Synthesis of 3-Substituted-3,4-dihydro-2H-1,3-benzothiazin- 2-ones via a Highly Regioselective Palladium-Catalyzed Carbonylation of 2-Substituted-2,3-dihydro-1,2-benzisothiazoles
Gwenaella Rescourio; Howard Alper; Journal of Organic Chemistry 73 (2008) 1612–1615; doi:10.1021/jo702146n

data_4023259
_publ_section_title
;
 Synthesis of 3-Substituted-3,4-dihydro-2H-1,3-benzothiazin- 2-ones
 via a Highly Regioselective Palladium-Catalyzed Carbonylation of
 2-Substituted-2,3-dihydro-1,2-benzisothiazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1612
_journal_page_last               1615
_journal_paper_doi               10.1021/jo702146n
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C15 H13 N O S'
_chemical_formula_weight         255.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.542(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.222(3)
_cell_length_b                   6.1059(15)
_cell_length_c                   18.885(5)
_cell_measurement_reflns_used    353
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      21.92
_cell_measurement_theta_min      2.34
_cell_volume                     1267.9(5)
_computing_cell_refinement       'SMART, Bruker (2000)'
_computing_data_collection       'SMART, Bruker (2000)'
_computing_data_reduction        'XPREP, Bruker (2000)'
_computing_molecular_graphics    'SHELXTL, Bruker (2000)'
_computing_publication_material  'SHELXTL, Bruker (2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5455
_diffrn_reflns_theta_full        21.99
_diffrn_reflns_theta_max         21.99
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                995
_reflns_number_total             1499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702146n-File003.cif
_cod_data_source_block           ha19
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023259