Received 22 April 2013
The title compound, C25H26Cl2FN3O4S, contains two bio-active moieties (thiobarbituric acid and fluoroquinolone). In the crystal, molecules are linked via C-HO and C-HF hydrogen bonds, forming two-dimensional slab-like networks lying parallel to the bc plane. The benzene ring substituted by F and Cl atoms and the 4-chlorobutyl group seem to be partly disordered, however attempts to model the disorder were unsuccessful.
For the biological activity of fluoroquinolone derivatives, see: Li et al. (2000); Baker et al. (2004); Mitscher (2005). For the crystal structures of some fluoroquinolone and 1,3-diethyl-2-thiobarbituric acid derivatives, see: Al-Qawasmeh (2012); Sweidan et al. (2012); Shishkin et al. (1997).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2478 ).
The authors gratefully acknowledge financial support from the Deanship of Scientific Research at the University of Jordan. The X-ray structural work was done at the Hamdi Mango Center for Scientific Research of The University of Jordan, Amman 11942, Jordan.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Qawasmeh, R. A. (2012). Acta Cryst. E68, o2533.
Baker, W. R., Cai, S. P., Dimitroff, M., Fang, L. M., Huh, K. K., Ryckman, D. R., Shang, X., Shawar, R. M. & Therrien, J. H. (2004). J. Med. Chem. 47, 4693-4709.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Li, Q., Mitscher, L. A. & Shen, L. L. (2000). Med. Res. Rev. 20, 231-293.
Mitscher, L. A. (2005). Chem. Rev. 105, 559-592.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shishkin, O. V., Solomovich, E. V., Vakula, V. M. & Yaremenko, F. G. (1997). Russ. Chem. Bull. 46, 1838-1843.
Sweidan, K., AlDamen, M. A., Maichle-Mö\, C. & Mubarak, M. S. (2012). J. Chem. Crystallogr. 42, 427-431.