N′-[(E)-1-(5-Bromo-2-hy­droxy­phen­yl)ethyl­idene]-4-nitro­benzohydrazide

Chang-Zheng Zheng; Liang Wang; Juan Liu; Yu-Jie Wang

doi:10.1107/S1600536811023609

. 2011 Jun 25;67(Pt 7):o1809. doi: 10.1107/S1600536811023609

N′-[(E)-1-(5-Bromo-2-hydroxyphenyl)ethylidene]-4-nitrobenzohydrazide

Chang-Zheng Zheng ^a, Liang Wang ^a,^*, Juan Liu ^a, Yu-Jie Wang ^a

PMCID: PMC3152073 PMID: 21837180

Abstract

The title compound, C₁₅H₁₂BrN₃O₄, displays a trans conformation with respect to the C=N double bond. The central atoms around the C=N double bond are not coplanar, in contrast to the aromatic rings, which exhibit a dihedral angle of 1.80 (4)° between their mean planes. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, molecules are connected via intermolecular N—H⋯O hydrogen bonding into chains along the a axis.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Zhang et al. (2011 ▶); Zheng et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₂BrN₃O₄
M _r = 378.19
Orthorhombic,
a = 40.381 (13) Å
b = 5.0598 (16) Å
c = 7.168 (2) Å
V = 1464.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 298 K
0.35 × 0.23 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.441, T _max = 0.689
6753 measured reflections
2520 independent reflections
2074 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.157
S = 0.95
2520 reflections
210 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.75 e Å⁻³
Absolute structure: Flack (1983), 1075 Friedel pairs
Flack parameter: 0.01 (2)

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); 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) I, global. DOI: 10.1107/S1600536811023609/zq2106sup1.cif

e-67-o1809-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023609/zq2106Isup2.hkl

e-67-o1809-Isup2.hkl^{(123.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023609/zq2106Isup3.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
N2—H2A⋯O2ⁱ	0.86	2.23	2.981 (6)	146
O1—H1⋯N1	0.82	1.81	2.531 (7)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation of Shaanxi Province, China (2009JM2012) for financial support.

supplementary crystallographic information

Comment

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Zhang et al., 2011; Zheng et al., 2008; Ali et al., 2004) and their biological activity (Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound, C₁₅H₁₂N₃O₄Br, was synthesized and its crystal structure is reported here.

The title compound, C₁₅H₁₂N₃O₄Br, displays a trans conformation with respect to the C=N double bond (Fig. 1). The central atoms around the C=N double bond are not coplanar since the dihedral angle C7—N1—N2—C9 is 154.7 (5)° in contrast to the aromatic rings which exhibit a dihedral angle of 1.80 (4)° between their mean planes. In the crystal structure, one intramolecular O—H···N hydrogen bond occurs (Table 1). The molecules are connected via intermolecular N—H···O into one-dimensional linear chains along the a axis (Table 1; Fig. 2).

Experimental

Ethyl 4-nitrobenzoate (9.76 g, 0.05 mol) was dissolved in ethanol (40 ml) at room temperature and heated at 363 K, followed by the addition of hydrazine hydrate (2.50 g, 0.05 mol). Subsequently, the mixture was refluxed for 10 h, and then cooled to room temperature. The crystals were precipitated and collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to give compound of 4-nitrobenzhydrazide. 4-Nitrobenzhydrazide (4.53 g, 0.025 mol) was dissolved in ethanol (20 ml) at room temperature and heated at 363 K, followed by the addition of 5-bromo-2-hydroxyphenyl ethyl ketone (5.38 g, 0.025 mol). Subsequently, the mixture was refluxed for 9 h, and then cooled to room temperature. The crystals were precipitated and collected by filtration. The product was recrystallized from ethanol and dried under reduced pressure to the title compound.