Methyl (2Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(naphthalen-1-yl)prop-2-enoate

In the title compound, C29H25NO5S, the sulfonyl-bound benzene ring forms dihedral angles of 42.1 (1) and 48.5 (1)°, respectively, with the formyl-substituted benzene ring and the naphthalene residue. In the crystal, pairs of C—H⋯O interactions lead to the formation of R 2 2(10) inversion dimers, which are linked by further C—H⋯O interactions into supramolecular tapes running along [100]. The crystal packing is further stabilized by C—H⋯π interactions.

In the title compound, C 29 H 25 NO 5 S, the sulfonyl-bound benzene ring forms dihedral angles of 42.1 (1) and 48.5 (1) , respectively, with the formyl-substituted benzene ring and the naphthalene residue. In the crystal, pairs of C-HÁ Á ÁO interactions lead to the formation of R 2 2 (10) inversion dimers, which are linked by further C-HÁ Á ÁO interactions into supramolecular tapes running along [100]. The crystal packing is further stabilized by C-HÁ Á Á interactions.

Comment
Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988, Mandell & Sande, 1992. In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here. Å respectively for these bonds (Varghese et al., 1986). The sum of bond angles around N1 (350.6°) indicates that N1 is in sp 2 hybridization. The sulfonyl-bound benzene (C8-C13) ring forms dihedral angles of 42.1 (1)° and 48.5 (1)° respectively, with the formyl phenyl (C1-C6) and naphthalene (C18-C23/C26-C29) rings. The dihedral angle between formyl phenyl and naphthalene rings is 8.9 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Madhanraj et al., 2011;Aziz-ur-Rehman et al., 2010).
The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.450 g, 90% yield). Recrystallization was carried out using ethylacetate as solvent.

Refinement
All the H atoms were positioned geometrically, with C-H = 0.93-0.97 Å and constrained to ride on their parent atom, with U iso (H) =1.5U eq for methyl H atoms and 1.2U eq (C) for other H atoms.

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.