Keto–enol tautomerism in crystals of 3-[hydroxy(phenyl)methyl]-2,5,7-trimethyl-2,3-dihydropyrido[3,2-<i>e</i>][1,2]thiazin-4-one 1,1-dioxide and 3-(1-hydroxyethylidene)-2,5,7-trimethyl-2,3-dihydropyrido[3,2-<i>e</i>][1,2]thiazin-4-one 1,1-dioxide
Karczmarzyk, Zbigniew; Acta Crystallographica Section C 64 (2008) o590–o594; doi:10.1107/S010827010803206X

data_2016842
_publ_section_title
;Keto--enol tautomerism in crystals of
 3-[hydroxy(phenyl)methyl]-2,5,7-trimethyl-2,3-dihydropyrido[3,2-<i>e</i>][1,2]thiazin-4-one
 1,1-dioxide and
 3-(1-hydroxyethylidene)-2,5,7-trimethyl-2,3-dihydropyrido[3,2-<i>e</i>][1,2]thiazin-4-one
 1,1-dioxide
;
_journal_coeditor_code           SF3092
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o590
_journal_page_last               o594
_journal_paper_doi               10.1107/S010827010803206X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H14 N2 O4 S'
_chemical_formula_moiety         'C12 H14 N2 O4 S'
_chemical_formula_sum            'C12 H14 N2 O4 S'
_chemical_formula_weight         282.31
_chemical_melting_point_gt       430
_chemical_melting_point_lt       431
_chemical_name_systematic
;
3-(1-hydroxyethylidene)-2,5,7-trimethyl-2,3-
dihydropyrido[3,2-<i>e</i>][1,2]thiazin-4-one 1,1-dioxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.817(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9023(2)
_cell_length_b                   14.3095(3)
_cell_length_c                   10.6151(2)
_cell_measurement_reflns_used    655
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      2.44
_cell_volume                     1301.03(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18200
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9353
_exptl_absorpt_correction_T_min  0.8459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.3499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2924
_reflns_number_total             3097
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3092.cif
_cod_data_source_block           II
_cod_database_code               2016842
_cod_database_fobs_code          2016842