(1R,2R,7S,8R,9R)-N-(2-Hydroxy-2,6,6,9-tetramethyl-12-oxatricyclo[7.2.1.01,7]dodecan-8-yl)acetamide

Amed Benharref (1) , Mustapha Ait Elhad (1) , Noureddine Mazoir (1) , Jean-Claude Daran (2) , Abdelouahd Oukhrib (1) , Moha Berraho (1)

1 Laboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16
2 LCC - Laboratoire de chimie de coordination

The title compound, C17H29NO3, was synthesized in two steps from [beta]-himachalene (2,6,6,9-tetramethylbicyclo[5.4.01,7]undeca-1,8-diene), which was isolated from an oil of the Atlas cedar (Cedrus Atlantica). The asymmetric unit contains two independent molecules (A and B): B features an intramolecular O-H...O hydrogen bond whereas A forms an intermolecular O-H...O link to B. Each molecule is built up from a seven-membered ring to which a bridged six-membered ring is fused: the cycloheptane rings have twist-chair conformations, while the bridged cyclohexane rings display near-perfect boat conformations. In the crystal, the molecules are linked by N-H...O and O-H...O hydrogen bonds forming helical chains propagating along the b-axis direction. Some weak C-H...O interactions are also observed.

Mots clés: Crystal structure; [beta]-himachalene; Two fused rings; Hydrogen bonding

Domaines: Chimie de coordination

Amed Benharref, Mustapha Ait Elhad, Noureddine Mazoir, Jean-Claude Daran, Abdelouahd Oukhrib, et al.. (1R,2R,7S,8R,9R)-N-(2-Hydroxy-2,6,6,9-tetramethyl-12-oxatricyclo[7.2.1.01,7]dodecan-8-yl)acetamide. IUCrData, 2017, 2 (7), pp.x170970. ⟨10.1107/S2414314617009701⟩. ⟨hal-02272835⟩