Ethyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate

Guang-Hai Xu; Wei Wang

doi:10.1107/S160053680802672X

. 2008 Aug 23;64(Pt 9):o1811. doi: 10.1107/S160053680802672X

Ethyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate

Guang-Hai Xu ^a, Wei Wang ^a,^*

PMCID: PMC2960733 PMID: 21201788

Abstract

A new benzimidazole compound, C₁₂H₁₄N₂O₂, has been synthesized by the reaction of 2-methyl-1H-benzimidazole and ethyl 2-bromoacetate. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains. π⋯π Contacts (centroid⋯centroid distance = 3.713 Å) are observed. A C—H⋯π interaction is also present. The N—C—C—O torsion angle is 178.4 (2)°.

Related literature

For related literature, see: Aaker et al. (2005 ▶).

Experimental

Crystal data

C₁₂H₁₄N₂O₂
M _r = 218.25
Monoclinic,
a = 10.854 (2) Å
b = 4.7959 (10) Å
c = 11.842 (2) Å
β = 111.42 (3)°
V = 573.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.2 × 0.1 × 0.1 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.990, T _max = 1.000 (expected range = 0.981–0.991)
5696 measured reflections
1323 independent reflections
1085 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.089
S = 1.12
1323 reflections
145 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.15 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, New_Global_Publ_Block. DOI: 10.1107/S160053680802672X/wn2276sup1.cif

e-64-o1811-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802672X/wn2276Isup2.hkl

e-64-o1811-Isup2.hkl^{(65.3KB, 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
C9—H9B⋯N1ⁱ	0.97	2.61	3.532 (3)	159
C8—H8C⋯Cg1ⁱⁱ	0.97	2.74	3.633 (5)	155

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the imidazole ring.

Acknowledgments

The authors are grateful to the Starter Fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig. 1. The benzimidazole system is essentially planar, with a dihedral angle of 0.88 (14)° between the planes of the benzene and imidazole rings. The N2—C9—C10—O2 torsion angle is 178.4 (2)°.

In the crystal structure, molecules are connected by weak intermolecular C—H···N hydrogen bonds, forming a polymeric chain (see Table 1 and Fig. 2). A C—H···π contact (see Table 1, Cg1 is the centroid of the imidazole ring) and π···π stacking (centroid···centroid distance = 3.713 Å) between neighboring benzimidazoles further stabilize the structure.

Experimental

The synthesis of 2-methyl-1H-benzimidazole was reported previously (Aaker et al., 2005). Ethyl 2-bromoacetate (1.65 g, 10 mmol) was added to a solution of 2-methyl-1H-benzimidazole (1.32 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. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.