Structures of two isomeric phenylethanolamine analogs containing the benzobicyclo[3.2.1]octane skeleton

Abstract

e/ido-8-Amino-6,7,8,9-tetrahydro-5,8- methano-5//-benzocyclohepten-9-ol hydrochloride, C1 2H1 6N0+.C1- Mr = 225-72, tetragonal, IAja, a = b = 24-641(3), c= 7-709 (1) A, F = 4681 (1) A3, Z = 16, D x = 1-281 Mgm~3 , A(MoKa) = 0-71069 A, /u = 0-3032 mm"1 , F(000) = 1920, T=297K. R = 0-0324 for 1543 independent reflections collected. exo-8-Amino~6,7,8,9-tetrahydro-5,8-methano-5Hbenzocyclohepten- 9-ol, C1 2H1 3NO, Mr= 189-26, monoclinic, Pljc, a = 13-863 (3), 6 = 6-910(2), c = 13-437 (3) A, V= 1018-2 (5) A3, Z = 4, Dx = 1-235 Mg m~3, A(Mo Ka) = 0-71069 A, ju = 0-08456 mm"1 , ,F(000) = 408, T= 297 K. R = 0-0378 for 1340 independent reflections collected. The torsion angles N-C(8)-C(9)-C(9a) of the two isomers are 0108-2701/87/122418-03501.50 174-0(2) and 173-4 (1)°, respectively, which are very close to those observed for epinephrine (172°) and norepinephrine (179°) with the side chain in a fully extended conformation. The cyclohexene moiety has a half-chair conformation as found in tetralols.