A novel synthesis of (di)-benzazocinones via an endocyclic N-acyliminium ion cyclisation.
King, Frank D.; Aliev, Abil E.; Caddick, Stephen; Tocher, D. A.; Organic & biomolecular chemistry 9 (2011) 1547–1554; doi:10.1039/C0OB00559B

data_7151656
_publ_section_title
;
 A novel synthesis of (di)-benzazocinones via an endocyclic
 N-acyliminium ion cyclisation.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1547
_journal_page_last               1554
_journal_paper_doi               10.1039/C0OB00559B
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C14 H15 Br2 N O'
_chemical_formula_weight         373.09
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.759(3)
_cell_angle_beta                 84.820(3)
_cell_angle_gamma                73.866(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6309(10)
_cell_length_b                   8.4895(16)
_cell_length_c                   14.660(3)
_cell_measurement_temperature    150(2)
_cell_volume                     670.4(2)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.872
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5409
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    6.033
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.1598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.036(3)
_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   0.755
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.755
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0384
_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^)+(0.1028P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2476
_reflns_number_total             2933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00559B.TXT
_cod_data_source_block           str0837
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151656