Synthesis, investigation of the crystal structure, DFT calculations, and in silico medicinal potential of hydrazono- and aminomethylene substituted pyrazolidine-3,5-diones as potential anticancer scaffolds
El Bakri, Youness; Siddique, Sabir Ali; Mohamed, Shaaban K.; Sarfraz, Muhammad; Abuelizz, Hatem A.; Al-Salahi, Rashad; Mague, Joel T.; Ahmed, Eman A.; New Journal of Chemistry 48 (2024) 12591–12608; doi:10.1039/D4NJ01839G

data_7063291
_publ_section_title
;
 Synthesis, investigation of the crystal structure, DFT calculations, and
 in silico medicinal potential of hydrazono- and aminomethylene
 substituted pyrazolidine-3,5-diones as potential anticancer scaffolds
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12591
_journal_page_last               12608
_journal_paper_doi               10.1039/D4NJ01839G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 N4 O2'
_chemical_formula_sum            'C15 H12 N4 O2'
_chemical_formula_weight         280.29
_chemical_name_systematic
(<i>E</i>)-1-phenyl-4-((pyridin-2-ylamino)methylene)pyrazolidine-3,5-dione
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-04-20 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                102.548(4)
_cell_angle_beta                 94.531(4)
_cell_angle_gamma                95.302(4)
_cell_formula_units_Z            4
_cell_length_a                   6.1973(8)
_cell_length_b                   10.2465(13)
_cell_length_c                   20.461(3)
_cell_measurement_reflns_used    8011
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.208
_cell_measurement_theta_min      2.490
_cell_volume                     1256.2(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2021)'
_computing_data_collection       '<i>APEX4</i> (Bruker, 2021)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2021)'
_computing_molecular_graphics    '<i>DIAMOND</i> (Brandenburg & Putz, 2012)'
_computing_publication_material  '<i>SHELXTL</i> (Bruker, 2021)'
_computing_structure_refinement
'<i>SHELXL-2018/1</i> (Sheldrick, 2015<i>b</i>)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device       'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6336
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.750
_diffrn_reflns_theta_max         28.512
_diffrn_reflns_theta_min         2.049
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>TWINABS</i> (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   0.942
_exptl_transmission_factor_min   0.831
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0856
_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^)+(0.0577P)^2^+4.9083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4661
_reflns_number_total             6336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01839g2.cif
_cod_data_source_block           jtm1543_5
_cod_depositor_comments
'Adding full bibliography for 7063290--7063291.cif.'
_cod_original_cell_volume        1256.3(3)
_cod_database_code               7063291
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.994
_iucr_geom_hbonds_special_details
;
Cg3 and Cg5 are the centroids, respectively, of the C1...C6 and the 
C26...C30/N8 rings.
;
_shelx_res_checksum              75558
_shelx_hkl_checksum              62468