(E)-4-Bromo-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)benzohydrazide

Diao, Y.-P.; Zhang, Q.-H.; Wang, D.-C.; Deng, X.-M.

doi:10.1107/S1600536808031395

Volume 64
Part 11
Page o2070
November 2008

Received 21 September 2008
Accepted 28 September 2008
Online 4 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.040
wR = 0.101
Data-to-parameter ratio = 14.7
Details

(E)-4-Bromo-N'-(2-hydroxy-1-naphthylmethylene)benzohydrazide

Yun-Peng Diao,^a,^b Qi-Hui Zhang,^c Da-Cheng Wang ^a and Xu-Ming Deng ^a ^*

^aCollege of Animal Science and Veterinary Medicine, Jilin University, Jilin 130062, People's Republic of China,^bCollege of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China, and ^cSchool of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China
Correspondence e-mail: xumingdeng08@126.com

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide. This Schiff base molecule has an E configuration about the C=N bond and is almost planar, the dihedral angle between the mean planes through the substituted benzene ring and the naphthyl system being 6.6 (2)°. There is an intramolecular O-HN hydrogen bond involving the naphthyl hydroxy substituent and the N' atom of the hydrazide group. In the crystal structure, molecules are linked through intermolecular N--HO hydrogen bonds to form chains extending along the b direction.

Related literature

For related structures, see: Brückner et al. (2000); Diao (2007); Diao et al. (2007, 2008); Harrop et al. (2003); Huang et al. (2007); Li et al. (2007); Ren et al. (2002).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M_r = 369.21
Monoclinic, P c
a = 6.185 (2) Å
b = 4.7638 (19) Å
c = 25.689 (10) Å
= 95.449 (7)°
V = 753.5 (5) Å³
Z = 2
Mo K radiation
= 2.74 mm^-1
T = 298 (2) K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.494, T_max = 0.514 (expected range = 0.446-0.464)
5817 measured reflections
3119 independent reflections
2443 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.101
S = 0.90
3119 reflections
212 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.24 e Å^-3
Absolute structure: Flack (1983), 1493 Friedel pairs
Flack parameter: 0.026 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.89 (3)	1.99 (3)	2.841 (4)	160 (6)
O2-H2N2	0.82	1.86	2.580 (4)	145
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SU2066 ).

References

Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100-6106.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Diao, Y.-P. (2007). Acta Cryst. E63, m1453-m1454.
Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816.
Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008). Acta Cryst. E64, o101.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410-411.
Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659.
Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291.
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds