Crystal structure of difenoconazole

In the title compound difenoconazole [systematic name: 1-({2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole], C19H17Cl2N3O3, the dihedral angle between the planes of the 4-chlorophenyl and 2-chlorophenyl 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 molecules, 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).


S2. Experimental
The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH 2 Cl 2 gave single crystals suitable for X-ray analysis.

S3. Refinement
During refinement, the C15 atom of the dioxolanyl group was disordered and was refined using a split model. The corresponding site-occupation factors were refined so that their sum was unity [0.566 (17) and 0.434 (17)]. All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.98 Å, U iso = 1.5U eq (C) for methyl group, d(C-H) = 0.99 Å, U iso = 1.2U eq (C) for Csp 3 -H, d(C-H) = 0.95 Å, U iso = 1.2U eq (C) for aromatic C-H, and d(C -H) = 1.00 Å, U iso = 1.5U eq (C) for Csp 3 -H. 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.

Figure 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.

1-({2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole
Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ.