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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 25;67(Pt 7):o1797. doi: 10.1107/S1600536811024251

1,4-Bis(1H-benzimidazol-1-yl)but-2-ene

Gui-Ying Dong a,*, Tong-Fei Liu a, Cui-Huan Jiao a, Xiao-Chen Deng b, Xiao-Ge Shi b
PMCID: PMC3152113  PMID: 21837170

Abstract

In the pseudo-centrosymmetric mol­ecule of the title compound, C18H16N4, two benzimidazole fragments form the dihedral angles of 83.49 (7) and 79.37 (7)°, with the mean plane of the linking butene chain. No classical inter­molecular inter­actions are observed. The porous crystal packing exhibits voids of 85 Å3.

Related literature

For applications of benzimidazole derivatives, see: Tidwell et al. (1993 ▶); Santra & Dogra (1999 ▶). For related structures, see: Su et al. (2003 ▶); Chen et al. (2007 ▶); Liu et al. (2011 ▶).graphic file with name e-67-o1797-scheme1.jpg

Experimental

Crystal data

  • C18H16N4

  • M r = 288.35

  • Monoclinic, Inline graphic

  • a = 12.564 (3) Å

  • b = 9.140 (2) Å

  • c = 18.131 (3) Å

  • β = 127.281 (12)°

  • V = 1656.7 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 295 K

  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.996

  • 12226 measured reflections

  • 2925 independent reflections

  • 1639 reflections with I > 2σ(I)

  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052

  • wR(F 2) = 0.133

  • S = 1.01

  • 2925 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024251/cv5116sup1.cif

e-67-o1797-sup1.cif (22.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024251/cv5116Isup2.hkl

e-67-o1797-Isup2.hkl (143.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811024251/cv5116Isup3.cml

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

Acknowledgments

The authors thank Hebei United University for support of this work.

supplementary crystallographic information

Comment

Bis-benzimidazole compounds have have been widely used due to their anti-viral activities (Tidwell et al., 1993), photochemical and photophysical properties (Santra & Dogra, 1999). They have found applications in supramolecular coordination chemistry to generate various coordination architectures (Su et al., 2003; Chen et al., 2007; Liu et al., 2011). Herewith we report the crystal structure of the title bis-benzimidazole compound (I).

In (I) (Fig. 1), the molecule adopts a trans conformation. Two benzimidazole fragments form the dihedral angles of 83.49 (7) and 79.37 (7) °, respectively, with the mean plane of linking them butene chain. The C11—C10—C9—C8 torsion angle is 176.5 (3)°. The average bond distances and angles for the benzimidazole ring are in agreement with those in related benzimidazole compounds (Chen et al., 2007; Liu et al.2011). In the absence of classical intermolecular interactions, the porous crystal packing exhibits voids of 85 Å3.

Experimental

The title compound was prepared according to the literature (Liu et al., 2011). Single crystals were grown from an ethanol solution over a period of several days at room temperature.

Refinement

H atoms were placed in calculated positions (C—H 0.93-0.97 Å), and refined with a riding model, with Uiso(H) = 1.2Ueq(C). The program Squeeze in PLATON (Spek, 2009) was applied to remove regions of diffuse electron density that could not be satisfactorily modeled.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), showing displacement ellipsoids at the 30% probability level.

Crystal data

C18H16N4 F(000) = 608
Mr = 288.35 Dx = 1.156 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 4528 reflections
a = 12.564 (3) Å θ = 3.5–20.3°
b = 9.140 (2) Å µ = 0.07 mm−1
c = 18.131 (3) Å T = 295 K
β = 127.281 (12)° Block, colourless
V = 1656.7 (6) Å3 0.20 × 0.18 × 0.17 mm
Z = 4
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Data collection

Bruker SMART CCD area-detector diffractometer 2925 independent reflections
Radiation source: fine–focus sealed tube 1639 reflections with I > 2σ(I)
graphite Rint = 0.056
φ and ω scans θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −14→14
Tmin = 0.956, Tmax = 0.996 k = −10→10
12226 measured reflections l = −21→21
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0545P)2] where P = (Fo2 + 2Fc2)/3
2925 reflections (Δ/σ)max < 0.001
199 parameters Δρmax = 0.19 e Å−3
0 restraints Δρmin = −0.14 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.93808 (17) −0.12271 (19) 0.16716 (12) 0.0514 (5)
N2 1.0262 (2) −0.1093 (2) 0.31752 (13) 0.0646 (6)
N3 0.55655 (17) 0.1198 (2) −0.20779 (12) 0.0533 (5)
N4 0.4402 (2) 0.1102 (2) −0.36219 (14) 0.0724 (6)
C1 1.0390 (2) −0.0742 (2) 0.25325 (18) 0.0632 (7)
H1 1.1111 −0.0206 0.2655 0.076*
C2 0.9075 (2) −0.1874 (2) 0.27030 (15) 0.0528 (6)
C3 0.8415 (3) −0.2500 (3) 0.30264 (17) 0.0650 (7)
H3 0.8766 −0.2436 0.3648 0.078*
C4 0.7230 (3) −0.3217 (3) 0.2396 (2) 0.0710 (7)
H4 0.6771 −0.3641 0.2595 0.085*
C5 0.6706 (2) −0.3319 (3) 0.14720 (18) 0.0662 (7)
H5 0.5907 −0.3822 0.1068 0.079*
C6 0.7322 (2) −0.2708 (2) 0.11317 (16) 0.0567 (6)
H6 0.6962 −0.2778 0.0509 0.068*
C7 0.8516 (2) −0.1974 (2) 0.17686 (14) 0.0474 (6)
C8 0.9207 (2) −0.0957 (2) 0.08116 (15) 0.0592 (6)
H8A 0.8973 −0.1865 0.0469 0.071*
H8B 1.0043 −0.0612 0.0955 0.071*
C9 0.8136 (2) 0.0152 (3) 0.02248 (17) 0.0590 (6)
H9 0.8277 0.1096 0.0460 0.071*
C10 0.7016 (2) −0.0108 (2) −0.05950 (17) 0.0600 (6)
H10 0.6902 −0.1037 −0.0843 0.072*
C11 0.5908 (2) 0.0964 (3) −0.11649 (16) 0.0678 (7)
H11B 0.5122 0.0616 −0.1235 0.081*
H11A 0.6166 0.1892 −0.0839 0.081*
C12 0.4456 (2) 0.0739 (3) −0.2902 (2) 0.0684 (7)
H12 0.3783 0.0207 −0.2953 0.082*
C13 0.5584 (2) 0.1877 (2) −0.32404 (15) 0.0548 (6)
C14 0.6068 (3) 0.2551 (3) −0.36690 (17) 0.0738 (8)
H14 0.5599 0.2508 −0.4308 0.089*
C15 0.7263 (3) 0.3282 (3) −0.3115 (2) 0.0797 (8)
H15 0.7597 0.3761 −0.3388 0.096*
C16 0.7985 (2) 0.3327 (3) −0.2160 (2) 0.0699 (7)
H16 0.8794 0.3827 −0.1807 0.084*
C17 0.7535 (2) 0.2653 (2) −0.17234 (16) 0.0545 (6)
H17 0.8021 0.2673 −0.1082 0.065*
C18 0.6318 (2) 0.1941 (2) −0.22858 (14) 0.0443 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0494 (11) 0.0484 (11) 0.0549 (12) −0.0002 (9) 0.0308 (11) 0.0018 (9)
N2 0.0630 (13) 0.0578 (13) 0.0591 (13) −0.0018 (11) 0.0297 (11) −0.0044 (10)
N3 0.0467 (11) 0.0536 (12) 0.0573 (12) 0.0023 (10) 0.0303 (10) 0.0052 (10)
N4 0.0592 (14) 0.0724 (15) 0.0568 (13) −0.0074 (12) 0.0201 (11) −0.0030 (11)
C1 0.0531 (15) 0.0533 (16) 0.0684 (18) −0.0049 (12) 0.0291 (15) −0.0048 (13)
C2 0.0570 (15) 0.0439 (13) 0.0556 (15) 0.0049 (12) 0.0331 (13) −0.0007 (11)
C3 0.084 (2) 0.0591 (16) 0.0631 (16) 0.0103 (14) 0.0507 (16) 0.0061 (12)
C4 0.0794 (19) 0.0583 (17) 0.094 (2) 0.0030 (15) 0.0625 (18) 0.0055 (15)
C5 0.0515 (15) 0.0570 (16) 0.084 (2) −0.0026 (13) 0.0376 (15) 0.0007 (13)
C6 0.0537 (15) 0.0529 (15) 0.0532 (14) 0.0025 (12) 0.0269 (13) 0.0030 (11)
C7 0.0455 (13) 0.0417 (13) 0.0488 (14) 0.0046 (11) 0.0253 (12) 0.0022 (10)
C8 0.0641 (15) 0.0595 (15) 0.0607 (15) 0.0039 (13) 0.0413 (13) 0.0064 (12)
C9 0.0732 (16) 0.0531 (15) 0.0619 (16) 0.0067 (13) 0.0468 (15) 0.0067 (12)
C10 0.0753 (17) 0.0540 (15) 0.0641 (16) 0.0089 (14) 0.0492 (15) 0.0122 (12)
C11 0.0686 (17) 0.0706 (17) 0.0766 (18) 0.0148 (14) 0.0504 (15) 0.0169 (13)
C12 0.0478 (15) 0.0543 (16) 0.082 (2) −0.0080 (12) 0.0285 (16) 0.0017 (14)
C13 0.0522 (15) 0.0512 (14) 0.0527 (14) 0.0033 (12) 0.0274 (13) −0.0001 (11)
C14 0.083 (2) 0.082 (2) 0.0539 (16) 0.0163 (16) 0.0402 (16) 0.0155 (14)
C15 0.080 (2) 0.079 (2) 0.105 (2) 0.0119 (17) 0.0691 (19) 0.0235 (17)
C16 0.0555 (15) 0.0593 (17) 0.092 (2) −0.0005 (13) 0.0430 (16) 0.0075 (14)
C17 0.0485 (14) 0.0457 (14) 0.0588 (15) 0.0036 (11) 0.0271 (13) 0.0026 (11)
C18 0.0420 (13) 0.0384 (12) 0.0490 (14) 0.0039 (11) 0.0258 (11) 0.0027 (10)
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Geometric parameters (Å, °)

N1—C1 1.358 (3) C8—C9 1.495 (3)
N1—C7 1.382 (2) C8—H8A 0.9700
N1—C8 1.458 (2) C8—H8B 0.9700
N2—C1 1.309 (3) C9—C10 1.308 (3)
N2—C2 1.387 (3) C9—H9 0.9300
N3—C12 1.352 (3) C10—C11 1.491 (3)
N3—C18 1.389 (2) C10—H10 0.9300
N3—C11 1.452 (3) C11—H11B 0.9700
N4—C12 1.308 (3) C11—H11A 0.9700
N4—C13 1.393 (3) C12—H12 0.9300
C1—H1 0.9300 C13—C18 1.384 (3)
C2—C7 1.389 (3) C13—C14 1.387 (3)
C2—C3 1.395 (3) C14—C15 1.372 (3)
C3—C4 1.375 (3) C14—H14 0.9300
C3—H3 0.9300 C15—C16 1.387 (3)
C4—C5 1.383 (3) C15—H15 0.9300
C4—H4 0.9300 C16—C17 1.365 (3)
C5—C6 1.368 (3) C16—H16 0.9300
C5—H5 0.9300 C17—C18 1.383 (3)
C6—C7 1.391 (3) C17—H17 0.9300
C6—H6 0.9300
C1—N1—C7 105.92 (18) H8A—C8—H8B 108.0
C1—N1—C8 127.2 (2) C10—C9—C8 124.8 (2)
C7—N1—C8 126.83 (18) C10—C9—H9 117.6
C1—N2—C2 104.1 (2) C8—C9—H9 117.6
C12—N3—C18 105.52 (19) C9—C10—C11 125.3 (2)
C12—N3—C11 127.5 (2) C9—C10—H10 117.3
C18—N3—C11 126.95 (19) C11—C10—H10 117.3
C12—N4—C13 103.8 (2) N3—C11—C10 113.18 (19)
N2—C1—N1 114.2 (2) N3—C11—H11B 108.9
N2—C1—H1 122.9 C10—C11—H11B 108.9
N1—C1—H1 122.9 N3—C11—H11A 108.9
N2—C2—C7 110.3 (2) C10—C11—H11A 108.9
N2—C2—C3 130.0 (2) H11B—C11—H11A 107.8
C7—C2—C3 119.7 (2) N4—C12—N3 114.8 (2)
C4—C3—C2 117.8 (2) N4—C12—H12 122.6
C4—C3—H3 121.1 N3—C12—H12 122.6
C2—C3—H3 121.1 C18—C13—C14 119.7 (2)
C3—C4—C5 121.3 (2) C18—C13—N4 110.2 (2)
C3—C4—H4 119.3 C14—C13—N4 130.1 (2)
C5—C4—H4 119.3 C15—C14—C13 117.6 (2)
C6—C5—C4 122.3 (2) C15—C14—H14 121.2
C6—C5—H5 118.8 C13—C14—H14 121.2
C4—C5—H5 118.8 C14—C15—C16 121.7 (2)
C5—C6—C7 116.3 (2) C14—C15—H15 119.1
C5—C6—H6 121.9 C16—C15—H15 119.1
C7—C6—H6 121.9 C17—C16—C15 121.6 (2)
N1—C7—C2 105.48 (19) C17—C16—H16 119.2
N1—C7—C6 131.9 (2) C15—C16—H16 119.2
C2—C7—C6 122.6 (2) C16—C17—C18 116.5 (2)
N1—C8—C9 111.31 (18) C16—C17—H17 121.8
N1—C8—H8A 109.4 C18—C17—H17 121.8
C9—C8—H8A 109.4 C17—C18—C13 122.9 (2)
N1—C8—H8B 109.4 C17—C18—N3 131.3 (2)
C9—C8—H8B 109.4 C13—C18—N3 105.72 (19)
C2—N2—C1—N1 0.1 (3) C12—N3—C11—C10 108.2 (3)
C7—N1—C1—N2 −0.3 (2) C18—N3—C11—C10 −71.6 (3)
C8—N1—C1—N2 176.94 (19) C9—C10—C11—N3 123.4 (2)
C1—N2—C2—C7 0.2 (2) C13—N4—C12—N3 −0.2 (3)
C1—N2—C2—C3 −178.6 (2) C18—N3—C12—N4 −0.1 (3)
N2—C2—C3—C4 179.6 (2) C11—N3—C12—N4 −179.9 (2)
C7—C2—C3—C4 0.8 (3) C12—N4—C13—C18 0.4 (2)
C2—C3—C4—C5 0.2 (3) C12—N4—C13—C14 −178.9 (2)
C3—C4—C5—C6 −0.7 (4) C18—C13—C14—C15 −1.1 (3)
C4—C5—C6—C7 0.2 (3) N4—C13—C14—C15 178.1 (2)
C1—N1—C7—C2 0.4 (2) C13—C14—C15—C16 1.4 (4)
C8—N1—C7—C2 −176.86 (18) C14—C15—C16—C17 −0.5 (4)
C1—N1—C7—C6 −179.6 (2) C15—C16—C17—C18 −0.7 (3)
C8—N1—C7—C6 3.1 (3) C16—C17—C18—C13 1.0 (3)
N2—C2—C7—N1 −0.4 (2) C16—C17—C18—N3 −177.8 (2)
C3—C2—C7—N1 178.58 (19) C14—C13—C18—C17 −0.1 (3)
N2—C2—C7—C6 179.66 (19) N4—C13—C18—C17 −179.48 (19)
C3—C2—C7—C6 −1.3 (3) C14—C13—C18—N3 178.9 (2)
C5—C6—C7—N1 −179.1 (2) N4—C13—C18—N3 −0.4 (2)
C5—C6—C7—C2 0.8 (3) C12—N3—C18—C17 179.2 (2)
C1—N1—C8—C9 −104.7 (2) C11—N3—C18—C17 −0.9 (3)
C7—N1—C8—C9 72.0 (3) C12—N3—C18—C13 0.3 (2)
N1—C8—C9—C10 −116.2 (2) C11—N3—C18—C13 −179.85 (19)
C8—C9—C10—C11 176.37 (19)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5116).

References

  1. Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Chen, C.-L., Zhang, J.-Y. & Su, C.-Y. (2007). Eur. J. Inorg. Chem. pp. 2997– 3010.
  3. Liu, T.-F., Wu, W.-F., Wan, C.-Q., He, C.-H., Jiao, C.-H. & Cui, G.-H. (2011). J. Coord. Chem. 64, 975–986.
  4. Santra, S. & Dogra, S. K. (1999). J. Mol. Struct. 476, 223–233.
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  8. Su, C.-Y., Cai, Y.-P., Chen, C.-L., Smith, M. D., Kaim, W. & zur Loye, H.-C. (2003). J. Am. Chem. Soc. 125, 8595–8613. [DOI] [PubMed]
  9. Tidwell, R. R., Jones, S. K., Naiman, N. A., Berger, L. C., Brake, W. B., Dykstra, C. C. & Hall, J. E. (1993). Antimicrob. Agents Chemother. 37, 1713–1716. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024251/cv5116sup1.cif

e-67-o1797-sup1.cif (22.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024251/cv5116Isup2.hkl

e-67-o1797-Isup2.hkl (143.6KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811024251/cv5116Isup3.cml

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

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

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