1-[(6-Chloro-3-pyrid­yl)meth­yl]-5-eth­oxy-8-nitro-1,2,3,5,6,7-hexa­hydro­imidazo[1,2-a]pyridine

Tian, Z.; Li, D.; Li, Z.

doi:10.1107/S1600536809037660

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2517

doi:10.1107/S1600536809037660

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1-[(6-Chloro-3-pyridyl)methyl]-5-ethoxy-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine

Zhongzhen Tian,^a ^* Dongmei Li ^a and Zhong Li ^b ^*

^aInstitute of Chemistry and Chemical Engineering, University of Jinan, 106 Jiwei Road, Jinan 250022, People's Republic of China, and ^bShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China
^*Correspondence e-mail: chm_tianzz@ujn.edu.cn, lizhong@ecust.edu.cn

(Received 26 July 2009; accepted 17 September 2009; online 26 September 2009)

In the title compound, C₁₅H₁₉ClN₄O₃, an active agrochemical possessing insecticidal activity, the dihedral angle between the mean planes passing through the pyridine ring and the five-membered ring is 87.3 (2)°. The fused pyridine ring adopts a twisted sofa conformation. The molecular structure features close intramolecular C—H⋯N and C—H⋯O hydrogen bonding.

Related literature

For related literature, see: Kagabu et al. (2002 ); Moriya et al. (1992 ); Tian et al. (2007 ); Tokumitsu (1990 ).

Experimental

Crystal data

C₁₅H₁₉ClN₄O₃
M_r = 338.79
Monoclinic, P 2₁ /c
a = 17.021 (3) Å
b = 5.5737 (8) Å
c = 18.334 (3) Å
β = 112.097 (3)°
V = 1611.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 290 K
0.50 × 0.24 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.922, T_max = 0.969
8970 measured reflections
3486 independent reflections
1870 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 0.82
3486 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O3	0.97	2.35	2.803 (3)	108
C13—H13⋯N1	0.93	2.54	2.891 (3)	103

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037660/bx2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037660/bx2230Isup2.hkl

checkCIF report

Comment top

Since the debut of Imidacloprid in the 1990 decade (Moriya et al., 1992), neonicotinoid insecticides have become rapidly an important chemical class of insecticides. Nitromethylene compounds (Kagabu et al., 2002) exhibited remarkably higher biological activity but poor photostability compared with Imidacloprid. Our synthetic interest was introducing dicyclic ring into the lead structure to improve its photostability and synthesizing a series of new compounds, in which compound (I) exhibited good insecticidal activities against pea aphids and was slightly weaker than that of imidacloprid (Tian et al., 2007).The dihedral angle between the mean planes passing through the pyridine ring and the five membered ring is 87.3 (2)°. The six membered N2/C3/C4/C5/C6/C7 ring adopts a twist sofa conformation. The title compound C₁₅H₁₉ClN₄O₃ , is an active agrochemical possessing insecticidal activity. The dihedral angle between the mean planes passing through the pyridine ring and the five membered ring is 87.3 (2)°. The six membered N2/C3/C4/C5/C6/C7 ring adopts a twist sofa conformation.The molecular structure is stabilized by intramolecular C— H··· N and C— H··· O hydrogen bond, Table 1.

Related literature top

For related literature, see: Kagabu et al. (2002); Moriya et al. (1992); Tian et al. (2007); Tokumitsu (1990).

Experimental top

The synthesis of the title compoud was following the reported method by Tokumitsu, 1990. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solution of dichloromethane and petroleum ether of the title compound. m.p. 399.8–400.8 K.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (a) with atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are shown as circles of arbitrary size and intramolecular hydrogen bonds are indicated by dotted lines.

1-[(6-Chloro-3-pyridyl)methyl]-5-ethoxy-8-nitro-1,2,3,5,6,7- hexahydroimidazo[1,2-a]pyridine top

Crystal data top

C₁₅H₁₉ClN₄O₃	F(000) = 712
M_r = 338.79	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1727 reflections
a = 17.021 (3) Å	θ = 4.8–47.4°
b = 5.5737 (8) Å	µ = 0.26 mm⁻¹
c = 18.334 (3) Å	T = 290 K
β = 112.097 (3)°	Prismatic, colourless
V = 1611.6 (4) Å³	0.50 × 0.24 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→21
T_min = 0.922, T_max = 0.969	k = −7→7
8970 measured reflections	l = −23→13

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max = 0.044
3486 reflections	Δρ_max = 0.32 e Å⁻³
210 parameters	Δρ_min = −0.24 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: 0.020 (2)

Crystal data top

C₁₅H₁₉ClN₄O₃	V = 1611.6 (4) Å³
M_r = 338.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.021 (3) Å	µ = 0.26 mm⁻¹
b = 5.5737 (8) Å	T = 290 K
c = 18.334 (3) Å	0.50 × 0.24 × 0.12 mm
β = 112.097 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1870 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.969	R_int = 0.082
8970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 0.82	Δρ_max = 0.32 e Å⁻³
3486 reflections	Δρ_min = −0.24 e Å⁻³
210 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
Cl	1.20916 (4)	0.34129 (13)	0.43476 (5)	0.0742 (3)
O1	0.58663 (11)	0.9036 (4)	0.35790 (10)	0.0669 (5)
O2	0.69588 (12)	0.4707 (4)	0.16844 (11)	0.0739 (6)
O3	0.81680 (12)	0.5033 (3)	0.26680 (11)	0.0653 (5)
N1	0.84352 (11)	0.9213 (3)	0.35853 (10)	0.0428 (5)
N2	0.71934 (11)	1.0384 (4)	0.35902 (11)	0.0484 (5)
N3	0.74299 (13)	0.5777 (4)	0.22900 (12)	0.0517 (5)
N4	1.05820 (12)	0.4680 (4)	0.42526 (12)	0.0542 (5)
C1	0.86309 (14)	1.0659 (5)	0.43064 (14)	0.0528 (6)
H1A	0.9076	1.1814	0.4361	0.063*
H1B	0.8806	0.9645	0.4770	0.063*
C2	0.77991 (15)	1.1909 (5)	0.41832 (15)	0.0594 (7)
H2A	0.7687	1.1946	0.4664	0.071*
H2B	0.7793	1.3533	0.3991	0.071*
C3	0.75815 (13)	0.9028 (4)	0.32102 (13)	0.0406 (5)
C4	0.71043 (14)	0.7723 (4)	0.25471 (13)	0.0451 (6)
C5	0.61813 (14)	0.8220 (5)	0.21354 (14)	0.0582 (7)
H5A	0.5857	0.6921	0.2236	0.070*
H5B	0.6045	0.8293	0.1572	0.070*
C6	0.59349 (15)	1.0563 (5)	0.24097 (15)	0.0602 (7)
H6A	0.5322	1.0689	0.2210	0.072*
H6B	0.6150	1.1890	0.2197	0.072*
C7	0.62807 (15)	1.0737 (5)	0.32935 (15)	0.0552 (7)
H7	0.6161	1.2340	0.3445	0.066*
C8	0.59553 (18)	0.9382 (6)	0.43754 (16)	0.0753 (9)
H8A	0.5732	1.0941	0.4433	0.090*
H8B	0.6551	0.9334	0.4715	0.090*
C9	0.5492 (2)	0.7483 (7)	0.46073 (19)	0.1023 (12)
H9A	0.4896	0.7620	0.4299	0.123*
H9B	0.5587	0.7652	0.5155	0.123*
H9C	0.5691	0.5940	0.4519	0.123*
C11	0.89956 (13)	0.9436 (4)	0.31525 (13)	0.0455 (6)
H11A	0.9131	1.1118	0.3130	0.055*
H11B	0.8695	0.8891	0.2617	0.055*
C12	0.98050 (13)	0.8050 (4)	0.35017 (12)	0.0393 (5)
C13	0.98935 (14)	0.6091 (4)	0.39838 (13)	0.0490 (6)
H13	0.9443	0.5719	0.4134	0.059*
C14	1.12093 (14)	0.5302 (4)	0.40378 (13)	0.0454 (6)
C15	1.12235 (14)	0.7269 (4)	0.35956 (13)	0.0465 (6)
H15	1.1699	0.7651	0.3486	0.056*
C16	1.05008 (14)	0.8655 (4)	0.33212 (13)	0.0462 (6)
H16	1.0480	1.0000	0.3014	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0596 (4)	0.0681 (5)	0.0967 (6)	0.0181 (3)	0.0313 (4)	0.0041 (4)
O1	0.0668 (11)	0.0879 (15)	0.0610 (12)	−0.0114 (10)	0.0413 (10)	−0.0097 (10)
O2	0.0778 (12)	0.0823 (14)	0.0702 (13)	−0.0259 (11)	0.0374 (11)	−0.0376 (11)
O3	0.0691 (12)	0.0575 (12)	0.0737 (13)	0.0125 (9)	0.0320 (10)	−0.0075 (9)
N1	0.0411 (11)	0.0494 (12)	0.0425 (11)	−0.0023 (8)	0.0210 (9)	−0.0026 (9)
N2	0.0439 (11)	0.0575 (13)	0.0477 (12)	0.0013 (9)	0.0216 (9)	−0.0130 (10)
N3	0.0583 (13)	0.0558 (13)	0.0503 (13)	−0.0090 (11)	0.0311 (11)	−0.0095 (11)
N4	0.0553 (12)	0.0513 (13)	0.0624 (14)	0.0059 (10)	0.0293 (11)	0.0106 (10)
C1	0.0529 (14)	0.0594 (16)	0.0473 (14)	−0.0102 (12)	0.0201 (12)	−0.0093 (12)
C2	0.0641 (16)	0.0623 (18)	0.0556 (16)	−0.0076 (13)	0.0269 (13)	−0.0186 (13)
C3	0.0447 (13)	0.0413 (13)	0.0407 (13)	0.0016 (10)	0.0216 (11)	0.0027 (10)
C4	0.0475 (13)	0.0493 (15)	0.0436 (14)	−0.0033 (11)	0.0231 (11)	−0.0055 (11)
C5	0.0476 (14)	0.081 (2)	0.0484 (15)	−0.0038 (13)	0.0204 (12)	−0.0060 (13)
C6	0.0466 (14)	0.082 (2)	0.0545 (16)	0.0109 (13)	0.0218 (12)	0.0084 (14)
C7	0.0500 (14)	0.0604 (17)	0.0626 (17)	0.0079 (12)	0.0297 (13)	−0.0033 (13)
C8	0.0739 (19)	0.104 (3)	0.0543 (18)	0.0098 (17)	0.0314 (15)	0.0030 (17)
C9	0.111 (3)	0.143 (3)	0.071 (2)	−0.020 (2)	0.055 (2)	0.006 (2)
C11	0.0480 (13)	0.0474 (14)	0.0479 (14)	−0.0009 (11)	0.0257 (11)	0.0059 (11)
C12	0.0426 (12)	0.0410 (13)	0.0379 (12)	−0.0033 (10)	0.0193 (10)	−0.0017 (10)
C13	0.0483 (14)	0.0533 (16)	0.0545 (15)	−0.0001 (11)	0.0299 (12)	0.0080 (12)
C14	0.0433 (13)	0.0477 (15)	0.0453 (14)	0.0016 (11)	0.0167 (11)	−0.0066 (11)
C15	0.0435 (13)	0.0538 (15)	0.0494 (14)	−0.0068 (11)	0.0257 (11)	−0.0048 (12)
C16	0.0488 (14)	0.0493 (14)	0.0451 (14)	−0.0073 (11)	0.0230 (11)	0.0045 (11)

Geometric parameters (Å, º) top

Cl—C14	1.745 (2)	C5—H5A	0.9700
O1—C7	1.396 (3)	C5—H5B	0.9700
O1—C8	1.423 (3)	C6—C7	1.505 (4)
O2—N3	1.250 (2)	C6—H6A	0.9700
O3—N3	1.255 (2)	C6—H6B	0.9700
N1—C3	1.358 (3)	C7—H7	0.9800
N1—C11	1.458 (3)	C8—C9	1.475 (4)
N1—C1	1.475 (3)	C8—H8A	0.9700
N2—C3	1.356 (3)	C8—H8B	0.9700
N2—C7	1.453 (3)	C9—H9A	0.9600
N2—C2	1.457 (3)	C9—H9B	0.9600
N3—C4	1.379 (3)	C9—H9C	0.9600
N4—C14	1.316 (3)	C11—C12	1.497 (3)
N4—C13	1.342 (3)	C11—H11A	0.9700
C1—C2	1.517 (3)	C11—H11B	0.9700
C1—H1A	0.9700	C12—C13	1.377 (3)
C1—H1B	0.9700	C12—C16	1.386 (3)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.369 (3)
C3—C4	1.387 (3)	C15—C16	1.378 (3)
C4—C5	1.491 (3)	C15—H15	0.9300
C5—C6	1.514 (4)	C16—H16	0.9300

C7—O1—C8	114.8 (2)	H6A—C6—H6B	108.0
C3—N1—C11	121.70 (18)	O1—C7—N2	112.8 (2)
C3—N1—C1	109.47 (18)	O1—C7—C6	108.2 (2)
C11—N1—C1	117.89 (18)	N2—C7—C6	108.9 (2)
C3—N2—C7	122.79 (19)	O1—C7—H7	108.9
C3—N2—C2	111.33 (18)	N2—C7—H7	108.9
C7—N2—C2	123.86 (19)	C6—C7—H7	108.9
O2—N3—O3	120.5 (2)	O1—C8—C9	109.7 (3)
O2—N3—C4	118.2 (2)	O1—C8—H8A	109.7
O3—N3—C4	121.2 (2)	C9—C8—H8A	109.7
C14—N4—C13	115.5 (2)	O1—C8—H8B	109.7
N1—C1—C2	103.53 (17)	C9—C8—H8B	109.7
N1—C1—H1A	111.1	H8A—C8—H8B	108.2
C2—C1—H1A	111.1	C8—C9—H9A	109.5
N1—C1—H1B	111.1	C8—C9—H9B	109.5
C2—C1—H1B	111.1	H9A—C9—H9B	109.5
H1A—C1—H1B	109.0	C8—C9—H9C	109.5
N2—C2—C1	101.66 (19)	H9A—C9—H9C	109.5
N2—C2—H2A	111.4	H9B—C9—H9C	109.5
C1—C2—H2A	111.4	N1—C11—C12	114.11 (18)
N2—C2—H2B	111.4	N1—C11—H11A	108.7
C1—C2—H2B	111.4	C12—C11—H11A	108.7
H2A—C2—H2B	109.3	N1—C11—H11B	108.7
N2—C3—N1	109.43 (19)	C12—C11—H11B	108.7
N2—C3—C4	120.32 (19)	H11A—C11—H11B	107.6
N1—C3—C4	130.3 (2)	C13—C12—C16	116.7 (2)
N3—C4—C3	122.3 (2)	C13—C12—C11	123.00 (19)
N3—C4—C5	117.1 (2)	C16—C12—C11	120.3 (2)
C3—C4—C5	120.3 (2)	N4—C13—C12	124.8 (2)
C4—C5—C6	111.3 (2)	N4—C13—H13	117.6
C4—C5—H5A	109.4	C12—C13—H13	117.6
C6—C5—H5A	109.4	N4—C14—C15	125.8 (2)
C4—C5—H5B	109.4	N4—C14—Cl	116.08 (18)
C6—C5—H5B	109.4	C15—C14—Cl	118.11 (18)
H5A—C5—H5B	108.0	C14—C15—C16	117.0 (2)
C5—C6—C7	111.6 (2)	C14—C15—H15	121.5
C5—C6—H6A	109.3	C16—C15—H15	121.5
C7—C6—H6A	109.3	C15—C16—C12	120.1 (2)
C5—C6—H6B	109.3	C15—C16—H16	119.9
C7—C6—H6B	109.3	C12—C16—H16	119.9

C3—N1—C1—C2	−16.3 (3)	C8—O1—C7—N2	75.1 (3)
C11—N1—C1—C2	128.5 (2)	C8—O1—C7—C6	−164.3 (2)
C3—N2—C2—C1	−19.3 (3)	C3—N2—C7—O1	91.2 (3)
C7—N2—C2—C1	176.5 (2)	C2—N2—C7—O1	−106.4 (3)
N1—C1—C2—N2	20.5 (2)	C3—N2—C7—C6	−28.9 (3)
C7—N2—C3—N1	174.3 (2)	C2—N2—C7—C6	133.5 (2)
C2—N2—C3—N1	9.9 (3)	C5—C6—C7—O1	−67.8 (3)
C7—N2—C3—C4	−6.0 (3)	C5—C6—C7—N2	55.2 (3)
C2—N2—C3—C4	−170.4 (2)	C7—O1—C8—C9	180.0 (2)
C11—N1—C3—N2	−138.6 (2)	C3—N1—C11—C12	−140.6 (2)
C1—N1—C3—N2	4.7 (3)	C1—N1—C11—C12	79.0 (2)
C11—N1—C3—C4	41.7 (4)	N1—C11—C12—C13	23.2 (3)
C1—N1—C3—C4	−175.0 (2)	N1—C11—C12—C16	−159.4 (2)
O2—N3—C4—C3	−179.6 (2)	C14—N4—C13—C12	1.3 (3)
O3—N3—C4—C3	3.1 (3)	C16—C12—C13—N4	−3.6 (3)
O2—N3—C4—C5	7.1 (3)	C11—C12—C13—N4	173.9 (2)
O3—N3—C4—C5	−170.2 (2)	C13—N4—C14—C15	2.3 (3)
N2—C3—C4—N3	−158.8 (2)	C13—N4—C14—Cl	−177.37 (17)
N1—C3—C4—N3	20.8 (4)	N4—C14—C15—C16	−3.2 (3)
N2—C3—C4—C5	14.3 (3)	Cl—C14—C15—C16	176.44 (17)
N1—C3—C4—C5	−166.1 (2)	C14—C15—C16—C12	0.6 (3)
N3—C4—C5—C6	−173.1 (2)	C13—C12—C16—C15	2.4 (3)
C3—C4—C5—C6	13.5 (3)	C11—C12—C16—C15	−175.1 (2)
C4—C5—C6—C7	−48.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3	0.97	2.35	2.803 (3)	108
C13—H13···N1	0.93	2.54	2.891 (3)	103

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉ClN₄O₃
M_r	338.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	17.021 (3), 5.5737 (8), 18.334 (3)
β (°)	112.097 (3)
V (Å³)	1611.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.50 × 0.24 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.922, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	8970, 3486, 1870
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 0.82
No. of reflections	3486
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3	0.97	2.35	2.803 (3)	108.1
C13—H13···N1	0.93	2.54	2.891 (3)	103

Acknowledgements

The authors thank the Opening Fund of Shanghai Key Laboratory of Chemical Biology (grant No. SKLCB-2008-08) and the Doctoral Foundation of the University of Jinan (grant No. XBS0823, B0542) for financial support.

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kagabu, S., Nishiwaki, H., Sato, K., Hibi, M., Yamaoka, N. & Nakagawa, Y. (2002). Pest. Manag. Sci. 58, 483–490. Web of Science CrossRef PubMed CAS Google Scholar
Moriya, K., Shibuya, K., Hattori, Y., Tsuboi, S., Shiokawa, K. & Kagabu, S. (1992). Biosci. Biotechnol. Biochem. 56, 364–365. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food. Chem. 55, 2288–2292. Web of Science CrossRef PubMed CAS Google Scholar
Tokumitsu, T. (1990). Bull. Chem. Soc. Jpn, 63, 1921–1924. CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 10| October 2009| Page o2517

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

1-[(6-Chloro-3-pyrid­yl)meth­yl]-5-eth­­oxy-8-nitro-1,2,3,5,6,7-hexa­hydro­imidazo[1,2-a]pyridine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(6-Chloro-3-pyridyl)methyl]-5-ethoxy-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine