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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(...

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Autores principales: Bhardwaj, Minakshi, Ai, Qianxiang, Parkin, Sean R., Grossman, Robert B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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