Research Article: 1-[4-(Difluoromethoxy)phenyl]-N-(2,3-dimethylphenyl)-1H-1,2,4-triazole-3-carboxamide

Date Published: May 01, 2009

Publisher: International Union of Crystallography

Author(s): Yu-Guang Wang, Guo-Bo Huang, Bing-Chun Zhu.

http://doi.org/10.1107/S160053680901263X

Abstract

In the mol­ecule of the title compound, C18H16F2N4O2, the 1,2,4-triazole ring forms dihedral angles of 3.6 (2) and 14.9 (6)° with the 4-difluoro­meth­oxy-substituted benzene ring and the 2,3-dimethyl-substituted benzene ring, respectively. The OCHF2 group is twisted away from the plane of the benzene ring, as shown by the C—O—C—C torsion angle of 145.8 (2)°. The conformation is stabilized by an inter­molecular N—H⋯N hydrogen bond. In the crystal, short C—H⋯O inter­actions lead to chains of mol­ecules.

Partial Text

For general background regarding the biological and pharmacological activities of 1,2,4-triazoles and their derivatives, see: Wahbi et al. (1995 ▶); Chai et al. (2003 ▶); Hashimoto et al. (1990 ▶); Kalluraya et al. (1996 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Kanazawa et al. (1988 ▶); Vlasova et al. (1971 ▶); Labanauskas et al. (2004 ▶); Tozkoparan et al. (2007 ▶). For a related synthesis, see: Drutkowski et al. (2002 ▶); Frohberg et al. (2002 ▶).

Source:

http://doi.org/10.1107/S160053680901263X