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Order and Disorder in the Structures of Two Crystal Polymorphs of the Adduct Bis(Quinolinium-2-Carboxylate) DL-Malic Acid

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Abstract

The structures of two polymorphs of the anhydrous cocrystal adduct of bis(quinolinium-2-carboxylate) DL-malic acid, one triclinic the other monoclinic and disordered, have been determined at 200 K. Crystals of the triclinic polymorph 1 have space group P-1, with Z = 1 in a cell with dimensions a = 4.4854(4), b = 9.8914(7), c = 12.4670(8) Å, α = 79.671(5), β = 83.094(6), γ = 88.745(6)°. Crystals of the monoclinic polymorph 2 have space group P21/c, with Z = 2 in a cell with dimensions a = 13.3640(4), b = 4.4237(12), c = 18.4182(5) Å, β = 100.782(3)°. Both structures comprise centrosymmetric cyclic hydrogen-bonded quinolinic acid zwitterion dimers [graph set R 22 (10)] and 50% disordered malic acid molecules which lie across crystallographic inversion centres. However, the oxygen atoms of the malic acid carboxylic groups in 2 are 50% rotationally disordered whereas in 1 these are ordered. There are similar primary malic acid carboxyl O–H···Oquinaldic acid hydrogen-bonding chain interactions in each polymorph, extended into two-dimensional structures but in 1 this involves centrosymmetric cyclic head-to-head malic acid hydroxyl-carboxyl O–H···O interactions [graph set R 22 (10)] whereas in 2 the links are through single hydroxy-carboxyl hydrogen bonds.

Graphical Abstract

The structure determinations of two crystal polymorphs of the 2:1 adduct of quinolinium-2-carboxylate with DL-malic acid has shown one to be triclinic and ordered while in the second monoclinic form the carboxylic acid groups of the malic acid moiety are disordered.

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Acknowledgments

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

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Authors and Affiliations

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

    Graham Smith

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

    Urs D. Wermuth

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  1. Graham Smith
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  2. Urs D. Wermuth
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Correspondence to Graham Smith.

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Smith, G., Wermuth, U.D. Order and Disorder in the Structures of Two Crystal Polymorphs of the Adduct Bis(Quinolinium-2-Carboxylate) DL-Malic Acid. J Chem Crystallogr 41, 241–246 (2011). https://doi.org/10.1007/s10870-010-9871-y

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  • DOI: https://doi.org/10.1007/s10870-010-9871-y

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