N-aminopyridinium salts as precursors for N-centered radicals - direct amidation of arenes and heteroarenes.
Greulich, Tobias W.; Daniliuc, Constantin G.; Studer, Armido; Organic letters 17 (2015) 254–257; doi:10.1021/ol503338b

data_1518492
_publ_section_title
;
 N-aminopyridinium salts as precursors for N-centered radicals - direct
 amidation of arenes and heteroarenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              254
_journal_page_last               257
_journal_paper_doi               10.1021/ol503338b
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C32 H22 B Cl3 F4 N2 O2'
_chemical_formula_weight         659.67
_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
_cell_angle_alpha                90
_cell_angle_beta                 113.7440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.8526(5)
_cell_length_b                   11.9970(2)
_cell_length_c                   18.7562(3)
_cell_measurement_reflns_used    5605
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      67.8037
_cell_measurement_theta_min      4.0035
_cell_volume                     6354.75(19)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 v.2014.5-0 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5827
_diffrn_reflns_theta_full        68.34
_diffrn_reflns_theta_max         68.34
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.097
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                4163
_reflns_number_total             5827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503338b_si_002.cif
_cod_data_source_block           stu7772
_cod_depositor_comments
'Adding full bibliography for 1518492--1518494.cif.'
_cod_original_cell_volume        6354.75(18)
_cod_database_code               1518492
_shelx_res_checksum              66025
_shelx_hkl_checksum              38136