2-[(E)-2-(4-Methyl­benzene­sulfonamido)ethyl­iminiometh­yl]-4-nitro­phenolate

Marife Tüfekçi; Gökhan Alpaslan; Mustafa Macit; Ahmet Erdönmez

doi:10.1107/S1600536809031481

. 2009 Aug 15;65(Pt 9):o2143. doi: 10.1107/S1600536809031481

2-[(E)-2-(4-Methylbenzenesulfonamido)ethyliminiomethyl]-4-nitrophenolate

Marife Tüfekçi ^a, Gökhan Alpaslan ^a,^*, Mustafa Macit ^b, Ahmet Erdönmez ^a

PMCID: PMC2969864 PMID: 21577552

Abstract

The molecule of the title compound, C₁₆H₁₇N₃O₅S, crystallizes in a zwitterionic form, with a strong intramolecular N—H⋯O hydrogen bond. The dihedral angle between the two benzene rings is 7.06 (9)°. In the crystal, molecules are linked into chains along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Calligaris et al. (1972 ▶); Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶); Karabıyık et al. (2008 ▶). For the crystal structure of 2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate, see: Ali et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₇N₃O₅S
M _r = 363.39
Monoclinic,
a = 17.915 (5) Å
b = 7.342 (5) Å
c = 13.055 (5) Å
β = 103.928 (5)°
V = 1666.7 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.68 × 0.50 × 0.26 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.887, T _max = 0.956
22908 measured reflections
3272 independent reflections
2845 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.094
S = 1.07
3272 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32; 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 datablocks I, global. DOI: 10.1107/S1600536809031481/ci2882sup1.cif

e-65-o2143-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031481/ci2882Isup2.hkl

e-65-o2143-Isup2.hkl^{(157.3KB, 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
N3—H1⋯O3ⁱ	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A⋯O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

Schiff bases have been extensively used as ligands in the field of coordination chemistry (Calligaris et al., 1972). Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al., 1964). These properties result from a proton transfer from the hydroxyl O atom to the imine N atom (Hadjoudis et al., 1987). Schiff bases exhibit two well known tautomeric forms viz. OH and NH tautomers, and they also exist in zwitterionic form (Karabıyık et al., 2008). Our investigations show that the title compund has a zwitterionic form with a strong intramolecular N—H···O hydrogen bond (Fig. 1).

The C7N2 [1.292 (2) Å] and C6—03 [1.272 (2) Å] bond distances in the title compound are comparable to those [1.292 (2) and 1.264 (2) Å] observed in a related zwitterionic structure (Ali et al., 2008). The molecule adopts a folded conformation. The dihedral angle between the two benzene rings is 7.06 (9)°.

The intramolecular N2—H1A···O3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The molecules are linked into chains (Fig. 2) along the c axis by intermolecular N—H···O hydrogen bonds (Table 1).

Experimental

2-Hydroxy-5-nitrobenzaldehyde (10 mg, 5.98× 10^-2 mmol) in ethanol (20 ml) was added to a solution of N-p-tolyl-sulfonylethylenediamine (12.7 mg, 5.98× 10^-2 mmol) in ethanol (20 ml). The reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound were obtained by slow evaporation of an ethylacetate solution (yield 55%; m.p. 446–447 K).