Electrochemical Dearomative 2,3-Difunctionalization of Indoles.
Wu, Ju; Dou, Yingchao; Guillot, Régis; Kouklovsky, Cyrille; Vincent, Guillaume; Journal of the American Chemical Society 141 (2019) 2832–2837; doi:10.1021/jacs.8b13371

data_4128502
_publ_section_title
;
 Electrochemical Dearomative 2,3-Difunctionalization of Indoles.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2832
_journal_page_last               2837
_journal_paper_doi               10.1021/jacs.8b13371
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C20 H20 Br N O3 S'
_chemical_formula_sum            'C20 H20 Br N O3 S'
_chemical_formula_weight         434.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.593(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4325(7)
_cell_length_b                   13.3190(11)
_cell_length_c                   16.3809(13)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      36.40
_cell_measurement_theta_min      2.52
_cell_volume                     1814.1(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            117620
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.472
_diffrn_reflns_theta_min         2.522
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  0.9211
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.941
_refine_diff_density_min         -1.407
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         8867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+2.3923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7179
_reflns_number_total             8867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3e.cif
_cod_data_source_block           3e
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4128502
_shelx_estimated_absorpt_t_min   0.761
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              42337
_shelx_hkl_checksum              97118