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Supramolecular architecture of crystals of perfluorinated 3-alkylphthalides

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Abstract

The molecular and crystal structures of perfluoro-3-alkylphthalides (3-hydroxyperfluoro-3-methylphthalide and its hydrate, two polymorphs of 3-hydroxyperfluoro-3-ethylphthalide and 3-hydroxyperfluoro-3-isopropylphthalide) are determined by single crystal X-ray diffraction. In the crystals, the supramolecular O–Н…O=C synthon occurs leading, except the crystallohydrate, to the formation of C 11 (6) hydrogen bonded chains (supramolecular 1D motifs). According to the DFT/M06-2X/TZV calculations, the interaction energy of hydrogen bonded molecular pairs increases in this series, which can be explained by additional C=O…π, O…π, and C–F…π interactions.

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Authors and Affiliations

  1. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. V. Rybalova, Yu. V. Gatilov, Ya. V. Zonov & V. M. Karpov

  2. Novosibirsk National Research State University, Novosibirsk, Russia

    T. V. Rybalova, Yu. V. Gatilov & Ya. V. Zonov

Authors
  1. T. V. Rybalova
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  2. Yu. V. Gatilov
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  3. Ya. V. Zonov
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  4. V. M. Karpov
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Corresponding author

Correspondence to Yu. V. Gatilov.

Additional information

Translated from Zhurnal Strukturnoi Khimii, Vol. 57, No. 4, pp. 815-821, May-June, 2016.

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Rybalova, T.V., Gatilov, Y.V., Zonov, Y.V. et al. Supramolecular architecture of crystals of perfluorinated 3-alkylphthalides. J Struct Chem 57, 777–783 (2016). https://doi.org/10.1134/S0022476616040223

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  • DOI: https://doi.org/10.1134/S0022476616040223

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