#------------------------------------------------------------------------------ #$Date: 2025-01-10 01:45:50 +0200 (Fri, 10 Jan 2025) $ #$Revision: 297250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573654.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_1573654 _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 direct _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 16.0628(9) _cell_length_b 11.0945(4) _cell_length_c 17.7070(6) _cell_measurement_reflns_used 5564 _cell_measurement_temperature 295.5(3) _cell_measurement_theta_max 24.5360 _cell_measurement_theta_min 2.0580 _cell_volume 3155.5(2) _computing_cell_refinement 'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)' _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 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment 'Diamond Anvil Cell filled with silicone oil' _diffrn_ambient_pressure 330000 _diffrn_ambient_temperature 295.5(3) _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 0.919 _diffrn_measured_fraction_theta_max 0.914 _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 10.00 35.00 1.00 60.00 -- 22.04 53.00 -17.00 25 2 \w -20.00 51.00 1.00 90.00 -- 22.04 -53.00 17.00 71 3 \w -27.00 51.00 1.00 90.00 -- 22.04 -39.00-167.00 78 4 \w -50.00 45.00 1.00 90.00 -- 22.04 26.00 -8.00 95 5 \w -13.00 17.00 1.00 90.00 -- 22.04 97.00 143.00 30 6 \w -20.00 7.00 1.00 90.00 -- 22.04 114.00 -45.00 27 7 \w -32.00 -6.00 1.00 90.00 -- 22.04 39.00 167.00 26 8 \w -67.00 -13.00 1.00 90.00 -- -22.19 135.00 123.00 54 9 \w -23.00 28.00 1.00 90.00 -- -22.19 39.00 -12.00 51 10 \w -85.00 1.00 1.00 90.00 -- -22.19 114.00 -45.00 86 11 \w -45.00 48.00 1.00 90.00 -- -22.19 -26.00 8.00 93 12 \w -34.00 29.00 1.00 90.00 -- -22.19 53.00 162.00 63 13 \w -17.00 21.00 1.00 90.00 -- -22.19 -97.00-143.00 38 14 \w -16.00 21.00 1.00 90.00 -- -22.19 -97.00 35.00 37 15 \w -50.00 45.00 1.00 15.00 -- 22.04 26.00 -8.00 95 ; _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 51 deg.' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0280698018 _diffrn_orient_matrix_UB_12 0.0291718516 _diffrn_orient_matrix_UB_13 0.0039395935 _diffrn_orient_matrix_UB_21 0.0085926994 _diffrn_orient_matrix_UB_22 -0.0262371656 _diffrn_orient_matrix_UB_23 0.0258332096 _diffrn_orient_matrix_UB_31 0.0187233879 _diffrn_orient_matrix_UB_32 -0.0316895172 _diffrn_orient_matrix_UB_33 -0.0177534866 _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 0.0850 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_Laue_measured_fraction_full 0.919 _diffrn_reflns_Laue_measured_fraction_max 0.914 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 35162 _diffrn_reflns_point_group_measured_fraction_full 0.919 _diffrn_reflns_point_group_measured_fraction_max 0.914 _diffrn_reflns_theta_full 19.665 _diffrn_reflns_theta_max 20.510 _diffrn_reflns_theta_min 1.815 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Ag) X-ray Source' _exptl_absorpt_coefficient_mu 5.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.36a (Rigaku Oxford Diffraction, 2021) 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 1.879 _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 0.33 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 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 1.075 _refine_diff_density_min -1.755 _refine_diff_density_rms 0.151 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 2939 _refine_ls_number_restraints 204 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0522 _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^)+(0.0739P)^2^+10.8659P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1311 _refine_ls_wR_factor_ref 0.1734 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1505 _reflns_number_total 2939 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4dt03036b2.cif _cod_data_source_block appr5_0p33GPa _cod_database_code 1573654 _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. ; _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 C3A \\sim C3 \\sim C8A \\sim C8 \\sim C7A \\sim C7 \\sim C6A \\sim C6 \\sim C5A \\sim C5 \\sim C4A \\sim C4: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A C9A \\sim C9 \\sim O1A \\sim O1: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A 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(C8A)=Sof(H8A)=Sof(C7A)= Sof(H7A)=Sof(C6A)=Sof(C5A)=Sof(H5A)=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) 4.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C10(H10A,H10B), C14(H14C,H14D), C14(H14A,H14B) 4.b Me refined with riding coordinates: C15A(H15A,H15B,H15C) 4.c Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C4(H4), C5(H5), C8A(H8A), C7A(H7A), C5A(H5A), C4A(H4A) 4.d Fitted hexagon refined as free rotating group: C3A(C8A,C7A,C6A,C5A,C4A) 4.e Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C9A(H9AA,H9AB, H9AC), C15(H15D,H15E,H15F) ; _shelx_res_file ; TITL appr5_0p33GPa in Pbca #61 appr5_0p33GPa.res created by SHELXL-2018/3 at 15:28:05 on 08-Feb-2024 REM reset to Pbca #61 CELL 0.56087 16.062834 11.094471 17.706985 90 90 90 ZERR 8 0.000857 0.000432 0.000582 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H Au O P 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 C3A C3 C8A C8 C7A C7 C6A C6 C5A C5 C4A C4 SIMU 0.04 0.08 1.7 C9A C9 O1A O1 L.S. 20 PLAN 8 TEMP 22 CONF BOND MORE -1 BOND $H fmap -2 acta SHEL 200 0.8 REM REM REM WGHT 0.073900 10.865901 FVAR 0.49566 0.74707 AU1 3 0.388343 0.753050 0.325895 11.00000 0.06227 0.06945 = 0.07286 0.00510 0.00510 0.00030 P1 5 0.402692 0.930319 0.262041 11.00000 0.07368 0.06909 = 0.07682 0.00804 0.01648 0.00239 PART 1 C7 1 0.446207 0.227991 0.520386 21.00000 0.08751 0.09572 = 0.05332 0.01610 -0.01838 -0.02501 AFIX 43 H7 2 0.489470 0.204343 0.551990 21.00000 -1.20000 AFIX 0 C8 1 0.443743 0.343752 0.494746 21.00000 0.08500 0.07583 = 0.06125 0.01064 -0.00774 -0.02905 AFIX 43 H8 2 0.484318 0.397686 0.510924 21.00000 -1.20000 AFIX 0 C3 1 0.382329 0.384072 0.444997 21.00000 0.05908 0.06903 = 0.06188 0.00770 0.00298 -0.02075 C4 1 0.323900 0.299747 0.426582 21.00000 0.06644 0.08190 = 0.07191 0.00488 -0.01382 -0.00906 AFIX 43 H4 2 0.280649 0.322338 0.394664 21.00000 -1.20000 AFIX 0 C5 1 0.325699 0.181551 0.453135 21.00000 0.08448 0.08219 = 0.07522 -0.01423 -0.00579 -0.02977 AFIX 43 H5 2 0.284927 0.127100 0.438082 21.00000 -1.20000 AFIX 0 C6 1 0.386758 0.146002 0.500813 21.00000 0.09107 0.08444 = 0.06383 0.00910 -0.00680 -0.01960 PART 0 C12 1 0.311707 1.024658 0.267693 11.00000 0.09472 0.08684 = 0.10507 0.01821 0.00999 0.01791 AFIX 23 H12A 2 0.265085 0.980823 0.246295 11.00000 -1.20000 H12B 2 0.299303 1.038664 0.320582 11.00000 -1.20000 AFIX 0 PART 1 O1 4 0.396533 0.032439 0.530985 21.00000 0.15617 0.07573 = 0.09859 0.01221 -0.02776 -0.00596 PART 0 C2 1 0.378651 0.498112 0.411017 11.00000 0.05926 0.06938 = 0.07176 0.00271 -0.00454 -0.00591 C1 1 0.379795 0.597327 0.381210 11.00000 0.04824 0.09047 = 0.08068 -0.00491 -0.00055 0.00601 C10 1 0.423298 0.913115 0.161581 11.00000 0.10482 0.07799 = 0.08934 0.00069 0.01880 -0.01262 AFIX 23 H10A 2 0.430382 0.992214 0.139145 11.00000 -1.20000 H10B 2 0.474936 0.869038 0.154947 11.00000 -1.20000 AFIX 0 C13 1 0.317621 1.146232 0.228290 11.00000 0.15386 0.09716 = 0.16157 0.03903 0.01712 0.04180 AFIX 137 H13A 2 0.327648 1.134072 0.175388 11.00000 -1.50000 H13B 2 0.362579 1.191865 0.249705 11.00000 -1.50000 H13C 2 0.266368 1.189466 0.234916 11.00000 -1.50000 AFIX 0 C11 1 0.353564 0.846793 0.120426 11.00000 0.19370 0.14205 = 0.09248 -0.00209 -0.00163 -0.04520 AFIX 137 H11A 2 0.372045 0.824795 0.070743 11.00000 -1.50000 H11B 2 0.305790 0.898415 0.116550 11.00000 -1.50000 H11C 2 0.338975 0.775431 0.148084 11.00000 -1.50000 AFIX 0 C14 1 0.490263 1.020061 0.296376 11.00000 0.09090 0.09106 = 0.11283 0.00306 0.00353 -0.02399 PART 2 AFIX 23 H14C 2 0.540745 0.972591 0.292006 -21.00000 -1.20000 H14D 2 0.496475 1.090246 0.264200 -21.00000 -1.20000 AFIX 23 PART 1 H14A 2 0.494209 1.093049 0.266431 21.00000 -1.20000 H14B 2 0.479418 1.043603 0.348208 21.00000 -1.20000 AFIX 0 PART 2 C15A 1 0.480501 1.065332 0.384366 -21.00000 0.32699 0.09184 = 0.24456 -0.05602 -0.08315 0.07240 AFIX 33 H15A 2 0.528515 1.111688 0.398461 -21.00000 -1.50000 H15B 2 0.431484 1.114263 0.389083 -21.00000 -1.50000 H15C 2 0.475806 0.996473 0.416921 -21.00000 -1.50000 AFIX 0 PART 1 C9 1 0.343232 -0.057252 0.508299 21.00000 0.19263 0.05177 = 0.10736 0.00197 0.01136 -0.00716 AFIX 137 H9A 2 0.331948 -0.048853 0.455320 21.00000 -1.50000 H9B 2 0.292106 -0.051283 0.536126 21.00000 -1.50000 H9C 2 0.368370 -0.134343 0.517589 21.00000 -1.50000 AFIX 0 PART 2 C9A 1 0.292143 -0.025641 0.545780 -21.00000 0.16940 0.05604 = 0.15929 -0.00112 -0.01815 -0.05860 AFIX 137 H9AA 2 0.324483 -0.089336 0.523736 -21.00000 -1.50000 H9AB 2 0.253580 0.004888 0.509042 -21.00000 -1.50000 H9AC 2 0.262011 -0.056197 0.588508 -21.00000 -1.50000 AFIX 0 O1A 4 0.347359 0.071141 0.570165 -21.00000 0.12678 0.06842 = 0.12026 0.02810 -0.03833 -0.03694 AFIX 66 C3A 1 0.363970 0.377413 0.447172 -21.00000 0.06525 0.07285 = 0.06193 0.00439 -0.01116 -0.01387 C8A 1 0.417414 0.357488 0.507637 -21.00000 0.07267 0.07058 = 0.06117 0.01076 -0.00843 -0.02600 AFIX 43 H8A 2 0.457860 0.414314 0.519663 -21.00000 -1.20000 AFIX 65 C7A 1 0.410406 0.252631 0.550127 -21.00000 0.08307 0.08947 = 0.05789 0.00500 -0.00961 -0.01561 AFIX 43 H7A 2 0.446163 0.239301 0.590581 -21.00000 -1.20000 AFIX 65 C6A 1 0.349954 0.167698 0.532153 -21.00000 0.08183 0.08763 = 0.07060 0.01000 -0.00968 -0.02420 C5A 1 0.296510 0.187622 0.471689 -21.00000 0.08183 0.09029 = 0.07087 0.00219 0.00343 -0.01296 AFIX 43 H5A 2 0.256064 0.130796 0.459663 -21.00000 -1.20000 AFIX 65 C4A 1 0.303517 0.292479 0.429198 -21.00000 0.06820 0.07281 = 0.07248 -0.00505 -0.01332 -0.01614 AFIX 43 H4A 2 0.267760 0.305809 0.388743 -21.00000 -1.20000 AFIX 0 PART 1 C15 1 0.572275 0.954851 0.293105 21.00000 0.07703 0.15520 = 0.08386 0.03503 -0.00506 -0.01381 AFIX 137 H15D 2 0.572503 0.890827 0.329576 21.00000 -1.50000 H15E 2 0.616557 1.010216 0.304168 21.00000 -1.50000 H15F 2 0.580112 0.921889 0.243483 21.00000 -1.50000 AFIX 0 HKLF 4 REM appr5_0p33GPa in Pbca #61 REM wR2 = 0.1734, GooF = S = 1.040, Restrained GooF = 1.005 for all data REM R1 = 0.0522 for 1505 Fo > 4sig(Fo) and 0.1092 for all 2939 data REM 238 parameters refined using 204 restraints END WGHT 0.0740 10.8728 REM Highest difference peak 1.075, deepest hole -1.755, 1-sigma level 0.151 Q1 1 0.3897 0.6815 0.3459 11.00000 0.05 -1.76 Q2 1 0.3895 0.8215 0.3491 11.00000 0.05 -1.51 Q3 1 0.4112 0.8208 0.3323 11.00000 0.05 -1.48 Q4 1 0.3335 0.7514 0.1719 11.00000 0.05 1.07 Q5 1 0.3520 0.7552 0.2881 11.00000 0.05 -1.03 Q6 1 0.4223 0.7505 0.2840 11.00000 0.05 -0.95 Q7 1 0.3895 0.7502 0.0219 11.00000 0.05 0.93 Q8 1 0.3475 0.7521 0.3645 11.00000 0.05 -0.92 ; _shelx_res_checksum 87868 _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 2.051 _oxdiff_exptl_absorpt_empirical_full_min 0.763 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.38834(3) 0.75305(4) 0.32590(3) 0.0682(3) Uani 1 1 d . . . . . P1 P 0.4027(2) 0.9303(3) 0.26204(18) 0.0732(10) Uani 1 1 d . . . . . C7 C 0.4462(16) 0.2280(17) 0.5204(10) 0.079(6) Uani 0.747(19) 1 d . U P A 1 H7 H 0.489470 0.204343 0.551990 0.095 Uiso 0.747(19) 1 calc R U P A 1 C8 C 0.4437(17) 0.344(2) 0.4947(13) 0.074(7) Uani 0.747(19) 1 d . U P A 1 H8 H 0.484318 0.397686 0.510924 0.089 Uiso 0.747(19) 1 calc R U P A 1 C3 C 0.3823(19) 0.384(2) 0.4450(16) 0.063(6) Uani 0.747(19) 1 d . U P A 1 C4 C 0.3239(19) 0.300(3) 0.4266(15) 0.073(6) Uani 0.747(19) 1 d . U P A 1 H4 H 0.280649 0.322338 0.394664 0.088 Uiso 0.747(19) 1 calc R U P A 1 C5 C 0.3257(15) 0.182(2) 0.4531(12) 0.081(7) Uani 0.747(19) 1 d . U P A 1 H5 H 0.284927 0.127100 0.438082 0.097 Uiso 0.747(19) 1 calc R U P A 1 C6 C 0.3868(16) 0.146(2) 0.5008(11) 0.080(6) Uani 0.747(19) 1 d . U P A 1 C12 C 0.3117(10) 1.0247(11) 0.2677(8) 0.096(5) Uani 1 1 d . . . . . H12A H 0.265085 0.980823 0.246295 0.115 Uiso 1 1 calc R U . . . H12B H 0.299303 1.038664 0.320582 0.115 Uiso 1 1 calc R U . . . O1 O 0.3965(14) 0.0324(15) 0.5310(10) 0.110(6) Uani 0.747(19) 1 d . U P A 1 C2 C 0.3787(8) 0.4981(12) 0.4110(6) 0.067(4) Uani 1 1 d . . . . . C1 C 0.3798(8) 0.5973(12) 0.3812(7) 0.073(4) Uani 1 1 d . . . . . C10 C 0.4233(10) 0.9131(12) 0.1616(7) 0.091(5) Uani 1 1 d . . . . . H10A H 0.430382 0.992214 0.139145 0.109 Uiso 1 1 calc R U . . . H10B H 0.474936 0.869038 0.154947 0.109 Uiso 1 1 calc R U . . . C13 C 0.3176(12) 1.1462(13) 0.2283(9) 0.138(7) Uani 1 1 d . . . . . H13A H 0.327648 1.134072 0.175388 0.206 Uiso 1 1 calc R U . . . H13B H 0.362579 1.191865 0.249705 0.206 Uiso 1 1 calc R U . . . H13C H 0.266368 1.189466 0.234916 0.206 Uiso 1 1 calc R U . . . C11 C 0.3536(13) 0.8468(17) 0.1204(8) 0.143(7) Uani 1 1 d . . . . . H11A H 0.372045 0.824795 0.070743 0.214 Uiso 1 1 calc R U . . . H11B H 0.305790 0.898415 0.116550 0.214 Uiso 1 1 calc R U . . . H11C H 0.338975 0.775431 0.148084 0.214 Uiso 1 1 calc R U . . . C14 C 0.4903(11) 1.0201(13) 0.2964(8) 0.098(5) Uani 1 1 d . . . . . H14C H 0.540745 0.972591 0.292006 0.118 Uiso 0.253(19) 1 calc R U P A 2 H14D H 0.496475 1.090246 0.264200 0.118 Uiso 0.253(19) 1 calc R U P A 2 H14A H 0.494209 1.093049 0.266431 0.118 Uiso 0.747(19) 1 calc R U P A 1 H14B H 0.479418 1.043603 0.348208 0.118 Uiso 0.747(19) 1 calc R U P A 1 C15A C 0.481(7) 1.065(6) 0.384(5) 0.22(6) Uani 0.253(19) 1 d . . P A 2 H15A H 0.528515 1.111688 0.398461 0.332 Uiso 0.253(19) 1 calc R U P A 2 H15B H 0.431484 1.114263 0.389083 0.332 Uiso 0.253(19) 1 calc R U P A 2 H15C H 0.475806 0.996473 0.416921 0.332 Uiso 0.253(19) 1 calc R U P A 2 C9 C 0.343(2) -0.0573(19) 0.5083(14) 0.117(10) Uani 0.747(19) 1 d . U P A 1 H9A H 0.331948 -0.048853 0.455320 0.176 Uiso 0.747(19) 1 calc R U P A 1 H9B H 0.292106 -0.051283 0.536126 0.176 Uiso 0.747(19) 1 calc R U P A 1 H9C H 0.368370 -0.134343 0.517589 0.176 Uiso 0.747(19) 1 calc R U P A 1 C9A C 0.292(6) -0.026(6) 0.546(5) 0.13(2) Uani 0.253(19) 1 d . U P A 2 H9AA H 0.324483 -0.089336 0.523736 0.192 Uiso 0.253(19) 1 calc R U P A 2 H9AB H 0.253580 0.004888 0.509042 0.192 Uiso 0.253(19) 1 calc R U P A 2 H9AC H 0.262011 -0.056197 0.588508 0.192 Uiso 0.253(19) 1 calc R U P A 2 O1A O 0.347(4) 0.071(4) 0.570(3) 0.105(14) Uani 0.253(19) 1 d . U P A 2 C3A C 0.364(6) 0.377(6) 0.447(5) 0.067(11) Uani 0.253(19) 1 d G U P A 2 C8A C 0.417(4) 0.357(5) 0.508(4) 0.068(11) Uani 0.253(19) 1 d G U P A 2 H8A H 0.457860 0.414314 0.519663 0.082 Uiso 0.253(19) 1 calc R U P A 2 C7A C 0.410(3) 0.253(5) 0.550(3) 0.077(10) Uani 0.253(19) 1 d G U P A 2 H7A H 0.446163 0.239301 0.590581 0.092 Uiso 0.253(19) 1 calc R U P A 2 C6A C 0.350(4) 0.168(4) 0.532(3) 0.080(10) Uani 0.253(19) 1 d G U P A 2 C5A C 0.297(4) 0.188(6) 0.472(3) 0.081(11) Uani 0.253(19) 1 d G U P A 2 H5A H 0.256064 0.130796 0.459663 0.097 Uiso 0.253(19) 1 calc R U P A 2 C4A C 0.304(5) 0.292(8) 0.429(4) 0.071(11) Uani 0.253(19) 1 d G U P A 2 H4A H 0.267760 0.305809 0.388743 0.085 Uiso 0.253(19) 1 calc R U P A 2 C15 C 0.5723(14) 0.955(2) 0.2931(10) 0.105(8) Uani 0.747(19) 1 d . . P A 1 H15D H 0.572503 0.890827 0.329576 0.158 Uiso 0.747(19) 1 calc R U P A 1 H15E H 0.616557 1.010216 0.304168 0.158 Uiso 0.747(19) 1 calc R U P A 1 H15F H 0.580112 0.921889 0.243483 0.158 Uiso 0.747(19) 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 0.0623(5) 0.0695(4) 0.0729(4) 0.0051(2) 0.0051(2) 0.0003(3) P1 0.074(3) 0.069(2) 0.0768(19) 0.0080(17) 0.0165(19) 0.0024(17) C7 0.088(17) 0.096(12) 0.053(9) 0.016(9) -0.018(9) -0.025(11) C8 0.085(18) 0.076(10) 0.061(11) 0.011(8) -0.008(10) -0.029(11) C3 0.059(16) 0.069(10) 0.062(9) 0.008(8) 0.003(9) -0.021(9) C4 0.066(18) 0.082(11) 0.072(10) 0.005(8) -0.014(10) -0.009(12) C5 0.084(18) 0.082(11) 0.075(11) -0.014(9) -0.006(11) -0.030(12) C6 0.091(17) 0.084(11) 0.064(10) 0.009(9) -0.007(10) -0.020(11) C12 0.095(15) 0.087(10) 0.105(10) 0.018(8) 0.010(9) 0.018(8) O1 0.16(2) 0.076(10) 0.099(11) 0.012(8) -0.028(11) -0.006(10) C2 0.059(11) 0.069(9) 0.072(7) 0.003(6) -0.005(6) -0.006(6) C1 0.048(10) 0.090(9) 0.081(8) -0.005(7) -0.001(6) 0.006(6) C10 0.105(14) 0.078(9) 0.089(9) 0.001(7) 0.019(9) -0.013(8) C13 0.15(2) 0.097(12) 0.162(15) 0.039(11) 0.017(13) 0.042(11) C11 0.19(2) 0.142(15) 0.092(11) -0.002(11) -0.002(13) -0.045(14) C14 0.091(16) 0.091(10) 0.113(11) 0.003(9) 0.004(10) -0.024(9) C15A 0.33(16) 0.09(5) 0.24(10) -0.06(6) -0.08(10) 0.07(7) C9 0.19(3) 0.052(13) 0.107(17) 0.002(11) 0.011(17) -0.007(15) C9A 0.17(5) 0.06(3) 0.16(5) 0.00(3) -0.02(4) -0.06(3) O1A 0.13(3) 0.07(2) 0.12(3) 0.03(2) -0.04(2) -0.04(2) C3A 0.07(2) 0.073(18) 0.062(17) 0.004(17) -0.011(18) -0.014(18) C8A 0.07(2) 0.071(17) 0.061(18) 0.011(16) -0.008(18) -0.026(18) C7A 0.08(2) 0.089(18) 0.058(18) 0.005(17) -0.010(17) -0.016(18) C6A 0.08(2) 0.088(18) 0.071(19) 0.010(18) -0.010(18) -0.024(18) C5A 0.08(2) 0.090(18) 0.071(18) 0.002(17) 0.003(18) -0.013(19) C4A 0.07(2) 0.073(17) 0.072(17) -0.005(16) -0.013(18) -0.016(18) C15 0.08(2) 0.16(2) 0.084(12) 0.035(13) -0.005(12) -0.014(14) 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' Au Au -0.6570 6.0260 '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' 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 178.1(4) . . ? C12 P1 Au1 113.1(5) . . ? C12 P1 C10 105.2(7) . . ? C12 P1 C14 106.8(8) . . ? C10 P1 Au1 114.4(4) . . ? C10 P1 C14 104.0(7) . . ? C14 P1 Au1 112.5(5) . . ? C8 C7 H7 119.2 . . ? C8 C7 C6 121.6(19) . . ? C6 C7 H7 119.2 . . ? C7 C8 H8 118.9 . . ? C7 C8 C3 122.2(16) . . ? C3 C8 H8 118.9 . . ? C8 C3 C2 126.1(19) . . ? C4 C3 C8 114.6(17) . . ? C4 C3 C2 119(2) . . ? C3 C4 H4 118.3 . . ? C3 C4 C5 123.4(17) . . ? C5 C4 H4 118.3 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.0(17) . . ? C6 C5 H5 120.0 . . ? C7 C6 O1 115.6(19) . . ? C5 C6 C7 118.2(18) . . ? C5 C6 O1 126(2) . . ? P1 C12 H12A 108.3 . . ? P1 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C13 C12 P1 116.1(11) . . ? C13 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C9 O1 C6 118.6(18) . . ? C1 C2 C3 176.7(18) . . ? C1 C2 C3A 172(4) . . ? C2 C1 Au1 175.0(11) . . ? P1 C10 H10A 109.1 . . ? P1 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C11 C10 P1 112.6(11) . . ? C11 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? 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 108.7 . . ? P1 C14 H14D 108.7 . . ? P1 C14 H14A 108.9 . . ? P1 C14 H14B 108.9 . . ? H14C C14 H14D 107.6 . . ? H14A C14 H14B 107.7 . . ? C15A C14 P1 114(4) . . ? C15A C14 H14C 108.7 . . ? C15A C14 H14D 108.7 . . ? C15 C14 P1 113.5(13) . . ? C15 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? 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 119(5) . . ? C8A C3A C2 112(4) . . ? C8A C3A C4A 120.0 . . ? C4A C3A C2 128(4) . . ? C3A C8A H8A 120.0 . . ? C3A C8A C7A 120.0 . . ? C7A C8A H8A 120.0 . . ? C8A C7A H7A 120.0 . . ? C8A C7A C6A 120.0 . . ? C6A C7A H7A 120.0 . . ? O1A C6A C7A 118(4) . . ? O1A C6A C5A 122(4) . . ? C5A C6A C7A 120.0 . . ? C6A C5A H5A 120.0 . . ? C6A C5A C4A 120.0 . . ? C4A C5A H5A 120.0 . . ? C3A C4A H4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C5A C4A H4A 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(3) . ? Au1 C1 1.991(14) . ? P1 C12 1.800(14) . ? P1 C10 1.819(12) . ? P1 C14 1.827(15) . ? C7 H7 0.9300 . ? C7 C8 1.36(2) . ? C7 C6 1.36(2) . ? C8 H8 0.9300 . ? C8 C3 1.40(2) . ? C3 C4 1.36(2) . ? C3 C2 1.40(3) . ? C4 H4 0.9300 . ? C4 C5 1.39(3) . ? C5 H5 0.9300 . ? C5 C6 1.35(3) . ? C6 O1 1.38(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C13 1.522(16) . ? O1 C9 1.37(3) . ? C2 C1 1.221(15) . ? C2 C3A 1.50(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.53(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 1.64(8) . ? C14 C15 1.50(2) . ? 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 1.46(7) . ? O1A C6A 1.27(5) . ? C3A C8A 1.3900 . ? C3A C4A 1.3900 . ? C8A H8A 0.9300 . ? C8A C7A 1.3900 . ? C7A H7A 0.9300 . ? C7A C6A 1.3900 . ? C6A C5A 1.3900 . ? C5A H5A 0.9300 . ? C5A C4A 1.3900 . ? 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(10) . . . . ? Au1 P1 C10 C11 60.7(14) . . . . ? Au1 P1 C14 C15A -64(3) . . . . ? Au1 P1 C14 C15 57.1(13) . . . . ? C7 C8 C3 C4 2(3) . . . . ? C7 C8 C3 C2 -175(3) . . . . ? C7 C6 O1 C9 -174(2) . . . . ? C8 C7 C6 C5 2(3) . . . . ? C8 C7 C6 O1 -179.7(19) . . . . ? C8 C3 C4 C5 -2(3) . . . . ? C3 C4 C5 C6 1(3) . . . . ? C4 C5 C6 C7 -1(3) . . . . ? C4 C5 C6 O1 -180(2) . . . . ? C5 C6 O1 C9 4(4) . . . . ? C6 C7 C8 C3 -2(3) . . . . ? C12 P1 C10 C11 -64.0(13) . . . . ? C12 P1 C14 C15A 61(3) . . . . ? C12 P1 C14 C15 -178.3(12) . . . . ? C2 C3 C4 C5 175(3) . . . . ? C2 C3A C8A C7A 177(7) . . . . ? C2 C3A C4A C5A -177(8) . . . . ? C10 P1 C12 C13 -56.2(13) . . . . ? C10 P1 C14 C15A 172(3) . . . . ? C10 P1 C14 C15 -67.2(13) . . . . ? C14 P1 C12 C13 54.0(13) . . . . ? C14 P1 C10 C11 -176.2(13) . . . . ? C9A O1A C6A C7A -172(6) . . . . ? C9A O1A C6A C5A 6(9) . . . . ? O1A C6A C5A C4A -177(6) . . . . ? C3A C8A C7A C6A 0.0 . . . . ? C8A C3A C4A C5A 0.0 . . . . ? C8A C7A C6A O1A 177(6) . . . . ? C8A C7A C6A C5A 0.0 . . . . ? C7A C6A C5A C4A 0.0 . . . . ? C6A C5A C4A C3A 0.0 . . . . ? C4A C3A C8A C7A 0.0 . . . . ?