1-[(6-Chloro­pyridin-3-yl)meth­yl]-10-nitro-1,2,3,5,6,7,8,9-octa­hydro-5,9-methano­imidazo[1,2-a]azocin-5-ol

Cui, S.-X.; Zhang, G.-Y.; Tian, Z.-Z.

doi:10.1107/S1600536813014402

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1015

https://doi.org/10.1107/S1600536813014402

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1-[(6-Chloropyridin-3-yl)methyl]-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-methanoimidazo[1,2-a]azocin-5-ol

Shu-Xia Cui,^a Guang-You Zhang ^a and Zhong-Zhen Tian ^a ^*

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

(Received 10 April 2013; accepted 24 May 2013; online 8 June 2013)

In the title compound, C₁₆H₁₉ClN₄O₃, the cyclohexane ring displays a chair formation and the tetrahydropyridine ring displays an envelope conformation with the methylene C atom as the flap; the imidazolidine ring also displays an envelope conformation with a methylene C atom as the flap. In the crystal, O—H⋯N hydrogen bonds between hydroxy groups and pyridine rings link inversion-related molecules into dimers. Weak C—H⋯O hydrogen bonds further link the dimers into supramolecular chains running along the c axis.

Related literature

For background to the title compound, see: Jeschkel & Nauen (2008 ). For the synthesis, see: Tian et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₉ClN₄O₃
M_r = 350.80
Monoclinic, P 2₁ /c
a = 13.3975 (14) Å
b = 18.7124 (18) Å
c = 6.5721 (8) Å
β = 97.897 (10)°
V = 1632.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.38 × 0.24 × 0.23 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.93, T_max = 0.94
7705 measured reflections
2921 independent reflections
1727 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.217
S = 1.05
2921 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N4ⁱ	0.82	2.04	2.855 (4)	174
C11—H11A⋯O1ⁱⁱ	0.97	2.53	3.467 (5)	161
C13—H13⋯O2ⁱⁱ	0.93	2.48	3.265 (5)	142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813014402/xu5695sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014402/xu5695Isup2.hkl

checkCIF report

Comment top

The past decades have witnessed the great power and versatile ability of neonicotinoids as a novel class of insecticides (Jeschkel & Nauen, 2008), Several commercial neonicotinoid compounds were launched successively in the latest two decades, and they presented a broad spectrum performance in controlling various insects. Our interest was introducing bicyclic struture to fix the direction of the nitro group, and synthesized a class of novel cis-neonicotinoid compounds with carbon bicyclic, in which the title compound exhibited good insecticidal activities against pea aphids.

The structure of compound is shown in Fig. 1 with the atom-numbering scheme. In the title compound, the the cyclohexane ring displays a chair formation while the hexahydroazocine ring displays an envelope conformation with the methylene C atom on the flap; the imidazolidine ring also displays an envelope confromation with a methylene C atom on the flap. In the crystal, intermolecular O—H···N hydrogen bonds between hydroxyl groups and pyridine rings link inversion-related molecules into dimer. Weak C—H···O hydrogen bonds further link the dimers into the supramolecular arichiecture.

Related literature top

For background to the title compound, see: Jeschkel & Nauen (2008). For the synthesis, see: Tian et al. (2007).

Experimental top

The title compound was synthesized according to the literature (Tian et al., 2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solution of dichloromethane and ether of the title compound.

Structure description top

For background to the title compound, see: Jeschkel & Nauen (2008). For the synthesis, see: Tian et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

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 circles of arbitrary size.

1-[(6-Chloropyridin-3-yl)methyl]-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-methanoimidazo[1,2-a]azocin-5-ol top

Crystal data top

C₁₆H₁₉ClN₄O₃	F(000) = 736
M_r = 350.80	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1166 reflections
a = 13.3975 (14) Å	θ = 2.6–25.2°
b = 18.7124 (18) Å	µ = 0.26 mm⁻¹
c = 6.5721 (8) Å	T = 296 K
β = 97.897 (10)°	Prism, colourless
V = 1632.0 (3) Å³	0.38 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2921 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 16.03 pixels mm^-1	θ_max = 25.2°, θ_min = 2.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −21→22
T_min = 0.93, T_max = 0.94	l = −7→6
7705 measured reflections

Refinement top

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1042P)² + 0.1363P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₉ClN₄O₃	V = 1632.0 (3) Å³
M_r = 350.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3975 (14) Å	µ = 0.26 mm⁻¹
b = 18.7124 (18) Å	T = 296 K
c = 6.5721 (8) Å	0.38 × 0.24 × 0.23 mm
β = 97.897 (10)°

Data collection top

Bruker APEXII diffractometer	2921 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1727 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.94	R_int = 0.056
7705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.217	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
2921 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	−0.41200 (9)	0.65584 (9)	0.0781 (3)	0.0997 (6)
N1	0.1452 (3)	0.65779 (16)	0.7861 (5)	0.0462 (9)
N2	0.2189 (2)	0.53441 (15)	0.4048 (5)	0.0366 (8)
N3	0.0721 (2)	0.59219 (15)	0.3726 (5)	0.0437 (8)
N4	−0.2457 (2)	0.63479 (18)	0.3227 (6)	0.0571 (10)
O1	0.1870 (2)	0.69232 (16)	0.9378 (5)	0.0673 (9)
O2	0.0505 (2)	0.65481 (15)	0.7522 (5)	0.0588 (8)
O3	0.35157 (19)	0.45270 (13)	0.4224 (4)	0.0510 (8)
H3	0.3216	0.4252	0.4901	0.077*
C1	0.1637 (3)	0.58526 (18)	0.4877 (6)	0.0373 (9)
C2	0.1721 (3)	0.5161 (2)	0.1983 (6)	0.0533 (11)
H2A	0.1769	0.4653	0.1716	0.064*
H2B	0.2017	0.5427	0.0949	0.064*
C3	0.0639 (3)	0.5387 (2)	0.2069 (7)	0.0563 (12)
H3A	0.0341	0.5594	0.0774	0.068*
H3B	0.0233	0.4984	0.2386	0.068*
C4	0.2050 (3)	0.62191 (19)	0.6634 (6)	0.0388 (9)
C5	0.3162 (3)	0.61790 (18)	0.7288 (6)	0.0443 (10)
H5	0.3302	0.6297	0.8751	0.053*
C6	0.3494 (3)	0.54049 (19)	0.6983 (6)	0.0455 (10)
H6A	0.4208	0.5352	0.7467	0.055*
H6B	0.3123	0.5080	0.7752	0.055*
C7	0.3281 (3)	0.52359 (18)	0.4689 (6)	0.0388 (9)
C8	0.3893 (3)	0.57185 (19)	0.3484 (7)	0.0477 (10)
H8A	0.3741	0.5609	0.2032	0.057*
H8B	0.4605	0.5630	0.3904	0.057*
C9	0.3664 (3)	0.65028 (19)	0.3831 (7)	0.0515 (11)
H9A	0.4128	0.6797	0.3188	0.062*
H9B	0.2987	0.6609	0.3177	0.062*
C10	0.3751 (3)	0.6691 (2)	0.6090 (7)	0.0564 (12)
H10A	0.3502	0.7173	0.6229	0.068*
H10B	0.4455	0.6682	0.6680	0.068*
C11	0.0317 (3)	0.66343 (18)	0.3105 (6)	0.0400 (9)
H11A	0.0647	0.6811	0.1980	0.048*
H11B	0.0465	0.6963	0.4248	0.048*
C12	−0.0792 (3)	0.66095 (16)	0.2453 (6)	0.0347 (9)
C13	−0.1215 (3)	0.68244 (19)	0.0504 (6)	0.0450 (10)
H13	−0.0801	0.6977	−0.0435	0.054*
C14	−0.2246 (3)	0.6813 (2)	−0.0049 (7)	0.0539 (11)
H14	−0.2539	0.6961	−0.1346	0.065*
C15	−0.2822 (3)	0.6576 (2)	0.1372 (8)	0.0518 (11)
C16	−0.1457 (3)	0.6367 (2)	0.3742 (7)	0.0495 (11)
H16	−0.1190	0.6208	0.5044	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0386 (7)	0.1346 (13)	0.1228 (14)	0.0014 (7)	0.0000 (7)	0.0343 (10)
N1	0.055 (2)	0.042 (2)	0.042 (2)	0.0066 (15)	0.0090 (17)	−0.0048 (16)
N2	0.0401 (17)	0.0310 (17)	0.0390 (18)	0.0055 (12)	0.0071 (14)	−0.0050 (14)
N3	0.0452 (19)	0.0319 (17)	0.052 (2)	0.0061 (13)	−0.0022 (15)	−0.0140 (16)
N4	0.039 (2)	0.056 (2)	0.078 (3)	−0.0026 (15)	0.0113 (18)	0.014 (2)
O1	0.081 (2)	0.070 (2)	0.048 (2)	0.0147 (15)	0.0004 (16)	−0.0235 (16)
O2	0.0499 (19)	0.071 (2)	0.059 (2)	0.0059 (14)	0.0197 (14)	−0.0108 (15)
O3	0.0569 (18)	0.0363 (16)	0.064 (2)	0.0123 (12)	0.0222 (14)	0.0068 (13)
C1	0.034 (2)	0.032 (2)	0.047 (2)	−0.0027 (15)	0.0071 (16)	−0.0003 (18)
C2	0.067 (3)	0.042 (2)	0.049 (3)	0.0120 (19)	0.002 (2)	−0.012 (2)
C3	0.057 (3)	0.046 (2)	0.062 (3)	0.0052 (18)	−0.007 (2)	−0.017 (2)
C4	0.042 (2)	0.041 (2)	0.033 (2)	0.0023 (16)	0.0033 (16)	−0.0090 (17)
C5	0.050 (2)	0.041 (2)	0.040 (2)	0.0053 (17)	−0.0041 (18)	−0.0069 (18)
C6	0.044 (2)	0.045 (2)	0.046 (3)	0.0069 (17)	0.0016 (18)	0.0036 (19)
C7	0.045 (2)	0.026 (2)	0.047 (2)	0.0073 (15)	0.0114 (18)	0.0043 (17)
C8	0.044 (2)	0.046 (2)	0.055 (3)	0.0071 (17)	0.0116 (19)	0.005 (2)
C9	0.050 (2)	0.037 (2)	0.069 (3)	0.0002 (17)	0.012 (2)	0.014 (2)
C10	0.043 (2)	0.043 (2)	0.080 (3)	−0.0032 (17)	−0.003 (2)	−0.007 (2)
C11	0.043 (2)	0.033 (2)	0.046 (2)	−0.0023 (15)	0.0127 (17)	−0.0021 (17)
C12	0.041 (2)	0.0219 (18)	0.041 (2)	−0.0019 (14)	0.0067 (17)	0.0027 (16)
C13	0.045 (2)	0.040 (2)	0.050 (3)	0.0013 (16)	0.0093 (18)	0.0104 (19)
C14	0.050 (3)	0.057 (3)	0.053 (3)	0.002 (2)	0.001 (2)	0.018 (2)
C15	0.043 (2)	0.043 (2)	0.069 (3)	0.0056 (17)	0.007 (2)	0.013 (2)
C16	0.046 (2)	0.047 (2)	0.056 (3)	−0.0001 (17)	0.005 (2)	0.008 (2)

Geometric parameters (Å, º) top

Cl1—C15	1.729 (4)	C5—H5	0.9800
N1—O1	1.254 (4)	C6—C7	1.529 (5)
N1—O2	1.258 (4)	C6—H6A	0.9700
N1—C4	1.386 (5)	C6—H6B	0.9700
N2—C1	1.363 (5)	C7—C8	1.515 (5)
N2—C2	1.456 (5)	C8—C9	1.523 (5)
N2—C7	1.480 (4)	C8—H8A	0.9700
N3—C1	1.357 (4)	C8—H8B	0.9700
N3—C3	1.472 (5)	C9—C10	1.515 (6)
N3—C11	1.475 (4)	C9—H9A	0.9700
N4—C15	1.320 (6)	C9—H9B	0.9700
N4—C16	1.337 (5)	C10—H10A	0.9700
O3—C7	1.407 (4)	C10—H10B	0.9700
O3—H3	0.8200	C11—C12	1.490 (5)
C1—C4	1.391 (5)	C11—H11A	0.9700
C2—C3	1.518 (5)	C11—H11B	0.9700
C2—H2A	0.9700	C12—C16	1.387 (5)
C2—H2B	0.9700	C12—C13	1.387 (5)
C3—H3A	0.9700	C13—C14	1.380 (5)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.495 (5)	C14—C15	1.364 (6)
C5—C10	1.527 (6)	C14—H14	0.9300
C5—C6	1.537 (5)	C16—H16	0.9300

O1—N1—O2	119.6 (3)	N2—C7—C8	110.8 (3)
O1—N1—C4	118.7 (3)	O3—C7—C6	113.1 (3)
O2—N1—C4	121.6 (3)	N2—C7—C6	107.2 (3)
C1—N2—C2	110.4 (3)	C8—C7—C6	110.5 (3)
C1—N2—C7	123.4 (3)	C7—C8—C9	111.2 (3)
C2—N2—C7	121.0 (3)	C7—C8—H8A	109.4
C1—N3—C3	108.5 (3)	C9—C8—H8A	109.4
C1—N3—C11	120.6 (3)	C7—C8—H8B	109.4
C3—N3—C11	115.0 (3)	C9—C8—H8B	109.4
C15—N4—C16	117.1 (4)	H8A—C8—H8B	108.0
C7—O3—H3	109.5	C10—C9—C8	112.4 (3)
N3—C1—N2	110.0 (3)	C10—C9—H9A	109.1
N3—C1—C4	129.9 (3)	C8—C9—H9A	109.1
N2—C1—C4	120.0 (3)	C10—C9—H9B	109.1
N2—C2—C3	101.0 (3)	C8—C9—H9B	109.1
N2—C2—H2A	111.6	H9A—C9—H9B	107.9
C3—C2—H2A	111.6	C9—C10—C5	112.6 (3)
N2—C2—H2B	111.6	C9—C10—H10A	109.1
C3—C2—H2B	111.6	C5—C10—H10A	109.1
H2A—C2—H2B	109.4	C9—C10—H10B	109.1
N3—C3—C2	104.0 (3)	C5—C10—H10B	109.1
N3—C3—H3A	110.9	H10A—C10—H10B	107.8
C2—C3—H3A	110.9	N3—C11—C12	111.4 (3)
N3—C3—H3B	110.9	N3—C11—H11A	109.4
C2—C3—H3B	110.9	C12—C11—H11A	109.4
H3A—C3—H3B	109.0	N3—C11—H11B	109.4
N1—C4—C1	121.8 (3)	C12—C11—H11B	109.4
N1—C4—C5	119.4 (3)	H11A—C11—H11B	108.0
C1—C4—C5	118.7 (3)	C16—C12—C13	116.4 (3)
C4—C5—C10	112.7 (3)	C16—C12—C11	122.2 (3)
C4—C5—C6	107.8 (3)	C13—C12—C11	121.4 (3)
C10—C5—C6	110.2 (4)	C14—C13—C12	120.4 (4)
C4—C5—H5	108.7	C14—C13—H13	119.8
C10—C5—H5	108.7	C12—C13—H13	119.8
C6—C5—H5	108.7	C15—C14—C13	117.7 (4)
C7—C6—C5	107.8 (3)	C15—C14—H14	121.2
C7—C6—H6A	110.2	C13—C14—H14	121.2
C5—C6—H6A	110.2	N4—C15—C14	124.4 (4)
C7—C6—H6B	110.2	N4—C15—Cl1	115.8 (3)
C5—C6—H6B	110.2	C14—C15—Cl1	119.8 (3)
H6A—C6—H6B	108.5	N4—C16—C12	124.0 (4)
O3—C7—N2	108.0 (3)	N4—C16—H16	118.0
O3—C7—C8	107.2 (3)	C12—C16—H16	118.0

C3—N3—C1—N2	3.5 (4)	C1—N2—C7—C8	−87.0 (4)
C11—N3—C1—N2	−132.3 (3)	C2—N2—C7—C8	65.2 (4)
C3—N3—C1—C4	−177.8 (4)	C1—N2—C7—C6	33.7 (4)
C11—N3—C1—C4	46.5 (6)	C2—N2—C7—C6	−174.1 (3)
C2—N2—C1—N3	13.0 (4)	C5—C6—C7—O3	−177.5 (3)
C7—N2—C1—N3	167.8 (3)	C5—C6—C7—N2	−58.5 (4)
C2—N2—C1—C4	−165.9 (3)	C5—C6—C7—C8	62.4 (4)
C7—N2—C1—C4	−11.1 (5)	O3—C7—C8—C9	178.1 (3)
C1—N2—C2—C3	−22.7 (4)	N2—C7—C8—C9	60.5 (4)
C7—N2—C2—C3	−178.2 (3)	C6—C7—C8—C9	−58.3 (4)
C1—N3—C3—C2	−17.4 (4)	C7—C8—C9—C10	51.5 (4)
C11—N3—C3—C2	121.1 (3)	C8—C9—C10—C5	−50.4 (5)
N2—C2—C3—N3	23.3 (4)	C4—C5—C10—C9	−65.2 (4)
O1—N1—C4—C1	−177.1 (3)	C6—C5—C10—C9	55.2 (4)
O2—N1—C4—C1	5.0 (5)	C1—N3—C11—C12	−162.0 (3)
O1—N1—C4—C5	7.4 (5)	C3—N3—C11—C12	64.9 (4)
O2—N1—C4—C5	−170.6 (3)	N3—C11—C12—C16	58.0 (4)
N3—C1—C4—N1	20.4 (6)	N3—C11—C12—C13	−121.5 (4)
N2—C1—C4—N1	−160.9 (3)	C16—C12—C13—C14	2.0 (5)
N3—C1—C4—C5	−164.0 (4)	C11—C12—C13—C14	−178.5 (3)
N2—C1—C4—C5	14.7 (5)	C12—C13—C14—C15	−0.8 (6)
N1—C4—C5—C10	−103.5 (4)	C16—N4—C15—C14	1.5 (6)
C1—C4—C5—C10	80.8 (4)	C16—N4—C15—Cl1	−178.9 (3)
N1—C4—C5—C6	134.7 (4)	C13—C14—C15—N4	−1.1 (7)
C1—C4—C5—C6	−41.0 (5)	C13—C14—C15—Cl1	179.3 (3)
C4—C5—C6—C7	63.1 (4)	C15—N4—C16—C12	0.0 (6)
C10—C5—C6—C7	−60.2 (4)	C13—C12—C16—N4	−1.7 (5)
C1—N2—C7—O3	155.9 (3)	C11—C12—C16—N4	178.8 (3)
C2—N2—C7—O3	−51.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N4ⁱ	0.82	2.04	2.855 (4)	174
C11—H11A···O1ⁱⁱ	0.97	2.53	3.467 (5)	161
C13—H13···O2ⁱⁱ	0.93	2.48	3.265 (5)	142

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉ClN₄O₃
M_r	350.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.3975 (14), 18.7124 (18), 6.5721 (8)
β (°)	97.897 (10)
V (Å³)	1632.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.38 × 0.24 × 0.23

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.93, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	7705, 2921, 1727
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.217, 1.05
No. of reflections	2921
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N4ⁱ	0.82	2.04	2.855 (4)	174
C11—H11A···O1ⁱⁱ	0.97	2.53	3.467 (5)	161
C13—H13···O2ⁱⁱ	0.93	2.48	3.265 (5)	142

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20902037), the Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (grant No. BS2010NY001), and the Opening Fund of Shanghai Key Laboratory of Chemical Biology (grant No. SKLCB-2008-08).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jeschkel, P. & Nauen, R. (2008). Pest Manage. Sci. 64, 1084–1098. 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

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

1-[(6-Chloro­pyridin-3-yl)meth­yl]-10-nitro-1,2,3,5,6,7,8,9-octa­hydro-5,9-methano­imidazo[1,2-a]azocin-5-ol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(6-Chloropyridin-3-yl)methyl]-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-methanoimidazo[1,2-a]azocin-5-ol