Date Published: April 01, 2012
Publisher: International Union of Crystallography
Author(s): Abdullah M. Asiri, Hassan M. Faidallah, Khalid A. Alamry, Seik Weng Ng, Edward R. T. Tiekink.
In the title compound, C24H19N3O2, the partially saturated ring adopts a distorted half-chair conformation with the methylene-C atom closest to the aminobenzene ring lying 0.664 (3) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429 Å. The dihedral angle [32.01 (10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the molecule. The dimethoxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The molecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873–o2873]. Supramolecular chains with base vector  are formed in the crystal structure via N—H⋯O hydrogen bonds between the amino H atoms of one molecule interacting with the methoxy O atoms of a neighbouring molecule. The chains are linked into a three-dimensional architecture by C—H⋯π interactions.
For background to the biological activity of related phenanthrene compounds, see: Wang et al. (2010 ▶); Rostom et al. (2011 ▶). For related structures, see: Asiri et al. (2011a ▶,b ▶); Al-Youbi et al. (2012 ▶).