[Journal logo]

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 [sigma](C-C) = 0.005 Å
R = 0.068
wR = 0.189
Data-to-parameter ratio = 13.1
Details
Open access

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

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-H...O interactions and the connected pairs are expanded through C-H...N hydrogen bonds and C-H...[pi] interactions along the b axis.

Related literature

For the synthesis, see: Cao et al. (2012[Cao, X. Q., Lin, X. H., Zhu, Y. & Ge, Y. Q. (2012). Spectrochim. Acta Part A, 98, 76-80.]). For applications of nitrogen-containing heterocyclic compounds in the agrochemical and pharmaceutical fields, see: Ge et al. (2009[Ge, Y. Q., Jia, J., Yang, H., Zhao, G. L., Zhan, F. X. & Wang, J. W. (2009). Heterocycles, 78, 725-736.], 2011[Ge, Y. Q., Hao, B. Q., Duan, G. Y. & Wang, J. W. (2011). J. Lumin. 131, 1070-1076.]). For a related structure, see: Sun et al. (2012[Sun, T., Xie, J.-W., Zhao, R.-Y., Zhu, A.-G. & Ge, Y.-Q. (2012). Acta Cryst. E68, o2947.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O

  • Mr = 250.29

  • Triclinic, [P \overline 1]

  • a = 6.1307 (10) Å

  • b = 6.5226 (12) Å

  • c = 34.739 (6) Å

  • [alpha] = 90.021 (3)°

  • [beta] = 92.749 (3)°

  • [gamma] = 110.674 (3)°

  • V = 1298.0 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.985

  • 6666 measured reflections

  • 4523 independent reflections

  • 3775 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.189

  • S = 1.05

  • 4523 reflections

  • 345 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C5-H5...N2i 0.93 2.62 3.517 (4) 161
C16-H16...O1ii 0.93 2.58 3.427 (4) 152
C21-H21...N4iii 0.93 2.62 3.513 (4) 161
C32-H32...O2ii 0.93 2.57 3.410 (4) 150
C1-H1C...Cg1iv 0.96 2.61 3.487 (4) 151
C17-H17A...Cg2iv 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort]
Ge, Y. Q., Hao, B. Q., Duan, G. Y. & Wang, J. W. (2011). J. Lumin. 131, 1070-1076.  [ISI] [CrossRef] [ChemPort]
Ge, Y. Q., Jia, J., Yang, H., Zhao, G. L., Zhan, F. X. & Wang, J. W. (2009). Heterocycles, 78, 725-736.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, T., Xie, J.-W., Zhao, R.-Y., Zhu, A.-G. & Ge, Y.-Q. (2012). Acta Cryst. E68, o2947.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3340  [ doi:10.1107/S1600536812043875 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.