Date Published: July 01, 2012
Publisher: International Union of Crystallography
Author(s): Huang Tang, Zhi-Yu Wang, Yan-Cheng Liu.
The title compound, C18H14N2O2, is a new oxoisoaporphine derivative synthesized by alkylation of 6-chloro-1-azabenzanthrone. The oxoisoaporphine fragment deviates significantly from planarity with a dihedral angle of 5.1 (1)° between the heterocycle and the remote benzene ring. The amino and oxo groups are involved in an intramolecular N—H⋯O hydrogen bond, while the hydroxy groups form intermolecular O—H⋯N hydrogen bonds, which link pairs of molecules into inversion dimers. In the dimer, two approximately parallel oxoisoaporphine fragments exhibit π–π interactions between the aromatic rings, the shortest centroid–centroid distance being 3.649 (3) Å.
For related oxoisoaporphine alkaloids, see: Tang et al. (2011 ▶, 2012 ▶). For background to the synthesis of 6-chloro-1-azabenzanthrone, see: Iwashima et al. (1984 ▶).