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(1S,2S,6R,7aR)-2-Benzyl-1,6-dihy-droxy-hexa-hydro-pyrrolizin-3-one.

ABSTRACT: In the title compound, C(14)H(17)NO(3), the dihedral angles show that the H atoms at two stereocenters are in a trans-diaxial configuration. In the crystal, the molecules are linked by O-H?O hydrogen bonds. The absolute configuration of the molecule has been established on the basis of refinement of the Hooft and Flack parameters.

SUBMITTER: Oliveira FL

PROVIDER: S-EPMC3297313 | biostudies-other | 2012 Mar

REPOSITORIES: biostudies-other

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(1S,2S,6R,7aR)-2-Benzyl-1,6-dihy-droxy-hexa-hydro-pyrrolizin-3-one.

Oliveira F L FL Freire K R L KR Aparicio R R Coelho F F

Acta crystallographica. Section E, Structure reports online 20120204 Pt 3

In the title compound, C(14)H(17)NO(3), the dihedral angles show that the H atoms at two stereocenters are in a trans-diaxial configuration. In the crystal, the molecules are linked by O-H⋯O hydrogen bonds. The absolute configuration of the molecule has been established on the basis of refinement of the Hooft and Flack parameters. ...[more]

PMID: 22412503

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(1S,2E,6R,7aR)-2-Benzyl-idene-1,6-dihy-droxy-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

Project description:In the title compound, C(14)H(15)NO(3), the conformation of the double bond was determined to be E, confirming the result obtained from two-dimensional NMR data. The five-membered rings of the pyrrolizine unit exhibit C-envelope conformations, with C atoms displaced from the mean planes formed by the remaining rings atoms by 0.1468?(15) and 0.5405?(17)?Å. The mean planes of these rings (through all ring atoms) have a dihedral angle of 49.03?(10)°. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds. The absolute configuration of the mol-ecule was established, as judged by the, as judged by the obtained values for the Hooft and Flack parameters.

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Project description: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.

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