data_sm12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; JA037713C ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N2 O2' _chemical_formula_weight 314.33 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 5.9430(9) _cell_length_b 8.6856(13) _cell_length_c 14.988(2) _cell_angle_alpha 74.255(2) _cell_angle_beta 81.050(2) _cell_angle_gamma 83.614(2) _cell_volume 733.64(19) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9322 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2472 _reflns_number_gt 2125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1124P)^2^+0.0739P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2472 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.003 _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 O1 O 1.41149(19) 0.90868(14) 0.17761(8) 0.0328(3) Uani 1 1 d . . . H1O1 H 1.356(3) 0.878(3) 0.1316(15) 0.048(6) Uiso 1 1 d . . . O2 O 0.4079(2) 0.47705(14) 0.23502(8) 0.0341(3) Uani 1 1 d . . . H1O2 H 0.490(4) 0.526(3) 0.1748(16) 0.059(6) Uiso 1 1 d . . . N1 N 0.7517(2) 0.61567(15) 0.12268(9) 0.0268(3) Uani 1 1 d . . . N2 N 1.1134(2) 0.80585(15) 0.09723(9) 0.0272(3) Uani 1 1 d . . . C1 C 0.9961(2) 0.75590(18) 0.18115(10) 0.0252(4) Uani 1 1 d . . . C2 C 0.8295(2) 0.63787(18) 0.19602(10) 0.0248(4) Uani 1 1 d . . . C3 C 0.8569(3) 0.68069(18) 0.03469(10) 0.0269(4) Uani 1 1 d . . . C4 C 0.7795(3) 0.65394(18) -0.04393(11) 0.0290(4) Uani 1 1 d . . . H4A H 0.6420 0.6031 -0.0371 0.035 Uiso 1 1 calc R . . C5 C 0.9048(3) 0.70205(18) -0.13023(11) 0.0306(4) Uani 1 1 d . . . H5A H 0.8541 0.6835 -0.1832 0.037 Uiso 1 1 calc R . . C6 C 1.1080(3) 0.77878(19) -0.14127(11) 0.0310(4) Uani 1 1 d . . . H6A H 1.1954 0.8078 -0.2013 0.037 Uiso 1 1 calc R . . C7 C 1.1812(3) 0.81210(19) -0.06683(11) 0.0294(4) Uani 1 1 d . . . H7A H 1.3163 0.8664 -0.0752 0.035 Uiso 1 1 calc R . . C8 C 1.0537(3) 0.76489(18) 0.02261(11) 0.0267(4) Uani 1 1 d . . . C9 C 1.0307(3) 0.83767(17) 0.25217(10) 0.0261(4) Uani 1 1 d . . . C10 C 1.2327(3) 0.91367(18) 0.24550(11) 0.0278(4) Uani 1 1 d . . . C11 C 1.2532(3) 0.99995(19) 0.30972(11) 0.0297(4) Uani 1 1 d . . . H11A H 1.3925 1.0459 0.3073 0.036 Uiso 1 1 calc R . . C12 C 1.0724(3) 1.01883(19) 0.37674(11) 0.0307(4) Uani 1 1 d . . . H12A H 1.0872 1.0792 0.4194 0.037 Uiso 1 1 calc R . . C13 C 0.8685(3) 0.94983(18) 0.38214(10) 0.0290(4) Uani 1 1 d . . . H13A H 0.7435 0.9642 0.4278 0.035 Uiso 1 1 calc R . . C14 C 0.8493(3) 0.86024(18) 0.32057(10) 0.0277(4) Uani 1 1 d . . . H14A H 0.7102 0.8129 0.3247 0.033 Uiso 1 1 calc R . . C15 C 0.7486(3) 0.53168(19) 0.28852(11) 0.0272(4) Uani 1 1 d . . . C16 C 0.5433(3) 0.45572(19) 0.30334(11) 0.0279(4) Uani 1 1 d . . . C17 C 0.4731(3) 0.35464(19) 0.39010(11) 0.0297(4) Uani 1 1 d . . . H17A H 0.3319 0.3069 0.4003 0.036 Uiso 1 1 calc R . . C18 C 0.6067(3) 0.32258(19) 0.46192(11) 0.0311(4) Uani 1 1 d . . . H18A H 0.5560 0.2544 0.5212 0.037 Uiso 1 1 calc R . . C19 C 0.8142(3) 0.39009(19) 0.44714(11) 0.0297(4) Uani 1 1 d . . . H19A H 0.9082 0.3658 0.4957 0.036 Uiso 1 1 calc R . . C20 C 0.8842(3) 0.49309(18) 0.36144(11) 0.0278(4) Uani 1 1 d . . . H20A H 1.0270 0.5386 0.3518 0.033 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 O1 0.0269(6) 0.0364(7) 0.0370(7) -0.0137(5) -0.0001(5) -0.0053(5) O2 0.0305(6) 0.0395(7) 0.0330(6) -0.0063(5) -0.0066(5) -0.0092(5) N1 0.0245(7) 0.0267(7) 0.0293(7) -0.0072(5) -0.0043(5) -0.0014(5) N2 0.0275(7) 0.0247(7) 0.0280(7) -0.0045(5) -0.0028(5) -0.0023(5) C1 0.0221(8) 0.0234(8) 0.0279(8) -0.0042(6) -0.0021(6) -0.0007(6) C2 0.0218(8) 0.0239(8) 0.0286(8) -0.0074(6) -0.0043(6) 0.0013(6) C3 0.0274(8) 0.0231(8) 0.0277(8) -0.0035(6) -0.0039(6) 0.0020(6) C4 0.0293(8) 0.0251(8) 0.0339(8) -0.0074(7) -0.0073(7) -0.0034(6) C5 0.0374(9) 0.0263(8) 0.0278(8) -0.0060(6) -0.0076(7) 0.0010(7) C6 0.0363(9) 0.0260(8) 0.0274(8) -0.0033(6) -0.0011(7) -0.0009(6) C7 0.0298(8) 0.0254(8) 0.0303(8) -0.0038(6) -0.0020(7) -0.0025(6) C8 0.0278(8) 0.0223(8) 0.0297(8) -0.0059(6) -0.0056(6) 0.0005(6) C9 0.0284(8) 0.0215(8) 0.0273(8) -0.0032(6) -0.0056(6) -0.0029(6) C10 0.0268(8) 0.0254(8) 0.0289(8) -0.0032(6) -0.0044(6) -0.0010(6) C11 0.0308(8) 0.0277(8) 0.0311(8) -0.0034(7) -0.0109(7) -0.0047(6) C12 0.0391(9) 0.0264(8) 0.0276(8) -0.0055(6) -0.0089(7) -0.0042(7) C13 0.0335(9) 0.0269(8) 0.0249(7) -0.0037(6) -0.0044(6) -0.0026(6) C14 0.0291(8) 0.0267(8) 0.0258(8) -0.0033(6) -0.0046(6) -0.0032(6) C15 0.0270(8) 0.0266(8) 0.0287(8) -0.0094(6) -0.0009(6) -0.0036(6) C16 0.0276(8) 0.0272(8) 0.0294(8) -0.0080(6) -0.0038(6) -0.0020(6) C17 0.0275(8) 0.0269(8) 0.0338(8) -0.0073(7) 0.0000(6) -0.0056(6) C18 0.0363(9) 0.0257(8) 0.0278(8) -0.0033(6) 0.0005(7) -0.0029(7) C19 0.0322(9) 0.0279(8) 0.0282(8) -0.0056(6) -0.0055(6) -0.0004(6) C20 0.0275(8) 0.0252(8) 0.0307(8) -0.0076(6) -0.0041(6) -0.0006(6) _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 O1 C10 1.3579(19) . ? O2 C16 1.3605(19) . ? N1 C2 1.3236(19) . ? N1 C3 1.366(2) . ? N2 C1 1.325(2) . ? N2 C8 1.368(2) . ? C1 C2 1.454(2) . ? C1 C9 1.480(2) . ? C2 C15 1.484(2) . ? C3 C8 1.410(2) . ? C3 C4 1.412(2) . ? C4 C5 1.370(2) . ? C5 C6 1.410(2) . ? C6 C7 1.368(2) . ? C7 C8 1.412(2) . ? C9 C14 1.403(2) . ? C9 C10 1.411(2) . ? C10 C11 1.397(2) . ? C11 C12 1.380(2) . ? C12 C13 1.393(2) . ? C13 C14 1.383(2) . ? C15 C20 1.404(2) . ? C15 C16 1.411(2) . ? C16 C17 1.389(2) . ? C17 C18 1.386(2) . ? C18 C19 1.385(2) . ? C19 C20 1.384(2) . ? 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 C2 N1 C3 119.78(13) . . ? C1 N2 C8 119.73(13) . . ? N2 C1 C2 119.50(13) . . ? N2 C1 C9 116.16(13) . . ? C2 C1 C9 124.09(13) . . ? N1 C2 C1 118.95(14) . . ? N1 C2 C15 116.68(13) . . ? C1 C2 C15 124.27(13) . . ? N1 C3 C8 119.89(14) . . ? N1 C3 C4 120.27(14) . . ? C8 C3 C4 119.68(14) . . ? C5 C4 C3 119.33(14) . . ? C4 C5 C6 120.76(14) . . ? C7 C6 C5 120.96(14) . . ? C6 C7 C8 119.21(15) . . ? N2 C8 C3 119.36(14) . . ? N2 C8 C7 120.68(14) . . ? C3 C8 C7 119.90(14) . . ? C14 C9 C10 118.13(14) . . ? C14 C9 C1 119.94(13) . . ? C10 C9 C1 121.34(14) . . ? O1 C10 C11 117.41(14) . . ? O1 C10 C9 122.65(14) . . ? C11 C10 C9 119.94(14) . . ? C12 C11 C10 120.45(14) . . ? C11 C12 C13 120.38(14) . . ? C14 C13 C12 119.48(15) . . ? C13 C14 C9 121.50(14) . . ? C20 C15 C16 117.96(14) . . ? C20 C15 C2 120.76(14) . . ? C16 C15 C2 121.06(14) . . ? O2 C16 C17 117.62(14) . . ? O2 C16 C15 122.37(14) . . ? C17 C16 C15 120.01(15) . . ? C18 C17 C16 120.77(15) . . ? C19 C18 C17 119.93(14) . . ? C20 C19 C18 119.82(14) . . ? C19 C20 C15 121.37(15) . . ? 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 C8 N2 C1 C2 9.7(2) . . . . ? C8 N2 C1 C9 -164.78(13) . . . . ? C3 N1 C2 C1 11.8(2) . . . . ? C3 N1 C2 C15 -164.65(13) . . . . ? N2 C1 C2 N1 -18.6(2) . . . . ? C9 C1 C2 N1 155.39(14) . . . . ? N2 C1 C2 C15 157.55(14) . . . . ? C9 C1 C2 C15 -28.4(2) . . . . ? C2 N1 C3 C8 2.8(2) . . . . ? C2 N1 C3 C4 178.18(14) . . . . ? N1 C3 C4 C5 -171.50(14) . . . . ? C8 C3 C4 C5 3.8(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C7 -2.3(2) . . . . ? C5 C6 C7 C8 1.7(2) . . . . ? C1 N2 C8 C3 5.0(2) . . . . ? C1 N2 C8 C7 -177.78(14) . . . . ? N1 C3 C8 N2 -11.8(2) . . . . ? C4 C3 C8 N2 172.82(14) . . . . ? N1 C3 C8 C7 170.93(14) . . . . ? C4 C3 C8 C7 -4.4(2) . . . . ? C6 C7 C8 N2 -175.53(14) . . . . ? C6 C7 C8 C3 1.7(2) . . . . ? N2 C1 C9 C14 146.65(14) . . . . ? C2 C1 C9 C14 -27.6(2) . . . . ? N2 C1 C9 C10 -24.5(2) . . . . ? C2 C1 C9 C10 161.33(14) . . . . ? C14 C9 C10 O1 -175.23(13) . . . . ? C1 C9 C10 O1 -4.0(2) . . . . ? C14 C9 C10 C11 4.0(2) . . . . ? C1 C9 C10 C11 175.24(14) . . . . ? O1 C10 C11 C12 175.73(13) . . . . ? C9 C10 C11 C12 -3.5(2) . . . . ? C10 C11 C12 C13 1.1(2) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C12 C13 C14 C9 -0.3(2) . . . . ? C10 C9 C14 C13 -2.1(2) . . . . ? C1 C9 C14 C13 -173.48(14) . . . . ? N1 C2 C15 C20 151.67(15) . . . . ? C1 C2 C15 C20 -24.6(2) . . . . ? N1 C2 C15 C16 -22.8(2) . . . . ? C1 C2 C15 C16 160.92(14) . . . . ? C20 C15 C16 O2 -175.59(14) . . . . ? C2 C15 C16 O2 -1.0(2) . . . . ? C20 C15 C16 C17 4.2(2) . . . . ? C2 C15 C16 C17 178.88(14) . . . . ? O2 C16 C17 C18 177.57(14) . . . . ? C15 C16 C17 C18 -2.3(2) . . . . ? C16 C17 C18 C19 -0.8(2) . . . . ? C17 C18 C19 C20 1.9(2) . . . . ? C18 C19 C20 C15 0.2(2) . . . . ? C16 C15 C20 C19 -3.3(2) . . . . ? C2 C15 C20 C19 -177.91(14) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.581 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.072