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Crystal structure and absolute configuration of (4 S ,5 R ,6 S )-4,5,6-trihy ­ droxy-3-methyl ­ cyclo ­ hex-2-enone (gabosine H)

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ABSTRACT

The mol­ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo­hexene skeleton with an envelope conformation, substituted by carbonyl, methyl and hydroxyl groups. The crystal structure is controlled mainly by a combination of strong O—H⋯O and weak C—H⋯O hydrogen bonds, forming nearly perpendicular chains running parallel to the [110] and [-110] directions. This perpendicularity is caused by a tetra­gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770 (10)° of the β angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

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The mol­ecular structure of the title compound, showing the anisotropic displacement ellipsoids drawn at the 50% probability level.
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fig1: The mol­ecular structure of the title compound, showing the anisotropic displacement ellipsoids drawn at the 50% probability level.

Mentions: Fig. 1 ▸ shows the mol­ecule of the title compound. The absolute configuration of gabosine H with the carbonyl, methyl and hydroxyl groups in equatorial positions, determined as 4S,5R,6S on the basis of synthetic pathway, was confirmed by X-ray diffraction on the basis of anomalous dispersion of light atoms only. The six-membered ring (C1–C6) in the mol­ecule adopts an envelope conformation with atom C5 as the flap [deviating from the plane through the other ring atoms by 0.639 (2) Å] and puckering parameters Q = 0.4653 (19) Å, θ = 129.5 (2)° and φ = 66.7 (3)°.


Crystal structure and absolute configuration of (4 S ,5 R ,6 S )-4,5,6-trihy ­ droxy-3-methyl ­ cyclo ­ hex-2-enone (gabosine H)
The mol­ecular structure of the title compound, showing the anisotropic displacement ellipsoids drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382632&req=5

fig1: The mol­ecular structure of the title compound, showing the anisotropic displacement ellipsoids drawn at the 50% probability level.
Mentions: Fig. 1 ▸ shows the mol­ecule of the title compound. The absolute configuration of gabosine H with the carbonyl, methyl and hydroxyl groups in equatorial positions, determined as 4S,5R,6S on the basis of synthetic pathway, was confirmed by X-ray diffraction on the basis of anomalous dispersion of light atoms only. The six-membered ring (C1–C6) in the mol­ecule adopts an envelope conformation with atom C5 as the flap [deviating from the plane through the other ring atoms by 0.639 (2) Å] and puckering parameters Q = 0.4653 (19) Å, θ = 129.5 (2)° and φ = 66.7 (3)°.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The mol­ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo­hexene skeleton with an envelope conformation, substituted by carbonyl, methyl and hydroxyl groups. The crystal structure is controlled mainly by a combination of strong O—H⋯O and weak C—H⋯O hydrogen bonds, forming nearly perpendicular chains running parallel to the [110] and [-110] directions. This perpendicularity is caused by a tetra­gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770 (10)° of the β angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

No MeSH data available.