N-(2,3-Dihydro-1,3-thia­zol-2-yl­idene)-4-[(2-hydroxy­benzyl­idene)amino]benzene­sulfonamide

Xin-Li Zhang

doi:10.1107/S1600536809033704

. 2009 Aug 29;65(Pt 9):o2274. doi: 10.1107/S1600536809033704

N-(2,3-Dihydro-1,3-thiazol-2-ylidene)-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide

Xin-Li Zhang ^a,^*

PMCID: PMC2969909 PMID: 21577669

Abstract

The title compound, C₁₆H₁₃N₃O₃S₂, was prepared by reaction of salicylaldehyde and sulfathiazole in methanol. The dihedral angle between the central benzene ring and the thiazole ring is 85.2 (2)° and that between the two benzene rings is 17.9 (2)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are held together by intermolecular N—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of Schiff bases, see: Billson et al. (2000 ▶); Carlton et al. (1995 ▶). For a related structure, see: Li et al. (2006 ▶).

Experimental

Crystal data

C₁₆H₁₃N₃O₃S₂
M _r = 359.41
Monoclinic,
a = 16.1693 (18) Å
b = 9.1211 (11) Å
c = 11.0292 (13) Å
β = 101.896 (1)°
V = 1591.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.40 × 0.37 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.871, T _max = 0.932
7737 measured reflections
2806 independent reflections
1927 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.108
S = 1.04
2806 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 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 I, global. DOI: 10.1107/S1600536809033704/ci2883sup1.cif

e-65-o2274-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033704/ci2883Isup2.hkl

e-65-o2274-Isup2.hkl^{(137.8KB, 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—H3A⋯N1	0.97 (4)	1.73 (4)	2.636 (4)	154 (4)
N2—H2A⋯N3ⁱ	0.89 (3)	1.97 (3)	2.856 (3)	179 (3)
C6—H6⋯O1ⁱⁱ	0.93	2.58	3.334 (4)	139
C16—H16⋯O2ⁱⁱⁱ	0.93	2.52	3.351 (4)	148

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The work was supported financially by research grant No. 09JS068 from the Phytochemistry Key Laboratory of Shaanxi Province.

supplementary crystallographic information

Comment

The synthesis and characterization of Schiff base compounds have received a great deal of attention due to their biological activities, such as anti-bacterial, anti-cancer and anti-virus (Billson et al., 2000; Carlton et al., 1995). In this paper, we report the crystal structure of the title compound, a new Schiff-base ligand, (I).

Bbond lengths and angles in (I) are normal and they agree with those observed in a salicylaldehyde Schiff base (Li et al., 2006). The C7db// N1 bond length of 1.269 (4) Å conforms to the value for a double bond. The dihedral angle between C1-C6 benzene ring and thiazole ring is 85.2 (2)°. The dihedral angle between the two benzene rings is 17.9 (2)°. An intramolecular O3—H3A···N1 hydrogen bond generates an S(6) ring motif (Fig. 1).

The molecules are held together by N—H···N and C—H···O intermolecular hydrogen bonds (Table 1), forming a two-dimensional network parallel to the bc plane (Fig. 2).

Experimental

All chemicals were of reagent grade and commercially available from the Beijing Chemical Reagents Company of China, and were used without further purification. A methanol solution (10 ml) of salicylaldehyde (0.1 mmol, 12.2 mg) and sulfathiazloe (0.1 mmol, 25.5 mg) was stirred at room temperature for 30 min and then filtered. The filtrate was left to stand in air for 7 d, and the title compound was formed in slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 64%).