Tetrameric triphenylsilanol, (Ph(3)SiOH)(4), and the adduct (Ph(3)SiOH)(2)-dimethyl sulfoxide, both at 120 K, and the adduct (Ph(3)SiOH)(4)-1,4-dioxan at 150 K: interplay of O[bond]H...O and C[bond]H...pi(arene) interactions.

The structure of tetrameric triphenylsilanol, C(18)H(16)OSi, (I), has been re-investigated at 120 (2) K. The hydroxyl H atoms were readily located and one of the arene rings is disordered over two closely positioned sets of sites. The molecules are linked into cyclic tetramers, having approximate 4 (S(4)) symmetry, via O[bond]H...O hydrogen bonds [H...O 1.81-1.85 A, O...O 2.634 (3)-2.693 (3) A and O[bond]H...O 156-166 degrees ]. At ambient temperature, there are indications of multiple disorder of the phenyl-ring sites. In bis(triphenylsilanol) dimethyl sulfoxide solvate, 2C(18)H(16)OSi x C(2)H(6)OS, (II), the dimethyl sulfoxide component is disordered across a twofold rotation axis in C2/c, and the molecular components are linked by a single O[bond]H...O hydrogen bond [H...O 1.85 A, O...O 2.732 (2) A and O[bond]H...O 172 degrees ] into three-molecule aggregates, which are themselves linked into a single three-dimensional framework by two C[bond]H...pi(arene) interactions. In tetrakis(triphenylsilanol) 1,4-dioxan solvate, 4C(18)H(16)OSi x C(4)H(8)O(2), (III), the 1,4-dioxan component lies across an inversion centre in space group P-1 and centrosymmetric five-molecule aggregates are linked by paired C[bond]H...pi(arene) interactions to form molecular ladders.