4-[(E)-(5-Chloro-2-hydroxy­benzyl­idene)amino]benzene­sulfonamide

Zahid H Chohan; Hazoor A Shad; M Nawaz Tahir

doi:10.1107/S1600536808040853

. 2008 Dec 10;65(Pt 1):o57. doi: 10.1107/S1600536808040853

4-[(E)-(5-Chloro-2-hydroxybenzylidene)amino]benzenesulfonamide

Zahid H Chohan ^a, Hazoor A Shad ^a, M Nawaz Tahir ^b,^*

PMCID: PMC2967971 PMID: 21581698

Abstract

In the molecule of title compound, C₁₃H₁₁ClN₂O₃S, the aromatic rings are oriented at a dihedral angle of 12.27 (3)°. An intramolecular O—H⋯N hydrogen bond results in the formation of a planar (mean deviation 0.0083 Å) six-membered ring, which is nearly coplanar with the adjacent ring at a dihedral angle of 2.36 (13)°. In the sulfonamide group, the S atom is 0.457 (3) Å from the plane through the O and N atoms. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules.

Related literature

For general background, see: Chohan (2008 ▶); Chohan & Shad (2008 ▶); Chohan & Supuran (2008 ▶); Nishimori et al. (2005 ▶). For related structures, see: Chohan et al. (2008a ▶,b ▶); Shad et al. (2008 ▶); Gelbrich et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₁₁ClN₂O₃S
M _r = 310.76
Monoclinic,
a = 6.1936 (9) Å
b = 4.6002 (7) Å
c = 23.252 (3) Å
β = 95.699 (7)°
V = 659.22 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 296 (2) K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.904, T _max = 0.935
7850 measured reflections
3172 independent reflections
1842 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.132
S = 1.02
3172 reflections
193 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ▶), 1125 Friedel pairs
Flack parameter: 0.09 (13)

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: 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/S1600536808040853/hk2593sup1.cif

e-65-00o57-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040853/hk2593Isup2.hkl

e-65-00o57-Isup2.hkl^{(53.3KB, 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
O1—H1⋯N1	0.82	1.87	2.603 (5)	148
N2—H21⋯O3ⁱ	0.87 (4)	2.16 (4)	2.986 (6)	160 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Sulfonamides have gained much attention due to their extensive use in medicine. Many novel sulfonamide derived compounds have been synthesized and reported (Chohan, 2008; Chohan & Shad, 2008; Chohan & Supuran, 2008; Nishimori et al., 2005) that are expected to attack the selective targets. This approach is supportive in controlling undesirable effects and producing distinctive pharmacological and clinical responses. In continuation to synthesize Schiff base ligands of 5-chlorosalicylaldehyde with different sulfonamides (Chohan et al., 2008a, 2008b; Shad et al., 2008), we have synthesized the title compound having the sulfanilamide, which is also a member of sulfonamides, and reported herein its crystal structure. The crystal structures of the individual moieties of δ-sulfanilamide have also been reported (Gelbrich et al., 2008) .

In the molecule of title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C8-C13) are, of course, planar, and the dihedral angle between them is A/B = 12.27 (3)°. The intramolecular O-H···N hydrogen bond (Table 1) results in the formation of a planar six-membered ring C (O1/N1/C1/C2/C7/H1), which is oriented with respect to rings A and B at dihedral angles of A/C = 2.36 (13)° and B/C = 13.22 (13)°. So, rings A and C are also nearly coplanar. In the sulfonamide group, the S1 atom is 0.457 (3) Å away from the plane of (O2/O3/N2).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, sulfanilamide (344.4 mg, 2 mmol) in ethanol (20 ml) was mixed with 5-chlorosalicylaldehyde (313.1 mg, 2 mmol) in ethanol (10 ml). The resultant mixture was refluxed for 3 h by monitoring through TLC. During refluxing the solution turned from colorless to bright orange. After completion of reaction, it was cooled to room temperature, filtered and volume reduced to about one-third using rotary evaporator. It was then allowed to stand for 6 d at room temperature. After which, a crystallized product was formed that was filtered, washed with ethanol (2x5 ml), dried and recrystallized in a mixture of methanol/ethanol (1:1) to afford the orange crystals of the title compound (m.p. 469-471 K).