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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...

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Detalles Bibliográficos
Autores principales: Haines, Alan H., Hughes, David L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
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.
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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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