Two enantiomerically pure cyclic arenesulfonamide hydrochloride salts
Kiefer, Lionel; Dauban, Philippe; Dodd, Robert H.; Retailleau, Pascal; Acta Crystallographica Section C 65 (2009) o46–o50; doi:10.1107/S010827010804287X

data_2016960
_publ_section_title
;
 Two enantiomerically pure cyclic arenesulfonamide hydrochloride salts
;
_journal_coeditor_code           GD3257
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o46
_journal_page_last               o50
_journal_paper_doi               10.1107/S010827010804287X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H21 N2 O2 S +, Cl -'
_chemical_formula_moiety         'C20 H21 N2 O2 S +, Cl -'
_chemical_formula_sum            'C20 H21 Cl N2 O2 S'
_chemical_formula_weight         388.90
_chemical_name_systematic
;<i>N</i>-[(1<i>R</i>)-1-(1-naphthyl)ethyl]-3,4-dihydro-2<i>H</i>-1,2-benzothiazin-4-aminium
 1,1-dioxide chloride
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.90(2)
_cell_angle_beta                 106.62(3)
_cell_angle_gamma                96.94(2)
_cell_formula_units_Z            2
_cell_length_a                   8.230(2)
_cell_length_b                   10.927(2)
_cell_length_c                   11.633(3)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      1.00
_cell_volume                     952.7(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_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  0.025
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7330
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Scalepack; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details 'Flack (1983), 2356 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         5771
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0361P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                4862
_reflns_number_total             5771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gd3257.cif
_cod_data_source_block           I
_cod_database_code               2016960
_cod_database_fobs_code          2016960