Abstract
In the title mol-ecule, C24H21N5O·H2O, the di-hydro-benzo-diazole moiety is not quite planar, while the whole mol-ecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. In the crystal, chains of alternating mol-ecules and lattice water extending along [201] are formed by O-HUncoordW⋯ODhyr and O-HUncoordW⋯NTrz (UncoordW = uncoordinated water, Dhyr = di-hydro and Trz = triazole) hydrogen bonds. The chains are connected into layers parallel to (010) by C-HTrz⋯OUncoordW hydrogen bonds with the di-hydro-benzo-diazole units in adjacent layers inter-calating to form head-to-tail π-stacking [centroid-to-centroid distance = 3.5694 (11) Å] inter-actions 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%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions 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 mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
Chemical contextNitrogen heterocyclic compounds are known to exhibit excellent biological and pharmaceutical activities (Olesen et al, 1994; Baxter & Clarke, 1992; Saber et al, 2020; Remond et al, 1997)
Asmaa Saber,a Nada Kheira Sebbar,b,a* Tuncer Hokelek,c Mohamed Labd Taha,b Joel T
C24H21N5OÁH2O, 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
Summary
Nitrogen heterocyclic compounds are known to exhibit excellent biological and pharmaceutical activities (Olesen et al, 1994; Baxter & Clarke, 1992; Saber et al, 2020; Remond et al, 1997). With respect to the biological applications of benzimidazolone derivatives, it has been shown that these compounds are found to possess potent antioxidant (Gaba et al, 2014), antiparasitic (Ayhan-Kılcıgil et al, 2007), anthelmintic (Navarrete-Vazquez et al, 2001), antiproliferative (Ravina et al, 1993), anti-HIV (Garuti et al, 2000), anticonvulsant (Rao et al, 2002), anti-inflammatory (Thakurdesai et al, 2007), antihypertensive (Serafin et al, 1989) and antitrichinellosis (Mavrova et al, 2007) activities. They are considered to be important moieties for the development of molecules of pharmaceutical interest As a continuation of our research devoted to the study of the cycloaddition reactions involving benzimidazolone derivatives (Sebbar et al, 2016; Saber et al, 2020), we report the synthesis, the molecular and crystal structures of the title compound along with the results of the Hirshfeld surface analysis and the density functional theory (DFT) computational calculations carried out at the B3LYP/6–311 G(d,p) level in order to compare the theoretical and experimentally determined molecular structures in the solid state
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