title: Dendrobine support studies. The structure of a novel 3-azatricyclo[6.2.1.0(4,11)]-undecane derivative.
abstract: (1S*, 4R*, 8S*, 11R*)-3-Diphenylmethyl-11-methyl-3- azatricyclo[6.2.1.0(4,11)]undec-5-en-2-one, C24H25NO, Mr = 343.47, monoclinic, P2(1), a = 10.248 (3), b = 8.859 (2), c = 10.344 (2) A, beta = 99.816 (14) degrees, V = 925.4 (3) A3, Z = 2, D chi = 1.23 g cm-1 (163 K), lambda(Mo K alpha) = 0.7107 A, mu = 0.6927 cm-1, F(000) = 368, T = 163 K, R = 0.0423 for 2569 reflections. The compound is spontaneously resolved upon crystallization. The N atom appears to be sp2 hybridized [N is 0.0901 (13) A from plane through three ligand atoms] and in conjugation with the carbonyl group [short N--C bond 1.351 (2) A]. The tricyclic ring system is concave. Ring strain appears to affect C--C bond lengths of the central atom of the 3-ring system. The average C--C bond length for this atom to other ring atoms is 1.551 (2) while the average for all other sp3 C--sp3 C bonds is 1.530 (2) A.
authors.affiliation: Department of Chemistry, University of Texas, Austin 78712.
authors.forename: V M
authors.initials: VM
authors.lastname: Lynch
authors.forename: W
authors.initials: W
authors.lastname: Li
authors.forename: S F
authors.initials: SF
authors.lastname: Martin
authors.forename: B E
authors.initials: BE
authors.lastname: Davis
mesh_terms: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D000697:Central Nervous System Stimulants; D015394:Molecular Structure; D014961:X-Ray Diffraction
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D000697:Central Nervous System Stimulants; C065570:3-diphenylmethyl-11-methyl-3-azatricyclo(6.2.1.0(4,11))undec-5-en-2-one; C002077:dendrobine