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

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Abstract

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.

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Scheme 1
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Data Availability

CCDC-1,815,572 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac.uk/ or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; email: deposit@ccdc.cam.ac.uk.

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Acknowledgements

The authors acknowledge the muwinina people, the traditional owners of the land on which this research was conducted. The authors acknowledge the Central Science Laboratory at the University of Tasmania for access to their services. Additional unpublished datasets of the title compound were collected on the MX1 beamline at the Australian Synchrotron, part of ANSTO.

Funding

This research was supported under the Australian Research Council’s Discovery Early Career Research Award funding scheme (Project Number DE150100263).

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  1. School of Natural Sciences - Chemistry, College of Sciences and Engineering, University of Tasmania, Hobart, TAS, 7005, Australia

    Chloe M. Taylor & Nathan L. Kilah

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Correspondence to Nathan L. Kilah.

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Taylor, C.M., Kilah, N.L. The Structure of N-(Chloromethyl)Strychninium Chloride, a Spontaneously Crystallized Product Relevant to Analytical Chemistry, Bioprospecting, and Chiral Separations. J Chem Crystallogr 53, 379–385 (2023). https://doi.org/10.1007/s10870-022-00977-7

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