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

Abstract

The crystal structure of the title compound, C6H16N2O3 2+·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.

Tris(cis-2-hydroxycyclohexane-1,3,5-triaminium) hydrogen sulfate octachloride dihydrate

“…O2 does, however, not act as an acceptor. A similar behaviour has recently been noted in related structures Neis, Merten & Altenhofer et al, 2012).…”

1,3-Diammonio-1,2,3-trideoxy-cis-inositol sulfate

“…The crystal structure of a corresponding hydrochloride C 6 H 14 N 2 O 3 . 2HCl has recently been reported (Neis et al, 2012). Similar to this chloride salt, the title compound contains 1,3-diammonio-1,2,3-trideoxy-cis-inositol dications with the cyclohexane ring adopting an almost ideal chair conformation (puckering parameters: Q = 0.59 Å, θ = 178.3 °, φ = 89.0 °).…”

“…The synthesis of the chloride salt, as well as formation of a Cu II complex of 1,3-diamino-1,2,3-trideoxy-cis-inositol, was reported by Merten et al (2012). A crystal structure determination of the chloride salt was performed by Neis et al (2012). The importance of intramolecular hydrogen bonding in syn-1,3,5-trisubstituted cyclohexane derivatives has been discussed by Gencheva et al (2000), Kramer et al (1998), Kuppert et al (2006), and Neis et al (2010).…”

“…The title compound has been obtained following the protocol given by Merten et al (2012). 1 H-NMR and 13 C-NMR properties are identical with the chloride salt (Neis et al, 2012). Single crystals were grown from an aqueous solution (pH 2) by slow evaporation at 298 K.…”