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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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Main Authors: Tan, Sang Loon *, Tiekink, Edward R. T. *
Format: Article
Language:English
Published: International Union of Crystallography 2020
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/1223/1/Tiekink%20Acta%20Cryst%202020%20E76%20102.pdf
http://eprints.sunway.edu.my/1223/
http://doi.org/10.1107/S2056989019016840
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spelling my.sunway.eprints.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
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
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
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.
format Article
author Tan, Sang Loon *
Tiekink, Edward R. T. *
author_facet Tan, Sang Loon *
Tiekink, Edward R. T. *
author_sort Tan, Sang Loon *
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_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_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_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
publisher International Union of Crystallography
publishDate 2020
url http://eprints.sunway.edu.my/1223/1/Tiekink%20Acta%20Cryst%202020%20E76%20102.pdf
http://eprints.sunway.edu.my/1223/
http://doi.org/10.1107/S2056989019016840
_version_ 1683233347816390656
score 13.211869

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