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Zeitschrift für Kristallographie - Crystalline Materials

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Volume 232, Issue 4 (Apr 2017)

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Competition between intermolecular hydrogen bonding and stacking in the crystals of 4-Hydroxy-N-(pyridin-2-yl)-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides

Svitlana V. Shishkina
  • Corresponding author
  • SSI “Institute for Single Crystals” National Academy of Science of Ukraine, 60 Nauki ave., Kharkiv, 61001, Ukraine
  • Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv 61077, Ukraine
  • Email:
/ Igor V. Ukrainets
  • Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska str., Kharkiv 61002, Ukraine
/ Lidiya A. Petrushova
  • Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska str., Kharkiv 61002, Ukraine
Published Online: 2017-01-25 | DOI: https://doi.org/10.1515/zkri-2016-2011

Abstract

The traditional crystal packing study based on the analysis of geometrical characteristics of intermolecular interactions is found to be not informative enough. The application of quantum-chemical calculations for the evaluation of pairwise interaction energies between molecules allows to get much more information about supramolecular architecture. The staking interactions between π-systems of neighboring molecules form the building unit of the crystal packing in the absence of any strong interactions as well as in the presence of the N–H…O classical hydrogen bond. Unexpectedly the hydrogen bonds play the secondary role in the crystal packing formation as compared to stacking. Analysis of the total interaction energy of the basic molecule with all the molecules of its first coordination sphere and the pairwise interaction energies allows to evaluate the extent of crystal isotropy from point of view of interaction energies.

This article offers supplementary material which is provided at the end of the article.

Keywords: crystal packing; hydrogen bonding; intermolecular interactions; stacking

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About the article

Received: 2016-10-13

Accepted: 2016-12-02

Published Online: 2017-01-25

Published in Print: 2017-04-01



Citation Information: Zeitschrift für Kristallographie - Crystalline Materials, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2016-2011. Export Citation

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