Chain, Sheet and Framework Structures in the Adducts of Phenylphosphonic Acid with 4,4 prime -Bipyridyl (1/1), Piperazine (2/1) and 1,4-Diazabicyclo[2.2.2]octane (2/1)

Phenylphosphonic acid-4,4 prime -bipyridyl (1/1), (1), C6H7O3P.C10H8N 2, triclinic, P1, a = 6.9026 (8), b = 9.7086 (9), c = 12.201 (2) A, α = 77.138 (9), β = 74.345 (10), γ = 75.477 (8)°, with Z = 2, is a salt, C10H9N2+.[C6H 5PO2(OH)]-, containing singly protonated 4,4 prime -bipyridyl cations: the cations and anions are linked by N-H [midline ellipsis] O and C-H [midline ellipsis] O hydrogen bonds in an R22(7) motif and these aggregates are linked into centrosymmetric R22(8) dimers by O-H [midline ellipsis] O hydrogen bonds; the dimer units are linked into chains by C-H [midline ellipsis] O hydrogen bonds. Phenylphosphonic acid-piperazine (2/1), (C6H7O3P)2.C4H 10N2 (2), monoclinic, P21/n a = 6.0042 (9), b = 19.746 (3), c = 8.651 (2) A, β = 105.63 (2)°, with Z = 2, is a salt, C4H12N22+.-[{C6H 5PO2(OH)}-]2, containing doubly protonated piperazine: the anions are linked by O-H [midline ellipsis] O hydrogen bonds into centrosymmetric R22(8) dimers and these dimers are linked to the centrosymmetric cations by N-H [midline ellipsis] O hydrogen bonds: each cation is hydrogen-bonded to four different anion dimers and each anion dimer is hydrogen-bonded to four different cations; the overall structure consists of two-dimensional sheets built from R46(16) and R44(18) rings. Phenylphosphonic acid-1,4-diazabicyclo[2.2.2]octane (2/1), (3), (C6H7O3P)2.C6H 12N2, monoclinic, P21/n, a = 6.3607 (3), b = 21.8300 (11), c = 14.5965 (9) A, β = 92.558 (6)° with Z = 4, is a salt in which one nitrogen of the diamine is fully protonated and the other is partially protonated: the anionic components are linked into C(4) chains by O-H [midline ellipsis] O hydrogen bonds, and these chains are cross-linked via the diamines by means of N-H [midline ellipsis] O and O-H [midline ellipsis] N hydrogen bonds. The resulting sheets built from R88(34) rings are linked by C-H [midline ellipsis] O hydrogen bonds into a three-dimensional framework.