(E)-N′-(3-Hy­droxy­benzyl­idene)-3-nitro­benzohydrazide

Fu-Lin Mao; Chun-Hua Dai

doi:10.1107/S1600536810049482

. 2010 Dec 4;67(Pt 1):o7. doi: 10.1107/S1600536810049482

(E)-N′-(3-Hydroxybenzylidene)-3-nitrobenzohydrazide

Fu-Lin Mao ^a,^*, Chun-Hua Dai ^a

PMCID: PMC3050236 PMID: 21522781

Abstract

The title compound, C₁₄H₁₁N₃O₄, was prepared by the reaction of 3-nitrobenzohydrazide with 3-hydroxybenzaldehyde. The molecule adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 32.3 (2)°. In the crystal, the molecules are linked through intermolecular N—H⋯O, O—H⋯N, and O—H⋯O hydrogen bonds, forming chains in the a-axis direction.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For similar compounds that we have reported recently, see: Dai & Mao (2010a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M _r = 285.26
Monoclinic,
a = 16.154 (3) Å
b = 13.295 (3) Å
c = 13.537 (2) Å
β = 120.324 (2)°
V = 2509.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.28 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.969, T _max = 0.974
6631 measured reflections
2738 independent reflections
1588 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.144
S = 1.03
2738 reflections
196 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 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/S1600536810049482/sj5070sup1.cif

e-67-000o7-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049482/sj5070Isup2.hkl

e-67-000o7-Isup2.hkl^{(134.5KB, 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⋯N1ⁱ	0.85 (1)	2.58 (3)	2.986 (2)	111 (2)
O1—H1⋯O2ⁱ	0.85 (1)	1.91 (1)	2.758 (2)	174 (3)
N2—H2A⋯O4ⁱⁱ	0.89 (1)	2.47 (1)	3.354 (3)	171 (2)

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

Acknowledgments

We acknowledge the Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection for financial support (Project No. JLCBE07026).

supplementary crystallographic information

Comment

In the last few years, medical applications of a number of hydrazone compounds have been received much attention (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The structures of several hydrazone derivatives have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on this area (Dai & Mao, 2010a,b), in this paper, we report the structure of the new derivative N'-(3-hydroxybenzylidene)-3-nitrobenzohydrazide.

In the molecule of the title compound, the dihedral angle between the C1···C6 and C9···C14 benzene rings is 32.3 (2)°. The O3/N3/O4 plane forms a dihedral angle of 4.8 (2)° with the C9···C14 benzene ring. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above. In the crystal structure, the hydrazone molecules are linked through intermolecular N—H···O, O–H···N, and O—H···O hydrogen bonds (Table 1), to form one-dimensional chains in the a direction, Fig. 2.

Experimental

The reaction of 3-nitrobenzohydrazide (0.181 g, 1 mmol) with 3-hydroxybenzaldehyde (0.122 g, 1 mmol) in 50 ml methanol at room temperature afforded the title compound. Yellow block-shaped single crystals were formed by slow evaporation of the clear solution in air.