#------------------------------------------------------------------------------ #$Date: 2024-06-22 01:16:25 +0300 (Sat, 22 Jun 2024) $ #$Revision: 292518 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571957.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_1571957 loop_ _publ_author_name 'Kharraz, Haia' 'Alemany, Pere' 'Canadell, Enric' 'Le Gal, Yann' 'Roisnel, Thierry' 'Cui, Hengbo' 'Kim, Kee Hoon' 'Fourmigue, Marc' 'Lorcy, Dominique' _publ_section_title ; Mixed-ligand, radical, gold bis(dithiolene) complexes: from single-component conductors to controllable NIR-II absorbers ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC03238A _journal_year 2024 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C11 H9 Au N S6, C16 H36 N' _chemical_formula_sum 'C27 H45 Au N2 S6' _chemical_formula_weight 786.97 _chemical_name_common (Bu4N)[Au(bdt)(Et-thiazdt)] _chemical_name_systematic Tetrabutylammonium,(benzene-1,2-dithiolate)(N-Ethyl-thiazoline-2-one-4,5-dithiolate)aurate _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_update_record ; 2024-04-16 deposited with the CCDC. 2024-06-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.821(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5242(11) _cell_length_b 22.193(3) _cell_length_c 16.2006(17) _cell_measurement_reflns_used 7837 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4426 _cell_measurement_theta_min 2.2530 _cell_measurement_wavelength 0.710730 _cell_volume 3294.6(7) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'Bruker APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2023)' _computing_structure_refinement 'SHELXL-2019_2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector CMOS-PHOTON70 _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 -0.0334441 _diffrn_orient_matrix_UB_12 -0.0282066 _diffrn_orient_matrix_UB_13 0.0389031 _diffrn_orient_matrix_UB_21 0.0486458 _diffrn_orient_matrix_UB_22 -0.0342460 _diffrn_orient_matrix_UB_23 -0.0213962 _diffrn_orient_matrix_UB_31 0.0917845 _diffrn_orient_matrix_UB_32 0.0078725 _diffrn_orient_matrix_UB_33 0.0463119 _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_unetI/netI 0.0485 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 25969 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.502 _diffrn_reflns_theta_min 2.223 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 4.865 _exptl_absorpt_correction_T_max 0.823 _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.587 _exptl_crystal_description prism _exptl_crystal_F_000 1584 _exptl_crystal_size_max 0.070 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.040 _refine_diff_density_max 5.992 _refine_diff_density_min -1.941 _refine_diff_density_rms 0.575 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 331 _refine_ls_number_reflns 7559 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0451 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1311 _refine_ls_wR_factor_ref 0.1463 _reflns_number_gt 5912 _reflns_number_total 7559 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d4sc03238a2.cif _cod_data_source_block HK270_2 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1571957 _shelx_res_file ; TITL HK270_2 [Space group= P2(1)/n] job.res created by SHELXL-2019/3 at 13:48:44 on 03-Oct-2023 CELL 0.71073 9.5242 22.1928 16.2006 90.000 105.821 90.000 ZERR 4.00 0.0011 0.0028 0.0017 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H AU N S UNIT 108 180 4 8 24 MERG 2 FMAP 2 SIZE 0.04 0.06 0.07 ACTA TWIN -1 0 0 0 -1 0 0.927 0 1 HTAB 2.00000 BOND $H CONF OMIT 0 2 1 LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.100000 BASF 0.00009 FVAR 0.13357 MOLE 1 AU1 3 0.009472 0.691791 0.665819 11.00000 0.03592 0.03823 = 0.01911 -0.00125 0.00531 0.00358 S1 5 -0.107842 0.783153 0.638829 11.00000 0.03035 0.03579 = 0.03221 0.00226 0.00141 -0.00267 S2 5 0.219798 0.735829 0.650844 11.00000 0.03685 0.05828 = 0.03291 0.00014 0.01054 0.00012 S3 5 -0.200319 0.647824 0.688004 11.00000 0.04386 0.03010 = 0.02943 0.00243 0.00633 -0.00039 S4 5 0.137031 0.601651 0.688568 11.00000 0.05900 0.04842 = 0.05435 0.00159 0.02438 0.01819 S5 5 0.028627 0.481141 0.733406 11.00000 0.09225 0.03628 = 0.04635 -0.00316 0.01760 0.01581 S6 5 -0.207273 0.409866 0.777580 11.00000 0.12271 0.03430 = 0.03952 -0.00199 0.01473 -0.01095 C1 1 0.030309 0.832246 0.622701 11.00000 0.04177 0.04851 = 0.02302 -0.00499 0.00133 -0.00993 C2 1 -0.003969 0.892137 0.606206 11.00000 0.04783 0.04505 = 0.06264 -0.00429 0.01228 -0.01258 AFIX 43 H2 2 -0.098063 0.906557 0.605817 11.00000 -1.20000 AFIX 0 C3 1 0.099019 0.931496 0.590129 11.00000 0.07423 0.04796 = 0.06342 -0.00572 0.01412 -0.02217 AFIX 43 H3 2 0.074477 0.972443 0.576220 11.00000 -1.20000 AFIX 0 C4 1 0.240091 0.910068 0.594663 11.00000 0.08673 0.05107 = 0.05480 -0.01505 0.02914 -0.03107 AFIX 43 H4 2 0.311105 0.936271 0.582876 11.00000 -1.20000 AFIX 0 C5 1 0.273530 0.852022 0.615885 11.00000 0.05285 0.06374 = 0.04104 -0.01084 0.01719 -0.01938 AFIX 43 H5 2 0.370882 0.838592 0.623236 11.00000 -1.20000 AFIX 0 C6 1 0.168682 0.810991 0.627388 11.00000 0.03967 0.05484 = 0.02446 -0.00865 0.01015 -0.01366 C7 1 0.004215 0.556938 0.708482 11.00000 0.06857 0.03290 = 0.02434 -0.00420 0.00149 0.01525 C8 1 -0.129997 0.574338 0.711455 11.00000 0.06854 0.03461 = 0.01908 -0.00057 0.00215 -0.00303 N9 4 -0.214012 0.528391 0.733218 11.00000 0.07367 0.03507 = 0.02741 -0.00336 0.01294 -0.00756 C10 1 -0.352784 0.537963 0.748331 11.00000 0.06371 0.04637 = 0.04547 0.01088 0.00236 -0.01852 AFIX 23 H10A 2 -0.412637 0.501193 0.731589 11.00000 -1.20000 H10B 2 -0.402797 0.571286 0.711156 11.00000 -1.20000 AFIX 0 C11 1 -0.344878 0.553186 0.841704 11.00000 0.08540 0.04751 = 0.05295 -0.00541 0.02767 0.00010 AFIX 137 H11A 2 -0.283542 0.523457 0.879768 11.00000 -1.50000 H11B 2 -0.443298 0.552397 0.849574 11.00000 -1.50000 H11C 2 -0.302735 0.593443 0.855513 11.00000 -1.50000 AFIX 0 C12 1 -0.141938 0.474443 0.748810 11.00000 0.11009 0.03069 = 0.02337 -0.00545 0.00065 -0.00218 MOLE 2 N21 4 0.554229 0.285677 0.571178 11.00000 0.02403 0.02703 = 0.02076 -0.00098 0.00529 -0.00061 C21 1 0.484584 0.231616 0.520596 11.00000 0.02624 0.03679 = 0.02466 -0.00946 -0.00175 -0.00121 AFIX 23 H21A 2 0.548324 0.218013 0.485126 11.00000 -1.20000 H21B 2 0.390808 0.244463 0.480843 11.00000 -1.20000 AFIX 0 C22 1 0.454905 0.177940 0.571584 11.00000 0.02834 0.03787 = 0.03143 -0.00477 0.00464 -0.00432 AFIX 23 H22A 2 0.542175 0.169358 0.619623 11.00000 -1.20000 H22B 2 0.372714 0.187267 0.595958 11.00000 -1.20000 AFIX 0 C23 1 0.417661 0.123267 0.513629 11.00000 0.06750 0.03731 = 0.04119 0.00309 0.00322 -0.00981 AFIX 23 H23A 2 0.335051 0.133509 0.463589 11.00000 -1.20000 H23B 2 0.502496 0.113297 0.491937 11.00000 -1.20000 AFIX 0 C24 1 0.377847 0.069011 0.556950 11.00000 0.07804 0.04846 = 0.04476 0.00278 -0.00400 -0.01938 AFIX 137 H24A 2 0.462678 0.055800 0.602631 11.00000 -1.50000 H24B 2 0.347032 0.036513 0.514949 11.00000 -1.50000 H24C 2 0.297709 0.079125 0.581691 11.00000 -1.50000 AFIX 0 C25 1 0.700317 0.269375 0.633371 11.00000 0.02005 0.02894 = 0.01950 0.00387 -0.00374 -0.00040 AFIX 23 H25A 2 0.747958 0.306840 0.660348 11.00000 -1.20000 H25B 2 0.682087 0.243819 0.679463 11.00000 -1.20000 AFIX 0 C26 1 0.804849 0.236435 0.593084 11.00000 0.02219 0.04336 = 0.02306 -0.00243 0.00241 0.00069 AFIX 23 H26A 2 0.822077 0.261030 0.545803 11.00000 -1.20000 H26B 2 0.760764 0.197742 0.568611 11.00000 -1.20000 AFIX 0 C27 1 0.950095 0.224328 0.659603 11.00000 0.02178 0.03618 = 0.03322 0.00087 0.00113 -0.00287 AFIX 23 H27A 2 0.992622 0.262891 0.685524 11.00000 -1.20000 H27B 2 0.933383 0.198528 0.705871 11.00000 -1.20000 AFIX 0 C28 1 1.055917 0.193362 0.618441 11.00000 0.02340 0.05127 = 0.04185 0.00379 0.00588 0.00605 AFIX 137 H28A 2 1.013056 0.155521 0.591967 11.00000 -1.50000 H28B 2 1.147228 0.184833 0.662321 11.00000 -1.50000 H28C 2 1.075861 0.219720 0.574433 11.00000 -1.50000 AFIX 0 C29 1 0.573654 0.332469 0.505926 11.00000 0.02629 0.03730 = 0.02112 0.00642 0.00803 0.00242 AFIX 23 H29A 2 0.637626 0.314944 0.473183 11.00000 -1.20000 H29B 2 0.477212 0.339810 0.464827 11.00000 -1.20000 AFIX 0 C30 1 0.636689 0.392343 0.541452 11.00000 0.03065 0.03335 = 0.03266 0.00870 0.00679 0.00024 AFIX 23 H30A 2 0.734249 0.386182 0.581949 11.00000 -1.20000 H30B 2 0.572981 0.411245 0.573257 11.00000 -1.20000 AFIX 0 C31 1 0.649529 0.433362 0.469668 11.00000 0.06282 0.04628 = 0.04040 0.01284 0.02121 -0.00547 AFIX 23 H31A 2 0.704166 0.411993 0.434580 11.00000 -1.20000 H31B 2 0.550388 0.441705 0.432351 11.00000 -1.20000 AFIX 0 C32 1 0.722455 0.490986 0.498080 11.00000 0.05100 0.04167 = 0.07310 0.02071 0.02150 0.00044 AFIX 137 H32A 2 0.668650 0.512870 0.532286 11.00000 -1.50000 H32B 2 0.725047 0.515152 0.447887 11.00000 -1.50000 H32C 2 0.822349 0.483402 0.533033 11.00000 -1.50000 AFIX 0 C33 1 0.457746 0.310196 0.624071 11.00000 0.02297 0.03076 = 0.02269 0.00039 0.00747 -0.00274 AFIX 23 H33A 2 0.444486 0.278221 0.663891 11.00000 -1.20000 H33B 2 0.509459 0.344054 0.659332 11.00000 -1.20000 AFIX 0 C34 1 0.308351 0.332088 0.573348 11.00000 0.02103 0.03425 = 0.02397 0.00257 0.00269 0.00681 AFIX 23 H34A 2 0.319756 0.366757 0.537267 11.00000 -1.20000 H34B 2 0.257733 0.299507 0.534860 11.00000 -1.20000 AFIX 0 C35 1 0.217211 0.350769 0.631615 11.00000 0.02495 0.04102 = 0.03187 -0.00899 0.00472 -0.00180 AFIX 23 H35A 2 0.263809 0.385621 0.666657 11.00000 -1.20000 H35B 2 0.213034 0.317199 0.671118 11.00000 -1.20000 AFIX 0 C36 1 0.063401 0.367726 0.581460 11.00000 0.02576 0.04664 = 0.05041 -0.00651 0.00958 0.00212 AFIX 137 H36A 2 0.065970 0.404954 0.549370 11.00000 -1.50000 H36B 2 0.003483 0.373944 0.621234 11.00000 -1.50000 H36C 2 0.021333 0.335241 0.541359 11.00000 -1.50000 AFIX 0 HKLF 4 REM HK270_2 [Space group= P2(1)/n] REM wR2 = 0.1463, GooF = S = 1.005, Restrained GooF = 1.005 for all data REM R1 = 0.0451 for 5912 Fo > 4sig(Fo) and 0.0639 for all 7559 data REM 331 parameters refined using 0 restraints END WGHT 0.0384 16.5466 REM Instructions for potential hydrogen bonds EQIV $1 -x-1/2, y+1/2, -z+3/2 HTAB C2 S6_$1 EQIV $2 -x, -y+1, -z+1 HTAB C21 S1_$2 EQIV $3 x+1, y, z HTAB C25 S6_$3 EQIV $4 -x+1/2, y-1/2, -z+3/2 HTAB C25 S3_$4 EQIV $5 -x+1, -y+1, -z+1 HTAB C29 S2_$5 REM Highest difference peak 5.992, deepest hole -1.941, 1-sigma level 0.575 Q1 1 -0.0275 0.6559 0.6645 11.00000 0.05 5.99 Q2 1 0.1907 0.6972 0.6622 11.00000 0.05 2.20 Q3 1 0.0997 0.7318 0.6599 11.00000 0.05 1.71 Q4 1 1.0440 0.1506 0.4998 11.00000 0.05 1.66 Q5 1 -0.0381 0.2816 0.5003 11.00000 0.05 1.63 Q6 1 0.1000 0.6317 0.6595 11.00000 0.05 1.61 Q7 1 0.0329 0.9275 0.5004 11.00000 0.05 1.61 Q8 1 0.0983 0.8123 0.6595 11.00000 0.05 1.59 Q9 1 1.0367 0.2302 0.4987 11.00000 0.05 1.58 Q10 1 0.0084 0.9614 0.6596 11.00000 0.05 1.57 Q11 1 0.9612 0.1187 0.5005 11.00000 0.05 1.57 Q12 1 1.0406 0.1969 0.4994 11.00000 0.05 1.56 Q13 1 -0.0430 0.9637 0.5003 11.00000 0.05 1.56 Q14 1 0.0439 0.3493 0.5001 11.00000 0.05 1.55 Q15 1 0.7501 0.2538 0.6215 11.00000 0.05 1.53 Q16 1 0.0407 0.5741 0.6609 11.00000 0.05 1.53 Q17 1 1.0997 0.1666 0.6589 11.00000 0.05 1.52 Q18 1 0.0227 0.8269 0.6576 11.00000 0.05 1.52 Q19 1 -0.5944 0.5385 0.8399 11.00000 0.05 1.52 Q20 1 -0.0461 0.8953 0.5004 11.00000 0.05 1.50 ; _shelx_res_checksum 15324 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.00947(3) 0.69179(2) 0.66582(2) 0.03151(11) Uani 1 1 d . . . . . S1 S -0.10784(17) 0.78315(7) 0.63883(10) 0.0342(3) Uani 1 1 d . . . . . S2 S 0.21980(19) 0.73583(9) 0.65084(11) 0.0425(4) Uani 1 1 d . . . . . S3 S -0.20032(19) 0.64782(7) 0.68800(10) 0.0352(3) Uani 1 1 d . . . . . S4 S 0.1370(2) 0.60165(9) 0.68857(13) 0.0522(5) Uani 1 1 d . . . . . S5 S 0.0286(3) 0.48114(9) 0.73341(13) 0.0585(5) Uani 1 1 d . . . . . S6 S -0.2073(3) 0.40987(9) 0.77758(13) 0.0670(7) Uani 1 1 d . . . . . C1 C 0.0303(8) 0.8322(3) 0.6227(4) 0.0392(15) Uani 1 1 d . . . . . C2 C -0.0040(9) 0.8921(3) 0.6062(5) 0.0524(19) Uani 1 1 d . . . . . H2 H -0.098063 0.906557 0.605817 0.063 Uiso 1 1 calc R U . . . C3 C 0.0990(10) 0.9315(4) 0.5901(6) 0.063(2) Uani 1 1 d . . . . . H3 H 0.074477 0.972443 0.576220 0.075 Uiso 1 1 calc R U . . . C4 C 0.2401(11) 0.9101(4) 0.5947(5) 0.062(2) Uani 1 1 d . . . . . H4 H 0.311105 0.936271 0.582876 0.075 Uiso 1 1 calc R U . . . C5 C 0.2735(9) 0.8520(4) 0.6159(5) 0.0517(19) Uani 1 1 d . . . . . H5 H 0.370882 0.838592 0.623236 0.062 Uiso 1 1 calc R U . . . C6 C 0.1687(8) 0.8110(3) 0.6274(4) 0.0394(16) Uani 1 1 d . . . . . C7 C 0.0042(9) 0.5569(3) 0.7085(4) 0.0441(17) Uani 1 1 d . . . . . C8 C -0.1300(9) 0.5743(3) 0.7115(4) 0.0427(16) Uani 1 1 d . . . . . N9 N -0.2140(7) 0.5284(3) 0.7332(3) 0.0455(14) Uani 1 1 d . . . . . C10 C -0.3528(9) 0.5380(4) 0.7483(5) 0.054(2) Uani 1 1 d . . . . . H10A H -0.412637 0.501193 0.731589 0.065 Uiso 1 1 calc R U . . . H10B H -0.402797 0.571286 0.711156 0.065 Uiso 1 1 calc R U . . . C11 C -0.3449(11) 0.5532(4) 0.8417(5) 0.060(2) Uani 1 1 d . . . . . H11A H -0.283542 0.523457 0.879768 0.090 Uiso 1 1 calc R U . . . H11B H -0.443298 0.552397 0.849574 0.090 Uiso 1 1 calc R U . . . H11C H -0.302735 0.593443 0.855513 0.090 Uiso 1 1 calc R U . . . C12 C -0.1419(11) 0.4744(3) 0.7488(4) 0.058(2) Uani 1 1 d . . . . . N21 N 0.5542(5) 0.2857(2) 0.5712(3) 0.0241(9) Uani 1 1 d . . . . . C21 C 0.4846(6) 0.2316(3) 0.5206(4) 0.0309(12) Uani 1 1 d . . . . . H21A H 0.548324 0.218013 0.485126 0.037 Uiso 1 1 calc R U . . . H21B H 0.390808 0.244463 0.480843 0.037 Uiso 1 1 calc R U . . . C22 C 0.4549(7) 0.1779(3) 0.5716(4) 0.0332(13) Uani 1 1 d . . . . . H22A H 0.542175 0.169358 0.619623 0.040 Uiso 1 1 calc R U . . . H22B H 0.372714 0.187267 0.595958 0.040 Uiso 1 1 calc R U . . . C23 C 0.4177(9) 0.1233(3) 0.5136(5) 0.0509(18) Uani 1 1 d . . . . . H23A H 0.335051 0.133509 0.463589 0.061 Uiso 1 1 calc R U . . . H23B H 0.502496 0.113297 0.491937 0.061 Uiso 1 1 calc R U . . . C24 C 0.3778(10) 0.0690(4) 0.5569(5) 0.061(2) Uani 1 1 d . . . . . H24A H 0.462678 0.055800 0.602631 0.092 Uiso 1 1 calc R U . . . H24B H 0.347032 0.036513 0.514949 0.092 Uiso 1 1 calc R U . . . H24C H 0.297709 0.079125 0.581691 0.092 Uiso 1 1 calc R U . . . C25 C 0.7003(6) 0.2694(2) 0.6334(3) 0.0246(11) Uani 1 1 d . . . . . H25A H 0.747958 0.306840 0.660348 0.030 Uiso 1 1 calc R U . . . H25B H 0.682087 0.243819 0.679463 0.030 Uiso 1 1 calc R U . . . C26 C 0.8048(6) 0.2364(3) 0.5931(4) 0.0303(12) Uani 1 1 d . . . . . H26A H 0.822077 0.261030 0.545803 0.036 Uiso 1 1 calc R U . . . H26B H 0.760764 0.197742 0.568611 0.036 Uiso 1 1 calc R U . . . C27 C 0.9501(6) 0.2243(3) 0.6596(4) 0.0316(13) Uani 1 1 d . . . . . H27A H 0.992622 0.262891 0.685524 0.038 Uiso 1 1 calc R U . . . H27B H 0.933383 0.198528 0.705871 0.038 Uiso 1 1 calc R U . . . C28 C 1.0559(7) 0.1934(3) 0.6184(5) 0.0394(15) Uani 1 1 d . . . . . H28A H 1.013056 0.155521 0.591967 0.059 Uiso 1 1 calc R U . . . H28B H 1.147228 0.184833 0.662321 0.059 Uiso 1 1 calc R U . . . H28C H 1.075861 0.219720 0.574433 0.059 Uiso 1 1 calc R U . . . C29 C 0.5737(6) 0.3325(3) 0.5059(3) 0.0279(12) Uani 1 1 d . . . . . H29A H 0.637626 0.314944 0.473183 0.034 Uiso 1 1 calc R U . . . H29B H 0.477212 0.339810 0.464827 0.034 Uiso 1 1 calc R U . . . C30 C 0.6367(7) 0.3923(3) 0.5415(4) 0.0326(13) Uani 1 1 d . . . . . H30A H 0.734249 0.386182 0.581949 0.039 Uiso 1 1 calc R U . . . H30B H 0.572981 0.411245 0.573257 0.039 Uiso 1 1 calc R U . . . C31 C 0.6495(9) 0.4334(3) 0.4697(5) 0.0484(18) Uani 1 1 d . . . . . H31A H 0.704166 0.411993 0.434580 0.058 Uiso 1 1 calc R U . . . H31B H 0.550388 0.441705 0.432351 0.058 Uiso 1 1 calc R U . . . C32 C 0.7225(9) 0.4910(3) 0.4981(6) 0.054(2) Uani 1 1 d . . . . . H32A H 0.668650 0.512870 0.532286 0.082 Uiso 1 1 calc R U . . . H32B H 0.725047 0.515152 0.447887 0.082 Uiso 1 1 calc R U . . . H32C H 0.822349 0.483402 0.533033 0.082 Uiso 1 1 calc R U . . . C33 C 0.4577(6) 0.3102(2) 0.6241(4) 0.0252(11) Uani 1 1 d . . . . . H33A H 0.444486 0.278221 0.663891 0.030 Uiso 1 1 calc R U . . . H33B H 0.509459 0.344054 0.659332 0.030 Uiso 1 1 calc R U . . . C34 C 0.3084(6) 0.3321(3) 0.5733(4) 0.0271(11) Uani 1 1 d . . . . . H34A H 0.319756 0.366757 0.537267 0.033 Uiso 1 1 calc R U . . . H34B H 0.257733 0.299507 0.534860 0.033 Uiso 1 1 calc R U . . . C35 C 0.2172(6) 0.3508(3) 0.6316(4) 0.0332(13) Uani 1 1 d . . . . . H35A H 0.263809 0.385621 0.666657 0.040 Uiso 1 1 calc R U . . . H35B H 0.213034 0.317199 0.671118 0.040 Uiso 1 1 calc R U . . . C36 C 0.0634(7) 0.3677(3) 0.5815(5) 0.0411(15) Uani 1 1 d . . . . . H36A H 0.065970 0.404954 0.549370 0.062 Uiso 1 1 calc R U . . . H36B H 0.003483 0.373944 0.621234 0.062 Uiso 1 1 calc R U . . . H36C H 0.021333 0.335241 0.541359 0.062 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 0.03592(16) 0.03823(16) 0.01911(15) -0.00125(8) 0.00531(10) 0.00358(9) S1 0.0303(8) 0.0358(8) 0.0322(8) 0.0023(6) 0.0014(6) -0.0027(6) S2 0.0369(9) 0.0583(11) 0.0329(8) 0.0001(7) 0.0105(7) 0.0001(8) S3 0.0439(9) 0.0301(7) 0.0294(8) 0.0024(6) 0.0063(6) -0.0004(6) S4 0.0590(12) 0.0484(10) 0.0544(11) 0.0016(8) 0.0244(9) 0.0182(9) S5 0.0923(16) 0.0363(9) 0.0463(11) -0.0032(8) 0.0176(10) 0.0158(10) S6 0.123(2) 0.0343(10) 0.0395(11) -0.0020(8) 0.0147(11) -0.0110(11) C1 0.042(4) 0.049(4) 0.023(3) -0.005(3) 0.001(3) -0.010(3) C2 0.048(4) 0.045(4) 0.063(5) -0.004(3) 0.012(4) -0.013(3) C3 0.074(6) 0.048(5) 0.063(5) -0.006(4) 0.014(4) -0.022(4) C4 0.087(7) 0.051(5) 0.055(5) -0.015(4) 0.029(5) -0.031(4) C5 0.053(5) 0.064(5) 0.041(4) -0.011(3) 0.017(3) -0.019(4) C6 0.040(4) 0.055(4) 0.024(3) -0.009(3) 0.010(3) -0.014(3) C7 0.069(5) 0.033(3) 0.024(3) -0.004(2) 0.001(3) 0.015(3) C8 0.069(5) 0.035(3) 0.019(3) -0.001(2) 0.002(3) -0.003(3) N9 0.074(4) 0.035(3) 0.027(3) -0.003(2) 0.013(3) -0.008(3) C10 0.064(5) 0.046(4) 0.045(4) 0.011(3) 0.002(4) -0.019(4) C11 0.085(6) 0.048(4) 0.053(5) -0.005(4) 0.028(4) 0.000(4) C12 0.110(7) 0.031(3) 0.023(3) -0.005(3) 0.001(4) -0.002(4) N21 0.024(2) 0.027(2) 0.021(2) -0.0010(18) 0.0053(18) -0.0006(19) C21 0.026(3) 0.037(3) 0.025(3) -0.009(2) -0.002(2) -0.001(2) C22 0.028(3) 0.038(3) 0.031(3) -0.005(2) 0.005(2) -0.004(2) C23 0.068(5) 0.037(4) 0.041(4) 0.003(3) 0.003(3) -0.010(3) C24 0.078(6) 0.048(4) 0.045(4) 0.003(3) -0.004(4) -0.019(4) C25 0.020(3) 0.029(3) 0.020(3) 0.004(2) -0.004(2) 0.000(2) C26 0.022(3) 0.043(3) 0.023(3) -0.002(2) 0.002(2) 0.001(2) C27 0.022(3) 0.036(3) 0.033(3) 0.001(2) 0.001(2) -0.003(2) C28 0.023(3) 0.051(4) 0.042(4) 0.004(3) 0.006(3) 0.006(3) C29 0.026(3) 0.037(3) 0.021(3) 0.006(2) 0.008(2) 0.002(2) C30 0.031(3) 0.033(3) 0.033(3) 0.009(2) 0.007(2) 0.000(2) C31 0.063(5) 0.046(4) 0.040(4) 0.013(3) 0.021(3) -0.005(3) C32 0.051(5) 0.042(4) 0.073(5) 0.021(4) 0.022(4) 0.000(3) C33 0.023(3) 0.031(3) 0.023(3) 0.000(2) 0.007(2) -0.003(2) C34 0.021(3) 0.034(3) 0.024(3) 0.003(2) 0.003(2) 0.007(2) C35 0.025(3) 0.041(3) 0.032(3) -0.009(3) 0.005(2) -0.002(2) C36 0.026(3) 0.047(4) 0.050(4) -0.007(3) 0.010(3) 0.002(3) 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' S S 0.1246 0.1234 '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 S1 Au1 S2 89.84(6) . . ? S1 Au1 S4 176.64(6) . . ? S2 Au1 S4 87.12(7) . . ? S1 Au1 S3 90.34(6) . . ? S2 Au1 S3 177.30(6) . . ? S4 Au1 S3 92.76(7) . . ? C1 S1 Au1 103.1(3) . . ? C6 S2 Au1 103.2(2) . . ? C8 S3 Au1 97.4(3) . . ? C7 S4 Au1 98.5(2) . . ? C12 S5 C7 92.6(4) . . ? C2 C1 C6 120.8(7) . . ? C2 C1 S1 118.2(6) . . ? C6 C1 S1 121.0(6) . . ? C1 C2 C3 120.0(8) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 119.3(8) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 119.4(8) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.8(8) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 118.3(7) . . ? C1 C6 S2 122.8(5) . . ? C5 C6 S2 118.8(6) . . ? C8 C7 S4 126.8(5) . . ? C8 C7 S5 109.8(6) . . ? S4 C7 S5 123.4(5) . . ? C7 C8 N9 114.4(6) . . ? C7 C8 S3 124.4(6) . . ? N9 C8 S3 121.2(6) . . ? C12 N9 C8 113.0(7) . . ? C12 N9 C10 122.7(7) . . ? C8 N9 C10 123.8(6) . . ? N9 C10 C11 113.9(7) . . ? N9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? N9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N9 C12 S6 126.4(7) . . ? N9 C12 S5 110.1(6) . . ? S6 C12 S5 123.5(5) . . ? C21 N21 C33 110.4(4) . . ? C21 N21 C25 111.1(4) . . ? C33 N21 C25 107.2(4) . . ? C21 N21 C29 106.5(4) . . ? C33 N21 C29 110.7(4) . . ? C25 N21 C29 111.0(4) . . ? N21 C21 C22 116.7(5) . . ? N21 C21 H21A 108.1 . . ? C22 C21 H21A 108.1 . . ? N21 C21 H21B 108.1 . . ? C22 C21 H21B 108.1 . . ? H21A C21 H21B 107.3 . . ? C23 C22 C21 109.7(5) . . ? C23 C22 H22A 109.7 . . ? C21 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? C21 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C24 C23 C22 113.6(6) . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23B 108.8 . . ? C22 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 N21 114.7(4) . . ? C26 C25 H25A 108.6 . . ? N21 C25 H25A 108.6 . . ? C26 C25 H25B 108.6 . . ? N21 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C25 C26 C27 110.8(4) . . ? C25 C26 H26A 109.5 . . ? C27 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 108.1 . . ? C28 C27 C26 110.6(5) . . ? C28 C27 H27A 109.5 . . ? C26 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N21 116.5(5) . . ? C30 C29 H29A 108.2 . . ? N21 C29 H29A 108.2 . . ? C30 C29 H29B 108.2 . . ? N21 C29 H29B 108.2 . . ? H29A C29 H29B 107.3 . . ? C29 C30 C31 110.2(5) . . ? C29 C30 H30A 109.6 . . ? C31 C30 H30A 109.6 . . ? C29 C30 H30B 109.6 . . ? C31 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C30 114.5(6) . . ? C32 C31 H31A 108.6 . . ? C30 C31 H31A 108.6 . . ? C32 C31 H31B 108.6 . . ? C30 C31 H31B 108.6 . . ? H31A C31 H31B 107.6 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N21 115.6(5) . . ? C34 C33 H33A 108.4 . . ? N21 C33 H33A 108.4 . . ? C34 C33 H33B 108.4 . . ? N21 C33 H33B 108.4 . . ? H33A C33 H33B 107.4 . . ? C35 C34 C33 111.4(5) . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C36 111.8(5) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 S1 2.2988(16) . ? Au1 S2 2.3004(18) . ? Au1 S4 2.3172(18) . ? Au1 S3 2.3378(17) . ? S1 C1 1.782(7) . ? S2 C6 1.750(7) . ? S3 C8 1.765(7) . ? S4 C7 1.706(9) . ? S5 C12 1.716(10) . ? S5 C7 1.731(7) . ? S6 C12 1.678(8) . ? C1 C2 1.377(10) . ? C1 C6 1.382(10) . ? C2 C3 1.390(11) . ? C2 H2 0.9500 . ? C3 C4 1.408(13) . ? C3 H3 0.9500 . ? C4 C5 1.349(12) . ? C4 H4 0.9500 . ? C5 C6 1.401(10) . ? C5 H5 0.9500 . ? C7 C8 1.349(11) . ? C8 N9 1.399(9) . ? N9 C12 1.369(10) . ? N9 C10 1.424(10) . ? C10 C11 1.532(11) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N21 C21 1.502(7) . ? N21 C33 1.518(7) . ? N21 C25 1.522(7) . ? N21 C29 1.529(7) . ? C21 C22 1.519(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.516(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.494(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.519(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.528(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.516(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.506(8) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.508(8) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.468(11) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.516(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.504(8) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.516(9) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 S1 C1 C2 -178.9(5) . . . . ? Au1 S1 C1 C6 0.5(6) . . . . ? C6 C1 C2 C3 3.0(11) . . . . ? S1 C1 C2 C3 -177.6(6) . . . . ? C1 C2 C3 C4 -2.8(12) . . . . ? C2 C3 C4 C5 -1.1(13) . . . . ? C3 C4 C5 C6 4.9(12) . . . . ? C2 C1 C6 C5 0.7(10) . . . . ? S1 C1 C6 C5 -178.7(5) . . . . ? C2 C1 C6 S2 178.3(5) . . . . ? S1 C1 C6 S2 -1.1(8) . . . . ? C4 C5 C6 C1 -4.7(11) . . . . ? C4 C5 C6 S2 177.6(6) . . . . ? Au1 S2 C6 C1 1.0(6) . . . . ? Au1 S2 C6 C5 178.6(5) . . . . ? Au1 S4 C7 C8 -2.0(6) . . . . ? Au1 S4 C7 S5 -178.7(4) . . . . ? C12 S5 C7 C8 -0.7(5) . . . . ? C12 S5 C7 S4 176.5(4) . . . . ? S4 C7 C8 N9 -177.1(5) . . . . ? S5 C7 C8 N9 0.0(7) . . . . ? S4 C7 C8 S3 4.3(9) . . . . ? S5 C7 C8 S3 -178.6(4) . . . . ? Au1 S3 C8 C7 -3.6(6) . . . . ? Au1 S3 C8 N9 177.9(5) . . . . ? C7 C8 N9 C12 1.0(8) . . . . ? S3 C8 N9 C12 179.7(4) . . . . ? C7 C8 N9 C10 173.6(6) . . . . ? S3 C8 N9 C10 -7.8(9) . . . . ? C12 N9 C10 C11 82.9(8) . . . . ? C8 N9 C10 C11 -88.9(8) . . . . ? C8 N9 C12 S6 179.2(5) . . . . ? C10 N9 C12 S6 6.6(9) . . . . ? C8 N9 C12 S5 -1.6(7) . . . . ? C10 N9 C12 S5 -174.2(5) . . . . ? C7 S5 C12 N9 1.3(5) . . . . ? C7 S5 C12 S6 -179.4(5) . . . . ? C33 N21 C21 C22 -60.4(6) . . . . ? C25 N21 C21 C22 58.5(6) . . . . ? C29 N21 C21 C22 179.4(5) . . . . ? N21 C21 C22 C23 -167.2(6) . . . . ? C21 C22 C23 C24 -176.5(7) . . . . ? C21 N21 C25 C26 51.7(6) . . . . ? C33 N21 C25 C26 172.4(5) . . . . ? C29 N21 C25 C26 -66.6(6) . . . . ? N21 C25 C26 C27 177.7(5) . . . . ? C25 C26 C27 C28 -178.0(5) . . . . ? C21 N21 C29 C30 177.6(5) . . . . ? C33 N21 C29 C30 57.5(6) . . . . ? C25 N21 C29 C30 -61.4(6) . . . . ? N21 C29 C30 C31 179.8(5) . . . . ? C29 C30 C31 C32 -174.6(6) . . . . ? C21 N21 C33 C34 -61.7(6) . . . . ? C25 N21 C33 C34 177.1(5) . . . . ? C29 N21 C33 C34 56.0(6) . . . . ? N21 C33 C34 C35 175.4(5) . . . . ? C33 C34 C35 C36 -175.2(5) . . . . ?