Crystal engineering using bisphenols: interwoven ladders, sheet and framework structures in the binary adducts of 4,4 '-sulfonyldiphenol with pyrazine (2/1), 4,4 '-bipyridyl (1/1), trans-1,2-bis(4-pyridyl)ethene (1/1), 1,2-bis(4-pyridyl)ethane (1/1) and 4,4 '-trimethylenedipyridine (1/1), and in 4,4 '-sulfonyldiphenol-4,4 '-trimethylenedipiperidine-water (2/2/1)

G Ferguson, C Glidewell, R M Gregson, E S Lavender

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38 Citations (Scopus)

Abstract

The structures of six hydrogen-bonded adducts of 4,4'-sulfonyldiphenol with heteroaromatic amines have been determined. In 4,4'-sulfonyldiphenol-pyrazine (2/1) the pyrazine molecules lie across centres of inversion. The bisphenol molecules are linked into C(8) chains parallel to [100] by means of O-H ... O=S hydrogen bonds, and antiparallel pairs of these chains are cross-linked by the pyrazine molecules, via O-H ... N hydrogen bonds, to form molecular ladders containing R-6(6)(50) rings between the rungs of the ladders. Each ladder is interwoven with two neighbouring ladders, thus producing a continuous two-dimensional sheet. The structure of 4,4'-sulfonyldiphenol-4,4'-bipyridyl (1/1) consists of spiral C-2(2)(21) chains parallel to [010] containing alternating bisphenol and bipyridyl molecules linked by O-H ... N hydrogen bonds: these chains are linked by two types of C-H ... O=S hydrogen bonds which form C(5) chains along [001] and C-2(2)(10) chains along [101], thus generating two interconnected nets characterized in the one case by a chequerboard pattern of R-6(6)(44) and R-6(6)(52) rings, and in the other by a single type of R-6(6)(46) ring. 4,4'-Sulfonyldiphenol-trans-1,2-bis(4-pyridyl) ethene (1/1) [systematic name: 4,4'-sulfonyldiphenol-trans-4,4'-vinylenedipyridine (1/1)] and 4,4'-sulfonyldiphenol-1,2-bis(4-pyridyl)ethane (1/1) [systematic name: 4,4'-sulfonyldiphenol-trans-4 ,4'-ethylenedipyridine (1/1)] are isomorphous: the 1,2-bis(4-pyridyl)ethene component exhibits orientational disorder, corresponding approximately to a 180 degrees rotation of cn 23% of the molecules about the NN vector; in each compound the structure is built from C-2(2)(23) chains of alternating bisphenol and bis(pyridyl) molecules connected by O-H ... N hydrogen bonds, running parallel to [112] and generated by translation. The [112] chains are linked by C-H ... O hydrogen bonds which generate C-2(2)(12) chains parallel to [101], so forming a two-dimensional net built from R-6(6)(50) rings. The structure of 4,4'-sulfonyldiphenol-4,4'-trimethylenedipyridine (1/1) consists of C-2(2)(24) chains parallel to [100] generated by translation and consisting of alternating bisphenol and bis(pyridyl) molecules linked by O-H ... N hydrogen bonds. Pairs of such chains are coiled together to form double helices, and pairs of such double helices, of opposite hand, are linked together by paired C-H ... O hydrogen bonds in R-2(2)(10) rings to form pairs of interwoven ladders in which the C-2(2)(24) chains form the uprights and the R-2(2)(10) rings form the rungs, between which are R-6(6)(50) rings: an R-2(2)(10) ring belonging to one ladder lies at the centre of an R-6(6)(50) ring belonging to the other. 4,4'-Sulfonyldiphenol-4, 4'-trimethylenedipiperidine-water (2/2/1) is a salt, 2C(13)H(27)N(2)(+). 2C(12)H(9)O(4)S(-). H2O, containing two independent singly protonated diamine cations, two independent bisphenolate anions, and neutral water molecules. The two independent diamine cations are linked by N-H ... N hydrogen bonds into C-2(2)(24) chains running parallel to [001] and generated by translation, and each type of bisphenolate anion forms an independent spiral C(12) chain, also parallel to [001].

The three types of chain are linked by the water molecules: the two types of bisphenolate chain are linked by water molecules acting as double donors in O-H ... O- hydrogen bonds in a C-6(4)(32) chain parallel to [100], thus generating a two-dimensional net built from R-8(6)(56) rings; the diamine chains are linked to these nets by means of N-H ... O hydrogen bonds in which the water molecules act as accepters and further hydrogen bonds, of N-H ... O- and N-H ... O=S types, link these two-dimensional nets into a continuous three-dimensional framework.

Original languageEnglish
Pages (from-to)573-590
Number of pages18
JournalActa Crystallographica. Section B, Structural Science
Volume55
Publication statusPublished - 1 Aug 1999

Keywords

  • HYDROGEN-BONDED STRUCTURE
  • ORGANIC-COMPOUNDS
  • HYDRATED ADDUCT
  • TRIS-PHENOLS
  • 1,1,1-TRIS(4-HYDROXYPHENYL)ETHANE
  • TRIPHENYLMETHANOL
  • PIPERAZINE
  • CHAINS
  • NETS
  • 1,4-DIAZABICYCLO<2.2.2>OCTANE

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