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Weak but strong: role of weak C–H···X (X=O, N) hydrogen bonds in organization of crystals of (1S,2S,3S,4R,5R,8S)-diethyl 2,4-dicyano-3-(furan-2-yl)-8-morpholino-6-oxobicyclo[3.2.1]octane-2,4-dicarboxylate

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Abstract

An X-ray diffraction study of (1S,2S,3S,4R,5R,8S)-diethyl 2,4-dicyano-3-(furan-2-yl)-8-morpholino-6-oxobicyclo[3.2.1]octane-2,4-dicarboxylate reveals the absence of strong specific intermolecular interactions in the crystal. Application of quantum-chemical calculations allows estimating the interaction energy between basic molecule located in the asymmetric part of the unit cell and molecules belonging to its first coordination sphere. This analysis clearly indicates the layered structure of crystals where the total interaction energy between the basic molecule and neighboring molecules belonging to the layer is significantly higher as compared to the energy of the interactions with molecules of neighboring layers.

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Acknowledgments

This work was performed using computational facilities of joint computational cluster of SSI “Institute for Single Crystals” and Institute for Scintillation Materials of National Academy of Science of Ukraine incorporated into Ukrainian National Grid.

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Authors and Affiliations

  1. SSI “Institute for Single Crystals” of National Academy of Science of Ukraine, 60 Lenina Ave., Kharkiv, 61001, Ukraine

    Svitlana V. Shishkina, Oleg V. Shishkin, Volodymyr V. Medviediev & Irina V. Omelchenko

  2. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61122, Ukraine

    Svitlana V. Shishkina & Oleg V. Shishkin

  3. Baku State University, 23 Xalilova Ave., 1148, Baku, Azerbaijan

    Arif I. Ismiev & Abel M. Magerramov

Authors
  1. Svitlana V. Shishkina
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  2. Oleg V. Shishkin
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  3. Volodymyr V. Medviediev
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  4. Irina V. Omelchenko
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  5. Arif I. Ismiev
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  6. Abel M. Magerramov
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Correspondence to Svitlana V. Shishkina.

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Shishkina, S.V., Shishkin, O.V., Medviediev, V.V. et al. Weak but strong: role of weak C–H···X (X=O, N) hydrogen bonds in organization of crystals of (1S,2S,3S,4R,5R,8S)-diethyl 2,4-dicyano-3-(furan-2-yl)-8-morpholino-6-oxobicyclo[3.2.1]octane-2,4-dicarboxylate. Struct Chem 27, 315–321 (2016). https://doi.org/10.1007/s11224-015-0698-1

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  • DOI: https://doi.org/10.1007/s11224-015-0698-1

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