Concise Approach to Benzisothiazol-3(2H)-one via Copper-Catalyzed Tandem Reaction of o-Bromobenzamide and Potassium Thiocyanate in Water
Fei Wang; Chao Chen; Geng Deng; Chanjuan Xi; Journal of Organic Chemistry 77 (2012) 4148–4151; doi:10.1021/jo300250x

data_4027156
_publ_contact_author
;
Chanjuan_Xi
Department_of_Chemistry
Tsinghua_University
Beijing_100084
China
;
_publ_section_title
;
 Concise Approach to Benzisothiazol-3(2H)-one via Copper-Catalyzed Tandem
 Reaction of o-Bromobenzamide and Potassium Thiocyanate in Water
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4148
_journal_page_last               4151
_journal_paper_doi               10.1021/jo300250x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C7 H5 N O S'
_chemical_formula_weight         151.18
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.66(3)
_cell_angle_beta                 92.96(3)
_cell_angle_gamma                96.79(3)
_cell_formula_units_Z            4
_cell_length_a                   6.9074(14)
_cell_length_b                   8.0365(16)
_cell_length_c                   12.211(2)
_cell_measurement_reflns_used    2366
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      1.71
_cell_volume                     657.2(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5902
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8228
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.574
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0463
_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^)+(0.1312P)^2^+2.5126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                2747
_reflns_number_total             2992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300250x_si_002.cif
_cod_data_source_block           3a
_cod_database_code               4027156