Stereoselective Synthesis of Both Enantiomers of N-Aryl Indoles with Axially Chiral N-C Bonds
Ken Kamikawa; Shunsuke Kinoshita; Masaru Furusyo; Shin Takemoto; Hiroyuki Matsuzaka; Motokazu Uemura; Journal of Organic Chemistry 72 (2007) 3394–3402; doi:10.1021/jo0700427

data_4022881
_publ_section_title
;
 Stereoselective Synthesis of Both Enantiomers of
 N-Aryl Indoles with Axially Chiral N-C Bonds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3394
_journal_page_last               3402
_journal_paper_doi               10.1021/jo0700427
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C22 H19 Cr N O5'
_chemical_formula_weight         429.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   14.681(2)
_cell_length_b                   14.7727(19)
_cell_length_c                   37.150(6)
_cell_measurement_temperature    296(2)
_cell_volume                     8057(2)
_computing_cell_refinement       'RIGAKU PROCESS AUTO'
_computing_data_collection       'RIGAKU PROCESS AUTO'
_computing_data_reduction        'RIGAKU PROCESS AUTO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'RIGAKU RAXIS RAPID'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1681
_diffrn_reflns_av_sigmaI/netI    0.0921
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            73240
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ABSCOR
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             3552
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                3931
_reflns_number_total             9217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0700427si20070212_113648.cif
_cod_data_source_block           4ga
_cod_database_code               4022881