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_7708572
_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         'C14 H20 N2 O S'
_chemical_formula_sum            'C14 H20 N2 O S'
_chemical_formula_weight         264.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-12
_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                96.577(4)
_cell_angle_beta                 99.785(4)
_cell_angle_gamma                96.172(4)
_cell_formula_units_Z            4
_cell_length_a                   9.5041(11)
_cell_length_b                   10.2883(11)
_cell_length_c                   15.1931(17)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      25.758
_cell_measurement_theta_min      2.275
_cell_volume                     1442.1(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX 3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9748
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        22.500
_diffrn_reflns_theta_max         22.500
_diffrn_reflns_theta_min         2.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1416 before and 0.0861 after correction. The Ratio of minimum to maximum transmission is 0.7628. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.124
_refine_diff_density_max         1.172
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     334
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0770
_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^)+(0.0334P)^2^+6.0505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3017
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt02611a2.cif
_cod_data_source_block           svshcan
_cod_database_code               7708572
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.950
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13B-C14B = C13B-C12B = C11B-C12B = C11B-C10B = C10B-C9B
 1.54 with sigma of 0.005
 C9B-C11B = C10B-C12B = C11B-C13B = C12B-C14B
 2.5 with sigma of 0.005
 C10-C12 = C9-C11 = C11-C13 = C9-C11A = C10-C12A = C11A-C13
 2.5 with sigma of 0.02
 C11A-C10 \\sim C11-C10 \\sim C12A-C11A \\sim C12-C11 \\sim C13-C12 \\sim
C13-C12A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C13 \\sim C14 \\sim C11 \\sim C12 \\sim C11A \\sim C12A \\sim C9B
\\sim C10B \\sim C11B \\sim C12B \\sim C13B \\sim C14B \\sim C10C \\sim C11C
\\sim C12C \\sim C13C \\sim C14C: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C10, C13, C14, C11, C12, C11A, C12A, C9B, C10B, C11B, C12B, C13B, C14B, C10C,
 C11C, C12C, C13C, C14C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Same fragment restrains
{C10B, C11B, C12B, C13B, C14B} sigma for 1-2: 0.005, 1-3: 0.04
as
{C10C, C11C, C12C, C13C, C14C}
6. Others
 Sof(H9BC)=Sof(H9BD)=Sof(C10C)=Sof(H10C)=Sof(H10D)=Sof(C11C)=Sof(H11C)=
 Sof(H11D)=Sof(C12C)=Sof(H12C)=Sof(H12D)=Sof(C13C)=Sof(H13C)=Sof(H13D)=
 Sof(C14C)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H9BA)=Sof(H9BB)=Sof(C10B)=Sof(H10A)=Sof(H10B)=Sof(C11B)=Sof(H11A)=
 Sof(H11B)=Sof(C12B)=Sof(H12A)=Sof(H12B)=Sof(C13B)=Sof(H13A)=Sof(H13B)=
 Sof(C14B)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(H10G)=Sof(H10H)=Sof(H13G)=Sof(H13H)=Sof(C11A)=Sof(H11G)=Sof(H11H)=
 Sof(C12A)=Sof(H12G)=Sof(H12H)=1-FVAR(2)
 Sof(H10E)=Sof(H10F)=Sof(H13E)=Sof(H13F)=Sof(C11)=Sof(H11E)=Sof(H11F)=Sof(C12)=
 Sof(H12E)=Sof(H12F)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10E,H10F), C10(H10G,H10H), C13(H13E,H13F), C13(H13G,H13H),
 C11(H11E,H11F), C12(H12E,H12F), C11A(H11G,H11H), C12A(H12G,H12H), C9B(H9BA,
 H9BB), C9B(H9BC,H9BD), C10B(H10A,H10B), C11B(H11A,H11B), C12B(H12A,H12B),
 C13B(H13A,H13B), C10C(H10C,H10D), C11C(H11C,H11D), C12C(H12C,H12D), C13C(H13C,
 H13D)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), N1B(H1B), N2B(H2B),
 C2B(H2BA), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B)
7.c Idealised Me refined as rotating group:
 C14(H14G,H14H,H14I), C14B(H14A,H14B,H14C), C14C(H14D,H14E,H14F)
;
_shelx_res_checksum              55026
_shelx_hkl_checksum              58130
_olex2_submission_special_instructions 'No special instructions were received'