4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}benzenesulfonamide

In the title compound, C22H19NO3S, the terminal phenyl and methylphenyl rings are twisted by 37.35 (12) and 49.08 (13)°, respectively, to the central benzene ring. In the crystal, molecules are linked by classical N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds into a three-dimensional supramolecular network.


Structural commentary
For related structures, see: Murugavel et al. (2012);Zhang et al. (2010). Sulfonamides, which are already known as sulfa drugs, are an important class of compounds in the field of chemistry, biology and pharmacology. Several sulfonamide derivatives are used as chemotherapeutic agents for their antibacterial, antifungal, antitumor and hypoglycemic (Chohan et al., 2010;El-Sayed et al., 2011;Seri et al., 2000). In addition, some sulfonamide derivatives have been shown to inhibit on carbonic anhydrases (Suparan et al., 2000). In view of these potential applications and in continuation of our work, the structure of the title compound has been carried out and the results are presented here.
X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around atoms S and N are distorted tetrahedral and planar trigonal, respectively. The average S-O bond length is 1.427 (2) Å, while the S-N and S-C bond lengths are 1.638 (3) and 1.757 (3), respectively. The dihedral angle between the vinylphenyl ring (C1-C6) and the methylphenyl ring (C16-C21) is 49.08 (13) o , and the dihedral angle between the vinylphenyl ring (C1-C6) and ketophenyl (C10-C15) ring is 37.35 (12) o . The sulfonamide torsion angle 1s 64.0 (2) o for C2 -N1-S1-C16. The C==C double bond is in an E conformation and the vinylcarbonyl groups adopt extended conformations.

Synthesis and crystallization
A solution of 4 M Na 2 CO 3 in water (10 mL) was added to a solution of 2-aminobenzyl alcohol (5.0 mmol) and p-toluenesulfonyl chloride (5.5 mmol) in THF (10 mL). After stirring at room temperature for 24 h, the reaction mixture was poured into cold water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO 4 . The resulting residue was purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzyl alcohol.
Next, to solutionof 2-(toluensulfonylamino)benzyl alcohol (3.0 mmol) in CH 2 Cl 2 (10 mL) was added excess MnO 2 (15 mmol). After stirring for at room temperature for 36 h, the reaction mixture was filtered under celite pad and purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzaldehyde. To a solution of phenacyltriphenylphosphonium bromide (1.1 mmol) in toluene (5 mL) was added NaH (1.2 mmol) at 273 K. After stirring at 273 K for 1 h, to the reactin mixture, 2-(toluensulfonylamino)benzaldehyde (1.0 mmol) was added. After stirring at room temperature for 24 h, the reaction mixture was poured into water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO 4 . Theresulting residue was purified by silica gel chromatography to afford the title compound.

Refinement
All H atoms were positioned geometrically, (C-H = 0.95-0.96 Å) and constrained to ride on their parent atoms, with U iso (H) = xUeq(C), where x = 1.2 for all other H atoms.

Figure 1
A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A partial view of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity.  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.46 e Å −3 Δρ min = −0.43 e Å −3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq C1