Abstract
•Novel tetrahydrodiazepine derivative was synthesized and characterized.•The crystal structures of the compound was elucidated by single crystal X-ray diffraction method.•Hirshfeld surface analysis was done to check the interaction on the surface of the molecule.•A good agreement is found between DFT findings and experimental data.•Docking outputs reveal moderate Checkpoint Kinase inhibition by tetrahydrodiazepine derivative.
The tetrahydrodiazepine ring in the title molecule, C11H12N2O, adopts a twisted envelope conformation. In the crystal, inversion dimers are formed by NH⋯O hydrogen bonds which are connected into corrugated layers by NH⋯O hydrogen bonds and CH⋯π(ring) interactions. However, the Hirshfeld surface analysis indicated that the most important intermolecular interaction for the title compound is the H⋯H contact. Moreover, the DFT-B3LYP study showed that the title compound should have a slightly different geometry in the gas phase with respect to that in the solid phase. The antitumor activity of the novel tetrahydrodiazepine derivative is investigated by investigating its binding affinity into the active site of Checkpoint Kinase Chk1/SB218078. Docking outputs reveal moderate Checkpoint Kinase inhibition by tetrahydrodiazepine derivative.