Crystal structure of chlorfluazuron

Seonghwa Cho; Jineun Kim; Sangjin Lee; Tae Ho Kim

doi:10.1107/S2056989014026632

. 2015 Jan 1;71(Pt 1):o55. doi: 10.1107/S2056989014026632

Crystal structure of chlorfluazuron

Seonghwa Cho ^a, Jineun Kim ^a,^*, Sangjin Lee ^a, Tae Ho Kim ^a,^*

PMCID: PMC4331875 PMID: 25705506

Abstract

The title compound (systematic name: 1-{3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yloxy]phenyl}-3-(2,6-difluorobenzoyl)urea), C₂₀H₉Cl₃F₅N₃O₃, is a benzoylphenylurea insecticide. The dihedral angles between the planes of the central dichlorophenyl and the terminal difluorophenyl and chloropyridyl rings are 79.51 (6) and 78.84 6)°, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link adjacent molecules, forming R ₂ ²(8) inversion dimers. In addition, the dimers are linked by short F⋯Cl [3.1060 (16) Å] and Cl⋯Cl [3.2837 (7) Å] contacts, as well as weak intermolecular π–π interactions [ring centroid separation = 3.6100 (11) and 3.7764 (13) Å], resulting in a two-dimensional architecture parallel to (111).

Keywords: crystal structure, chlorfluazuron, urea, insecticidal properties, Cl⋯Cl contacts

Related literature

For information on the insecticidal properties of the title compound, see: Choi et al. (2011 ▸); Lee et al. (2013 ▸). For a related crystal structure, see: Jeon et al. (2014 ▸). graphic file with name e-71-00o55-scheme1.jpg

Experimental

Crystal data

C₂₀H₉Cl₃F₅N₃O₃
M _r = 540.65
Triclinic,
a = 8.5805 (3) Å
b = 10.1281 (4) Å
c = 12.5883 (4) Å
α = 79.498 (2)°
β = 82.930 (2)°
γ = 83.485 (2)°
V = 1062.82 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 173 K
0.28 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.872, T _max = 0.975
19710 measured reflections
5259 independent reflections
4090 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.127
S = 1.06
5259 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014026632/sj5431sup1.cif

e-71-00o55-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026632/sj5431Isup2.hkl

e-71-00o55-Isup2.hkl^{(257.5KB, hkl)}

Click here for additional data file.^{(7.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014026632/sj5431Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989014026632/sj5431fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.^{(1.3MB, tif)}

a . DOI: 10.1107/S2056989014026632/sj5431fig2.tif

Crystal packing viewed along the a axis. The intermolecular N—H⋯O hydrogen bonds, short F⋯Cl, Cl⋯Cl contacts and π–π interactions are shown as dashed lines.

CCDC reference: 1037499

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1O2ⁱ	0.88	1.96	2.837(2)	175

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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. 2014R1A1A4A01009105).

supplementary crystallographic information

S1. Comment

Chlorfluazuron, C₂₀H₉Cl₃F₅N₃O₃, is a benzoylphenylurea which has been recognized as one of the promising insecticides with great potential for use in controlling insect attack on a broad range of fruits and vegetables (Lee et al., 2013; Choi et al., 2011). Its crystal structure is reported herein. In this compound (Scheme 1, Fig. 1), the dihedral angles between the central dichlorophenyl and the terminal difluorophenyland chloropyridyl rings are 79.51 (6) and 78.84 (6)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Jeon et al., 2014).

The crystal structure, (Fig. 2), is stabilized by N—H···O hydrogen bonds (Table 1), forming R₂²(8) inversion dimers. In addition, the dimers are linked by short F2···Cl3ⁱⁱ [3.1060 (16) Å] and Cl1···Cl1ⁱⁱⁱ [3.2837 (7) Å] contacts as well as two weak intermolecular offset π–π stacking interactions [Cg1···Cg3^iv = 3.7764 (13)Å. Cg1 and Cg3 are the centroids of the C1—C2—C3—C4—C5—C6 and C15—C16—C17—C18—C19—N3 rings, respectively. Cg2···Cg2ⁱⁱ = 3.6100 (11) Å. Cg2 is the centroid of the C9—C10—C11—C12—C13—C14 ring. (Symmetry codes: (ii), -x + 1, -y + 2, -z + 1; (iii) -x + 1, -y + 1, -z + 1 and (iv) x, y + 1, z - 1)], resulting in a two-dimensional architecture parallel to the (111) plane.

S2. Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CHCl₃ gave single crystals suitable for X-ray analysis.