1-[4-(Difluoromethoxy)phenyl]-N-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamide

Abstract

Two crystallographically independent mol­ecules, A and B, with similar conformations are present in the asymmetric unit of the title compound, C18H16F2N4O4. In mol­ecule A, the plane of the 1,2,4-triazole ring is tilted relative of the 4-difluoro­meth­oxy-substituted and the 3,4-dimeth­oxy-substituted benzene rings by 6.5 (2) and 16.4 (1)°, respectively. The –CHF2 group is twisted away from the plane of the benzene ring, with a dihedral angle between the O—C bond of the OCHF2 group and the plane of the adjacent phenyl ring of 38.6 (3)°. The corresponding parameters for mol­ecule B are 7.7 (1), 9.5 (2) and 25.2 (2)°. In both mol­ecules, the conformations are stabilized by intra­molecular N—H⋯N and C—H⋯O hydrogen bonds. There are also C—H⋯π contacts between the methyl groups and the benzene rings, and π–π stacking inter­actions between the benzene rings of adjacent parallel A mol­ecules [centroid–centroid distance = 3.8942 (17) Å]. π–π inter­actions are also observed between the triazole ring and one of the benzene rings of parallel B mol­ecules [centroid–centroid distance = 3.7055 (16) Å].

N′-(3,4-Dichlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide

“…The dihedral angle between the nitro-substituted (C1-C6) and dichlorosubstituted (C11-C16) phenyl rings is 6.68 (5)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Fun et al, 2011;Wang et al, 2010).…”

“…For aryl hydrazones, see: Sridhar & Perumal (2003); Bedia et al (2006); Rollas et al (2002); Terzioglu & Gü rsoy (2003). For related structures, see: Fun et al (2011); Wang et al (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).…”