Impact of aliphatic acyl and aromatic thioamide substituents on the anticancer activity of Ru(II)-p-cymene complexes carrying acylthiourea ligands – In vitro and in vivo studies
Swaminathan, Srividya; Haribabu, Jebiti; Mohamed Kasim, Mohamed Subarkhan; dasararaju, gayathri; Balakrishnan, Nithya; Bhuvanesh, Nattamai; Echeverria, Cesar; Karvembu, R.; Dalton Transactions  (2021) –; doi:10.1039/D1DT02611A

data_7708577
_publ_section_title
;
 Impact of aliphatic acyl and aromatic thioamide substituents on the
 anticancer activity of Ru(II)-p-cymene complexes carrying acylthiourea
 ligands -- In vitro and in vivo studies
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02611A
_journal_year                    2021
_chemical_formula_moiety         'C26 H38 Cl2 N2 O Ru S'
_chemical_formula_sum            'C26 H38 Cl2 N2 O Ru S'
_chemical_formula_weight         598.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-18 deposited with the CCDC.	2021-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.562(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5533(13)
_cell_length_b                   13.3945(13)
_cell_length_c                   24.754(2)
_cell_measurement_reflns_used    9468
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.576
_cell_measurement_theta_min      2.884
_cell_volume                     5484.2(8)
_computing_cell_refinement
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       'APEX 3 (Bruker AXS)'
_computing_data_reduction
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            83206
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1436 before and 0.0889 after correction. The Ratio of minimum to maximum transmission is 0.7159. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       plate
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.405
_exptl_crystal_size_min          0.107
_refine_diff_density_max         1.111
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6343
_refine_ls_number_restraints     538
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0257P)^2^+19.3902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5792
_reflns_number_total             6343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt02611a2.cif
_cod_data_source_block           svpncana
_cod_original_cell_volume        5484.1(8)
_cod_database_code               7708577
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.718
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11A-C10 = C11-C10 = C12A-C11A = C12-C11 = C13A-C12A = C13-C12 = C14A-C13A =
 C14-C13 = C15A-C14A = C15-C14 = C16A-C15A = C16-C15
 1.54 with sigma of 0.01
 N1-C2 \\sim N1-C2A
 with sigma of 0.02
 C11A-C10 \\sim C11-C10 \\sim C12A-C11A \\sim C12-C11 \\sim C13A-C12A \\sim
C13-C12 \\sim C14A-C13A ~
 C14-C13 \\sim C15A-C14A \\sim C15-C14 \\sim C16A-C15A \\sim C16-C15
 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
C2 \\sim C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2A \\sim C7A \\sim C6A
\\sim C5A \\sim C4A \\sim C3A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C11A \\sim C12A
\\sim C13A \\sim C14A \\sim C15A \\sim C16A: within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(C2) = Uanis(C2A)
Uanis(C16) = Uanis(C16A)
Uanis(C11) = Uanis(C11A)
4. Rigid body (RIGU) restrains
 C2, C7, C6, C5, C4, C3, C2A, C7A, C6A, C5A, C4A, C3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C12, C13, C14, C15, C16, C11A, C12A, C13A, C14A, C15A, C16A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Same fragment restrains
{C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.02, 1-3: 0.04
as
{C11A, C12A, C13A, C14A, C15A, C16A}
6. Others
 Sof(H1B)=Sof(H10C)=Sof(H10D)=Sof(C2A)=Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A)=
 Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(H1A)=Sof(H10A)=Sof(H10B)=Sof(C2)=Sof(C7)=Sof(H7)=Sof(C6)=Sof(H6)=Sof(C5)=
 Sof(H5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(H3)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C23(H23)
7.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C11A(H11C,H11D), C12A(H12C,
 H12D), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,H15D)
7.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N1(H1B), N2(H2), C18(H18), C19(H19), C21(H21), C22(H22), C7(H7),
 C6(H6), C5(H5), C4(H4), C3(H3), C7A(H7A), C6A(H6A), C5A(H5A), C4A(H4A),
 C3A(H3A)
7.d Fitted hexagon refined as free rotating group:
 C2(C7,C6,C5,C4,C3), C2A(C7A,C6A,C5A,C4A,C3A)
7.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C16(H16A,H16B,
 H16C), C16A(H16D,H16E,H16F)
;
_shelx_res_checksum              83985
_shelx_hkl_checksum              75311
_olex2_submission_special_instructions 'No special instructions were received'