N-[4-(Propylsulfamoyl)phenyl]acetamide

In the title compound, C11H16N2O3S, the S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.48 (15)°]. The dihedral angles between the benzene ring and its propylsulfonamide and methylamide substituents are 71.8 (2) and 5.8 (1)°, respectively. In the crystal, molecules are linked by Nm—H⋯Os (m = methylamide and s = sulfonamide) hydrogen bonds, forming C(8) chains along the a axis. The two molecule chains are connected by N—H⋯O hydrogen bonds, generating R 3 2(18) rings. The crystal packing is further stabilized by weak intermolecular C—H⋯O hydrogen bonds.

In the title compound, C 11 H 16 N 2 O 3 S, the S atom has a distorted tetrahedral geometry [maximum deviation: O-S-O = 119.48 (15) ]. The dihedral angles between the benzene ring and its propylsulfonamide and methylamide substituents are 71.8 (2) and 5.8 (1) , respectively. In the crystal, molecules are linked by N m -HÁ Á ÁO s (m = methylamide and s = sulfonamide) hydrogen bonds, forming C(8) chains along the a axis. The two molecule chains are connected by N-HÁ Á ÁO hydrogen bonds, generating R 3 2 (18) rings. The crystal packing is further stabilized by weak intermolecular C-HÁ Á ÁO hydrogen bonds.

Comment
Sulfonamides are derivatives of p-aminobenzene sulfonic acid (Ahrens, 1996) belong to the oldest group of antibiotics which are also being used now-a-days. These are white crystalline powder derived from azo dye (Adams, 2001) and have weak organic acid characteristics with a structural resemblance to p-aminobenzoic acid which is an intermediate required for the synthesis of folic acid in bacteria (Ahrens, 1996). The sensitivity of sulfonamides is dependent on the mode in which organisms fulfill their folic acid requirements. Sulfonamides are considered as bacteriostatic drugs (Mayers, 2009& Betts et al., 2003 which are used for the treatment of systematic infections and are absorbed in the gastrointestinal tract (Root, 1999).
As part of our ongoing studies (Faryal et al., 2011, Ahmad et al. (2011a, we synthesized the title compound, (I), and report herein its crystal structure.
Experimental 10 mM of 4-acetamido benzene sulfonyl chloride was taken in the reaction flask and about 20 ml distilled water was added in it. Mixed it well. Then 10 mM of propylamine hydrochloride was added in it. 3% Na 2 CO 3 was used to maintain the pH at 8-10. The reaction was stirred for about 2 h to get the maximum yield. Precipitates obtained was filtered and dried. They are recrystallized in the mixture of methanol and ethyl acetate 1:1. The reaction was monitored by TLC.

Refinement
The N-bound H atoms were located in difference Fourier maps and isotropically refined with the N-H distance restraint