Cargando…
Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine
The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine, namely, bis(2-pyridone) chloranilic acid, 2C(5)H(5)NO·C(6)H(2)Cl(2)O(4), (I), bis(3-hydroxypyridinium) chlo...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730315/ https://www.ncbi.nlm.nih.gov/pubmed/29250378 http://dx.doi.org/10.1107/S2056989017013536 |
_version_ | 1783286342435733504 |
---|---|
author | Gotoh, Kazuma Ishida, Hiroyuki |
author_facet | Gotoh, Kazuma Ishida, Hiroyuki |
author_sort | Gotoh, Kazuma |
collection | PubMed |
description | The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine, namely, bis(2-pyridone) chloranilic acid, 2C(5)H(5)NO·C(6)H(2)Cl(2)O(4), (I), bis(3-hydroxypyridinium) chloranilate, 2C(5)H(6)NO(+)·C(6)Cl(2)O(4) (2−), (II), and bis(4-hydroxypyridinium) chloranilate, 2C(5)H(6)NO(+)·C(6)Cl(2)O(4) (2−), (III), have been determined at 120 K. In the crystal of (I), the base molecule is in the lactam form and no acid–base interaction involving H-atom transfer is observed. The acid molecule lies on an inversion centre and the asymmetric unit consists of one half-molecule of chloranilic acid and one 2-pyridone molecule, which are linked via a short O—H⋯O hydrogen bond. 2-Pyridone molecules form a head-to-head dimer via a pair of N—H⋯O hydrogen bonds, resulting in a tape structure along [201]. In the crystals of (II) and (III), acid–base interactions involving H-atom transfer are observed and the divalent cations lie on an inversion centre. The asymmetric unit of (II) consists of one half of a chloranilate anion and one 3-hydroxypyridinium cation, while that of (III) comprises two independent halves of anions and two 4-hydroxypyridinium cations. The primary intermolecular interaction in (II) is a bifurcated O—H⋯(O,O) hydrogen bond between the cation and the anion. The hydrogen-bonded units are further linked via N—H⋯O hydrogen bonds, forming a layer parallel to the bc plane. In (III), one anion is surrounded by four cations via O—H⋯O and C—H⋯O hydrogen bonds, while the other is surrounded by four cations via N—H⋯O and C—H⋯Cl hydrogen bonds. These interactions link the cations and the anions into a layer parallel to (301). |
format | Online Article Text |
id | pubmed-5730315 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-57303152017-12-15 Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine Gotoh, Kazuma Ishida, Hiroyuki Acta Crystallogr E Crystallogr Commun Research Communications The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine, namely, bis(2-pyridone) chloranilic acid, 2C(5)H(5)NO·C(6)H(2)Cl(2)O(4), (I), bis(3-hydroxypyridinium) chloranilate, 2C(5)H(6)NO(+)·C(6)Cl(2)O(4) (2−), (II), and bis(4-hydroxypyridinium) chloranilate, 2C(5)H(6)NO(+)·C(6)Cl(2)O(4) (2−), (III), have been determined at 120 K. In the crystal of (I), the base molecule is in the lactam form and no acid–base interaction involving H-atom transfer is observed. The acid molecule lies on an inversion centre and the asymmetric unit consists of one half-molecule of chloranilic acid and one 2-pyridone molecule, which are linked via a short O—H⋯O hydrogen bond. 2-Pyridone molecules form a head-to-head dimer via a pair of N—H⋯O hydrogen bonds, resulting in a tape structure along [201]. In the crystals of (II) and (III), acid–base interactions involving H-atom transfer are observed and the divalent cations lie on an inversion centre. The asymmetric unit of (II) consists of one half of a chloranilate anion and one 3-hydroxypyridinium cation, while that of (III) comprises two independent halves of anions and two 4-hydroxypyridinium cations. The primary intermolecular interaction in (II) is a bifurcated O—H⋯(O,O) hydrogen bond between the cation and the anion. The hydrogen-bonded units are further linked via N—H⋯O hydrogen bonds, forming a layer parallel to the bc plane. In (III), one anion is surrounded by four cations via O—H⋯O and C—H⋯O hydrogen bonds, while the other is surrounded by four cations via N—H⋯O and C—H⋯Cl hydrogen bonds. These interactions link the cations and the anions into a layer parallel to (301). International Union of Crystallography 2017-09-29 /pmc/articles/PMC5730315/ /pubmed/29250378 http://dx.doi.org/10.1107/S2056989017013536 Text en © Gotoh and Ishida 2017 http://creativecommons.org/licenses/by/2.0/uk/ 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/2.0/uk/ |
spellingShingle | Research Communications Gotoh, Kazuma Ishida, Hiroyuki Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title | Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title_full | Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title_fullStr | Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title_full_unstemmed | Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title_short | Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
title_sort | crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730315/ https://www.ncbi.nlm.nih.gov/pubmed/29250378 http://dx.doi.org/10.1107/S2056989017013536 |
work_keys_str_mv | AT gotohkazuma crystalstructuresofthreehydrogenbonded12compoundsofchloranilicacidwith2pyridone3hydroxypyridineand4hyroxypyridine AT ishidahiroyuki crystalstructuresofthreehydrogenbonded12compoundsofchloranilicacidwith2pyridone3hydroxypyridineand4hyroxypyridine |