2-Hydr­oxy-N′-(2-hydr­oxy-3-meth­oxy-5-nitro­benzyl­idene)-3-methyl­benzo­hydrazide

Han, Y.-Y.; Li, Y.-H.; Zhao, Q.-R.

doi:10.1107/S1600536810012912

Volume 66
Part 5
Page o1084
May 2010

Received 6 April 2010
Accepted 7 April 2010
Online 14 April 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 11.2
Details

2-Hydroxy-N'-(2-hydroxy-3-methoxy-5-nitrobenzylidene)-3-methylbenzohydrazide

You-Yue Han,^a ^* Yong-Hong Li ^a and Qiu-Rong Zhao ^a

^aDepartment of Chemistry and Life Science, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
Correspondence e-mail: hanyouyue@126.com

In the title compound, C₁₆H₁₅N₃O₆, the dihedral angle between the two benzene rings is 0.9 (2)°. The molecule adopts an E configuration with respect to the C=N bond. There are intramolecular O-HN and O-HO hydrogen bonds in the molecule. In the crystal structure, molecules are linked through intermolecular N-HO hydrogen bonds to form chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010). For the hydrazone compounds we reported recently, see: Han & Zhao (2010a,b). For bond-length data, see: Allen et al. (1987). For similar compounds, see: Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009).

Experimental

Crystal data

C₁₆H₁₅N₃O₆
M_r = 345.31
Monoclinic, P 2₁ /n
a = 7.482 (1) Å
b = 17.158 (1) Å
c = 12.250 (1) Å
= 91.565 (1)°
V = 1572.0 (3) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.10 × 0.07 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.989, T_max = 0.994
14545 measured reflections
2612 independent reflections
2165 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.108
S = 1.07
2612 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O6ⁱ	0.90 (1)	2.22 (1)	3.0190 (17)	147 (2)
O4-H4O3	0.82	1.79	2.5192 (15)	148
O1-H1N2	0.82	1.90	2.6166 (17)	145
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: 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: HG2671 ).

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187C).

References

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 (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201-207.
Han, Y.-Y. & Zhao, Q.-R. (2010a). Acta Cryst. E66, o1025.
Han, Y.-Y. & Zhao, Q.-R. (2010b). Acta Cryst. E66, o1026.
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o876.
Lin, X.-S. & Sang, Y.-L. (2009). Acta Cryst. E65, o1650.
Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o969.
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o190.
Ning, J.-H. & Xu, X.-W. (2009). Acta Cryst. E65, o905-o906.
Patil, S. A., Naik, V. H., Kulkarni, A. D., Kamble, U., Bagihalli, G. B. & Badami, P. S. (2010). J. Coord. Chem. 63, 688-699.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suleiman Gwaram, N., Khaledi, H., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o721.
Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.

organic compounds