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_4128503
_publ_section_title
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 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         'C19 H23 N3 O2 S'
_chemical_formula_sum            'C19 H23 N3 O2 S'
_chemical_formula_weight         357.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                78.839(2)
_cell_angle_beta                 74.149(2)
_cell_angle_gamma                83.650(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8984(7)
_cell_length_b                   10.0654(8)
_cell_length_c                   11.7138(10)
_cell_measurement_reflns_used    9788
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      36.36
_cell_measurement_theta_min      2.52
_cell_volume                     877.25(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            74499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         36.414
_diffrn_reflns_theta_min         2.518
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         8532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0433P)^2^+0.3019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7514
_reflns_number_total             8532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7.cif
_cod_data_source_block           7
_cod_database_code               4128503
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              91564
_shelx_hkl_checksum              75971