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_1543407
_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 H17 Br N2 O4 S'
_chemical_formula_weight         401.27
_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_space_group_name_Hall  '-P 2yn'
_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                 97.322(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0538(6)
_cell_length_b                   6.7288(3)
_cell_length_c                   16.4896(7)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.49
_cell_volume                     1656.68(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45884
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.491
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         2.241
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0403P)^2^+5.4195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3492
_reflns_number_total             3812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01166_si_002.cif
_cod_data_source_block           304TS_a
_cod_depositor_comments
'Adding full bibliography for 1543407--1543408.cif.'
_cod_database_code               1543407
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.435
_shelx_estimated_absorpt_t_max   0.837
_shelx_res_checksum              91596
_shelx_hkl_checksum              34923