1-(2,6-Difluoro­benzo­yl)-3-(2,3,5-tri­chloro­phen­yl)urea

Sheng-Jiao Yan; Chao Huang; Yan-Mei Li; Yu-Yun Yan; Jun Lin

doi:10.1107/S1600536808032029

. 2008 Oct 11;64(Pt 11):o2102. doi: 10.1107/S1600536808032029

1-(2,6-Difluorobenzoyl)-3-(2,3,5-trichlorophenyl)urea

Sheng-Jiao Yan ^a,^*, Chao Huang ^a, Yan-Mei Li ^a, Yu-Yun Yan ^a, Jun Lin ^a,^*

PMCID: PMC2959602 PMID: 21580966

Abstract

The asymmetric unit of the title compound, C₁₄H₇Cl₃F₂N₂O₂, contains two unique molecules. The 2,3,5-trichlorophenyl ring is almost coplanar with the urea group in both molecules, whereas the 2,6-difluorophenyl ring is twisted from the urea plane by 54.83 (10)° in one molecule and 60.58 (10)° in the other. An intramolecular N—H—O hydrogen bond stabilizes the molecular conformation. The crystal packing is formed by intermolecular N—H—O hydrogen bonds and F⋯F interactions [2.841 (2) Å].

Related literature

For general background, see: Yan et al. (2003 ▶). For synthetic details, see: Lin et al. (2003 ▶, 2005 ▶). graphic file with name e-64-o2102-scheme1.jpg

Experimental

Crystal data

C₁₄H₇Cl₃F₂N₂O₂
M _r = 379.57
Monoclinic,
a = 7.1669 (4) Å
b = 22.8228 (12) Å
c = 18.2885 (10) Å
β = 94.768 (2)°
V = 2981.1 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 113 (2) K
0.24 × 0.14 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2006 ▶) T _min = 0.860, T _max = 0.927
27779 measured reflections
7091 independent reflections
6011 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.089
S = 1.07
7091 reflections
431 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2006 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032029/jh2065sup1.cif

e-64-o2102-sup1.cif^{(26KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032029/jh2065Isup2.hkl

e-64-o2102-Isup2.hkl^{(347KB, hkl)}

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
N1—H1⋯Cl1	0.89 (2)	2.46 (2)	2.9126 (15)	111.8 (16)
N1—H1⋯O2	0.89 (2)	1.88 (2)	2.641 (2)	141.5 (19)
N2—H2⋯O1ⁱ	0.82 (2)	2.00 (2)	2.8205 (19)	173 (2)
N3—H3⋯Cl4	0.80 (2)	2.43 (2)	2.8944 (16)	118.2 (19)
N3—H3⋯O4	0.80 (2)	1.99 (2)	2.658 (2)	140 (2)
N4—H4⋯O3ⁱⁱ	0.91 (2)	1.93 (2)	2.8378 (18)	176 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This project was supported by the 11th Five-Year Construction Item for Yunnan University Teachers (grant No. 0030-WX069051).

supplementary crystallographic information

Comment

Derivatives of benzoylphenylureas (BPUs) are kind of insect growth regulators (IGRs), interferes the chitin synthesis in target pests, causing death or abortive development. BPUs posses high selectivity, low acute toxicity for mammals. At the time, the different groups on the phenyl that have different bioactivity. So research the configuration of the different compound is important to find more potent insecticide. The title compound (I) (Fig. 1), C₁₄H₇Cl₃F₂N₂O₂, which possesses high bioactivity to pests (Yan et al., 2003).

The geometrical parameters for (I) (Table 1) show the conjugation present: the length of the C1═O1 and C═O2 double bond is greater than that of a normal C═O double bond. The lengths of the C1—N1, C1—N2, C8—N2 bonds are shorter than that of normal C—N single bonds. The 2,3,5-trichlorophenyl ring of the title compound is almost coplanar with the urea group, whereas the 2,6-difluorophenyl ring is twisted from the urea plane by 60.58 (10)°. An intramolecular N—H—O hydrogen bond stabilizes the molecular conformation. The crystal packing of the title compound formed by intermolecular N—H—O hydrogen bonds and F···F bond (Fig 2).

Experimental

A solution of 2,6-difluorobenzoyl isocyanate (II) (10 mmol, 1.0 equiv.) in 1,2-dichloroethane (10 ml) was added to a stirred solution of 2,3,5-trichloroaniline (III) (10 mmol, 1.0 equiv.) in dry 1,2-dichloroethane (20 ml) and stirred at room temperature for 24 hrs, the solvent was removed in vacuo and the residue was recrystallized with ethyl acetate to give desired compounds as white needle-crystals (I) in 93% yield (Lin et al., 2003; Lin et al., 2005). The desire product recrystallized from acetone (m.p. 517 K).