(E)-N′-(3-Fluoro­benzyl­idene)-4-methyl­benzohydrazide

Hu, H.-N.; Liu, S.-Y.

doi:10.1107/S1600536812019484

Volume 68
Part 6
Page o1643
June 2012

Received 30 April 2012
Accepted 1 May 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.123
Data-to-parameter ratio = 13.8
Details

(E)-N'-(3-Fluorobenzylidene)-4-methylbenzohydrazide

Hua-Nan Hu ^a and Shi-Yong Liu ^a ^*

^aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China
Correspondence e-mail: liushiyong2012@yahoo.cn

In the title compound, C₁₅H₁₃FN₂O, the dihedral angle between the benzene rings is 16.9 (2)°. The F atom and the O atom are in a syn conformation. In the crystal, molecules are linked by N-HO hydrogen bonds to generate C(4) chains propagating along the b-axis direction.

Related literature

For hydrazones that we have reported previously, see: Liu & You (2010); Liu & Wang (2010). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental

Crystal data

C₁₅H₁₃FN₂O
M_r = 256.27
Orthorhombic, P b c a
a = 13.2629 (5) Å
b = 7.9118 (3) Å
c = 24.9235 (8) Å
V = 2615.31 (16) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.984, T_max = 0.986
26269 measured reflections
2424 independent reflections
1997 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.123
S = 1.04
2424 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.90 (1)	2.04 (1)	2.9322 (17)	169 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6775 ).

Acknowledgements

The authors acknowledge the Zhejiang Provincial Natural Science Foundation of China (project No. Y12B020017).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Liu, S.-Y. & Wang, X. (2010). Acta Cryst. E66, o1775.
Liu, S.-Y. & You, Z. (2010). Acta Cryst. E66, o1652.
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564-1569.
Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412.

organic compounds