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

Yoon, Y.K.; Ali, M.A.; Tan, S.C.; Rosli, M.M.; Razak, I.A.

doi:10.1107/S1600536813001116

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.064
wR = 0.134
Data-to-parameter ratio = 19.0
Details

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

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Soo Choon Tan,^a Mohd Mustaqim Rosli ^b and Ibrahim Abdul Razak ^b ^*

^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-HN hydrogen bonds generate R₂²(16) loops. C-HO interactions link the dimers into a three-dimensional network.

Related literature

For a related structure and background to benzimidazoles, see: Yoon et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₄H₂₅N₃O₅
M_r = 435.47
Monoclinic, P 2₁ /c
a = 9.3097 (3) Å
b = 24.8252 (7) Å
c = 9.6761 (3) Å
= 112.322 (1)°
V = 2068.71 (11) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.963, T_max = 0.992
23636 measured reflections
6010 independent reflections
3706 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H1O2N2ⁱ	1.04 (4)	1.66 (4)	2.675 (2)	166 (3)
C5-H5AO3ⁱ	0.95	2.57	3.367 (2)	141
C9-H9AO2ⁱ	0.95	2.46	3.177 (2)	132
C15-H15AO3ⁱⁱ	0.99	2.34	3.314 (3)	167
C17-H17BO5ⁱⁱⁱ	0.99	2.51	3.429 (3)	154
C20-H20BO4^iv	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); 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: 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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.

organic compounds