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Volume 68 
Part 11 
Page o3109  
November 2012  

Received 12 September 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 15.7
Details
Open access

3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-one

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bNational Research Centre for Grapes, Pune 412 307, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title compound, C8H10ClN3O2S, the oxadiazinane ring is in a sofa conformation with the ring O atom deviating from the best plane of the remaining five atoms by 0.636 (2) Å. A short intramolecular C-S...O=C contact [S...O 3.122 (2) Å, C-S...O 80.0 (2)°] is observed between the two molecular fragments bridged by the methylene group. In the crystal, C-H...O hydrogen bonds link molecules, forming chains along the b axis.

Related literature

For the biological activity of thiamethoxam, see: Maienfisch et al. (2001[Maienfisch, P., Huerlimann, H., Rindlisbacher, A., Gsell, L., Dettwiler, H., Haettenschwiler, J., Sieger, E. & Walti, M. (2001). Pest. Manag. Sci. 57, 165-176.], 2006[Maienfisch, P. (2006). Z. Naturforsch. Teil B, 61, 353-359.]); Suchail et al. (2001[Suchail, S., De Sousa, G. & Belzunces, L. P. (2001). Environ. Toxicol. Chem. 20, 2482-2486.]); Ford & Casida (2006[Ford, K. A. & Casida, J. E. (2006). Chem. Res. Toxicol. 19, 1549-1556.]). For the structure of thiamethoxam, see: Chopra et al. (2004[Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2413-o2414.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10ClN3O2S

  • Mr = 247.70

  • Orthorhombic, P 21 21 21

  • a = 4.6141 (2) Å

  • b = 11.7335 (4) Å

  • c = 20.1460 (8) Å

  • V = 1090.70 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.53 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.925, Tmax = 1.000

  • 22323 measured reflections

  • 2147 independent reflections

  • 1974 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.07

  • 2147 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 856 Friedel pairs

  • Flack parameter: 0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O7i 0.93 2.60 3.443 (3) 151
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2519 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2413-o2414.  [CSD] [CrossRef] [details]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Ford, K. A. & Casida, J. E. (2006). Chem. Res. Toxicol. 19, 1549-1556.  [CrossRef] [PubMed] [ChemPort]
Maienfisch, P. (2006). Z. Naturforsch. Teil B, 61, 353-359.  [ChemPort]
Maienfisch, P., Huerlimann, H., Rindlisbacher, A., Gsell, L., Dettwiler, H., Haettenschwiler, J., Sieger, E. & Walti, M. (2001). Pest. Manag. Sci. 57, 165-176.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suchail, S., De Sousa, G. & Belzunces, L. P. (2001). Environ. Toxicol. Chem. 20, 2482-2486.  [ISI] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3109  [ doi:10.1107/S1600536812042031 ]

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