3-Hydr­oxy-N′-(2-hydroxy­benzyl­idene)benzohydrazide

San-Jun Peng; Hai-Yun Hou

doi:10.1107/S1600536808027426

. 2008 Sep 6;64(Pt 10):o1864. doi: 10.1107/S1600536808027426

3-Hydroxy-N′-(2-hydroxybenzylidene)benzohydrazide

San-Jun Peng ^a,^*, Hai-Yun Hou ^b

PMCID: PMC2959272 PMID: 21201081

Abstract

The title compound, C₁₄H₁₂N₂O₃, was synthesized by the condensation of salicylaldehyde with 3-hydroxybenzohydrazide. The dihedral angle between the two benzene rings is 12.4 (2)°. The 2-hydroxy group forms an intramolecular O—H⋯N hydrogen bond with the imide N atom. Molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds into a two-dimensional polymeric structure parallel to the ab plane.

Related literature

For related literature, see: Ali et al. (2005 ▶); Eltayeb et al. (2008 ▶); Habibi et al. (2007 ▶); Jing et al. (2006 ▶); Ling et al. (2008 ▶); Peng & You (2007 ▶); Peng & Zhou (2007 ▶); Peng, Ping & Song (2007 ▶); Peng, Yang & Zhou (2006 ▶); Peng, Zhou & Yang (2006 ▶); Yehye et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₃
M _r = 256.26
Orthorhombic,
a = 14.405 (2) Å
b = 9.661 (1) Å
c = 17.905 (2) Å
V = 2491.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.978, T _max = 0.981
13415 measured reflections
2720 independent reflections
1869 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.03
2720 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027426/gk2164sup1.cif

e-64-o1864-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027426/gk2164Isup2.hkl

e-64-o1864-Isup2.hkl^{(133.7KB, 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
O1—H1⋯N1	0.82	1.88	2.6010 (19)	146
O3—H3⋯O2ⁱ	0.82	1.81	2.5946 (16)	159
N2—H2⋯O3ⁱⁱ	0.895 (9)	2.119 (10)	3.0062 (18)	171.0 (18)

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

Acknowledgments

We acknowledge Changsha University of Science and Technology for research grants.

supplementary crystallographic information

Comment

Schiff bases derived from the condensation of aldehydes with primary amines play an important role in coordination chemistry (Ali et al., 2005; Eltayeb et al., 2008; Habibi et al., 2007). Recently, we have reported synthesis and crystal structure of some Schiff base complexes (Peng, Yang & Zhou, 2006; Peng, Zhou & Yang, 2006; Peng et al., 2007; Peng & You, 2007; Peng & Zhou, 2007). We report herein the crystal structure of the title compound, Fig. 1.

All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006; Ling et al., 2008). The molecule is not planar and the dihedral angle between the two benzene rings is 12.4 (2)°. There is an intramolecular O–H···N hydrogen bond (Table 1) in each molecule of the compound. The molecules are linked through intermolecular O–H···O and N–H···O hydrogen bonds (Table 1), forming layers parallel to the ab plane (Fig. 2).

Experimental

3-Hydroxybenzohydrazide (0.1 mmol, 15.2 mg) and salicylaldehyde (0.1 mmol, 12.2 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept open to slowly evaporate for a few days, depositing colorless block-like crystals of the title compound.