Molecular structure and spectroscopic study of N,N-dimethylisoindoline-2-carboxamide – A new unsymmetrical urea obtained in one-pot synthesis

A new unsymmetrical urea (N,N-dimethylisoindoline-2-carboxamide, DMIA), which is a potential candidate for urea herbicides, has been obtained in an efficient, one-pot reaction between 1,2-bis(bromomethyl)benzene and 1,1,3,3-tetramethylguanidine. The structure of the title compound has been studied by X-ray diffraction, ESI-MS, EI-MS, FT-IR and multinuclear NMR spectroscopy. The title compound crystallises in the centrosymmetric P21/c space group of monoclinic system with a = 10.686(2)Å, b = 9.5519(19)Å, c = 11.179(2)Å, β = 117.36(1)o and Z = 4. X-ray single crystal analysis of DMIA shows the non-planar conformation of this molecule. Both nitrogen atoms exhibit distorted tetrahedral geometry. Between the molecules in the crystal there are no direction-specific interactions like hydrogen bonds. Arrangement of DMIA molecules is determined by the van der Waals interactions.