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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.

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The crystal packing diagram of the major component of the title compound, viewed along the c axis. Only H atoms involving in the hydrogen bonds (dashed lines) are shown.
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Fap3: The crystal packing diagram of the major component of the title compound, viewed along the c axis. Only H atoms involving in the hydrogen bonds (dashed lines) are shown.


Absolute configuration of xerophenone A.

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

The crystal packing diagram of the major component of the title compound, viewed along the c axis. Only H atoms involving in the hydrogen bonds (dashed lines) are shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Fap3: The crystal packing diagram of the major component of the title compound, viewed along the c axis. Only H atoms involving in the hydrogen bonds (dashed lines) are shown.
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