Patterns of soft C-H center dot center dot center dot O hydrogen bonding in diaryl sulfones

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

Research output: Contribution to journalArticle

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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-H . . .O 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-H . . .O 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-H . . .O 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-H . . .O hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.

Original languageEnglish
Pages (from-to)190-200
Number of pages11
JournalActa Crystallographica Section B, Structural Science
Volume57
Publication statusPublished - 2001

Keywords

  • CRYSTAL PACKING
  • 4,4'-SULFONYLDIPHENOL
  • LADDERS

Cite this

Patterns of soft C-H center dot center dot center dot O hydrogen bonding in diaryl sulfones. / Glidewell, C ; Harrison, W T A ; Low, J N ; Sime, J G ; Wardell, J L .

In: Acta Crystallographica Section B, Structural Science, Vol. 57, 2001, p. 190-200.

Research output: Contribution to journalArticle

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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-H . . .O 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-H . . .O 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-H . . .O 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-H . . .O hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.",
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TY - JOUR

T1 - Patterns of soft C-H center dot center dot center dot O hydrogen bonding in diaryl sulfones

AU - Glidewell, C

AU - Harrison, W T A

AU - Low, J N

AU - Sime, J G

AU - Wardell, J L

PY - 2001

Y1 - 2001

N2 - 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-H . . .O 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-H . . .O 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-H . . .O 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-H . . .O hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.

AB - 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-H . . .O 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-H . . .O 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-H . . .O 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-H . . .O hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.

KW - CRYSTAL PACKING

KW - 4,4'-SULFONYLDIPHENOL

KW - LADDERS

M3 - Article

VL - 57

SP - 190

EP - 200

JO - Acta Crystallographica Section B, Structural Science

JF - Acta Crystallographica Section B, Structural Science

SN - 0108-7681

ER -