3-[(E)-3,7-Dimethyl­octa-2,6-dien­yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

Kang, T.-N.; Zhang, L.; Ling, Y.; Yang, X.-L.

doi:10.1107/S160053680801492X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1154

doi:10.1107/S160053680801492X

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3-[(E)-3,7-Dimethylocta-2,6-dienyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

Tie-Niu Kang,^a Li Zhang,^a Yun Ling ^a and Xin-Ling Yang ^a ^*

^aDepartment of Applied Chemistry, China Agricultural University, Beijing 100094, People's Republic of China
^*Correspondence e-mail: yangxl@cau.edu.cn

(Received 17 March 2008; accepted 16 May 2008; online 24 May 2008)

The title compound, C₁₄H₂₄N₄O₃, was synthesized by the reaction of geranyl and 3-methyl-4-nitroimino-1,3,5-oxadiazinane. In the crystal structure, molecules are assembled by weak intermolecular C—H⋯O hydrogen bonds. The nitryl and the long carbon chain are located on the same side of the C=N bond due to the two weak intramolecular C—H⋯N hydrogen bonds; the configuration of the oxadiazinane is Z.

Related literature

For background literature, see: Bowers et al. (1972 ). For related literature, see: Yang et al. (2004 ); Van Oosten et al. (1990 ).

Experimental

Crystal data

C₁₄H₂₄N₄O₃
M_r = 296.37
Monoclinic, P 2₁ /c
a = 7.9318 (16) Å
b = 6.6423 (13) Å
c = 31.191 (7) Å
β = 99.55 (3)°
V = 1620.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.60 × 0.30 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.943, T_max = 0.993
7692 measured reflections
2825 independent reflections
1306 reflections with I > 2σ(I)
R_int = 0.0508

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.152
S = 0.84
2825 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1ⁱ	0.97	2.48	3.257 (4)	136
C3—H3A⋯N2ⁱⁱ	0.97	2.43	3.336 (4)	155
C3—H3B⋯O1ⁱⁱⁱ	0.97	2.38	3.264 (4)	151
C5—H5B⋯N1	0.97	2.53	3.117 (4)	119
C5—H5B⋯N2	0.97	2.55	2.960 (4)	105
C13—H13C⋯O2^iv	0.96	2.59	3.425 (5)	145
Symmetry codes: (i) x, y-1, z; (ii) $[-x-1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2000 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2000 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801492X/rk2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801492X/rk2083Isup2.hkl

checkCIF report

Comment top

E-b-farnesene (EBF), the primary component of aphides alarm pheromone, not only stimulate the movement of aphid (Bowers et al., 1972), but also possess the acute activity to many economically aphid species at a dose of 100 ng/aphid (Van Oosten et al., 1990). However, EBF is limited in field application due to its high volatility, readily air oxidation and degradation under field conditions. In order to improve its chemical stability and biological efficacy, the pharmacophore of neonicotinoids was introduced to substitute the conjugated double bond of EBF (Yang et al., 2004). The title compound (I), in which 3-methyl-5-(E)-3,7-dimethylocta-2,6-dienyl connect to N-nitro-1,3,5-oxadiazinan-4-imine instead of the conjugated double bond, was synthesized as EBF analogue with potent insecticidal activity. To study the further structure-activity relationship, we reported here its molecular and crystal structure. The molecular structure showed Z-isomer by the interaction forces of weak intramolecular C5–H5b···N1 and C5–H5b···N2 hydrogen bonds (Fig. 1). The compound was assembled by four weak intermolecular hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For background literature, see: Bowers et al. (1972). For related literature, see: Yang et al. (2004); Van Oosten et al. (1990).

Experimental top

To a solution of 3-methyl-N-nitro-1,3,5-oxadiazinan-4-imine (1.60 g, 10.0 mmol) dissolved in anhydrous acetonitrile (15 ml), geranyl (1.89 g, 10.1 mmol) was added. Then the reaction solution was slowly heated to reflux for 7h. After removing the solvent, the residue was purified by column chromatography on silica gel (200-300 mesh) with petroleum ether/ethylacetate (2.5:1v/v) as eluent to obtain the title compound I. Then, 50 mg I was dissolved in 20 ml me thanol. The solution was kept at room temperature for 20 d by natural evaporation to give colorless single crystals of I, suitable for X-Ray analysis.

¹H NMR (CDCl₃, 300 MHz) 1.60 (s, 3H, CH₃–C═C), 1.68 [s, 6H, (CH₃)₂C═C], 2.07~2.10 (t, J = 5.27 Hz, 4H, -CH₂–CH₂-), 3.05 (s, 3H, N–CH₃), 4.11 (d, J = 7.26, 2H,-CH₂–N), 4.09 (s, 2H, N–CH₂–O), 4.12 (s, 2H, O–CH₂–N), 5.03~5.18 (m, 2H, 2CH═C); Calc. for C₁₄H₂₄N₄O₃: C 56.74, H 8.16, N 18.90; found C 56.69, H 8.19, N 18.80.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO (Rigaku, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I with the atom numbering scheme. The displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of I. Hydrogen bonds are shown as dashed lines. Symmetry codes: (i) x, y-1, z; (ii) -x-1, y-1/2, -z+3/2; (iii) -x, y-1/2, -z+3/2; (iv) x+1, y, z.

3-[(E)-3,7-Dimethylocta-2,6-dienyl]-5-methyl-N-nitro- 1,3,5-oxadiazinan-4-imine top

Crystal data top

C₁₄H₂₄N₄O₃	F(000) = 640
M_r = 296.37	D_x = 1.215 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7693 reflections
a = 7.9318 (16) Å	θ = 2.6–25.0°
b = 6.6423 (13) Å	µ = 0.09 mm⁻¹
c = 31.191 (7) Å	T = 293 K
β = 99.55 (3)°	Block, colourless
V = 1620.5 (6) Å³	0.60 × 0.30 × 0.08 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2825 independent reflections
Radiation source: Fine-focus sealed tube	1306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 10.00 pixels mm^-1	θ_max = 25.0°, θ_min = 1.3°
ω scans	h = 0→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→0
T_min = 0.943, T_max = 0.993	l = −37→35
2825 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 0.84	w = 1/[σ²(F_o²) + (0.0843P)²] where P = (F_o² + 2F_c²)/3
2825 reflections	(Δ/σ)_max = 0.014
194 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₂₄N₄O₃	V = 1620.5 (6) Å³
M_r = 296.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9318 (16) Å	µ = 0.09 mm⁻¹
b = 6.6423 (13) Å	T = 293 K
c = 31.191 (7) Å	0.60 × 0.30 × 0.08 mm
β = 99.55 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2825 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1306 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.993	R_int = 0.051
2825 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 0.84	Δρ_max = 0.28 e Å⁻³
2825 reflections	Δρ_min = −0.30 e Å⁻³
194 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.0768 (3)	0.9179 (3)	0.82543 (8)	0.0604 (7)
O2	−0.2995 (3)	1.0170 (4)	0.85187 (8)	0.0670 (7)
O3	−0.1951 (2)	0.2689 (3)	0.74730 (7)	0.0512 (6)
N1	−0.2308 (3)	0.9002 (4)	0.82899 (8)	0.0459 (7)
N2	−0.3292 (3)	0.7617 (4)	0.80698 (8)	0.0453 (7)
N3	−0.1290 (3)	0.4939 (4)	0.80512 (8)	0.0414 (6)
N4	−0.3001 (3)	0.6021 (4)	0.74324 (8)	0.0392 (6)
C1	−0.2455 (3)	0.6227 (4)	0.78538 (9)	0.0362 (7)
C2	−0.0594 (4)	0.3511 (5)	0.77744 (10)	0.0472 (8)
H2a	0.0212	0.4183	0.7621	0.057*
H2b	0.0004	0.2445	0.7950	0.057*
C3	−0.2672 (4)	0.4183 (5)	0.71928 (10)	0.0501 (9)
H3a	−0.3739	0.3699	0.7027	0.060*
H3b	−0.1907	0.4502	0.6990	0.060*
C4	−0.4042 (4)	0.7564 (5)	0.71773 (10)	0.0560 (9)
H4a	−0.3882	0.7482	0.6879	0.084*
H4b	−0.3700	0.8871	0.7291	0.084*
H4c	−0.5225	0.7348	0.7195	0.084*
C5	−0.0734 (3)	0.4762 (5)	0.85230 (9)	0.0439 (8)
H5a	−0.1016	0.3433	0.8619	0.053*
H5b	−0.1332	0.5747	0.8672	0.053*
C6	0.1153 (4)	0.5098 (5)	0.86376 (10)	0.0474 (8)
H6	0.1567	0.6275	0.8532	0.057*
C7	0.2293 (4)	0.3932 (5)	0.88694 (10)	0.0499 (8)
C8	0.4169 (4)	0.4518 (6)	0.89472 (10)	0.0608 (10)
H8a	0.4835	0.3403	0.8864	0.073*
H8b	0.4328	0.5654	0.8763	0.073*
C9	0.4840 (4)	0.5072 (7)	0.94162 (11)	0.0740 (11)
H9a	0.4240	0.6254	0.9494	0.089*
H9b	0.4615	0.3976	0.9604	0.089*
C10	0.6736 (4)	0.5496 (6)	0.94863 (11)	0.0624 (10)
H10	0.7444	0.4383	0.9483	0.075*
C11	0.7505 (4)	0.7241 (6)	0.95516 (10)	0.0597 (9)
C12	0.9427 (5)	0.7390 (6)	0.96099 (13)	0.0838 (13)
H12a	0.9742	0.8405	0.9419	0.126*
H12b	0.9892	0.6117	0.9542	0.126*
H12c	0.9870	0.7744	0.9906	0.126*
C13	0.6634 (6)	0.9221 (6)	0.95783 (15)	0.0974 (14)
H13a	0.7091	0.9870	0.9848	0.146*
H13b	0.5430	0.9007	0.9565	0.146*
H13c	0.6824	1.0058	0.9340	0.146*
C14	0.1868 (5)	0.2002 (6)	0.90720 (13)	0.0861 (14)
H14a	0.2656	0.0975	0.9016	0.129*
H14b	0.0725	0.1605	0.8950	0.129*
H14c	0.1950	0.2183	0.9380	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0374 (12)	0.0485 (14)	0.0951 (18)	−0.0067 (11)	0.0103 (12)	−0.0033 (13)
O2	0.0714 (16)	0.0645 (16)	0.0645 (15)	0.0175 (13)	0.0094 (12)	−0.0191 (13)
O3	0.0433 (12)	0.0422 (12)	0.0677 (14)	−0.0059 (11)	0.0082 (11)	−0.0098 (12)
N1	0.0461 (17)	0.0434 (16)	0.0465 (16)	0.0077 (14)	0.0025 (13)	0.0017 (14)
N2	0.0296 (13)	0.0510 (16)	0.0534 (16)	0.0058 (13)	0.0011 (12)	−0.0096 (14)
N3	0.0336 (13)	0.0400 (14)	0.0478 (15)	0.0059 (12)	−0.0012 (11)	−0.0038 (13)
N4	0.0296 (12)	0.0432 (15)	0.0435 (15)	−0.0001 (11)	0.0027 (11)	−0.0017 (13)
C1	0.0183 (14)	0.0412 (18)	0.0479 (19)	−0.0034 (13)	0.0021 (13)	0.0002 (15)
C2	0.0379 (18)	0.0395 (18)	0.062 (2)	0.0052 (15)	0.0016 (15)	−0.0042 (17)
C3	0.0330 (17)	0.061 (2)	0.056 (2)	−0.0053 (16)	0.0070 (15)	−0.0113 (19)
C4	0.0399 (17)	0.074 (2)	0.0498 (19)	0.0089 (18)	−0.0048 (15)	0.0077 (18)
C5	0.0368 (16)	0.0465 (19)	0.0465 (18)	−0.0003 (15)	0.0014 (14)	0.0047 (16)
C6	0.0393 (17)	0.0513 (19)	0.0485 (18)	−0.0036 (16)	−0.0022 (14)	0.0069 (17)
C7	0.0458 (18)	0.056 (2)	0.0440 (18)	0.0006 (17)	−0.0053 (14)	−0.0021 (17)
C8	0.0424 (18)	0.082 (3)	0.053 (2)	0.0028 (18)	−0.0071 (16)	0.0019 (19)
C9	0.053 (2)	0.108 (3)	0.056 (2)	−0.015 (2)	−0.0043 (17)	−0.010 (2)
C10	0.046 (2)	0.072 (3)	0.065 (2)	−0.0023 (19)	−0.0049 (17)	−0.008 (2)
C11	0.057 (2)	0.066 (3)	0.053 (2)	0.000 (2)	−0.0002 (17)	−0.0038 (19)
C12	0.059 (2)	0.097 (3)	0.091 (3)	−0.022 (2)	0.002 (2)	−0.011 (3)
C13	0.100 (3)	0.084 (3)	0.105 (4)	0.010 (3)	0.008 (3)	−0.007 (3)
C14	0.078 (3)	0.067 (3)	0.097 (3)	−0.005 (2)	−0.032 (2)	0.027 (2)

Geometric parameters (Å, º) top

O1—N1	1.251 (3)	C6—H6	0.9300
O2—N1	1.240 (3)	C7—C14	1.493 (5)
O3—C3	1.382 (3)	C7—C8	1.518 (4)
O3—C2	1.416 (3)	C8—C9	1.517 (4)
N1—N2	1.323 (3)	C8—H8a	0.9700
N2—C1	1.376 (3)	C8—H8b	0.9700
N3—C1	1.333 (3)	C9—C10	1.510 (4)
N3—C2	1.452 (4)	C9—H9a	0.9700
N3—C5	1.469 (4)	C9—H9b	0.9700
N4—C1	1.321 (3)	C10—C11	1.310 (5)
N4—C4	1.465 (4)	C10—H10	0.9300
N4—C3	1.477 (4)	C11—C13	1.494 (5)
C2—H2a	0.9700	C11—C12	1.508 (5)
C2—H2b	0.9700	C12—H12a	0.9600
C3—H3a	0.9700	C12—H12b	0.9600
C3—H3b	0.9700	C12—H12c	0.9600
C4—H4a	0.9600	C13—H13a	0.9600
C4—H4b	0.9600	C13—H13b	0.9600
C4—H4c	0.9600	C13—H13c	0.9600
C5—C6	1.496 (4)	C14—H14a	0.9600
C5—H5a	0.9700	C14—H14b	0.9600
C5—H5b	0.9700	C14—H14c	0.9600
C6—C7	1.313 (4)

C3—O3—C2	109.4 (2)	C5—C6—H6	116.1
O2—N1—O1	121.4 (3)	C6—C7—C14	123.8 (3)
O2—N1—N2	117.2 (3)	C6—C7—C8	120.3 (3)
O1—N1—N2	121.3 (3)	C14—C7—C8	115.9 (3)
N1—N2—C1	115.5 (2)	C9—C8—C7	113.2 (3)
C1—N3—C2	116.6 (2)	C9—C8—H8a	108.9
C1—N3—C5	125.7 (2)	C7—C8—H8a	108.9
C2—N3—C5	117.6 (2)	C9—C8—H8b	108.9
C1—N4—C4	122.0 (2)	C7—C8—H8b	108.9
C1—N4—C3	122.2 (2)	H8a—C8—H8b	107.8
C4—N4—C3	115.7 (2)	C10—C9—C8	111.5 (3)
N4—C1—N3	118.7 (3)	C10—C9—H9a	109.3
N4—C1—N2	116.8 (2)	C8—C9—H9a	109.3
N3—C1—N2	123.9 (3)	C10—C9—H9b	109.3
O3—C2—N3	108.9 (2)	C8—C9—H9b	109.3
O3—C2—H2a	109.9	H9a—C9—H9b	108.0
N3—C2—H2a	109.9	C11—C10—C9	127.9 (4)
O3—C2—H2b	109.9	C11—C10—H10	116.0
N3—C2—H2b	109.9	C9—C10—H10	116.0
H2a—C2—H2b	108.3	C10—C11—C13	125.4 (3)
O3—C3—N4	111.3 (2)	C10—C11—C12	120.8 (3)
O3—C3—H3a	109.4	C13—C11—C12	113.7 (3)
N4—C3—H3a	109.4	C11—C12—H12a	109.5
O3—C3—H3b	109.4	C11—C12—H12b	109.5
N4—C3—H3b	109.4	H12a—C12—H12b	109.5
H3a—C3—H3b	108.0	C11—C12—H12c	109.5
N4—C4—H4a	109.5	H12a—C12—H12c	109.5
N4—C4—H4b	109.5	H12b—C12—H12c	109.5
H4a—C4—H4b	109.5	C11—C13—H13a	109.5
N4—C4—H4c	109.5	C11—C13—H13b	109.5
H4a—C4—H4c	109.5	H13a—C13—H13b	109.5
H4b—C4—H4c	109.5	C11—C13—H13c	109.5
N3—C5—C6	110.5 (2)	H13a—C13—H13c	109.5
N3—C5—H5a	109.6	H13b—C13—H13c	109.5
C6—C5—H5a	109.6	C7—C14—H14a	109.5
N3—C5—H5b	109.6	C7—C14—H14b	109.5
C6—C5—H5b	109.6	H14a—C14—H14b	109.5
H5a—C5—H5b	108.1	C7—C14—H14c	109.5
C7—C6—C5	127.9 (3)	H14a—C14—H14c	109.5
C7—C6—H6	116.1	H14b—C14—H14c	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.48	3.257 (4)	136
C3—H3A···N2ⁱⁱ	0.97	2.43	3.336 (4)	155
C3—H3B···O1ⁱⁱⁱ	0.97	2.38	3.264 (4)	151
C5—H5B···N1	0.97	2.53	3.117 (4)	119
C5—H5B···N2	0.97	2.55	2.960 (4)	105
C13—H13C···O2^iv	0.96	2.59	3.425 (5)	145

Symmetry codes: (i) x, y−1, z; (ii) −x−1, y−1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₄N₄O₃
M_r	296.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9318 (16), 6.6423 (13), 31.191 (7)
β (°)	99.55 (3)
V (Å³)	1620.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.30 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.943, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	2825, 2825, 1306
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.153, 0.84
No. of reflections	2825
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: RAPID-AUTO (Rigaku, 2000), CrystalStructure (Rigaku/MSC, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ⁱ	0.97	2.48	3.257 (4)	136
C3—H3A···N2ⁱⁱ	0.97	2.43	3.336 (4)	155
C3—H3B···O1ⁱⁱⁱ	0.97	2.38	3.264 (4)	151
C5—H5B···N1	0.97	2.53	3.117 (4)	119
C5—H5B···N2	0.97	2.55	2.960 (4)	105
C13—H13C···O2^iv	0.96	2.59	3.425 (5)	145

Symmetry codes: (i) x, y−1, z; (ii) −x−1, y−1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2; (iv) x+1, y, z.

Acknowledgements

This work was supported by the National Basic Research Program of China (grant No. 2003CB 114400), the National High Technology Research and Development Program of China (grant No. 2006 A A10A209) and the `11th Five-Year Plan' Scientific and Technological Support Project on Pesticide Development Engineering (grant No. 2006BAE01A01). The authors acknowledge Shi-Wei Zhang for carrying out the X-ray diffraction at the College of Chemistry and Molecular Engineering, Peking University, Beijing, People's Republic of China.

References

Bowers, W. S., Nault, L. R., Webb, R. E. & Dutky, S. R. (1972). Science, 177, 1121–1122. CrossRef PubMed CAS Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2000). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2000). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Van Oosten, A. M., Gut, J., Harrewijn, P. & Piron, P. G. M. (1990). Acta Phytopathol. Entomol. Hung. 25, 331–342. CAS Google Scholar
Yang, X. L., Huang, W. Y., Ling, Y., Kan, W., Fang, Y. L. & Zhang, Z. N. (2004). Chem. J. Chin. Univ. 25, 1657–1661. CAS Google Scholar

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Volume 64| Part 6| June 2008| Page o1154

doi:10.1107/S160053680801492X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[(E)-3,7-Di­methyl­octa-2,6-dien­yl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

3-[(E)-3,7-Dimethylocta-2,6-dienyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine