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2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate

In the title salt, C(6)H(10)N(3)O(+)·C(6)H(2)N(3)O(7) (−), the dihedral angle between the mean planes of the benzene and pyridine rings is 3.1 (1)°. In the cation, the meth­oxy group is almost coplanar with the pyridine ring [C—O—C—N = −0.6 (2)°]. The p-nitro [C—C—N—O = −1.17 (19)°] and one o-nitro...

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Autores principales: Jasinski, Jerry P., Butcher, Ray J., Yathirajan, H. S., Narayana, B., Prakash Kamath, K.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979045/
https://www.ncbi.nlm.nih.gov/pubmed/21579227
http://dx.doi.org/10.1107/S1600536810014583
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author Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Narayana, B.
Prakash Kamath, K.
author_facet Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Narayana, B.
Prakash Kamath, K.
author_sort Jasinski, Jerry P.
collection PubMed
description In the title salt, C(6)H(10)N(3)O(+)·C(6)H(2)N(3)O(7) (−), the dihedral angle between the mean planes of the benzene and pyridine rings is 3.1 (1)°. In the cation, the meth­oxy group is almost coplanar with the pyridine ring [C—O—C—N = −0.6 (2)°]. The p-nitro [C—C—N—O = −1.17 (19)°] and one o-nitro [C—C—N—O = 1.83 (19)°] group in the anion are essentially coplanar with the benzene ring. The other disordered o-nitro group containing the major occupancy [0.868 (6)] O atom is twisted −29.0 (2)° from the mean plane of the benzene ring. A bifurcated N—H⋯(O.O) hydrogen bond and weak C—H⋯O intermolecular inter­action between the cation and anion produce a network of infinite O—H⋯O—H⋯O—H chains along the c axis in the [101] plane which helps to establish crystal packing. Comparison to a DFT computational calculation indicates that significant conformational changes occur in the free state.
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spelling pubmed-29790452010-12-30 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Prakash Kamath, K. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title salt, C(6)H(10)N(3)O(+)·C(6)H(2)N(3)O(7) (−), the dihedral angle between the mean planes of the benzene and pyridine rings is 3.1 (1)°. In the cation, the meth­oxy group is almost coplanar with the pyridine ring [C—O—C—N = −0.6 (2)°]. The p-nitro [C—C—N—O = −1.17 (19)°] and one o-nitro [C—C—N—O = 1.83 (19)°] group in the anion are essentially coplanar with the benzene ring. The other disordered o-nitro group containing the major occupancy [0.868 (6)] O atom is twisted −29.0 (2)° from the mean plane of the benzene ring. A bifurcated N—H⋯(O.O) hydrogen bond and weak C—H⋯O intermolecular inter­action between the cation and anion produce a network of infinite O—H⋯O—H⋯O—H chains along the c axis in the [101] plane which helps to establish crystal packing. Comparison to a DFT computational calculation indicates that significant conformational changes occur in the free state. International Union of Crystallography 2010-04-28 /pmc/articles/PMC2979045/ /pubmed/21579227 http://dx.doi.org/10.1107/S1600536810014583 Text en © Jasinski et al. 2010 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.
Yathirajan, H. S.
Narayana, B.
Prakash Kamath, K.
2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title_full 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title_fullStr 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title_full_unstemmed 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title_short 2-Amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
title_sort 2-amino-4-meth­oxy-6-methyl­pyrimidin-1-ium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979045/
https://www.ncbi.nlm.nih.gov/pubmed/21579227
http://dx.doi.org/10.1107/S1600536810014583
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