(E)-3-[1-(2,4-Difluoro­phen­yl)eth­yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

Zhong, Y.; Li, C.; Xu, L.

doi:10.1107/S1600536810026425

Volume 66
Part 8
Page o1981
August 2010

Received 24 June 2010
Accepted 5 July 2010
Online 10 July 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.106
Data-to-parameter ratio = 13.3
Details

(E)-3-[1-(2,4-Difluorophenyl)ethyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

Yuan-yuan Zhong,^a Cong-cong Li ^a and Liang-zhong Xu ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: qknhs@yahoo.com.cn

The 1,3,5-oxadiazinane ring in the title compound, C₁₂H₁₄F₂N₄O₃, has a conformation intermediate between half-chair and screw-boat. The crystal structure is stabilized by weak intermolecular C-HO hydrogen bonds. Weak [pi] - [pi] interactions are indicated by the relatively long centroid-centroid distance of 3.9199 (12) Å and interplanar distance of 3.803 Å between symmetry-related benzene rings from neighbouring molecules.

Related literature

An important type of insecticide, oxadiazine compounds are highly efficient and of low toxicity, see: Gsell et al.(1998). The title compound has been used to synthesize many similar insecticides, see: Maienfisch et al. (1994). For the preparation of the title compound, see: Gottfied et al.(2001). For the related structures, see: Chopra et al., (2004); Kang et al. (2008). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₂H₁₄F₂N₄O₃
M_r = 300.27
Monoclinic, P 2₁ /c
a = 13.385 (3) Å
b = 6.7470 (13) Å
c = 15.073 (3) Å
= 101.25 (3)°
V = 1335.0 (5) Å³
Z = 4
Cu K radiation
= 1.11 mm^-1
T = 113 K
0.26 × 0.24 × 0.22 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: numerical (CrystalClear; Rigaku, 2005) T_min = 0.762, T_max = 0.793
13266 measured reflections
2567 independent reflections
2168 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.106
S = 1.09
2567 reflections
193 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1AO3ⁱ	0.99	2.50	3.1908 (16)	127
C3-H3AO2ⁱⁱ	0.99	2.51	3.4439 (18)	156
C4-H4CO2ⁱⁱⁱ	0.98	2.49	3.1665 (17)	126
C6-H6AO3^iv	0.98	2.39	3.2046 (18)	140
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2586 ).

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Chopra, D., Mohan, T. P., Rao, K. S. & Guru Row, T. N. (2004). Acta Cryst. E60, o2413-o2414.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gottfied, S., Thomas, R. & Verena, G. (2001). WO Patent 0100623.
Gsell, L. & Maientisch, P. (1998). WO Patent 9806710.
Kang, T.-N., Zhang, L., Ling, Y. & Yang, X.-L. (2008). Acta Cryst. E64, o1154.
Maienfisch, P. & Huerlimann, H. (1994). CN Patent 1084171.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds