Diversity in a simple co-crystal: racemic and kryptoracemic behaviour

U. B. Rao Khandavilli; Matteo Lusi; Balakrishna R. Bhogala; Anita R. Maguire; Matthias Stein; Simon E. Lawrence

doi:10.1039/C6CC04148E

Diversity in a simple co-crystal: racemic and kryptoracemic behaviour†

U. B. Rao Khandavilli,^a Matteo Lusi,

^b Balakrishna R. Bhogala,^a Anita R. Maguire,^c Matthias Stein^d and Simon E. Lawrence*^a

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* Corresponding authors

^a Department of Chemistry, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Ireland
E-mail: simon.lawrence@ucc.ie

^b Department of Chemical & Environmental Sciences, University of Limerick, Limerick, Ireland

^c Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Cork, Ireland

^d Molecular Simulations and Design Group, Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg, Germany

Abstract

The crystal structure containing (±)-3-methyl-2-phenylbutyramide with salicylic acid is the first example of a kryptoracemate co-crystal. It exhibits the first temperature mediated reversible single-crystal to single-crystal transition between two kryptoracemate forms, in addition to crystallising in another, racemic, form. Theoretical calculations and structural analysis reveal that there are only small differences in both energy and packing arrangements between the three forms. These results suggest that co-crystals can be an opportunity to investigate kryptoracemate behaviour.

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DOI: https://doi.org/10.1039/C6CC04148E
Article type: Communication
Submitted: 17 May 2016
Accepted: 08 Jun 2016
First published: 08 Jun 2016
This article is Open Access

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Chem. Commun., 2016,52, 8309-8312

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Diversity in a simple co-crystal: racemic and kryptoracemic behaviour

U. B. Rao Khandavilli, M. Lusi, B. R. Bhogala, A. R. Maguire, M. Stein and S. E. Lawrence, Chem. Commun., 2016, 52, 8309 DOI: 10.1039/C6CC04148E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Diversity in a simple co-crystal: racemic and kryptoracemic behaviour†

Abstract

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Diversity in a simple co-crystal: racemic and kryptoracemic behaviour

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