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Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid
The asymmetric unit of the title 1:2 co-crystal, C(14)H(14)N(4)O(2)·2C(7)H(5)ClO(2), comprises a half-molecule of oxalamide ((4) LH(2)), being located about a centre of inversion, and a molecule of3-chlorobenzoic acid (3-ClBA) in a general position. From symmetry, the (4) LH(2) molecule has a (+...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7274012/ https://www.ncbi.nlm.nih.gov/pubmed/32523755 http://dx.doi.org/10.1107/S2056989020006568 |
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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 |
collection | PubMed |
description | The asymmetric unit of the title 1:2 co-crystal, C(14)H(14)N(4)O(2)·2C(7)H(5)ClO(2), comprises a half-molecule of oxalamide ((4) LH(2)), being located about a centre of inversion, and a molecule of3-chlorobenzoic acid (3-ClBA) in a general position. From symmetry, the (4) LH(2) molecule has a (+)antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, planar C(2)N(2)O(2) chromophore with the dihedral angle between the core and pyridyl ring being 74.69 (11)°; intramolecular amide-N—H⋯O(amide) hydrogen bonds are noted. The 3-ClBA molecule exhibits a small twist as seen in the C(6)/CO(2) dihedral angle of 8.731 (12)°. In the molecular packing, three-molecule aggregates are formed via carboxylic acid-O—H⋯N(pyridyl) hydrogen bonding. These are connected into a supramolecular tape along [111] through amide-N—H⋯O(carbonyl) hydrogen bonding. Additional points of contact between molecules include pyridyl and benzoic acid-C—H⋯O(amide), methylene-C—H⋯O(carbonyl) and C—Cl⋯π(pyridyl) interactions so a three-dimensional architecture results. The contributions to the calculated Hirshfeld surface are dominated by H⋯H (28.5%), H⋯O/O⋯H (23.2%), H⋯C/C⋯H (23.3%), H⋯Cl/Cl⋯H (10.0%) and C⋯Cl/C⋯Cl (6.2%) contacts. Computational chemistry confirms the C—Cl⋯π interaction is weak, and the importance of both electrostatic and dispersion terms in sustaining the molecular packing despite the strong electrostatic term provided by the carboxylic acid-O—H⋯N(pyridyl) hydrogen bonds. |
format | Online Article Text |
id | pubmed-7274012 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-72740122020-06-09 Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid Tan, Sang Loon Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the title 1:2 co-crystal, C(14)H(14)N(4)O(2)·2C(7)H(5)ClO(2), comprises a half-molecule of oxalamide ((4) LH(2)), being located about a centre of inversion, and a molecule of3-chlorobenzoic acid (3-ClBA) in a general position. From symmetry, the (4) LH(2) molecule has a (+)antiperiplanar conformation with the 4-pyridyl residues lying to either side of the central, planar C(2)N(2)O(2) chromophore with the dihedral angle between the core and pyridyl ring being 74.69 (11)°; intramolecular amide-N—H⋯O(amide) hydrogen bonds are noted. The 3-ClBA molecule exhibits a small twist as seen in the C(6)/CO(2) dihedral angle of 8.731 (12)°. In the molecular packing, three-molecule aggregates are formed via carboxylic acid-O—H⋯N(pyridyl) hydrogen bonding. These are connected into a supramolecular tape along [111] through amide-N—H⋯O(carbonyl) hydrogen bonding. Additional points of contact between molecules include pyridyl and benzoic acid-C—H⋯O(amide), methylene-C—H⋯O(carbonyl) and C—Cl⋯π(pyridyl) interactions so a three-dimensional architecture results. The contributions to the calculated Hirshfeld surface are dominated by H⋯H (28.5%), H⋯O/O⋯H (23.2%), H⋯C/C⋯H (23.3%), H⋯Cl/Cl⋯H (10.0%) and C⋯Cl/C⋯Cl (6.2%) contacts. Computational chemistry confirms the C—Cl⋯π interaction is weak, and the importance of both electrostatic and dispersion terms in sustaining the molecular packing despite the strong electrostatic term provided by the carboxylic acid-O—H⋯N(pyridyl) hydrogen bonds. International Union of Crystallography 2020-05-19 /pmc/articles/PMC7274012/ /pubmed/32523755 http://dx.doi.org/10.1107/S2056989020006568 Text en © Tan and Tiekink 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Tan, Sang Loon Tiekink, Edward R. T. Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title | Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title_full | Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title_fullStr | Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title_short | Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
title_sort | crystal structure, hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between n,n′-bis[(pyridin-4-yl)methyl]ethanediamide and 3-chlorobenzoic acid |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7274012/ https://www.ncbi.nlm.nih.gov/pubmed/32523755 http://dx.doi.org/10.1107/S2056989020006568 |
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