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A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile

A new monoclinic form of the title compound, C(14)H(17)N(3)O(3)S, has been found upon slow crystallization from water. Another monoclinic form of the compound was obtained previously from a mixture of dichloro­methane and diethyl ether [Clerici et al. (2002 ▶). Tetra­hedron, 58, 5173–5178]. Both pha...

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Detalles Bibliográficos
Autores principales: Orlando, Ahmed M., Lo Presti, Leonardo, Soave, Raffaella
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007251/
https://www.ncbi.nlm.nih.gov/pubmed/21588342
http://dx.doi.org/10.1107/S1600536810027558
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author Orlando, Ahmed M.
Lo Presti, Leonardo
Soave, Raffaella
author_facet Orlando, Ahmed M.
Lo Presti, Leonardo
Soave, Raffaella
author_sort Orlando, Ahmed M.
collection PubMed
description A new monoclinic form of the title compound, C(14)H(17)N(3)O(3)S, has been found upon slow crystallization from water. Another monoclinic form of the compound was obtained previously from a mixture of dichloro­methane and diethyl ether [Clerici et al. (2002 ▶). Tetra­hedron, 58, 5173–5178]. Both phases crystallize in space group P2(1)/n with one mol­ecule in the asymmetric unit. The formally single exocyclic C—N bond that connects the –NEt(2) unit with the thia­zete ring is considerably shorter than the adjacent, formally double, endocyclic C=N bond. This is likely to be due to the extended conjugated system between the electron-donor diethyl­ammine fragment and the electron-withdrawing sulfonyl group. In the newly discovered polymorph, the meth­oxy group is rotated by almost 180° around the phen­yl–OCH(3) bond, resulting in a different mol­ecular conformation.
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spelling pubmed-30072512010-12-30 A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile Orlando, Ahmed M. Lo Presti, Leonardo Soave, Raffaella Acta Crystallogr Sect E Struct Rep Online Organic Papers A new monoclinic form of the title compound, C(14)H(17)N(3)O(3)S, has been found upon slow crystallization from water. Another monoclinic form of the compound was obtained previously from a mixture of dichloro­methane and diethyl ether [Clerici et al. (2002 ▶). Tetra­hedron, 58, 5173–5178]. Both phases crystallize in space group P2(1)/n with one mol­ecule in the asymmetric unit. The formally single exocyclic C—N bond that connects the –NEt(2) unit with the thia­zete ring is considerably shorter than the adjacent, formally double, endocyclic C=N bond. This is likely to be due to the extended conjugated system between the electron-donor diethyl­ammine fragment and the electron-withdrawing sulfonyl group. In the newly discovered polymorph, the meth­oxy group is rotated by almost 180° around the phen­yl–OCH(3) bond, resulting in a different mol­ecular conformation. International Union of Crystallography 2010-07-17 /pmc/articles/PMC3007251/ /pubmed/21588342 http://dx.doi.org/10.1107/S1600536810027558 Text en © Orlando 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
Orlando, Ahmed M.
Lo Presti, Leonardo
Soave, Raffaella
A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title_full A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title_fullStr A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title_full_unstemmed A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title_short A new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4H-1λ(6),2-thia­zete-4-carbonitrile
title_sort new monoclinic polymorph of 3-diethyl­amino-4-(4-meth­oxy­phen­yl)-1,1-dioxo-4h-1λ(6),2-thia­zete-4-carbonitrile
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007251/
https://www.ncbi.nlm.nih.gov/pubmed/21588342
http://dx.doi.org/10.1107/S1600536810027558
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