4-Benzene­sulfonamido­benzoic acid

Hafiz Muhammad Adeel Sharif; Gui-Ying Dong; Muhammad Nadeem Arshad; Islam Ullah Khan

doi:10.1107/S1600536809047291

. 2009 Nov 14;65(Pt 12):o3086. doi: 10.1107/S1600536809047291

4-Benzenesulfonamidobenzoic acid

Hafiz Muhammad Adeel Sharif ^a, Gui-Ying Dong ^b, Muhammad Nadeem Arshad ^a, Islam Ullah Khan ^a,^*

PMCID: PMC2972151 PMID: 21578816

Abstract

In the molecule of the title sulfonamide compound, C₁₃H₁₁NO₄S, the dihedral angle between the planes of the benzene ring and the carboxyl substituent group is 6.7 (4)°. The two aromatic rings are inclined at 45.36 (15)° to one another. In the crystal, adjacent molecules are linked via classical intermolecular N—H⋯O and O—H⋯O, and non-classical C—H⋯O hydrogen bonds, which stabilize the crystal structure.

Related literature

For the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Innocenti et al. (2004 ▶); Parai et al. (2008 ▶); Rathish et al. (2009 ▶); Selvam et al. (2001 ▶). For related structures of sulfonamide derivatives with 4–aminobenzoic acid, see: Arshad et al. (2009 ▶); Khan et al. (2009 ▶); Nan & Xing (2006 ▶). graphic file with name e-65-o3086-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₁NO₄S
M _r = 277.30
Monoclinic,
a = 5.2050 (3) Å
b = 37.726 (2) Å
c = 7.3781 (4) Å
β = 117.510 (3)°
V = 1284.98 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.26 × 0.21 × 0.19 mm

Data collection

Bruker CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.935, T _max = 0.958
13550 measured reflections
3185 independent reflections
2633 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.199
S = 1.10
3185 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536809047291/rk2179sup1.cif

e-65-o3086-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047291/rk2179Isup2.hkl

e-65-o3086-Isup2.hkl^{(156.3KB, 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
N2—H2⋯O8ⁱ	0.81	2.28	3.054 (4)	162
O5—H5⋯O6ⁱⁱ	0.82	1.82	2.625 (3)	168
C18—H18⋯O5ⁱⁱⁱ	0.93	2.58	3.413 (4)	150
C19—H19⋯O6^iv	0.93	2.48	3.348 (4)	155

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

Acknowledgments

The authors thank Government College University and the Scientific Research Fund of Hebei Provincial Education Department (project 2006114) for financial support.

supplementary crystallographic information

Comment

Benzene sulfonamide derivative have shown antimalarial (Parai et al., 2008), carbonic anhydrase inhibitors (Innocenti et al., 2004), antiHIV (Selvam et al., 2001) and antiinflamatory (Rathish et al., 2009) activities. In continuation of synthesis and structural studies of different benzene sulfonamide derivative (Khan et al., 2009; Arshad et al., 2009), we report here the molecular and crystal structures of title compound. The molecular structure of the title compound, I, is illustrated in Fig. 1. In I, phenyl and p–aminobenzoic acid moieties are connected through the SO₂ group. The structure of I is comparable with 4–(tosylamino)benzoic acid, (Nan & Xing, 2006). The dihedral angle between the planes of the benzene ring and the carboxyl substituent group is 6.7 (4)°. The two aromatic rings (C20–C25 and C14–C19) are inclined at 45.36 (15)° to one another. The torsion angle C14—N2—S1—C20 in the central part of the molecule is 70 (1)°.

In the crystal, adjacent molecules are linked via intermolecular classical N—H···O and O—H···O and non–classical C—H···O hydrogen bonds (Tab. 1, Fig. 2), which stabilize the crystal structure.

Experimental

The 4–amino benzoic acid (1 g, 7.3 mmol) was dissolved in distilled water (10 ml). The pH of the solution was adjusted at 8–9 using 1M Na₂CO₃. Benzene sulfonylchloride (1.29 g, 7.3 mmol) was added to the above solution and stirred at room temperature until all the suspended benzene sulfonyl chloride was consumed. On completion of the reaction the pH was adjusted 1–2, using 1N HCl acid. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in methanol to yield colourless crystals.