3-Chloro-N-(4-sulfamoylphenyl)propanamide

In the title compound, C9H11ClN2O3S, the dihedral angle between the benzene ring and the amido –NHCO– plane is 15.0 (2)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the amino NH2 group is involved in intermolecular N—H⋯O hydrogen bonds, which connect the molecules into a double layer structure expanding parallel to the bc plane. The layers are further linked by an amido N—H⋯O hydrogen bond. Between the layers, a weak π–π interaction with a centroid–centroid distance of 3.7447 (12) Å is also observed.

In the title compound, C 9 H 11 ClN 2 O 3 S, the dihedral angle between the benzene ring and the amido -NHCO-plane is 15.0 (2) . An intramolecular C-HÁ Á ÁO hydrogen bond generates an S(6) ring motif. In the crystal structure, the amino NH 2 group is involved in intermolecular N-HÁ Á ÁO hydrogen bonds, which connect the molecules into a double layer structure expanding parallel to the bc plane. The layers are further linked by an amido N-HÁ Á ÁO hydrogen bond. Between the layers, a weakinteraction with a centroidcentroid distance of 3.7447 (12) Å is also observed.
Sulfonamides and their derivatives have been the subject of investigation for many reasons. The amides are important constituent of many biologically significant compounds. The chemistry of sulfonamides is of interest as they show distinct physical, chemical and biological properties. The sulfonamide derivatives are known for their numerous pharmacological activities, antibacterial, antitumor, insulin-release stimulation and antithyroid properties (Maren, 1976). In addition, the unsubstituted aromatic/heterocyclic sulfonamides act as carbonic anhydrase inhibitors (Supuran & Scozzafava, 2001;Türkmen et al., 2005;Supuran et al., 2003) whereas other types of derivatives show diuretic activity (high-ceiling diuretics or thiadiazine diuretics), hypoglycemic activity and anti-cancer properties . Although sulfonamides are best known as bacteriostatic (Silverman, 1992) and antimalarial agents (Albala et al., 1994), there is now a range of drugs, possessing very different pharmacological activities, in which the sulfonamide group is present (Reynolds, 1996). Due to their significant pharmacology applications and widespread use in medicine, these compounds have gained attention in bio-inorganic and metal-based drug chemistry. In this work we report the crystal structure of 3-chloro-N-(4sulfamoylphenyl)propanamide.
In the title molecule (I), (Fig. 1 are within the normal range as the values of the other geometric parameters of the molecule. The dihedral angle between the benzene ring and the amido -NHCO-plane is 15.0 (2)°.

Refinement
The H-atoms of the NH 2 group were located in a difference Fourier map, and were refined with distance restraints of N-H = 0.86 (2) Å; their temperature factors were freely refined. The other H-atoms were placed in calculated positions with C-H = 0.93-0.97 Å and N-H = 0.86 Å, and were included in the refinement in the riding model approximation, with U iso (H) = 1.2U eq (C, N).
Figures Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.