Synthesis, crystal structure and computational analysis of 2,7-bis(4-chlorophenyl)-3,3-dimethyl1,4-diazepan-5-one.

In the title compound, C19H20Cl2N2O, the seven-membered 1,4-diazepane ring adopts a chair conformation while the 4-chloro­phenyl substituents adopt equatorial orientations. The chloro­phenyl ring at position 7 is disordered over two positions [site occupancies 0.480 (16):0.520 (16)]. The dihedral angle between the two benzene rings is 63.0 (4)°. The methyl groups at position 3 have an axial and an equatorial orientation. The compound exists as a dimer exhibiting inter­molecular N—HO hydrogen bonding with R²2(8) graph-set motifs. The crystal structure is further stabilized by C—HO hydrogen bonds together with two C—Clπ (ring) inter­actions. The geometry was optimized by DFT using the B3LYP/6–31 G(d,p) level basis set. In addition, the HOMO and LUMO energies, chemical reactivity parameters and mol­ecular electrostatic potential were calculated at the same level of theory. Hirshfeld surface analysis indicated that the most important contributions to the crystal packing are from HH (45.6%), ClH/HCl (23.8%), HC/CH (12.6%), HO/OH (8.7%) and CCl/ClC (7.1%) inter­actions. Analysis of the inter­action energies showed that the dispersion energy is greater than the electrostatic energy. A crystal void volume of 237.16 ų is observed. A mol­ecular docking study with the human oestrogen receptor 3ERT protein revealed good docking with a score of −8.9 kcal mol−1. [ABSTRACT FROM AUTHOR]