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The Synthesis and Structure of Two Novel N-(Benzothiazol-2-yl)benzamides

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Abstract

Two novel benzothiazoles 2-chloro-N-(benzothiazol-2-yl)benzamide (1) and 2-chloro-N-(6-cyanobenzothiazol-2-yl)benzamide (2) were obtained in multistep synthesis. They were characterised by means of IR, 1H- and 13C-NMR spectroscopy and also by single-crystal X-ray diffraction. The compound 1 crystallises with triclinic space group P \( \bar 1 \), a = 9.5923(8) Å, b = 9.8583(8) Å, c = 13.8962(10) Å, α = 89.162(6)°, β = 77.741(7)°, γ = 80.064(7)°, V = 1264.5(2) Å3, Z = 4 and compound 2 crystallises as methanol solvate with monoclinic space group P 21/n, a = 7.5093(9) Å, b = 13.0211(14) Å, c = 16.032(2) Å, β = 92.717(10)°, V = 1565.9(3) Å3, Z = 4. Both crystal structures consist of discrete dimers connected into a three-dimensional network by intermolecular C–H···O and C–H···X (X = Cl or S) hydrogen bonds and by face-to-face π–π stacking interactions.

Index Abstract

The synthesis and structure of two novel N-(benzothiazol-2-yl)benzamides. Irena Ćaleta, Dominik Cinčić, GraceKarminski-Zamola and Branko Kaitner. Hydrogen bonds and π–π interactions in N-(benzothiazol-2-yl)benzamides N-(benzothiazol-2-yl)benzamides.

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Acknowledgements

This research was supported by grants from the Ministry of Science and Technology of the Republic of Croatia (Grant Nos. 125-0982464-1356 and 119-1193079-3069).

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, 10000, Zagreb, Croatia

    Irena Ćaleta & Grace Karminski-Zamola

  2. Laboratory of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102 a, 10000, Zagreb, Croatia

    Dominik Cinčić & Branko Kaitner

Authors
  1. Irena Ćaleta
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  2. Dominik Cinčić
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  3. Grace Karminski-Zamola
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  4. Branko Kaitner
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Corresponding author

Correspondence to Branko Kaitner.

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Ćaleta, I., Cinčić, D., Karminski-Zamola, G. et al. The Synthesis and Structure of Two Novel N-(Benzothiazol-2-yl)benzamides. J Chem Crystallogr 38, 775–780 (2008). https://doi.org/10.1007/s10870-008-9389-8

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  • DOI: https://doi.org/10.1007/s10870-008-9389-8

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