1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1 H -benzimidazol-2(3 H )-one

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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.

“…For asymmetric reactions of oxazolidin-2-ones, see: Evans et al (1993); Matsunaga et al (2005). For oxazolidin-2-one derivatives, see: Ouzidan et al (2011); Dardouri et al (2011)…”

Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

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

Bouayad

Rodi²,

Ouzidan³

et al. 2015

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“…As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives Ouzidan, Kandri Rodi, Fronczek et al, 2011;Belaziz et al 2012), we reported in this paper the synthesis of benzimidazol-2-one derivative by action of propargyl bromide with 1Hbenzo[d]imidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish two compounds: di-substituted (Ouzidan, Kandri Rodi, Jasinski et al, 2011) and mono-substituted (Scheme 1).…”

Section: Sup-1mentioning

confidence: 99%

1-(Prop-2-ynyl)-1H-benzimidazol-2(3H)-one

Ouzidan¹,

Rodi²,

Chahdi³

et al. 2012

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“…As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Ouzidan et al, 2011a(Ouzidan et al, , 2011b, we report in this paper the synthesis of a new benzimidazol-2-one derivative by action of benzyl chloride with 1H-benzimidazol-2-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish the title compound (Scheme 1).…”

Section: Data Collectionmentioning

confidence: 99%

1-Benzyl-1H-benzimidazol-2(3H)-one

Ouzidan¹,

Essassi²,

Luis

et al. 2011

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The fused five- and six-membered rings in the title compound, C14H12N2O, are essentially planar, the largest deviation from the mean plane being 0.023 (2) Å. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 68.50 (6)°. In the crystal, each molecule is linked to its symmetry equivalent created by a crystallographic inversion center by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.