3-Amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile

Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o1118-9. doi: 10.1107/S1600536812011129. Epub 2012 Mar 21.

Abstract

In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl-ene-C atom closest to the amino-benzene 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 mol-ecule. The dimeth-oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The mol-ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873-o2873]. Supra-molecular chains with base vector [201] are formed in the crystal structure via N-H⋯O hydrogen bonds between the amino H atoms of one mol-ecule inter-acting with the meth-oxy O atoms of a neighbouring mol-ecule. The chains are linked into a three-dimensional architecture by C-H⋯π inter-actions.