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

Zhen Zhang

doi:10.1107/S1600536811000201

. 2011 Jan 8;67(Pt 2):o301. doi: 10.1107/S1600536811000201

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

Zhen Zhang ^a,^*

PMCID: PMC3051712 PMID: 21522991

Abstract

The title compound, C₁₄H₁₁N₃O₅, crystallized with two independent molecules per asymmetric unit. Each molecule assumes an E configuration with respect to the methylidene unit. Intramolecular O—H⋯O and N—H⋯O hydrogen bonds are present in each molecule and they are linked by an O—H⋯O hydrogen bond. The dihedral angles between the mean planes of the two benzene rings are 4.45 (16) and 1.7 (2)° in the two molecules. The crystal structure is stabilized by intermolecular O—H⋯O 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 = 13.769 (2) Å
b = 13.089 (2) Å
c = 19.999 (3) Å
β = 131.426 (3)°
V = 2702.5 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.974, T _max = 0.977
20705 measured reflections
5704 independent reflections
3336 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.165
S = 1.07
5704 reflections
407 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (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/S1600536811000201/su2244sup1.cif

e-67-0o301-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000201/su2244Isup2.hkl

e-67-0o301-Isup2.hkl^{(279.3KB, 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⋯O7ⁱ	0.82	1.86	2.650 (3)	162
O5—H5⋯O4	0.82	1.94	2.621 (3)	140
O5—H5⋯O4ⁱⁱ	0.82	2.30	2.997 (3)	143
O5—H5⋯N3	0.82	2.51	2.928 (3)	112
O6—H6⋯O2	0.82	1.91	2.713 (3)	168
O10—H10⋯O9	0.82	1.91	2.596 (3)	140
O10—H10⋯N6	0.82	2.50	2.909 (4)	112
N4—H4⋯O6	0.90 (1)	1.93 (3)	2.640 (3)	134 (3)
N1—H1⋯O1	0.90 (1)	1.84 (2)	2.599 (3)	141 (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 continuous work on the hydrazone compounds, a new hydrazone compound, N'-(4-hydroxy-3-nitrobenzylidene)-2-hydroxybenzohydrazide, was prepared and structurally characterized.

The title compound contains two independent molecules (Fig. 1). Each molecule (A abd B) assumes an E configuration with respect to the methylidene unit. Intramolecular O—H···O and N—H···O hydrogen bonds are present in the molecules and they are linked by a O-H···O hydrogen bond (Table 1 and Fig. 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 dihedral angles between the mean planes of the two benzene rings are 4.45 (16)) and 1.7 (2)° for molecules A and B, respectively.

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

Experimental

An ethanol solution (50 ml) of 2-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.