Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide
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 th...
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De Gruyter
2016
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| Online Access: | http://eprints.sunway.edu.my/659/1/Z.%20Kristallogr.%202016%20231%20415.pdf http://eprints.sunway.edu.my/659/ http://dx.doi.org/10.1515/zkri-2016-1933 |
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| author | Jotani, Mukesh M. Zukerman-Schpector, Julio Sousa Madureira, Lucas Poplaukhin, Pavel Arman, Hadi D. Miller, Tyler Tiekink, Edward R. T. * |
| author_facet | Jotani, Mukesh M. Zukerman-Schpector, Julio Sousa Madureira, Lucas Poplaukhin, Pavel Arman, Hadi D. Miller, Tyler Tiekink, Edward R. T. * |
| author_sort | Jotani, Mukesh M. |
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| continent | Asia |
| country | Malaysia |
| description | 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. |
| format | Article |
| id | my.sunway.eprints.659 |
| institution | Sunway University |
| language | en |
| publishDate | 2016 |
| publisher | De Gruyter |
| record_format | eprints |
| spelling | my.sunway.eprints.6592020-10-07T09:50:05Z http://eprints.sunway.edu.my/659/ Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide Jotani, Mukesh M. Zukerman-Schpector, Julio Sousa Madureira, Lucas Poplaukhin, Pavel Arman, Hadi D. Miller, Tyler Tiekink, Edward R. T. * QD Chemistry 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. De Gruyter 2016-07 Article PeerReviewed text en http://eprints.sunway.edu.my/659/1/Z.%20Kristallogr.%202016%20231%20415.pdf 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 http://dx.doi.org/10.1515/zkri-2016-1933 doi:10.1515/zkri-2016-1933 |
| spellingShingle | QD Chemistry Jotani, Mukesh M. Zukerman-Schpector, Julio Sousa Madureira, Lucas Poplaukhin, Pavel Arman, Hadi D. Miller, Tyler Tiekink, Edward R. T. * Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title | Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title_full | Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title_fullStr | Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title_full_unstemmed | Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title_short | Structural, Hirshfeld surface and theoretical analysis of two conformational polymorphs of N,N′-bis(pyridin-3-ylmethyl)oxalamide |
| title_sort | structural, hirshfeld surface and theoretical analysis of two conformational polymorphs of n,n′-bis(pyridin-3-ylmethyl)oxalamide |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/659/1/Z.%20Kristallogr.%202016%20231%20415.pdf http://eprints.sunway.edu.my/659/ http://dx.doi.org/10.1515/zkri-2016-1933 |
| url_provider | http://eprints.sunway.edu.my/ |