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The staple role of hydrogen and halogen bonds in crystalline (E)-8-((2,3-diiodo-4-(quinolin-8-ylthio)but-2-en-1-yl)thio)quinolin-1-ium triiodide

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Abstract

The crystal structure of (E)-8-((2,3-diiodo-4-(quinolin-8-ylthio)but-2-en-1-yl)thio)quinolin-1-ium triiodide, determined at 100 K in the space group C2/c, contains the bridge hydrogen bond [N···H···N]+ linking two neighboring quinolinium fragments; the distance N···N is 2.6927(15) Å. The experimental difference Fourier maps at 293 and 100 K lead to a conclusion about the dynamic nature of the H atom disorder. Calculated vibrational modes obtained for the same compound in the space groups C2/c and Cc are in agreement with the experimental Raman spectrum in the low-frequency region; together, they are consistent with a previous supposition about the dynamic nature of the H atom disorder. We have found that the cation–anion interactions are realized through the charge-assisted iodine–iodine halogen bond.

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Acknowledgments

The authors express their gratitude to Professor B.A. Kolesov, Institute of Inorganic Chemistry, Novosibirsk, Russia, and D.G. Pikhulya, South Ural State University, Chelyabinsk, for constructive assistance in the collection of Raman spectroscopy data. This work is supported by the Ministry of Education and Science of the Russian Federation, GZ729.

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Authors and Affiliations

  1. South Ural State University, Lenin Pr., 76, Chelyabinsk, Russia, 454080

    E. V. Bartashevich, V. I. Batalov & I. D. Yushina

  2. L.Ya. Karpov Institute of Physical Chemistry, ul. Vorontsovo Pole 10, Moscow, Russia, 105064

    A. I. Stash

  3. Novosibirsk State University, ul. Pirogova, 2, Novosibirsk, Russia, 630090

    T. N. Drebushchak

  4. Institute of Solid State Chemistry and Mechanochemistry, SB RAS, ul. Kutateladze, 18, Novosibirsk, Russia, 630128

    T. N. Drebushchak & E. V. Boldyreva

  5. D.I. Mendeleev University of Chemical Technology, Miusskaya Sq. 9, Moscow, Russia, 125047

    V. G. Tsirelson

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  1. E. V. Bartashevich
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  2. A. I. Stash
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  3. V. I. Batalov
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  4. I. D. Yushina
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  5. T. N. Drebushchak
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  6. E. V. Boldyreva
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Correspondence to E. V. Bartashevich.

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Bartashevich, E.V., Stash, A.I., Batalov, V.I. et al. The staple role of hydrogen and halogen bonds in crystalline (E)-8-((2,3-diiodo-4-(quinolin-8-ylthio)but-2-en-1-yl)thio)quinolin-1-ium triiodide. Struct Chem 27, 1553–1560 (2016). https://doi.org/10.1007/s11224-016-0785-y

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