Potassium N-bromo-4-chloro­benzene­sulfonamidate monohydrate

B Thimme Gowda; Sabine Foro; K Shakuntala

doi:10.1107/S1600536811023610

. 2011 Jun 22;67(Pt 7):m962. doi: 10.1107/S1600536811023610

Potassium N-bromo-4-chlorobenzenesulfonamidate monohydrate

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

PMCID: PMC3152022 PMID: 21836940

Abstract

In the structure of the title compound, K⁺·C₆H₄BrClNO₂S⁻·H₂O, the K⁺ cation is heptacoordinated. It is connected to two water O atoms, four sulfonyl O atoms and one Br atom. Further, the sulfonyl and water O atoms in the structure are bridged in a bidentate fashion. The S—N distance of 1.584 (6) Å is consistent with an S—N double bond, The crystal structure is stabilized by intermolecular O—H⋯N hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2007 ▶, 2011a ▶,b ▶); and on the oxidative strengths of N-halolarylsulfonamides, see: Usha & Gowda (2006 ▶). For similar structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶). For the preparation of the title compound, see: Gowda & Usha (2003 ▶).

Experimental

Crystal data

K⁺·C₆H₄BrClNO₂S⁻·H₂O
M _r = 326.64
Monoclinic,
a = 15.596 (1) Å
b = 10.188 (1) Å
c = 6.7649 (7) Å
β = 99.947 (9)°
V = 1058.73 (17) Å³
Z = 4
Mo Kα radiation
μ = 4.70 mm⁻¹
T = 293 K
0.34 × 0.34 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.298, T _max = 0.333
3796 measured reflections
2147 independent reflections
1984 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.156
S = 1.19
2147 reflections
134 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.22 e Å⁻³
Δρ_min = −0.95 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/S1600536811023610/ds2118sup1.cif

e-67-0m962-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023610/ds2118Isup2.hkl

e-67-0m962-Isup2.hkl^{(105.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023610/ds2118Isup3.cml

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	0.82 (2)	2.25 (5)	3.005 (8)	152 (8)
O3—H32⋯N1ⁱⁱ	0.82 (2)	2.16 (3)	2.967 (8)	166 (9)

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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

To explore the effect of substitution and replacing sodium ion by potassium ion in the solid state structures of N-chloroarylsulfonamides (Gowda et al., 2007; 2011a,b; Usha & Gowda, 2006), in the present work, the structure of potassium N-bromo-4-chloro- benzenesulfonamidate monohydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chloro- benzenesulfonamidate sesquihydrate(II)(Gowda et al., 2011b), potassium N,4-dichloro-benzenesulfonamidate monohydrate (III) (Gowda et al., 2011a), sodium N-bromo-4-chloro- benzenesulfonamidate sesquihydrate (IV)(Gowda et al., 2007) and other sodium N-chloro-arylsulfonamdes (George et al., 2000; Olmstead & Power, 1986). In particular, there is no interaction between the nitrogen and potassium atom in the molecule. Further, K⁺ is hepta co-ordinated in contrast to hexa co-ordination with Na⁺

K⁺ hepta coordination involves two O atoms from water molecules, four sulfonyl O atoms of N-bromo-4-chlorobenzenesulfonamide anions and one Br, in contrast to octahedral coordination of Na⁺ in (IV) by three O atoms of water molecules and by three sulfonyl O atoms of N-bromo-4-chloro- benzenesulfonamide anions (Gowda et al., 2007).

The S—N distance of N1—S1, 1.584 (6) 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 N1—S1, 1.574 (5)Å and N2—S2 1.579 (4)Å in (IV).

K⁺ ion coordination in the structure gives rise to several hydrogen bonding between coordinated water molecules and nitrogen atoms. The packing diagram consists of a two-dimensional polymeric layer running parallel to the b-axis (Fig. 2). The molecular packing is stabilized by O3—H31···N1 and O3—H32···N1 hydrogen bonds (Table 1).

Experimental

The title compound was prepared similar to the literature method (Gowda & Usha, 2003). The purity of the compound was checked by determining its melting point (184 ° C). It was characterized by recording its infrared and NMR spectra.

Yellow prisms of the title compound used in X-ray diffraction studies were obtained from its aqueous solution at room temperature.