A concise and efficient concurrent synthesis of 6,11-dihydrodibenzo[<i>b</i>,<i>e</i>]azepines and 5,6,11,12-tetrahydrodibenzo[<i>b</i>,<i>f</i>]azocines and their conversion to 4-oxo-8,13-dihydro-4<i>H</i>-benzo[5,6]azepino[3,2,1-<i>ij</i>]quinoline-5-carboxylates and <i>N</i>-acetyl-5,6,11,12-tetrahydrodibenzo[<i>b</i>,<i>f</i>]azocines: synthetic sequence, spectroscopic characterization and the structures of two products
Acosta Quintero, Lina M.; Palma, Alirio; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619005746

data_2021620
_publ_section_title
;
 A concise and efficient concurrent synthesis of
 6,11-dihydrodibenzo[<i>b</i>,<i>e</i>]azepines and
 5,6,11,12-tetrahydrodibenzo[<i>b</i>,<i>f</i>]azocines and their
 conversion to
 4-oxo-8,13-dihydro-4<i>H</i>-benzo[5,6]azepino[3,2,1-<i>ij</i>]quinoline-5-carboxylates
 and
 <i>N</i>-acetyl-5,6,11,12-tetrahydrodibenzo[<i>b</i>,<i>f</i>]azocines:
 synthetic sequence, spectroscopic characterization and the structures of
 two products
;
_journal_coeditor_code           YF3175
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619005746
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C22 H20 F N O3'
_chemical_formula_moiety         'C22 H20 F N O3'
_chemical_formula_sum            'C22 H20 F N O3'
_chemical_formula_weight         365.39
_chemical_name_systematic
'Ethyl (<i>RS</i>)-13-ethyl-2-fluoro-4-oxo-8,13-dihydro-4<i>H</i>-benzo[5,6]azepino[3,2,1-<i>ij</i>]quinoline-5-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.290(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5920(6)
_cell_length_b                   13.4325(7)
_cell_length_c                   14.2186(8)
_cell_measurement_reflns_used    4414
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.281
_cell_measurement_theta_min      2.182
_cell_volume                     1782.93(18)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33534
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.182
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.9921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                3808
_reflns_number_total             4414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yf3175sup1.cif
_cod_data_source_block           IVa
_cod_database_code               2021620
_cod_database_fobs_code          2021620
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              16078
_shelx_res_checksum              68887
_shelxl_version_number           2.014