Research Article: Benzyl N-(2-hy­droxy-1-{N′-[(1E)-2-hy­droxy­benzyl­idene]hydrazinecarbon­yl}eth­yl)carbamate

Date Published: July 01, 2011

Publisher: International Union of Crystallography

Author(s): Edward R. T. Tiekink, Marcus V. N. de Souza, Alessandra C. Pinheiro, Solange M. S. V. Wardell, James L. Wardell.


The mol­ecule of the title compound, C18H19N3O5, adopts a curved arrangement with the terminal benzene rings lying to the same side. The hydroxyl­benzene ring is close to coplanar with the adjacent hydrazine residue [dihedral angle = 11.14 (12)°], an observation which correlates with the presence of an intra­molecular O—H⋯N hydrogen bond. The benzyl ring forms a dihedral angle of 50.84 (13)° with the adjacent carbamate group. A twist in the mol­ecule, at the chiral C atom, is reflected in the dihedral angle of 80.21 (12)° formed between the amide residues. In the crystal, two-dimensional arrays in the ac plane are mediated by O—H⋯O and N—H⋯O hydrogen bonds.

Partial Text

For background to the use of l-serine derivatives in anti-tumour therapy, see: Jiao et al. (2009 ▶); Yakura et al. (2007 ▶). For background to N-acyl­hydrazone derivatives from l-serine for anti-tumour testing, see: Pinheiro et al. (2010 ▶, 2011a ▶,b ▶); de Souza et al. (2010 ▶, 2011 ▶); Howie et al. (2011 ▶).




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