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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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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. |
format | Text |
id | pubmed-2971333 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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