N′-(3,5-Dichloro-2-hy­droxy­benzyl­idene)-4-nitro­benzohydrazide methanol solvate

Zhu, H.-Y.

doi:10.1107/S1600536810036184

Volume 66
Part 10
Page o2562
October 2010

Received 6 September 2010
Accepted 8 September 2010
Online 15 September 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.124
Data-to-parameter ratio = 14.9
Details

N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-nitrobenzohydrazide methanol solvate

Hai-Yun Zhu ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, People's Republic of China
Correspondence e-mail: zhuzhuhaiyun@126.com

In the title compound, C₁₄H₉Cl₂N₃O₄·CH₄O, the dihedral angle between the two benzene rings in the hydrazone molecule is 6.3 (3)°. An intramolecular N-HO hydrogen bond stabilizes the molecular conformation. In the crystal, centrosymmetrically related molecules are linked through intermolecular O-HO and N-HO hydrogen bonds.

Related literature

For general background to hydrazone compounds, see: Rasras et al. (2010); Fan et al. (2010); Ajani et al. (2010); Avaji et al. (2009). For the crystal structures of related hydrazone compounds, see: Khaledi et al. (2010); Han et al. (2010); Hussain et al. (2010); Ji & Lu (2010). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₉Cl₂N₃O₄·CH₄O
M_r = 386.18
Monoclinic, P 2₁ /n
a = 7.415 (3) Å
b = 13.408 (3) Å
c = 16.674 (2) Å
= 99.716 (3)°
V = 1634.0 (8) Å³
Z = 4
Mo K radiation
= 0.43 mm^-1
T = 298 K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.938, T_max = 0.958
8410 measured reflections
3467 independent reflections
2099 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.124
S = 1.02
3467 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.92	2.633 (3)	145
N2-H2O5	0.90 (1)	1.91 (1)	2.793 (3)	167 (3)
O5-H5O2ⁱ	0.82	2.15	2.903 (3)	153
Symmetry code: (i) -x+1, -y, -z+1.

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: RZ2485 ).

Acknowledgements

This work was supported by the Science Research Foundation of Baoji University of Arts and Sciences (grant No. ZK085).

References

Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.
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.
Avaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552-3559.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fan, C. D., Su, H., Zhao, J., Zhao, B. X., Zhang, S. L. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 1438-1446.
Han, Y.-Y., Li, Y.-H. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1085-o1086.
Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888.
Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.
Khaledi, H., Alhadi, A. A., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o105-o106.
Rasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307-2313.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds