#------------------------------------------------------------------------------
#$Date: 2025-11-29 21:53:55 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303795 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/97/7719759.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_7719759
loop_
_publ_author_name
'Tang, Haiming'
'Chen, Chen'
'Fu, Yuhang'
'Sun, Tong'
'Yin, Li'
'He, Mingyuan'
'Fu, Qin'
'Li, Qin'
'Liu, Yu'
'Chen, Ziyun'
'Jamieson, Stephen M. F.'
'Söhnel, Tilo'
'Hartinger, Christian G.'
_publ_section_title
;
 Platinum(II) complexes of fluorinated pyrrole carbothioamides: enhanced
 anticancer activity and overcoming cisplatin resistance.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17112
_journal_page_last               17120
_journal_paper_doi               10.1039/d5dt02290h
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C12 H9 F3 N2 S'
_chemical_formula_sum            'C12 H9 F3 N2 S'
_chemical_formula_weight         270.27
_chemical_name_systematic        1
_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
_audit_creation_date             2025-08-07
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_audit_update_record
;
2025-08-07 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.031(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9637(4)
_cell_length_b                   8.9883(2)
_cell_length_c                   10.1085(3)
_cell_measurement_reflns_used    6103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7730
_cell_measurement_theta_min      3.2540
_cell_volume                     1236.05(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  59.00   0.50    0.50    --   42.30 -82.00  30.00   52
  2  ω    -25.00  28.00   0.50    0.50    --   42.30 -54.00 120.00  106
  3  ω     87.00 130.00   0.50    0.50    --   42.30  77.00 -30.00   86
  4  ω     42.00  67.00   0.50    0.50    --   42.30 -65.00  30.00   50
  5  ω    -27.00  20.00   0.50    0.50    --   42.30 -65.00  30.00   94
  6  ω    -44.00  -4.00   0.50    0.50    --   42.30 -82.00-180.00   80
  7  ω     18.00  90.00   0.50    0.50    --   42.30  77.00  60.00  144
  8  ω    -47.00  10.00   0.50    0.50    --   42.30 -77.00 -90.00  114
  9  ω     95.00 132.00   0.50    0.50    --   42.30  77.00  60.00   74
 10  ω     11.00  70.00   0.50    0.50    --   42.30 -82.00-180.00  118
 11  ω     21.00  76.00   0.50    0.50    --   42.30  77.00 -30.00  110
 12  ω    -32.00  -7.00   0.50    0.50    --   42.30 -82.00  30.00   50
 13  ω     32.00  65.00   0.50    0.50    --   42.30 -65.00 -60.00   66
 14  ω    -46.00   6.00   0.50    0.50    --   42.30 -65.00 -60.00  104
 15  ω     20.00  63.00   0.50    0.50    --   42.30 -77.00 -90.00   86
 16  ω     37.00  62.00   0.50    0.50    --   42.30 -77.00  30.00   50
 17  ω     32.00  57.00   0.50    0.50    --   42.30 -77.00 150.00   50
 18  ω      4.00  29.00   0.50    0.50    --   42.30 -77.00 150.00   50
 19  ω     36.00  62.00   0.50    0.67    --   93.70 -82.00-180.00   52
 20  ω     24.00  56.00   0.50    0.67    --   93.70 -82.00  30.00   64
 21  ω      7.00 101.00   0.50    0.67    --   93.70 -82.00  90.00  188
 22  ω    111.00 137.00   0.50    0.67    --   93.70  59.00 -90.00   52
 23  ω     69.00 177.00   0.50    0.67    --   93.70  68.00  30.00  216
 24  ω     66.00 182.00   0.50    0.67    --   93.70  59.00 -60.00  232
 25  ω      6.00 121.00   0.50    0.67    --   93.70 -82.00 150.00  230
 26  ω     70.00  96.00   0.50    0.67    --   93.70 -82.00 -90.00   52
 27  ω     23.00  49.00   0.50    0.67    --   93.70 -82.00 -90.00   52
 28  ω     85.00 110.00   0.50    0.67    --   93.70 -82.00  30.00   50
 29  ω     84.00 151.00   0.50    0.67    --   93.70  68.00  60.00  134
 30  ω     68.00  94.00   0.50    0.67    --   93.70 -82.00-180.00   52
 31  ω     37.00 101.00   0.50    0.67    --   93.70 -82.00 -60.00  128
 32  ω     72.00 181.00   0.50    0.67    --   93.70  59.00 -30.00  218
 33  ω     68.00 183.00   0.50    0.67    --   93.70  59.00   0.00  230
 34  ω     69.00 133.00   0.50    0.67    --   93.70  33.00 120.00  128
 35  ω     45.00  84.00   0.50    0.67    --   93.70 -82.00-120.00   78
 36  ω     20.00 103.00   0.50    0.67    --   93.70 -82.00   0.00  166
 37  ω      6.00  93.00   0.50    0.67    --   93.70 -82.00  60.00  174
 38  ω      8.00  93.00   0.50    0.67    --   93.70 -82.00 120.00  170
 39  ω     43.00 110.00   0.50    0.67    --   93.70 -82.00-150.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10766
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.407
_diffrn_reflns_theta_min         3.249
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0135(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0438
_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)+(0.0660P)²+0.1493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1947
_reflns_number_total             2254
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02290h2.cif
_cod_data_source_block           2022-5-23_auto
_cod_depositor_comments
'Adding full bibliography for 7719759--7719760.cif.'
_cod_database_code               7719759
_shelx_shelxl_version_number     2019/3
_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_max   0.905
_shelx_estimated_absorpt_t_min   0.862
_diffrn_oxdiff_digest_hkl
;
01f90e9ede8921c4c14f8c2278d1e6acdd4c6c
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C12-F1 = C12-F2 = C12-F3 = C12-F1A = C12-F2A = C12-F3A
 1.335 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3: within 2A with sigma of 0.02 and sigma for terminal atoms
of 0.01 within 2A
F1A \\sim F2A \\sim F3A: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.01 within 2A
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C3(H3), C10(H10), C7(H7), C8(H8), C2(H2A), C1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.679
_oxdiff_exptl_absorpt_empirical_full_min 0.609
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
S1 S 0.47391(4) 0.80375(6) 0.55149(6) 0.0842(3) Uani 1 1 d . . . . .
N2 N 0.51598(10) 0.59140(19) 0.73695(16) 0.0722(4) Uani 1 1 d . . . . .
H2 H 0.496059 0.526978 0.787649 0.087 Uiso 1 1 calc R U . . .
N1 N 0.27224(11) 0.7347(2) 0.5987(2) 0.0944(6) Uani 1 1 d . . . . .
H1 H 0.278033 0.806418 0.544727 0.113 Uiso 1 1 calc R U . . .
C6 C 0.61934(12) 0.5985(2) 0.74462(19) 0.0656(4) Uani 1 1 d . . . . .
C4 C 0.34752(12) 0.6487(2) 0.66861(19) 0.0686(5) Uani 1 1 d . . . . .
C5 C 0.44740(12) 0.6763(2) 0.65771(18) 0.0625(4) Uani 1 1 d . . . . .
C9 C 0.81908(13) 0.6070(2) 0.7656(2) 0.0725(5) Uani 1 1 d . . . . .
C11 C 0.68116(14) 0.6393(3) 0.8650(2) 0.0825(6) Uani 1 1 d . . . . .
H11 H 0.655652 0.664079 0.939558 0.099 Uiso 1 1 calc R U . . .
C3 C 0.30627(14) 0.5464(3) 0.7403(2) 0.0845(6) Uani 1 1 d . . . . .
H3 H 0.339785 0.472589 0.796817 0.101 Uiso 1 1 calc R U . . .
C10 C 0.78101(15) 0.6433(3) 0.8748(2) 0.0883(6) Uani 1 1 d . . . . .
H10 H 0.822953 0.670965 0.956219 0.106 Uiso 1 1 calc R U . . .
C7 C 0.65699(14) 0.5615(3) 0.6370(2) 0.0972(8) Uani 1 1 d . . . . .
H7 H 0.615114 0.532914 0.555805 0.117 Uiso 1 1 calc R U . . .
C12 C 0.92716(15) 0.6126(3) 0.7748(3) 0.0954(7) Uani 1 1 d D . . . .
C8 C 0.75694(16) 0.5658(3) 0.6468(3) 0.0967(7) Uani 1 1 d . . . . .
H8 H 0.782191 0.540534 0.572204 0.116 Uiso 1 1 calc R U . . .
C2 C 0.20546(16) 0.5728(3) 0.7134(3) 0.1001(8) Uani 1 1 d . . . . .
H2A H 0.159382 0.519924 0.748095 0.120 Uiso 1 1 calc R U . . .
C1 C 0.18732(16) 0.6890(3) 0.6280(4) 0.1088(9) Uani 1 1 d . . . . .
H1A H 0.125881 0.731261 0.594287 0.131 Uiso 1 1 calc R U . . .
F1 F 0.9536(4) 0.6246(18) 0.6622(6) 0.163(4) Uani 0.573(13) 1 d D . P A 1
F2 F 0.9699(4) 0.7240(7) 0.8506(10) 0.144(3) Uani 0.573(13) 1 d D U P A 1
F3 F 0.9748(3) 0.5019(8) 0.8394(9) 0.131(2) Uani 0.573(13) 1 d D U P A 1
F1A F 0.9470(6) 0.7151(13) 0.6958(14) 0.149(4) Uani 0.427(13) 1 d D . P A 2
F2A F 0.9797(5) 0.644(3) 0.8910(8) 0.219(9) Uani 0.427(13) 1 d D . P A 2
F3A F 0.9579(6) 0.4902(12) 0.729(3) 0.221(9) Uani 0.427(13) 1 d D . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6 N2 H2 117.1 . . ?
C5 N2 H2 117.1 . . ?
C5 N2 C6 125.73(16) . . ?
C4 N1 H1 125.5 . . ?
C1 N1 H1 125.5 . . ?
C1 N1 C4 109.0(2) . . ?
C11 C6 N2 119.02(17) . . ?
C7 C6 N2 121.08(17) . . ?
C7 C6 C11 119.87(18) . . ?
N1 C4 C5 120.45(19) . . ?
N1 C4 C3 106.62(17) . . ?
C3 C4 C5 132.92(18) . . ?
N2 C5 S1 122.93(13) . . ?
N2 C5 C4 115.40(17) . . ?
C4 C5 S1 121.66(14) . . ?
C10 C9 C12 120.88(19) . . ?
C8 C9 C10 119.27(18) . . ?
C8 C9 C12 119.9(2) . . ?
C6 C11 H11 120.2 . . ?
C6 C11 C10 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C4 C3 H3 126.0 . . ?
C4 C3 C2 107.9(2) . . ?
C2 C3 H3 126.0 . . ?
C9 C10 C11 120.52(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
F1 C12 C9 116.0(3) . . ?
F2 C12 C9 112.4(3) . . ?
F2 C12 F1 105.6(6) . . ?
F3 C12 C9 113.9(3) . . ?
F3 C12 F1 107.2(5) . . ?
F3 C12 F2 100.2(4) . . ?
F1A C12 C9 109.9(4) . . ?
F1A C12 F2A 104.7(9) . . ?
F2A C12 C9 115.5(5) . . ?
F3A C12 C9 111.0(4) . . ?
F3A C12 F1A 104.5(8) . . ?
F3A C12 F2A 110.4(8) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C3 C2 H2A 126.4 . . ?
C1 C2 C3 107.1(2) . . ?
C1 C2 H2A 126.4 . . ?
N1 C1 H1A 125.4 . . ?
C2 C1 N1 109.3(2) . . ?
C2 C1 H1A 125.4 . . ?
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
S1 C5 1.668(2) . ?
N2 H2 0.8600 . ?
N2 C6 1.429(2) . ?
N2 C5 1.340(2) . ?
N1 H1 0.8600 . ?
N1 C4 1.366(3) . ?
N1 C1 1.350(3) . ?
C6 C11 1.374(3) . ?
C6 C7 1.352(3) . ?
C4 C5 1.445(2) . ?
C4 C3 1.375(3) . ?
C9 C10 1.368(3) . ?
C9 C12 1.492(3) . ?
C9 C8 1.365(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.393(3) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.377(3) . ?
C12 F1 1.278(5) . ?
C12 F2 1.319(5) . ?
C12 F3 1.289(5) . ?
C12 F1A 1.289(6) . ?
C12 F2A 1.269(7) . ?
C12 F3A 1.302(6) . ?
C8 H8 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C1 1.342(4) . ?
C1 H1A 0.9300 . ?
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
N2 C6 C11 C10 178.5(2) . . . . ?
N2 C6 C7 C8 -178.6(2) . . . . ?
N1 C4 C5 S1 -4.8(3) . . . . ?
N1 C4 C5 N2 176.05(18) . . . . ?
N1 C4 C3 C2 -0.5(3) . . . . ?
C6 N2 C5 S1 1.3(3) . . . . ?
C6 N2 C5 C4 -179.61(16) . . . . ?
C6 C11 C10 C9 0.0(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C4 N1 C1 C2 -1.3(3) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C5 N2 C6 C11 116.4(2) . . . . ?
C5 N2 C6 C7 -65.6(3) . . . . ?
C5 C4 C3 C2 179.3(2) . . . . ?
C11 C6 C7 C8 -0.6(4) . . . . ?
C3 C4 C5 S1 175.48(19) . . . . ?
C3 C4 C5 N2 -3.7(3) . . . . ?
C3 C2 C1 N1 1.0(3) . . . . ?
C10 C9 C12 F1 -158.2(9) . . . . ?
C10 C9 C12 F2 -36.6(6) . . . . ?
C10 C9 C12 F3 76.6(6) . . . . ?
C10 C9 C12 F1A -114.2(8) . . . . ?
C10 C9 C12 F2A 3.9(13) . . . . ?
C10 C9 C12 F3A 130.6(14) . . . . ?
C10 C9 C8 C7 0.3(4) . . . . ?
C7 C6 C11 C10 0.5(4) . . . . ?
C12 C9 C10 C11 179.4(2) . . . . ?
C12 C9 C8 C7 -179.5(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C9 C12 F1 21.6(9) . . . . ?
C8 C9 C12 F2 143.2(6) . . . . ?
C8 C9 C12 F3 -103.7(6) . . . . ?
C8 C9 C12 F1A 65.5(9) . . . . ?
C8 C9 C12 F2A -176.3(13) . . . . ?
C8 C9 C12 F3A -49.6(15) . . . . ?
C1 N1 C4 C5 -178.7(2) . . . . ?
C1 N1 C4 C3 1.1(3) . . . . ?
