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

Kant, R.; Gupta, V.K.; Kapoor, K.; Shripanavar, C.S.; Banerjee, K.

doi:10.1107/S1600536812042031

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 (C-C) = 0.004 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 15.7
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Chetan S. Shripanavar ^b and Kaushik Banerjee ^b

^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-SO=C contact [SO 3.122 (2) Å, C-SO 80.0 (2)°] is observed between the two molecular fragments bridged by the methylene group. In the crystal, C-HO hydrogen bonds link molecules, forming chains along the b axis.

Related literature

For the biological activity of thiamethoxam, see: Maienfisch et al. (2001, 2006); Suchail et al. (2001); Ford & Casida (2006). For the structure of thiamethoxam, see: Chopra et al. (2004). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₈H₁₀ClN₃O₂S
M_r = 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 radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.925, T_max = 1.000
22323 measured reflections
2147 independent reflections
1974 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.081
S = 1.07
2147 reflections
137 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 856 Friedel pairs
Flack parameter: 0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O7ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Ford, K. A. & Casida, J. E. (2006). Chem. Res. Toxicol. 19, 1549-1556.
Maienfisch, P. (2006). Z. Naturforsch. Teil B, 61, 353-359.
Maienfisch, P., Huerlimann, H., Rindlisbacher, A., Gsell, L., Dettwiler, H., Haettenschwiler, J., Sieger, E. & Walti, M. (2001). Pest. Manag. Sci. 57, 165-176.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suchail, S., De Sousa, G. & Belzunces, L. P. (2001). Environ. Toxicol. Chem. 20, 2482-2486.

organic compounds