Research Article: 6-[(2-Hy­droxy­eth­yl)amino]-7H-dibenzo[de,h]quinolin-7-one

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.

Partial Text

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 ▶).




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