Potassium N,2-dichloro-benzene-sulfonamidate sesquihydrate.

In the title compound, K(+)·C(6)H(4)Cl(2)NO(2)S(-)·1.5H(2)O, one water mol-ecule has crystallographically imposed twofold symmetry. The K(+) ion is heptacoordinated by three O atoms from water mol-ecules and by four sulfonyl O atoms of N-chloro-2-chloro-benzene-sulfonamide 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 inter-molecular 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 ▶, 2011 ▶); 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 = 291.19

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 1.19

2298 reflections

142 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.46 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/S1600536811021891/sj5159sup1.cif

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

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

K+·C6H4Cl2NO2S−·1.5H2O	F(000) = 1176
Mr = 291.19	Dx = 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

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

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(Fo2) + (0.0457P)2 + 5.0762P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.002
2298 reflections	Δρmax = 0.47 e Å−3
142 parameters	Δρmin = −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)

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
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)

	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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1iv	0.80 (2)	2.23 (2)	2.962 (3)	152 (4)
O3—H32···Cl1v	0.81 (2)	2.73 (2)	3.517 (3)	165 (4)
O4—H41···N1iv	0.81 (2)	2.19 (2)	2.978 (3)	165 (4)

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) ; (ii) .