The coordination chemistry and anticancer activity of organo-ruthenium(II), -iridium(III) and -rhodium(III) complexes with sulfonyl-substituted thiourea ligands.
Risi, Matthew C.; Stjärnhage, Julia; Henderson, William; Lane, Joseph R.; Hartinger, Christian G.; Saunders, Graham C.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 539–549; doi:10.1039/d4dt02733g

data_7717546
_publ_section_title
;
 The coordination chemistry and anticancer activity of
 organo-ruthenium(II), -iridium(III) and -rhodium(III) complexes with
 sulfonyl-substituted thiourea ligands.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              539
_journal_page_last               549
_journal_paper_doi               10.1039/d4dt02733g
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C19 H25 Cl N2 O2 Ru S2'
_chemical_formula_sum            'C19 H25 Cl N2 O2 Ru S2'
_chemical_formula_weight         514.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-10-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                103.603(2)
_cell_angle_beta                 92.669(2)
_cell_angle_gamma                100.473(2)
_cell_formula_units_Z            2
_cell_length_a                   7.10950(10)
_cell_length_b                   10.2048(2)
_cell_length_c                   14.9475(3)
_cell_measurement_reflns_used    19737
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      73.8190
_cell_measurement_theta_min      3.0350
_cell_volume                     1031.94(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9749
_diffrn_measured_fraction_theta_max 0.9749
_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     23.00  98.00   0.50    0.10    --   47.23  19.00 -30.00  150
  2  \w     79.00 130.00   0.50    0.10    --   47.23   7.00-134.00  102
  3  \w     29.00  56.00   0.50    0.10    --   47.23   7.00-134.00   54
  4  \w     27.00  59.00   0.50    0.10    --   47.23  57.00 -90.00   64
  5  \w    -18.00  24.00   0.50    0.10    --   47.23  -7.00  49.00   84
  6  \w     40.00  67.00   0.50    0.20    --  100.91 -77.00  60.00   54
  7  \w     74.00 102.00   0.50    0.20    --  100.91 -77.00 150.00   56
  8  \w     30.00  65.00   0.50    0.20    --  100.91 -77.00 150.00   70
  9  \w     74.00 104.00   0.50    0.20    --  100.91 -77.00  60.00   60
 10  \w     34.00  84.00   0.50    0.20    --  100.91 -77.00 -90.00  100
 11  \w     28.00  69.00   0.50    0.20    --  100.91 -61.00 -90.00   82
 12  \w     74.00 105.00   0.50    0.20    --  100.91 -77.00-180.00   62
 13  \w     26.00  69.00   0.50    0.20    --  100.91 -77.00-180.00   86
 14  \w     28.00  53.00   0.50    0.20    --  100.91 -61.00-150.00   50
 15  \w     24.00  49.00   0.50    0.20    --  100.91 -45.00-150.00   50
 16  \w      6.00  43.00   0.50    0.10    --   47.23 -38.00 -60.00   74
 17  \w     24.00  49.00   0.50    0.20    --  100.91 -45.00 150.00   50
 18  \w     20.00  83.00   0.50    0.20    --  100.91   0.00  30.00  126
 19  \w     34.00  60.00   0.50    0.10    --   62.00  80.00 -59.26   52
 20  \w     46.00  72.00   0.50    0.10    --   74.00  80.00  51.61   52
 21  \w     44.00  70.00   0.50    0.10    --   70.00  79.00 129.50   52
 22  \w     38.00  72.00   0.50    0.10    --   66.00  80.00 103.28   68
 23  \w     30.00  62.00   0.50    0.10    --   58.00  79.00  57.30   64
 24  \w     34.00  65.00   0.50    0.10    --   58.00  78.00   7.64   62
 25  \w     74.00 172.00   0.50    0.20    --  100.91  77.00  60.00  196
 26  \w     76.00 147.00   0.50    0.20    --  100.91  77.00-150.00  142
 27  \w     36.00  62.00   0.50    0.10    --   62.00  77.00-178.82   52
 28  \w     41.00  67.00   0.50    0.10    --   66.00  76.00-163.31   52
 29  \w     32.00  57.00   0.50    0.10    --   58.00  77.00 -99.05   50
 30  \w     83.00 121.00   0.50    0.20    --  100.91  61.00-150.00   76
 31  \w     32.00  58.00   0.50    0.20    --  100.91   7.00-134.00   52
 32  \w    125.00 176.00   0.50    0.20    --  100.91   7.00-134.00  102
 33  \w     91.00 143.00   0.50    0.20    --  100.91  61.00  60.00  104
 34  \w     79.00 138.00   0.50    0.20    --  100.91  61.00 120.00  118
 35  \w     87.00 169.00   0.50    0.20    --  100.91   0.00  30.00  164
 36  \w      8.00  33.00   0.50    0.10    --   42.00  93.00  -4.77   50
 37  \w     13.00  38.00   0.50    0.10    --   46.00  91.00 -65.02   50
 38  \w     16.00  41.00   0.50    0.10    --   50.00  92.00-145.62   50
 39  \w     16.00  41.00   0.50    0.10    --   50.00  92.00 -46.77   50
 40  \w     17.00  42.00   0.50    0.10    --   50.00  90.00  -9.29   50
 41  \w     17.00  42.00   0.50    0.10    --   50.00  90.00  81.68   50
 42  \w     13.00  38.00   0.50    0.10    --   46.00  91.00 156.24   50
 43  \w     17.00  42.00   0.50    0.10    --   50.00  90.00 165.76   50
 44  \w    -57.00 -26.00   0.50    0.10    --  -47.23 -60.00 -77.25   62
 45  \w    -54.00 -26.00   0.50    0.10    --  -47.23 -38.00 -60.00   56
 46  \w    -87.00 -60.00   0.50    0.10    --  -47.23 -38.00 -60.00   54
 47  \w   -127.00 -71.00   0.50    0.10    --  -47.23  -7.00  49.00  112
 48  \w    -66.00  -7.00   0.50    0.10    --  -47.23  -7.00  49.00  118
 49  \w    -19.00   7.00   0.50    0.10    --  -47.23   7.00-134.00   52
 50  \w    -53.00 -26.00   0.50    0.10    --  -47.23 -57.00  90.00   54
 51  \w    -61.00 -26.00   0.50    0.10    --  -47.23 -57.00 150.00   70
 52  \w   -120.00 -95.00   0.50    0.10    --  -47.23 -57.00  90.00   50
 53  \w   -115.00 -90.00   0.50    0.20    --  -90.25  -7.00  49.00   50
 54  \w    -93.00 -63.00   0.50    0.20    --  -90.25 -78.00 -65.62   60
 55  \w   -116.00 -62.00   0.50    0.20    --  -90.25 -80.00 -73.81  108
 56  \w   -167.00-125.00   0.50    0.20    --  -90.25 -80.00 -73.81   84
 57  \w   -153.00-121.00   0.50    0.20    --  -78.00 -78.00  35.91   64
 58  \w    -76.00 -51.00   0.50    0.20    --  -78.00 -78.00 -62.53   50
 59  \w    -75.00 -50.00   0.50    0.20    --  -78.00 -78.00  35.91   50
 60  \w   -109.00 -63.00   0.50    0.20    --  -90.25 -77.00  30.00   92
 61  \w    -80.00 -46.00   0.50    0.20    --  -74.00 -79.00 157.98   68
 62  \w   -154.00-105.00   0.50    0.20    --  -90.25 -77.00  53.54   98
 63  \w   -157.00-121.00   0.50    0.20    --  -90.25 -77.00  30.00   72
 64  \w   -166.00-120.00   0.50    0.20    --  -90.25 -77.00 -30.00   92
 65  \w    -96.00 -63.00   0.50    0.20    --  -90.25 -77.00-120.00   66
 66  \w    -81.00 -55.00   0.50    0.20    --  -82.00 -77.00-153.24   52
 67  \w   -116.00 -91.00   0.50    0.20    --  -82.00 -77.00-153.24   50
 68  \w   -144.00-119.00   0.50    0.20    --  -90.25 -77.00-120.00   50
 69  \w    -94.00 -65.00   0.50    0.20    --  -90.25 -77.00 -30.00   58
 70  \w   -108.00 -63.00   0.50    0.20    --  -90.25 -77.00 -90.00   90
 71  \w    -90.00 -65.00   0.50    0.20    --  -90.25 -77.00-150.00   50
 72  \w   -148.00-102.00   0.50    0.20    --  -90.25 -77.00-150.00   92
 73  \w   -166.00 -65.00   0.50    0.20    --  -90.25 -76.00 -17.73  202
 74  \w    -77.00 -52.00   0.50    0.20    --  -78.00 -76.00-172.85   50
 75  \w   -128.00 -63.00   0.50    0.20    --  -90.25 -77.00   0.00  130
 76  \w    -83.00 -58.00   0.50    0.20    --  -82.00 -75.00-114.39   50
 77  \w    -68.00 -43.00   0.50    0.20    --  -70.00 -76.00-136.88   50
 78  \w    -95.00 -63.00   0.50    0.20    --  -90.25 -77.00  53.54   64
 79  \w   -131.00 -64.00   0.50    0.20    --  -90.25 -77.00 150.00  134
 80  \w    -93.00 -60.00   0.50    0.20    --  -86.00 -75.00 126.53   66
 81  \w    -92.00 -66.00   0.50    0.20    --  -90.25 -74.00 108.16   52
 82  \w    -78.00 -53.00   0.50    0.20    --  -78.00 -76.00 141.08   50
 83  \w   -165.00 -66.00   0.50    0.20    --  -90.25 -75.00 166.82  198
 84  \w   -156.00-114.00   0.50    0.20    --  -90.25 -74.00  66.34   84
 85  \w    -91.00 -66.00   0.50    0.20    --  -90.25 -74.00  66.34   50
 86  \w    -78.00 -53.00   0.50    0.20    --  -78.00 -72.00  58.19   50
 87  \w   -102.00 -66.00   0.50    0.20    --  -90.25 -71.00   4.80   72
 88  \w    -93.00 -64.00   0.50    0.20    --  -90.25 -74.00 -55.05   58
 89  \w    -71.00 -46.00   0.50    0.20    --  -70.00 -73.00-167.23   50
 90  \w    -69.00 -44.00   0.50    0.20    --  -70.00 -75.00 -43.00   50
 91  \w    -76.00 -51.00   0.50    0.20    --  -74.00 -68.00 -12.49   50
 92  \w    -84.00 -59.00   0.50    0.20    --  -82.00 -66.00  71.86   50
 93  \w    -98.00 -67.00   0.50    0.20    --  -90.25 -67.00 111.69   62
 94  \w   -124.00 -67.00   0.50    0.20    --  -90.25 -70.00 174.82  114
 95  \w   -162.00-133.00   0.50    0.20    --  -90.25 -67.00 111.69   58
 96  \w    -40.00 -13.00   0.50    0.20    --  -90.25  -7.00  49.00   54
 97  \w     44.00  97.00   0.50    0.10    --   47.23-125.00 -30.00  106
 98  \w     25.00 106.00   0.50    0.20    --  100.91-111.00  60.00  162
 99  \w     27.00 107.00   0.50    0.20    --  100.91-111.00   0.00  160
100  \w     25.00  58.00   0.50    0.20    --  100.91-108.00 -89.25   66
101  \w     60.00 109.00   0.50    0.20    --  100.91-108.00 -89.25   98
102  \w     78.00 108.00   0.50    0.20    --  100.91-111.00-180.00   60
103  \w     22.00  77.00   0.50    0.20    --  100.91 -95.00   0.00  110
104  \w     72.00 106.00   0.50    0.20    --  100.91 -95.00  60.00   68
105  \w     25.00  60.00   0.50    0.20    --  100.91 -95.00  60.00   70
106  \w     37.00 102.00   0.50    0.20    --  100.91 -95.00 150.00  130
107  \w    120.00 145.00   0.50    0.20    --  100.91 178.00  90.00   50
108  \w     73.00 102.00   0.50    0.20    --  100.91 178.00  90.00   58
109  \w     63.00 113.00   0.50    0.20    --  100.91 178.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1349770000
_diffrn_orient_matrix_UB_12      -0.1326951000
_diffrn_orient_matrix_UB_13      0.0073016000
_diffrn_orient_matrix_UB_21      0.1704554000
_diffrn_orient_matrix_UB_22      -0.0748325000
_diffrn_orient_matrix_UB_23      -0.0070392000
_diffrn_orient_matrix_UB_31      0.0413901000
_diffrn_orient_matrix_UB_32      0.0436584000
_diffrn_orient_matrix_UB_33      0.1060212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29157
_diffrn_reflns_theta_full        74.0606
_diffrn_reflns_theta_max         74.06
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.6543
_exptl_crystal_description       block
_exptl_crystal_F_000             527.3406
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3844
_refine_diff_density_min         -0.5716
_refine_diff_density_rms         0.0825
_refine_ls_d_res_high            0.8017
_refine_ls_d_res_low             14.4646
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0267
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0187P)^2^+0.9765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3811
_reflns_number_total             4084
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4dt02733g2.cif
_cod_data_source_block           MCR_16
_cod_depositor_comments
'Adding full bibliography for 7717543--7717550.cif.'
_cod_original_cell_volume        1031.94(4)
_cod_database_code               7717546
_chemical_oxdiff_formula         C19H26Cl2N2O2RuS2
_diffrn_oxdiff_digest_frames
;
010e1818e447275f80903ff861b6593d9d083424c16
;
_diffrn_oxdiff_digest_hkl
;
01dcf64b9972e28d68b1043d7dbfd22a7fce00
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C26(H26), C23(H23), C12(H12), C27(H27), C13(H13), C14(H14), C15(H15),
 C24(H24), C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C21(H21a,H21b,H21c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
;
_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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.700