Catalytic generation of cesium acetylide by CsF: synthesis of 1,3-benzothiazines from cyclic sulfenamides.
Spitz, Cédric; Lohier, Jean-François; Reboul, Vincent; Metzner, Patrick; Organic letters 11 (2009) 2776–2779; doi:10.1021/ol9009333

data_1503978
_publ_section_title
;
 Catalytic generation of cesium acetylide by CsF: synthesis of
 1,3-benzothiazines from cyclic sulfenamides.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2776
_journal_page_last               2779
_journal_paper_doi               10.1021/ol9009333
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 N O4 S3'
_chemical_formula_sum            'C26 H27 N O4 S3'
_chemical_formula_weight         513.67
_chemical_melting_point          423
_chemical_name_systematic
;(R)-[4-Iso-propyl-3-(toluene-4-sulfonyl)-2
-(toluene-4-sulfonylmethylene)-3,4-dihydro-2H-benzo
[e][1,3]thiazine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 95.938(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9756(13)
_cell_length_b                   12.987(2)
_cell_length_c                   11.917(2)
_cell_measurement_reflns_used    9044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.30
_cell_measurement_theta_min      2.57
_cell_volume                     1227.7(3)
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Nonius KAPPA CCD'
_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  0.0777
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            84916
_diffrn_reflns_theta_full        36.62
_diffrn_reflns_theta_max         36.62
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.95623
_exptl_absorpt_correction_T_min  0.89248
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983),  5760 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         11944
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0588P)^2^+0.0485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                11343
_reflns_number_total             11944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9009333_si_003.cif
_cod_data_source_block           16a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '423K' was changed to '423' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1227.8(4)
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1503978