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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029824/ob6440sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029824/ob6440Isup2.hkl
Contains datablock I

CCDC reference: 243117

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

Computing details top

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) top
Crystal data top
C9H10ClN5O2F(000) = 528
Mr = 255.67Dx = 1.564 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 865 reflections
a = 19.290 (8) Åθ = 1.4–25.7°
b = 4.839 (2) ŵ = 0.35 mm1
c = 11.784 (5) ÅT = 293 K
β = 99.220 (6)°Prism, colorless
V = 1085.8 (8) Å30.51 × 0.18 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
2364 independent reflections
Radiation source: fine-focus sealed tube1822 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 27.8°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.842, Tmax = 0.953k = 66
8430 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162All H-atom parameters refined
S = 1.12 w = 1/[σ2(Fo2) + (0.0928P)2 + 0.1346P]
where P = (Fo2 + 2Fc2)/3
2364 reflections(Δ/σ)max < 0.001
194 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

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
xyzUiso*/Ueq
Cl10.54482 (4)0.38258 (16)0.67771 (7)0.0577 (3)
N10.64941 (13)0.0440 (6)0.69919 (19)0.0554 (6)
N20.80624 (10)0.3374 (4)0.52725 (17)0.0366 (5)
N30.91593 (12)0.3125 (5)0.59913 (19)0.0442 (5)
N40.83835 (11)0.6260 (4)0.67863 (17)0.0406 (5)
N50.88983 (13)0.7327 (5)0.75567 (17)0.0475 (6)
O10.87200 (13)0.9065 (5)0.82000 (19)0.0751 (7)
O20.95102 (12)0.6611 (5)0.7630 (2)0.0692 (7)
C10.60029 (13)0.1517 (5)0.6243 (2)0.0406 (6)
C20.58924 (14)0.0939 (6)0.5092 (2)0.0470 (7)
C30.63288 (14)0.0941 (6)0.4706 (2)0.0439 (6)
C40.68547 (12)0.2145 (5)0.54596 (19)0.0356 (5)
C50.69141 (15)0.1358 (7)0.6584 (2)0.0547 (8)
C60.73371 (13)0.4252 (6)0.5086 (2)0.0397 (6)
C70.83139 (14)0.1185 (6)0.4613 (2)0.0394 (6)
C80.90970 (14)0.1174 (6)0.5052 (2)0.0441 (6)
C90.85659 (11)0.4331 (5)0.60789 (18)0.0319 (5)
H3N0.9512 (15)0.348 (5)0.637 (3)0.041 (8)*
H20.5520 (16)0.180 (6)0.459 (3)0.063 (9)*
H30.6257 (15)0.151 (6)0.388 (3)0.061 (9)*
H50.727 (2)0.211 (8)0.711 (3)0.087 (11)*
H6A0.7309 (12)0.590 (5)0.553 (2)0.027 (6)*
H6B0.7162 (14)0.468 (6)0.426 (3)0.050 (8)*
H7A0.8100 (14)0.049 (6)0.474 (2)0.045 (7)*
H7B0.8245 (13)0.171 (5)0.387 (3)0.041 (7)*
H8A0.9286 (15)0.060 (6)0.532 (3)0.052 (8)*
H8B0.9364 (14)0.187 (6)0.450 (2)0.042 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0544 (5)0.0648 (5)0.0554 (5)0.0078 (3)0.0134 (3)0.0096 (3)
N10.0545 (14)0.0799 (17)0.0293 (10)0.0144 (12)0.0014 (9)0.0058 (11)
N20.0332 (10)0.0436 (11)0.0318 (10)0.0013 (8)0.0013 (8)0.0075 (8)
N30.0351 (12)0.0583 (14)0.0350 (11)0.0053 (10)0.0070 (9)0.0037 (10)
N40.0448 (12)0.0452 (12)0.0298 (10)0.0050 (9)0.0005 (8)0.0068 (8)
N50.0637 (15)0.0475 (13)0.0282 (10)0.0103 (11)0.0019 (9)0.0015 (9)
O10.105 (2)0.0702 (15)0.0483 (12)0.0120 (13)0.0070 (12)0.0306 (11)
O20.0550 (13)0.0809 (15)0.0619 (14)0.0065 (11)0.0207 (10)0.0188 (12)
C10.0390 (13)0.0458 (14)0.0377 (13)0.0032 (10)0.0080 (10)0.0028 (10)
C20.0432 (15)0.0603 (17)0.0341 (12)0.0123 (12)0.0039 (11)0.0022 (12)
C30.0437 (14)0.0569 (16)0.0276 (12)0.0059 (12)0.0047 (10)0.0012 (11)
C40.0325 (12)0.0430 (13)0.0300 (11)0.0042 (10)0.0005 (9)0.0019 (10)
C50.0521 (16)0.080 (2)0.0277 (12)0.0205 (15)0.0053 (11)0.0037 (12)
C60.0350 (13)0.0444 (14)0.0371 (13)0.0011 (10)0.0021 (10)0.0006 (11)
C70.0482 (15)0.0386 (14)0.0307 (12)0.0006 (11)0.0040 (10)0.0025 (10)
C80.0477 (15)0.0468 (15)0.0382 (13)0.0075 (12)0.0079 (11)0.0025 (11)
C90.0345 (12)0.0368 (12)0.0231 (10)0.0030 (9)0.0004 (8)0.0061 (9)
Geometric parameters (Å, º) top
Cl1—C11.734 (3)C4—C31.367 (3)
N2—C91.328 (3)C4—C61.494 (4)
N2—C71.443 (3)C6—H6A0.96 (2)
N2—C61.445 (3)C6—H6B1.00 (3)
N3—C91.304 (3)C3—C21.366 (4)
N3—C81.445 (3)C3—H31.00 (3)
N3—H3N0.77 (3)C7—C81.516 (4)
O2—N51.220 (3)C7—H7A0.93 (3)
N4—C91.336 (3)C7—H7B0.91 (3)
N4—N51.337 (3)C1—C21.368 (4)
N5—O11.218 (3)C8—H8A0.97 (3)
N1—C11.296 (3)C8—H8B0.95 (3)
N1—C51.330 (4)C2—H20.95 (3)
C4—C51.365 (3)C5—H50.92 (4)
C9—N2—C7111.8 (2)C2—C3—H3120.7 (17)
C9—N2—C6125.8 (2)C4—C3—H3119.2 (17)
C7—N2—C6122.4 (2)N2—C7—C8102.8 (2)
C9—N3—C8112.8 (2)N2—C7—H7A111.1 (18)
C9—N3—H3N124 (2)C8—C7—H7A112.6 (17)
C8—N3—H3N123 (2)N2—C7—H7B107.9 (17)
C9—N4—N5116.9 (2)C8—C7—H7B108.4 (17)
O1—N5—O2121.2 (2)H7A—C7—H7B113 (2)
O1—N5—N4115.9 (2)N1—C1—C2125.0 (2)
O2—N5—N4122.9 (2)N1—C1—Cl1115.98 (19)
C1—N1—C5116.0 (2)C2—C1—Cl1119.0 (2)
N3—C9—N2109.7 (2)N3—C8—C7102.4 (2)
N3—C9—N4133.2 (2)N3—C8—H8A110.3 (18)
N2—C9—N4117.0 (2)C7—C8—H8A114.7 (17)
C5—C4—C3116.7 (2)N3—C8—H8B107.6 (17)
C5—C4—C6121.1 (2)C7—C8—H8B112.8 (16)
C3—C4—C6122.2 (2)H8A—C8—H8B109 (2)
N2—C6—C4112.8 (2)C3—C2—C1117.4 (2)
N2—C6—H6A107.5 (14)C3—C2—H2122 (2)
C4—C6—H6A108.5 (14)C1—C2—H2120 (2)
N2—C6—H6B112.0 (16)N1—C5—C4124.9 (2)
C4—C6—H6B107.4 (16)N1—C5—H5116 (2)
H6A—C6—H6B108 (2)C4—C5—H5119 (2)
C2—C3—C4120.0 (2)
C9—N4—N5—O1179.4 (2)C5—C4—C3—C20.3 (4)
C9—N4—N5—O20.0 (4)C6—C4—C3—C2178.8 (2)
C8—N3—C9—N20.8 (3)C9—N2—C7—C86.9 (3)
C8—N3—C9—N4178.6 (2)C6—N2—C7—C8176.0 (2)
C7—N2—C9—N34.1 (3)C5—N1—C1—C20.0 (4)
C6—N2—C9—N3178.9 (2)C5—N1—C1—Cl1179.2 (2)
C7—N2—C9—N4176.3 (2)C9—N3—C8—C75.0 (3)
C6—N2—C9—N40.6 (3)N2—C7—C8—N36.7 (3)
N5—N4—C9—N32.9 (4)C4—C3—C2—C10.5 (4)
N5—N4—C9—N2176.5 (2)N1—C1—C2—C30.7 (4)
C9—N2—C6—C4107.0 (3)Cl1—C1—C2—C3178.4 (2)
C7—N2—C6—C469.6 (3)C1—N1—C5—C41.0 (5)
C5—C4—C6—N263.0 (3)C3—C4—C5—N11.2 (5)
C3—C4—C6—N2118.0 (3)C6—C4—C5—N1177.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.77 (3)2.12 (3)2.572 (3)118 (3)
N3—H3N···O2i0.77 (3)2.25 (3)2.903 (4)143 (2)
C7—H7B···O1ii0.90 (3)2.42 (3)3.015 (4)123 (2)
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x, y+3/2, z1/2.
 

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