Crystal structure of 2-(4-fluoro-3-methylphenyl)-5-{[(naphthalen-1-yl)oxy]methyl}-1,3,4-oxadiazole

The title compound, C20H15FN2O2, adopts an almost planar conformation. The oxadiazole ring makes dihedral angles of 13.90 (1) and 7.93 (1)° with the naphthalene ring system and benzene ring, respectively, while the naphthalene ring system and benzene ring are inclined to one another by 6.35 (1)°. In the crystal, adjacent molecules are linked via C—H⋯N hydrogen bonds, forming chains propagating along [100]. There are also π–π interactions present [intercentroid distances = 3.5754 (9) and 3.7191 (12) Å], linking the chains to form ribbons lying parallel to (011).


S2. Experimental
Iodobenzene diacetate (2.0 mol eq) was added to a solution of naphthalen -1-yloxy-acetic acid (4-fluoro-3-methylbenzylidene)-hydrazide (1.0 mole eq) in dioxane (10mL) at 298 -303 K, and stirred at the same temperature for 15-30 min. Completion of the reaction was confirmed by TLC (Mobile phase Ethyl acetate/hexane, 3:7) and dioxane was distilled off in a rota-vapor. The obtained residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution, followed by water and brine solution. The organic layer was collected and dried over anhydrous sodium sulphate and distilled under vacuum. The crude product obtained was purified by column chromatography over silica gel (60-120 mesh) using hexane and ethyl acetate as a eluent to afford the title compound as an off-white solid. It was crystallised in methanol by slow evaporation giving colourless block-like crystals.
supporting information

S3. Refinement
The H atoms were placed in calculated positions and refined as riding atoms: C-H = 0.93 -0.97 Å, with U iso (H) = 1.5U eq (C) for methyl H atoms and = 1.2U eq (C) for other H atoms.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table   1 for details). H atoms not involved in hydrogen bonds have been omitted for clarity.

sup-3
Acta Cryst. (2015). E71, o229-o230 where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.16 e Å −3 Δρ min = −0.22 e Å −3 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.