The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study
The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2-2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 A˚ ). The be...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020
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| Online Access: | http://eprints.sunway.edu.my/1223/ http://eprints.sunway.edu.my/1223/1/Tiekink%20Acta%20Cryst%202020%20E76%20102.pdf |
| _version_ | 1848802001086840832 |
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| author | Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_facet | Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_sort | Tan, Sang Loon * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2-2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central,
almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 A˚ ). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)]. The formation of hydroxy-O—HN(pyridyl)
hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetrically related aggregates assemble into a six-molecule aggregate via amide-N—HO(amide)
hydrogen bonds through a 10-membered {HNC2O}2 synthon. These are linked into a supramolecular tape via amide-N—HO(carbonyl) hydrogen bonds and 22-membered {HOCONC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methylene-C—HO(amide) and pyridyl-C—HO(carbonyl). These interactions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces. |
| first_indexed | 2025-11-14T21:16:24Z |
| format | Article |
| id | sunway-1223 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:16:24Z |
| publishDate | 2020 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
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| spelling | sunway-12232020-10-12T07:20:35Z http://eprints.sunway.edu.my/1223/ The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study Tan, Sang Loon * Tiekink, Edward R. T. * QD Chemistry The crystal and molecular structures of the title 1:2 co-crystal, C14H14N4O2-2C7H6O2, are described. The oxalamide molecule has a (+)-antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, almost planar C2N2O2 chromophore (r.m.s. deviation = 0.0555 A˚ ). The benzoic acid molecules have equivalent, close to planar conformations [C6/CO2 dihedral angle = 6.33 (14) and 3.43 (10)]. The formation of hydroxy-O—HN(pyridyl) hydrogen bonds between the benzoic acid molecules and the pyridyl residues of the diamide leads to a three-molecule aggregate. Centrosymmetrically related aggregates assemble into a six-molecule aggregate via amide-N—HO(amide) hydrogen bonds through a 10-membered {HNC2O}2 synthon. These are linked into a supramolecular tape via amide-N—HO(carbonyl) hydrogen bonds and 22-membered {HOCONC4NH}2 synthons. The contacts between tapes to consolidate the three-dimensional architecture are of the type methylene-C—HO(amide) and pyridyl-C—HO(carbonyl). These interactions are largely electrostatic in nature. Additional non-covalent contacts are identified from an analysis of the calculated Hirshfeld surfaces. International Union of Crystallography 2020 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1223/1/Tiekink%20Acta%20Cryst%202020%20E76%20102.pdf Tan, Sang Loon * and Tiekink, Edward R. T. * (2020) The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 76 (1). pp. 102-110. ISSN 2056-9890 http://doi.org/10.1107/S2056989019016840 doi:10.1107/S2056989019016840 |
| spellingShingle | QD Chemistry Tan, Sang Loon * Tiekink, Edward R. T. * The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title | The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | 1:2 co-crystal formed between n,n′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, hirshfeld surface analysis and computational study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1223/ http://eprints.sunway.edu.my/1223/ http://eprints.sunway.edu.my/1223/ http://eprints.sunway.edu.my/1223/1/Tiekink%20Acta%20Cryst%202020%20E76%20102.pdf |