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. 2015 Aug 6;71(Pt 9):1013-6.
doi: 10.1107/S2056989015014590. eCollection 2015 Sep 1.

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetra-hydro-1,3-benzodioxole-4,5-diol

Affiliations

Crystal structure and absolute configuration of (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a-tetra-hydro-1,3-benzodioxole-4,5-diol

Mario A Macías et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The absolute configuration of the title compound, C10H16O4, determined as 3aS,4S,5R,7aR on the basis of the synthetic pathway, was confirmed by X-ray diffraction. The mol-ecule contains a five- and a six-membered ring that adopt twisted and envelope conformations, respectively. The dihedral angle between the mean planes of the rings is 76.80 (11)° as a result of their cis-fusion. In the crystal, mol-ecules are linked by two pairs of O-H⋯O hydrogen bonds, forming chains along [010]. These chains are further connected by weaker C-H⋯O inter-actions along [100], creating (001) sheets that inter-act only by weak van der Waals forces.

Keywords: absolute configuration; chemoenzymatic strategy; chiral crystal; crystal structure; ep­oxy­cyclo­hexenones.

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Figures

Figure 1
Figure 1
Synthesis pathway and structural scheme of the chiral C10H16O4 compound.
Figure 2
Figure 2
The mol­ecular structure of the title compound, showing the anisotropic displacement ellipsoids drawn at the 50% probability level.
Figure 3
Figure 3
Packing of the title compound, viewed along [100], showing hydrogen-bonded chains of mol­ecules

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