N-{(1Z)-1-[(6-Chloro­pyridin-3-ylmeth­yl)(eth­yl)amino]-3-(3-chloro­phen­yl)-2-nitro-5-oxohex-1-en­yl}-N-methyl­acetamide

Sun, C.-W.; Wu, Y.; Wang, J.

doi:10.1107/S1600536812043358

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3229

doi:10.1107/S1600536812043358

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N-{(1Z)-1-[(6-Chloropyridin-3-ylmethyl)(ethyl)amino]-3-(3-chlorophenyl)-2-nitro-5-oxohex-1-enyl}-N-methylacetamide

Chuan-Wen Sun,^a ^* Ying Wu ^a and Jing Wang ^a

^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

(Received 21 September 2012; accepted 18 October 2012; online 27 October 2012)

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

C₂₃H₂₆Cl₂N₄O₄
M_r = 493.38
Triclinic, $[P \overline 1]$
a = 7.7948 (13) Å
b = 12.649 (2) Å
c = 13.021 (2) Å
α = 91.364 (3)°
β = 98.765 (2)°
γ = 107.878 (3)°
V = 1204.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.970
7096 measured reflections
4200 independent reflections
3870 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.148
S = 1.17
4200 reflections
302 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043358/jj2153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043358/jj2153Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043358/jj2153Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

The title compound was prepared by the literature method (Zhang et al., 2010). It was obtained using volatilization 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%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

N-{(1Z)-1-[(6-Chloropyridin-3-ylmethyl)(ethyl)amino]-3-(3- chlorophenyl)-2-nitro-5-oxohex-1-enyl}-N-methylacetamide top

Crystal data top

C₂₃H₂₆Cl₂N₄O₄	Z = 2
M_r = 493.38	F(000) = 516
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	3870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.943, T_max = 0.970	k = −15→13
7096 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0453P)² + 0.9109P] where P = (F_o² + 2F_c²)/3
4200 reflections	(Δ/σ)_max = 0.011
302 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₃H₂₆Cl₂N₄O₄	γ = 107.878 (3)°
M_r = 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)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4200 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3870 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.970	R_int = 0.020
7096 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.17	Δρ_max = 0.47 e Å⁻³
4200 reflections	Δρ_min = −0.38 e Å⁻³
302 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.943, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	7096, 4200, 3870
R_int	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
Δρ_max, Δρ_min (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
Kashiwada, Y. (1996). Agrochem. Jpn, 68, 18–19. Google Scholar
Minamida, I., Iwanaga, K. & Tabuchi, T. (1993). J. Pestic. Sci. 18, 31–40. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tomizawa, M. & Casida, J. E. (2000). Toxicol. Appl. Pharmacol. 169, 114–120. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, W. W., Yang, X. B., Chen, W. D., Xu, X. Y., Li, L., Zhai, H. B. & Li, Z. (2010). J. Agric. Food Chem. 58, 2741–2745. Web of Science CrossRef CAS PubMed Google Scholar

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