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2-Methyl­imidazolium picrate

In both ionic components of the title salt, C(4)H(7)N(2) (+)·C(6)H(2)N(3)O(7) (−), the rings are approximately planar; the maximum deviation from the mean plane is an order of magnitude larger in the picrate ring [0.0289 (10) Å] than in the imidazolium ring [0.0028 (10) Å. The nitro groups are twist...

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Autores principales: Dutkiewicz, Grzegorz, Samshuddin, S., Narayana, B., Yathirajan, H. S., Kubicki, Maciej
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050384/
https://www.ncbi.nlm.nih.gov/pubmed/21522735
http://dx.doi.org/10.1107/S1600536810053390
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author Dutkiewicz, Grzegorz
Samshuddin, S.
Narayana, B.
Yathirajan, H. S.
Kubicki, Maciej
author_facet Dutkiewicz, Grzegorz
Samshuddin, S.
Narayana, B.
Yathirajan, H. S.
Kubicki, Maciej
author_sort Dutkiewicz, Grzegorz
collection PubMed
description In both ionic components of the title salt, C(4)H(7)N(2) (+)·C(6)H(2)N(3)O(7) (−), the rings are approximately planar; the maximum deviation from the mean plane is an order of magnitude larger in the picrate ring [0.0289 (10) Å] than in the imidazolium ring [0.0028 (10) Å. The nitro groups are twisted with respect to the six-atom ring plane; the NO(2) groups next to the oxide O atom, at the 2- and 6-positions, are twisted more [by 53.59 (9) and 18.46 (12)°] than the NO(2) group at the 4-postition, for which the twist angle is 7.28 (16)°. In the crystal, N—H⋯O hydrogen bonds, in which the hydroxyl O atom acts as a double acceptor and one of the O atoms from a nitro group acts as an additional acceptor, connect mol­ecules into chains along the c-axis direction. Relatively short C—H⋯O contacts and π–π inter­actions between symmetry-related six-membered rings [centroid–centroid distances = 3.5938 (10) and 3.6223 (10) Å] also occur.
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spelling pubmed-30503842011-04-26 2-Methyl­imidazolium picrate Dutkiewicz, Grzegorz Samshuddin, S. Narayana, B. Yathirajan, H. S. Kubicki, Maciej Acta Crystallogr Sect E Struct Rep Online Organic Papers In both ionic components of the title salt, C(4)H(7)N(2) (+)·C(6)H(2)N(3)O(7) (−), the rings are approximately planar; the maximum deviation from the mean plane is an order of magnitude larger in the picrate ring [0.0289 (10) Å] than in the imidazolium ring [0.0028 (10) Å. The nitro groups are twisted with respect to the six-atom ring plane; the NO(2) groups next to the oxide O atom, at the 2- and 6-positions, are twisted more [by 53.59 (9) and 18.46 (12)°] than the NO(2) group at the 4-postition, for which the twist angle is 7.28 (16)°. In the crystal, N—H⋯O hydrogen bonds, in which the hydroxyl O atom acts as a double acceptor and one of the O atoms from a nitro group acts as an additional acceptor, connect mol­ecules into chains along the c-axis direction. Relatively short C—H⋯O contacts and π–π inter­actions between symmetry-related six-membered rings [centroid–centroid distances = 3.5938 (10) and 3.6223 (10) Å] also occur. International Union of Crystallography 2010-12-24 /pmc/articles/PMC3050384/ /pubmed/21522735 http://dx.doi.org/10.1107/S1600536810053390 Text en © Dutkiewicz 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
Dutkiewicz, Grzegorz
Samshuddin, S.
Narayana, B.
Yathirajan, H. S.
Kubicki, Maciej
2-Methyl­imidazolium picrate
title 2-Methyl­imidazolium picrate
title_full 2-Methyl­imidazolium picrate
title_fullStr 2-Methyl­imidazolium picrate
title_full_unstemmed 2-Methyl­imidazolium picrate
title_short 2-Methyl­imidazolium picrate
title_sort 2-methyl­imidazolium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050384/
https://www.ncbi.nlm.nih.gov/pubmed/21522735
http://dx.doi.org/10.1107/S1600536810053390
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