Abstract
The title compound, C15H13ClN2O3S, is one of a series of N 1-benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethylbenzene ring and the benzimidazolone ring system, is 88 (1)°, giving a butterfly-like conformation to the molecule. The molecular packing is characterized by a bifurcated N—H⋯(O,O) hydrogen bond and short Cl⋯O contacts of 3.122 (2) Å. In addition, π–π stacking of the benzimidazolone rings is also present, with interplanar separations of 3.95 (1) Å.
Highlights
The title compound, C15H13ClN2O3S, is one of a series of N1benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors
The molecular packing is characterized by a bifurcated N—HÁ Á Á(O,O) hydrogen bond and short ClÁ Á ÁO contacts of 3.122 (2) A
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2178)
Summary
Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.005 A; R factor = 0.057; wR factor = 0.133; data-to-parameter ratio = 18.3. The title compound, C15H13ClN2O3S, is one of a series of N1benzyl-1,3-dihydro-2H-benzimidazol-2-one derivatives, a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors. The dihedral angle between the two pharmacophoric groups, the dimethylbenzene ring and the benzimidazolone ring system, is 88 (1), giving a butterfly-like conformation to the molecule. – stacking of the benzimidazolone rings is present, with interplanar separations of 3.95 (1) A. Related literature For the role of the substituents on the benzene nucleus in antiHIV-1 compounds, see: Barreca et al (2007). See: Barreca et al (2005); Beddoes et al (1986); Liu et al (2007)
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