Cookies on this website
We use cookies to ensure that we give you the best experience on our website. If you click 'Continue' we'll assume that you are happy to receive all cookies and you won't see this message again. Click 'Find out more' for information on how to change your cookie settings.

Abstract: (RS,RS,RS,RS)-3-(N-4′-Methoxyphenyl-N-methylamino)cyclohexane-1,2-diol N-oxide 10 and (1R,2S,3S,4R,7R,7aS,1′R)-1,2-dihydroxy-1,2-O-isopropylidene-3-(1′-hydroxy-2′-tert-butoxy-2′-oxoethyl)-7-(phenylthio)hexahydro-1H-pyrrolizine N(4)-oxide 14 were synthesised and studied by X-ray diffraction. The structure of 10·0.5CHCl3 crystallizes in the monoclinic space group P21/c with cell parameters of a = 22.8016(5) Å, b = 11.9666(2) Å, c = 11.6835(2) Å, β = 99.8698(9)°, V = 3140.75(10) Å3 and Z = 8, whereas N-oxide 14 crystallizes in the orthorhombic space group P212121 with cell parameters of a = 5.8296(1) Å, b = 16.0362(1) Å, c = 23.7167(2) Å, V = 2217.147(19) Å3 and Z = 4. These studies served to establish unambiguously the configurations within these substrates. In both cases, adjacent molecules are linked by a series of O–H···O–N hydrogen-bonds, with the N-oxide moieties participating as hydrogen-bond acceptors, to form tape-like arrangements.

Original publication




Journal article


Journal of Chemical Crystallography


Springer New York LLC

Publication Date



Hydrogen-bonding, N-Oxidation, N-Oxide