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Resolution of the Chiral (1R,2S) Enantiomer of cis-Cyclohexane-1,2-dicarboxylic Acid in the Brucinium Salt 2,3-Dimethoxy-10-oxostrychnidinium (1R,2S)-2-carboxycyclohexane-1-carboxylate Dihydrate

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Abstract

The structure of the 1:1 brucinium salt of cis-cyclohexane-1,2-dicarboxylic acid, 2,3-dimethoxy-10-oxostrychnidinium (1R,2S)-2-carboxycyclohexane-1-carboxylate dihydrate, has revealed the resolved (1R,2S) enantiomer of the acid. Crystals of the compound are orthorhombic, space group P212121, with unit cell dimensions a = 8.1955(3), b = 12.4034(3), c = 29.9073(9) Å, and Z = 4. The asymmetric unit comprises the brucinium cation, the hydrogen cis-cyclohexane-1,2-dicarboxylate anion, in which the carboxylate group is disordered over two sites (58, 42%), and two water molecules of solvation, one of which is occupies two 50% occupancy sites. The classic undulating brucinium cation substructures are present with the anion and the water molecules occupying the interstitial cavities and are hydrogen-bonded to them in a two-dimensional network structure.

Graphical Abstract

The structure determination of the 1:1 proton-transfer hydrate salt of cis-cyclohexane-1,2-dicarboxylic acid with brucine has revealed the presence of the (1R,2S) enantiomeric form of the acid in a hydrogen-bonded structure.

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Acknowledgments

The authors acknowledge financial support from the Australian Research Council, the Science and Engineering Faculty (Queensland University of Technology) and Griffith University.

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Authors and Affiliations

  1. Science and Engineering Faculty, Queensland University of Technology, G.P.O. Box 2434, Brisbane, QLD, 4001, Australia

    Graham Smith & Urs D. Wermuth

  2. School of Biomolecular and Physical Sciences, Griffith University, Nathan, QLD, 4111, Australia

    Michael L. Williams

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  1. Graham Smith
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  2. Urs D. Wermuth
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  3. Michael L. Williams
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Correspondence to Graham Smith.

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Smith, G., Wermuth, U.D. & Williams, M.L. Resolution of the Chiral (1R,2S) Enantiomer of cis-Cyclohexane-1,2-dicarboxylic Acid in the Brucinium Salt 2,3-Dimethoxy-10-oxostrychnidinium (1R,2S)-2-carboxycyclohexane-1-carboxylate Dihydrate. J Chem Crystallogr 42, 555–559 (2012). https://doi.org/10.1007/s10870-012-0278-9

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  • DOI: https://doi.org/10.1007/s10870-012-0278-9

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