Two new heterocyclic [3.3.3.01,5]-propellanoid compounds: 2,8-dioxatricyclo[3.3.3.01,5]undecane-3,7-dione and a related dimer

Jonglin F. Tsao; Sana R. Faruqi; Hugh W. Thompson; Roger A. Lalancette

doi:10.1107/S0108270102022369

Two new heterocyclic [3.3.3.0^1,5]-propellanoid compounds: 2,8-dioxatricyclo[3.3.3.0^1,5]undecane-3,7-dione and a related dimer

Jonglin F. Tsao, Sana R. Faruqi, Hugh W. Thompson, Roger A. Lalancette

Rutgers Newark, Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

2,8-Dioxatricyclo[3.3.3.0^1.5]undecane-3,7-dione, C₉H₁₀O₄. (I), is the dilactone acylal of cyclopentanone-2,2-diacetic acid. Both molecules in the asymmetric unit have conformational chirality and differ principally in the flexing of the carbon ring, which produces a resolvable conformational disorder in one of the molecules. Three intermolecular C-H ⋯ O close contacts exist. 7,7′-Oxybis(2,8-dioxatricyclo[3.3.3.0^1,5]undecan-3-one), C₁₈H₂₂O₇, (II), a racemate, lies on a C₂ axis and is a non-meso furanosyl furanoside dimer derived from the monoacid monoaldehyde corresponding to (I). One intermolecular C - H ⋯ O close contact exists. Diminished intramolecular void space in these small propellanoids generates unusually high crystal density in both species, particularly (I).

Original language	English (US)
Pages (from-to)	o57-o59
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	59
Issue number	2
DOIs	https://doi.org/10.1107/S0108270102022369
State	Published - Feb 2003

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Biochemistry, Genetics and Molecular Biology(all)

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title = "Two new heterocyclic [3.3.3.01,5]-propellanoid compounds: 2,8-dioxatricyclo[3.3.3.01,5]undecane-3,7-dione and a related dimer",

abstract = "2,8-Dioxatricyclo[3.3.3.01.5]undecane-3,7-dione, C9H10O4. (I), is the dilactone acylal of cyclopentanone-2,2-diacetic acid. Both molecules in the asymmetric unit have conformational chirality and differ principally in the flexing of the carbon ring, which produces a resolvable conformational disorder in one of the molecules. Three intermolecular C-H ⋯ O close contacts exist. 7,7′-Oxybis(2,8-dioxatricyclo[3.3.3.01,5]undecan-3-one), C18H22O7, (II), a racemate, lies on a C2 axis and is a non-meso furanosyl furanoside dimer derived from the monoacid monoaldehyde corresponding to (I). One intermolecular C - H ⋯ O close contact exists. Diminished intramolecular void space in these small propellanoids generates unusually high crystal density in both species, particularly (I).",

author = "Tsao, {Jonglin F.} and Faruqi, {Sana R.} and Thompson, {Hugh W.} and Lalancette, {Roger A.}",

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T1 - Two new heterocyclic [3.3.3.01,5]-propellanoid compounds

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AU - Tsao, Jonglin F.

AU - Faruqi, Sana R.

AU - Thompson, Hugh W.

AU - Lalancette, Roger A.

PY - 2003/2

Y1 - 2003/2

N2 - 2,8-Dioxatricyclo[3.3.3.01.5]undecane-3,7-dione, C9H10O4. (I), is the dilactone acylal of cyclopentanone-2,2-diacetic acid. Both molecules in the asymmetric unit have conformational chirality and differ principally in the flexing of the carbon ring, which produces a resolvable conformational disorder in one of the molecules. Three intermolecular C-H ⋯ O close contacts exist. 7,7′-Oxybis(2,8-dioxatricyclo[3.3.3.01,5]undecan-3-one), C18H22O7, (II), a racemate, lies on a C2 axis and is a non-meso furanosyl furanoside dimer derived from the monoacid monoaldehyde corresponding to (I). One intermolecular C - H ⋯ O close contact exists. Diminished intramolecular void space in these small propellanoids generates unusually high crystal density in both species, particularly (I).

AB - 2,8-Dioxatricyclo[3.3.3.01.5]undecane-3,7-dione, C9H10O4. (I), is the dilactone acylal of cyclopentanone-2,2-diacetic acid. Both molecules in the asymmetric unit have conformational chirality and differ principally in the flexing of the carbon ring, which produces a resolvable conformational disorder in one of the molecules. Three intermolecular C-H ⋯ O close contacts exist. 7,7′-Oxybis(2,8-dioxatricyclo[3.3.3.01,5]undecan-3-one), C18H22O7, (II), a racemate, lies on a C2 axis and is a non-meso furanosyl furanoside dimer derived from the monoacid monoaldehyde corresponding to (I). One intermolecular C - H ⋯ O close contact exists. Diminished intramolecular void space in these small propellanoids generates unusually high crystal density in both species, particularly (I).

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Two new heterocyclic [3.3.3.0^1,5]-propellanoid compounds: 2,8-dioxatricyclo[3.3.3.0^1,5]undecane-3,7-dione and a related dimer

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