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_4031971
_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            'C17 H15 Br N2 O2'
_chemical_formula_weight         359.22
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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            8
_cell_length_a                   9.62840(13)
_cell_length_b                   9.62840(13)
_cell_length_c                   34.5870(7)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.1200
_cell_measurement_theta_min      6.3810
_cell_volume                     3206.43(9)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            6282
_diffrn_reflns_theta_full        72.19
_diffrn_reflns_theta_max         72.19
_diffrn_reflns_theta_min         4.77
_exptl_absorpt_coefficient_mu    3.566
_exptl_absorpt_correction_T_max  0.4143
_exptl_absorpt_correction_T_min  0.3683
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.00207(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+1.6020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                3014
_reflns_number_total             3090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00123_si_002.cif
_cod_data_source_block           p
_cod_original_cell_volume        3206.42(9)
_cod_original_sg_symbol_H-M      P43212
_cod_database_code               4031971