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Volume 68 
Part 1 
Page o59  
January 2012  

Received 30 November 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.069
wR = 0.197
Data-to-parameter ratio = 25.8
Details
Open access

Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

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-H...O interactions, forming sheets propagating in (011). The crystal packing also features weak [pi]-[pi] stacking interactions [centroid-centroid = 3.6746 (12) Å].

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002[Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Farmaco, 57, 819-823.]); Ali et al. (2007[Ali, M. A., Shahar Yar, M. & Siddiqui, A. A. (2007). Eur. J. Med. Chem. 42, 268-275.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24N4O5

  • Mr = 436.46

  • Triclinic, [P \overline 1]

  • a = 9.3125 (1) Å

  • b = 10.0941 (1) Å

  • c = 12.9955 (2) Å

  • [alpha] = 91.958 (1)°

  • [beta] = 107.752 (1)°

  • [gamma] = 114.465 (1)°

  • V = 1040.67 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.34 × 0.20 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.987

  • 27734 measured reflections

  • 7466 independent reflections

  • 5375 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.197

  • S = 1.04

  • 7466 reflections

  • 289 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15A...O3i 0.99 2.41 3.355 (3) 159
C15-H15B...O3ii 0.99 2.38 3.186 (3) 139
C19-H19A...O2iii 0.99 2.38 3.312 (3) 156
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x, -y, -z+1; (iii) -x-1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6545 ).


Acknowledgements

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.

References

Ali, M. A., Shahar Yar, M. & Siddiqui, A. A. (2007). Eur. J. Med. Chem. 42, 268-275.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Farmaco, 57, 819-823.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o59  [ doi:10.1107/S1600536811052408 ]

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