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Zeitschrift für Kristallographie - Crystalline Materials

Editor-in-Chief: Pöttgen, Rainer

Ed. by Antipov, Evgeny / Boldyreva, Elena V. / Friese, Karen / Huppertz, Hubert / Jahn, Sandro / Tiekink, E. R. T.


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Volume 231, Issue 7

Issues

Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide

Mukesh M. Jotani
  • Corresponding author
  • Department of Physics, Bhavan’s Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India
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/ Julio Zukerman-Schpector
  • Corresponding author
  • Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P. 676, São Carlos, SP, 13565-905, Brazil
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/ Lucas Sousa Madureira
  • Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P. 676, São Carlos, SP, 13565-905, Brazil
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/ Pavel Poplaukhin / Hadi D. Arman
  • Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA
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/ Tyler Miller
  • Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA
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/ Edward R.T. Tiekink
  • Corresponding author
  • Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
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Published Online: 2016-05-14 | DOI: https://doi.org/10.1515/zkri-2016-1933

Abstract

The common feature of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide is their crystallisation in the monoclinic space group P21/c with Z=4. In low symmetry form 1, the central core is effectively planar and the terminal pyridyl rings adopt a syn-periplanar conformation. In the high symmetry form, 2, there are two independent molecules in the asymmetric unit but each is located about a centre of inversion. The rings again are almost perpendicular to the central plane but, from symmetry are anti-periplanar. Computational chemistry shows that symmetric molecules with syn (two-fold) and anti (centrosymmetric) conformations have nearly identical energies. In the molecular packing of each of 1 and 2, supramolecular tapes based on amide-N–H···O(amide) hydrogen bonding are found. In 1, these are connected into layers by C–H···N(pyridyl) interactions, while in 2, the chains are linked into a three-dimensional architecture by C–H···N(pyridyl) interactions. The importance of hydrogen bonding is emphasised in the analysis of the Hirshfeld surfaces.

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

Keywords: crystal structure analysis; DFT; Hirshfeld surface; oxalamide; X-ray diffraction

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About the article

Received: 2016-02-14

Accepted: 2016-04-15

Published Online: 2016-05-14

Published in Print: 2016-07-01


Citation Information: Zeitschrift für Kristallographie - Crystalline Materials, Volume 231, Issue 7, Pages 415–425, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2016-1933.

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