Efficient and Stereoselective Syntheses of Isomerically Pure 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives
Mizojiri, Ryo; Takami, Kazuaki; Ito, Tatsuya; Maeda, Hiroyuki; Yamano, Mitsuhisa; Kawamoto, Tetsuji; Organic Process Research & Development 21 (2017) 1034–; doi:10.1021/acs.oprd.7b00147

data_1546762
_publ_section_title
;
 Efficient and Stereoselective Syntheses of Isomerically Pure
 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives
;
_journal_issue                   7
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1034
_journal_paper_doi               10.1021/acs.oprd.7b00147
_journal_volume                  21
_journal_year                    2017
_chemical_formula_moiety         'C11 H14 N2 O5 S2 '
_chemical_formula_sum            'C11 H14 N2 O5 S2'
_chemical_formula_weight         318.36
_chemical_name_systematic
;
cis-2-Nitro-N-(1-oxidotetrahydro-2H-thiopyran-4-yl)benzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.411(3)
_cell_length_b                   14.986(4)
_cell_length_c                   19.855(6)
_cell_measurement_reflns_used    25992
_cell_measurement_temperature    100.2
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.0
_cell_volume                     2800.2(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.00
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  ' graphite '
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.4649
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            28975
_diffrn_reflns_theta_max         68.12
_exptl_absorpt_coefficient_mu    3.659
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     181
_refine_ls_number_reflns         438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.177
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.0010P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                438
_reflns_number_total             2468
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            op7b00147_si_003.cif
_cod_data_source_block           compound_4a
_cod_original_cell_volume        2800(5)
_cod_original_formula_sum        'C11 H14 N2 O5 S2 '
_cod_database_code               1546762