New synthesis of benzothiazines and benzoisothiazoles containing a sulfoximine functional group.
Harmata, Michael; Rayanil, Kanok-On; Gomes, Maria G.; Zheng, Pinguan; Calkins, Nathan L.; Kim, Soo-Yeun; Fan, Yimin; Bumbu, Valentina; Lee, Dong Reyoul; Wacharasindhu, Sumrit; Hong, Xuechuan; Organic letters 7 (2005) 143–145; doi:10.1021/ol047781j

data_1506487
_publ_section_title
;
 New synthesis of benzothiazines and benzoisothiazoles containing a
 sulfoximine functional group.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              143
_journal_page_last               145
_journal_paper_doi               10.1021/ol047781j
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C8 H7 N O2 S'
_chemical_formula_weight         181.21
_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                 102.1290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2041(7)
_cell_length_b                   8.0433(7)
_cell_length_c                   12.2666(10)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.5
_cell_volume                     791.38(12)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       '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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5489
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.4153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1507
_reflns_number_total             1753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol047781jsi20041028_100238.cif
_cod_data_source_block           MG-III-016c
_cod_original_sg_symbol_H-M      P2~1~/c
_cod_database_code               1506487