One-pot cascade leading to direct α-imidation of ketones by a combination of N-bromosuccinimide and 1,8-diazabicyclo[5.4.1]undec-7-ene
Wei, Ying; Lin, Shaoxia; Liang, Fushun; Organic Letters 14 (2012) 4202–4205; doi:10.1021/ol301871s

data_1508349
_publ_section_title
;
 One-pot cascade leading to direct \a-imidation of ketones by a
 combination of N-bromosuccinimide and 1,8-diazabicyclo[5.4.1]undec-7-ene
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   16
_journal_name_full               'Organic Letters'
_journal_page_first              4202
_journal_page_last               4205
_journal_paper_doi               10.1021/ol301871s
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C26 H26 N4 O6'
_chemical_formula_sum            'C13 H13 N2 O3'
_chemical_formula_weight         490.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 108.049(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.369(5)
_cell_length_b                   19.662(5)
_cell_length_c                   11.036(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2551.9(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.851
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10693
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.027(2)
_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   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.4837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                3655
_reflns_number_total             5861
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol301871s_si_002.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_sg_symbol_H-M      p2(1)/c
_cod_database_code               1508349