2-Hy­droxy-N′-(4-hy­droxy­benzyl­idene)-3-methyl­benzohydrazide

Xi-Hai Shen; Li-Xue Zhu; Li-Juen Shao; Zhao-Fu Zhu

doi:10.1107/S1600536811055930

. 2012 Jan 7;68(Pt 2):o297. doi: 10.1107/S1600536811055930

2-Hydroxy-N′-(4-hydroxybenzylidene)-3-methylbenzohydrazide

Xi-Hai Shen ^a, Li-Xue Zhu ^a,^*, Li-Juen Shao ^a, Zhao-Fu Zhu ^a

PMCID: PMC3274990 PMID: 22346935

Abstract

The title compound, C₁₅H₁₄N₂O₃, was prepared by condensing 4-hydroxybenzaldehyde and 2-hydroxy-3-methylbenzohydrazide in methanol. The two benzene rings make a dihedral angle of 19.03 (11)°. An intramolecular O—H⋯O hydrogen bond is observed. The crystal structure is stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds and C—H⋯O interactions, which lead to the formation of a three-dimensional network.

Related literature

For the crystal structures of similar hydrazone compounds, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Zhi et al. (2011 ▶); Huang & Wu (2010 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M _r = 270.28
Orthorhombic,
a = 7.3872 (17) Å
b = 13.012 (2) Å
c = 13.592 (2) Å
V = 1306.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.981, T _max = 0.984
6296 measured reflections
2663 independent reflections
1953 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.103
S = 0.99
2663 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811055930/su2356sup1.cif

e-68-0o297-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055930/su2356Isup2.hkl

e-68-0o297-Isup2.hkl^{(130.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055930/su2356Isup3.cml

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
O3—H3⋯O2	0.82	1.86	2.575 (2)	146
O1—H1⋯O2ⁱ	0.82	2.00	2.809 (2)	167
N2—H2A⋯O1ⁱⁱ	0.86	2.36	3.067 (2)	139
C3—H3A⋯O2ⁱ	0.93	2.51	3.208 (2)	132

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

supplementary crystallographic information

Comment

In the last few years, the crystal structures of a number of hydrazone compounds have been reported (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010). As an extension of work on such compounds, we report herein on the synthesis and crystal structure of the title compound.

In the title molecule, Fig. 1, there is an intramolecular O3—H3···O2 hydrogen bond (Table 1). The benzene rings, (C1—C6) and (C9—C14), make a dihedral angle of 19.03 (11)°. All the geometrical parameters are within normal ranges and are comparable with those in similar compounds, mentioned above.

In the crystal, molecules are linked via O—H···O and N—H···O hydrogen bonds and C-H···O interactions, leading to the formation of a three-dimensional network (Table 1 and Fig. 2).

Experimental

4-Hydroxybenzaldehyde (122.1 mg, 1.0 mmol) and 2-hydroxy-3-methylbenzohydrazide (166.2 mg, 1.0 mmol) were mixed in methanol (60 ml). The mixture was refluxed for 30 min, then cooled to room temperature, yielding a colourless solution. Colourless crystals were formed when the solution was left to evaporate in air for several days.