#------------------------------------------------------------------------------ #$Date: 2020-08-13 04:55:43 +0300 (Thu, 13 Aug 2020) $ #$Revision: 255284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705135.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_7705135 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 'C33 H29 Au N3 P' _chemical_formula_weight 695.53 _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 107.9050(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.2164(17) _cell_length_b 8.9192(8) _cell_length_c 17.6329(17) _cell_measurement_reflns_used 8179 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.83 _cell_measurement_theta_min 4.35 _cell_volume 2726.2(4) _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 0.998 _diffrn_measured_fraction_theta_max 0.974 _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 0.0590 _diffrn_reflns_av_unetI/netI 0.0578 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 23312 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.832 _diffrn_reflns_theta_min 2.350 _exptl_absorpt_coefficient_mu 5.483 _exptl_absorpt_correction_T_max 0.8528 _exptl_absorpt_correction_T_min 0.1783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.695 _exptl_crystal_description plate _exptl_crystal_F_000 1368 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.340 _exptl_crystal_size_min 0.030 _exptl_transmission_factor_max 0.8528 _exptl_transmission_factor_min 0.1783 _refine_diff_density_max 1.549 _refine_diff_density_min -1.973 _refine_diff_density_rms 0.158 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 343 _refine_ls_number_reflns 6304 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0386 _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^)+(0.0219P)^2^+10.0409P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.0834 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5038 _reflns_number_total 6304 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02113j2.cif _cod_data_source_block con254 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7705135 _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 0.178 _shelx_estimated_absorpt_t_max 0.853 _shelx_res_file ; TITL con254 in P2(1)/c con254.res created by SHELXL-2016/6 at 13:12:06 on 20-Jul-2020 CELL 0.71073 18.2164 8.9192 17.6329 90.000 107.905 90.000 ZERR 4.00 0.0017 0.0008 0.0017 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N P Au UNIT 132 116 12 4 4 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT 1 0 0 OMIT -14 0 4 OMIT -9 0 2 OMIT -14 0 10 OMIT -14 2 2 OMIT -17 3 7 OMIT -12 0 8 OMIT -10 0 2 OMIT -11 0 6 OMIT -21 4 13 OMIT -1 0 22 L.S. 20 ACTA BOND FMAP 2 PLAN 5 SIZE 0.48 0.34 0.03 TEMP -173 WGHT 0.021900 10.040900 FVAR 0.06694 MOLE 1 AU1 5 0.216953 0.313858 0.257211 11.00000 0.02258 0.01777 = 0.01950 -0.00133 0.00551 -0.00109 P1 4 0.136125 0.179142 0.156492 11.00000 0.02111 0.01660 = 0.01896 -0.00089 0.00558 0.00188 N1 3 0.368838 0.645247 0.526578 11.00000 0.02962 0.02252 = 0.02638 -0.00120 0.01312 0.00006 N2 3 0.371541 0.329132 0.661344 11.00000 0.03572 0.03364 = 0.02657 0.00368 0.01222 0.00102 N3 3 0.347466 0.924268 0.399328 11.00000 0.04094 0.03737 = 0.03274 0.00665 0.00624 -0.00598 C1 1 0.289894 0.435575 0.345559 11.00000 0.01470 0.01104 = 0.02538 0.00193 0.00236 0.00416 C2 1 0.334237 0.501683 0.397126 11.00000 0.02772 0.01924 = 0.03028 0.00338 0.01087 0.00809 C3 1 0.393792 0.578223 0.462792 11.00000 0.02411 0.02439 = 0.02696 -0.00167 0.00506 -0.00184 AFIX 23 H3A 2 0.434912 0.504575 0.487272 11.00000 -1.20000 H3B 2 0.417281 0.658310 0.438979 11.00000 -1.20000 AFIX 0 C4 1 0.337162 0.533428 0.568099 11.00000 0.02823 0.02729 = 0.02504 0.00190 0.00907 0.00197 AFIX 23 H4A 2 0.302413 0.466140 0.528306 11.00000 -1.20000 H4B 2 0.305906 0.584824 0.597317 11.00000 -1.20000 AFIX 0 C5 1 0.398472 0.439945 0.626331 11.00000 0.03083 0.02888 = 0.02230 -0.00135 0.00857 -0.00065 C6 1 0.477022 0.468429 0.643549 11.00000 0.03111 0.03114 = 0.02299 -0.00263 0.00539 -0.00218 AFIX 43 H6 2 0.494534 0.548536 0.618055 11.00000 -1.20000 AFIX 0 C7 1 0.530000 0.377367 0.699017 11.00000 0.03362 0.03971 = 0.02991 0.00050 0.01001 0.00160 AFIX 43 H7 2 0.583939 0.393605 0.711295 11.00000 -1.20000 AFIX 0 C8 1 0.502187 0.265018 0.734862 11.00000 0.03841 0.04619 = 0.03707 0.01629 0.00971 0.01165 AFIX 43 H8 2 0.536542 0.201003 0.772487 11.00000 -1.20000 AFIX 0 C9 1 0.422648 0.245307 0.715571 11.00000 0.04977 0.03678 = 0.03564 0.01082 0.01918 -0.00167 AFIX 43 H9 2 0.403808 0.168771 0.742158 11.00000 -1.20000 AFIX 0 C10 1 0.313829 0.767757 0.495111 11.00000 0.03068 0.02762 = 0.02803 -0.00261 0.01023 0.00180 AFIX 23 H10A 2 0.288343 0.795641 0.535241 11.00000 -1.20000 H10B 2 0.273498 0.733013 0.446645 11.00000 -1.20000 AFIX 0 C11 1 0.353696 0.903335 0.475056 11.00000 0.02456 0.02537 = 0.03624 0.00359 0.00866 0.00668 C12 1 0.394005 0.999748 0.534652 11.00000 0.03724 0.03028 = 0.04815 -0.00771 0.01796 -0.00098 AFIX 43 H12 2 0.397606 0.980023 0.588622 11.00000 -1.20000 AFIX 0 C13 1 0.428909 1.124578 0.515278 11.00000 0.04411 0.02621 = 0.06475 -0.01826 0.01849 -0.00453 AFIX 43 H13 2 0.454769 1.194658 0.555112 11.00000 -1.20000 AFIX 0 C14 1 0.425569 1.145592 0.437423 11.00000 0.03670 0.02282 = 0.08639 0.01157 0.01526 0.00045 AFIX 43 H14 2 0.451219 1.227830 0.422409 11.00000 -1.20000 AFIX 0 C15 1 0.384396 1.045344 0.381622 11.00000 0.04364 0.04987 = 0.05194 0.02545 0.00766 -0.00601 AFIX 43 H15 2 0.381505 1.061387 0.327518 11.00000 -1.20000 AFIX 0 C16 1 0.166809 -0.013061 0.150417 11.00000 0.01901 0.01937 = 0.02596 0.00132 0.01305 0.00019 C17 1 0.139965 -0.098125 0.080380 11.00000 0.02021 0.02282 = 0.02514 -0.00406 0.00527 -0.00121 AFIX 43 H17 2 0.108264 -0.053061 0.032736 11.00000 -1.20000 AFIX 0 C18 1 0.160081 -0.249554 0.081014 11.00000 0.03005 0.02488 = 0.03583 -0.00788 0.01485 -0.00260 AFIX 43 H18 2 0.140461 -0.308453 0.034248 11.00000 -1.20000 AFIX 0 C19 1 0.208361 -0.313479 0.149441 11.00000 0.02741 0.01984 = 0.04411 0.00459 0.02140 -0.00077 AFIX 43 H19 2 0.221848 -0.416366 0.149435 11.00000 -1.20000 AFIX 0 C20 1 0.237226 -0.229780 0.217766 11.00000 0.02919 0.02933 = 0.02477 0.00978 0.01098 0.00470 AFIX 43 H20 2 0.271195 -0.274818 0.264172 11.00000 -1.20000 AFIX 0 C21 1 0.216878 -0.079037 0.219284 11.00000 0.02204 0.02827 = 0.02144 0.00394 0.01059 0.00109 AFIX 43 H21 2 0.236764 -0.021609 0.266548 11.00000 -1.20000 AFIX 0 C22 1 0.125120 0.260788 0.059011 11.00000 0.02645 0.01395 = 0.02710 0.00124 0.01400 -0.00199 C23 1 0.053258 0.302188 0.006255 11.00000 0.02482 0.02425 = 0.02358 0.00239 0.00689 0.00295 AFIX 43 H23 2 0.007607 0.287844 0.020670 11.00000 -1.20000 AFIX 0 C24 1 0.049160 0.364192 -0.067086 11.00000 0.03190 0.02887 = 0.02939 0.00253 0.00462 0.00283 AFIX 43 H24 2 0.000548 0.392035 -0.103034 11.00000 -1.20000 AFIX 0 C25 1 0.115935 0.385732 -0.088170 11.00000 0.05620 0.02073 = 0.02318 0.00401 0.01529 -0.00297 AFIX 43 H25 2 0.112826 0.428833 -0.138330 11.00000 -1.20000 AFIX 0 C26 1 0.186886 0.344622 -0.036363 11.00000 0.03758 0.02623 = 0.03473 -0.00306 0.01997 -0.00423 AFIX 43 H26 2 0.232264 0.357517 -0.051448 11.00000 -1.20000 AFIX 0 C27 1 0.191807 0.284542 0.037647 11.00000 0.02768 0.02210 = 0.02203 -0.00152 0.01050 0.00018 AFIX 43 H27 2 0.240759 0.259530 0.073856 11.00000 -1.20000 AFIX 0 C28 1 0.039245 0.162683 0.163716 11.00000 0.01843 0.02130 = 0.01799 0.00340 0.00759 0.00019 C29 1 0.013465 0.271722 0.207158 11.00000 0.03015 0.02184 = 0.02418 -0.00604 0.00811 -0.00365 AFIX 43 H29 2 0.046944 0.351021 0.232303 11.00000 -1.20000 AFIX 0 C30 1 -0.059795 0.264671 0.213600 11.00000 0.03425 0.02909 = 0.03056 -0.00316 0.01503 0.00304 AFIX 43 H30 2 -0.076462 0.339081 0.243200 11.00000 -1.20000 AFIX 0 C31 1 -0.109708 0.149544 0.177155 11.00000 0.02404 0.02992 = 0.02315 0.00286 0.01307 0.00332 AFIX 43 H31 2 -0.160335 0.145015 0.181581 11.00000 -1.20000 AFIX 0 C32 1 -0.084594 0.041491 0.134286 11.00000 0.03053 0.02161 = 0.02577 -0.00062 0.00833 -0.00294 AFIX 43 H32 2 -0.118374 -0.037382 0.109126 11.00000 -1.20000 AFIX 0 C33 1 -0.011568 0.047195 0.127799 11.00000 0.02856 0.02098 = 0.01888 -0.00490 0.00843 0.00264 AFIX 43 H33 2 0.004771 -0.028268 0.098526 11.00000 -1.20000 AFIX 0 HKLF 4 REM con254 in P2(1)/c REM R1 = 0.0386 for 5038 Fo > 4sig(Fo) and 0.0558 for all 6304 data REM 343 parameters refined using 0 restraints END WGHT 0.0216 10.1041 REM Highest difference peak 1.549, deepest hole -1.973, 1-sigma level 0.158 Q1 1 0.1713 0.3139 0.1815 11.00000 0.05 1.55 Q2 1 0.1743 0.3504 0.2257 11.00000 0.05 1.45 Q3 1 0.2606 0.2774 0.2850 11.00000 0.05 1.42 Q4 1 0.2332 0.3132 0.2208 11.00000 0.05 1.38 Q5 1 0.1630 0.2455 0.2775 11.00000 0.05 1.33 ; _shelx_res_checksum 93814 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 0.21695(2) 0.31386(2) 0.25721(2) 0.02017(7) Uani 1 1 d . . . . . P1 P 0.13612(8) 0.17914(15) 0.15649(8) 0.0190(3) Uani 1 1 d . . . . . N1 N 0.3688(3) 0.6452(5) 0.5266(3) 0.0251(10) Uani 1 1 d . . . . . N2 N 0.3715(3) 0.3291(6) 0.6613(3) 0.0314(11) Uani 1 1 d . . . . . N3 N 0.3475(3) 0.9243(6) 0.3993(3) 0.0382(13) Uani 1 1 d . . . . . C1 C 0.2899(3) 0.4356(5) 0.3456(3) 0.0179(10) Uani 1 1 d . . . . . C2 C 0.3342(3) 0.5017(6) 0.3971(3) 0.0253(12) Uani 1 1 d . . . . . C3 C 0.3938(3) 0.5782(6) 0.4628(3) 0.0258(12) Uani 1 1 d . . . . . H3A H 0.434912 0.504575 0.487272 0.031 Uiso 1 1 calc R U . . . H3B H 0.417281 0.658310 0.438979 0.031 Uiso 1 1 calc R U . . . C4 C 0.3372(3) 0.5334(6) 0.5681(3) 0.0267(12) Uani 1 1 d . . . . . H4A H 0.302413 0.466140 0.528306 0.032 Uiso 1 1 calc R U . . . H4B H 0.305906 0.584824 0.597317 0.032 Uiso 1 1 calc R U . . . C5 C 0.3985(3) 0.4399(7) 0.6263(3) 0.0272(12) Uani 1 1 d . . . . . C6 C 0.4770(4) 0.4684(6) 0.6435(3) 0.0291(13) Uani 1 1 d . . . . . H6 H 0.494534 0.548536 0.618055 0.035 Uiso 1 1 calc R U . . . C7 C 0.5300(4) 0.3774(7) 0.6990(4) 0.0344(14) Uani 1 1 d . . . . . H7 H 0.583939 0.393605 0.711295 0.041 Uiso 1 1 calc R U . . . C8 C 0.5022(4) 0.2650(8) 0.7349(4) 0.0410(17) Uani 1 1 d . . . . . H8 H 0.536542 0.201003 0.772487 0.049 Uiso 1 1 calc R U . . . C9 C 0.4226(4) 0.2453(7) 0.7156(4) 0.0394(16) Uani 1 1 d . . . . . H9 H 0.403808 0.168771 0.742158 0.047 Uiso 1 1 calc R U . . . C10 C 0.3138(4) 0.7678(6) 0.4951(4) 0.0285(13) Uani 1 1 d . . . . . H10A H 0.288343 0.795641 0.535241 0.034 Uiso 1 1 calc R U . . . H10B H 0.273498 0.733013 0.446645 0.034 Uiso 1 1 calc R U . . . C11 C 0.3537(3) 0.9033(6) 0.4751(4) 0.0289(13) Uani 1 1 d . . . . . C12 C 0.3940(4) 0.9997(7) 0.5347(4) 0.0375(15) Uani 1 1 d . . . . . H12 H 0.397606 0.980023 0.588622 0.045 Uiso 1 1 calc R U . . . C13 C 0.4289(4) 1.1246(7) 0.5153(5) 0.0446(18) Uani 1 1 d . . . . . H13 H 0.454769 1.194658 0.555112 0.054 Uiso 1 1 calc R U . . . C14 C 0.4256(4) 1.1456(7) 0.4374(5) 0.049(2) Uani 1 1 d . . . . . H14 H 0.451219 1.227830 0.422409 0.059 Uiso 1 1 calc R U . . . C15 C 0.3844(4) 1.0453(8) 0.3816(5) 0.050(2) Uani 1 1 d . . . . . H15 H 0.381505 1.061387 0.327518 0.060 Uiso 1 1 calc R U . . . C16 C 0.1668(3) -0.0131(6) 0.1504(3) 0.0201(11) Uani 1 1 d . . . . . C17 C 0.1400(3) -0.0981(6) 0.0804(3) 0.0231(12) Uani 1 1 d . . . . . H17 H 0.108264 -0.053061 0.032736 0.028 Uiso 1 1 calc R U . . . C18 C 0.1601(4) -0.2496(6) 0.0810(4) 0.0292(13) Uani 1 1 d . . . . . H18 H 0.140461 -0.308453 0.034248 0.035 Uiso 1 1 calc R U . . . C19 C 0.2084(3) -0.3135(6) 0.1494(4) 0.0281(12) Uani 1 1 d . . . . . H19 H 0.221848 -0.416366 0.149435 0.034 Uiso 1 1 calc R U . . . C20 C 0.2372(4) -0.2298(6) 0.2178(3) 0.0272(13) Uani 1 1 d . . . . . H20 H 0.271195 -0.274818 0.264172 0.033 Uiso 1 1 calc R U . . . C21 C 0.2169(3) -0.0790(6) 0.2193(3) 0.0230(11) Uani 1 1 d . . . . . H21 H 0.236764 -0.021609 0.266548 0.028 Uiso 1 1 calc R U . . . C22 C 0.1251(3) 0.2608(5) 0.0590(3) 0.0212(11) Uani 1 1 d . . . . . C23 C 0.0533(3) 0.3022(6) 0.0063(3) 0.0243(11) Uani 1 1 d . . . . . H23 H 0.007607 0.287844 0.020670 0.029 Uiso 1 1 calc R U . . . C24 C 0.0492(4) 0.3642(6) -0.0671(4) 0.0311(14) Uani 1 1 d . . . . . H24 H 0.000548 0.392035 -0.103034 0.037 Uiso 1 1 calc R U . . . C25 C 0.1159(4) 0.3857(6) -0.0882(4) 0.0327(15) Uani 1 1 d . . . . . H25 H 0.112826 0.428833 -0.138330 0.039 Uiso 1 1 calc R U . . . C26 C 0.1869(4) 0.3446(6) -0.0364(4) 0.0308(14) Uani 1 1 d . . . . . H26 H 0.232264 0.357517 -0.051448 0.037 Uiso 1 1 calc R U . . . C27 C 0.1918(3) 0.2845(6) 0.0376(3) 0.0233(12) Uani 1 1 d . . . . . H27 H 0.240759 0.259530 0.073856 0.028 Uiso 1 1 calc R U . . . C28 C 0.0392(3) 0.1627(5) 0.1637(3) 0.0188(11) Uani 1 1 d . . . . . C29 C 0.0135(4) 0.2717(6) 0.2072(3) 0.0254(12) Uani 1 1 d . . . . . H29 H 0.046944 0.351021 0.232303 0.031 Uiso 1 1 calc R U . . . C30 C -0.0598(4) 0.2647(6) 0.2136(4) 0.0302(13) Uani 1 1 d . . . . . H30 H -0.076462 0.339081 0.243200 0.036 Uiso 1 1 calc R U . . . C31 C -0.1097(3) 0.1495(6) 0.1772(3) 0.0244(12) Uani 1 1 d . . . . . H31 H -0.160335 0.145015 0.181581 0.029 Uiso 1 1 calc R U . . . C32 C -0.0846(3) 0.0415(6) 0.1343(3) 0.0260(12) Uani 1 1 d . . . . . H32 H -0.118374 -0.037382 0.109126 0.031 Uiso 1 1 calc R U . . . C33 C -0.0116(3) 0.0472(6) 0.1278(3) 0.0225(11) Uani 1 1 d . . . . . H33 H 0.004771 -0.028268 0.098526 0.027 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 0.02258(11) 0.01777(9) 0.01950(10) -0.00133(9) 0.00551(7) -0.00109(9) P1 0.0211(7) 0.0166(6) 0.0190(6) -0.0009(5) 0.0056(5) 0.0019(6) N1 0.030(3) 0.023(2) 0.026(2) -0.0012(19) 0.013(2) 0.0001(19) N2 0.036(3) 0.034(3) 0.027(2) 0.004(2) 0.012(2) 0.001(2) N3 0.041(3) 0.037(3) 0.033(3) 0.007(2) 0.006(3) -0.006(3) C1 0.015(3) 0.011(2) 0.025(3) 0.002(2) 0.002(2) 0.0042(19) C2 0.028(3) 0.019(2) 0.030(3) 0.003(2) 0.011(3) 0.008(2) C3 0.024(3) 0.024(3) 0.027(3) -0.002(2) 0.005(2) -0.002(2) C4 0.028(3) 0.027(3) 0.025(3) 0.002(2) 0.009(2) 0.002(2) C5 0.031(3) 0.029(3) 0.022(3) -0.001(2) 0.009(2) -0.001(3) C6 0.031(3) 0.031(3) 0.023(3) -0.003(2) 0.005(3) -0.002(3) C7 0.034(4) 0.040(3) 0.030(3) 0.001(3) 0.010(3) 0.002(3) C8 0.038(4) 0.046(4) 0.037(4) 0.016(3) 0.010(3) 0.012(3) C9 0.050(4) 0.037(3) 0.036(4) 0.011(3) 0.019(3) -0.002(3) C10 0.031(3) 0.028(3) 0.028(3) -0.003(2) 0.010(3) 0.002(2) C11 0.025(3) 0.025(3) 0.036(3) 0.004(2) 0.009(3) 0.007(2) C12 0.037(4) 0.030(3) 0.048(4) -0.008(3) 0.018(3) -0.001(3) C13 0.044(4) 0.026(3) 0.065(5) -0.018(3) 0.018(4) -0.005(3) C14 0.037(4) 0.023(3) 0.086(6) 0.012(3) 0.015(4) 0.000(3) C15 0.044(4) 0.050(4) 0.052(4) 0.025(4) 0.008(4) -0.006(4) C16 0.019(3) 0.019(2) 0.026(3) 0.001(2) 0.013(2) 0.000(2) C17 0.020(3) 0.023(3) 0.025(3) -0.004(2) 0.005(2) -0.001(2) C18 0.030(3) 0.025(3) 0.036(3) -0.008(3) 0.015(3) -0.003(2) C19 0.027(3) 0.020(2) 0.044(3) 0.005(3) 0.021(3) -0.001(2) C20 0.029(3) 0.029(3) 0.025(3) 0.010(2) 0.011(3) 0.005(2) C21 0.022(3) 0.028(3) 0.021(3) 0.004(2) 0.011(2) 0.001(2) C22 0.026(3) 0.014(2) 0.027(3) 0.001(2) 0.014(2) -0.002(2) C23 0.025(3) 0.024(3) 0.024(3) 0.002(2) 0.007(2) 0.003(2) C24 0.032(3) 0.029(3) 0.029(3) 0.003(2) 0.005(3) 0.003(3) C25 0.056(4) 0.021(3) 0.023(3) 0.004(2) 0.015(3) -0.003(3) C26 0.038(4) 0.026(3) 0.035(3) -0.003(2) 0.020(3) -0.004(3) C27 0.028(3) 0.022(3) 0.022(3) -0.002(2) 0.011(2) 0.000(2) C28 0.018(3) 0.021(2) 0.018(2) 0.003(2) 0.008(2) 0.000(2) C29 0.030(3) 0.022(3) 0.024(3) -0.006(2) 0.008(2) -0.004(2) C30 0.034(4) 0.029(3) 0.031(3) -0.003(2) 0.015(3) 0.003(3) C31 0.024(3) 0.030(3) 0.023(3) 0.003(2) 0.013(2) 0.003(2) C32 0.031(3) 0.022(3) 0.026(3) -0.001(2) 0.008(2) -0.003(2) C33 0.029(3) 0.021(2) 0.019(3) -0.005(2) 0.008(2) 0.003(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' 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' Au Au -2.0133 8.8022 '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 178.95(15) . . ? C28 P1 C16 104.6(2) . . ? C28 P1 C22 105.8(2) . . ? C16 P1 C22 105.6(2) . . ? C28 P1 Au1 113.50(17) . . ? C16 P1 Au1 114.09(19) . . ? C22 P1 Au1 112.55(18) . . ? C4 N1 C3 111.8(4) . . ? C4 N1 C10 111.6(5) . . ? C3 N1 C10 110.5(4) . . ? C5 N2 C9 118.0(6) . . ? C11 N3 C15 116.8(6) . . ? C2 C1 Au1 177.4(5) . . ? C1 C2 C3 176.6(6) . . ? N1 C3 C2 117.5(5) . . ? N1 C4 C5 113.2(5) . . ? N2 C5 C6 122.2(6) . . ? N2 C5 C4 114.9(5) . . ? C6 C5 C4 122.8(5) . . ? C5 C6 C7 119.2(6) . . ? C8 C7 C6 118.4(6) . . ? C7 C8 C9 119.1(6) . . ? N2 C9 C8 123.1(6) . . ? N1 C10 C11 111.3(5) . . ? N3 C11 C12 122.9(6) . . ? N3 C11 C10 117.0(5) . . ? C12 C11 C10 120.2(6) . . ? C13 C12 C11 119.5(7) . . ? C14 C13 C12 118.6(7) . . ? C13 C14 C15 118.5(7) . . ? N3 C15 C14 123.7(7) . . ? C17 C16 C21 119.5(5) . . ? C17 C16 P1 122.1(4) . . ? C21 C16 P1 118.3(4) . . ? C18 C17 C16 119.7(5) . . ? C19 C18 C17 120.1(6) . . ? C20 C19 C18 120.7(5) . . ? C19 C20 C21 120.4(5) . . ? C20 C21 C16 119.5(5) . . ? C27 C22 C23 119.6(5) . . ? C27 C22 P1 117.6(4) . . ? C23 C22 P1 122.8(4) . . ? C24 C23 C22 119.7(6) . . ? C23 C24 C25 120.2(6) . . ? C26 C25 C24 120.2(6) . . ? C25 C26 C27 120.0(6) . . ? C26 C27 C22 120.2(6) . . ? C33 C28 C29 118.1(5) . . ? C33 C28 P1 123.4(4) . . ? C29 C28 P1 118.5(4) . . ? C30 C29 C28 120.6(5) . . ? C29 C30 C31 120.6(5) . . ? C32 C31 C30 119.1(6) . . ? C33 C32 C31 120.7(5) . . ? C32 C33 C28 120.9(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 C1 2.024(5) . ? Au1 P1 2.2711(13) . ? P1 C28 1.814(5) . ? P1 C16 1.816(5) . ? P1 C22 1.820(6) . ? N1 C4 1.457(7) . ? N1 C3 1.464(7) . ? N1 C10 1.471(7) . ? N2 C5 1.336(7) . ? N2 C9 1.339(8) . ? N3 C11 1.318(8) . ? N3 C15 1.358(8) . ? C1 C2 1.173(7) . ? C2 C3 1.487(8) . ? C4 C5 1.514(8) . ? C5 C6 1.392(8) . ? C6 C7 1.403(8) . ? C7 C8 1.363(9) . ? C8 C9 1.394(10) . ? C10 C11 1.508(8) . ? C11 C12 1.381(9) . ? C12 C13 1.376(9) . ? C13 C14 1.368(11) . ? C14 C15 1.370(10) . ? C16 C17 1.403(7) . ? C16 C21 1.404(7) . ? C17 C18 1.399(7) . ? C18 C19 1.379(8) . ? C19 C20 1.377(8) . ? C20 C21 1.397(8) . ? C22 C27 1.394(8) . ? C22 C23 1.402(8) . ? C23 C24 1.387(8) . ? C24 C25 1.390(9) . ? C25 C26 1.383(9) . ? C26 C27 1.388(8) . ? C28 C33 1.399(7) . ? C28 C29 1.405(7) . ? C29 C30 1.375(8) . ? C30 C31 1.391(8) . ? C31 C32 1.386(7) . ? C32 C33 1.371(8) . ?