Cargando…
2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex
In the crystal structure of the title compound (systematic name: 2,3-dichlorobenzene-1,4-diol 2,3-dichlorocyclohexa-2,5-diene-1,4-dione monohydrate), C(6)H(4)Cl(2)O(2)·C(6)H(2)Cl(2)O(2)·H(2)O, the 2,3-dichloro-1,4-hydroquinone donor (D) and the 2,3-dichloro-1,4-benzoquinone acceptor (A) molecul...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247373/ https://www.ncbi.nlm.nih.gov/pubmed/22219991 http://dx.doi.org/10.1107/S1600536811041377 |
_version_ | 1782220092364292096 |
---|---|
author | Guégano, Xavier Hauser, Jürg Liu, Shi-Xia Decurtins, Silvio |
author_facet | Guégano, Xavier Hauser, Jürg Liu, Shi-Xia Decurtins, Silvio |
author_sort | Guégano, Xavier |
collection | PubMed |
description | In the crystal structure of the title compound (systematic name: 2,3-dichlorobenzene-1,4-diol 2,3-dichlorocyclohexa-2,5-diene-1,4-dione monohydrate), C(6)H(4)Cl(2)O(2)·C(6)H(2)Cl(2)O(2)·H(2)O, the 2,3-dichloro-1,4-hydroquinone donor (D) and the 2,3-dichloro-1,4-benzoquinone acceptor (A) molecules form alternating stacks along [100]. Their molecular planes [maximum deviations for non-H atoms: 0.0133 (14) (D) and 0.0763 (14) Å (A)] are inclined to one another by 1.45 (3)° and are thus almost parallel. There are π–π interactions involving the D and A molecules, with centroid–centroid distances of 3.5043 (9) and 3.9548 (9) Å. Intermolecular O—H⋯O hydrogen bonds involving the water molecule and the hydroxy and ketone groups lead to the formation of two-dimensional networks lying parallel to (001). These networks are linked by C—H⋯O interactions, forming a three-dimensional structure. |
format | Online Article Text |
id | pubmed-3247373 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32473732012-01-04 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex Guégano, Xavier Hauser, Jürg Liu, Shi-Xia Decurtins, Silvio Acta Crystallogr Sect E Struct Rep Online Organic Papers In the crystal structure of the title compound (systematic name: 2,3-dichlorobenzene-1,4-diol 2,3-dichlorocyclohexa-2,5-diene-1,4-dione monohydrate), C(6)H(4)Cl(2)O(2)·C(6)H(2)Cl(2)O(2)·H(2)O, the 2,3-dichloro-1,4-hydroquinone donor (D) and the 2,3-dichloro-1,4-benzoquinone acceptor (A) molecules form alternating stacks along [100]. Their molecular planes [maximum deviations for non-H atoms: 0.0133 (14) (D) and 0.0763 (14) Å (A)] are inclined to one another by 1.45 (3)° and are thus almost parallel. There are π–π interactions involving the D and A molecules, with centroid–centroid distances of 3.5043 (9) and 3.9548 (9) Å. Intermolecular O—H⋯O hydrogen bonds involving the water molecule and the hydroxy and ketone groups lead to the formation of two-dimensional networks lying parallel to (001). These networks are linked by C—H⋯O interactions, forming a three-dimensional structure. International Union of Crystallography 2011-10-12 /pmc/articles/PMC3247373/ /pubmed/22219991 http://dx.doi.org/10.1107/S1600536811041377 Text en © Guégano et al. 2011 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 | Organic Papers Guégano, Xavier Hauser, Jürg Liu, Shi-Xia Decurtins, Silvio 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title | 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title_full | 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title_fullStr | 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title_full_unstemmed | 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title_short | 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D—A] charge-transfer complex |
title_sort | 2,3-dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [d—a] charge-transfer complex |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247373/ https://www.ncbi.nlm.nih.gov/pubmed/22219991 http://dx.doi.org/10.1107/S1600536811041377 |
work_keys_str_mv | AT gueganoxavier 23dichloro14hydroquinone23dichloro14benzoquinonemonohydrateaquinhydronetype11donoracceptordachargetransfercomplex AT hauserjurg 23dichloro14hydroquinone23dichloro14benzoquinonemonohydrateaquinhydronetype11donoracceptordachargetransfercomplex AT liushixia 23dichloro14hydroquinone23dichloro14benzoquinonemonohydrateaquinhydronetype11donoracceptordachargetransfercomplex AT decurtinssilvio 23dichloro14hydroquinone23dichloro14benzoquinonemonohydrateaquinhydronetype11donoracceptordachargetransfercomplex |