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-hydroxyphenyl)-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; RM Gregson; CF Campana

doi:10.1107/s0108768199009714

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-hydroxyphenyl)-ethane and 3,5-dihydroxybenzoic acid, and in the methanol-solvated adduct of tris(2-aminoethyl)-amine with 4,4'-biphenol

Acta Crystallogr B. 2000 Feb:56 (Pt 1):68-84. doi: 10.1107/s0108768199009714.

Authors

C Glidewell¹, G Ferguson, RM Gregson, CF Campana

Affiliation

¹ School of Chemistry, University of St. Andrews, Fife, Scotland. [email protected]

PMID: 10735445
DOI: 10.1107/s0108768199009714

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-.[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 R4(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-1,1,1-tris(4-hydroxyphenyl)ethane-methanol (1/4/1) (2) (triclinic P1 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 R4(4)(48) rings: these ladders are linked by the amine units, firstly into sheets and thence into a three-dimensional framework. Bis(2-aminoethyl)amine-3,5-dihydroxybenzoic acid (1/2) (3) (monoclinic P2(1)/c with Z' = 1) is a salt [HN(CH2CH2NH3)2]2+.[[(HO)2C6H3COO]-]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 from both cations 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, can 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(1) screw axes link neighbouring sheets together into a three-dimensional framework.