#------------------------------------------------------------------------------
#$Date: 2023-02-25 10:36:17 +0200 (Sat, 25 Feb 2023) $
#$Revision: 281138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/23/7712397.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_7712397
loop_
_publ_author_name
'Salvador, Daniel'
'Herrera, Raquel'
'Gimeno, Maria Concepcion'
_publ_section_title
;
 Free-Catalysed Synthesis of Thiazolidine-Thiourea Ligands for Metal
 Coordination (Au and Ag) and Preliminary Cytotoxic Studies
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00079F
_journal_year                    2023
_chemical_formula_sum            'C25 H19 Au F5 N3 S2'
_chemical_formula_weight         717.52
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-01-05 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.4153(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8378(2)
_cell_length_b                   12.77496(15)
_cell_length_c                   14.0307(2)
_cell_measurement_reflns_used    27385
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9280
_cell_measurement_theta_min      3.4240
_cell_volume                     2402.16(7)
_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_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 0.954
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            64899
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.929
_diffrn_reflns_theta_min         3.215
_exptl_absorpt_coefficient_mu    6.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21062
_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    1.984
_exptl_crystal_description       prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   3.001
_exptl_transmission_factor_min   0.576
_refine_diff_density_max         0.932
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0195
_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/[σ²(Fo²)+(0.0231P)²+1.7691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5650
_reflns_number_total             6047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00079f2.cif
_cod_data_source_block           c558
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7712397
_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   0.166
_shelx_estimated_absorpt_t_max   0.516
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 0.25042(2) 0.55262(2) 0.43398(2) 0.01687(4) Uani 1 1 d . . . . .
S1 S 0.12431(5) 0.59319(4) 0.48239(5) 0.02401(13) Uani 1 1 d . . . . .
S2 S -0.19354(4) 0.82465(4) 0.31984(4) 0.01935(11) Uani 1 1 d . . . . .
N1 N -0.01705(13) 0.73685(14) 0.40336(14) 0.0152(4) Uani 1 1 d . . . . .
N2 N -0.01605(14) 0.92087(14) 0.38228(14) 0.0157(4) Uani 1 1 d . . . . .
N3 N 0.14274(14) 0.80049(15) 0.45753(16) 0.0206(4) Uani 1 1 d . . . . .
F1 F 0.37464(11) 0.34034(11) 0.47528(12) 0.0264(3) Uani 1 1 d . . . . .
F2 F 0.51711(11) 0.27798(11) 0.41785(13) 0.0330(3) Uani 1 1 d . . . . .
F3 F 0.57932(11) 0.40595(13) 0.30442(12) 0.0330(3) Uani 1 1 d . . . . .
F4 F 0.49802(11) 0.60129(13) 0.24985(12) 0.0316(3) Uani 1 1 d . . . . .
F5 F 0.35465(11) 0.66421(11) 0.30369(12) 0.0302(3) Uani 1 1 d . . . . .
C1 C 0.35796(16) 0.50519(18) 0.39173(17) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.40228(17) 0.40733(18) 0.41768(18) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.47543(17) 0.37326(18) 0.38946(19) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.50786(18) 0.43844(19) 0.33250(19) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.46704(18) 0.53672(19) 0.30534(19) 0.0223(5) Uani 1 1 d . . . . .
C6 C 0.39362(18) 0.56696(18) 0.33486(19) 0.0213(5) Uani 1 1 d . . . . .
C7 C 0.08366(17) 0.71986(17) 0.44481(17) 0.0171(4) Uani 1 1 d . . . . .
C8 C -0.08640(17) 0.64767(17) 0.37969(18) 0.0200(5) Uani 1 1 d . . . . .
H8A H -0.066705 0.601901 0.442374 0.024 Uiso 1 1 calc R U . . .
H8B H -0.085161 0.605762 0.320909 0.024 Uiso 1 1 calc R U . . .
C9 C -0.18880(17) 0.69096(18) 0.34969(18) 0.0205(5) Uani 1 1 d . . . . .
C10 C -0.2670(2) 0.6380(2) 0.3449(2) 0.0357(7) Uani 1 1 d . . . . .
H10A H -0.261052 0.565413 0.361306 0.043 Uiso 1 1 calc R U . . .
H10B H -0.329248 0.672353 0.324917 0.043 Uiso 1 1 calc R U . . .
C11 C -0.06276(16) 0.83586(17) 0.37366(16) 0.0149(4) Uani 1 1 d . . . . .
C12 C -0.07902(16) 1.01442(17) 0.34783(18) 0.0181(4) Uani 1 1 d . . . . .
H12A H -0.115137 1.022413 0.392562 0.022 Uiso 1 1 calc R U . . .
H12B H -0.129511 1.003322 0.274411 0.022 Uiso 1 1 calc R U . . .
C13 C -0.02434(17) 1.11483(16) 0.35199(16) 0.0163(4) Uani 1 1 d . . . . .
C14 C 0.07782(17) 1.12138(18) 0.38649(17) 0.0202(5) Uani 1 1 d . . . . .
H14 H 0.117345 1.059742 0.407627 0.024 Uiso 1 1 calc R U . . .
C15 C 0.12343(18) 1.21807(19) 0.39052(18) 0.0238(5) Uani 1 1 d . . . . .
H15 H 0.193751 1.221981 0.414708 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0663(2) 1.30812(18) 0.35931(18) 0.0239(5) Uani 1 1 d . . . . .
H16 H 0.097303 1.373854 0.362242 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0361(2) 1.30218(18) 0.32386(19) 0.0250(5) Uani 1 1 d . . . . .
H17 H -0.075493 1.363870 0.302254 0.030 Uiso 1 1 calc R U . . .
C18 C -0.08144(18) 1.20598(18) 0.31980(18) 0.0212(5) Uani 1 1 d . . . . .
H18 H -0.151852 1.202238 0.294914 0.025 Uiso 1 1 calc R U . . .
C19 C 0.25236(18) 0.7984(2) 0.5109(3) 0.0355(7) Uani 1 1 d . . . . .
H19A H 0.277420 0.738165 0.484873 0.043 Uiso 1 1 calc R U . . .
H19B H 0.274533 0.789442 0.587800 0.043 Uiso 1 1 calc R U . . .
C20 C 0.29471(16) 0.89824(17) 0.49049(19) 0.0204(5) Uani 1 1 d . . . . .
C21 C 0.3233(2) 0.9049(2) 0.4099(2) 0.0373(7) Uani 1 1 d . . . . .
H21 H 0.314135 0.846751 0.364478 0.045 Uiso 1 1 calc R U . . .
C22 C 0.3656(3) 0.9966(3) 0.3947(3) 0.0511(9) Uani 1 1 d . . . . .
H22 H 0.385650 1.000941 0.338963 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3786(2) 1.0809(2) 0.4599(3) 0.0462(8) Uani 1 1 d . . . . .
H23 H 0.407851 1.143409 0.449445 0.055 Uiso 1 1 calc R U . . .
C24 C 0.3495(2) 1.0750(2) 0.5396(2) 0.0336(6) Uani 1 1 d . . . . .
H24 H 0.358169 1.133633 0.584390 0.040 Uiso 1 1 calc R U . . .
C25 C 0.30775(18) 0.9843(2) 0.55546(19) 0.0238(5) Uani 1 1 d . . . . .
H25 H 0.287687 0.980646 0.611208 0.029 Uiso 1 1 calc R U . . .
H3 H 0.110(3) 0.856(3) 0.436(3) 0.050(10) Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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 S1 175.51(6) . . ?
C7 S1 Au1 109.97(8) . . ?
C9 S2 C11 93.04(11) . . ?
C7 N1 C11 124.51(18) . . ?
C7 N1 C8 120.16(18) . . ?
C11 N1 C8 115.19(17) . . ?
C11 N2 C12 115.01(19) . . ?
C7 N3 C19 125.6(2) . . ?
C6 C1 C2 114.3(2) . . ?
C6 C1 Au1 123.09(17) . . ?
C2 C1 Au1 122.62(17) . . ?
F1 C2 C3 116.7(2) . . ?
F1 C2 C1 119.7(2) . . ?
C3 C2 C1 123.6(2) . . ?
F2 C3 C2 121.3(2) . . ?
F2 C3 C4 119.2(2) . . ?
C2 C3 C4 119.4(2) . . ?
F3 C4 C5 120.6(2) . . ?
F3 C4 C3 120.0(2) . . ?
C5 C4 C3 119.4(2) . . ?
F4 C5 C4 120.1(2) . . ?
F4 C5 C6 120.9(2) . . ?
C4 C5 C6 119.0(2) . . ?
F5 C6 C5 116.2(2) . . ?
F5 C6 C1 119.5(2) . . ?
C5 C6 C1 124.3(2) . . ?
N3 C7 N1 118.46(19) . . ?
N3 C7 S1 124.56(17) . . ?
N1 C7 S1 116.91(16) . . ?
N1 C8 C9 107.68(18) . . ?
C10 C9 C8 126.1(2) . . ?
C10 C9 S2 122.9(2) . . ?
C8 C9 S2 111.03(16) . . ?
N2 C11 N1 124.5(2) . . ?
N2 C11 S2 124.64(17) . . ?
N1 C11 S2 110.82(15) . . ?
N2 C12 C13 115.17(18) . . ?
C14 C13 C18 119.0(2) . . ?
C14 C13 C12 123.86(19) . . ?
C18 C13 C12 117.1(2) . . ?
C13 C14 C15 120.5(2) . . ?
C16 C15 C14 120.1(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C13 120.5(2) . . ?
N3 C19 C20 110.4(2) . . ?
C21 C20 C25 119.2(2) . . ?
C21 C20 C19 120.9(2) . . ?
C25 C20 C19 119.9(2) . . ?
C20 C21 C22 120.0(3) . . ?
C23 C22 C21 120.2(3) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C25 C20 120.4(2) . . ?
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 2.019(2) . ?
Au1 S1 2.3069(6) . ?
S1 C7 1.728(2) . ?
S2 C9 1.753(2) . ?
S2 C11 1.760(2) . ?
N1 C7 1.368(3) . ?
N1 C11 1.411(3) . ?
N1 C8 1.474(3) . ?
N2 C11 1.266(3) . ?
N2 C12 1.465(3) . ?
N3 C7 1.314(3) . ?
N3 C19 1.470(3) . ?
F1 C2 1.356(3) . ?
F2 C3 1.346(3) . ?
F3 C4 1.345(3) . ?
F4 C5 1.344(3) . ?
F5 C6 1.361(3) . ?
C1 C6 1.379(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.376(4) . ?
C8 C9 1.498(3) . ?
C9 C10 1.320(3) . ?
C12 C13 1.505(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.383(4) . ?
C17 C18 1.390(3) . ?
C19 C20 1.503(3) . ?
C20 C21 1.370(4) . ?
C20 C25 1.388(3) . ?
C21 C22 1.388(5) . ?
C22 C23 1.372(5) . ?
C23 C24 1.363(5) . ?
C24 C25 1.376(4) . ?
