1-(4-Methylbenzyl)-1 H -benzimidazol-2(3 H )-one

Self Cite

In the title compound, C21H19N3O5, the phthalimide and benzamidazole ring systems are linked by a propyl chain. The benzamidazole unit also carries an ethoxycarbonyl substituent. The phthalimido and benzimidazole ring systems are essentially planar, the maximum deviations from their mean planes being 0.008 (2) and 0.020 (2) Å, respectively. The two ring systems are almost orthogonal to one another, making a dihedral angle of 82.37 (8)°. In the crystal, C—H⋯O hydrogen bonds and C—H⋯π contacts stack the molecules along the b axis.

“…For their use as ligands to transition metals, see: Bouwman et al (1990). For a related structure, see: Belaziz et al (2013).…”

Section: Related Literaturementioning

confidence: 99%

Section: Data Collectionmentioning

confidence: 99%

Ethyl 2-oxo-3-(3-phthalimidopropyl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxylate

Belaziz¹,

Rodi²,

Rodi³

et al. 2013

Self Cite

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

Saber¹,

Srhir²,

Hökelek

et al. 2019

Self Cite

The dihydrobenzimidazol-2-one moiety is essentially planar with the prop-2-yn- 1-yl substituent rotated well out of this plane. In the crystal, C—H⋯π(ring) interactions and C—H⋯O hydrogen bonds form corrugated layers parallel to (10), which are associated through additional C—H⋯O hydrogen bonds and head-to-tail, slipped, π-stacking interactions between dihydrobenzimidazol-2-one moieties

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

Saber¹,

Sebbar

Hökelek

et al. 2020

Self Cite

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.