Received 1 February 2008
The title compound, C18H16ClN3O4S, is a Schiff base ligand in which the H atom of the hydroxy group has moved to the N atom of the imine group, resulting in a zwitterion. The structure is stabilized by an intramolecular (N-HO) and five intermolecular (C-HO, C-HN and N-HO) hydrogen bonds. The molecules are linked to each other by hydrogen bonds and form a three-dimensional polymeric network. In addition, the aromatic rings are also involved in - interactions [centroid-centroid distance between aromatic rings = 3.7525 (11) Å].
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2068 ).
The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer.
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.
Chatterjee, C., Dattagupta, J. K. & Saha, N. N. (1982). Acta Cryst. B38, 1845-1847.
Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64 Submitted.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hämäläinen, R., Lehtinen, M. & Turpeinen, U. (1986). Arch. Pharm. 319, 415-420.
Nishimori, I., Vullo, D., Innocenti, A., Scozzafava, A., Mastrolorenz, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 3828-3833.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.