Potassium N-chlorobenzene­sulfon­amidate monohydrate

Gowda, B.T.; Foro, S.; Kožíšek, J.; Fuess, H.

doi:10.1107/S1600536807024178

Potassium N-chlorobenzenesulfonamidate monohydrate

B. T. Gowda, S. Foro, J. Kožíšek and H. Fuess

In the title compound, K⁺·C₆H₅ClNO₂S⁻·H₂O, the S—N distance of 1.581 (4) Å is consistent with an S=N double bond. The ions and molecules in the crystal structure are held together by O—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024178/bt2364sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024178/bt2364Isup2.hkl Contains datablock I

CCDC reference: 614963

checkCIF report

Key indicators

Single-crystal X-ray study
T = 303 K
Mean (C-C) = 0.009 Å
R factor = 0.046
wR factor = 0.123
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.849(10) ......       4.00 su-Ra
              O3   -H31O    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.846(10) ......       4.00 su-Ra
              O3   -H32O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.849(10) ......       4.00 su-Ra
              O3   -H31O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.846(10) ......       4.00 su-Ra
              O3   -H32O    1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.71 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.70 Deg.
              O2   -S1   -K1      1.555   1.555   7.765

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of arylsulfonamides and their N-halo compounds is of interest as they show distinct physical, chemical and biological properties. Many of these compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. Thus, N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2005; Gowda & Shetty, 2004). In the present work, the structure of potassium N- chlorobenzenesulfonamde has been determined to explore the effect of substitution and replacing a sodium ion by a potassium ion on the solid state structures of N-chloroarylsulfonamides (Gowda, Jyothi et al., 2007; Gowda, Kozisek et al., 2007; Gowda, Savitha et al., 2007; Gowda, Srilatha et al., 2007). The structure of the title compound (Fig. 1) resembles those of sodium N-chloro- benzenesulfonamde (George et al., 2000) and other sodium N-chloro-arylsulfonamdes (Olmstead & Power, 1986; Gowda, Jyothi et al., 2007; Gowda, Kozisek et al., 2007; Gowda, Savitha et al., 2007; Gowda, Srilatha et al., 2007). The S—N distance of 1.581 (4)Å is consistent with a S—N double bond. The molecules in the structure are held together by O—H^···N hydrogen bonds.

Related literature top

For related literature, see: George et al. (2000); Gowda & Shetty (2004); Gowda et al. (2003, 2005); Gowda, Jyothi et al. (2007); Gowda, Kozisek et al. (2007); Gowda, Savitha et al. (2007); Gowda, Srilatha et al. (2007); Jyothi & Gowda (2004); Olmstead & Power (1986).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003; Jyothi & Gowda, 2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR (Jyothi & Gowda, 2004) and NQR spectra (Gowda et al., 2003). Single crystals of the title compound were obtained from a slow evaporation of its chloroform solution and used for X-ray diffraction studies at room temperature.

Structure description top

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram viewed down the axis b

Potassium N-chlorobenzenesulfonamidate monohydrate top

Crystal data top

K⁺.C₆H₅ClNO₂S⁻.H₂O	F(000) = 1008
M_r = 247.74	D_x = 1.669 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 10.214 (1) Å	θ = 8.7–25.0°
b = 6.8111 (4) Å	µ = 9.03 mm⁻¹
c = 28.336 (1) Å	T = 303 K
V = 1971.3 (2) Å³	Laminar, colourless
Z = 8	0.22 × 0.13 × 0.03 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1102 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 66.9°, θ_min = 3.1°
ω/2θ scans	h = 0→12
Absorption correction: psi-scan (North et al., 1968)	k = 0→8
T_min = 0.305, T_max = 0.798	l = −3→33
1953 measured reflections	3 standard reflections every 120 min
1756 independent reflections	intensity decay: 4.8%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0611P)²] where P = (F_o² + 2F_c²)/3
1756 reflections	(Δ/σ)_max < 0.001
124 parameters	Δρ_max = 0.27 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

K⁺.C₆H₅ClNO₂S⁻.H₂O	V = 1971.3 (2) Å³
M_r = 247.74	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 10.214 (1) Å	µ = 9.03 mm⁻¹
b = 6.8111 (4) Å	T = 303 K
c = 28.336 (1) Å	0.22 × 0.13 × 0.03 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1102 reflections with I > 2σ(I)
Absorption correction: psi-scan (North et al., 1968)	R_int = 0.035
T_min = 0.305, T_max = 0.798	3 standard reflections every 120 min
1953 measured reflections	intensity decay: 4.8%
1756 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.27 e Å⁻³
1756 reflections	Δρ_min = −0.38 e Å⁻³
124 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	0.9541 (5)	0.7329 (6)	0.35902 (15)	0.0416 (10)
C2	0.8421 (5)	0.7230 (8)	0.33231 (18)	0.0579 (14)
H2	0.7687	0.6566	0.3434	0.070*
C3	0.8404 (8)	0.8127 (10)	0.2891 (2)	0.083 (2)
H3	0.7651	0.8057	0.2707	0.100*
C4	0.9464 (10)	0.9120 (9)	0.2723 (2)	0.090 (2)
H4	0.9435	0.9736	0.2430	0.108*
C5	1.0569 (8)	0.9193 (9)	0.2992 (2)	0.081 (2)
H5	1.1301	0.9855	0.2879	0.097*
C6	1.0622 (5)	0.8313 (8)	0.34244 (19)	0.0566 (13)
H6	1.1381	0.8378	0.3605	0.068*
N1	1.0836 (4)	0.4749 (6)	0.41555 (14)	0.0477 (10)
O1	0.9920 (3)	0.7666 (5)	0.44928 (11)	0.0544 (9)
O2	0.8372 (3)	0.5189 (5)	0.42122 (12)	0.0524 (9)
O3	0.7965 (4)	−0.1477 (6)	0.52779 (12)	0.0558 (9)
H31O	0.744 (4)	−0.130 (8)	0.5507 (12)	0.067*
H32O	0.823 (5)	−0.260 (4)	0.5366 (19)	0.067*
S1	0.96138 (11)	0.61724 (16)	0.41499 (4)	0.0386 (3)
Cl1	1.06255 (14)	0.2980 (2)	0.37111 (5)	0.0634 (4)
K1	0.88083 (10)	0.14650 (14)	0.46609 (4)	0.0455 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.049 (2)	0.036 (2)	0.039 (2)	0.004 (2)	0.003 (2)	−0.001 (2)
C2	0.068 (3)	0.050 (3)	0.056 (3)	0.004 (3)	−0.009 (3)	0.001 (3)
C3	0.115 (6)	0.072 (4)	0.062 (4)	0.026 (4)	−0.034 (4)	−0.001 (4)
C4	0.170 (8)	0.054 (4)	0.046 (3)	0.026 (5)	0.008 (5)	0.005 (3)
C5	0.128 (6)	0.050 (3)	0.064 (4)	−0.001 (4)	0.046 (4)	0.011 (3)
C6	0.063 (3)	0.049 (3)	0.058 (3)	−0.007 (3)	0.006 (3)	−0.003 (3)
N1	0.049 (2)	0.039 (2)	0.055 (2)	0.0110 (18)	−0.011 (2)	−0.013 (2)
O1	0.071 (2)	0.0441 (18)	0.0480 (19)	0.0053 (18)	−0.0023 (17)	−0.0096 (16)
O2	0.0446 (17)	0.0498 (19)	0.063 (2)	−0.0084 (16)	0.0104 (16)	0.0080 (18)
O3	0.060 (2)	0.049 (2)	0.058 (2)	0.003 (2)	0.0111 (17)	0.007 (2)
S1	0.0419 (6)	0.0346 (5)	0.0392 (5)	0.0010 (5)	0.0016 (5)	−0.0005 (5)
Cl1	0.0751 (9)	0.0501 (7)	0.0651 (8)	0.0151 (7)	−0.0009 (7)	−0.0155 (7)
K1	0.0518 (6)	0.0368 (5)	0.0480 (5)	−0.0006 (5)	−0.0067 (5)	0.0033 (5)

Geometric parameters (Å, º) top

C1—C2	1.373 (7)	O2—S1	1.445 (3)
C1—C6	1.375 (7)	O2—K1ⁱⁱⁱ	2.708 (3)
C1—S1	1.772 (4)	O2—K1	2.872 (4)
C2—C3	1.370 (8)	O3—K1	2.795 (4)
C2—H2	0.9300	O3—K1^iv	2.881 (4)
C3—C4	1.362 (10)	O3—K1^v	3.301 (4)
C3—H3	0.9300	O3—H31O	0.849 (10)
C4—C5	1.362 (9)	O3—H32O	0.846 (10)
C4—H4	0.9300	S1—K1	3.6130 (15)
C5—C6	1.366 (8)	S1—K1ⁱⁱⁱ	3.7886 (15)
C5—H5	0.9300	Cl1—K1	3.4285 (18)
C6—H6	0.9300	K1—O2^iv	2.708 (3)
N1—S1	1.581 (4)	K1—O1ⁱ	2.791 (3)
N1—Cl1	1.756 (4)	K1—O1^vi	2.865 (3)
N1—K1	3.368 (4)	K1—O3ⁱⁱⁱ	2.881 (4)
O1—S1	1.441 (3)	K1—O3^v	3.301 (4)
O1—K1ⁱ	2.791 (3)	K1—K1^v	3.688 (2)
O1—K1ⁱⁱ	2.865 (3)	K1—S1^iv	3.7886 (15)

C2—C1—C6	120.3 (5)	O1ⁱ—K1—O2	105.39 (11)
C2—C1—S1	120.4 (4)	O3—K1—O2	149.56 (10)
C6—C1—S1	119.2 (4)	O1^vi—K1—O2	141.75 (10)
C3—C2—C1	118.8 (6)	O2^iv—K1—O3ⁱⁱⁱ	85.65 (11)
C3—C2—H2	120.6	O1ⁱ—K1—O3ⁱⁱⁱ	70.61 (10)
C1—C2—H2	120.6	O3—K1—O3ⁱⁱⁱ	77.03 (8)
C4—C3—C2	121.6 (6)	O1^vi—K1—O3ⁱⁱⁱ	142.11 (10)
C4—C3—H3	119.2	O2—K1—O3ⁱⁱⁱ	75.02 (10)
C2—C3—H3	119.2	O2^iv—K1—O3^v	147.86 (11)
C5—C4—C3	118.7 (6)	O1ⁱ—K1—O3^v	59.30 (10)
C5—C4—H4	120.6	O3—K1—O3^v	106.07 (9)
C3—C4—H4	120.6	O1^vi—K1—O3^v	67.38 (10)
C4—C5—C6	121.3 (6)	O2—K1—O3^v	100.14 (10)
C4—C5—H5	119.4	O3ⁱⁱⁱ—K1—O3^v	126.49 (7)
C6—C5—H5	119.4	O2^iv—K1—N1	121.29 (10)
C5—C6—C1	119.3 (6)	O1ⁱ—K1—N1	86.46 (10)
C5—C6—H6	120.4	O3—K1—N1	158.67 (10)
C1—C6—H6	120.4	O1^vi—K1—N1	106.57 (10)
S1—N1—Cl1	108.5 (2)	O2—K1—N1	47.22 (9)
S1—N1—K1	85.74 (16)	O3ⁱⁱⁱ—K1—N1	108.76 (10)
Cl1—N1—K1	76.94 (14)	O3^v—K1—N1	53.59 (9)
S1—O1—K1ⁱ	146.1 (2)	O2^iv—K1—Cl1	99.98 (8)
S1—O1—K1ⁱⁱ	131.57 (19)	O1ⁱ—K1—Cl1	111.02 (8)
K1ⁱ—O1—K1ⁱⁱ	81.38 (9)	O3—K1—Cl1	150.88 (8)
S1—O2—K1ⁱⁱⁱ	129.1 (2)	O1^vi—K1—Cl1	85.80 (8)
S1—O2—K1	109.11 (17)	O2—K1—Cl1	58.04 (7)
K1ⁱⁱⁱ—O2—K1	101.73 (10)	O3ⁱⁱⁱ—K1—Cl1	132.09 (8)
K1—O3—K1^iv	99.38 (11)	O3^v—K1—Cl1	59.99 (7)
K1—O3—K1^v	73.93 (9)	N1—K1—Cl1	29.93 (7)
K1^iv—O3—K1^v	131.37 (13)	O2^iv—K1—S1	106.50 (8)
K1—O3—H31O	125 (4)	O1ⁱ—K1—S1	92.88 (8)
K1^iv—O3—H31O	98 (4)	O3—K1—S1	163.14 (9)
K1^v—O3—H31O	126 (4)	O1^vi—K1—S1	130.12 (8)
K1—O3—H32O	137 (4)	O2—K1—S1	22.21 (6)
K1^iv—O3—H32O	87 (4)	O3ⁱⁱⁱ—K1—S1	87.40 (8)
K1^v—O3—H32O	71 (4)	O3^v—K1—S1	77.96 (7)
H31O—O3—H32O	96 (5)	N1—K1—S1	25.88 (6)
O1—S1—O2	115.8 (2)	Cl1—K1—S1	45.17 (3)
O1—S1—N1	104.8 (2)	O2^iv—K1—K1^v	127.87 (8)
O2—S1—N1	114.1 (2)	O1ⁱ—K1—K1^v	50.19 (7)
O1—S1—C1	107.4 (2)	O3—K1—K1^v	59.32 (8)
O2—S1—C1	106.2 (2)	O1^vi—K1—K1^v	48.43 (7)
N1—S1—C1	108.4 (2)	O2—K1—K1^v	144.19 (8)
O1—S1—K1	113.93 (14)	O3ⁱⁱⁱ—K1—K1^v	111.22 (8)
O2—S1—K1	48.69 (14)	O3^v—K1—K1^v	46.75 (7)
N1—S1—K1	68.38 (16)	N1—K1—K1^v	100.07 (7)
C1—S1—K1	138.02 (15)	Cl1—K1—K1^v	102.39 (5)
O1—S1—K1ⁱⁱⁱ	84.57 (15)	S1—K1—K1^v	122.60 (5)
O2—S1—K1ⁱⁱⁱ	33.70 (14)	O2^iv—K1—S1^iv	17.23 (7)
N1—S1—K1ⁱⁱⁱ	139.20 (16)	O1ⁱ—K1—S1^iv	140.27 (8)
C1—S1—K1ⁱⁱⁱ	106.24 (16)	O3—K1—S1^iv	85.24 (8)
K1—S1—K1ⁱⁱⁱ	71.54 (3)	O1^vi—K1—S1^iv	104.75 (8)
N1—Cl1—K1	73.13 (14)	O2—K1—S1^iv	74.58 (7)
O2^iv—K1—O1ⁱ	148.70 (11)	O3ⁱⁱⁱ—K1—S1^iv	71.19 (8)
O2^iv—K1—O3	79.05 (11)	O3^v—K1—S1^iv	160.31 (7)
O1ⁱ—K1—O3	76.00 (11)	N1—K1—S1^iv	116.09 (7)
O2^iv—K1—O1^vi	87.59 (10)	Cl1—K1—S1^iv	102.43 (4)
O1ⁱ—K1—O1^vi	98.62 (9)	S1—K1—S1^iv	95.94 (4)
O3—K1—O1^vi	65.09 (10)	K1^v—K1—S1^iv	141.23 (5)
O2^iv—K1—O2	87.02 (9)

C6—C1—C2—C3	0.0 (8)	S1—O2—K1—S1^iv	−163.7 (2)
S1—C1—C2—C3	−179.4 (4)	K1ⁱⁱⁱ—O2—K1—S1^iv	57.42 (9)
C1—C2—C3—C4	−0.5 (9)	S1—N1—K1—O2^iv	60.56 (19)
C2—C3—C4—C5	0.8 (10)	Cl1—N1—K1—O2^iv	−49.51 (17)
C3—C4—C5—C6	−0.7 (10)	S1—N1—K1—O1ⁱ	−104.06 (16)
C4—C5—C6—C1	0.2 (9)	Cl1—N1—K1—O1ⁱ	145.87 (14)
C2—C1—C6—C5	0.1 (7)	S1—N1—K1—O3	−138.5 (3)
S1—C1—C6—C5	179.6 (4)	Cl1—N1—K1—O3	111.4 (3)
K1ⁱ—O1—S1—O2	94.6 (4)	S1—N1—K1—O1^vi	158.00 (14)
K1ⁱⁱ—O1—S1—O2	−69.3 (3)	Cl1—N1—K1—O1^vi	47.93 (15)
K1ⁱ—O1—S1—N1	−31.9 (4)	S1—N1—K1—O2	10.75 (13)
K1ⁱⁱ—O1—S1—N1	164.2 (2)	Cl1—N1—K1—O2	−99.32 (17)
K1ⁱ—O1—S1—C1	−147.0 (4)	S1—N1—K1—O3ⁱⁱⁱ	−35.91 (17)
K1ⁱⁱ—O1—S1—C1	49.1 (3)	Cl1—N1—K1—O3ⁱⁱⁱ	−145.98 (13)
K1ⁱ—O1—S1—K1	40.6 (4)	S1—N1—K1—O3^v	−157.9 (2)
K1ⁱⁱ—O1—S1—K1	−123.28 (19)	Cl1—N1—K1—O3^v	92.03 (15)
K1ⁱ—O1—S1—K1ⁱⁱⁱ	107.7 (3)	S1—N1—K1—Cl1	110.1 (2)
K1ⁱⁱ—O1—S1—K1ⁱⁱⁱ	−56.2 (2)	Cl1—N1—K1—S1	−110.1 (2)
K1ⁱⁱⁱ—O2—S1—O1	23.9 (3)	S1—N1—K1—K1^v	−152.57 (13)
K1—O2—S1—O1	−100.1 (2)	Cl1—N1—K1—K1^v	97.36 (12)
K1ⁱⁱⁱ—O2—S1—N1	145.6 (2)	S1—N1—K1—S1^iv	41.80 (16)
K1—O2—S1—N1	21.6 (3)	Cl1—N1—K1—S1^iv	−68.27 (13)
K1ⁱⁱⁱ—O2—S1—C1	−95.2 (3)	N1—Cl1—K1—O2^iv	138.71 (15)
K1—O2—S1—C1	140.88 (18)	N1—Cl1—K1—O1ⁱ	−36.86 (15)
K1ⁱⁱⁱ—O2—S1—K1	123.9 (3)	N1—Cl1—K1—O3	−135.9 (2)
K1—O2—S1—K1ⁱⁱⁱ	−123.9 (3)	N1—Cl1—K1—O1^vi	−134.49 (15)
Cl1—N1—S1—O1	−175.0 (2)	N1—Cl1—K1—O2	58.61 (15)
K1—N1—S1—O1	110.29 (16)	N1—Cl1—K1—O3ⁱⁱⁱ	45.55 (17)
Cl1—N1—S1—O2	57.4 (3)	N1—Cl1—K1—O3^v	−68.25 (15)
K1—N1—S1—O2	−17.3 (2)	N1—Cl1—K1—S1	35.31 (13)
Cl1—N1—S1—C1	−60.6 (3)	N1—Cl1—K1—K1^v	−88.70 (13)
K1—N1—S1—C1	−135.32 (17)	N1—Cl1—K1—S1^iv	121.32 (13)
Cl1—N1—S1—K1	74.7 (2)	O1—S1—K1—O2^iv	133.79 (18)
Cl1—N1—S1—K1ⁱⁱⁱ	86.1 (3)	O2—S1—K1—O2^iv	29.67 (14)
K1—N1—S1—K1ⁱⁱⁱ	11.4 (2)	N1—S1—K1—O2^iv	−129.09 (17)
C2—C1—S1—O1	−122.0 (4)	C1—S1—K1—O2^iv	−35.3 (3)
C6—C1—S1—O1	58.6 (4)	K1ⁱⁱⁱ—S1—K1—O2^iv	58.70 (9)
C2—C1—S1—O2	2.5 (4)	O1—S1—K1—O1ⁱ	−21.3 (2)
C6—C1—S1—O2	−177.0 (4)	O2—S1—K1—O1ⁱ	−125.4 (2)
C2—C1—S1—N1	125.4 (4)	N1—S1—K1—O1ⁱ	75.80 (17)
C6—C1—S1—N1	−54.1 (4)	C1—S1—K1—O1ⁱ	169.6 (2)
C2—C1—S1—K1	47.6 (5)	K1ⁱⁱⁱ—S1—K1—O1ⁱ	−96.41 (7)
C6—C1—S1—K1	−131.9 (3)	O1—S1—K1—O3	26.7 (3)
C2—C1—S1—K1ⁱⁱⁱ	−32.7 (4)	O2—S1—K1—O3	−77.4 (4)
C6—C1—S1—K1ⁱⁱⁱ	147.9 (4)	N1—S1—K1—O3	123.8 (3)
S1—N1—Cl1—K1	−80.9 (2)	C1—S1—K1—O3	−142.4 (4)
K1^iv—O3—K1—O2^iv	16.83 (11)	K1ⁱⁱⁱ—S1—K1—O3	−48.4 (3)
K1^v—O3—K1—O2^iv	147.33 (11)	O1—S1—K1—O1^vi	−125.1 (2)
K1^iv—O3—K1—O1ⁱ	177.77 (13)	O2—S1—K1—O1^vi	130.8 (2)
K1^v—O3—K1—O1ⁱ	−51.73 (8)	N1—S1—K1—O1^vi	−28.01 (18)
K1^iv—O3—K1—O1^vi	−75.61 (12)	C1—S1—K1—O1^vi	65.8 (3)
K1^v—O3—K1—O1^vi	54.89 (9)	K1ⁱⁱⁱ—S1—K1—O1^vi	159.78 (10)
K1^iv—O3—K1—O2	81.1 (2)	O1—S1—K1—O2	104.1 (3)
K1^v—O3—K1—O2	−148.38 (19)	N1—S1—K1—O2	−158.8 (2)
K1^iv—O3—K1—O3ⁱⁱⁱ	104.84 (16)	C1—S1—K1—O2	−65.0 (3)
K1^v—O3—K1—O3ⁱⁱⁱ	−124.66 (8)	K1ⁱⁱⁱ—S1—K1—O2	29.03 (19)
K1^iv—O3—K1—O3^v	−130.50 (13)	O1—S1—K1—O3ⁱⁱⁱ	49.11 (18)
K1^v—O3—K1—O3^v	0.0	O2—S1—K1—O3ⁱⁱⁱ	−55.0 (2)
K1^iv—O3—K1—N1	−146.7 (2)	N1—S1—K1—O3ⁱⁱⁱ	146.23 (17)
K1^v—O3—K1—N1	−16.2 (3)	C1—S1—K1—O3ⁱⁱⁱ	−120.0 (2)
K1^iv—O3—K1—Cl1	−74.04 (19)	K1ⁱⁱⁱ—S1—K1—O3ⁱⁱⁱ	−25.98 (7)
K1^v—O3—K1—Cl1	56.46 (18)	O1—S1—K1—O3^v	−79.09 (17)
K1^iv—O3—K1—S1	127.9 (3)	O2—S1—K1—O3^v	176.8 (2)
K1^v—O3—K1—S1	−101.6 (3)	N1—S1—K1—O3^v	18.03 (16)
K1^iv—O3—K1—K1^v	−130.50 (13)	C1—S1—K1—O3^v	111.8 (2)
K1^iv—O3—K1—S1^iv	33.07 (9)	K1ⁱⁱⁱ—S1—K1—O3^v	−154.17 (7)
K1^v—O3—K1—S1^iv	163.57 (7)	O1—S1—K1—N1	−97.1 (2)
S1—O2—K1—O2^iv	−151.62 (13)	O2—S1—K1—N1	158.8 (2)
K1ⁱⁱⁱ—O2—K1—O2^iv	69.51 (17)	C1—S1—K1—N1	93.8 (3)
S1—O2—K1—O1ⁱ	57.6 (2)	K1ⁱⁱⁱ—S1—K1—N1	−172.21 (16)
K1ⁱⁱⁱ—O2—K1—O1ⁱ	−81.31 (12)	O1—S1—K1—Cl1	−138.48 (17)
S1—O2—K1—O3	146.03 (19)	O2—S1—K1—Cl1	117.4 (2)
K1ⁱⁱⁱ—O2—K1—O3	7.2 (3)	N1—S1—K1—Cl1	−41.36 (15)
S1—O2—K1—O1^vi	−69.3 (3)	C1—S1—K1—Cl1	52.4 (2)
K1ⁱⁱⁱ—O2—K1—O1^vi	151.81 (13)	K1ⁱⁱⁱ—S1—K1—Cl1	146.43 (5)
S1—O2—K1—O3ⁱⁱⁱ	122.1 (2)	O1—S1—K1—K1^v	−64.54 (17)
K1ⁱⁱⁱ—O2—K1—O3ⁱⁱⁱ	−16.78 (11)	O2—S1—K1—K1^v	−168.7 (2)
S1—O2—K1—O3^v	−3.2 (2)	N1—S1—K1—K1^v	32.58 (16)
K1ⁱⁱⁱ—O2—K1—O3^v	−142.05 (10)	C1—S1—K1—K1^v	126.4 (2)
S1—O2—K1—N1	−12.44 (15)	K1ⁱⁱⁱ—S1—K1—K1^v	−139.63 (4)
K1ⁱⁱⁱ—O2—K1—N1	−151.31 (18)	O1—S1—K1—S1^iv	119.89 (16)
S1—O2—K1—Cl1	−47.91 (15)	O2—S1—K1—S1^iv	15.8 (2)
K1ⁱⁱⁱ—O2—K1—Cl1	173.22 (14)	N1—S1—K1—S1^iv	−142.99 (15)
K1ⁱⁱⁱ—O2—K1—S1	−138.9 (3)	C1—S1—K1—S1^iv	−49.2 (2)
S1—O2—K1—K1^v	16.4 (3)	K1ⁱⁱⁱ—S1—K1—S1^iv	44.80 (4)
K1ⁱⁱⁱ—O2—K1—K1^v	−122.42 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31O···N1^vii	0.85 (1)	2.17 (3)	2.948 (5)	152 (5)
O3—H32O···N1^v	0.85 (1)	2.21 (3)	3.007 (5)	156 (5)

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

Experimental details

Crystal data
Chemical formula	K⁺.C₆H₅ClNO₂S⁻.H₂O
M_r	247.74
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	303
a, b, c (Å)	10.214 (1), 6.8111 (4), 28.336 (1)
V (Å³)	1971.3 (2)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	9.03
Crystal size (mm)	0.22 × 0.13 × 0.03

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	Psi-scan (North et al., 1968)
T_min, T_max	0.305, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	1953, 1756, 1102
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 0.99
No. of reflections	1756
No. of parameters	124
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)	0.27, −0.38

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.