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

Abstract

The compound N-phenyl-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (C₁₄H₁₁NO₃, Mr = 241.24) 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/c, with a = 9.4307(7), b = 8.3175(6), c = 14.3592(15) Å, β = 93.6000(10)º, V = 1124.11(17) ų, Z = 4, Dc = 1.425 g/cm3, λ = 0.71073 Å, μ(Mo K_α) = 0.101 mm^-1, F(000) = 504. The final refinement gave R = 0.0424, wR(F2) = 0.1058 for 1,975 observed reflections with I > 2σ(I). The structure of this 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 phenyl plane is 50.4 (2)º.