Structure of a New Bioactive Agent Containing Combined Antibacterial and Antifungal Pharmacophore Sites: 4-{[(E)-(5-Bromo-2-hydroxyphenyl)methylidene]amino}-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

Chohan Z. H., Shad H. A., Toupet L., Ben Hadda T., AKKURT M.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol.41, no.2, pp.159-162, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 41 Issue: 2
  • Publication Date: 2011
  • Doi Number: 10.1007/s10870-010-9856-x
  • Journal Name: JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.159-162
  • Erciyes University Affiliated: Yes

Abstract

The title compound (3), C17H14BrN3O4S, is a Schiff base compound of 5-bromosalicylaldehyde (1) and sulfamethoxazole (2). The structure of (3) was determined by spectral (IR, H-1 and C-13 NMR), elemental analyses and X-ray diffraction data. Compound (3) crystallizes in the monoclinic space group C2/c, with a = 31.936(3), b = 6.2571(5), c = 16.903(1) angstrom, beta = 94.867(8), V = 3365.5(5) angstrom(3), Z = 8. In the molecule of compound (3), the molecule is bent at the S atom with a C-SO2-NH-C torsion angle of -86.3(3)degrees. Pairs of molecules, related by inversion centres, form intermolecular N-H center dot center dot center dot N hydrogen bonds to produce a dimer. An intramolecular phenolic O-H center dot center dot center dot N hydrogen bond is also formed. Intermolecular hydrogen bonding and pi-pi stacking hold the molecules together. The average distance between stacked benzene ring planes is 3.625(2) angstrom.