A synthetic approach towards drug modification: 2-hydroxy-1-naphthaldehyde based imine-zwitterion preparation, single-crystal study, Hirshfeld surface analysis, and computational investigation
Malik, Abida Naseem; Ali, Akbar; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Alam, Mohammad Mahtab; Mostafa, Mohamed S.; Kuznetsov, Aleksey; RSC Advances 14 (2024) 6476–6493; doi:10.1039/D3RA08727A

data_7248209
_publ_section_title
;
 A synthetic approach towards drug modification:
 2-hydroxy-1-naphthaldehyde based imine-zwitterion preparation,
 single-crystal study, Hirshfeld surface analysis, and computational
 investigation
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              6476
_journal_page_last               6493
_journal_paper_doi               10.1039/D3RA08727A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_iupac          'C23 H19 Cl N4 O'
_chemical_formula_moiety         'C23 H19 Cl N4 O'
_chemical_formula_sum            'C23 H19 Cl N4 O'
_chemical_formula_weight         402.87
_chemical_name_systematic
;
(E)-1-(((4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl)iminio)methyl)
naphthalen-2-olate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2024-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                88.308(8)
_cell_angle_beta                 89.195(8)
_cell_angle_gamma                82.611(9)
_cell_formula_units_Z            2
_cell_length_a                   4.5436(6)
_cell_length_b                   12.5255(16)
_cell_length_c                   17.673(2)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      1.640
_cell_volume                     996.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.710
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            4351
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_min         1.640
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0763
_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^)+(0.0757P)^2^+0.7915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.2358
_reflns_number_gt                2397
_reflns_number_total             4351
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d3ra08727a2.cif
_cod_data_source_block           pymtvan_twnew
_cod_database_code               7248209
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              37675
_shelx_hkl_checksum              40181