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

Zhong-Feng Shi; Jia-Ming Li

doi:10.1107/S1600536812020855

. 2012 May 16;68(Pt 6):o1726. doi: 10.1107/S1600536812020855

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

Zhong-Feng Shi ^a,^b, Jia-Ming Li ^a,^*

PMCID: PMC3379316 PMID: 22719514

Abstract

The title Schiff base compound, C₁₄H₁₂N₄O₃, displays an E conformation with respect to the C=N double bond [1.268 (3) Å]. The dihedral angle between the benzene rings is 3.2 (5)°, consistent with an essentially planar molecule. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds, as well as C—H⋯O interactions, link the molecules into layers that stack along the c axis.

Related literature

For the coordination chemistry of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 ▶); Khattab et al. (2005 ▶); Karthikeyan et al. (2006 ▶). For a closely related 4-aminobenzohydrazide and its Schiff base structures and further background references, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶).

Experimental

Crystal data

C₁₄H₁₂N₄O₃
M _r = 284.28
Monoclinic,
a = 6.4594 (13) Å
b = 4.5998 (13) Å
c = 20.598 (5) Å
β = 95.08 (4)°
V = 609.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.25 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.989
4632 measured reflections
2710 independent reflections
1516 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.111
S = 1.05
2710 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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) global, I. DOI: 10.1107/S1600536812020855/tk5092sup1.cif

e-68-o1726-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020855/tk5092Isup2.hkl

e-68-o1726-Isup2.hkl^{(78.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812020855/tk5092Isup3.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
N1—H1A⋯N1ⁱ	0.89	2.44	3.287 (4)	162
N1—H1B⋯O1ⁱⁱ	0.89	2.35	3.164 (3)	153
N2—H2⋯O1ⁱⁱⁱ	0.86	2.13	2.843 (3)	142
C2—H2A⋯O1ⁱⁱ	0.93	2.56	3.329 (3)	140

Open in a new tab

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

Acknowledgments

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 2011GXNSFB018023) and the Natural Science Foundation of the Education Bureau of Guangxi Province (grant No. 201106LX535). This work was also supported by the Program for Excellent Talents in Guangxi Higher Education Institutions and the Dean’s project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (grant No. K011).

supplementary crystallographic information

Comment

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Khattab, 2005; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide and closely related to the title compound have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). In order to explore new anti-bacterial compounds, a new hydrazone derivative was prepared and characterized crystallographically.

As shown in Fig. 1, the asymmetric unit of the title compound, (I), contains one independent molecule displaying an E configuration with respect to its C═N double bond. The dihedral angle between the two benzene rings is 3.2 (5)°. The bond lengths and angles are as expected for a compound of this type and agree with the other ligands belonging to the hydrazone series. The C8═N3 and C7═O1 bond lengths of 1.268 (3) and 1.226 (3) Å, respectively, are the expected values for such double bonds. In the crystal packing, it is noted that amino-H (H1A, H1B) and amide-H2A atoms are involved in forming intermolecular N—H···O and N—H···N hydrogen bonds (Fig. 2 and Table 1), linking the molecules into a two-dimensional layer structure that stacks along the c axis. Weak C—H···O interactions are also noted within the layer.

Experimental

To a methanol solution (20 ml) of 2-nitrobenzaldehyde (1 mmol, 0.151 g) and 4-aminobenzohydrazide (1 mmol, 0.151 g), a few drops of acetic acid were added. The mixture was refluxed for 2 h and then cooled to room temperature to give a yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 6 days at room temperature.