1-(1-Benzyl-1H-benzimidazol-2-yl)ethanone

Zhang, C.-J.; Xu, X.-Z.; Yang, N.; Zhao, R.-Y.; Ge, Y.-Q.

doi:10.1107/S1600536812043875

Volume 68
Part 12
Page o3340
December 2012

Received 19 September 2012
Accepted 23 October 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.068
wR = 0.189
Data-to-parameter ratio = 13.1
Details

1-(1-Benzyl-1H-benzimidazol-2-yl)ethanone

Chuan-Jing Zhang,^a Xiu-Zhen Xu,^a Ning Yang,^a Ren-Ying Zhao ^a and Yan-Qing Ge ^a ^*

^aTaishan Medical University, Tai an 271016, People's Republic of China
Correspondence e-mail: yqge@yahoo.cn

In the title compound, C₁₆H₁₄N₂O, the benzimidazole ring system is essentially planar. The planes of the benzene rings make a dihedral angle of 85.92 (8)°. In the crystal, neighbouring molecule are connected into paris along the c axis by weak C-HO interactions and the connected pairs are expanded through C-HN hydrogen bonds and C-H [pi] interactions along the b axis.

Related literature

For the synthesis, see: Cao et al. (2012). For applications of nitrogen-containing heterocyclic compounds in the agrochemical and pharmaceutical fields, see: Ge et al. (2009, 2011). For a related structure, see: Sun et al. (2012).

Experimental

Crystal data

C₁₆H₁₄N₂O
M_r = 250.29
Triclinic, $[P \overline 1]$
a = 6.1307 (10) Å
b = 6.5226 (12) Å
c = 34.739 (6) Å
= 90.021 (3)°
= 92.749 (3)°
= 110.674 (3)°
V = 1298.0 (4) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.28 × 0.24 × 0.19 mm

Data collection

Brucker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.978, T_max = 0.985
6666 measured reflections
4523 independent reflections
3775 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.189
S = 1.05
4523 reflections
345 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4-C9 and C20-C25 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C5-H5N2ⁱ	0.93	2.62	3.517 (4)	161
C16-H16O1ⁱⁱ	0.93	2.58	3.427 (4)	152
C21-H21N4ⁱⁱⁱ	0.93	2.62	3.513 (4)	161
C32-H32O2ⁱⁱ	0.93	2.57	3.410 (4)	150
C1-H1CCg1^iv	0.96	2.61	3.487 (4)	151
C17-H17ACg2^iv	0.96	2.61	3.491 (4)	153
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z; (iii) -x, -y, -z+1; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2103 ).

Acknowledgements

This study was supported by theShandong Natural Science Foundation (No. ZR2012BL04)

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, X. Q., Lin, X. H., Zhu, Y. & Ge, Y. Q. (2012). Spectrochim. Acta Part A, 98, 76-80.
Ge, Y. Q., Hao, B. Q., Duan, G. Y. & Wang, J. W. (2011). J. Lumin. 131, 1070-1076.
Ge, Y. Q., Jia, J., Yang, H., Zhao, G. L., Zhan, F. X. & Wang, J. W. (2009). Heterocycles, 78, 725-736.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, T., Xie, J.-W., Zhao, R.-Y., Zhu, A.-G. & Ge, Y.-Q. (2012). Acta Cryst. E68, o2947.

organic compounds

1-(1-Benzyl-1H-benzimidazol-2-yl)ethanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References