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Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate

In the structure of the title 2:1 proton-transfer compound, 2C(12)H(8)N(3)O(2) (+)·C(10)H(4)O(8) (2−), the 6-nitro-1,10-phenanthroline mol­ecules act as proton sponges, accepting protons from pyromellitic acid. The –NO(2) group of one of the 6-nitro-1,10-phenanthrolin-1-ium cations is disordered and...

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Autores principales: Zhong, Kai-Long, Ni, Chao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998480/
https://www.ncbi.nlm.nih.gov/pubmed/24764973
http://dx.doi.org/10.1107/S1600536814002414
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author Zhong, Kai-Long
Ni, Chao
author_facet Zhong, Kai-Long
Ni, Chao
author_sort Zhong, Kai-Long
collection PubMed
description In the structure of the title 2:1 proton-transfer compound, 2C(12)H(8)N(3)O(2) (+)·C(10)H(4)O(8) (2−), the 6-nitro-1,10-phenanthroline mol­ecules act as proton sponges, accepting protons from pyromellitic acid. The –NO(2) group of one of the 6-nitro-1,10-phenanthrolin-1-ium cations is disordered and was refined with a site-occupancy ratio of 0.624 (15):0.376 (15). Two –COOH(–COO(−)) groups of the 2,5-di­carb­oxy­terephthalate dianion are disordered and were refined with site-occupancy ratios of 0.769 (4):0.231 (4) and 0.766 (5):0.234 (5). The –NO(2) group of the second cation is also disordered about a pseudo-twofold rotation axis and was refined with a site-occupancy ratio of 0.903 (3):0.097 (3). There is an intra­molecular O—H⋯O hydrogen bond in the anion. The phenanthroline rings of the two cations are inclined to one another by 31.3 (1)°. In the anions, considering the major components only, the carb­oxy­lic acid groups (–COOH) are inclined to the benzene ring by 17.3 (2) and 22.3 (3)°. The carboxyl­ate groups (–COO(−)) are twisted by 9.3 (2) and 13.6 (6)° with respect to the benzene ring. In the crystal, adjacent 2,5-di­carb­oxy­terephthalate anions are linked via O—H⋯O hydrogen bonds, forming chains propagating along [010]. The cations are attached to the chain of anions by N—H⋯O hydrogen bonds.
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spelling pubmed-39984802014-04-24 Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate Zhong, Kai-Long Ni, Chao Acta Crystallogr Sect E Struct Rep Online Organic Papers In the structure of the title 2:1 proton-transfer compound, 2C(12)H(8)N(3)O(2) (+)·C(10)H(4)O(8) (2−), the 6-nitro-1,10-phenanthroline mol­ecules act as proton sponges, accepting protons from pyromellitic acid. The –NO(2) group of one of the 6-nitro-1,10-phenanthrolin-1-ium cations is disordered and was refined with a site-occupancy ratio of 0.624 (15):0.376 (15). Two –COOH(–COO(−)) groups of the 2,5-di­carb­oxy­terephthalate dianion are disordered and were refined with site-occupancy ratios of 0.769 (4):0.231 (4) and 0.766 (5):0.234 (5). The –NO(2) group of the second cation is also disordered about a pseudo-twofold rotation axis and was refined with a site-occupancy ratio of 0.903 (3):0.097 (3). There is an intra­molecular O—H⋯O hydrogen bond in the anion. The phenanthroline rings of the two cations are inclined to one another by 31.3 (1)°. In the anions, considering the major components only, the carb­oxy­lic acid groups (–COOH) are inclined to the benzene ring by 17.3 (2) and 22.3 (3)°. The carboxyl­ate groups (–COO(−)) are twisted by 9.3 (2) and 13.6 (6)° with respect to the benzene ring. In the crystal, adjacent 2,5-di­carb­oxy­terephthalate anions are linked via O—H⋯O hydrogen bonds, forming chains propagating along [010]. The cations are attached to the chain of anions by N—H⋯O hydrogen bonds. International Union of Crystallography 2014-02-08 /pmc/articles/PMC3998480/ /pubmed/24764973 http://dx.doi.org/10.1107/S1600536814002414 Text en © Zhong and Ni 2014 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
Zhong, Kai-Long
Ni, Chao
Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title_full Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title_fullStr Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title_full_unstemmed Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title_short Bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
title_sort bis(6-nitro-1,10-phenanthrolin-1-ium) 2,5-di­carb­oxy­terephthalate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998480/
https://www.ncbi.nlm.nih.gov/pubmed/24764973
http://dx.doi.org/10.1107/S1600536814002414
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