N-(4-Acetylphenyl)acetohydroxamic acid

Abstract

C10HuNO s, Mr= 193.20, monoclinic, P2~/n, a=23.539(5), b=8.473(2), c=9.540A, fl=99.44(2) ° , V=1876.9 (7) A 3, z=8, D x- 1.367 gcm -3, Ni-filtered Cu K~ 2 -- 1.5418 A, /t -- 7-55 cm -~, F(000) = 816, T= 138 (2) K, R = 0.057 for 3018 data. The hydroxamate groups of the two crystallographically unique molecules have a trans conformation. Both molecules are roughly planar and have similar molecular conformations and identical dimensions, which are compared with those of other N-substituted acetohydroxamic acids. The molecules are linked by two intermolecular hydrogen bonds with lengths 2.631 (2)and 2.636 (2)A. Introduction. Under iron-limiting conditions, micro- organisms produce a variety of small chelating agents which solubilize ferric iron in the environment and transport the iron to the cell. Many of these metabolites chelate the iron through hydroxamic acid groups. Both naturally occurring and synthetic hydroxamic acids have been used as therapeutic agents for treatment of iron overload (Anderson & Hiller, 1977). Crystal structures of synthetic hydroxamic acids with a trans conformation include N,N'-dihydroxy-N,N'-diiso- propylhexanediamide (hipa) (Smith & Raymond, 1980), N-(4-cyanophenyl)acetohydroxamic acid (p- cnpa) (Mocherla, Powell, Barnes & van der Helm, 1983) and N-(3-cyanophenyl)acetohydroxamic acid (m-cnpa) (Mocharla, Powell & van der Helm, 1984). This article describes the crystal and molecular struc- ture of N-(4-acetylphenyl)acetohydroxamic acid (apa).