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

Chong-Gui Ren

doi:10.1107/S1600536809020820

. 2009 Jun 6;65(Pt 7):o1503–o1504. doi: 10.1107/S1600536809020820

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

Chong-Gui Ren ^a,^*

PMCID: PMC2969228 PMID: 21582802

Abstract

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—H⋯N interaction is present. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O 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,
a = 8.030 (1) Å
b = 13.546 (2) Å
c = 13.433 (2) Å
β = 107.247 (2)°
V = 1395.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.107
S = 1.03
3039 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020820/bx2214sup1.cif

e-65-o1503-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020820/bx2214Isup2.hkl

e-65-o1503-Isup2.hkl^{(149.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.6164 (19)	145
O3—H3⋯O2ⁱ	0.82	1.85	2.658 (2)	168
N2—H2⋯O3ⁱⁱ	0.899 (10)	2.204 (16)	3.000 (2)	147 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The author acknowledges Zaozhuang University for funding this study.

supplementary crystallographic information

Comment

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound. In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 5.1 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (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). —H···N OIn the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), Fig. 2.

Experimental

All the starting materials were obtained with AR grade from Lancaster. 3,5-Dichloro-2-hydroxybenzaldehyde (1.0 mmol, 192.2 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were refluxed in 30 ml methanol solution for 30 min giving a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for a week at room temperature.