Potassium N-bromo-2-chloro-benzene-sulfonamidate sesquihydrate.

In the structure of the title compound, K(+)·C(6)H(4)BrClNO(2)S(-)·1.5H(2)O, the K(+) ion is hepta-coordinated by three O atoms from water mol-ecules and by four sulfonyl O atoms of N-bromo-2-chloro-benzene-sulfonamidate anions. The S-N distance of 1.582 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by inter-molecular O-H⋯Br and O-H⋯N hydrogen bonds. The asymmetric unit consits of one potassium cation, one N-bromo-2-chloro-benzene-sulfonamidate anion and one water mol-ecule in general positions and one water mol-ecule located on a twofold rotation axis.

Related literature

For preparation of N-haloaryl­sulfonamides, see: Usha & Gowda (2006 ▶). For our study of the effect of substituents on the structures of N-haloaryl­sulfonamides, see: Gowda et al. (2010 ▶, 2011a ▶,b ▶). For related structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶).

Experimental

Crystal data

K+·C6H4BrClNO2S−·1.5H2O

M = 335.65

Orthorhombic,

a = 12.343 (2) Å

b = 52.066 (6) Å

c = 6.942 (1) Å

V = 4461.3 (11) Å3

Z = 16

Mo Kα radiation

μ = 4.47 mm−1

T = 293 K

0.44 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.244, T max = 0.468

4075 measured reflections

1909 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.06

1909 reflections

141 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.52 e Å−3

Absolute structure: Flack (1983 ▶), 671 Friedel pairs

Flack parameter: 0.019 (9)

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/S1600536811022136/nc2232sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022136/nc2232Isup2.hkl

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

K+·C6H4BrClNO2S−·1.5H2O	F(000) = 2640
Mr = 335.65	Dx = 1.999 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2515 reflections
a = 12.343 (2) Å	θ = 2.9–27.9°
b = 52.066 (6) Å	µ = 4.47 mm−1
c = 6.942 (1) Å	T = 293 K
V = 4461.3 (11) Å3	Prism, yellow
Z = 16	0.44 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1909 independent reflections
Radiation source: fine-focus sealed tube	1841 reflections with I > 2σ(I)
graphite	Rint = 0.026
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→15
Tmin = 0.244, Tmax = 0.468	k = −56→64
4075 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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0419P)2 + 7.9401P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
1909 reflections	Δρmax = 0.42 e Å−3
141 parameters	Δρmin = −0.52 e Å−3
4 restraints	Absolute structure: Flack (1983), 671 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.019 (9)

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	0.1277 (3)	0.07221 (6)	0.8359 (5)	0.0279 (7)
C2	0.2039 (3)	0.08804 (7)	0.7551 (6)	0.0366 (8)
C3	0.2302 (4)	0.11022 (8)	0.8473 (8)	0.0527 (12)
H3	0.2811	0.1213	0.7935	0.063*
C4	0.1824 (4)	0.11628 (8)	1.0178 (9)	0.0620 (14)
H4	0.2017	0.1315	1.0788	0.074*
C5	0.1081 (4)	0.10099 (9)	1.1015 (8)	0.0568 (13)
H5	0.0766	0.1055	1.2184	0.068*
C6	0.0802 (3)	0.07872 (7)	1.0103 (7)	0.0383 (8)
H6	0.0291	0.0678	1.0655	0.046*
Br1	−0.06844 (3)	0.067404 (8)	0.49856 (7)	0.04826 (13)
Cl1	0.26996 (9)	0.08136 (2)	0.54056 (16)	0.0559 (3)
K1	0.34639 (6)	0.007514 (14)	0.52051 (13)	0.03396 (18)
N1	0.0549 (2)	0.04684 (5)	0.5150 (5)	0.0326 (6)
O1	0.0081 (2)	0.03366 (5)	0.8608 (4)	0.0389 (6)
O2	0.1870 (2)	0.02816 (5)	0.7239 (5)	0.0386 (6)
O3	0.2768 (2)	−0.03195 (5)	0.7376 (5)	0.0412 (6)
H31	0.315 (3)	−0.0386 (9)	0.817 (6)	0.049*
H32	0.247 (4)	−0.0416 (8)	0.666 (6)	0.049*
O4	0.5000	0.0000	0.8095 (6)	0.0466 (10)
H41	0.505 (4)	0.0112 (7)	0.892 (6)	0.056*
S1	0.09016 (6)	0.043209 (13)	0.73226 (12)	0.02646 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0302 (16)	0.0232 (15)	0.0302 (17)	0.0029 (13)	−0.0063 (14)	0.0003 (13)
C2	0.0397 (18)	0.0328 (16)	0.037 (2)	−0.0047 (13)	−0.0093 (19)	0.0048 (18)
C3	0.060 (3)	0.030 (2)	0.068 (3)	−0.0135 (19)	−0.023 (2)	0.004 (2)
C4	0.078 (3)	0.032 (2)	0.075 (4)	0.001 (2)	−0.028 (3)	−0.019 (2)
C5	0.073 (3)	0.044 (2)	0.053 (3)	0.019 (2)	−0.013 (2)	−0.022 (2)
C6	0.048 (2)	0.0327 (17)	0.035 (2)	0.0119 (15)	−0.0027 (19)	−0.0056 (18)
Br1	0.0399 (2)	0.0498 (2)	0.0551 (3)	0.00658 (16)	−0.0060 (2)	0.0135 (2)
Cl1	0.0568 (6)	0.0659 (7)	0.0449 (6)	−0.0265 (5)	0.0108 (5)	0.0044 (5)
K1	0.0342 (4)	0.0329 (4)	0.0348 (4)	0.0038 (3)	0.0060 (3)	0.0016 (3)
N1	0.0353 (14)	0.0298 (13)	0.0328 (16)	0.0011 (11)	0.0023 (14)	−0.0036 (14)
O1	0.0466 (15)	0.0280 (12)	0.0421 (16)	−0.0063 (11)	0.0119 (12)	0.0061 (11)
O2	0.0422 (13)	0.0306 (11)	0.0429 (16)	0.0119 (10)	0.0037 (12)	0.0029 (12)
O3	0.0528 (16)	0.0311 (13)	0.0396 (16)	−0.0014 (11)	−0.0041 (15)	−0.0001 (13)
O4	0.070 (3)	0.038 (2)	0.031 (2)	−0.0152 (19)	0.000	0.000
S1	0.0315 (4)	0.0186 (3)	0.0293 (4)	0.0007 (3)	0.0042 (3)	0.0006 (3)

C1—C2	1.371 (5)	K1—O3ii	2.790 (3)
C1—C6	1.387 (6)	K1—O2ii	2.803 (3)
C1—S1	1.736 (3)	K1—O1ii	3.008 (3)
C2—C3	1.360 (6)	K1—S1ii	3.4047 (11)
C2—Cl1	1.733 (5)	K1—H32	3.01 (4)
C3—C4	1.360 (8)	N1—S1	1.582 (4)
C3—H3	0.9300	O1—S1	1.438 (3)
C4—C5	1.346 (8)	O1—K1iii	2.659 (3)
C4—H4	0.9300	O1—K1iv	3.008 (3)
C5—C6	1.365 (6)	O2—S1	1.431 (3)
C5—H5	0.9300	O2—K1iv	2.803 (3)
C6—H6	0.9300	O3—K1iv	2.790 (3)
Br1—N1	1.864 (3)	O3—H31	0.804 (19)
K1—O2	2.649 (3)	O3—H32	0.796 (19)
K1—O1i	2.659 (3)	O4—K1v	2.788 (3)
K1—O3	2.689 (3)	O4—H41	0.819 (19)
K1—O4	2.788 (3)	S1—K1iv	3.4047 (11)
C2—C1—C6	120.0 (3)	O1i—K1—S1ii	88.82 (6)
C2—C1—S1	122.4 (3)	O3—K1—S1ii	79.06 (7)
C6—C1—S1	117.5 (3)	O4—K1—S1ii	99.07 (5)
C3—C2—C1	118.8 (4)	O3ii—K1—S1ii	93.74 (7)
C3—C2—Cl1	117.5 (3)	O2ii—K1—S1ii	24.26 (5)
C1—C2—Cl1	123.6 (3)	O1ii—K1—S1ii	24.95 (5)
C2—C3—C4	120.2 (4)	O2—K1—H32	82.2 (9)
C2—C3—H3	119.9	O1i—K1—H32	151.7 (9)
C4—C3—H3	119.9	O3—K1—H32	14.7 (6)
C5—C4—C3	122.3 (4)	O4—K1—H32	85.2 (7)
C5—C4—H4	118.9	O3ii—K1—H32	113.7 (7)
C3—C4—H4	118.9	O2ii—K1—H32	67.9 (6)
C4—C5—C6	118.3 (5)	O1ii—K1—H32	76.2 (9)
C4—C5—H5	120.9	S1ii—K1—H32	68.4 (8)
C6—C5—H5	120.9	S1—N1—Br1	110.60 (17)
C5—C6—C1	120.4 (4)	S1—O1—K1iii	164.64 (17)
C5—C6—H6	119.8	S1—O1—K1iv	93.13 (13)
C1—C6—H6	119.8	K1iii—O1—K1iv	85.96 (7)
O2—K1—O1i	124.89 (9)	S1—O2—K1	149.8 (2)
O2—K1—O3	76.94 (8)	S1—O2—K1iv	102.12 (15)
O1i—K1—O3	149.87 (9)	K1—O2—K1iv	103.41 (8)
O2—K1—O4	100.27 (10)	K1—O3—K1iv	102.72 (8)
O1i—K1—O4	82.02 (8)	K1—O3—H31	122 (4)
O3—K1—O4	72.95 (7)	K1iv—O3—H31	92 (4)
O2—K1—O3ii	77.62 (10)	K1—O3—H32	106 (4)
O1i—K1—O3ii	83.23 (9)	K1iv—O3—H32	118 (4)
O3—K1—O3ii	124.66 (5)	H31—O3—H32	116 (5)
O4—K1—O3ii	160.21 (6)	K1—O4—K1v	87.96 (13)
O2—K1—O2ii	123.44 (5)	K1—O4—H41	117 (4)
O1i—K1—O2ii	98.26 (9)	K1v—O4—H41	123 (4)
O3—K1—O2ii	81.86 (9)	O2—S1—O1	115.10 (17)
O4—K1—O2ii	122.39 (7)	O2—S1—N1	104.89 (17)
O3ii—K1—O2ii	72.84 (8)	O1—S1—N1	116.06 (16)
O2—K1—O1ii	158.24 (8)	O2—S1—C1	105.67 (17)
O1i—K1—O1ii	76.30 (9)	O1—S1—C1	103.37 (17)
O3—K1—O1ii	81.53 (9)	N1—S1—C1	111.42 (15)
O4—K1—O1ii	76.07 (7)	O2—S1—K1iv	53.61 (12)
O3ii—K1—O1ii	113.00 (8)	O1—S1—K1iv	61.92 (11)
O2ii—K1—O1ii	49.09 (7)	N1—S1—K1iv	135.78 (10)
O2—K1—S1ii	143.01 (7)	C1—S1—K1iv	111.69 (11)
C6—C1—C2—C3	−1.1 (5)	O1i—K1—O4—K1v	−41.28 (6)
S1—C1—C2—C3	−178.8 (3)	O3—K1—O4—K1v	121.76 (7)
C6—C1—C2—Cl1	178.7 (3)	O3ii—K1—O4—K1v	−83.5 (3)
S1—C1—C2—Cl1	0.9 (5)	O2ii—K1—O4—K1v	53.47 (8)
C1—C2—C3—C4	0.8 (6)	O1ii—K1—O4—K1v	36.50 (6)
Cl1—C2—C3—C4	−178.9 (3)	S1ii—K1—O4—K1v	46.24 (2)
C2—C3—C4—C5	−0.2 (7)	K1—O2—S1—O1	139.5 (3)
C3—C4—C5—C6	−0.2 (7)	K1iv—O2—S1—O1	−7.7 (2)
C4—C5—C6—C1	0.0 (6)	K1—O2—S1—N1	10.7 (4)
C2—C1—C6—C5	0.7 (6)	K1iv—O2—S1—N1	−136.49 (13)
S1—C1—C6—C5	178.5 (3)	K1—O2—S1—C1	−107.1 (3)
O1i—K1—O2—S1	71.6 (4)	K1iv—O2—S1—C1	105.67 (15)
O3—K1—O2—S1	−131.4 (3)	K1—O2—S1—K1iv	147.2 (4)
O4—K1—O2—S1	159.0 (3)	K1iii—O1—S1—O2	−79.1 (7)
O3ii—K1—O2—S1	−1.0 (3)	K1iv—O1—S1—O2	7.01 (19)
O2ii—K1—O2—S1	−60.5 (3)	K1iii—O1—S1—N1	43.9 (7)
O1ii—K1—O2—S1	−122.9 (3)	K1iv—O1—S1—N1	130.04 (12)
S1ii—K1—O2—S1	−80.6 (3)	K1iii—O1—S1—C1	166.2 (6)
O1i—K1—O2—K1iv	−141.38 (9)	K1iv—O1—S1—C1	−107.68 (12)
O3—K1—O2—K1iv	15.65 (9)	K1iii—O1—S1—K1iv	−86.2 (6)
O4—K1—O2—K1iv	−53.99 (9)	Br1—N1—S1—O2	−177.66 (15)
O3ii—K1—O2—K1iv	146.08 (11)	Br1—N1—S1—O1	54.1 (2)
O2ii—K1—O2—K1iv	86.54 (16)	Br1—N1—S1—C1	−63.8 (2)
O1ii—K1—O2—K1iv	24.1 (3)	Br1—N1—S1—K1iv	129.71 (11)
S1ii—K1—O2—K1iv	66.47 (16)	C2—C1—S1—O2	60.1 (3)
O2—K1—O3—K1iv	−15.68 (9)	C6—C1—S1—O2	−117.8 (3)
O1i—K1—O3—K1iv	124.69 (15)	C2—C1—S1—O1	−178.6 (3)
O4—K1—O3—K1iv	89.55 (10)	C6—C1—S1—O1	3.6 (3)
O3ii—K1—O3—K1iv	−80.34 (16)	C2—C1—S1—N1	−53.3 (3)
O2ii—K1—O3—K1iv	−142.87 (10)	C6—C1—S1—N1	128.9 (3)
O1ii—K1—O3—K1iv	167.49 (10)	C2—C1—S1—K1iv	116.6 (3)
S1ii—K1—O3—K1iv	−167.32 (9)	C6—C1—S1—K1iv	−61.2 (3)
O2—K1—O4—K1v	−165.44 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1iv	0.80 (2)	2.16 (2)	2.937 (4)	164 (5)
O3—H32···Br1vi	0.80 (2)	2.83 (3)	3.574 (3)	156 (4)
O4—H41···N1vii	0.82 (2)	2.13 (3)	2.905 (4)	157 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1i	0.80 (2)	2.16 (2)	2.937 (4)	164 (5)
O3—H32⋯Br1ii	0.80 (2)	2.83 (3)	3.574 (3)	156 (4)
O4—H41⋯N1iii	0.82 (2)	2.13 (3)	2.905 (4)	157 (5)

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