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(S)-2-Oxotetra­hydro­furan-3-aminium bromide

In the title HBr salt of (S)-homoserine lactone, C(4)H(8)NO(2) (+)·Br(−), the five-membered ring has an envelope conformation, with the –CH(2)– C atom adjacent to the N-substituted C atom at the flap position. The four-atom mean plane (r.m.s. deviation = 0.005 Å) of the envelope forms a dihedral ang...

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Autores principales: Sandifer, Jace D., Fronczek, Frank R., Watkins, Steven F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3414985/
https://www.ncbi.nlm.nih.gov/pubmed/22904972
http://dx.doi.org/10.1107/S1600536812032552
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author Sandifer, Jace D.
Fronczek, Frank R.
Watkins, Steven F.
author_facet Sandifer, Jace D.
Fronczek, Frank R.
Watkins, Steven F.
author_sort Sandifer, Jace D.
collection PubMed
description In the title HBr salt of (S)-homoserine lactone, C(4)H(8)NO(2) (+)·Br(−), the five-membered ring has an envelope conformation, with the –CH(2)– C atom adjacent to the N-substituted C atom at the flap position. The four-atom mean plane (r.m.s. deviation = 0.005 Å) of the envelope forms a dihedral angle of 32.12 (9)° with the three-atom flap plane. The distorted square-pyramidal coordination about the anion involves five surrounding cations, with the square base defined by three N—H⋯Br hydrogen bonds [Br⋯N = 3.3046 (10), 3.3407 (12) and 3.3644 (13) Å] and near-contact with an H atom attached to C [Br⋯C = 3.739 (1) Å]. Another Br⋯C contact of 3.427 (1) Å defines the apex. There is also an N—H⋯O hydrogen bond present linking the cations.
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spelling pubmed-34149852012-08-17 (S)-2-Oxotetra­hydro­furan-3-aminium bromide Sandifer, Jace D. Fronczek, Frank R. Watkins, Steven F. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title HBr salt of (S)-homoserine lactone, C(4)H(8)NO(2) (+)·Br(−), the five-membered ring has an envelope conformation, with the –CH(2)– C atom adjacent to the N-substituted C atom at the flap position. The four-atom mean plane (r.m.s. deviation = 0.005 Å) of the envelope forms a dihedral angle of 32.12 (9)° with the three-atom flap plane. The distorted square-pyramidal coordination about the anion involves five surrounding cations, with the square base defined by three N—H⋯Br hydrogen bonds [Br⋯N = 3.3046 (10), 3.3407 (12) and 3.3644 (13) Å] and near-contact with an H atom attached to C [Br⋯C = 3.739 (1) Å]. Another Br⋯C contact of 3.427 (1) Å defines the apex. There is also an N—H⋯O hydrogen bond present linking the cations. International Union of Crystallography 2012-07-25 /pmc/articles/PMC3414985/ /pubmed/22904972 http://dx.doi.org/10.1107/S1600536812032552 Text en © Sandifer et al. 2012 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
Sandifer, Jace D.
Fronczek, Frank R.
Watkins, Steven F.
(S)-2-Oxotetra­hydro­furan-3-aminium bromide
title (S)-2-Oxotetra­hydro­furan-3-aminium bromide
title_full (S)-2-Oxotetra­hydro­furan-3-aminium bromide
title_fullStr (S)-2-Oxotetra­hydro­furan-3-aminium bromide
title_full_unstemmed (S)-2-Oxotetra­hydro­furan-3-aminium bromide
title_short (S)-2-Oxotetra­hydro­furan-3-aminium bromide
title_sort (s)-2-oxotetra­hydro­furan-3-aminium bromide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3414985/
https://www.ncbi.nlm.nih.gov/pubmed/22904972
http://dx.doi.org/10.1107/S1600536812032552
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