Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate

Xue-qun Fu; Guang-hai Xu

doi:10.1107/S1600536809019825

. 2009 Jun 10;65(Pt 7):o1535. doi: 10.1107/S1600536809019825

Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate

Xue-qun Fu ^a,^*, Guang-hai Xu ^a

PMCID: PMC2969365 PMID: 21582824

Abstract

In the title compound, C₁₉H₁₈NO₂, the dihedral angle between the benzimidazole and phenyl ring planes is 18.18 (17)°. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.50:0.50 ratio. In the crystal, intermolecular C—H⋯O hydrogen bonds and C—H⋯π contacts help to consolidate the packing.

Related literature

For further synthetic details, see: Hang & Ye (2008 ▶). For background on benzimidazoles, see: Göker et al. (1999 ▶); Özbey et al. (1998 ▶).

Experimental

Crystal data

C₁₉H₁₈N₂O₂
M _r = 307.36
Orthorhombic,
a = 12.021 (2) Å
b = 14.369 (3) Å
c = 9.7517 (18) Å
V = 1684.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T _min = 0.884, T _max = 0.984
16640 measured reflections
2046 independent reflections
1545 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.151
S = 1.07
2046 reflections
215 parameters
43 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019825/hb2982sup1.cif

e-65-o1535-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019825/hb2982Isup2.hkl

e-65-o1535-Isup2.hkl^{(100.7KB, 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
C4—H4B⋯O1ⁱ	0.97	2.47	3.409 (4)	162
C4—H4A⋯Cg2ⁱⁱ	0.97	2.67	3.577 (4)	156

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

Acknowledgments

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

The benzimidazole ring system is of great interest because of its diverse biological activities while the synthesis and crystal structure analyses of several benzimidazoles have already been reported (Göker et al., 1999; Özbey et al., 1998).

In the structure of the title compound (Fig. 1), the benzimidazole system is essentially planar (dihedral angle 1.17 (2)°). The dihedral angle between the benzimidazole and styryl groups is 17.78 (1)°. The molecule is twisted with the N1—C4—C3—O1 torsion angle of 13.61 (4)° between the ethyl acetate and benzimidazole groups.

In the crystal, intermolecular C—H···O hydrogen bonds (Fig.2) link the molecules to chains along the b axis. In addition the C—H···π contacts (Table 1) further stabilize the crystal structure.

Experimental

The synthesis of (E)-2-styryl-1H-benzimidazole was reported previously (Hang & Ye, 2008). Ethyl 2-bromoacetate (1.65 g. 10 mmol) was added to a solution of (E)-2-styryl-1H-benzo[d]imidazole (2.2 g,10 mmol) and NaH (0.6 g, 26 mmol) in THF (30 ml). After the mixture was stirred for 12 h at room temperature, the precipitate was filtered off and the solution was evaporated in vacuum. The crude product was then crystallized from ethanol to yield colourless prisms of (I).