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[2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis

1,3-Benzo­thia­zin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piper­id­in-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a...

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Autores principales: Eckhardt, Tamira, Goddard, Richard, Rudolph, Ines, Richter, Adrian, Lehmann, Christoph, Imming, Peter, Seidel, Rüdiger W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472761/
https://www.ncbi.nlm.nih.gov/pubmed/32939297
http://dx.doi.org/10.1107/S2056989020010658
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author Eckhardt, Tamira
Goddard, Richard
Rudolph, Ines
Richter, Adrian
Lehmann, Christoph
Imming, Peter
Seidel, Rüdiger W.
author_facet Eckhardt, Tamira
Goddard, Richard
Rudolph, Ines
Richter, Adrian
Lehmann, Christoph
Imming, Peter
Seidel, Rüdiger W.
author_sort Eckhardt, Tamira
collection PubMed
description 1,3-Benzo­thia­zin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piper­id­in-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(tri­fluoro­meth­yl)-1,3-benzo­thia­zin-4-one, following the original synthetic route, whereby the corresponding benzoyl iso­thio­cyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The tri­fluoro­methyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for inter­molecular weak C—H⋯O hydrogen bonds.
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spelling pubmed-74727612020-09-15 [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis Eckhardt, Tamira Goddard, Richard Rudolph, Ines Richter, Adrian Lehmann, Christoph Imming, Peter Seidel, Rüdiger W. Acta Crystallogr E Crystallogr Commun Research Communications 1,3-Benzo­thia­zin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piper­id­in-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(tri­fluoro­meth­yl)-1,3-benzo­thia­zin-4-one, following the original synthetic route, whereby the corresponding benzoyl iso­thio­cyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The tri­fluoro­methyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for inter­molecular weak C—H⋯O hydrogen bonds. International Union of Crystallography 2020-08-11 /pmc/articles/PMC7472761/ /pubmed/32939297 http://dx.doi.org/10.1107/S2056989020010658 Text en © Eckhardt et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Eckhardt, Tamira
Goddard, Richard
Rudolph, Ines
Richter, Adrian
Lehmann, Christoph
Imming, Peter
Seidel, Rüdiger W.
[2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title_full [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title_fullStr [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title_full_unstemmed [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title_short [2-Chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
title_sort [2-chloro-3-nitro-5-(tri­fluoro­meth­yl)phen­yl](piperidin-1-yl)methanone: structural characterization of a side product in benzo­thia­zinone synthesis
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472761/
https://www.ncbi.nlm.nih.gov/pubmed/32939297
http://dx.doi.org/10.1107/S2056989020010658
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