2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles.
Abe, Takumi; Suzuki, Takuro; Anada, Masahiro; Matsunaga, Shigeki; Yamada, Koji; Organic letters 19 (2017) 4275–4278; doi:10.1021/acs.orglett.7b01940

data_1547074
_publ_section_title
;
 2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal
 C3-Electrophilic Reactions of Indoles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4275
_journal_page_last               4278
_journal_paper_doi               10.1021/acs.orglett.7b01940
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C21 H29 Br N2 O3 S'
_chemical_formula_sum            'C21 H29 Br N2 O3 S'
_chemical_formula_weight         469.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.015(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   37.0871(9)
_cell_length_b                   18.9011(4)
_cell_length_c                   13.1357(3)
_cell_measurement_reflns_used    42029
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.50
_cell_volume                     8850.6(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45470
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         4.108
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.606
_exptl_absorpt_correction_T_max  0.566
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3904.00
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.71
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0798P)^2^+6.3081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5978
_reflns_number_total             8080
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b01940_si_002.cif
_cod_data_source_block           Ammonium_Bromide_Salt
_cod_database_code               1547074
_shelx_res_checksum              33395
_shelx_hkl_checksum              83118
_shelx_fab_checksum              37670