Acta Crystallographica Section B

Structural Science

Volume 57, Part 2 (April 2001)

research papers

Acta Cryst. (2001). B57, 190-200 [ doi:10.1107/S0108768100015494 ]

Patterns of soft C-HO hydrogen bonding in diaryl sulfones

C. Glidewell, W. T. A. Harrison, J. N. Low, J. G. Sime and J. L. Wardell

Abstract: In bis(4-tolyl) sulfone, C₁₄H₁₄O₂S (1), 2,5,4'-trimethyldiphenyl sulfone, C₁₅H₁₆O₂S (2), and 4-chlorodiphenyl sulfone, C₁₂H₉ClO₂S (3), the molecules are linked by soft C-HO hydrogen bonds into three different types of one-dimensional aggregate: simple chains in (1), molecular ladders in (2) and chains of fused rings in (3). In each of 3,4-dimethyl-4'-chlorodiphenyl sulfone, C₁₄H₁₃ClO₂S (4), and 2,5-dimethyldiphenyl sulfone, C₁₄H₁₄O₂S (5), the C-HO hydrogen bonds link the molecules into two different types of two-dimensional sheet, based on a (4,4) net in (4) and a (3,6) net in (5). The patterns of soft C-HO hydrogen bonds in (1)-(5) are compared with those in other diaryl sulfones, mainly retrieved from the Cambridge Structural Database, whose substitution patterns preclude the formation of hard hydrogen bonds. Observed aggregation modes range from the formation of no C-HO hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.

Keywords: hydrogen bonding; sulfones; aggregates.