Britvin Sergey N, Rumyantsev Andrey M
Department of Crystallography, Saint-Petersburg State University, Universitetskaya Nab. 7/9, 199034 St Petersburg, Russian Federation.
Department of Genetics and Biotechnology, Saint-Petersburg State University, Universitetskaya Nab. 7/9, 199034 St Petersburg, Russian Federation.
Acta Crystallogr E Crystallogr Commun. 2017 Aug 30;73(Pt 9):1385-1388. doi: 10.1107/S2056989017012105. eCollection 2017 Sep 1.
7-Aza-bicyclo-[2.2.1]heptane (7-aza-norbornane) is a bridged heterocyclic nucleus found in epibatidine, the alkaloid isolated from the skin of the tropical poison frog . Since epibatidine is known as one of the most potent acetyl-choline nicotinic receptor agonists, a plethora of literature has been devoted to this alkaloid. However, there are no structural data on the unsubstituted 7-aza-norbornane, the parent bicyclic ring of epibatidine and its derivatives. We herein present the structural characterization of the 7-aza-bicyclo-[2.2.1]heptane parent ring as its hydro-chloride salt, namely 7-aza-bicyclo-[2.2.1]heptan-7-ium chloride, CHN·Cl. The compete cation is generated by a crystallographic mirror plane with the N atom lying on the mirror, as does the chloride anion. In the crystal, the cations are linked to the anions by N-H⋯Cl hydrogen bonds, which generate [001] chains.
7-氮杂双环-[2.2.1]庚烷(7-氮杂降冰片烷)是在从热带毒蛙皮肤中分离出的生物碱埃博霉素中发现的一种桥连杂环核。由于埃博霉素是已知最强效的乙酰胆碱烟碱受体激动剂之一,因此大量文献都围绕这种生物碱展开。然而,关于未取代的7-氮杂降冰片烷(埃博霉素及其衍生物的母体双环)却没有结构数据。我们在此展示了7-氮杂双环-[2.2.1]庚烷母体环盐酸盐的结构表征,即7-氮杂双环-[2.2.1]庚烷-7-鎓氯化物,CHN·Cl。完整的阳离子由一个晶体学镜面生成,N原子位于镜面上,氯离子阴离子也是如此。在晶体中,阳离子通过N-H⋯Cl氢键与阴离子相连,形成[001]链。