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An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine
The title compound [systematic name: (1R*, 8S)-2-acetamidooctahydropyrrolizin-4-ium chloride–N-[(1R, 8S)-hexahydro-1H-pyrrolizin-2-yl)acetamide (1/1)], 2(C(9)H(16)N(2)O)·HCl or C(9)H(17)N(2)O(+)·Cl(−)·C(9)H(16)N(2)O, arose as an unexpected product when 1-exo-acetamidopyrrolizidine (AcAP; C(9)H(...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944077/ https://www.ncbi.nlm.nih.gov/pubmed/31921456 http://dx.doi.org/10.1107/S2056989019016517 |
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author | Bhardwaj, Minakshi Ai, Qianxiang Parkin, Sean R. Grossman, Robert B. |
author_facet | Bhardwaj, Minakshi Ai, Qianxiang Parkin, Sean R. Grossman, Robert B. |
author_sort | Bhardwaj, Minakshi |
collection | PubMed |
description | The title compound [systematic name: (1R*, 8S)-2-acetamidooctahydropyrrolizin-4-ium chloride–N-[(1R, 8S)-hexahydro-1H-pyrrolizin-2-yl)acetamide (1/1)], 2(C(9)H(16)N(2)O)·HCl or C(9)H(17)N(2)O(+)·Cl(−)·C(9)H(16)N(2)O, arose as an unexpected product when 1-exo-acetamidopyrrolizidine (AcAP; C(9)H(16)N(2)O) was dissolved in CHCl(3). Within the AcAP pyrrolizidine group, the unsubstituted five-membered ring is disordered over two orientations in a 0.897 (5):0.103 (5) ratio. Two AcAP molecules related by a crystallographic twofold axis link to H(+) and Cl(−) ions lying on the rotation axis, thereby forming N—H⋯N and N—H⋯Cl⋯H—N hydrogen bonds. The first of these has an unusually short N⋯N separation of 2.616 (2) Å: refinement of different models against the present data set could not distinguish between a symmetrical hydrogen bond (H atom lying on the twofold axis and equidistant from the N atoms) or static or dynamic disorder models (i.e. N—H⋯N + N⋯H—N). Computational studies suggest that the disorder model is slightly more stable, but the energy difference is very small. |
format | Online Article Text |
id | pubmed-6944077 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-69440772020-01-09 An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine Bhardwaj, Minakshi Ai, Qianxiang Parkin, Sean R. Grossman, Robert B. Acta Crystallogr E Crystallogr Commun Research Communications The title compound [systematic name: (1R*, 8S)-2-acetamidooctahydropyrrolizin-4-ium chloride–N-[(1R, 8S)-hexahydro-1H-pyrrolizin-2-yl)acetamide (1/1)], 2(C(9)H(16)N(2)O)·HCl or C(9)H(17)N(2)O(+)·Cl(−)·C(9)H(16)N(2)O, arose as an unexpected product when 1-exo-acetamidopyrrolizidine (AcAP; C(9)H(16)N(2)O) was dissolved in CHCl(3). Within the AcAP pyrrolizidine group, the unsubstituted five-membered ring is disordered over two orientations in a 0.897 (5):0.103 (5) ratio. Two AcAP molecules related by a crystallographic twofold axis link to H(+) and Cl(−) ions lying on the rotation axis, thereby forming N—H⋯N and N—H⋯Cl⋯H—N hydrogen bonds. The first of these has an unusually short N⋯N separation of 2.616 (2) Å: refinement of different models against the present data set could not distinguish between a symmetrical hydrogen bond (H atom lying on the twofold axis and equidistant from the N atoms) or static or dynamic disorder models (i.e. N—H⋯N + N⋯H—N). Computational studies suggest that the disorder model is slightly more stable, but the energy difference is very small. International Union of Crystallography 2020-01-01 /pmc/articles/PMC6944077/ /pubmed/31921456 http://dx.doi.org/10.1107/S2056989019016517 Text en © Bhardwaj et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Bhardwaj, Minakshi Ai, Qianxiang Parkin, Sean R. Grossman, Robert B. An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title | An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title_full | An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title_fullStr | An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title_full_unstemmed | An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title_short | An unusually short intermolecular N—H⋯N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
title_sort | unusually short intermolecular n—h⋯n hydrogen bond in crystals of the hemi-hydrochloride salt of 1-exo-acetamidopyrrolizidine |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944077/ https://www.ncbi.nlm.nih.gov/pubmed/31921456 http://dx.doi.org/10.1107/S2056989019016517 |
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