data_publication_text _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Yusuke Kobayashi' _publ_contact_author_address ;Tokushima Bunri University Shido 1314-1, Sanuki, Kagawa, Japan ; _publ_contact_author_email ykobayashi@kph.bunri-u.ac.jp _publ_contact_author_phone '+81 87 894 5111' _publ_contact_author_fax '+81 87 894 0181' loop_ _publ_author_name _publ_author_address 'Kobayashi, Yusuke' ;Tokushima Bunri University Shido 1314-1, Sanuki, Kagawa, Japan ; 'Katagiri, Kosuke' ;Tokushima Bunri University Shido 1314-1, Sanuki, Kagawa, Japan ; 'Azumaya, Isao' ;Tokushima Bunri University Shido 1314-1, Sanuki, Kagawa, Japan ; 'Harayama, Takashi' ;Tokushima Bunri University Shido 1314-1, Sanuki, Kagawa, Japan ; data_0014kka _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O2' _chemical_formula_weight 216.24 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 'Triclinic' _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.095(9) _cell_length_b 8.508(11) _cell_length_c 9.717(13) _cell_angle_alpha 89.029(15) _cell_angle_beta 75.838(17) _cell_angle_gamma 85.883(17) _cell_volume 567.2(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 1992 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.08 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _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 Smart1000 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3242 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2414 _reflns_number_gt 2091 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart (Bruker AXS)' _computing_cell_refinement 'Smart (Bruker AXS)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0866P)^2^+0.9234P] 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 2414 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2193 _refine_ls_wR_factor_gt 0.2146 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.004 _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 N1 N 0.3235(3) 0.9518(2) 0.3801(2) 0.0180(5) Uani 1 1 d . . . N2 N 0.3867(4) 0.4958(3) 0.3429(2) 0.0269(5) Uani 1 1 d . . . O1 O 0.1710(3) 0.9751(2) 0.61217(19) 0.0227(4) Uani 1 1 d . . . O2 O 0.0670(3) 0.7523(2) 0.76794(19) 0.0269(5) Uani 1 1 d . . . H2 H 0.0882 0.8455 0.7425 0.040 Uiso 1 1 calc R . . C8 C 0.2392(3) 0.8861(3) 0.5045(3) 0.0171(5) Uani 1 1 d . . . C10 C 0.3169(4) 0.5975(3) 0.4205(3) 0.0194(5) Uani 1 1 d . . . C9 C 0.2274(4) 0.7132(3) 0.5259(3) 0.0175(5) Uani 1 1 d . . . C1 C 0.3720(4) 0.8693(3) 0.2454(2) 0.0173(5) Uani 1 1 d . . . C11 C 0.1407(4) 0.6564(3) 0.6600(3) 0.0208(5) Uani 1 1 d . . . C6 C 0.2227(4) 0.8225(3) 0.1878(3) 0.0229(6) Uani 1 1 d . . . H6 H 0.0902 0.8441 0.2365 0.027 Uiso 1 1 calc R . . C7 C 0.3424(4) 1.1237(3) 0.3734(3) 0.0243(6) Uani 1 1 d . . . H7A H 0.2280 1.1766 0.3483 0.036 Uiso 1 1 calc R . . H7B H 0.4602 1.1469 0.3014 0.036 Uiso 1 1 calc R . . H7C H 0.3514 1.1617 0.4661 0.036 Uiso 1 1 calc R . . C2 C 0.5671(4) 0.8452(3) 0.1723(3) 0.0251(6) Uani 1 1 d . . . H2A H 0.6671 0.8815 0.2107 0.030 Uiso 1 1 calc R . . C12 C 0.1227(4) 0.4864(3) 0.6961(3) 0.0287(6) Uani 1 1 d . . . H12A H 0.2166 0.4519 0.7514 0.043 Uiso 1 1 calc R . . H12B H 0.1493 0.4244 0.6086 0.043 Uiso 1 1 calc R . . H12C H -0.0097 0.4711 0.7522 0.043 Uiso 1 1 calc R . . C5 C 0.2710(5) 0.7433(3) 0.0577(3) 0.0290(6) Uani 1 1 d . . . H5 H 0.1709 0.7091 0.0183 0.035 Uiso 1 1 calc R . . C4 C 0.4649(5) 0.7147(3) -0.0143(3) 0.0330(7) Uani 1 1 d . . . H4 H 0.4970 0.6593 -0.1020 0.040 Uiso 1 1 calc R . . C3 C 0.6135(5) 0.7671(4) 0.0420(3) 0.0321(7) Uani 1 1 d . . . H3 H 0.7458 0.7494 -0.0087 0.039 Uiso 1 1 calc R . . 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 N1 0.0231(11) 0.0138(10) 0.0168(10) -0.0018(8) -0.0045(8) 0.0003(8) N2 0.0391(14) 0.0176(11) 0.0219(11) 0.0001(9) -0.0041(10) 0.0000(10) O1 0.0262(10) 0.0214(10) 0.0187(9) -0.0073(7) -0.0031(7) 0.0027(7) O2 0.0291(10) 0.0331(11) 0.0156(9) -0.0003(8) 0.0001(7) -0.0021(8) C8 0.0163(11) 0.0179(12) 0.0177(11) -0.0034(9) -0.0057(9) 0.0017(9) C10 0.0229(12) 0.0178(12) 0.0165(11) 0.0028(9) -0.0027(9) -0.0023(9) C9 0.0183(11) 0.0181(12) 0.0159(11) -0.0015(9) -0.0043(9) 0.0003(9) C1 0.0241(12) 0.0137(11) 0.0131(11) 0.0016(8) -0.0027(9) -0.0002(9) C11 0.0180(11) 0.0264(14) 0.0183(12) 0.0019(10) -0.0052(9) -0.0017(10) C6 0.0280(13) 0.0204(13) 0.0201(12) 0.0006(10) -0.0063(10) -0.0002(10) C7 0.0308(14) 0.0137(12) 0.0298(14) -0.0015(10) -0.0099(11) -0.0011(10) C2 0.0250(13) 0.0233(13) 0.0246(13) 0.0006(10) -0.0016(10) -0.0016(10) C12 0.0279(14) 0.0317(16) 0.0248(14) 0.0100(11) -0.0026(11) -0.0059(11) C5 0.0455(17) 0.0246(14) 0.0193(13) 0.0001(10) -0.0121(12) -0.0042(12) C4 0.057(2) 0.0240(14) 0.0133(12) 0.0003(10) 0.0000(12) -0.0040(13) C3 0.0359(16) 0.0275(15) 0.0247(14) 0.0001(11) 0.0075(11) 0.0002(12) _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 N1 C8 1.342(4) . ? N1 C1 1.449(3) . ? N1 C7 1.478(4) . ? N2 C10 1.157(4) . ? O1 C8 1.276(3) . ? O2 C11 1.318(3) . ? O2 H2 0.8400 . ? C8 C9 1.488(4) . ? C10 C9 1.431(4) . ? C9 C11 1.393(4) . ? C1 C2 1.395(4) . ? C1 C6 1.397(4) . ? C11 C12 1.489(4) . ? C6 C5 1.398(4) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C2 C3 1.395(4) . ? C2 H2A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C5 C4 1.388(5) . ? C5 H5 0.9500 . ? C4 C3 1.403(5) . ? C4 H4 0.9500 . ? C3 H3 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 C8 N1 C1 124.0(2) . . ? C8 N1 C7 119.1(2) . . ? C1 N1 C7 116.2(2) . . ? C11 O2 H2 109.5 . . ? O1 C8 N1 118.9(2) . . ? O1 C8 C9 117.5(2) . . ? N1 C8 C9 123.5(2) . . ? N2 C10 C9 175.0(3) . . ? C11 C9 C10 116.3(2) . . ? C11 C9 C8 119.2(2) . . ? C10 C9 C8 124.2(2) . . ? C2 C1 C6 121.2(2) . . ? C2 C1 N1 119.2(2) . . ? C6 C1 N1 119.5(2) . . ? O2 C11 C9 121.5(3) . . ? O2 C11 C12 114.0(2) . . ? C9 C11 C12 124.5(2) . . ? C1 C6 C5 119.1(3) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C2 C1 119.1(3) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.552 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.097