(E)-1-(3-Hydroxyphenyl)-3-[4-(tetradecyloxy)phenyl]prop-2-en-1-one

In the title compound, C29H40O3, the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33 (5)° The least-squares mean line through the tetradecyl side chain forms a dihedral angle of 83.99 (7)° with the normal to the attached benzene ring. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds involving the keto and the hydroxy O atoms form ribbons along [-41-1]. The crystal structure also features C—H⋯π interactions.


Experimental
A mixture of 3-hydroxyacetophenone (1.36 g, 10 mmol) and 4-tetradecyloxybenzaldehyde (3.19 ml, 10 mmol) in methanol (40 ml) was heated at reflux for 12 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane-ethanol (7:1 v/v) followed by few days of slow evaporation, crystals were collected.

Refinement
The O-bound H atom was located in a difference Fourier map and refined freely with O-H = 0.927 (19) Å. The remaining H atoms were placed in calculated positions with C-H = 0.93-0.97 Å. The U iso values were constrained to be 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for other H atoms. The rotating model group was applied to the methyl group. Two supplementary materials sup-2 Acta Cryst. (2012). E68, o2911-o2912 outliers (0 0 1) and (1 0 1) were omitted.

Figure 1
The structure of the title compound, showing 50% probability displacement ellipsoids.

Figure 2
Packing diagram of the title compound viewed down the a axis, showing the alternately interconnected extended chains parallel to the [4 -1 1] direction. Hydrogen atoms not involved in hydrogen bonds (dashed lines) are omitted.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1