Synthesis and Reactivity of (C~6~F~5~)~3~B-N-Heterocycle Complexes. 1. Generation of Highly Acidic sp^3^ Carbons in Pyrroles and Indoles
Simona Guidotti; Isabella Camurati; Francesca Focante; Luca Angellini; Gilberto Moscardi; Luigi Resconi; Rino Leardini; Daniele Nanni; Pierluigi Mercandelli; Angelo Sironi; Tiziana Beringhelli; Daniela Maggioni; Journal of Organic Chemistry 68 (2003) 5445–5465; doi:10.1021/jo020647x

data_4022282
_publ_section_title
;
 Synthesis and Reactivity of (C~6~F~5~)~3~B-N-Heterocycle Complexes.
 1. Generation of Highly Acidic sp^3^ Carbons in
 Pyrroles and Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5445
_journal_page_last               5465
_journal_paper_doi               10.1021/jo020647x
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C6 H16 N 1+, C26 H6 B F15 N 1-'
_chemical_formula_sum            'C32 H22 B F15 N2'
_chemical_formula_weight         730.33
_chemical_name_systematic
;
triethylammonium 1H-indol-1-yltris(pentafluorophenyl)borate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.058(5)
_cell_length_b                   18.061(8)
_cell_length_c                   14.683(7)
_cell_measurement_reflns_used    4323
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.25
_cell_volume                     3191(2)
_computing_structure_refinement
;
Sheldrick, G. M. (1997). SHELX97. Universit\"at G\"ottingen, Germany.
;
_computing_structure_solution
;
SIR97: Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R.
(1999). J. Appl. Cryst. 32, 115-119.
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
A full sphere of reciprocal space was scanned by 0.3\% \w steps, 
collecting 1800
frames each at 20 s exposure. The detector was kept at 3.98(2) cm from the
sample. Intensity decay was monitored by recollecting the initial 50 frames at
the end of data collection and analysing the duplicate reflections.
;
_diffrn_measurement_device_type  'Siemens SMART'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26047
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
Sheldrick, G. M. (1996). SADABS. Universit\"at G\"ottingen, Germany.
11594 symmetry equivalent reflection intensities.
Average redundancy: 3.80.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.05P)^2^+1.8P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_reflns_number_gt                3896
_reflns_number_total             5640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo020647x_s2.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022282