Benzothiazines in organic synthesis. Stereoselectivity in the intermolecular Michael addition reactions of benzothiazines.
Harmata, Michael; Chen, Yugang; Barnes, Charles L.; Organic letters 9 (2007) 4701–4704; doi:10.1021/ol701863y

data_1505563
_publ_section_title
;
 Benzothiazines in organic synthesis. Stereoselectivity in the
 intermolecular Michael addition reactions of benzothiazines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4701
_journal_page_last               4704
_journal_paper_doi               10.1021/ol701863y
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C25 H32 N2 O4 S'
_chemical_formula_weight         456.59
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.388(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   14.267(3)
_cell_length_b                   7.6190(16)
_cell_length_c                   34.013(7)
_cell_measurement_reflns_used    5813
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.4
_cell_volume                     3696.1(13)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24976
_diffrn_reflns_theta_full        27.20
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 G\"ottingen, Germany).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         14072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+3.0555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                10664
_reflns_number_total             14072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701863y-file005.cif
_cod_data_source_block           YC-II-136
_cod_original_cell_volume        3696.2(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505563