Water-mediated inter­molecular inter­actions in 1,2-O-cyclo­hexyl­idene-myo-inositol: a qu­anti­tative analysis

Abstract

The syntheses of new myo-inositol derivatives have received much attention due to their important biological activities. 1,2-O-Cyclo­hexyl­idene-myo-inositol is an important inter­mediate formed during the syntheses of certain myo-inositol derivatives. We report herein the crystal structure of 1,2-O-cyclo­hexyl­idene-myo-inositol dihydrate, C12H20O6·2H2O, which is an inter­mediate formed during the syntheses of myo-inositol phosphate derivatives, to demonstrate the participation of water mol­ecules and hy­droxy groups in the formation of several inter­molecular O-H...O inter­actions, and to determine a low-energy conformation. The title myo-inositol derivative crystallizes with two water mol­ecules in the asymmetric unit in the space group C2/c, with Z = 8. The water mol­ecules facilitate the formation of an extensive O-H...O hydrogen-bonding network that assists in the formation of a dense crystal packing. Furthermore, geometrical optimization and frequency analysis was carried out using density functional theory (DFT) calculations with B3LYP hybrid functionals and 6-31G(d), 6-31G(d,p) and 6-311G(d,p) basis sets. The theoretical and experimental structures were found to be very similar, with only slight deviations. The inter­molecular inter­actions were qu­anti­tatively analysed using Hirshfeld surface analysis and 2D (two-dimensional) fingerplot plots, and the total lattice energy was calculated.