Two pseudo-enantiomeric forms of <i>N</i>-benzyl-4-hydroxy-1-methyl-2,2-dioxo-1<i>H</i>-2λ^6^,1-benzothiazine-3-carboxamide and their analgesic properties
Ukrainets, Igor V.; Shishkina, Svitlana V.; Baumer, Vyacheslav N.; Gorokhova, Olga V.; Petrushova, Lidiya A.; Sim, Galina; Acta Crystallographica Section C 72 (2016) 411–415; doi:10.1107/S2053229616005453

data_2020531
_publ_section_title
;
 Two pseudo-enantiomeric forms of
 <i>N</i>-benzyl-4-hydroxy-1-methyl-2,2-dioxo-1<i>H</i>-2\l^6^,1-benzothiazine-3-carboxamide
 and their analgesic properties
;
_journal_coeditor_code           FN3216
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              411
_journal_page_last               415
_journal_paper_doi               10.1107/S2053229616005453
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C17 H16 N2 O4 S'
_chemical_formula_moiety         'C17 H16 N2 O4 S'
_chemical_formula_sum            'C17 H16 N2 O4 S'
_chemical_formula_weight         344.39
_chemical_name_systematic
<i>N</i>-Benzyl-4-hydroxy-1-methyl-2,2-dioxo-1<i>H</i>-2\l6,1-benzothiazine-3-carboxamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4469(3)
_cell_length_b                   15.8455(10)
_cell_length_c                   18.2412(9)
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.2290
_cell_measurement_theta_min      3.4050
_cell_volume                     1574.38(15)
_computing_cell_refinement
;
CrysAlis RED (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis CCD (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis RED (Agilent, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
olex2.refine (Bourhis <i>et al.</i>,  2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16325
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4529
_exptl_crystal_description       stick
_exptl_crystal_F_000             720.8596
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.2013
_refine_diff_density_min         -0.2148
_refine_ls_abs_structure_details
;
Flack x determined using 839 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.16(9)
_refine_ls_goodness_of_fit_ref   0.8353
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8353
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                2296
_reflns_number_total             2777
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            fn3216sup1.cif
_cod_data_source_block           II
_cod_database_code               2020531
_cod_database_fobs_code          2020531
_shelx_res_checksum              61122