3-[4-(Acetamido)­benzene­sulfonamido]­benzoic acid

Sidra Muzaffar Mirza; Ghulam Mustafa; Islam Ullah Khan; Muhammad Zia-ur-Rehman; Muhammad Shafiq

doi:10.1107/S1600536810048397

. 2010 Dec 4;67(Pt 1):o25–o26. doi: 10.1107/S1600536810048397

3-[4-(Acetamido)benzenesulfonamido]benzoic acid

Sidra Muzaffar Mirza ^a, Ghulam Mustafa ^a, Islam Ullah Khan ^a, Muhammad Zia-ur-Rehman ^b,^*, Muhammad Shafiq ^a

PMCID: PMC3050169 PMID: 21522739

Abstract

In the title compound, C₁₅H₁₄N₂O₅S, the dihedral angle between the aromatic rings is 63.20 (11) Å. The crystal structure displays classical intermolecular O—H⋯O hydrogen bonding typical for carboxylic acids, forming centrosymmetric dimers. These dimers are further connected by N—H⋯O and C—H⋯O hydrogen bonds to form an extended network.

Related literature

For the synthesis of related compounds, see: Khan et al. (2009 ▶); Arshad et al. (2008 ▶). For the biological activity of sulfonamides, see: Esteve & Bidal (2002 ▶); Hanson et al. (1999 ▶); Lee & Lee (2002 ▶); Moree et al. (1991 ▶); Ozbek et al. (2007 ▶); Parari et al. (2008 ▶); Ratish et al. (2009 ▶); Rough et al. (1998 ▶); Selnam et al. (2001 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶). For related structures, see: Gowda et al. (2007a ▶,b ▶,c ▶); Haider et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₅S
M _r = 334.34
Triclinic,
a = 7.9829 (3) Å
b = 8.4143 (3) Å
c = 12.6554 (5) Å
α = 70.888 (2)°
β = 81.553 (2)°
γ = 77.104 (2)°
V = 780.44 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
13620 measured reflections
3835 independent reflections
2928 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.150
S = 1.02
3835 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.47 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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048397/sj5052sup1.cif

e-67-00o25-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048397/sj5052Isup2.hkl

e-67-00o25-Isup2.hkl^{(188KB, 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
O5—H7⋯O4ⁱ	0.88	1.74	2.617 (4)	170
N1—H1⋯O16ⁱⁱ	0.86	2.31	2.860 (2)	122
N3—H3⋯O1ⁱⁱⁱ	0.86	2.13	2.974 (2)	165
C11—H11⋯O2^iv	0.93	2.59	3.379 (3)	143

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamides are well known in literature for their potential as biologically active compounds (Hanson et al., 1999; Moree et al.,1991; Rough et al., 1998). These have been reported to display anti-hypertensive, anti-convulsant, herbicidal and anti-malarial activities (Esteve & Bidal, 2002; Soledade et al., 2006; Xiao & Timberlake, 2000; Lee & Lee, 2002). In addition the sulfonamide unit has been found in a number of compounds possessing anti-HIV (Selnam et al.,2001), anti-inflammatory (Ratish et al., 2009) and anti-microbial (Ozbek et al., 2007; Parari et al., 2008) activities.

In continuation of our work regarding the synthesis of various sulfur containing heterocycles (Arshad et al., 2008; Khan et al., 2009), the structure of 3-({[4-(acetylamino)phenyl]sulfonyl}amino)benzoic acid (I) has been determined. Bond lengths and bond angles of the title molecule (Fig 1) are similar to those in related compounds (Gowda et al., 2007a,b,c; Haider et al., 2009) and are within normal ranges (Allen et al., 1987). In the crystal structure, each molecule is linked to an adjacent one through classical O5—H7···O4 intermolecular hydrogen bonds forming centrosymmetric dimers typical of carboxylic acids, Table 1. These dimers are further connected by N—H···O and C—H···O hydrogen bonds to form an extended network, Fig 2.

Experimental

To an aqueous solution (10.0 ml) of 4-amino benzoic acid (1.0 g; 7.3 mmoles) maintained at pH 9 with aqueous sodium bicarbonate solution, 4-(acetylamino)benzenesulfonyl chloride (2.21 g, 9.48 mmol) was added. Contents were stirred at room temperature until the complete consumption of the sulfonyl chloride (as indicated by TLC). The pH of the reaction mixture was changed to 1 using hydrochloric acid (1 M) and the precipitate obtained was filtered, washed with water and dried. The resulting solid was recrystallized from methanol to get suitable crystals.