Crystal structure of 5-chloro-1,3-bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol-2(3H)-one

Abstract

In the title compound, C17H19ClN4O5, the benzimidazole fused-ring system is essentially planar, the maximum deviation from the mean plane being 0.06 (1) Å. Both oxazolidine rings are nearly planar, the maximum deviations from the mean planes are 0.071 (13) and 0.070 (10) Å. The dihedral angle between the mean planes of the oxazolidine rings is 69.9 (7)°. The benzimidazole mean plane makes the dihedral angles of 43.9 (6) and 45.6 (6)° with the two oxazolidine rings. In the crystal, the mol­ecules are linked together by weak C—H⋯O hydrogen bonds building zigzag tapes running along the c axis. The Cl atom is split over two positions with an occupancy ratio of 0.567 (7):0.433 (7). This means that the reaction yields two isomers, A and B; the A component has the Cl-atom substituent in the 5-position of the benzimidazolone ring and the B component has the Cl atom in the 6-position. The two isomers form the disordered co-crystal, with a nearly half Cl atom in each of them, as indicated by the occupancy ratio. The crystal structure was refined as an inversion twin.

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

“…An N-substituted benzoimidazol-2-one analogue (Saber et al, 2018a,b;Saber et al, 2020) and other similar compounds have also been reported (Belaziz et al, 2012(Belaziz et al, , 2013Bouayad et al, 2015). In derivatives of benzimidazolin-2-one in which both nitrogen atoms form exocyclic C-N bonds, the bicyclic ring system is either planar, has a slight twist end-to-end, or, in the cases where the exocyclic substituents form a ring, has a very shallow bowl shape.…”

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

“…The syntheses of several N-substituted benzimidazol-2-one analogues have been reported (Saber et al, 2018a,b;2020;Belaziz et al, 2012;Bouayad et al, 2015;Belaziz et al, 2013). In a search of the Cambridge Crystallographic Database (CSD; Version 5.40, update of September 2019; Groom et al, 2016) using benzimidazol-2-one with an exocyclic carbon atom bound to each nitrogen generated 94 hits.…”