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_4514315
_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            'C30 H28 N2 O2 S'
_chemical_formula_weight         480.60
_chemical_name_common
;
(R)-N-(1-(1-benzyl-1H-indol-3-yl)-1-phenylethyl)
-4-methylbenzenesulfonamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                94.682(5)
_cell_angle_beta                 100.658(5)
_cell_angle_gamma                98.889(5)
_cell_formula_units_Z            2
_cell_length_a                   9.528(3)
_cell_length_b                   10.803(3)
_cell_length_c                   12.452(3)
_cell_measurement_reflns_used    4691
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.026
_cell_volume                     1236.4(6)
_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 0.962
_diffrn_measured_fraction_theta_max 0.934
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10622
_diffrn_reflns_point_group_measured_fraction_full 0.718
_diffrn_reflns_point_group_measured_fraction_max 0.673
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.025
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         7606
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0627P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.440
_reflns_Friedel_fraction_full    0.473
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                6969
_reflns_number_total             7606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b03708_si_002.cif
_cod_data_source_block           CrystalClear
_cod_depositor_comments
;
Adding full bibliography for 4514315--4514316.cif.

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C60 H56 N4 O4 S2'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     961.20
_cod_database_code               4514315
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2014/6
_shelx_res_checksum              27931
_shelx_hkl_checksum              90679