2-(3,4,5-Trimethoxy­phen­yl)-1H-benzimidazole

Khalaji, A.D.; Jian, F.; Xiao, H.; Harrison, W.T.A.

doi:10.1107/S1600536808014189

Volume 64
Part 6
Page o1093
June 2008

Received 29 April 2008
Accepted 12 May 2008
Online 17 May 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.052
wR = 0.144
Data-to-parameter ratio = 14.4
Details

2-(3,4,5-Trimethoxyphenyl)-1H-benzimidazole

Aliakbar Dehno Khalaji,^a Fangfang Jian,^b Hailian Xiao ^b and William T. A. Harrison ^c ^*

^aDepartment of Science, Gorgan University of Agricultrual Sciences and Natural Resources, Gorgan 49189-43464, Iran,^bNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: w.harrison@abdn.ac.uk

In the title compound, C₁₆H₁₆N₂O₃, the dihedral angle between the mean planes of the aromatic ring systems is 30.90 (15)°. In the crystal structure, the molecules form [010] chains by way of N-HN hydrogen bonds.

Related literature

For a related structure, see: Rashid et al. (2007). For background, see: Gupta et al. (2004). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M_r = 284.31
Orthorhombic, P b c a
a = 8.2270 (16) Å
b = 9.5750 (19) Å
c = 37.375 (7) Å
V = 2944.2 (10) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 295 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
5421 measured reflections
2733 independent reflections
960 reflections with I > 2(I)
R_int = 0.085
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.143
S = 0.94
2733 reflections
190 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.86	2.07	2.918 (4)	169
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2706 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Gupta, P., Hameed, S. & Jain, R. (2004). Eur. J. Med. Chem. 39, 805-814.
Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds