2-Benzenesulfonamidobenzoic acid

Abdullah Mohamed Asiri; Mehmet Akkurt; Salman A Khan; Muhammad Nadeem Arshad; Islam Ullah Khan; Hafiz Muhammad Adeel Sharif

doi:10.1107/S1600536809016900

. 2009 May 14;65(Pt 6):o1246–o1247. doi: 10.1107/S1600536809016900

2-Benzenesulfonamidobenzoic acid

Abdullah Mohamed Asiri ^a, Mehmet Akkurt ^b,^*, Salman A Khan ^a, Muhammad Nadeem Arshad ^c, Islam Ullah Khan ^c, Hafiz Muhammad Adeel Sharif ^c

PMCID: PMC2969753 PMID: 21583112

Abstract

In the title compound, C₁₃H₁₁NO₄S, the dihedral angle between the planes of the benzene ring and the carboxyl group is 13.7 (1)°. The molecular structure contains intramolecular N—H⋯O and C—H⋯O hydrogen-bonding interactions, while the crystal packing is stabilized by C—H⋯O and O—H⋯O hydrogen bonds and C—H⋯π interactions. The O—H⋯O hydrogen bonds form a cyclic dimer, with graph-set motif R ² ₂(8), about a centre of symmetry.

Related literature

For background to sulfonamide derivatives, see: Sheppard et al. (2006 ▶). For similar structures, see: Arshad et al. (2009 ▶); Sethu Sankar et al. (2002 ▶); Wijeyesakere et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₃H₁₁NO₄S
M _r = 277.30
Monoclinic,
a = 27.271 (3) Å
b = 8.7223 (9) Å
c = 11.0077 (10) Å
β = 106.149 (3)°
V = 2515.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.36 × 0.26 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: none
12048 measured reflections
2989 independent reflections
1824 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.105
S = 1.00
2989 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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 ▶); 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/S1600536809016900/fj2215sup1.cif

e-65-o1246-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016900/fj2215Isup2.hkl

e-65-o1246-Isup2.hkl^{(143.8KB, 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
N1—H1⋯O3	0.86	1.99	2.644 (2)	132
O4—H4⋯O3ⁱ	0.82	1.89	2.712 (2)	178
C5—H5⋯O1ⁱⁱ	0.93	2.47	3.372 (3)	162
C6—H6⋯O2	0.93	2.50	2.878 (3)	104
C9—H9⋯O4	0.93	2.35	2.700 (3)	102
C11—H11⋯O1ⁱⁱⁱ	0.93	2.55	3.429 (3)	159
C12—H12⋯O2	0.93	2.37	3.032 (3)	128
C4—H4A⋯Cg2^iv	0.93	2.84	3.765 (3)	174

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C7–C12 ring.

Acknowledgments

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing laboratories and facilities.

supplementary crystallographic information

Comment

The title compound is sulfonamide derivative and prepared by the simple condensation of anthranilic acid and benzene sulfonylchloride. The anthranilic sulfonamide derivative has been investigated as an inhibitors of Methionine aminopeptidase-2 (MetAP2), a novel target for cancer therapy (Sheppard et al. 2006). The title compound is reported as in countinuation of our studies on the synthesis of sulfonamide derivatives (Arshad et al., 2009).

In the compound, (I), (Fig. 1), the C—O distances are as expected. The S—C_Ph distance of 1.763 (2)Å compare well with the literature value of 1.763 (9)Å (Allen et al., 1987). The S1—N1 distance of 1.6213 (18) Å is shorter than the literature value of 1.6458 (11) Å (Wijeyesakere et al., 2008). The mean S=O distance of 1.4248 (16) Å is comparable with the reported value of 1.436 (2)Å (Sethu Sankar et al., 2002). The interplanar angle between the phenyl rings in (I) is 89.01 (12)°. The slight increases in the N1—C7—C8 [119.10 (16)°] and C7—C8—C13 [121.97 (17)°] angles, from the ideal value of 120°, can be attributed to the steric interaction of the N1 and C13 substituents.

The molecular structures are stabilized by intramolecular N—H···O and C—H···O hydrogen bonding interactions. The crystal packing is stabilized by C—H···O and O—H···O hydrogen bonds, and C—H···π interactions (Table 1). The O—H···O hydrogen bond forms a cyclic dimer, with graph-set motif R²₂(8), about a centre of symmetry (Fig. 2). Fig. 3 shows the molecular packing for (I) viewed down the b axis.

Experimental

Anthranilic acid (1 g, 7.3 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. Benzene sulfonylchloride (1.29 g, 7.3 mmol) was then added to the above solution and stirred atroom temperature until all the benzene sulfonyl chloride was consumed. 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 recrystalized in methanol to yield brownish black crystals.