(E)-3-(4-Decyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

In the title compound, C25H32O3, the enone group is in an s–cis configuration. The dihedral angle between the benzene rings is 8.84 (7)°. An intramolecular O—H⋯O interaction between the keto and hydroxy groups forms an S(6) ring motif. Intermolecular C—H⋯O interactions link the molecules into supramolecular chains along the c axis which are subsequently stacked down the b axis; the crystal structure is further consolidated by C—H⋯π interactions.

In the title compound, C 25 H 32 O 3 , the enone group is in an s-cis configuration. The dihedral angle between the benzene rings is 8.84 (7) . An intramolecular O-HÁ Á ÁO interaction between the keto and hydroxy groups forms an S(6) ring motif. Intermolecular C-HÁ Á ÁO interactions link the molecules into supramolecular chains along the c axis which are subsequently stacked down the b axis; the crystal structure is further consolidated by C-HÁ Á Á interactions.

Comment
Chalcone is one of the important intermediates in the biosynthesis of flavonoid. Chalcones derivatives are reported to exhibit biological properties such as an anti-malarial (Xue et al., 2004), anti-cancer (Bhat et al., 2005, anti-inflammatory (Won et al., 2005), anti-platelet (Zhao et al., 2005), and as well as anti-hyperglycemic (Satyanarayana et al., 2004) activities.
Chalcone derivatives possessing alkyl chains of varying length have been synthesized in our laboratory. They were tested against E. coli ATCC 8739 for their anti-bacterial activities and showed anti-microbial activity. In this paper, we report the structure of one of the chalcone derivatives mentioned above.
In the crystal structure, C15-H15A···O3 (x, -y + 1/2, z + 1/2) intermolecular interactions link the molecules into extended chains along the c axis (Table 1 and Fig. 2). These chains are subsequently stacked down the b axis. The crystal packing is further stabilized by the presence of C-H···π interactions formed between atoms C16, C20 and C22 in the alkoxyl tail and the benzene rings (Table 1).

Experimental
A mixture of 2-hydroxyacetophenone (2.72 ml, 20 mmol), 4-decyloxybenzaldehyde (5.25 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in methanol (60 ml) was heated at reflux for 10 h. The reaction mixture was cooled to room temperature and acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane and followed by few days of slow evaporation, crystals were collected.