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Volume 69 
Part 2 
Page o304  
February 2013  

Received 20 December 2012
Accepted 11 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.064
wR = 0.134
Data-to-parameter ratio = 19.0
Details
Open access

3-{5-Ethoxycarbonyl-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazol-2-yl}benzoic acid

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title compound, C24H25N3O5, the ethoxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap. In the crystal, inversion dimers linked by pairs of O-H...N hydrogen bonds generate R22(16) loops. C-H...O interactions link the dimers into a three-dimensional network.

Related literature

For a related structure and background to benzimidazoles, see: Yoon et al. (2012[Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.]). 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 puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25N3O5

  • Mr = 435.47

  • Monoclinic, P 21 /c

  • a = 9.3097 (3) Å

  • b = 24.8252 (7) Å

  • c = 9.6761 (3) Å

  • [beta] = 112.322 (1)°

  • V = 2068.71 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.39 × 0.23 × 0.08 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 = 0.963, Tmax = 0.992

  • 23636 measured reflections

  • 6010 independent reflections

  • 3706 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.134

  • S = 1.03

  • 6010 reflections

  • 317 parameters

  • 69 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1O2...N2i 1.04 (4) 1.66 (4) 2.675 (2) 166 (3)
C5-H5A...O3i 0.95 2.57 3.367 (2) 141
C9-H9A...O2i 0.95 2.46 3.177 (2) 132
C15-H15A...O3ii 0.99 2.34 3.314 (3) 167
C17-H17B...O5iii 0.99 2.51 3.429 (3) 154
C20-H20B...O4iv 0.99 2.55 3.340 (3) 137
Symmetry codes: (i) -x, -y, -z-1; (ii) x, y, z+1; (iii) -x+1, -y, -z+1; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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: HB7017 ).


Acknowledgements

The authors thank the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Molecular Medicine, Universiti Sains Malaysia (USM), Penang, for supporting this work. This work was funded through Research Grant (RUC) No. 1001/PSK/8620012 and HiCoE Research Grant No. 311.CIPPM.4401005. IAR also thanks USM for the Research University Grant No. 1001/PFIZIK/811151.

References

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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.  [CrossRef] [details]


Acta Cryst (2013). E69, o304  [ doi:10.1107/S1600536813001116 ]

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