Sodium 2-iodo­benzene­sulfonate monohydrate

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

doi:10.1107/S1600536808039202

. 2008 Nov 29;64(Pt 12):m1628. doi: 10.1107/S1600536808039202

Sodium 2-iodobenzenesulfonate monohydrate

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

PMCID: PMC2960107 PMID: 21581218

Abstract

In the title compound, Na⁺·C₆H₄IO₃S⁻·H₂O, the Na atom is hexacoordinated by O atoms, forming a two-dimensional sheet-like structure in the bc plane, with the iodobenzene rings protruding above and below. Na⋯O contact distances are in the range 2.419 (2)–2.7218 (18) Å and O⋯Na⋯O angles are in the range 73.70 (5)–158.64 (7)°. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions. The I atom is disordered over two positions with occupancies of 0.78 (2) and 0.22 (2).

Related literature

For related literature on the synthesis of biologically active benzothiazine derivatives, see: Arshad et al. (2008 ▶); Chau & Kice (1977 ▶); Shafiq, Khan et al. (2008 ▶); Shafiq, Tahir et al. (2008 ▶); Tahir et al. (2008 ▶).

Experimental

Crystal data

Na⁺·C₆H₄IO₃S⁻·H₂O
M _r = 324.06
Monoclinic,
a = 13.6141 (4) Å
b = 8.8233 (3) Å
c = 7.8493 (3) Å
β = 92.171 (1)°
V = 942.19 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.64 mm⁻¹
T = 296 (2) K
0.25 × 0.17 × 0.15 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.482, T _max = 0.580
10141 measured reflections
2339 independent reflections
2135 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.019
wR(F ²) = 0.047
S = 1.05
2339 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 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/S1600536808039202/su2075sup1.cif

e-64-m1628-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039202/su2075Isup2.hkl

e-64-m1628-Isup2.hkl^{(112.6KB, 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
O4—H4A⋯O2ⁱ	0.85	1.98	2.824 (2)	174
C6—H6⋯O1	0.93	2.42	2.834 (3)	107
C5—H5⋯Cgⁱ	0.93	2.79	3.661 (3)	156

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Symmetry code: (i) Inline graphic . Cg is the centroid of the benzene ring.

Acknowledgments

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

supplementary crystallographic information

Comment

In the continuation to our research work on the synthesis of biologically active benzothiazine derivatives (Arshad et al., 2008; Shafiq, Khan, Tahir & Siddiqui, 2008; Shafiq, Tahir, Khan, Ahmad & Siddiqui, 2008; Tahir et al., 2008), we synthesized the title compound, (I).

The molecular structure of compound (I) is illustrated in Fig. 1. The bond lengths and bond angles, as far as the 2-iodobenzenesulfonate is concerned, are similar to those reported for the potassium salt analogue, reported on recently (Arshad et al., 2008). The Na-atom is hexa-coordinated with O-atoms, involving four from the sulfonic groups and two water molecules. The range of the Na···O distances is 2.419 (2)–2.7218 (18) Å, whereas the range of O···Na···O angles is 73.70 (5)–158.64 (7)°. In this way a two-dimensional sheet-like structure in the bc plane is formed, with the iodobenzene rings protruding above and below.

It is interesting that one of the O-atoms of the sulfonic group is not involved in coordination with the Na-atom, but makes an intermolecular hydrogen bond with a water molecule, similar to the situation on the potassium salt analogue mentioned above. Also, one of the H-atoms of the H₂O molecule is not involved in intra or intermolecular H-bonding.

In the crystal structure of compound (I) a two dimensional polymeric network extending along the b axis is formed (Fig. 2). There exist O-H···O and C-H···O hydrogen bonds, and C-H···π-interactions involving the centroid, Cg, of the benzene ring, see Table 1 for details.

Experimental

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