4-[(E)-3-(4-Methylphenyl)-3-oxoprop-1-en-1-yl]benzonitrile

In the title molecule, the phenyl rings areinclined to one another by 48.04 (9)°. In the crystal, weak C—H⋯π(ring) interactions form a layered structure.

In the title molecule C 17 H 13 NO, the phenyl rings are inclined to one another by 48.04 (9) . In the crystal, weak C-HÁ Á Á(ring) interactions form a layered structure parallel to the ab plane.

Structure description
Chalcones are compounds that can be easily synthesized, and their analogs can also be isolated from natural products (Dhar, 1981). Apart from their biological applications, some chalcones with appropriate substituents are also reported to be good NLO materials (Shettigar et al., 2006). As part of our work in this area, we now describe the synthesis and structure of the title compound (Fig. 1).
The 4-cyanophenyl and 4-methylbenzoyl units are disposed in a trans fashion about the C7 C8 double bond. The dihedral angle between the planes of the C1-C6 and C10-C15 benzene rings is 48.04 (9) and these benzene rings are inclined to the plane defined by the propene atoms C7, C8 and C9 by 16.0 (1) and 32.6 (1) , respectively, while O1 lies 0.24 (1) Å away from the propene plane.
In the crystal, stacked molecules form layers parallel to the ab plane with the para substituents on the phenyl rings on the outside surfaces of the layers (Figs. 2 and 3). The molecules constituting each layer are associated through very weak C2-H2Á Á ÁCg2, C5-H5Á Á ÁCg2, C12-H12Á Á ÁCg1 and C15-H15Á Á ÁCg1 interactions across centers of symmetry (Table 1; Cg1 and Cg2 are the centroids of rings C1-C6 and C10-C15, respectively).

data reports Synthesis and crystallization
An equimolar mixture of 4-methylacetophenone (0.01 mol) and 4-cyanobenzaldehyde (0.01 mol) in ethanol (30 ml) was View of a portion of one layer viewed along the b-axis direction with C-HÁ Á Á(ring) interactions depicted by dashed lines. Table 1 Hydrogen-bond geometry (Å , ).

Figure 2
Elevation view of a portion of one layer viewed along the a-axis direction with C-HÁ Á Á(ring) interactions depicted by dashed lines.

Figure 1
The title molecule showing 30% probability ellipsoids.
stirred for 3 h in the presence of NaOH (5 ml, 30%) at 283 K. The crude solid obtained was collected by filtration and dried. It was purified by repeated recrystallization. Thin layer chromatography was used to check the purity of the compound. Single crystals were grown from ethanol solution by slow evaporation, yield 86%, m.p. 415 K.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2.

4-[(E)-3-(4-Methylphenyl)-3-oxoprop-1-en-1-yl]benzonitrile
Dandavathi Arunkumar, Seranthimata Samshuddin, Mhammed Ansar, Joel T. Mague and Youssef 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. Hatoms attached to carbon were placed in calculated positions (C-H = 0.95 -0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms.