Potassium N,2-dichloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Foro, S.; Shakuntala, K.

doi:10.1107/S1600536811021891

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m914

doi:10.1107/S1600536811021891

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Potassium N,2-dichlorobenzenesulfonamidate sesquihydrate

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 June 2011; accepted 7 June 2011; online 11 June 2011)

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, C 2/c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.042
wR(F²) = 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

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)
Symmetry codes: (i) x, y+1, z; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021891/sj5159sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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-halolarylsulfonamides, 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 top

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.

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme for the asymmetric unit and extended to show the coordination geometry for the K⁺ cation. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii (i) -x+1/2, y-1/2, -z+3/2; (ii) -x+1, y, -z+3/2; (iii) -x+1/2, y+1/2, -z+3/2.
	Fig. 2. Molecular packing of the title compound with hydrogen bonds drawn as dashed lines.

Potassium N,2-dichlorobenzenesulfonamidate sesquihydrate top

Crystal data top

K⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	F(000) = 1176
M_r = 291.19	D_x = 1.716 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2350 reflections
a = 12.301 (2) Å	θ = 3.0–27.8°
b = 6.8277 (6) Å	µ = 1.12 mm⁻¹
c = 27.965 (3) Å	T = 293 K
β = 106.28 (1)°	Prism, colourless
V = 2254.5 (5) Å³	0.44 × 0.44 × 0.38 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2298 independent reflections
Radiation source: fine-focus sealed tube	2181 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans.	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→10
T_min = 0.640, T_max = 0.677	k = −6→8
4174 measured reflections	l = −34→34

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0457P)² + 5.0762P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max = 0.002
2298 reflections	Δρ_max = 0.47 e Å⁻³
142 parameters	Δρ_min = −0.46 e Å⁻³
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0234 (10)

Crystal data top

K⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	V = 2254.5 (5) Å³
M_r = 291.19	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.301 (2) Å	µ = 1.12 mm⁻¹
b = 6.8277 (6) Å	T = 293 K
c = 27.965 (3) Å	0.44 × 0.44 × 0.38 mm
β = 106.28 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2298 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2181 reflections with I > 2σ(I)
T_min = 0.640, T_max = 0.677	R_int = 0.015
4174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	3 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.47 e Å⁻³
2298 reflections	Δρ_min = −0.46 e Å⁻³
142 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2790 (2)	0.2499 (4)	0.60429 (9)	0.0268 (5)
C2	0.1789 (2)	0.1729 (4)	0.57347 (10)	0.0346 (6)
C3	0.1218 (3)	0.2695 (6)	0.53041 (12)	0.0510 (8)
H3	0.0551	0.2173	0.5100	0.061*
C4	0.1633 (4)	0.4426 (6)	0.51767 (13)	0.0599 (10)
H4	0.1241	0.5075	0.4887	0.072*
C5	0.2620 (3)	0.5203 (5)	0.54735 (13)	0.0545 (9)
H5	0.2899	0.6373	0.5384	0.065*
C6	0.3204 (3)	0.4242 (4)	0.59073 (11)	0.0383 (6)
H6	0.3874	0.4769	0.6108	0.046*
N1	0.38459 (19)	−0.0793 (3)	0.65478 (9)	0.0328 (5)
O1	0.27693 (18)	0.1323 (3)	0.69244 (7)	0.0380 (5)
O2	0.45006 (17)	0.2695 (3)	0.68135 (7)	0.0402 (5)
O3	0.2321 (2)	0.6414 (3)	0.68516 (8)	0.0431 (5)
H31	0.260 (3)	0.704 (5)	0.6675 (12)	0.052*
H32	0.181 (3)	0.584 (5)	0.6658 (12)	0.052*
O4	0.5000	0.7199 (5)	0.7500	0.0478 (8)
H41	0.477 (3)	0.791 (5)	0.7260 (10)	0.057*
K1	0.35556 (5)	0.42956 (9)	0.76528 (2)	0.0342 (2)
Cl1	0.48019 (7)	−0.09326 (13)	0.61910 (3)	0.0478 (2)
Cl2	0.12087 (7)	−0.04411 (13)	0.58723 (4)	0.0561 (3)
S1	0.35458 (5)	0.14187 (9)	0.66219 (2)	0.0262 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0265 (11)	0.0307 (13)	0.0240 (11)	0.0051 (10)	0.0085 (9)	0.0003 (10)
C2	0.0302 (13)	0.0381 (14)	0.0329 (13)	0.0059 (11)	0.0047 (11)	−0.0060 (11)
C3	0.0414 (17)	0.067 (2)	0.0359 (16)	0.0174 (16)	−0.0028 (13)	−0.0059 (15)
C4	0.072 (2)	0.069 (2)	0.0342 (17)	0.032 (2)	0.0082 (16)	0.0163 (16)
C5	0.071 (2)	0.0499 (19)	0.0461 (18)	0.0114 (17)	0.0224 (17)	0.0192 (15)
C6	0.0433 (16)	0.0370 (15)	0.0360 (14)	0.0002 (12)	0.0133 (12)	0.0035 (12)
N1	0.0325 (12)	0.0327 (12)	0.0339 (12)	0.0018 (9)	0.0104 (9)	0.0021 (9)
O1	0.0449 (11)	0.0444 (11)	0.0309 (10)	−0.0048 (9)	0.0208 (9)	−0.0007 (8)
O2	0.0373 (11)	0.0430 (11)	0.0341 (10)	−0.0127 (9)	−0.0002 (8)	−0.0018 (9)
O3	0.0455 (12)	0.0427 (12)	0.0387 (12)	−0.0017 (10)	0.0079 (9)	0.0016 (9)
O4	0.0565 (19)	0.0343 (16)	0.0420 (17)	0.000	−0.0038 (15)	0.000
K1	0.0325 (3)	0.0354 (3)	0.0366 (3)	0.0065 (2)	0.0129 (2)	0.0028 (2)
Cl1	0.0399 (4)	0.0590 (5)	0.0472 (4)	0.0057 (3)	0.0164 (3)	−0.0102 (4)
Cl2	0.0364 (4)	0.0480 (5)	0.0718 (6)	−0.0112 (3)	−0.0049 (4)	−0.0054 (4)
S1	0.0271 (3)	0.0299 (3)	0.0206 (3)	−0.0043 (2)	0.0053 (2)	0.0000 (2)

Geometric parameters (Å, º) top

C1—C6	1.388 (4)	O1—K1	2.846 (2)
C1—C2	1.393 (4)	O2—S1	1.440 (2)
C1—S1	1.785 (2)	O2—K1ⁱⁱ	2.672 (2)
C2—C3	1.380 (4)	O2—K1	3.096 (2)
C2—Cl2	1.734 (3)	O3—K1	2.741 (2)
C3—C4	1.373 (6)	O3—K1ⁱⁱⁱ	2.791 (2)
C3—H3	0.9300	O3—H31	0.797 (19)
C4—C5	1.372 (6)	O3—H32	0.806 (19)
C4—H4	0.9300	O4—K1	2.774 (2)
C5—C6	1.389 (4)	O4—K1ⁱⁱ	2.774 (2)
C5—H5	0.9300	O4—H41	0.811 (18)
C6—H6	0.9300	K1—O1ⁱⁱⁱ	2.655 (2)
N1—S1	1.582 (2)	K1—O2ⁱⁱ	2.672 (2)
N1—Cl1	1.745 (2)	K1—O3ⁱ	2.791 (2)
O1—S1	1.4442 (19)	K1—S1	3.4859 (9)
O1—K1ⁱ	2.655 (2)

C6—C1—C2	118.9 (2)	O2ⁱⁱ—K1—O3	151.25 (7)
C6—C1—S1	117.7 (2)	O1ⁱⁱⁱ—K1—O4	101.28 (7)
C2—C1—S1	123.4 (2)	O2ⁱⁱ—K1—O4	82.34 (6)
C3—C2—C1	120.3 (3)	O3—K1—O4	74.28 (6)
C3—C2—Cl2	117.5 (2)	O1ⁱⁱⁱ—K1—O3ⁱ	77.05 (7)
C1—C2—Cl2	122.2 (2)	O2ⁱⁱ—K1—O3ⁱ	81.03 (7)
C4—C3—C2	120.2 (3)	O3—K1—O3ⁱ	125.11 (4)
C4—C3—H3	119.9	O4—K1—O3ⁱ	158.97 (5)
C2—C3—H3	119.9	O1ⁱⁱⁱ—K1—O1	124.24 (4)
C5—C4—C3	120.4 (3)	O2ⁱⁱ—K1—O1	100.34 (7)
C5—C4—H4	119.8	O3—K1—O1	77.99 (7)
C3—C4—H4	119.8	O4—K1—O1	120.21 (5)
C4—C5—C6	119.9 (3)	O3ⁱ—K1—O1	75.62 (6)
C4—C5—H5	120.0	O1ⁱⁱⁱ—K1—O2	158.33 (6)
C6—C5—H5	120.0	O2ⁱⁱ—K1—O2	79.15 (7)
C1—C6—C5	120.3 (3)	O3—K1—O2	78.84 (6)
C1—C6—H6	119.9	O4—K1—O2	75.08 (6)
C5—C6—H6	119.9	O3ⁱ—K1—O2	114.01 (7)
S1—N1—Cl1	110.28 (13)	O1—K1—O2	47.94 (5)
S1—O1—K1ⁱ	150.89 (13)	O1ⁱⁱⁱ—K1—S1	143.30 (5)
S1—O1—K1	103.85 (10)	O2ⁱⁱ—K1—S1	91.52 (5)
K1ⁱ—O1—K1	100.43 (6)	O3—K1—S1	75.44 (5)
S1—O2—K1ⁱⁱ	164.66 (13)	O4—K1—S1	97.42 (4)
S1—O2—K1	93.17 (10)	O3ⁱ—K1—S1	95.81 (5)
K1ⁱⁱ—O2—K1	84.23 (6)	O1—K1—S1	23.72 (4)
K1—O3—K1ⁱⁱⁱ	99.72 (7)	O2—K1—S1	24.36 (4)
K1—O3—H31	124 (3)	O2—S1—O1	114.44 (12)
K1ⁱⁱⁱ—O3—H31	103 (3)	O2—S1—N1	115.50 (13)
K1—O3—H32	116 (3)	O1—S1—N1	104.51 (12)
K1ⁱⁱⁱ—O3—H32	110 (3)	O2—S1—C1	104.51 (12)
H31—O3—H32	103 (4)	O1—S1—C1	106.75 (12)
K1—O4—K1ⁱⁱ	88.78 (10)	N1—S1—C1	110.93 (12)
K1—O4—H41	118 (3)	O2—S1—K1	62.47 (9)
K1ⁱⁱ—O4—H41	113 (3)	O1—S1—K1	52.43 (9)
O1ⁱⁱⁱ—K1—O2ⁱⁱ	121.97 (7)	N1—S1—K1	134.37 (9)
O1ⁱⁱⁱ—K1—O3	79.63 (7)	C1—S1—K1	113.42 (8)

C6—C1—C2—C3	−0.4 (4)	K1—O2—S1—O1	−7.24 (13)
S1—C1—C2—C3	176.7 (2)	K1ⁱⁱ—O2—S1—N1	−49.0 (5)
C6—C1—C2—Cl2	179.9 (2)	K1—O2—S1—N1	−128.69 (10)
S1—C1—C2—Cl2	−3.0 (3)	K1ⁱⁱ—O2—S1—C1	−171.1 (5)
C1—C2—C3—C4	−0.1 (5)	K1—O2—S1—C1	109.15 (9)
Cl2—C2—C3—C4	179.6 (3)	K1ⁱⁱ—O2—S1—K1	79.7 (5)
C2—C3—C4—C5	0.5 (5)	K1ⁱ—O1—S1—O2	−137.6 (2)
C3—C4—C5—C6	−0.4 (6)	K1—O1—S1—O2	8.11 (15)
C2—C1—C6—C5	0.6 (4)	K1ⁱ—O1—S1—N1	−10.2 (3)
S1—C1—C6—C5	−176.7 (2)	K1—O1—S1—N1	135.42 (10)
C4—C5—C6—C1	−0.2 (5)	K1ⁱ—O1—S1—C1	107.3 (3)
K1ⁱⁱⁱ—O3—K1—O1ⁱⁱⁱ	16.67 (7)	K1—O1—S1—C1	−106.99 (11)
K1ⁱⁱⁱ—O3—K1—O2ⁱⁱ	−125.10 (13)	K1ⁱ—O1—S1—K1	−145.7 (3)
K1ⁱⁱⁱ—O3—K1—O4	−88.29 (7)	Cl1—N1—S1—O2	−52.68 (17)
K1ⁱⁱⁱ—O3—K1—O3ⁱ	82.64 (12)	Cl1—N1—S1—O1	−179.33 (13)
K1ⁱⁱⁱ—O3—K1—O1	145.25 (8)	Cl1—N1—S1—C1	65.98 (16)
K1ⁱⁱⁱ—O3—K1—O2	−165.75 (8)	Cl1—N1—S1—K1	−128.22 (10)
K1ⁱⁱⁱ—O3—K1—S1	169.49 (7)	C6—C1—S1—O2	−2.1 (2)
K1ⁱⁱ—O4—K1—O1ⁱⁱⁱ	164.53 (5)	C2—C1—S1—O2	−179.2 (2)
K1ⁱⁱ—O4—K1—O2ⁱⁱ	43.34 (5)	C6—C1—S1—O1	119.5 (2)
K1ⁱⁱ—O4—K1—O3	−119.75 (6)	C2—C1—S1—O1	−57.6 (2)
K1ⁱⁱ—O4—K1—O3ⁱ	81.31 (19)	C6—C1—S1—N1	−127.2 (2)
K1ⁱⁱ—O4—K1—O1	−54.21 (6)	C2—C1—S1—N1	55.7 (2)
K1ⁱⁱ—O4—K1—O2	−37.41 (4)	C6—C1—S1—K1	63.8 (2)
K1ⁱⁱ—O4—K1—S1	−47.208 (16)	C2—C1—S1—K1	−113.3 (2)
S1—O1—K1—O1ⁱⁱⁱ	149.55 (9)	O1ⁱⁱⁱ—K1—S1—O2	143.82 (13)
K1ⁱ—O1—K1—O1ⁱⁱⁱ	−46.65 (10)	O2ⁱⁱ—K1—S1—O2	−58.97 (8)
S1—O1—K1—O2ⁱⁱ	−69.62 (12)	O3—K1—S1—O2	95.08 (11)
K1ⁱ—O1—K1—O2ⁱⁱ	94.17 (7)	O4—K1—S1—O2	23.50 (11)
S1—O1—K1—O3	81.10 (11)	O3ⁱ—K1—S1—O2	−140.10 (11)
K1ⁱ—O1—K1—O3	−115.10 (8)	O1—K1—S1—O2	−171.67 (15)
S1—O1—K1—O4	17.48 (14)	O1ⁱⁱⁱ—K1—S1—O1	−44.51 (11)
K1ⁱ—O1—K1—O4	−178.72 (6)	O2ⁱⁱ—K1—S1—O1	112.70 (12)
S1—O1—K1—O3ⁱ	−147.47 (12)	O3—K1—S1—O1	−93.24 (12)
K1ⁱ—O1—K1—O3ⁱ	16.33 (7)	O4—K1—S1—O1	−164.82 (12)
S1—O1—K1—O2	−4.61 (8)	O3ⁱ—K1—S1—O1	31.57 (12)
K1ⁱ—O1—K1—O2	159.19 (11)	O2—K1—S1—O1	171.67 (15)
K1ⁱ—O1—K1—S1	163.80 (15)	O1ⁱⁱⁱ—K1—S1—N1	−116.44 (14)
S1—O2—K1—O1ⁱⁱⁱ	−72.9 (2)	O2ⁱⁱ—K1—S1—N1	40.78 (13)
K1ⁱⁱ—O2—K1—O1ⁱⁱⁱ	122.30 (16)	O3—K1—S1—N1	−165.17 (13)
S1—O2—K1—O2ⁱⁱ	119.28 (6)	O4—K1—S1—N1	123.25 (13)
K1ⁱⁱ—O2—K1—O2ⁱⁱ	−45.55 (9)	O3ⁱ—K1—S1—N1	−40.36 (13)
S1—O2—K1—O3	−79.32 (10)	O1—K1—S1—N1	−71.93 (16)
K1ⁱⁱ—O2—K1—O3	115.85 (7)	O2—K1—S1—N1	99.75 (16)
S1—O2—K1—O4	−155.84 (10)	O1ⁱⁱⁱ—K1—S1—C1	49.10 (13)
K1ⁱⁱ—O2—K1—O4	39.33 (5)	O2ⁱⁱ—K1—S1—C1	−153.68 (10)
S1—O2—K1—O3ⁱ	44.31 (12)	O3—K1—S1—C1	0.37 (11)
K1ⁱⁱ—O2—K1—O3ⁱ	−120.52 (7)	O4—K1—S1—C1	−71.21 (10)
S1—O2—K1—O1	4.50 (8)	O3ⁱ—K1—S1—C1	125.18 (10)
K1ⁱⁱ—O2—K1—O1	−160.33 (10)	O1—K1—S1—C1	93.61 (15)
K1ⁱⁱ—O2—K1—S1	−164.83 (13)	O2—K1—S1—C1	−94.71 (13)
K1ⁱⁱ—O2—S1—O1	72.5 (5)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^iv	0.80 (2)	2.23 (2)	2.962 (3)	152 (4)
O3—H32···Cl1^v	0.81 (2)	2.73 (2)	3.517 (3)	165 (4)
O4—H41···N1^iv	0.81 (2)	2.19 (2)	2.978 (3)	165 (4)

Symmetry codes: (iv) x, y+1, z; (v) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O
M_r	291.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.301 (2), 6.8277 (6), 27.965 (3)
β (°)	106.28 (1)
V (Å³)	2254.5 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.44 × 0.44 × 0.38

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.640, 0.677
No. of measured, independent and observed [I > 2σ(I)] reflections	4174, 2298, 2181
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.19
No. of reflections	2298
No. of parameters	142
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.46

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), CrysAlis RED, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1ⁱ	0.797 (19)	2.23 (2)	2.962 (3)	152 (4)
O3—H32···Cl1ⁱⁱ	0.806 (19)	2.73 (2)	3.517 (3)	165 (4)
O4—H41···N1ⁱ	0.811 (18)	2.19 (2)	2.978 (3)	165 (4)

Symmetry codes: (i) x, y+1, z; (ii) x−1/2, y+1/2, z.

Acknowledgements

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

References

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