Synthesis of a 6-CF<sub>3</sub>-Substituted 2-Amino-dihydro-1,3-thiazine β-Secretase Inhibitor by N, N-Diethylaminosulfur Trifluoride-Mediated Chemoselective Cyclization.
Oguma, Takuya; Anan, Kosuke; Suzuki, Shinji; Hisakawa, Shinya; Takada, Akihiro; Ogawa, Masayoshi; Kusakabe, Ken-Ichi; The Journal of organic chemistry 84 (2019) 4893–4897; doi:10.1021/acs.joc.8b02179

data_4035939
_publ_section_title
;
 Synthesis of a 6-CF<sub>3</sub>-Substituted 2-Amino-dihydro-1,3-thiazine
 \b-Secretase Inhibitor by N, N-Diethylaminosulfur Trifluoride-Mediated
 Chemoselective Cyclization.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4893
_journal_page_last               4897
_journal_paper_doi               10.1021/acs.joc.8b02179
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C20.5 H18 F4 N5 O2 S'
_chemical_formula_sum            'C20.5 H18 F4 N5 O2 S'
_chemical_formula_weight         474.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.610(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   42.959(6)
_cell_length_b                   12.0548(17)
_cell_length_c                   8.2298(16)
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      25.90
_cell_volume                     4261.7(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27545
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.423
_diffrn_reflns_theta_min         6.585
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1952.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.27
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
;
 Flack x determined using 3044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.058(17)
_refine_ls_extinction_coef       0.00041(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     591
_refine_ls_number_reflns         7527
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0712P)^2^+19.6717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                7162
_reflns_number_total             7527
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b02179_si_002.cif
_cod_data_source_block           X3368r2
_cod_database_code               4035939
_shelx_res_checksum              25345
_shelx_hkl_checksum              71670