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Zeitschrift für Kristallographie - Crystalline Materials

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Volume 225, Issue 1


Two polymorphs of bis(4-benzoylthio-1,3-dithiole-2-thione)-5,5′-disulphide

Nadia M. Comerlato
  • 1 Universidade Federal do Rio de Janeiro, Departamento de Quimica Inorganica, Rio de Janeiro, Brasilien
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/ Lucas G. Carreira
  • 2 Universidade Federal do Rio de Janeiro, Departamento de Quimica Inorganica, Rio de Janeira, Brasilien
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/ R. Alan Howie
  • 3 University of Aberdeen, Department of Chemistry, Old Aberdeen, AB24 3UE, Scotland, Großbritannien
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/ Lourinaldo da S. Junior / James L. Wardell
Published Online: 2010-04-19 | DOI: https://doi.org/10.1524/zkri.2010.1195


Reaction of caesium 4-benzoyl-1,3-dithiole-2-thione-5-thiolate with iodine produced bis(4-benzoylthio-1,3-dithiole2-thione)-5,5′-disulfide, 6. Compound, 6 has been obtained in two crystalline forms, on recrytsallisation from different organic solvent systems, designated 6X with space group P21/c and 6Y with space group P21. Two enantiomers of the molecule of 6 are observed but both polymorphs are racemates, 6X because of the centrosymmetric space group P21/c and 6Y because of the presence of both enantiomers in the bimolecular asymmetric unit. The polymorphs differ in molecular packing, the resulting intermolecular contacts and the disposition of the enantiomers. In 6X the enantiomers are found in separate stacks of face to face molecules which combine to create channels containing intermolecular C–H · · · O hydrogen-bonds along with π · · · π overlap of rings within and between the stacks. In 6Y the enantiomers are found in separate chains with intermolecular C–H · · · S hydrogen-bonds providing connnectivity within and between the chains and, overall, two-dimensional connectivity in well defined layers of molecules. Stacking of the layers creates stacks of face to face molecules similar to, but less regular than those observed in 6X, in which the enantiomers alternate along the length of the stack.

Keywords: 4-benzoyl-1,3-dithiole-5-thiolate; Polymorphs; dmit species; X-ray diffraction; Single crystal structure analysis

About the article

* Correspondence address: Fundação Oswaldo Cruz, Centro de Desenvolvimento Tecnológico em Saúde, Av. Brasil 4365, Casa Amarela, Campus de Manguinhos, 21040-900 Rio de Janeiro, Brasilien,

Published Online: 2010-04-19

Published in Print: 2010-02-01

Citation Information: Zeitschrift für Kristallographie International journal for structural, physical, and chemical aspects of crystalline materials, Volume 225, Issue 1, Pages 29–35, ISSN (Print) 0044-2968, DOI: https://doi.org/10.1524/zkri.2010.1195.

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