Crystal structure and conformation of N, N′-bis (3,5-dichlorosalicylidene)-2-hydroxy 1,3 diamino-2-propan

Abstract

N, N′-bis(3,5-dichlorosalicylidene)-2-hydroxy-1,3-diamino-2-propan (C 17H 14Cl 4N 2O 3) was synthesized and its crystal structure determined. It crystallizes in the monoclinic space group, C2/ c, with a=29.734(8), b=4.541(1), c=14.694(2) Å, β=115.85(2), R( F 2)=0.048 for 1704 independent reflections. The title compound has a twofold axis passing through the central C9 atom. The intramolecular hydrogen bond occurs between the pairs of atoms N1 and O1 [2.648(5) Å] and the hydrogen atom is essentially being bonded to the nitrogen atom. There is no intermolecular proximity between molecules. Conformations of the title compound were investigated by semi-empirical quantum mechanical AM1 calculations. The optimized geometry of the molecular structure corresponding to the non-planar conformation is the most stable conformation in the theoretical calculations. The results strongly indicate that the minimum energy conformation is primarily determined by non-bonded steric interactions.