Exo-Selective Diels-Alder Reactions of Vinylazepines. Origin of Divergent Stereoselectivity in Diels-Alder Reactions of Vinylazepines, Vinylpiperideines, and Vinylcycloalkenes
Brant Boren; Jennifer S. Hirschi; Joseph H. Reibenspies; Matthew D. Tallant; Daniel A. Singleton; Gary A. Sulikowski; Journal of Organic Chemistry 68 (2003) 8991–8995; doi:10.1021/jo034462h

data_4022469
_publ_section_title
;
 Exo-Selective Diels-Alder Reactions of Vinylazepines.
 Origin of Divergent Stereoselectivity in Diels-Alder Reactions of
 Vinylazepines, Vinylpiperideines, and Vinylcycloalkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8991
_journal_page_last               8995
_journal_paper_doi               10.1021/jo034462h
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C23 H28 N2 O4'
_chemical_formula_weight         396.47
_chemical_name_common            gs39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 122.856(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.149(16)
_cell_length_b                   7.157(4)
_cell_length_c                   23.908(13)
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     4334(4)
_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      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25884
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+1.1323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                1989
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034462hsi20030925_105519.cif
_cod_data_source_block           F:\structures\gs39\gs39.CIF
_cod_original_sg_symbol_H-M      'C 2/c'
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