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Volume 69 
Part 2 
Page o229  
February 2013  

Received 17 December 2012
Accepted 6 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.140
Data-to-parameter ratio = 15.6
Details
Open access

2-Chloro-N-methyl-N-[2-(methylamino)phenyl]acetamide

aCollege of Science, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China
Correspondence e-mail: jinminggao@nwsuaf.edu.cn

The title compound, C10H13ClN2O, was obtained as a by-product in the reaction of 2-chloromethyl-1H-benzimidazole, dimethyl sulfate and toluene to synthesise 2-chloromethyl-1-methylbenzimidazole. The dihedral angle between the benzene ring and the acetamide group is 89.72  (6)° while that between the aromatic ring and the chloracetyl group is 84.40 (4)°. In the crystal, adjacent molecules are linked by pairs of N-H...O hydrogen bonds into inversion dimers.

Related literature

For the synthesis of similar compounds, see: Turner & Wood (1965[Turner, A. B. & Wood, H. C. S. (1965). J. Chem. Soc. pp. 5270-5275.]); Bai et al. (2008[Bai, Y., Li, C., Sun, W., Zhao, G. & Shi, Z. (2008). Hua Xue Shiji, 30, 409-411.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13ClN2O

  • Mr = 212.67

  • Monoclinic, P 21 /n

  • a = 9.2483 (18) Å

  • b = 6.6630 (13) Å

  • c = 17.622 (3) Å

  • [beta] = 94.377 (2)°

  • V = 1082.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 296 K

  • 0.50 × 0.35 × 0.21 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.855, Tmax = 0.935

  • 7714 measured reflections

  • 2011 independent reflections

  • 1487 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.140

  • S = 1.01

  • 2011 reflections

  • 129 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.23 2.926 (2) 138
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconin, 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: NC2302 ).


Acknowledgements

This work was supported financially by grants from the National Natural Science Foundation of China (No. 30971882), the Program of Natural Science Basis Research in Shaanxi (No. 2009JM3010) and Shaanxi Province Science and Technology (No. 2011k02-07).

References

Bai, Y., Li, C., Sun, W., Zhao, G. & Shi, Z. (2008). Hua Xue Shiji, 30, 409-411.  [ChemPort]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Turner, A. B. & Wood, H. C. S. (1965). J. Chem. Soc. pp. 5270-5275.  [CrossRef]


Acta Cryst (2013). E69, o229  [ doi:10.1107/S1600536813000494 ]

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