1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole

In the molecule of the title compound, C15H13Cl2N3O2, the triazole ring is oriented at dihedral angles of 2.54 (13) and 44.43 (12)°, respectively with respect to the furan and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and furan rings is 46.75 (12)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers and π–π contacts between dichlorobenzene rings [centroid–centroid distance = 3.583 (2) Å] may further stabilize the structure. Intermolecular C—H⋯π contacts between the triazole and furan rings also occur.

In the molecule of the title compound, C 15 H 13 Cl 2 N 3 O 2 , the triazole ring is oriented at dihedral angles of 2.54 (13) and 44.43 (12) , respectively with respect to the furan and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and furan rings is 46.75 (12) . In the crystal structure, intermolecular C-HÁ Á ÁO hydrogen bonds link the molecules into centrosymmetric dimers andcontacts between dichlorobenzene rings [centroid-centroid distance = 3.583 (2) Å ] may further stabilize the structure. Intermolecular C-HÁ Á Á contacts between the triazole and furan rings also occur.
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contact between the dichlorobenzene rings, Cg3-Cg3 i [symmetry code: (i) -x, -y, 1 -z, where Cg3 is centroid of the ring (C10-C15)] may further stabilize the structure, with centroid-centroid distance of 3.583 (2) Å. Intermolecular C-H···π interactions (Table 1) are also observed between the triazole and furan rings.

Experimental
The title compound was synthesized by the reaction of 1-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (unpublished results) with NaH and appropriate benzyl halide. To a solution of alcohol (500 mg, 2.791 mmol) in DMF (4 ml) was added NaH (112 mg, 2.791 mmol) in small fractions. The appropriate benzyl halide (669 mg, 2.791 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, and excess hydride was decomposed with methyl alcohol (5 ml). After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude residue was supplementary materials sup-2 purified by chromatography on a silica-gel column using chloroform as eluent. Crystals suitable for X-ray analysis were obtained by the recrystallization of the ether from isopropanol solution (yield; 500 mg, 53%).

Refinement
H atoms were positioned geometrically, with C-H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H, respectively, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.

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 in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.