2-Chloro-5-(2-iodo­benzene­sulfonamido)­benzoic acid

Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Waseeq Ahmad Siddiqui; Muhammad Shafiq

doi:10.1107/S1600536808043869

. 2009 Jan 10;65(Pt 2):o281. doi: 10.1107/S1600536808043869

2-Chloro-5-(2-iodobenzenesulfonamido)benzoic acid

Muhammad Nadeem Arshad ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^a, Waseeq Ahmad Siddiqui ^c, Muhammad Shafiq ^a

PMCID: PMC2968399 PMID: 21581894

Abstract

In the molecule of the title compound, C₁₃H₉ClINO₄S, the coordination around the S atom is distorted tetrahedral. The aromatic rings are oriented at a dihedral angle of 74.46 (9)°. Intramolecular C—H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings, which adopt planar, envelope and twisted conformations, respectively. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules to form R ₂ ²(8) ring motifs, which are further linked by C—H⋯O hydrogen bonds. π–π contacts between the benzene rings [centroid–centroid distances = 3.709 (3) and 3.772 (3) Å] may further stabilize the structure. The I atom is disordered over two positions, refined with occupancies of ca 0.75 and 0.25.

Related literature

For related structures, see: Arshad, Tahir, Khan, Ahmad & Shafiq (2008 ▶); Arshad, Tahir, Khan, Shafiq & Siddiqui (2008 ▶); Arshad et al. (2009 ▶); Deng & Mani (2006 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₉ClINO₄S
M _r = 437.62
Monoclinic,
a = 26.6375 (9) Å
b = 8.5532 (2) Å
c = 14.2696 (5) Å
β = 111.923 (2)°
V = 3016.03 (17) Å³
Z = 8
Mo Kα radiation
μ = 2.45 mm⁻¹
T = 296 (2) K
0.25 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.708, T _max = 0.819
16794 measured reflections
3738 independent reflections
2909 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.069
S = 1.05
3738 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.31 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043869/hk2607sup1.cif

e-65-0o281-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043869/hk2607Isup2.hkl

e-65-0o281-Isup2.hkl^{(179.6KB, 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⋯O4ⁱ	0.86	2.07	2.903 (3)	164
O3—H3O⋯O2ⁱⁱ	0.76 (4)	1.95 (4)	2.714 (3)	176 (5)
C4—H4⋯O1ⁱⁱⁱ	0.93	2.48	3.293 (4)	146
C6—H6⋯O1	0.93	2.36	2.792 (3)	108
C8—H8⋯O1	0.93	2.57	3.193 (3)	125
C8—H8⋯O3	0.93	2.28	2.631 (3)	102

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

Acknowledgments

MNA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042-120607-PS2-183).

supplementary crystallographic information

Comment

In continuation to our researches with sulfonamides (Arshad, Tahir, Khan, Ahmad & Shafiq, 2008; Arshad, Tahir, Khan, Shafiq & Siddiqui, 2008; Arshad et al., 2009), the title compound has been synthesized, and we report herein its crystal structure.

The structure of the title compound, (I), (Fig 1), differs from 4-[(2-iodo- phenyl)sulfonyl]aminobenzoic acid hydrate, (II) (Arshad et al., 2009), due to the attachment of Cl atom and the change of the position of carboxylate group. Also in (I), there is no water molecule. The coordination around the S atom is a distorted tetrahedral. Rings A(C1-C6) and B(C7-C12) are oriented at a dihedral angle of 74.46 (9)°, which is nearly the same with the corresponding value [74.18 (17)°] in (II). The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of two five- and one six-membered rings: C (S1/O1/C1/C6/H6), D (O3/C8/C9/C13/H8) and E (S1/O1/N1/C7/C8/H8). Ring C is planar. Ring D adopts envelope conformation with O3 atom displaced by -0.260 (4) Å from the plane of the other rings atoms, while ring E has twisted conformation. The dihedral angle between rings A and C is 2.18 (3)°.

In the crystal structure, intermolecular N-H···O and O-H···O hydrogen bonds (Table 1) link the molecules to form R₂²(8) ring motifs (Bernstein et al., 1995), they are further linked by C-H···O hydrogen bonds (Table 1, Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the phenyl rings and the benzene rings, Cg1—Cg1ⁱ and Cg2—Cg2ⁱⁱ [symmetry codes: (i) 1/2 - x, 3/2 - y, 1 - z; (ii) -x, 2 - y, -z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B(C7-C12), respectively] may further stabilize the structure, with centroid-centroid distances of 3.709 (3) Å and 3.772 (3) Å.

Experimental

The title compound was synthesized according to a literature method (Deng & Mani, 2006). 5-Amino-2-chlorobenzoic acid (0.28 g, 1.66 mmol) was suspended in distilled water (10 ml) in a round bottom flask. The pH of the solution was adjusted to 8-9 using Na₂CO₃ (1 M). Then, 2-iodobenzene sulfonyl chloride (0.5 g, 1.66 mmol) was added, and stirred at room temperature. The reaction pH was maintained at 8-9. Completion of reaction was indicated by the dissolvation of the suspended 2-iodobenzene sulfonyl chloride. Then, pH was adjusted to 2-3 using HCl (2 N). The precipitate formed was filtered, washed with distilled water, and then recrystalyzed in methanol.