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4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate

The title hydrated salt, C(8)H(11)N(2)O(+)·C(2)HO(4) (−)·H(2)O, was synthesized by a reaction of 4-meth­oxy­benzamidine (4-amidino­anisole) and oxalic acid in water solution. In the cation, the amidinium group forms a dihedral angle of 15.60 (6)° with the mean plane of the benzene ring. In the cryst...

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Autores principales: Irrera, Simona, Portalone, Gustavo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588951/
https://www.ncbi.nlm.nih.gov/pubmed/23476187
http://dx.doi.org/10.1107/S1600536812046351
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author Irrera, Simona
Portalone, Gustavo
author_facet Irrera, Simona
Portalone, Gustavo
author_sort Irrera, Simona
collection PubMed
description The title hydrated salt, C(8)H(11)N(2)O(+)·C(2)HO(4) (−)·H(2)O, was synthesized by a reaction of 4-meth­oxy­benzamidine (4-amidino­anisole) and oxalic acid in water solution. In the cation, the amidinium group forms a dihedral angle of 15.60 (6)° with the mean plane of the benzene ring. In the crystal, each amidinium unit is bound to three acetate anions and one water mol­ecule by six distinct N—H⋯O hydrogen bonds. The ion pairs of the asymmetric unit are joined by two N—H⋯O hydrogen bonds into ionic dimers in which the carbonyl O atom of the semi-oxalate anion acts as a bifurcated acceptor, thus generating an R (1) (2)(6) motif. These subunits are then joined through the remaining N—H⋯O hydrogen bonds to adjacent semi-oxalate anions into linear tetra­meric chains running approximately along the b axis. The structure is stabilized by N—H⋯O and O—H⋯O inter­molecular hydrogen bonds. The water mol­ecule plays an important role in the cohesion and the stability of the crystal structure being involved in three hydrogen bonds connecting two semi-oxalate anions as donor and a benzamidinium cation as acceptor.
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spelling pubmed-35889512013-03-08 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate Irrera, Simona Portalone, Gustavo Acta Crystallogr Sect E Struct Rep Online Organic Papers The title hydrated salt, C(8)H(11)N(2)O(+)·C(2)HO(4) (−)·H(2)O, was synthesized by a reaction of 4-meth­oxy­benzamidine (4-amidino­anisole) and oxalic acid in water solution. In the cation, the amidinium group forms a dihedral angle of 15.60 (6)° with the mean plane of the benzene ring. In the crystal, each amidinium unit is bound to three acetate anions and one water mol­ecule by six distinct N—H⋯O hydrogen bonds. The ion pairs of the asymmetric unit are joined by two N—H⋯O hydrogen bonds into ionic dimers in which the carbonyl O atom of the semi-oxalate anion acts as a bifurcated acceptor, thus generating an R (1) (2)(6) motif. These subunits are then joined through the remaining N—H⋯O hydrogen bonds to adjacent semi-oxalate anions into linear tetra­meric chains running approximately along the b axis. The structure is stabilized by N—H⋯O and O—H⋯O inter­molecular hydrogen bonds. The water mol­ecule plays an important role in the cohesion and the stability of the crystal structure being involved in three hydrogen bonds connecting two semi-oxalate anions as donor and a benzamidinium cation as acceptor. International Union of Crystallography 2012-11-14 /pmc/articles/PMC3588951/ /pubmed/23476187 http://dx.doi.org/10.1107/S1600536812046351 Text en © Irrera and Portalone 2012 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
Irrera, Simona
Portalone, Gustavo
4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title_full 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title_fullStr 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title_full_unstemmed 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title_short 4-Meth­oxy­benzamidinium hydrogen oxalate monohydrate
title_sort 4-meth­oxy­benzamidinium hydrogen oxalate monohydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588951/
https://www.ncbi.nlm.nih.gov/pubmed/23476187
http://dx.doi.org/10.1107/S1600536812046351
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