N′-(2-Hydr­oxy-5-nitro­benzyl­idene)benzene­sulfonohydrazide

Juahir Yusnita; Hapipah M Ali; Subramaniam Puvaneswary; Ward T Robinson; Seik Weng Ng

doi:10.1107/S1600536808022691

. 2008 Jul 23;64(Pt 8):o1583. doi: 10.1107/S1600536808022691

N′-(2-Hydroxy-5-nitrobenzylidene)benzenesulfonohydrazide

Juahir Yusnita ^a, Hapipah M Ali ^a, Subramaniam Puvaneswary ^a, Ward T Robinson ^a, Seik Weng Ng ^a,^*

PMCID: PMC2962200 PMID: 21203281

Abstract

The molecule of the title compound, C₁₃H₁₁N₃O₅S, shows a phenyl group and an almost planar intramolecularly hydrogen-bonded N′-(2-hydroxy-5-phenylebenzylidene)hydrazino group disposed about the S atom. Adjacent molecules are linked by N—H⋯O_nitro hydrogen bonds, producing a linear chain that runs along the b axis of the unit cell.

Related literature

For 2′-[1-(2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide, see: Tai et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₁₁N₃O₅S
M _r = 321.31
Monoclinic,
a = 7.8188 (1) Å
b = 14.5904 (2) Å
c = 11.9083 (1) Å
β = 98.159 (1)°
V = 1344.74 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 (2) K
0.47 × 0.40 × 0.33 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.883, T _max = 0.916
16761 measured reflections
3089 independent reflections
2972 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.088
S = 1.03
3089 reflections
243 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022691/im2077sup1.cif

e-64-o1583-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022691/im2077Isup2.hkl

e-64-o1583-Isup2.hkl^{(151.6KB, 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—H1o⋯N2	0.84 (1)	1.86 (1)	2.628 (1)	153 (2)
N3—H3n⋯O3ⁱ	0.88 (1)	2.13 (1)	2.978 (1)	163 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The molecules of benzenesulfonic acid-(2-hydroxy-5-nitro-benzylidene)-hydrazide adopt a linear chain-like structure in which the individual molecules are linked by N–H···O hydrogen bonds [3.093 (3) Å] (Tai et al., 2008). The title compound exhibits a phenyl group and an almost planar, intramolecularly hydrogen-bonded (2-hydroxy-5-phenyl)ethylidenehydrazidyl group disposed about the sulfur atom. The nitro group is situated para with respect to the OH donor site (Scheme I, Fig. 1). The nitro group also acts as an acceptor towards the amino group of an adjacent molecule to furnish a chain-like structure that runs along the b-axis of the unit cell (Fig. 2).

Experimental

2-Hydroxy-5-nitrobenzaldehyde (0.50 g, 3 mmol) and benzene sulfonylhydrazide (0.52 g, 0.3 mmol) were condensed in refluxing ethanol (100 ml) for two hours. The solvent was removed to give the Schiff base, which was collected in nearly quantative yield. and dried. Crystals were obtained by recrystallization from ethanol.