Potassium N-bromo-4-chloro-benzene-sulfonamidate monohydrate.

In the structure of the title compound, K(+)·C(6)H(4)BrClNO(2)S(-)·H(2)O, the K(+) cation is hepta-coordinated. It is connected to two water O atoms, four sulfonyl O atoms and one Br atom. Further, the sulfonyl and water O atoms in the structure are bridged in a bidentate fashion. The S-N distance of 1.584 (6) Å is consistent with an S-N double bond, The crystal structure is stabilized by inter-molecular O-H⋯N hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-haloaryl­sulfonamides, see: Gowda et al. (2007 ▶, 2011 ▶); and on the oxidative strengths of N-halolaryl­sulfonamides, see: Usha & Gowda (2006 ▶). For similar structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶). For the preparation of the title compound, see: Gowda & Usha (2003 ▶).

Experimental

Crystal data

K+·C6H4BrClNO2S−·H2O

M = 326.64

Monoclinic,

a = 15.596 (1) Å

b = 10.188 (1) Å

c = 6.7649 (7) Å

β = 99.947 (9)°

V = 1058.73 (17) Å3

Z = 4

Mo Kα radiation

μ = 4.70 mm−1

T = 293 K

0.34 × 0.34 × 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 = 0.298, T max = 0.333

3796 measured reflections

2147 independent reflections

1984 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.156

S = 1.19

2147 reflections

134 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.22 e Å−3

Δρmin = −0.95 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/S1600536811023610/ds2118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023610/ds2118Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023610/ds2118Isup3.cml

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

K+·C6H4BrClNO2S−·H2O	F(000) = 640
Mr = 326.64	Dx = 2.049 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2989 reflections
a = 15.596 (1) Å	θ = 3.0–27.8°
b = 10.188 (1) Å	µ = 4.70 mm−1
c = 6.7649 (7) Å	T = 293 K
β = 99.947 (9)°	Prism, yellow
V = 1058.73 (17) Å3	0.34 × 0.34 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2147 independent reflections
Radiation source: fine-focus sealed tube	1984 reflections with I > 2σ(I)
graphite	Rint = 0.035
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −19→17
Tmin = 0.298, Tmax = 0.333	k = −5→12
3796 measured reflections	l = −8→6

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0614P)2 + 8.645P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.014
2147 reflections	Δρmax = 1.22 e Å−3
134 parameters	Δρmin = −0.95 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: 0.044 (3)

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
Br1	0.25575 (4)	0.43815 (7)	−0.31985 (10)	0.0299 (3)
K1	0.44027 (9)	0.61960 (15)	−0.3785 (2)	0.0252 (4)
Cl1	−0.02963 (13)	0.5964 (3)	0.2758 (3)	0.0534 (6)
S1	0.34113 (9)	0.53777 (15)	0.0566 (2)	0.0190 (4)
O1	0.3587 (3)	0.6607 (5)	−0.0369 (7)	0.0310 (11)
O2	0.4024 (3)	0.5053 (6)	0.2355 (7)	0.0329 (11)
O3	0.5513 (3)	0.7034 (5)	−0.6370 (8)	0.0318 (11)
H31	0.572 (5)	0.692 (9)	−0.739 (8)	0.038*
H32	0.589 (4)	0.753 (7)	−0.578 (12)	0.038*
N1	0.3390 (4)	0.4126 (6)	−0.0831 (8)	0.0258 (12)
C1	0.2367 (4)	0.5577 (6)	0.1250 (9)	0.0197 (12)
C2	0.1965 (4)	0.4475 (7)	0.1854 (11)	0.0278 (14)
H2	0.2239	0.3662	0.1914	0.033*
C3	0.1148 (5)	0.4602 (8)	0.2370 (11)	0.0341 (16)
H3	0.0867	0.3879	0.2806	0.041*
C4	0.0755 (4)	0.5829 (8)	0.2223 (10)	0.0306 (15)
C5	0.1156 (5)	0.6906 (8)	0.1639 (11)	0.0371 (17)
H5	0.0885	0.7721	0.1573	0.044*
C6	0.1977 (5)	0.6771 (7)	0.1141 (10)	0.0286 (14)
H6	0.2260	0.7499	0.0733	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.0227 (4)	0.0383 (5)	0.0267 (4)	−0.0011 (3)	−0.0019 (3)	−0.0082 (3)
K1	0.0199 (7)	0.0332 (8)	0.0234 (7)	0.0037 (5)	0.0062 (5)	0.0010 (6)
Cl1	0.0198 (9)	0.0954 (18)	0.0479 (11)	0.0083 (10)	0.0137 (8)	0.0025 (11)
S1	0.0136 (7)	0.0251 (8)	0.0178 (7)	−0.0009 (5)	0.0013 (5)	−0.0026 (5)
O1	0.032 (3)	0.029 (2)	0.034 (3)	−0.009 (2)	0.014 (2)	−0.005 (2)
O2	0.019 (2)	0.052 (3)	0.024 (2)	0.006 (2)	−0.0043 (18)	−0.003 (2)
O3	0.023 (2)	0.042 (3)	0.032 (3)	−0.005 (2)	0.008 (2)	0.000 (2)
N1	0.021 (3)	0.032 (3)	0.024 (3)	0.005 (2)	0.002 (2)	−0.003 (2)
C1	0.018 (3)	0.025 (3)	0.016 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C2	0.020 (3)	0.027 (3)	0.037 (4)	0.002 (2)	0.007 (3)	0.002 (3)
C3	0.028 (4)	0.040 (4)	0.036 (4)	−0.010 (3)	0.009 (3)	0.002 (3)
C4	0.016 (3)	0.056 (5)	0.020 (3)	0.003 (3)	0.003 (2)	0.000 (3)
C5	0.036 (4)	0.040 (4)	0.036 (4)	0.015 (3)	0.010 (3)	0.002 (3)
C6	0.029 (3)	0.026 (3)	0.033 (3)	0.002 (3)	0.012 (3)	0.006 (3)

Br1—N1	1.897 (5)	O2—K1ii	2.784 (5)
Br1—K1	3.5001 (16)	O2—K1vi	2.827 (5)
K1—O1i	2.704 (5)	O3—K1i	2.818 (6)
K1—O2ii	2.784 (5)	O3—K1v	3.295 (6)
K1—O3	2.799 (5)	O3—H31	0.82 (2)
K1—O3iii	2.818 (6)	O3—H32	0.82 (2)
K1—O2iv	2.827 (5)	C1—C6	1.356 (9)
K1—O1	2.855 (5)	C1—C2	1.382 (9)
K1—O3v	3.295 (6)	C2—C3	1.384 (10)
K1—N1	3.468 (6)	C2—H2	0.9300
Cl1—C4	1.745 (7)	C3—C4	1.388 (11)
S1—O2	1.446 (5)	C3—H3	0.9300
S1—O1	1.450 (5)	C4—C5	1.355 (11)
S1—N1	1.584 (6)	C5—C6	1.386 (10)
S1—C1	1.780 (6)	C5—H5	0.9300
O1—K1iii	2.704 (5)	C6—H6	0.9300
N1—Br1—K1	73.28 (18)	O2—S1—C1	108.1 (3)
O1i—K1—O2ii	147.39 (17)	O1—S1—C1	105.3 (3)
O1i—K1—O3	78.43 (15)	N1—S1—C1	108.7 (3)
O2ii—K1—O3	75.72 (16)	S1—O1—K1iii	130.8 (3)
O1i—K1—O3iii	84.28 (16)	S1—O1—K1	111.7 (3)
O2ii—K1—O3iii	71.01 (15)	K1iii—O1—K1	101.36 (15)
O3—K1—O3iii	77.42 (11)	S1—O2—K1ii	144.2 (3)
O1i—K1—O2iv	88.05 (16)	S1—O2—K1vi	133.0 (3)
O2ii—K1—O2iv	99.40 (13)	K1ii—O2—K1vi	80.60 (12)
O3—K1—O2iv	66.52 (15)	K1—O3—K1i	99.95 (16)
O3iii—K1—O2iv	143.94 (16)	K1—O3—K1v	72.59 (13)
O1i—K1—O1	87.38 (13)	K1i—O3—K1v	132.42 (18)
O2ii—K1—O1	105.97 (15)	K1—O3—H31	149 (6)
O3—K1—O1	150.63 (16)	K1i—O3—H31	84 (6)
O3iii—K1—O1	75.66 (14)	K1v—O3—H31	82 (6)
O2iv—K1—O1	139.19 (15)	K1—O3—H32	110 (6)
O1i—K1—O3v	148.56 (15)	K1i—O3—H32	102 (6)
O2ii—K1—O3v	60.31 (15)	K1v—O3—H32	125 (6)
O3—K1—O3v	107.41 (13)	H31—O3—H32	98 (9)
O3iii—K1—O3v	127.12 (10)	S1—N1—Br1	109.5 (3)
O2iv—K1—O3v	67.58 (15)	S1—N1—K1	83.6 (2)
O1—K1—O3v	98.14 (14)	Br1—N1—K1	75.12 (18)
O1i—K1—N1	120.12 (14)	C6—C1—C2	121.5 (6)
O2ii—K1—N1	89.06 (15)	C6—C1—S1	120.7 (5)
O3—K1—N1	159.76 (16)	C2—C1—S1	117.8 (5)
O3iii—K1—N1	110.52 (14)	C1—C2—C3	118.9 (6)
O2iv—K1—N1	103.80 (15)	C1—C2—H2	120.6
O1—K1—N1	46.50 (13)	C3—C2—H2	120.6
O3v—K1—N1	52.68 (13)	C2—C3—C4	118.7 (7)
O1i—K1—Br1	98.17 (12)	C2—C3—H3	120.7
O2ii—K1—Br1	114.30 (12)	C4—C3—H3	120.7
O3—K1—Br1	147.31 (12)	C5—C4—C3	122.0 (7)
O3iii—K1—Br1	135.01 (11)	C5—C4—Cl1	119.6 (6)
O2iv—K1—Br1	80.94 (11)	C3—C4—Cl1	118.4 (6)
O1—K1—Br1	59.70 (10)	C4—C5—C6	118.8 (7)
O3v—K1—Br1	59.85 (9)	C4—C5—H5	120.6
N1—K1—Br1	31.60 (9)	C6—C5—H5	120.6
O2—S1—O1	114.6 (3)	C1—C6—C5	120.1 (7)
O2—S1—N1	105.0 (3)	C1—C6—H6	120.0
O1—S1—N1	114.9 (3)	C5—C6—H6	120.0
N1—Br1—K1—O1i	−137.2 (2)	O3iii—K1—O3—K1v	125.32 (11)
N1—Br1—K1—O2ii	39.8 (2)	O2iv—K1—O3—K1v	−55.11 (13)
N1—Br1—K1—O3	141.5 (3)	O1—K1—O3—K1v	149.3 (3)
N1—Br1—K1—O3iii	−47.2 (2)	O3v—K1—O3—K1v	0.0
N1—Br1—K1—O2iv	136.1 (2)	N1—K1—O3—K1v	9.7 (4)
N1—Br1—K1—O1	−55.1 (2)	Br1—K1—O3—K1v	−60.9 (2)
N1—Br1—K1—O3v	66.8 (2)	O2—S1—N1—Br1	177.0 (3)
O2—S1—O1—K1iii	−27.2 (5)	O1—S1—N1—Br1	−56.3 (4)
N1—S1—O1—K1iii	−148.9 (3)	C1—S1—N1—Br1	61.5 (4)
C1—S1—O1—K1iii	91.5 (4)	O2—S1—N1—K1	−111.3 (2)
O2—S1—O1—K1	101.4 (3)	O1—S1—N1—K1	15.5 (3)
N1—S1—O1—K1	−20.3 (4)	C1—S1—N1—K1	133.2 (2)
C1—S1—O1—K1	−139.9 (3)	K1—Br1—N1—S1	77.5 (3)
O1i—K1—O1—S1	148.80 (19)	O1i—K1—N1—S1	−61.2 (3)
O2ii—K1—O1—S1	−61.4 (3)	O2ii—K1—N1—S1	103.5 (2)
O3—K1—O1—S1	−150.6 (3)	O3—K1—N1—S1	144.3 (4)
O3iii—K1—O1—S1	−126.4 (3)	O3iii—K1—N1—S1	34.2 (2)
O2iv—K1—O1—S1	64.8 (4)	O2iv—K1—N1—S1	−157.0 (2)
O3v—K1—O1—S1	−0.1 (3)	O1—K1—N1—S1	−9.74 (19)
N1—K1—O1—S1	11.4 (2)	O3v—K1—N1—S1	155.9 (3)
Br1—K1—O1—S1	47.7 (2)	Br1—K1—N1—S1	−112.2 (3)
O1i—K1—O1—K1iii	−68.3 (3)	O1i—K1—N1—Br1	51.0 (2)
O2ii—K1—O1—K1iii	81.47 (19)	O2ii—K1—N1—Br1	−144.32 (18)
O3—K1—O1—K1iii	−7.7 (4)	O3—K1—N1—Br1	−103.5 (4)
O3iii—K1—O1—K1iii	16.46 (16)	O3iii—K1—N1—Br1	146.39 (17)
O2iv—K1—O1—K1iii	−152.3 (2)	O2iv—K1—N1—Br1	−44.9 (2)
O3v—K1—O1—K1iii	142.81 (15)	O1—K1—N1—Br1	102.4 (2)
N1—K1—O1—K1iii	154.3 (3)	O3v—K1—N1—Br1	−91.9 (2)
Br1—K1—O1—K1iii	−169.3 (2)	O2—S1—C1—C6	112.9 (6)
O1—S1—O2—K1ii	−88.7 (6)	O1—S1—C1—C6	−10.0 (6)
N1—S1—O2—K1ii	38.3 (6)	N1—S1—C1—C6	−133.7 (6)
C1—S1—O2—K1ii	154.2 (5)	O2—S1—C1—C2	−68.3 (6)
O1—S1—O2—K1vi	66.9 (5)	O1—S1—C1—C2	168.8 (5)
N1—S1—O2—K1vi	−166.1 (4)	N1—S1—C1—C2	45.1 (6)
C1—S1—O2—K1vi	−50.2 (5)	C6—C1—C2—C3	−0.4 (10)
O1i—K1—O3—K1i	−16.53 (16)	S1—C1—C2—C3	−179.2 (5)
O2ii—K1—O3—K1i	−176.5 (2)	C1—C2—C3—C4	1.2 (11)
O3iii—K1—O3—K1i	−103.2 (2)	C2—C3—C4—C5	−1.6 (11)
O2iv—K1—O3—K1i	76.40 (17)	C2—C3—C4—Cl1	176.9 (6)
O1—K1—O3—K1i	−79.2 (3)	C3—C4—C5—C6	1.1 (11)
O3v—K1—O3—K1i	131.51 (17)	Cl1—C4—C5—C6	−177.4 (6)
N1—K1—O3—K1i	141.2 (4)	C2—C1—C6—C5	−0.1 (10)
Br1—K1—O3—K1i	70.6 (3)	S1—C1—C6—C5	178.6 (5)
O1i—K1—O3—K1v	−148.04 (15)	C4—C5—C6—C1	−0.2 (11)
O2ii—K1—O3—K1v	52.01 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1v	0.82 (2)	2.25 (5)	3.005 (8)	152 (8)
O3—H32···N1vii	0.82 (2)	2.16 (3)	2.967 (8)	166 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1i	0.82 (2)	2.25 (5)	3.005 (8)	152 (8)
O3—H32⋯N1ii	0.82 (2)	2.16 (3)	2.967 (8)	166 (9)

Symmetry codes: (i) ; (ii) .