2-Chloro-N′-(4-nitro­benzyl­idene)benzo­hydrazide

Cong-Shan Zhou; Tao Yang

doi:10.1107/S1600536809055330

. 2010 Jan 9;66(Pt 2):o290. doi: 10.1107/S1600536809055330

2-Chloro-N′-(4-nitrobenzylidene)benzohydrazide

Cong-Shan Zhou ^a, Tao Yang ^a,^*

PMCID: PMC2979746 PMID: 21579725

Abstract

The title Schiff base compound, C₁₄H₁₀ClN₃O₃, exists in a trans configuration with respect to the C=N bond. The dihedral angle between the two benzene rings is 15.9 (2)°. In the crystal, the molecules are linked into chains along [101] by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff bases, see: Mohamed et al. (2009 ▶); Ritter et al. (2009 ▶); Bagihalli et al. (2008 ▶). For the crystal structures of Schiff base compounds, see: Fun et al. (2008 ▶); Shafiq et al. (2009 ▶); Goh et al. (2010 ▶). For other related structures, see: Zhou et al. (2009 ▶); Zhou & Yang (2009 ▶).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₃
M _r = 303.70
Monoclinic,
a = 7.2752 (3) Å
b = 26.4081 (9) Å
c = 7.7284 (3) Å
β = 113.000 (2)°
V = 1366.78 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.936, T _max = 0.944
7876 measured reflections
2763 independent reflections
1934 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.113
S = 1.03
2763 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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/S1600536809055330/ci5003sup1.cif

e-66-0o290-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055330/ci5003Isup2.hkl

e-66-0o290-Isup2.hkl^{(135.7KB, 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—H2A⋯O3ⁱ	0.90 (1)	1.97 (1)	2.855 (2)	169 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Hunan Provincial Natural Science Foundation of China (grant No. 09 J J6022) and the Scientific Research Fund of Hunan Provincial Education Department, China (grant No. 08B031).

supplementary crystallographic information

Comment

Schiff bases are a kind of interesting compounds, which possess excellent biological properties, such as antibacterial, antimicrobial, and antitumor (Mohamed et al., 2009; Ritter et al., 2009; Bagihalli et al., 2008). Recently, a large number of Schiff bases derived from the reaction of aldehydes with benzohydrazides have been reported (Fun et al., 2008; Shafiq et al., 2009; Goh et al., 2010). In this paper, the crystal structure of the title new Schiff base compound is reported.

In the title compound (Fig. 1), bond lengths are comparable with those observed in related structures (Zhou et al., 2009; Zhou & Yang, 2009). The molecule exists in a trans configuration with respect to the acyclic C═N bond. The molecule is distorted from planarity, with a dihedral angle between the two benzene rings of 15.9 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link adjacent molecules into chains along the [101] (Table 1 and Fig. 2).

Experimental

4-Nitrobenzaldehyde (1.0 mmol, 151.0 mg) and 2-chlorobenzohydrazide (1.0 mmol, 170.0 mg) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding colourless block-shaped crystals.