organic compounds
N-{(1Z)-1-[(6-Chloropyridin-3-ylmethyl)(ethyl)amino]-3-(3-chlorophenyl)-2-nitro-5-oxohex-1-enyl}-N-methylacetamide
aDepartment of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai, 200234, People's Republic of China
*Correspondence e-mail: xiaobuling123@126.com
In the title compound, C23H26Cl2N4O4,the dihedral angle between the mean planes of the pyridine and 3-chlorophenyl rings is 22.63 (2)°. The nitro group is in a Z conformation.
Related literature
For general background to neonicotinoid compounds and their application as insecticides, see: Tomizawa & Casida, (2000); Minamida et al. (1993); Kashiwada et al. (1996). For the synthesis, see: Zhang et al. (2010).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812043358/jj2153sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043358/jj2153Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043358/jj2153Isup3.cml
The title compound was prepared by the literature method (Zhang et al., 2010). It was obtained using
of petroleum ether and ethyl acetate solution at room temperature, giving yellow crystals (yield 78.6%). Anal. calcd. for C23H26Cl2N4O4 C 55.99, H 5.31, N 11.36%. found, C 55.97, H 5.32, N 11.38%.In (I), H atoms bonded to C and N atoms were located at their ideal positions and subsequently treated as riding modes with C–H distances of 0.93Å (aromatic), 0.97Å (methylene), 0.98Å (methine) and 0.96Å (methyl) with Uiso(H) = 1.2Ueq(aromatic, methylene methine C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C23H26Cl2N4O4 | Z = 2 |
Mr = 493.38 | F(000) = 516 |
Triclinic, P1 | Dx = 1.361 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7948 (13) Å | Cell parameters from 4525 reflections |
b = 12.649 (2) Å | θ = 2.2–28.3° |
c = 13.021 (2) Å | µ = 0.31 mm−1 |
α = 91.364 (3)° | T = 298 K |
β = 98.765 (2)° | Block, yellow |
γ = 107.878 (3)° | 0.16 × 0.12 × 0.10 mm |
V = 1204.1 (3) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4200 independent reflections |
Radiation source: fine-focus sealed tube | 3870 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
phi and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→9 |
Tmin = 0.943, Tmax = 0.970 | k = −15→13 |
7096 measured reflections | l = −15→15 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.9109P] where P = (Fo2 + 2Fc2)/3 |
4200 reflections | (Δ/σ)max = 0.011 |
302 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C23H26Cl2N4O4 | γ = 107.878 (3)° |
Mr = 493.38 | V = 1204.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7948 (13) Å | Mo Kα radiation |
b = 12.649 (2) Å | µ = 0.31 mm−1 |
c = 13.021 (2) Å | T = 298 K |
α = 91.364 (3)° | 0.16 × 0.12 × 0.10 mm |
β = 98.765 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 4200 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3870 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.970 | Rint = 0.020 |
7096 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.17 | Δρmax = 0.47 e Å−3 |
4200 reflections | Δρmin = −0.38 e Å−3 |
302 parameters |
Experimental. 1H NMR (CDCl3, 400 Hz): 8.47 (d, J = 1.9 Hz,1H, Py—H), 7.83 (dd, J = 8.2, 2.4 Hz, 1H, Py—H), 7.42 (d, J = 8.2 Hz, 1H, Py—H), 7.12 (d, J = 10.2 Hz, 1H, Ph—H), 7.01–6.91 (m, 3H, Ph—H), 4.27 (d, J = 14.7 Hz, 1H), 4.12 (d, J = 7.7 Hz, 1H), 4.00 (dd, J = 10.8, 3.8 Hz, 1H), 3.78 (d, J = 14.8 Hz, 1H), 3.31 (s, 3H, NCH3), 3.09 (dd, J = 14.4, 7.2 Hz, 1H, NCH2), 2.89 (d, J = 3.9Hz, 1H, NCH2), 2.26 (s, 1H), 2.13 (s, 3H), 1.67 (s, 3H), 1.17 (t, J = 7.2 Hz, 3H, NCH2CH3). IR(KBr, cm-1) 2945 (CH3), 1710 (C=O), 1658 (C=C), 1378, 1390(NO2), 1660, 1621, 1538(benzene). |
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 > 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 | ||
C1 | 0.9628 (4) | 0.8187 (2) | 0.8649 (3) | 0.0521 (7) | |
C2 | 0.9304 (4) | 0.8215 (3) | 0.7596 (2) | 0.0559 (8) | |
H2 | 1.0030 | 0.8779 | 0.7259 | 0.067* | |
C3 | 0.7857 (4) | 0.7376 (3) | 0.7052 (2) | 0.0540 (8) | |
H3 | 0.7581 | 0.7367 | 0.6331 | 0.065* | |
C4 | 0.6813 (4) | 0.6546 (2) | 0.7573 (2) | 0.0427 (6) | |
C5 | 0.7293 (4) | 0.6599 (3) | 0.8637 (2) | 0.0596 (8) | |
H5 | 0.6613 | 0.6036 | 0.8995 | 0.071* | |
C6 | 0.5256 (4) | 0.5591 (2) | 0.6992 (2) | 0.0451 (6) | |
H6A | 0.5205 | 0.5665 | 0.6249 | 0.054* | |
H6B | 0.5492 | 0.4896 | 0.7142 | 0.054* | |
C7 | 0.3021 (4) | 0.6592 (2) | 0.7287 (2) | 0.0480 (7) | |
H7A | 0.4057 | 0.7180 | 0.7664 | 0.058* | |
H7B | 0.1998 | 0.6501 | 0.7655 | 0.058* | |
C8 | 0.2535 (6) | 0.6925 (3) | 0.6212 (3) | 0.0785 (11) | |
H8A | 0.3540 | 0.7011 | 0.5843 | 0.118* | |
H8B | 0.2277 | 0.7618 | 0.6258 | 0.118* | |
H8C | 0.1475 | 0.6360 | 0.5846 | 0.118* | |
C9 | 0.2212 (3) | 0.4559 (2) | 0.73211 (18) | 0.0348 (5) | |
C10 | 0.1460 (5) | 0.4994 (3) | 0.9036 (2) | 0.0550 (8) | |
H10A | 0.0962 | 0.5579 | 0.9175 | 0.083* | |
H10B | 0.2771 | 0.5277 | 0.9188 | 0.083* | |
H10C | 0.1029 | 0.4395 | 0.9465 | 0.083* | |
C11 | −0.0970 (4) | 0.4176 (3) | 0.7564 (2) | 0.0519 (7) | |
C12 | −0.1607 (4) | 0.3915 (3) | 0.6418 (3) | 0.0650 (9) | |
H12A | −0.2290 | 0.3138 | 0.6283 | 0.098* | |
H12B | −0.0569 | 0.4085 | 0.6066 | 0.098* | |
H12C | −0.2373 | 0.4353 | 0.6169 | 0.098* | |
C13 | 0.2214 (3) | 0.3532 (2) | 0.69263 (19) | 0.0368 (6) | |
C14 | 0.1557 (4) | 0.2493 (2) | 0.7497 (2) | 0.0421 (6) | |
H14 | 0.1153 | 0.2752 | 0.8105 | 0.051* | |
C15 | 0.3084 (4) | 0.2029 (2) | 0.7966 (2) | 0.0542 (7) | |
H15A | 0.2532 | 0.1285 | 0.8171 | 0.065* | |
H15B | 0.3801 | 0.1969 | 0.7433 | 0.065* | |
C16 | 0.4344 (4) | 0.2730 (2) | 0.8897 (2) | 0.0500 (7) | |
C17 | 0.5633 (6) | 0.2214 (3) | 0.9493 (3) | 0.0795 (11) | |
H17A | 0.6664 | 0.2789 | 0.9873 | 0.119* | |
H17B | 0.6046 | 0.1792 | 0.9019 | 0.119* | |
H17C | 0.5019 | 0.1731 | 0.9972 | 0.119* | |
C18 | −0.0129 (4) | 0.1572 (2) | 0.6946 (2) | 0.0454 (6) | |
C19 | −0.0443 (5) | 0.1205 (3) | 0.5905 (3) | 0.0766 (11) | |
H19 | 0.0405 | 0.1535 | 0.5483 | 0.092* | |
C20 | −0.2016 (6) | 0.0346 (4) | 0.5483 (3) | 0.0891 (13) | |
H20 | −0.2201 | 0.0106 | 0.4782 | 0.107* | |
C21 | −0.3293 (5) | −0.0151 (3) | 0.6078 (3) | 0.0746 (11) | |
H21 | −0.4345 | −0.0724 | 0.5793 | 0.090* | |
C22 | −0.2985 (5) | 0.0214 (3) | 0.7100 (3) | 0.0661 (9) | |
C23 | −0.1431 (4) | 0.1059 (2) | 0.7539 (3) | 0.0581 (8) | |
H23 | −0.1258 | 0.1286 | 0.8242 | 0.070* | |
Cl1 | 1.14377 (13) | 0.92531 (8) | 0.93748 (8) | 0.0793 (3) | |
Cl2 | −0.45945 (18) | −0.04123 (10) | 0.78826 (12) | 0.1249 (6) | |
N1 | 0.8686 (4) | 0.7416 (2) | 0.9194 (2) | 0.0676 (8) | |
N2 | 0.3480 (3) | 0.55437 (17) | 0.72679 (16) | 0.0377 (5) | |
N3 | 0.0879 (3) | 0.45855 (18) | 0.79346 (17) | 0.0416 (5) | |
N4 | 0.2894 (3) | 0.34678 (19) | 0.59894 (18) | 0.0459 (6) | |
O1 | −0.2039 (3) | 0.4098 (2) | 0.8168 (2) | 0.0819 (8) | |
O2 | 0.2890 (3) | 0.41880 (18) | 0.53559 (15) | 0.0616 (6) | |
O3 | 0.3403 (3) | 0.26542 (19) | 0.57805 (18) | 0.0650 (6) | |
O4 | 0.4321 (3) | 0.36466 (18) | 0.91429 (17) | 0.0595 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0429 (16) | 0.0456 (16) | 0.0630 (19) | 0.0094 (13) | 0.0035 (14) | 0.0074 (14) |
C2 | 0.0512 (17) | 0.0492 (17) | 0.0596 (19) | 0.0001 (14) | 0.0176 (15) | 0.0138 (14) |
C3 | 0.0560 (18) | 0.0566 (18) | 0.0424 (16) | 0.0040 (14) | 0.0158 (14) | 0.0045 (13) |
C4 | 0.0409 (14) | 0.0416 (14) | 0.0454 (15) | 0.0103 (12) | 0.0126 (12) | 0.0029 (12) |
C5 | 0.0566 (19) | 0.0544 (18) | 0.0537 (19) | −0.0035 (15) | 0.0088 (15) | 0.0142 (14) |
C6 | 0.0449 (15) | 0.0438 (15) | 0.0470 (16) | 0.0104 (12) | 0.0166 (12) | −0.0009 (12) |
C7 | 0.0543 (17) | 0.0365 (14) | 0.0537 (17) | 0.0151 (13) | 0.0096 (13) | 0.0014 (12) |
C8 | 0.104 (3) | 0.062 (2) | 0.072 (2) | 0.034 (2) | 0.004 (2) | 0.0170 (18) |
C9 | 0.0377 (13) | 0.0398 (13) | 0.0273 (12) | 0.0119 (11) | 0.0069 (10) | 0.0048 (10) |
C10 | 0.0659 (19) | 0.0668 (19) | 0.0377 (15) | 0.0243 (16) | 0.0184 (14) | −0.0012 (13) |
C11 | 0.0449 (16) | 0.0550 (17) | 0.0609 (19) | 0.0194 (14) | 0.0162 (14) | 0.0080 (14) |
C12 | 0.0472 (18) | 0.080 (2) | 0.066 (2) | 0.0234 (17) | −0.0005 (15) | −0.0007 (18) |
C13 | 0.0363 (13) | 0.0391 (14) | 0.0337 (13) | 0.0075 (11) | 0.0109 (10) | 0.0009 (10) |
C14 | 0.0458 (15) | 0.0363 (14) | 0.0398 (14) | 0.0068 (11) | 0.0067 (12) | 0.0007 (11) |
C15 | 0.0574 (18) | 0.0411 (15) | 0.0588 (18) | 0.0132 (13) | −0.0013 (15) | 0.0030 (13) |
C16 | 0.0471 (16) | 0.0479 (17) | 0.0512 (17) | 0.0095 (13) | 0.0079 (13) | 0.0063 (13) |
C17 | 0.084 (3) | 0.064 (2) | 0.079 (3) | 0.0224 (19) | −0.022 (2) | 0.0009 (18) |
C18 | 0.0453 (15) | 0.0348 (14) | 0.0536 (17) | 0.0101 (12) | 0.0059 (13) | 0.0043 (12) |
C19 | 0.072 (2) | 0.080 (2) | 0.052 (2) | −0.0111 (19) | 0.0038 (17) | 0.0028 (17) |
C20 | 0.086 (3) | 0.089 (3) | 0.057 (2) | −0.010 (2) | −0.013 (2) | −0.005 (2) |
C21 | 0.055 (2) | 0.053 (2) | 0.094 (3) | −0.0023 (16) | −0.0104 (19) | 0.0010 (19) |
C22 | 0.0543 (19) | 0.0384 (16) | 0.098 (3) | 0.0009 (14) | 0.0198 (18) | −0.0028 (17) |
C23 | 0.0622 (19) | 0.0373 (15) | 0.069 (2) | 0.0038 (14) | 0.0196 (16) | −0.0040 (14) |
Cl1 | 0.0610 (5) | 0.0625 (5) | 0.0888 (7) | −0.0048 (4) | −0.0140 (5) | 0.0050 (5) |
Cl2 | 0.1075 (9) | 0.0734 (7) | 0.1642 (13) | −0.0375 (6) | 0.0766 (9) | −0.0304 (7) |
N1 | 0.0650 (18) | 0.0645 (17) | 0.0553 (16) | −0.0018 (14) | 0.0001 (13) | 0.0126 (13) |
N2 | 0.0418 (12) | 0.0355 (11) | 0.0369 (11) | 0.0115 (9) | 0.0115 (9) | 0.0027 (9) |
N3 | 0.0413 (12) | 0.0477 (13) | 0.0389 (12) | 0.0151 (10) | 0.0144 (10) | 0.0016 (10) |
N4 | 0.0456 (13) | 0.0450 (13) | 0.0420 (13) | 0.0053 (10) | 0.0122 (10) | −0.0092 (11) |
O1 | 0.0523 (14) | 0.118 (2) | 0.0845 (18) | 0.0287 (14) | 0.0336 (13) | 0.0132 (16) |
O2 | 0.0865 (16) | 0.0549 (13) | 0.0370 (11) | 0.0071 (11) | 0.0221 (11) | 0.0050 (10) |
O3 | 0.0679 (14) | 0.0622 (14) | 0.0711 (15) | 0.0237 (11) | 0.0270 (12) | −0.0149 (11) |
O4 | 0.0589 (13) | 0.0600 (14) | 0.0574 (13) | 0.0196 (11) | 0.0041 (10) | −0.0119 (10) |
C1—N1 | 1.321 (4) | C11—C12 | 1.494 (4) |
C1—C2 | 1.359 (4) | C12—H12A | 0.9600 |
C1—Cl1 | 1.751 (3) | C12—H12B | 0.9600 |
C2—C3 | 1.373 (4) | C12—H12C | 0.9600 |
C2—H2 | 0.9300 | C13—N4 | 1.412 (3) |
C3—C4 | 1.379 (4) | C13—C14 | 1.513 (4) |
C3—H3 | 0.9300 | C14—C18 | 1.527 (4) |
C4—C5 | 1.374 (4) | C14—C15 | 1.536 (4) |
C4—C6 | 1.510 (4) | C14—H14 | 0.9800 |
C5—N1 | 1.344 (4) | C15—C16 | 1.508 (4) |
C5—H5 | 0.9300 | C15—H15A | 0.9700 |
C6—N2 | 1.466 (3) | C15—H15B | 0.9700 |
C6—H6A | 0.9700 | C16—O4 | 1.202 (3) |
C6—H6B | 0.9700 | C16—C17 | 1.492 (5) |
C7—N2 | 1.476 (3) | C17—H17A | 0.9600 |
C7—C8 | 1.498 (4) | C17—H17B | 0.9600 |
C7—H7A | 0.9700 | C17—H17C | 0.9600 |
C7—H7B | 0.9700 | C18—C23 | 1.380 (4) |
C8—H8A | 0.9600 | C18—C19 | 1.383 (4) |
C8—H8B | 0.9600 | C19—C20 | 1.391 (5) |
C8—H8C | 0.9600 | C19—H19 | 0.9300 |
C9—N2 | 1.343 (3) | C20—C21 | 1.364 (6) |
C9—C13 | 1.387 (3) | C20—H20 | 0.9300 |
C9—N3 | 1.412 (3) | C21—C22 | 1.359 (5) |
C10—N3 | 1.467 (3) | C21—H21 | 0.9300 |
C10—H10A | 0.9600 | C22—C23 | 1.378 (4) |
C10—H10B | 0.9600 | C22—Cl2 | 1.749 (4) |
C10—H10C | 0.9600 | C23—H23 | 0.9300 |
C11—O1 | 1.215 (4) | N4—O2 | 1.244 (3) |
C11—N3 | 1.377 (4) | N4—O3 | 1.249 (3) |
N1—C1—C2 | 125.7 (3) | C9—C13—C14 | 121.2 (2) |
N1—C1—Cl1 | 115.7 (2) | N4—C13—C14 | 119.8 (2) |
C2—C1—Cl1 | 118.6 (2) | C13—C14—C18 | 117.0 (2) |
C1—C2—C3 | 117.1 (3) | C13—C14—C15 | 114.0 (2) |
C1—C2—H2 | 121.4 | C18—C14—C15 | 111.8 (2) |
C3—C2—H2 | 121.4 | C13—C14—H14 | 104.1 |
C2—C3—C4 | 120.2 (3) | C18—C14—H14 | 104.1 |
C2—C3—H3 | 119.9 | C15—C14—H14 | 104.1 |
C4—C3—H3 | 119.9 | C16—C15—C14 | 113.8 (2) |
C5—C4—C3 | 117.3 (3) | C16—C15—H15A | 108.8 |
C5—C4—C6 | 121.4 (2) | C14—C15—H15A | 108.8 |
C3—C4—C6 | 121.3 (3) | C16—C15—H15B | 108.8 |
N1—C5—C4 | 124.1 (3) | C14—C15—H15B | 108.8 |
N1—C5—H5 | 118.0 | H15A—C15—H15B | 107.7 |
C4—C5—H5 | 118.0 | O4—C16—C17 | 122.0 (3) |
N2—C6—C4 | 112.9 (2) | O4—C16—C15 | 122.3 (3) |
N2—C6—H6A | 109.0 | C17—C16—C15 | 115.7 (3) |
C4—C6—H6A | 109.0 | C16—C17—H17A | 109.5 |
N2—C6—H6B | 109.0 | C16—C17—H17B | 109.5 |
C4—C6—H6B | 109.0 | H17A—C17—H17B | 109.5 |
H6A—C6—H6B | 107.8 | C16—C17—H17C | 109.5 |
N2—C7—C8 | 112.1 (2) | H17A—C17—H17C | 109.5 |
N2—C7—H7A | 109.2 | H17B—C17—H17C | 109.5 |
C8—C7—H7A | 109.2 | C23—C18—C19 | 117.6 (3) |
N2—C7—H7B | 109.2 | C23—C18—C14 | 117.3 (3) |
C8—C7—H7B | 109.2 | C19—C18—C14 | 125.2 (3) |
H7A—C7—H7B | 107.9 | C18—C19—C20 | 120.6 (3) |
C7—C8—H8A | 109.5 | C18—C19—H19 | 119.7 |
C7—C8—H8B | 109.5 | C20—C19—H19 | 119.7 |
H8A—C8—H8B | 109.5 | C21—C20—C19 | 121.2 (4) |
C7—C8—H8C | 109.5 | C21—C20—H20 | 119.4 |
H8A—C8—H8C | 109.5 | C19—C20—H20 | 119.4 |
H8B—C8—H8C | 109.5 | C22—C21—C20 | 118.1 (3) |
N2—C9—C13 | 126.1 (2) | C22—C21—H21 | 120.9 |
N2—C9—N3 | 115.3 (2) | C20—C21—H21 | 120.9 |
C13—C9—N3 | 118.3 (2) | C21—C22—C23 | 121.8 (3) |
N3—C10—H10A | 109.5 | C21—C22—Cl2 | 119.1 (3) |
N3—C10—H10B | 109.5 | C23—C22—Cl2 | 119.1 (3) |
H10A—C10—H10B | 109.5 | C22—C23—C18 | 120.7 (3) |
N3—C10—H10C | 109.5 | C22—C23—H23 | 119.6 |
H10A—C10—H10C | 109.5 | C18—C23—H23 | 119.6 |
H10B—C10—H10C | 109.5 | C1—N1—C5 | 115.6 (3) |
O1—C11—N3 | 119.2 (3) | C9—N2—C6 | 120.5 (2) |
O1—C11—C12 | 121.7 (3) | C9—N2—C7 | 121.1 (2) |
N3—C11—C12 | 119.0 (3) | C6—N2—C7 | 117.4 (2) |
C11—C12—H12A | 109.5 | C11—N3—C9 | 122.8 (2) |
C11—C12—H12B | 109.5 | C11—N3—C10 | 117.8 (2) |
H12A—C12—H12B | 109.5 | C9—N3—C10 | 119.3 (2) |
C11—C12—H12C | 109.5 | O2—N4—O3 | 120.6 (2) |
H12A—C12—H12C | 109.5 | O2—N4—C13 | 119.8 (2) |
H12B—C12—H12C | 109.5 | O3—N4—C13 | 119.5 (2) |
C9—C13—N4 | 118.9 (2) | ||
N1—C1—C2—C3 | 0.7 (5) | C20—C21—C22—C23 | −0.3 (6) |
Cl1—C1—C2—C3 | −179.0 (2) | C20—C21—C22—Cl2 | −179.7 (3) |
C1—C2—C3—C4 | −0.6 (5) | C21—C22—C23—C18 | 0.5 (5) |
C2—C3—C4—C5 | −0.4 (5) | Cl2—C22—C23—C18 | 179.9 (3) |
C2—C3—C4—C6 | −177.9 (3) | C19—C18—C23—C22 | −0.2 (5) |
C3—C4—C5—N1 | 1.3 (5) | C14—C18—C23—C22 | −179.5 (3) |
C6—C4—C5—N1 | 178.7 (3) | C2—C1—N1—C5 | 0.1 (5) |
C5—C4—C6—N2 | 64.1 (4) | Cl1—C1—N1—C5 | 179.8 (3) |
C3—C4—C6—N2 | −118.5 (3) | C4—C5—N1—C1 | −1.1 (5) |
N2—C9—C13—N4 | −35.2 (4) | C13—C9—N2—C6 | −14.8 (4) |
N3—C9—C13—N4 | 152.1 (2) | N3—C9—N2—C6 | 158.1 (2) |
N2—C9—C13—C14 | 143.0 (3) | C13—C9—N2—C7 | 153.5 (3) |
N3—C9—C13—C14 | −29.7 (4) | N3—C9—N2—C7 | −33.6 (3) |
C9—C13—C14—C18 | 116.5 (3) | C4—C6—N2—C9 | −143.8 (2) |
N4—C13—C14—C18 | −65.4 (3) | C4—C6—N2—C7 | 47.4 (3) |
C9—C13—C14—C15 | −110.5 (3) | C8—C7—N2—C9 | −94.4 (3) |
N4—C13—C14—C15 | 67.7 (3) | C8—C7—N2—C6 | 74.3 (3) |
C13—C14—C15—C16 | 71.6 (3) | O1—C11—N3—C9 | 170.8 (3) |
C18—C14—C15—C16 | −152.9 (3) | C12—C11—N3—C9 | −13.3 (4) |
C14—C15—C16—O4 | −10.8 (4) | O1—C11—N3—C10 | −4.9 (4) |
C14—C15—C16—C17 | 169.4 (3) | C12—C11—N3—C10 | 170.9 (3) |
C13—C14—C18—C23 | −137.1 (3) | N2—C9—N3—C11 | 126.2 (3) |
C15—C14—C18—C23 | 88.9 (3) | C13—C9—N3—C11 | −60.3 (3) |
C13—C14—C18—C19 | 43.7 (4) | N2—C9—N3—C10 | −58.1 (3) |
C15—C14—C18—C19 | −90.4 (4) | C13—C9—N3—C10 | 115.4 (3) |
C23—C18—C19—C20 | −0.3 (6) | C9—C13—N4—O2 | −24.5 (4) |
C14—C18—C19—C20 | 179.0 (3) | C14—C13—N4—O2 | 157.2 (2) |
C18—C19—C20—C21 | 0.4 (7) | C9—C13—N4—O3 | 159.3 (2) |
C19—C20—C21—C22 | −0.2 (7) | C14—C13—N4—O3 | −18.9 (4) |
Experimental details
Crystal data | |
Chemical formula | C23H26Cl2N4O4 |
Mr | 493.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.7948 (13), 12.649 (2), 13.021 (2) |
α, β, γ (°) | 91.364 (3), 98.765 (2), 107.878 (3) |
V (Å3) | 1204.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.16 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.943, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7096, 4200, 3870 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.148, 1.17 |
No. of reflections | 4200 |
No. of parameters | 302 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.38 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The coauthors thank the National Natural Science Foundation of China (21042010, 21102092 and 30870560) for financial support.
References
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Neonicotinoid insecticides have gained worldwide attention for being the fastest growing class of insecticides in modern crop protection, with wide spread use against sucking and chewing pests. Since imidacloprid (IMI) was first introduced to the market in 1991, many new neonicotinoid insecticides (NNSs) are now being sold. Nitenpyram, a chloronicotinyl derivative marketed in 1995, was characterized with a much lower toxicity against the mammals than imidacloprid (Tomizawa & Casida, 2000; Minamida et al., 1993; Kashiwada et al., 1996). In this paper, the title compound, (I), a new derivative, has been synthesized and characterized by X-ray diffraction.
In the title compound, C23H26Cl2N4O4, there is one molecule in the asymmetric unit (Fig. 1). The dihedral angle between the mean planes of the pyridine and 3-chlorophenyl rings is 22.63 (2)°. As compared with the (E) configuration of the nitro group in the crystal structure of nitenpyram, the nitro group in the title compound is in the (Z) configuration as anticipated.