Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via rhodium-catalyzed carbonylation of N-alkylisothiazolidines.
Dong, Chune; Alper, Howard; Organic letters 6 (2004) 3489–3492; doi:10.1021/ol048706b

data_1507026
_publ_section_title
;
 Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via
 rhodium-catalyzed carbonylation of N-alkylisothiazolidines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3489
_journal_page_last               3492
_journal_paper_doi               10.1021/ol048706b
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C12 H15 N O2 S'
_chemical_formula_weight         237.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.236(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.640(3)
_cell_length_b                   5.7416(7)
_cell_length_c                   9.5059(12)
_cell_measurement_reflns_used    961
_cell_measurement_temperature    206(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.83
_cell_volume                     1180.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      206(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7653
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.
_exptl_absorpt_correction_T_min  .9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.6682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                1627
_reflns_number_total             2398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048706bsi20040707_114912.cif
_cod_data_source_block           ha403
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507026