Platinum(II) complexes of fluorinated pyrrole carbothioamides: enhanced anticancer activity and overcoming cisplatin resistance.
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.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 17112–17120; doi:10.1039/d5dt02290h

data_7719759
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     33.00  59.00   0.50    0.50    --   42.30 -82.00  30.00   52
  2  \w    -25.00  28.00   0.50    0.50    --   42.30 -54.00 120.00  106
  3  \w     87.00 130.00   0.50    0.50    --   42.30  77.00 -30.00   86
  4  \w     42.00  67.00   0.50    0.50    --   42.30 -65.00  30.00   50
  5  \w    -27.00  20.00   0.50    0.50    --   42.30 -65.00  30.00   94
  6  \w    -44.00  -4.00   0.50    0.50    --   42.30 -82.00-180.00   80
  7  \w     18.00  90.00   0.50    0.50    --   42.30  77.00  60.00  144
  8  \w    -47.00  10.00   0.50    0.50    --   42.30 -77.00 -90.00  114
  9  \w     95.00 132.00   0.50    0.50    --   42.30  77.00  60.00   74
 10  \w     11.00  70.00   0.50    0.50    --   42.30 -82.00-180.00  118
 11  \w     21.00  76.00   0.50    0.50    --   42.30  77.00 -30.00  110
 12  \w    -32.00  -7.00   0.50    0.50    --   42.30 -82.00  30.00   50
 13  \w     32.00  65.00   0.50    0.50    --   42.30 -65.00 -60.00   66
 14  \w    -46.00   6.00   0.50    0.50    --   42.30 -65.00 -60.00  104
 15  \w     20.00  63.00   0.50    0.50    --   42.30 -77.00 -90.00   86
 16  \w     37.00  62.00   0.50    0.50    --   42.30 -77.00  30.00   50
 17  \w     32.00  57.00   0.50    0.50    --   42.30 -77.00 150.00   50
 18  \w      4.00  29.00   0.50    0.50    --   42.30 -77.00 150.00   50
 19  \w     36.00  62.00   0.50    0.67    --   93.70 -82.00-180.00   52
 20  \w     24.00  56.00   0.50    0.67    --   93.70 -82.00  30.00   64
 21  \w      7.00 101.00   0.50    0.67    --   93.70 -82.00  90.00  188
 22  \w    111.00 137.00   0.50    0.67    --   93.70  59.00 -90.00   52
 23  \w     69.00 177.00   0.50    0.67    --   93.70  68.00  30.00  216
 24  \w     66.00 182.00   0.50    0.67    --   93.70  59.00 -60.00  232
 25  \w      6.00 121.00   0.50    0.67    --   93.70 -82.00 150.00  230
 26  \w     70.00  96.00   0.50    0.67    --   93.70 -82.00 -90.00   52
 27  \w     23.00  49.00   0.50    0.67    --   93.70 -82.00 -90.00   52
 28  \w     85.00 110.00   0.50    0.67    --   93.70 -82.00  30.00   50
 29  \w     84.00 151.00   0.50    0.67    --   93.70  68.00  60.00  134
 30  \w     68.00  94.00   0.50    0.67    --   93.70 -82.00-180.00   52
 31  \w     37.00 101.00   0.50    0.67    --   93.70 -82.00 -60.00  128
 32  \w     72.00 181.00   0.50    0.67    --   93.70  59.00 -30.00  218
 33  \w     68.00 183.00   0.50    0.67    --   93.70  59.00   0.00  230
 34  \w     69.00 133.00   0.50    0.67    --   93.70  33.00 120.00  128
 35  \w     45.00  84.00   0.50    0.67    --   93.70 -82.00-120.00   78
 36  \w     20.00 103.00   0.50    0.67    --   93.70 -82.00   0.00  166
 37  \w      6.00  93.00   0.50    0.67    --   93.70 -82.00  60.00  174
 38  \w      8.00  93.00   0.50    0.67    --   93.70 -82.00 120.00  170
 39  \w     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       '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0660P)^2^+0.1493P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              79977
_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