Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels-Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides
Ciby J. Abraham; Daniel H. Paull; Michael T. Scerba; James W. Grebinski; Thomas Lectka; Journal of the American Chemical Society 128 (2006) 13370–13371; doi:10.1021/ja065754d

data_4110977
_publ_section_title
;
 Catalytic, Enantioselective Bifunctional Inverse Electron Demand
 Hetero-Diels-Alder Reactions of Ketene Enolates and o-Benzoquinone
 Diimides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13370
_journal_page_last               13371
_journal_paper_doi               10.1021/ja065754d
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C30 H20 Br F3 N2 O3'
_chemical_formula_weight         593.39
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 97.487(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.1358(7)
_cell_length_b                   14.8678(7)
_cell_length_c                   26.791(7)
_cell_volume                     5187.7(14)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26947
_diffrn_reflns_resolution_max    0.83
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.84
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             2400
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         9369
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0120P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0567
_reflns_number_gt                6380
_reflns_number_total             9369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja065754dsi20060808_123413.cif
_cod_data_source_block           x0242
_cod_database_code               4110977