Divergent Synthesis of 1,2-Benzo[ e]thiazine and Benzo[ d]thiazole Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation and New Properties of the Adachi Reagent.
Barthelemy, Anne-Laure; Anselmi, Elsa; Le, Thanh-Nghi; Vo-Thanh, Giang; Guillot, Régis; Miqueu, Karinne; Magnier, Emmanuel; The Journal of organic chemistry 84 (2019) 4086–4094; doi:10.1021/acs.joc.9b00079

data_4034238
_publ_section_title
;
 Divergent Synthesis of 1,2-Benzo[ e]thiazine and Benzo[ d]thiazole
 Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation
 and New Properties of the Adachi Reagent.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4086
_journal_page_last               4094
_journal_paper_doi               10.1021/acs.joc.9b00079
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C15 H10 F3 N O S'
_chemical_formula_sum            'C15 H10 F3 N O S'
_chemical_formula_weight         309.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   10.4534(5)
_cell_length_c                   13.9478(6)
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_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      36.35
_cell_measurement_theta_min      2.45
_cell_volume                     1301.63(10)
_computing_cell_refinement       'Bruker SAINT'
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
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_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
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_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45767
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.409
_diffrn_reflns_theta_min         2.450
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.9458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         6320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.6834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5416
_reflns_number_total             6320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00079_si_002.cif
_cod_data_source_block           5e
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034238
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              23847
_shelx_hkl_checksum              12670