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

ABSTRACT: The mol-ecule of the title keto carbasugar, C7H10O4, is formed by a cyclo-hexene 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 tetra-gonal pseudosymmetry influenced by the similarity between the a and b axes, the value of 90.9770?(10)° of the ? angle and the action of a 21 screw axis, which transform each chain into its corresponding nearly orthogonal one.

SUBMITTER: Tibhe GD 

PROVIDER: S-EPMC5382632 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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

Tibhe Gaurao D GD   Macías Mario A MA   Pandolfi Enrique E   Schapiro Valeria V   Suescun Leopoldo L  

Acta crystallographica. Section E, Crystallographic communications 20170328 Pt 4

The mol-ecule of the title keto carbasugar, C<sub>7</sub>H<sub>10</sub>O<sub>4</sub>, is formed by a cyclo-hexene 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 tetra-gonal pseudosymmetry influenced by the similarity betw  ...[more]

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