(E)-1-[(1,3-Dioxan-4-yl)meth-yl]-2-(nitro-methyl-idene)imidazolidine.

In the title compound, C(9)H(15)N(3)O(4), the 1,3-dioxane ring displays a chair conformation and the five-membered ring is close to planar (r.m.s. deviation = 0.054 Å). An intra-molecular N-H⋯O hydrogen bond to one of the nitro-group O atoms generates an S(6) ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into C(6) chains propagating in [010] and a C-H⋯O link also occurs.

Related literature

For a related structure, see Tian et al. (2009 ▶). For background to neonicotinoid insecticides, see Mori et al. (2001 ▶); Ohno et al. (2009 ▶); Jeschke & Nauen (2008 ▶); Kagabu (1997 ▶); Tian et al. (2007 ▶).

Experimental

Crystal data

C9H15N3O4

M = 229.24

Monoclinic,

a = 5.0138 (4) Å

b = 9.8092 (9) Å

c = 21.7162 (18) Å

V = 1068.03 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.42 × 0.26 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.954, T max = 0.982

5866 measured reflections

1933 independent reflections

1395 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.174

S = 1.10

1933 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 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/S1600536810032691/hb5607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032691/hb5607Isup2.hkl

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

C9H15N3O4	F(000) = 488
Mr = 229.24	Dx = 1.426 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2831 reflections
a = 5.0138 (4) Å	θ = 3.5–28.7°
b = 9.8092 (9) Å	µ = 0.11 mm−1
c = 21.7162 (18) Å	T = 296 K
β = 90°	Prism, colourless
V = 1068.03 (16) Å3	0.42 × 0.26 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	1933 independent reflections
Radiation source: fine-focus sealed tube	1395 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.954, Tmax = 0.982	k = −11→11
5866 measured reflections	l = −26→26

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1126P)2] where P = (Fo2 + 2Fc2)/3
1933 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
O2	0.7955 (3)	0.71286 (16)	0.23056 (8)	0.0532 (5)
N1	0.7422 (4)	0.58813 (19)	0.22961 (9)	0.0420 (5)
C2	0.3945 (4)	0.6124 (2)	0.30617 (10)	0.0343 (5)
O3	0.2691 (4)	0.39753 (16)	0.44986 (7)	0.0536 (5)
N2	0.4042 (4)	0.74655 (19)	0.31417 (9)	0.0435 (5)
H2	0.5038	0.8003	0.2930	0.052*
C1	0.5501 (4)	0.5344 (2)	0.26581 (10)	0.0390 (6)
H1	0.5196	0.4409	0.2638	0.047*
N3	0.2104 (4)	0.55718 (19)	0.34370 (8)	0.0421 (5)
O1	0.8720 (4)	0.51016 (18)	0.19406 (9)	0.0640 (6)
C5	0.1287 (5)	0.4153 (2)	0.34624 (11)	0.0432 (6)
H5A	0.1514	0.3753	0.3057	0.052*
H5B	−0.0597	0.4115	0.3563	0.052*
C6	0.2786 (5)	0.3314 (2)	0.39185 (10)	0.0406 (6)
H6	0.4653	0.3268	0.3787	0.049*
O4	0.2921 (5)	0.1954 (2)	0.50513 (9)	0.0741 (7)
C7	0.1743 (5)	0.1882 (2)	0.39737 (11)	0.0453 (6)
H7A	0.2109	0.1387	0.3596	0.054*
H7B	−0.0175	0.1904	0.4032	0.054*
C4	0.0734 (5)	0.6627 (3)	0.37948 (11)	0.0474 (6)
H4B	0.0835	0.6438	0.4233	0.057*
H4A	−0.1125	0.6699	0.3675	0.057*
C3	0.2257 (5)	0.7920 (2)	0.36326 (11)	0.0507 (7)
H3A	0.1061	0.8629	0.3488	0.061*
H3B	0.3255	0.8258	0.3984	0.061*
C9	0.4109 (7)	0.3220 (3)	0.49462 (13)	0.0653 (8)
H9A	0.5930	0.3086	0.4808	0.078*
H9B	0.4163	0.3731	0.5328	0.078*
C8	0.3037 (7)	0.1152 (3)	0.45115 (13)	0.0651 (8)
H8B	0.2132	0.0293	0.4583	0.078*
H8A	0.4885	0.0956	0.4413	0.078*

	U11	U22	U33	U12	U13	U23
O2	0.0554 (11)	0.0286 (10)	0.0756 (13)	−0.0030 (7)	0.0114 (9)	0.0037 (8)
N1	0.0450 (11)	0.0278 (11)	0.0533 (12)	0.0051 (8)	0.0010 (9)	0.0052 (9)
C2	0.0377 (11)	0.0255 (12)	0.0397 (12)	0.0020 (9)	−0.0111 (9)	0.0038 (9)
O3	0.0719 (11)	0.0445 (11)	0.0443 (10)	−0.0009 (9)	−0.0041 (8)	−0.0026 (8)
N2	0.0474 (11)	0.0262 (10)	0.0569 (12)	0.0006 (8)	0.0004 (9)	0.0001 (9)
C1	0.0458 (13)	0.0261 (12)	0.0451 (13)	−0.0020 (9)	−0.0025 (10)	0.0019 (10)
N3	0.0524 (12)	0.0317 (11)	0.0423 (11)	−0.0025 (8)	0.0010 (9)	0.0015 (8)
O1	0.0772 (13)	0.0398 (11)	0.0750 (13)	0.0116 (9)	0.0302 (10)	0.0017 (10)
C5	0.0450 (13)	0.0410 (14)	0.0437 (13)	−0.0091 (11)	−0.0063 (10)	0.0035 (10)
C6	0.0441 (12)	0.0376 (13)	0.0399 (12)	−0.0056 (10)	−0.0015 (9)	0.0002 (10)
O4	0.1233 (19)	0.0549 (12)	0.0441 (10)	−0.0022 (12)	0.0030 (11)	0.0089 (9)
C7	0.0536 (14)	0.0350 (13)	0.0471 (14)	−0.0038 (10)	0.0041 (11)	−0.0019 (10)
C4	0.0462 (13)	0.0482 (15)	0.0477 (13)	0.0052 (11)	−0.0027 (10)	−0.0031 (12)
C3	0.0677 (17)	0.0349 (14)	0.0494 (14)	0.0088 (12)	−0.0027 (12)	−0.0024 (11)
C9	0.095 (2)	0.0565 (18)	0.0446 (15)	0.0001 (15)	−0.0174 (14)	0.0038 (13)
C8	0.096 (2)	0.0411 (16)	0.0584 (17)	0.0051 (15)	0.0003 (15)	0.0049 (13)

O2—N1	1.253 (2)	C6—H6	0.9800
N1—C1	1.350 (3)	C6—C7	1.504 (3)
N1—O1	1.267 (2)	O4—C9	1.396 (4)
C2—N2	1.329 (3)	O4—C8	1.413 (3)
C2—C1	1.401 (3)	C7—H7A	0.9700
C2—N3	1.345 (3)	C7—H7B	0.9700
O3—C6	1.418 (3)	C7—C8	1.516 (4)
O3—C9	1.414 (3)	C4—H4B	0.9700
N2—H2	0.8600	C4—H4A	0.9700
N2—C3	1.462 (3)	C4—C3	1.522 (4)
C1—H1	0.9300	C3—H3A	0.9700
N3—C5	1.452 (3)	C3—H3B	0.9700
N3—C4	1.465 (3)	C9—H9A	0.9700
C5—H5A	0.9700	C9—H9B	0.9700
C5—H5B	0.9700	C8—H8B	0.9700
C5—C6	1.491 (3)	C8—H8A	0.9700
O2—N1—C1	121.61 (19)	H5A—C5—H5B	107.6
O2—N1—O1	119.35 (19)	C6—C5—H5A	108.7
N1—C1—C2	123.2 (2)	C6—C5—H5B	108.7
N1—C1—H1	118.4	C6—C7—H7A	109.5
C2—N2—H2	124.0	C6—C7—H7B	109.5
C2—N2—C3	112.0 (2)	C6—C7—C8	110.7 (2)
C2—C1—H1	118.4	O4—C9—O3	111.3 (2)
C2—N3—C5	127.03 (19)	O4—C9—H9A	109.4
C2—N3—C4	111.03 (19)	O4—C9—H9B	109.4
O3—C6—C5	108.72 (19)	O4—C8—C7	111.0 (2)
O3—C6—H6	108.2	O4—C8—H8B	109.4
O3—C6—C7	110.17 (18)	O4—C8—H8A	109.4
O3—C9—H9A	109.4	C7—C6—H6	108.2
O3—C9—H9B	109.4	C7—C8—H8B	109.4
N2—C2—C1	127.1 (2)	C7—C8—H8A	109.4
N2—C2—N3	110.1 (2)	H7A—C7—H7B	108.1
N2—C3—C4	102.82 (18)	C4—C3—H3A	111.2
N2—C3—H3A	111.2	C4—C3—H3B	111.2
N2—C3—H3B	111.2	H4B—C4—H4A	109.1
N3—C2—C1	122.80 (19)	C3—N2—H2	124.0
N3—C5—H5A	108.7	C3—C4—H4B	111.1
N3—C5—H5B	108.7	C3—C4—H4A	111.1
N3—C5—C6	114.35 (18)	H3A—C3—H3B	109.1
N3—C4—H4B	111.1	C9—O3—C6	110.8 (2)
N3—C4—H4A	111.1	C9—O4—C8	110.0 (2)
N3—C4—C3	103.34 (19)	H9A—C9—H9B	108.0
O1—N1—C1	119.04 (19)	C8—C7—H7A	109.5
C5—N3—C4	121.66 (19)	C8—C7—H7B	109.5
C5—C6—H6	108.2	H8B—C8—H8A	108.0
C5—C6—C7	113.16 (18)
O2—N1—C1—C2	0.9 (3)	N3—C5—C6—O3	52.3 (3)
C2—N2—C3—C4	−7.0 (2)	N3—C5—C6—C7	175.06 (19)
C2—N3—C5—C6	92.4 (3)	N3—C4—C3—N2	7.6 (2)
C2—N3—C4—C3	−6.3 (2)	O1—N1—C1—C2	−179.4 (2)
O3—C6—C7—C8	−49.0 (3)	C5—N3—C4—C3	179.39 (19)
N2—C2—C1—N1	1.8 (3)	C5—C6—C7—C8	−170.9 (2)
N2—C2—N3—C5	176.06 (19)	C6—O3—C9—O4	−64.4 (3)
N2—C2—N3—C4	2.1 (2)	C6—C7—C8—O4	49.6 (3)
C1—C2—N2—C3	−176.0 (2)	C4—N3—C5—C6	−94.3 (3)
C1—C2—N3—C5	−4.5 (3)	C9—O3—C6—C5	−179.5 (2)
C1—C2—N3—C4	−178.49 (19)	C9—O3—C6—C7	56.0 (3)
N3—C2—N2—C3	3.4 (2)	C9—O4—C8—C7	−56.4 (3)
N3—C2—C1—N1	−177.49 (18)	C8—O4—C9—O3	64.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	2.17	2.694 (3)	119
N2—H2···O1i	0.86	2.17	2.824 (3)	133
C1—H1···O2ii	0.93	2.42	3.249 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	2.17	2.694 (3)	119
N2—H2⋯O1i	0.86	2.17	2.824 (3)	133
C1—H1⋯O2ii	0.93	2.42	3.249 (3)	148

Symmetry codes: (i) ; (ii) .