Potassium N,4-dichloro-benzene-sulfonamidate monohydrate.

The structure of the title salt hydrate, K(+)·C(6)H(4)Cl(2)NO(2)S(-)·H(2)O, shows each of the sulfonyl O and water O atoms to be bidentate bridging. The hepta-coordinated 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. (2007 ▶) 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 = 282.18

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.067

S = 1.04

2139 reflections

134 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.28 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/S1600536811020319/tk2749sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811020319/tk2749Isup3.cml

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

K+·C6H4Cl2NO2S·H2O	F(000) = 568
Mr = 282.18	Dx = 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

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	Rint = 0.009
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→19
Tmin = 0.633, Tmax = 0.715	k = −8→12
3796 measured reflections	l = −6→8

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(Fo2) + (0.0355P)2 + 0.5896P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.046
2139 reflections	Δρmax = 0.39 e Å−3
134 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—K1iv	2.8714 (15)
C4—C5	1.380 (3)	O3—K1v	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—O2iv	2.6940 (13)
C6—H6	0.9300	K1—O1i	2.7965 (13)
N1—S1	1.5883 (15)	K1—O1vi	2.8547 (13)
N1—Cl2	1.7620 (15)	K1—O3iii	2.8714 (15)
N1—K1	3.4014 (16)	K1—O3v	3.1905 (16)
O1—S1	1.4460 (13)	K1—Cl2	3.3944 (6)
C6—C1—C2	120.77 (15)	O2iv—K1—O1vi	86.74 (4)
C6—C1—S1	118.90 (13)	O1i—K1—O1vi	100.42 (3)
C2—C1—S1	120.32 (13)	O3—K1—O1vi	65.66 (4)
C3—C2—C1	119.51 (17)	O2iv—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)	O1vi—K1—O2	140.52 (4)
C4—C3—H3	120.4	O2iv—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)	O1vi—K1—O3iii	142.71 (4)
C5—C4—Cl1	119.05 (15)	O2—K1—O3iii	75.11 (4)
C4—C5—C6	119.05 (17)	O2iv—K1—O3v	148.33 (4)
C4—C5—H5	120.5	O1i—K1—O3v	61.43 (4)
C6—C5—H5	120.5	O3—K1—O3v	106.31 (3)
C1—C6—C5	119.64 (17)	O1vi—K1—O3v	68.17 (4)
C1—C6—H6	120.2	O2—K1—O3v	99.95 (4)
C5—C6—H6	120.2	O3iii—K1—O3v	127.16 (3)
S1—N1—Cl2	108.69 (8)	O2iv—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)	O1vi—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)	O3v—K1—Cl2	60.54 (3)
S1—O2—K1	110.21 (7)	O2iv—K1—N1	120.37 (4)
K1iii—O2—K1	102.77 (4)	O1i—K1—N1	90.00 (4)
K1—O3—K1iv	99.34 (4)	O3—K1—N1	159.60 (4)
K1—O3—K1v	73.69 (3)	O1vi—K1—N1	105.39 (4)
K1iv—O3—K1v	132.78 (5)	O2—K1—N1	47.20 (4)
K1—O3—H31	140.3 (17)	O3iii—K1—N1	110.31 (4)
K1iv—O3—H31	90.1 (17)	O3v—K1—N1	53.77 (3)
K1v—O3—H31	71.8 (17)	Cl2—K1—N1	30.05 (3)
K1—O3—H32	110.2 (17)	N1—Cl2—K1	75.20 (5)
K1iv—O3—H32	102.1 (17)	O1—S1—O2	115.65 (8)
K1v—O3—H32	124.4 (17)	O1—S1—N1	104.35 (8)
H31—O3—H32	105 (2)	O2—S1—N1	114.45 (8)
O2iv—K1—O1i	145.96 (4)	O1—S1—C1	107.86 (8)
O2iv—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—O1vi	156.60 (5)
C2—C3—C4—Cl1	177.31 (14)	Cl2—N1—K1—O1vi	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—O3v	−156.23 (8)
K1iv—O3—K1—O2iv	15.72 (4)	Cl2—N1—K1—O3v	92.80 (6)
K1v—O3—K1—O2iv	147.72 (4)	S1—N1—K1—Cl2	110.97 (8)
K1iv—O3—K1—O1i	174.75 (5)	S1—N1—Cl2—K1	−79.04 (8)
K1v—O3—K1—O1i	−53.25 (3)	O2iv—K1—Cl2—N1	138.20 (6)
K1iv—O3—K1—O1vi	−75.88 (5)	O1i—K1—Cl2—N1	−37.47 (6)
K1v—O3—K1—O1vi	56.11 (4)	O3—K1—Cl2—N1	−138.93 (8)
K1iv—O3—K1—O2	78.94 (9)	O1vi—K1—Cl2—N1	−136.11 (6)
K1v—O3—K1—O2	−149.06 (7)	O2—K1—Cl2—N1	57.27 (6)
K1iv—O3—K1—O3iii	102.66 (7)	O3iii—K1—Cl2—N1	47.15 (7)
K1v—O3—K1—O3iii	−125.35 (3)	O3v—K1—Cl2—N1	−67.72 (6)
K1iv—O3—K1—O3v	−132.00 (5)	K1i—O1—S1—O2	85.59 (16)
K1v—O3—K1—O3v	0.0	K1ii—O1—S1—O2	−67.43 (12)
K1iv—O3—K1—Cl2	−72.81 (7)	K1i—O1—S1—N1	−41.06 (17)
K1v—O3—K1—Cl2	59.19 (7)	K1ii—O1—S1—N1	165.92 (10)
K1iv—O3—K1—N1	−143.50 (10)	K1i—O1—S1—C1	−156.25 (14)
K1v—O3—K1—N1	−11.50 (12)	K1ii—O1—S1—C1	50.73 (13)
S1—O2—K1—O2iv	−149.02 (5)	K1iii—O2—S1—O1	26.81 (12)
K1iii—O2—K1—O2iv	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—O1vi	−67.75 (10)	Cl2—N1—S1—O1	−176.41 (8)
K1iii—O2—K1—O1vi	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—O3v	−0.13 (8)	Cl2—N1—S1—C1	−61.63 (10)
K1iii—O2—K1—O3v	−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—O2iv	61.26 (7)	C6—C1—S1—N1	−51.24 (16)
Cl2—N1—K1—O2iv	−49.71 (6)	C2—C1—S1—N1	127.66 (14)
S1—N1—K1—O1i	−102.59 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1v	0.81 (2)	2.22 (2)	2.987 (2)	160 (2)
O3—H32···N1vii	0.81 (2)	2.18 (2)	2.967 (2)	166 (2)

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—O3iv	2.8714 (15)
K1—O3v	3.1905 (16)
K1—Cl2	3.3944 (6)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1v	0.81 (2)	2.22 (2)	2.987 (2)	160 (2)
O3—H32⋯N1vi	0.81 (2)	2.18 (2)	2.967 (2)	166 (2)

Symmetry codes: (v) ; (vi) .