Stereoselectivities and Regioselectivities of (4 + 3) Cycloadditions Between Allenamide-Derived Chiral Oxazolidinone-Stabilized Oxyallyls and Furans: Experiment and Theory
Jennifer E. Antoline; Elizabeth H. Krenske; Andrew G. Lohse; K. N. Houk; Richard P. Hsung; Journal of the American Chemical Society 133 (2011) 14443–14451; doi:10.1021/ja205700p

data_4106754
_publ_section_title
;
 Stereoselectivities and Regioselectivities of (4 + 3) Cycloadditions
 Between Allenamide-Derived Chiral Oxazolidinone-Stabilized Oxyallyls and
 Furans: Experiment and Theory
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14443
_journal_page_last               14451
_journal_paper_doi               10.1021/ja205700p
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 Br N O4'
_chemical_formula_sum            'C16 H14 Br N O4'
_chemical_formula_weight         364.19
_chemical_name_common            07152a
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 111.8480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6952(10)
_cell_length_b                   5.5834(5)
_cell_length_c                   11.8252(11)
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.09
_cell_volume                     716.71(11)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8358
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.886
_exptl_absorpt_correction_T_max  0.6246
_exptl_absorpt_correction_T_min  0.3263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_description       Needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0205P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                2949
_reflns_number_total             3170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205700p_si_004.cif
_cod_data_source_block           07152a
_cod_database_code               4106754