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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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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-3007251 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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