Structure of a tricyclic subunit of manzamine A.
(4a alpha,7a beta,10a beta)-2-Benzyl-1,2,3,4,4a,7,7a,8,9,10-decahydro-8,8- dimethylpyrrolo[2,3-i]isoquinolinium iodide, C20H29N2+.I-, M(r) = 424.37, monoclinic, P2(1)/n, a = 9.441 (4), b = 10.378 (4), c = 20.023 (9) A, beta = 91.56 (3) degrees, V = 1961 (1) A3, Z = 4, Dx = 1.44 g cm-3 (188 K), lambda(Mo K alpha) = 0.7107 A, mu = 16.16 cm-1, F(000) = 864, T = 188 K, R = 0.0288 for 3070 reflections [Fo greater than or equal to 4 sigma(Fo)]. The crystal structure determination was undertaken in order to establish the configuration around C10a. The rings of the isoquinoline group are trans, with the pyrrole moiety cis fused. The A ring is in the chair conformation, while the cyclohexene ring, B, is in the boat conformation owing to the cis fusion of the five-membered pyrrole ring. The pyrrole ring, C, assumes the half-chair conformation. The C-N bonds of the quaternary N atom, N8, are longer than those of the tertiary N atom, N2 [1.517 (2) for N8 and 1.463 (2) A for N2].
Lynch
V M
VM
Department of Chemistry and Biochemistry, University of Texas, Austin 78712.
Liao
Y
Y
Martin
S F
SF
Davis
B E
BE
D002227:Carbazoles; D007211:Indoles / Q000737:chemistry*; D046911:Macromolecular Substances; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D014961:X-Ray Diffraction
D002227:Carbazoles; D007211:Indoles; D046911:Macromolecular Substances; D011758:Pyrroles; C078290:manzamine A