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(2R,3R)-3-O-Benzoyl-N-benzyl-tartramide.

ABSTRACT: The title compound, C(18)H(17)NO(6) [systematic name: (2R,3R)-4-benzyl-amino-2-benzo-yloxy-3-hy-droxy-4-oxobutanoic acid], is the first structurally characterized unsymmetrical monoamide-monoacyl tartaric acid derivative. The mol-ecule shows a staggered conformation around the tartramide Csp(3)-Csp(3) bond with trans-oriented carboxyl and amide groups. The mol-ecular conformation is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, mol-ecules are linked by O-H?O hydrogen bonds between the carboxyl and amide carbonyl groups, forming translational chains along [001]. Further O-H?O and N-H?O hydrogen bonds as well as weaker C-H?O and C-H?? inter-molecular inter-actions extend the supra-molecular assembly into a double-layer structure parallel to (100). There are no directional inter-actions between the double layers.

SUBMITTER: Madura ID

PROVIDER: S-EPMC3379450 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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(2R,3R)-3-O-Benzoyl-N-benzyl-tartramide.

Madura Izabela D ID Zachara Janusz J Bernaś Urszula U Hajmowicz Halina H Synoradzki Ludwik L

Acta crystallographica. Section E, Structure reports online 20120526 Pt 6

The title compound, C(18)H(17)NO(6) [systematic name: (2R,3R)-4-benzyl-amino-2-benzo-yloxy-3-hy-droxy-4-oxobutanoic acid], is the first structurally characterized unsymmetrical monoamide-monoacyl tartaric acid derivative. The mol-ecule shows a staggered conformation around the tartramide Csp(3)-Csp(3) bond with trans-oriented carboxyl and amide groups. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bond ...[more]

PMID: 22719648

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