Methyl (Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-phenylprop-2-enoate

In the title compound, C25H23NO5S, the sulfonyl-bound benzene ring forms dihedral angles of 37.2 (1) and 67.0 (1)°, respectively, with the formylphenyl and phenyl rings. The molecular conformation is stabilized by an intramolecular C—H⋯π interaction. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a two-dimensional network in the (110) plane in which R 4 4(38) ring motifs are generated.

In the title compound, C 25 H 23 NO 5 S, the sulfonyl-bound benzene ring forms dihedral angles of 37.2 (1) and 67.0 (1) , respectively, with the formylphenyl and phenyl rings. The molecular conformation is stabilized by an intramolecular C-HÁ Á Á interaction. In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds, forming a two-dimensional network in the (110) plane in which R 4 4 (38) ring motifs are generated.

Experimental
A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.28 g) and potassium carbonate (1.5 mmol, 0.21 g) in acetonitrile solvent was stirred for 15 minutes at room temperature. To this solution, (z)-methyl-2-(bromomethyl)-3phenylprop-2-enoate (1.2 mmol, 0.30 g) was added dropwise till the addition is complete. After the completion of the reaction, as indicated by TLC, acetonitile was evaporated. ETOAc (15 ml) were added to the crude mass. 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 (0.40 g, 88 % 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.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title compound with intramolecular C-H···π interactions shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability levels. H atoms are presented as a small spheres of arbitrary radius. Cg is the centroid of the C18-C23 ring.

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.