Date Published: June 01, 2012
Publisher: International Union of Crystallography
Author(s): Ewa Wolińska, Zbigniew Karczmarzyk, Andrzej Rykowski, Zofia Urbańczyk-Lipkowska, Przemysław Kalicki.
The title compound, C19H17ClN4, was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intramolecular C—H⋯N interactions occur. In the crystal, molecules related by a c-glide plane are linked into zigzag chains along  by N—H⋯N hydrogen bonds.
For background information, see: Hargaden & Guiry (2009 ▶); Konno et al. (1987 ▶); Rykowski et al. (2000 ▶). For the synthesis, see: Coeffard et al. (2009 ▶); Fujisawa et al. (1995 ▶). For a related structure, see: Ayato et al. (1981 ▶).