(E)-3-Bromo-N′-(2-hydr­oxy-1-naphthyl­idene)benzohydrazide

Cao, G.-B.; Lu, X.-H.

doi:10.1107/S1600536809022533

Volume 65
Part 7
Page o1600
July 2009

Received 10 June 2009
Accepted 12 June 2009
Online 17 June 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.049
wR = 0.130
Data-to-parameter ratio = 16.0
Details

(E)-3-Bromo-N'-(2-hydroxy-1-naphthylidene)benzohydrazide

Guo-Biao Cao ^a ^* and Xu-Hui Lu ^a

^aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
Correspondence e-mail: guobiao_cao@126.com

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 18.3 (2)°. An intramolecular O-HN hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N-HO and C-HO hydrogen bonds, forming a chain running along [101].

Related literature

For crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For hydrazone compounds reported previously by our group, see: Qu et al. (2008); Yang et al. (2008).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M_r = 369.21
Monoclinic, P 2₁ /n
a = 7.257 (1) Å
b = 31.229 (2) Å
c = 7.327 (1) Å
= 109.186 (2)°
V = 1568.3 (3) Å³
Z = 4
Mo K radiation
= 2.63 mm^-1
T = 298 K
0.27 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.505, T_max = 0.548
9563 measured reflections
3393 independent reflections
2177 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.130
S = 1.03
3393 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.95 e Å^-3
_min = -0.74 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.86	2.584 (4)	146
N2-H2O2ⁱ	0.90 (3)	1.99 (2)	2.840 (4)	159 (4)
C11-H11O2ⁱ	0.92	2.42	3.138 (4)	134
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: 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: RZ2335 ).

Acknowledgements

The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189.
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o1466.
Qu, L.-Z., Yang, T., Cao, G.-B. & Wang, X.-Y. (2008). Acta Cryst. E64, o2061.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343-348.
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.
You, Z.-L., Dai, W.-M., Xu, X.-Q. & Hu, Y.-Q. (2008). Pol. J. Chem. 82, 2215-2219.
Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.

organic compounds