One-Pot Synthesis of Benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study of the S-N Type Smiles Rearrangement Mechanism
Yongmei Zhao; Yanmiao Wu; Jiong Jia; Dongju Zhang; Chen Ma; Journal of Organic Chemistry 77 (2012) 8501–8506; doi:10.1021/jo3014287

data_4027559
_publ_section_title
;
 One-Pot Synthesis of Benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study
 of the S-N Type Smiles Rearrangement Mechanism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8501
_journal_page_last               8506
_journal_paper_doi               10.1021/jo3014287
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C10 H8 N2 O S'
_chemical_formula_weight         204.24
_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
_audit_update_record
;
2012-06-08 # Formatted by publCIF
;
_cell_angle_alpha                101.664(2)
_cell_angle_beta                 90.914(2)
_cell_angle_gamma                115.710(2)
_cell_formula_units_Z            4
_cell_length_a                   8.3539(13)
_cell_length_b                   9.2782(14)
_cell_length_c                   13.883(2)
_cell_measurement_temperature    273(2)
_cell_volume                     942.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6606
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0581P)^2^+0.1800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2522
_reflns_number_total             3273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014287_si_001.cif
_cod_data_source_block           p
_cod_database_code               4027559