(±)-1-(1H-Benzimidazol-2-yl)ethanol

Rong Xia; Hai-Jun Xu

doi:10.1107/S1600536808013871

. 2008 Jun 7;64(Pt 7):o1223. doi: 10.1107/S1600536808013871

(±)-1-(1H-Benzimidazol-2-yl)ethanol

Rong Xia ^a, Hai-Jun Xu ^a,^*

PMCID: PMC2961813 PMID: 21202860

Abstract

The asymmetric unit of the title molecule, C₉H₁₀N₂O, contains two molecules. The fused benzene and imidazole rings are nearly coplanar, the largest deviations from the mean plane being 0.025 (3) Å at the non-bridgehead imidazole C atom of one molecule and 0.018 (3) Å at one of the bridgehead C atoms in the other molecule. Intermolecular O—H⋯N and N—H⋯O hydrogen bonds result in the formation of a sheet parallel to the (010) plane.

Related literature

For related literature, see: Allen et al. (1987 ▶); Chen & Ruan (2007 ▶); Garuti et al. (1999 ▶); Matsuno et al. (2000 ▶); Tlahuext et al. (2007 ▶).

Experimental

Crystal data

C₉H₁₀N₂O
M _r = 162.19
Orthorhombic,
a = 13.734 (3) Å
b = 15.376 (3) Å
c = 7.9163 (16) Å
V = 1671.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.912, T _max = 1.00 (expected range = 0.908–0.996)
17487 measured reflections
2199 independent reflections
1380 reflections with I > 2σ(I)
R _int = 0.115

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.123
S = 1.07
2199 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013871/dn2341sup1.cif

e-64-o1223-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013871/dn2341Isup2.hkl

e-64-o1223-Isup2.hkl^{(108.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.91	2.713 (4)	165
N4—H4⋯O1ⁱ	0.86	1.97	2.828 (4)	178
O2—H2⋯N2ⁱⁱ	0.82	1.93	2.743 (4)	170
N1—H1A⋯O2ⁱⁱⁱ	0.86	1.93	2.751 (4)	160

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

HJX acknowledges a Start-up Grant from Southeast University, P. R. China

supplementary crystallographic information

Comment

Imidazole and benzimidazole derivatives are important heteroaromatic compounds and have attracted considerable attention because of good biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999). These compounds also play an important role in the development of coordination chemistry. Many derivatives of benzimidazole have been prepared and their complexes have been studied (Tlahuext et al., 2007; Chen & Ruan, 2007). In this paper, we report the crystal structure of the title compound.

There are two crystallographically independent molecules, A and B, linked by a O-H···N hydrogen bond in the asymmetric unit . The bond lengths and angles in A and B are within normal ranges (Allen et al., 1987). The two fused benzene and imidazole rings are nearly planar with the largest deviations from the mean plane being 0.025 (3) Å at C7 and 0.018 (3) Å at C10 . These two fused rings make a dihedral angle of 35.01 (9)°.

The molecules are further connected through O-H···N and N-H···O hydrogen bond buiding up a two dimmensional network which is parallel to the (0 1 0) plane (Table 1, Fig. 2).

Only the relative absolute configuration could be determined, the C8 and C17 have the same absolute configuration (S,S) or (R,R). The (S,S) configuration is represented in Fig. 1.

Experimental

All chemicals were obtained from commercial sources and used directly without further purification. Benzene-1, 2-diamine (2.16 g, 20 mmol) was dissolved in hydrochloric acid (25 mL, 4 M) at 100°C, and ethyl 2-hydroxypropanoate (2.48 g, 21 mmol) was added to the solution. The mixture were then heated to reflux for 7 h at 115°C. After cooling to room temperature, the product was divided by neutralizing the mixture solution using NaOH to make the pH 7–9. Solid product was collected by filtration and the yield was 80%. ¹H-NMR(CDCl₃, 300 MHz): δ1.72 (d, 3 H), 5.22 (q, 1 H), 7.47(m, 1 H), 7.58 (m, 2 H), 7.81 (m, 1 H). Esi-MS: calcd for C₁₄H₉N₂O–H m/z 161.19, found 161.18. Deep-red single crystals of the title compound suitable for X-ray diffraction analysis were obtained from methanol solution by slow evaporation after a week.