6-[(2-Chloro-pyridin-5-ylmeth-yl)(eth-yl)-azan-yl]-4-(2-fluoro-phen-yl)-1-methyl-5-nitro-1,2,3,4-tetra-hydro-pyridin-2-one.

In the title compound, C(20)H(20)ClFN(4)O(3), the tetra-hydro-pyridone ring adopts a skew boat conformation. The dihedral angle between the mean planes of the benzene and pyridine rings is 80.7 (3)°. In the crystal, weak C-H⋯O inter-actions are observed.

Related literature

For general background to neonicotinoid compounds and their application as insecticides, see: Jeschke & Nauen (2008 ▶); Kagabu & Matsuno (1997 ▶); Ohno et al. (2009 ▶); Shao et al. (2008 ▶); Tian et al. (2007 ▶); Tomizawa & Casida (2009 ▶). For the synthesis of the title compound, see: Zhang et al. (2010 ▶). For puckering parameters, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H20ClFN4O3

M = 418.85

Triclinic,

a = 6.750 (2) Å

b = 8.262 (3) Å

c = 17.853 (6) Å

α = 94.981 (6)°

β = 91.302 (7)°

γ = 100.593 (7)°

V = 974.2 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.938, T max = 0.954

5691 measured reflections

3391 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.151

S = 0.96

3391 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005776/jj2119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005776/jj2119Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005776/jj2119Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812005776/jj2119Isup4.cml

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

C20H20ClFN4O3	Z = 2
Mr = 418.85	F(000) = 436
Triclinic, P1	Dx = 1.428 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.750 (2) Å	Cell parameters from 906 reflections
b = 8.262 (3) Å	θ = 2.3–19.9°
c = 17.853 (6) Å	µ = 0.24 mm−1
α = 94.981 (6)°	T = 298 K
β = 91.302 (7)°	Block, yellow
γ = 100.593 (7)°	0.23 × 0.20 × 0.20 mm
V = 974.2 (6) Å3

Bruker SMART CCD area-detector diffractometer	3391 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→8
Tmin = 0.938, Tmax = 0.954	k = −9→9
5691 measured reflections	l = −21→16

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0497P)2] where P = (Fo2 + 2Fc2)/3
3391 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cl1	−0.0482 (2)	0.19595 (18)	1.06337 (7)	0.0963 (5)
F1	0.0556 (4)	−0.3141 (3)	0.57751 (14)	0.0768 (8)
O1	0.1183 (4)	0.3810 (3)	0.70839 (17)	0.0579 (8)
O2	0.0164 (4)	0.1954 (4)	0.61628 (17)	0.0745 (10)
O3	0.4797 (4)	−0.1603 (3)	0.82425 (15)	0.0613 (8)
N1	0.0698 (5)	0.3252 (5)	0.9407 (2)	0.0677 (11)
N2	0.5075 (4)	0.3694 (3)	0.76441 (15)	0.0358 (7)
N3	0.5073 (4)	0.0931 (3)	0.78309 (15)	0.0367 (7)
N4	0.1287 (5)	0.2474 (4)	0.67181 (19)	0.0457 (8)
C1	0.1333 (7)	0.2582 (5)	0.9985 (2)	0.0579 (12)
C2	0.3272 (8)	0.2367 (5)	1.0112 (2)	0.0620 (13)
H2	0.3632	0.1866	1.0528	0.074*
C3	0.2101 (7)	0.3769 (5)	0.8917 (2)	0.0595 (12)
H3	0.1690	0.4245	0.8501	0.071*
C4	0.4110 (6)	0.3647 (4)	0.8982 (2)	0.0431 (10)
C5	0.4664 (6)	0.2921 (5)	0.9599 (2)	0.0539 (11)
H5	0.5998	0.2804	0.9669	0.065*
C6	0.5569 (6)	0.4366 (4)	0.8427 (2)	0.0475 (11)
H6A	0.5631	0.5553	0.8461	0.057*
H6B	0.6899	0.4176	0.8567	0.057*
C7	0.5241 (6)	0.4907 (4)	0.7083 (2)	0.0468 (10)
H7A	0.4291	0.5638	0.7190	0.056*
H7B	0.4883	0.4331	0.6588	0.056*
C8	0.7339 (6)	0.5922 (5)	0.7079 (3)	0.0664 (13)
H8A	0.7682	0.6524	0.7563	0.100*
H8B	0.7388	0.6686	0.6701	0.100*
H8C	0.8283	0.5204	0.6970	0.100*
C9	0.4199 (5)	0.2097 (4)	0.74628 (18)	0.0333 (9)
C10	0.2653 (5)	0.1481 (4)	0.6955 (2)	0.0360 (9)
C11	0.2062 (5)	−0.0340 (4)	0.6735 (2)	0.0387 (9)
H11	0.0674	−0.0550	0.6527	0.046*
C12	0.2044 (5)	−0.1165 (4)	0.7469 (2)	0.0444 (10)
H12A	0.0999	−0.0843	0.7782	0.053*
H12B	0.1738	−0.2357	0.7359	0.053*
C13	0.4050 (6)	−0.0674 (5)	0.78885 (19)	0.0401 (9)
C14	0.7233 (5)	0.1245 (5)	0.8024 (2)	0.0539 (11)
H14A	0.7442	0.1457	0.8560	0.081*
H14B	0.7887	0.2190	0.7787	0.081*
H14C	0.7789	0.0297	0.7852	0.081*
C15	0.3356 (5)	−0.1057 (4)	0.6151 (2)	0.0371 (9)
C16	0.2525 (6)	−0.2468 (5)	0.5697 (2)	0.0491 (11)
C17	0.3578 (7)	−0.3229 (5)	0.5167 (2)	0.0621 (13)
H17	0.2958	−0.4175	0.4870	0.074*
C18	0.5569 (7)	−0.2557 (5)	0.5088 (2)	0.0590 (12)
H18	0.6323	−0.3060	0.4740	0.071*
C19	0.6450 (6)	−0.1144 (5)	0.5521 (2)	0.0500 (11)
H19	0.7796	−0.0685	0.5462	0.060*
C20	0.5345 (6)	−0.0401 (5)	0.6044 (2)	0.0418 (10)
H20	0.5957	0.0563	0.6330	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.1069 (11)	0.1166 (12)	0.0622 (9)	0.0018 (9)	0.0239 (8)	0.0258 (8)
F1	0.0722 (17)	0.0626 (16)	0.0813 (18)	−0.0162 (13)	0.0080 (14)	−0.0141 (14)
O1	0.0526 (17)	0.0505 (18)	0.077 (2)	0.0280 (15)	−0.0045 (15)	0.0027 (16)
O2	0.074 (2)	0.072 (2)	0.077 (2)	0.0232 (17)	−0.0420 (18)	−0.0028 (17)
O3	0.087 (2)	0.0429 (17)	0.0585 (19)	0.0198 (16)	−0.0108 (16)	0.0156 (15)
N1	0.062 (2)	0.098 (3)	0.044 (2)	0.014 (2)	0.0000 (19)	0.013 (2)
N2	0.0406 (18)	0.0324 (17)	0.0344 (17)	0.0059 (14)	0.0014 (14)	0.0049 (14)
N3	0.0360 (17)	0.0358 (17)	0.0382 (18)	0.0071 (14)	−0.0067 (14)	0.0046 (14)
N4	0.0395 (19)	0.045 (2)	0.054 (2)	0.0081 (16)	−0.0040 (17)	0.0101 (17)
C1	0.073 (3)	0.059 (3)	0.038 (3)	0.006 (2)	0.003 (2)	−0.001 (2)
C2	0.089 (4)	0.059 (3)	0.038 (3)	0.010 (3)	−0.007 (2)	0.010 (2)
C3	0.067 (3)	0.077 (3)	0.037 (2)	0.015 (3)	−0.002 (2)	0.013 (2)
C4	0.050 (3)	0.040 (2)	0.036 (2)	0.008 (2)	−0.0077 (19)	−0.0111 (18)
C5	0.064 (3)	0.056 (3)	0.042 (3)	0.015 (2)	−0.012 (2)	0.004 (2)
C6	0.055 (3)	0.037 (2)	0.046 (2)	0.0004 (19)	−0.008 (2)	−0.0034 (18)
C7	0.056 (3)	0.037 (2)	0.050 (2)	0.0093 (19)	0.004 (2)	0.0132 (19)
C8	0.059 (3)	0.054 (3)	0.089 (4)	0.007 (2)	0.017 (3)	0.028 (3)
C9	0.036 (2)	0.035 (2)	0.031 (2)	0.0089 (17)	0.0030 (17)	0.0075 (16)
C10	0.033 (2)	0.035 (2)	0.041 (2)	0.0104 (17)	−0.0037 (17)	0.0038 (17)
C11	0.032 (2)	0.040 (2)	0.042 (2)	0.0021 (17)	−0.0060 (17)	0.0020 (18)
C12	0.046 (2)	0.040 (2)	0.045 (2)	0.0019 (18)	0.0107 (19)	0.0051 (18)
C13	0.056 (3)	0.039 (2)	0.026 (2)	0.012 (2)	0.0009 (18)	0.0049 (17)
C14	0.043 (2)	0.052 (3)	0.068 (3)	0.014 (2)	−0.010 (2)	0.003 (2)
C15	0.042 (2)	0.035 (2)	0.035 (2)	0.0100 (18)	−0.0018 (17)	0.0062 (17)
C16	0.054 (3)	0.041 (2)	0.048 (3)	−0.003 (2)	−0.001 (2)	0.006 (2)
C17	0.089 (4)	0.046 (3)	0.049 (3)	0.013 (3)	0.011 (3)	−0.006 (2)
C18	0.076 (3)	0.065 (3)	0.044 (3)	0.031 (3)	0.009 (2)	0.010 (2)
C19	0.054 (3)	0.064 (3)	0.037 (2)	0.022 (2)	0.001 (2)	0.009 (2)
C20	0.049 (2)	0.046 (2)	0.032 (2)	0.011 (2)	−0.0010 (18)	0.0057 (18)

Cl1—C1	1.744 (4)	C7—H7B	0.9700
F1—C16	1.358 (4)	C8—H8A	0.9600
O1—N4	1.247 (4)	C8—H8B	0.9600
O2—N4	1.231 (4)	C8—H8C	0.9600
O3—C13	1.206 (4)	C9—C10	1.360 (4)
N1—C1	1.312 (5)	C10—C11	1.499 (5)
N1—C3	1.342 (5)	C11—C15	1.526 (5)
N2—C9	1.352 (4)	C11—C12	1.527 (5)
N2—C6	1.467 (4)	C11—H11	0.9800
N2—C7	1.469 (4)	C12—C13	1.503 (5)
N3—C13	1.391 (4)	C12—H12A	0.9700
N3—C9	1.417 (4)	C12—H12B	0.9700
N3—C14	1.461 (4)	C14—H14A	0.9600
N4—C10	1.422 (4)	C14—H14B	0.9600
C1—C2	1.370 (6)	C14—H14C	0.9600
C2—C5	1.373 (5)	C15—C20	1.376 (5)
C2—H2	0.9300	C15—C16	1.381 (5)
C3—C4	1.381 (5)	C16—C17	1.373 (5)
C3—H3	0.9300	C17—C18	1.372 (5)
C4—C5	1.374 (5)	C17—H17	0.9300
C4—C6	1.495 (5)	C18—C19	1.371 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—H6A	0.9700	C19—C20	1.381 (5)
C6—H6B	0.9700	C19—H19	0.9300
C7—C8	1.508 (5)	C20—H20	0.9300
C7—H7A	0.9700
C1—N1—C3	115.8 (4)	N2—C9—N3	115.0 (3)
C9—N2—C6	121.8 (3)	C10—C9—N3	116.8 (3)
C9—N2—C7	121.2 (3)	C9—C10—N4	121.7 (3)
C6—N2—C7	116.1 (3)	C9—C10—C11	121.2 (3)
C13—N3—C9	122.3 (3)	N4—C10—C11	116.0 (3)
C13—N3—C14	115.9 (3)	C10—C11—C15	115.7 (3)
C9—N3—C14	120.6 (3)	C10—C11—C12	105.8 (3)
O2—N4—O1	121.0 (3)	C15—C11—C12	112.4 (3)
O2—N4—C10	118.5 (3)	C10—C11—H11	107.5
O1—N4—C10	120.4 (3)	C15—C11—H11	107.5
N1—C1—C2	125.1 (4)	C12—C11—H11	107.5
N1—C1—Cl1	115.6 (4)	C13—C12—C11	110.8 (3)
C2—C1—Cl1	119.3 (4)	C13—C12—H12A	109.5
C1—C2—C5	117.3 (4)	C11—C12—H12A	109.5
C1—C2—H2	121.4	C13—C12—H12B	109.5
C5—C2—H2	121.4	C11—C12—H12B	109.5
N1—C3—C4	125.0 (4)	H12A—C12—H12B	108.1
N1—C3—H3	117.5	O3—C13—N3	120.4 (3)
C4—C3—H3	117.5	O3—C13—C12	123.4 (3)
C5—C4—C3	116.0 (4)	N3—C13—C12	116.2 (3)
C5—C4—C6	123.5 (4)	N3—C14—H14A	109.5
C3—C4—C6	120.3 (4)	N3—C14—H14B	109.5
C2—C5—C4	120.8 (4)	H14A—C14—H14B	109.5
C2—C5—H5	119.6	N3—C14—H14C	109.5
C4—C5—H5	119.6	H14A—C14—H14C	109.5
N2—C6—C4	114.6 (3)	H14B—C14—H14C	109.5
N2—C6—H6A	108.6	C20—C15—C16	116.4 (4)
C4—C6—H6A	108.6	C20—C15—C11	124.4 (3)
N2—C6—H6B	108.6	C16—C15—C11	119.2 (3)
C4—C6—H6B	108.6	F1—C16—C17	118.1 (4)
H6A—C6—H6B	107.6	F1—C16—C15	118.4 (4)
N2—C7—C8	112.1 (3)	C17—C16—C15	123.6 (4)
N2—C7—H7A	109.2	C18—C17—C16	118.3 (4)
C8—C7—H7A	109.2	C18—C17—H17	120.9
N2—C7—H7B	109.2	C16—C17—H17	120.9
C8—C7—H7B	109.2	C19—C18—C17	120.1 (4)
H7A—C7—H7B	107.9	C19—C18—H18	119.9
C7—C8—H8A	109.5	C17—C18—H18	119.9
C7—C8—H8B	109.5	C18—C19—C20	120.2 (4)
H8A—C8—H8B	109.5	C18—C19—H19	119.9
C7—C8—H8C	109.5	C20—C19—H19	119.9
H8A—C8—H8C	109.5	C15—C20—C19	121.4 (4)
H8B—C8—H8C	109.5	C15—C20—H20	119.3
N2—C9—C10	128.1 (3)	C19—C20—H20	119.3
C3—N1—C1—C2	−0.7 (7)	O2—N4—C10—C11	−24.8 (5)
C3—N1—C1—Cl1	178.5 (3)	O1—N4—C10—C11	152.5 (3)
N1—C1—C2—C5	1.1 (7)	C9—C10—C11—C15	−80.5 (4)
Cl1—C1—C2—C5	−178.1 (3)	N4—C10—C11—C15	111.0 (3)
C1—N1—C3—C4	−0.2 (7)	C9—C10—C11—C12	44.6 (4)
N1—C3—C4—C5	0.7 (6)	N4—C10—C11—C12	−123.9 (3)
N1—C3—C4—C6	−175.9 (4)	C10—C11—C12—C13	−56.2 (4)
C1—C2—C5—C4	−0.5 (6)	C15—C11—C12—C13	70.9 (4)
C3—C4—C5—C2	−0.3 (6)	C9—N3—C13—O3	−175.8 (3)
C6—C4—C5—C2	176.2 (3)	C14—N3—C13—O3	17.0 (5)
C9—N2—C6—C4	−34.4 (5)	C9—N3—C13—C12	6.1 (5)
C7—N2—C6—C4	134.8 (3)	C14—N3—C13—C12	−161.1 (3)
C5—C4—C6—N2	124.5 (4)	C11—C12—C13—O3	−143.5 (4)
C3—C4—C6—N2	−59.1 (5)	C11—C12—C13—N3	34.5 (4)
C9—N2—C7—C8	−131.8 (4)	C10—C11—C15—C20	27.1 (5)
C6—N2—C7—C8	58.8 (4)	C12—C11—C15—C20	−94.5 (4)
C6—N2—C9—C10	136.3 (4)	C10—C11—C15—C16	−153.7 (3)
C7—N2—C9—C10	−32.4 (5)	C12—C11—C15—C16	84.6 (4)
C6—N2—C9—N3	−46.4 (4)	C20—C15—C16—F1	−179.0 (3)
C7—N2—C9—N3	144.8 (3)	C11—C15—C16—F1	1.8 (5)
C13—N3—C9—N2	160.7 (3)	C20—C15—C16—C17	0.9 (6)
C14—N3—C9—N2	−32.6 (4)	C11—C15—C16—C17	−178.4 (4)
C13—N3—C9—C10	−21.8 (5)	F1—C16—C17—C18	−179.8 (4)
C14—N3—C9—C10	144.9 (3)	C15—C16—C17—C18	0.4 (6)
N2—C9—C10—N4	−21.6 (6)	C16—C17—C18—C19	−1.2 (6)
N3—C9—C10—N4	161.2 (3)	C17—C18—C19—C20	0.7 (6)
N2—C9—C10—C11	170.6 (3)	C16—C15—C20—C19	−1.4 (5)
N3—C9—C10—C11	−6.6 (5)	C11—C15—C20—C19	177.8 (3)
O2—N4—C10—C9	166.7 (3)	C18—C19—C20—C15	0.7 (5)
O1—N4—C10—C9	−16.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O1i	0.96	2.46	3.383 (5)	161
C6—H6A···O3ii	0.97	2.57	3.506 (5)	161
C3—H3···O1	0.93	2.53	3.320 (5)	143
C2—H2···O3iii	0.93	2.46	3.344 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯O1i	0.96	2.46	3.383 (5)	161
C6—H6A⋯O3ii	0.97	2.57	3.506 (5)	161
C3—H3⋯O1	0.93	2.53	3.320 (5)	143
C2—H2⋯O3iii	0.93	2.46	3.344 (5)	159

Symmetry codes: (i) ; (ii) ; (iii) .