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Volume 66 
Part 8 
Page o2017  
August 2010  

Received 26 June 2010
Accepted 8 July 2010
Online 14 July 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.111
Data-to-parameter ratio = 15.4
Details
Open access

2-Chloro-N-isopropyl-N-phenylacetamide

aCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China, and bCollege of Life Sciences, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
Correspondence e-mail: yuanms@nwsuaf.edu.cn

In the title compound, C11H14ClNO, the herbicide propachlor, there are significant differences between the three N-C bond lengths [N-Ccarbonyl = 1.354 (3) Å, N-Cphenyl = 1.444 (2) Å and N-Cisopropyl = 1.496 (3) Å], indicating the presence of [pi] delocalization involving the carbonyl group. The N atom lies 0.074 (2) Å from the plane defined by the the three bonded C atoms.

Related literature

For studies of propachlor and its derivatives, see: Dhillon & Anderson (1972[Dhillon, N. S. & Anderson, J. L. (1972). Weed Res. 12, 182-189.]); Kleudgen (1980[Kleudgen, H. K. (1980). Weed Res. 20, 41-46.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14ClNO

  • Mr = 211.68

  • Monoclinic, P 21 /n

  • a = 11.9190 (11) Å

  • b = 7.8042 (8) Å

  • c = 12.3789 (13) Å

  • [beta] = 98.963 (1)°

  • V = 1137.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 298 K

  • 0.47 × 0.45 × 0.44 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 0.878

  • 5426 measured reflections

  • 2004 independent reflections

  • 1501 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.111

  • S = 1.03

  • 2004 reflections

  • 130 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: SMART (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SMART. 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: ZS2048 ).


Acknowledgements

This work was supported by the PhD Programs Foundation of the Ministry of Education of China (No. 20090204120033)

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dhillon, N. S. & Anderson, J. L. (1972). Weed Res. 12, 182-189.  [CrossRef] [ChemPort] [ISI]
Kleudgen, H. K. (1980). Weed Res. 20, 41-46.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o2017  [ doi:10.1107/S1600536810027157 ]

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