HYDROGEN-BONDING IN DIPHENYLMETHANOLS, RCPH(2)OH - STRUCTURES OF MONOMERIC (4-BIPHENYL)DIPHENYLMETHANOL AND DIPHENYL(2-PYRIDYL)METHANOL, DIMERIC 1,1,3-TRIPHENYLPROPYN-1-OL, TRIMERIC 2-METHYL-1,1-DIPHENYLPROPAN-1-OL, TETRAMERIC DIPHENYL(2-THIENYL)METHANOL, HEXAMERIC BIS(PENTAFLUOROPHENYL)METHANOL (AT 293 AND 173 K) AND POLYMERIC DIPHENYLMETHANOL

(4-Biphenyl)diphenylmethanol (1), C25H20O, orthorhombic, P2(1)2(1)2(1), a = 8.3580 (11), b = 13.8976 (17), c = 15.5915 (12)Angstrom, Z = 4, R = 0.032 for 1146 observations [I > 3 sigma(I)]: the structure contains isolated monomers with no hydrogen bonding. Diphenyl(2-pyridyl)methanol (2), C18H15NO, monoclinic, P2(1)/c, a = 8.1899 (8), b = 14.855 (2), c = 11.6069 (15)Angstrom, beta = 96.344 (8)degrees, Z = 4, R = 0.049 for 879 observations [I > 3 sigma(1)]: the structure consists of isolated monomers in which the intramolecular O-H ... N hydrogen-bond motif has graph set S(5). 1,1,3-Triphenylpropyn-1-ol (3), C21H16O, monoclinic, P2(1)/c, a = 5.9794 (12), b = 9.953 (3), c = 26.420 (3)Angstrom, beta = 91.365 (12)degrees, Z = 4, R = 0.039 for 971 observations [I > 2 sigma(I)]: the structure contains centrosymmetric dimers held together by O-H ...pi(arene) hydrogen bonds involving one of the phenyl groups, rather than the propargyl group. 2-Methyl-1,1-diphenylpropan-1-ol (4), C16H18O, trigonal, P31c, a = 13.9232 (17), c = 12.0200 (19)Angstrom, Z = 6, R = 0.031 for 763 observations [I > 3 sigma(I)]: the structure consists of cyclic hydrogen-bonded trimers with crystallographic threefold symmetry and disordered hydroxyl H atoms in a motif with graph set R(3)(3)(6): the O ... O distance in the trimers is 2.864 (7)Angstrom. Diphenyl(2-thienyl)methanol (5), C17H14OS, rhombohedral, R $($) over bar$$ 3, a = 19.20 (1), c = 26.48 (1)Angstrom, Z = 24: this compound is isomorphous and isostructural with triphenylmethanol, Ph,COH, and forms hydrogen-bonded tetrahedral tetramers. Bis(pentafluorophenyl)methanol (6), C13H2F10O, rhombohedral, R $($) over bar$$ 3, a = 26.113 (3), c = 9.788 (3)Angstrom (at 293 K), R = 0.068 for 1214 observations [I > 2 sigma(I)]; a = 26.006 (4), c = 9.5941 (11)Angstrom (at 173 K), R = 0.072 for 1889 observations [I > 2 sigma(I)], Z = 18; the structure consists of coaxial stacks of cyclic hydrogen-bonded hexamers, each of ($) over bar 3 symmetry, and with a hydrogen-bond motif of graph set R(6)(6)(12). Within the hexamers, the molecules are disordered over two orientations in the ratio 0.779 (3):0.221 (3) at 293 K and 0.776 (2):0.224 (2) at 173 K: the O ... O distance is 2.702 (4)Angstrom at 293 K and 2.683 (4)Angstrom at 173 K. Diphenylmethanol (7), C13H12O, orthorhombic, P22(1)2(1), a = 5.1300 (10), b = 18.650 (5), c = 21.168 (6)Angstrom, Z = 8, R = 0.035 for 1487 observations [I > 3 sigma(I)]: there are two molecules in the asymmetric unit and the molecules are linked by hydrogen bonds into spiral chains having graph set C(4) and lying parallel to the a-axis; the O ... O distances within the chains are 2.826 (3) and 2.878 (3)Angstrom.