Wood Matthew R, Brettell Thomas A, Thompson Hugh W, Lalancette Roger A
Acta Crystallogr Sect E Struct Rep Online. 2008 Jan 30;64(Pt 2):o525. doi: 10.1107/S1600536808002535.
The title compound, (1R,2R,3S,5S,8S)-3-hydr-oxy-8-methyl-8-azoniabicyclo-[3.2.1]octane-2-carboxylic acid chloride, C(9)H(16)NO(3) (+)·Cl(-), is both a metabolite and a precursor of the tropane alkaloid l-cocaine. The carboxyl group is not involved in dimerization, but instead donates a hydrogen bond to the chloride counter-ion, which participates in two additional hydrogen bonds. The chloride ion is thus trigonally hydrogen bonded to three l-ecgonine cations. The quarternary N proton is intra-molecularly hydrogen bonded to the carboxyl C=O group, an arrangement identical to that reported for both (-)-nor-cocaine and the tetrachloroaurate(III) salt of l-cocaine. One close inter-molecular C-H⋯O contact exists.
标题化合物，(1R,2R,3S,5S,8S)-3-羟基-8-甲基-8-氮杂双环-[3.2.1]辛烷-2-羧酸氯化物，C(9)H(16)NO(3) (+)·Cl(-)，既是托烷生物碱l-可卡因的代谢产物又是其前体。羧基不参与二聚作用，而是向氯离子抗衡离子提供一个氢键，该氯离子参与另外两个氢键。因此，氯离子通过三角氢键与三个l-爱康宁阳离子相连。季铵N质子通过分子内氢键与羧基C=O基团相连，这种排列与报道的(-)-去甲可卡因和l-可卡因的四氯金(III)盐相同。存在一个紧密的分子间C-H⋯O接触。
