Crystal structure of potential antidotes against nerve-gas poisoning

Abstract

Abstract Compound (1), 2-hydroxyiminomethyl-1-benzylimidazole, C11H11N3O, Mr = 201.23, space group orthorhombic P212121, a = 9.496(3) Å, b = 9.850(4) Å, c = 11.024(8) Å, V = 1031.1(9) Å−3, Z = 4, Dx = 1.296 Mgm−3, λ(MoKα ) = 0.7107 Å, μ = 0.81 cm−1, F(000) = 424, T = 293 K, final R = 0.0364 for 625 independent observed reflections. An intermolecular hydrogen bond O–H … N of 2.700(4) Å stabilizes the structure. Compound (2), 2-hydroxyiminomethyl-1-benzyl-3-methylimidazolium-iodide, C12H14IN3O, Mr = 343.17, space group orthorhombic Pbca, a = 12.484(5) Å, b = 17.339(5) Å, c = 12.616(5) Å, V = 2731(2) Å3, Z = 8, Dx = 1.669 Mgm−3, λ(MoK α) = 0.7107 Å, μ = 23.08 cm−1, F(000) = 1344, T = 293 K, final R = 0.0287 for 2104 independent observed reflections. The iodide anion is linked to the oxime-oxygen by hydrogen bond of 3.397(4) Å. Quaternization of the imidazolium ring causes the rotation of the oxime group about C–C bond connecting the imidazolium ring and oxime group. Compound (3), 4-[(hydroxyimino)methyl]-1-[[[2-[(hydroxyimino)methyl]-3-phenyl-1 H-imidazolium-1-yl]methoxy]methyl]pyridinium diiodide, C18H19I2N5O3, Mr = 607.19, monoclinic, P21/c, a = 13.547(3) Å, b = 14.501 (3) Å, c = 11.781(2) Å, β = 102.75(2)°, V = 2257.3(8) Å3, Z = 4, Dx = 1.787 Mgm−3, λ(MoK α) = 0.7107 Å, μ = 27.82 cm−1, F(000) = 1168, T = 293 K, final R = 0.0480 for 2835 independent observed reflections. The iodide anions are linked to oxime-oxygens of the cation by hydrogen bonds of 3.336(6) and 3.388(5) Å, respectively. It has been found that the geometry of the oxime group of the imidazolium ring in the investigated structure can be compared with that of the oxime group of compound (2).