Synthesis, structural studies, interaction with DNA/HSA and antitumor evaluation of new Cu(ii) complexes containing 2-(1H-imidazol-2-yl)pyridine and amino acids
Cai, Dai-Hong; Chen, Bai-Hua; Liu, Qi-Yan; Le, Xue-Yi; He, Liang; Dalton Transactions  (2022) –; doi:10.1039/D2DT02985E

data_7711519
_publ_section_title
;
 Synthesis, structural studies, interaction with DNA/HSA and antitumor
 evaluation of new Cu(ii) complexes containing
 2-(1H-imidazol-2-yl)pyridine and amino acids
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02985E
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H17 Cu N4 O2, Cl O4, H2 O'
_chemical_formula_sum            'C13 H19 Cl Cu N4 O7'
_chemical_formula_weight         442.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-31 deposited with the CCDC.	2022-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.81416(6)
_cell_length_b                   11.08865(10)
_cell_length_c                   20.48225(14)
_cell_measurement_reflns_used    38479
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      73.3040
_cell_measurement_theta_min      4.3030
_cell_volume                     1774.76(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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      1.00  28.00   1.00    2.00    --   40.00  92.00   6.07   27
  2  \w   -114.00 -10.00   1.00    2.00    --  -40.09 -57.00  30.00  104
  3  \w    -92.00  -2.00   1.00    2.00    --  -40.09 125.00 150.00   90
  4  \w   -122.00   6.00   1.00    2.00    --  -40.09 -19.00 150.00  128
  5  \w   -119.00  -6.00   1.00    2.00    --  -40.09 -77.00 -90.00  113
  6  \w     23.00  97.00   1.00    2.00    --   40.09-125.00  30.00   74
  7  \w      7.00  34.00   1.00    2.00    --   44.00  87.00 -76.21   27
  8  \w     13.00  40.00   1.00    2.00    --   48.00  83.00-161.42   27
  9  \w     12.00  38.00   1.00    2.00    --   48.00  84.00 107.45   26
 10  \w     17.00  45.00   1.00    2.00    --   52.00  82.00  -0.99   28
 11  \w     27.00 138.00   1.00    2.00    --   60.00  76.00  73.90  111
 12  \w     27.00 138.00   1.00    2.00    --   60.00  76.00 119.48  111
 13  \w     31.00 142.00   1.00    2.00    --   64.00  76.00 -90.99  111
 14  \w     30.00 143.00   1.00    2.00    --   64.00  77.00  36.46  113
 15  \w     31.00 142.00   1.00    2.00    --   64.00  75.00 -50.43  111
 16  \w     31.00 142.00   1.00    2.00    --   64.00  76.00-174.87  111
 17  \w     30.00 143.00   1.00    2.00    --   64.00  77.00 149.39  113
 18  \w     39.00 150.00   1.00    2.00    --   72.00  76.00  -7.66  111
 19  \w     39.00 150.00   1.00    2.00    --   72.00  76.00-156.74  111
 20  \w     38.00 151.00   1.00    2.00    --   72.00  77.00-132.44  113
 21  \w     42.00 155.00   1.00    8.00    --   76.00  77.00 -35.48  113
 22  \w     33.00 118.00   1.00    8.00    --  107.60-125.00 150.00   85
 23  \w     77.00 178.00   1.00    8.00    --  107.60  61.00  30.00  101
 24  \w     74.00 178.00   1.00    8.00    --  107.60  77.00   0.00  104
 25  \w     74.00 178.00   1.00    8.00    --  107.60  77.00-180.00  104
 26  \w     29.00 141.00   1.00    8.00    --  107.60 -77.00 -60.00  112
 27  \w     29.00 141.00   1.00    8.00    --  107.60 -77.00 150.00  112
 28  \w     74.00 178.00   1.00    8.00    --  107.60  77.00 -90.00  104
 29  \w     77.00 178.00   1.00    8.00    --  107.60  61.00-180.00  101
 30  \w     74.00 178.00   1.00    8.00    --  107.60  77.00  60.00  104
 31  \w     77.00 178.00   1.00    8.00    --  107.60  61.00  60.00  101
 32  \w     74.00 178.00   1.00    8.00    --  107.60  77.00-150.00  104
 33  \w     77.00 178.00   1.00    8.00    --  107.60  61.00 -90.00  101
 34  \w     33.00 118.00   1.00    8.00    --  107.60-125.00 -60.00   85
 35  \w     74.00 178.00   1.00    8.00    --  107.60  77.00 -60.00  104
 36  \w     74.00 178.00   1.00    8.00    --  107.60  77.00 120.00  104
 37  \w     77.00 178.00   1.00    8.00    --  107.60  61.00  90.00  101
 38  \w     74.00 178.00   1.00    8.00    --  107.60  77.00 150.00  104
 39  \w     74.00 178.00   1.00    8.00    --  107.60  77.00 -30.00  104
 40  \w     74.00 178.00   1.00    8.00    --  107.60  77.00  90.00  104
 41  \w     74.00 178.00   1.00    8.00    --  107.60  77.00  30.00  104
 42  \w     74.00 178.00   1.00    8.00    --  107.60  77.00-120.00  104
 43  \w   -116.00 -14.00   1.00    2.00    --  -40.09 -37.00  60.00  102
 44  \w    -49.00 129.00   1.00    2.00    --   40.09   0.00 -90.00  178
 45  \w    -49.00  62.00   1.00    2.00    --   40.09   0.00 -60.00  111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1171077000
_diffrn_orient_matrix_UB_12      0.0501023000
_diffrn_orient_matrix_UB_13      0.0541119000
_diffrn_orient_matrix_UB_21      -0.1312771000
_diffrn_orient_matrix_UB_22      0.0390872000
_diffrn_orient_matrix_UB_23      -0.0519943000
_diffrn_orient_matrix_UB_31      -0.0889042000
_diffrn_orient_matrix_UB_32      -0.1235098000
_diffrn_orient_matrix_UB_33      0.0055497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            47774
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.449
_diffrn_reflns_theta_min         4.317
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.010(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0196
_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^)+(0.0281P)^2^+0.5092P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0535
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3559
_reflns_number_total             3572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02985e2.cif
_cod_data_source_block           a20102205a0826
_cod_database_code               7711519
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         CHONCu
_chemical_oxdiff_usercomment     Ipy-Val
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3B = O3-H3A
 0.95 with sigma of 0.01
 N3-H3
 0.7 with sigma of 0.01
3. Restrained angles
 H3B-O3-H3A
 fixed at 120 with sigma of 0.02
4. Others
 Fixed Sof: O7A(0.5) O5A(0.5) O4A(0.5) O5B(0.5) O4B(0.5) O7B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.829