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

Yan, S.-J.; Huang, C.; Li, Y.-M.; Yan, Y.-Y.; Lin, J.

doi:10.1107/S1600536808032029

Volume 64
Part 11
Page o2102
November 2008

Received 1 May 2008
Accepted 6 October 2008
Online 11 October 2008

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.089
Data-to-parameter ratio = 16.5
Details

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 and Jun Lin ^a ^*

^aSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resources, (Ministry of Education), Yunnan University, Kunming 650091, People's Republic of China
Correspondence e-mail: yanshengjiao@126.com,

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 FF interactions [2.841 (2) Å].

Related literature

For general background, see: Yan et al. (2003). For synthetic details, see: Lin et al. (2003, 2005).

Experimental

Crystal data

C₁₄H₇Cl₃F₂N₂O₂
M_r = 379.57
Monoclinic, P 2₁ /c
a = 7.1669 (4) Å
b = 22.8228 (12) Å
c = 18.2885 (10) Å
= 94.768 (2)°
V = 2981.1 (3) Å³
Z = 8
Mo K radiation
= 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 > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.089
S = 1.07
7091 reflections
431 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1Cl1	0.89 (2)	2.46 (2)	2.9126 (15)	111.8 (16)
N1-H1O2	0.89 (2)	1.88 (2)	2.641 (2)	141.5 (19)
N2-H2O1ⁱ	0.82 (2)	2.00 (2)	2.8205 (19)	173 (2)
N3-H3Cl4	0.80 (2)	2.43 (2)	2.8944 (16)	118.2 (19)
N3-H3O4	0.80 (2)	1.99 (2)	2.658 (2)	140 (2)
N4-H4O3ⁱⁱ	0.91 (2)	1.93 (2)	2.8378 (18)	176 (2)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: JH2065 ).

Acknowledgements

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

References

Lin, J., Yan, S. J., Mao, D. S., Xu, R., Yang, L. J. & Liu, F. C. (2003). Chin. Chem. Lett. 14, 1219-1222.
Lin, J., Yan, S. J., Yang, L. J., Li, J. F. & Liu, F. C. (2005). Chin. J. Org. Chem. 25, 304-307.
Rigaku (2006). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yan, S. J., Lin, J., Bi, F. C., Rang, L. J. & Cheng, Y. P. (2003). J. Yunnan Univ. 25, 438-441.

organic compounds