Received 14 December 2011
In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methylene C atom at the flap. In the crystal, C-HO and C-HN interactions link the molecules into a ribbon along the a axis. The crystal packing is further stabilized by weak - stacking interactions [centroid-centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C-H interactions.
For the biological activity of benzimidazole derivatives, see: Grassmann et al. (2002); Demirayak et al. (2002). For puckering parameters, see: Cremer & Pople (1975). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For a related structure, see: Yoon et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5032 ).
The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants Nos. 1001/PFIZIK/811151 and (1001/PSK/8620012). The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malaysia, Penang.
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