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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1535.
Published online 2009 June 10. doi:  10.1107/S1600536809019825
PMCID: PMC2969365

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

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 [triangle]). For background on benzimidazoles, see: Göker et al. (1999 [triangle]); Özbey et al. (1998 [triangle]).

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Object name is e-65-o1535-scheme1.jpg

Experimental

Crystal data

  • C19H18N2O2
  • M r = 307.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1535-efi1.jpg
  • 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
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.25 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, global. DOI: 10.1107/S1600536809019825/hb2982sup1.cif

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

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refimenent. The positional parameters of all the H atoms were calculated geometrically and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity).
Fig. 2.
A view of the packing of the title compound, stacking along the b axis. Dashed lines indicate hydrogen bonds.

Crystal data

C19H18N2O2F(000) = 652
Mr = 307.36Dx = 1.212 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3237 reflections
a = 12.021 (2) Åθ = 2.5–27.5°
b = 14.369 (3) ŵ = 0.08 mm1
c = 9.7517 (18) ÅT = 298 K
V = 1684.4 (5) Å3Prism, colourless
Z = 40.25 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer2046 independent reflections
Radiation source: fine-focus sealed tube1545 reflections with I > 2σ(I)
graphiteRint = 0.056
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.8°
CCD_Profile_fitting scansh = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −18→18
Tmin = 0.884, Tmax = 0.984l = −12→12
16640 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0802P)2 + 0.1398P] where P = (Fo2 + 2Fc2)/3
2046 reflections
215 parametersΔρmax = 0.16 e Å3
43 restraintsΔρmin = −0.25 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
N10.1633 (2)0.13879 (18)0.1323 (3)0.0509 (6)
N20.0004 (2)0.14329 (18)0.0204 (3)0.0558 (7)
C50.1630 (2)0.0626 (2)0.0454 (3)0.0500 (7)
O10.3290 (2)0.2529 (2)0.0215 (3)0.0743 (7)
O20.4352 (2)0.2271 (2)0.2042 (3)0.0925 (10)
C30.3424 (3)0.2197 (2)0.1332 (4)0.0570 (8)
C60.0611 (3)0.0668 (2)−0.0229 (4)0.0543 (8)
C110.0644 (2)0.1847 (2)0.1111 (3)0.0493 (7)
C120.0354 (3)0.2693 (2)0.1853 (4)0.0559 (8)
H12A0.07990.28730.25860.067*
C13−0.0510 (3)0.3216 (2)0.1534 (4)0.0587 (8)
H13A−0.09240.30240.07800.070*
C14−0.0894 (3)0.4059 (2)0.2221 (4)0.0586 (8)
C40.2583 (3)0.1664 (2)0.2144 (3)0.0539 (7)
H4A0.29320.11130.25240.065*
H4B0.23290.20460.29030.065*
C70.0364 (3)−0.0019 (3)−0.1204 (4)0.0675 (10)
H7A−0.0309−0.0015−0.16750.081*
C15−0.1778 (4)0.4562 (3)0.1668 (5)0.0794 (12)
H15A−0.21050.43600.08560.095*
C19−0.0430 (3)0.4385 (3)0.3420 (4)0.0715 (10)
H19A0.01710.40720.38060.086*
C90.2151 (4)−0.0720 (3)−0.0755 (4)0.0763 (11)
H9A0.2658−0.1190−0.09530.092*
C18−0.0843 (4)0.5169 (3)0.4058 (5)0.0863 (13)
H18A−0.05190.53780.48670.104*
C80.1142 (4)−0.0697 (3)−0.1441 (5)0.0804 (12)
H8A0.0987−0.1157−0.20850.096*
C100.2420 (3)−0.0058 (2)0.0215 (4)0.0652 (9)
H10A0.3094−0.00700.06840.078*
C16−0.2178 (4)0.5352 (3)0.2300 (6)0.0944 (14)
H16A−0.27570.56860.19020.113*
C17−0.1726 (5)0.5644 (3)0.3512 (6)0.0941 (15)
H17A−0.20150.61610.39620.113*
C10.5262 (14)0.283 (2)0.143 (3)0.128 (3)0.50
H1A0.52130.28200.04370.153*0.50
H1B0.52180.34700.17380.153*0.50
C20.628 (3)0.241 (2)0.188 (3)0.137 (8)0.50
H2B0.68990.27320.14680.206*0.50
H2C0.62960.17690.16060.206*0.50
H2D0.63360.24530.28580.206*0.50
C1'0.5333 (14)0.271 (2)0.137 (3)0.128 (3)0.50
H1'A0.55640.23380.05900.153*0.50
H1'B0.51470.33270.10580.153*0.50
C2'0.621 (3)0.275 (2)0.237 (3)0.137 (8)0.50
H2'A0.68390.30700.19820.206*0.50
H2'B0.64290.21300.26220.206*0.50
H2'C0.59580.30780.31670.206*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0473 (13)0.0574 (15)0.0480 (13)−0.0008 (12)−0.0054 (12)−0.0040 (13)
N20.0486 (13)0.0628 (16)0.0560 (15)−0.0030 (13)−0.0017 (13)−0.0031 (15)
C50.0513 (17)0.0551 (17)0.0434 (17)−0.0044 (15)0.0014 (14)−0.0030 (14)
O10.0745 (16)0.0925 (18)0.0560 (14)−0.0139 (14)−0.0052 (14)0.0121 (15)
O20.0618 (15)0.125 (2)0.090 (2)−0.0270 (16)−0.0254 (16)0.043 (2)
C30.0547 (18)0.0639 (19)0.0525 (19)−0.0027 (16)−0.0054 (15)−0.0003 (17)
C60.0513 (18)0.0607 (18)0.0510 (17)−0.0093 (15)0.0032 (14)−0.0006 (16)
C110.0451 (16)0.0533 (16)0.0495 (17)−0.0047 (14)0.0063 (14)0.0020 (15)
C120.0571 (19)0.0557 (18)0.0550 (19)−0.0045 (16)0.0044 (15)0.0012 (16)
C130.0571 (19)0.0631 (19)0.0560 (19)0.0008 (16)−0.0026 (15)−0.0011 (17)
C140.0614 (19)0.0538 (17)0.0604 (19)0.0014 (16)0.0056 (18)0.0043 (17)
C40.0559 (18)0.0615 (16)0.0442 (15)−0.0003 (17)−0.0074 (15)0.0007 (16)
C70.060 (2)0.074 (2)0.068 (2)−0.0138 (19)−0.0028 (18)−0.015 (2)
C150.082 (3)0.071 (2)0.085 (3)0.016 (2)−0.010 (2)−0.005 (2)
C190.075 (2)0.073 (2)0.067 (2)0.0104 (19)0.0006 (19)−0.005 (2)
C90.082 (3)0.068 (2)0.079 (2)0.010 (2)0.002 (2)−0.017 (2)
C180.105 (3)0.080 (3)0.074 (3)0.006 (3)−0.003 (3)−0.016 (2)
C80.089 (3)0.072 (2)0.080 (3)−0.010 (2)0.000 (2)−0.027 (2)
C100.0597 (18)0.0716 (19)0.064 (2)0.0050 (18)−0.0025 (18)−0.0081 (19)
C160.100 (4)0.082 (3)0.101 (3)0.034 (3)−0.008 (3)−0.003 (3)
C170.112 (4)0.074 (3)0.096 (3)0.025 (3)0.022 (3)−0.004 (3)
C10.078 (3)0.160 (7)0.145 (6)−0.048 (4)−0.024 (4)0.068 (6)
C20.086 (5)0.18 (2)0.151 (19)−0.025 (9)−0.005 (10)0.031 (12)
C1'0.078 (3)0.160 (7)0.145 (6)−0.048 (4)−0.024 (4)0.068 (6)
C2'0.086 (5)0.18 (2)0.151 (19)−0.025 (9)−0.005 (10)0.031 (12)

Geometric parameters (Å, °)

N1—C111.376 (4)C15—H15A0.9300
N1—C51.384 (4)C19—C181.380 (6)
N1—C41.450 (4)C19—H19A0.9300
N2—C111.314 (4)C9—C101.380 (5)
N2—C61.385 (4)C9—C81.387 (6)
C5—C101.387 (5)C9—H9A0.9300
C5—C61.395 (4)C18—C171.369 (7)
O1—C31.200 (5)C18—H18A0.9300
O2—C31.318 (4)C8—H8A0.9300
O2—C11.482 (9)C10—H10A0.9300
O2—C1'1.485 (9)C16—C171.367 (8)
C3—C41.495 (5)C16—H16A0.9300
C6—C71.402 (5)C17—H17A0.9300
C11—C121.457 (5)C1—C21.434 (10)
C12—C131.318 (5)C1—H1A0.9700
C12—H12A0.9300C1—H1B0.9700
C13—C141.459 (5)C2—H2B0.9600
C13—H13A0.9300C2—H2C0.9600
C14—C191.378 (5)C2—H2D0.9600
C14—C151.393 (5)C1'—C2'1.436 (10)
C4—H4A0.9700C1'—H1'A0.9700
C4—H4B0.9700C1'—H1'B0.9700
C7—C81.370 (6)C2'—H2'A0.9600
C7—H7A0.9300C2'—H2'B0.9600
C15—C161.378 (6)C2'—H2'C0.9600
C11—N1—C5106.6 (2)C10—C9—C8121.3 (4)
C11—N1—C4129.2 (3)C10—C9—H9A119.3
C5—N1—C4123.8 (3)C8—C9—H9A119.3
C11—N2—C6104.9 (3)C17—C18—C19120.7 (5)
N1—C5—C10131.4 (3)C17—C18—H18A119.6
N1—C5—C6105.1 (3)C19—C18—H18A119.6
C10—C5—C6123.5 (3)C7—C8—C9122.2 (4)
C3—O2—C1117.2 (11)C7—C8—H8A118.9
C3—O2—C1'118.4 (10)C9—C8—H8A118.9
C1—O2—C1'8(3)C9—C10—C5116.3 (4)
O1—C3—O2124.0 (3)C9—C10—H10A121.8
O1—C3—C4126.4 (3)C5—C10—H10A121.8
O2—C3—C4109.6 (3)C17—C16—C15120.0 (5)
N2—C6—C5110.6 (3)C17—C16—H16A120.0
N2—C6—C7130.8 (3)C15—C16—H16A120.0
C5—C6—C7118.7 (3)C16—C17—C18119.4 (4)
N2—C11—N1112.9 (3)C16—C17—H17A120.3
N2—C11—C12124.9 (3)C18—C17—H17A120.3
N1—C11—C12122.2 (3)C2—C1—O2106 (2)
C13—C12—C11123.1 (3)C2—C1—H1A110.5
C13—C12—H12A118.4O2—C1—H1A110.5
C11—C12—H12A118.4C2—C1—H1B110.5
C12—C13—C14127.9 (3)O2—C1—H1B110.5
C12—C13—H13A116.1H1A—C1—H1B108.6
C14—C13—H13A116.1C1—C2—H2B109.5
C19—C14—C15117.4 (4)C1—C2—H2C109.5
C19—C14—C13122.9 (3)H2B—C2—H2C109.5
C15—C14—C13119.6 (3)C1—C2—H2D109.5
N1—C4—C3112.3 (3)H2B—C2—H2D109.5
N1—C4—H4A109.1H2C—C2—H2D109.5
C3—C4—H4A109.1C2'—C1'—O2108 (2)
N1—C4—H4B109.1C2'—C1'—H1'A110.1
C3—C4—H4B109.1O2—C1'—H1'A110.1
H4A—C4—H4B107.9C2'—C1'—H1'B110.1
C8—C7—C6118.0 (4)O2—C1'—H1'B110.1
C8—C7—H7A121.0H1'A—C1'—H1'B108.4
C6—C7—H7A121.0C1'—C2'—H2'A109.5
C16—C15—C14121.4 (5)C1'—C2'—H2'B109.5
C16—C15—H15A119.3H2'A—C2'—H2'B109.5
C14—C15—H15A119.3C1'—C2'—H2'C109.5
C14—C19—C18121.0 (4)H2'A—C2'—H2'C109.5
C14—C19—H19A119.5H2'B—C2'—H2'C109.5
C18—C19—H19A119.5
C11—N1—C5—C10178.2 (4)C12—C13—C14—C15174.9 (4)
C4—N1—C5—C104.8 (5)C11—N1—C4—C3−91.5 (4)
C11—N1—C5—C6−0.8 (3)C5—N1—C4—C380.3 (4)
C4—N1—C5—C6−174.2 (3)O1—C3—C4—N113.5 (5)
C1—O2—C3—O12.3 (17)O2—C3—C4—N1−167.8 (3)
C1'—O2—C3—O1−6.5 (17)N2—C6—C7—C8178.9 (4)
C1—O2—C3—C4−176.4 (16)C5—C6—C7—C8−0.3 (5)
C1'—O2—C3—C4174.8 (16)C19—C14—C15—C16−0.4 (6)
C11—N2—C6—C50.7 (4)C13—C14—C15—C16178.8 (4)
C11—N2—C6—C7−178.6 (4)C15—C14—C19—C181.2 (6)
N1—C5—C6—N20.1 (3)C13—C14—C19—C18−177.9 (4)
C10—C5—C6—N2−179.0 (3)C14—C19—C18—C170.0 (7)
N1—C5—C6—C7179.5 (3)C6—C7—C8—C9−0.1 (7)
C10—C5—C6—C70.4 (5)C10—C9—C8—C70.4 (7)
C6—N2—C11—N1−1.2 (4)C8—C9—C10—C5−0.3 (6)
C6—N2—C11—C12180.0 (3)N1—C5—C10—C9−178.9 (3)
C5—N1—C11—N21.3 (4)C6—C5—C10—C9−0.1 (5)
C4—N1—C11—N2174.2 (3)C14—C15—C16—C17−1.7 (8)
C5—N1—C11—C12−179.8 (3)C15—C16—C17—C182.9 (8)
C4—N1—C11—C12−7.0 (5)C19—C18—C17—C16−2.0 (8)
N2—C11—C12—C13−11.1 (5)C3—O2—C1—C2−147.8 (16)
N1—C11—C12—C13170.2 (3)C1'—O2—C1—C2−47 (14)
C11—C12—C13—C14178.3 (3)C3—O2—C1'—C2'177.1 (14)
C12—C13—C14—C19−5.9 (6)C1—O2—C1'—C2'94 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4B···O1i0.972.473.409 (4)162
C4—H4A···Cg2ii0.972.673.577 (4)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2982).

References

  • Göker, H., Ayhan-Kõlcõgil, G., Tuncëbilek, M., Kusë, C., Ertan, R., Kendi, E., Özbey, S., Fort, M., Garcia, C. & Farre, A. (1999). J. Heterocycl. Chem.51, 2561–2573.
  • Hang, T. & Ye, Q. (2008). Acta Cryst. E64, o964. [PMC free article] [PubMed]
  • Özbey, S., Kendi, E., Göker, H. & Tuncëbilek, M. (1998). J. Chem. Crystallogr.28, 461–464.
  • 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