Abstract
Tricyclic dibenzo derivatives of the seven-membered oxepine, azepine and cycloheptatriene rings are the parent systems of several clinically-active psychotropic drugs [1,2]. In six- and seven-membered-ring derivatives with central-nervous-system psychopharmacological activity [3, 4, 5], ability to induce such action may be associated with a degree of non-planarity and low aromaticity of the central ring. In the crystalline state, dibenz[ b, f ] oxepine (I) [6] and the isoelectronic dibenz [ b,f ] azepine (II) (studied independently [7], but found to have remarkably similar dimensions) take up an overall butterfly or saddle shape with the heterocyclic rings in boat conformation. The dihedral angle between the almost planar benzene rings in the crystal structure of I [6] is 134° and 145° in II [7]. Photo-electron [8] and electronic [9] spectra provide some evidence for the non-planarity of I and II in the gas phase and in methanol solution.
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