The syntheses of (Z)-3,4,4-trimethyl-l-(triphenylstannyl)-l-pentene-3-ol ( 1) and (Z)-3,4,4trimethyl-l-(iododiphenylstannyl)-l-penten-3-ol (2) are reported. The solid-state structures of these tetra-and triorganotin compounds were determined by X-ray diffraction methods. The tin atom in 1 exists in a tetrahedral geometry distorted toward a trigonal bipyramidal one, with the distortion due to the close approach of the OH atom, i.e. 2.772(5) Á. A trigonal bipyramidal geometry is found in 2 where the oxygen atom, which forms significant 0-Sn interactions of 2.498(4) and 2.550(4) Á for the two independent molecules, respectively, is in an apical position as is the iodine atom. The different strengths of the HO-Sn interactions are related to the Lewis acidities of the respective tin centers. Crystals of 1 are triclinic, space group PI, with a = 11.120(6) k,b -11.652(6) k,c -9.998(5) Á, a = 110.15(5)°, ß -106.39(4)°, = 87.74(6)°, V = 1164(1) Á3, and Z = 2. Crystals of 2 are triclinic, space group PI, with a = 12.631(4) k,b = 13.887(1) k,c = 12.252(4) Á, a = 95.91(2)°, ß = 107.00(3)°, y = 74.67(2)°, V = 1981(1) Á3, and Z = 2. The structures were refined to final R -0.048 for 1 and R = 0.038 for 2. These compounds were characterized in solution by , 13C, and 119Sn NMR spectroscopy. The existence of an intramolecular HO-Sn coordination in solution was assessed by 13C and 119Sn secondary isotope multiplet of partially labeled entities (SIMPLE-NMR) experiments.