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3-(1H-Imidazol-1-yl)propanaminium picrate

In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-tri­nitro­phenolate], C(6)H(12)N(3) (+)·C(6)H(2)N(3)O(7) (−), there are five independent cation–anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the amino­propyl group...

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Autores principales: Yamuna, T. S., Jasinski, Jerry P., Duff, Courtney E., Yathirajan, H. S., Kaur, Manpreet
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790432/
https://www.ncbi.nlm.nih.gov/pubmed/24098251
http://dx.doi.org/10.1107/S1600536813025646
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author Yamuna, T. S.
Jasinski, Jerry P.
Duff, Courtney E.
Yathirajan, H. S.
Kaur, Manpreet
author_facet Yamuna, T. S.
Jasinski, Jerry P.
Duff, Courtney E.
Yathirajan, H. S.
Kaur, Manpreet
author_sort Yamuna, T. S.
collection PubMed
description In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-tri­nitro­phenolate], C(6)H(12)N(3) (+)·C(6)H(2)N(3)O(7) (−), there are five independent cation–anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the amino­propyl group nearly at right angles to the mean plane of the imidazole ring showing C—N—C—C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H⋯O cation–anion and N—H⋯N cation–cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C—H⋯O cation–anion inter­actions occur.
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spelling pubmed-37904322013-10-04 3-(1H-Imidazol-1-yl)propanaminium picrate Yamuna, T. S. Jasinski, Jerry P. Duff, Courtney E. Yathirajan, H. S. Kaur, Manpreet Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-tri­nitro­phenolate], C(6)H(12)N(3) (+)·C(6)H(2)N(3)O(7) (−), there are five independent cation–anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the amino­propyl group nearly at right angles to the mean plane of the imidazole ring showing C—N—C—C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H⋯O cation–anion and N—H⋯N cation–cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C—H⋯O cation–anion inter­actions occur. International Union of Crystallography 2013-09-21 /pmc/articles/PMC3790432/ /pubmed/24098251 http://dx.doi.org/10.1107/S1600536813025646 Text en © Yamuna et al. 2013 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
Yamuna, T. S.
Jasinski, Jerry P.
Duff, Courtney E.
Yathirajan, H. S.
Kaur, Manpreet
3-(1H-Imidazol-1-yl)propanaminium picrate
title 3-(1H-Imidazol-1-yl)propanaminium picrate
title_full 3-(1H-Imidazol-1-yl)propanaminium picrate
title_fullStr 3-(1H-Imidazol-1-yl)propanaminium picrate
title_full_unstemmed 3-(1H-Imidazol-1-yl)propanaminium picrate
title_short 3-(1H-Imidazol-1-yl)propanaminium picrate
title_sort 3-(1h-imidazol-1-yl)propanaminium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790432/
https://www.ncbi.nlm.nih.gov/pubmed/24098251
http://dx.doi.org/10.1107/S1600536813025646
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