(E)-1-Ferrocenyl-3-(4-methoxyphenyl)prop-2-en-1-one

In the title compound, [Fe(C5H5)(C15H13O2)], a conjugated substituent group bridges a five-membered η5-C5H4 ring and a benzene ring. In the ferrocene unit, the substituted (Cps) and unsubstituted (Cp) cyclopentadienyl rings are eclipsed and almost parallel [Cps—Fe—Cps angle = 176.1 (2)°]. The molecule is linked into an S(5) motif via intramolecular C—H⋯O hydrogen bonds. The molecules are arranged into a three-dimensional framework by five intermolecular C—H⋯O hydrogen bonds and one intermolecular C—H⋯π(Cps) interaction.

In the title compound, [Fe(C 5 H 5 )(C 15 H 13 O 2 )], a conjugated substituent group bridges a five-membered 5 -C 5 H 4 ring and a benzene ring. In the ferrocene unit, the substituted (Cps) and unsubstituted (Cp) cyclopentadienyl rings are eclipsed and almost parallel [Cps-Fe-Cps angle = 176.1 (2) ]. The molecule is linked into an S(5) motif via intramolecular C-HÁ Á ÁO hydrogen bonds. The molecules are arranged into a three-dimensional framework by five intermolecular C-HÁ Á ÁO hydrogen bonds and one intermolecular C-HÁ Á Á(Cps) interaction.
Cg1 is the centroid of the substituted cyclopentadienyl ring.

Comment
Chalcone and its derivatives, as natural products, have attracted considerable attention for their stronge antibacterial, antifungal, antitumor and anti-inflammatory properties, especially antileishmanial and antimalarial (Zhai et al.,1999;Liu et al., 2001Liu et al., , 2003 over the past years. Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). It was proved that the replacement of the aromatic group by the ferrocenyl moiety in penicillins and cephalosporins improves their antibiotic activity (Edwards et al., 1975). As part of our search for new biologically active compounds (Liu et al.,2008;Shi et al., 2004;Liang et al., 1998), we have synthesized the title compound (I) and describe its structure in this paper.
The molecule of the title compound (I) exists as the most stable configuration of (E)-isomer (Scheme 1, Fig.1) and all carbon atoms (except that of methoxyl group) and O1 are sp 2 -hybridized and form two large conjugated systems; one is formed by C1 to C5 and the other C6 to C19 including O1, just as its parent compound II (Scheme 2) (Liu et al., 2008). In the molecule there is a C(5) (Bernstein et al., 1995) C-H···O intra-molecular hydrogen-bond which makes the four atoms O1, C11, C12 and C13 be coplanar (plane-1). The Cps (the substituted cyclopentadienyl ring) plane, the plane-1 and plane-2 (the phenyl ring plane) are not coplanar. In the ferrocene moiety, the Cps and the Cp (the unsubstituted cyclopentadienyl  Table 1). All of the above mentioned inter-molecular hydrogen-bonds link the molecules into a three-dimensional structure of considerable complexity.

Experimental
The title compound was synthesized according to the literature procedure (Huang et al. 1998). Crystals of I suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in dichloromethane / ether (5:1 v/v) at room temperature over a period of 6 days.

Refinement
After their location in a difference map, all H atoms were fixed geometrically at ideal positions and allowed to ride on the parent C atoms, with C-H distances of 0.93 -0.96, and with U ĩso (H) values of 1.2U eq (C). Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. The C-H···O intra-molecular hydrogen bond is shown as dashed lines.