Asymmetric Friedel-Crafts Reaction of Indoles with Imines by an Organic Catalyst
Yong-Qiang Wang; Jun Song; Ran Hong; Hongming Li; Li Deng; Journal of the American Chemical Society 128 (2006) 8156–8157; doi:10.1021/ja062700v

data_4110674
_publ_section_title
;
 Asymmetric Friedel-Crafts Reaction of Indoles with Imines by an Organic
 Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8156
_journal_page_last               8157
_journal_paper_doi               10.1021/ja062700v
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C23 H19 F3 N2 O2 S'
_chemical_formula_weight         444.46
_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                 105.690(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.346(4)
_cell_length_b                   8.6134(16)
_cell_length_c                   27.741(6)
_cell_measurement_reflns_used    877
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.82
_cell_volume                     4220.3(15)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13935
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         0.76
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         8981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1531
_reflns_number_gt                6204
_reflns_number_total             8981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062700vrom20060425_025056.cif
_cod_data_source_block           ld11t
_cod_original_cell_volume        4220.4(14)
_cod_database_code               4110674