Fluazinam

Youngeun Jeon; Jineun Kim; Sangjin Lee; Tae Ho Kim

doi:10.1107/S1600536813023210

. 2013 Aug 23;69(Pt 9):o1467. doi: 10.1107/S1600536813023210

Fluazinam

Youngeun Jeon ^a, Jineun Kim ^a,^*, Sangjin Lee ^a, Tae Ho Kim ^a,^*

PMCID: PMC3884378 PMID: 24427089

Abstract

In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,6-dinitro-4-(trifluoromethyl)aniline}, C₁₃H₄Cl₂F₆N₄O₄, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)°. In the crystal, pairs of N—H⋯F hydrogen bonds link the molecules into inversion dimers which are linked by C—Cl⋯π [Cl⋯ring centroid = 3.3618 (4) A °] and N—O⋯π [O⋯ring centroid = 3.1885 (16) Å] interactions into chains along [100]. In addition, short Cl⋯Cl, O⋯Cl, and F⋯F contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) Å] are present which connect the chains, yielding a three-dimensional network.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993 ▶); Draper et al. (2003 ▶). For a related structure, see: McCullough et al. (1972 ▶). graphic file with name e-69-o1467-scheme1.jpg

Experimental

Crystal data

C₁₃H₄Cl₂F₆N₄O₄
M _r = 465.10
Triclinic,
a = 8.9546 (1) Å
b = 9.0724 (1) Å
c = 10.6818 (2) Å
α = 79.556 (1)°
β = 75.420 (1)°
γ = 83.451 (1)°
V = 823.79 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 173 K
0.30 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T _min = 0.867, T _max = 0.930
15193 measured reflections
4096 independent reflections
3662 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.085
S = 1.04
4096 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023210/kj2230sup1.cif

e-69-o1467-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023210/kj2230Isup2.hkl

e-69-o1467-Isup2.hkl^{(200.7KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813023210/kj2230Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯F3ⁱ	0.88	2.52	3.0690 (15)	121

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Symmetry code: (i) Inline graphic .

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

supplementary crystallographic information

1. Comment

The title compound fluazinam, C₁₃H₄Cl₂F₆N₄O₄, is a broad spectrum contact fungicide that can be applied as a foliar spray or soil treatment (Yoshida et al., 1993; Draper et al., 2003) and its crystal structure is reported herein. In this compound (Fig. 1), the dihedral angle between the pyridyl ring and the phenyl ring is 42.20 (4)°. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of a similar compound (McCullough et al., 1972). In the crystal structure (Fig. 2), an intermolecular N—H···F hydrogen bond is observed (Table 1), giving a dimer structure. In this structure there are both a C3—Cl1···π interaction with the pyridyl ring [Cl1···Cg1ⁱⁱ = 3.3618 (4) Å] and a N1—O1···π interaction with the phenyl ring [O1···Cg2ⁱⁱ = 3.1885 (16) Å]. In addition, short Cl···Cl, O···Cl, and F···F contacts [Cl2···Cl2ⁱⁱⁱ, 3.4676 (7) Å, O3···Cl1^iv, 3.2371 (13) Å, and F3···F6^v, 2.7910 (15) Å] are present [for symmetry codes: (ii), -x+1, -y+1, -z+1, (iii), -x+1, -y+1, -z+2, (iv), x, y - 1, z, and (v), x + 1, y + 1, z + 1]. A three-dimensional network is formed by the hydrogen bond and these interactions.

2. Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.