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_2020530
_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'
_atom_sites_solution_hydrogens   mixed
_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                   5.4764(3)
_cell_length_b                   15.9117(8)
_cell_length_c                   18.3228(10)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.5670
_cell_measurement_theta_min      3.5660
_cell_volume                     1596.63(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)
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_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16369
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         3.392
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' '
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.276
_refine_ls_abs_structure_details
;
Flack x determined using 910 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0350P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                3004
_reflns_number_total             4658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fn3216sup1.cif
_cod_data_source_block           I
_cod_database_code               2020530
_cod_database_fobs_code          2020530
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              24649