1-(2,2-Dimeth-oxy-eth-yl)-8-nitro-1,2,3,5,6,7-hexa-hydro-imidazo[1,2-a]pyridin-5-ol.

In the title compound, C(11)H(19)N(3)O(5), the six-membered ring displays a half-chair conformation and the imidazolidine ring is essentially planar (r.m.s. deviation = 0.088 Å). An inter-molecular hydrogen bond between the hy-droxy O atom and a nitro O atom stabilizes the crystal packing.

Related literature

For related structures, see: Tian et al. (2010 ▶); Li et al. (2010 ▶). For background to neonicotinoid insecticides, see: Mori et al. (2001 ▶); Ohno et al. (2009 ▶); Jeschke et al. (2008 ▶); Tian et al. (2007 ▶).

Experimental

Crystal data

C11H19N3O5

M = 273.29

Monoclinic,

a = 11.2337 (6) Å

b = 9.0903 (3) Å

c = 14.2618 (7) Å

β = 113.124 (6)°

V = 1339.36 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.46 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.929, T max = 1.0

37886 measured reflections

2723 independent reflections

2100 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.06

2723 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 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: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033660/bt5332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033660/bt5332Isup2.hkl

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

C11H19N3O5	F(000) = 584
Mr = 273.29	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 15115 reflections
a = 11.2337 (6) Å	θ = 3.0–28.9°
b = 9.0903 (3) Å	µ = 0.11 mm−1
c = 14.2618 (7) Å	T = 293 K
β = 113.124 (6)°	Prism, colourless
V = 1339.36 (11) Å3	0.46 × 0.20 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2723 independent reflections
Radiation source: fine-focus sealed tube	2100 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 16.0355 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.929, Tmax = 1.0	l = −17→17
37886 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.2341P] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max = 0.005
175 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 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
N1	0.29875 (12)	0.55756 (14)	0.22689 (9)	0.0425 (3)
O1	0.63771 (13)	0.70130 (14)	0.20749 (9)	0.0628 (4)
H1	0.6117	0.7331	0.1491	0.094*
N2	0.47152 (13)	0.53178 (15)	0.19064 (9)	0.0445 (3)
C5	0.42919 (14)	0.56183 (15)	0.26436 (10)	0.0371 (3)
O4	0.38448 (13)	0.73086 (14)	0.41241 (9)	0.0600 (3)
N3	0.49381 (14)	0.67236 (15)	0.43224 (9)	0.0480 (3)
O5	0.58619 (14)	0.69576 (16)	0.51820 (8)	0.0707 (4)
O2	0.02213 (12)	0.59831 (16)	0.16524 (10)	0.0721 (4)
C8	0.22221 (16)	0.51751 (18)	0.28522 (12)	0.0475 (4)
H8B	0.2773	0.5183	0.3573	0.057*
H8A	0.1892	0.4184	0.2671	0.057*
C1	0.52149 (15)	0.59073 (16)	0.36427 (10)	0.0406 (4)
C4	0.60599 (16)	0.55202 (18)	0.20530 (12)	0.0487 (4)
H4	0.6219	0.5029	0.1502	0.058*
C6	0.36474 (16)	0.5264 (2)	0.09100 (11)	0.0533 (4)
H6A	0.3731	0.4436	0.0511	0.064*
H6B	0.3589	0.6166	0.0531	0.064*
C2	0.66126 (16)	0.5530 (2)	0.39249 (12)	0.0550 (4)
H2A	0.6892	0.4865	0.4503	0.066*
H2B	0.7126	0.6420	0.4133	0.066*
O3	0.05036 (15)	0.58840 (17)	0.33329 (12)	0.0822 (5)
C9	0.10981 (17)	0.6218 (2)	0.26575 (14)	0.0533 (4)
H9	0.1401	0.7240	0.2748	0.064*
C7	0.25036 (17)	0.5085 (2)	0.11957 (12)	0.0583 (5)
H7B	0.1784	0.5690	0.0767	0.070*
H7A	0.2226	0.4066	0.1133	0.070*
C3	0.68676 (18)	0.4813 (2)	0.30524 (14)	0.0593 (5)
H3B	0.7777	0.4911	0.3176	0.071*
H3A	0.6665	0.3772	0.3024	0.071*
C11	−0.0810 (2)	0.7013 (3)	0.12986 (19)	0.0959 (8)
H11A	−0.1268	0.6905	0.0575	0.144*
H11C	−0.0469	0.7992	0.1449	0.144*
H11B	−0.1391	0.6837	0.1632	0.144*
C10	0.0604 (3)	0.6935 (3)	0.40618 (19)	0.1038 (9)
H10C	0.0242	0.7846	0.3732	0.156*
H10B	0.1499	0.7079	0.4495	0.156*
H10A	0.0140	0.6611	0.4464	0.156*

	U11	U22	U33	U12	U13	U23
N1	0.0463 (7)	0.0455 (7)	0.0367 (7)	−0.0014 (6)	0.0174 (5)	0.0008 (5)
O1	0.0799 (9)	0.0637 (8)	0.0487 (7)	−0.0237 (7)	0.0295 (7)	−0.0008 (6)
N2	0.0509 (7)	0.0518 (8)	0.0352 (6)	−0.0067 (6)	0.0216 (6)	−0.0049 (6)
C5	0.0503 (8)	0.0298 (7)	0.0356 (7)	0.0001 (6)	0.0216 (6)	0.0037 (6)
O4	0.0738 (9)	0.0590 (8)	0.0535 (7)	0.0098 (6)	0.0316 (6)	−0.0076 (6)
N3	0.0638 (9)	0.0476 (8)	0.0355 (7)	−0.0002 (7)	0.0224 (6)	0.0012 (6)
O5	0.0843 (9)	0.0892 (10)	0.0313 (6)	−0.0007 (8)	0.0149 (6)	−0.0112 (6)
O2	0.0559 (7)	0.0772 (9)	0.0729 (9)	0.0166 (6)	0.0144 (6)	−0.0202 (7)
C8	0.0528 (9)	0.0441 (9)	0.0526 (9)	−0.0010 (7)	0.0284 (7)	0.0035 (7)
C1	0.0515 (9)	0.0403 (8)	0.0330 (7)	0.0005 (6)	0.0200 (6)	0.0033 (6)
C4	0.0579 (10)	0.0517 (10)	0.0464 (9)	−0.0060 (8)	0.0312 (8)	−0.0083 (7)
C6	0.0636 (11)	0.0617 (11)	0.0350 (8)	−0.0065 (8)	0.0197 (7)	−0.0068 (7)
C2	0.0541 (10)	0.0666 (11)	0.0409 (8)	0.0061 (8)	0.0150 (7)	0.0070 (8)
O3	0.0895 (10)	0.0801 (10)	0.1065 (12)	−0.0016 (8)	0.0702 (10)	−0.0059 (9)
C9	0.0553 (10)	0.0478 (10)	0.0646 (11)	−0.0009 (8)	0.0319 (8)	−0.0056 (8)
C7	0.0587 (10)	0.0735 (12)	0.0402 (8)	−0.0090 (9)	0.0166 (8)	−0.0065 (8)
C3	0.0579 (10)	0.0598 (11)	0.0643 (11)	0.0100 (8)	0.0284 (9)	0.0031 (9)
C11	0.0779 (15)	0.114 (2)	0.0836 (16)	0.0394 (14)	0.0185 (12)	−0.0119 (14)
C10	0.132 (2)	0.120 (2)	0.0766 (16)	0.0389 (18)	0.0594 (16)	−0.0029 (14)

N1—C5	1.3488 (19)	C6—H6A	0.9700
N1—C8	1.4579 (19)	C6—H6B	0.9700
N1—C7	1.4777 (19)	C6—C7	1.502 (2)
O1—H1	0.8200	C2—H2A	0.9700
O1—C4	1.400 (2)	C2—H2B	0.9700
N2—C5	1.3412 (19)	C2—C3	1.528 (2)
N2—C4	1.453 (2)	O3—C9	1.404 (2)
N2—C6	1.4566 (19)	O3—C10	1.384 (3)
C5—C1	1.419 (2)	C9—H9	0.9800
O4—N3	1.2643 (18)	C7—H7B	0.9700
N3—O5	1.2751 (17)	C7—H7A	0.9700
N3—C1	1.350 (2)	C3—H3B	0.9700
O2—C9	1.400 (2)	C3—H3A	0.9700
O2—C11	1.419 (2)	C11—H11A	0.9600
C8—H8B	0.9700	C11—H11C	0.9600
C8—H8A	0.9700	C11—H11B	0.9600
C8—C9	1.515 (2)	C10—H10C	0.9600
C1—C2	1.500 (2)	C10—H10B	0.9600
C4—H4	0.9800	C10—H10A	0.9600
C4—C3	1.501 (2)
N1—C5—C1	130.90 (13)	C1—C2—H2A	109.0
N1—C8—H8B	109.2	C1—C2—H2B	109.0
N1—C8—H8A	109.2	C1—C2—C3	112.98 (14)
N1—C8—C9	112.03 (13)	C4—O1—H1	109.5
N1—C7—C6	104.03 (13)	C4—N2—C6	123.77 (12)
N1—C7—H7B	111.0	C4—C3—C2	110.73 (14)
N1—C7—H7A	111.0	C4—C3—H3B	109.5
O1—C4—N2	111.53 (14)	C4—C3—H3A	109.5
O1—C4—H4	109.5	C6—C7—H7B	111.0
O1—C4—C3	109.90 (14)	C6—C7—H7A	111.0
N2—C5—N1	110.37 (13)	H6A—C6—H6B	109.3
N2—C5—C1	118.73 (14)	C2—C3—H3B	109.5
N2—C4—H4	109.5	C2—C3—H3A	109.5
N2—C4—C3	106.79 (13)	H2A—C2—H2B	107.8
N2—C6—H6A	111.4	O3—C9—C8	109.02 (15)
N2—C6—H6B	111.4	O3—C9—H9	110.4
N2—C6—C7	101.74 (12)	O3—C10—H10C	109.5
C5—N1—C8	125.00 (12)	O3—C10—H10B	109.5
C5—N1—C7	108.64 (13)	O3—C10—H10A	109.5
C5—N2—C4	122.00 (13)	C9—O2—C11	114.29 (15)
C5—N2—C6	111.22 (13)	C9—C8—H8B	109.2
C5—C1—C2	120.14 (13)	C9—C8—H8A	109.2
O4—N3—O5	119.82 (13)	C7—C6—H6A	111.4
O4—N3—C1	123.22 (13)	C7—C6—H6B	111.4
N3—C1—C5	122.62 (14)	H7B—C7—H7A	109.0
N3—C1—C2	116.43 (14)	C3—C4—H4	109.5
O5—N3—C1	116.87 (14)	C3—C2—H2A	109.0
O2—C9—C8	107.03 (13)	C3—C2—H2B	109.0
O2—C9—O3	109.65 (15)	H3B—C3—H3A	108.1
O2—C9—H9	110.4	H11A—C11—H11C	109.5
O2—C11—H11A	109.5	H11A—C11—H11B	109.5
O2—C11—H11C	109.5	H11C—C11—H11B	109.5
O2—C11—H11B	109.5	C10—O3—C9	116.47 (18)
C8—N1—C7	117.14 (13)	H10C—C10—H10B	109.5
C8—C9—H9	110.4	H10C—C10—H10A	109.5
H8B—C8—H8A	107.9	H10B—C10—H10A	109.5
N1—C5—C1—N3	−25.8 (2)	O5—N3—C1—C2	−7.5 (2)
N1—C5—C1—C2	164.90 (15)	C8—N1—C5—N2	150.28 (14)
N1—C8—C9—O2	68.81 (18)	C8—N1—C5—C1	−29.3 (2)
N1—C8—C9—O3	−172.66 (14)	C8—N1—C7—C6	−164.17 (14)
O1—C4—C3—C2	61.14 (19)	C1—C2—C3—C4	38.9 (2)
N2—C5—C1—N3	154.74 (15)	C4—N2—C5—N1	169.82 (14)
N2—C5—C1—C2	−14.6 (2)	C4—N2—C5—C1	−10.6 (2)
N2—C4—C3—C2	−59.99 (19)	C4—N2—C6—C7	−178.50 (15)
N2—C6—C7—N1	19.23 (18)	C6—N2—C5—N1	8.77 (17)
C5—N1—C8—C9	135.02 (15)	C6—N2—C5—C1	−171.63 (13)
C5—N1—C7—C6	−15.63 (19)	C6—N2—C4—O1	86.66 (18)
C5—N2—C4—O1	−71.99 (18)	C6—N2—C4—C3	−153.26 (15)
C5—N2—C4—C3	48.10 (19)	C7—N1—C5—N2	4.82 (17)
C5—N2—C6—C7	−17.84 (18)	C7—N1—C5—C1	−174.72 (15)
C5—C1—C2—C3	−1.2 (2)	C7—N1—C8—C9	−82.11 (18)
O4—N3—C1—C5	−0.8 (2)	C11—O2—C9—C8	−171.90 (18)
O4—N3—C1—C2	168.94 (14)	C11—O2—C9—O3	70.0 (2)
N3—C1—C2—C3	−171.20 (15)	C10—O3—C9—O2	−129.9 (2)
O5—N3—C1—C5	−177.19 (14)	C10—O3—C9—C8	113.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5i	0.82	1.89	2.6966 (16)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5i	0.82	1.89	2.6966 (16)	169

Symmetry code: (i) .