1-Cyano-N-(2,4,5-trichloro­phen­yl)cyclo­propane-1-carboxamide

Liu, H.-J.; Weng, J.-Q.; Tan, C.-X.; Liu, X.-H.

doi:10.1107/S1600536811026225

Volume 67
Part 8
Page o1940
August 2011

Received 23 June 2011
Accepted 1 July 2011
Online 6 July 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.107
Data-to-parameter ratio = 13.8
Details

1-Cyano-N-(2,4,5-trichlorophenyl)cyclopropane-1-carboxamide

Hui-Jun Liu,^a Jian-Quan Weng,^a Cheng-Xia Tan ^a and Xing-Hai Liu ^a ^*

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: xhliu@zjut.edu.cn

In the title compound, C₁₁H₇Cl₃N₃O, the dihedral angle between the benzene and cyclopropane rings is 85.8 (2)°. In the crystal, molecules are linked by C-HO interactions, generating C(5) chains propagating in the a-axis direction.

Related literature

For the synthesis, see: Liu et al. (2007). For the biological activity of related compounds, see: Liu et al. (2009).

Experimental

Crystal data

C₁₁H₇Cl₃N₂O
M_r = 289.54
Triclinic, $[P \overline 1]$
a = 6.0068 (18) Å
b = 7.420 (2) Å
c = 14.047 (4) Å
= 77.531 (5)°
= 86.958 (5)°
= 84.483 (5)°
V = 608.1 (3) Å³
Z = 2
Mo K radiation
= 0.74 mm^-1
T = 294 K
0.24 × 0.22 × 0.18 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.614, T_max = 1.000
3103 measured reflections
2130 independent reflections
1619 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.107
S = 1.04
2130 reflections
154 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10BO1ⁱ	0.97	2.56	3.439 (3)	151
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5931 ).

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (Nos. 21002090, 31000008, 30900959), the Key Laboratory of Pesticide Chemistry and Applications, Ministry of Agriculture (MOA), Beijing 100193, People's Republic of China (No. MOAPCA201005) and the Scientific Research Fund of Zhejiang Education Department (Y201018479).

References

Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007). Bioorg. Med. Chem. Lett. 17, 3784-3788.
Liu, X. H., Shi, Y. X., Ma, Y., Zhang, C. Y., Dong, W. L., Li, P., Wang, B. L., li, B. J. & li, Z. M. (2009). Eur. J. Med. Chem. 44, 2782-2786.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds