X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one

R Alan Aitken; Joe S. Logan; Alexandra Martha Zoya Slawin

doi:10.3390/M1445

X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one

R Alan Aitken^*, Joe S. Logan, Alexandra Martha Zoya Slawin

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4, exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor.

Original language	English
Article number	M1445
Number of pages	6
Journal	Molbank
Volume	2022
Issue number	3
DOIs	https://doi.org/10.3390/M1445
Publication status	Published - 14 Sept 2022

Keywords

Oxazolidin-2-one
Oxazolin-2(3H)-one
X-ray structure
Hydrogen bonding

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10.3390/M1445Licence: CC BY

Aitken_2022_molbank_X-ray-structures_CC
Copyright: © 2022 by the authors. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 2.11 MBLicence: CC BY

https://www.mdpi.com/1422-8599/2022/3/M1445/htmLicence: CC BY

CCDC 2194101 - 2194103: Experimental Crystal Structure Determination
Aitken, R. A. (Creator), Logan, J. S. (Creator) & Slawin, A. M. Z. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2cn4gn, https://dx.doi.org/10.5517/ccdc.csd.cc2cn4hp and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc2cn4jq (show fewer)
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@article{ceed206a6896456e86ff1a1fa136cd8b,

title = "X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one",

abstract = "The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4, exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor. ",

keywords = "Oxazolidin-2-one, Oxazolin-2(3H)-one, X-ray structure, Hydrogen bonding",

author = "Aitken, {R Alan} and Logan, {Joe S.} and Slawin, {Alexandra Martha Zoya}",

year = "2022",

month = sep,

day = "14",

doi = "10.3390/M1445",

language = "English",

volume = "2022",

journal = "Molbank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "3",

}

TY - JOUR

T1 - X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one

AU - Aitken, R Alan

AU - Logan, Joe S.

AU - Slawin, Alexandra Martha Zoya

PY - 2022/9/14

Y1 - 2022/9/14

N2 - The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4, exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor.

AB - The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4, exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor.

KW - Oxazolidin-2-one

KW - Oxazolin-2(3H)-one

KW - X-ray structure

KW - Hydrogen bonding

U2 - 10.3390/M1445

DO - 10.3390/M1445

M3 - Article

SN - 1422-8599

VL - 2022

JO - Molbank

JF - Molbank

IS - 3

M1 - M1445

ER -

X-ray structures of 3-acetyloxazolidin-2-one, 3-acetyloxazolin-2-one and oxazolin-2(3H)-one

Abstract

Keywords

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Datasets

CCDC 2194101 - 2194103: Experimental Crystal Structure Determination

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