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

In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hydroxyphenyl ring and 11.5 (1)° with the chlorophenyl ring. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].

Cg1 is the centroid of the C1-C6 ring.
BKS thanks the P. A. College of Engineering for the research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5108).
erties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives. Chalcones have been reported to possess many useful properties, including antiinflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Nowakowska, 2007).
Certain chalcone derivatives are reported to inhibit the polymerization of tubulin to form microtubules and are therefore antimitotic agents which can be used as antigout agents. The chalcone derivatives are also reported to inhibit the destruction of the myelin sheath in the central nervous system of multiple sclerosis patients and are thus useful in controlling the progressive nature of the disease (Edwards et al., 1989).
In a continuation of our studies on the crystal structures of chalcones (Jasinski et al., 2010(Jasinski et al., , 2011a(Jasinski et al., , 2011b, we report here the synthesis and crystal structure of the title compound, C 15 H 11 ClO 2 , (I), Fig. 2. The dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 18.0 (1)° with the hydroxy benzene and 11.5 (1)° with the chlorobenzene rings, respectively. Bond lengths are normal (Allen et al., 1987) and correspond to those observed in related compounds (Butcher et al., 2007a(Butcher et al., , 2007bNarayana et al., 2007;Sarojini et al., 2007aSarojini et al., , 2007b. Crystal packing is stabilized by O-H···O hydrogen bonds, weak C-H···O, C-H···Cg π-ring (Table 1) and π-π intermolecular stacking interactions ( Table 2