Biological properties of two enantiomorphic forms of <i>N</i>-(2,6-dimethylphenyl)-4-hydroxy-2,2-dioxo-1<i>H</i>-2λ^6^,1-benzothiazine-3-carboxamide, a structural analogue of piroxicam
Shishkina, Svitlana V.; Ukrainets, Igor V.; Vashchenko, Olga V.; Voloshchuk, Natali I.; Bondarenko, Pavlo S.; Petrushova, Lidiya A.; Sim, Galina; Acta Crystallographica Section C 76 (2020) 69–74; doi:10.1107/S2053229619016450

data_2021943
_publ_section_title
;
 Biological properties of two enantiomorphic forms of
 <i>N</i>-(2,6-dimethylphenyl)-4-hydroxy-2,2-dioxo-1<i>H</i>-2\l^6^,1-benzothiazine-3-carboxamide,
 a structural analogue of piroxicam
;
_journal_coeditor_code           KU3258
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              69
_journal_page_last               74
_journal_paper_doi               10.1107/S2053229619016450
_journal_volume                  76
_journal_year                    2020
_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         344.38
_chemical_name_systematic
;
<i>N</i>-(2,6-Dimethylphenyl)-4-hydroxy-2,2-dioxo-1<i>H</i>-2\l^6^,1-\
benzothiazine-3-carboxamide
;
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.3735(3)
_cell_length_b                   8.3735(3)
_cell_length_c                   20.0299(8)
_cell_measurement_reflns_used    2136
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.824
_cell_measurement_theta_min      4.137
_cell_volume                     1216.25(8)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12184
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.946
_diffrn_reflns_theta_min         2.987
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.212
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3771
_reflns_number_total             4687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ku3258sup1.cif
_cod_data_source_block           1B
_cod_original_cell_volume        1216.25(10)
_cod_database_code               2021943
_cod_database_fobs_code          2021943
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.978
_shelx_hkl_checksum              90894
_shelx_res_checksum              27926