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1-Piperonylpiperazinium picrate

In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmeth­yl)piperazin-1-ium 2,4,6-tri­nitro­phen­o­late], C(12)H(17)N(2)O(2) (+)·C(6)H(2)N(3)O(7) (−), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are tw...

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Autores principales: Kavitha, Channappa N., Kaur, Manpreet, Anderson, Brian J., Jasinski, Jerry P., Yathirajan, H. S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998354/
https://www.ncbi.nlm.nih.gov/pubmed/24764915
http://dx.doi.org/10.1107/S1600536814001524
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author Kavitha, Channappa N.
Kaur, Manpreet
Anderson, Brian J.
Jasinski, Jerry P.
Yathirajan, H. S.
author_facet Kavitha, Channappa N.
Kaur, Manpreet
Anderson, Brian J.
Jasinski, Jerry P.
Yathirajan, H. S.
author_sort Kavitha, Channappa N.
collection PubMed
description In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmeth­yl)piperazin-1-ium 2,4,6-tri­nitro­phen­o­late], C(12)H(17)N(2)O(2) (+)·C(6)H(2)N(3)O(7) (−), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter­act through N—H⋯O hydrogen bonds and a weak C—H⋯O inter­action. Weak C—H⋯O inter­actions are also observed between the anions, forming R (2) (2)(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking inter­action between the aromatic rings of the cation and the anion, with an inter­centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1).
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spelling pubmed-39983542014-04-24 1-Piperonylpiperazinium picrate Kavitha, Channappa N. Kaur, Manpreet Anderson, Brian J. Jasinski, Jerry P. Yathirajan, H. S. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmeth­yl)piperazin-1-ium 2,4,6-tri­nitro­phen­o­late], C(12)H(17)N(2)O(2) (+)·C(6)H(2)N(3)O(7) (−), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter­act through N—H⋯O hydrogen bonds and a weak C—H⋯O inter­action. Weak C—H⋯O inter­actions are also observed between the anions, forming R (2) (2)(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking inter­action between the aromatic rings of the cation and the anion, with an inter­centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). International Union of Crystallography 2014-01-29 /pmc/articles/PMC3998354/ /pubmed/24764915 http://dx.doi.org/10.1107/S1600536814001524 Text en © Kavitha et al. 2014 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
Kavitha, Channappa N.
Kaur, Manpreet
Anderson, Brian J.
Jasinski, Jerry P.
Yathirajan, H. S.
1-Piperonylpiperazinium picrate
title 1-Piperonylpiperazinium picrate
title_full 1-Piperonylpiperazinium picrate
title_fullStr 1-Piperonylpiperazinium picrate
title_full_unstemmed 1-Piperonylpiperazinium picrate
title_short 1-Piperonylpiperazinium picrate
title_sort 1-piperonylpiperazinium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998354/
https://www.ncbi.nlm.nih.gov/pubmed/24764915
http://dx.doi.org/10.1107/S1600536814001524
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