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_7063290
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H11 Br N4 O2'
_chemical_formula_sum            'C15 H11 Br N4 O2'
_chemical_formula_weight         359.19
_chemical_name_systematic
(<i>Z</i>)-4-(2-(4-bromophenyl)hydrazineylidene)-1-phenylpyrazolidine-3,5-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 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                90
_cell_angle_beta                 94.755(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.1068(17)
_cell_length_b                   5.7977(6)
_cell_length_c                   7.4341(8)
_cell_measurement_reflns_used    9684
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      32.0623
_cell_measurement_theta_min      2.5379
_cell_volume                     691.82(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28969
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        32.100
_diffrn_reflns_theta_max         32.131
_diffrn_reflns_theta_min         2.538
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '<i>SADABS</i> (Krause <i>et al.</i>, 2015)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.616
_exptl_transmission_factor_min   0.317
_refine_diff_density_max         1.215
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.046(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4805
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0640P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4278
_reflns_number_total             4805
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {400f9b57-2044-4ccd-9b02-0a24087acf1b}
_cod_data_source_file            d4nj01839g2.cif
_cod_data_source_block           skm361a_a
_cod_depositor_comments
'Adding full bibliography for 7063290--7063291.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7063290
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.447
_shelx_estimated_absorpt_t_max   0.916
_iucr_geom_hbonds_special_details
;
Cg2 and Cg3 are , respectively, the centroids of the C1...C6 and 
C10...C15 benzene rings.
;
_shelx_res_checksum              29416
_shelx_hkl_checksum              71175
_publcif_funding_html
;
;