Abstract
Our work in the area of synthesis of metal-organic frameworks (MOFs) based on organic N-oxides led to the crystallization of pyridine-4-carboxamidoxime N-oxide. Herein we report the first crystal structure of the title compound, C6H7N3O2 [systematic name: (Z)-4-(N'-hy-droxy-carbamimido-yl)pyridine N-oxide]. The hy-droxy-carbamimidoyl group is essentially coplanar with the aromatic ring, r.m.s.d. = 0.112 Å. The compound crystallizes in hydrogen-bonding layers built from the formation of strong O-H⋯O hydrogen bonds between the oxime oxygen atom and the oxygen atom of the N-oxide, and the formation of N-H⋯O hydrogen bonds between one amine nitro-gen atom and the N-oxide oxygen atom. These combined build R 3 4(24) ring motifs in the crystal. The crystal structure has no π-π inter-actions.
Highlights
Our work in the area of synthesis of metal–organic frameworks (MOFs) based on organic N-oxides led to the crystallization of pyridine-4-carboxamidoxime
The compound crystallizes in hydrogenbonding layers built from the formation of strong O—HÁ Á ÁO hydrogen bonds between the oxime oxygen atom and the oxygen atom of the N-oxide, and the formation of N—HÁ Á ÁO hydrogen bonds between one amine nitrogen atom and the N-oxide oxygen atom
We have previously reported N-oxides used in coordination polymers of Mn (Kang et al, 2017 and Lynch et al, 2018)
Summary
Since their first reported syntheses (Meisenheimer et al, 1926), pyridine N-oxide and related compounds have garnered much interest in chemistry. We are interested in their uses in coordination polymers and as potential catalysts The utility of these aromatic N-oxides to facilitate organic oxotransfer reactions has been well documented over the years (see, for example: Espenson, 2003). Many of these reactions are catalyzed by transition-metal interactions with the N-oxide ligands (see, for example: Moustafa et al, 2014). Others have reported their use as coordination polymers (Ren et al, 2018).
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