1,4-Bis(benzimidazol-2-yl)benzene dimethyl­formamide disolvate

Wu, D.-H.; Hu, L.

doi:10.1107/S1600536809004759

Volume 65
Part 3
Page o522
March 2009

Received 21 January 2009
Accepted 10 February 2009
Online 13 February 2009

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.158
Data-to-parameter ratio = 17.7
Details

1,4-Bis(benzimidazol-2-yl)benzene dimethylformamide disolvate

De-Hong Wu ^a ^* and Ling Hu ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: wudh1971@sohu.com

The aromatic molecule of the title compound, C₂₀H₁₄N₄·2C₃H₇NO, occupies a special position on an inversion center. The benzimidazole unit (planar to within 0.008 Å) forms a dihedral angle of 9.1 (2)° with the central benzene ring. The benzimidazole H atom participates in a hydrogen bond with the dimethylformamide solvent molecule, thus giving rise to the title 1:2 aggregate. These aggregates are further linked in the crystal structure by aromatic [pi] - [pi] stacking interactions [centroid-centroid distance = 6.356 (2) Å].

Related literature

For background literature concerning benzimidazole compounds, see: Zarrinmayeh et al. (1998); Gallagher et al. (2001); Howarth & Hanlon (2001). For the unsolvated structure, see: Bei et al. (2000); Dudd et al. (2003).

Experimental

Crystal data

C₂₀H₁₄N₄·2C₃H₇NO
M_r = 456.54
Monoclinic, P 2₁ /n
a = 6.3556 (13) Å
b = 20.931 (2) Å
c = 9.0097 (18) Å
= 98.26 (2)°
V = 1186.1 (4) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 291 K
0.32 × 0.26 × 0.24 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.970, T_max = 0.990
12310 measured reflections
2723 independent reflections
1718 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.158
S = 1.00
2723 reflections
154 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO1ⁱ	0.86	1.95	2.787 (3)	165
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2086 ).

Acknowledgements

The authors appreciate the help of Professor Dr Rengen Xiong and the financial support of Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0802003B).

References

Bei, F., Jian, F., Yang, X., Lu, L., Wang, X., Shanmuga Sundara Raj, S. & Fun, H.-K. (2000). Acta Cryst. C56, 718-719.
Dudd, L. M., Venardou, E., Garcia-Verdugo, E., Licence, P., Blake, A. J., Wilson, C. & Poliakoff, M. (2003). Green Chem. 5, 187-192.
Gallagher, J. F., Hanlon, K. & Howarth, J. (2001). Acta Cryst. C57, 1410-1414.
Howarth, J. & Hanlon, K. (2001). Tetrahedron Lett. 42, 271-274.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709-2719.

organic compounds