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A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide

The alkynyl bond of the title compound, C(14)H(19)NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O—C—N—H of −176 (2)°. There is an inter­molecular N—H⋯O hydrogen bond between the amide function and...

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Detalles Bibliográficos
Autores principales: Frey, Wolfgang, Schetter, Stefanie, Rominger, Frank, Hashmi, A. Stephen K.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962125/
https://www.ncbi.nlm.nih.gov/pubmed/21203207
http://dx.doi.org/10.1107/S1600536808021466
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author Frey, Wolfgang
Schetter, Stefanie
Rominger, Frank
Hashmi, A. Stephen K.
author_facet Frey, Wolfgang
Schetter, Stefanie
Rominger, Frank
Hashmi, A. Stephen K.
author_sort Frey, Wolfgang
collection PubMed
description The alkynyl bond of the title compound, C(14)H(19)NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O—C—N—H of −176 (2)°. There is an inter­molecular N—H⋯O hydrogen bond between the amide function and the carbonyl group. In addition, weak inter­molecular hydrogen bonds stabilize the crystal structure. A comparison with a polymorphic structure shows conformational differences with regard to the orientation of the carbonyl groups with respect to the adamantyl group [O—C—C—C = 96.2 (3)° in the title compound and 123.7 (2)° in the polymorph] and the orientations of the propargyl groups in relation to the carbonyl groups [O—C—C—C = −87.7 (3) and −58.7 (2)°, respectively].
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spelling pubmed-29621252010-12-30 A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide Frey, Wolfgang Schetter, Stefanie Rominger, Frank Hashmi, A. Stephen K. Acta Crystallogr Sect E Struct Rep Online Organic Papers The alkynyl bond of the title compound, C(14)H(19)NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O—C—N—H of −176 (2)°. There is an inter­molecular N—H⋯O hydrogen bond between the amide function and the carbonyl group. In addition, weak inter­molecular hydrogen bonds stabilize the crystal structure. A comparison with a polymorphic structure shows conformational differences with regard to the orientation of the carbonyl groups with respect to the adamantyl group [O—C—C—C = 96.2 (3)° in the title compound and 123.7 (2)° in the polymorph] and the orientations of the propargyl groups in relation to the carbonyl groups [O—C—C—C = −87.7 (3) and −58.7 (2)°, respectively]. International Union of Crystallography 2008-07-16 /pmc/articles/PMC2962125/ /pubmed/21203207 http://dx.doi.org/10.1107/S1600536808021466 Text en © Frey et al. 2008 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
Frey, Wolfgang
Schetter, Stefanie
Rominger, Frank
Hashmi, A. Stephen K.
A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title_full A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title_fullStr A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title_full_unstemmed A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title_short A new polymorph of N-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
title_sort new polymorph of n-(prop-2-yn­yl)tricyclo­[3.3.1.1(3,7)]decane-1-carbox­amide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962125/
https://www.ncbi.nlm.nih.gov/pubmed/21203207
http://dx.doi.org/10.1107/S1600536808021466
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