4-(2-Iodo­benzene­sulfonamido)benzoic acid monohydrate

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

doi:10.1107/S1600536808043754

. 2009 Jan 8;65(Pt 2):o230. doi: 10.1107/S1600536808043754

4-(2-Iodobenzenesulfonamido)benzoic acid monohydrate

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

PMCID: PMC2968366 PMID: 21581847

Abstract

In the molecule of the title compound, C₁₃H₁₀INO₄S·H₂O, the coordination around the S atom is distorted tetrahedral. The aromatic rings are oriented at a dihedral angle of 74.18 (17)°. Intramolecular C—H⋯O hydrogen bonds result in the formation of non-planar five- and six-membered rings, which adopt envelope and twist conformations, respectively. In the crystal structure, intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the molecules. π–π Contacts between the phenyl rings [centroid–centroid distance = 3.726 (3) Å] may further stabilize the structure. There is also a C—H⋯π interaction.

Related literature

For general background, see: Medina et al. (1999 ▶). For related structures, see: Arshad et al. (2008a ▶,b ▶); Nan & Xing (2006 ▶); Deng & Mani (2006 ▶).

Experimental

Crystal data

C₁₃H₁₀INO₄S·H₂O
M _r = 421.20
Monoclinic,
a = 13.8049 (9) Å
b = 8.2756 (5) Å
c = 14.7928 (10) Å
β = 117.472 (3)°
V = 1499.42 (17) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 296 (2) K
0.28 × 0.10 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.754, T _max = 0.849
9099 measured reflections
3687 independent reflections
2022 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.112
S = 1.01
3687 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.54 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/S1600536808043754/hk2605sup1.cif

e-65-0o230-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043754/hk2605Isup2.hkl

e-65-0o230-Isup2.hkl^{(177.1KB, 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	2.03	2.860 (6)	161.00
O3—H3O⋯O5ⁱⁱ	0.91 (7)	1.73 (7)	2.616 (6)	165 (7)
O5—H5A⋯O2ⁱⁱⁱ	0.81	2.20	2.924 (6)	149.00
O5—H5B⋯O1	0.88	1.98	2.791 (6)	152.00
C6—H6⋯O1	0.93	2.36	2.793 (7)	108.00
C11—H11⋯O2^iv	0.93	2.52	3.437 (6)	171.00
C12—H12⋯O1	0.93	2.54	3.035 (7)	114.00
C3—H3⋯Cg2^v	0.93	2.90	3.818 (7)	168.00

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

Acknowledgments

MNA greatfully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2–183).

supplementary crystallographic information

Comment

The title compound belongs to the sulfonamide family of the organic compounds. This class of compounds is used as antibecterial agent. The halogenated sulfonamide is used as an inhibitor for the growth of multidrug resistant MCF-7/ADR cancer cells (Medina et al., 1999). In continuation to our researches with sulfonamides (Arshad et al., 2008a,b), the title compound has been prepared, which will be utilized for the syntheses of biologically active heterocyclic molecules with thiazine moiety, and we report herein its crystal structure.

In the title compound, (I), (Fig 1), 2-iodophenyl and p-aminobenzoic acid moieties are connected through the SO₂ group. The structure of (I) differs from 4-(tosylamino)benzoic acid, (II) (Nan & Xing, 2006), mainly due to the attachment of the iodo group at ortho position instead of methyl group at the para-position. 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 74.18 (17)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of nonplanar five- and six-membered rings: C (S1/O1/C1/C6/H6) and D (S1/O1/N1/C7/C12/H12). Ring C adopts envelope conformation with O1 atom displaced by -0.172 (3) Å from the plane of the other rings atoms, while ring D has twisted conformation.

In the crystal structure, intermolecular N-H···O, O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contact between the phenyl rings, Cg1—Cg1ⁱ [symmetry code: (i) -x, -y, -z, where Cg1 is centroid of the ring A (C1-C6)] may further stabilize the structure, with centroid-centroid distance of 3.726 (3) Å. There also exists a C–H···π interaction (Table 1).

Experimental

The title compound was synthesized according to a literature method (Deng & Mani, 2006). 4-Aminobenzoic acid (0.23 g, 1.67 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.