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Zeitschrift für Kristallographie - Crystalline Materials

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Volume 231, Issue 4


Crystal structure and Hirshfeld analysis of the kryptoracemate: bis(mefloquinium) chloride p-fluorobenzenesulphonate

Mukesh M. Jotani
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  • Bhavan’s Sheth R. A. College of Science, Department of Physics, Ahmedabad, Gujarat 380001, India
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/ James L. Wardell
  • Corresponding author
  • Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil
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/ Edward R.T. Tiekink
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  • Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
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Published Online: 2016-01-21 | DOI: https://doi.org/10.1515/zkri-2015-1914


The crystal structure analysis of the bis(mefloquinium) chloride p-fluorobenzenesulphonate salt reveals a rare example of a kryptoracemate given that the cations exhibit a non-crystallographic enantiomeric relationship. The conformations of the cations are based on a skewed letter L with the (piperidinium-2-yl)methanol group sitting almost normal to and directed away from the quinolinyl residue. The most prominent feature of the molecular packing is the formation of supramolecular helical chains along the a-axis, being sustained by pairs of hydroxyl-O–H···O (sulphonate), piperidinium-N–H···O (sulphonate) and piperidinium-N–H···Cl hydrogen bonds. Geometric and Hirshfeld surface analyses of the crystal structure shows significant differences in supramolecular aggregation between the cations due to the presence of different anions and this is the likely reason for the observed kryptoracemic behaviour.

This article offers supplementary material which is provided at the end of the article.

Keywords: crystal structure analysis; Hirshfeld surface; kryptoracemate; Mefloquine; X-ray diffraction


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About the article

Received: 2015-11-19

Accepted: 2015-12-15

Published Online: 2016-01-21

Published in Print: 2016-04-01

Citation Information: Zeitschrift für Kristallographie - Crystalline Materials, Volume 231, Issue 4, Pages 247–255, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2015-1914.

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