#------------------------------------------------------------------------------ #$Date: 2020-09-06 12:36:57 +0300 (Sun, 06 Sep 2020) $ #$Revision: 256083 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705137.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_7705137 loop_ _publ_author_name 'Johnson, Alice' 'Marzo, Isabel' 'Gimeno, M Concepci\'on' _publ_section_title ; Heterobimetallic propargyl gold complexes with \p-bound copper or silver with enhanced anticancer activity. ; _journal_issue 33 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 11736 _journal_page_last 11742 _journal_paper_doi 10.1039/d0dt02113j _journal_volume 49 _journal_year 2020 _chemical_formula_sum 'C33 H25 Au N P' _chemical_formula_weight 663.47 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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 88.70(3) _cell_angle_beta 77.31(3) _cell_angle_gamma 78.99(3) _cell_formula_units_Z 2 _cell_length_a 8.7346(17) _cell_length_b 9.4044(19) _cell_length_c 16.195(3) _cell_measurement_reflns_used 33396 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.0920 _cell_measurement_theta_min 3.3600 _cell_volume 1273.7(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_molecular_graphics Diamond _computing_publication_material 'ShelXL (Sheldrick, 2015)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution SHELXS _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.0655 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.935 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'w rotations' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.935 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 46269 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.935 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.162 _diffrn_reflns_theta_min 3.135 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 5.861 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45975 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.730 _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.180 _exptl_transmission_factor_max 1.00000 _exptl_transmission_factor_min 0.45975 _refine_diff_density_max 0.616 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.093 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 325 _refine_ls_number_reflns 7697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0175 _refine_ls_R_factor_gt 0.0163 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0128P)^2^+1.1318P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0345 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7417 _reflns_number_total 7697 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02113j2.cif _cod_data_source_block c517 _cod_depositor_comments 'Adding full bibliography for 7705135--7705141.cif.' _cod_database_code 7705137 _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 0.311 _shelx_estimated_absorpt_t_max 0.418 _shelx_res_file ; TITL c517 in P1 New: P-1 c517.res created by SHELXL-2016/6 at 13:03:58 on 20-Jul-2020 CELL 0.71073 8.7346 9.4044 16.1950 88.700 77.310 78.990 ZERR 2 0.0017 0.0019 0.0030 0.030 0.030 0.030 LATT 1 SFAC C H Au N P UNIT 66 50 2 2 2 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT 0 4 3 OMIT 0 2 2 OMIT -1 3 3 OMIT 1 -1 5 OMIT 2 0 3 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 CONF SIZE 0.26 0.20 0.18 TEMP -173 WGHT 0.012800 1.131800 FVAR 3.80346 AU1 3 0.309736 0.137790 0.218247 11.00000 0.01451 0.01436 = 0.01344 0.00185 -0.00378 -0.00175 C1 1 0.428652 -0.019703 0.278092 11.00000 0.01518 0.01720 = 0.01560 -0.00032 -0.00177 -0.00362 C2 1 0.496069 -0.115783 0.314655 11.00000 0.01617 0.01675 = 0.01518 0.00110 -0.00151 -0.00501 C3 1 0.564025 -0.228895 0.367766 11.00000 0.01474 0.01766 = 0.01946 0.00418 -0.00338 -0.00287 AFIX 23 H3A 2 0.640532 -0.305464 0.331024 11.00000 -1.20000 H3B 2 0.623362 -0.186272 0.403246 11.00000 -1.20000 AFIX 0 C4 1 0.414937 -0.432894 0.416687 11.00000 0.02042 0.01402 = 0.01822 0.00436 -0.01075 -0.00450 C5 1 0.508027 -0.549385 0.366096 11.00000 0.02267 0.01865 = 0.02305 0.00071 -0.01160 -0.00003 AFIX 43 H5 2 0.604570 -0.539999 0.327602 11.00000 -1.20000 AFIX 0 C6 1 0.454149 -0.679771 0.374149 11.00000 0.03087 0.01544 = 0.03203 -0.00167 -0.01789 0.00105 AFIX 43 H6 2 0.515352 -0.761296 0.340673 11.00000 -1.20000 AFIX 0 C7 1 0.312005 -0.693562 0.430376 11.00000 0.03291 0.01637 = 0.03651 0.00572 -0.02113 -0.00804 AFIX 43 H7 2 0.277503 -0.783807 0.433713 11.00000 -1.20000 AFIX 0 C8 1 0.220572 -0.578795 0.481215 11.00000 0.02619 0.02070 = 0.02688 0.00837 -0.01429 -0.01052 AFIX 43 H8 2 0.124795 -0.589933 0.519825 11.00000 -1.20000 AFIX 0 C9 1 0.271046 -0.446023 0.475014 11.00000 0.01974 0.01863 = 0.01798 0.00543 -0.00994 -0.00677 C10 1 0.206980 -0.305317 0.515864 11.00000 0.01861 0.02016 = 0.01546 0.00433 -0.00806 -0.00687 C11 1 0.070748 -0.248345 0.577370 11.00000 0.01994 0.02965 = 0.01540 0.00399 -0.00475 -0.01060 AFIX 43 H11 2 -0.001593 -0.308366 0.603228 11.00000 -1.20000 AFIX 0 C12 1 0.042975 -0.103062 0.599980 11.00000 0.02061 0.03106 = 0.01558 -0.00168 -0.00278 -0.00362 AFIX 43 H12 2 -0.050803 -0.062738 0.640540 11.00000 -1.20000 AFIX 0 C13 1 0.151146 -0.014818 0.563906 11.00000 0.02553 0.02184 = 0.01740 -0.00262 -0.00534 -0.00267 AFIX 43 H13 2 0.129441 0.084532 0.580502 11.00000 -1.20000 AFIX 0 C14 1 0.289376 -0.069320 0.504437 11.00000 0.02098 0.01778 = 0.01726 0.00092 -0.00439 -0.00566 AFIX 43 H14 2 0.363926 -0.009884 0.480839 11.00000 -1.20000 AFIX 0 C15 1 0.314332 -0.214547 0.480783 11.00000 0.01629 0.01776 = 0.01425 0.00298 -0.00579 -0.00369 C16 1 0.090745 0.481748 0.190833 11.00000 0.01434 0.01546 = 0.01415 0.00060 -0.00212 -0.00201 C17 1 0.164290 0.535249 0.248506 11.00000 0.02082 0.02095 = 0.01863 0.00006 -0.00772 -0.00307 AFIX 43 H17 2 0.248735 0.474243 0.267811 11.00000 -1.20000 AFIX 0 C18 1 0.113613 0.678210 0.277673 11.00000 0.03165 0.02331 = 0.02263 -0.00461 -0.01053 -0.00477 AFIX 43 H18 2 0.164264 0.715197 0.316477 11.00000 -1.20000 AFIX 0 C19 1 -0.010942 0.766838 0.250096 11.00000 0.03073 0.01922 = 0.01938 -0.00456 -0.00255 0.00052 AFIX 43 H19 2 -0.043281 0.865154 0.268885 11.00000 -1.20000 AFIX 0 C20 1 -0.088483 0.712445 0.195174 11.00000 0.02166 0.02177 = 0.01822 -0.00148 -0.00333 0.00336 AFIX 43 H20 2 -0.176028 0.772489 0.177987 11.00000 -1.20000 AFIX 0 C21 1 -0.037886 0.570348 0.165477 11.00000 0.01775 0.02082 = 0.01671 -0.00149 -0.00435 -0.00127 AFIX 43 H21 2 -0.090727 0.533118 0.127825 11.00000 -1.20000 AFIX 0 C22 1 0.004413 0.234630 0.120821 11.00000 0.01411 0.01390 = 0.01852 0.00176 -0.00545 -0.00246 C23 1 -0.015243 0.217662 0.038756 11.00000 0.01877 0.01871 = 0.01886 -0.00019 -0.00547 -0.00339 AFIX 43 H23 2 0.057293 0.247631 -0.008027 11.00000 -1.20000 AFIX 0 C24 1 -0.141430 0.156678 0.025373 11.00000 0.02340 0.02300 = 0.02660 -0.00422 -0.01149 -0.00343 AFIX 43 H24 2 -0.155231 0.145606 -0.030545 11.00000 -1.20000 AFIX 0 C25 1 -0.246608 0.112251 0.093425 11.00000 0.01946 0.02008 = 0.03977 -0.00204 -0.00986 -0.00608 AFIX 43 H25 2 -0.332100 0.070127 0.084110 11.00000 -1.20000 AFIX 0 C26 1 -0.227576 0.129033 0.175090 11.00000 0.01913 0.02503 = 0.03205 0.00466 -0.00296 -0.00847 AFIX 43 H26 2 -0.300257 0.098695 0.221670 11.00000 -1.20000 AFIX 0 C27 1 -0.102817 0.189948 0.189024 11.00000 0.02229 0.02580 = 0.01921 0.00437 -0.00421 -0.00709 AFIX 43 H27 2 -0.090202 0.201343 0.245142 11.00000 -1.20000 AFIX 0 C28 1 0.293817 0.331761 0.040566 11.00000 0.01256 0.01771 = 0.01455 -0.00006 -0.00392 -0.00262 C29 1 0.289543 0.466900 0.003394 11.00000 0.01572 0.01840 = 0.01881 0.00101 -0.00357 -0.00271 AFIX 43 H29 2 0.225416 0.550680 0.033611 11.00000 -1.20000 AFIX 0 C30 1 0.379321 0.479640 -0.078238 11.00000 0.01949 0.02488 = 0.02082 0.00505 -0.00419 -0.00751 AFIX 43 H30 2 0.376235 0.572009 -0.103503 11.00000 -1.20000 AFIX 0 C31 1 0.472550 0.357980 -0.122209 11.00000 0.01974 0.03359 = 0.01659 0.00073 -0.00077 -0.00885 AFIX 43 H31 2 0.531923 0.366617 -0.178144 11.00000 -1.20000 AFIX 0 C32 1 0.479923 0.223149 -0.085076 11.00000 0.02458 0.02593 = 0.01972 -0.00633 0.00025 -0.00112 AFIX 43 H32 2 0.545299 0.139844 -0.115248 11.00000 -1.20000 AFIX 0 C33 1 0.391760 0.210232 -0.003909 11.00000 0.02281 0.01824 = 0.01968 -0.00211 -0.00343 -0.00112 AFIX 43 H33 2 0.397982 0.118010 0.021683 11.00000 -1.20000 AFIX 0 N1 4 0.439984 -0.292927 0.422045 11.00000 0.01636 0.01345 = 0.01633 0.00230 -0.00251 -0.00325 P1 5 0.172515 0.302914 0.143676 11.00000 0.01358 0.01379 = 0.01353 0.00107 -0.00386 -0.00195 HKLF 4 REM c517 in P1 New: P-1 REM R1 = 0.0163 for 7417 Fo > 4sig(Fo) and 0.0175 for all 7697 data REM 325 parameters refined using 0 restraints END WGHT 0.0132 1.1135 REM Highest difference peak 0.616, deepest hole -0.934, 1-sigma level 0.093 Q1 1 0.3186 0.1979 0.2730 11.00000 0.05 0.62 Q2 1 0.1783 0.1429 0.2626 11.00000 0.05 0.59 Q3 1 0.2375 0.1875 0.1621 11.00000 0.05 0.57 Q4 1 0.4000 0.0973 0.2648 11.00000 0.05 0.53 Q5 1 0.3790 0.0212 0.2401 11.00000 0.05 0.53 ; _shelx_res_checksum 38353 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.30974(2) 0.13779(2) 0.21825(2) 0.01416(2) Uani 1 1 d . . . . . C1 C 0.42865(19) -0.01970(18) 0.27809(10) 0.0162(3) Uani 1 1 d . . . . . C2 C 0.4961(2) -0.11578(18) 0.31465(10) 0.0161(3) Uani 1 1 d . . . . . C3 C 0.5640(2) -0.22890(18) 0.36777(11) 0.0174(3) Uani 1 1 d . . . . . H3A H 0.640532 -0.305464 0.331024 0.021 Uiso 1 1 calc R U . . . H3B H 0.623362 -0.186272 0.403246 0.021 Uiso 1 1 calc R U . . . C4 C 0.4149(2) -0.43289(18) 0.41669(11) 0.0164(3) Uani 1 1 d . . . . . C5 C 0.5080(2) -0.54939(19) 0.36610(12) 0.0210(3) Uani 1 1 d . . . . . H5 H 0.604570 -0.539999 0.327602 0.025 Uiso 1 1 calc R U . . . C6 C 0.4541(2) -0.6798(2) 0.37415(13) 0.0251(4) Uani 1 1 d . . . . . H6 H 0.515352 -0.761296 0.340673 0.030 Uiso 1 1 calc R U . . . C7 C 0.3120(2) -0.6936(2) 0.43038(13) 0.0261(4) Uani 1 1 d . . . . . H7 H 0.277503 -0.783807 0.433713 0.031 Uiso 1 1 calc R U . . . C8 C 0.2206(2) -0.5788(2) 0.48121(12) 0.0226(4) Uani 1 1 d . . . . . H8 H 0.124795 -0.589933 0.519825 0.027 Uiso 1 1 calc R U . . . C9 C 0.2710(2) -0.44602(19) 0.47501(11) 0.0175(3) Uani 1 1 d . . . . . C10 C 0.2070(2) -0.30532(19) 0.51586(10) 0.0170(3) Uani 1 1 d . . . . . C11 C 0.0707(2) -0.2483(2) 0.57737(11) 0.0208(3) Uani 1 1 d . . . . . H11 H -0.001593 -0.308366 0.603228 0.025 Uiso 1 1 calc R U . . . C12 C 0.0430(2) -0.1031(2) 0.59998(11) 0.0227(4) Uani 1 1 d . . . . . H12 H -0.050803 -0.062738 0.640540 0.027 Uiso 1 1 calc R U . . . C13 C 0.1511(2) -0.0148(2) 0.56391(11) 0.0217(3) Uani 1 1 d . . . . . H13 H 0.129441 0.084532 0.580502 0.026 Uiso 1 1 calc R U . . . C14 C 0.2894(2) -0.06932(19) 0.50444(11) 0.0184(3) Uani 1 1 d . . . . . H14 H 0.363926 -0.009884 0.480839 0.022 Uiso 1 1 calc R U . . . C15 C 0.31433(19) -0.21455(18) 0.48078(10) 0.0157(3) Uani 1 1 d . . . . . C16 C 0.09074(19) 0.48175(18) 0.19083(10) 0.0149(3) Uani 1 1 d . . . . . C17 C 0.1643(2) 0.53525(19) 0.24851(11) 0.0197(3) Uani 1 1 d . . . . . H17 H 0.248735 0.474243 0.267811 0.024 Uiso 1 1 calc R U . . . C18 C 0.1136(2) 0.6782(2) 0.27767(12) 0.0251(4) Uani 1 1 d . . . . . H18 H 0.164264 0.715197 0.316477 0.030 Uiso 1 1 calc R U . . . C19 C -0.0109(2) 0.7668(2) 0.25010(12) 0.0242(4) Uani 1 1 d . . . . . H19 H -0.043281 0.865154 0.268885 0.029 Uiso 1 1 calc R U . . . C20 C -0.0885(2) 0.7124(2) 0.19517(11) 0.0217(3) Uani 1 1 d . . . . . H20 H -0.176028 0.772489 0.177987 0.026 Uiso 1 1 calc R U . . . C21 C -0.0379(2) 0.57035(19) 0.16548(11) 0.0186(3) Uani 1 1 d . . . . . H21 H -0.090727 0.533118 0.127825 0.022 Uiso 1 1 calc R U . . . C22 C 0.00441(19) 0.23463(17) 0.12082(10) 0.0153(3) Uani 1 1 d . . . . . C23 C -0.0152(2) 0.21766(19) 0.03876(11) 0.0186(3) Uani 1 1 d . . . . . H23 H 0.057293 0.247631 -0.008027 0.022 Uiso 1 1 calc R U . . . C24 C -0.1414(2) 0.1567(2) 0.02537(12) 0.0234(4) Uani 1 1 d . . . . . H24 H -0.155231 0.145606 -0.030545 0.028 Uiso 1 1 calc R U . . . C25 C -0.2466(2) 0.1123(2) 0.09343(13) 0.0256(4) Uani 1 1 d . . . . . H25 H -0.332100 0.070127 0.084110 0.031 Uiso 1 1 calc R U . . . C26 C -0.2276(2) 0.1290(2) 0.17509(13) 0.0253(4) Uani 1 1 d . . . . . H26 H -0.300257 0.098695 0.221670 0.030 Uiso 1 1 calc R U . . . C27 C -0.1028(2) 0.1899(2) 0.18902(12) 0.0222(3) Uani 1 1 d . . . . . H27 H -0.090202 0.201343 0.245142 0.027 Uiso 1 1 calc R U . . . C28 C 0.29382(19) 0.33176(18) 0.04057(10) 0.0148(3) Uani 1 1 d . . . . . C29 C 0.2895(2) 0.46690(19) 0.00339(11) 0.0178(3) Uani 1 1 d . . . . . H29 H 0.225416 0.550680 0.033611 0.021 Uiso 1 1 calc R U . . . C30 C 0.3793(2) 0.4796(2) -0.07824(11) 0.0214(3) Uani 1 1 d . . . . . H30 H 0.376235 0.572009 -0.103503 0.026 Uiso 1 1 calc R U . . . C31 C 0.4725(2) 0.3580(2) -0.12221(11) 0.0233(4) Uani 1 1 d . . . . . H31 H 0.531923 0.366617 -0.178144 0.028 Uiso 1 1 calc R U . . . C32 C 0.4799(2) 0.2231(2) -0.08508(12) 0.0246(4) Uani 1 1 d . . . . . H32 H 0.545299 0.139844 -0.115248 0.030 Uiso 1 1 calc R U . . . C33 C 0.3918(2) 0.21023(19) -0.00391(11) 0.0208(3) Uani 1 1 d . . . . . H33 H 0.397982 0.118010 0.021683 0.025 Uiso 1 1 calc R U . . . N1 N 0.43998(17) -0.29293(15) 0.42204(9) 0.0155(3) Uani 1 1 d . . . . . P1 P 0.17251(5) 0.30291(4) 0.14368(3) 0.01360(7) Uani 1 1 d . . . . . 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 0.01451(3) 0.01436(3) 0.01344(3) 0.00185(2) -0.00378(2) -0.00175(2) C1 0.0152(7) 0.0172(7) 0.0156(7) -0.0003(6) -0.0018(6) -0.0036(6) C2 0.0162(7) 0.0168(7) 0.0152(7) 0.0011(6) -0.0015(6) -0.0050(6) C3 0.0147(7) 0.0177(8) 0.0195(8) 0.0042(6) -0.0034(6) -0.0029(6) C4 0.0204(8) 0.0140(7) 0.0182(7) 0.0044(6) -0.0108(6) -0.0045(6) C5 0.0227(8) 0.0187(8) 0.0231(8) 0.0007(6) -0.0116(7) 0.0000(7) C6 0.0309(10) 0.0154(8) 0.0320(10) -0.0017(7) -0.0179(8) 0.0010(7) C7 0.0329(10) 0.0164(8) 0.0365(10) 0.0057(7) -0.0211(8) -0.0080(7) C8 0.0262(9) 0.0207(8) 0.0269(9) 0.0084(7) -0.0143(7) -0.0105(7) C9 0.0197(8) 0.0186(8) 0.0180(7) 0.0054(6) -0.0099(6) -0.0068(6) C10 0.0186(7) 0.0202(8) 0.0155(7) 0.0043(6) -0.0081(6) -0.0069(6) C11 0.0199(8) 0.0296(9) 0.0154(7) 0.0040(7) -0.0048(6) -0.0106(7) C12 0.0206(8) 0.0311(10) 0.0156(8) -0.0017(7) -0.0028(6) -0.0036(7) C13 0.0255(9) 0.0218(8) 0.0174(8) -0.0026(6) -0.0053(7) -0.0027(7) C14 0.0210(8) 0.0178(8) 0.0173(7) 0.0009(6) -0.0044(6) -0.0057(6) C15 0.0163(7) 0.0178(7) 0.0143(7) 0.0030(6) -0.0058(6) -0.0037(6) C16 0.0143(7) 0.0155(7) 0.0141(7) 0.0006(6) -0.0021(6) -0.0020(6) C17 0.0208(8) 0.0209(8) 0.0186(8) 0.0001(6) -0.0077(6) -0.0031(7) C18 0.0317(10) 0.0233(9) 0.0226(9) -0.0046(7) -0.0105(7) -0.0048(8) C19 0.0307(10) 0.0192(8) 0.0194(8) -0.0046(7) -0.0025(7) 0.0005(7) C20 0.0217(8) 0.0218(8) 0.0182(8) -0.0015(6) -0.0033(6) 0.0034(7) C21 0.0178(8) 0.0208(8) 0.0167(7) -0.0015(6) -0.0044(6) -0.0013(6) C22 0.0141(7) 0.0139(7) 0.0185(7) 0.0018(6) -0.0054(6) -0.0025(6) C23 0.0188(8) 0.0187(8) 0.0189(8) -0.0002(6) -0.0055(6) -0.0034(6) C24 0.0234(9) 0.0230(9) 0.0266(9) -0.0042(7) -0.0115(7) -0.0034(7) C25 0.0195(8) 0.0201(8) 0.0398(11) -0.0020(8) -0.0099(8) -0.0061(7) C26 0.0191(8) 0.0250(9) 0.0321(10) 0.0047(8) -0.0030(7) -0.0085(7) C27 0.0223(8) 0.0258(9) 0.0192(8) 0.0044(7) -0.0042(7) -0.0071(7) C28 0.0126(7) 0.0177(7) 0.0146(7) -0.0001(6) -0.0039(5) -0.0026(6) C29 0.0157(7) 0.0184(8) 0.0188(8) 0.0010(6) -0.0036(6) -0.0027(6) C30 0.0195(8) 0.0249(9) 0.0208(8) 0.0050(7) -0.0042(6) -0.0075(7) C31 0.0197(8) 0.0336(10) 0.0166(8) 0.0007(7) -0.0008(6) -0.0088(7) C32 0.0246(9) 0.0259(9) 0.0197(8) -0.0063(7) 0.0002(7) -0.0011(7) C33 0.0228(8) 0.0182(8) 0.0197(8) -0.0021(6) -0.0034(7) -0.0011(7) N1 0.0164(6) 0.0135(6) 0.0163(6) 0.0023(5) -0.0025(5) -0.0033(5) P1 0.01358(18) 0.01379(18) 0.01353(18) 0.00107(14) -0.00386(14) -0.00195(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' N N 0.0061 0.0033 '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 C1 Au1 P1 175.56(5) . . ? C2 C1 Au1 178.12(15) . . ? C1 C2 C3 173.60(17) . . ? N1 C3 C2 111.44(14) . . ? N1 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N1 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N1 C4 C5 129.58(16) . . ? N1 C4 C9 108.62(15) . . ? C5 C4 C9 121.80(16) . . ? C6 C5 C4 117.38(18) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C5 C6 C7 121.39(18) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 121.33(17) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 118.93(18) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C4 119.17(17) . . ? C8 C9 C10 134.21(17) . . ? C4 C9 C10 106.61(15) . . ? C11 C10 C15 119.08(16) . . ? C11 C10 C9 134.48(16) . . ? C15 C10 C9 106.44(15) . . ? C12 C11 C10 118.94(16) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.90(17) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 121.39(17) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 117.24(16) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? N1 C15 C14 128.24(15) . . ? N1 C15 C10 109.35(15) . . ? C14 C15 C10 122.42(16) . . ? C17 C16 C21 119.73(16) . . ? C17 C16 P1 119.48(13) . . ? C21 C16 P1 120.63(13) . . ? C18 C17 C16 119.82(16) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 120.04(17) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.32(17) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 119.88(17) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C16 120.13(16) . . ? C20 C21 H21 119.9 . . ? C16 C21 H21 119.9 . . ? C23 C22 C27 119.48(16) . . ? C23 C22 P1 122.84(13) . . ? C27 C22 P1 117.57(13) . . ? C22 C23 C24 119.94(17) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.08(17) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.16(17) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C27 120.16(18) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C22 120.17(17) . . ? C26 C27 H27 119.9 . . ? C22 C27 H27 119.9 . . ? C29 C28 C33 119.18(15) . . ? C29 C28 P1 123.31(13) . . ? C33 C28 P1 117.47(13) . . ? C28 C29 C30 120.14(16) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C31 C30 C29 119.98(17) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 120.29(17) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C33 C32 C31 119.87(17) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C32 C33 C28 120.49(17) . . ? C32 C33 H33 119.8 . . ? C28 C33 H33 119.8 . . ? C4 N1 C15 108.97(14) . . ? C4 N1 C3 126.78(15) . . ? C15 N1 C3 123.74(14) . . ? C16 P1 C28 105.73(8) . . ? C16 P1 C22 106.04(8) . . ? C28 P1 C22 104.78(8) . . ? C16 P1 Au1 117.82(6) . . ? C28 P1 Au1 111.54(6) . . ? C22 P1 Au1 110.00(6) . . ? 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 C1 2.0004(18) . ? Au1 P1 2.2686(8) . ? C1 C2 1.200(2) . ? C2 C3 1.472(2) . ? C3 N1 1.455(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.383(2) . ? C4 C5 1.393(3) . ? C4 C9 1.421(2) . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.396(2) . ? C8 H8 0.9500 . ? C9 C10 1.448(3) . ? C10 C11 1.398(3) . ? C10 C15 1.407(2) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 C13 1.399(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 C15 1.390(2) . ? C14 H14 0.9500 . ? C15 N1 1.385(2) . ? C16 C17 1.395(2) . ? C16 C21 1.398(2) . ? C16 P1 1.8115(18) . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(3) . ? C18 H18 0.9500 . ? C19 C20 1.389(3) . ? C19 H19 0.9500 . ? C20 C21 1.387(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.393(2) . ? C22 C27 1.396(2) . ? C22 P1 1.8207(17) . ? C23 C24 1.394(2) . ? C23 H23 0.9500 . ? C24 C25 1.384(3) . ? C24 H24 0.9500 . ? C25 C26 1.385(3) . ? C25 H25 0.9500 . ? C26 C27 1.385(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.391(2) . ? C28 C33 1.396(2) . ? C28 P1 1.8157(17) . ? C29 C30 1.397(2) . ? C29 H29 0.9500 . ? C30 C31 1.380(3) . ? C30 H30 0.9500 . ? C31 C32 1.387(3) . ? C31 H31 0.9500 . ? C32 C33 1.385(3) . ? C32 H32 0.9500 . ? C33 H33 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 N1 C4 C5 C6 179.57(16) . . . . ? C9 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C7 C8 C9 C4 -0.1(2) . . . . ? C7 C8 C9 C10 178.88(18) . . . . ? N1 C4 C9 C8 -179.89(14) . . . . ? C5 C4 C9 C8 -0.7(2) . . . . ? N1 C4 C9 C10 0.91(18) . . . . ? C5 C4 C9 C10 -179.89(15) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C4 C9 C10 C11 179.40(18) . . . . ? C8 C9 C10 C15 -179.15(18) . . . . ? C4 C9 C10 C15 -0.12(17) . . . . ? C15 C10 C11 C12 2.0(2) . . . . ? C9 C10 C11 C12 -177.46(18) . . . . ? C10 C11 C12 C13 -1.8(3) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C15 1.4(3) . . . . ? C13 C14 C15 N1 178.59(16) . . . . ? C13 C14 C15 C10 -1.1(2) . . . . ? C11 C10 C15 N1 179.68(14) . . . . ? C9 C10 C15 N1 -0.71(18) . . . . ? C11 C10 C15 C14 -0.6(2) . . . . ? C9 C10 C15 C14 179.00(15) . . . . ? C21 C16 C17 C18 -2.7(3) . . . . ? P1 C16 C17 C18 172.73(14) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? C17 C18 C19 C20 1.8(3) . . . . ? C18 C19 C20 C21 -2.2(3) . . . . ? C19 C20 C21 C16 0.1(3) . . . . ? C17 C16 C21 C20 2.3(3) . . . . ? P1 C16 C21 C20 -173.07(13) . . . . ? C27 C22 C23 C24 0.1(3) . . . . ? P1 C22 C23 C24 176.16(13) . . . . ? C22 C23 C24 C25 -0.4(3) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C24 C25 C26 C27 -0.2(3) . . . . ? C25 C26 C27 C22 0.0(3) . . . . ? C23 C22 C27 C26 0.1(3) . . . . ? P1 C22 C27 C26 -176.16(14) . . . . ? C33 C28 C29 C30 1.6(2) . . . . ? P1 C28 C29 C30 -176.26(13) . . . . ? C28 C29 C30 C31 0.0(3) . . . . ? C29 C30 C31 C32 -1.2(3) . . . . ? C30 C31 C32 C33 0.8(3) . . . . ? C31 C32 C33 C28 0.8(3) . . . . ? C29 C28 C33 C32 -2.0(3) . . . . ? P1 C28 C33 C32 176.00(14) . . . . ? C5 C4 N1 C15 179.51(16) . . . . ? C9 C4 N1 C15 -1.37(18) . . . . ? C5 C4 N1 C3 7.5(3) . . . . ? C9 C4 N1 C3 -173.36(15) . . . . ? C14 C15 N1 C4 -178.39(16) . . . . ? C10 C15 N1 C4 1.31(18) . . . . ? C14 C15 N1 C3 -6.1(3) . . . . ? C10 C15 N1 C3 173.59(14) . . . . ? C2 C3 N1 C4 112.05(18) . . . . ? C2 C3 N1 C15 -58.8(2) . . . . ? C17 C16 P1 C28 -98.15(14) . . . . ? C21 C16 P1 C28 77.23(15) . . . . ? C17 C16 P1 C22 150.95(14) . . . . ? C21 C16 P1 C22 -33.67(16) . . . . ? C17 C16 P1 Au1 27.29(15) . . . . ? C21 C16 P1 Au1 -157.33(12) . . . . ? C29 C28 P1 C16 -12.23(16) . . . . ? C33 C28 P1 C16 169.90(13) . . . . ? C29 C28 P1 C22 99.56(15) . . . . ? C33 C28 P1 C22 -78.31(15) . . . . ? C29 C28 P1 Au1 -141.46(13) . . . . ? C33 C28 P1 Au1 40.67(15) . . . . ? C23 C22 P1 C16 109.77(15) . . . . ? C27 C22 P1 C16 -74.10(15) . . . . ? C23 C22 P1 C28 -1.79(16) . . . . ? C27 C22 P1 C28 174.33(13) . . . . ? C23 C22 P1 Au1 -121.81(14) . . . . ? C27 C22 P1 Au1 54.32(15) . . . . ?