Enantioselective Friedel-Crafts Alkylations of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) Triflate Complexes
David A. Evans; Keith R. Fandrick; Hyun-Ji Song; Journal of the American Chemical Society 127 (2005) 8942–8943; doi:10.1021/ja052433d

data_4111796
_publ_section_title
;
 Enantioselective Friedel-Crafts Alkylations of \a,\b-Unsaturated 2-Acyl
 Imidazoles Catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) Triflate
 Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8942
_journal_page_last               8943
_journal_paper_doi               10.1021/ja052433d
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C16 H20 N2 O'
_chemical_formula_weight         256.34
_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                 115.890(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.059(5)
_cell_length_b                   4.8678(11)
_cell_length_c                   16.912(4)
_cell_measurement_temperature    193(2)
_cell_volume                     1485.6(6)
_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_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4011
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      0
_exptl_crystal_description       rod
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.138
_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   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0532P)^2^+0.2460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                1797
_reflns_number_total             2306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja052433dsi20050414_113315.cif
_cod_data_source_block           jwu91sad
_cod_database_code               4111796