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

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Asik, S.I.J.; Razak, I.A.

doi:10.1107/S1600536811052408

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 (C-C) = 0.003 Å
R = 0.069
wR = 0.197
Data-to-parameter ratio = 25.8
Details

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

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Safra Izuani Jama Asik ^b and Ibrahim Abdul Razak ^b ^*⁺

^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-HO 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); 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).

Experimental

Crystal data

C₂₃H₂₄N₄O₅
M_r = 436.46
Triclinic, $[P \overline 1]$
a = 9.3125 (1) Å
b = 10.0941 (1) Å
c = 12.9955 (2) Å
= 91.958 (1)°
= 107.752 (1)°
= 114.465 (1)°
V = 1040.67 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.967, T_max = 0.987
27734 measured reflections
7466 independent reflections
5375 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.197
S = 1.04
7466 reflections
289 parameters
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15AO3ⁱ	0.99	2.41	3.355 (3)	159
C15-H15BO3ⁱⁱ	0.99	2.38	3.186 (3)	139
C19-H19AO2ⁱⁱⁱ	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); 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 ).

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.
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.

organic compounds