Ethyl 2-[N-(2-Formylphenyl)benzenesulfonamido]acetate

In the title compound, C17H17NO5S, the N atom is sp 3-hybridized and the S atom has a distorted tetrahedral configuration. The dihedral angle between the two aromatic rings is 30.0 (1)°, and that between the ethyl acetate group and the formylphenyl ring is 77.4 (1)°. The molecules are linked into chains along [100] by C—H⋯O hydrogen bonds and the chains are linked via C—H⋯π interactions.

In the title compound, C 17 H 17 NO 5 S, the N atom is sp 3hybridized and the S atom has a distorted tetrahedral configuration. The dihedral angle between the two aromatic rings is 30.0 (1) , and that between the ethyl acetate group and the formylphenyl ring is 77.4 (1) . The molecules are linked into chains along [100] by C-HÁ Á ÁO hydrogen bonds and the chains are linked via C-HÁ Á Á interactions. Orthorhombic, P2 1 2 1 2 1 a = 11.3442 (5) Å b = 11.7731 (6) Å c = 12.7809 (6) Table 1 Hydrogen-bond geometry (Å , ).  (Brown, 1971). Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). In view of this medicinal importance, the crystal structure determination of the title compound ( Fig.1) was carried out and the results are presented here.

D-HÁ
The angles around atom S1 deviate significantly from the regular tetrahedral value, with the largest deviation of 120.6 (1)°f or O1-S1-O2 angle. This may be due to non-bonding interactions between S═O bonds (Cotton & Stokley, 1970). The sulfonyl oxygen O1 is syn-clinal and O2 is syn-periplanar to the phenyl ring. The dihedral angle between the best planes through the ethylacetate group (O3/O4/C14/C15/C16) and formyl phenyl ring (C7-C12) is 77.4 (1)°. The aldyhyde group is slightly twisted from the plane of the ring to which it is attached as evidenced by the torsion angle C11-C12-C13-O5 of -8.5 (3)°. The relative orientations of C/N/S and O/S/O planes is determined by the hybridization nature of atom N1. The angles between planes C14/N1/S1 and O1/S1/O2 and between C7/N1/S1 and O1/S1/O2 planes are 59° and 56°, respectively.
These values are close to 58° reported for sp 3 N atoms [87° for sp 2 N atoms] (Cameron et al., 1975). The geometrical parameters agree well with those reported for related sulfonamide structures (Usha et al., 2005;Zhu et al., 2008).
In addition to van der Waals interactions, the crystal structure is stabilized by C-H···O and C-H···π interactions (Table   1).

Refinement
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C-H = 0.93-0.97 Å and U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for other H atoms. as those based on F, and R-factors based on ALL data will be even larger.