Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1782189146137165824 |
---|---|
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]. |
format | Text |
id | pubmed-2962125 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT freywolfgang anewpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT schetterstefanie anewpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT romingerfrank anewpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT hashmiastephenk anewpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT freywolfgang newpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT schetterstefanie newpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT romingerfrank newpolymorphofnprop2ynyltricyclo331137decane1carboxamide AT hashmiastephenk newpolymorphofnprop2ynyltricyclo331137decane1carboxamide |