Regioselective Synthesis of 3-Benzazepinones and Unexpected 5-Bromo-3-benzazepinones
Lei Zhang; Deju Ye; Yu Zhou; Guannan Liu; Enguang Feng; Hualiang Jiang; Hong Liu; Journal of Organic Chemistry 75 (2010) 3671–3677; doi:10.1021/jo100378u

data_4025449
_publ_section_title
;
 Regioselective Synthesis of 3-Benzazepinones and Unexpected
 5-Bromo-3-benzazepinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3671
_journal_page_last               3677
_journal_paper_doi               10.1021/jo100378u
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23
_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                 105.566(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7440(12)
_cell_length_b                   14.3064(14)
_cell_length_c                   17.7456(17)
_cell_measurement_reflns_used    3238
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.015
_cell_measurement_theta_min      4.372
_cell_volume                     3116.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16260
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59607
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3259
_reflns_number_total             5785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100378u_si_002.cif
_cod_data_source_block           cd29285
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025449