2-(4-Acetamido­benzene­sulfonamido)­benzoic acid

Shahzad Sharif; Islam Ullah Khan; Tariq Mahmood; Sung Kwon Kang

doi:10.1107/S1600536811020307

. 2011 Jun 4;67(Pt 7):o1570. doi: 10.1107/S1600536811020307

2-(4-Acetamidobenzenesulfonamido)benzoic acid

Shahzad Sharif ^a, Islam Ullah Khan ^a, Tariq Mahmood ^b, Sung Kwon Kang ^c,^*

PMCID: PMC3151891 PMID: 21836982

Abstract

In the title compound, C₁₅H₁₄N₂O₅S, two similar molecules comprise the asymmetric unit, which are linked by strong intermolecular C—H⋯π interactions. Both molecules are bent, with dihedral angles of 71.94 (16) and 74.62 (15)° between the benzene rings. An intramolecular N—H⋯O hydrogen bond occurs in each molecule. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For our previous studies on sulfonamide derivatives, see: Khan et al. (2011 ▶); Sharif et al. (2010 ▶). For background to the pharmacological use of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₅S
M _r = 334.34
Monoclinic,
a = 9.3721 (19) Å
b = 13.036 (3) Å
c = 13.132 (3) Å
β = 109.47 (3)°
V = 1512.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.92, T _max = 0.931
2926 measured reflections
2926 independent reflections
1470 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.092
S = 0.82
2926 reflections
415 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 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 publication routines (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020307/tk2747sup1.cif

e-67-o1570-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020307/tk2747Isup2.hkl

e-67-o1570-Isup2.hkl^{(140.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020307/tk2747Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C37–C42 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O22ⁱ	0.82	1.84	2.649 (6)	168
N10—H10⋯O8	0.86	2.13	2.624 (7)	116
N20—H20⋯O13ⁱⁱ	0.86	2.24	3.073 (6)	164
O31—H31⋯O45ⁱⁱⁱ	0.82	1.81	2.623 (6)	174
N33—H33⋯O32	0.86	2.17	2.641 (7)	114
N43—H43⋯O36ⁱ	0.86	2.11	2.958 (7)	168
C23—H23B⋯Cg1	0.96	2.74	3.6110 (15)	151
C46—H46C⋯Cg2	0.96	2.71	3.5821 (13)	151

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

supplementary crystallographic information

Comment

In continuation of our structural studies of sulfonamides (Khan et al., 2011; Sharif et al., 2010) of the interest owing to their potential as biologically active molecules (Korolkovas, 1988; Mandell & Sande, 1992), herein, we report the crystal structure of the title compound, (I).

Two independent but similar molecules comprise the asymmetric unit, Fig. 1. The phenyl carboxyl moieties are almost planar with r.m.s. deviations of 0.012 and 0.023 Å from the corresponding least-squares plane defined by the eight constituent atoms. The dihedral angles between the benzene rings are 71.94 (16) and 74.62 (15) °. The two independent molecules are linked by intermolecular C—H···π interactions (centroid—H distance = 2.711 (3) and 2.740 (3) Å) (Fig. 1). In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds link the molecules into a three-dimensional network (Table 1, Fig. 2).

Experimental

To anthranilic acid (137 mg, 1 mmol) in distilled water (10 ml) was added 4-acetamidobenzenesulfonyl chloride (234 mg, 1 mmol). The pH = 8 was maintained by 3% Na₂CO₃ with stirring at room temperature. The reaction was monitored by TLC. After completion of reaction, the solution was adjusted to pH =3 with 3 N HCl solution. The white precipitate that formed was filtered and washed with water. Crystallization was from methanol.