6-[(2-Chloro­pyridin-5-ylmeth­yl)(eth­yl)­azan­yl]-4-(2-fluoro­phen­yl)-1-methyl-5-nitro-1,2,3,4-tetra­hydro­pyridin-2-one

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

doi:10.1107/S1600536812005776

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o753

doi:10.1107/S1600536812005776

Open

access

6-[(2-Chloropyridin-5-ylmethyl)(ethyl)azanyl]-4-(2-fluorophenyl)-1-methyl-5-nitro-1,2,3,4-tetrahydropyridin-2-one

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

^aDepartment of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, People's Republic of China
^*Correspondence e-mail: jingwangchemistry@163.com

(Received 5 January 2012; accepted 9 February 2012; online 17 February 2012)

In the title compound, C₂₀H₂₀ClFN₄O₃, the tetrahydropyridone 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 interactions 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_r = 418.85
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.151
S = 0.96
3391 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) x+1, y, z; (ii) x, y+1, z; (iii) -x+1, -y, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005776/jj2119sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812005776/jj2119Isup3.mol

Supporting information file. DOI: 10.1107/S1600536812005776/jj2119Isup4.cml

checkCIF report

Comment top

In recent years, neonicotinoid insecticide compounds have rapidly grown and become a new chemical class of insecticides because of their novel structure and mode of action (Jeschke & Nauen,2008; Kagabu & Matsuno,1997; Ohno et al., 2009; Shao et al., 2008; Tian et al., 2007; Tomizawa & Casida, 2009). We report here the synthesis and crystal structure of one of these compounds, C₂₀H₂₀ClFN₄O₃, the title compound, (I).

In (I) the tetrahydropyridone ring adopts a skew boat conformation with puckering paramers (Cremer & Pople, 1975) Q, θ and ϕ of 0.526 (4)Å, 113.2 (4)° and 22.0 (4)°) and a N2/C9/C10/N4 dihedral angle of -21.6 (6)° (Fig.1). In the tetrahydropyridone moiety, C11—C10, C12—C11 and C13—C12 bond lengths (1.499 (5) Å, 1.527 (5) Å and 1.503 (5) Å) are slightly shorter than normal. The C13—N3, C9—N3, and C10—N4 bond lengths (1.391 (4)Å, 1.417 (4)Å, and 1.422 (4)Å, respectively) are slightly shorter than normal while the C9═C10 bond length (1.360 (4)Å) is slightly longer than normal. The dihedral angle between the mean planes of the benzene and pryidine rings is 80.7 (3)°. In the crystal structure weak C2—H2···O3, C8—H8C···O1 and C6—H6A···O3 intermolecular interactions are observed which may influence crystal packing (Fig.2).

Related literature top

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 top

In the preparation of the title compound, a solution of 2-fluorobenzaldehyde (15 mmol), Meldrum's acid (15 mmol) in ethanol (30 ml), with piperidine (0.1 mmol) used as catalyst, was added dropwise and the solution was stirred at room temperature for 2 h. Nitenpyram (2.75 g, 10 mmol) was added to the reaction mixture, heated to 65 °C for 6 h and then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and treated with 20 ml of water whereby the solution was extracted three times with CH₂Cl₂, and the combined extracts were dried over MgSO₄. The organic phase was evaporated under reduced pressure and the crude product was subjected to flash chromatography on silica gel, eluting with ethyl acetate /petroleum ether to afford pure yellow crystals (yield 81%). Anal. calcd. for C₂₀H₂₀ClFN₄O₃ C 57.33, H 4.80, N 13.36% found, C 57.35, H 4.81, N 13.38%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing of the title compound, (I), viewed along the a axis. Weak C2—H2···O3, C8—H8C···O1 and C6—H6A···O3 intermolecular interactions are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

6-[(2-Chloropyridin-5-ylmethyl)(ethyl)azanyl]-4-(2-fluorophenyl)- 1-methyl-5-nitro-1,2,3,4-tetrahydropyridin-2-one top

Crystal data top

C₂₀H₂₀ClFN₄O₃	Z = 2
M_r = 418.85	F(000) = 436
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0497P)²] where P = (F_o² + 2F_c²)/3
3391 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₂₀ClFN₄O₃	γ = 100.593 (7)°
M_r = 418.85	V = 974.2 (6) Å³
Triclinic, P1	Z = 2
a = 6.750 (2) Å	Mo Kα radiation
b = 8.262 (3) Å	µ = 0.24 mm⁻¹
c = 17.853 (6) Å	T = 298 K
α = 94.981 (6)°	0.23 × 0.20 × 0.20 mm
β = 91.302 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3391 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1943 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.954	R_int = 0.073
5691 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 0.96	Δρ_max = 0.23 e Å⁻³
3391 reflections	Δρ_min = −0.25 e Å⁻³
264 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀ClFN₄O₃
M_r	418.85
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.750 (2), 8.262 (3), 17.853 (6)
α, β, γ (°)	94.981 (6), 91.302 (7), 100.593 (7)
V (Å³)	974.2 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.938, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	5691, 3391, 1943
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.151, 0.96
No. of reflections	3391
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y, −z+2.

Acknowledgements

This work was supported mostly by the National Natural Science Foundation of China (grant Nos 21042010, 21102092 and 30870560).

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Jeschke, P. & Nauen, R. (2008). Pest Manage. Sci. 64, 1084–1098. Web of Science CrossRef CAS Google Scholar
Kagabu, S. & Matsuno, H. (1997). J. Agric. Food Chem. 45, 276–281. CrossRef CAS Web of Science Google Scholar
Ohno, I., Tomizawa, M., Durkin, K. A., Naruse, Y., Casida, J. E. & Kagabu, S. (2009). Chem. Res. Toxicol. 22, 476–482. Web of Science CrossRef PubMed CAS Google Scholar
Shao, X. S., Zhang, W. W., Peng, Y. Q., Li, Z., Tian, Z. Z. & Qian, X. H. (2008). Bioorg. Med. Chem. Lett. 18, 6513–6516. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2003). 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
Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food Chem. 55, 2288–2292. Web of Science CrossRef PubMed CAS Google Scholar
Tomizawa, M. & Casida, J. E. (2009). Acc. Chem. Res. 42, 260–269. 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

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o753

doi:10.1107/S1600536812005776

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-[(2-Chloro­pyridin-5-ylmeth­yl)(eth­yl)­azan­yl]-4-(2-fluoro­phen­yl)-1-methyl-5-nitro-1,2,3,4-tetra­hydro­pyridin-2-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-[(2-Chloropyridin-5-ylmethyl)(ethyl)azanyl]-4-(2-fluorophenyl)-1-methyl-5-nitro-1,2,3,4-tetrahydropyridin-2-one