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_1503977
_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         'C24 H21 N O4 S2'
_chemical_formula_sum            'C24 H21 N O4 S2'
_chemical_formula_weight         451.54
_chemical_melting_point          458
_chemical_name_systematic
; 
(R)-[4-Phenyl-3-(toluene-4-sulfonyl)-3,4-dihydro-benzo[e][1,3]
thiazin-2-ylidene]-acetic acid methyl ester 
;
_space_group_IT_number           19
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_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                   8.0696(2)
_cell_length_b                   11.8879(2)
_cell_length_c                   22.2809(4)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.51
_cell_volume                     2137.42(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48551
_diffrn_reflns_theta_full        29.79
_diffrn_reflns_theta_max         29.79
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 'Flack H D (1983), 2650 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0608P)^2^+0.3124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                5552
_reflns_number_total             6100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9009333_si_002.cif
_cod_data_source_block           6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '458K' was changed to '458' - the
value should be numeric and without a unit
designator.

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

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1503977