Crystal structure of the tetra-ethyl-ammonium salt of the non-steroidal anti-inflammatory drug nimesulide (polymorph II).
Rybczyńska, Małgorzata; Sikorski, Artur; Acta crystallographica. Section E, Crystallographic communications 80 (2024) 314–317; doi:10.1107/S2056989024001300

data_2023035
_publ_section_title
;
 Crystal structure of the tetra-ethyl-ammonium salt of the non-steroidal
 anti-inflammatory drug nimesulide (polymorph II).
;
_journal_coeditor_code           DX2059
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              314
_journal_page_last               317
_journal_paper_doi               10.1107/S2056989024001300
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C8 H20 N +, C13 H11 N2 O5 S -'
_chemical_formula_moiety         'C8 H20 N +, C13 H11 N2 O5 S -'
_chemical_formula_sum            'C21 H31 N3 O5 S'
_chemical_formula_weight         437.55
_chemical_melting_point          388
_chemical_name_systematic
;
Tetraethylammonium <i>N</i>-methanesulfonyl-4-nitro-2-phenoxyanilinide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 91.792(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0276(10)
_cell_length_b                   10.7661(8)
_cell_length_c                   19.635(2)
_cell_measurement_reflns_used    15531
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.002
_cell_measurement_theta_min      3.327
_cell_volume                     2330.0(4)
_computing_cell_refinement
;
CrysAlis RED Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2017/1</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 10.4002
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       \w
_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  0.0727
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15531
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         3.327
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0316P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                2549
_reflns_number_total             4094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2059sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023035.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023035
_cod_database_fobs_code          2023035
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              97052
_shelx_res_checksum              56355