Chain, sheet and framework structures in the adducts of phenylphosphonic acid with 4,4′-bipyridyl (1/1), piperazine (2/1) and 1,4-diazabicyclo[2.2.2]octane (2/1)

Phenylphosphonic acid-4,4'-bipyridyl (1/1), (1), C6H7O3P C10H8N2, triclinic, P (1) over bar, a = 6.9026(8), b= 9.7086(9), c = 12.201(2)Angstrom, alpha = 77.138(9), beta= 74.345(10), gamma = 75.477(8)degrees with Z = 2, is a salt, C10H9N2+[C6H5PO2(OH)](-), containing singly protonated 4,4'-bipyridyl cations: the cations and anions are linked by N-H ... O and C-H ... O hydrogen bonds in an R-2(2)(7) motif and these aggregates are linked into centrosymmetric R-2(2)(8) dimers by O-H ... O hydrogen bonds; the dimer units are linked into chains by CH ... O hydrogen bonds. Phenylphosphonic acid-piperazine (2/1), (C6H7O3P)(2) . C4H10N2 (2), monoclinic, P2(1)/n, a = 6.0042(9), b = 19.746(3), c = 8.651 (2) Angstrom, beta = 105.63(2)degrees with Z = 2, is a salt, C4H12N22+ - [{C6H5PO2(OH)}(-)](2), containing doubly protonated piperazine: the anions are linked by O-H ... O hydrogen bonds into centrosymmetric R-2(2)(8) dimers and these dimers are linked to the centrosymmetric cations by N-H ... 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 R-6(4)(16) and R-4(4)(18) rings. Phenylphosphonic acid-1,4-diazabicyclo [2.2.2] octane (2/1), (3), (C6H7O3P)(2) . C6H12N2, monoclinic, P2(1)/n, a= 6.3607(3), b = 21.8300(11), c = 14.5965(9)Angstrom, beta = 92.558 (6)degrees, 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 ... O hydrogen bonds, and these chains are cross-linked via the diamines by means of N-H ... O and O-H ... N hydrogen bonds. The resulting sheets built from R-8(8)(34) rings are linked by C-H ... O hydrogen bonds into a three-dimensional framework.