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

J Am Chem Soc. 2004 Jun 9;126(22):7071-81. doi: 10.1021/ja0498235.

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 (P2(1)/a). The structure of form 2 was solved and refined from powder diffraction data, giving a disordered structure in the Rm (166) space group (Z = 3). It could also be refined against a P1 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 P2(1) (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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Computer Simulation*
  • Crystallization
  • Fungicides, Industrial / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • X-Ray Diffraction

Substances

  • Fungicides, Industrial
  • Nitriles
  • tetrachloroisophthalonitrile