Fluoride Ion and Phosphines as Nucleophilic Catalysts: Synthesis of 1,4-Benzothiazepines from Cyclic Sulfenamides
Cédric Spitz; Jean-François Lohier; Jana Sopkova-de Oliveira Santos; Vincent Reboul; Patrick Metzner; Journal of Organic Chemistry 74 (2009) 3936–3939; doi:10.1021/jo900449a

data_4024547
_publ_contact_author_address
;     Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507
      ENSICAEN - Universit\'e de Caen
      14050 Caen
      France
;
_publ_contact_author_email       vincent.reboul@ensicaen.fr
_publ_contact_author_fax         '332 31 45 28 65'
_publ_contact_author_name        'Reboul, Vincent'
_publ_contact_author_phone       '332 31 45 28 84'
_publ_section_title
;
Fluoride Ion and Phosphines as Nucleophilic Catalysts: Synthesis of
1,4-Benzothiazepines from Cyclic Sulfenamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3936
_journal_page_last               3939
_journal_paper_doi               10.1021/jo900449a
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O2 S2'
_chemical_formula_sum            'C17 H19 N O2 S2'
_chemical_formula_weight         333.45
_chemical_name_systematic
;(R)-2,3-Dihydro-3-iso-propyl-2-(toluene-4-sulfonyl)
benzo[d]isothiazole  
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5861(3)
_cell_length_b                   11.4848(4)
_cell_length_c                   16.5942(5)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.59
_cell_measurement_theta_min      2.16
_cell_volume                     1636.35(9)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software'
_computing_data_reduction        'APEX2 software'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius ApexII KAPPA CCD'
_diffrn_measurement_method       '\w scans and \f 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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            56881
_diffrn_reflns_theta_full        33.59
_diffrn_reflns_theta_max         33.59
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), 2802 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         6425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0212
_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^)+(0.0417P)^2^+0.1124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                6286
_reflns_number_total             6425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900449a_si_002.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4024547