Research Article: Redetermination of 1,3-diammonio-1,2,3-tride­oxy-cis-inositol dichloride

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Christian Neis, Günter J. Merten, Philipp Altenhofer, Kaspar Hegetschweiler.


The crystal structure of the title compound, C6H16N2O32+·2Cl−, has been reported previously by Palm [Acta Cryst. (1967 ▶), 22, 209–216] from Weisenberg camera data, with R1 = 10.5%, isotropic refinement of non-H atoms and H atoms not located. We remeasured a data set of the title compound and present a more precise structure determination. The asymmetric unit contains two unique 1,3-diammonio-1,2,3-tride­oxy-cis-inositol cations and four Cl− counter-ions. The cyclo­hexane rings of both inositol cations adopt chair conformations with two axial hy­droxy groups. An extended network of hydrogen bonds is formed. The four chloride counter ions are hydrogen bonded to the hydroxy and ammonium groups of the cations by N—H⋯Cl and O—H⋯Cl interactions. The cations are aligned into wavy layers by cation⋯cation interactions of the form N—H⋯O(ax), N—H⋯O(eq) and O(ax)—H⋯O(eq). Intramolecular hydrogen bonding between the axial hydroxy groups is, however, not observed.

Partial Text

An earlier, less accurate structure determination of the title compound was performed by Palm (1967 ▶). The crystal structure of 1,3-diammonio-1,2,3-tride­oxy-cis-inositol sulfate has been reported by Neis et al. (2012 ▶). The importance of intra­molecular hydrogen bonding in 1,3,5-tris­ubstituted cyclo­hexane derivatives has been described by Gencheva et al. (2000 ▶), Saaidi et al. (2008 ▶) and Neis et al. (2010 ▶), and the implication of increased 1,3-diaxial repulsion on the conformation of a cyclo­hexane ring has been discussed by Fritsche-Lang et al. (1985 ▶), Kramer et al. (1998 ▶) and Kuppert et al. (2006 ▶). For the synthesis, see: Merten et al. (2012 ▶). For the treatment of hydrogen atoms in SHELXL, see: Müller et al. (2006 ▶).