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_7116082
_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         'C23 H16 N2'
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38
_chemical_name_common            dibenzonaphthyridine
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 90.257(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   36.980(18)
_cell_length_b                   5.904(3)
_cell_length_c                   15.103(7)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.31
_cell_volume                     3297(3)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Rigaku_Saturn724+
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10985
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9812
_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    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0707
_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^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                1561
_reflns_number_total             3208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07807a2.cif
_cod_data_source_block           110719
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7116082