Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: rearrangements of isatins, acridines, and indoles.
Elliott, Emma-Claire; Bowkett, Elizabeth R.; Maggs, James L.; Bacsa, John; Park, B. Kevin; Regan, Sophie L.; O'Neill, Paul M; Stachulski, Andrew V.; Organic letters 13 (2011) 5592–5595; doi:10.1021/ol202318w

data_1501602
_publ_section_title
;
 Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines:
 rearrangements of isatins, acridines, and indoles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5592
_journal_page_last               5595
_journal_paper_doi               10.1021/ol202318w
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H10 F N'
_chemical_formula_sum            'C14 H10 F N'
_chemical_formula_weight         211.23
_chemical_name_common            EB7721
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2094(19)
_cell_length_b                   21.264(5)
_cell_length_c                   5.9988(13)
_cell_measurement_reflns_used    488
_cell_measurement_temperature    218(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.1
_cell_volume                     1047.2(4)
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'IPDS (Stoe & Cie, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      218(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '200\% f scan, \f-incr 2.0 \%, 100 exposures'
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5675
_diffrn_reflns_theta_full        24.15
_diffrn_reflns_theta_max         24.15
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (R.H. Blessing, (1989)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.079
_refine_diff_density_rms         0.022
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         842
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.0559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                602
_reflns_number_total             842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202318w_si_002.cif
_cod_data_source_block           eb7721
_cod_depositor_comments          'Adding full bibliography for 1501602.cif.'
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               1501602