Unpredicted formation of copper(ii) complexes containing 2-thiophen-2-yl-1-thiophen-2-ylmethyl-1H-benzoimidazole and their most promising in vitro cytotoxicity in MCF-7 and HeLa cell lines over cisplatin
Naveen, P.; Jain, Ruchi; Kalaivani, P.; Shankar, R.; Dallemer, F.; Prabhakaran, R.; New J. Chem. 41 (2017) 8885–8898; doi:10.1039/C7NJ01273J

data_7056461
_publ_section_title
;
 Unpredicted formation of copper(ii) complexes containing
 2-thiophen-2-yl-1-thiophen-2-ylmethyl-1H-benzoimidazole and their most
 promising in vitro cytotoxicity in MCF-7 and HeLa cell lines over
 cisplatin
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              8885
_journal_page_last               8898
_journal_paper_doi               10.1039/C7NJ01273J
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C16 H12 Cl Cu N5 S2'
_chemical_formula_sum            'C16 H12 Cl Cu N5 S2'
_chemical_formula_weight         437.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.203(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4150(7)
_cell_length_b                   15.5947(12)
_cell_length_c                   11.9725(10)
_cell_measurement_reflns_used    7566
_cell_measurement_temperature    293
_cell_measurement_theta_max      67.9390
_cell_measurement_theta_min      4.6520
_cell_volume                     1944.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;

  1 omega  -50.00   40.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600   38.0000   60.0000 90

  2 omega  -10.00   15.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       36.0000  102.0000   -7.2622 25

  3 omega   10.00   35.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       48.0000   85.0000   83.9332 25

  4 omega   25.00   50.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       60.0000   77.0000   42.4474 25

  5 omega   36.00   74.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -       72.0000   77.0000   12.5076 38

  6 omega   67.00  178.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000   30.0000 111

  7 omega  134.00  177.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  -30.0000 43

  8 omega  111.00  149.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   76.0000   74.7002 38

  9 omega  107.00  178.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000   90.0000 71

 10 omega  109.00  138.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393  178.0000   60.0000 29

 11 omega   76.00  103.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       60.0000   77.0000  141.0512 27

 12 omega   67.00   93.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000   90.0000 26

 13 omega   71.00  101.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   61.0000  120.0000 30

 14 omega   67.00  178.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000   60.0000 111

 15 omega   97.00  161.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  -90.0000 64

 16 omega   67.00  132.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  -30.0000 65

 17 omega   67.00   93.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  -90.0000 26

 18 omega   67.00  173.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  -60.0000 106

 19 omega   69.00  157.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000    0.0000 88

 20 omega   69.00  147.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  120.0000 78

 21 omega   67.00  177.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000  150.0000 110

 22 omega   45.00  135.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393  -77.0000  120.0000 90

 23 omega   56.00  127.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       37.5600 -178.0000   30.0000 71

 24 omega   73.00  112.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393 -111.0000  -90.0000 39

 25 omega   76.00  124.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       37.5600 -178.0000 -150.0000 48

 26 omega   31.00  102.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393 -111.0000   30.0000 71

 27 omega   34.00  109.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393  -94.0000   60.0000 75

 28 omega   20.00   45.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       56.0000   79.0000 -111.3621 25

 29 omega   32.00   58.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   75.0000 -108.2562 26

 30 omega   32.00   72.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   76.0000  -79.6213 40

 31 omega   67.00  175.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000 -150.0000 108

 32 omega   67.00  152.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000 -180.0000 85

 33 omega   67.00  178.00   1.0000   20.0000

omega____ theta____ kappa____ phi______ frames

    -      103.0393   77.0000 -120.0000 111

 34 omega   32.00   80.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   76.0000   74.7002 48

 35 omega   32.00   58.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   77.0000  -14.0435 26

 36 omega   19.00   44.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       56.0000   82.0000  -65.7083 25

 37 omega   19.00   44.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       56.0000   81.0000  -13.2351 25

 38 omega   19.00   44.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       56.0000   82.0000    6.8080 25

 39 omega   -3.00   22.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       40.0000   94.0000 -118.1183 25

 40 omega   19.00   44.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       56.0000   82.0000 -157.0251 25

 41 omega   32.00   63.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       68.0000   77.0000 -166.8933 31

 42 omega  -49.00   38.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600   38.0000 -120.0000 87

 43 omega  -64.00   -6.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600  -38.0000 -180.0000 58

 44 omega  -89.00    8.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600   19.0000 -150.0000 97

 45 omega  -95.00  -68.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600  -38.0000 -180.0000 27

 46 omega -116.00   -5.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -37.5600  -57.0000   90.0000 111

 47 omega   24.00   60.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       60.0000   77.0000  141.0512 36

 48 omega   15.00   42.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       52.0000   82.0000  151.8559 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0453957000
_diffrn_orient_matrix_UB_12      -0.0536700000
_diffrn_orient_matrix_UB_13      0.1014733000
_diffrn_orient_matrix_UB_21      -0.1405731000
_diffrn_orient_matrix_UB_22      -0.0121792000
_diffrn_orient_matrix_UB_23      0.0345232000
_diffrn_orient_matrix_UB_31      -0.0087585000
_diffrn_orient_matrix_UB_32      -0.0819181000
_diffrn_orient_matrix_UB_33      -0.0714266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2045
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.532
_diffrn_reflns_theta_min         4.657
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       prism
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         9751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.1049
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3133
_refine_ls_wR_factor_ref         0.3486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5847
_reflns_number_total             9751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj01273j2.cif
_cod_data_source_block           cun2s2n3
_cod_original_cell_volume        1944.1(2)
_cod_database_code               7056461
_shelx_shelxl_version_number     2016/4
_diffrn_oxdiff_twin_integration_method simultaneous
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.481(6)
 0.299(4) 0.220(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'