Issue 8, 2009

Co-crystallisation of organic α,ω-dicarboxylic acids with the cyclic amides2-pyrrolidinone and 2-imidazolidinone

Abstract

Crystallisation of a selection of α,ω-alkanedicarboxylic acids (HOOC–(CH2)n–COOH, n = 0–6), maleic acid, fumaric acid, L-tartaric acid and DL-tartaric acid with 2-pyrrolidinone and 2-imidazolidinone yielded 11 new mixed systems which were shown to be co-crystals by single crystal X-ray diffraction at 120(2) K. The crystal structures are stabilised predominantly by amide–acid and amideamide N–H⋯O hydrogen bonds and acid–amide O–H⋯O hydrogen bonds, but the synthons formed are not always as expected from the hydrogen bond hierarchy described by Etter's rules (M. C. Etter, J. Phys. Chem., 1991, 95, 4601–4610). In the case of the 2-imidazolidinone and alkanediacid co-crystals, alternation in supramolecular structure is observed across the series.

Graphical abstract: Co-crystallisation of organic α,ω-dicarboxylic acids with the cyclic amides 2-pyrrolidinone and 2-imidazolidinone

Supplementary files

Article information

Article type
Paper
Submitted
22 Jan 2009
Accepted
24 Mar 2009
First published
16 Apr 2009

CrystEngComm, 2009,11, 1609-1614

Co-crystallisation of organic α,ω-dicarboxylic acids with the cyclic amides 2-pyrrolidinone and 2-imidazolidinone

S. K. Callear, M. B. Hursthouse and T. L. Threlfall, CrystEngComm, 2009, 11, 1609 DOI: 10.1039/B901453E

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