Crystal structure and theoretical charge density studies of dilantin molecule

Abstract

Dilantin molecule is an inhibitor of multiple protein targets such as prostate-specific antigen, lung cancer cells and it also reduces the tumor growth and invasion of the breast metastatic cancer cells. Understanding the precise geometry, charge density distribution and electrostatic properties of inhibitor pertain to predict the active site interaction between the inhibitor and receptor. Hence, the present study is aimed to determine these parameters through experimental and theoretical studies. Dilantin molecule crystallizes in orthorhombic system with Pna21 space group. The crystal and the molecular structure of dilantin molecule has been redetermined using X-ray crystal structure analysis. The two phenyl rings and imidazolidine ring in the molecule are not in coplanar and oriented in different directions, the dihedral angles are 66.6(3) and 65.3(3)°. The molecular packing of crystal is stabilized by strong NH⋯O and weak CH⋯O intermolecular hydrogen bonding interactions. A theoretical charge density analysis has been performed for the molecule lifted from the crystal, reveals the charge density distribution of dilantin molecule, this result has been compared with the corresponding gas phase studies. The electrostatic properties of the molecule also calculated. The calculated dipole moment of dilantin molecule in the crystal phase is (2.88 D), which is not very much different from its gas phase value (2.68 D). The electrostatic potential map displays strong electronegative regions near the O and N atoms, which are the possible reactive locations of the molecule.