rac-1-(Furan-2-ylmeth­yl)-N-nitro-5-(oxolan-2-ylmeth­yl)-1,3,5-triazinan-2-imine

Sun, C.-W.; Ma, X.-B.; Bu, H.-F.

doi:10.1107/S1600536810036561

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2581

doi:10.1107/S1600536810036561

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rac-1-(Furan-2-ylmethyl)-N-nitro-5-(oxolan-2-ylmethyl)-1,3,5-triazinan-2-imine

Chuan-Wen Sun,^a ^* Xu-Bo Ma ^a and Hong-Fei Bu ^a

^aDepartment of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, People's Republic of China
^*Correspondence e-mail: maxubo6688@yahoo.com.cn

(Received 1 September 2010; accepted 13 September 2010; online 18 September 2010)

In the title compound C₁₃H₁₉N₅O₄, which belongs to the insecticidally active neonicotinoid group of compounds, the triazane ring exhibits a half-chair conformation. The large discrepancy between the two nitro O—N—N bond angles [116.1 (2) and 123.98 (19)°] may be attributed to intramolecular N—H⋯O hydrogen bonding involving one of the nitro O atoms as the acceptor. The delocalization of the electrons extends as far as the nitro group, forming coplanar π-electron networks. In the crystal, inversion dimers lined by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For general background to neonicotinoids, see: Kagabu et al. (2005 ); Peter & Ralf (2008 ); Riley & Merz (2007 ); Tian et al. (2007 ); Tomizawa et al. (2000 ). For the synthesis, see: Zhu et al. (2010 ).

Experimental

Crystal data

C₁₃H₁₉N₅O₄
M_r = 309.33
Monoclinic, P 2₁ /n
a = 11.1898 (12) Å
b = 9.262 (1) Å
c = 14.4863 (15) Å
β = 99.276 (2)°
V = 1481.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
9196 measured reflections
2902 independent reflections
2615 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.164
S = 1.18
2902 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.82 (3)	1.97 (3)	2.563 (3)	128 (2)
N2—H2⋯O1ⁱ	0.82 (3)	2.43 (3)	3.035 (3)	132 (2)
Symmetry code: (i) -x, -y+2, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036561/zs2064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036561/zs2064Isup2.hkl

checkCIF report

Comment top

In recent years, the neonicotinoids have been the fastest-growing class of insecticides used in modern crop protection (Tomizawa et al., 2000; Kagabu et al., 2005; Tian et al., 2007; Peter & Ralf, 2008). We report here crystal structure of one of these compounds, C₁₃H₁₉N₅O₄, the title compound (I). In the structure of (I) (Fig. 1), the triazine ring exhibits a half-chair conformation with a dihedral angle of 50.62° between plane A (C8, N3, C7, N2, C6) and plane B (C6, N1, C8). The bond angles C8–N1–C6, N1–C6–N2, C6–N2–C7, N2–C7–N3, C7–N3–C8 and N3–C8–N1 are 108.15 (19), 111.20 (18), 122.69 (19), 118.54 (19), 119.94 (18) and 111.98 (18)° respectively, in turn indicating asymmetry and strong tensility in the 1,3,5-hexahydrotriazine ring. The large discrepancy between the nitro O3–N5–N4 and O4–N5–N4 bond angles [116.1 (2) and 123.98 (19)° respectively] may be attributed to the intramolecular N2–H···O3 hydrogen bond (Table 1). There is also a single intermolecular N–H···O hydrogen bond associated with N2 (Fig. 2).

Interestingly, due to the transfer of the lone-pair of electrons from the hetero-N atoms to the C7═N4 double bond, the C7–N2 and C7–N3 bond lengths (1.327 (3) Å and 1.338 (3) Å), are both remarkably shorter than the pure C–N single bond (1.49 Å), but close to the C═C value (1.33 Å). The delocalization of the electrons extends as far as the electron-withdrawing nitro group, forming a coplanar π-electron network. A six-membered plane C (C7, N4, N5, O3, H2 and N2) is established by the intramolecular N2–H···O3 hydrogen bond. In addition, planes A and C form an enlarged plane D (comprising C6, C8, N3, C7, N2, H2, N4, O3 and O4).

Related literature top

For general background to neonicotinoids, see: Kagabu et al. (2005); Peter & Ralf (2008); Riley & Merz (2007); Tian et al. (2007); Tomizawa et al. (2000). For the synthesis, see: Zhu et al. (2010).

Experimental top

The title compound was prepared by the literature method (Zhu et al., 2010) and was recrystallized from ethanol-water (10:1), giving colorless crystals (yield 79.6%). ¹HNMR(CDCl₃, 400 Hz): 9.61 (1H, s, NH), 7.37–7.36 (2H, d, J = 0.8 Hz, furan—H), 6.38–6.34 (3H,m,furan—H), 4.49–4.47(6H, m, CH₂—furan, triazine–H), 3.97–3.85 (2H, m, CH₂—tetrahydrofuran), 3.53–3.12 (3H, m, tetrahydrofuran—H) 1.86–1.64(4H, m, tetrahydrofuran—H); IR(KBr, cm^-1) 3278(N—H), 1588 (C═N), 1195 (C—O—C), 1060 (C—N), Anal.: calcd. for C₁₃H₁₉N₅O₄: C 50.48, H 6.19, N 22.64%; found, C 51.03, H 6.17, N 22.75%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme with non-H atoms shown as 50% probability displacement ellipsoids.
	Fig. 2. A perspective view of the packing of the title compound (I). Hydrogen bonds are shown as dashed lines.

rac-1-(Furan-2-ylmethyl)-N-nitro-5-(oxolan-2-ylmethyl)- 1,3,5-triazinan-2-imine top

Crystal data top

C₁₃H₁₉N₅O₄	F(000) = 656
M_r = 309.33	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4051 reflections
a = 11.1898 (12) Å	θ = 2.5–28.3°
b = 9.262 (1) Å	µ = 0.11 mm⁻¹
c = 14.4863 (15) Å	T = 298 K
β = 99.276 (2)°	Block, colorless
V = 1481.7 (3) Å³	0.16 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 26.0°, θ_min = 2.1°
ϕ and ω scans	h = −12→13
9196 measured reflections	k = −9→11
2902 independent reflections	l = −17→17

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0599P)² + 0.7103P] where P = (F_o² + 2F_c²)/3
2902 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₉N₅O₄	V = 1481.7 (3) Å³
M_r = 309.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1898 (12) Å	µ = 0.11 mm⁻¹
b = 9.262 (1) Å	T = 298 K
c = 14.4863 (15) Å	0.16 × 0.12 × 0.10 mm
β = 99.276 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2615 reflections with I > 2σ(I)
9196 measured reflections	R_int = 0.054
2902 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.34 e Å⁻³
2902 reflections	Δρ_min = −0.21 e Å⁻³
202 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
C1	0.1890 (2)	1.0871 (3)	−0.01634 (16)	0.0487 (6)
H1	0.1262	1.0589	−0.0684	0.058*
C2	0.2996 (3)	1.1394 (3)	−0.0536 (2)	0.0696 (8)
H2A	0.3568	1.0614	−0.0561	0.084*
H2B	0.2777	1.1802	−0.1157	0.084*
C3	0.3511 (3)	1.2516 (4)	0.0146 (2)	0.0736 (9)
H3A	0.3924	1.3257	−0.0156	0.088*
H3B	0.4078	1.2094	0.0651	0.088*
C4	0.2436 (3)	1.3124 (3)	0.0502 (2)	0.0615 (7)
H4A	0.2630	1.3307	0.1169	0.074*
H4B	0.2191	1.4027	0.0188	0.074*
C5	0.2134 (2)	0.9639 (3)	0.05245 (16)	0.0473 (6)
H5A	0.2792	0.9902	0.1017	0.057*
H5B	0.1420	0.9468	0.0809	0.057*
C6	0.1429 (2)	0.7399 (3)	−0.02488 (15)	0.0482 (6)
H6A	0.1663	0.6655	−0.0656	0.058*
H6B	0.0791	0.7970	−0.0608	0.058*
C7	0.16647 (19)	0.6493 (2)	0.13610 (15)	0.0382 (5)
C8	0.3341 (2)	0.7465 (3)	0.06578 (16)	0.0476 (6)
H8A	0.4025	0.8074	0.0900	0.057*
H8B	0.3630	0.6705	0.0290	0.057*
C9	0.3679 (2)	0.6694 (3)	0.23428 (16)	0.0532 (6)
H9A	0.3267	0.6217	0.2798	0.064*
H9B	0.3899	0.7657	0.2574	0.064*
C10	0.4795 (2)	0.5882 (3)	0.22556 (16)	0.0482 (6)
C11	0.5939 (2)	0.6300 (3)	0.23025 (18)	0.0540 (6)
H11	0.6233	0.7234	0.2408	0.065*
C12	0.6623 (2)	0.5070 (4)	0.2163 (2)	0.0693 (8)
H12	0.7454	0.5036	0.2161	0.083*
C13	0.5869 (3)	0.3982 (4)	0.2035 (3)	0.0808 (10)
H13	0.6081	0.3034	0.1925	0.097*
N1	0.24528 (17)	0.8309 (2)	0.00685 (12)	0.0440 (5)
N2	0.09726 (18)	0.6721 (2)	0.05406 (13)	0.0434 (5)
H2	0.024 (2)	0.659 (3)	0.0503 (18)	0.052*
N3	0.28447 (16)	0.6810 (2)	0.14521 (12)	0.0442 (5)
N4	0.13154 (16)	0.5958 (2)	0.21520 (13)	0.0463 (5)
N5	0.01557 (17)	0.5609 (2)	0.21385 (14)	0.0486 (5)
O1	0.14841 (15)	1.20885 (19)	0.03162 (12)	0.0540 (5)
O2	0.47092 (18)	0.4451 (2)	0.20884 (18)	0.0799 (7)
O3	−0.06477 (17)	0.5800 (3)	0.14598 (15)	0.0902 (8)
O4	−0.00984 (17)	0.5099 (2)	0.28658 (14)	0.0709 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0558 (14)	0.0487 (14)	0.0407 (12)	−0.0013 (11)	0.0050 (10)	0.0002 (10)
C2	0.092 (2)	0.0565 (17)	0.0706 (18)	−0.0087 (16)	0.0424 (17)	0.0028 (14)
C3	0.0628 (17)	0.078 (2)	0.084 (2)	−0.0169 (16)	0.0242 (16)	−0.0094 (17)
C4	0.0651 (17)	0.0516 (16)	0.0669 (17)	−0.0046 (13)	0.0075 (13)	−0.0092 (13)
C5	0.0543 (14)	0.0514 (14)	0.0384 (11)	−0.0023 (11)	0.0141 (10)	0.0002 (10)
C6	0.0558 (14)	0.0530 (14)	0.0361 (11)	0.0010 (11)	0.0086 (10)	−0.0008 (10)
C7	0.0385 (11)	0.0360 (11)	0.0409 (11)	0.0031 (9)	0.0088 (9)	−0.0005 (9)
C8	0.0448 (12)	0.0543 (14)	0.0470 (12)	0.0011 (11)	0.0175 (10)	0.0064 (11)
C9	0.0432 (13)	0.0758 (18)	0.0407 (12)	−0.0032 (12)	0.0072 (10)	0.0061 (12)
C10	0.0418 (12)	0.0613 (16)	0.0393 (11)	−0.0063 (11)	0.0004 (9)	0.0113 (11)
C11	0.0406 (12)	0.0648 (16)	0.0580 (14)	−0.0129 (12)	0.0121 (11)	0.0088 (12)
C12	0.0416 (14)	0.093 (2)	0.0730 (18)	0.0042 (15)	0.0090 (13)	0.0168 (17)
C13	0.0614 (18)	0.069 (2)	0.108 (3)	0.0143 (17)	0.0027 (17)	0.0073 (19)
N1	0.0493 (11)	0.0454 (11)	0.0393 (9)	0.0019 (9)	0.0125 (8)	0.0025 (8)
N2	0.0386 (10)	0.0493 (12)	0.0416 (10)	−0.0025 (9)	0.0046 (8)	0.0033 (8)
N3	0.0370 (10)	0.0562 (12)	0.0403 (10)	0.0008 (8)	0.0091 (8)	0.0102 (8)
N4	0.0369 (10)	0.0568 (12)	0.0465 (10)	−0.0022 (9)	0.0099 (8)	0.0112 (9)
N5	0.0423 (11)	0.0519 (12)	0.0523 (12)	−0.0010 (9)	0.0101 (9)	0.0095 (9)
O1	0.0495 (10)	0.0493 (10)	0.0636 (11)	0.0033 (8)	0.0104 (8)	−0.0040 (8)
O2	0.0524 (12)	0.0665 (14)	0.1163 (19)	−0.0084 (10)	−0.0001 (11)	0.0061 (12)
O3	0.0461 (11)	0.154 (2)	0.0675 (13)	−0.0258 (13)	0.0006 (10)	0.0314 (14)
O4	0.0549 (11)	0.0947 (16)	0.0677 (12)	−0.0047 (10)	0.0235 (9)	0.0345 (11)

Geometric parameters (Å, º) top

C1—O1	1.436 (3)	C7—N4	1.362 (3)
C1—C2	1.508 (4)	C8—N1	1.433 (3)
C1—C5	1.510 (3)	C8—N3	1.485 (3)
C1—H1	0.9800	C8—H8A	0.9700
C2—C3	1.485 (4)	C8—H8B	0.9700
C2—H2A	0.9700	C9—N3	1.469 (3)
C2—H2B	0.9700	C9—C10	1.481 (3)
C3—C4	1.494 (4)	C9—H9A	0.9700
C3—H3A	0.9700	C9—H9B	0.9700
C3—H3B	0.9700	C10—C11	1.329 (3)
C4—O1	1.426 (3)	C10—O2	1.348 (3)
C4—H4A	0.9700	C11—C12	1.405 (4)
C4—H4B	0.9700	C11—H11	0.9300
C5—N1	1.469 (3)	C12—C13	1.309 (4)
C5—H5A	0.9700	C12—H12	0.9300
C5—H5B	0.9700	C13—O2	1.382 (4)
C6—N1	1.436 (3)	C13—H13	0.9300
C6—N2	1.467 (3)	N2—H2	0.82 (3)
C6—H6A	0.9700	N4—N5	1.335 (3)
C6—H6B	0.9700	N5—O4	1.229 (3)
C7—N2	1.327 (3)	N5—O3	1.233 (3)
C7—N3	1.338 (3)

O1—C1—C2	105.2 (2)	N1—C8—N3	111.98 (18)
O1—C1—C5	108.15 (18)	N1—C8—H8A	109.2
C2—C1—C5	114.1 (2)	N3—C8—H8A	109.2
O1—C1—H1	109.7	N1—C8—H8B	109.2
C2—C1—H1	109.7	N3—C8—H8B	109.2
C5—C1—H1	109.7	H8A—C8—H8B	107.9
C3—C2—C1	103.8 (2)	N3—C9—C10	112.8 (2)
C3—C2—H2A	111.0	N3—C9—H9A	109.0
C1—C2—H2A	111.0	C10—C9—H9A	109.0
C3—C2—H2B	111.0	N3—C9—H9B	109.0
C1—C2—H2B	111.0	C10—C9—H9B	109.0
H2A—C2—H2B	109.0	H9A—C9—H9B	107.8
C2—C3—C4	104.2 (2)	C11—C10—O2	109.6 (2)
C2—C3—H3A	110.9	C11—C10—C9	131.8 (3)
C4—C3—H3A	110.9	O2—C10—C9	118.6 (2)
C2—C3—H3B	110.9	C10—C11—C12	107.4 (3)
C4—C3—H3B	110.9	C10—C11—H11	126.3
H3A—C3—H3B	108.9	C12—C11—H11	126.3
O1—C4—C3	107.4 (2)	C13—C12—C11	106.9 (3)
O1—C4—H4A	110.2	C13—C12—H12	126.6
C3—C4—H4A	110.2	C11—C12—H12	126.6
O1—C4—H4B	110.2	C12—C13—O2	109.9 (3)
C3—C4—H4B	110.2	C12—C13—H13	125.1
H4A—C4—H4B	108.5	O2—C13—H13	125.1
N1—C5—C1	111.59 (18)	C8—N1—C6	108.15 (19)
N1—C5—H5A	109.3	C8—N1—C5	112.63 (19)
C1—C5—H5A	109.3	C6—N1—C5	113.40 (19)
N1—C5—H5B	109.3	C7—N2—C6	122.69 (19)
C1—C5—H5B	109.3	C7—N2—H2	117.9 (18)
H5A—C5—H5B	108.0	C6—N2—H2	118.7 (18)
N1—C6—N2	111.20 (18)	C7—N3—C9	123.22 (18)
N1—C6—H6A	109.4	C7—N3—C8	119.94 (18)
N2—C6—H6A	109.4	C9—N3—C8	116.49 (18)
N1—C6—H6B	109.4	N5—N4—C7	119.09 (19)
N2—C6—H6B	109.4	O4—N5—O3	119.9 (2)
H6A—C6—H6B	108.0	O4—N5—N4	116.1 (2)
N2—C7—N3	118.54 (19)	O3—N5—N4	123.98 (19)
N2—C7—N4	127.3 (2)	C4—O1—C1	109.54 (19)
N3—C7—N4	114.15 (19)	C10—O2—C13	106.2 (2)

O1—C1—C2—C3	29.5 (3)	N1—C6—N2—C7	−25.4 (3)
C5—C1—C2—C3	−88.8 (3)	N2—C7—N3—C9	175.7 (2)
C1—C2—C3—C4	−30.1 (3)	N4—C7—N3—C9	−4.3 (3)
C2—C3—C4—O1	20.2 (3)	N2—C7—N3—C8	2.8 (3)
O1—C1—C5—N1	175.01 (18)	N4—C7—N3—C8	−177.2 (2)
C2—C1—C5—N1	−68.3 (3)	C10—C9—N3—C7	130.5 (2)
N3—C9—C10—C11	110.1 (3)	C10—C9—N3—C8	−56.4 (3)
N3—C9—C10—O2	−69.1 (3)	N1—C8—N3—C7	28.7 (3)
O2—C10—C11—C12	−0.3 (3)	N1—C8—N3—C9	−144.7 (2)
C9—C10—C11—C12	−179.6 (2)	N2—C7—N4—N5	−0.1 (4)
C10—C11—C12—C13	0.3 (3)	N3—C7—N4—N5	179.9 (2)
C11—C12—C13—O2	−0.2 (4)	C7—N4—N5—O4	178.3 (2)
N3—C8—N1—C6	−56.5 (3)	C7—N4—N5—O3	−3.5 (4)
N3—C8—N1—C5	69.6 (2)	C3—C4—O1—C1	−1.6 (3)
N2—C6—N1—C8	54.5 (2)	C2—C1—O1—C4	−17.4 (3)
N2—C6—N1—C5	−71.2 (2)	C5—C1—O1—C4	104.8 (2)
C1—C5—N1—C8	144.4 (2)	C11—C10—O2—C13	0.2 (3)
C1—C5—N1—C6	−92.4 (2)	C9—C10—O2—C13	179.6 (2)
N3—C7—N2—C6	−4.4 (3)	C12—C13—O2—C10	0.0 (4)
N4—C7—N2—C6	175.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.82 (3)	1.97 (3)	2.563 (3)	128 (2)
N2—H2···O1ⁱ	0.82 (3)	2.43 (3)	3.035 (3)	132 (2)

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉N₅O₄
M_r	309.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.1898 (12), 9.262 (1), 14.4863 (15)
β (°)	99.276 (2)
V (Å³)	1481.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9196, 2902, 2615
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.164, 1.18
No. of reflections	2902
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
N2—H2···O3	0.82 (3)	1.97 (3)	2.563 (3)	128 (2)
N2—H2···O1ⁱ	0.82 (3)	2.43 (3)	3.035 (3)	132 (2)

Symmetry code: (i) −x, −y+2, −z.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kagabu, S., Ito, N., Imai, R., Hieta, Y. & Nishimura, K. (2005). J. Pestic. Sci. 30, 409–413. Web of Science CrossRef CAS Google Scholar
Peter, J. & Ralf, N. (2008). J. Pest. Manag. Sci. A, 64, 1064–1098. Google Scholar
Riley, K. E. Jr & Merz, K. M. (2007). J. Phys. Chem. A, 111, 1688–1694. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Z. Z., Jiang, Z. X., Li, Z., Song, G. H. & Huang, Q. C. (2007). J. Agric. Food Chem. 55, 143–147. Web of Science CrossRef PubMed CAS Google Scholar
Tomizawa, M., Lee, D. L. & Casida, J. E. (2000). J. Agric. Food Chem. 48, 6016–6024. Web of Science CrossRef PubMed CAS Google Scholar
Zhu, J., Xue, S. J., Wang, H. F., Yang, D. R. & Jin, J. (2010). Chin. J. Struct. Chem. 29, 400–406. CAS Google Scholar

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Volume 66| Part 10| October 2010| Page o2581

doi:10.1107/S1600536810036561

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

rac-1-(Furan-2-ylmeth­yl)-N-nitro-5-(oxolan-2-ylmeth­yl)-1,3,5-triazinan-2-imine

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Experimental

Crystal data

Data collection

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Supporting information

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organic compounds

rac-1-(Furan-2-ylmethyl)-N-nitro-5-(oxolan-2-ylmethyl)-1,3,5-triazinan-2-imine