Potassium N-bromo-2-chloro­benzene­sulfonamidate sesquihydrate

B Thimme Gowda; Sabine Foro; K Shakuntala

doi:10.1107/S1600536811022136

. 2011 Jun 18;67(Pt 7):m926. doi: 10.1107/S1600536811022136

Potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate

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

PMCID: PMC3151922 PMID: 21836910

Abstract

In the structure of the title compound, K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O, the K⁺ ion is heptacoordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-bromo-2-chlorobenzenesulfonamidate anions. The S—N distance of 1.582 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by intermolecular O—H⋯Br and O—H⋯N hydrogen bonds. The asymmetric unit consits of one potassium cation, one N-bromo-2-chlorobenzenesulfonamidate anion and one water molecule in general positions and one water molecule located on a twofold rotation axis.

Related literature

For preparation of N-haloarylsulfonamides, see: Usha & Gowda (2006 ▶). For our study of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2010 ▶, 2011a ▶,b ▶). For related structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶).

Experimental

Crystal data

K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O
M _r = 335.65
Orthorhombic,
a = 12.343 (2) Å
b = 52.066 (6) Å
c = 6.942 (1) Å
V = 4461.3 (11) Å³
Z = 16
Mo Kα radiation
μ = 4.47 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.244, T _max = 0.468
4075 measured reflections
1909 independent reflections
1841 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.067
S = 1.06
1909 reflections
141 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ▶), 671 Friedel pairs
Flack parameter: 0.019 (9)

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/S1600536811022136/nc2232sup1.cif

e-67-0m926-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022136/nc2232Isup2.hkl

e-67-0m926-Isup2.hkl^{(94.2KB, 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)	2.16 (2)	2.937 (4)	164 (5)
O3—H32⋯Br1ⁱⁱ	0.80 (2)	2.83 (3)	3.574 (3)	156 (4)
O4—H41⋯N1ⁱⁱⁱ	0.82 (2)	2.13 (3)	2.905 (4)	157 (5)

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

Acknowledgments

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

supplementary crystallographic information

Comment

To explore the effect of replacing sodium by potassium on the solid state structures of N-haloarylsulfonamidates (Gowda et al., 2011a,b), the structure of potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of I resembles those of sodium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011b), sodium N-chloro-2-chloro- benzenesulfonamidate sesquihydrate (III)(Gowda et al., 2010), potassium N-chloro-4-chloro-benzenesulfonamidate monohydrate (IV)(Gowda et al., 2011a), and other sodium N-chloro- arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the structure of the title compound the K⁺ ion is hepta coordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-bromo-2-chloro-benzenesulfonamide anions. The replacement of Na⁺ by K⁺ changes the coordination from hexa to hepta coordination (Gowda et al., 2011b).

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 1.579 (6) Å in (II), 1.588 (2) Å in (III) and 1.588 (2) Å in (IV)

In the crystal structure two-dimensional polymeric layer are found that are located parallel to the ac plane (Fig. 2). The molecular packing is stabilized by O3—H31···N1, O3—H32···Br1 and O4—H41···N1 hydrogen bonds (Table 1).

Experimental

The title compound was prepared according to the literature method (Usha & Gowda, 2006). The purity of the compound was checked by determining its melting point (176 °). 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.