title: Structure and conformational analysis of the opioid antagonist (-)-(1R,5R,9R)-5,9-diethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorpha n (Mr2266).
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.
authors.affiliation: Instituut voor Farmaceutische Wetenschappen, Katholieke Universiteit, Leuven, Belgium.
authors.forename: C L
authors.initials: CL
authors.lastname: Verlinde
authors.forename: N M
authors.initials: NM
authors.lastname: Blaton
authors.forename: O M
authors.initials: OM
authors.lastname: Peeters
authors.forename: C J
authors.initials: CJ
authors.lastname: De Ranter
mesh_terms: D001575:Benzomorphans; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004723:Endorphins / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D015394:Molecular Structure; D009019:Morphinans; D014961:X-Ray Diffraction
chemical_list: D001575:Benzomorphans; D004723:Endorphins; D009019:Morphinans; C027247:MR 2266