Acta Cryst. (2009). E65, o96  [ doi:10.1107/S1600536808040373 ]

(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea

Ú. Peña, S. Bernès and R. Gutiérrez

Abstract: The title compound, C₁₁H₂₀N₂O₂S, is an enantiomerically pure heterocycle-substituted thiourea synthesized under solvent-free conditions. The thiourea unit adopts a ZZ conformation, with the HN-(C=S)-NH core almost planar and the tetrahydrofurfuryl groups placed below and above this plane. The whole molecule thus approximates to noncrystallographic C₂ symmetry. Unexpectedly, the C=S group is not involved in intermolecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, molecules form a one-dimensional network based on weak N-HO(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 2₁ screw axis along [100].

Online 13 December 2008

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