HYDROGEN-BONDING IN ALPHA-FERROCENYL ALCOHOLS - STRUCTURES OF 1-FERROCENYLETHANOL, 1-FERROCENYL-2-PHENYLETHANOL, 1-FERROCENYL-1-PHENYLPROPAN-1-OL, 1-FERROCENYL-1-PHENY1-2-METHYLPROPAN-1-OL, 1-FERROCENYL-1-PHENYL-2,2-DIMETHYLPROPAN 1-FERROCENYL-1,2-DIPHENYLETHANOL AND DIFERROCENYL(PHENYL)METHANOL

The structure of 1-ferrocenylethanol (1a), C12H14FeO, tetragonal, I4(1 )cd, a = 23.3334(18), c = 7.7186(11)Angstrom, Z = 16, R = 0.025 for 85 0 observations [I > 3 sigma(I)], contains spiral chains generated by a 4(1) axis, in which the molecules are connected by O-H...O hydrogen b onds in a motif with graph set C(2) with an O...O distance of 2.724(3) Angstrom. 1-Ferrocenyl-2-phenylethanol (1f), C18H18FeO, orthorhombic, Pnaa, a = 9.8589(7), b = 15.2800(17), c = 19.1399(17)Angstrom, Z = 8, R = 0.036 for 1508 observations [I > 3 sigma(I)], crystallizes as dime ric aggregates lying across a crystallographic twofold axis and held t ogether by O-H...O hydrogen bonds in a motif with graph set R(2)(2)(4) with an O...O distance of 2.868(8)Angstrom; there are also intramolec ular O-H...pi(C5H5) interactions. 1-Ferrocenyl-1-phenylpropan-1-ol (2b ), C19H20FeO, monoclinic, P2(1)/c, a = 10.2443(13), b = 10.5811(17), c = 14.2487(12)Angstrom, beta = 100.190(9)degrees, Z = 4, R = 0.029 for 2289 observations [I > 3 sigma(I)], crystallizes as isolated molecule s containing O-H...pi(C5H5) interactions. In 1-ferrocenyl-1-phenyl-2-m ethylpropan-1-ol (2c), C20H22FeO, monoclinic, Cc, a = 25.387(4), b = 7 .6825(6), c = 17.803(3)Angstrom, beta = 108.217(17)degrees, Z = 8, R = 0.022 for 3286 observations [I > 3 sigma(I)], there are two molecules in the asymmetric unit, but the structure consists of isolated molecu les containing O-H...pi(C5H5) interactions. 1-Ferrocenyl-1-phenyl-2,2- dimethylpropan-1-ol (2d), C21H24FeO, monoclinic, P2(1)/n, a = 8.007(4) , b = 13.002(2), c = 66.24(1)Angstrom, beta = 91.96(3)degrees, Z = 16, R = 0.072 for 4130 observations [I > 3 sigma(I)], has four molecules in the asymmetric unit, but there is no intermolecular hydrogen bondin g. The structure of 1-ferrocenyl-1,2-diphenylethanol (2f), C24H22FeO, monoclinic, C2/c a = 26.229(2) b = 5.889(2), c = 24.553(2)Angstrom, be ta = 104.114(11)degrees, Z = 8, R = 0.036 for 1733 observations [I > 2 .5 sigma(I)], consists of isolated molecules in which the hydroxyl H a tom is disordered unequally over three sites, each of which is trans t o one of the C-C bonds involving C1; H atoms in two of these sites are involved in intramolecular O-H...pi(C5H5) interactions and the H atom in the third is involved in an O-H...pi(arene) interaction. The struc ture of diferrocenyl(phenyl)methanol (2g), C27H24Fe2O, triclinic, <P(1 )over bar>, a = 9.3999(11), b = 11.1988(16), c = 11.9720(16)Angstrom, alpha = 117.844(11), beta = 98.890(10), gamma = 102.362(11)degrees, Z = 2, R = 0.031 for 3435 observations [I > 2.5 sigma(I)], consists of c entrosymmetric dimers held together by O-H...O hydrogen bonds in a mot if with graph set R(2)(2)(4) with an O...O distance of 2.926(4)Angstro m; there are also intramolecular O-H...pi(C5H5) interactions. Closed d imers containing the R(2)(2)(4) (OH)(2) hydrogen-bonding motif, while unknown for purely organic alcohols, are a common occurrence in alpha- ferrocenyl alcohols (five examples from 13 known structures).