Effect of cysteine thiols on the catalytic and anticancer activity of Ru(ii) sulfonyl-ethylenediamine complexes
Chen, Feng; Romero-Canelón, Isolda; Habtemariam, Abraha; Song, Ji-Inn; Banerjee, Samya; Clarkson, Guy J.; Song, Lijiang; Prokes, Ivan; Sadler, Peter J.; Dalton Transactions  (2022) –; doi:10.1039/D1DT03856G

data_7709618
_publ_section_title
;
 Effect of cysteine thiols on the catalytic and anticancer activity of
 Ru(ii) sulfonyl-ethylenediamine complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03856G
_journal_year                    2022
_chemical_formula_moiety         'C28 H29 I N2 O2 Ru S'
_chemical_formula_sum            'C28 H29 I N2 O2 Ru S'
_chemical_formula_weight         685.56
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2021-10-25 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.2296(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.91549(4)
_cell_length_b                   9.33603(4)
_cell_length_c                   13.28373(5)
_cell_measurement_reflns_used    33443
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4420
_cell_measurement_theta_min      4.0690
_cell_volume                     1339.770(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -114.00 -14.00   1.00    2.00    --  -41.82 -57.00  90.00  100
  2  \w   -116.00 -17.00   1.00    2.00    --  -41.82 -37.00-180.00   99
  3  \w   -114.00 -14.00   1.00    2.00    --  -41.82 -57.00 150.00  100
  4  \w   -116.00 -17.00   1.00    2.00    --  -41.82 -37.00  30.00   99
  5  \w   -118.00  -9.00   1.00    2.00    --  -41.82 -77.00 150.00  109
  6  \w    -96.00  -2.00   1.00    2.00    --  -41.82 125.00 -90.00   94
  7  \w      1.00  83.00   1.00    2.00    --   41.82 -99.00-120.00   82
  8  \w     74.00 178.00   1.00    8.00    --  107.00  77.00 120.00  104
  9  \w     35.00 136.00   1.00    8.00    --  107.00 -61.00-180.00  101
 10  \w     78.00 178.00   1.00    8.00    --  107.00  61.00-120.00  100
 11  \w     81.00 178.00   1.00    8.00    --  107.00  45.00 -90.00   97
 12  \w     74.00 178.00   1.00    8.00    --  107.00  77.00 150.00  104
 13  \w     94.00 178.00   1.00    8.00    --  107.00 125.00 -60.00   84
 14  \w     74.00 178.00   1.00    8.00    --  107.00  77.00-180.00  104
 15  \w     25.00 160.00   1.00    8.00    --  107.00 -15.00 120.00  135
 16  \w     78.00 178.00   1.00    8.00    --  107.00  61.00-150.00  100
 17  \w     74.00 178.00   1.00    8.00    --  107.00  77.00-150.00  104
 18  \w     78.00 178.00   1.00    8.00    --  107.00  61.00 150.00  100
 19  \w     78.00 178.00   1.00    8.00    --  107.00  61.00 120.00  100
 20  \w     78.00 178.00   1.00    8.00    --  107.00  61.00-180.00  100
 21  \w     24.00 109.00   1.00    8.00    --  107.00 -94.00  90.00   85
 22  \w     79.00 178.00   1.00    8.00    --  107.00  30.00 -90.00   99
 23  \w     81.00 178.00   1.00    8.00    --  107.00  45.00-120.00   97
 24  \w     74.00 178.00   1.00    8.00    --  107.00  77.00-120.00  104
 25  \w     79.00 178.00   1.00    8.00    --  107.00  30.00 -60.00   99
 26  \w     81.00 178.00   1.00    8.00    --  107.00  45.00 150.00   97
 27  \w   -118.00  -9.00   1.00    2.00    --  -41.82 -77.00-120.00  109
 28  \w   -118.00  -9.00   1.00    2.00    --  -41.82 -77.00 -30.00  109
 29  \w   -114.00 -14.00   1.00    2.00    --  -41.82 -57.00 -60.00  100
 30  \w   -118.00  -9.00   1.00    2.00    --  -41.82 -77.00  30.00  109
 31  \w   -118.00  -9.00   1.00    2.00    --  -41.82 -77.00  60.00  109
 32  \w      1.00  83.00   1.00    2.00    --   41.82 -99.00 150.00   82
 33  \w      1.00  83.00   1.00    2.00    --   41.82 -99.00  90.00   82
 34  \w     34.00 121.00   1.00    8.00    --  107.00-125.00 -90.00   87
 35  \w     78.00 178.00   1.00    8.00    --  107.00  61.00   0.00  100
 36  \w     74.00 178.00   1.00    8.00    --  107.00  77.00 -90.00  104
 37  \w     74.00 178.00   1.00    8.00    --  107.00  77.00  60.00  104
 38  \w     74.00 178.00   1.00    8.00    --  107.00  77.00 -30.00  104
 39  \w     78.00 178.00   1.00    8.00    --  107.00  61.00 -30.00  100
 40  \w     78.00 178.00   1.00    8.00    --  107.00  61.00  90.00  100
 41  \w     74.00 178.00   1.00    8.00    --  107.00  77.00  30.00  104
 42  \w     78.00 178.00   1.00    8.00    --  107.00  61.00  30.00  100
 43  \w     24.00 109.00   1.00    8.00    --  107.00 -94.00  30.00   85
 44  \w     74.00 178.00   1.00    8.00    --  107.00  77.00   0.00  104
 45  \w     74.00 178.00   1.00    8.00    --  107.00  77.00 -60.00  104
 46  \w     74.00 178.00   1.00    8.00    --  107.00  77.00  90.00  104
 47  \w     78.00 178.00   1.00    8.00    --  107.00  61.00  60.00  100
 48  \w     78.00 150.00   1.00    8.00    --  107.00  61.00 -60.00   72
 49  \w     24.00 109.00   1.00    8.00    --  107.00 -94.00 -30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0719157000
_diffrn_orient_matrix_UB_12      0.0584516000
_diffrn_orient_matrix_UB_13      -0.0828828000
_diffrn_orient_matrix_UB_21      0.1176613000
_diffrn_orient_matrix_UB_22      0.0118061000
_diffrn_orient_matrix_UB_23      0.0788312000
_diffrn_orient_matrix_UB_31      0.0363272000
_diffrn_orient_matrix_UB_32      -0.1538438000
_diffrn_orient_matrix_UB_33      -0.0254823000
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38933
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.594
_diffrn_reflns_theta_min         4.737
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 2611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
The molecule has crystalised in a polar space group but the handedness is not 
important to the refinement.
Hooft y: 0.0012(11) Olex2
Flack x: -0.006(2) Shelx2018
;
_refine_ls_abs_structure_Flack   -0.0059(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0168
_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/[\s^2^(Fo^2^)+(0.0303P)^2^+0.3037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0426
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5335
_reflns_number_total             5343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03856g2.cif
_cod_data_source_block           jc8
_cod_original_cell_volume        1339.768(9)
_cod_database_code               7709618
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P Ru'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
The NH was located in a difference map and refined with restraints.
The molecule has crystalised in a polar space group but the handedness is not 
important to the refinement.

1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H22 of C22, H21 of C21, H20 of C20, H19 of C19, H18 of
  C18, H17 of C17, H16 of C16, H15 of C15, H3 of C3, H4 of C4, H6 of C6, H7 of
  C7, H23 of C23, H24 of C24, H27 of C27, H28 of C28, H29 of C29, H30 of C30,
  H31 of C31
 At 1.5 times of:
  All C(H,H,H) groups, H12 of C31
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              2165
_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 2.608
_oxdiff_exptl_absorpt_empirical_full_min 0.615