2,4-Dihydr­oxy-N′-(2-hydr­oxy-4-methoxy­benzyl­idene)benzohydrazide

You-Yue Han; Qiu-Rong Zhao

doi:10.1107/S1600536810012420

. 2010 Apr 10;66(Pt 5):o1041. doi: 10.1107/S1600536810012420

2,4-Dihydroxy-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide

You-Yue Han ^a,^*, Qiu-Rong Zhao ^a

PMCID: PMC2979259 PMID: 21579102

Abstract

In the title compound, C₁₅H₁₄N₂O₅, the dihedral angle between the two benzene rings is 4.3 (3)° and the molecule adopts an E configuration with respect to the C=N bond. Intramolecular O—H⋯N and N—H⋯O hydrogen bonds are observed. In the crystal structure, the molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds to form layers parallel to the ac plane.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶); Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₅
M _r = 302.28
Monoclinic,
a = 10.560 (3) Å
b = 12.752 (3) Å
c = 11.313 (2) Å
β = 112.853 (3)°
V = 1403.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.968, T _max = 0.973
7972 measured reflections
3030 independent reflections
1023 reflections with I > 2σ(I)
R _int = 0.127

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.182
S = 0.74
3030 reflections
206 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 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/S1600536810012420/ci5074sup1.cif

e-66-o1041-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012420/ci5074Isup2.hkl

e-66-o1041-Isup2.hkl^{(148.7KB, 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	1.92	2.635 (3)	145
N2—H2⋯O4	0.91 (1)	2.03 (3)	2.670 (3)	126 (3)
N2—H2⋯O1ⁱ	0.91 (1)	2.43 (2)	3.240 (4)	149 (3)
O5—H5⋯O2ⁱⁱ	0.82	2.05	2.865 (4)	172
O4—H4⋯O3ⁱ	0.82	1.79	2.607 (3)	174

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

Acknowledgments

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187 C). The authors thank Mr Gang Wu of Chuzhou University for his help with the crystal growth.

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). In the present work, the title new hydrazone compound is reported.

In the molecule of the title compound (Fig. 1), the dihedral angle between the two benzene rings is 4.3 (3)°. The molecule adopts an E configuration with respect to the C═N bond. There are intramolecular O–H···N and N–H···O hydrogen bonds (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987) and are comparable with those observed in related structures (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N—H···O and O–H···O hydrogen bonds (Table 1) to form layers parallel to the ac plane (Fig. 2).

Experimental

A mixture of 2-hydroxy-4-methoxybenzaldehyde (0.152 g, 1 mmol) and 2,4-dihydroxybenzohydrazide (0.168 g, 1 mmol) in methanol (50 ml) was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, single crystals of the title compound, suitable for X-ray diffraction, were formed.