Synthesis and Structural Characterization of N-(2-Carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide

Abstract

The compound N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (C₁₅H₁₁NO₅, M_r = 285.25) was synthesized and characterized by elemental analysis, ¹H NMR spectra, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 8.4994(8), b = 14.6499(15), c = 10.2880(10) Å, b = 101.5890(10)º, V = 1254.9(2) ų, Z = 4, D_c = 1.510 g/cm³, l = 0.71073 Å, (MoK_a) = 0.115 mm^-1, F₍₀₀₀₎ = 592. The final refinement gave R = 0.0374, wR(F²) = 0.0856 for 2,201 observed reflections with I > 2s(I). The structure of the compound comprises a racemic mixture of chiral molecules containing four stereogenic centres. X-Ray diffraction analysis reveals that the cyclohexane ring tends towards a boat conformation, the tetrahydrofuran ring and the dihydrofuran ring adopt envelope conformations. The dihedral angle between the pyrrolidine-2,5-dione plane and the aromatic ring is 65.0 (1)º. The crystal structure is stabilized by O-H···O and C-H···O hydrogen bonds.