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_4110090
_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_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C13 H21 N3 S'
_chemical_formula_moiety         'C13 H21 N3 S'
_chemical_formula_structural     'C13 H21 N3 S'
_chemical_formula_sum            'C13 H21 N3 S'
_chemical_formula_weight         251.39
_chemical_name_systematic
; 
(4aS)-(E)-2-(4a-methyl-3,4,4a,5,6,7,8,9-octahydrobenzo[7]annulen-2-
ylidene)hydrazinecarbothioamide
;
_space_group_IT_number           4
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_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
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_cell_angle_beta                 90.616(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3944(2)
_cell_length_b                   8.0872(1)
_cell_length_c                   10.3921(2)
_cell_measurement_reflns_used    8999
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.43
_cell_volume                     705.45(2)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_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 APEX II CCD'
_diffrn_measurement_method       '\w scans, 3202 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20332
_diffrn_reflns_theta_full        27.76
_diffrn_reflns_theta_max         27.76
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       Plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.0974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3100
_reflns_number_total             3340
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja0765262si20070829_113952.cif
_cod_data_source_block           ejc142
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4110090