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Absolute configuration of xerophenone A.

Fun HK, Tantapakul C, Laphookhieo S, Boonnak N, Chantrapromma S - Acta Crystallogr Sect E Struct Rep Online (2012)

Bottom Line: An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif.In the crystal, mol-ecules are linked by O-H⋯O and weak C-H⋯O inter-actions into a chain along the a axis.A very weak C-H⋯π inter-action and C⋯O short contact [2.989 (2) Å] are also present.

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ABSTRACT
The title compound, C(33)H(42)O(5), known as xerophenone A {systematic name: (1R,3R,4R,6S,8E,10R)-10-hy-droxy-8-[hy-droxy(phen-yl)methyl-ene]-4-methyl-1,6-bis-(3-methyl-but-2-en-1-yl)-3-(3-methyl-but-3-en-1-yl)-11-oxatricyclo-[4.3.1.1(4,10)]undecane-7,9-dione} is a naturally occurring rearranged benzophenone compound which was isolated from the twigs of Garcinia propinqua. The absolute configuration was determined by refining the Flack parameter to 0.18 (16). The absolute configurations at positions 1, 3, 4, 6 and 10 of the xerophenone A are R, R, R, S and R. In the mol-ecule, the cyclo-hexane-1,3-dione, tetra-hydro-2H-pyran and tetra-hydro-furan rings adopt twisted boat, standard chair and envelope conformations, respectively. The 3-methyl-but-3-en-1-yl substituent is disordered over two sets of sites in a 0.771 (11):0.229 (11) ratio. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O and weak C-H⋯O inter-actions into a chain along the a axis. A very weak C-H⋯π inter-action and C⋯O short contact [2.989 (2) Å] are also present.

No MeSH data available.


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The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular O—H···O hydrogen bond was shown as a dashed line. Only H atoms of the hydroxy groups and the disordered side chain substituent are shown for clarity.
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Fap2: The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular O—H···O hydrogen bond was shown as a dashed line. Only H atoms of the hydroxy groups and the disordered side chain substituent are shown for clarity.


Absolute configuration of xerophenone A.

Fun HK, Tantapakul C, Laphookhieo S, Boonnak N, Chantrapromma S - Acta Crystallogr Sect E Struct Rep Online (2012)

The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular O—H···O hydrogen bond was shown as a dashed line. Only H atoms of the hydroxy groups and the disordered side chain substituent are shown for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3344568&req=5

Fap2: The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular O—H···O hydrogen bond was shown as a dashed line. Only H atoms of the hydroxy groups and the disordered side chain substituent are shown for clarity.
Bottom Line: An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif.In the crystal, mol-ecules are linked by O-H⋯O and weak C-H⋯O inter-actions into a chain along the a axis.A very weak C-H⋯π inter-action and C⋯O short contact [2.989 (2) Å] are also present.

View Article: PubMed Central - HTML - PubMed

ABSTRACT
The title compound, C(33)H(42)O(5), known as xerophenone A {systematic name: (1R,3R,4R,6S,8E,10R)-10-hy-droxy-8-[hy-droxy(phen-yl)methyl-ene]-4-methyl-1,6-bis-(3-methyl-but-2-en-1-yl)-3-(3-methyl-but-3-en-1-yl)-11-oxatricyclo-[4.3.1.1(4,10)]undecane-7,9-dione} is a naturally occurring rearranged benzophenone compound which was isolated from the twigs of Garcinia propinqua. The absolute configuration was determined by refining the Flack parameter to 0.18 (16). The absolute configurations at positions 1, 3, 4, 6 and 10 of the xerophenone A are R, R, R, S and R. In the mol-ecule, the cyclo-hexane-1,3-dione, tetra-hydro-2H-pyran and tetra-hydro-furan rings adopt twisted boat, standard chair and envelope conformations, respectively. The 3-methyl-but-3-en-1-yl substituent is disordered over two sets of sites in a 0.771 (11):0.229 (11) ratio. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O and weak C-H⋯O inter-actions into a chain along the a axis. A very weak C-H⋯π inter-action and C⋯O short contact [2.989 (2) Å] are also present.

No MeSH data available.


Related in: MedlinePlus