2-Fluoro-N′-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide

Wang, D.-Y.; Meng, X.-F.; Ma, J.-J.

doi:10.1107/S1600536811050896

Volume 68
Part 1
Page o21
January 2012

Received 18 November 2011
Accepted 26 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 12.5
Details

2-Fluoro-N'-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide

Dong-Yue Wang,^a Xu-Feng Meng ^a and Jing-Jun Ma ^a ^*

^aHebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, People's Republic of China
Correspondence e-mail: majingjun71@yahoo.cn

In the title molecule, C₁₈H₁₃FN₂O₂, the hydroxy group is involved in an intramolecular O-HN hydrogen bond. The naphthyl ring system and the benzene ring form a dihedral angle of 31.0 (2)°. In the crystal, N-HO hydrogen bonds link the molecules into chains propagating in [101].

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011); Horiuchi et al. (2009). For coordination compounds with benzohydrazide ligands, see: El-Dissouky et al. (2010); Zhang et al. (2010). For standard bond lengths, see: Allen et al. (1987). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010); Liu et al. (2011); Zhou et al. (2011); Meng et al. (2011).

Experimental

Crystal data

C₁₈H₁₃FN₂O₂
M_r = 308.30
Monoclinic, C c
a = 7.078 (3) Å
b = 29.1953 (16) Å
c = 7.3013 (10) Å
= 106.521 (3)°
V = 1446.5 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.980, T_max = 0.983
4745 measured reflections
2641 independent reflections
1777 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.133
S = 1.03
2641 reflections
212 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.91 (1)	1.91 (2)	2.785 (3)	163 (4)
O2-H2N2	0.82	1.83	2.545 (4)	145
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: CV5206 ).

Acknowledgements

This project was sponsored by the Natural Development Foundation of Hebei Province (grant No. B2011204051), the Development Foundation of the Department of Education of Hebei Province (grant No. 2010137) and the Research Development Foundation of the Agricultural University of Hebei.

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 (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Dissouky, A., Al-Fulaij, O., Awad, M. K. & Rizk, S. (2010). J. Coord. Chem. 63, 330-345.
El-Sayed, M. A. A., Abdel-Aziz, N. I., Abdel-Aziz, A. A. M., El-Azab, A. S., Asiri, Y. A. & ElTahir, K. E. H. (2011). Bioorg. Med. Chem. 19, 3416-3424.
Suleiman Gwaram, N., Khaledi, H., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o721.
Horiuchi, T., Nagata, M., KitagawaB, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850-7860.
Liu, W.-H., Song, S.-J. & Ma, J.-J. (2011). Acta Cryst. E67, o2198.
Meng, X.-F., Wang, D.-Y. & Ma, J.-J. (2011). Acta Cryst. E67, o3109.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, S.-P., Wei, Y. & Shao, S.-C. (2010). Acta Cryst. E66, m1635.
Zhou, X., Gao, S.-T. & Ma, J.-J. (2011). Acta Cryst. E67, o2275.

organic compounds