Ethyl 3-[(6-chloro-pyridin-3-yl)meth-yl]-2-oxoimidazolidine-1-carboxyl-ate.

In the title compound, C(12)H(14)ClN(3)O(3), the imidazole ring adopts a half-chair conformation. The dihedral angle between the pyridine and imidazole rings is 70.0 (1)°. In the crystal, the molecules are linked by C-H⋯O inter-actions, forming chains parallel to the c axis.

Related literature

For background to the insecticidal applications of imidacloprid [systematic name: N-[1-[(6-chloro-3-pyrid­yl)meth­yl]-4,5-dihydro­imidazol-2-yl]nitramide], see: Samaritoni et al. (2003 ▶); Kagabu et al. (1997 ▶, 2007 ▶); Zhao et al. (2010 ▶). For ring conformations, see: Duax & Norton (1975 ▶). For related structures, see: Kapoor et al. (2011 ▶); Kant et al. (2012 ▶).

Experimental

Crystal data

C12H14ClN3O3

M = 283.71

Monoclinic,

a = 13.3926 (14) Å

b = 8.4991 (8) Å

c = 12.3361 (12) Å

β = 106.538 (10)°

V = 1346.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.941, T max = 1.000

6112 measured reflections

2645 independent reflections

1537 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.191

S = 1.05

2645 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; 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/S1600536812001948/gg2073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001948/gg2073Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001948/gg2073Isup3.cml

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

C12H14ClN3O3	F(000) = 592
Mr = 283.71	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Melting point: 362 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.3926 (14) Å	Cell parameters from 1920 reflections
b = 8.4991 (8) Å	θ = 3.4–29.0°
c = 12.3361 (12) Å	µ = 0.29 mm−1
β = 106.538 (10)°	T = 293 K
V = 1346.1 (2) Å3	Plate, white
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2645 independent reflections
Radiation source: fine-focus sealed tube	1537 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→9
Tmin = 0.941, Tmax = 1.000	l = −15→15
6112 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0878P)2 + 0.0871P] where P = (Fo2 + 2Fc2)/3
2645 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.42 e Å−3
1 restraint	Δρmin = −0.21 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	−0.37380 (8)	0.08507 (14)	−0.01623 (10)	0.0948 (5)
O1	0.06757 (17)	−0.2327 (3)	0.42795 (18)	0.0656 (7)
O2	0.22097 (18)	−0.0437 (3)	0.57542 (18)	0.0692 (7)
N1	−0.2183 (2)	−0.0963 (4)	−0.0205 (2)	0.0647 (8)
C2	−0.1521 (3)	−0.1394 (4)	0.2107 (3)	0.0606 (9)
H2	−0.1303	−0.1540	0.2887	0.073*
C3	−0.0976 (2)	−0.2097 (3)	0.1434 (2)	0.0488 (8)
C4	−0.1347 (3)	−0.1827 (4)	0.0290 (3)	0.0597 (9)
H4	−0.0987	−0.2282	−0.0173	0.072*
C5	−0.2373 (3)	−0.0491 (4)	0.1629 (3)	0.0626 (9)
H5	−0.2745	−0.0006	0.2070	0.075*
C6	−0.2664 (2)	−0.0322 (4)	0.0476 (3)	0.0585 (9)
C7	−0.0017 (2)	−0.3089 (4)	0.1925 (3)	0.0588 (9)
H7A	−0.0165	−0.3841	0.2451	0.071*
H7B	0.0140	−0.3677	0.1320	0.071*
N8	0.0890 (2)	−0.2170 (3)	0.2508 (2)	0.0515 (7)
C9	0.1498 (2)	−0.1287 (4)	0.1924 (2)	0.0552 (8)
H9A	0.1105	−0.0411	0.1509	0.066*
H9B	0.1735	−0.1950	0.1406	0.066*
C10	0.2408 (3)	−0.0717 (4)	0.2892 (3)	0.0537 (8)
H10A	0.3021	−0.1365	0.2968	0.064*
H10B	0.2579	0.0370	0.2782	0.064*
N11	0.20128 (18)	−0.0880 (3)	0.3875 (2)	0.0475 (6)
C12	0.1124 (2)	−0.1855 (3)	0.3619 (2)	0.0471 (7)
C13	0.2523 (3)	−0.0357 (4)	0.4938 (3)	0.0538 (8)
O14	0.34333 (19)	0.0302 (3)	0.4922 (2)	0.0733 (7)
C15	0.4057 (3)	0.0951 (5)	0.5990 (4)	0.0937 (14)
H15A	0.3606	0.1450	0.6379	0.112*
H15B	0.4527	0.1742	0.5850	0.112*
C16	0.4668 (3)	−0.0327 (6)	0.6709 (4)	0.1119 (17)
H16A	0.4200	−0.1055	0.6906	0.168*
H16B	0.5122	0.0120	0.7386	0.168*
H16C	0.5075	−0.0869	0.6299	0.168*

	U11	U22	U33	U12	U13	U23
Cl1	0.0669 (7)	0.1178 (9)	0.0857 (9)	0.0107 (6)	−0.0010 (6)	0.0055 (6)
O1	0.0580 (15)	0.0992 (17)	0.0429 (13)	−0.0119 (13)	0.0197 (11)	0.0150 (12)
O2	0.0746 (17)	0.1006 (17)	0.0353 (13)	−0.0080 (13)	0.0204 (12)	−0.0088 (12)
N1	0.0613 (19)	0.094 (2)	0.0381 (16)	−0.0072 (16)	0.0124 (14)	0.0020 (14)
C2	0.065 (2)	0.088 (2)	0.0290 (17)	−0.0102 (19)	0.0121 (15)	−0.0066 (16)
C3	0.0470 (18)	0.0610 (18)	0.0385 (17)	−0.0136 (15)	0.0122 (14)	−0.0050 (14)
C4	0.062 (2)	0.081 (2)	0.0403 (19)	−0.0085 (19)	0.0225 (17)	−0.0091 (17)
C5	0.057 (2)	0.089 (2)	0.045 (2)	−0.0033 (18)	0.0180 (16)	−0.0080 (18)
C6	0.0461 (19)	0.075 (2)	0.051 (2)	−0.0093 (16)	0.0088 (16)	−0.0010 (17)
C7	0.062 (2)	0.063 (2)	0.050 (2)	−0.0107 (17)	0.0131 (17)	−0.0077 (16)
N8	0.0525 (16)	0.0653 (16)	0.0366 (15)	−0.0100 (13)	0.0122 (12)	−0.0006 (12)
C9	0.059 (2)	0.076 (2)	0.0357 (18)	−0.0088 (16)	0.0213 (15)	−0.0047 (15)
C10	0.0527 (19)	0.076 (2)	0.0366 (17)	−0.0077 (16)	0.0200 (14)	−0.0029 (15)
N11	0.0430 (14)	0.0696 (16)	0.0304 (14)	−0.0031 (12)	0.0115 (11)	0.0012 (11)
C12	0.0425 (17)	0.0619 (19)	0.0367 (17)	0.0062 (14)	0.0113 (14)	0.0110 (14)
C13	0.054 (2)	0.071 (2)	0.0355 (18)	−0.0015 (17)	0.0117 (15)	0.0011 (16)
O14	0.0653 (16)	0.1055 (19)	0.0469 (15)	−0.0273 (14)	0.0124 (12)	−0.0147 (13)
C15	0.085 (3)	0.130 (4)	0.058 (3)	−0.035 (3)	0.006 (2)	−0.020 (3)
C16	0.073 (3)	0.174 (5)	0.075 (3)	−0.019 (3)	0.000 (3)	−0.024 (3)

Cl1—C6	1.743 (3)	N8—C9	1.443 (3)
O1—C12	1.209 (3)	C9—C10	1.522 (4)
O2—C13	1.198 (3)	C9—H9A	0.9700
N1—C6	1.315 (4)	C9—H9B	0.9700
N1—C4	1.333 (4)	C10—N11	1.462 (3)
C2—C5	1.364 (5)	C10—H10A	0.9700
C2—C3	1.387 (4)	C10—H10B	0.9700
C2—H2	0.9300	N11—C13	1.368 (4)
C3—C4	1.375 (4)	N11—C12	1.411 (4)
C3—C7	1.512 (4)	C13—O14	1.347 (4)
C4—H4	0.9300	O14—C15	1.452 (4)
C5—C6	1.371 (5)	C15—C16	1.491 (5)
C5—H5	0.9300	C15—H15A	0.9700
C7—N8	1.451 (4)	C15—H15B	0.9700
C7—H7A	0.9700	C16—H16A	0.9600
C7—H7B	0.9700	C16—H16B	0.9600
N8—C12	1.343 (4)	C16—H16C	0.9600
C6—N1—C4	115.8 (3)	H9A—C9—H9B	109.2
C5—C2—C3	120.1 (3)	N11—C10—C9	102.9 (2)
C5—C2—H2	119.9	N11—C10—H10A	111.2
C3—C2—H2	119.9	C9—C10—H10A	111.2
C4—C3—C2	116.4 (3)	N11—C10—H10B	111.2
C4—C3—C7	121.5 (3)	C9—C10—H10B	111.2
C2—C3—C7	122.1 (3)	H10A—C10—H10B	109.1
N1—C4—C3	125.0 (3)	C13—N11—C12	124.4 (2)
N1—C4—H4	117.5	C13—N11—C10	124.3 (2)
C3—C4—H4	117.5	C12—N11—C10	110.6 (2)
C2—C5—C6	117.6 (3)	O1—C12—N8	127.2 (3)
C2—C5—H5	121.2	O1—C12—N11	126.4 (3)
C6—C5—H5	121.2	N8—C12—N11	106.4 (2)
N1—C6—C5	125.0 (3)	O2—C13—O14	124.8 (3)
N1—C6—Cl1	116.1 (3)	O2—C13—N11	126.0 (3)
C5—C6—Cl1	118.9 (3)	O14—C13—N11	109.2 (3)
N8—C7—C3	113.2 (2)	C13—O14—C15	115.8 (3)
N8—C7—H7A	108.9	O14—C15—C16	109.9 (3)
C3—C7—H7A	108.9	O14—C15—H15A	109.7
N8—C7—H7B	108.9	C16—C15—H15A	109.7
C3—C7—H7B	108.9	O14—C15—H15B	109.7
H7A—C7—H7B	107.7	C16—C15—H15B	109.7
C12—N8—C9	113.9 (2)	H15A—C15—H15B	108.2
C12—N8—C7	122.2 (2)	C15—C16—H16A	109.5
C9—N8—C7	123.0 (3)	C15—C16—H16B	109.5
N8—C9—C10	102.3 (2)	H16A—C16—H16B	109.5
N8—C9—H9A	111.3	C15—C16—H16C	109.5
C10—C9—H9A	111.3	H16A—C16—H16C	109.5
N8—C9—H9B	111.3	H16B—C16—H16C	109.5
C10—C9—H9B	111.3
C5—C2—C3—C4	−0.1 (5)	C9—C10—N11—C13	−173.1 (3)
C5—C2—C3—C7	179.1 (3)	C9—C10—N11—C12	16.0 (3)
C6—N1—C4—C3	0.8 (5)	C9—N8—C12—O1	173.2 (3)
C2—C3—C4—N1	−0.6 (5)	C7—N8—C12—O1	4.0 (5)
C7—C3—C4—N1	−179.8 (3)	C9—N8—C12—N11	−7.7 (3)
C3—C2—C5—C6	0.4 (5)	C7—N8—C12—N11	−177.0 (2)
C4—N1—C6—C5	−0.5 (5)	C13—N11—C12—O1	2.1 (5)
C4—N1—C6—Cl1	178.4 (2)	C10—N11—C12—O1	173.0 (3)
C2—C5—C6—N1	−0.1 (5)	C13—N11—C12—N8	−177.0 (3)
C2—C5—C6—Cl1	−179.0 (2)	C10—N11—C12—N8	−6.1 (3)
C4—C3—C7—N8	106.3 (3)	C12—N11—C13—O2	−12.3 (5)
C2—C3—C7—N8	−72.9 (4)	C10—N11—C13—O2	178.0 (3)
C3—C7—N8—C12	91.0 (3)	C12—N11—C13—O14	169.1 (3)
C3—C7—N8—C9	−77.3 (4)	C10—N11—C13—O14	−0.6 (4)
C12—N8—C9—C10	17.3 (3)	O2—C13—O14—C15	−0.1 (5)
C7—N8—C9—C10	−173.5 (3)	N11—C13—O14—C15	178.6 (3)
N8—C9—C10—N11	−18.9 (3)	C13—O14—C15—C16	82.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.93	2.53	3.366 (5)	150
C9—H9B···O2i	0.97	2.50	3.395 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.53	3.366 (5)	150
C9—H9B⋯O2i	0.97	2.50	3.395 (4)	152

Symmetry code: (i) .