4-Hy­droxy-N′-(4-hy­droxy-3-nitro­benzyl­idene)benzohydrazide

Zhen Zhang

doi:10.1107/S1600536811000195

. 2011 Jan 8;67(Pt 2):o300. doi: 10.1107/S1600536811000195

4-Hydroxy-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide

Zhen Zhang ^a,^*

PMCID: PMC3051539 PMID: 21522990

Abstract

The molecule of the title compound, C₁₄H₁₁N₃O₅, assumes an E configuration with respect to the methylidene unit. An intramolecular O—H⋯O hydrogen bond is present in the molecule. The dihedral angle between the mean planes of the two benzene rings is 5.46 (15)°. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯N, and N—H⋯O hydrogen bonds.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Fan et al. (2010 ▶); Rasras et al. (2010 ▶). For similar hydrazone compounds, see: Ahmad et al. (2010 ▶); Ban (2010 ▶); Ji & Lu (2010 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₁N₃O₅
M _r = 301.26
Monoclinic,
a = 8.786 (3) Å
b = 14.882 (2) Å
c = 10.3064 (17) Å
β = 91.100 (2)°
V = 1347.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.964, T _max = 0.967
7079 measured reflections
2952 independent reflections
1353 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.137
S = 1.06
2952 reflections
204 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 global, I. DOI: 10.1107/S1600536811000195/su2243sup1.cif

e-67-0o300-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000195/su2243Isup2.hkl

e-67-0o300-Isup2.hkl^{(144.9KB, 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—H1A⋯O2ⁱ	0.82	1.93	2.736 (3)	169
O1—H1A⋯N2ⁱ	0.82	2.61	3.121 (3)	122
O3—H3⋯O4	0.82	1.90	2.592 (4)	142
N1—H1⋯O5ⁱⁱ	0.90 (1)	2.32 (1)	3.203 (4)	167 (3)

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

Acknowledgments

The author thanks the Experimental Center of Linyi University for supporting this work.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuatio of our work on the hydrazone compounds, the new title hydrazone compound was prepared and structurally characterized.

The molecule of the title compound assumes an E configuration with respect to the methylidene unit (Fig. 1). The dihedral angle between the best mean planes of the two benzene rings is 5.46 (15)°. An intramolecular O—H···O hydrogen bond is present in the molecule (Table 1). The bond lengths are comparable to those observed in similar hydrazone compounds (Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010).

The crystal structure is stabilized by intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

An ethanol solution (50 ml) of 4-hydroxybenzohydrazide (0.01 mol) and 4-hydroxy-3-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals, suitable for X-ray diffraction, were formed by slow evaporation of the solution in air.