(E)-3-[2-(4-Chlorophenylsulfonyl)vinyl]-6-methyl-4H-chromen-4-one

In the title compound, C18H13ClO4S, the mean planes of the chlorophenyl ring and the S—C=C—C chain are oriented at angles of 52.7 (2) and 51.3 (2)°, respectively, with respect to the sulfonyl (O=S=O) plane. The dihedral angle between the mean planes of the chlorophenyl group and the benzopyran ring is 80.7 (1)°. The crystal structure is stabilized by two intermolecular C—H⋯O interactions, forming centrosymmetrc dimers, which are linked via a second C—H⋯O interaction into a chain structure.

In the title compound, C 18 H 13 ClO 4 S, the mean planes of the chlorophenyl ring and the S-C C-C chain are oriented at angles of 52.7 (2) and 51.3 (2) , respectively, with respect to the sulfonyl (O S O) plane. The dihedral angle between the mean planes of the chlorophenyl group and the benzopyran ring is 80.7 (1) . The crystal structure is stabilized by two intermolecular C-HÁ Á ÁO interactions, forming centrosymmetrc dimers, which are linked via a second C-HÁ Á ÁO interaction into a chain structure.

Related literature
For the biological properties of sulfonones and for related structures, see: Alonso et al. (2002); Raju et al. (1996); Chen et al. (1996); Mukundam (1990); Krishnaiah et al. (1995); Sethu Sankar et al. (2002). For bond-length data, see: Allen et al. (1987);Sethu Sankar et al. (2002). For double-bond character, see: Cruickshank (1961 Table 1 Hydrogen-bond geometry (Å , ). Sulfones are useful building blocks in the preparation and functionalization of a wide variety of products (Alonso et al., 2002). They are similarly to sulfonamides, showing strong in vitro and in vivo antibacterial activity, and for almost 60 years have been used successfully in medicine. Certain sulfones also display anti-bacterial and anti-fungal properties (Raju et al., 1996). The anti-fungal activity of some unsaturated sulfones has been found to be dependent upon the substituents and stereochemical effects (Chen et al., 1996). The title compound has been observed to display anti-fungal activity against curularia luneta and furasium oxysporum (Mukundam, 1990). The determination of the structure of the title compound was undertaken to study the conformation of the molecule and to contribute to the growing structural data becoming available for the characterization of the structure activity relationships.
The molecular structure of the title compound is illustrated in Fig In the crystal structure of the title compound symmetry related molecules are linked via C-H···O interactions (Table   1), forming centrosymmetric dimers (via interaction C10-H10···O3). These in turn are linked via a second interaction (C2-H2···O2) to form a chain like structure (Fig. 2).
The title compound was synthesized accordng to the procedure descibed by (Mukundam, 1990). To a solution of 1.74 mg (0.01 mol) of 6-methyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde and 2.35 mg (0.01 mol) of 4 chlorophenylsulfonylacetic acid in 10 ml of glacial acetic acid was added 0.2 ml of benzyl amine. The resulting solution was refluxed for 3 h. The reaction mixture was cooled and yielded 1.5 mg of the title compound. It was recrystallized from glacial acetic acid, affording colourless crystals (m.p.500-504 k), suitable for X-ray diffraction analysis.

Refinement
All the H-atoms were included in calculated positions and treated as riding atoms: C-H (aromatic)= 0.93 Å, (C-methyl) C-H = 0.96 Å, with U iso (H) = 1.2Ueq(C-aromatic) and = 1.5Ueq(C-methyl). Fig. 1. A view of the molecular structure of the title compound, showing the atom-labelling scheme and the displacement ellipsoids drawn at the 50% probability level.  Table 1 for details).  as those based on F, and R-factors based on ALL data will be even larger.