Research Article: 3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

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 [201] 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.

Partial Text

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 ▶).