N-(2-Methylphenyl)maleamic acid

作者:Gowda B Thimme*; Tokarcik Miroslav; Shakuntala K; Kozisek Jozef; Fuess Hartmut
来源:Acta Crystallographica Section E-Structure Reports Online, 2010, 66: O1554-U424.
DOI:10.1107/S160053681002012X

摘要

In the title compound, C(11)H(11)NO(3), the conformation of the N-H bond is anti to the C=O bond in the amide segment, while it is syn to the ortho-methyl group in the phenyl ring. In the maleamic acid unit, the amide C=O bond is anti to the adjacent C-H bond, while the carboxyl C=O bond is syn to the adjacent C-H bond. The C=O and O-H bonds of the acid group are in the relatively rare anti position to each other. This is an obvious consequence of the intramolecular O-H center dot center dot center dot O hydrogen bond donated to the amide carbonyl group. The ortho-substituted phenyl ring makes a dihedral angle of 12.7 (1)degrees with the mean plane of the maleamic acid unit. In the crystal structure, intermolecular N-H center dot center dot center dot O hydrogen bonds link the molecules into zigzag chains parallel to [001]. These chains are further linked into sheet by weak pi-pi interactions [centroid-centroid distance = 3.425 (2) angstrom].

  • 出版日期2010-7