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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 [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 12.9
Details
Open access

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

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-H...N hydrogen bond involving the naphthalene hydroxy substituent and a hydrazide N atom. In the crystal structure, symmetry-related molecules are linked through intermolecular N-H...O hydrogen bonds, forming chains propagating in [101].

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000[Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]); Karthikeyan et al. (2006[Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.]). For the coordination chemistry of Schiff bases, see: Ali et al. (2008[Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.]); Kargar et al. (2009[Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.]); Yeap et al. (2009[Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.]). For the crystal structures of Schiff base compounds, see: Fun et al. (2009[Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349-o350.]); Nadeem et al. (2009[Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.]); Eltayeb et al. (2008[Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.]). For Schiff base compounds reported by the author, see: Hao (2009a[Hao, Y.-M. (2009a). Acta Cryst. E65, o1400.],b[Hao, Y.-M. (2009b). Acta Cryst. E65, o2098.],c[Hao, Y.-M. (2009c). Acta Cryst. E65, o2600.],d[Hao, Y.-M. (2009d). Acta Cryst. E65, o2990.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13N3O4

  • Mr = 335.31

  • Monoclinic, P 21 /n

  • a = 7.4473 (6) Å

  • b = 29.068 (2) Å

  • c = 7.8504 (6) Å

  • [beta] = 113.963 (4)°

  • V = 1553.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.970, Tmax = 0.973

  • 8499 measured reflections

  • 2972 independent reflections

  • 1856 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.87 2.5881 (18) 146
N2-H2...O2i 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[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.  [CSD] [CrossRef] [details]
Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349-o350.  [CSD] [CrossRef] [details]
Hao, Y.-M. (2009a). Acta Cryst. E65, o1400.  [CSD] [CrossRef] [details]
Hao, Y.-M. (2009b). Acta Cryst. E65, o2098.  [CSD] [CrossRef] [details]
Hao, Y.-M. (2009c). Acta Cryst. E65, o2600.  [CSD] [CrossRef] [details]
Hao, Y.-M. (2009d). Acta Cryst. E65, o2990.  [CrossRef] [details]
Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.  [CSD] [CrossRef] [details]
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.  [CrossRef] [PubMed] [ChemPort]
Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.  [CrossRef] [PubMed] [ChemPort]
Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o1177  [ doi:10.1107/S160053681001490X ]

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