(2Z)-2-{[N-(2-Formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-(4-methylphenyl)prop-2-enenitrile

In the title compound, C25H22N2O3S, the sulfonyl-bound benzene ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formylbenzene and methylbenzene rings. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C—H⋯O hydrogen bonds, which generate C(11) chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.927 (2) Å].

In the title compound, C 25 H 22 N 2 O 3 S, the sulfonyl-bound benzene ring forms dihedral angles of 36.8 (2) and 81.4 (2) , respectively, with the formylbenzene and methylbenzene rings. The molecular conformation is stabilized by an intramolecular C-HÁ Á ÁO hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C-HÁ Á ÁO hydrogen bonds, which generate C(11) chains along the b axis. The crystal packing is further stabilized byinteractions [centroid-centroid distance = 3.927 (2) Å ].

Experimental
A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.275 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile was stirred for 15 minutes at room temperature. To this solution, (E)-2-(bromomethyl)-3-(4methylphenyl)prop-2-enenitrile (1.2 mmol, 0.283 g) was added drop wise until the addition was completed. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated off. Ethylacetate (15 ml) and water (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 a 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 (0.41 g, 95% yield). Recrystallization was carried out using ethylacetate as solvent.

Refinement
H atoms were positioned geometrically, with C-H = 0.93-0.98 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.

Figure 1
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. H atoms are presented as a small cycles of arbitrary radius.

Figure 2
Part of the crystal structure of (I) showing C-H···O hydrogen bonds (dotted lines), with the formation of C(11) chains

Figure 3
A view of the π-π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denotes centroids of the C8-C13 benzene ring and C18-C23 benzene ring, respectively. [Symmetry codes: (iv)-x, 1/2 + y, 3/2 -z; (v)-x, -1/2 + y, 3/2 -z]. 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 > σ(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.