Synthesis, structures, DNA/protein binding, molecular docking, anticancer activity and ROS generation of Ni(II), Cu(II) and Zn(II) 5,5-diethylbarbiturate complexes with bis(2-pyridylmethyl)amine and terpyridine
Yilmaz, Veysel T.; Icsel, Ceyda; Suyunova, Feruza; Aygün, Muhittin; Cevatemre, Buse; Ulukaya, Engin; New J. Chem. 41 (2017) 8092–8106; doi:10.1039/C7NJ00887B

data_7056433
_publ_section_title
;
 Synthesis, structures, DNA/protein binding, molecular docking, anticancer
 activity and ROS generation of Ni(II), Cu(II) and Zn(II)
 5,5-diethylbarbiturate complexes with bis(2-pyridylmethyl)amine and
 terpyridine
;
_journal_issue                   16
_journal_name_full               'New J. Chem.'
_journal_page_first              8092
_journal_page_last               8106
_journal_paper_doi               10.1039/C7NJ00887B
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C28 H37 N7 Ni O7, H2 O, 2(C8 H12 N2 O3)'
_chemical_formula_sum            'C44 H63 N11 Ni O14'
_chemical_formula_weight         1028.76
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-22 deposited with the CCDC.
2017-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                101.496(3)
_cell_angle_beta                 96.128(3)
_cell_angle_gamma                101.120(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6756(3)
_cell_length_b                   12.8419(4)
_cell_length_c                   19.8099(7)
_cell_measurement_reflns_used    8121
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.2520
_cell_measurement_theta_min      3.4880
_cell_volume                     2581.45(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -50.00  44.00   1.00   29.43    --   20.07 -57.00 150.00   94
  2  \w     -3.00  89.00   1.00   29.43    --   20.07  57.00 -60.00   92
  3  \w    -53.00  40.00   1.00   29.43    --   20.07 -37.00  30.00   93
  4  \w     50.00  98.00   1.00   29.43    --   20.07 178.00  90.00   48
  5  \w    -33.00   4.00   1.00   29.43    --  -22.02  37.00  60.00   37
  6  \w    -31.00  -5.00   1.00   29.43    --  -22.02  57.00  90.00   26
  7  \w    -25.00  19.00   1.00   29.43    --  -22.02 -99.00  90.00   44
  8  \w    -17.00   8.00   1.00   29.43    --  -22.02 -99.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0267126000
_diffrn_orient_matrix_UB_12      0.0034478000
_diffrn_orient_matrix_UB_13      -0.0336271000
_diffrn_orient_matrix_UB_21      -0.0146861000
_diffrn_orient_matrix_UB_22      0.0505415000
_diffrn_orient_matrix_UB_23      0.0145285000
_diffrn_orient_matrix_UB_31      0.0613411000
_diffrn_orient_matrix_UB_32      0.0277813000
_diffrn_orient_matrix_UB_33      -0.0049331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_min         2.975
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.217
_refine_diff_density_max         1.415
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         10555
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0816P)^2^+2.3890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8408
_reflns_number_total             10555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj00887b2.cif
_cod_data_source_block           CCDC_1511706
_cod_original_cell_volume        2581.44(16)
_cod_database_code               7056433
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C44 H63 N11 Ni O14'
_reflns_odcompleteness_completeness 96.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O14W-H14C
 0.86 with sigma of 0.02
 O14W-H14D
 0.86 with sigma of 0.02
 C31-C32
 1.54 with sigma of 0.04
 C30-C31
 1.54 with sigma of 0.04
 H13A-O13W
 0.86 with sigma of 0.02
 O13W-H13B
 0.86 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C30) = Uanis(C32) = Uanis(C33)
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C16(H16A,H16B), C22(H22A,H22B),
 C24(H24A,H24B), C38(H38A,H38B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B)
4.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C1(H1), C2(H2A), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11),
 C12(H12), N8(H8), N9(H9A), N10(H10A), N11(H11A)
4.d Idealised Me refined as rotating group:
 C13(H13C,H13D,H13E), C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C25(H25A,H25B,
 H25C), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C29(H29A,H29B,H29C), C33(H33A,
 H33B,H33C)
;
_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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.931