Enantioselective Trapping of an a-Chiral Carbanion of Acyclic Nitrile by a Carbon Electrophile
Michiko Sasaki; Tomo Takegawa; Hidaka Ikemoto; Masatoshi Kawahata; Kentaro Yamaguchi; Kei Takeda; Chem.Commun. 48 (2012) 2897–; doi:10.1039/c2cc00082b

data_7107452
_publ_section_title
;
 Enantioselective Trapping of an a-Chiral Carbanion of Acyclic Nitrile by
 a Carbon Electrophile
;
_journal_name_full               Chem.Commun.
_journal_page_first              2897
_journal_paper_doi               10.1039/c2cc00082b
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H15 Br N2 O4'
_chemical_formula_weight         355.19
_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                 97.455(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4223(14)
_cell_length_b                   6.1123(11)
_cell_length_c                   14.743(3)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.44
_cell_volume                     752.5(2)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       '\f and \w 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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8516
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.748
_exptl_absorpt_correction_T_max  0.8101
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0171P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                2963
_reflns_number_total             3402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc00082b.txt
_cod_data_source_block           TMT-IV-685B
_cod_original_cell_volume        752.6(2)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7107452