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Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1)
The asymmetric unit of the title co-crystal, 2C(14)H(13)N(2) (+)·C(10)H(4)O(8) (2−)·2C(14)H(12)N(2)·C(10)H(6)O(8), comprises a 2,9-dimethyl-1,10-phenanthrolin-1-ium cation (Me(2)PhenH(+)) and a 2,9-dimethyl-1,10-phenanthroline molecule (Me(2)Phen), each in a general position, and half each of a 2,5...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884443/ https://www.ncbi.nlm.nih.gov/pubmed/24427073 http://dx.doi.org/10.1107/S1600536813022691 |
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author | Arman, Hadi D. Kaulgud, Trupta Tiekink, Edward R. T. |
author_facet | Arman, Hadi D. Kaulgud, Trupta Tiekink, Edward R. T. |
author_sort | Arman, Hadi D. |
collection | PubMed |
description | The asymmetric unit of the title co-crystal, 2C(14)H(13)N(2) (+)·C(10)H(4)O(8) (2−)·2C(14)H(12)N(2)·C(10)H(6)O(8), comprises a 2,9-dimethyl-1,10-phenanthrolin-1-ium cation (Me(2)PhenH(+)) and a 2,9-dimethyl-1,10-phenanthroline molecule (Me(2)Phen), each in a general position, and half each of a 2,5-dicarboxybenzene-1,4-dicarboxylate dianion (LH(2) (2−)) and a benzene-1,2,4,5-tetracarboxylic acid molecule (LH(4)), each being disposed about a centre of inversion. Small twists are evident in the dianion [the C—C—C—O torsion angles are 168.41 (18) and 16.2 (3)°], whereas a major twist is found for one carboxylic acid group in the neutral molecule [C—C—C—O = 66.3 (2) and 18.2 (3)°]. The most prominent feature of the crystal packing is the formation of linear supramolecular chains along [001] mediated by charge-assisted O—H⋯O(−) hydrogen bonding between alternating LH(4) and LH(2) (2−). These are connected to the Me(2)PhenH(+) and Me(2)Phen species by N—H⋯O and O—H⋯N hydrogen bonds, respectively. A three-dimensional architecture is formed by C—H⋯O and π–π interactions [inter-centroid distance = 3.5337 (17) Å]. |
format | Online Article Text |
id | pubmed-3884443 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-38844432014-01-14 Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) Arman, Hadi D. Kaulgud, Trupta Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The asymmetric unit of the title co-crystal, 2C(14)H(13)N(2) (+)·C(10)H(4)O(8) (2−)·2C(14)H(12)N(2)·C(10)H(6)O(8), comprises a 2,9-dimethyl-1,10-phenanthrolin-1-ium cation (Me(2)PhenH(+)) and a 2,9-dimethyl-1,10-phenanthroline molecule (Me(2)Phen), each in a general position, and half each of a 2,5-dicarboxybenzene-1,4-dicarboxylate dianion (LH(2) (2−)) and a benzene-1,2,4,5-tetracarboxylic acid molecule (LH(4)), each being disposed about a centre of inversion. Small twists are evident in the dianion [the C—C—C—O torsion angles are 168.41 (18) and 16.2 (3)°], whereas a major twist is found for one carboxylic acid group in the neutral molecule [C—C—C—O = 66.3 (2) and 18.2 (3)°]. The most prominent feature of the crystal packing is the formation of linear supramolecular chains along [001] mediated by charge-assisted O—H⋯O(−) hydrogen bonding between alternating LH(4) and LH(2) (2−). These are connected to the Me(2)PhenH(+) and Me(2)Phen species by N—H⋯O and O—H⋯N hydrogen bonds, respectively. A three-dimensional architecture is formed by C—H⋯O and π–π interactions [inter-centroid distance = 3.5337 (17) Å]. International Union of Crystallography 2013-08-17 /pmc/articles/PMC3884443/ /pubmed/24427073 http://dx.doi.org/10.1107/S1600536813022691 Text en © Arman et al. 2013 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 Arman, Hadi D. Kaulgud, Trupta Tiekink, Edward R. T. Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title | Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title_full | Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title_fullStr | Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title_full_unstemmed | Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title_short | Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
title_sort | bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate–2,9-dimethyl-1,10-phenanthroline–benzene-1,2,4,5-tetracarboxylic acid (1/2/1) |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884443/ https://www.ncbi.nlm.nih.gov/pubmed/24427073 http://dx.doi.org/10.1107/S1600536813022691 |
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