2-(4-Bromo­benzene­sulfonamido)benzoic acid

Muhammad Nadeem Arshad; Islam Ullah Khan; Mehmet Akkurt; Muhammad Shafiq; Ghulam Mustafa

doi:10.1107/S1600536809022545

. 2009 Jun 17;65(Pt 7):o1610–o1611. doi: 10.1107/S1600536809022545

2-(4-Bromobenzenesulfonamido)benzoic acid

Muhammad Nadeem Arshad ^a, Islam Ullah Khan ^a, Mehmet Akkurt ^b,^*, Muhammad Shafiq ^a, Ghulam Mustafa ^a

PMCID: PMC2969408 PMID: 21582883

Abstract

In the title compound, C₁₃H₁₀BrNO₄S, the dihedral angle between the benzene rings is 82.75 (15)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, two molecules form an R ₂ ²(8) centrosymmetric dimer through a pair of O—H⋯O hydrogen bonds. Intra- and intermolecular C—H⋯O hydrogen bonds are also observed.

Related literature

For background to sulfonamide derivatives, see: Allison et al. (2006 ▶); Sheppard et al. (2006 ▶). For related structures, see: Arshad et al. (2009 ▶); Shafiq et al. (2009 ▶); Asiri et al. (2009 ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₃H₁₀BrNO₄S
M _r = 356.19
Monoclinic,
a = 27.8316 (11) Å
b = 8.5684 (4) Å
c = 11.6632 (5) Å
β = 98.196 (2)°
V = 2752.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 3.15 mm⁻¹
T = 296 K
0.23 × 0.19 × 0.11 mm

Data collection

Bruker Kappa-APEXII CCD area-detector diffractometer
Absorption correction: refined from ΔF [Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995 ▶] T _min = 0.497, T _max = 0.707
14822 measured reflections
3416 independent reflections
1764 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.093
S = 0.98
3416 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022545/is2431sup1.cif

e-65-o1610-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022545/is2431Isup2.hkl

e-65-o1610-Isup2.hkl^{(164.2KB, 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
N1—H1⋯O1	0.86	2.13	2.670 (3)	121
O2—H2A⋯O1ⁱ	0.82	1.89	2.703 (3)	173
C6—H6⋯O4ⁱⁱ	0.93	2.56	3.185 (4)	125
C11—H11⋯O3ⁱⁱⁱ	0.93	2.47	3.369 (3)	164
C12—H12⋯O4	0.93	2.31	2.987 (3)	130

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

Acknowledgments

The authors MNA, IUK, MS and GM acknowledge the Higher Education Commission, Pakistan, for support under the indigenous PhD 5000 Fellowship Programme.

supplementary crystallographic information

Comment

Sulfonamides are biologically active organic compounds. The anthranilic sulfonamide derivative has been reported as inhibitors of Methionine aminopeptidase-2 (MetAP2) (Sheppard et al., 2006) and halogenated anthranilic sulfonamide derivatives have been identified as novel, selective Cholecystokinin-2 Receptor Antagonists (Allison et al., 2006). The title compound is halogenated sulfonamide in countinuation of our studies on the synthesis of sulfonamide derivatives (Arshad et al., 2009) and benzothiazines (Shafiq et al., 2009).

In the title compound, (I), (Fig. 1), the values of the geometric parameters are normal, and they are comparable with those in the reported structure of the isomorf compound 2-benzenesulfonamidobenzoic acid (Asiri et al., 2009). The angle between the benzene rings is 82.75 (15)°.

The crystal packing is stabilized by C—H···O and O—H···O hydrogen bonds (Table 1). The intramolecular N—H···O hydrogen bond generates a graph set motif S(6). The O—H···O hydrogen bond forms a cyclic dimer, with a R²₂(8) motif (Bernstein et al., 1995; Etter, 1990), about a inversion centre (Fig. 2). Figure 3 shows the molecular packing for (I) viewed down the b axis, generating a zigzag layer running along the a axis.

Experimental

Anthranilic acid (2 g, 14.6 mmol) was dissolved in distilled water (10 ml) in a round bottom flask (25 ml). The pH of the solution was maintained at 8–9 using 1M, Na₂CO₃. 4- Bromobenzene sulfonylchloride (3.72 g, 14.6 mmol) was suspended to the above solution and stirred at room temperature until all the 4-bromobenzene sulfonyl chloride was consumed. Progress of the reaction was observed by disappearing of suspension to clear solution. On completion of the reaction the pH was adjusted 1–2, using 1 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystallized in methanol to yield dark brown crystals.