Synthesis of unsymmetrical 3,3'-biquinazoline-2,2'-diones by condensation of 3-aminoquinazolinones with benzoxazinones; fortuitous discovery, and further syntheses of 4-H-3-oxo-1,9a,10-triazaanthracen-9-ones.
Coogan, Michael P.; Ooi, Li-ling; Pertusati, Fabrizio; Organic & biomolecular chemistry 3 (2005) 1134–1139; doi:10.1039/b419108k

data_7150130
_publ_section_title
;
 Synthesis of unsymmetrical 3,3'-biquinazoline-2,2'-diones by
 condensation of 3-aminoquinazolinones with benzoxazinones; fortuitous
 discovery, and further syntheses of
 4-H-3-oxo-1,9a,10-triazaanthracen-9-ones.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1134
_journal_page_last               1139
_journal_paper_doi               10.1039/b419108k
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C13 H13 N3 O2'
_chemical_formula_sum            'C13 H13 N3 O2'
_chemical_formula_weight         243.26
_chemical_melting_point          230
_chemical_name_common
4-isopropyl-4H-3-oxo-1,9a,10-triazaanthracen-9-one
_chemical_name_systematic
;
4-isopropyl-4H-3-oxo-1,9a,10-triazaanthracen-9-one
;
_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
_cell_angle_alpha                90.000
_cell_angle_beta                 96.743(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   9.891(5)
_cell_length_b                   10.066(5)
_cell_length_c                   11.732(5)
_cell_measurement_reflns_used    6081
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.91
_cell_volume                     1160.0(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-97 (A. Altomare et al., 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8656
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0734P)^2^+0.1722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                2161
_reflns_number_total             3323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419108k.txt
_cod_data_source_block           C13H13N3O2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150130