The Structure of N-(Chloromethyl)Strychninium Chloride, a Spontaneously Crystallized Product Relevant to Analytical Chemistry, Bioprospecting, and Chiral Separations

Strychnine is well known as a highly toxic alkaloid derived from the plant Strychnos nux-vomica. It has been applied for chiral separations as a resolving agent for co-crystallizations, as a standard for chromatographic separations, as a rodenticide, as a natural therapy and stimulant, and as a poisonous plot device in works of fiction. Dissolving strychnine into the common organic solvent dichloromethane results in the spontaneous crystallization of the title compound N-(chloromethyl)strychninium chloride. Crystals of the compound were isolated in the orthorhombic space group P2₁2₁2₁ with a = 7.6819(2) Å, b = 7.9621(2) Å, c = 30.7170(9) Å, α = 90°, β = 90°, γ = 90°. The crystal structure has bilayers of N-(chloromethyl)strychninium cations with corresponding bilayers of chloride ions interacting to the cations through C–H hydrogen bonds.

Graphical Abstract