Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Coogan, Michael Peter' _publ_contact_author_email cooganmp@cf.ac.uk _publ_contact_author_address ; Department of Chemistry Cardiff University Department of Chemistry Cardiff University Park Place Cardiff Wales CF10 3TB UNITED KINGDOM ; _publ_section_title ; Synthesis Of Unsymmetrical 3,3'-Biquinazoline-2,2'-Diones By Condensation Of 3-Aminoquinazolinones With Benzoxazinones Fortuitous Discovery, And Further Synthesis Of 4-H-3-Oxo-1,9a,10-Triazaanthracen-9-Ones. ; loop_ _publ_author_name 'Michael Coogan' 'Li-ling Ooi.' 'Fabrizio Pertusati' data_C13H13N3O2 _database_code_depnum_ccdc_archive 'CCDC 259058' _chemical_name_systematic ; 4-isopropyl-4H-3-oxo-1,9a,10-triazaanthracen-9-one ; _chemical_name_common 4-isopropyl-4H-3-oxo-1,9a,10-triazaanthracen-9-one _chemical_melting_point 230 _chemical_formula_moiety 'C13 H13 N3 O2' _chemical_formula_sum 'C13 H13 N3 O2' _chemical_formula_weight 243.26 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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' _cell_length_a 9.891(5) _cell_length_b 10.066(5) _cell_length_c 11.732(5) _cell_angle_alpha 90.000 _cell_angle_beta 96.743(5) _cell_angle_gamma 90.000 _cell_volume 1160.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6081 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.034 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8656 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 30.02 _reflns_number_total 3323 _reflns_number_gt 2161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'Sir-97 (A. Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.1722P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3323 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1609 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0207(8) 0.0190(7) 0.0165(7) -0.0007(6) 0.0020(6) 0.0027(6) C2 0.0177(8) 0.0186(7) 0.0176(7) 0.0012(6) 0.0032(6) 0.0030(6) C3 0.0216(8) 0.0215(7) 0.0196(7) -0.0026(6) 0.0010(6) 0.0010(6) C4 0.0236(9) 0.0181(7) 0.0274(8) -0.0020(7) 0.0035(6) -0.0015(6) C5 0.0272(9) 0.0200(8) 0.0261(8) 0.0056(6) 0.0039(7) 0.0020(7) C6 0.0281(9) 0.0230(8) 0.0175(7) 0.0037(6) -0.0015(6) 0.0012(7) C7 0.0197(8) 0.0170(7) 0.0186(7) -0.0002(6) 0.0018(6) 0.0030(6) C8 0.0200(8) 0.0198(7) 0.0171(7) -0.0017(6) 0.0018(6) 0.0024(6) C9 0.0288(9) 0.0177(7) 0.0198(7) -0.0004(6) 0.0002(6) 0.0000(6) C10 0.0222(9) 0.0252(8) 0.0354(9) -0.0039(7) -0.0010(7) -0.0020(7) C11 0.0358(13) 0.0601(15) 0.0908(18) -0.0305(14) 0.0262(12) -0.0072(11) C12 0.0319(11) 0.0333(10) 0.0490(11) -0.0089(9) -0.0054(9) -0.0066(8) C13 0.0385(11) 0.0209(8) 0.0215(8) 0.0020(6) 0.0024(7) 0.0015(7) N1 0.0280(8) 0.0195(6) 0.0174(6) -0.0006(5) -0.0016(5) 0.0003(5) N2 0.0251(7) 0.0165(6) 0.0145(6) 0.0010(5) 0.0023(5) 0.0011(5) N3 0.0392(9) 0.0188(6) 0.0191(6) 0.0055(5) 0.0018(6) -0.0007(6) O1 0.0424(8) 0.0233(6) 0.0156(5) 0.0006(5) -0.0039(5) 0.0003(5) O2 0.0909(13) 0.0202(6) 0.0274(7) 0.0054(5) -0.0168(7) -0.0095(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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_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_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) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.333 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.063