N-{(1Z)-1-[(6-Chloro-pyridin-3-ylmeth-yl)(eth-yl)amino]-3-(3-chloro-phen-yl)-2-nitro-5-oxohex-1-en-yl}-N-methyl-acetamide.

In the title compound, C(23)H(26)Cl(2)N(4)O(4),the dihedral angle between the mean planes of the pyridine and 3-chloro-phenyl 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 = 493.38

Triclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.148

S = 1.17

4200 reflections

302 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043358/jj2153sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043358/jj2153Isup3.cml

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

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

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)