SUPRAMOLECULAR ARCHITECTURE OF CRYSTALS OF PERFLUORINATED 3-ALKYLPHTHALIDES
T.V. Rybalova1,2, Yu.V. Gatilov1,2, Ya.V. Zonov1,2, V.M. Karpov1
1Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia
2Novosibirsk National Research State University, Novosibirsk, Russia
Keywords: 3-гидрокси-перфтор-3-алкилфталиды, рентгеноструктурный анализ, межмолекулярные взаимодействия, квантово-химические расчеты, супрамолекулярная архитектура, полиморфы, 3-hydroxyperfluoro-3-alkylphthalides, single crystal X-ray diffraction study, intermolecular interactions, quantum chemical calculations, supramolecular architecture, polymorphs
Abstract
The molecular and crystal structures of perfluoro-3-alkylphthalides (3-hydroxyperfluoro-3-methylphthalide and its hydrate, two polymorps 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 for the crystallohydrate, to the formation of hydrogen bonded chains (6) (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 the additional C=O…π, O…π and C-F…π interactions.
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