1-[(6-Chloro-pyridin-3-yl)meth-yl]-imidazolidin-2-one.

In the title mol-ecule, C(9)H(10)ClN(3)O, the dihedral angle between the pyridine ring and imidazoline ring mean plane [maximum deviation = 0.031-(3) Å] is 76.2 (1)°. In the crystal, N-H⋯O hydrogen bonds link pairs of mol-ecules to form inversion dimers. In addition, weak C-H⋯N hydrogen bonds and π-π stacking inter-actions between pyridine rings [centroid-centroid distance = 3.977 (2) Å] are observed.

Related literature

For the background to the insecticidal applications of imidacloprid (N-{1-[(6-chloro-3-pyrid­yl)meth­yl]-4,5-dihydro­imidazol-2-yl}nitramide), see: Samaritoni et al. (2003 ▶); Suchail et al. (2001 ▶, 2004 ▶); Schulz-Jander & Casida (2002 ▶); Kagabu et al. (2007 ▶); Pandey et al. (2009 ▶). For related structures, see: Kapoor et al. (2011 ▶, 2012 ▶); Kant et al. (2012 ▶).

Experimental

Crystal data

C9H10ClN3O

M = 211.65

Triclinic,

a = 5.9864 (3) Å

b = 7.4724 (5) Å

c = 11.0235 (8) Å

α = 83.103 (6)°

β = 80.040 (5)°

γ = 80.020 (5)°

V = 476.26 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.835, T max = 1.000

6991 measured reflections

1876 independent reflections

1127 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.205

S = 0.98

1876 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023537/lh5478sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023537/lh5478Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023537/lh5478Isup3.cml

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

C9H10ClN3O	Z = 2
Mr = 211.65	F(000) = 220
Triclinic, P1	Dx = 1.476 Mg m−3
Hall symbol: -P 1	Melting point: 416 K
a = 5.9864 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4724 (5) Å	Cell parameters from 2653 reflections
c = 11.0235 (8) Å	θ = 3.5–28.9°
α = 83.103 (6)°	µ = 0.37 mm−1
β = 80.040 (5)°	T = 293 K
γ = 80.020 (5)°	Block, white
V = 476.26 (5) Å3	0.3 × 0.2 × 0.1 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1876 independent reflections
Radiation source: fine-focus sealed tube	1127 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.835, Tmax = 1.000	l = −13→13
6991 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.1095P)2] where P = (Fo2 + 2Fc2)/3
1876 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.4849 (2)	0.45046 (14)	−0.23011 (9)	0.0729 (5)
N1	0.5214 (5)	0.2659 (4)	−0.0175 (3)	0.0489 (8)
C4	0.0675 (6)	0.2139 (5)	0.0355 (4)	0.0542 (10)
H4	−0.0858	0.1979	0.0528	0.065*
C3	0.2141 (5)	0.1420 (4)	0.1179 (3)	0.0410 (8)
C2	0.4371 (5)	0.1719 (5)	0.0871 (3)	0.0432 (8)
H2	0.5374	0.1237	0.1427	0.052*
C5	0.1490 (6)	0.3105 (5)	−0.0738 (3)	0.0496 (9)
H5	0.0535	0.3601	−0.1316	0.059*
C6	0.3766 (6)	0.3299 (4)	−0.0931 (3)	0.0436 (8)
C7	0.1389 (6)	0.0288 (5)	0.2357 (4)	0.0528 (9)
H7A	0.0729	−0.0717	0.2158	0.063*
H7B	0.2721	−0.0224	0.2747	0.063*
N8	−0.0276 (5)	0.1334 (4)	0.3217 (3)	0.0539 (8)
C9	0.0273 (6)	0.2816 (5)	0.3778 (3)	0.0489 (9)
H9A	0.0401	0.3877	0.3185	0.059*
H9B	0.1703	0.2460	0.4108	0.059*
C10	−0.1757 (6)	0.3212 (5)	0.4818 (4)	0.0556 (10)
H10A	−0.1250	0.3054	0.5619	0.067*
H10B	−0.2575	0.4442	0.4688	0.067*
N11	−0.3167 (6)	0.1876 (5)	0.4724 (3)	0.0645 (10)
C12	−0.2227 (6)	0.0748 (5)	0.3831 (3)	0.0456 (9)
O12	−0.2977 (4)	−0.0596 (4)	0.3591 (2)	0.0627 (8)
H11	−0.435 (8)	0.156 (6)	0.518 (4)	0.091 (15)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0942 (9)	0.0714 (8)	0.0479 (7)	−0.0244 (6)	0.0061 (6)	0.0070 (5)
N1	0.0365 (16)	0.0625 (18)	0.0457 (19)	−0.0145 (13)	0.0013 (14)	0.0024 (15)
C4	0.0285 (17)	0.068 (2)	0.068 (3)	−0.0144 (16)	−0.0060 (17)	−0.005 (2)
C3	0.0331 (17)	0.0449 (17)	0.044 (2)	−0.0102 (14)	0.0038 (15)	−0.0095 (15)
C2	0.0330 (17)	0.056 (2)	0.040 (2)	−0.0110 (14)	−0.0023 (15)	−0.0025 (16)
C5	0.043 (2)	0.058 (2)	0.048 (2)	−0.0045 (16)	−0.0123 (17)	−0.0026 (18)
C6	0.048 (2)	0.0440 (18)	0.036 (2)	−0.0116 (15)	0.0023 (16)	−0.0025 (15)
C7	0.048 (2)	0.052 (2)	0.053 (2)	−0.0131 (16)	0.0096 (18)	−0.0017 (18)
N8	0.0459 (16)	0.0637 (19)	0.051 (2)	−0.0266 (14)	0.0192 (14)	−0.0135 (16)
C9	0.051 (2)	0.052 (2)	0.043 (2)	−0.0176 (16)	0.0032 (17)	−0.0041 (17)
C10	0.060 (2)	0.063 (2)	0.040 (2)	−0.0163 (18)	0.0084 (18)	−0.0049 (18)
N11	0.054 (2)	0.090 (2)	0.052 (2)	−0.0363 (19)	0.0183 (17)	−0.0188 (19)
C12	0.0399 (18)	0.064 (2)	0.034 (2)	−0.0194 (16)	−0.0016 (15)	0.0038 (17)
O12	0.0553 (16)	0.0826 (19)	0.0558 (18)	−0.0392 (14)	0.0077 (13)	−0.0107 (15)

Cl1—C6	1.746 (3)	C7—H7B	0.9700
N1—C6	1.298 (4)	N8—C12	1.359 (4)
N1—C2	1.344 (4)	N8—C9	1.442 (4)
C4—C3	1.371 (5)	C9—C10	1.534 (5)
C4—C5	1.386 (5)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C3—C2	1.370 (4)	C10—N11	1.437 (5)
C3—C7	1.507 (5)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C5—C6	1.373 (5)	N11—C12	1.357 (5)
C5—H5	0.9300	N11—H11	0.85 (4)
C7—N8	1.444 (5)	C12—O12	1.241 (4)
C7—H7A	0.9700
C6—N1—C2	115.8 (3)	C12—N8—C9	111.8 (3)
C3—C4—C5	119.6 (3)	C12—N8—C7	123.6 (3)
C3—C4—H4	120.2	C9—N8—C7	122.2 (3)
C5—C4—H4	120.2	N8—C9—C10	103.9 (3)
C2—C3—C4	117.2 (3)	N8—C9—H9A	111.0
C2—C3—C7	120.5 (3)	C10—C9—H9A	111.0
C4—C3—C7	122.3 (3)	N8—C9—H9B	111.0
N1—C2—C3	124.7 (3)	C10—C9—H9B	111.0
N1—C2—H2	117.6	H9A—C9—H9B	109.0
C3—C2—H2	117.6	N11—C10—C9	102.9 (3)
C6—C5—C4	117.1 (3)	N11—C10—H10A	111.2
C6—C5—H5	121.4	C9—C10—H10A	111.2
C4—C5—H5	121.4	N11—C10—H10B	111.2
N1—C6—C5	125.5 (3)	C9—C10—H10B	111.2
N1—C6—Cl1	116.2 (3)	H10A—C10—H10B	109.1
C5—C6—Cl1	118.3 (3)	C12—N11—C10	112.8 (3)
N8—C7—C3	112.5 (3)	C12—N11—H11	114 (3)
N8—C7—H7A	109.1	C10—N11—H11	133 (3)
C3—C7—H7A	109.1	O12—C12—N11	127.2 (3)
N8—C7—H7B	109.1	O12—C12—N8	124.5 (3)
C3—C7—H7B	109.1	N11—C12—N8	108.3 (3)
H7A—C7—H7B	107.8
C5—C4—C3—C2	0.6 (5)	C3—C7—N8—C12	134.0 (3)
C5—C4—C3—C7	−177.3 (3)	C3—C7—N8—C9	−64.8 (4)
C6—N1—C2—C3	−0.5 (5)	C12—N8—C9—C10	−4.1 (4)
C4—C3—C2—N1	−0.1 (5)	C7—N8—C9—C10	−167.3 (3)
C7—C3—C2—N1	177.8 (3)	N8—C9—C10—N11	1.1 (4)
C3—C4—C5—C6	−0.4 (5)	C9—C10—N11—C12	2.2 (4)
C2—N1—C6—C5	0.6 (5)	C10—N11—C12—O12	175.2 (4)
C2—N1—C6—Cl1	−179.4 (2)	C10—N11—C12—N8	−4.9 (4)
C4—C5—C6—N1	−0.2 (5)	C9—N8—C12—O12	−174.4 (3)
C4—C5—C6—Cl1	179.8 (3)	C7—N8—C12—O12	−11.5 (6)
C2—C3—C7—N8	115.6 (3)	C9—N8—C12—N11	5.7 (4)
C4—C3—C7—N8	−66.6 (4)	C7—N8—C12—N11	168.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12i	0.85 (5)	2.08 (5)	2.924 (4)	174 (5)
C4—H4···N1ii	0.93	2.55	3.369 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O12i	0.85 (5)	2.08 (5)	2.924 (4)	174 (5)
C4—H4⋯N1ii	0.93	2.55	3.369 (5)	147

Symmetry codes: (i) ; (ii) .