One-pot synthesis of dibenzo[b,h][1,6]naphthyridines from 2-acetylaminobenzaldehyde: application to a fluorescent DNA-binding compound
Kentaro Okuma; Tomohiro Koga; Saori Ozaki; Yutaro Suzuki; Kenta Horigami; Noriyoshi Nagahora; Kosei Shioji; Masatora Fukuda; Masanobu Deshimaru; Chem.Commun. 50 (2014) 15525–; doi:10.1039/C4cc07807A

data_7116081
_publ_section_title
;
 One-pot synthesis of dibenzo[b,h][1,6]naphthyridines from
 2-acetylaminobenzaldehyde: application to a fluorescent DNA-binding
 compound
;
_journal_name_full               Chem.Commun.
_journal_page_first              15525
_journal_paper_doi               10.1039/C4cc07807A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C24 H19 Br N2 O2'
_chemical_formula_sum            'C24 H19 Br N2 O2'
_chemical_formula_weight         447.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.546(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.424(16)
_cell_length_b                   9.834(11)
_cell_length_c                   16.368(19)
_cell_measurement_temperature    293(2)
_cell_volume                     1981(4)
_computing_cell_refinement       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_data_collection       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_data_reduction        'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'yadokari-XG (Wakita, 2005)'
_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  'Rigaku Mercury'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            16408
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  0.8176
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, RA (1998). REQAB. Version 1.1. Molecular Structure Corporation,
 9009 Research Forest Drive, The Woodlands, TX 77381, USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0902
_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^)+(0.1643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2539
_refine_ls_wR_factor_ref         0.3358
_reflns_number_gt                2031
_reflns_number_total             3661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07807a2.cif
_cod_data_source_block           101102
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7116081