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_1518493
_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            'C15 H10 Cl N O3'
_chemical_formula_weight         287.69
_chemical_name_common            TOG579B
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.6320(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5347(2)
_cell_length_b                   14.9824(4)
_cell_length_c                   10.2813(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.3198
_cell_measurement_theta_min      5.2417
_cell_volume                     1305.88(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_publication_material
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17869
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         5.24
_diffrn_source                   'Cu ImS'
_exptl_absorpt_coefficient_mu    2.659
_exptl_absorpt_correction_T_max  0.73
_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            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0299P)^2^+0.8256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2140
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503338b_si_002.cif
_cod_data_source_block           stu7710
_cod_depositor_comments
'Adding full bibliography for 1518492--1518494.cif.'
_cod_database_code               1518493