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

Bai, Y.-B.; Chen, X.-H.; Ma, Y.-T.; Zhang, A.-L.; Gao, J.-M.

doi:10.1107/S1600536813000494

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 (C-C) = 0.003 Å
R = 0.045
wR = 0.140
Data-to-parameter ratio = 15.6
Details

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

Yu-Bin Bai,^a Xia-Hui Chen,^a Ya-Tuan Ma,^a An-Ling Zhang ^a and Jin-Ming Gao ^a ^*

^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-HO hydrogen bonds into inversion dimers.

Related literature

For the synthesis of similar compounds, see: Turner & Wood (1965); Bai et al. (2008).

Experimental

Crystal data

C₁₀H₁₃ClN₂O
M_r = 212.67
Monoclinic, P 2₁ /n
a = 9.2483 (18) Å
b = 6.6630 (13) Å
c = 17.622 (3) Å
= 94.377 (2)°
V = 1082.8 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.855, T_max = 0.935
7714 measured reflections
2011 independent reflections
1487 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.140
S = 1.01
2011 reflections
129 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.23	2.926 (2)	138
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: 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.
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.
Turner, A. B. & Wood, H. C. S. (1965). J. Chem. Soc. pp. 5270-5275.

organic compounds