4-(4-Meth­oxy­benzene­sulfonamido)­benzoic acid

Islam Ullah Khan; Ghulam Mustafa; Mehmet Akkurt

doi:10.1107/S1600536811025098

. 2011 Jun 30;67(Pt 7):o1857. doi: 10.1107/S1600536811025098

4-(4-Methoxybenzenesulfonamido)benzoic acid

Islam Ullah Khan ^a,^*, Ghulam Mustafa ^a, Mehmet Akkurt ^b,^*

PMCID: PMC3151892 PMID: 21837222

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃NO₅S, contains two independent molecules in which the dihedral angles between the aromatic rings are 83.45 (11) and 86.65 (9)°. In the crystal, the independent molecules are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a double-chain structure along [401]. A weak π–π stacking interaction with a centroid–centroid distance of 3.7509 (13) Å and C—H⋯O hydrogen bonds are also observed.

Related literature

For background to the biological activity of sulfonamides, see: Hanson et al. (1999 ▶). For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₅S
M _r = 307.32
Monoclinic,
a = 8.6980 (3) Å
b = 21.7471 (8) Å
c = 14.5824 (6) Å
β = 95.153 (2)°
V = 2747.21 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.38 × 0.31 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T _min = 0.909, T _max = 0.931
25188 measured reflections
6806 independent reflections
5475 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.120
S = 1.04
6806 reflections
394 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 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 datablock(s) global, I. DOI: 10.1107/S1600536811025098/is2741sup1.cif

e-67-o1857-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025098/is2741Isup2.hkl

e-67-o1857-Isup2.hkl^{(333.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811025098/is2741Isup3.cml

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—HN1⋯O8ⁱ	0.84 (2)	2.31 (2)	3.122 (2)	165 (2)
O2—HO1⋯O7ⁱⁱ	0.81 (2)	1.78 (2)	2.583 (2)	172 (2)
N2—HN2⋯O3ⁱⁱⁱ	0.82 (2)	2.15 (2)	2.959 (2)	173 (2)
O6—HO2⋯O1^iv	0.82 (2)	2.02 (2)	2.8338 (19)	173 (2)
C4—H4⋯O4	0.93	2.54	3.149 (2)	123
C9—H9⋯O7	0.93	2.32	3.224 (3)	165
C13—H13⋯O10^v	0.93	2.57	3.381 (3)	146
C14—H14A⋯O8^iv	0.96	2.42	3.370 (3)	169
C23—H23⋯O2	0.93	2.52	3.286 (2)	140
C26—H26⋯O1^vi	0.93	2.57	3.197 (2)	125

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

Acknowledgments

The authors are grateful to Mr Shahzad Shrif for his assistance and the Higher Education Commission (HEC), Pakistan, for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

supplementary crystallographic information

Comment

Sulfonamides are well known for their various types of biological activities (e.g. Hanson et al., 1999). In the present paper, the structure of the title compound, (I), is reported.

As shown in Fig. 1, the asymmetric unit of the title compound (I) contains two crystallographically independent molecules A (with S1) and B (with S2). All the bond lengths (Allen et al., 1987) and angles are within normal ranges and they are similar to those of the related molecules (Mustafa et al., 2010, 2011). The dihedral angles between the aromatic rings of (I) is 83.45 (11)° for molecule A and 86.65 (9)° for molecule B.

The crystal packing (Fig. 2, Table 1) is stabilized by C—H···O, N—H···O and O—H···O hydrogen bonds and a weak π–π interaction between the benzene rings attached with the methoxy group of the symmetry independent molecules [Cg2···Cg4^iv = 3.7509 (13) Å; symmetry code: (iv) x - 1, -y + 1/2, z - 1/2; Cg2 and Cg4 are the centroid of the C8–C13 and C22–C27 benzene rings, respectively].

Experimental

To a mixture of p-amino benzoic acid (1.0 g, 7.3 mmoles) and distilled water (10 ml) in a round bottomflask (25 ml) 1M aqueous sodium carbonate solution was added to maintain the pH between 8–9. 4-Methoxy benzenesulfonyl chloride (1.51 g, 7.3 mmol) was added to this solution and was kept stirred at room temperature for 5 h. pH of the reaction mixture was adjusted to 1–2, using 1 N HCl and the precipitates obtained were filtered, washed with distilled water, dried and recrystallized from methanol to yield light brown crystals of (I).