Potassium 2-iodo­benzene­sulfonate monohydrate

Muhammad Nadeem Arshad; Islam Ullah Khan; Saeed Ahmad; Muhammad Shafiq; Helen Stoeckli-Evans

doi:10.1107/S1600536808019429

. 2008 Jul 5;64(Pt 8):m994. doi: 10.1107/S1600536808019429

Potassium 2-iodobenzenesulfonate monohydrate

Muhammad Nadeem Arshad ^a,^*, Islam Ullah Khan ^a, Saeed Ahmad ^b, Muhammad Shafiq ^a, Helen Stoeckli-Evans ^c,^*

PMCID: PMC2961920 PMID: 21203089

Abstract

In the crystal structure of the title compound, K⁺·C₆H₄IO₃S⁻·H₂O, the potasium cation is 2.693 (3)–2.933 (3) Å from the sulfonate and water O atoms (including symmetry-related atoms) and forms a two-dimensional sheet-like structure in the bc plane, with the iodobenzene rings protruding above and below. The water molecule of crystallization is hydrogen-bonded to sulfonate O atoms within this two-dimensional arrangement. Symmetry-related iodobenzene rings are arranged perpendicular to one another with the I atom ca 4.1 Å from the centroid of the neighbouring benzene ring. In the crystal structure, these two-dimensional sheet-like supramolecular structures are arranged parallel to one another, stacked along the a-axis direction, with the benzene rings interdigitated.

Related literature

For related literature see: Chau & Kice (1977 ▶); Re et al. (1999 ▶); Yoshiizumi et al.(2004 ▶); Siddiqui et al. (2006 ▶, 2007 ▶); Gowda et al. (2007 ▶).

Experimental

Crystal data

K⁺·C₆H₄IO₃S⁻·H₂O
M _r = 340.17
Monoclinic,
a = 13.8993 (4) Å
b = 9.0678 (3) Å
c = 8.1654 (2) Å
β = 92.260 (2)°
V = 1028.33 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.70 mm⁻¹
T = 296 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker Kappa-APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.543, T _max = 0.754
12144 measured reflections
2804 independent reflections
1961 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.113
S = 1.00
2804 reflections
118 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −0.68 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019429/cs2082sup1.cif

e-64-0m994-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019429/cs2082Isup2.hkl

e-64-0m994-Isup2.hkl^{(137.7KB, 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
O1W—H1WB⋯O1ⁱ	0.86	2.03	2.855 (5)	160
O1W—H1WA⋯O3ⁱⁱ	0.86	2.41	3.266 (5)	179

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

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for funding under its Indigenous 5000 PhD Scholarship Scheme, Batch II (PIN 042-120607-Ps2-183).

supplementary crystallographic information

Comment

Sulfonic acids belong to an important class of organic compounds particularly the aromatics which have wide applications in different areas (Re et al., 1999). Derivatives of the sodium salt of benzene sulfonic acid were reported as being a scavenger receptor inhibitor (Yoshiizumi et al., 2004). Herein, we report on the crystal structure of the title compound, the potassium salt of 2-iodobenzenesulfoninc acid, in continuation of our research work on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2006, 2007).

The molecular stucture of the title compound is shown in Fig. 1. The bond lengths and angles are similar to those reported for other benzene sulfonates, for example, potassium 4-chlorobenzenesulfonate (Gowda et al., 2007). The potasium cation is between 2.693 (3) to 2.933 (3) Å from the sulfonate and water O atoms (including symmetry related O atoms) and forms a two-dimensional sheet-like structure in the bc plane, with the iodobenzene rings protruding above and below (Fig. 2). Symmetry related iodobenzene rings are arranged perpendicular to one another, with the iodine atom ca 4.1 Å from the centroid of the neighbouring benzene ring (Fig. 3). The water molecule of crystallization is hydrogen bonded to sulfonate O-atoms (one normal interaction to atom O1, and one rather long interaction to atom O3), within this two-dimensional arrangement (Table 1).

In the crystal structure these 2-D sheet-like supermolecular structures are arranged parallel to one another up the a direction, with the benzene rings interdigited (Fig. 3).

Experimental

The title compound was prepared following the method used by Chau & Kice (1977), and suitable crystals for X-ray analysis were obtained from the reaction mixture.