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1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate

In the structure of the 1:1 proton-transfer compound of 1,10-phenanthroline with 4,5-dichloro­phthalic acid, C(12)H(9)N(2) (+)·C(8)H(3)Cl(2)O(4) (−), determined at 130 K, the 1,10-phenanthrolinium cation and the hydrogen 4,5-dichloro­phthalate anion associate through a single N—H⋯O(carbox­yl) hydrog...

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Detalles Bibliográficos
Autores principales: Smith, Graham, Wermuth, Urs D., White, Jonathan M.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970357/
https://www.ncbi.nlm.nih.gov/pubmed/21577804
http://dx.doi.org/10.1107/S1600536809034448
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author Smith, Graham
Wermuth, Urs D.
White, Jonathan M.
author_facet Smith, Graham
Wermuth, Urs D.
White, Jonathan M.
author_sort Smith, Graham
collection PubMed
description In the structure of the 1:1 proton-transfer compound of 1,10-phenanthroline with 4,5-dichloro­phthalic acid, C(12)H(9)N(2) (+)·C(8)H(3)Cl(2)O(4) (−), determined at 130 K, the 1,10-phenanthrolinium cation and the hydrogen 4,5-dichloro­phthalate anion associate through a single N—H⋯O(carbox­yl) hydrogen bond giving discrete units which have no extension except through a number of weak cation C—H⋯O(anion) associations and weak cation–anion aromatic ring π–π inter­actions [minimum centroid–centroid separation = 3.6815 (12) Å]. The anions are essentially planar "[maximum deviation 0.214 (1) Å (a carboxyl O)] with the syn-related H atom of the carboxyl group, forming a short intra­molecular O—H⋯O(carbox­yl) hydrogen bond.
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spelling pubmed-29703572010-12-30 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate Smith, Graham Wermuth, Urs D. White, Jonathan M. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the structure of the 1:1 proton-transfer compound of 1,10-phenanthroline with 4,5-dichloro­phthalic acid, C(12)H(9)N(2) (+)·C(8)H(3)Cl(2)O(4) (−), determined at 130 K, the 1,10-phenanthrolinium cation and the hydrogen 4,5-dichloro­phthalate anion associate through a single N—H⋯O(carbox­yl) hydrogen bond giving discrete units which have no extension except through a number of weak cation C—H⋯O(anion) associations and weak cation–anion aromatic ring π–π inter­actions [minimum centroid–centroid separation = 3.6815 (12) Å]. The anions are essentially planar "[maximum deviation 0.214 (1) Å (a carboxyl O)] with the syn-related H atom of the carboxyl group, forming a short intra­molecular O—H⋯O(carbox­yl) hydrogen bond. International Union of Crystallography 2009-09-05 /pmc/articles/PMC2970357/ /pubmed/21577804 http://dx.doi.org/10.1107/S1600536809034448 Text en © Smith et al. 2009 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
Smith, Graham
Wermuth, Urs D.
White, Jonathan M.
1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title_full 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title_fullStr 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title_full_unstemmed 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title_short 1,10-Phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
title_sort 1,10-phenanthrolin-1-ium 2-carb­oxy-4,5-dichloro­benzoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970357/
https://www.ncbi.nlm.nih.gov/pubmed/21577804
http://dx.doi.org/10.1107/S1600536809034448
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