(E)-4-Hydr­oxy-N′-(4-nitro­benzyl­idene)benzohydrazide

Cong-Ming Li; Hong-Yan Ban

doi:10.1107/S1600536809020066

. 2009 Jun 6;65(Pt 7):o1466. doi: 10.1107/S1600536809020066

(E)-4-Hydroxy-N′-(4-nitrobenzylidene)benzohydrazide

Cong-Ming Li ^a,^*, Hong-Yan Ban ^b

PMCID: PMC2969308 PMID: 21582769

Abstract

The molecule of the title compound, C₁₄H₁₁N₃O₄, is approximately planar, the dihedral angle between the planes of the two substituted benzene rings being 2.54 (7)°. The molecule exists in a trans configuration with respect to the central methylidene unit. In the crystal structure, molecules are linked through intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming layers parallel to (101). The O/N—H⋯O and C—H⋯O interactions form a pair of bifurcated acceptor bonds involving the cabonyl/nitro O atom, generating an R ₂ ¹(6) motif.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M _r = 285.26
Monoclinic,
a = 7.659 (1) Å
b = 13.587 (2) Å
c = 12.561 (2) Å
β = 92.784 (5)°
V = 1305.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.979, T _max = 0.981
7862 measured reflections
2835 independent reflections
2109 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.04
2835 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809020066/ci2812sup1.cif

e-65-o1466-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020066/ci2812Isup2.hkl

e-65-o1466-Isup2.hkl^{(139.2KB, 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
O2—H2⋯O1ⁱ	0.82	2.02	2.8131 (15)	164
N2—H2B⋯O4ⁱⁱ	0.90 (1)	2.22 (1)	3.0513 (17)	155 (2)
C7—H7⋯O4ⁱⁱ	0.93	2.41	3.235 (2)	148
C13—H13⋯O1ⁱ	0.93	2.35	3.0713 (19)	134

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

Acknowledgments

The authors acknowledge financial support by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Schiff bases derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of Schiff bases have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported a few such compounds (Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the title new compound.

The title Schiff base molecule (Fig. 1) is nearly planar, with the dihedral angle between the two benzene rings being 2.54 (7)°. The molecule exists in a trans configuration with respect to the central methylidene (C7═N1) unit. The N2—N1—C7—C1 torsion angle is 179.12 (14)°.

In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming layers parallel to the (101) (Fig. 2). Within the layer, C—H···O hydrogen bonds are also observed.

Experimental

The title compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 4-hydroxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution by slow evaporation in air.