(S)-1-(1-Ferrocenylmethyl-1H-benz­imidazol-2-yl)ethanol monohydrate

Rong Xia

doi:10.1107/S1600536809023575

. 2009 Jun 27;65(Pt 7):m835. doi: 10.1107/S1600536809023575

(S)-1-(1-Ferrocenylmethyl-1H-benzimidazol-2-yl)ethanol monohydrate

Rong Xia ^a,^*

PMCID: PMC2969406 PMID: 21582752

Abstract

In the structure of the title compound, [Fe(C₅H₅)(C₁₅H₁₅N₂O)]·H₂O, the unsubstituted cyclopentadiene (Cp) ring is disordered over two positions, with site-occupancy factors of 0.636 (12) and 0.364 (12). The dihedral angles between the planes of the substituted Cp ring and the major and minor components of the disordered ring are 0.8 (3) and 3.4 (6)°, respectively. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds, forming zigzag chains running parallel to the a axis.

Related literature

For applications of ferrocene compounds, see: Savage et al. (2006 ▶); Carr et al. (2001 ▶). For the biological and pharmaceutical activity of imidazole and benzimidazole derivatives, see: Matsuno et al. (2000 ▶); Garuti et al. (1999 ▶). For the synthesis and crystal structure of (±)-1-(1H-benzimidazol-2-yl)ethanol, see: Xia & Xu (2008 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₅N₂O)]·H₂O
M _r = 378.25
Orthorhombic,
a = 7.678 (5) Å
b = 12.480 (8) Å
c = 19.428 (12) Å
V = 1862 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.30 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.724, T _max = 0.785
19049 measured reflections
4236 independent reflections
3622 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.113
S = 1.05
4236 reflections
243 parameters
146 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1811 Friedel pairs
Flack parameter: 0.03 (2)

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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023575/rz2334sup1.cif

e-65-0m835-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023575/rz2334Isup2.hkl

e-65-0m835-Isup2.hkl^{(207.6KB, 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
OW—HWB⋯O1ⁱ	0.85	2.37	2.806 (5)	112
O1—H1′′⋯OW	0.82	2.34	3.016 (5)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support by the start-up fund of Southeast University is gratefully acknowledged.

supplementary crystallographic information

Comment

The organometallic compound ferrocene has found several novel applications due to its stability, spectroscopic properties, electrochemical properties and ease of use (Savage et al., 2006). The ferrocene unit can affect the properties of the binding site and likewise binding event can affect the properties of ferrocene (Carr et al., 2001). Imidazole and benzimidazole derivatives are important heteroaromatic compounds and have attracted considerable attention because of their good biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999).

In the title compound (Fig. 1), the unsubstituted cyclopentadiene (Cp) ring is disordered over two positions, with site-occupancy factors of 0.636 (12) and 0.364 (12) for the major and minor components respectively. The dihedral angles between the substituted Cp ring and the major and minor components of the disordered ring are 0.8 (3)° and 3.4 (6)°, respectively. All bond lengths and angels are normal. The dihedral angle between the benzimidazole ring system and the substituted Cp ring is 72.92 (9)°. In the crystal structure (Fig. 2), the molecules are connected through intermolecular O—H···O hydrogen bonds (Table 1) to form zigzag chains running parallel to the a axis.

Experimental

The title compound was synthesized by the reaction of L-(-)-1-(1H-benzimidazol-2-yl)ethanol (10 mmol) with a solution of FeCH₂N⁺(CH₃)₃I^- (10 mmol) in water (20 ml) at 105 °C. L-(-)-1-(1H-Benzimidazol-2-yl)ethanol was synthesized by the reaction of benzene-1,2-diamine and ethyl L-(-)-lactate at 115°C according to the literature method (Xia & Xu, 2008). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature over a period of one week.