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

Jotani, Mukesh M. and Zukerman-Schpector, Julio and Sousa Madureira, Lucas and Poplaukhin, Pavel and Arman, Hadi D. and Miller, Tyler and Tiekink, Edward R. T. * (2016) Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide. Zeitschrift für Kristallographie - Crystalline Materials, 231 (7). pp. 415-425. ISSN 2194-4946

Z. Kristallogr. 2016 231 415.pdf - Accepted Version

Download (1MB) | Preview
Official URL:


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.

Item Type: Article
Additional Information: First author is with Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad; 2nd and 3rd authors are with Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos; 4th author is with Chemical Abstracts Service, Columbus, Ohio, USA; 5th & 6th authors are with Department of Chemistry, The University of Texas at San Antonio; 7th author is with Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University
Uncontrolled Keywords: crystal structure analysis; DFT; Hirshfeld surface; oxalamide; X-ray diffraction
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Ms. Molly Chuah
Related URLs:
Date Deposited: 02 Nov 2017 01:47
Last Modified: 07 Oct 2020 09:50

Actions (login required)

View Item View Item