N′-(2,4-Dichloro­benzyl­idene)-2-fluoro­benzohydrazide

Wang, H.-T.; Yuan, L.; Nan, Y.; Wang, R.; Zhou, L.; Niu, Y.

doi:10.1107/S1600536810053249

Volume 67
Part 2
Page o252
February 2011

Received 17 December 2010
Accepted 18 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.056
wR = 0.163
Data-to-parameter ratio = 16.1
Details

N'-(2,4-Dichlorobenzylidene)-2-fluorobenzohydrazide

Hai-Tao Wang,^a Ling Yuan,^b,^c Yi Nan,^d Rong Wang,^d Li Zhou ^b and Yang Niu ^d ^*

^aThe Second Hospital of Jilin University, Changchun Jilin 130041, People's Republic of China,^bPharmacy College of Ningxia Medical University, Yinchuan Ningxia 750004, People's Republic of China,^cMinority Traditional Medical Center of Minzu University of China, Beijing 100081, People's Republic of China, and ^dTraditional Chinese Medicine College of Ningxia Medical University, Yinchuan Ningxia 750004, People's Republic of China
Correspondence e-mail: niuyang750@126.com

The molecule of the title compound, C₁₄H₉Cl₂FN₂O, exists in a trans configuration with respect to the methylidene unit and the benzene rings form a dihedral angle of 8.1 (2)°. In the crystal, molecules are linked through N-HO hydrogen bonds into C(4) chains propagating in [100].

Related literature

For related structures and background to the pharmacological properties of hydrazone compounds, see: Xu et al. (2011a,b). For reference bond-length values, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₉Cl₂FN₂O
M_r = 311.13
Monoclinic, P 2₁ /n
a = 7.2310 (14) Å
b = 26.145 (5) Å
c = 8.0590 (16) Å
= 115.033 (3)°
V = 1380.5 (5) Å³
Z = 4
Mo K radiation
= 0.48 mm^-1
T = 298 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.898, T_max = 0.911
9842 measured reflections
2963 independent reflections
2236 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.163
S = 1.05
2963 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.66 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.89 (1)	2.19 (1)	3.054 (3)	162 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5775 ).

Acknowledgements

This project was supported by the 2008 Ningxia science and technology key projects (No. 222) and the 2009 Ningxia science and technology key projects (No. 232).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xu, C.-B., Wang, Z.-G., Nan, Y., Yuan, L., Wang, R. & Zhang, S.-X. (2011a). Acta Cryst. E67, o69.
Xu, C.-B., Wang, Z.-G., Nan, Y., Yuan, L., Wang, R. & Zhang, S.-X. (2011b). Acta Cryst. E67, o70.

organic compounds