Abstract
The title compound, C14H13ClN2O3S, features an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring motif. Intermolecular N—H⋯O hydrogen bonds and C—H⋯O close contacts link neighbouring molecules forming R 2 2(13) ring motifs. In the crystal structure, molecules are further linked by C—H⋯Cl interactions, forming one-dimensional extended chains along the c axis. The dihedral angle between the two benzene rings is 86.06 (3)°. The crystal structure is further stabilized by weak intermolecular π–π interactions [interplanar stacking distance = 3.357 (7) Å].
Highlights
Molecules are further linked by C—H Cl interactions, forming onedimensional extended chains along the c axis
Sulfonamides are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid (Kayser et al, 2004)
These agents are generally used in combination with other drugs to prevent or treat a number of bacterial and parasitic infections (Tierney et al, 2006)
Summary
H atoms treated by a mixture of independent and constrained refinement max = 0.44 e Å3. R factor = 0.031; wR factor = 0.093; data-to-parameter ratio = 26.5. The title compound, C14H13ClN2O3S, features an intramolecular O—H N hydrogen bond which generates an. Intermolecular N—H O hydrogen bonds and C—H O close contacts link neighbouring molecules forming R22(13) ring motifs. Molecules are further linked by C—H Cl interactions, forming onedimensional extended chains along the c axis. The dihedral angle between the two benzene rings is 86.06 (3). The crystal structure is further stabilized by weak intermolecular – interactions [interplanar stacking distance = 3.357 (7) Å]
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