4-{2-[(5-Chloro-2-hydroxy­benzyl­idene)amino]eth­yl}benzene­sulfonamide

Zahid H Chohan; Hazoor A Shad; M Nawaz Tahir; Islam Ullah Khan

doi:10.1107/S1600536808005084

. 2008 Mar 20;64(Pt 4):o725. doi: 10.1107/S1600536808005084

4-{2-[(5-Chloro-2-hydroxybenzylidene)amino]ethyl}benzenesulfonamide

Zahid H Chohan ^a, Hazoor A Shad ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^c

PMCID: PMC2960939 PMID: 21202115

Abstract

In the molecule of the title compound, C₁₅H₁₅ClN₂O₃S, the S atom adopts a distorted tetrahedral coordination geometry with two O atoms, one N atom of the amide group and one C atom of the aromatic ring. An intramolecular O—H⋯N hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the adjacent aromatic ring at a dihedral angle of 3.38 (11)°. Thus, the two rings are nearly coplanar. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Supuran & Scozzafava (2001 ▶); Chohan & Shad (2007 ▶). For related literature, see: Chohan et al. (2008 ▶); Shad et al. (2008 ▶); Tahir et al. (2008 ▶); Li (2006 ▶).

Experimental

Crystal data

C₁₅H₁₅ClN₂O₃S
M _r = 338.80
Monoclinic,
a = 21.069 (2) Å
b = 4.8125 (6) Å
c = 30.838 (3) Å
β = 99.942 (9)°
V = 3079.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 (2) K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.920, T _max = 0.940
16002 measured reflections
4067 independent reflections
1851 reflections with I > 3σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.185
S = 1.02
4067 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005084/hk2428sup1.cif

e-64-0o725-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005084/hk2428Isup2.hkl

e-64-0o725-Isup2.hkl^{(195.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

S1—O2	1.430 (2)
S1—O3	1.423 (3)
S1—N2	1.616 (3)
S1—C13	1.752 (3)

Open in a new tab

O2—S1—O3	118.15 (14)
O2—S1—N2	105.67 (16)
O2—S1—C13	109.21 (15)
O3—S1—N2	108.20 (17)
O3—S1—C13	108.29 (15)
N2—S1—C13	106.76 (15)

Open in a new tab

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.554 (4)	147.00
N2—H2⋯O2ⁱ	0.77 (4)	2.30 (4)	3.016 (4)	156 (4)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer.

supplementary crystallographic information

Comment

The significance of sulfonamide was realised when sulfanilamide was first time reported as antibacterial drug. Later on, many sulfanilamide derivatives were synthesized, characterized and tested for antibacterial, anti-tumour, anti-carbonic anhydrase (Supuran & Scozzafava 2001), diuretic, hypoglycemic, anti-thyroid or protease inhibitory activity. Thus, sulfanilamide is performing a leading role for the development and expansion of all other types of medicinally important sulfonamides (Chohan & Shad, 2007).

The title compound, (I), is a reaction product of 5-chlorosalicylaldehyde and 4-(2-aminoethyl)benzenesulfonamide. The 4-(2-aminoethyl)benzenesulfonamide moiety is present in 4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolidine-1-carboxamido)- ethyl]benzenesulfonamide (Li, 2006) and 5-chlorosalicylaldehyde exists in 4-[(5-chloro-2-hydroxybenzylidene)amino]-N-(3,4-dimethylisoxazol-5-yl)benzene- sulfonamide (Chohan et al., 2008). In continuation of synthesizing Schiff base ligands of substituted halogen salicylaldehydes and various sulfonamides (Chohan et al., 2008; Shad et al., 2008; Tahir et al., 2008), we report herein the crystal structure of the title compound, (I).

In the molecule of (I), S1 atom has a distorted tetrahedral coordination completed by the two O atoms, one N atom of amide group and one C atom of the adjacent aromatic ring B (C10—C15) (Table 1, Fig. 1). The two aromatic rings A (C1—C6) and B are connected by C=N—C—C group in a zigzag way, in which they are oriented at a dihedral angle of A/B = 23.95 (18)°. The intramolecular O—H···N hydrogen bond (Table 2) results in the formation of a planar six-membered ring C (O1/H1/N1/C7/C1/C2), which is oriented with respect to the aromatic rings at dihedral angles of A/C = 3.38 (11)° and B/C = 22.33 (13)°. So, rings A and C are also nearly coplanar.

In (I), C7—N1 [1.278 (5) Å] bond has double bond character. The C2=O1 [1.343 (5) Å] bond is a little longer than the corresponding value [1.328 (4) Å], as reported by Chohan et al. (2008). All other bonds in 5-chlorosalicylaldehyde moiety remain nearly same. The bond angles around S1 atom of sulfonamide group are a little smaller, having the range of 106.76 (15)° - 118.15 (14)°, compared to the values, in the range of 105.91 (13)°-119.68 (12)°, as reported by Li (2006).

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, an ethanol solution (15 ml) of 4-(2-aminoethyl)benzenesulfonamide (400.5 mg, 2 mmol) was added to an ethanol solution (10 ml) of 5-chlorosalicylaldehyde (313.1 mg, 2 mmol). The reaction mixture was refluxed for 3 h. The colour of the solution gradually changed from colorless to greenish yellow. The solution was cooled to room temperature, filtered and the volume was reduced to about one-third on the rotary evaporator. It was allowed to stand for 10 d, bright yellow crystals of the title compound were obtained (m.p. 441 K).