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Volume 66 
Part 1 
Page o95  
January 2010  

Received 2 November 2009
Accepted 3 December 2009
Online 9 December 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.148
Data-to-parameter ratio = 12.8
Details
Open access

(E)-N'-[(2-Hydroxy-1-naphthyl)methylene]benzohydrazide monohydrate

aDongchang College, Liaocheng University, Liaocheng, 250059, People's Republic of China
Correspondence e-mail: konglingqian08@163.com

In the title compound, C18H14N2O2·H2O, the dihedral angle between the benzene ring and the naphthalene system is 5.18 (10)°. Intramolecular N-H...O hydrogen bonds influence the molecular conformation. In the crystal, intermolecular N-H...O and O-H...O hydrogen bonds are observed as well as [pi]-[pi] interactions between the phenyl ring and the substituted ring of the naphthalene [centroid-centroid distance = 3.676 (11) Å].

Related literature

For background to Schiff bases in coordination chemistry, see: Chakraborty & Patel (1996[Chakraborty, J. & Patel, R. N. (1996). J. Indian Chem. Soc. 73, 191-195.]); Jeewoth et al. (1999[Jeewoth, T., Bhowon, M. G. & Wah, H. L. K. (1999). Transition Met. Chem. 24, 445-448.]). For their biological activity, see: Das et al. (1999[Das, A., Trousdale, M. D., Ren, S. & Lien, E. J. (1999). Antiviral Res. 44, 201-208.]). For related structures, see: Fun et al.(2008[Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.]); Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]).

[Scheme 1]

Experimental

Crystal data
  • C18H14N2O2·H2O

  • Mr = 308.33

  • Monoclinic, P 21 /c

  • a = 16.346 (6) Å

  • b = 7.192 (3) Å

  • c = 13.880 (5) Å

  • [beta] = 111.949 (4)°

  • V = 1513.5 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.50 × 0.48 × 0.43 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.955, Tmax = 0.961

  • 7296 measured reflections

  • 2669 independent reflections

  • 1648 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.148

  • S = 1.07

  • 2669 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3 0.86 2.11 2.899 (3) 152
O2-H2...N2 0.82 1.89 2.604 (3) 145
O3-H3C...O1i 0.85 2.03 2.882 (3) 179
O3-H3D...O1ii 0.85 1.88 2.734 (3) 179
Symmetry codes: (i) -x, -y, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, 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: SHELXTL .


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2175 ).


Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

Chakraborty, J. & Patel, R. N. (1996). J. Indian Chem. Soc. 73, 191-195.  [ChemPort]
Das, A., Trousdale, M. D., Ren, S. & Lien, E. J. (1999). Antiviral Res. 44, 201-208.  [ISI] [CrossRef] [PubMed] [ChemPort]
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.  [CSD] [CrossRef] [details]
Jeewoth, T., Bhowon, M. G. & Wah, H. L. K. (1999). Transition Met. Chem. 24, 445-448.  [ISI] [CrossRef] [ChemPort]
Nie, Y. (2008). Acta Cryst. E64, o471.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.


Acta Cryst (2010). E66, o95  [ doi:10.1107/S160053680905212X ]

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