Received 30 November 2011
In the title compound, C23H24N4O5, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitrobenzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, molecules are connected by C-HO interactions, forming sheets propagating in (011). The crystal packing also features weak - stacking interactions [centroid-centroid = 3.6746 (12) Å].
For applications of benzimidazole compounds, see: Rao et al. (2002); Ali et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For ring conformations, see: Cremer & Pople (1975).
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: HB6545 ).
The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant (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.
Ali, M. A., Shahar Yar, M. & Siddiqui, A. A. (2007). Eur. J. Med. Chem. 42, 268-275.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Farmaco, 57, 819-823.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.