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#$Date: 2024-08-05 21:49:42 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/64/7716462.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_7716462
loop_
_publ_author_name
'Vitré, Constantin'
'Le Gal, Yann'
'Vacher, Antoine'
'Roisnel, Thierry'
'Lorcy, Dominique'
'Santana, Sofia'
'Prudêncio, Miguel'
'Pinheiro, Teresa'
'Marques, Fernanda'
_publ_section_title
;
 Structure-activity relationship of anticancer and antiplasmodial gold
 bis(dithiolene) complexes.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11903
_journal_page_last               11913
_journal_paper_doi               10.1039/d4dt01458h
_journal_volume                  53
_journal_year                    2024
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H34 Au N2 S8, C24 H20 P'
_chemical_formula_sum            'C46 H54 Au N2 P S8'
_chemical_formula_weight         1119.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2024-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.075(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.043(4)
_cell_length_b                   8.3744(9)
_cell_length_c                   17.891(2)
_cell_measurement_reflns_used    8697
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4753
_cell_measurement_theta_min      2.3193
_cell_measurement_wavelength     0.710730
_cell_volume                     4790.7(9)
_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, 2024)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0088014
_diffrn_orient_matrix_UB_12      0.1121420
_diffrn_orient_matrix_UB_13      0.0167650
_diffrn_orient_matrix_UB_21      -0.0117037
_diffrn_orient_matrix_UB_22      -0.0097576
_diffrn_orient_matrix_UB_23      0.0439879
_diffrn_orient_matrix_UB_31      0.0276341
_diffrn_orient_matrix_UB_32      -0.0398494
_diffrn_orient_matrix_UB_33      0.0364081
_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  0.0552
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24341
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         2.514
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    3.487
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         4.440
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0569P)²+17.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                4140
_reflns_number_total             5478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4dt01458h2.cif
_cod_data_source_block           AuNC8new
_cod_depositor_comments          'Adding full bibliography for 7716462.cif.'
_cod_original_cell_volume        4790.6(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7716462
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.750000 0.250000 0.000000 0.02214(9) Uani 1 2 d S . P . .
C1 C 0.65718(16) 0.2623(6) -0.0163(3) 0.0262(10) Uani 1 1 d . . . . .
C2 C 0.67600(17) 0.3060(6) 0.0601(3) 0.0267(11) Uani 1 1 d . . . . .
N3 N 0.64828(14) 0.3336(5) 0.1019(3) 0.0274(9) Uani 1 1 d . . . . .
C4 C 0.60753(18) 0.3041(7) 0.0594(3) 0.0301(12) Uani 1 1 d . . . . .
C5 C 0.66120(18) 0.3978(6) 0.1825(3) 0.0307(12) Uani 1 1 d . . . . .
H5A H 0.638671 0.467553 0.187139 0.037 Uiso 1 1 calc R U . . .
H5B H 0.686355 0.464920 0.191532 0.037 Uiso 1 1 calc R U . . .
C6 C 0.67103(19) 0.2703(6) 0.2476(3) 0.0311(12) Uani 1 1 d . . . . .
H6A H 0.647475 0.193844 0.235525 0.037 Uiso 1 1 calc R U . . .
H6B H 0.696375 0.210368 0.249186 0.037 Uiso 1 1 calc R U . . .
C7 C 0.67806(19) 0.3474(6) 0.3276(3) 0.0325(12) Uani 1 1 d . . . . .
H7A H 0.652931 0.409698 0.325153 0.039 Uiso 1 1 calc R U . . .
H7B H 0.701932 0.422360 0.339716 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6870(2) 0.2237(6) 0.3942(3) 0.0321(12) Uani 1 1 d . . . . .
H8A H 0.665227 0.139815 0.377977 0.038 Uiso 1 1 calc R U . . .
H8B H 0.714271 0.172284 0.401392 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6881(2) 0.2934(7) 0.4727(3) 0.0333(13) Uani 1 1 d . . . . .
H9A H 0.661675 0.351473 0.464774 0.040 Uiso 1 1 calc R U . . .
H9B H 0.711306 0.371561 0.490978 0.040 Uiso 1 1 calc R U . . .
C10 C 0.69407(19) 0.1660(6) 0.5376(3) 0.0324(12) Uani 1 1 d . . . . .
H10A H 0.671797 0.084643 0.517952 0.039 Uiso 1 1 calc R U . . .
H10B H 0.721251 0.112061 0.547445 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6929(2) 0.2328(6) 0.6159(3) 0.0332(12) Uani 1 1 d . . . . .
H11A H 0.666082 0.289260 0.606135 0.040 Uiso 1 1 calc R U . . .
H11B H 0.715782 0.311546 0.636751 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6976(2) 0.1035(8) 0.6778(4) 0.0432(15) Uani 1 1 d . . . . .
H12A H 0.674516 0.027096 0.658180 0.065 Uiso 1 1 calc R U . . .
H12B H 0.697027 0.152083 0.727288 0.065 Uiso 1 1 calc R U . . .
H12C H 0.724249 0.047797 0.688047 0.065 Uiso 1 1 calc R U . . .
C21 C 0.46932(17) 0.4148(6) 0.1718(3) 0.0300(11) Uani 1 1 d . . . . .
C22 C 0.46836(17) 0.4311(7) 0.0939(3) 0.0323(12) Uani 1 1 d . . . . .
H22 H 0.482611 0.517635 0.080152 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4469(2) 0.3229(8) 0.0366(4) 0.0411(14) Uani 1 1 d . . . . .
H23 H 0.446225 0.335224 -0.016663 0.049 Uiso 1 1 calc R U . . .
C24 C 0.4263(2) 0.1952(8) 0.0567(4) 0.0429(15) Uani 1 1 d . . . . .
H24 H 0.411641 0.119713 0.017343 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4271(2) 0.1787(8) 0.1345(4) 0.0434(15) Uani 1 1 d . . . . .
H25 H 0.412723 0.092468 0.148120 0.052 Uiso 1 1 calc R U . . .
C26 C 0.4489(2) 0.2879(7) 0.1926(4) 0.0394(14) Uani 1 1 d . . . . .
H26 H 0.449862 0.275631 0.245979 0.047 Uiso 1 1 calc R U . . .
C27 C 0.53241(17) 0.6750(7) 0.2168(3) 0.0296(11) Uani 1 1 d . . . . .
C28 C 0.57508(18) 0.6610(7) 0.2426(3) 0.0331(12) Uani 1 1 d . . . . .
H28 H 0.588384 0.576255 0.277374 0.040 Uiso 1 1 calc R U . . .
C29 C 0.59902(19) 0.7699(7) 0.2183(4) 0.0388(14) Uani 1 1 d . . . . .
H29 H 0.628597 0.759558 0.236263 0.047 Uiso 1 1 calc R U . . .
C30 C 0.57955(19) 0.8936(7) 0.1678(3) 0.0378(13) Uani 1 1 d . . . . .
H30 H 0.595885 0.968262 0.151133 0.045 Uiso 1 1 calc R U . . .
C31 C 0.5369(2) 0.9090(8) 0.1415(4) 0.0447(15) Uani 1 1 d . . . . .
H31 H 0.523758 0.994063 0.106795 0.054 Uiso 1 1 calc R U . . .
C32 C 0.5131(2) 0.8016(8) 0.1654(4) 0.0411(14) Uani 1 1 d . . . . .
H32 H 0.483504 0.812702 0.147304 0.049 Uiso 1 1 calc R U . . .
P1 P 0.500000 0.5448(2) 0.250000 0.0286(4) Uani 1 2 d S T P . .
S1 S 0.73005(4) 0.32307(17) 0.10700(7) 0.0282(3) Uani 1 1 d . . . . .
S2 S 0.68134(4) 0.22301(15) -0.08471(7) 0.0271(3) Uani 1 1 d . . . . .
S3 S 0.60326(4) 0.24662(17) -0.03675(8) 0.0324(3) Uani 1 1 d . . . . .
S4 S 0.56625(5) 0.3208(2) 0.08894(9) 0.0409(4) Uani 1 1 d . . . . .
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'
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
S2 Au1 S2 180.00(4) . 7_655 ?
S2 Au1 S1 87.13(5) . 7_655 ?
S2 Au1 S1 92.87(5) 7_655 7_655 ?
S2 Au1 S1 92.87(5) . . ?
S2 Au1 S1 87.13(5) 7_655 . ?
S1 Au1 S1 180.0 7_655 . ?
C2 C1 S2 126.6(4) . . ?
C2 C1 S3 109.4(4) . . ?
S2 C1 S3 124.0(3) . . ?
C1 C2 N3 114.3(5) . . ?
C1 C2 S1 124.4(4) . . ?
N3 C2 S1 121.3(4) . . ?
C4 N3 C2 114.5(4) . . ?
C4 N3 C5 121.7(4) . . ?
C2 N3 C5 123.7(5) . . ?
N3 C4 S4 128.1(4) . . ?
N3 C4 S3 109.0(4) . . ?
S4 C4 S3 122.8(4) . . ?
N3 C5 C6 114.1(4) . . ?
N3 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N3 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 110.1(4) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.8(4) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 113.4(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 112.9(4) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 113.7(4) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 112.4(5) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 C21 C22 120.2(5) . . ?
C26 C21 P1 117.7(4) . . ?
C22 C21 P1 121.9(4) . . ?
C23 C22 C21 120.5(6) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.9(6) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.8(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.3(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.3(6) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 C32 119.2(5) . . ?
C28 C27 P1 122.6(4) . . ?
C32 C27 P1 118.1(4) . . ?
C27 C28 C29 120.5(5) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 119.7(6) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 120.5(6) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.1(6) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.1(6) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C27 P1 C27 105.0(4) 2_655 . ?
C27 P1 C21 111.6(2) 2_655 . ?
C27 P1 C21 111.7(2) . . ?
C27 P1 C21 111.7(2) 2_655 2_655 ?
C27 P1 C21 111.5(2) . 2_655 ?
C21 P1 C21 105.4(4) . 2_655 ?
C2 S1 Au1 98.10(18) . . ?
C1 S2 Au1 97.86(18) . . ?
C4 S3 C1 92.7(3) . . ?
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 S2 2.3194(14) . ?
Au1 S2 2.3194(14) 7_655 ?
Au1 S1 2.3221(13) 7_655 ?
Au1 S1 2.3221(13) . ?
C1 C2 1.347(7) . ?
C1 S2 1.724(5) . ?
C1 S3 1.749(5) . ?
C2 N3 1.409(7) . ?
C2 S1 1.747(6) . ?
N3 C4 1.356(7) . ?
N3 C5 1.459(7) . ?
C4 S4 1.668(6) . ?
C4 S3 1.743(6) . ?
C5 C6 1.530(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.513(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.510(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.539(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C21 C26 1.389(8) . ?
C21 C22 1.389(8) . ?
C21 P1 1.797(5) . ?
C22 C23 1.375(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.370(8) . ?
C27 C32 1.410(8) . ?
C27 P1 1.791(6) . ?
C28 C29 1.388(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.371(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(9) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
