Chiral Bicycle Imidazole Nucleophilic Catalysts: Rational Design, Facile Synthesis, and Successful Application in Asymmetric Steglich Rearrangement
Zhenfeng Zhang; Fang Xie; Jia Jia; Wanbin Zhang; Journal of the American Chemical Society 132 (2010) 15939–15941; doi:10.1021/ja109069k

data_4103529
_publ_section_title
;
 Chiral Bicycle Imidazole Nucleophilic Catalysts: Rational Design, Facile
 Synthesis, and Successful Application in Asymmetric Steglich
 Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15939
_journal_page_last               15941
_journal_paper_doi               10.1021/ja109069k
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C6 H8 N2 O'
_chemical_formula_weight         124.14
_space_group_IT_number           4
_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                 91.179(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.6610(15)
_cell_length_b                   10.065(2)
_cell_length_c                   16.229(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1251.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.902
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4093
_diffrn_reflns_theta_full        60.46
_diffrn_reflns_theta_max         60.46
_diffrn_reflns_theta_min         5.17
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.9414
_exptl_absorpt_correction_T_min  0.8940
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.209
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0820P)^2^+0.0094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                3877
_reflns_number_total             4093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109069k_si_001.cif
_cod_data_source_block           00708a
_cod_original_cell_volume        1251.2(4)
_cod_database_code               4103529