Ethyl 1-sec-butyl-2-(4-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Abdul Rahim, A.S.; Osman, H.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810007634

Volume 66
Part 4
Page o845
April 2010

Received 24 February 2010
Accepted 1 March 2010
Online 17 March 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.066
wR = 0.150
Data-to-parameter ratio = 18.9
Details

Ethyl 1-sec-butyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Aisyah Saad Abdul Rahim,^a ⁺ Hasnah Osman,^b Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*⁺⁺

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title molecule, C₂₁H₂₄N₂O₃, the dihedral angle between the benzene and imidazole rings is 66.33 (13)°. The imidazole ring is essentially planar, with a maximum deviation of 0.004 (2) Å. In the crystal structure, molecules are connected by weak C-HO hydrogen bonds, forming chains along the b axis

Related literature

For the benzimidazole nucleus as a key building block for compounds showing biologically activity, see: Tanious et al. (2004). For the therapeutic properties of benzimidazole derivatives, see: Kohara et al. (1996); Mader et al. (2008). For 2-substituted-phenylbenzimidazoles with biological activity, see: Coburn et al. (1987); Roth et al. (1997).

Experimental

Crystal data

C₂₁H₂₄N₂O₃
M_r = 352.42
Monoclinic, P 2₁ /c
a = 10.5815 (3) Å
b = 12.1079 (3) Å
c = 15.1050 (3) Å
= 93.678 (2)°
V = 1931.26 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.40 × 0.31 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.968, T_max = 0.994
19216 measured reflections
4437 independent reflections
2266 reflections with I > 2s(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.150
S = 1.04
4437 reflections
235 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C21-H21CO1ⁱ	0.96	2.47	3.389 (4)	161
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: TK2635 ).

Acknowledgements

NA, ASAR and HO are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry research under the USM Research University grant (1001/PFARMASI/815026). NA thanks USM for the award of postdoctoral fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks USM for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Coburn, R. A., Clark, M. T., Evans, R. T. & Genco, R. J. (1987). J. Med. Chem. 30, 205-208.
Kohara, Y., Kubo, K., Imamiya, E., Wada, T., Inada, Y. & Naka, T. (1996). J. Med. Chem. 39, 5228-5235.
Mader, M., de Dios, A., Shih, C. & Anderson, B. D. (2008). Bioorg. Med. Chem. Lett. 18, 179-183.
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tanious, F. A., Hamelberg, D., Bailly, C., Czarny, A., Boykin, D. W. & Wilson, W. D. (2004). J. Am. Chem. Soc. 126, 143-153.

organic compounds