2-Chloro-N′-(2-hy­droxy-3,5-diiodo­benzyl­idene)benzohydrazide

Fei Wang; Da-Yong Liu; Hai-Bo Wang; Xian-Sheng Meng; Ting-Guo Kang

doi:10.1107/S1600536811007653

. 2011 Mar 9;67(Pt 4):o810. doi: 10.1107/S1600536811007653

2-Chloro-N′-(2-hydroxy-3,5-diiodobenzylidene)benzohydrazide

Fei Wang ^a, Da-Yong Liu ^b, Hai-Bo Wang ^a, Xian-Sheng Meng ^a,^*, Ting-Guo Kang ^a,^*

PMCID: PMC3099825 PMID: 21754096

Abstract

In the title compound, C₁₄H₉ClI₂N₂O₂, the dihedral angle between the benzene rings is 65.9 (2)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. The molecule has an E conformation about the C=N bond. In the crystal, molecules are linked into C(4) chains propagating in [001] by N—H⋯O hydrogen bonds.

Related literature

For background to hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006 ▶); Khattab (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For reference bond-length values, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₉ClI₂N₂O₂
M _r = 526.48
Monoclinic,
a = 14.311 (3) Å
b = 11.469 (2) Å
c = 9.736 (2) Å
β = 90.032 (2)°
V = 1598.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 4.11 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.525, T _max = 0.542
7381 measured reflections
3383 independent reflections
1747 reflections with I > 2σ(I)
R _int = 0.069

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.112
S = 0.95
3383 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.80 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/S1600536811007653/hb5809sup1.cif

e-67-0o810-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007653/hb5809Isup2.hkl

e-67-0o810-Isup2.hkl^{(165.9KB, 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
O1—H1⋯N1	0.82	1.83	2.556 (8)	146
N2—H2⋯O2ⁱ	0.91 (4)	1.88 (2)	2.768 (8)	168 (8)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported in part by a grant from the Department of Education of Liaoning, China (L2010357).

supplementary crystallographic information

Comment

Hydrazones have been 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; Yang, 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). In this paper, the title new hydrazone compound is reported.

The molecular structure of the title compound is shown in Fig. 1. The bond distances and angles are normal (Allen et al., 1987). The dihedral angle between the two benzene rings is 65.9 (2)°. The molecule of the compound displays an E geometry about the C═N bond. The molecules are linked into chains along the c axis by intermolecular N—H···O hydrogen bonds (Fig. 2 and Table 1).

Experimental

2-Hydroxy-3,5-diiodobenzaldehyde (1.0 mmol, 373.9 mg) was dissolved in methanol (50 ml), then 2-chlorobenzohydrazide (1.0 mmol, 170.6 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 2 h. After the solution had cooled to room temperature colourless powder crystals appeared. The powder crystals were filtered and washed with methanol for three times. Recrystallization from absolute methanol yielded colourless block-shaped single crystals of the title compound.