Abstract
In the title compound, 3-[(2-acetamido-phen-yl)imino]-butan-2-one, C12H14N2O2, the imine C=N bond is essentially coplanar with the ketone C=O bond in an s-trans conformation. The benzene ring is twisted away from the plane of the C=N bond by 53.03 (14)°. The acetamido unit is essentially coplanar with the benzene ring. In the crystal, mol-ecules are connected into chains along the c axis through C-H⋯O hydrogen bonds, with two adjacent chains being hinged by C-H⋯O hydrogen bonds.
Highlights
3-[(2-acetamidophenyl)imino]butan-2-one, C12H14N2O2, the imine C N bond is essentially coplanar with the ketone C O bond in an s-trans conformation
Molecules are connected into chains along the c axis through C—HÁ Á ÁO hydrogen bonds, with two adjacent chains being hinged by C—HÁ Á ÁO hydrogen bonds
The imine plane is twisted from the plane of the aryl ring (C5– C10) by a dihedral angle of 53.03 (14) [defined by atoms C3/ N1/C5/C6]
Summary
-(Arylimino)ketone compounds, resulting from condensation between -diketones and anilines in a 1:1 fashion, are useful bidentate ligands in transition metal coordination chemistry (Binotti et al, 2004) and important synthetic intermediates toward -diimines (Schmid et al, 2002) and iminebased multidentate ligands (Schmiege et al, 2007). Structural reports on (arylimino)ketone compounds derived from aliphatic -diketones are rare (Azoulay et al, 2009). The molecular structure of I features intramolecular C9— H9Á Á ÁO2 hydrogen bond (Table 1). This bond, in combination with conjugation between the amide group and the aryl ring, is likely responsible for the coplanarity between the acetamido and the aryl groups. 3. Supramolecular features In the crystal, C8—H8Á Á ÁO1ii [symmetry code: (ii) x, y, z À 1 hydrogen bonds arrange the molecules into chains along the c axis (Fig. 2, Table 2). Two chains in close proximity are linked by C12—H12BÁ Á ÁO2i hydrogen bonds [symmetry code: (i) x, Ày + 12, z + 12]. There are no other significant contacts between the chains (Fig. 3)
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