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#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150130.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150130
loop_
_publ_author_name
'Coogan, Michael P.'
'Ooi, Li-ling'
'Pertusati, Fabrizio'
_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 & 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/[σ²(Fo²)+(0.0734P)²+0.1722P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.87817(16) -0.03422(15) 0.13882(12) 0.0188(3) Uani 1 1 d . . .
C2 C 0.87118(16) 0.08164(15) 0.06405(12) 0.0179(3) Uani 1 1 d . . .
C3 C 0.92228(16) 0.20438(15) 0.10675(13) 0.0210(3) Uani 1 1 d . . .
H3 H 0.9631 0.2118 0.1839 0.025 Uiso 1 1 calc R . .
C4 C 0.91273(17) 0.31393(15) 0.03581(13) 0.0230(4) Uani 1 1 d . . .
H4 H 0.9466 0.3973 0.0644 0.028 Uiso 1 1 calc R . .
C5 C 0.85341(17) 0.30311(16) -0.07805(13) 0.0243(4) Uani 1 1 d . . .
H5 H 0.8467 0.3793 -0.1262 0.029 Uiso 1 1 calc R . .
C6 C 0.80469(17) 0.18258(15) -0.12068(13) 0.0232(4) Uani 1 1 d . . .
H6 H 0.7659 0.1760 -0.1985 0.028 Uiso 1 1 calc R . .
C7 C 0.81184(16) 0.06982(15) -0.05053(12) 0.0185(3) Uani 1 1 d . . .
C8 C 0.77139(16) -0.15290(15) -0.03019(12) 0.0190(3) Uani 1 1 d . . .
C9 C 0.72534(17) -0.28585(15) -0.08155(13) 0.0223(4) Uani 1 1 d . . .
H9 H 0.7877 -0.3084 -0.1399 0.027 Uiso 1 1 calc R . .
C10 C 0.58145(17) -0.28396(17) -0.14365(15) 0.0279(4) Uani 1 1 d . . .
H10 H 0.5773 -0.2132 -0.2038 0.034 Uiso 1 1 calc R . .
C11 C 0.4770(2) -0.2498(2) -0.0622(2) 0.0608(7) Uani 1 1 d . . .
H11A H 0.4772 -0.3190 -0.0035 0.091 Uiso 1 1 calc R . .
H11B H 0.3863 -0.2441 -0.1057 0.091 Uiso 1 1 calc R . .
H11C H 0.5003 -0.1642 -0.0253 0.091 Uiso 1 1 calc R . .
C12 C 0.5501(2) -0.41703(19) -0.20443(17) 0.0389(5) Uani 1 1 d . . .
H12A H 0.6217 -0.4375 -0.2528 0.058 Uiso 1 1 calc R . .
H12B H 0.4622 -0.4114 -0.2523 0.058 Uiso 1 1 calc R . .
H12C H 0.5465 -0.4873 -0.1471 0.058 Uiso 1 1 calc R . .
C13 C 0.77969(19) -0.36809(16) 0.11069(14) 0.0271(4) Uani 1 1 d . . .
H13 H 0.7780 -0.4418 0.1611 0.032 Uiso 1 1 calc R . .
N1 N 0.76278(14) -0.05080(12) -0.09732(10) 0.0219(3) Uani 1 1 d . . .
N2 N 0.82283(13) -0.14957(12) 0.08451(10) 0.0187(3) Uani 1 1 d . . .
N3 N 0.82335(15) -0.26089(13) 0.15706(11) 0.0258(3) Uani 1 1 d . . .
O1 O 0.92612(13) -0.03639(11) 0.23983(9) 0.0277(3) Uani 1 1 d . . .
O2 O 0.73581(17) -0.39242(12) 0.00158(10) 0.0480(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 120.71(13) . . ?
O1 C1 C2 125.68(14) . . ?
N2 C1 C2 113.61(13) . . ?
C3 C2 C7 120.48(14) . . ?
C3 C2 C1 120.00(13) . . ?
C7 C2 C1 119.52(13) . . ?
C4 C3 C2 119.48(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.38(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.32(14) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.64(14) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
N1 C7 C6 118.89(13) . . ?
N1 C7 C2 122.41(13) . . ?
C6 C7 C2 118.69(14) . . ?
N1 C8 N2 124.39(14) . . ?
N1 C8 C9 117.71(13) . . ?
N2 C8 C9 117.88(13) . . ?
O2 C9 C8 113.12(12) . . ?
O2 C9 C10 108.75(14) . . ?
C8 C9 C10 113.58(13) . . ?
O2 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C10 C9 H9 107.0 . . ?
C9 C10 C11 111.55(17) . . ?
C9 C10 C12 109.80(14) . . ?
C11 C10 C12 111.94(16) . . ?
C9 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C12 C10 H10 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 O2 129.14(15) . . ?
N3 C13 H13 115.4 . . ?
O2 C13 H13 115.4 . . ?
C8 N1 C7 117.22(13) . . ?
C8 N2 C1 122.76(13) . . ?
C8 N2 N3 123.00(13) . . ?
C1 N2 N3 114.24(12) . . ?
C13 N3 N2 116.34(13) . . ?
C13 O2 C9 120.27(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2238(18) . ?
C1 N2 1.404(2) . ?
C1 C2 1.456(2) . ?
C2 C3 1.405(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(2) . ?
C6 H6 0.9500 . ?
C7 N1 1.396(2) . ?
C8 N1 1.291(2) . ?
C8 N2 1.3821(19) . ?
C8 C9 1.516(2) . ?
C9 O2 1.445(2) . ?
C9 C10 1.521(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.527(3) . ?
C10 C12 1.532(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N3 1.262(2) . ?
C13 O2 1.325(2) . ?
C13 H13 0.9500 . ?
N2 N3 1.4068(17) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.0(3) . . . . ?
N2 C1 C2 C3 179.79(14) . . . . ?
O1 C1 C2 C7 -179.41(15) . . . . ?
N2 C1 C2 C7 0.4(2) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 C4 -178.75(14) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 N1 -179.27(15) . . . . ?
C5 C6 C7 C2 -0.7(2) . . . . ?
C3 C2 C7 N1 178.41(15) . . . . ?
C1 C2 C7 N1 -2.2(2) . . . . ?
C3 C2 C7 C6 -0.1(2) . . . . ?
C1 C2 C7 C6 179.30(14) . . . . ?
N1 C8 C9 O2 -178.40(15) . . . . ?
N2 C8 C9 O2 3.1(2) . . . . ?
N1 C8 C9 C10 -53.8(2) . . . . ?
N2 C8 C9 C10 127.74(16) . . . . ?
O2 C9 C10 C11 64.96(19) . . . . ?
C8 C9 C10 C11 -62.0(2) . . . . ?
O2 C9 C10 C12 -59.73(18) . . . . ?
C8 C9 C10 C12 173.36(14) . . . . ?
N2 C8 N1 C7 1.5(2) . . . . ?
C9 C8 N1 C7 -176.84(14) . . . . ?
C6 C7 N1 C8 179.79(15) . . . . ?
C2 C7 N1 C8 1.3(2) . . . . ?
N1 C8 N2 C1 -3.4(2) . . . . ?
C9 C8 N2 C1 174.92(14) . . . . ?
N1 C8 N2 N3 176.08(14) . . . . ?
C9 C8 N2 N3 -5.6(2) . . . . ?
O1 C1 N2 C8 -177.95(14) . . . . ?
C2 C1 N2 C8 2.2(2) . . . . ?
O1 C1 N2 N3 2.5(2) . . . . ?
C2 C1 N2 N3 -177.30(13) . . . . ?
O2 C13 N3 N2 1.8(3) . . . . ?
C8 N2 N3 C13 3.3(2) . . . . ?
C1 N2 N3 C13 -177.17(15) . . . . ?
N3 C13 O2 C9 -4.0(3) . . . . ?
C8 C9 O2 C13 1.2(2) . . . . ?
C10 C9 O2 C13 -125.96(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9393804
