Crystal structure of difenoconazole

Abstract

In the title compound difenoconazole [systematic name: 1-({2-[2-chloro-4-(4-chloro-phen-oxy)phen-yl]-4-methyl-1,3-dioxolan-2-yl}meth-yl)-1H-1,2,4-triazole], C19H17Cl2N3O3, the dihedral angle between the planes of the 4-chloro-phenyl and 2-chloro-phenyl rings is 79.34 (9)°, while the dihedral angle between the planes of the triazole ring and the dioxolanyl group is 59.45 (19)°. In the crystal, pairs of C-H⋯N hydrogen bonds link adjacent mol-ecules, forming dimers with R 2 (2)(6) loops. In addition, the dimers are linked by C-H⋯O hydrogen bonds, resulting in a three-dimensional architecture. Disorder was modeled for one C atom of the dioxolanyl group over two sets of sites with an occupancy ratio of 0.566 (17):0.434 (17).

Keywords: crystal structure; difenoconazole; hydrogen bonds; triazole fungicide.

Fig. 1.

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. Only atoms of the major disorder components are shown.

Fig. 2.

Crystal packing of the title compound with C—H···N and C—H···O hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of hydrogen bonds. Only atoms of the major disorder components are shown.