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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 [sigma](C-C) = 0.007 Å
R = 0.055
wR = 0.128
Data-to-parameter ratio = 8.1
Details
Open access

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

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-H...N hydrogen bonds, forming chains propagating along [010]. Molecules 3 and 4 are linked to these chains via O-H...O hydrogen bonds.

Related literature

For background to the pharmaceutical properties and applications of benzimidazole derivatives, see: Garuti et al. (1999[Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525-2530.]); Matsuno et al. (2000[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.]); Stibrany (2001[Stibrany, R. T. (2001). US Patent No. 6,180,788.]); Stibrany et al. (2002[Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.]). For the synthesis of the title compound, see Xia & Xu (2008[Xia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N2O

  • Mr = 202.25

  • Triclinic, P 1

  • a = 8.7816 (18) Å

  • b = 9.1233 (18) Å

  • c = 14.773 (3) Å

  • [alpha] = 96.66 (3)°

  • [beta] = 107.15 (3)°

  • [gamma] = 90.83 (3)°

  • V = 1121.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.988

  • 10277 measured reflections

  • 8368 independent reflections

  • 4897 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.128

  • S = 1.02

  • 4404 reflections

  • 541 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1B...N3i 0.82 1.99 2.801 (4) 167
O2-H2B...N1ii 0.82 2.05 2.811 (4) 155
O3-H3B...O1iii 0.82 1.99 2.808 (4) 175
O4-H4B...O2i 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
Xia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3254  [ doi:10.1107/S1600536812044340 ]

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