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

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

doi:10.1107/S1600536811052391

Volume 68
Part 1
Pages o87-o88
January 2012

Received 30 November 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.185
Data-to-parameter ratio = 21.4
Details

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

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, C₂₄H₂₇N₃O₅·H₂O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intramolecular C-H [pi] interaction is observed. In the crystal, O-HO and O-HN hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak [pi] - [pi] stacking [centroid-centroid distance = 3.6632 (9) Å] and C-HO interactions.

Related literature

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002); Thakurdesai et al. (2007); Dubey & Sanyal (2010). For related structures, see: Yoon et al. (2011). For the ring conformation, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₄H₂₇N₃O₅·H₂O
M_r = 455.50
Triclinic, $[P \overline 1]$
a = 9.7460 (8) Å
b = 10.0436 (8) Å
c = 12.6072 (10) Å
= 85.737 (1)°
= 89.684 (2)°
= 70.238 (1)°
V = 1157.91 (16) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.960, T_max = 0.985
18195 measured reflections
6686 independent reflections
4485 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.185
S = 1.07
6686 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C8-C13 benzene ring.

D-HA	D-H	HA	DA	D-HA
O1W-H2W1O2ⁱ	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W-H1W1N1ⁱⁱ	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4-H1O4O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16-H16AO5ⁱⁱⁱ	0.96	2.44	3.380 (3)	166
C20-H20BCg4	0.97	2.86	3.750 (3)	153
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -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: IS5022 ).

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

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dubey, A. K. & Sanyal, P. K. (2010). Vet Scan, 5, 63.
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.
Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacol. Online, 1, 314-329.
Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405.

organic compounds