Enantioselective Friedel-Crafts Alkylation Reactions of 3-Substituted Indoles with Electron-Deficient Alkenes.
Weng, Jian-Quan; Fan, Ren-Jie; Deng, Qiao-Man; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia; The Journal of organic chemistry 81 (2016) 3023–3030; doi:10.1021/acs.joc.6b00123

data_4031970
_publ_section_title
;
 Enantioselective Friedel-Crafts Alkylation Reactions of 3-Substituted
 Indoles with Electron-Deficient Alkenes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3023
_journal_page_last               3030
_journal_paper_doi               10.1021/acs.joc.6b00123
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C24 H24 Br N O5'
_chemical_formula_weight         486.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.8030(10)
_cell_angle_beta                 99.9820(10)
_cell_angle_gamma                116.4220(10)
_cell_formula_units_Z            2
_cell_length_a                   10.9290(3)
_cell_length_b                   11.0375(3)
_cell_length_c                   11.7658(4)
_cell_measurement_reflns_used    5188
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.19
_cell_volume                     1138.79(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13305
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.839
_exptl_absorpt_correction_T_max  0.6176
_exptl_absorpt_correction_T_min  0.4722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+0.8771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                3305
_reflns_number_total             3984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00123_si_001.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4031970