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Volume 66 
Part 3 
Page o707  
March 2010  

Received 29 January 2010
Accepted 21 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.045
wR = 0.129
Data-to-parameter ratio = 15.6
Details
Open access

Ethyl N-[3-(N,N-dimethylcarbamoyl)pyridin-2-ylsulfonyl]carbamate

aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hljusunzhizhong@163.com

In the molecular structure of the title compound, C11H15N3O5S, the amide group is nearly perpendicular to the pyridine ring, making a dihedral angle of 86.30 (13)°. The terminal ethyl group is disordered over two sites of equal occupancy. Intermolecular N-H...O hydrogen bonding is present in the crystal structure.

Related literature

The title compound is used in the preparation of nicosulfuron, a member of the sulfonylurea family of herbicides, see: Green & Ulrich (1993[Green, J. M. & Ulrich, J. F. (1993). Weed Sci.. 41, 508-516.]). For the synthesis, see: Murai et al. (1992[Murai, S., Nakamura, Y., Akagi, T., Sakashita, T. & Haga, T. (1992). Synthesis and Chemistry of Agrochemicals III, ACS Symposium Series, Vol. 504, edited by D. R., Baker, J. G. Fenyes & J. J. Steffens, pp. 43-55. Washington: American Chemical Society.]).

[Scheme 1]

Experimental

Crystal data
  • C11H15N3O5S

  • Mr = 301.32

  • Monoclinic, P 21 /n

  • a = 8.4370 (11) Å

  • b = 11.1141 (15) Å

  • c = 15.074 (2) Å

  • [beta] = 100.594 (2)°

  • V = 1389.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.17 × 0.16 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.963

  • 7979 measured reflections

  • 3036 independent reflections

  • 2384 reflections with I > 2[sigma](I)

  • Rint = 0.026

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

  • wR(F2) = 0.129

  • S = 1.04

  • 3036 reflections

  • 195 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O1i 0.87 (2) 1.91 (3) 2.773 (2) 172 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2723 ).


Acknowledgements

We thank the National Natural Science Foundation of China (No. 20872030) and Heilongjiang University of China for supporting this study.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Green, J. M. & Ulrich, J. F. (1993). Weed Sci.. 41, 508-516.  [ChemPort]
Murai, S., Nakamura, Y., Akagi, T., Sakashita, T. & Haga, T. (1992). Synthesis and Chemistry of Agrochemicals III, ACS Symposium Series, Vol. 504, edited by D. R., Baker, J. G. Fenyes & J. J. Steffens, pp. 43-55. Washington: American Chemical Society.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). publCIF. In preparation.


Acta Cryst (2010). E66, o707  [ doi:10.1107/S160053681000663X ]

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