N′-[(2-Hydr­oxy-1-naphth­yl)methyl­idene]-2-nitro­benzohydrazide

Hao, Y.-M.

doi:10.1107/S160053681001490X

Volume 66
Part 5
Page o1177
May 2010

Received 15 April 2010
Accepted 22 April 2010
Online 28 April 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 12.9
Details

N'-[(2-Hydroxy-1-naphthyl)methylidene]-2-nitrobenzohydrazide

Yu-Mei Hao ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
Correspondence e-mail: jyxygzb@163.com

In the title Schiff base compound, C₁₈H₁₃N₃O₄, prepared by the reaction of 2-hydroxy-1-naphthaldehyde with 2-nitrobenzohydrazide, the dihedral angle between the benzene ring and naphthyl ring system is 23.0 (2)°. There is an intramolecular O-HN hydrogen bond involving the naphthalene hydroxy substituent and a hydrazide N atom. In the crystal structure, symmetry-related molecules are linked through intermolecular N-HO hydrogen bonds, forming chains propagating in [101].

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000); Sriram et al. (2006); Karthikeyan et al. (2006). For the coordination chemistry of Schiff bases, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For the crystal structures of Schiff base compounds, see: Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008). For Schiff base compounds reported by the author, see: Hao (2009a,b,c,d). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₈H₁₃N₃O₄
M_r = 335.31
Monoclinic, P 2₁ /n
a = 7.4473 (6) Å
b = 29.068 (2) Å
c = 7.8504 (6) Å
= 113.963 (4)°
V = 1553.0 (2) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.970, T_max = 0.973
8499 measured reflections
2972 independent reflections
1856 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.111
S = 1.05
2972 reflections
230 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.87	2.5881 (18)	146
N2-H2O2ⁱ	0.90 (1)	1.94 (1)	2.8133 (19)	164 (2)
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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2174 ).

References

Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.
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). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.
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Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.
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Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.

organic compounds