N′-[(E)-2-Hy­droxy-5-iodo­benzyl­idene]-4-methyl­benzene­sulfono­hydrazide

Massomeh Ghorbanloo; Behrouz Notash

doi:10.1107/S1600536812035738

. 2012 Aug 23;68(Pt 9):o2760. doi: 10.1107/S1600536812035738

N′-[(E)-2-Hydroxy-5-iodobenzylidene]-4-methylbenzenesulfonohydrazide

Massomeh Ghorbanloo ^a,^*, Behrouz Notash ^b

PMCID: PMC3435795 PMID: 22969641

Abstract

In the title molecule, C₁₄H₁₃IN₂O₃S, the dihedral angle between the planes of the benzene and toluene rings is 84.3 (3)°. The molecule displays a trans conformation with respect to the C=N bond. There is an intramolecular O—H⋯N hydrogen bond with the azomethine N atom as acceptor. In the crystal, N—H⋯O hydrogen bonds connect the molecules into chains running along the b axis.

Related literature

For background to sulfonamides, see: Kayser et al. (2004 ▶). For related structures and their applications, see: Shahverdizadeh et al. (2011 ▶); Ali et al. (2007 ▶); Tierney et al. (2006 ▶); Silva et al. (2006 ▶). For polymorphism in sulfonohydrazides, see: Kia et al. (2008 ▶); Tai et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₁₃IN₂O₃S
M _r = 416.23
Monoclinic,
a = 6.2467 (12) Å
b = 10.394 (2) Å
c = 11.971 (2) Å
β = 92.42 (3)°
V = 776.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.21 mm⁻¹
T = 298 K
0.50 × 0.40 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ▶) T _min = 0.405, T _max = 0.667
6035 measured reflections
3841 independent reflections
2791 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.114
S = 0.92
3841 reflections
197 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.99 e Å⁻³
Absolute structure: Flack (1983 ▶), 1641 Friedel pairs
Flack parameter: −0.06 (3)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035738/bt5993sup1.cif

e-68-o2760-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035738/bt5993Isup2.hkl

e-68-o2760-Isup2.hkl^{(188.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035738/bt5993Isup3.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
O1—H1⋯N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A⋯O1ⁱ	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the University of Zanjan for financial support.

supplementary crystallographic information

Comment

Sulfonyl hydrazones are found to exhibit large medicinal applications. Similar to sulfonamides, sulfonyl hydrazones also have various biological activities (Kayser et al., 2004). For example, imidosulfonylhydrazones have antibacterial and antineociceptive properties (Silva et al., 2006). Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory activities. On the other hand, polymorphism is a phenomenon wherein the same substances exhibits different crystal packing arrangements and is of practical importance e.g., pharmaceutical processes where different physical properties of polymorphic forms can substantially alter the viability and quality of product. Plymorphism is another interesting subject in sulfonyl hydrazones. sulfonyl hydrazones derived from the condensation of O-hydroxy aldehydes and sulfonyl acid hydrazides can form different polymorphs. Kia et al. (2008) and Tai et al. (2009) have reported two polymorph of these type of compounds.

We report here the crystal structure of (E)-N'-(2-hydroxy-5-iodobenzylidene)-4-methylbenzenesulfonohydrazide. The asymmetric unit of the title compound contains one molecule, which is shown in Fig. 1. Bond distances and bond angles are in the normal range of similar compounds (Shahverdizadeh et al., 2011; Ali et al., 2007; Tierney et al., 2006). The molecule displays trans configuration with respect to the C=N bond. The packing diagram of the title compound is shown in Fig. 2. In the title compound, the dihedral angle between the planes of benzene and toluene rings is 84.3 (3)°. There is an intramolecular O—H···N hydrogen bond in which the nitrogen of the azomethine group (–C=N–) acting as hydrogen bond acceptor. Intermolecular N—H···O hydrogen bond stabilize the crystal structure (Fig. 2 & Table 1).

Experimental

For preparing the title compound, a methanol (10 ml) solution of 2-hydroxy-5-iodobenzaldehyde (2 mmol) was dropwise added to a methanol solution (10 ml) of 4-methyl-benzenesulfonic acid hydrazide (2 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature. A white precipitate of the title compound was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 90%. Selected IR (cm^-1): 3464 (w, broad), 3140 (m), 1619 (s), 1481 (vs), 1359 (s), 1329 (vs), 1264 (vs), 1177 (s), 1087 (s), 956 (vs), 869 (vs) 772 (s), 666 (s), 545 (s), 458 (m).