Supramolecular chemistry of amine-phenol adducts; novel three-dimensional framework structures in adducts of bis(2-aminoethyl)amine with 4,4 '-sulfonyldiphenol, 1,1,1-tris(4-hydroxypenyl)ethane and 3,5-dihydroxybenzoic acid, and in the methanol-solvated adduct of tris(2-aminoethyl) amine with 4,4 '-biphenol

C Glidewell, G Ferguson, R M Gregson, C G Campana

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Bis(2-aminoethyl)amine-4,4'-sulfonyldiphenol (1/3) (1) (orthorhombic Pccn with Z' = 0.5) is a salt, [HN(CH2CH2NH3)(2)](2+). [O2S(C6H4O)(2)](2-).[O2S(C6H4OH)(2)](2), containing both dianionic and neutral bis-phenol units, The neutral and anionic bis-phenol units are linked by strong O- H...O- hydrogen bonds to form ladders built from R-4(4)(48) rings: each ladder is interwoven with its two nearest neighbours to form a continuous two-dimensional sheet, The amine cations play two roles: they link each ladder to its two next-nearest neighbours by means of N-H...O hydrogen bonds and they also link each sheet to the two neighbouring sheets, again via N-H...O hydrogen bonds, thus generating a three-dimensional framework, Bis(2-aminoethyl)amine-l,1,1-tris(4-hyclroxyphenyl)ethane-methanol (1/4/1) (2) (triclinic P (1) over bar with Z' = 0.5) consists entirely of neutral Fragments The tris-phenol units are linked by O-H...O hydrogen bonds into molecular ladders built from R-4(4)(48) rings: these ladders are linked by the amine units, firstly into sheets and thence into a three-dimensional framework. Bis(2-aminoethyl)amino-3,5-dihydroxybenzoic acid (1/2) (3) (monoclinic P2(1)/c with Z' = 1) is a salt [HN(CH2CH2NH3)(2)](2+).[{(HO)(2)C6H3COO}(-)](2). The 3,5-dihydroxybenzoate anions are linked by O-H...O hydrogen bonds into interwoven and cross-connected (001) sheets linked by further O-H...O hydrogen bonds into a three-dimensional framework, The (001) sheets are further linked by ladders formed Front both cat-ions and anions. Tris(2-aminoethyl)amine-4,4'-biphenol-methanol (1/3/1), (4) (monoclinic P2(1)), is a salt[{(H2NCH2CH2)(2)-N(CH2CH2NH3)}(+)](2).[OC6H4C6H4O](2-).[HOC6H4C6H4OH](5.-) [MeOH](2), with Z' = 1. The asymmetric unit, containing ten independent molecular components, cart be regarded as a supermolecule held together by a total of 13 independent hydrogen bonds, of O-H...O, O-H...N and N-H...O types. The supermolecules are linked by O-H...O and N-H...O hydrogen bonds into two-dimensional sheets, generated by translation; further N-H...O hydrogen bonds around the 2, screw axes link neighbouring sheets together into a three-dimensional framework.

Original languageEnglish
Pages (from-to)68-84
Number of pages17
JournalActa Crystallographica. Section B, Structural Science
Volume56
Publication statusPublished - Feb 2000

Keywords

  • HYDROGEN-BOND PATTERNS
  • 1,3,5-BENZENETRICARBOXYLIC ACID
  • CRYSTAL PACKING
  • TRIMESIC ACID
  • 1,2-DIAMINOETHANE
  • 1,4-DIAZABICYCLO<2.2.2>OCTANE
  • MOLECULES

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