An unexpected tautomer: synthesis and crystal structure of <i>N</i>-[6-amino-4-(methyl-sulfan-yl)-1,2-di-hydro-1,3,5-triazin-2-yl-idene]benzenesulfonamide.
Mohamed-Ezzat, Reham A; Elgemeie, Galal H.; Jones, Peter G.; Acta crystallographica. Section E, Crystallographic communications 80 (2024) 120–124; doi:10.1107/S2056989023011076

data_2022998
_publ_section_title
;
 An unexpected tautomer: synthesis and crystal structure of
 <i>N</i>-[6-amino-4-(methyl-sulfan-yl)-1,2-di-hydro-1,3,5-triazin-2-yl-idene]benzenesulfonamide.
;
_journal_coeditor_code           YZ2047
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              120
_journal_page_last               124
_journal_paper_doi               10.1107/S2056989023011076
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C10 H11 N5 O2 S2'
_chemical_formula_moiety         'C10 H11 N5 O2 S2'
_chemical_formula_sum            'C10 H11 N5 O2 S2'
_chemical_formula_weight         297.36
_chemical_name_systematic
<i>N</i>-[6-Amino-4-(methylsulfanyl)-1,2-dihydro-1,3,5-triazin-2-ylidene]benzenesulfonamide
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 92.9914(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.44832(9)
_cell_length_b                   9.03714(14)
_cell_length_c                   26.1141(4)
_cell_measurement_reflns_used    32085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.6610
_cell_measurement_theta_min      3.3680
_cell_volume                     1284.03(4)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
XP, Version 5.1 (Bruker, 1998)
;
_computing_publication_material
;
<i>SHELXL2019/3</i> (Sheldrick, 2015b)
;
_computing_structure_refinement
;
<i>SHELXL2019/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            49520
_diffrn_reflns_theta_full        77.500
_diffrn_reflns_theta_max         80.250
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.9076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                2713
_reflns_number_total             2789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yz2047sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022998.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022998
_cod_database_fobs_code          2022998
_shelx_estimated_absorpt_t_min   0.597
_shelx_estimated_absorpt_t_max   0.927
_shelx_hkl_checksum              49116
_shelx_res_checksum              50207