#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:45:50 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573660.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_1573660 _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 16.168(2) _cell_length_b 10.9575(12) _cell_length_c 17.526(4) _cell_measurement_reflns_used 1342 _cell_measurement_temperature 295.3(4) _cell_measurement_theta_max 23.5910 _cell_measurement_theta_min 1.9630 _cell_volume 3104.9(9) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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 450000 _diffrn_ambient_temperature 295.3(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 0.723 _diffrn_measured_fraction_theta_max 0.564 _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 -0.0205951765 _diffrn_orient_matrix_UB_12 0.0026452197 _diffrn_orient_matrix_UB_13 -0.0255761282 _diffrn_orient_matrix_UB_21 -0.0037449549 _diffrn_orient_matrix_UB_22 -0.0507445881 _diffrn_orient_matrix_UB_23 0.0004702167 _diffrn_orient_matrix_UB_31 -0.0275903959 _diffrn_orient_matrix_UB_32 0.0048684908 _diffrn_orient_matrix_UB_33 0.0190472492 _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 0.0783 _diffrn_reflns_av_unetI/netI 0.1466 _diffrn_reflns_Laue_measured_fraction_full 0.723 _diffrn_reflns_Laue_measured_fraction_max 0.564 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10035 _diffrn_reflns_point_group_measured_fraction_full 0.723 _diffrn_reflns_point_group_measured_fraction_max 0.564 _diffrn_reflns_theta_full 19.665 _diffrn_reflns_theta_max 25.495 _diffrn_reflns_theta_min 1.988 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Ag) X-ray Source' _exptl_absorpt_coefficient_mu 5.172 _exptl_absorpt_correction_T_max 0.08698 _exptl_absorpt_correction_T_min 0.06629 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Spherical absorption correction using equivalent radius and absorption coefficient. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.909 _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 0.45 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 0.637 _refine_diff_density_min -0.843 _refine_diff_density_rms 0.106 _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 3319 _refine_ls_number_restraints 206 _refine_ls_restrained_S_all 0.897 _refine_ls_R_factor_all 0.2449 _refine_ls_R_factor_gt 0.0537 _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^)+(0.0312P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0892 _refine_ls_wR_factor_ref 0.1402 _reflns_Friedel_coverage 0.000 _reflns_number_gt 921 _reflns_number_total 3319 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b2.cif _cod_data_source_block appr4_0p45GPa _cod_original_cell_volume 3104.8(10) _cod_database_code 1573660 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C14 H19 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. ; _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 C14-C15 \\sim C14-C15A with sigma of 0.02 O1-C9 \\sim O1A-C9A with sigma of 0.02 C6-C9 \\sim C6A-C9A with sigma of 0.04 C8-C6 \\sim C8A-C6A with sigma of 0.04 C2-C3 \\sim C2-C3A with sigma of 0.02 C7-C8 \\sim C7A-C8A with sigma of 0.02 C7-C6 \\sim C7A-C6A with sigma of 0.02 C8-C3 \\sim C8A-C3A with sigma of 0.02 C3-C4 \\sim C3A-C4A with sigma of 0.02 C4-C6 \\sim C4A-C6A with sigma of 0.04 C4-C5 \\sim C4A-C5A with sigma of 0.02 C5-C6 \\sim C5A-C6A with sigma of 0.02 C8-C4 \\sim C8A-C4A with sigma of 0.04 C6-O1 \\sim C6A-O1A with sigma of 0.02 C3-C5 \\sim C3A-C5A with sigma of 0.04 C5-O1 \\sim C5A-O1A with sigma of 0.04 C2-C8 \\sim C2-C8A with sigma of 0.04 C2-C4 \\sim C2-C4A with sigma of 0.04 C7-C3 \\sim C7A-C3A with sigma of 0.04 C7-C5 \\sim C7A-C5A with sigma of 0.04 C7-O1 \\sim C7A-O1A with sigma of 0.04 3. Uiso/Uaniso restraints and constraints C9A \\sim C9: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C5A \\sim C5: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C3 \\sim C3A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C11: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C7A \\sim C7: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C4A \\sim C4: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A O1A \\sim O1: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C8A \\sim C8: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C15 \\sim C15A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C6A \\sim C6: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C12: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C13: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A Uanis(C3) = Uanis(C3A) Uanis(C8) = Uanis(C8A) Uanis(C4A) = Uanis(C4) Uanis(C5) = Uanis(C5A) 4. Rigid body (RIGU) restrains C3, C4, C5, C6, C8, C7, O1, C9 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 C3A, C4A, C5A, C6A, C7A, C8A, C9A, O1A with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 C14, C15, C15A, P1, C12, C13, C10, C11 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C9A)= Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(O1A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)= Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=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(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1) 6.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C14(H14C,H14D) 6.b Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C4(H4), C5(H5), C7A(H7A), C8A(H8A), C4A(H4A), C5A(H5A) 6.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C15A(H15D,H15E, H15F), C11(H11A,H11B,H11C), C9A(H9AA,H9AB,H9AC) ; _shelx_res_file ; TITL appr4_0p45GPa_a.res in Pbca appr4_0p45GPa.res created by SHELXL-2018/3 at 17:24:40 on 15-May-2023 REM Old TITL appr4_0p45GPa in Pbca #61 REM SHELXT solution in Pbca: R1 0.193, Rweak 0.141, Alpha 0.028 REM 0.453 for 180 systematic absences, Orientation as input REM Formula found by SHELXT: C11 P Au CELL 0.56087 16.1677 10.9575 17.5259 90 90 90 ZERR 8 0.0023 0.0012 0.0044 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 C14 C15 C14 C15A SADI O1 C9 O1A C9A SADI 0.04 C6 C9 C6A C9A SADI 0.04 C8 C6 C8A C6A SADI C2 C3 C2 C3A SIMU 0.04 0.08 1.7 C9A C9 SADI C7 C8 C7A C8A RIGU C3 C4 C5 C6 C8 C7 O1 C9 RIGU C3A C4A C5A C6A C7A C8A C9A O1A SADI C7 C6 C7A C6A SADI C8 C3 C8A C3A SADI C3 C4 C3A C4A SADI 0.04 C4 C6 C4A C6A SADI C4 C5 C4A C5A SADI C5 C6 C5A C6A SADI 0.04 C8 C4 C8A C4A SADI C6 O1 C6A O1A SADI 0.04 C3 C5 C3A C5A SADI 0.04 C5 O1 C5A O1A SADI 0.04 C2 C8 C2 C8A SADI 0.04 C2 C4 C2 C4A SADI 0.04 C7 C3 C7A C3A SADI 0.04 C7 C5 C7A C5A SADI 0.04 C7 O1 C7A O1A SIMU 0.04 0.08 1.7 C5A C5 SIMU 0.04 0.08 1.7 C3 C3A SIMU 0.04 0.08 1.7 C11 SIMU 0.04 0.08 1.7 C7A C7 SIMU 0.02 0.04 1.7 C4A C4 SIMU 0.04 0.08 1.7 O1A O1 SIMU 0.04 0.08 1.7 C8A C8 SIMU 0.04 0.08 1.7 C15 C15A SIMU 0.04 0.08 1.7 C6A C6 SIMU 0.04 0.08 1.7 C12 SIMU 0.04 0.08 1.7 C13 RIGU C14 C15 C15A P1 C12 C13 C10 C11 EADP C3 C3A EADP C8 C8A EADP C4A C4 EADP C5 C5A L.S. 50 PLAN 6 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT 8 3 0 REM REM REM WGHT 0.031200 FVAR 0.20531 0.73155 AU1 5 0.387219 0.756625 0.326079 11.00000 0.08307 0.08918 = 0.09082 0.00647 0.00844 0.00146 P1 4 0.400882 0.935560 0.261821 11.00000 0.09932 0.09332 = 0.09665 0.01052 0.01847 -0.00146 C2 1 0.377705 0.499248 0.411079 11.00000 0.10127 0.08074 = 0.05002 0.00374 -0.00117 0.00304 C1 1 0.378577 0.599300 0.382859 11.00000 0.08175 0.10516 = 0.06458 -0.00848 -0.00721 0.00746 PART 1 C7 1 0.448857 0.229144 0.520961 21.00000 0.09833 0.10600 = 0.13829 0.03862 -0.03376 -0.01356 AFIX 43 H7 2 0.491402 0.207899 0.554112 21.00000 -1.20000 AFIX 0 C8 1 0.446022 0.343713 0.492045 21.00000 0.06452 0.08994 = 0.08513 0.00346 -0.00674 -0.01218 AFIX 43 H8 2 0.489024 0.397582 0.502426 21.00000 -1.20000 AFIX 0 C3 1 0.380712 0.382090 0.447551 21.00000 0.06082 0.09982 = 0.08247 0.00387 -0.00219 -0.00389 C4 1 0.321424 0.294495 0.429239 21.00000 0.07320 0.10186 = 0.11219 0.00181 -0.03266 -0.00255 AFIX 43 H4 2 0.278684 0.315532 0.396249 21.00000 -1.20000 AFIX 0 C5 1 0.324072 0.176342 0.458751 21.00000 0.08183 0.08905 = 0.09568 -0.01648 0.00192 0.00496 AFIX 43 H5 2 0.281483 0.121570 0.448773 21.00000 -1.20000 AFIX 0 C6 1 0.389225 0.142555 0.501962 21.00000 0.09602 0.07720 = 0.11252 0.01146 -0.00668 -0.00011 PART 0 C10 1 0.421492 0.913820 0.160382 11.00000 0.15685 0.11661 = 0.09064 -0.00644 0.01497 0.01422 AFIX 23 H10A 2 0.431646 0.992903 0.137344 11.00000 -1.20000 H10B 2 0.471534 0.865784 0.154890 11.00000 -1.20000 AFIX 0 PART 1 O1 3 0.399937 0.028374 0.534521 21.00000 0.17275 0.08610 = 0.17184 0.03320 -0.05356 -0.02662 PART 0 C12 1 0.309651 1.029869 0.266912 11.00000 0.14079 0.10655 = 0.11499 0.02535 0.02638 0.03639 AFIX 23 H12A 2 0.264003 0.985776 0.243890 11.00000 -1.20000 H12B 2 0.296046 1.042719 0.320215 11.00000 -1.20000 AFIX 0 C13 1 0.316820 1.155560 0.227694 11.00000 0.21865 0.12309 = 0.21410 0.06644 0.07833 0.06585 AFIX 137 H13A 2 0.326512 1.144318 0.174112 11.00000 -1.50000 H13B 2 0.362024 1.200208 0.249656 11.00000 -1.50000 H13C 2 0.266384 1.200326 0.234925 11.00000 -1.50000 AFIX 0 C14 1 0.487986 1.025962 0.293618 11.00000 0.14828 0.12869 = 0.11163 0.01691 0.01790 -0.02326 PART 1 AFIX 23 H14A 2 0.492211 1.097824 0.261533 21.00000 -1.20000 H14B 2 0.477453 1.053375 0.345339 21.00000 -1.20000 AFIX 23 PART 2 H14C 2 0.539124 0.981596 0.285350 -21.00000 -1.20000 H14D 2 0.490541 1.101731 0.265095 -21.00000 -1.20000 AFIX 0 PART 1 C9 1 0.343217 -0.062355 0.510309 21.00000 0.15536 0.09063 = 0.23060 0.00295 -0.00186 -0.03238 AFIX 137 H9A 2 0.337037 -0.058429 0.455886 21.00000 -1.50000 H9B 2 0.290578 -0.048636 0.534160 21.00000 -1.50000 H9C 2 0.363622 -0.141445 0.524484 21.00000 -1.50000 AFIX 0 C15 1 0.572602 0.956898 0.291980 21.00000 0.11376 0.21293 = 0.10731 0.00787 -0.01674 -0.02191 AFIX 137 H15A 2 0.573930 0.897650 0.332313 21.00000 -1.50000 H15B 2 0.616876 1.014230 0.298865 21.00000 -1.50000 H15C 2 0.578950 0.916413 0.243758 21.00000 -1.50000 AFIX 0 PART 2 C15A 1 0.476439 1.053463 0.380949 -21.00000 0.13993 0.17299 = 0.11895 -0.03842 -0.01708 -0.06933 AFIX 137 H15D 2 0.422635 1.026641 0.396938 -21.00000 -1.50000 H15E 2 0.481597 1.139622 0.389665 -21.00000 -1.50000 H15F 2 0.518029 1.010930 0.409606 -21.00000 -1.50000 AFIX 0 PART 0 C11 1 0.353765 0.852540 0.117867 11.00000 0.33089 0.17475 = 0.10415 0.00336 -0.05201 -0.08967 AFIX 137 H11A 2 0.374054 0.825397 0.069266 11.00000 -1.50000 H11B 2 0.309090 0.908954 0.110258 11.00000 -1.50000 H11C 2 0.334365 0.783652 0.146592 11.00000 -1.50000 AFIX 0 PART 2 C9A 1 0.288255 -0.027661 0.547561 -21.00000 0.17547 0.08347 = 0.21870 0.05378 -0.08621 -0.03304 AFIX 137 H9AA 2 0.274078 -0.013484 0.495113 -21.00000 -1.50000 H9AB 2 0.238946 -0.026710 0.578072 -21.00000 -1.50000 H9AC 2 0.314827 -0.105645 0.552277 -21.00000 -1.50000 AFIX 0 O1A 3 0.343023 0.065601 0.573111 -21.00000 0.16057 0.10336 = 0.16619 0.03806 -0.06031 -0.03827 C7A 1 0.413430 0.244024 0.542734 -21.00000 0.10556 0.10253 = 0.11565 0.02263 -0.02288 -0.01891 AFIX 43 H7A 2 0.458727 0.211796 0.568496 -21.00000 -1.20000 AFIX 0 C8A 1 0.417114 0.358600 0.513124 -21.00000 0.06452 0.08994 = 0.08513 0.00346 -0.00674 -0.01218 AFIX 43 H8A 2 0.448174 0.419282 0.536691 -21.00000 -1.20000 AFIX 0 C3A 1 0.373388 0.382300 0.447014 -21.00000 0.06082 0.09982 = 0.08247 0.00387 -0.00219 -0.00389 C4A 1 0.308201 0.303383 0.430790 -21.00000 0.07320 0.10186 = 0.11219 0.00181 -0.03266 -0.00255 AFIX 43 H4A 2 0.275070 0.319618 0.388616 -21.00000 -1.20000 AFIX 0 C5A 1 0.290542 0.200928 0.475213 -21.00000 0.08183 0.08905 = 0.09568 -0.01648 0.00192 0.00496 AFIX 43 H5A 2 0.245045 0.151960 0.464400 -21.00000 -1.20000 AFIX 0 C6A 1 0.341169 0.174620 0.534320 -21.00000 0.10059 0.07504 = 0.11803 0.00264 -0.01501 -0.00660 HKLF 4 REM appr4_0p45GPa_a.res in Pbca REM wR2 = 0.1402, GooF = S = 0.923, Restrained GooF = 0.897 for all data REM R1 = 0.0537 for 921 Fo > 4sig(Fo) and 0.2449 for all 3319 data REM 227 parameters refined using 206 restraints END WGHT 0.0310 0.0000 REM Highest difference peak 0.637, deepest hole -0.843, 1-sigma level 0.106 Q1 1 0.3096 0.6819 0.3276 11.00000 0.05 0.64 Q2 1 0.3405 0.7556 0.2745 11.00000 0.05 0.63 Q3 1 0.4414 0.7556 0.3854 11.00000 0.05 0.61 Q4 1 0.3318 0.7565 0.1778 11.00000 0.05 0.61 Q5 1 0.4704 0.6851 0.3299 11.00000 0.05 0.59 Q6 1 0.3155 0.8308 0.3296 11.00000 0.05 0.58 ; _shelx_res_checksum 61264 _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 2.758 _oxdiff_exptl_absorpt_empirical_full_min 0.681 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 0.38722(3) 0.75663(4) 0.32608(4) 0.0877(3) Uani 1 1 d . . . . . P1 P 0.4009(2) 0.9356(3) 0.2618(3) 0.0964(16) Uani 1 1 d . . . . . C2 C 0.3777(8) 0.4992(12) 0.4111(9) 0.077(5) Uani 1 1 d D . . . . C1 C 0.3786(7) 0.5993(12) 0.3829(10) 0.084(5) Uani 1 1 d . . . . . C7 C 0.4489(15) 0.2291(17) 0.5210(18) 0.114(13) Uani 0.732(18) 1 d D U P A 1 H7 H 0.491402 0.207899 0.554112 0.137 Uiso 0.732(18) 1 calc R U P A 1 C8 C 0.4460(12) 0.3437(14) 0.4920(13) 0.080(7) Uani 0.732(18) 1 d D U P A 1 H8 H 0.489024 0.397582 0.502426 0.096 Uiso 0.732(18) 1 calc R U P A 1 C3 C 0.381(3) 0.382(3) 0.448(3) 0.081(5) Uani 0.732(18) 1 d D U P A 1 C4 C 0.321(3) 0.294(3) 0.429(3) 0.096(7) Uani 0.732(18) 1 d D U P A 1 H4 H 0.278684 0.315532 0.396249 0.115 Uiso 0.732(18) 1 calc R U P A 1 C5 C 0.3241(13) 0.1763(15) 0.4588(14) 0.089(7) Uani 0.732(18) 1 d D U P A 1 H5 H 0.281483 0.121570 0.448773 0.107 Uiso 0.732(18) 1 calc R U P A 1 C6 C 0.3892(14) 0.1426(15) 0.5020(14) 0.095(8) Uani 0.732(18) 1 d D U P A 1 C10 C 0.4215(10) 0.9138(13) 0.1604(12) 0.121(6) Uani 1 1 d . . . . . H10A H 0.431646 0.992903 0.137344 0.146 Uiso 1 1 calc R U . . . H10B H 0.471534 0.865784 0.154890 0.146 Uiso 1 1 calc R U . . . O1 O 0.3999(12) 0.0284(12) 0.5345(13) 0.144(9) Uani 0.732(18) 1 d D U P A 1 C12 C 0.3097(9) 1.0299(11) 0.2669(11) 0.121(6) Uani 1 1 d . . . . . H12A H 0.264003 0.985776 0.243890 0.145 Uiso 1 1 calc R U . . . H12B H 0.296046 1.042719 0.320215 0.145 Uiso 1 1 calc R U . . . C13 C 0.3168(10) 1.1556(12) 0.2277(14) 0.185(10) Uani 1 1 d . . . . . H13A H 0.326512 1.144318 0.174112 0.278 Uiso 1 1 calc R U . . . H13B H 0.362024 1.200208 0.249656 0.278 Uiso 1 1 calc R U . . . H13C H 0.266384 1.200326 0.234925 0.278 Uiso 1 1 calc R U . . . C14 C 0.4880(10) 1.0260(13) 0.2936(13) 0.130(7) Uani 1 1 d D . . . . H14A H 0.492211 1.097824 0.261533 0.155 Uiso 0.732(18) 1 calc R U P A 1 H14B H 0.477453 1.053375 0.345339 0.155 Uiso 0.732(18) 1 calc R U P A 1 H14C H 0.539124 0.981596 0.285350 0.155 Uiso 0.268(18) 1 calc R U P A 2 H14D H 0.490541 1.101731 0.265095 0.155 Uiso 0.268(18) 1 calc R U P A 2 C9 C 0.3432(16) -0.0624(18) 0.510(2) 0.159(15) Uani 0.732(18) 1 d D U P A 1 H9A H 0.337037 -0.058429 0.455886 0.238 Uiso 0.732(18) 1 calc R U P A 1 H9B H 0.290578 -0.048636 0.534160 0.238 Uiso 0.732(18) 1 calc R U P A 1 H9C H 0.363622 -0.141445 0.524484 0.238 Uiso 0.732(18) 1 calc R U P A 1 C15 C 0.5726(12) 0.957(2) 0.2920(16) 0.145(11) Uani 0.732(18) 1 d D . P A 1 H15A H 0.573930 0.897650 0.332313 0.217 Uiso 0.732(18) 1 calc R U P A 1 H15B H 0.616876 1.014230 0.298865 0.217 Uiso 0.732(18) 1 calc R U P A 1 H15C H 0.578950 0.916413 0.243758 0.217 Uiso 0.732(18) 1 calc R U P A 1 C15A C 0.476(4) 1.053(5) 0.381(2) 0.14(3) Uani 0.268(18) 1 d D . P A 2 H15D H 0.422635 1.026641 0.396938 0.216 Uiso 0.268(18) 1 calc R U P A 2 H15E H 0.481597 1.139622 0.389665 0.216 Uiso 0.268(18) 1 calc R U P A 2 H15F H 0.518029 1.010930 0.409606 0.216 Uiso 0.268(18) 1 calc R U P A 2 C11 C 0.3538(13) 0.8525(17) 0.1179(15) 0.203(11) Uani 1 1 d . . . . . H11A H 0.374054 0.825397 0.069266 0.305 Uiso 1 1 calc R U . . . H11B H 0.309090 0.908954 0.110258 0.305 Uiso 1 1 calc R U . . . H11C H 0.334365 0.783652 0.146592 0.305 Uiso 1 1 calc R U . . . C9A C 0.288(4) -0.028(4) 0.548(6) 0.16(3) Uani 0.268(18) 1 d D U P A 2 H9AA H 0.274078 -0.013484 0.495113 0.239 Uiso 0.268(18) 1 calc R U P A 2 H9AB H 0.238946 -0.026710 0.578072 0.239 Uiso 0.268(18) 1 calc R U P A 2 H9AC H 0.314827 -0.105645 0.552277 0.239 Uiso 0.268(18) 1 calc R U P A 2 O1A O 0.343(3) 0.066(3) 0.573(3) 0.143(16) Uani 0.268(18) 1 d D U P A 2 C7A C 0.413(4) 0.244(5) 0.543(5) 0.11(2) Uani 0.268(18) 1 d D U P A 2 H7A H 0.458727 0.211796 0.568496 0.129 Uiso 0.268(18) 1 calc R U P A 2 C8A C 0.417(3) 0.359(4) 0.513(3) 0.080(7) Uani 0.268(18) 1 d D U P A 2 H8A H 0.448174 0.419282 0.536691 0.096 Uiso 0.268(18) 1 calc R U P A 2 C3A C 0.373(7) 0.382(7) 0.447(8) 0.081(5) Uani 0.268(18) 1 d D U P A 2 C4A C 0.308(7) 0.303(8) 0.431(7) 0.096(7) Uani 0.268(18) 1 d D U P A 2 H4A H 0.275070 0.319618 0.388616 0.115 Uiso 0.268(18) 1 calc R U P A 2 C5A C 0.291(3) 0.201(4) 0.475(3) 0.089(7) Uani 0.268(18) 1 d D U P A 2 H5A H 0.245045 0.151960 0.464400 0.107 Uiso 0.268(18) 1 calc R U P A 2 C6A C 0.341(3) 0.175(3) 0.534(3) 0.098(14) Uani 0.268(18) 1 d D 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 0.0831(5) 0.0892(4) 0.0908(7) 0.0065(4) 0.0084(3) 0.0015(3) P1 0.099(3) 0.093(2) 0.097(6) 0.011(3) 0.018(3) -0.001(2) C2 0.101(12) 0.081(8) 0.050(17) 0.004(8) -0.001(7) 0.003(8) C1 0.082(11) 0.105(10) 0.065(17) -0.008(10) -0.007(8) 0.007(8) C7 0.098(19) 0.106(10) 0.14(3) 0.039(14) -0.034(19) -0.014(10) C8 0.065(13) 0.090(7) 0.085(15) 0.003(9) -0.007(10) -0.012(8) C3 0.061(11) 0.100(8) 0.082(13) 0.004(8) -0.002(8) -0.004(6) C4 0.073(13) 0.102(8) 0.112(13) 0.002(8) -0.033(9) -0.003(8) C5 0.082(15) 0.089(8) 0.096(16) -0.016(9) 0.002(10) 0.005(9) C6 0.096(16) 0.077(8) 0.11(2) 0.011(11) -0.007(12) 0.000(8) C10 0.157(17) 0.117(11) 0.09(2) -0.006(10) 0.015(10) 0.014(9) O1 0.17(2) 0.086(8) 0.17(2) 0.033(11) -0.054(14) -0.027(9) C12 0.141(12) 0.107(9) 0.11(2) 0.025(10) 0.026(10) 0.036(9) C13 0.22(2) 0.123(12) 0.21(3) 0.066(14) 0.078(16) 0.066(12) C14 0.148(13) 0.129(11) 0.11(2) 0.017(13) 0.018(12) -0.023(10) C9 0.16(3) 0.091(13) 0.23(5) 0.003(18) 0.00(2) -0.032(15) C15 0.114(18) 0.21(2) 0.11(3) 0.01(2) -0.017(15) -0.022(14) C15A 0.14(6) 0.17(5) 0.12(3) -0.04(4) -0.02(3) -0.07(4) C11 0.33(3) 0.175(17) 0.10(3) 0.003(17) -0.052(19) -0.090(17) C9A 0.18(6) 0.08(3) 0.22(8) 0.05(4) -0.09(5) -0.03(3) O1A 0.16(4) 0.103(19) 0.17(4) 0.04(2) -0.06(3) -0.038(18) C7A 0.11(3) 0.103(16) 0.12(4) 0.02(2) -0.02(3) -0.019(18) C8A 0.065(13) 0.090(7) 0.085(15) 0.003(9) -0.007(10) -0.012(8) C3A 0.061(11) 0.100(8) 0.082(13) 0.004(8) -0.002(8) -0.004(6) C4A 0.073(13) 0.102(8) 0.112(13) 0.002(8) -0.033(9) -0.003(8) C5A 0.082(15) 0.089(8) 0.096(16) -0.016(9) 0.002(10) 0.005(9) C6A 0.10(2) 0.075(19) 0.12(3) 0.003(19) -0.02(2) -0.007(16) 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_ _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 178.4(4) . . ? C10 P1 Au1 112.8(5) . . ? C12 P1 Au1 113.0(5) . . ? C12 P1 C10 105.8(8) . . ? C12 P1 C14 107.9(8) . . ? C14 P1 Au1 113.3(6) . . ? C14 P1 C10 103.3(8) . . ? C1 C2 C3 176.6(17) . . ? C1 C2 C3A 177(8) . . ? C2 C1 Au1 173.4(14) . . ? C8 C7 H7 119.4 . . ? C8 C7 C6 121.2(17) . . ? C6 C7 H7 119.4 . . ? C7 C8 H8 119.3 . . ? C7 C8 C3 121.4(14) . . ? C3 C8 H8 119.3 . . ? C8 C3 C2 123.4(16) . . ? C8 C3 C4 116.5(18) . . ? C4 C3 C2 119.4(15) . . ? C3 C4 H4 118.9 . . ? C5 C4 C3 122.2(17) . . ? C5 C4 H4 118.9 . . ? C4 C5 H5 120.4 . . ? C6 C5 C4 119.1(16) . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 119.2(16) . . ? C5 C6 O1 125.2(17) . . ? O1 C6 C7 115.5(16) . . ? P1 C10 H10A 108.7 . . ? P1 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C10 P1 114.4(16) . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C6 O1 C9 115.4(17) . . ? P1 C12 H12A 108.4 . . ? P1 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C13 C12 P1 115.3(10) . . ? C13 C12 H12A 108.4 . . ? C13 C12 H12B 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? P1 C14 H14A 108.7 . . ? P1 C14 H14B 108.7 . . ? P1 C14 H14C 110.1 . . ? P1 C14 H14D 110.1 . . ? H14A C14 H14B 107.6 . . ? H14C C14 H14D 108.4 . . ? C15 C14 P1 114.2(13) . . ? C15 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C15A C14 P1 108(2) . . ? C15A C14 H14C 110.1 . . ? C15A C14 H14D 110.1 . . ? 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 . . ? 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 . . ? 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 . . ? 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 117(3) . . ? C8A C7A H7A 120.1 . . ? C8A C7A C6A 120(3) . . ? C6A C7A H7A 120.1 . . ? C7A C8A H8A 120.9 . . ? C7A C8A C3A 118(3) . . ? C3A C8A H8A 120.9 . . ? C8A C3A C2 121(4) . . ? C8A C3A C4A 116(4) . . ? C4A C3A C2 120(3) . . ? C3A C4A H4A 118.6 . . ? C3A C4A C5A 123(3) . . ? C5A C4A H4A 118.6 . . ? C4A C5A H5A 120.8 . . ? C6A C5A C4A 118(2) . . ? C6A C5A H5A 120.8 . . ? O1A C6A C7A 114(3) . . ? C5A C6A O1A 125(3) . . ? C5A C6A C7A 118(3) . . ? 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 2.272(4) . ? Au1 C1 1.995(15) . ? P1 C10 1.82(2) . ? P1 C12 1.803(12) . ? P1 C14 1.810(16) . ? C2 C1 1.203(16) . ? C2 C3 1.435(19) . ? C2 C3A 1.43(2) . ? C7 H7 0.9300 . ? C7 C8 1.355(17) . ? C7 C6 1.39(2) . ? C8 H8 0.9300 . ? C8 C3 1.38(2) . ? C3 C4 1.394(16) . ? C4 H4 0.9300 . ? C4 C5 1.39(2) . ? C5 H5 0.9300 . ? C5 C6 1.35(2) . ? C6 O1 1.386(18) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.48(2) . ? O1 C9 1.418(16) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.544(18) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C14 H14D 0.9700 . ? C14 C15 1.56(2) . ? C14 C15A 1.57(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15A H15D 0.9600 . ? C15A H15E 0.9600 . ? C15A H15F 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9A H9AA 0.9600 . ? C9A H9AB 0.9600 . ? C9A H9AC 0.9600 . ? C9A O1A 1.42(2) . ? O1A C6A 1.37(2) . ? C7A H7A 0.9300 . ? C7A C8A 1.36(2) . ? C7A C6A 1.40(3) . ? C8A H8A 0.9300 . ? C8A C3A 1.38(3) . ? C3A C4A 1.39(2) . ? C4A H4A 0.9300 . ? C4A C5A 1.40(3) . ? C5A H5A 0.9300 . ? C5A C6A 1.35(3) . ? 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 63.6(14) . . . . ? Au1 P1 C12 C13 177.0(14) . . . . ? Au1 P1 C14 C15 54.6(17) . . . . ? Au1 P1 C14 C15A -59(3) . . . . ? C2 C3 C4 C5 176(5) . . . . ? C2 C3A C4A C5A -166(14) . . . . ? C7 C8 C3 C2 -175(4) . . . . ? C7 C8 C3 C4 -5(7) . . . . ? C7 C6 O1 C9 -175(2) . . . . ? C8 C7 C6 C5 -5(4) . . . . ? C8 C7 C6 O1 179(2) . . . . ? C8 C3 C4 C5 5(8) . . . . ? C3 C4 C5 C6 -5(7) . . . . ? C4 C5 C6 C7 5(5) . . . . ? C4 C5 C6 O1 -180(4) . . . . ? C5 C6 O1 C9 10(4) . . . . ? C6 C7 C8 C3 5(5) . . . . ? C10 P1 C12 C13 -59.0(17) . . . . ? C10 P1 C14 C15 -67.8(16) . . . . ? C10 P1 C14 C15A 179(3) . . . . ? C12 P1 C10 C11 -60.5(14) . . . . ? C12 P1 C14 C15 -179.6(15) . . . . ? C12 P1 C14 C15A 67(3) . . . . ? C14 P1 C10 C11 -173.7(13) . . . . ? C14 P1 C12 C13 51.0(19) . . . . ? C9A O1A C6A C7A -158(7) . . . . ? C9A O1A C6A C5A 1(10) . . . . ? C7A C8A C3A C2 -177(11) . . . . ? C7A C8A C3A C4A 21(17) . . . . ? C8A C7A C6A O1A -174(7) . . . . ? C8A C7A C6A C5A 25(11) . . . . ? C8A C3A C4A C5A -4(22) . . . . ? C3A C4A C5A C6A -3(19) . . . . ? C4A C5A C6A O1A -166(9) . . . . ? C4A C5A C6A C7A -7(12) . . . . ? C6A C7A C8A C3A -32(12) . . . . ?