N-(2-Formylphenyl)benzenesulfonamide

In the title compound, C13H11NO3S, the two aromatic rings are oriented at an angle of 88.18 (8)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds are observed, each of which generates an S(6) ring motif. In the crystal, molecules are linked into C(7) chains along [010] by intermolecular C—H⋯O hydrogen bonds. The structure is further stabilized by intermolecular C—H⋯π interactions involving the sulfonyl-bound phenyl ring.

In the title compound, C 13 H 11 NO 3 S, the two aromatic rings are oriented at an angle of 88.18 (8) . Intramolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds are observed, each of which generates an S(6) ring motif. In the crystal, molecules are linked into C(7) chains along [010] by intermolecular C-HÁ Á ÁO hydrogen bonds. The structure is further stabilized by intermolecular C-HÁ Á Á interactions involving the sulfonylbound phenyl ring.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2869). anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activities. Sulfonamides particularly sulfadiazine and sulfadoxine have been used clinically as antimalarial agents (Zareef et al., 2007). Due to their significant pharmacological applications and widespread use in medicine, these compounds have also gained attention in bioinorganic and metal-based drug chemistry (Chohan et al., 2007). Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. The antibacterial action of this group of drugs is exerted by the complete inhibition of dihydropteroate synthase enzyme towards the p-amino benzonate (Brown, 1971). Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003). The sulfonamides inhibit the growth of bacterial organism and are also useful for treating urinary and gastrointestinal infections (Sethu Sankar et al., 2002). 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.
Intermolecular C-H···O hydrogen bonds involving atoms C3 and O2 link molecules into C(7) chains running along the [010] (Fig. 2). The crystal packing is further stabilized by C-H···π interactions involving the sulfonyl-bound phenyl ring.
Experimental N-[2-(Hydroxymethyl)phenyl]benzenesulfonamide (2 g, 7.6 mmol) was added to a solution of pyridinium chlorochromate (3.25 g, 15.11 mmol) in dry dichloromethane (20 ml) at room temperature and the reaction mixture was stirred for 4 h. The solvent was removed to obtain a crude aldehyde as a white solid. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Refinement
Atom H1 was located in a difference map and refined freely. All other H atoms were positioned geometrically and constrained to ride on their parent atoms, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are shown as dashed lines.  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 Rfactors(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.