One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision, Synthesis, and NMR Shift Dependence of Thiasporine A.
Seitz, Tobias; Fu, Peng; Haut, Franz-Lucas; Adam, Lutz; Habicht, Marija; Lentz, Dieter; MacMillan, John B.; Christmann, Mathias; Organic letters 18 (2016) 3070–3073; doi:10.1021/acs.orglett.6b01166

data_1543779
_publ_section_title
;
 One-Pot Synthesis of 5-Hydroxy-4H-1,3-thiazin-4-ones: Structure Revision,
 Synthesis, and NMR Shift Dependence of Thiasporine A.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3070
_journal_page_last               3073
_journal_paper_doi               10.1021/acs.orglett.6b01166
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.393(4)
_cell_angle_beta                 94.388(4)
_cell_angle_gamma                95.960(4)
_cell_formula_units_Z            4
_cell_length_a                   9.9165(14)
_cell_length_b                   12.3529(18)
_cell_length_c                   13.2009(19)
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.47
_cell_measurement_theta_min      3.76
_cell_volume                     1533.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'D8 Venture, Bruker Photon CMOS Detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41120
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.464
_diffrn_reflns_theta_min         3.762
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5680
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0202P)^2^+3.3495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5368
_reflns_number_total             5593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01166_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1543779
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.465
_shelx_estimated_absorpt_t_max   0.821
_shelx_res_checksum              39820
_shelx_hkl_checksum              92686