N′-(5-Chloro-2-hydroxy­benzyl­idene)-4-hydroxy­benzohydrazide

Xiao-Yang Qiu

doi:10.1107/S160053680901215X

. 2009 Apr 8;65(Pt 5):o975. doi: 10.1107/S160053680901215X

N′-(5-Chloro-2-hydroxybenzylidene)-4-hydroxybenzohydrazide

Xiao-Yang Qiu ^a,^*

PMCID: PMC2977672 PMID: 21584015

Abstract

The title Schiff base compound, C₁₄H₁₁ClN₂O₃, was prepared by the reaction of 5-chlorosalicylaldehyde and 4-hydroxybenzohydrazide. The molecule exists in a trans configuration with respect to the methylidene group. The dihedral angle between the two benzene rings is 40.1 (2)°. An intramolecular O—H⋯N hydrogen bond helps to stabilize the molecular conformation. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Fun et al. (2008 ▶). For the structures of hydrazone compounds we have reported previously, see: Qiu, Fang et al. (2006 ▶); Qiu, Luo et al., (2006a ▶,b ▶); Qiu, Xu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures see: Singh et al. (2007 ▶); Narayana et al. (2007 ▶); Cui et al. (2007 ▶); Diao et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₃
M _r = 290.70
Orthorhombic,
a = 9.423 (1) Å
b = 9.839 (1) Å
c = 13.770 (1) Å
V = 1276.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.950, T _max = 0.955
7398 measured reflections
2231 independent reflections
2144 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.071
S = 1.06
2231 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ▶), 784 Friedel pairs
Flack parameter: −0.01 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901215X/sj2605sup1.cif

e-65-0o975-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901215X/sj2605Isup2.hkl

e-65-0o975-Isup2.hkl^{(109.7KB, 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
N2—H2⋯O2ⁱ	0.892 (10)	2.121 (11)	3.0065 (18)	172 (3)
O3—H3⋯O2ⁱⁱ	0.82	1.98	2.7479 (19)	157
O1—H1⋯N1	0.82	1.89	2.6057 (19)	145

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

Acknowledgments

The author acknowledges the Natural Science Foundation of the Education Office of Anhui Province (Project No. 2009 A150020).

supplementary crystallographic information

Comment

Hyrazone compounds, derived from the reaction of aldehydes with hydrazides, have been widely studied due to their excellent biological properties (Bedia et al., 2006; Rollas et al., 2002; Fun et al., 2008). Recently, we have reported several Schiff base hydrazone compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006a,b; Qiu, Xu et al., 2006), and we report herein the crystal structure of the new title compound, (I), Fig. 1.

The molecule in (I) exists in a trans configuration with respect to the methylidene group. The dihedral angle between the two benzene rings is 40.1 (2)°. The bond lengths in (I) are found to have normal values (Allen et al., 1987) and are comparable to the values found in similar compounds (Singh et al., 2007; Narayana et al., 2007; Cui et al., 2007; Diao et al., 2008).

An intramolecular O–H···N hydrogen bond (Table 1) helps to stabilize the molecular conformation. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N–H···O and O–H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of equimolar amounts (0.5 mmol each) of 5-chlorosalicylaldehyde and 4-hydroxybenzohydrazide in methanol (20 ml). Excess methanol was removed from the reaction mixture by distillation. The colourless solid was filtered and dried in air. Colourless block-shaped crystals suitable for X-ray diffraction were obtained from a methanol solution.