Ru(II)-diphosphine/N,S-mercapto complexes and their anti-melanoma properties.
da Silva, Nádija N P; Palmeira-Mello, Marcos V; Acésio, Nathália O; Moraes, Carlos A. F.; Honorato, João; Castellano, Eduardo E.; Tavares, Denise C.; Oliveira, Katia M.; Batista, Alzir A.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 605–615; doi:10.1039/d4dt02575j

data_7717505
_publ_section_title
;
 Ru(II)-diphosphine/N,S-mercapto complexes and their anti-melanoma
 properties.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              605
_journal_page_last               615
_journal_paper_doi               10.1039/d4dt02575j
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C58 H49 N2 O P4 Ru S, C3 H6 O, F6 P, 1[C2H6O]'
_chemical_formula_sum            'C63 H61 F6 N2 O3 P5 Ru S'
_chemical_formula_weight         1296.188
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_Int_Tables_number      7
_audit_creation_date             2024-05-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0784(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.2901(3)
_cell_length_b                   11.7639(3)
_cell_length_c                   16.7665(2)
_cell_measurement_reflns_used    30366
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      77.8750
_cell_measurement_theta_min      3.7430
_cell_volume                     3008.17(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9995
_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   -119.00 -37.00   0.50    0.94    --  -48.82 -29.00 146.00  164
  2  \w    -27.00  25.00   0.50    0.94    --  -48.82  29.00 -51.00  104
  3  \w    -19.00   6.00   0.50    0.94    --   48.82 -29.00 146.00   50
  4  \w     42.00 122.00   0.50    0.94    --   48.82  29.00 -51.00  160
  5  \w   -145.00-120.00   0.50    3.78    --  -90.00 -29.00 146.00   50
  6  \w    103.00 156.00   0.50    3.78    --  111.50  29.00 -51.00  106
  7  \w    -25.00  24.00   0.50    0.94    --  -48.82  19.00  90.00   98
  8  \w   -118.00 -85.00   0.50    0.94    --  -48.82-125.00 120.00   66
  9  \w    -62.00  -4.00   0.50    0.94    --  -48.82  57.00-180.00  116
 10  \w   -113.00 -76.00   0.50    0.94    --  -48.82-125.00 -60.00   74
 11  \w   -118.00 -74.00   0.50    0.94    --  -48.82-125.00  90.00   88
 12  \w     52.00  94.00   0.50    0.94    --   48.82-125.00   0.00   84
 13  \w    -21.00   4.00   0.50    0.94    --   48.82 -19.00 -60.00   50
 14  \w    -83.00 -21.00   0.50    3.78    --  -90.00 125.00   0.00  124
 15  \w     72.00 107.00   0.50    3.78    --  111.50-103.00 -37.30   70
 16  \w    101.00 157.00   0.50    3.78    --  111.50  15.00 120.00  112
 17  \w     40.00  69.00   0.50    3.78    --  111.50 -61.00 -30.00   58
 18  \w     59.00  85.00   0.50    3.78    --  111.50-125.00  60.00   52
 19  \w     63.00 104.00   0.50    3.78    --  111.50-110.00-145.30   82
 20  \w    111.00 144.00   0.50    3.78    --  111.50  45.00 150.00   66
 21  \w     40.00  71.00   0.50    3.78    --  111.50 -61.00 -60.00   62
 22  \w     63.00 105.00   0.50    3.78    --  111.50 -77.00 150.00   84
 23  \w     55.00 103.00   0.50    3.78    --  111.50-118.00  10.89   96
 24  \w    109.00 178.00   0.50    3.78    --  111.50  79.00 158.73  138
 25  \w    115.00 165.00   0.50    3.78    --  111.50  15.00-120.00  100
 26  \w     42.00  68.00   0.50    3.78    --  111.50 -61.00 150.00   52
 27  \w     42.00  93.00   0.50    3.78    --  111.50-125.00  90.00  102
 28  \w     60.00 104.00   0.50    3.78    --  111.50-107.00-125.40   88
 29  \w     61.00 109.00   0.50    3.78    --  111.50-125.00 -30.00   96
 30  \w     43.00 105.00   0.50    3.78    --  111.50 -95.00  30.00  124
 31  \w     95.00 125.00   0.50    3.78    --  111.50 125.00-150.00   60
 32  \w    131.00 171.00   0.50    3.78    --  111.50 125.00-150.00   80
 33  \w    108.00 134.00   0.50    3.78    --  111.50 -87.00 -16.52   52
 34  \w    126.00 177.00   0.50    3.78    --  111.50  61.00   0.00  102
 35  \w     41.00 115.00   0.50    3.78    --  111.50-132.00 174.65  148
 36  \w    101.00 172.00   0.50    3.78    --  111.50  45.00  90.00  142
 37  \w     45.00  99.00   0.50    3.78    --  111.50 -95.00 120.00  108
 38  \w     81.00 122.00   0.50    3.78    --  111.50-139.00  84.03   82
 39  \w    101.00 140.00   0.50    3.78    --  111.50  45.00-150.00   78
 40  \w     43.00  70.00   0.50    3.78    --  111.50 -61.00-120.00   54
 41  \w     42.00  67.00   0.50    3.78    --  111.50 -59.00-165.14   50
 42  \w     60.00 104.00   0.50    3.78    --  111.50-106.00  93.35   88
 43  \w     61.00  87.00   0.50    3.78    --  111.50 -77.00 -60.00   52
 44  \w    119.00 155.00   0.50    3.78    --  111.50  36.00 -80.86   72
 45  \w    118.00 161.00   0.50    3.78    --  111.50  30.00 -30.00   86
 46  \w     40.00  70.00   0.50    3.78    --  111.50 -61.00  30.00   60
 47  \w    137.00 177.00   0.50    3.78    --  111.50 125.00  60.00   80
 48  \w     44.00  73.00   0.50    3.78    --  111.50-125.00-120.00   58
 49  \w     83.00 111.00   0.50    3.78    --  111.50-125.00-120.00   56
 50  \w    104.00 177.00   0.50    3.78    --  111.50  45.00  60.00  146
 51  \w     68.00  94.00   0.50    3.78    --  111.50-149.00-179.69   52
 52  \w    103.00 129.00   0.50    3.78    --  111.50-149.00-179.69   52
 53  \w     79.00 108.00   0.50    3.78    --  111.50-111.00-175.60   58
 54  \w    107.00 155.00   0.50    3.78    --  111.50  15.00  30.00   96
 55  \w     81.00 106.00   0.50    3.78    --  111.50-100.00 -93.28   50
 56  \w     68.00 105.00   0.50    3.78    --  111.50 -77.00-150.00   74
 57  \w     56.00  96.00   0.50    3.78    --  111.50 -95.00   0.00   80
 58  \w     63.00  88.00   0.50    3.78    --  111.50-169.00  -4.08   50
 59  \w    102.00 143.00   0.50    3.78    --  111.50-169.00  -4.08   82
 60  \w     63.00  89.00   0.50    3.78    --  111.50 -87.00 -16.52   52
 61  \w     41.00  75.00   0.50    3.78    --  111.50-111.00-175.60   68
 62  \w     57.00  83.00   0.50    3.78    --  111.50 -77.00  30.00   52
 63  \w     53.00  78.00   0.50    3.78    --  111.50 -77.00  90.00   50
 64  \w     64.00  97.00   0.50    3.78    --  111.50 -95.00  90.00   66
 65  \w     81.00 107.00   0.50    3.78    --  111.50 -83.00-102.87   52
 66  \w     42.00  69.00   0.50    3.78    --  111.50 -61.00 -90.00   54
 67  \w     43.00  68.00   0.50    3.78    --  111.50 -61.00-180.00   50
 68  \w    147.00 174.00   0.50    3.78    --  111.50  15.00-180.00   54
 69  \w    134.00 160.00   0.50    3.78    --  111.50 125.00 120.00   52
 70  \w     41.00  76.00   0.50    3.78    --  111.50-100.00 -93.28   70
 71  \w     53.00  79.00   0.50    3.78    --  111.50 -81.00 140.26   52
 72  \w     64.00 105.00   0.50    3.78    --  111.50 -95.00 -90.00   82
 73  \w     47.00  73.00   0.50    3.78    --  111.50 -95.00 -30.00   52
 74  \w     40.00  77.00   0.50    3.78    --  111.50-125.00 -60.00   74
 75  \w    132.00 171.00   0.50    3.78    --  111.50  45.00  30.00   78
 76  \w     72.00 107.00   0.50    3.78    --  111.50-106.00  84.45   70
 77  \w     40.00  72.00   0.50    3.78    --  111.50 -84.00 108.49   64
 78  \w     84.00 110.00   0.50    3.78    --  111.50 -84.00 108.49   52
 79  \w     45.00  71.00   0.50    3.78    --  111.50 -95.00-120.00   52
 80  \w     49.00  74.00   0.50    3.78    --  111.50-125.00   0.00   50
 81  \w     47.00  73.00   0.50    3.78    --  111.50-125.00 120.00   52
 82  \w    105.00 140.00   0.50    3.78    --  111.50  45.00 -30.00   70
 83  \w    115.00 153.00   0.50    3.78    --  111.50  45.00 120.00   76
 84  \w     62.00 127.00   0.50    3.78    --  111.50-146.00  54.19  130
 85  \w    104.00 138.00   0.50    3.78    --  111.50  61.00-120.00   68
 86  \w    130.00 177.00   0.50    3.78    --  111.50  61.00 -60.00   94
 87  \w    102.00 143.00   0.50    3.78    --  111.50  61.00 120.00   82
 88  \w    140.00 168.00   0.50    3.78    --  111.50 125.00   0.00   56
 89  \w     83.00 109.00   0.50    3.78    --  111.50 -78.00 110.34   52
 90  \w     91.00 126.00   0.50    3.78    --  111.50  74.00 135.81   70
 91  \w    136.00 178.00   0.50    3.78    --  111.50  74.00 135.81   84
 92  \w     85.00 111.00   0.50    3.78    --  111.50 -84.00 155.05   52
 93  \w     90.00 116.00   0.50    3.78    --  111.50 -86.00 -10.04   52
 94  \w     79.00 105.00   0.50    3.78    --  111.50-108.00-102.80   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0843511000
_diffrn_orient_matrix_UB_12      0.0674242000
_diffrn_orient_matrix_UB_13      0.0235341000
_diffrn_orient_matrix_UB_21      -0.0555583000
_diffrn_orient_matrix_UB_22      0.1009656000
_diffrn_orient_matrix_UB_23      0.0252686000
_diffrn_orient_matrix_UB_31      0.0009454000
_diffrn_orient_matrix_UB_32      -0.0489919000
_diffrn_orient_matrix_UB_33      0.0853919000
_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  0.0874
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            71455
_diffrn_reflns_point_group_measured_fraction_full 0.8559
_diffrn_reflns_point_group_measured_fraction_max 0.8557
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.60
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       prism
_exptl_crystal_F_000             1339.950
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.069
_refine_diff_density_max         1.1786
_refine_diff_density_min         -0.4145
_refine_diff_density_rms         0.0960
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.020(7)
_refine_ls_d_res_high            0.8200
_refine_ls_d_res_low             9.6219
_refine_ls_goodness_of_fit_ref   1.0444
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    105
_refine_ls_number_parameters     724
_refine_ls_number_reflns         9784
_refine_ls_number_restraints     215
_refine_ls_restrained_S_all      1.0323
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+1.0487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.712
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              20
_reflns_limit_l_min              -18
_reflns_number_gt                9261
_reflns_number_total             9784
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4dt02575j2.cif
_cod_data_source_block           Ru2-nadija
_cod_depositor_comments
'Adding full bibliography for 7717503--7717505.cif.'
_cod_original_cell_volume        3008.18(10)
_cod_original_sg_symbol_Hall     ' P -2yac'
_cod_original_formula_sum        'C63 H61 F6 N2 O3 P5 Ru1 S1'
_cod_database_code               7717505
_chemical_oxdiff_formula         ' C33 H6 O3 P3 F6 Ru1 S1 N4'
_chemical_oxdiff_usercomment     'Alzir - Nadija'
_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. Restrained distances
 O1S-C1S
 1.21 with sigma of 0.02
 C1S-C2S = C1S-C3S
 1.5 with sigma of 0.02
 P1-F2 = P1-F3 = P1-F1 = P1-F5 = P1-F6 = P1-F4
 1.65 with sigma of 0.02
 O1S-C2S = O1S-C3S
 2.38 with sigma of 0.04
 C1S-C2S \\sim C1S-C3S
 with sigma of 0.02
 C2S-O1S \\sim C3S-O1S
 with sigma of 0.04
 F2-F1 \\sim F3-F5 \\sim F4-F6
 with sigma of 0.05
 P1-F2 \\sim P1-F3 \\sim P1-F1 \\sim P1-F5 \\sim P1-F6 \\sim P1-F4
 with sigma of 0.02
 F2-F3 \\sim F2-F5 \\sim F2-F6 \\sim F2-F4 \\sim F1-F3 \\sim F1-F5 \\sim F1-F6
\\sim F1-F4
 with sigma of 0.04
3. Restrained planarity
 O1S, C1S, C2S, C3S
 with sigma of 0.05
4. Uiso/Uaniso restraints and constraints
O1S \\sim C1S \\sim C2S \\sim C3S: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
P1 \\sim F2 \\sim F3 \\sim F1 \\sim F5 \\sim F6 \\sim F4: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
N1 \\sim C2 \\sim C3 \\sim C8 \\sim N2 \\sim C1: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
Uanis(N1) = Uanis(N2)
5. Rigid body (RIGU) restrains
 O1S, C1S, C2S, C3S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P1, F2, F3, F1, F5, F6, F4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C3, C8, N2, C1, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C34(H34a,H34b)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), N2(H2), C112(H112), C113(H113), C114(H114),
 C115(H115), C116(H116), C122(H122), C123(H123), C124(H124), C125(H125),
 C126(H126), C212(H212), C213(H213), C214(H214), C215(H215), C216(H216),
 C222(H222), C223(H223), C224(H224), C225(H225), C226(H226), C312(H312),
 C313(H313), C314(H314), C315(H315), C316(H316), C323(H323), C324(H324),
 C325(H325), C326(H326), C327(H327), C412(H412), C413(H413), C414(H414),
 C415(H415), C416(H416), C422(H422), C423(H423), C424(H424), C425(H425),
 C426(H426)
6.c Idealised Me refined as rotating group:
 C2S(H2Sa,H2Sb,H2Sc), C3S(H3Sa,H3Sb,H3Sc)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.387
_oxdiff_exptl_absorpt_empirical_full_min 0.421