Metal-free (Boc)2O-mediated C4-selective direct indolation of pyridines using TEMPO.
Qin, Wen-Bing; Zhu, Jia-Yi; Kong, Yu-Bo; Bao, Yun-Hong; Chen, Zheng-Wang; Liu, Liang-Xian; Organic & biomolecular chemistry 12 (2014) 4252–4259; doi:10.1039/c4ob00356j

data_7153778
_publ_section_title
;
 Metal-free (Boc)2O-mediated C4-selective direct indolation of pyridines
 using TEMPO.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4252
_journal_page_last               4259
_journal_paper_doi               10.1039/c4ob00356j
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C13 H8 Br N2'
_chemical_formula_weight         272.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.433(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8956(2)
_cell_length_b                   18.5240(6)
_cell_length_c                   12.7557(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1137.64(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7878
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    3.584
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                1327
_reflns_number_total             2722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00356j2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7153778.cif.'
_cod_database_code               7153778