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A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis
The asymmetric unit of the title 2:1 co-crystal, 2C(8)H(8)O(2)·C(14)H(14)N(4)O(2), comprises an acid molecule in a general position and half a diamide molecule, the latter being located about a centre of inversion. In the acid, the carboxylic acid group is twisted out of the plane of the benzen...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778829/ https://www.ncbi.nlm.nih.gov/pubmed/27006815 http://dx.doi.org/10.1107/S2056989016002735 |
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author | Syed, Sabrina Jotani, Mukesh M. Halim, Siti Nadiah Abdul Tiekink, Edward R. T. |
author_facet | Syed, Sabrina Jotani, Mukesh M. Halim, Siti Nadiah Abdul Tiekink, Edward R. T. |
author_sort | Syed, Sabrina |
collection | PubMed |
description | The asymmetric unit of the title 2:1 co-crystal, 2C(8)H(8)O(2)·C(14)H(14)N(4)O(2), comprises an acid molecule in a general position and half a diamide molecule, the latter being located about a centre of inversion. In the acid, the carboxylic acid group is twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 28.51 (8)°] and the carbonyl O atom and methyl group lie approximately to the same side of the molecule [hydroxy-O—C—C—C(H) torsion angle = −27.92 (17)°]. In the diamide, the central C(4)N(2)O(2) core is almost planar (r.m.s. deviation = 0.031 Å), and the pyridyl rings are perpendicular, lying to either side of the central plane [central residue/pyridyl dihedral angle = 88.60 (5)°]. In the molecular packing, three-molecule aggregates are formed via hydroxy-O—H⋯N(pyridyl) hydrogen bonds. These are connected into a supramolecular layer parallel to (12[Image: see text]) via amide-N—H⋯O(carbonyl) hydrogen bonds, as well as methylene-C—H⋯O(amide) interactions. Significant π–π interactions occur between benzene/benzene, pyridyl/benzene and pyridyl/pyridyl rings within and between layers to consolidate the three-dimensional packing. |
format | Online Article Text |
id | pubmed-4778829 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47788292016-03-22 A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis Syed, Sabrina Jotani, Mukesh M. Halim, Siti Nadiah Abdul Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the title 2:1 co-crystal, 2C(8)H(8)O(2)·C(14)H(14)N(4)O(2), comprises an acid molecule in a general position and half a diamide molecule, the latter being located about a centre of inversion. In the acid, the carboxylic acid group is twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 28.51 (8)°] and the carbonyl O atom and methyl group lie approximately to the same side of the molecule [hydroxy-O—C—C—C(H) torsion angle = −27.92 (17)°]. In the diamide, the central C(4)N(2)O(2) core is almost planar (r.m.s. deviation = 0.031 Å), and the pyridyl rings are perpendicular, lying to either side of the central plane [central residue/pyridyl dihedral angle = 88.60 (5)°]. In the molecular packing, three-molecule aggregates are formed via hydroxy-O—H⋯N(pyridyl) hydrogen bonds. These are connected into a supramolecular layer parallel to (12[Image: see text]) via amide-N—H⋯O(carbonyl) hydrogen bonds, as well as methylene-C—H⋯O(amide) interactions. Significant π–π interactions occur between benzene/benzene, pyridyl/benzene and pyridyl/pyridyl rings within and between layers to consolidate the three-dimensional packing. International Union of Crystallography 2016-02-20 /pmc/articles/PMC4778829/ /pubmed/27006815 http://dx.doi.org/10.1107/S2056989016002735 Text en © Syed et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Syed, Sabrina Jotani, Mukesh M. Halim, Siti Nadiah Abdul Tiekink, Edward R. T. A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title | A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title_full | A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title_fullStr | A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title_short | A 2:1 co-crystal of 2-methylbenzoic acid and N,N′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis |
title_sort | 2:1 co-crystal of 2-methylbenzoic acid and n,n′-bis(pyridin-4-ylmethyl)ethanediamide: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778829/ https://www.ncbi.nlm.nih.gov/pubmed/27006815 http://dx.doi.org/10.1107/S2056989016002735 |
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