Synthesis, structure and sulfonamide–sulfonimide tautomerism of sulfonamide–1,2,4-triazine derivatives
Branowska, Danuta; Wysocki, Waldemar; Wolińska, Ewa; Koc, Karolina; Stańska, Katarzyna; Mirosław, Barbara; Karczmarzyk, Zbigniew; Acta Crystallographica Section C Structural Chemistry 78 (2022) –; doi:10.1107/S2053229622007781

data_2022651
_publ_section_title
;
 Synthesis, structure and sulfonamide--sulfonimide tautomerism of
 sulfonamide--1,2,4-triazine derivatives
;
_journal_coeditor_code           EF3031
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229622007781
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C24 H20 N4 O4 S'
_chemical_formula_moiety         'C24 H20 N4 O4 S'
_chemical_formula_sum            'C24 H20 N4 O4 S'
_chemical_formula_weight         460.50
_chemical_name_systematic
;
Methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamoyl]methyl}benzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.919(2)
_cell_length_b                   8.0871(16)
_cell_length_c                   24.875(5)
_cell_measurement_reflns_used    3956
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.5870
_cell_measurement_theta_min      4.6140
_cell_volume                     2181.8(7)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent SuperNova Single Source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8470
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.455
_diffrn_reflns_theta_min         3.578
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.637
_refine_diff_density_min         -1.157
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1280P)^2^+2.0409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2526
_reflns_number_gt                3507
_reflns_number_total             4438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ef3031sup1.cif
_cod_data_source_block           3b
_cod_original_cell_volume        2181.9(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022651
_shelx_hkl_checksum              10419
_shelx_res_checksum              94413
_cod_database_fobs_code 2022651