1-(1-Benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one

In the title compound, C17H11ClO2, the benzofuran ring system is almost planar (r.m.s. deviation = 0.011 Å) and forms a dihedral angle of 10.53 (6)° with the chlorophenyl ring. No significant intermolecular interactions are observed.

In the title compound, C 17 H 11 ClO 2 , the benzofuran ring system is almost planar (r.m.s. deviation = 0.011 Å ) and forms a dihedral angle of 10.53 (6) with the chlorophenyl ring. No significant intermolecular interactions are observed.

Related literature
For general background to chalcone, see: Dhar (1981).  1-(1-Benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one S. Jeyaseelan, H. C. Devarajegowda, G. Venkatarama, M. Vinduvahini and A. D'souza Comment Chalcones have been recognized as a significant field of study for a long time because of a variety of biological activities as well as they serve as intermediates in the synthesis of a variety of heterocyclic compounds. Several heterocyclic analogues of chalcones have been reported to possess antibacterial, bacteriostatic tuberculostatic, insecticidal, antiparasitic, coronary vasodilating and choleretic activities (Dhar, 1981). Further, benzofuran derivatives have been reported to possess sedative and hypnotic (Nasef et al., 1992), antiinflammatory (Bogolyubsakaya & Perovich, 1964), antidepressant (Deshmukh et al., 2004), analgesic (Stanislav et al., 2000, hypoglycemic (Brady et al., 1973), anticonvulsant (Kamal et al., 2006), antibacterial (Alejandro et al., 2008 and antifungal activities (Rajesh et al., 2006). Owing to these biological activities of benzofuran propenones and in an attempt to study the structure-activity relationship of benzofuran and related systems, it was contemplated to synthesize benzofuryl propenones and the crystal structure of one of them, the title compound, is reported. The benzofuran ring system is almost planar (r.m.s. deviation 0.011 Å). The dihedral angle between the benzofuran ring system and the chlorophenyl ring is 10.53 (6)°. Bond distances within the aromatic rings are in agreement with those observed in related structures (Devarajegowda et al., 2001;Kant et al., 2009).

Experimental
A mixture of 2-acetylbenzofuran (0.01 mol) and p-chlorobenzaldehyde (0.01 mol) in ethanol (20 ml) was stirred for 24 h in aqueous NaOH (8 ml). It was then diluted with water (100 ml) and acidified with concentrated HCl. The course of the reaction was monitored by TLC using chloroform-carbon disulfide (1:1). The product obtained was filtered, washed with water and recrystallised from ethanol (m.p. 398 K). Spectral data IR (KBr) cm -1 : 1650 (C═O), 1620 (C═C stretching in   supplementary materials sup-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.