One-pot synthesis of benzothiazolines and napthathiazolines via cascade ortho-lithiation, cyclisation and elimination of N-arylsulfonyl lactams.
Harling, John D.; Steel, Patrick G.; Woods, Tom M.; Yufit, Dmitry S.; Organic & biomolecular chemistry 5 (2007) 3472–3476; doi:10.1039/b708967h

data_7151159
_publ_section_title
;
 One-pot synthesis of benzothiazolines and napthathiazolines via
 cascade ortho-lithiation, cyclisation and elimination of
 N-arylsulfonyl lactams.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3472
_journal_page_last               3476
_journal_paper_doi               10.1039/b708967h
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C12 H12 Br N O2 S'
_chemical_formula_sum            'C12 H12 Br N O2 S'
_chemical_formula_weight         314.20
_chemical_melting_point          199.5(5)
_chemical_name_systematic
;
3-bromo-4,5,6,7-tetrahydroazepinobenzisothiazole-1,1-dioxide
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5525(3)
_cell_length_b                   10.1393(2)
_cell_length_c                   14.0826(3)
_cell_measurement_reflns_used    5877
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.35
_cell_volume                     2363.49(8)
_computing_cell_refinement       'SAINT Ver. 6.45 (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.630 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.45'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30330
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.643
_exptl_absorpt_correction_T_max  0.7593
_exptl_absorpt_correction_T_min  0.3099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0260P)^2^+2.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                3023
_reflns_number_total             3450
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b708967h.txt
_cod_data_source_block           s020
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 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:

'_chemical_melting_point' value '199-200' was changed to '199.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2n 2ab '
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               7151159