data_5w _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 N3 O' _chemical_formula_sum 'C20 H15 N3 O' _chemical_formula_weight 313.35 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2601(7) _cell_length_b 8.3406(6) _cell_length_c 18.1111(13) _cell_angle_alpha 90.00 _cell_angle_beta 97.908(2) _cell_angle_gamma 90.00 _cell_volume 1535.13(19) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3177 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 30.79 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11426 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 31.03 _reflns_number_total 4714 _reflns_number_gt 3679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0671P)^2^+0.3918P] 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 4714 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 -0.09393(11) 0.64465(14) 0.03798(7) 0.0139(2) Uani 1 1 d . . . C2 C -0.05446(11) 0.74052(14) -0.02412(7) 0.0138(2) Uani 1 1 d . . . C3 C -0.12988(12) 0.78857(15) -0.08976(7) 0.0177(3) Uani 1 1 d . . . H3 H -0.2197 0.7583 -0.1011 0.021 Uiso 1 1 calc R . . C4 C -0.06913(13) 0.88296(16) -0.13848(7) 0.0201(3) Uani 1 1 d . . . H4 H -0.1176 0.9164 -0.1844 0.024 Uiso 1 1 calc R . . C5 C 0.06220(12) 0.92905(15) -0.12066(7) 0.0188(3) Uani 1 1 d . . . H5 H 0.1015 0.9936 -0.1548 0.023 Uiso 1 1 calc R . . C6 C 0.13744(12) 0.88246(14) -0.05373(7) 0.0159(2) Uani 1 1 d . . . H6 H 0.2264 0.9156 -0.0414 0.019 Uiso 1 1 calc R . . C7 C 0.07703(11) 0.78578(13) -0.00595(7) 0.0128(2) Uani 1 1 d . . . C8 C 0.12454(11) 0.71831(14) 0.06889(7) 0.0128(2) Uani 1 1 d . . . C9 C 0.01656(11) 0.56807(14) 0.16531(7) 0.0147(2) Uani 1 1 d . . . H9A H 0.1051 0.5240 0.1826 0.018 Uiso 1 1 calc R . . H9B H -0.0470 0.4782 0.1615 0.018 Uiso 1 1 calc R . . C10 C -0.01927(12) 0.68846(14) 0.22173(7) 0.0140(2) Uani 1 1 d . . . C11 C -0.15082(12) 0.71515(15) 0.22961(7) 0.0171(2) Uani 1 1 d . . . H11 H -0.2181 0.6580 0.1992 0.020 Uiso 1 1 calc R . . C12 C -0.18408(13) 0.82503(16) 0.28176(8) 0.0207(3) Uani 1 1 d . . . H12 H -0.2739 0.8414 0.2872 0.025 Uiso 1 1 calc R . . C13 C -0.08689(14) 0.91079(16) 0.32583(7) 0.0219(3) Uani 1 1 d . . . H13 H -0.1099 0.9850 0.3617 0.026 Uiso 1 1 calc R . . C14 C 0.04429(13) 0.88754(16) 0.31726(7) 0.0204(3) Uani 1 1 d . . . H14 H 0.1111 0.9476 0.3466 0.024 Uiso 1 1 calc R . . C15 C 0.07784(12) 0.77645(15) 0.26580(7) 0.0168(2) Uani 1 1 d . . . H15 H 0.1678 0.7603 0.2606 0.020 Uiso 1 1 calc R . . C16 C 0.35076(11) 0.77861(14) 0.08988(7) 0.0138(2) Uani 1 1 d . . . C17 C 0.41759(12) 0.90230(16) 0.13044(7) 0.0191(3) Uani 1 1 d . . . H17 H 0.3811 0.9531 0.1698 0.023 Uiso 1 1 calc R . . C18 C 0.53875(13) 0.94977(16) 0.11204(8) 0.0217(3) Uani 1 1 d . . . H18 H 0.5825 1.0362 0.1392 0.026 Uiso 1 1 calc R . . C19 C 0.53199(12) 0.76193(15) 0.02052(7) 0.0177(2) Uani 1 1 d . . . H19 H 0.5716 0.7119 -0.0179 0.021 Uiso 1 1 calc R . . C20 C 0.40981(11) 0.70642(15) 0.03363(7) 0.0157(2) Uani 1 1 d . . . H20 H 0.3675 0.6212 0.0049 0.019 Uiso 1 1 calc R . . N1 N 0.01590(9) 0.64077(12) 0.09198(6) 0.0131(2) Uani 1 1 d . . . N2 N 0.23365(10) 0.71923(12) 0.11213(6) 0.0147(2) Uani 1 1 d . . . N3 N 0.59800(10) 0.88178(14) 0.05859(7) 0.0205(2) Uani 1 1 d . . . O1 O -0.19793(8) 0.57840(11) 0.04327(5) 0.0188(2) 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 0.0130(5) 0.0112(5) 0.0175(6) -0.0028(4) 0.0022(4) -0.0002(4) C2 0.0138(5) 0.0114(5) 0.0163(6) -0.0014(4) 0.0028(4) -0.0009(4) C3 0.0160(5) 0.0171(6) 0.0190(6) -0.0003(5) -0.0018(5) -0.0006(4) C4 0.0227(6) 0.0182(6) 0.0182(6) 0.0027(5) -0.0010(5) 0.0015(5) C5 0.0223(6) 0.0157(6) 0.0190(6) 0.0035(5) 0.0053(5) 0.0001(5) C6 0.0159(5) 0.0133(5) 0.0188(6) 0.0001(4) 0.0038(4) -0.0006(4) C7 0.0128(5) 0.0109(5) 0.0148(5) -0.0012(4) 0.0024(4) 0.0004(4) C8 0.0131(5) 0.0113(5) 0.0147(5) -0.0017(4) 0.0046(4) -0.0013(4) C9 0.0157(5) 0.0131(5) 0.0159(6) 0.0017(4) 0.0046(4) -0.0008(4) C10 0.0166(5) 0.0119(5) 0.0141(5) 0.0031(4) 0.0040(4) 0.0011(4) C11 0.0163(5) 0.0149(6) 0.0205(6) 0.0022(5) 0.0043(5) -0.0006(4) C12 0.0211(6) 0.0183(6) 0.0239(7) 0.0033(5) 0.0079(5) 0.0057(5) C13 0.0300(7) 0.0188(6) 0.0168(6) 0.0003(5) 0.0033(5) 0.0085(5) C14 0.0246(6) 0.0173(6) 0.0175(6) -0.0003(5) -0.0035(5) 0.0024(5) C15 0.0164(5) 0.0175(6) 0.0162(6) 0.0025(4) 0.0010(4) 0.0014(4) C16 0.0116(5) 0.0149(5) 0.0146(5) 0.0014(4) 0.0004(4) -0.0006(4) C17 0.0191(6) 0.0199(6) 0.0189(6) -0.0048(5) 0.0043(5) -0.0043(5) C18 0.0195(6) 0.0212(6) 0.0242(7) -0.0050(5) 0.0022(5) -0.0073(5) C19 0.0144(5) 0.0188(6) 0.0203(6) -0.0010(5) 0.0038(4) -0.0005(4) C20 0.0136(5) 0.0156(5) 0.0177(6) -0.0018(4) 0.0019(4) -0.0009(4) N1 0.0120(4) 0.0139(5) 0.0137(5) 0.0010(4) 0.0028(4) -0.0018(3) N2 0.0131(4) 0.0154(5) 0.0159(5) 0.0000(4) 0.0029(4) -0.0011(4) N3 0.0153(5) 0.0222(6) 0.0243(6) -0.0006(4) 0.0038(4) -0.0036(4) O1 0.0134(4) 0.0172(4) 0.0260(5) -0.0003(4) 0.0035(3) -0.0036(3) _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 1.2171(14) . ? C1 N1 1.3871(15) . ? C1 C2 1.4810(17) . ? C2 C3 1.3855(16) . ? C2 C7 1.3960(16) . ? C3 C4 1.3923(19) . ? C3 H3 0.9500 . ? C4 C5 1.3957(18) . ? C4 H4 0.9500 . ? C5 C6 1.3996(17) . ? C5 H5 0.9500 . ? C6 C7 1.3896(17) . ? C6 H6 0.9500 . ? C7 C8 1.4865(17) . ? C8 N2 1.2749(15) . ? C8 N1 1.4014(15) . ? C9 N1 1.4591(16) . ? C9 C10 1.5136(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3945(16) . ? C10 C15 1.3962(17) . ? C11 C12 1.3917(18) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.3895(19) . ? C13 H13 0.9500 . ? C14 C15 1.3907(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.3912(17) . ? C16 C20 1.3919(17) . ? C16 N2 1.4087(15) . ? C17 C18 1.3882(18) . ? C17 H17 0.9500 . ? C18 N3 1.3379(18) . ? C18 H18 0.9500 . ? C19 N3 1.3435(16) . ? C19 C20 1.3871(16) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 N1 124.74(12) . . ? O1 C1 C2 129.73(11) . . ? N1 C1 C2 105.52(10) . . ? C3 C2 C7 122.11(11) . . ? C3 C2 C1 128.97(11) . . ? C7 C2 C1 108.87(10) . . ? C2 C3 C4 117.49(11) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? C3 C4 C5 120.75(12) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 121.59(12) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 117.41(11) . . ? C7 C6 H6 121.3 . . ? C5 C6 H6 121.3 . . ? C6 C7 C2 120.64(11) . . ? C6 C7 C8 132.00(10) . . ? C2 C7 C8 107.31(10) . . ? N2 C8 N1 119.13(11) . . ? N2 C8 C7 135.06(11) . . ? N1 C8 C7 105.80(9) . . ? N1 C9 C10 111.58(10) . . ? N1 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N1 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C15 118.83(12) . . ? C11 C10 C9 120.22(11) . . ? C15 C10 C9 120.94(11) . . ? C12 C11 C10 120.38(12) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.40(12) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.63(12) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.05(12) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 120.69(12) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C17 C16 C20 118.34(11) . . ? C17 C16 N2 119.18(11) . . ? C20 C16 N2 122.11(11) . . ? C18 C17 C16 118.51(12) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? N3 C18 C17 124.32(12) . . ? N3 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? N3 C19 C20 124.34(12) . . ? N3 C19 H19 117.8 . . ? C20 C19 H19 117.8 . . ? C19 C20 C16 118.39(11) . . ? C19 C20 H20 120.8 . . ? C16 C20 H20 120.8 . . ? C1 N1 C8 112.40(10) . . ? C1 N1 C9 123.58(10) . . ? C8 N1 C9 124.00(10) . . ? C8 N2 C16 122.54(11) . . ? C18 N3 C19 116.07(11) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.510 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.059 _publ_contact_author ; Dr Shunsuke Chiba Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ; _publ_contact_author_phone '+65 6513 8013' _publ_contact_author_fax '+65 6791 1961' _publ_contact_author_email 'shunsuke@ntu.edu.sg' _publ_requested_journal 'Organic Letters' _publ_section_title ; 'Oxidative Radical Skeletal Rearrangement Induced by Molecular Oxygen: Synthesis of Quinazolinones' ; loop_ _publ_author_name _publ_author_address 'Yi-Feng Wang' ;Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ; 'Feng-Lian Zhang' ;Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ; 'Shunsuke Chiba' ;Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ;