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1-(2-Methyl-5-nitro­phenyl)guanidinium picrate

In the crystal structure of the title salt, C(8)H(11)N(4)O(2) (+)·C(6)H(2)N(3)O(7) (−), the pictrate anion participates in extensive hydrogen bonding with the guanidinium ion group of the cation, linking the mol­ecules through N(+)—H⋯O(−) hydrogen bonds and inter­molecular N—H⋯O and C—H⋯O inter­acti...

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Autores principales: Jasinski, Jerry P., Butcher, Ray J., Swamy, M. T., Yathirajan, H. S., Ramesha, A. R.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971333/
https://www.ncbi.nlm.nih.gov/pubmed/21578381
http://dx.doi.org/10.1107/S1600536809037647
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author Jasinski, Jerry P.
Butcher, Ray J.
Swamy, M. T.
Yathirajan, H. S.
Ramesha, A. R.
author_facet Jasinski, Jerry P.
Butcher, Ray J.
Swamy, M. T.
Yathirajan, H. S.
Ramesha, A. R.
author_sort Jasinski, Jerry P.
collection PubMed
description In the crystal structure of the title salt, C(8)H(11)N(4)O(2) (+)·C(6)H(2)N(3)O(7) (−), the pictrate anion participates in extensive hydrogen bonding with the guanidinium ion group of the cation, linking the mol­ecules through N(+)—H⋯O(−) hydrogen bonds and inter­molecular N—H⋯O and C—H⋯O inter­actions. These hydrogen-bonding configurations involve two three-centre/bifurcated bonds [N—H⋯(O,O)] that are observed between two N atoms from the guanidinium ion group of the cation and the o-NO(2) and phenolate O atoms of the picrate anion. In addition, π–π inter­actions also contribute to the crystal packing, with a centroid-to-centroid distance of 3.693 (6) Å and a slippage angle of 1.614°. A significant number of conformational differences are observed between the salt in the crystal structure and the models obtained by density functional theory (DFT) calculations of the geometry-optimized structure.
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spelling pubmed-29713332010-12-30 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate Jasinski, Jerry P. Butcher, Ray J. Swamy, M. T. Yathirajan, H. S. Ramesha, A. R. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the crystal structure of the title salt, C(8)H(11)N(4)O(2) (+)·C(6)H(2)N(3)O(7) (−), the pictrate anion participates in extensive hydrogen bonding with the guanidinium ion group of the cation, linking the mol­ecules through N(+)—H⋯O(−) hydrogen bonds and inter­molecular N—H⋯O and C—H⋯O inter­actions. These hydrogen-bonding configurations involve two three-centre/bifurcated bonds [N—H⋯(O,O)] that are observed between two N atoms from the guanidinium ion group of the cation and the o-NO(2) and phenolate O atoms of the picrate anion. In addition, π–π inter­actions also contribute to the crystal packing, with a centroid-to-centroid distance of 3.693 (6) Å and a slippage angle of 1.614°. A significant number of conformational differences are observed between the salt in the crystal structure and the models obtained by density functional theory (DFT) calculations of the geometry-optimized structure. International Union of Crystallography 2009-10-17 /pmc/articles/PMC2971333/ /pubmed/21578381 http://dx.doi.org/10.1107/S1600536809037647 Text en © Jasinski 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
Jasinski, Jerry P.
Butcher, Ray J.
Swamy, M. T.
Yathirajan, H. S.
Ramesha, A. R.
1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title_full 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title_fullStr 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title_full_unstemmed 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title_short 1-(2-Methyl-5-nitro­phenyl)guanidinium picrate
title_sort 1-(2-methyl-5-nitro­phenyl)guanidinium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971333/
https://www.ncbi.nlm.nih.gov/pubmed/21578381
http://dx.doi.org/10.1107/S1600536809037647
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