Crystal engineering using bisphenols and trisphenols. Complexes with 1,10-phenanthroline: hydrogen-bonded chains in adducts with 4,4 '-biphenol (1/1) and 4,4 '-sulfonyldiphenol (2/3), pi-pi stacked chains in the (1/2) adduct with 4,4 '-thiodiphenol, and pairwise-interwoven nets in 1,1,1-tris(4-hydroxyphenyl)ethane-1,10-phenanthroline-methanol (1/1/1)

G Ferguson, C Glidewell, E S Lavender

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73 Citations (Scopus)

Abstract

In 4,4'-biphenol-1,10-phenanthroline (1/1) [systematic name: 4,4'-biphenyldiol-1,10-phenanthroline (1/1)] the diphenol molecules lie across centres of inversion and the phenanthroline molecules lie across twofold rotation axes; the phenanthroline molecules act as chain-building units and the molecular components are linked into steeply zigzag C(16) chains parallel to [101] by means of O-H ... N hydrogen bonds. In the structure of 4,4'-thiodiphenol-1,10-phenanthroline (1/2) the phenanthroline molecules act as chain-terminating units; the supramolecular aggregation is finite, with the bisphenol linked to each phenanthroline molecule by means of a single O-H ... N hydrogen bond. pi-pi stacking interactions between the phenanthroline molecules in neighbouring hydrogen-bonded aggregates serve to link these aggregates into a continuous two-dimensional array. The phenanthroline molecules in 4,4'-sulfonyldiphenol-1,10-phenanthroline (2/3) play two roles: molecules in general positions act as chain-terminating units and are linked to the sulfonyldiphenol molecules by means of three-centre O-H ...(N)(2) hydrogen bonds, while those lying across twofold rotation axes act as chain builders and are linked to two different sulfonyldiphenol molecules by means of a two-centre O-H ... N hydrogen bond in each case; the resulting U-shaped five-component aggregates are further linked by C-H ... O=S hydrogen bonds into a C-3(3)(17)[R-2(2)(12)] 'chain of rings' along [001]. In 1,1,1-tris(4-hydroxyphenyl)ethane-1,10-phenanthroline -methanol (1/1/1) [systematic name: 4,4',4 "-ethylidynetriphenol-1, 10-phenanthroline-methanol (1/1/1)] the phenanthroline molecules again act as chain-terminating units: the trisphenol molecules and the methanol molecules are linked by O-H ... O hydrogen bonds into two-dimensional nets built from R-6(6)(42) rings, and pairs of these nets are interwoven. The formation of each net utilizes two hydroxyl groups per trisphenol molecule as hydrogen-bond donors and the remaining hydroxyl group acts as donor to the phenanthroline molecule in a three-centre O-H ...(N)(2) hydrogen bond.

Original languageEnglish
Pages (from-to)591-600
Number of pages10
JournalActa Crystallographica. Section B, Structural Science
Volume55
Publication statusPublished - 1 Aug 1999

Keywords

  • MOLECULAR-STRUCTURE
  • 1,2-DIAMINOETHANE
  • RINGS

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