P A 2 H5A H 0.252740 0.148275 0.454216 0.068 Uiso 0.286(9) 1 calc R U P A 2 C7A C 0.413(2) 0.257(3) 0.5484(19) 0.064(7) Uani 0.286(9) 1 d D U P A 2 H7A H 0.451168 0.240439 0.586389 0.077 Uiso 0.286(9) 1 calc R U P A 2 C8A C 0.416(3) 0.359(5) 0.506(3) 0.051(8) Uani 0.286(9) 1 d . U P A 2 H8A H 0.449871 0.420226 0.522524 0.061 Uiso 0.286(9) 1 calc R U P A 2 C3A C 0.374(10) 0.379(11) 0.443(9) 0.060(9) Uani 0.286(9) 1 d D U P A 2 C4A C 0.306(4) 0.295(8) 0.437(4) 0.058(9) Uani 0.286(9) 1 d . U P A 2 H4A H 0.264227 0.317380 0.403498 0.069 Uiso 0.286(9) 1 calc R U P A 2 C15 C 0.5717(6) 0.9481(9) 0.2908(6) 0.110(4) Uani 0.714(9) 1 d . U P A 1 H15D H 0.570585 0.879782 0.323335 0.166 Uiso 0.714(9) 1 calc R U P A 1 H15E H 0.616066 1.000144 0.305439 0.166 Uiso 0.714(9) 1 calc R U P A 1 H15F H 0.580125 0.922363 0.239889 0.166 Uiso 0.714(9) 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 0.06226(16) 0.06253(13) 0.0753(2) 0.00663(15) 0.00716(12) -0.00067(16) P1 0.0760(12) 0.0636(8) 0.0776(16) 0.0081(9) 0.0150(10) -0.0022(9) C7 0.095(11) 0.080(10) 0.073(11) 0.018(7) -0.027(7) -0.015(8) C8 0.067(11) 0.078(9) 0.064(11) 0.012(7) -0.023(8) -0.019(9) C3 0.063(11) 0.061(8) 0.064(10) -0.003(8) 0.006(8) -0.010(7) C4 0.066(13) 0.079(8) 0.060(12) 0.012(8) -0.005(8) -0.011(9) C5 0.061(11) 0.065(7) 0.076(10) -0.011(6) 0.008(7) -0.012(7) C6 0.102(11) 0.061(6) 0.071(10) 0.013(6) -0.020(7) -0.015(7) C12 0.090(6) 0.095(4) 0.099(7) 0.017(4) 0.019(4) 0.018(4) O1 0.160(9) 0.076(5) 0.085(8) 0.023(5) -0.034(6) -0.024(5) C2 0.054(4) 0.074(4) 0.059(6) -0.006(3) 0.004(3) -0.003(3) C1 0.063(5) 0.069(4) 0.076(6) 0.005(4) 0.003(3) -0.003(3) C10 0.110(7) 0.081(4) 0.089(7) 0.001(4) 0.022(4) -0.006(4) C13 0.163(9) 0.091(5) 0.154(10) 0.050(5) 0.033(6) 0.040(5) C11 0.196(10) 0.136(6) 0.088(9) -0.006(6) -0.003(6) -0.057(7) C14 0.104(7) 0.089(5) 0.103(8) 0.009(5) 0.010(5) -0.026(4) C15A 0.10(2) 0.115(18) 0.20(3) -0.04(2) 0.01(2) -0.008(16) C9 0.21(2) 0.061(8) 0.096(16) 0.004(8) -0.006(11) -0.047(10) C9A 0.17(4) 0.07(2) 0.09(4) 0.01(2) -0.03(2) -0.02(2) O1A 0.099(14) 0.076(11) 0.079(15) 0.026(10) -0.027(10) -0.032(10) C6A 0.072(16) 0.065(13) 0.072(16) 0.008(13) -0.002(13) -0.019(13) C5A 0.050(18) 0.067(14) 0.054(18) -0.010(13) -0.014(14) -0.016(14) C7A 0.067(15) 0.073(14) 0.053(16) 0.008(13) -0.011(10) -0.021(13) C8A 0.052(18) 0.052(12) 0.048(15) -0.006(11) 0.000(14) -0.006(14) C3A 0.054(17) 0.065(16) 0.060(17) 0.007(16) 0.000(15) -0.006(16) C4A 0.047(17) 0.064(13) 0.063(18) -0.006(15) -0.007(16) -0.028(13) C15 0.064(8) 0.161(10) 0.106(10) 0.031(8) 0.002(6) -0.029(7) 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 177.90(17) . . ? C12 P1 Au1 113.1(2) . . ? C12 P1 C10 106.6(3) . . ? C12 P1 C14 106.5(4) . . ? C10 P1 Au1 113.8(2) . . ? C10 P1 C14 104.1(4) . . ? C14 P1 Au1 111.9(2) . . ? C8 C7 H7 118.1 . . ? C8 C7 C6 123.7(14) . . ? C6 C7 H7 118.1 . . ? C7 C8 H8 120.1 . . ? C7 C8 C3 119.7(18) . . ? C3 C8 H8 120.1 . . ? C8 C3 C2 123(2) . . ? C4 C3 C8 117(3) . . ? C4 C3 C2 119(2) . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 120(3) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.0(17) . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 118.8(13) . . ? C7 C6 O1 117.5(12) . . ? C5 C6 O1 123.7(12) . . ? P1 C12 H12A 108.1 . . ? P1 C12 H12B 108.1 . . ? H12A C12 H12B 107.3 . . ? C13 C12 P1 116.7(5) . . ? C13 C12 H12A 108.1 . . ? C13 C12 H12B 108.1 . . ? C6 O1 C9 117.7(12) . . ? C1 C2 C3 177(3) . . ? C1 C2 C3A 176(8) . . ? C2 C1 Au1 176.8(6) . . ? P1 C10 H10A 108.7 . . ? P1 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C10 P1 114.3(5) . . ? 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 108.8 . . ? P1 C14 H14D 108.8 . . ? P1 C14 H14A 109.1 . . ? P1 C14 H14B 109.1 . . ? H14C C14 H14D 107.7 . . ? H14A C14 H14B 107.8 . . ? C15A C14 P1 113.8(10) . . ? C15A C14 H14C 108.8 . . ? C15A C14 H14D 108.8 . . ? C15 C14 P1 112.6(6) . . ? C15 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? 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 118(3) . . ? O1A C6A C5A 127(3) . . ? O1A C6A C7A 112(3) . . ? C5A C6A C7A 121(3) . . ? C6A C5A H5A 121.6 . . ? C4A C5A C6A 117(5) . . ? C4A C5A H5A 121.6 . . ? C6A C7A H7A 123.2 . . ? C8A C7A C6A 114(3) . . ? C8A C7A H7A 123.2 . . ? C7A C8A H8A 116.8 . . ? C3A C8A C7A 126(5) . . ? C3A C8A H8A 116.8 . . ? C8A C3A C2 118(7) . . ? C8A C3A C4A 110(6) . . ? C4A C3A C2 127(7) . . ? C5A C4A C3A 130(7) . . ? C5A C4A H4A 115.0 . . ? C3A C4A H4A 115.0 . . ? 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 2.2798(15) . ? Au1 C1 1.999(6) . ? P1 C12 1.796(6) . ? P1 C10 1.796(7) . ? P1 C14 1.833(7) . ? C7 H7 0.9300 . ? C7 C8 1.34(2) . ? C7 C6 1.350(17) . ? C8 H8 0.9300 . ? C8 C3 1.43(3) . ? C3 C4 1.37(4) . ? C3 C2 1.44(2) . ? C4 H4 0.9300 . ? C4 C5 1.44(3) . ? C5 H5 0.9300 . ? C5 C6 1.36(2) . ? C6 O1 1.374(13) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.531(7) . ? O1 C9 1.412(18) . ? C2 C1 1.189(7) . ? C2 C3A 1.48(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.514(8) . ? 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 1.61(3) . ? C14 C15 1.515(10) . ? 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 1.41(4) . ? O1A C6A 1.35(3) . ? C6A C5A 1.37(6) . ? C6A C7A 1.47(4) . ? C5A H5A 0.9300 . ? C5A C4A 1.22(8) . ? C7A H7A 0.9300 . ? C7A C8A 1.38(6) . ? C8A H8A 0.9300 . ? C8A C3A 1.33(9) . ? C3A C4A 1.45(8) . ? C4A H4A 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 178.3(5) . . . . ? Au1 P1 C10 C11 61.5(6) . . . . ? Au1 P1 C14 C15A -63.7(12) . . . . ? Au1 P1 C14 C15 58.7(6) . . . . ? C7 C8 C3 C4 -7(9) . . . . ? C7 C8 C3 C2 -176(5) . . . . ? C7 C6 O1 C9 -175.1(13) . . . . ? C8 C7 C6 C5 -3(2) . . . . ? C8 C7 C6 O1 179.6(13) . . . . ? C8 C3 C4 C5 7(9) . . . . ? C3 C4 C5 C6 -5(5) . . . . ? C4 C5 C6 C7 3(2) . . . . ? C4 C5 C6 O1 -179.9(15) . . . . ? C5 C6 O1 C9 8(2) . . . . ? C6 C7 C8 C3 5(5) . . . . ? C12 P1 C10 C11 -64.0(6) . . . . ? C12 P1 C14 C15A 60.5(12) . . . . ? C12 P1 C14 C15 -177.2(6) . . . . ? C2 C3 C4 C5 176(5) . . . . ? C2 C3A C4A C5A -170(11) . . . . ? C10 P1 C12 C13 -55.8(6) . . . . ? C10 P1 C14 C15A 173.0(11) . . . . ? C10 P1 C14 C15 -64.7(6) . . . . ? C14 P1 C12 C13 54.9(7) . . . . ? C14 P1 C10 C11 -176.4(5) . . . . ? C9A O1A C6A C5A 14(5) . . . . ? C9A O1A C6A C7A -162(3) . . . . ? O1A C6A C5A C4A -179(4) . . . . ? O1A C6A C7A C8A -180(3) . . . . ? C6A C5A C4A C3A 11(15) . . . . ? C6A C7A C8A C3A -13(14) . . . . ? C5A C6A C7A C8A 4(4) . . . . ? C7A C6A C5A C4A -3(5) . . . . ? C7A C8A C3A C2 173(8) . . . . ? C7A C8A C3A C4A 18(22) . . . . ? C8A C3A C4A C5A -18(24) . . . . ?