Structure and conformational analysis of the opioid antagonist (-)-(1R,5R,9R)-5,9-diethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorpha n (Mr2266)

Acta Crystallogr C. 1989 Nov 15:45 ( Pt 11):1797-802. doi: 10.1107/s010827018900394x.

Abstract

C21H27NO2, Mr = 325.449, monoclinic, P2(1), a = 16.3916 (7), b = 12.7460 (5), c = 8.9806 (5) A, beta = 107.191 (4) degrees, V = 1792.5 (2) A3, Z = 4, Dm = 1.22 (2), D chi = 1.206 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu(Cu K alpha) = 0.566 mm-1, F(000) = 704, T = 291 K, final R = 0.048 for 4225 observed reflections. The two molecules present in the asymmetric unit adopt a different conformation with respect to the N-side chain. Starting from the asymmetric carbon and proceeding along the allyl moiety the conformations are antiperiplanar/(-)-anticlinal for molecule 1 and antiperiplanar/(+)-synclinal for molecule 2. The furyl rings engage in aromatic-aromatic interactions which are compared with results from a theoretical study from the literature. Finally, the 3-furyl geometry is evaluated through a Cambridge Structural Database search and CNDO/2 calculations.

MeSH terms

  • Benzomorphans*
  • Chemical Phenomena
  • Chemistry, Physical
  • Endorphins / antagonists & inhibitors*
  • Molecular Conformation
  • Molecular Structure
  • Morphinans*
  • X-Ray Diffraction

Substances

  • Benzomorphans
  • Endorphins
  • Morphinans
  • MR 2266