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_7248208
_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          'C20 H15 N3 O3 S2'
_chemical_formula_moiety         'C20 H15 N3 O3 S2'
_chemical_formula_sum            'C20 H15 N3 O3 S2'
_chemical_formula_weight         409.47
_chemical_name_systematic
1-((Z)-((4-((E)-N-(thiazol-2(3H)-ylidene)sulfamoyl)phenyl)iminio)methylnaphthalen-2-olate
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 94.032(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8389(8)
_cell_length_b                   13.8151(16)
_cell_length_c                   17.198(2)
_cell_measurement_reflns_used    2548
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.000
_cell_measurement_theta_min      2.374
_cell_volume                     1857.9(4)
_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 7.828
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15333
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.374
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.314
_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            red
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0429P)^2^+0.3132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                2548
_reflns_number_total             4040
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d3ra08727a2.cif
_cod_data_source_block           napsuly_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248208
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              89624
_shelx_hkl_checksum              4861