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

Qiao, Y.; Ju, X.; Gao, Z.; Kong, L.

doi:10.1107/S160053680905212X

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 (C-C) = 0.004 Å
R = 0.046
wR = 0.148
Data-to-parameter ratio = 12.8
Details

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

Yan Qiao,^a Xiuping Ju,^a Zhiqing Gao ^a and Lingqian Kong ^a ^*

^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-HO hydrogen bonds influence the molecular conformation. In the crystal, intermolecular N-HO and O-HO 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); Jeewoth et al. (1999). For their biological activity, see: Das et al. (1999). For related structures, see: Fun et al.(2008); Nie (2008).

Experimental

Crystal data

C₁₈H₁₄N₂O₂·H₂O
M_r = 308.33
Monoclinic, P 2₁ /c
a = 16.346 (6) Å
b = 7.192 (3) Å
c = 13.880 (5) Å
= 111.949 (4)°
V = 1513.5 (10) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.955, T_max = 0.961
7296 measured reflections
2669 independent reflections
1648 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.148
S = 1.07
2669 reflections
208 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3	0.86	2.11	2.899 (3)	152
O2-H2N2	0.82	1.89	2.604 (3)	145
O3-H3CO1ⁱ	0.85	2.03	2.882 (3)	179
O3-H3DO1ⁱⁱ	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); cell refinement: SAINT (Siemens, 1996); 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: 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.
Das, A., Trousdale, M. D., Ren, S. & Lien, E. J. (1999). Antiviral Res. 44, 201-208.
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.
Jeewoth, T., Bhowon, M. G. & Wah, H. L. K. (1999). Transition Met. Chem. 24, 445-448.
Nie, Y. (2008). Acta Cryst. E64, o471.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.

organic compounds