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Synthesis and Crystal Structures of 2-Azido-4-aminocyclohexane-1,3-diols

Research paper by Méabh B. Brennan, Stephen G. Davies, James A. Lee, Amber L. Thompson, James E. Thomson

Indexed on: 14 Sep '15Published on: 14 Sep '15Published in: Journal of chemical crystallography



Abstract

2-Azido-4-aminocyclohexane-1,3-diols 12, 14 and 16 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 12 crystallizes in the monoclinic space group P21/n with cell parameters of a = 13.7059(2) Å, b = 10.8861(2) Å, c = 13.8675(3) Å, β = 117.2365(10)°, V = 1839.67(6) Å3 and Z = 4. Compound 14 crystallizes in the orthorhombic space group Pcab with cell parameters of a = 9.9508(1) Å, b = 10.9839(2) Å, c = 24.7035(4) Å, V = 2700.06(7) Å3 and Z = 8. Compound 16 crystallizes in the triclinic space group \(\text{P}\bar{\it{1}}\) with cell parameters of a = 10.9511(3) Å, b = 11.3148(3) Å, c = 15.9545(5) Å, α = 86.3487(11)°, β = 87.4723(11)°, γ = 89.3398(10)°, V = 1970.91(10) Å3 and Z = 4. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies also revealed their conformations, which gave valuable information into the regioselectivity of epoxide ring-opening during their formation.

Graphical abstract 10.1007/s10870-015-0607-x.gif