Metal-free electrochemical [3 + 2] heteroannulation of anilines with pyridines enabled by dual C–H radical aminations
Luo, Mu-Jia; Ouyang, Xuan-Hui; Zhu, Yan-Ping; Li, Yang; Li, Jin-Heng; Green Chemistry 23 (2021) 9024–9029; doi:10.1039/D1GC02922C

data_7243738
_publ_section_title
;
 Metal-free electrochemical [3 + 2] heteroannulation of anilines with
 pyridines enabled by dual C--H radical aminations
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              9024
_journal_page_last               9029
_journal_paper_doi               10.1039/D1GC02922C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         C15H13FN2O3
_chemical_formula_sum            'C15 H13 F N2 O3'
_chemical_formula_weight         288.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-17 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.00(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.35(3)
_cell_length_b                   13.16(3)
_cell_length_c                   8.567(18)
_cell_measurement_reflns_used    1475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.56
_cell_measurement_theta_min      2.26
_cell_volume                     1390(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2033
_diffrn_reflns_av_unetI/netI     0.2062
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7959
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.263
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.7512
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.2881
_refine_ls_R_factor_gt           0.1215
_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^)+(0.0694P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                923
_reflns_number_total             2498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02922c2.cif
_cod_data_source_block           A
_cod_depositor_comments          'Adding full bibliography for 7243738.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7243738
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              31330