(E)-1-(2,2-Dimeth-oxy-eth-yl)-2-(nitro-methyl-idene)imidazolidine.

In the title compound, C(8)H(15)N(3)O(4), the 2-(nitro-methyl-ene)imidazolidine fragment is close to being planar (r.m.s. deviation = 0.027 Å), which may be correlated with delocalization of the electrons and the effect of the strongly electron-withdrawing NO(2) group. An intra-molecular N-H⋯O link generates an S(6) ring. The same H atom also forms a weak inter-molecular N-H⋯O hydrogen bond, which results in C(7) chains propagating in [010].

Related literature

For background to neonicotinoid insecticides, see Moriya et al. (1992 ▶). For the synthesis, see: Tian et al. (2007 ▶).

Experimental

Crystal data

C8H15N3O4

M = 217.23

Monoclinic,

a = 10.444 (2) Å

b = 6.8676 (17) Å

c = 14.441 (3) Å

β = 99.953 (14)°

V = 1020.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.32 × 0.26 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.983

8629 measured reflections

2330 independent reflections

1849 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.06

2330 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030266/hb5567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030266/hb5567Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H15N3O4	F(000) = 464
Mr = 217.23	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3493 reflections
a = 10.444 (2) Å	θ = 2.9–27.3°
b = 6.8676 (17) Å	µ = 0.11 mm−1
c = 14.441 (3) Å	T = 296 K
β = 99.953 (14)°	Prism, colourless
V = 1020.2 (4) Å3	0.32 × 0.26 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	2330 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.965, Tmax = 0.983	k = −8→8
8629 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1844P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2330 reflections	Δρmax = 0.25 e Å−3
139 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.00359 (12)	0.08330 (19)	0.63950 (8)	0.0427 (3)
H1A	0.0562	0.0860	0.5937	0.051*
C2	0.06233 (12)	0.08637 (17)	0.73529 (8)	0.0406 (3)
C3	0.09094 (16)	0.0794 (2)	0.89827 (9)	0.0563 (4)
H3A	0.0816	−0.0387	0.9333	0.068*
H3B	0.0774	0.1913	0.9364	0.068*
C4	0.22254 (15)	0.0880 (2)	0.86762 (9)	0.0597 (4)
H4A	0.2701	0.2036	0.8921	0.072*
H4B	0.2741	−0.0262	0.8888	0.072*
C5	0.29097 (12)	0.08628 (19)	0.70666 (9)	0.0461 (3)
H5A	0.2533	0.0386	0.6447	0.055*
H5B	0.3573	−0.0057	0.7342	0.055*
C6	0.35394 (11)	0.28135 (19)	0.69663 (8)	0.0414 (3)
H6	0.3643	0.3483	0.7574	0.050*
C7	0.31179 (18)	0.5845 (2)	0.62367 (12)	0.0641 (4)
H7A	0.3323	0.6410	0.6853	0.096*
H7B	0.2446	0.6594	0.5860	0.096*
H7C	0.3880	0.5846	0.5948	0.096*
C8	0.48007 (15)	0.1666 (3)	0.58408 (11)	0.0699 (5)
H8A	0.4495	0.0354	0.5873	0.105*
H8B	0.5676	0.1650	0.5719	0.105*
H8C	0.4252	0.2349	0.5343	0.105*
N1	−0.12619 (11)	0.07657 (17)	0.61267 (8)	0.0481 (3)
N2	0.00157 (12)	0.0812 (2)	0.80881 (8)	0.0569 (3)
H2	−0.0816	0.0792	0.8041	0.068*
N3	0.19059 (11)	0.09392 (17)	0.76437 (7)	0.0473 (3)
O1	−0.17315 (10)	0.07294 (17)	0.52580 (7)	0.0654 (3)
O2	−0.20198 (10)	0.0741 (2)	0.67215 (8)	0.0725 (4)
O3	0.26831 (8)	0.39078 (13)	0.63099 (6)	0.0476 (3)
O4	0.47709 (8)	0.26264 (15)	0.67127 (6)	0.0524 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (6)	0.0489 (7)	0.0367 (6)	−0.0019 (5)	0.0030 (5)	0.0045 (5)
C2	0.0448 (6)	0.0371 (6)	0.0384 (6)	−0.0040 (5)	0.0029 (5)	0.0046 (5)
C3	0.0749 (10)	0.0563 (9)	0.0359 (6)	−0.0084 (7)	0.0049 (6)	0.0040 (6)
C4	0.0647 (9)	0.0703 (10)	0.0380 (7)	−0.0080 (7)	−0.0082 (6)	0.0071 (6)
C5	0.0418 (6)	0.0450 (7)	0.0487 (7)	−0.0006 (5)	0.0001 (5)	−0.0001 (5)
C6	0.0349 (6)	0.0491 (7)	0.0379 (6)	−0.0021 (5)	−0.0001 (4)	−0.0028 (5)
C7	0.0774 (11)	0.0510 (9)	0.0627 (9)	−0.0060 (7)	0.0084 (8)	0.0084 (7)
C8	0.0467 (8)	0.1033 (13)	0.0602 (9)	0.0017 (8)	0.0108 (7)	−0.0211 (9)
N1	0.0461 (6)	0.0522 (7)	0.0437 (6)	−0.0003 (5)	0.0008 (5)	0.0042 (5)
N2	0.0519 (6)	0.0807 (9)	0.0379 (6)	−0.0050 (6)	0.0073 (5)	0.0037 (6)
N3	0.0450 (6)	0.0570 (7)	0.0368 (5)	−0.0083 (5)	−0.0013 (4)	0.0060 (5)
O1	0.0562 (6)	0.0879 (8)	0.0445 (5)	0.0038 (5)	−0.0124 (4)	0.0015 (5)
O2	0.0446 (6)	0.1143 (11)	0.0590 (6)	−0.0025 (6)	0.0096 (5)	0.0061 (6)
O3	0.0438 (5)	0.0477 (5)	0.0479 (5)	−0.0010 (4)	−0.0014 (4)	0.0026 (4)
O4	0.0342 (5)	0.0713 (7)	0.0495 (5)	−0.0050 (4)	0.0010 (4)	−0.0086 (5)

C1—N1	1.3447 (17)	C5—H5B	0.9700
C1—C2	1.4131 (17)	C6—O4	1.4028 (15)
C1—H1A	0.9300	C6—O3	1.4036 (15)
C2—N2	1.3282 (17)	C6—H6	0.9800
C2—N3	1.3339 (16)	C7—O3	1.4159 (18)
C3—N2	1.4573 (17)	C7—H7A	0.9600
C3—C4	1.516 (2)	C7—H7B	0.9600
C3—H3A	0.9700	C7—H7C	0.9600
C3—H3B	0.9700	C8—O4	1.4265 (18)
C4—N3	1.4711 (17)	C8—H8A	0.9600
C4—H4A	0.9700	C8—H8B	0.9600
C4—H4B	0.9700	C8—H8C	0.9600
C5—N3	1.4485 (18)	N1—O2	1.2647 (15)
C5—C6	1.5104 (18)	N1—O1	1.2658 (14)
C5—H5A	0.9700	N2—H2	0.8600
N1—C1—C2	121.87 (12)	O4—C6—H6	108.2
N1—C1—H1A	119.1	O3—C6—H6	108.2
C2—C1—H1A	119.1	C5—C6—H6	108.2
N2—C2—N3	110.00 (11)	O3—C7—H7A	109.5
N2—C2—C1	126.55 (12)	O3—C7—H7B	109.5
N3—C2—C1	123.45 (12)	H7A—C7—H7B	109.5
N2—C3—C4	102.41 (11)	O3—C7—H7C	109.5
N2—C3—H3A	111.3	H7A—C7—H7C	109.5
C4—C3—H3A	111.3	H7B—C7—H7C	109.5
N2—C3—H3B	111.3	O4—C8—H8A	109.5
C4—C3—H3B	111.3	O4—C8—H8B	109.5
H3A—C3—H3B	109.2	H8A—C8—H8B	109.5
N3—C4—C3	103.81 (11)	O4—C8—H8C	109.5
N3—C4—H4A	111.0	H8A—C8—H8C	109.5
C3—C4—H4A	111.0	H8B—C8—H8C	109.5
N3—C4—H4B	111.0	O2—N1—O1	119.47 (11)
C3—C4—H4B	111.0	O2—N1—C1	121.53 (11)
H4A—C4—H4B	109.0	O1—N1—C1	119.00 (12)
N3—C5—C6	113.17 (11)	C2—N2—C3	112.80 (12)
N3—C5—H5A	108.9	C2—N2—H2	123.6
C6—C5—H5A	108.9	C3—N2—H2	123.6
N3—C5—H5B	108.9	C2—N3—C5	127.22 (11)
C6—C5—H5B	108.9	C2—N3—C4	110.95 (11)
H5A—C5—H5B	107.8	C5—N3—C4	121.47 (11)
O4—C6—O3	112.25 (10)	C6—O3—C7	112.24 (10)
O4—C6—C5	112.21 (11)	C6—O4—C8	115.70 (10)
O3—C6—C5	107.61 (9)
N1—C1—C2—N2	0.7 (2)	C1—C2—N3—C5	−4.8 (2)
N1—C1—C2—N3	−179.68 (12)	N2—C2—N3—C4	1.74 (15)
N2—C3—C4—N3	0.09 (15)	C1—C2—N3—C4	−177.89 (12)
N3—C5—C6—O4	158.56 (10)	C6—C5—N3—C2	105.58 (14)
N3—C5—C6—O3	−77.48 (13)	C6—C5—N3—C4	−81.94 (15)
C2—C1—N1—O2	0.51 (19)	C3—C4—N3—C2	−1.09 (15)
C2—C1—N1—O1	−179.59 (12)	C3—C4—N3—C5	−174.68 (12)
N3—C2—N2—C3	−1.71 (16)	O4—C6—O3—C7	−62.38 (14)
C1—C2—N2—C3	177.90 (12)	C5—C6—O3—C7	173.69 (12)
C4—C3—N2—C2	0.95 (16)	O3—C6—O4—C8	−61.01 (16)
N2—C2—N3—C5	174.88 (12)	C5—C6—O4—C8	60.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	2.09	2.6394 (17)	121
N2—H2···O3i	0.86	2.64	3.3554 (16)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	2.09	2.6394 (17)	121
N2—H2⋯O3i	0.86	2.64	3.3554 (16)	141

Symmetry code: (i) .