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_4024548
_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_formula_sum            'C20 H17 N O2 S2'
_chemical_formula_weight         367.47
_space_group_IT_number           19
_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                   10.8068(3)
_cell_length_b                   11.1270(3)
_cell_length_c                   14.8373(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1784.14(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62605
_diffrn_reflns_theta_full        36.24
_diffrn_reflns_theta_max         36.24
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.311
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         8575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0463P)^2^+0.1128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                7920
_reflns_number_total             8575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900449a_si_003.cif
_cod_data_source_block           spitz10f_0m
_cod_database_code               4024548