Synthesis of dimeric 1,2-benzothiazine 1,1-dioxide scaffolds: molecular structures, Hirshfeld surface analysis, DFT and enzyme inhibition studies
Fatima, Muqudis; Siddiqui, Waseeq Ahmad; Choudhary, Muhammad Iqbal; Ashraf, Adnan; Niaz, Shanawer; Raza, Muhammad Asam; Alam, Seikh Mafiz; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Dahlous, Kholood Ahmed; RSC Advances 14 (2024) 16935–16944; doi:10.1039/D4RA02009J

data_7248725
_publ_section_title
;
 Synthesis of dimeric 1,2-benzothiazine 1,1-dioxide scaffolds: molecular
 structures, Hirshfeld surface analysis, DFT and enzyme inhibition studies
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              16935
_journal_page_last               16944
_journal_paper_doi               10.1039/D4RA02009J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_iupac          'C22 H20 N2 O10 S2'
_chemical_formula_moiety         'C22 H20 N2 O10 S2'
_chemical_formula_sum            'C22 H20 N2 O10 S2'
_chemical_formula_weight         536.52
_chemical_name_systematic
'Methyl 4-((3-(methoxycarbonyl)-2-methyl-1,1-dioxido-4-oxo-3,4-dihydro-2H-benzo[e][1,2]thiazin-3-yl)oxy)-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxylate1,1-dioxide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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
;
2023-09-15 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.971(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1249(17)
_cell_length_b                   12.094(2)
_cell_length_c                   10.995(2)
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.034
_cell_measurement_theta_min      2.583
_cell_volume                     1147.5(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, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.60
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7722
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.034
_diffrn_reflns_theta_min         2.583
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0386P)^2^+0.0131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                3805
_reflns_number_total             5003
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d4ra02009j2.cif
_cod_data_source_block           mqf53uos_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7248725
_shelx_shelxl_version_number     2019/2
_shelx_res_checksum              21977