Research Article: 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methyl­propane­nitrile

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 [001] by N—H⋯N hydrogen bonds.

Partial Text

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 ▶).




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