4,4′-Bis(benzimidazol-1-yl)biphen­yl

Zuo-Xi Li; Yi Zuo; Tong-Liang Hu

doi:10.1107/S1600536807063350

. 2007 Dec 6;64(Pt 1):o141. doi: 10.1107/S1600536807063350

4,4′-Bis(benzimidazol-1-yl)biphenyl

Zuo-Xi Li ^a, Yi Zuo ^a, Tong-Liang Hu ^a,^*

PMCID: PMC2915210 PMID: 21200706

Abstract

The molecule of the title compound, C₂₆H₁₈N₄, resides on a crystallographic inversion centre with a dihedral angle of 44.94 (5)° between the benzimidazole ring system and the benzene ring. The primary hydrogen bond is C—H⋯N and inversion-related pairs of these generate a chain of rings along the c-axis direction; π⋯π stacking involving the benzimidazole groups with interplanar separations of ca 3.4 Å complete the interactions.

Related literature

For related literature, see: Bu et al. (2007 ▶); Buchwald et al. (2001 ▶); Cristau et al. (2004 ▶); Su et al. (2003 ▶).

Experimental

Crystal data

C₂₆H₁₈N₄
M _r = 386.44
Monoclinic,
a = 19.628 (4) Å
b = 6.8964 (14) Å
c = 13.760 (3) Å
β = 90.74 (3)°
V = 1862.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.26 × 0.22 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.904, T _max = 1.000 (expected range = 0.897–0.992)
9091 measured reflections
1644 independent reflections
1415 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.103
S = 1.10
1644 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063350/gg2046sup1.cif

e-64-0o141-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063350/gg2046Isup2.hkl

e-64-0o141-Isup2.hkl^{(81.1KB, 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
C6—H6⋯N1ⁱ	0.93	2.61	3.425 (2)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Nankai University for supporting this work.

supplementary crystallographic information

Comment

In recent years, benzimidazole derivatives have been found a wide range of application in the area of coordination chemistry, because they exhibit a strong networking ability (Bu et al., 2007; Su et al., 2003). The title compound has been designed for building polymer architectures. We report here the structure and conformation, towards an understanding of the ligand coordination. As shown in Fig. 1, the title compound has trans-conformation and therefore a tendency to trans-coordination. The molecule resides on an inversion centre, and the dihedral angle between the benzimidazole ring and the phenyl ring is 40.97 (17)°. There are weak H-bonding interactions in the crystal structure of (I) (C6—H6···N1B, 3.425 (17) Å, C—H···N of 146.82 (13)°, B= x,-y + 2,z + 1/2) (Fig. 2).

Experimental

The ligand 4,4'-di(benzimidazol-1-yl)biphenyl was prepared by a modified method (Buchwald et al., 2001; Cristau et al., 2004). A mixture of 4,4'-dibromobiphenyl (3.75 g, 12.0 mmol), benzimidazole (7.08 g, 60.0 mmol), CuI (0.47 g, 2.5 mmol), 1,10-phenanthroline (1.19 g, 6.0 mmol), and K₂CO₃ (13.27 g, 96.0 mmol) was suspended in DMF (120 ml) and refluxed for 4 days to afford (I) as light-yellow powder, yield: 30% (based on 4,4'-dibromobiphenyl). M.p.: 566 K. MS (ESI): m/z=387.45. Anal calcd for C₂₆H₁₈N₄: C, 80.81%; H, 4.69%; N, 14.50%. Found: C, 80.56%; H, 4.48%; N, 14.31%. Single crystals were obtained by recrystallizing from a mixture of CHCl₃ and CH₃OH (1:1).