Highly active copper(i) complexes of aroylthiourea ligands against cancer cells – synthetic and biological studies
Jeyalakshmi, Kumaramangalam; Haribabu, Jebiti; Balachandran, Chandrasekar; Narmatha, Eswaramoorthi; Bhuvanesh, Nattamai S. P.; Aoki, Shin; Awale, Suresh; Karvembu, Ramasamy; New Journal of Chemistry 43 (2019) 3188–; doi:10.1039/C8NJ04246B

data_7058103
_publ_section_title
;
 Highly active copper(i) complexes of aroylthiourea ligands against cancer
 cells -- synthetic and biological studies
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3188
_journal_paper_doi               10.1039/C8NJ04246B
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C36 H30 Br0.72 Cl0.29 Cu N6 O6 S3'
_chemical_formula_sum            'C36 H30 Br0.72 Cl0.29 Cu N6 O6 S3'
_chemical_formula_weight         870.19
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2018-06-21 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.087(2)
_cell_angle_beta                 97.217(2)
_cell_angle_gamma                111.760(2)
_cell_formula_units_Z            2
_cell_length_a                   9.942(2)
_cell_length_b                   10.631(2)
_cell_length_c                   19.827(4)
_cell_measurement_reflns_used    7371
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.401
_cell_measurement_theta_min      2.255
_cell_volume                     1874.1(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      110.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21812
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.067
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.592
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0858 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8050.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             886
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         8455
_refine_ls_number_restraints     768
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0349P)^2^+1.7365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6338
_reflns_number_total             8455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj04246b2.cif
_cod_data_source_block           kjcuftu
_cod_depositor_comments
'Adding full bibliography for 7058102--7058103.cif.'
_cod_original_cell_volume        1874.1(7)
_cod_database_code               7058103
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.617
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Shared sites
{C15, C15A}
3. Restrained distances
 C15A-C14 \\sim C15-C14
 with sigma of 0.005
 N4-C19 \\sim N4-C19A
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
N6 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim N6A \\sim
C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
O4 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim O4A \\sim C15A \\sim C16A
\\sim C17A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C19A \\sim C20A
\\sim C21A \\sim C22A \\sim C23A \\sim C24A: within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(C15) = Uanis(C15A)
Uanis(Br1) = Uanis(Cl1)
5. Rigid body (RIGU) restrains
 N6, C31, C32, C33, C34, C35, C36, N6A, C31A, C32A, C33A, C34A, C35A, C36A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O4, C15, C16, C17, C18, O4A, C15A, C16A, C17A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C19, C20, C21, C22, C23, C24, C19A, C20A, C21A, C22A, C23A, C24A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Same fragment restrains
{O4, C15, C16, C17, C18} sigma for 1-2: 0.005, 1-3: 0.04
as
{O4A, C15A, C16A, C17A, C18A}
{N6, C31, C32, C33, C34, C35, C36} sigma for 1-2: 0.02, 1-3: 0.04
as
{N6A, C31A, C32A, C33A, C34A, C35A, C36A}
7. Others
 Sof(N6A)=Sof(H6AA)=Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=
 Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=1-FVAR(1)
 Sof(N6)=Sof(H6A)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=
 Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=Sof(H36)=FVAR(1)
 Sof(O4A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=
 Sof(H18A)=1-FVAR(2)
 Sof(O4)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=FVAR(2)
 Sof(H4)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(3)
 Sof(H4A)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(3)
 Fixed Sof: Br1(0.72) Cl1(0.29)
8.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4A), N4(H4), N5(H5), C4(H4B), C5(H5A), C6(H6),
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C16A(H16A), C17A(H17A), C18A(H18A), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C24A(H24A), C28(H28),
  C29(H29), C30(H30), N6(H6A), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
  N6A(H6AA), C32A(H32A), C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A)
8.b Fitted hexagon refined as free rotating group:
 C19(C20,C21,C22,C23,C24), C19A(C20A,C21A,C22A,C23A,C24A)
;
_shelx_res_checksum              21475
_shelx_hkl_checksum              2140
_olex2_submission_special_instructions 'No special instructions were received'