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(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile
The title compound, C(7)H(8)N(2)O(2), formed by dehydration of the corresponding dicarboxamide, crystallizes as rectangular prisms. The molecules have a C (2) axis of symmetry through the C atom bearing the methyl groups and the mid-point of the ring C—C bond, and the 1,3-dioxolane ring adopts the...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770379/ https://www.ncbi.nlm.nih.gov/pubmed/24046664 http://dx.doi.org/10.1107/S1600536813015973 |
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author | Haines, Alan H. Hughes, David L. |
author_facet | Haines, Alan H. Hughes, David L. |
author_sort | Haines, Alan H. |
collection | PubMed |
description | The title compound, C(7)H(8)N(2)O(2), formed by dehydration of the corresponding dicarboxamide, crystallizes as rectangular prisms. The molecules have a C (2) axis of symmetry through the C atom bearing the methyl groups and the mid-point of the ring C—C bond, and the 1,3-dioxolane ring adopts the extreme twist conformation of the two possible with this symmetry. This brings the two nitrile groups nearest to a linear arrangement when the molecule is viewed along the ring C—C bond. The correct absolute configuration of the molecule was defined by that of the original starting material, (2R,3R)-tartaric acid. The packing is largely controlled by a number of C—H⋯N interactions. |
format | Online Article Text |
id | pubmed-3770379 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37703792013-09-17 (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile Haines, Alan H. Hughes, David L. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(7)H(8)N(2)O(2), formed by dehydration of the corresponding dicarboxamide, crystallizes as rectangular prisms. The molecules have a C (2) axis of symmetry through the C atom bearing the methyl groups and the mid-point of the ring C—C bond, and the 1,3-dioxolane ring adopts the extreme twist conformation of the two possible with this symmetry. This brings the two nitrile groups nearest to a linear arrangement when the molecule is viewed along the ring C—C bond. The correct absolute configuration of the molecule was defined by that of the original starting material, (2R,3R)-tartaric acid. The packing is largely controlled by a number of C—H⋯N interactions. International Union of Crystallography 2013-06-15 /pmc/articles/PMC3770379/ /pubmed/24046664 http://dx.doi.org/10.1107/S1600536813015973 Text en © Haines and Hughes 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 Haines, Alan H. Hughes, David L. (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title | (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title_full | (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title_fullStr | (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title_full_unstemmed | (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title_short | (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
title_sort | (4s,5s)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbonitrile |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770379/ https://www.ncbi.nlm.nih.gov/pubmed/24046664 http://dx.doi.org/10.1107/S1600536813015973 |
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