Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-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/S1600536811054572

Volume 68
Part 1
Pages o247-o248
January 2012

Received 14 December 2011
Accepted 19 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.051
wR = 0.126
Data-to-parameter ratio = 20.6
Details

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-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, C₂₃H₂₂N₄O₄, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methylene C atom at the flap. In the crystal, C-HO and C-HN interactions link the molecules into a ribbon along the a axis. The crystal packing is further stabilized by weak [pi] - [pi] stacking interactions [centroid-centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C-H [pi] interactions.

Related literature

For the biological activity of benzimidazole derivatives, see: Grassmann et al. (2002); Demirayak et al. (2002). For puckering parameters, see: Cremer & Pople (1975). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For a related structure, see: Yoon et al. (2011).

Experimental

Crystal data

C₂₃H₂₂N₄O₄
M_r = 418.45
Orthorhombic, P b c a
a = 15.8554 (2) Å
b = 15.3988 (2) Å
c = 16.2292 (2) Å
V = 3962.43 (9) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.42 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.960, T_max = 0.981
39067 measured reflections
5782 independent reflections
4429 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.126
S = 1.06
5782 reflections
280 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of C11/C12/O3/C23/O4 and C1-C6 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C2-H2AO3ⁱ	0.95	2.48	3.3922 (17)	162
C15-H15BO4ⁱⁱ	0.99	2.49	3.213 (2)	130
C23-H23AN4ⁱⁱⁱ	0.99	2.43	3.379 (2)	159
C10-H10ACg4^iv	0.95	2.65	3.3005 (16)	126
C16-H16CCg1^v	0.98	2.91	3.7282 (19)	142
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+1; (iv) $[-x, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y+2, -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: IS5032 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants 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, Penang.

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.
Demirayak, S., Abu Mohsen, U. & Çaqri Karaburun, A. (2002). Eur. J. Med. Chem. 37, 255-260.
Grassmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C. R., Arrang, J. M., Schwartz, J. C., Stark, H. & Schunack, W. (2002). Eur. J. Pharm. Sci. 15, 367-378.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405.