Cargando…

Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K

The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not...

Descripción completa

Detalles Bibliográficos
Autores principales: Sledz, Pawel, Minor, Thomas, Chruszcz, Maksymilian
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971979/
https://www.ncbi.nlm.nih.gov/pubmed/21578764
http://dx.doi.org/10.1107/S1600536809042512
_version_ 1782190715217903616
author Sledz, Pawel
Minor, Thomas
Chruszcz, Maksymilian
author_facet Sledz, Pawel
Minor, Thomas
Chruszcz, Maksymilian
author_sort Sledz, Pawel
collection PubMed
description The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not previously reported [Gao, Yin, Yang, & Xue (2004). Acta Cryst. E60, o1328–o1329]. The change of protonation state of the nitrogen atom significantly affects the intermolecular interactions in the HEPES crystal. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds and ionic inter­actions, as the title compound in solid state is a zwitterion. HEPES mol­ecules pack in layers that are held together by ionic and weak inter­actions, while a hydrogen-bonded network connects the layers.
format Text
id pubmed-2971979
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29719792010-12-30 Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K Sledz, Pawel Minor, Thomas Chruszcz, Maksymilian Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound (common name HEPES), C(8)H(18)N(2)O(4)S, has been redetermined at 100 K in order to properly elucidate the protonation state of the HEPES molecule. The piperazine ring has a chair conformation and one of the N atoms in the ring is protonated, which was not previously reported [Gao, Yin, Yang, & Xue (2004). Acta Cryst. E60, o1328–o1329]. The change of protonation state of the nitrogen atom significantly affects the intermolecular interactions in the HEPES crystal. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds and ionic inter­actions, as the title compound in solid state is a zwitterion. HEPES mol­ecules pack in layers that are held together by ionic and weak inter­actions, while a hydrogen-bonded network connects the layers. International Union of Crystallography 2009-11-07 /pmc/articles/PMC2971979/ /pubmed/21578764 http://dx.doi.org/10.1107/S1600536809042512 Text en © Sledz et al. 2009 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
Sledz, Pawel
Minor, Thomas
Chruszcz, Maksymilian
Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title_full Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title_fullStr Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title_full_unstemmed Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title_short Redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 K
title_sort redetermination of 2-[4-(2-hydroxy­ethyl)piperazin-1-ium-1-yl]ethanesul­fonate at 100 k
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2971979/
https://www.ncbi.nlm.nih.gov/pubmed/21578764
http://dx.doi.org/10.1107/S1600536809042512
work_keys_str_mv AT sledzpawel redeterminationof242hydroxyethylpiperazin1ium1ylethanesulfonateat100k
AT minorthomas redeterminationof242hydroxyethylpiperazin1ium1ylethanesulfonateat100k
AT chruszczmaksymilian redeterminationof242hydroxyethylpiperazin1ium1ylethanesulfonateat100k