Acta Crystallographica Section C

Crystal Structure Communications

Volume 58, Part 3 (March 2002)

Acta Cryst. (2002). C58, o183-o186 [doi:10.1107/S0108270102001099]

Dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1-oxide and dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1,1''-dioxide

M. Kaftory, V. Shteiman and M. Botoshansky

Abstract: Oxidation of tetrahydrodispirobenzimidazole by m-chloroperbenzoic acid did not produce dispiro-2H-benzimidazole, which is the product obtained by oxidation with MnO₂. Instead, a mixture of two compounds was identified, namely dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1-oxide, C₁₈H₁₆N₄O, (III), and dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole] 1,1''-dioxide, C₁₈H₁₆N₄O₂, (IV). In (III), the molecules are disordered about a twofold rotation axis and have 2/m site symmetry. In (IV), the crystals are triclinic and the molecules occupy crystallographic inversion centers. Although the two compounds are very similar and are arranged in layers, they adopt completely different packing modes within the layers, viz. herring-bone in (III) and parallel molecules in (IV). The molecules within the layers are held together by C-HO and C-HN hydrogen bonds.

Formula: C₁₈H₁₆N₄O and C₁₈H₁₆N₄O₂

Online 28 February 2002


	Structure factor file (CIF format) (45.0 kbytes) Contains datablock III

	Structure factor file (CIF format) (66.1 kbytes) Contains datablock IV

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