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(1S,2E,6R,7aR)-1,6-Dihy-droxy-2-(4-nitro-benzyl-idene)-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

Oliveira FL, Freire KR, Aparicio R, Coelho F - Acta Crystallogr Sect E Struct Rep Online (2012)

Bottom Line: The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings.Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data.In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

View Article: PubMed Central - HTML - PubMed

ABSTRACT
The crystal structure of the title compound, C(14)H(14)N(2)O(5), contains two distinct conformers in the asymmetric unit. The compound has three defined stereocenters, two of them contiguous, and a C=C double bond with an E conformation. The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings. A prominent feature is a change from almost coplanar rings in one conformer to a new conformation in the second conformer, in which the mean plane of a five-membered ring is almost perpendicular to the benzene ring, with a dihedral angle 87.19 (8)°; the corresponding angle in the first conformer is 14.02 (10)°. In the crystal, molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds. Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data. In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

No MeSH data available.


A view of molecule 2 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
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Fap2: A view of molecule 2 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.


(1S,2E,6R,7aR)-1,6-Dihy-droxy-2-(4-nitro-benzyl-idene)-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

Oliveira FL, Freire KR, Aparicio R, Coelho F - Acta Crystallogr Sect E Struct Rep Online (2012)

A view of molecule 2 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3344666&req=5

Fap2: A view of molecule 2 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
Bottom Line: The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings.Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data.In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

View Article: PubMed Central - HTML - PubMed

ABSTRACT
The crystal structure of the title compound, C(14)H(14)N(2)O(5), contains two distinct conformers in the asymmetric unit. The compound has three defined stereocenters, two of them contiguous, and a C=C double bond with an E conformation. The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings. A prominent feature is a change from almost coplanar rings in one conformer to a new conformation in the second conformer, in which the mean plane of a five-membered ring is almost perpendicular to the benzene ring, with a dihedral angle 87.19 (8)°; the corresponding angle in the first conformer is 14.02 (10)°. In the crystal, molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds. Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data. In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

No MeSH data available.