Expedient Synthesis of Furo[2,3-d][1,3]thiazinamines and Pyrano[2,3-d][1,3]thiazinamines from Enones and Thiourea.
Wu, Yong-Jin; Guernon, Jason; Park, Hyunsoo; Thompson, Lorin A.; The Journal of organic chemistry 81 (2016) 3386–3390; doi:10.1021/acs.joc.5b02705

data_4036550
_publ_section_title
;
 Expedient Synthesis of Furo[2,3-d][1,3]thiazinamines and
 Pyrano[2,3-d][1,3]thiazinamines from Enones and Thiourea.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3386
_journal_page_last               3390
_journal_paper_doi               10.1021/acs.joc.5b02705
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H20 F N3 O5 S'
_chemical_formula_sum            'C17 H20 F N3 O5 S'
_chemical_formula_weight         397.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8864(2)
_cell_length_b                   8.3268(3)
_cell_length_c                   38.2524(12)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.88
_cell_measurement_theta_min      6.95
_cell_volume                     1874.94(11)
_computing_cell_refinement       'Bruker APEX 2 (2012)'
_computing_data_collection       'Bruker APEX 2 (2012)'
_computing_data_reduction        'Bruker APEX 2 (2012)'
_computing_molecular_graphics    'Mercury 3.0.1 (2011)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  platform
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15618
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         2.310
_diffrn_source                   'Microfocusing source'
_diffrn_source_type              'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.6440
_exptl_absorpt_correction_T_min  0.5951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method EtOAc-hexanes
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+0.3621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0679
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3232
_reflns_number_total             3258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02705_si_002.cif
_cod_data_source_block           bmt-089511_peak2
_cod_database_code               4036550
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.595
_shelx_estimated_absorpt_t_max   0.644
_shelx_res_checksum              68909
_shelx_hkl_checksum              23219