(1H-1,2,4-Triazol-1-yl)methyl 2-(2,4-dichlorophenoxy)acetate

In the title compound, C11H9Cl2N3O3, the triazole and benzene rings are roughly parallel to one another [dihedral angle = 4.99 (2)°] because the C—O—C—C—O chain that links the two rings is folded [O—C—C—O = 8.60 (2)°] rather than fully extended. In the crystal, weak intermolecular C—H⋯N and C—H⋯O interactions are present, and π–π interactions are indicated by the short distances [3.749 (3) Å] between the centroids of the triazole and benzene rings.

In the title compound, C 11 H 9 Cl 2 N 3 O 3 , the triazole and benzene rings are roughly parallel to one another [dihedral angle = 4.99 (2) ] because the C-O-C-C-O chain that links the two rings is folded [O-C-C-O = 8.60 (2) ] rather than fully extended. In the crystal, weak intermolecular C-HÁ Á ÁN and C-HÁ Á ÁO interactions are present, andinteractions are indicated by the short distances [3.749 (3) Å ] between the centroids of the triazole and benzene rings.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2669).

Comment
Compounds containing the triazole ring system are well known as efficient fungicides in agriculture, where they act by inhibiting the biosynthesis of ergosterol (Xu et al., 2002). In order to search for new triazole compounds with higher bioactivity, the title compound was synthesized and its structure is reported here.

Experimental
To a 100 ml flask were added 10 mmol of (1H-1,2,4-triazol-1-yl)methanol and 11 mmol of triethylamine in 20 ml of dryed acetone, to which 10 mmol of 2-(2,4-dichlorophenoxy)acetyl chloride in 10 ml of acetone was then dropwise added with stirring on ice-cold water bath within 0.5 h. The reaction took place immediately, and a lot of white solid appeared. The mixture was heated and refluxed for 2 h, and then cooled to room temperature. After filtering and distilling in reduced pressure, a crude product was obtained and purified by flash column chromatography (silicagel, using ethyl ethanoate: cyclohexane = 1:3 as eluent) to afford the title compound. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Refinement
H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93 or 0.97 Å and with U iso (H) = 1.2 times U eq (C). Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds