Crystal structure, Hirshfeld surface analysis and DFT studies of 1-benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)methyl]-2,3-dihydro-1H-1,3-benzodiazol-2-one monohydrate

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2020-01, Vol.76 (1), p.95-101
• Main Authors: Asmaa Saber, Nada Kheira Sebbar, Tuncer Hökelek, Mohamed Labd Taha, Joel T. Mague, Noureddine Hamou Ahabchane, El Mokhtar Essassi
• Format: Article
• Language: English
• Subjects: crystal structure; dihydrobenzodiazole; hirshfeld surface; hydrogen bond; triazole; π-stacking
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989019016876

In the title molecule, C24H21N5O·H2O, the dihydrobenzodiazole moiety is not quite planar, while the whole molecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. In the crystal, chains of alternating molecules and lattice water extending along [201] are formed by O—HUncoordW...ODhyr and O—HUncoordW...NTrz (UncoordW = uncoordinated water, Dhyr = dihydro and Trz = triazole) hydrogen bonds. The chains are connected into layers parallel to (010) by C—HTrz...OUncoordW hydrogen bonds with the dihydrobenzodiazole units in adjacent layers intercalating to form head-to-tail π-stacking [centroid-to-centroid distance = 3.5694 (11) Å] interactions between them, which generates the overall three-dimensional structure. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (52.1%), H...C/C...H (23.8%) and O...H/H...O (11.2%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.