#------------------------------------------------------------------------------ #$Date: 2020-08-13 04:55:43 +0300 (Thu, 13 Aug 2020) $ #$Revision: 255284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705139.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_7705139 loop_ _publ_author_name 'Gimeno, Maria Concepcion' 'Johnson, Alice' 'Marzo, Isabel' _publ_section_title ; Heterobimetallic propargyl gold complexes with \p-bound copper or silver with enhanced anticancer activity ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02113J _journal_year 2020 _chemical_formula_sum 'C22 H20 Au O P' _chemical_formula_weight 528.32 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-07-29 deposited with the CCDC. 2020-08-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.08 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.413(4) _cell_length_b 10.891(4) _cell_length_c 13.413(4) _cell_measurement_reflns_used 9909 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.50 _cell_measurement_theta_min 2.42 _cell_volume 1929.1(11) _computing_cell_refinement SMART _computing_data_collection SMART _computing_data_reduction SMART _computing_molecular_graphics Diamond _computing_publication_material 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution SHELXS _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.26 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.933 _diffrn_measurement_device_type 'SMART APEX CCD' _diffrn_measurement_method 'w rotations with narrow frames' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1706 _diffrn_reflns_av_unetI/netI 0.0937 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.933 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 16809 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.933 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.608 _diffrn_reflns_theta_min 2.424 _exptl_absorpt_coefficient_mu 7.715 _exptl_absorpt_correction_T_max 0.337 _exptl_absorpt_correction_T_min 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.819 _exptl_crystal_description prism _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.360 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.180 _refine_diff_density_max 3.406 _refine_diff_density_min -2.475 _refine_diff_density_rms 0.270 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 4613 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0398 _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^)+(0.0558P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1092 _refine_ls_wR_factor_ref 0.1110 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4173 _reflns_number_total 4613 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02113j2.cif _cod_data_source_block con289 _cod_original_cell_volume 1929.2(11) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7705139 _shelx_shelxl_version_number 2016/6 _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. ; _shelx_estimated_absorpt_t_min 0.168 _shelx_estimated_absorpt_t_max 0.337 _shelx_res_file ; TITL con289 in P2(1)/c New:P21/c con289.res created by SHELXL-2016/6 at 09:30:46 on 21-Jul-2020 CELL 0.71073 13.4130 10.8910 13.4130 90.000 100.077 90.000 ZERR 4 0.0040 0.0040 0.0040 0.000 0.000 0.000 LATT 1 SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H Au O P UNIT 88 80 4 4 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT 14 8 2 OMIT -5 2 4 OMIT 13 9 2 OMIT 9 11 6 TEMP -173 SIZE 0.36 0.18 0.18 L.S. 20 FMAP 2 PLAN -20 ACTA CONF BOND $H WGHT 0.055800 FVAR 0.16501 RESI 0 AU1 3 0.270101 0.931381 0.141027 11.00000 0.01226 0.01386 = 0.01612 -0.00211 0.00162 0.00039 P1 5 0.250785 0.787826 0.014666 11.00000 0.01116 0.01252 = 0.01699 -0.00079 0.00179 0.00048 O1 4 0.313484 1.331674 0.397799 11.00000 0.03689 0.01292 = 0.02828 -0.00208 0.00451 -0.00192 C1 1 0.211347 1.340312 0.404862 11.00000 0.04433 0.02003 = 0.03973 -0.00496 0.01686 0.00663 AFIX 137 H1A 2 0.187886 1.424601 0.389773 11.00000 -1.50000 H1B 2 0.202253 1.318466 0.473580 11.00000 -1.50000 H1C 2 0.172039 1.283947 0.356201 11.00000 -1.50000 AFIX 0 C2 1 0.349983 1.209610 0.409017 11.00000 0.02859 0.01929 = 0.01928 -0.00163 -0.00222 -0.00199 AFIX 23 H2A 2 0.329615 1.173556 0.470173 11.00000 -1.20000 H2B 2 0.424908 1.211451 0.420206 11.00000 -1.20000 AFIX 0 C3 1 0.313071 1.128442 0.320960 11.00000 0.01714 0.01692 = 0.02030 0.00307 0.00222 0.00288 C4 1 0.291123 1.057895 0.251349 11.00000 0.01433 0.01220 = 0.01908 0.00185 0.00277 0.00334 C5 1 0.357459 0.777242 -0.050459 11.00000 0.01354 0.01290 = 0.01669 -0.00182 0.00038 -0.00097 C6 1 0.408361 0.885715 -0.068607 11.00000 0.01707 0.01782 = 0.01949 0.00062 0.00009 -0.00351 AFIX 43 H6 2 0.388297 0.962117 -0.044230 11.00000 -1.20000 AFIX 0 C7 1 0.488130 0.880946 -0.122309 11.00000 0.01827 0.02232 = 0.02145 0.00438 0.00152 -0.00181 AFIX 43 H7 2 0.522312 0.954180 -0.134978 11.00000 -1.20000 AFIX 0 C8 1 0.517762 0.769112 -0.157379 11.00000 0.01469 0.03089 = 0.01967 0.00270 0.00286 -0.00256 AFIX 43 H8 2 0.573109 0.765839 -0.192860 11.00000 -1.20000 AFIX 0 C9 1 0.466723 0.661733 -0.140781 11.00000 0.01461 0.02224 = 0.02763 -0.00644 0.00705 -0.00032 AFIX 43 H9 2 0.486214 0.585818 -0.166501 11.00000 -1.20000 AFIX 0 C10 1 0.387093 0.665326 -0.086517 11.00000 0.01229 0.01704 = 0.02780 -0.00158 0.00619 -0.00271 AFIX 43 H10 2 0.353147 0.591799 -0.074153 11.00000 -1.20000 AFIX 0 C11 1 0.231978 0.632390 0.057408 11.00000 0.01185 0.01441 = 0.01871 -0.00038 0.00562 -0.00184 C12 1 0.296922 0.589180 0.144146 11.00000 0.00976 0.02615 = 0.02375 0.00074 0.00555 -0.00172 AFIX 43 H12 2 0.349781 0.640268 0.177625 11.00000 -1.20000 AFIX 0 C13 1 0.284090 0.472215 0.181015 11.00000 0.02688 0.02594 = 0.02256 0.00439 0.00388 0.00787 AFIX 43 H13 2 0.327812 0.443384 0.239804 11.00000 -1.20000 AFIX 0 C14 1 0.207176 0.397608 0.131674 11.00000 0.03116 0.01621 = 0.02866 0.00467 0.00925 0.00140 AFIX 43 H14 2 0.198484 0.317499 0.156838 11.00000 -1.20000 AFIX 0 C15 1 0.142345 0.439293 0.045237 11.00000 0.02076 0.02226 = 0.03454 -0.00066 0.00686 -0.00399 AFIX 43 H15 2 0.089053 0.388040 0.012860 11.00000 -1.20000 AFIX 0 C16 1 0.155476 0.555550 0.006347 11.00000 0.00934 0.02044 = 0.02751 -0.00463 0.00036 -0.00065 AFIX 43 H16 2 0.113233 0.582636 -0.053987 11.00000 -1.20000 AFIX 0 C17 1 0.141768 0.818532 -0.082888 11.00000 0.01385 0.01385 = 0.02018 0.00186 0.00424 0.00051 C18 1 0.054147 0.861476 -0.053131 11.00000 0.01598 0.02018 = 0.02070 -0.00303 0.00387 0.00188 AFIX 43 H18 2 0.052001 0.872861 0.016682 11.00000 -1.20000 AFIX 0 C19 1 -0.030359 0.887774 -0.125527 11.00000 0.01653 0.01783 = 0.03445 -0.00061 0.00351 0.00247 AFIX 43 H19 2 -0.091205 0.914181 -0.105063 11.00000 -1.20000 AFIX 0 C20 1 -0.026304 0.875586 -0.228174 11.00000 0.01775 0.02757 = 0.02798 0.00330 -0.00247 0.00146 AFIX 43 H20 2 -0.083455 0.897545 -0.277318 11.00000 -1.20000 AFIX 0 C21 1 0.059131 0.832335 -0.258812 11.00000 0.01890 0.04052 = 0.02247 0.00166 -0.00152 -0.00099 AFIX 43 H21 2 0.060786 0.822022 -0.328834 11.00000 -1.20000 AFIX 0 C22 1 0.144501 0.803239 -0.185940 11.00000 0.01577 0.02907 = 0.02044 0.00314 0.00455 0.00712 AFIX 43 H22 2 0.204136 0.773150 -0.206683 11.00000 -1.20000 AFIX 0 HKLF 4 REM con289 in P2(1)/c New:P21/c REM R1 = 0.0398 for 4173 Fo > 4sig(Fo) and 0.0425 for all 4613 data REM 227 parameters refined using 0 restraints END WGHT 0.0559 0.0000 REM Highest difference peak 3.406, deepest hole -2.475, 1-sigma level 0.270 Q1 1 0.2539 0.9336 0.0832 11.00000 0.05 3.41 Q2 1 0.2808 0.9315 0.1976 11.00000 0.05 3.22 Q3 1 0.3130 0.9340 0.2018 11.00000 0.05 3.13 Q4 1 0.2224 0.8988 0.0240 11.00000 0.05 1.50 Q5 1 0.3212 0.8976 0.2587 11.00000 0.05 1.48 Q6 1 0.2153 0.9735 0.0217 11.00000 0.05 1.36 Q7 1 0.3202 0.9718 0.2607 11.00000 0.05 1.31 Q8 1 0.2068 1.0408 0.2220 11.00000 0.05 0.93 Q9 1 0.3617 0.9620 0.1119 11.00000 0.05 0.91 Q10 1 0.3335 1.0314 0.0594 11.00000 0.05 0.91 Q11 1 0.1629 0.9304 -0.0197 11.00000 0.05 0.89 Q12 1 0.3739 0.9321 0.2976 11.00000 0.05 0.88 Q13 1 0.1806 0.9004 0.1822 11.00000 0.05 0.83 Q14 1 0.3608 0.9014 0.1146 11.00000 0.05 0.82 Q15 1 0.3249 0.8288 0.0626 11.00000 0.05 0.82 Q16 1 0.2154 0.8136 -0.0323 11.00000 0.05 0.81 Q17 1 0.2739 0.5947 0.1555 11.00000 0.05 0.79 Q18 1 0.1747 0.9591 0.1640 11.00000 0.05 0.77 Q19 1 0.2073 0.8291 0.2216 11.00000 0.05 0.73 Q20 1 0.1212 0.9373 0.1692 11.00000 0.05 0.71 ; _shelx_res_checksum 73920 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 0.27010(2) 0.93138(2) 0.14103(2) 0.01418(10) Uani 1 1 d . . . . . P1 P 0.25078(8) 0.78783(11) 0.01467(8) 0.0136(2) Uani 1 1 d . . . . . O1 O 0.3135(3) 1.3317(4) 0.3978(2) 0.0262(8) Uani 1 1 d . . . . . C1 C 0.2113(5) 1.3403(6) 0.4049(4) 0.0336(13) Uani 1 1 d . . . . . H1A H 0.187886 1.424601 0.389773 0.050 Uiso 1 1 calc R U . . . H1B H 0.202253 1.318466 0.473580 0.050 Uiso 1 1 calc R U . . . H1C H 0.172039 1.283947 0.356201 0.050 Uiso 1 1 calc R U . . . C2 C 0.3500(4) 1.2096(5) 0.4090(3) 0.0232(10) Uani 1 1 d . . . . . H2A H 0.329615 1.173556 0.470173 0.028 Uiso 1 1 calc R U . . . H2B H 0.424908 1.211451 0.420206 0.028 Uiso 1 1 calc R U . . . C3 C 0.3131(4) 1.1284(5) 0.3210(3) 0.0182(9) Uani 1 1 d . . . . . C4 C 0.2911(4) 1.0579(4) 0.2513(3) 0.0152(9) Uani 1 1 d . . . . . C5 C 0.3575(3) 0.7772(4) -0.0505(3) 0.0146(8) Uani 1 1 d . . . . . C6 C 0.4084(4) 0.8857(5) -0.0686(3) 0.0185(9) Uani 1 1 d . . . . . H6 H 0.388297 0.962117 -0.044230 0.022 Uiso 1 1 calc R U . . . C7 C 0.4881(4) 0.8809(5) -0.1223(3) 0.0209(10) Uani 1 1 d . . . . . H7 H 0.522312 0.954180 -0.134978 0.025 Uiso 1 1 calc R U . . . C8 C 0.5178(3) 0.7691(5) -0.1574(3) 0.0218(10) Uani 1 1 d . . . . . H8 H 0.573109 0.765839 -0.192860 0.026 Uiso 1 1 calc R U . . . C9 C 0.4667(4) 0.6617(5) -0.1408(3) 0.0211(10) Uani 1 1 d . . . . . H9 H 0.486214 0.585818 -0.166501 0.025 Uiso 1 1 calc R U . . . C10 C 0.3871(3) 0.6653(5) -0.0865(3) 0.0187(9) Uani 1 1 d . . . . . H10 H 0.353147 0.591799 -0.074153 0.022 Uiso 1 1 calc R U . . . C11 C 0.2320(3) 0.6324(4) 0.0574(3) 0.0146(8) Uani 1 1 d . . . . . C12 C 0.2969(4) 0.5892(5) 0.1441(3) 0.0196(9) Uani 1 1 d . . . . . H12 H 0.349781 0.640268 0.177625 0.023 Uiso 1 1 calc R U . . . C13 C 0.2841(4) 0.4722(6) 0.1810(4) 0.0252(10) Uani 1 1 d . . . . . H13 H 0.327812 0.443384 0.239804 0.030 Uiso 1 1 calc R U . . . C14 C 0.2072(4) 0.3976(5) 0.1317(4) 0.0249(10) Uani 1 1 d . . . . . H14 H 0.198484 0.317499 0.156838 0.030 Uiso 1 1 calc R U . . . C15 C 0.1423(5) 0.4393(5) 0.0452(4) 0.0256(12) Uani 1 1 d . . . . . H15 H 0.089053 0.388040 0.012860 0.031 Uiso 1 1 calc R U . . . C16 C 0.1555(4) 0.5556(5) 0.0063(4) 0.0194(10) Uani 1 1 d . . . . . H16 H 0.113233 0.582636 -0.053987 0.023 Uiso 1 1 calc R U . . . C17 C 0.1418(3) 0.8185(4) -0.0829(3) 0.0158(9) Uani 1 1 d . . . . . C18 C 0.0541(3) 0.8615(5) -0.0531(3) 0.0189(9) Uani 1 1 d . . . . . H18 H 0.052001 0.872861 0.016682 0.023 Uiso 1 1 calc R U . . . C19 C -0.0304(4) 0.8878(5) -0.1255(4) 0.0230(10) Uani 1 1 d . . . . . H19 H -0.091205 0.914181 -0.105063 0.028 Uiso 1 1 calc R U . . . C20 C -0.0263(4) 0.8756(5) -0.2282(4) 0.0252(11) Uani 1 1 d . . . . . H20 H -0.083455 0.897545 -0.277318 0.030 Uiso 1 1 calc R U . . . C21 C 0.0591(4) 0.8323(6) -0.2588(4) 0.0279(11) Uani 1 1 d . . . . . H21 H 0.060786 0.822022 -0.328834 0.033 Uiso 1 1 calc R U . . . C22 C 0.1445(4) 0.8032(5) -0.1859(3) 0.0216(10) Uani 1 1 d . . . . . H22 H 0.204136 0.773150 -0.206683 0.026 Uiso 1 1 calc R U . . . 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 0.01226(13) 0.01386(14) 0.01612(13) -0.00211(5) 0.00162(7) 0.00039(5) P1 0.0112(5) 0.0125(6) 0.0170(5) -0.0008(4) 0.0018(4) 0.0005(4) O1 0.037(2) 0.0129(18) 0.0283(16) -0.0021(14) 0.0045(14) -0.0019(16) C1 0.044(3) 0.020(3) 0.040(3) -0.005(2) 0.017(2) 0.007(3) C2 0.029(3) 0.019(3) 0.019(2) -0.0016(18) -0.0022(17) -0.002(2) C3 0.017(2) 0.017(2) 0.020(2) 0.0031(17) 0.0022(16) 0.0029(19) C4 0.014(2) 0.012(2) 0.019(2) 0.0018(15) 0.0028(16) 0.0033(16) C5 0.014(2) 0.013(2) 0.0167(18) -0.0018(16) 0.0004(15) -0.0010(18) C6 0.017(2) 0.018(2) 0.019(2) 0.0006(18) 0.0001(16) -0.004(2) C7 0.018(2) 0.022(3) 0.021(2) 0.0044(19) 0.0015(17) -0.002(2) C8 0.015(2) 0.031(3) 0.020(2) 0.0027(19) 0.0029(16) -0.003(2) C9 0.015(2) 0.022(3) 0.028(2) -0.006(2) 0.0071(17) 0.000(2) C10 0.012(2) 0.017(2) 0.028(2) -0.0016(19) 0.0062(16) -0.0027(19) C11 0.012(2) 0.014(2) 0.0187(18) -0.0004(16) 0.0056(15) -0.0018(17) C12 0.010(2) 0.026(3) 0.024(2) 0.0007(19) 0.0055(16) -0.002(2) C13 0.027(3) 0.026(3) 0.023(2) 0.004(2) 0.0039(18) 0.008(2) C14 0.031(3) 0.016(2) 0.029(2) 0.005(2) 0.009(2) 0.001(2) C15 0.021(3) 0.022(3) 0.035(3) -0.0007(19) 0.007(2) -0.004(2) C16 0.009(2) 0.020(3) 0.028(2) -0.0046(18) 0.0004(17) -0.0006(18) C17 0.014(2) 0.014(2) 0.020(2) 0.0019(16) 0.0042(15) 0.0005(17) C18 0.016(2) 0.020(3) 0.021(2) -0.0030(18) 0.0039(16) 0.0019(19) C19 0.017(2) 0.018(3) 0.034(2) -0.001(2) 0.0035(19) 0.002(2) C20 0.018(2) 0.028(3) 0.028(2) 0.003(2) -0.0025(18) 0.001(2) C21 0.019(2) 0.041(3) 0.022(2) 0.002(2) -0.0015(17) -0.001(2) C22 0.016(2) 0.029(3) 0.020(2) 0.0031(19) 0.0045(16) 0.007(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 C4 Au1 P1 178.38(15) . . ? C5 P1 C17 105.6(2) . . ? C5 P1 C11 105.0(2) . . ? C17 P1 C11 105.1(2) . . ? C5 P1 Au1 113.92(15) . . ? C17 P1 Au1 112.39(16) . . ? C11 P1 Au1 113.99(14) . . ? C1 O1 C2 112.5(4) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 114.4(4) . . ? O1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? O1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 174.4(5) . . ? C3 C4 Au1 173.4(4) . . ? C10 C5 C6 119.8(4) . . ? C10 C5 P1 121.4(3) . . ? C6 C5 P1 118.7(3) . . ? C7 C6 C5 119.9(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 120.0(5) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 120.2(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.8(5) . . ? C9 C10 H10 120.1 . . ? C5 C10 H10 120.1 . . ? C16 C11 C12 119.8(4) . . ? C16 C11 P1 122.0(3) . . ? C12 C11 P1 118.2(4) . . ? C13 C12 C11 120.3(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.7(5) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 120.3(5) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 119.2(5) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C18 C17 C22 119.6(4) . . ? C18 C17 P1 118.1(3) . . ? C22 C17 P1 122.2(4) . . ? C17 C18 C19 119.9(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 120.2(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.6(5) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C17 C22 C21 120.1(4) . . ? C17 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C4 2.005(5) . ? Au1 P1 2.2870(12) . ? P1 C5 1.806(4) . ? P1 C17 1.815(5) . ? P1 C11 1.819(5) . ? O1 C1 1.393(7) . ? O1 C2 1.416(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.489(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.205(7) . ? C5 C10 1.395(6) . ? C5 C6 1.407(6) . ? C6 C7 1.391(6) . ? C6 H6 0.9500 . ? C7 C8 1.389(7) . ? C7 H7 0.9500 . ? C8 C9 1.393(7) . ? C8 H8 0.9500 . ? C9 C10 1.394(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.406(7) . ? C11 C12 1.407(6) . ? C12 C13 1.388(8) . ? C12 H12 0.9500 . ? C13 C14 1.387(8) . ? C13 H13 0.9500 . ? C14 C15 1.398(8) . ? C14 H14 0.9500 . ? C15 C16 1.392(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.387(6) . ? C17 C22 1.399(6) . ? C18 C19 1.387(6) . ? C18 H18 0.9500 . ? C19 C20 1.394(7) . ? C19 H19 0.9500 . ? C20 C21 1.367(7) . ? C20 H20 0.9500 . ? C21 C22 1.405(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C1 O1 C2 C3 72.1(5) . . . . ? C17 P1 C5 C10 -90.9(4) . . . . ? C11 P1 C5 C10 19.9(4) . . . . ? Au1 P1 C5 C10 145.2(3) . . . . ? C17 P1 C5 C6 86.3(4) . . . . ? C11 P1 C5 C6 -162.9(3) . . . . ? Au1 P1 C5 C6 -37.6(4) . . . . ? C10 C5 C6 C7 -0.1(7) . . . . ? P1 C5 C6 C7 -177.3(3) . . . . ? C5 C6 C7 C8 -0.4(7) . . . . ? C6 C7 C8 C9 1.2(7) . . . . ? C7 C8 C9 C10 -1.7(7) . . . . ? C8 C9 C10 C5 1.2(7) . . . . ? C6 C5 C10 C9 -0.3(7) . . . . ? P1 C5 C10 C9 176.9(3) . . . . ? C5 P1 C11 C16 -101.4(4) . . . . ? C17 P1 C11 C16 9.8(4) . . . . ? Au1 P1 C11 C16 133.3(3) . . . . ? C5 P1 C11 C12 78.4(4) . . . . ? C17 P1 C11 C12 -170.5(3) . . . . ? Au1 P1 C11 C12 -47.0(4) . . . . ? C16 C11 C12 C13 -1.7(7) . . . . ? P1 C11 C12 C13 178.5(4) . . . . ? C11 C12 C13 C14 0.3(8) . . . . ? C12 C13 C14 C15 -0.1(8) . . . . ? C13 C14 C15 C16 1.3(8) . . . . ? C14 C15 C16 C11 -2.6(8) . . . . ? C12 C11 C16 C15 2.8(7) . . . . ? P1 C11 C16 C15 -177.4(4) . . . . ? C5 P1 C17 C18 -164.1(4) . . . . ? C11 P1 C17 C18 85.2(4) . . . . ? Au1 P1 C17 C18 -39.3(4) . . . . ? C5 P1 C17 C22 14.3(5) . . . . ? C11 P1 C17 C22 -96.4(4) . . . . ? Au1 P1 C17 C22 139.1(4) . . . . ? C22 C17 C18 C19 0.6(8) . . . . ? P1 C17 C18 C19 179.0(4) . . . . ? C17 C18 C19 C20 -2.4(8) . . . . ? C18 C19 C20 C21 3.0(9) . . . . ? C19 C20 C21 C22 -1.8(9) . . . . ? C18 C17 C22 C21 0.6(8) . . . . ? P1 C17 C22 C21 -177.8(4) . . . . ? C20 C21 C22 C17 0.0(9) . . . . ?