N′-(2-Chloro-5-nitro­benzyl­idene)isonicotinohydrazide

Feng Zhi

doi:10.1107/S1600536809006588

. 2009 Feb 28;65(Pt 3):o623. doi: 10.1107/S1600536809006588

N′-(2-Chloro-5-nitrobenzylidene)isonicotinohydrazide

Feng Zhi ^a,^*

PMCID: PMC2968476 PMID: 21582275

Abstract

The title compound, C₁₃H₉ClN₄O₃, was synthesized by the condensation reaction of 2-chloro-5-nitrobenzaldehyde with isonicotinohydrazide in a methanol solution. The molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the benzene and pyridine rings is 12.1 (2)°. In the crystal structure, adjacent molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming dimers.

Related literature

For Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For the biological activity of Schiff base compounds, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For similar structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C₁₃H₉ClN₄O₃
M _r = 304.69
Tetragonal,
a = 18.586 (3) Å
c = 15.183 (3) Å
V = 5244.9 (15) Å³
Z = 16
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.964, T _max = 0.970
16616 measured reflections
2869 independent reflections
1685 reflections with I > 2σ(I)
R _int = 0.083

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.131
S = 1.03
2869 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006588/hg2481sup1.cif

e-65-0o623-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006588/hg2481Isup2.hkl

e-65-0o623-Isup2.hkl^{(141.1KB, 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
N2—H2⋯O3ⁱ	0.892 (10)	2.187 (13)	3.055 (3)	164 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

supplementary crystallographic information

Comment

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). In this paper, the crystal structure of a new Schiff base compound, (I), Fig. 1, derived from the condensation reaction of 2-chloro-5-nitrobenzaldehyde with isonicotinohydrazide is reported.

In (I), the molecular structure of the compound displays a trans configuration with respect to the C=N and C-N bonds. The dihedral angle between the benzene ring and the pyridine ring is 12.1 (2)°. The dihedral angle between the O1/N4/O2 plane and the benzene ring is 8.1 (2)°. All the bond lengths are within normal ranges and comparable to those in other similar compounds (Mohd Lair et al., 2009; Fun et al., 2008; Yang, 2008; Zhi, 2008; Zhi & Yang, 2007).

In the crystal structure, adjacent molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming dimers (Fig. 2).

Experimental

2-Chloro-5-nitrobenzaldehyde (0.01 mol, 1.85 g) and isonicotinohydrazide (0.01 mol, 1.37 g) were dissolved in a methanol solution (50 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent for a week at room temperature.