Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 7 (July 2005)

organic compounds

fg1843 scheme

Acta Cryst. (2005). C61, o417-o419 [doi:10.1107/S0108270105014745]

2-Acetamido-N-benzyl-2-(methoxyamino)acetamides: functionalized amino acid anticonvulsants

A. Camerman, A. Hempel, D. Mastropaolo and N. Camerman

Abstract: In the crystal structure of 2-acetamido-N-benzyl-2-(methoxyamino)acetamide (3L), C₁₂H₁₇N₃O₃, the 2-acetylaminoacetamide moiety has a linearly extended conformation, with an interplanar angle between the two amide groups of 157.3 (1)°. In 2-acetamido-N-benzyl-2-[methoxy(methyl)amino]acetamide (3N), C₁₃H₁₉N₃O₃, the planes of the two amide groups intersect at an angle of 126.4 (4)°, resulting in a chain that is slightly more bent. The replacement of the methoxyamino H atom of 3L with a methyl group to form 3N and concomitant loss of hydrogen bonding results in some positional/thermal disorder in the methoxy(methyl)amino group. In both structures, in addition to classical N-HO hydrogen bonds, there are also weak non-standard C-HO hydrogen bonds. The hydrogen bonds and packing interactions result in planar hydrophilic and hydrophobic areas perpendicular to the c axis in 3L and parallel to the ab plane in the N-methyl derivative. Stereochemical comparisons with phenytoin have identified two O atoms and a phenyl group as molecular features likely to be responsible for the anticonvulsant activities of these compounds.

Formula: C₁₂H₁₇N₃O₃ and C₁₃H₁₉N₃O₃


	Structure factor file (CIF format) (109.5 kbytes) Contains datablock 3L

	Structure factor file (CIF format) (56.7 kbytes) Contains datablock 3N

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