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X-ray and DFT calculated structures of 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-phenylthiosemicarbazone and 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-(4-chlorophenyl)thiosemicarbazone

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Abstract

Crystal and molecular structures of two new compounds 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-phenylthiosemicarbazone, C22H19N5S, (I) and 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-(4-chlorophenyl)thiosemicarbazone, C22H18ClN5S, (II) have been determined by single-crystal X-ray diffraction. Molecular geometries from X-ray experiment of I and II have been compared with those calculated using the Density Functional Theory (DFT) with B3LYP/6-31G(d,p) basis set. Both compounds crystallize in the monoclinic space group P21/c with Z = 4: a = 13.2880(5), 14.2648(3) Å, b = 9.4122(2), 9.3892(3) Å, c = 15.6341(6), 15.6268(4) Å, β = 101.779(3)°, 104.926(2)°, for I and II, respectively. An extensive two-dimensional network of N-H⋯N hydrogen bonds and π-ring interactions are responsible for crystal stabilization in both structures.

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Authors and Affiliations

  1. Faculty of Engineering and Architecture, Department of Energy Systems Engineering, Sinop University, Sinop, 57000, Turkey

    Z. S. Sahin & S. Isik

  2. Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Hacettepe University, Ankara, 06100, Turkey

    E. Septioglu & U. Calis

Authors
  1. Z. S. Sahin
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  2. E. Septioglu
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  3. U. Calis
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  4. S. Isik
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Correspondence to Z. S. Sahin.

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Sahin, Z.S., Septioglu, E., Calis, U. et al. X-ray and DFT calculated structures of 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-phenylthiosemicarbazone and 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-(4-chlorophenyl)thiosemicarbazone. Crystallogr. Rep. 59, 964–968 (2014). https://doi.org/10.1134/S1063774514070177

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  • DOI: https://doi.org/10.1134/S1063774514070177

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