Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction.
Allen, Jamie R.; Bahamonde, Ana; Furukawa, Yukino; Sigman, Matthew S.; Journal of the American Chemical Society 141 (2019) 8670–8674; doi:10.1021/jacs.9b01476

data_4127587
_publ_section_title
;
 Enantioselective N-Alkylation of Indoles via an Intermolecular
 Aza-Wacker-Type Reaction.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8670
_journal_page_last               8674
_journal_paper_doi               10.1021/jacs.9b01476
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C17 H15 Br2 N O'
_chemical_formula_weight         409.12
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 103.0460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6020(2)
_cell_length_b                   21.2549(6)
_cell_length_c                   11.3873(3)
_cell_measurement_temperature    103(2)
_cell_volume                     1556.68(8)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            63383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.632
_diffrn_reflns_theta_min         2.654
_exptl_absorpt_coefficient_mu    5.205
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.030(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         14346
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0298
_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^)+(0.0290P)^2^+0.2018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                11955
_reflns_number_total             14346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01476_si_001.cif
_cod_data_source_block           20181204MS_0m_b
_cod_database_code               4127587
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.394
_shelx_estimated_absorpt_t_max   0.574
_shelx_res_checksum              66012
_shelx_hkl_checksum              16582