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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o964.
Published online 2008 May 3. doi:  10.1107/S1600536808006405
PMCID: PMC2961456

(E)-2-[2-(2-Thien­yl)vin­yl]-1H-1,3-benzimidazole

Abstract

In the title compound, C13H10N2S, the dihedral angle between the imidazole and thio­phene rings is 16.89 (19)°, and the double bond adopts an E configuration. In the crystal structure, N—H(...)N hydrogen bonds link the mol­ecules into rows along b. There is also evidence of weak C—H(...)S inter­actions.

Related literature

For general background, see: Huang et al. (2003 [triangle]); Wang et al. (2005 [triangle]); Ye et al. (2006 [triangle], 2007 [triangle]). For the crystal structures of related compounds, see: Ozbey et al. (1998 [triangle]); Li & Clarkson (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o964-scheme1.jpg

Experimental

Crystal data

  • C13H10N2S
  • M r = 226.06
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o964-efi1.jpg
  • a = 12.239 (2) Å
  • b = 16.389 (3) Å
  • c = 11.487 (2) Å
  • V = 2304.1 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 293 (2) K
  • 0.15 × 0.10 × 0.07 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.796, T max = 1.000 (expected range = 0.782–0.983)
  • 21849 measured reflections
  • 2637 independent reflections
  • 1360 reflections with I > 2σ(I)
  • R int = 0.145

Refinement

  • R[F 2 > 2σ(F 2)] = 0.084
  • wR(F 2) = 0.214
  • S = 1.07
  • 2637 reflections
  • 145 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.28 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/S1600536808006405/sj2460sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006405/sj2460Isup2.hkl

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University (to YQ).

supplementary crystallographic information

Comment

It has been generally accepted that imidazole groups play an important role in coordination chemistry (Huang et al., 2003). A flexible ligand readily induces coordination compounds to crystallize in non-centrosymmetric space groups, which makes it possible to investigate their interesting physical properties such as second harmonic generation, ferroelectric and piezoelectric properties (Wang et al., 2005). As a continuation of our work in this field, (Ye et al., 2006, 2007), we have synthesized the title compound, 1, Fig 1.

The title compound, C12H10N2S, was successfully prepared through the reaction between 2-methyl-1H-benzo[d]imidazole and thiophene-2-carbaldehyde. It adopts a trans configuration about the C9?C11 bond and the dihedral angle between the mean plane of the imidazole ring and thiophenyl ring is 16.89 (19)°. The crystal packing is dominated by N—H···N interactions linking the molecules into rows along b, Fig 2. There is also evidence of weak C—H···S interactions.

Experimental

2-methyl-1H-benzo[d]imidazole (10 mmol, 1.32 g) and thiophene-2-carbaldehyde (45 mmol, 5.04 g) were reacted as a melt at 180°C with stirring for 18 h. Then 20 ml 2-propanol and 1.5 g oxalic acid were added to the reaction mixture, the solution filtered and the precipitate washed with copious quantities of boiling water. The pH was adjusted to 8–9 with ammonia to afford the title compound as a pale-yellow solid powder. Crystals suitable for single-crystal X-ray diffraction studies were obtained by slow evaporation of a solution in ethanol at room temperature over several days.

Refinement

All carbon-bound H atoms were positioned geometrically, with C—H = 0.93 Å and included in the refinement as riding, withUiso(H) = 1.2Ueq. The H atoms attached to N were found in the difference Fourier map and were subsequently treated as riding atoms, with N—H = 0.86 Å, and Uiso(H) = 1.2Ueq(N).

Figures

Fig. 1.
The molecular structure of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
Fig. 2.
The crystal packing of 1 with hydrogen bonds drawn as dashed lines.

Crystal data

C13H10N2SF000 = 944
Mr = 226.06Dx = 1.305 Mg m3
Orthorhombic, PnnaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2a 2bcCell parameters from 14820 reflections
a = 12.239 (2) Åθ = 3.0–29.2º
b = 16.389 (3) ŵ = 0.25 mm1
c = 11.487 (2) ÅT = 293 (2) K
V = 2304.1 (7) Å3Block, colorless
Z = 80.15 × 0.10 × 0.07 mm

Data collection

Mercury2 (2x2 bin mode) diffractometer2637 independent reflections
Radiation source: fine-focus sealed tube1360 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.145
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.3º
CCD profile fitting scansh = −15→15
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −21→21
Tmin = 0.796, Tmax = 1.000l = −14→14
21849 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)] = 0.084H-atom parameters constrained
wR(F2) = 0.214  w = 1/[σ2(Fo2) + (0.081P)2 + 0.7151P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2637 reflectionsΔρmax = 0.22 e Å3
145 parametersΔρmin = −0.28 e Å3
1 restraintExtinction 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 > σ(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)
S10.88515 (10)0.06908 (7)0.51647 (11)0.0801 (5)
N10.6821 (2)0.07121 (18)0.1000 (3)0.0577 (9)
H1B0.72640.03090.09240.069*0.50
N20.5945 (2)0.17665 (16)0.1790 (2)0.0452 (7)
H2B0.57510.21340.22830.054*0.50
C10.5111 (4)0.1178 (3)−0.1555 (4)0.0824 (14)
H1A0.49560.1028−0.23190.099*
C20.8179 (4)0.1317 (3)0.7051 (4)0.0898 (15)
H2A0.81360.14530.78360.108*
C30.8987 (5)0.0855 (3)0.6610 (4)0.0890 (16)
H3A0.95590.06470.70530.107*
C40.7391 (3)0.1583 (3)0.6209 (3)0.0653 (11)
H4A0.67900.19130.63640.078*
C50.5901 (4)0.0750 (3)−0.0942 (4)0.0753 (13)
H5A0.62780.0316−0.12770.090*
C60.4751 (3)0.2076 (2)0.0054 (3)0.0604 (11)
H6A0.43760.25140.03810.073*
C70.4546 (4)0.1825 (3)−0.1057 (4)0.0720 (12)
H7A0.40150.2094−0.14920.086*
C80.7672 (3)0.1264 (2)0.5105 (3)0.0581 (10)
C90.7079 (3)0.1380 (2)0.4039 (3)0.0532 (10)
H9A0.64610.17090.40740.064*
C100.6101 (3)0.0995 (2)0.0186 (3)0.0515 (9)
C110.7328 (3)0.1064 (2)0.3007 (3)0.0526 (10)
H11A0.79500.07400.29610.063*
C120.6700 (3)0.1188 (2)0.1941 (3)0.0479 (9)
C130.5538 (3)0.1655 (2)0.0678 (3)0.0461 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0830 (9)0.0654 (8)0.0918 (10)−0.0012 (6)−0.0304 (7)0.0032 (6)
N10.0607 (19)0.0583 (19)0.054 (2)0.0158 (16)−0.0072 (15)−0.0140 (16)
N20.0532 (17)0.0401 (16)0.0422 (17)0.0063 (13)0.0015 (13)−0.0027 (13)
C10.097 (3)0.096 (4)0.054 (3)0.004 (3)−0.017 (3)−0.015 (3)
C20.113 (4)0.106 (4)0.050 (3)−0.026 (3)−0.023 (2)0.013 (3)
C30.112 (4)0.076 (3)0.079 (4)−0.023 (3)−0.043 (3)0.023 (3)
C40.070 (3)0.081 (3)0.045 (2)−0.018 (2)−0.0037 (18)0.001 (2)
C50.083 (3)0.079 (3)0.064 (3)0.018 (2)−0.011 (2)−0.028 (2)
C60.072 (3)0.054 (2)0.055 (2)0.009 (2)−0.009 (2)0.001 (2)
C70.081 (3)0.071 (3)0.064 (3)0.009 (2)−0.021 (2)0.007 (2)
C80.063 (2)0.051 (2)0.061 (3)−0.0153 (19)−0.014 (2)0.0087 (19)
C90.055 (2)0.049 (2)0.056 (3)−0.0009 (18)−0.0023 (18)0.0054 (18)
C100.053 (2)0.051 (2)0.051 (2)0.0034 (18)−0.0051 (18)−0.0070 (18)
C110.051 (2)0.048 (2)0.059 (3)0.0005 (17)−0.0004 (19)−0.0009 (18)
C120.048 (2)0.049 (2)0.047 (2)−0.0011 (17)0.0016 (17)0.0022 (17)
C130.052 (2)0.0418 (19)0.044 (2)−0.0023 (17)0.0020 (17)0.0001 (16)

Geometric parameters (Å, °)

S1—C31.690 (5)C4—C81.415 (5)
S1—C81.723 (4)C4—H4A0.9300
N1—C121.341 (4)C5—C101.379 (5)
N1—C101.366 (4)C5—H5A0.9300
N1—H1B0.8600C6—C71.365 (5)
N2—C121.335 (4)C6—C131.385 (5)
N2—C131.383 (4)C6—H6A0.9300
N2—H2B0.8600C7—H7A0.9300
C1—C51.386 (6)C8—C91.436 (5)
C1—C71.390 (6)C9—C111.329 (5)
C1—H1A0.9300C9—H9A0.9300
C2—C31.344 (6)C10—C131.401 (5)
C2—C41.435 (6)C11—C121.461 (4)
C2—H2A0.9300C11—H11A0.9300
C3—H3A0.9300
C3—S1—C892.0 (3)C7—C6—H6A121.3
C12—N1—C10106.4 (3)C13—C6—H6A121.3
C12—N1—H1B126.8C6—C7—C1121.6 (4)
C10—N1—H1B126.8C6—C7—H7A119.2
C12—N2—C13106.0 (3)C1—C7—H7A119.2
C12—N2—H2B127.0C4—C8—C9126.3 (4)
C13—N2—H2B127.0C4—C8—S1111.7 (3)
C5—C1—C7121.6 (4)C9—C8—S1122.0 (3)
C5—C1—H1A119.2C11—C9—C8126.3 (4)
C7—C1—H1A119.2C11—C9—H9A116.8
C3—C2—C4114.3 (4)C8—C9—H9A116.8
C3—C2—H2A122.8N1—C10—C5131.2 (4)
C4—C2—H2A122.8N1—C10—C13107.7 (3)
C2—C3—S1112.8 (4)C5—C10—C13121.1 (4)
C2—C3—H3A123.6C9—C11—C12125.0 (3)
S1—C3—H3A123.6C9—C11—H11A117.5
C8—C4—C2109.2 (4)C12—C11—H11A117.5
C8—C4—H4A125.4N1—C12—N2112.7 (3)
C2—C4—H4A125.4N1—C12—C11122.5 (3)
C1—C5—C10117.0 (4)N2—C12—C11124.9 (3)
C1—C5—H5A121.5N2—C13—C6131.5 (3)
C10—C5—H5A121.5N2—C13—C10107.3 (3)
C7—C6—C13117.5 (4)C6—C13—C10121.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11A···S10.932.763.161 (4)107
N1—H1B···N1i0.862.012.865 (6)170
N2—H2B···N2ii0.862.112.906 (5)154

Symmetry codes: (i) −x+3/2, −y, z; (ii) x, −y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2460).

References

  • Huang, X.-C., Zhang, J.-P. & Chen, X.-M. (2003). Chin. Sci. Bull.48, 1531–1534.
  • Li, L. & Clarkson, G. J. (2007). Org. Lett.9, 497–500. [PubMed]
  • Ozbey, S., Ide, S. & Kendi, E. (1998). J. Mol. Struct.442, 23–30.
  • Rigaku (2005). CrystalClear Version 1.4.0. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X.-S., Song, Y.-M., Ye, Q. & Xiong, R.-G. (2005). Chin. Sci. Bull.50, 2317–2340.
  • Ye, Q., Song, Y.-M., Fu, D.-W., Wang, G.-X. & Xiong, R.-G. (2007). Cryst. Growth Des.7, 1568–1570.
  • Ye, Q., Song, Y.-M., Wang, G.-X. & Xiong, R.-G. (2006). J. Am. Chem. Soc.128, 6554–6555. [PubMed]

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