4-Hydr­oxy-N′-(3,5-dichloro-2-hydroxy­benzyl­idene)benzohydrazide

Ren, C.-G.

doi:10.1107/S1600536809020820

Volume 65
Part 7
Pages o1503-o1504
July 2009

Received 25 May 2009
Accepted 2 June 2009
Online 6 June 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.107
Data-to-parameter ratio = 15.6
Details

4-Hydroxy-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide

Chong-Gui Ren ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Zaozhuang University, Zaozhuang Shandong 277160, People's Republic of China
Correspondence e-mail: renchonggui@163.com

In the title compound, C₁₄H₁₀Cl₂N₂O₃, the dihedral angle between the two benzene rings is 5.1 (2)°. The molecule adopts an E configuration with respect to the C=N bond and an intramolecular O-HN interaction is present. In the crystal structure, molecules are linked through intermolecular N-HO and O-HO hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999); Ren et al. (2002); Eltayeb et al. (2008); Sinha et al. (2008). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008); Prabhakaran et al. (2006); Dhar et al. (2005). For related structures, see: Cui et al. (2007); Jing et al. (2007); Ma et al. (2008); Salhin et al. (2007); Lin et al. (2007); Alhadi et al. (2008); Xue et al. (2008); Wang et al. (2008); Lu (2008); Diao et al. (2008); Qiu (2009); Mohd Lair et al. (2009a,b). For reference structural data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O₃
M_r = 325.14
Monoclinic, P 2₁ /c
a = 8.030 (1) Å
b = 13.546 (2) Å
c = 13.433 (2) Å
= 107.247 (2)°
V = 1395.5 (3) Å³
Z = 4
Mo K radiation
= 0.48 mm^-1
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.911, T_max = 0.919
8463 measured reflections
3039 independent reflections
2324 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
3039 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.90	2.6164 (19)	145
O3-H3O2ⁱ	0.82	1.85	2.658 (2)	168
N2-H2O3ⁱⁱ	0.899 (10)	2.204 (16)	3.000 (2)	147 (2)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2214 ).

Acknowledgements

The author acknowledges Zaozhuang University for funding this study.

References

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organic compounds