Oxcarbazepine: structure and anticonvulsant activity

In the crystal structure of the title compound, 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide, C15H12N2O2, the azepine seven-membered ring adopts a classical but slightly twisted boat conformation, forcing the molecule to adopt a butterfly shape. In addition to one normal hydrogen bond, two non-standard weak hydrogen bonds of the C-H center dot center dot center dot O type also contribute to the molecular arrangement in the crystal structure. Stereochemical comparison with phenytoin indicates that oxcarbazepine may utilize the same mechanism for its anticonvulsant activity.