(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol

Li, D.-P.; Li, M.; Li, S.; Hu, H.-N.

doi:10.1107/S1600536812044340

Volume 68
Part 12
Page o3254
December 2012

Received 17 October 2012
Accepted 25 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.055
wR = 0.128
Data-to-parameter ratio = 8.1
Details

(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol

Dong-Ping Li,^a ^* Min Li,^a Shuai Li ^a and Hang-Na Hu ^a

^aDepartment of Chemistry, Nanchang University, Nanchang 330031, People's Republic of China
Correspondence e-mail: nculdp@126.com

The title compound, C₁₂H₁₄N₂O, was obtained by reaction of (±)-1-(1H-benzimidazol-2-yl)ethanol with 3-bromoprop-1-ene. The asymmetric unit contains four crystallographically independent molecules. In the crystal, molecules 1 and 2 are linked via O-HN hydrogen bonds, forming chains propagating along [010]. Molecules 3 and 4 are linked to these chains via O-HO hydrogen bonds.

Related literature

For background to the pharmaceutical properties and applications of benzimidazole derivatives, see: Garuti et al. (1999); Matsuno et al. (2000); Stibrany (2001); Stibrany et al. (2002). For the synthesis of the title compound, see Xia & Xu (2008).

Experimental

Crystal data

C₁₂H₁₄N₂O
M_r = 202.25
Triclinic, P 1
a = 8.7816 (18) Å
b = 9.1233 (18) Å
c = 14.773 (3) Å
= 96.66 (3)°
= 107.15 (3)°
= 90.83 (3)°
V = 1121.8 (4) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.24 × 0.22 × 0.15 mm

Data collection

Rigaku Mercury2 (2x2 bin mode) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.982, T_max = 0.988
10277 measured reflections
8368 independent reflections
4897 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.128
S = 1.02
4404 reflections
541 parameters
3 restraints
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1BN3ⁱ	0.82	1.99	2.801 (4)	167
O2-H2BN1ⁱⁱ	0.82	2.05	2.811 (4)	155
O3-H3BO1ⁱⁱⁱ	0.82	1.99	2.808 (4)	175
O4-H4BO2ⁱ	0.82	1.97	2.787 (4)	176
Symmetry codes: (i) x+1, y, z; (ii) x-1, y+1, z; (iii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5017 ).

References

Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525-2530.
Matsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778-1781.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stibrany, R. T. (2001). US Patent No. 6,180,788.
Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.
Xia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223.

organic compounds

(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol

Related literature

Experimental

Crystal data

Data collection

Refinement

References