N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study
The asymmetric unit of the title 1:1 solvate, C14H14N4O2·C6H6 [systematic name of the oxalamide molecule: N,N′-bis(pyridin-4-ylmethyl)ethanediamide], comprises a half molecule of each constituent as each is disposed about a centre of inversion. In the oxalamide molecule, the central C2N2O2 atoms are...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019009551 |
| _version_ | 1819290948432035840 |
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| author | Sang Loon Tan Nathan R. Halcovitch Edward R. T. Tiekink |
| author_facet | Sang Loon Tan Nathan R. Halcovitch Edward R. T. Tiekink |
| author_sort | Sang Loon Tan |
| collection | DOAJ |
| description | The asymmetric unit of the title 1:1 solvate, C14H14N4O2·C6H6 [systematic name of the oxalamide molecule: N,N′-bis(pyridin-4-ylmethyl)ethanediamide], comprises a half molecule of each constituent as each is disposed about a centre of inversion. In the oxalamide molecule, the central C2N2O2 atoms are planar (r.m.s. deviation = 0.0006 Å). An intramolecular amide-N—H...O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the molecule adopts an antiperiplanar disposition of the pyridyl rings, and an orthogonal relationship is evident between the central plane and each terminal pyridyl ring [dihedral angle = 86.89 (3)°]. In the crystal, supramolecular layers parallel to (10\overline{2}) are generated owing the formation of amide-N—H...N(pyridyl) hydrogen bonds. The layers stack encompassing benzene molecules which provide the links between layers via methylene-C—H...π(benzene) and benzene-C—H...π(pyridyl) interactions. The specified contacts are indicated in an analysis of the calculated Hirshfeld surfaces. The energy of stabilization provided by the conventional hydrogen bonding (approximately 40 kJ mol−1; electrostatic forces) is just over double that by the C—H...π contacts (dispersion forces). |
| first_indexed | 2024-12-24T03:30:51Z |
| format | Article |
| id | doaj.art-00989da3ffad436ba3c61c45311d1b3d |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:30:51Z |
| publishDate | 2019-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-00989da3ffad436ba3c61c45311d1b3d2022-12-21T17:17:11ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-08-017581133113910.1107/S2056989019009551hb7835N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational studySang Loon Tan0Nathan R. Halcovitch1Edward R. T. Tiekink2Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, MalaysiaDepartment of Chemistry, Lancaster University, Lancaster LA1 4YB, United KingdomResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, MalaysiaThe asymmetric unit of the title 1:1 solvate, C14H14N4O2·C6H6 [systematic name of the oxalamide molecule: N,N′-bis(pyridin-4-ylmethyl)ethanediamide], comprises a half molecule of each constituent as each is disposed about a centre of inversion. In the oxalamide molecule, the central C2N2O2 atoms are planar (r.m.s. deviation = 0.0006 Å). An intramolecular amide-N—H...O(amide) hydrogen bond is evident, which gives rise to an S(5) loop. Overall, the molecule adopts an antiperiplanar disposition of the pyridyl rings, and an orthogonal relationship is evident between the central plane and each terminal pyridyl ring [dihedral angle = 86.89 (3)°]. In the crystal, supramolecular layers parallel to (10\overline{2}) are generated owing the formation of amide-N—H...N(pyridyl) hydrogen bonds. The layers stack encompassing benzene molecules which provide the links between layers via methylene-C—H...π(benzene) and benzene-C—H...π(pyridyl) interactions. The specified contacts are indicated in an analysis of the calculated Hirshfeld surfaces. The energy of stabilization provided by the conventional hydrogen bonding (approximately 40 kJ mol−1; electrostatic forces) is just over double that by the C—H...π contacts (dispersion forces).http://scripts.iucr.org/cgi-bin/paper?S2056989019009551crystal structurebis(4-pyridylmethyl)oxalamidebenzene solvatehydrogen bondingHirshfeld surface analysiscomputational chemistry |
| spellingShingle | Sang Loon Tan Nathan R. Halcovitch Edward R. T. Tiekink N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study Acta Crystallographica Section E: Crystallographic Communications crystal structure bis(4-pyridylmethyl)oxalamide benzene solvate hydrogen bonding Hirshfeld surface analysis computational chemistry |
| title | N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | N,N′-Bis(pyridin-4-ylmethyl)oxalamide benzene monosolvate: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | n n bis pyridin 4 ylmethyl oxalamide benzene monosolvate crystal structure hirshfeld surface analysis and computational study |
| topic | crystal structure bis(4-pyridylmethyl)oxalamide benzene solvate hydrogen bonding Hirshfeld surface analysis computational chemistry |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019009551 |
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