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1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide

The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodo­nitro­benzene and 1,4-diaza­bicyclo­[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitro­phen­yl)pip...

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Detalles Bibliográficos
Autores principales: Peuronen, Anssi, Lahtinen, Manu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393262/
https://www.ncbi.nlm.nih.gov/pubmed/22807819
http://dx.doi.org/10.1107/S1600536812024531
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author Peuronen, Anssi
Lahtinen, Manu
author_facet Peuronen, Anssi
Lahtinen, Manu
author_sort Peuronen, Anssi
collection PubMed
description The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodo­nitro­benzene and 1,4-diaza­bicyclo­[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitro­phen­yl)piperazine with an iodide anion. The crystal structure determination was carried out as no crystal structure had been previously reported in the investigations describing the corresponding reaction with 4-chloro­nitro­benze. Indeed, the crystal structure of the title compound confirms the mol­ecular composition proposed earlier for the analogous chloride salt. The cation conformation is similar to the previously reported dinitro analogue 1-{2-[4-(2,4-dinitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane chloride [Clegg et al. (2004 ▶). Acta Cryst. E60, o291–o293]. The crystal packing is dominated by cation⋯I(−) inter­actions in addition to weak inter­molecular C—H⋯O(2)N and C—H⋯N inter­actions between the cations.
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spelling pubmed-33932622012-07-17 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide Peuronen, Anssi Lahtinen, Manu Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(28)N(5)O(2) (+)·I(−), was observed as a main product in an intended 1:1 reaction between 4-iodo­nitro­benzene and 1,4-diaza­bicyclo­[2.2.2]octane (DABCO). In the reaction, DABCO undergoes a ring opening to yield a quaternary salt of DABCO and 1-ethyl-4-(4-nitro­phen­yl)piperazine with an iodide anion. The crystal structure determination was carried out as no crystal structure had been previously reported in the investigations describing the corresponding reaction with 4-chloro­nitro­benze. Indeed, the crystal structure of the title compound confirms the mol­ecular composition proposed earlier for the analogous chloride salt. The cation conformation is similar to the previously reported dinitro analogue 1-{2-[4-(2,4-dinitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane chloride [Clegg et al. (2004 ▶). Acta Cryst. E60, o291–o293]. The crystal packing is dominated by cation⋯I(−) inter­actions in addition to weak inter­molecular C—H⋯O(2)N and C—H⋯N inter­actions between the cations. International Union of Crystallography 2012-06-02 /pmc/articles/PMC3393262/ /pubmed/22807819 http://dx.doi.org/10.1107/S1600536812024531 Text en © Peuronen and Lahtinen 2012 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
Peuronen, Anssi
Lahtinen, Manu
1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title_full 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title_fullStr 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title_full_unstemmed 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title_short 1-{2-[4-(4-Nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
title_sort 1-{2-[4-(4-nitro­phen­yl)piperazin-1-yl]eth­yl}-4-aza-1-azoniabicyclo­[2.2.2]octane iodide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393262/
https://www.ncbi.nlm.nih.gov/pubmed/22807819
http://dx.doi.org/10.1107/S1600536812024531
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