Access to [2,1]Benzothiazine <i>S</i>,<i>S</i>-Dioxides from β-Substituted <i>o</i>-Nitrostyrenes and Sulfur.
Nguyen, Thi Mo; Cao, Hoang Anh; Thuong Cao, Thi Thuong; Koyama, Satoki; Mac, Dinh Hung; Nguyen, Thanh Binh; The Journal of organic chemistry 85 (2020) 12058–12066; doi:10.1021/acs.joc.0c00918

data_4038754
_publ_section_title
;
 Access to [2,1]Benzothiazine <i>S</i>,<i>S</i>-Dioxides from
 \b-Substituted <i>o</i>-Nitrostyrenes and Sulfur.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12058
_journal_page_last               12066
_journal_paper_doi               10.1021/acs.joc.0c00918
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 F N2 O2 S'
_chemical_formula_sum            'C13 H9 F N2 O2 S'
_chemical_formula_weight         276.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.2656(16)
_cell_length_b                   33.470(3)
_cell_length_c                   7.2379(6)
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      3.07
_cell_volume                     4667.1(7)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11547
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.067
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0699 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9214.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.6861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                2011
_reflns_number_total             2254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00918_si_002.cif
_cod_data_source_block           pPy
_cod_depositor_comments
'Adding full bibliography for 4038753--4038754.cif.'
_cod_original_cell_volume        4667.2(7)
_cod_database_code               4038754
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              25023
_shelx_hkl_checksum              96027