4-(3-Methylanilino)-<i>N</i>-[<i>N</i>-(1-methylethyl)carbamoyl]pyridinium-3-sulfonamidate (torasemide T–N): a low temperature redetermination
Bartolucci, Gianluca; Bruni, Bruno; Coran, Silvia A.; Di Vaira, Massimo; Acta Crystallographica Section E 65 (2009) o972–o973; doi:10.1107/S1600536809012069

data_2221686
_publ_section_title
;4-(3-Methylanilino)-<i>N</i>-[<i>N</i>-(1-methylethyl)carbamoyl]pyridinium-3-sulfonamidate
 (torasemide T--N): a low temperature redetermination
;
_journal_coeditor_code           HB2935
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o972
_journal_page_last               o973
_journal_paper_doi               10.1107/S1600536809012069
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H20 N4 O3 S'
_chemical_formula_moiety         'C16 H20 N4 O3 S'
_chemical_formula_sum            'C16 H20 N4 O3 S'
_chemical_formula_weight         348.42
_chemical_name_common            torasemide
_chemical_name_systematic
;
4-(3-Methylanilino)-<i>N</i>-[<i>N</i>-(1-methylethyl)carbamoyl]pyridinium-3-
sulfonamidate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.33780(10)
_cell_length_b                   18.90550(10)
_cell_length_c                   16.49580(10)
_cell_measurement_reflns_used    43504
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.21
_cell_measurement_theta_min      4.55
_cell_volume                     3525.99(4)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999),
<i>GAUSSIAN03</i> (Frisch <i>et al.</i>,2004) and
PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare <i>et al.</i>,  1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur PX Ultra CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Oxford Diffraction, Enhance ULTRA assembly'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53231
_diffrn_reflns_theta_full        72.64
_diffrn_reflns_theta_max         72.64
_diffrn_reflns_theta_min         4.56
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSPACK; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.356
_refine_ls_extinction_coef       0.0029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+1.9103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                6840
_reflns_number_total             6941
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb2935.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221686
_cod_database_fobs_code          2221686