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

In the title compound, C25H32O3, the asymmetric unit contains two crystallographically independent molecules: both enone groups adopt an s-cis configuration. In the crystal, O—H⋯O and C—H⋯O intermolecular interactions form bifurcated hydrogen bonds, which generate R 1 2(6) ring motifs. These intermolecular interactions link the molecules into one-dimensional chains along the [10] direction. The crystal structure is further stabilized by C—H⋯π interactions.


Comment
Chalcone derivatives are reported to possess biological properties such as anticancer (Bhat et al., 2005), antimalarial (Xue et al., 2004), antioxidant and antimicrobial activities (Yayli et al., 2006), antiplatelet activity (Zhao et al., 2005) as well as antihyperglycemic activity (Satyanarayana et al., 2004). Chalcone derivatives possessing alkyl chains have been synthesized in our lab and their antibacterial activities were tested against E. coli ATCC 8739. All the synthesized chalcone derivatives showed antimicrobial activity. The structure reported in this paper, (I), is one of the chalcone derivatives mentioned above.
Similar feature was also discussed in structures reported by  and .

Experimental
A mixture of 4-hydroxybenzaldehyde (2.44 g, 20 mmol) and 4-decyloxyacethophenone (5.53 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in 60 ml of methanol was heated at reflux for 24 h. The reaction was cooled to room temperature and was acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. The precipitate was dissolved in hexane-ethanol (7:1) mixture. After a few days of slow evaporation, crystals suitable for X-ray analysis were collected.
supplementary materials sup-2 Refinement All the carbon-bound H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.97 Å.
The U iso values were constrained to be U iso (H) =1.5U equ (methyl H atoms) and U iso (H) =1.2U equ (other H atoms). The rotating model group was considered for the methyl group. In the case of O1A and O1B, the hydrogen atoms were located from a difference Fourier map and refined isotropically. Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.  Table 2.