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Zeitschrift für Kristallographie - Crystalline Materials

Editor-in-Chief: Pöttgen, Rainer

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


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Band 231, Heft 7

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

Mukesh M. Jotani / Julio Zukerman-Schpector
  • Korrespondenzautor
  • Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P. 676, São Carlos, SP, 13565-905, Brazil
  • E-Mail
  • Weitere Artikel des Autors:
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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
  • Weitere Artikel des Autors:
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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
  • Korrespondenzautor
  • Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
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Online erschienen: 14.05.2016 | 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.

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

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Artikelinformationen

Erhalten: 14.02.2016

Angenommen: 15.04.2016

Online erschienen: 14.05.2016

Erschienen im Druck: 01.07.2016


Quellenangabe: Zeitschrift für Kristallographie - Crystalline Materials, Band 231, Heft 7, Seiten 415–425, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2016-1933.

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