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(1S,2R,2′S,3′aS,5R)-2′-[(1R)-1-Hydroxy­ethyl]-2-isopropyl-5,5′-dimethyl-3′,3′a-dihydro-2′H-spiro­[cyclo­hexane-1,6′-imidazo[1,5-b]isoxazol]-4′(5′H)-one

✍ Scribed by Aouadi, Kaiss ;Jeanneau, Erwann ;Praly, Jean-Pierre

Publisher
International Union of Crystallography
Year
2007
Tongue
English
Weight
328 KB
Volume
63
Category
Article
ISSN
1600-5368

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✦ Synopsis

Cycloaddition of a (−)-menthone-derived nitrone to racemic but-3-en-2-ol led to two spirobicyclic heterocycles, with opposite configurations at the C atom attached to the OH group. This paper describes the S epimer of the 1-hydroxyethyl substituent in imidazoisoxazole C~17~H~30~N~2~O~3~, (I). The R epimer, (II), is presented in the previous article [Aouadi, Jeanneau & Praly (2007), Acta Cryst. E67, o1324–o1326]. The absolute configurations of both epimers were assigned from the known configuration of the starting (−)-menthone derived nitrone. In (I), there is an O—H...O hydrogen bond (O—H...O = 1.96 Å and O—H...O = 165°) that concatenates the molecules along the b axis. In addition, there are C—H...O and C—H...N hydrogen bonds.

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(1S,2R,2′S,3′aS,5R)-2′-[(1S)-1-Hydroxy­ethyl]-2-isopropyl-5,5′-dimethyl-3′,3′a-dihydro-2′H-spiro­[cyclo­hexane-1,6′-imidazo[1,5-b]isoxazol]-4′(5′H)-one
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Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.005 A Ê Disorder in main residue R factor = 0.047 wR factor = 0.124 Data-to-parameter ratio = 15.9 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

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