Selective Radical Amination of Aldehydic C(sp(2))-H Bonds with Fluoroaryl Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions.
Jin, Li-Mei; Lu, Hongjian; Cui, Yuan; Lizardi, Christopher L.; Arzua, Thiago N.; Wojtas, Lukasz; Cui, Xin; Zhang, X. Peter; Chemical science (Royal Society of Chemistry : 2010) 5 (2014) 2422–2427; doi:10.1039/C4SC00697F

data_1516564
_publ_section_title
;
 Selective Radical Amination of Aldehydic C(sp(2))-H Bonds with Fluoroaryl
 Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of
 N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative
 Conditions.
;
_journal_issue                   6
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              2422
_journal_page_last               2427
_journal_paper_doi               10.1039/C4SC00697F
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C20 H15 F5 N2 O3'
_chemical_formula_weight         426.34
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   24.8585(5)
_cell_length_b                   24.8585(5)
_cell_length_c                   16.8633(3)
_cell_measurement_temperature    228(2)
_cell_volume                     9024.5(3)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      228(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22245
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.8006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3924
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.000108(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0351P)^2^+5.9780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                2667
_reflns_number_total             3555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00697f3.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1516563--1516564.cif.'
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               1516564