Hydrogen-bonded adducts of ferrocene-1,1′-diylbis-(diphenylmethanol): crystal and molecular structures of adducts with methanol (1 : 1) and pyridine (1 : 2)

Abstract

Ferrocene-1,1′-diylbis(diphenylmethanol), [Fe(C₅H₄CPh₂OH)₂], forms hydrogen-bonded host–guest adducts with a wide range of hydrogen-bond donors and acceptors. Adducts with a diol: guest ratio of 1 : 1 were formed by MeOH, EtOH, Me₂SO, Me₂NCHO, piperazine, and 4,4′-bipyridyl and 1 : 2 adducts by Me₂SO, dioxane, pyridine and piperidine. The 1 : 1 adduct with MeOH has been shown to be triclinic, space group P with a= 8.7624(3), b= 12.2797(6), c= 14.8773(8)Å, α= 106.572(4), β= 97.879(4), γ= 100.873(4)° with a final R of 0.044 for 4982 observed reflections. The structure consists of a centrosymmetric assembly of two molecules of the host diol and two molecules of the guest MeOH, hydrogen bonded together to form a chair conformation (OH)₆ ring. The 1 : 2 adduct with pyridine has been shown to be monoclinic, space group C2/c with a= 16.6252(10), b= 11.1016(9), c= 20.9440(16)Å, β= 107.855(6)° with a final R of 0.042 for 3260 observed reflections. In the structure the diol lies on a two-fold rotation axis with its hydroxyl hydrogens disordered and participating in both intramolecular O–H ⋯ O and intermolecular O–H ⋯ N hydrogen bonding with the two pyridine guest molecules.