(E)-4-Bromo-N′-(2-nitro­benzyl­idene)benzohydrazide

Ming-Jun Zhang; Li-Zi Yin; Da-Cheng Wang; Xu-Ming Deng; Jing-Bo Liu

doi:10.1107/S1600536809002165

. 2009 Feb 11;65(Pt 3):o508. doi: 10.1107/S1600536809002165

(E)-4-Bromo-N′-(2-nitrobenzylidene)benzohydrazide

Ming-Jun Zhang ^a, Li-Zi Yin ^a, Da-Cheng Wang ^a, Xu-Ming Deng ^a, Jing-Bo Liu ^b,^*

PMCID: PMC2968684 PMID: 21582171

Abstract

The title compound, C₁₄H₁₀BrN₃O₃, was obtained by a condensation reaction between 2-nitrobenzaldehyde and 4-bromobenzohydrazide. The dihedral angle between the two benzene rings is 4.1 (2)°. The molecule displays an E configuration about the C=N bond. In the crystal, molecules are linked into a chain along [100] by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 ▶); Khattab et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₀BrN₃O₃
M _r = 348.16
Triclinic,
a = 4.8718 (17) Å
b = 6.842 (2) Å
c = 10.709 (4) Å
α = 98.014 (5)°
β = 93.258 (6)°
γ = 97.413 (5)°
V = 349.5 (2) Å³
Z = 1
Mo Kα radiation
μ = 2.95 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.590, T _max = 0.634
2347 measured reflections
1998 independent reflections
1584 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.064
S = 0.95
1998 reflections
193 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 235 Friedel pairs
Flack parameter: 0.021 (8)

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/S1600536809002165/ci2760sup1.cif

e-65-0o508-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002165/ci2760Isup2.hkl

e-65-0o508-Isup2.hkl^{(98.3KB, 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
N1—H1⋯O1ⁱ	0.900 (11)	1.909 (19)	2.791 (3)	166 (6)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This project was supported by Jilin University.

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab et al., 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). As part of the ongoing study, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings is 4.1 (2)°. The molecule of the compound displays an E configuration about the C═N bond. The bond values are typical (Allen et al., 1987). The molecules are linked into a chain along the [100] by intermolecular N—H···O hydrogen bonds.

Experimental

2-Nitrobenzaldehyde (1.0 mmol, 151.1 mg) was dissolved in methanol (50 ml) and then 4-bromobenzohydrazide (1.0 mmol, 215.0 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 1 h. After the solution had cooled to room temperature colourless crystals appeared. The crystals were filtered and washed with methanol for three times. Recrystallization from an absolute methanol yielded block-shaped single crystals of the title compound.