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Synthesis and Crystal Structure of a New Schiff Base 4-[(2-hydroxy-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide

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Abstract

The structure of the title compound (C17H15N3O4S)2 the schiff base, bis(N-(5-methyl-3-isoxazolyl)-4-[(2-hydroxy benzylidene)-amino]) benzene sulfonamide was elucidated by H1, C13 NMR, UV–VIS and IR spectroscopic techniques. The X-ray structure was determined in order to establish the conformation of the molecule. The compound crystallizes in the triclinic space group P-1, with a = 11.419(1), b = 11.426(0), c = 13.316(1) Å, α = 71.94(2), β = 89.79(1), γ = 89.14(2)° and Z = 4. Two benzene rings and azomethine group are practically coplanar, as a result of intramolecular hydrogen bonds involving the hydroxy O atom and azomethine N atom. The component species further interact via N–H···N and C–H···O hydrogen bonds and π–π stacking interactions.

Index Abstract

The title compound (C17H15N3O4S)2, Schiff base, bis(N-(5-methyl-3-isoxazolyl)-4-[(2-hydroxy benzylidene)-amino]) benzene sulfonamide was synthesized by the condensation of 4-amino-N-(5-methyl-3-isoxazolyl) benzene sulfonamide (SMZ) and 2-hydroxy benzaldehyde (SA). Its structure was confirmed by single crystal X-ray diffraction analysis.

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Acknowledgements

AS thanks Bharathidasan University, Tiruchirappalli, Tamil Nadu, India, for the Award of a Research Studentship (Ref No: CCCD/Ph.D-2/15504/2004). MH thanks the Council of Scientific and Industrial Research (CSIR), India, for the award of a Senior Research Fellowship (SRF) (Ref. No: 9/475(123)/2004-EMR-I).

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Authors and Affiliations

  1. School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India

    Annamalai Subashini, Madhukar Hemamalini & P. Thomas Muthiah

  2. IMEM-CNR, Parco Area delle Scienze-37a, I-43010, Fontanini Parma, Italy

    Gabriele Bocelli & Andrea Cantoni

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  1. Annamalai Subashini
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  2. Madhukar Hemamalini
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  3. P. Thomas Muthiah
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  4. Gabriele Bocelli
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  5. Andrea Cantoni
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Correspondence to P. Thomas Muthiah.

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Subashini, A., Hemamalini, M., Muthiah, P.T. et al. Synthesis and Crystal Structure of a New Schiff Base 4-[(2-hydroxy-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide. J Chem Crystallogr 39, 112–116 (2009). https://doi.org/10.1007/s10870-008-9437-4

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