Potassium N-chloro-o-toluene-sulfonamidate monohydrate.

In the crystal structure of the title compound, K(+)·C(7)H(7)ClNO(2)S(-)·H(2)O, the K(+) ion is hepta-coordinated by two O atoms from water mol-ecules, four sulfonyl O atoms and the Cl atom of the anion. The S-N distance of 1.584 (3) Å is consistent with an S-N double bond. In the crystal, anions are connected by K(+) cations into layers parallel to the ab plane. The water mol-ecules are coordinated to the K(+) cations and are additionally linked by inter-molecular O-H⋯Cl and O-H⋯N hydrogen bonding.

Related literature

For our studies of the effect of substituents on the structures of N-haloaryl­sulfonamides, see: Gowda et al. (2009 ▶, 2011 ▶); and on the oxidative strengths of N-halolaryl­sulfonamides, see: Gowda & Kumar (2003 ▶); 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+·C7H7ClNO2S−·H2O

M = 261.76

Orthorhombic,

a = 11.4968 (9) Å

b = 6.7990 (5) Å

c = 26.883 (2) Å

V = 2101.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.94 mm−1

T = 293 K

0.42 × 0.40 × 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 = 0.694, T max = 0.766

4396 measured reflections

2150 independent reflections

1992 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 0.92

2150 reflections

134 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.59 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023555/nc2234sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023555/nc2234Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

K+·C7H7ClNO2S−·H2O	F(000) = 1072
Mr = 261.76	Dx = 1.655 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2737 reflections
a = 11.4968 (9) Å	θ = 3.0–27.7°
b = 6.7990 (5) Å	µ = 0.94 mm−1
c = 26.883 (2) Å	T = 293 K
V = 2101.4 (3) Å3	Prism, colourless
Z = 8	0.42 × 0.40 × 0.30 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2150 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −2→14
Tmin = 0.694, Tmax = 0.766	k = −8→5
4396 measured reflections	l = −33→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0717P)2 + 5.301P] where P = (Fo2 + 2Fc2)/3
2150 reflections	(Δ/σ)max = 0.001
134 parameters	Δρmax = 0.42 e Å−3
4 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq
K1	0.63387 (6)	1.33711 (10)	0.02856 (2)	0.0327 (2)
Cl1	0.47408 (9)	1.20077 (12)	0.12455 (3)	0.0481 (3)
S1	0.55243 (6)	0.85908 (10)	0.08371 (2)	0.0260 (2)
O1	0.5175 (2)	0.6996 (3)	0.05138 (8)	0.0412 (5)
N1	0.4458 (2)	1.0067 (4)	0.08324 (10)	0.0368 (6)
O3	0.7703 (2)	1.1144 (4)	−0.03605 (9)	0.0494 (6)
H31	0.817 (3)	1.179 (6)	−0.0541 (12)	0.059*
H32	0.713 (2)	1.084 (7)	−0.0541 (12)	0.059*
O2	0.66241 (18)	0.9505 (3)	0.07163 (8)	0.0367 (5)
C1	0.5708 (2)	0.7601 (4)	0.14466 (10)	0.0251 (5)
C2	0.4782 (3)	0.6704 (4)	0.17010 (11)	0.0305 (6)
C3	0.5030 (3)	0.5932 (5)	0.21709 (12)	0.0426 (8)
H3	0.4441	0.5301	0.2346	0.051*
C4	0.6116 (4)	0.6073 (5)	0.23828 (12)	0.0492 (9)
H4	0.6249	0.5548	0.2697	0.059*
C5	0.7001 (3)	0.6985 (5)	0.21318 (13)	0.0466 (8)
H5	0.7732	0.7096	0.2277	0.056*
C6	0.6803 (3)	0.7742 (5)	0.16600 (11)	0.0348 (6)
H6	0.7406	0.8345	0.1487	0.042*
C7	0.3566 (3)	0.6577 (5)	0.15053 (14)	0.0427 (8)
H7A	0.3582	0.6144	0.1165	0.051*
H7B	0.3205	0.7849	0.1524	0.051*
H7C	0.3129	0.5657	0.1701	0.051*

	U11	U22	U33	U12	U13	U23
K1	0.0370 (4)	0.0316 (4)	0.0294 (3)	−0.0002 (3)	−0.0028 (2)	0.0026 (3)
Cl1	0.0630 (6)	0.0315 (4)	0.0497 (5)	0.0118 (4)	0.0137 (4)	−0.0022 (3)
S1	0.0319 (4)	0.0261 (4)	0.0199 (3)	0.0016 (3)	0.0016 (2)	0.0001 (2)
O1	0.0564 (14)	0.0378 (12)	0.0293 (11)	−0.0012 (11)	−0.0026 (10)	−0.0105 (10)
N1	0.0396 (14)	0.0365 (14)	0.0344 (13)	0.0095 (11)	−0.0050 (10)	0.0007 (11)
O3	0.0535 (15)	0.0560 (16)	0.0387 (12)	0.0129 (13)	0.0017 (11)	0.0097 (12)
O2	0.0377 (10)	0.0383 (12)	0.0340 (11)	−0.0015 (8)	0.0096 (9)	0.0056 (9)
C1	0.0325 (13)	0.0201 (12)	0.0228 (12)	0.0029 (11)	−0.0005 (10)	−0.0009 (10)
C2	0.0406 (15)	0.0216 (13)	0.0293 (14)	0.0025 (11)	0.0092 (12)	−0.0011 (11)
C3	0.062 (2)	0.0311 (16)	0.0344 (16)	0.0036 (15)	0.0161 (15)	0.0062 (13)
C4	0.079 (3)	0.0414 (18)	0.0274 (15)	0.0164 (18)	−0.0037 (16)	0.0082 (14)
C5	0.057 (2)	0.0455 (19)	0.0377 (17)	0.0096 (16)	−0.0175 (15)	0.0012 (15)
C6	0.0377 (15)	0.0324 (15)	0.0343 (15)	0.0002 (13)	−0.0037 (12)	0.0013 (12)
C7	0.0375 (16)	0.0408 (18)	0.0499 (19)	−0.0067 (14)	0.0107 (14)	−0.0013 (15)

K1—O2i	2.724 (2)	O3—H31	0.848 (10)
K1—O1ii	2.777 (2)	O3—H32	0.847 (10)
K1—O3	2.788 (3)	O2—K1v	2.724 (2)
K1—O3i	2.790 (3)	C1—C6	1.386 (4)
K1—O1iii	2.870 (2)	C1—C2	1.405 (4)
K1—O2	2.891 (2)	C2—C3	1.397 (4)
K1—Cl1	3.3006 (11)	C2—C7	1.497 (5)
K1—N1	3.447 (3)	C3—C4	1.375 (6)
K1—H31	3.25 (4)	C3—H3	0.9300
K1—H32	2.95 (4)	C4—C5	1.369 (6)
Cl1—N1	1.755 (3)	C4—H4	0.9300
S1—O1	1.446 (2)	C5—C6	1.388 (4)
S1—O2	1.446 (2)	C5—H5	0.9300
S1—N1	1.584 (3)	C6—H6	0.9300
S1—C1	1.784 (3)	C7—H7A	0.9600
O1—K1ii	2.777 (2)	C7—H7B	0.9600
O1—K1iv	2.870 (2)	C7—H7C	0.9600
O3—K1v	2.790 (3)
O2i—K1—O1ii	153.30 (7)	O1—S1—O2	115.46 (14)
O2i—K1—O3	86.25 (8)	O1—S1—N1	104.81 (15)
O1ii—K1—O3	79.74 (8)	O2—S1—N1	113.75 (14)
O2i—K1—O3i	74.57 (7)	O1—S1—C1	107.58 (13)
O1ii—K1—O3i	80.01 (7)	O2—S1—C1	105.34 (13)
O3—K1—O3i	75.94 (5)	N1—S1—C1	109.75 (13)
O2i—K1—O1iii	93.83 (7)	S1—O1—K1ii	134.92 (14)
O1ii—K1—O1iii	87.16 (6)	S1—O1—K1iv	130.02 (14)
O3—K1—O1iii	149.53 (7)	K1ii—O1—K1iv	92.84 (6)
O3i—K1—O1iii	74.75 (8)	S1—N1—Cl1	109.14 (15)
O2i—K1—O2	89.39 (6)	S1—N1—K1	86.03 (11)
O1ii—K1—O2	107.42 (7)	Cl1—N1—K1	70.34 (10)
O3—K1—O2	72.04 (7)	K1—O3—K1v	101.62 (8)
O3i—K1—O2	144.97 (8)	K1—O3—H31	116 (3)
O1iii—K1—O2	138.41 (7)	K1v—O3—H31	117 (3)
O2i—K1—Cl1	103.04 (5)	K1—O3—H32	93 (3)
O1ii—K1—Cl1	103.35 (6)	K1v—O3—H32	120 (3)
O3—K1—Cl1	130.37 (6)	H31—O3—H32	107.3 (16)
O3i—K1—Cl1	153.67 (7)	S1—O2—K1v	136.54 (13)
O1iii—K1—Cl1	79.32 (5)	S1—O2—K1	112.42 (12)
O2—K1—Cl1	59.65 (4)	K1v—O2—K1	100.64 (7)
O2i—K1—N1	122.85 (7)	C6—C1—C2	121.1 (3)
O1ii—K1—N1	83.01 (7)	C6—C1—S1	117.5 (2)
O3—K1—N1	105.34 (8)	C2—C1—S1	121.4 (2)
O3i—K1—N1	162.46 (7)	C3—C2—C1	116.6 (3)
O1iii—K1—N1	100.15 (7)	C3—C2—C7	119.1 (3)
O2—K1—N1	46.20 (6)	C1—C2—C7	124.2 (3)
Cl1—K1—N1	30.05 (5)	C4—C3—C2	122.2 (3)
O2i—K1—H31	80.0 (6)	C4—C3—H3	118.9
O1ii—K1—H31	81.2 (6)	C2—C3—H3	118.9
O3—K1—H31	13.6 (5)	C3—C4—C5	120.1 (3)
O3i—K1—H31	62.7 (6)	C3—C4—H4	119.9
O1iii—K1—H31	137.2 (6)	C5—C4—H4	119.9
O2—K1—H31	84.2 (6)	C4—C5—C6	119.8 (3)
Cl1—K1—H31	143.4 (6)	C4—C5—H5	120.1
N1—K1—H31	118.9 (5)	C6—C5—H5	120.1
O2i—K1—H32	102.8 (3)	C5—C6—C1	120.1 (3)
O1ii—K1—H32	63.8 (5)	C5—C6—H6	120.0
O3—K1—H32	16.6 (3)	C1—C6—H6	120.0
O3i—K1—H32	78.7 (8)	C2—C7—H7A	109.5
O1iii—K1—H32	143.6 (7)	C2—C7—H7B	109.5
O2—K1—H32	74.7 (8)	H7A—C7—H7B	109.5
Cl1—K1—H32	126.5 (7)	C2—C7—H7C	109.5
N1—K1—H32	97.6 (6)	H7A—C7—H7C	109.5
H31—K1—H32	24.8 (3)	H7B—C7—H7C	109.5
N1—Cl1—K1	79.61 (10)
O2i—K1—Cl1—N1	−135.35 (10)	N1—K1—O3—K1v	−57.22 (10)
O1ii—K1—Cl1—N1	48.70 (10)	O1—S1—O2—K1v	−29.4 (2)
O3—K1—Cl1—N1	−39.09 (12)	N1—S1—O2—K1v	−150.65 (16)
O3i—K1—Cl1—N1	143.14 (15)	C1—S1—O2—K1v	89.11 (19)
O1iii—K1—Cl1—N1	133.16 (10)	O1—S1—O2—K1	107.12 (14)
O2—K1—Cl1—N1	−53.88 (10)	N1—S1—O2—K1	−14.13 (17)
O2—S1—O1—K1ii	−99.9 (2)	C1—S1—O2—K1	−134.36 (11)
N1—S1—O1—K1ii	26.1 (2)	O2i—K1—O2—S1	147.79 (8)
C1—S1—O1—K1ii	142.86 (17)	O1ii—K1—O2—S1	−53.29 (14)
O2—S1—O1—K1iv	58.3 (2)	O3—K1—O2—S1	−125.95 (14)
N1—S1—O1—K1iv	−175.69 (16)	O3i—K1—O2—S1	−150.81 (12)
C1—S1—O1—K1iv	−58.93 (19)	O1iii—K1—O2—S1	52.71 (17)
O1—S1—N1—Cl1	176.31 (15)	Cl1—K1—O2—S1	42.26 (10)
O2—S1—N1—Cl1	−56.67 (19)	N1—K1—O2—S1	8.18 (10)
C1—S1—N1—Cl1	61.05 (19)	O2i—K1—O2—K1v	−60.99 (11)
O1—S1—N1—K1	−116.09 (11)	O1ii—K1—O2—K1v	97.93 (8)
O2—S1—N1—K1	10.93 (13)	O3—K1—O2—K1v	25.27 (8)
C1—S1—N1—K1	128.65 (10)	O3i—K1—O2—K1v	0.41 (16)
K1—Cl1—N1—S1	78.36 (14)	O1iii—K1—O2—K1v	−156.08 (8)
O2i—K1—N1—S1	−57.37 (13)	Cl1—K1—O2—K1v	−166.52 (9)
O1ii—K1—N1—S1	115.47 (11)	N1—K1—O2—K1v	159.39 (12)
O3—K1—N1—S1	38.17 (12)	O1—S1—C1—C6	119.2 (2)
O3i—K1—N1—S1	130.0 (2)	O2—S1—C1—C6	−4.5 (3)
O1iii—K1—N1—S1	−158.69 (10)	N1—S1—C1—C6	−127.3 (2)
O2—K1—N1—S1	−6.91 (9)	O1—S1—C1—C2	−60.5 (3)
Cl1—K1—N1—S1	−111.95 (14)	O2—S1—C1—C2	175.8 (2)
O2i—K1—N1—Cl1	54.58 (11)	N1—S1—C1—C2	53.0 (3)
O1ii—K1—N1—Cl1	−132.58 (10)	C6—C1—C2—C3	−1.4 (4)
O3—K1—N1—Cl1	150.12 (9)	S1—C1—C2—C3	178.3 (2)
O3i—K1—N1—Cl1	−118.0 (3)	C6—C1—C2—C7	177.1 (3)
O1iii—K1—N1—Cl1	−46.74 (10)	S1—C1—C2—C7	−3.2 (4)
O2—K1—N1—Cl1	105.04 (11)	C1—C2—C3—C4	1.5 (5)
O2i—K1—O3—K1v	65.85 (9)	C7—C2—C3—C4	−177.1 (3)
O1ii—K1—O3—K1v	−136.97 (10)	C2—C3—C4—C5	−0.3 (5)
O3i—K1—O3—K1v	140.87 (13)	C3—C4—C5—C6	−0.9 (5)
O1iii—K1—O3—K1v	157.04 (11)	C4—C5—C6—C1	1.0 (5)
O2—K1—O3—K1v	−24.72 (8)	C2—C1—C6—C5	0.2 (5)
Cl1—K1—O3—K1v	−38.10 (13)	S1—C1—C6—C5	−179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl1vi	0.85 (1)	2.74 (2)	3.568 (3)	166 (4)
O3—H32···N1ii	0.85 (1)	2.08 (1)	2.909 (4)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Cl1i	0.85 (1)	2.74 (2)	3.568 (3)	166 (4)
O3—H32⋯N1ii	0.85 (1)	2.08 (1)	2.909 (4)	167 (3)

Symmetry codes: (i) ; (ii) .