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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

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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, 1H and 13C 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) Å, β = 94.867(8), V = 3365.5(5) Å3, 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)°. Pairs of molecules, related by inversion centres, form intermolecular N–H···N hydrogen bonds to produce a dimer. An intramolecular phenolic O–H···N hydrogen bond is also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 3.625(2) Å.

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Acknowledgments

This work was financially supported by Higher Education Commission of Pakistan under Indegenous 5000 Fellowship Program. Authors gratefully acknowledge Rennes (CNRS, France)/Oujda (CNRST, Morocco) collaboration and the “Projet Global de Recherche de l’Université Mohammed Premier”/PGR-UMP-BH-2005.

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Authors and Affiliations

  1. Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan

    Zahid H. Chohan & Hazoor A. Shad

  2. Institut de Physique, IPR, UMR CNRS 6251, Université de Rennes 1, Rennes, France

    Loic Toupet

  3. Laboratoire de Chimie des Matériaux, Université Mohammed 1ER, 60000, Oujda, Morocco

    Taibi Ben Hadda

  4. Department of Physics, F.A.S., Erciyes University, 38039, Kayseri, Turkey

    Mehmet Akkurt

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  1. Zahid H. Chohan
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  2. Hazoor A. Shad
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  3. Loic Toupet
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  4. Taibi Ben Hadda
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  5. Mehmet Akkurt
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Correspondence to Zahid H. Chohan or Taibi Ben Hadda.

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Chohan, Z.H., Shad, H.A., Toupet, L. et al. 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. J Chem Crystallogr 41, 159–162 (2011). https://doi.org/10.1007/s10870-010-9856-x

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  • DOI: https://doi.org/10.1007/s10870-010-9856-x

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