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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1811.
Published online 2008 August 23. doi:  10.1107/S160053680802672X
PMCID: PMC2960733

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

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 [triangle]).

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Object name is e-64-o1811-scheme1.jpg

Experimental

Crystal data

  • C12H14N2O2
  • M r = 218.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1811-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680802672X/wn2276sup1.cif

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

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

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.

Refinement

All H atoms were positioned geometrically and were allowed to ride on the atoms to which they are bonded. C—H = 0.93–0.97 Å; Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A view of the packing of the title compound, with pi···pi stacking along the b axis. Dashed lines indicate hydrogen bonds.

Crystal data

C12H14N2O2F000 = 232
Mr = 218.25Dx = 1.263 Mg m3
Monoclinic, PnMo Kα radiation λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 6060 reflections
a = 10.854 (2) Åθ = 6.4–55.1º
b = 4.7959 (10) ŵ = 0.09 mm1
c = 11.842 (2) ÅT = 295 (2) K
β = 111.42 (3)ºPrism, colorless
V = 573.9 (2) Å30.2 × 0.1 × 0.1 mm
Z = 2

Data collection

Rigaku SCXmini diffractometer1323 independent reflections
Radiation source: fine-focus sealed tube1085 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 294(2) Kθmin = 3.2º
CCD_Profile_fitting scansh = −14→14
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −6→6
Tmin = 0.990, Tmax = 1.000l = −15→15
5696 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.090  w = 1/[σ2(Fo2) + (0.0435P)2 + 0.018P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
1323 reflectionsΔρmax = 0.10 e Å3
145 parametersΔρmin = −0.15 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O20.14135 (17)0.1457 (4)0.20123 (14)0.0515 (5)
C50.1006 (3)−0.1654 (5)−0.2701 (2)0.0449 (6)
C10.3029 (2)−0.2567 (6)−0.0948 (2)0.0471 (6)
H1A0.3572−0.2219−0.01480.056*
N20.12080 (19)0.0836 (4)−0.10788 (17)0.0412 (5)
C100.1019 (2)0.0363 (5)0.0906 (2)0.0413 (5)
C90.1639 (2)0.1907 (6)0.0146 (2)0.0425 (6)
H9A0.14090.38670.01210.051*
H9B0.25940.17530.05180.051*
N1−0.0107 (2)0.0004 (5)−0.30007 (18)0.0497 (6)
O10.0293 (2)−0.1587 (4)0.05777 (18)0.0685 (6)
C40.1383 (3)−0.3615 (6)−0.3381 (2)0.0576 (8)
H4A0.0850−0.3960−0.41840.069*
C60.1845 (2)−0.1163 (5)−0.1499 (2)0.0390 (6)
C70.0038 (2)0.1447 (5)−0.2017 (2)0.0454 (6)
C20.3361 (3)−0.4510 (7)−0.1649 (2)0.0540 (7)
H2A0.4147−0.5501−0.13110.065*
C30.2550 (3)−0.5027 (7)−0.2850 (3)0.0596 (7)
H3A0.2805−0.6350−0.32960.072*
C120.1640 (3)0.1400 (8)0.4080 (3)0.0737 (10)
H12A0.13220.06020.46660.111*
H12B0.15100.33830.40510.111*
H12C0.25650.09990.43060.111*
C8−0.0919 (3)0.3503 (6)−0.1883 (3)0.0598 (8)
H8A−0.16660.3635−0.26320.090*
H8B−0.05000.5293−0.16830.090*
H8C−0.12120.2914−0.12480.090*
C110.0894 (3)0.0179 (7)0.2857 (3)0.0617 (8)
H11A0.1016−0.18260.28730.074*
H11B−0.00440.05680.26170.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0623 (12)0.0550 (11)0.0392 (10)−0.0084 (9)0.0209 (9)−0.0061 (8)
C50.0512 (15)0.0505 (15)0.0271 (11)−0.0146 (12)0.0075 (11)0.0011 (11)
C10.0448 (14)0.0577 (16)0.0327 (12)−0.0087 (12)0.0070 (10)−0.0014 (12)
N20.0423 (11)0.0447 (12)0.0312 (10)−0.0065 (9)0.0069 (8)−0.0003 (9)
C100.0419 (13)0.0418 (13)0.0383 (13)0.0019 (11)0.0126 (10)−0.0012 (11)
C90.0452 (14)0.0437 (15)0.0345 (12)−0.0095 (11)0.0095 (10)−0.0074 (10)
N10.0493 (12)0.0502 (13)0.0363 (12)−0.0092 (11)0.0000 (9)0.0043 (10)
O10.0865 (15)0.0659 (14)0.0564 (12)−0.0334 (12)0.0301 (11)−0.0148 (10)
C40.0744 (19)0.0620 (18)0.0291 (13)−0.0186 (16)0.0102 (13)−0.0110 (13)
C60.0432 (13)0.0434 (14)0.0283 (12)−0.0123 (11)0.0104 (10)0.0010 (10)
C70.0426 (14)0.0450 (14)0.0395 (14)−0.0087 (12)0.0041 (11)0.0077 (11)
C20.0499 (15)0.0627 (19)0.0483 (17)0.0003 (14)0.0166 (13)−0.0013 (14)
C30.0726 (19)0.0613 (18)0.0468 (17)−0.0082 (15)0.0242 (15)−0.0129 (14)
C120.083 (2)0.095 (3)0.0472 (17)0.0068 (19)0.0283 (16)0.0017 (17)
C80.0515 (16)0.0546 (16)0.0659 (19)0.0001 (14)0.0127 (14)0.0089 (14)
C110.0716 (19)0.073 (2)0.0508 (18)−0.0011 (16)0.0346 (15)−0.0009 (15)

Geometric parameters (Å, °)

O2—C101.329 (3)C4—C31.370 (5)
O2—C111.451 (3)C4—H4A0.9300
C5—N11.380 (4)C7—C81.482 (4)
C5—C41.393 (4)C2—C31.395 (4)
C5—C61.401 (3)C2—H2A0.9300
C1—C21.380 (4)C3—H3A0.9300
C1—C61.385 (4)C12—C111.497 (4)
C1—H1A0.9300C12—H12A0.9600
N2—C61.376 (3)C12—H12B0.9600
N2—C71.379 (3)C12—H12C0.9600
N2—C91.446 (3)C8—H8A0.9600
C10—O11.193 (3)C8—H8B0.9600
C10—C91.502 (3)C8—H8C0.9600
C9—H9A0.9700C11—H11A0.9700
C9—H9B0.9700C11—H11B0.9700
N1—C71.315 (3)
C10—O2—C11116.5 (2)N1—C7—C8125.7 (2)
N1—C5—C4130.8 (2)N2—C7—C8122.1 (2)
N1—C5—C6110.3 (2)C1—C2—C3121.8 (3)
C4—C5—C6118.8 (3)C1—C2—H2A119.1
C2—C1—C6116.5 (2)C3—C2—H2A119.1
C2—C1—H1A121.7C4—C3—C2120.9 (3)
C6—C1—H1A121.7C4—C3—H3A119.5
C6—N2—C7107.06 (19)C2—C3—H3A119.5
C6—N2—C9126.07 (19)C11—C12—H12A109.5
C7—N2—C9126.7 (2)C11—C12—H12B109.5
O1—C10—O2124.6 (2)H12A—C12—H12B109.5
O1—C10—C9125.3 (2)C11—C12—H12C109.5
O2—C10—C9110.04 (19)H12A—C12—H12C109.5
N2—C9—C10112.00 (19)H12B—C12—H12C109.5
N2—C9—H9A109.2C7—C8—H8A109.5
C10—C9—H9A109.2C7—C8—H8B109.5
N2—C9—H9B109.2H8A—C8—H8B109.5
C10—C9—H9B109.2C7—C8—H8C109.5
H9A—C9—H9B107.9H8A—C8—H8C109.5
C7—N1—C5105.4 (2)H8B—C8—H8C109.5
C3—C4—C5119.0 (3)O2—C11—C12107.0 (3)
C3—C4—H4A120.5O2—C11—H11A110.3
C5—C4—H4A120.5C12—C11—H11A110.3
N2—C6—C1132.1 (2)O2—C11—H11B110.3
N2—C6—C5105.0 (2)C12—C11—H11B110.3
C1—C6—C5122.9 (2)H11A—C11—H11B108.6
N1—C7—N2112.2 (2)
C11—O2—C10—O1−1.1 (4)C2—C1—C6—C50.2 (3)
C11—O2—C10—C9180.0 (2)N1—C5—C6—N20.1 (3)
C6—N2—C9—C10−93.6 (3)C4—C5—C6—N2−179.8 (2)
C7—N2—C9—C1080.8 (3)N1—C5—C6—C1179.1 (2)
O1—C10—C9—N22.6 (4)C4—C5—C6—C1−0.8 (4)
O2—C10—C9—N2−178.4 (2)C5—N1—C7—N20.6 (3)
C4—C5—N1—C7179.5 (3)C5—N1—C7—C8−179.1 (2)
C6—C5—N1—C7−0.4 (3)C6—N2—C7—N1−0.6 (3)
N1—C5—C4—C3−179.0 (3)C9—N2—C7—N1−175.9 (2)
C6—C5—C4—C30.9 (4)C6—N2—C7—C8179.1 (2)
C7—N2—C6—C1−178.6 (3)C9—N2—C7—C83.9 (4)
C9—N2—C6—C1−3.3 (4)C6—C1—C2—C30.2 (4)
C7—N2—C6—C50.3 (2)C5—C4—C3—C2−0.5 (4)
C9—N2—C6—C5175.6 (2)C1—C2—C3—C4−0.1 (4)
C2—C1—C6—N2179.0 (3)C10—O2—C11—C12170.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···N1i0.972.613.532 (3)159
C8—H8C···Cg1ii0.972.743.633 (5)155

Symmetry codes: (i) x+1/2, −y, z+1/2; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2276).

References

  • Aaker, C. B., Desper, J. & Urbinam, J. F. (2005). Cryst. Growth Des.5, 1283–1293.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography