Characterization of complicated new polymorphs of chlorothalonil by X-ray diffraction and computer crystal structure prediction

Tremayne, Maryjane, Grice, Leanne, Pyatt, James C., Seaton, Colin C., Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Tsui, Helen H. Y., Price, Sarah L. and Cherryman, Julian C. 2004. Characterization of complicated new polymorphs of chlorothalonil by X-ray diffraction and computer crystal structure prediction. Journal of the American Chemical Society 126 (22) , pp. 7071-7081. 10.1021/ja0498235

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Abstract

A simultaneous experimental and computational search for polymorphs of chlorothalonil (2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile) has been conducted, leading to the first characterization of forms 2 and 3. The crystal structure prediction study, using a specifically developed anisotropic atom−atom potential for chlorothalonil, gave as the global minimum in the lattice energy a structure that was readily refined against powder diffraction data to the known form 1 (P21/a). The structure of form 2 was solved and refined from powder diffraction data, giving a disordered structure in the R3̄m (166) space group (Z = 3). It could also be refined against a P1̄ ordered model, starting from a low-energy hypothetical sheet structure found in the computational search. This shows that the disorder could be associated with the stacking of ordered sheets. The disordered structure for form 2 was later confirmed by single-crystal X-ray diffraction. The structure of form 3, determined from single-crystal diffraction, contains three independent molecules in the asymmetric unit in P21 (4) (Z = 6). Powder diffraction showed that this single-herringbone structure was similar to two low-energy structures found in the search. Further analysis confirmed that form 3 has a similar lattice energy and contains elements from both these predicted structures, which can be considered as good approximations to the form 3 structure.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	American Chemical Society
Last Modified:	24 Oct 2022 11:11
URI:	https://orca.cardiff.ac.uk/id/eprint/47212

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