Enantioselective Aza-Friedel‒Crafts Reaction of Indoles with Ketimines Catalyzed by Chiral Potassium Binaphthyldisulfonates
Hatano, Manabu; Mochizuki, Takuya; Nishikawa, Keisuke; Ishihara, Kazuaki; ACS Catalysis 8 (2017) 349–; doi:10.1021/acscatal.7b03708

data_4514316
_publ_section_title
;
 Enantioselective Aza-Friedel--Crafts Reaction of Indoles with Ketimines
 Catalyzed by Chiral Potassium Binaphthyldisulfonates
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              349
_journal_paper_doi               10.1021/acscatal.7b03708
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration (R)
_chemical_formula_sum            'C60 H48 Ca O10 S2'
_chemical_formula_weight         1033.18
_chemical_name_common
;
(R)-Ar2-BINSA calcium(II) salt
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 102.716(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.348(7)
_cell_length_b                   11.244(4)
_cell_length_c                   17.721(7)
_cell_measurement_reflns_used    5100
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      3.046
_cell_volume                     2983(2)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_unetI/netI     0.1488
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25283
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         3.046
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         11685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.200
_refine_ls_shift/su_mean         0.184
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1306P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2160
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                6156
_reflns_number_total             11685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03708_si_003.cif
_cod_data_source_block           CrystalClear
_cod_depositor_comments
'Adding full bibliography for 4514315--4514316.cif.'
_cod_database_code               4514316
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014/6
_shelx_res_checksum              38479
_shelx_hkl_checksum              28999