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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2451
https://doi.org/10.1107/S1600536810033660

1-(2,2-Dimeth­­oxy­eth­yl)-8-nitro-1,2,3,5,6,7-hexa­hydro­imidazo[1,2-a]pyridin-5-ol

Zhongzhen Tian,a* Gaolei Wanga and Haijun Dongb

aShandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, People's Republic of China, and bSchool of Sciences, University of Jinan, People's Republic of China
*Correspondence e-mail: chm_tianzz@ujn.edu.cn

(Received 19 August 2010; accepted 20 August 2010; online 28 August 2010)

In the title compound, C11H19N3O5, the six-membered ring displays a half-chair conformation and the imidazolidine ring is essentially planar (r.m.s. deviation = 0.088 Å). An inter­molecular hydrogen bond between the hy­droxy O atom and a nitro O atom stabilizes the crystal packing.

Related literature

For related structures, see: Tian et al. (2010[Tian, Z., Dong, H., Li, D. & Wang, G. (2010). Acta Cryst. E66, o2330.]); Li et al. (2010[Li, D., Tian, Z., Wang, G., Wei, P. & Zhang, Y. (2010). Acta Cryst. E66, o2216.]). For background to neonicotinoid insecticides, see: Mori et al. (2001[Mori, K., Okumoto, T., Kawahara, N. & Ozoe, Y. (2001). Pest. Manage. Sci. 46, 40-46.]); Ohno et al. (2009[Ohno, I., Tomizawa, M., Durkin, K. A., Naruse, Y., Casida, J. E. & Kagabu, S. (2009). Chem. Res. Toxicol. 22, 476-482.]); Jeschke et al. (2008[Jeschke, P. & Nauen, R. (2008). Pest Manag. Sci. 64, 1084-1098.]); Tian et al. (2007[Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food. Chem. 55, 2288-2292.]).

[Scheme 1]

Experimental

Crystal data

  • C11H19N3O5

  • Mr = 273.29

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 1.0

  • 37886 measured reflections

  • 2723 independent reflections

  • 2100 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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

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) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033660/bt5332Isup2.hkl

checkCIF report


Comment top

Neonicotinoid insecticides have rapidly grown and become a new chemical class of insecticides in recent years because of their novel structure and mode of action compared with conventional insecticides (Ohno et al., 2009; Jeschke et al., 2008). We have synthesized a series of new compounds by introducing a tetrahydropyridine ring into the lead structure to improve photostability, in which the title compound exhibited moderate insecticidal activities against pea aphids.

The structure of the title compound is shown in Fig. 1 with the atom-numbering scheme. The title compound is a homologue of (E)-1-(2,2-dimethoxyethyl)-2-(nitromethylene)imidazolidine (Li et al., 2010). The six-membered ring displays a half-chair conformation and the imidazolidine ring is essentially planar (r.m.s. deviation = 0.088 Å). An intermolecular hydrogen bond between the hydroxyl group O atom and the nitro-group O stabilizes the crystal packing.

Related literature top

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 top

To a mixture of 1-((1,3-dithiolan-2-yl)methyl)-2-(nitromethylene)imidazolidine (2 mmol) were added olefin aldehyde (2.2 mmol), acetonitrile (20 ml), and a drop of concentrated hydrochloric acid. The reaction was carried out at 40°, and the progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed under reduced pressure, and the crude oil was purified by flash chromatography to give the desired product. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of dichloromethane and ethyl acetate of the title compound.

Refinement top

All H atoms were placed in their calculated positions and then refined using riding model with C—H = 0.96–0.98 Å, Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Structure description top

Neonicotinoid insecticides have rapidly grown and become a new chemical class of insecticides in recent years because of their novel structure and mode of action compared with conventional insecticides (Ohno et al., 2009; Jeschke et al., 2008). We have synthesized a series of new compounds by introducing a tetrahydropyridine ring into the lead structure to improve photostability, in which the title compound exhibited moderate insecticidal activities against pea aphids.

The structure of the title compound is shown in Fig. 1 with the atom-numbering scheme. The title compound is a homologue of (E)-1-(2,2-dimethoxyethyl)-2-(nitromethylene)imidazolidine (Li et al., 2010). The six-membered ring displays a half-chair conformation and the imidazolidine ring is essentially planar (r.m.s. deviation = 0.088 Å). An intermolecular hydrogen bond between the hydroxyl group O atom and the nitro-group O stabilizes the crystal packing.

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are shown as spheres of arbitrary size.
[Figure 2] Fig. 2. Intermolecular hydrogen bonding in the crystal structure.
1-(2,2-Dimethoxyethyl)-8-nitro-1,2,3,5,6,7- hexahydroimidazo[1,2-a]pyridin-5-ol top
Crystal data top
C11H19N3O5F(000) = 584
Mr = 273.29Dx = 1.355 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 15115 reflections
a = 11.2337 (6) Åθ = 3.0–28.9°
b = 9.0903 (3) ŵ = 0.11 mm−1
c = 14.2618 (7) ÅT = 293 K
β = 113.124 (6)°Prism, colourless
V = 1339.36 (11) Å30.46 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2723 independent reflections
Radiation source: fine-focus sealed tube2100 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 16.0355 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −11→11
Tmin = 0.929, Tmax = 1.0l = −17→17
37886 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-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 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C11H19N3O5V = 1339.36 (11) Å3
Mr = 273.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.2337 (6) ŵ = 0.11 mm−1
b = 9.0903 (3) ÅT = 293 K
c = 14.2618 (7) Å0.46 × 0.20 × 0.16 mm
β = 113.124 (6)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2723 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2100 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 1.0Rint = 0.033
37886 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.06Δρmax = 0.18 e Å−3
2723 reflectionsΔρmin = −0.19 e Å−3
175 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
xyzUiso*/Ueq
N10.29875 (12)0.55756 (14)0.22689 (9)0.0425 (3)
O10.63771 (13)0.70130 (14)0.20749 (9)0.0628 (4)
H10.61170.73310.14910.094*
N20.47152 (13)0.53178 (15)0.19064 (9)0.0445 (3)
C50.42919 (14)0.56183 (15)0.26436 (10)0.0371 (3)
O40.38448 (13)0.73086 (14)0.41241 (9)0.0600 (3)
N30.49381 (14)0.67236 (15)0.43224 (9)0.0480 (3)
O50.58619 (14)0.69576 (16)0.51820 (8)0.0707 (4)
O20.02213 (12)0.59831 (16)0.16524 (10)0.0721 (4)
C80.22221 (16)0.51751 (18)0.28522 (12)0.0475 (4)
H8B0.27730.51830.35730.057*
H8A0.18920.41840.26710.057*
C10.52149 (15)0.59073 (16)0.36427 (10)0.0406 (4)
C40.60599 (16)0.55202 (18)0.20530 (12)0.0487 (4)
H40.62190.50290.15020.058*
C60.36474 (16)0.5264 (2)0.09100 (11)0.0533 (4)
H6A0.37310.44360.05110.064*
H6B0.35890.61660.05310.064*
C20.66126 (16)0.5530 (2)0.39249 (12)0.0550 (4)
H2A0.68920.48650.45030.066*
H2B0.71260.64200.41330.066*
O30.05036 (15)0.58840 (17)0.33329 (12)0.0822 (5)
C90.10981 (17)0.6218 (2)0.26575 (14)0.0533 (4)
H90.14010.72400.27480.064*
C70.25036 (17)0.5085 (2)0.11957 (12)0.0583 (5)
H7B0.17840.56900.07670.070*
H7A0.22260.40660.11330.070*
C30.68676 (18)0.4813 (2)0.30524 (14)0.0593 (5)
H3B0.77770.49110.31760.071*
H3A0.66650.37720.30240.071*
C11−0.0810 (2)0.7013 (3)0.12986 (19)0.0959 (8)
H11A−0.12680.69050.05750.144*
H11C−0.04690.79920.14490.144*
H11B−0.13910.68370.16320.144*
C100.0604 (3)0.6935 (3)0.40618 (19)0.1038 (9)
H10C0.02420.78460.37320.156*
H10B0.14990.70790.44950.156*
H10A0.01400.66110.44640.156*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0463 (7)0.0455 (7)0.0367 (7)−0.0014 (6)0.0174 (5)0.0008 (5)
O10.0799 (9)0.0637 (8)0.0487 (7)−0.0237 (7)0.0295 (7)−0.0008 (6)
N20.0509 (7)0.0518 (8)0.0352 (6)−0.0067 (6)0.0216 (6)−0.0049 (6)
C50.0503 (8)0.0298 (7)0.0356 (7)0.0001 (6)0.0216 (6)0.0037 (6)
O40.0738 (9)0.0590 (8)0.0535 (7)0.0098 (6)0.0316 (6)−0.0076 (6)
N30.0638 (9)0.0476 (8)0.0355 (7)−0.0002 (7)0.0224 (6)0.0012 (6)
O50.0843 (9)0.0892 (10)0.0313 (6)−0.0007 (8)0.0149 (6)−0.0112 (6)
O20.0559 (7)0.0772 (9)0.0729 (9)0.0166 (6)0.0144 (6)−0.0202 (7)
C80.0528 (9)0.0441 (9)0.0526 (9)−0.0010 (7)0.0284 (7)0.0035 (7)
C10.0515 (9)0.0403 (8)0.0330 (7)0.0005 (6)0.0200 (6)0.0033 (6)
C40.0579 (10)0.0517 (10)0.0464 (9)−0.0060 (8)0.0312 (8)−0.0083 (7)
C60.0636 (11)0.0617 (11)0.0350 (8)−0.0065 (8)0.0197 (7)−0.0068 (7)
C20.0541 (10)0.0666 (11)0.0409 (8)0.0061 (8)0.0150 (7)0.0070 (8)
O30.0895 (10)0.0801 (10)0.1065 (12)−0.0016 (8)0.0702 (10)−0.0059 (9)
C90.0553 (10)0.0478 (10)0.0646 (11)−0.0009 (8)0.0319 (8)−0.0056 (8)
C70.0587 (10)0.0735 (12)0.0402 (8)−0.0090 (9)0.0166 (8)−0.0065 (8)
C30.0579 (10)0.0598 (11)0.0643 (11)0.0100 (8)0.0284 (9)0.0031 (9)
C110.0779 (15)0.114 (2)0.0836 (16)0.0394 (14)0.0185 (12)−0.0119 (14)
C100.132 (2)0.120 (2)0.0766 (16)0.0389 (18)0.0594 (16)−0.0029 (14)
Geometric parameters (Å, º) top
N1—C51.3488 (19)C6—H6A0.9700
N1—C81.4579 (19)C6—H6B0.9700
N1—C71.4777 (19)C6—C71.502 (2)
O1—H10.8200C2—H2A0.9700
O1—C41.400 (2)C2—H2B0.9700
N2—C51.3412 (19)C2—C31.528 (2)
N2—C41.453 (2)O3—C91.404 (2)
N2—C61.4566 (19)O3—C101.384 (3)
C5—C11.419 (2)C9—H90.9800
O4—N31.2643 (18)C7—H7B0.9700
N3—O51.2751 (17)C7—H7A0.9700
N3—C11.350 (2)C3—H3B0.9700
O2—C91.400 (2)C3—H3A0.9700
O2—C111.419 (2)C11—H11A0.9600
C8—H8B0.9700C11—H11C0.9600
C8—H8A0.9700C11—H11B0.9600
C8—C91.515 (2)C10—H10C0.9600
C1—C21.500 (2)C10—H10B0.9600
C4—H40.9800C10—H10A0.9600
C4—C31.501 (2)
N1—C5—C1130.90 (13)C1—C2—H2A109.0
N1—C8—H8B109.2C1—C2—H2B109.0
N1—C8—H8A109.2C1—C2—C3112.98 (14)
N1—C8—C9112.03 (13)C4—O1—H1109.5
N1—C7—C6104.03 (13)C4—N2—C6123.77 (12)
N1—C7—H7B111.0C4—C3—C2110.73 (14)
N1—C7—H7A111.0C4—C3—H3B109.5
O1—C4—N2111.53 (14)C4—C3—H3A109.5
O1—C4—H4109.5C6—C7—H7B111.0
O1—C4—C3109.90 (14)C6—C7—H7A111.0
N2—C5—N1110.37 (13)H6A—C6—H6B109.3
N2—C5—C1118.73 (14)C2—C3—H3B109.5
N2—C4—H4109.5C2—C3—H3A109.5
N2—C4—C3106.79 (13)H2A—C2—H2B107.8
N2—C6—H6A111.4O3—C9—C8109.02 (15)
N2—C6—H6B111.4O3—C9—H9110.4
N2—C6—C7101.74 (12)O3—C10—H10C109.5
C5—N1—C8125.00 (12)O3—C10—H10B109.5
C5—N1—C7108.64 (13)O3—C10—H10A109.5
C5—N2—C4122.00 (13)C9—O2—C11114.29 (15)
C5—N2—C6111.22 (13)C9—C8—H8B109.2
C5—C1—C2120.14 (13)C9—C8—H8A109.2
O4—N3—O5119.82 (13)C7—C6—H6A111.4
O4—N3—C1123.22 (13)C7—C6—H6B111.4
N3—C1—C5122.62 (14)H7B—C7—H7A109.0
N3—C1—C2116.43 (14)C3—C4—H4109.5
O5—N3—C1116.87 (14)C3—C2—H2A109.0
O2—C9—C8107.03 (13)C3—C2—H2B109.0
O2—C9—O3109.65 (15)H3B—C3—H3A108.1
O2—C9—H9110.4H11A—C11—H11C109.5
O2—C11—H11A109.5H11A—C11—H11B109.5
O2—C11—H11C109.5H11C—C11—H11B109.5
O2—C11—H11B109.5C10—O3—C9116.47 (18)
C8—N1—C7117.14 (13)H10C—C10—H10B109.5
C8—C9—H9110.4H10C—C10—H10A109.5
H8B—C8—H8A107.9H10B—C10—H10A109.5
N1—C5—C1—N3−25.8 (2)O5—N3—C1—C2−7.5 (2)
N1—C5—C1—C2164.90 (15)C8—N1—C5—N2150.28 (14)
N1—C8—C9—O268.81 (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—C261.14 (19)C1—C2—C3—C438.9 (2)
N2—C5—C1—N3154.74 (15)C4—N2—C5—N1169.82 (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—N119.23 (18)C6—N2—C5—N18.77 (17)
C5—N1—C8—C9135.02 (15)C6—N2—C5—C1−171.63 (13)
C5—N1—C7—C6−15.63 (19)C6—N2—C4—O186.66 (18)
C5—N2—C4—O1−71.99 (18)C6—N2—C4—C3−153.26 (15)
C5—N2—C4—C348.10 (19)C7—N1—C5—N24.82 (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—C2168.94 (14)C11—O2—C9—O370.0 (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—C8113.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.821.892.6966 (16)169
Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC11H19N3O5
Mr273.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.2337 (6), 9.0903 (3), 14.2618 (7)
β (°) 113.124 (6)
V (Å3)1339.36 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.46 × 0.20 × 0.16
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.929, 1.0
No. of measured, independent and
observed [I > 2σ(I)] reflections		37886, 2723, 2100
Rint0.033
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.120, 1.06
No. of reflections2723
No. of parameters175
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.18, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5i0.821.892.6966 (16)168.8
Symmetry code: (i) x, −y+3/2, z−1/2.
 

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant 20902037) and the Doctoral Foundation of University of Jinan (B0542) for financial support.

References

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2451
https://doi.org/10.1107/S1600536810033660
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