Hydrogen Bonding in α-Ferrocenyl Alcohols: Structures of 1-Ferrocenylethanol, 1-Ferrocenyl-2-phenylethanol, 1-Ferrocenyl-1-phenylpropan-1-ol, 1-Ferrocenyl-1-phenyl-2. methylpropan-1-ol, 1-Ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol, 1-Ferrocenyl-1,2

摘要

The structure of 1-ferrocenylethanol (la), C12H14FeO, tetragonal, I4ycd, a = 23.3334(18), c = 7.7186(11)A, Z = 16, R = 0.025 for 850 observations [I > 3σ(I)], contains spiral chains generated by a 41 axis, in which the molecules are connected by O-H...O hydrogen bonds in a motif witho graph set C(2) with an O...O distance of 2.724 (3) A. 1-Ferrocenyl-2-phenylethanol (1f), C18H18FeO, orthorhombic, Pnaa, a - 9.8589 (7), b = 15.2800(17), c = 19.1399 (17) A, Z = 8, R = 0.036for 1508 observations [I > 3σ(I)], crystallizes as dimeric aggregates lying across a crystallographic twofold axis and held together by O-H...O hydrogen bonds in a motif witho graph set R22(4) with an O...O distance of 2.868 (8) A; there are also intramolecular O-H...π(C5H5) interactions. 1-Ferrocenyl-1-phenyl-propan-1-ol (2b), C19H20FeO, monoclinic, P21/c,a = 10.2443 (13), b = 10.5811 (17), c =14.2487 (12)A, β = 100.190 (9)°, Z = 4, R = 0.029 for 2289 observations [I > 3σ(I)], crystallizes as isolated molecules containing O-H...π(C5H5) interactions. In 1-ferrocenyl-1-phenyl-2-methylpropan-1-ol (2c), C20H22FeO, monoclinic, Cc, a = 25.387 (4), b = 7.6825 (6), c = 17.803 (3) A, β=108.217(17)°, Z = 8, R = 0.022 for 3286 observations [I> 3σ(I)], there are two molecules in the asymmetric unit, but the structure consists of isolated molecules containing O-H...π(C5H5) interactions. 1-Ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol (2d), C21H24FeO, monoclinic, P21, a = 8.007(4), b = 13.002(2), c = 66.24(1)A, β = 91.96(3)°, Z = 16, R = 0.072 for 4130 observations [I > 3σ(I)], has four molecules in the asymmetric unit, but there is no intermolecular hydrogen bonding. The structure of 1-ferrocenyl-1,2-diphenylethanol (2), CMH22FeO, monoclinic, C2/c, a = 26.229(2), b = 5.889(2), c = 24.553(2)A, β=104.114(11)°, Z = 8, R = 0.036 for 1733 observations [I > 2.5σ(I)], consists of isolated molecules in which the hydroxyl H atom is disordered unequally over three sites, each of which is trans to one of the C-C bonds involving C1; H atoms in two of these sites are involved in intramolecular O-H...π(C5H5) interactions and the H atom in the third is involved in an O-H...π(arene) interaction. The structure of diferrocenyl (phenyl)metha-nol (2g), C27H24Fe2O, triclinic, P1, a = 9.3999(11), b = 11.1988(16), c = 11.9720(16)A, α=117.844(11), β = 98.890(10), γ = 102.362(11)°, Z = 2, R = 0.031 for 3435 observations [I > 2.5σ(I)], consists of centro-symmetric dimers held together by O-H...O hydrogen bonds in a motif witho graph set Rl(4) with an O...O distance of 2.926 (4) A; there are also intramolecular O-H...π(C5H5) interactions. Closed dimers containing the R22(4) (OH)2 hydrogen-bonding motif, while unknown for purely organic alcohols, are a common occurrence in a-ferrocenyl alcohols (five examples from 13 known structures).