Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

Kossay Elasaad, Racha Alkhatib, Thierry Hennebelle, Bernadette Norberg, Johan Wouters

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Abstract

The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P212121; R1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.
Original languageEnglish
Pages (from-to)1441-1454
Number of pages14
JournalCrystals
Volume2
Issue number4
DOIs
Publication statusPublished - 26 Oct 2012

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Cyclodextrins
Crystallization
Crystal structure
inclusions
Pyranocoumarins
crystallization
crystal structure
Molecules
Crystallography
configurations
crystallography
molecules
cavities
Geometry
geometry
interactions
aegelinol

Cite this

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title = "Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin",
abstract = "The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) {\AA}, b = 15.281(1) {\AA}, c = 17.890(1) {\AA}, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R1 = 6.71{\%}) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) {\AA}, b = 11.4302(9) {\AA}, c = 44.964(3) {\AA}, P212121; R1 = 4.44{\%}) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.",
author = "Kossay Elasaad and Racha Alkhatib and Thierry Hennebelle and Bernadette Norberg and Johan Wouters",
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Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin. / Elasaad, Kossay; Alkhatib, Racha; Hennebelle, Thierry; Norberg, Bernadette; Wouters, Johan.

In: Crystals, Vol. 2, No. 4, 26.10.2012, p. 1441-1454.

Research output: Contribution to journalArticle

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AU - Alkhatib, Racha

AU - Hennebelle, Thierry

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AU - Wouters, Johan

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AB - The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P212121; R1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.

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