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2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis
The asymmetric unit of the title salt, C(14)H(16)N(4)O(2) (2+)·2C(9)H(5)O(6) (−), comprises half a dication, being located about a centre of inversion, and one anion, in a general position. The central C(4)N(2)O(2) group of atoms in the dication are almost planar (r.m.s. deviation = 0.009 Å), and th...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770948/ https://www.ncbi.nlm.nih.gov/pubmed/26958398 http://dx.doi.org/10.1107/S2056989016000980 |
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author | Jotani, Mukesh M. Syed, Sabrina Halim, Siti Nadiah Abdul Tiekink, Edward R. T. |
author_facet | Jotani, Mukesh M. Syed, Sabrina Halim, Siti Nadiah Abdul Tiekink, Edward R. T. |
author_sort | Jotani, Mukesh M. |
collection | PubMed |
description | The asymmetric unit of the title salt, C(14)H(16)N(4)O(2) (2+)·2C(9)H(5)O(6) (−), comprises half a dication, being located about a centre of inversion, and one anion, in a general position. The central C(4)N(2)O(2) group of atoms in the dication are almost planar (r.m.s. deviation = 0.009 Å), and the carbonyl groups lie in an anti disposition to enable the formation of intramolecular amide-N—H⋯O(carbonyl) hydrogen bonds. To a first approximation, the pyridinium and amide N atoms lie to the same side of the molecule [N(py)—C—C—N(amide) torsion angle = 34.8 (2)°], and the anti pyridinium rings are approximately perpendicular to the central part of the molecule [dihedral angle = 68.21 (8)°]. In the anion, one carboxylate group is almost coplanar with the ring to which it is connected [C(ben)—C(ben)—C(q)—O torsion angle = 2.0 (3)°], whereas the other carboxylate and carboxylic acid groups are twisted out of the plane [torsion angles = 16.4 (3) and 15.3 (3)°, respectively]. In the crystal, anions assemble into layers parallel to (10-4) via hydroxy-O—H⋯O(carbonyl) and charge-assisted hydroxy-O—H⋯O(carboxylate) hydrogen bonds. The dications are linked into supramolecular tapes by amide-N—H⋯O(amide) hydrogen bonds, and thread through the voids in the anionic layers, being connected by charge-assisted pyridinium-N—O(carboxylate) hydrogen bonds, so that a three-dimensional architecture ensues. An analysis of the Hirshfeld surface points to the importance of O—H⋯O hydrogen bonding in the crystal structure. |
format | Online Article Text |
id | pubmed-4770948 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47709482016-03-08 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis Jotani, Mukesh M. Syed, Sabrina Halim, Siti Nadiah Abdul Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric unit of the title salt, C(14)H(16)N(4)O(2) (2+)·2C(9)H(5)O(6) (−), comprises half a dication, being located about a centre of inversion, and one anion, in a general position. The central C(4)N(2)O(2) group of atoms in the dication are almost planar (r.m.s. deviation = 0.009 Å), and the carbonyl groups lie in an anti disposition to enable the formation of intramolecular amide-N—H⋯O(carbonyl) hydrogen bonds. To a first approximation, the pyridinium and amide N atoms lie to the same side of the molecule [N(py)—C—C—N(amide) torsion angle = 34.8 (2)°], and the anti pyridinium rings are approximately perpendicular to the central part of the molecule [dihedral angle = 68.21 (8)°]. In the anion, one carboxylate group is almost coplanar with the ring to which it is connected [C(ben)—C(ben)—C(q)—O torsion angle = 2.0 (3)°], whereas the other carboxylate and carboxylic acid groups are twisted out of the plane [torsion angles = 16.4 (3) and 15.3 (3)°, respectively]. In the crystal, anions assemble into layers parallel to (10-4) via hydroxy-O—H⋯O(carbonyl) and charge-assisted hydroxy-O—H⋯O(carboxylate) hydrogen bonds. The dications are linked into supramolecular tapes by amide-N—H⋯O(amide) hydrogen bonds, and thread through the voids in the anionic layers, being connected by charge-assisted pyridinium-N—O(carboxylate) hydrogen bonds, so that a three-dimensional architecture ensues. An analysis of the Hirshfeld surface points to the importance of O—H⋯O hydrogen bonding in the crystal structure. International Union of Crystallography 2016-01-27 /pmc/articles/PMC4770948/ /pubmed/26958398 http://dx.doi.org/10.1107/S2056989016000980 Text en © Jotani 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 Jotani, Mukesh M. Syed, Sabrina Halim, Siti Nadiah Abdul Tiekink, Edward R. T. 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title | 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title_full | 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title_fullStr | 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title_short | 2-({[(Pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and Hirshfeld surface analysis |
title_sort | 2-({[(pyridin-1-ium-2-ylmethyl)carbamoyl]formamido}methyl)pyridin-1-ium bis(3,5-dicarboxybenzoate): crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770948/ https://www.ncbi.nlm.nih.gov/pubmed/26958398 http://dx.doi.org/10.1107/S2056989016000980 |
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