(2E)-1-[(6-Chloro­pyridin-3-yl)­methyl]-N-nitro­imidazolidin-2-imine (imidachloprid)

The title compound (also known as imidachloprid), C₉H₁₀ClN₅O₂, is an active agrochemical possessing insecticidal activity. The dihedral angle between the mean planes passing through the pyridine ring and the imidazolidine ring is 76.9 (1)°. There are intramolecular and intermolecular N—H...O hydrogen bonds and C—H...O intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.162
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.22 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

(2E)-1-[(6-Chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine (imidachloprid)

Crystal data

C9H10ClN5O2	F(000) = 528
Mr = 255.67	Dx = 1.564 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 865 reflections
a = 19.290 (8) Å	θ = 1.4–25.7°
b = 4.839 (2) Å	µ = 0.35 mm^−1
c = 11.784 (5) Å	T = 293 K
β = 99.220 (6)°	Prism, colorless
V = 1085.8 (8) Å^3	0.51 × 0.18 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	2364 independent reflections
Radiation source: fine-focus sealed tube	1822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 27.8°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.842, Tmax = 0.953	k = −6→6
8430 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0928P)^2 + 0.1346P] where P = (Fo^2 + 2Fc^2)/3
2364 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.54482 (4)	−0.38258 (16)	0.67771 (7)	0.0577 (3)
N1	0.64941 (13)	−0.0440 (6)	0.69919 (19)	0.0554 (6)
N2	0.80624 (10)	0.3374 (4)	0.52725 (17)	0.0366 (5)
N3	0.91593 (12)	0.3125 (5)	0.59913 (19)	0.0442 (5)
N4	0.83835 (11)	0.6260 (4)	0.67863 (17)	0.0406 (5)
N5	0.88983 (13)	0.7327 (5)	0.75567 (17)	0.0475 (6)
O1	0.87200 (13)	0.9065 (5)	0.82000 (19)	0.0751 (7)
O2	0.95102 (12)	0.6611 (5)	0.7630 (2)	0.0692 (7)
C1	0.60029 (13)	−0.1517 (5)	0.6243 (2)	0.0406 (6)
C2	0.58924 (14)	−0.0939 (6)	0.5092 (2)	0.0470 (7)
C3	0.63288 (14)	0.0941 (6)	0.4706 (2)	0.0439 (6)
C4	0.68547 (12)	0.2145 (5)	0.54596 (19)	0.0356 (5)
C5	0.69141 (15)	0.1358 (7)	0.6584 (2)	0.0547 (8)
C6	0.73371 (13)	0.4252 (6)	0.5086 (2)	0.0397 (6)
C7	0.83139 (14)	0.1185 (6)	0.4613 (2)	0.0394 (6)
C8	0.90970 (14)	0.1174 (6)	0.5052 (2)	0.0441 (6)
C9	0.85659 (11)	0.4331 (5)	0.60789 (18)	0.0319 (5)
H3N	0.9512 (15)	0.348 (5)	0.637 (3)	0.041 (8)*
H2	0.5520 (16)	−0.180 (6)	0.459 (3)	0.063 (9)*
H3	0.6257 (15)	0.151 (6)	0.388 (3)	0.061 (9)*
H5	0.727 (2)	0.211 (8)	0.711 (3)	0.087 (11)*
H6A	0.7309 (12)	0.590 (5)	0.553 (2)	0.027 (6)*
H6B	0.7162 (14)	0.468 (6)	0.426 (3)	0.050 (8)*
H7A	0.8100 (14)	−0.049 (6)	0.474 (2)	0.045 (7)*
H7B	0.8245 (13)	0.171 (5)	0.387 (3)	0.041 (7)*
H8A	0.9286 (15)	−0.060 (6)	0.532 (3)	0.052 (8)*
H8B	0.9364 (14)	0.187 (6)	0.450 (2)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0544 (5)	0.0648 (5)	0.0554 (5)	−0.0078 (3)	0.0134 (3)	0.0096 (3)
N1	0.0545 (14)	0.0799 (17)	0.0293 (10)	−0.0144 (12)	−0.0014 (9)	0.0058 (11)
N2	0.0332 (10)	0.0436 (11)	0.0318 (10)	−0.0013 (8)	0.0013 (8)	−0.0075 (8)
N3	0.0351 (12)	0.0583 (14)	0.0350 (11)	0.0053 (10)	−0.0070 (9)	−0.0037 (10)
N4	0.0448 (12)	0.0452 (12)	0.0298 (10)	−0.0050 (9)	−0.0005 (8)	−0.0068 (8)
N5	0.0637 (15)	0.0475 (13)	0.0282 (10)	−0.0103 (11)	−0.0019 (9)	−0.0015 (9)
O1	0.105 (2)	0.0702 (15)	0.0483 (12)	−0.0120 (13)	0.0070 (12)	−0.0306 (11)
O2	0.0550 (13)	0.0809 (15)	0.0619 (14)	−0.0065 (11)	−0.0207 (10)	−0.0188 (12)
C1	0.0390 (13)	0.0458 (14)	0.0377 (13)	0.0032 (10)	0.0080 (10)	0.0028 (10)
C2	0.0432 (15)	0.0603 (17)	0.0341 (12)	−0.0123 (12)	−0.0039 (11)	−0.0022 (12)
C3	0.0437 (14)	0.0569 (16)	0.0276 (12)	−0.0059 (12)	−0.0047 (10)	0.0012 (11)
C4	0.0325 (12)	0.0430 (13)	0.0300 (11)	0.0042 (10)	0.0005 (9)	−0.0019 (10)
C5	0.0521 (16)	0.080 (2)	0.0277 (12)	−0.0205 (15)	−0.0053 (11)	−0.0037 (12)
C6	0.0350 (13)	0.0444 (14)	0.0371 (13)	0.0011 (10)	−0.0021 (10)	−0.0006 (11)
C7	0.0482 (15)	0.0386 (14)	0.0307 (12)	−0.0006 (11)	0.0040 (10)	−0.0025 (10)
C8	0.0477 (15)	0.0468 (15)	0.0382 (13)	0.0075 (12)	0.0079 (11)	0.0025 (11)
C9	0.0345 (12)	0.0368 (12)	0.0231 (10)	−0.0030 (9)	0.0004 (8)	0.0061 (9)

Geometric parameters (Å, º)

Cl1—C1	1.734 (3)	C4—C3	1.367 (3)
N2—C9	1.328 (3)	C4—C6	1.494 (4)
N2—C7	1.443 (3)	C6—H6A	0.96 (2)
N2—C6	1.445 (3)	C6—H6B	1.00 (3)
N3—C9	1.304 (3)	C3—C2	1.366 (4)
N3—C8	1.445 (3)	C3—H3	1.00 (3)
N3—H3N	0.77 (3)	C7—C8	1.516 (4)
O2—N5	1.220 (3)	C7—H7A	0.93 (3)
N4—C9	1.336 (3)	C7—H7B	0.91 (3)
N4—N5	1.337 (3)	C1—C2	1.368 (4)
N5—O1	1.218 (3)	C8—H8A	0.97 (3)
N1—C1	1.296 (3)	C8—H8B	0.95 (3)
N1—C5	1.330 (4)	C2—H2	0.95 (3)
C4—C5	1.365 (3)	C5—H5	0.92 (4)
C9—N2—C7	111.8 (2)	C2—C3—H3	120.7 (17)
C9—N2—C6	125.8 (2)	C4—C3—H3	119.2 (17)
C7—N2—C6	122.4 (2)	N2—C7—C8	102.8 (2)
C9—N3—C8	112.8 (2)	N2—C7—H7A	111.1 (18)
C9—N3—H3N	124 (2)	C8—C7—H7A	112.6 (17)
C8—N3—H3N	123 (2)	N2—C7—H7B	107.9 (17)
C9—N4—N5	116.9 (2)	C8—C7—H7B	108.4 (17)
O1—N5—O2	121.2 (2)	H7A—C7—H7B	113 (2)
O1—N5—N4	115.9 (2)	N1—C1—C2	125.0 (2)
O2—N5—N4	122.9 (2)	N1—C1—Cl1	115.98 (19)
C1—N1—C5	116.0 (2)	C2—C1—Cl1	119.0 (2)
N3—C9—N2	109.7 (2)	N3—C8—C7	102.4 (2)
N3—C9—N4	133.2 (2)	N3—C8—H8A	110.3 (18)
N2—C9—N4	117.0 (2)	C7—C8—H8A	114.7 (17)
C5—C4—C3	116.7 (2)	N3—C8—H8B	107.6 (17)
C5—C4—C6	121.1 (2)	C7—C8—H8B	112.8 (16)
C3—C4—C6	122.2 (2)	H8A—C8—H8B	109 (2)
N2—C6—C4	112.8 (2)	C3—C2—C1	117.4 (2)
N2—C6—H6A	107.5 (14)	C3—C2—H2	122 (2)
C4—C6—H6A	108.5 (14)	C1—C2—H2	120 (2)
N2—C6—H6B	112.0 (16)	N1—C5—C4	124.9 (2)
C4—C6—H6B	107.4 (16)	N1—C5—H5	116 (2)
H6A—C6—H6B	108 (2)	C4—C5—H5	119 (2)
C2—C3—C4	120.0 (2)
C9—N4—N5—O1	−179.4 (2)	C5—C4—C3—C2	0.3 (4)
C9—N4—N5—O2	0.0 (4)	C6—C4—C3—C2	−178.8 (2)
C8—N3—C9—N2	0.8 (3)	C9—N2—C7—C8	−6.9 (3)
C8—N3—C9—N4	−178.6 (2)	C6—N2—C7—C8	176.0 (2)
C7—N2—C9—N3	4.1 (3)	C5—N1—C1—C2	0.0 (4)
C6—N2—C9—N3	−178.9 (2)	C5—N1—C1—Cl1	−179.2 (2)
C7—N2—C9—N4	−176.3 (2)	C9—N3—C8—C7	−5.0 (3)
C6—N2—C9—N4	0.6 (3)	N2—C7—C8—N3	6.7 (3)
N5—N4—C9—N3	2.9 (4)	C4—C3—C2—C1	0.5 (4)
N5—N4—C9—N2	−176.5 (2)	N1—C1—C2—C3	−0.7 (4)
C9—N2—C6—C4	−107.0 (3)	Cl1—C1—C2—C3	178.4 (2)
C7—N2—C6—C4	69.6 (3)	C1—N1—C5—C4	1.0 (5)
C5—C4—C6—N2	63.0 (3)	C3—C4—C5—N1	−1.2 (5)
C3—C4—C6—N2	−118.0 (3)	C6—C4—C5—N1	177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2	0.77 (3)	2.12 (3)	2.572 (3)	118 (3)
N3—H3N···O2^i	0.77 (3)	2.25 (3)	2.903 (4)	143 (2)
C7—H7B···O1^ii	0.90 (3)	2.42 (3)	3.015 (4)	123 (2)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+3/2, z−1/2.