Potassium N,4-dichloro­benzene­sulfonamidate monohydrate

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

doi:10.1107/S1600536811020319

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m918

doi:10.1107/S1600536811020319

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Potassium N,4-dichlorobenzenesulfonamidate monohydrate

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 24 May 2011; accepted 27 May 2011; online 4 June 2011)

The structure of the title salt hydrate, K⁺·C₆H₄Cl₂NO₂S⁻·H₂O, shows each of the sulfonyl O and water O atoms to be bidentate bridging. The heptacoordinated K⁺ cation is connected to two water O atoms, four sulfonyl O atoms and one Cl atom. The crystal structure comprises sheets in the bc plane which are further stabilized by O—H⋯N hydrogen bonds.

Related literature

For our studies into the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2007a ,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

Crystal data

K⁺·C₆H₄Cl₂NO₂S·H₂O
M_r = 282.18
Monoclinic, P 2₁ /c
a = 15.487 (1) Å
b = 10.0620 (8) Å
c = 6.8061 (5) Å
β = 99.888 (7)°
V = 1044.84 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 293 K
0.42 × 0.42 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.633, T_max = 0.715
3796 measured reflections
2139 independent reflections
1962 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.067
S = 1.04
2139 reflections
134 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected bond lengths (Å)

K1—O2	2.8576 (13)
K1—O2ⁱ	2.6940 (13)
K1—O1ⁱⁱ	2.7965 (13)
K1—O1ⁱⁱⁱ	2.8547 (13)
K1—O3^iv	2.8714 (15)
K1—O3^v	3.1905 (16)
K1—Cl2	3.3944 (6)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) x, y, z-1; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1^v	0.81 (2)	2.22 (2)	2.987 (2)	160 (2)
O3—H32⋯N1^vi	0.81 (2)	2.18 (2)	2.967 (2)	166 (2)
Symmetry codes: (v) -x+1, -y+1, -z; (vi) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536811020319/tk2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020319/tk2749Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020319/tk2749Isup3.cml

checkCIF report

Comment top

The chemistry of arylsulfonamides and their N-halo compounds is of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda & Shetty, 2004; Usha & Gowda, 2006). To explore the effect of replacing the sodium ion by potassium ion on the solid state structures of N-chloroarylsulfonamides (Gowda et al., 2007a,b), in the present work, the structure of potassium N-chloro-4-chloro- benzenesulfonamidate monohydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of sodium N-chloro-benzenesulfonamide (George et al., 2000) and other sodium N-chloro-arylsulfonamides (Olmstead & Power, 1986; Gowda et al., 2007a,b). In particular, there is no interaction between the nitrogen and potassium atom in the molecule.

K⁺ hepta coordination involves two O atoms from bridging water molecules, four sulfonyl O1 atoms from bridging N-chloro-4-chlorobenzenesulfonamide anions, and one Cl atom (Table 1). This is in contrast to octahedral coordination of K⁺ in potassium N-chloro-benzenesulfonamidate monohydrate by two O atoms from water molecules and four sulfonyl O atoms of four different N-chlorobenzenesulfonamide anions (Gowda et al., 2007a), and octahedral coordination of Na⁺ in sodium N-chloro-4-chlorobenzenesulfonamidate sesquihydrate by three O atoms of water molecules and three sulfonyl O atoms of three different N-chloro- 4-chlorobenzenesulfonamide anions (Gowda et al., 2007b). The S—N distance of N1—S1, 1.588 (2) Å is consistent with a S—N double bond.

The crystal structure comprises sheets in the bc plane which are further stabilized by O—H···N hydrogen bonds (Table 2 and Fig. 2).

Related literature top

For our studies into the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2007a,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 according to the literature method (Jyothi & Gowda, 2004). The purity of the compound was checked by determining its melting point. Yellow 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 (Oxford Diffraction, 2009); 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 salt hydrate, showing the atom labelling scheme for the asymmetric unit and extended to show the coordination geometry for the K⁺ cation. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii. See Table 1 for symmetry operations.
	Fig. 2. Molecular packing of the title salt hydrate with hydrogen bonding shown as dashed lines.

Potassium N,4-dichlorobenzenesulfonamidate monohydrate top

Crystal data top

K⁺·C₆H₄Cl₂NO₂S·H₂O	F(000) = 568
M_r = 282.18	D_x = 1.794 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2944 reflections
a = 15.487 (1) Å	θ = 3.0–27.7°
b = 10.0620 (8) Å	µ = 1.20 mm⁻¹
c = 6.8061 (5) Å	T = 293 K
β = 99.888 (7)°	Prism, yellow
V = 1044.84 (13) Å³	0.42 × 0.42 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2139 independent reflections
Radiation source: fine-focus sealed tube	1962 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→19
T_min = 0.633, T_max = 0.715	k = −8→12
3796 measured reflections	l = −6→8

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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0355P)² + 0.5896P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.046
2139 reflections	Δρ_max = 0.39 e Å⁻³
134 parameters	Δρ_min = −0.28 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0241 (14)

Crystal data top

K⁺·C₆H₄Cl₂NO₂S·H₂O	V = 1044.84 (13) Å³
M_r = 282.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.487 (1) Å	µ = 1.20 mm⁻¹
b = 10.0620 (8) Å	T = 293 K
c = 6.8061 (5) Å	0.42 × 0.42 × 0.30 mm
β = 99.888 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2139 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1962 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.715	R_int = 0.009
3796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	2 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
2139 reflections	Δρ_min = −0.28 e Å⁻³
134 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.23433 (10)	0.44537 (16)	0.6229 (2)	0.0260 (3)
C2	0.18971 (12)	0.32599 (18)	0.5954 (3)	0.0342 (4)
H2	0.2152	0.2528	0.5447	0.041*
C3	0.10664 (13)	0.3162 (2)	0.6440 (3)	0.0394 (4)
H3	0.0760	0.2364	0.6266	0.047*
C4	0.07005 (11)	0.4256 (2)	0.7181 (3)	0.0346 (4)
C5	0.11456 (13)	0.5446 (2)	0.7494 (3)	0.0383 (4)
H5	0.0892	0.6170	0.8028	0.046*
C6	0.19736 (12)	0.55468 (18)	0.7003 (3)	0.0348 (4)
H6	0.2280	0.6344	0.7193	0.042*
N1	0.33843 (10)	0.58782 (15)	0.4143 (2)	0.0325 (3)
O1	0.40091 (8)	0.49624 (15)	0.73235 (19)	0.0411 (3)
O2	0.35592 (8)	0.33682 (13)	0.4620 (2)	0.0375 (3)
O3	0.55174 (9)	0.29958 (15)	−0.1344 (2)	0.0401 (3)
H31	0.5708 (15)	0.324 (2)	−0.231 (3)	0.048*
H32	0.5890 (13)	0.251 (2)	−0.076 (3)	0.048*
K1	0.43783 (2)	0.38377 (4)	0.12285 (5)	0.03214 (12)
Cl1	−0.03614 (3)	0.41509 (7)	0.76911 (8)	0.05237 (17)
Cl2	0.26012 (3)	0.56182 (5)	0.19737 (7)	0.04134 (14)
S1	0.33942 (3)	0.46167 (4)	0.55495 (6)	0.02637 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0254 (8)	0.0310 (8)	0.0227 (7)	−0.0002 (6)	0.0072 (6)	0.0017 (6)
C2	0.0348 (9)	0.0327 (9)	0.0374 (9)	−0.0024 (7)	0.0129 (7)	−0.0040 (7)
C3	0.0363 (10)	0.0435 (10)	0.0399 (10)	−0.0129 (8)	0.0110 (8)	−0.0030 (8)
C4	0.0251 (8)	0.0527 (11)	0.0274 (8)	−0.0012 (8)	0.0084 (6)	0.0046 (8)
C5	0.0378 (10)	0.0415 (10)	0.0390 (10)	0.0068 (8)	0.0161 (8)	−0.0020 (8)
C6	0.0359 (10)	0.0314 (9)	0.0393 (9)	−0.0032 (7)	0.0131 (8)	−0.0025 (7)
N1	0.0300 (7)	0.0362 (8)	0.0309 (7)	−0.0066 (6)	0.0045 (6)	0.0050 (6)
O1	0.0301 (6)	0.0599 (8)	0.0312 (7)	−0.0064 (6)	−0.0004 (5)	0.0055 (6)
O2	0.0377 (7)	0.0361 (7)	0.0424 (7)	0.0091 (5)	0.0172 (6)	0.0027 (5)
O3	0.0370 (7)	0.0464 (8)	0.0401 (7)	0.0061 (6)	0.0154 (6)	0.0044 (6)
K1	0.0309 (2)	0.0366 (2)	0.0309 (2)	−0.00472 (15)	0.01105 (14)	−0.00100 (15)
Cl1	0.0282 (2)	0.0845 (4)	0.0475 (3)	−0.0038 (2)	0.0153 (2)	0.0031 (3)
Cl2	0.0344 (2)	0.0542 (3)	0.0339 (2)	0.00022 (19)	0.00135 (17)	0.0115 (2)
S1	0.0224 (2)	0.0318 (2)	0.0258 (2)	0.00090 (15)	0.00658 (15)	0.00292 (15)

Geometric parameters (Å, º) top

C1—C6	1.385 (2)	O1—K1ⁱ	2.7965 (13)
C1—C2	1.382 (2)	O1—K1ⁱⁱ	2.8547 (13)
C1—S1	1.7742 (16)	O2—S1	1.4489 (13)
C2—C3	1.386 (3)	O2—K1ⁱⁱⁱ	2.6940 (13)
C2—H2	0.9300	O2—K1	2.8576 (13)
C3—C4	1.373 (3)	O3—K1	2.8204 (14)
C3—H3	0.9300	O3—K1^iv	2.8714 (15)
C4—C5	1.380 (3)	O3—K1^v	3.1905 (16)
C4—Cl1	1.7414 (18)	O3—H31	0.808 (16)
C5—C6	1.383 (3)	O3—H32	0.808 (16)
C5—H5	0.9300	K1—O2^iv	2.6940 (13)
C6—H6	0.9300	K1—O1ⁱ	2.7965 (13)
N1—S1	1.5883 (15)	K1—O1^vi	2.8547 (13)
N1—Cl2	1.7620 (15)	K1—O3ⁱⁱⁱ	2.8714 (15)
N1—K1	3.4014 (16)	K1—O3^v	3.1905 (16)
O1—S1	1.4460 (13)	K1—Cl2	3.3944 (6)

C6—C1—C2	120.77 (15)	O2^iv—K1—O1^vi	86.74 (4)
C6—C1—S1	118.90 (13)	O1ⁱ—K1—O1^vi	100.42 (3)
C2—C1—S1	120.32 (13)	O3—K1—O1^vi	65.66 (4)
C3—C2—C1	119.51 (17)	O2^iv—K1—O2	87.06 (3)
C3—C2—H2	120.2	O1ⁱ—K1—O2	106.27 (4)
C1—C2—H2	120.2	O3—K1—O2	149.71 (4)
C4—C3—C2	119.30 (17)	O1^vi—K1—O2	140.52 (4)
C4—C3—H3	120.4	O2^iv—K1—O3ⁱⁱⁱ	84.52 (4)
C2—C3—H3	120.4	O1ⁱ—K1—O3ⁱⁱⁱ	69.60 (4)
C3—C4—C5	121.72 (16)	O3—K1—O3ⁱⁱⁱ	77.07 (3)
C3—C4—Cl1	119.22 (15)	O1^vi—K1—O3ⁱⁱⁱ	142.71 (4)
C5—C4—Cl1	119.05 (15)	O2—K1—O3ⁱⁱⁱ	75.11 (4)
C4—C5—C6	119.05 (17)	O2^iv—K1—O3^v	148.33 (4)
C4—C5—H5	120.5	O1ⁱ—K1—O3^v	61.43 (4)
C6—C5—H5	120.5	O3—K1—O3^v	106.31 (3)
C1—C6—C5	119.64 (17)	O1^vi—K1—O3^v	68.17 (4)
C1—C6—H6	120.2	O2—K1—O3^v	99.95 (4)
C5—C6—H6	120.2	O3ⁱⁱⁱ—K1—O3^v	127.16 (3)
S1—N1—Cl2	108.69 (8)	O2^iv—K1—Cl2	99.11 (3)
S1—N1—K1	84.87 (6)	O1ⁱ—K1—Cl2	114.67 (3)
Cl2—N1—K1	74.75 (5)	O3—K1—Cl2	149.42 (3)
S1—O1—K1ⁱ	144.92 (8)	O1^vi—K1—Cl2	83.80 (3)
S1—O1—K1ⁱⁱ	132.84 (8)	O2—K1—Cl2	58.85 (3)
K1ⁱ—O1—K1ⁱⁱ	79.58 (3)	O3ⁱⁱⁱ—K1—Cl2	133.39 (3)
S1—O2—K1ⁱⁱⁱ	130.01 (8)	O3^v—K1—Cl2	60.54 (3)
S1—O2—K1	110.21 (7)	O2^iv—K1—N1	120.37 (4)
K1ⁱⁱⁱ—O2—K1	102.77 (4)	O1ⁱ—K1—N1	90.00 (4)
K1—O3—K1^iv	99.34 (4)	O3—K1—N1	159.60 (4)
K1—O3—K1^v	73.69 (3)	O1^vi—K1—N1	105.39 (4)
K1^iv—O3—K1^v	132.78 (5)	O2—K1—N1	47.20 (4)
K1—O3—H31	140.3 (17)	O3ⁱⁱⁱ—K1—N1	110.31 (4)
K1^iv—O3—H31	90.1 (17)	O3^v—K1—N1	53.77 (3)
K1^v—O3—H31	71.8 (17)	Cl2—K1—N1	30.05 (3)
K1—O3—H32	110.2 (17)	N1—Cl2—K1	75.20 (5)
K1^iv—O3—H32	102.1 (17)	O1—S1—O2	115.65 (8)
K1^v—O3—H32	124.4 (17)	O1—S1—N1	104.35 (8)
H31—O3—H32	105 (2)	O2—S1—N1	114.45 (8)
O2^iv—K1—O1ⁱ	145.96 (4)	O1—S1—C1	107.86 (8)
O2^iv—K1—O3	78.54 (4)	O2—S1—C1	105.79 (8)
O1ⁱ—K1—O3	74.49 (4)	N1—S1—C1	108.45 (8)

C6—C1—C2—C3	0.7 (3)	Cl2—N1—K1—O1ⁱ	146.44 (5)
S1—C1—C2—C3	−178.16 (14)	S1—N1—K1—O3	−142.50 (10)
C1—C2—C3—C4	0.2 (3)	Cl2—N1—K1—O3	106.52 (12)
C2—C3—C4—C5	−1.4 (3)	S1—N1—K1—O1^vi	156.60 (5)
C2—C3—C4—Cl1	177.31 (14)	Cl2—N1—K1—O1^vi	45.63 (6)
C3—C4—C5—C6	1.6 (3)	S1—N1—K1—O2	9.86 (5)
Cl1—C4—C5—C6	−177.09 (14)	Cl2—N1—K1—O2	−101.12 (6)
C2—C1—C6—C5	−0.5 (3)	S1—N1—K1—O3ⁱⁱⁱ	−34.41 (7)
S1—C1—C6—C5	178.40 (14)	Cl2—N1—K1—O3ⁱⁱⁱ	−145.38 (5)
C4—C5—C6—C1	−0.6 (3)	S1—N1—K1—O3^v	−156.23 (8)
K1^iv—O3—K1—O2^iv	15.72 (4)	Cl2—N1—K1—O3^v	92.80 (6)
K1^v—O3—K1—O2^iv	147.72 (4)	S1—N1—K1—Cl2	110.97 (8)
K1^iv—O3—K1—O1ⁱ	174.75 (5)	S1—N1—Cl2—K1	−79.04 (8)
K1^v—O3—K1—O1ⁱ	−53.25 (3)	O2^iv—K1—Cl2—N1	138.20 (6)
K1^iv—O3—K1—O1^vi	−75.88 (5)	O1ⁱ—K1—Cl2—N1	−37.47 (6)
K1^v—O3—K1—O1^vi	56.11 (4)	O3—K1—Cl2—N1	−138.93 (8)
K1^iv—O3—K1—O2	78.94 (9)	O1^vi—K1—Cl2—N1	−136.11 (6)
K1^v—O3—K1—O2	−149.06 (7)	O2—K1—Cl2—N1	57.27 (6)
K1^iv—O3—K1—O3ⁱⁱⁱ	102.66 (7)	O3ⁱⁱⁱ—K1—Cl2—N1	47.15 (7)
K1^v—O3—K1—O3ⁱⁱⁱ	−125.35 (3)	O3^v—K1—Cl2—N1	−67.72 (6)
K1^iv—O3—K1—O3^v	−132.00 (5)	K1ⁱ—O1—S1—O2	85.59 (16)
K1^v—O3—K1—O3^v	0.0	K1ⁱⁱ—O1—S1—O2	−67.43 (12)
K1^iv—O3—K1—Cl2	−72.81 (7)	K1ⁱ—O1—S1—N1	−41.06 (17)
K1^v—O3—K1—Cl2	59.19 (7)	K1ⁱⁱ—O1—S1—N1	165.92 (10)
K1^iv—O3—K1—N1	−143.50 (10)	K1ⁱ—O1—S1—C1	−156.25 (14)
K1^v—O3—K1—N1	−11.50 (12)	K1ⁱⁱ—O1—S1—C1	50.73 (13)
S1—O2—K1—O2^iv	−149.02 (5)	K1ⁱⁱⁱ—O2—S1—O1	26.81 (12)
K1ⁱⁱⁱ—O2—K1—O2^iv	69.17 (7)	K1—O2—S1—O1	−101.25 (8)
S1—O2—K1—O1ⁱ	62.84 (8)	K1ⁱⁱⁱ—O2—S1—N1	148.17 (8)
K1ⁱⁱⁱ—O2—K1—O1ⁱ	−78.97 (5)	K1—O2—S1—N1	20.11 (10)
S1—O2—K1—O3	149.81 (7)	K1ⁱⁱⁱ—O2—S1—C1	−92.49 (10)
K1ⁱⁱⁱ—O2—K1—O3	8.00 (11)	K1—O2—S1—C1	139.44 (7)
S1—O2—K1—O1^vi	−67.75 (10)	Cl2—N1—S1—O1	−176.41 (8)
K1ⁱⁱⁱ—O2—K1—O1^vi	150.44 (5)	K1—N1—S1—O1	111.60 (6)
S1—O2—K1—O3ⁱⁱⁱ	125.88 (8)	Cl2—N1—S1—O2	56.20 (11)
K1ⁱⁱⁱ—O2—K1—O3ⁱⁱⁱ	−15.93 (4)	K1—N1—S1—O2	−15.79 (8)
S1—O2—K1—O3^v	−0.13 (8)	Cl2—N1—S1—C1	−61.63 (10)
K1ⁱⁱⁱ—O2—K1—O3^v	−141.94 (4)	K1—N1—S1—C1	−133.62 (6)
S1—O2—K1—Cl2	−46.53 (6)	C6—C1—S1—O1	61.22 (16)
K1ⁱⁱⁱ—O2—K1—Cl2	171.66 (5)	C2—C1—S1—O1	−119.88 (15)
S1—O2—K1—N1	−11.49 (6)	C6—C1—S1—O2	−174.45 (14)
K1ⁱⁱⁱ—O2—K1—N1	−153.30 (7)	C2—C1—S1—O2	4.44 (16)
S1—N1—K1—O2^iv	61.26 (7)	C6—C1—S1—N1	−51.24 (16)
Cl2—N1—K1—O2^iv	−49.71 (6)	C2—C1—S1—N1	127.66 (14)
S1—N1—K1—O1ⁱ	−102.59 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^v	0.81 (2)	2.22 (2)	2.987 (2)	160 (2)
O3—H32···N1^vii	0.81 (2)	2.18 (2)	2.967 (2)	166 (2)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₄Cl₂NO₂S·H₂O
M_r	282.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.487 (1), 10.0620 (8), 6.8061 (5)
β (°)	99.888 (7)
V (Å³)	1044.84 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.42 × 0.42 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.633, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	3796, 2139, 1962
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.067, 1.04
No. of reflections	2139
No. of parameters	134
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.28

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

Selected bond lengths (Å) top

K1—O2ⁱ	2.6940 (13)	K1—O3^iv	2.8714 (15)
K1—O1ⁱⁱ	2.7965 (13)	K1—O3^v	3.1905 (16)
K1—O1ⁱⁱⁱ	2.8547 (13)	K1—Cl2	3.3944 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^v	0.808 (16)	2.215 (17)	2.987 (2)	160 (2)
O3—H32···N1^vi	0.808 (16)	2.177 (17)	2.967 (2)	166 (2)

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

Acknowledgements

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

References

George, E., Vivekanandan, S. & Sivakumar, K. (2000). Acta Cryst. C56, 1208–1209. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Kožíšek, J. & Fuess, H. (2007a). Acta Cryst. E63, m1688. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Foro, S., Kožíšek, J. & Fuess, H. (2007b). Acta Cryst. E63, m1644–m1645. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848–864. Web of Science CrossRef CAS Google Scholar
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64–68. CAS Google Scholar
Olmstead, M. M. & Power, P. P. (1986). Inorg. Chem. 25, 4057–4058. CSD CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359. Web of Science CrossRef CAS Google Scholar