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Issue 10, 2008
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Isostructural polymorphs of triiodophloroglucinol and triiodoresorcinol

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Triiodoresorcinol (TIR, 2,4,6-triiodoresorcinol) and triiodophloroglucinol (TIG, 2,4,6-triiodophloroglucinol) crystallized as orthorhombic (TIR-O and TIG-O in P212121) and monoclinic (TIR-M and TIG-M in P21/n) polymorphs mediated via inter-halogen I⋯I interactions. The orthorhombic polymorphs are isostructural and in turn similar to the crystal structure of 1,3,5-triiodobenzene (TIB). The isostructural monoclinic polymorphs are similar to the structure of 1,3,5-trifluoro-2,4,6-triiodobenzene (TIF). Triiodophenol (TIP) crystallized in a single orthorhombic form only. The monoclinic structures have tandem O–H⋯O hydrogen bonds in addition to inter-iodine interactions. The similarity of crystal structures was confirmed by the formation of 1 : 1 binary solid-solutions, TIP +  TIR-O and TIR + TIG-O, in orthorhombic space groupP212121. Dimorphs of TIR and TIG establish a structural link in the triiodobenzene series TIB (P212121) → TIP (P212121) → TIR (P212121 and P21/n) → TIG (P212121 and P21/n) → TIF (P21/n). The search for new polymorphs was initiated by isostructurality relationship in the series of compounds.

Graphical abstract: Isostructural polymorphs of triiodophloroglucinol and triiodoresorcinol

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Supplementary files

Article information

26 Mar 2008
02 May 2008
First published
01 Jul 2008

New J. Chem., 2008,32, 1693-1701
Article type

Isostructural polymorphs of triiodophloroglucinol and triiodoresorcinol

N. K. Nath, B. K. Saha and A. Nangia, New J. Chem., 2008, 32, 1693
DOI: 10.1039/B804905J

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