New bis-pyrazolate zinc(ii) complexes as potential anticancer drugs: from structure to anticancer activity
Hasić, Rušid; Serezlić, Majda Kolenović; Caković, Angelina; Bogojeski, Jovana; Nikodijević, Danijela; Milutinović, Milena; Stanojević, Aleksandra; Čavić, Milena; Egorov, Andrei V.; Komolkin, Andrei V.; Kornyakov, Ilya V.; Scheurer, Andreas; Puchta, Ralph; Soldatović, Tanja V.; New Journal of Chemistry 49 (2025) 3617–3632; doi:10.1039/D5NJ00043B

data_7063638
_publ_section_title
;
 New bis-pyrazolate zinc(ii) complexes as potential anticancer drugs: from
 structure to anticancer activity
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3617
_journal_page_last               3632
_journal_paper_doi               10.1039/D5NJ00043B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C26 H22 Cl2 N4 O2 Zn, 0.864(H2 O)'
_chemical_formula_sum            'C26 H23.73 Cl2 N4 O2.87 Zn'
_chemical_formula_weight         574.33
_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   mixed
_audit_creation_date             2024-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-12 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                103.771(3)
_cell_angle_beta                 109.047(3)
_cell_angle_gamma                102.951(3)
_cell_formula_units_Z            2
_cell_length_a                   10.2771(4)
_cell_length_b                   10.7950(3)
_cell_length_c                   13.1138(4)
_cell_measurement_reflns_used    6874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5870
_cell_measurement_theta_min      3.7800
_cell_volume                     1261.45(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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    -83.00  -5.00   0.50    3.00    --  -41.22 121.00  70.00  156
  2  \w    -91.00 -58.00   0.50    3.00    --  -41.22 152.00-129.00   66
  3  \w    -55.00 -24.00   0.50    3.00    --  -41.22 152.00-129.00   62
  4  \w     47.00  73.00   0.50    3.00    --   41.22-121.00 -11.00   52
  5  \w    118.00 143.00   0.50   15.00    --  100.00 121.00  70.00   50
  6  \w     47.00  73.00   0.50   15.00    --  100.00-121.00 -11.00   52
  7  \w     76.00 109.00   0.50   15.00    --  100.00-121.00 -11.00   66
  8  \w     93.00 120.00   0.50   15.00    --  100.00 152.00-129.00   54
  9  \w    -11.00  14.00   0.50    3.00    --  -41.22  32.00 -30.00   50
 10  \w    -42.00 -16.00   0.50    3.00    --  -41.22  32.00 -30.00   52
 11  \w    -39.00   4.00   0.50    3.00    --  -41.22  65.00-120.00   86
 12  \w   -106.00 -32.00   0.50    3.00    --  -41.22 -32.00  90.00  148
 13  \w    -83.00 -21.00   0.50    3.00    --  -41.22 -65.00-180.00  124
 14  \w   -100.00 -30.00   0.50    3.00    --  -41.22 -54.00 -30.00  140
 15  \w     28.00  69.00   0.50    3.00    --   41.22  43.00-150.00   82
 16  \w     40.00  65.00   0.50    3.00    --   41.22-138.00-150.00   50
 17  \w     -1.00  49.00   0.50    3.00    --   41.22 -32.00-180.00  100
 18  \w     39.00  66.00   0.50    3.00    --   41.22  21.00-180.00   54
 19  \w     44.00 104.00   0.50    3.00    --   41.22  54.00  60.00  120
 20  \w     73.00 102.00   0.50    3.00    --   41.22  43.00-150.00   58
 21  \w     64.00  89.00   0.50    3.00    --   41.22-152.00-172.00   50
 22  \w    -14.00  40.00   0.50    3.00    --   41.22 -65.00  30.00  108
 23  \w     74.00 108.00   0.50    3.00    --   41.22  21.00-180.00   68
 24  \w     33.00  59.00   0.50    3.00    --   41.22  32.00  60.00   52
 25  \w     71.00  96.00   0.50    3.00    --   41.22-138.00-150.00   50
 26  \w    115.00 141.00   0.50   15.00    --  100.00  50.00-150.00   52
 27  \w     85.00 110.00   0.50   15.00    --  100.00  50.00-150.00   50
 28  \w    127.00 156.00   0.50   15.00    --  100.00 133.00  30.00   58
 29  \w     48.00  90.00   0.50   15.00    --  100.00 -93.00  60.00   84
 30  \w    101.00 126.00   0.50   15.00    --  100.00 -77.00-180.00   50
 31  \w     41.00  67.00   0.50   15.00    --  100.00 -77.00 150.00   52
 32  \w    120.00 157.00   0.50   15.00    --  100.00  77.00 150.00   74
 33  \w     94.00 120.00   0.50   15.00    --  100.00  33.00-180.00   52
 34  \w     97.00 123.00   0.50   15.00    --  100.00  33.00-120.00   52
 35  \w     37.00  90.00   0.50   15.00    --  100.00-111.00  60.00  106
 36  \w     88.00 155.00   0.50   15.00    --  100.00  93.00-180.00  134
 37  \w     82.00 136.00   0.50   15.00    --  100.00  59.00 -30.00  108
 38  \w     36.00 106.00   0.50   15.00    --  100.00 -93.00 120.00  140
 39  \w     38.00  88.00   0.50   15.00    --  100.00 -50.00 -60.00  100
 40  \w     94.00 141.00   0.50   15.00    --  100.00  17.00-150.00   94
 41  \w     97.00 142.00   0.50   15.00    --  100.00 111.00  90.00   90
 42  \w    101.00 127.00   0.50   15.00    --  100.00 -87.00-150.00   52
 43  \w     32.00 109.00   0.50   15.00    --  100.00 -25.00  60.00  154
 44  \w    106.00 131.00   0.50   15.00    --  100.00  33.00   0.00   50
 45  \w     79.00 116.00   0.50   15.00    --  100.00-133.00 150.00   74
 46  \w     72.00 110.00   0.50   15.00    --  100.00 -50.00   0.00   76
 47  \w     70.00 119.00   0.50   15.00    --  100.00 -59.00 120.00   98
 48  \w     39.00  64.00   0.50   15.00    --  100.00-133.00 150.00   50
 49  \w     78.00 103.00   0.50   15.00    --  100.00-111.00-150.00   50
 50  \w     39.00  65.00   0.50   15.00    --  100.00-111.00-150.00   52
 51  \w    121.00 156.00   0.50   15.00    --  100.00  93.00  30.00   70
 52  \w     37.00  77.00   0.50   15.00    --  100.00-111.00  30.00   80
 53  \w     81.00 108.00   0.50   15.00    --  100.00-111.00  30.00   54
 54  \w     81.00 154.00   0.50   15.00    --  100.00   8.00 120.00  146
 55  \w     62.00 117.00   0.50   15.00    --  100.00-133.00 -60.00  110
 56  \w     96.00 124.00   0.50   15.00    --  100.00 -77.00 150.00   56
 57  \w     94.00 142.00   0.50   15.00    --  100.00  33.00 -60.00   96
 58  \w    110.00 135.00   0.50   15.00    --  100.00  42.00  30.00   50
 59  \w     70.00  96.00   0.50   15.00    --  100.00 -93.00 150.00   52
 60  \w     85.00 110.00   0.50   15.00    --  100.00  93.00  30.00   50
 61  \w     36.00  76.00   0.50   15.00    --  100.00 -93.00 -60.00   80
 62  \w    107.00 132.00   0.50   15.00    --  100.00  33.00 -90.00   50
 63  \w    127.00 157.00   0.50   15.00    --  100.00  33.00 -30.00   60
 64  \w     60.00 108.00   0.50   15.00    --  100.00-111.00   0.00   96
 65  \w     87.00 156.00   0.50   15.00    --  100.00  93.00  60.00  138
 66  \w     85.00 156.00   0.50   15.00    --  100.00  93.00-150.00  142
 67  \w     39.00  65.00   0.50   15.00    --  100.00 -59.00 120.00   52
 68  \w     68.00 101.00   0.50   15.00    --  100.00 -93.00-180.00   66
 69  \w     72.00 113.00   0.50   15.00    --  100.00 -59.00  60.00   82
 70  \w    107.00 133.00   0.50   15.00    --  100.00 178.00 -60.00   52
 71  \w    106.00 131.00   0.50   15.00    --  100.00-152.00-172.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134902000
_diffrn_orient_matrix_UB_12      0.0947900000
_diffrn_orient_matrix_UB_13      0.1139766000
_diffrn_orient_matrix_UB_21      0.1344069000
_diffrn_orient_matrix_UB_22      -0.0336919000
_diffrn_orient_matrix_UB_23      0.0651665000
_diffrn_orient_matrix_UB_31      0.0997432000
_diffrn_orient_matrix_UB_32      0.1186797000
_diffrn_orient_matrix_UB_33      -0.0140622000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13634
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.868
_diffrn_reflns_theta_min         3.789
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       prism
_exptl_crystal_F_000             589
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0551P)^2^+0.7753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4260
_reflns_number_total             4885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00043b2.cif
_cod_data_source_block           4ver0-26329_ii
_cod_depositor_comments
'Adding full bibliography for 7063638--7063639.cif.'
_cod_original_cell_volume        1261.45(8)
_cod_database_code               7063638
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'Zn Cl2 C26 H22 N4 O2'
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.841
_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 O(H,H) groups
2. Restrained distances
 O3-H3A
 0.96 with sigma of 0.02
 O3-H3B
 0.96 with sigma of 0.02
 H3A-H3B
 1.52 with sigma of 0.04
3. Others
 Sof(Cl2B)=1-FVAR(1)
 Sof(Cl2A)=Sof(O3)=Sof(H3A)=Sof(H3B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C1(H1), C2(H2A), C3(H3), C4(H4A), C5(H5), C8(H8), C12(H12),
 C13(H13), C14(H14), C15(H15), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
;
_shelx_res_checksum              42213
_shelx_hkl_checksum              93751
_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 3.886
_oxdiff_exptl_absorpt_empirical_full_min 0.690