2-Chloro-N′-(5-hydr­oxy-2-nitro­benzyl­idene)benzohydrazide

Cong-Shan Zhou; Tao Yang

doi:10.1107/S1600536810001303

. 2010 Jan 16;66(Pt 2):o365. doi: 10.1107/S1600536810001303

2-Chloro-N′-(5-hydroxy-2-nitrobenzylidene)benzohydrazide

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

PMCID: PMC2979760 PMID: 21579789

Abstract

The molecule of the title Schiff base compound, C₁₄H₁₀ClN₃O₄, exists in a trans configuration with respect to the acyclic C=N bond. The dihedral angle between the two benzene rings is 62.37 (9)°. An intramolecular C—H⋯O hydrogen bond is observed. In the crystal structure, adjacent molecules are linked into a ribbon along [1 Inline graphic 0] by O—H⋯O and 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 related structures, see: Fun et al. (2008 ▶); Shafiq et al. (2009 ▶); Goh et al. (2010 ▶); Zhou et al. (2009 ▶); Zhou & Yang (2009 ▶).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄
M _r = 319.70
Triclinic,
a = 7.2490 (2) Å
b = 9.4719 (3) Å
c = 10.4749 (4) Å
α = 100.623 (2)°
β = 97.433 (2)°
γ = 96.127 (2)°
V = 694.64 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.951, T _max = 0.957
4097 measured reflections
2900 independent reflections
2332 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.103
S = 1.03
2900 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 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/S1600536810001303/ci5018sup1.cif

e-66-0o365-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001303/ci5018Isup2.hkl

e-66-0o365-Isup2.hkl^{(142.3KB, 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
N2—H2⋯O2ⁱ	0.89 (1)	2.09 (1)	2.9591 (18)	165 (2)
O4—H4⋯O1ⁱⁱ	0.82	1.85	2.6708 (17)	176
C7—H7⋯O2	0.93	2.22	2.817 (2)	122

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

Acknowledgments

The authors acknowledge the Hunan Provincial Natural Science Foundation of China (grant No. 09 J J6022) and the Scientific Research Fund of Hunan Provincial Education Department (grant No. 08B031), China, for financial support.

supplementary crystallographic information

Comment

Schiff bases usually 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 derived from the condensing of 5-hydroxy-2-nitrobenzaldehyde with 2-chlorobenzohydrazide in methanol is reported.

Bond lengths in the title molecule (Fig. 1) are comparable to 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 dihedral angle between the two benzene rings is 62.37 (9)°. An intramolecular C—H···O hydrogen bond is observed.

In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds link adjacent molecules into a ribbon along [110] (Table 1 and Fig. 2).

Experimental

5-Hydroxy-2-nitrobenzaldehyde (1.0 mmol, 167.1 mg) and 2-chlorobenzohydrazide (1.0 mmol, 170.0 mg) were dissolved in a methanol solution (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.