Molecular structure of novel derivative of bicyclo [3.3.1] non-3-ene-2-one: Experimental and theoretical study

The synthesis and molecular structure of 5-ethoxycarbonyl-8-hydroxy-8-methyl-4-(4-nitrophenyl)-bicyclo [3.3.1] non-3-ene-2-one 5, C19H21NO6 is described here. Structure 5 has a bicyclic [3.3.1] cage with aryl ring (4-nitro-phenyl) substituted at C4 position in which a cyclohexenone (C1C2C3C4C5C9) and cyclohexane (C1C8C7C6C5C9) rings are described. The structural analysis of the title was carried out by experimental (single crystal X-ray diffraction, 1H and 13C NMR) and confirmed by theoretical calculations (DFT and NMR–DFT–GIAO). The good correlations between experimental NMR and DFT–GIAO values lead to the unequivocal assignment of the H and C atoms.