Potassium N,2-dichloro­benzene­sulfonamidate sesquihydrate

B Thimme Gowda; Sabine Foro; K Shakuntala

doi:10.1107/S1600536811021891

. 2011 Jun 11;67(Pt 7):m914. doi: 10.1107/S1600536811021891

Potassium N,2-dichlorobenzenesulfonamidate sesquihydrate

B Thimme Gowda ^a,^*, Sabine Foro ^b, K Shakuntala ^a

PMCID: PMC3151921 PMID: 21836899

Abstract

In the title compound, K⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O, one water molecule has crystallographically imposed twofold symmetry. The K⁺ ion is heptacoordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-chloro-2-chloro-benzenesulfonamide anions. The S—N distance of 1.582 (2) Å is consistent with an S—N double bond. In the structure, the sulfonyl-O and the water-O atoms bridge the K⁺ cations in a bidentate fashion. The crystal structure comprises sheets in the ac plane which are further stabilized by intermolecular O—H⋯Cl and O—H⋯N hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2010 ▶, 2011a ▶,b ▶); and on the oxidative strengths of N-haloarylsulfonamides, see: Gowda & Shetty (2004 ▶); Usha & Gowda (2006 ▶). For similar structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶). For the preparation of the title compound, see: Jyothi & Gowda (2004 ▶).

Experimental

Crystal data

K⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O
M _r = 291.19
Monoclinic,
a = 12.301 (2) Å
b = 6.8277 (6) Å
c = 27.965 (3) Å
β = 106.28 (1)°
V = 2254.5 (5) Å³
Z = 8
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.44 × 0.44 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.640, T _max = 0.677
4174 measured reflections
2298 independent reflections
2181 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.105
S = 1.19
2298 reflections
142 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021891/sj5159sup1.cif

e-67-0m914-sup1.cif^{(20KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021891/sj5159Isup2.hkl

e-67-0m914-Isup2.hkl^{(113KB, 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
O3—H31⋯N1ⁱ	0.80 (2)	2.23 (2)	2.962 (3)	152 (4)
O3—H32⋯Cl1ⁱⁱ	0.81 (2)	2.73 (2)	3.517 (3)	165 (4)
O4—H41⋯N1ⁱ	0.81 (2)	2.19 (2)	2.978 (3)	165 (4)

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

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a grant under the UGC–BSR one time grant to Faculty/Professors.

supplementary crystallographic information

Comment

Arylsulfonamides and their N-halo compounds are of interest in synthetic, mechanistic and analytical chemistry (Gowda & Shetty, 2004; Usha & Gowda, 2006). To explore the substituent effects and the effect of replacing sodium ions by potassium ions on the solid state structures of N-halo- arylsulfonamides (Gowda et al., 2010, 2011a,b), in the present work, the structure of potassium N,2-dichloro-benzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of (I) is isostructural with potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011b), and resembles those of potassium N,4-dichloro-benzenesulfonamidate monohydrate (III) (Gowda et al., 2011a), sodium N,2-dichloro-benzenesulfonamidate sesquihydrate (IV) (Gowda et al., 2010) and other sodium N-chloro-arylsulfonamides (George et al., 2000; Olmstead & Power, 1986).

In the title compound, K⁺ ion is hepta coordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-chloro-2-chloro- benzenesulfonamidate anions. This is in contrast to hepta coordination of K⁺ by two O atoms from water molecules, four sulfonyl O atoms from the N-chloro-4-chlorobenzenesulfonamidate anions and one Cl in (III), and octahedral coordination of Na⁺ by three O atoms of water molecules and three sulfonyl O atoms of three different N-chloro-2-chloro- benzenesulfonamidate anions.

The S—N distance of 1.582 (4)Å is consistent with an S—N double bond and is in agreement with the observed values of 1.582 (4)Å in (II), 1.588 (2) Å in (III) and 1.588 (2) Å in (IV)

The crystal structure comprises sheets in the ac plane (Fig. 2). The molecular packing is stabilized by O3—H31···N1, O3—H32···Cl1 and O4—H41···N1 hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the method similar to that reported in literature (Jyothi & Gowda, 2004). The purity of the compound was checked by determining its melting point. Colourless prisms of (I) were obtained from its aqueous solution at room temperature.