N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Xi-Shi Tai; Jun Xu; Yi-Min Feng; Zu-Pei Liang

doi:10.1107/S1600536808010970

. 2008 Apr 26;64(Pt 5):o904. doi: 10.1107/S1600536808010970

N′-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide

Xi-Shi Tai ^a,^*, Jun Xu ^b, Yi-Min Feng ^a, Zu-Pei Liang ^a

PMCID: PMC2961334 PMID: 21202386

Abstract

In the title compound, C₁₄H₁₄N₂O₃S, the conformation is stabilized by an intramoleclar O—H⋯N hydrogen bond and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds lead to [100] chains of molecules.

Related literature

For related literature, see: Tai et al. (2003 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O₃S
M _r = 290.33
Monoclinic,
a = 5.2435 (9) Å
b = 13.2515 (18) Å
c = 20.375 (2) Å
β = 90.531 (2)°
V = 1415.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.50 × 0.40 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.891, T _max = 0.918
7165 measured reflections
2484 independent reflections
1755 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.131
S = 1.04
2484 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010970/hb2723sup1.cif

e-64-0o904-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010970/hb2723Isup2.hkl

e-64-0o904-Isup2.hkl^{(122.1KB, 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
O3—H3⋯N2	0.82	1.85	2.561 (3)	145
N1—H1⋯O2ⁱ	0.90	2.20	3.093 (3)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60), and the Science and Technology Foundation of Weifang University for research grants.

supplementary crystallographic information

Comment

As part of our ongoing studies of the coordination chemistry of aroylhydrazones as potential ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecular conformation is stabilised by an intramoleclar O-H···N hydrogen bond (Table 1) and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal, an intermolecular N-H···O hydrogen bond lead to [100] chains of molecules.

Experimental

3 mmol of 2'-hydroxyacetophenone (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.