Highly Enantioselective [2+2]-Cycloaddition Reactions Catalyzed by a Chiral Aluminum Bromide Complex
Eda Canales; E. J. Corey; Journal of the American Chemical Society 129 (2007) 12686–12687; doi:10.1021/ja0765262

data_4110088
_publ_section_title
;
 Highly Enantioselective [2+2]-Cycloaddition Reactions Catalyzed by a
 Chiral Aluminum Bromide Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12686
_journal_page_last               12687
_journal_paper_doi               10.1021/ja0765262
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H14 Br N O2'
_chemical_formula_weight         296.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1605(13)
_cell_length_b                   7.972(2)
_cell_length_c                   29.258(7)
_cell_measurement_reflns_used    1021
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.65
_cell_volume                     1203.7(5)
_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      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_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  0.1435
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9556
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.404
_exptl_absorpt_correction_T_max  0.7724
_exptl_absorpt_correction_T_min  0.2809
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       bar
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.561
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0328P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                1988
_reflns_number_total             2117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0765262si20070829_113901.cif
_cod_data_source_block           ejc137
_cod_original_cell_volume        1203.8(5)
_cod_database_code               4110088