Potassium N-bromo-2,4-dichloro-benzene-sulfonamidate sesquihydrate.

The asymmetric unit of the title salt, K(+)·C(6)H(3)BrCl(2)NO(2)S(-)·1.5H(2)O, contains one K(+) cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion, one water molecule in general position and one water molecule located on a twofold rotation axis. The K(+) cation is hepta-coordinated by three water O atoms and four sulfonyl O atoms from three symmetry-related N-bromo-2,4-dichloro-benzene-sulfonamide anions. The S=N distance of 1.575 (3) Å is consistent with that of a double bond. In the crystal, the anions are linked by O-H⋯Br and O-H⋯N hydrogen bonds into layers parallel to the ac plane.

Related literature

For preparation of N-haloaryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶). For studies of the effect of substituents on the structures of N-haloaryl­sulfonamides, see: George et al. (2000 ▶); Gowda et al. (2007 ▶, 2011a ▶,b ▶); Olmstead & Power (1986 ▶).

Experimental

Crystal data

K+·C6H3BrCl2NO2S−·1.5H2O

M = 740.18

Monoclinic,

a = 12.5263 (7) Å

b = 6.7638 (4) Å

c = 29.703 (2) Å

β = 98.352 (5)°

V = 2489.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.22 mm−1

T = 293 K

0.32 × 0.32 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.345, T max = 0.384

4960 measured reflections

2535 independent reflections

2204 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.09

2535 reflections

150 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.76 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042456/nc2295sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042456/nc2295Isup2.hkl

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

K+·C6H3BrCl2NO2S−·1.5H2O	F(000) = 1448
Mr = 740.18	Dx = 1.975 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2489 reflections
a = 12.5263 (7) Å	θ = 3.0–27.7°
b = 6.7638 (4) Å	µ = 4.22 mm−1
c = 29.703 (2) Å	T = 293 K
β = 98.352 (5)°	Prism, yellow
V = 2489.9 (3) Å3	0.32 × 0.32 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2535 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→13
Tmin = 0.345, Tmax = 0.384	k = −8→5
4960 measured reflections	l = −37→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0429P)2 + 8.3581P] where P = (Fo2 + 2Fc2)/3
2535 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.76 e Å−3
3 restraints	Δρmin = −0.65 e Å−3

Experimental. 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	0.0780 (3)	0.4566 (5)	0.11591 (11)	0.0271 (7)
C2	0.1438 (3)	0.3775 (5)	0.08637 (12)	0.0317 (7)
C3	0.1538 (3)	0.4716 (6)	0.04598 (12)	0.0392 (9)
H3	0.1980	0.4192	0.0264	0.047*
C4	0.0974 (3)	0.6446 (6)	0.03496 (13)	0.0426 (9)
C5	0.0320 (3)	0.7248 (6)	0.06337 (14)	0.0447 (9)
H5	−0.0056	0.8413	0.0556	0.054*
C6	0.0228 (3)	0.6302 (5)	0.10361 (13)	0.0367 (8)
H6	−0.0214	0.6841	0.1230	0.044*
Br1	−0.11245 (3)	0.10625 (6)	0.130655 (14)	0.04440 (14)
Cl1	0.21550 (9)	0.15999 (15)	0.09788 (4)	0.0485 (3)
Cl2	0.10726 (10)	0.7571 (2)	−0.01671 (4)	0.0650 (4)
K1	0.34306 (6)	0.13766 (12)	0.23492 (3)	0.0366 (2)
N1	0.0277 (2)	0.1274 (4)	0.16389 (10)	0.0319 (6)
O1	0.1712 (2)	0.3416 (4)	0.19584 (8)	0.0386 (6)
O2	−0.0093 (2)	0.4804 (4)	0.18845 (8)	0.0383 (6)
O3	0.2037 (2)	−0.1486 (4)	0.19206 (10)	0.0426 (6)
H31	0.234 (3)	−0.195 (7)	0.1725 (12)	0.051*
H32	0.155 (3)	−0.088 (6)	0.1774 (14)	0.051*
O4	0.5000	0.4277 (6)	0.2500	0.0471 (10)
H41	0.490 (4)	0.502 (6)	0.2710 (11)	0.056*
S1	0.06429 (7)	0.34987 (12)	0.16983 (3)	0.02745 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0271 (16)	0.0256 (16)	0.0280 (16)	−0.0039 (13)	0.0014 (12)	−0.0003 (13)
C2	0.0261 (16)	0.0319 (18)	0.0371 (18)	−0.0031 (14)	0.0042 (14)	0.0000 (15)
C3	0.0350 (19)	0.048 (2)	0.0364 (19)	−0.0108 (17)	0.0109 (15)	−0.0008 (17)
C4	0.040 (2)	0.048 (2)	0.038 (2)	−0.0161 (18)	−0.0006 (16)	0.0113 (17)
C5	0.047 (2)	0.036 (2)	0.050 (2)	0.0043 (18)	0.0016 (18)	0.0116 (18)
C6	0.0359 (19)	0.0322 (18)	0.041 (2)	0.0040 (15)	0.0036 (15)	0.0029 (15)
Br1	0.0342 (2)	0.0494 (3)	0.0498 (2)	−0.00725 (17)	0.00672 (16)	−0.01193 (18)
Cl1	0.0484 (6)	0.0376 (5)	0.0645 (7)	0.0110 (4)	0.0250 (5)	0.0029 (5)
Cl2	0.0592 (7)	0.0857 (9)	0.0483 (6)	−0.0170 (6)	0.0024 (5)	0.0322 (6)
K1	0.0312 (4)	0.0354 (4)	0.0423 (4)	0.0051 (3)	0.0021 (3)	−0.0034 (3)
N1	0.0307 (15)	0.0279 (15)	0.0373 (16)	0.0006 (12)	0.0060 (12)	0.0047 (12)
O1	0.0373 (14)	0.0399 (14)	0.0353 (14)	0.0026 (11)	−0.0064 (11)	0.0010 (11)
O2	0.0444 (15)	0.0387 (14)	0.0339 (13)	0.0094 (12)	0.0130 (11)	−0.0046 (11)
O3	0.0475 (17)	0.0380 (15)	0.0434 (16)	0.0052 (12)	0.0099 (13)	0.0004 (12)
O4	0.073 (3)	0.031 (2)	0.041 (2)	0.000	0.022 (2)	0.000
S1	0.0302 (4)	0.0260 (4)	0.0260 (4)	0.0028 (3)	0.0033 (3)	0.0000 (3)

C1—C6	1.384 (5)	K1—O3	2.788 (3)
C1—C2	1.395 (5)	K1—O1iii	2.895 (3)
C1—S1	1.787 (3)	K1—O2iii	3.045 (3)
C2—C3	1.380 (5)	K1—S1iii	3.4910 (12)
C2—Cl1	1.732 (4)	N1—S1	1.575 (3)
C3—C4	1.381 (6)	O1—S1	1.447 (3)
C3—H3	0.9300	O1—K1ii	2.895 (3)
C4—C5	1.370 (6)	O2—S1	1.443 (3)
C4—Cl2	1.734 (4)	O2—K1iv	2.683 (2)
C5—C6	1.375 (5)	O2—K1ii	3.045 (3)
C5—H5	0.9300	O3—K1iii	2.740 (3)
C6—H6	0.9300	O3—H31	0.802 (19)
Br1—N1	1.890 (3)	O3—H32	0.808 (19)
K1—O1	2.675 (3)	O4—K1v	2.767 (3)
K1—O2i	2.683 (2)	O4—H41	0.820 (19)
K1—O3ii	2.740 (3)	S1—K1ii	3.4910 (12)
K1—O4	2.767 (3)
C6—C1—C2	118.5 (3)	O3—K1—K1v	130.38 (6)
C6—C1—S1	118.0 (3)	O1iii—K1—K1v	90.06 (6)
C2—C1—S1	123.4 (3)	O2iii—K1—K1v	43.27 (5)
C3—C2—C1	120.4 (3)	S1iii—K1—K1v	66.97 (2)
C3—C2—Cl1	117.0 (3)	O1—K1—K1iii	94.01 (7)
C1—C2—Cl1	122.6 (3)	O2i—K1—K1iii	103.41 (6)
C2—C3—C4	119.3 (4)	O3ii—K1—K1iii	93.78 (7)
C2—C3—H3	120.4	O4—K1—K1iii	157.36 (5)
C4—C3—H3	120.4	O3—K1—K1iii	38.92 (6)
C5—C4—C3	121.4 (4)	O1iii—K1—K1iii	38.01 (5)
C5—C4—Cl2	119.8 (3)	O2iii—K1—K1iii	84.35 (5)
C3—C4—Cl2	118.8 (3)	S1iii—K1—K1iii	61.08 (2)
C4—C5—C6	118.9 (4)	K1v—K1—K1iii	120.90 (2)
C4—C5—H5	120.5	O1—K1—K1ii	41.78 (6)
C6—C5—H5	120.5	O2i—K1—K1ii	149.20 (6)
C5—C6—C1	121.5 (4)	O3ii—K1—K1ii	39.74 (6)
C5—C6—H6	119.2	O4—K1—K1ii	78.55 (6)
C1—C6—H6	119.2	O3—K1—K1ii	108.70 (7)
O1—K1—O2i	123.54 (8)	O1iii—K1—K1ii	107.85 (6)
O1—K1—O3ii	79.66 (9)	O2iii—K1—K1ii	117.01 (6)
O2i—K1—O3ii	149.20 (9)	S1iii—K1—K1ii	113.48 (3)
O1—K1—O4	102.28 (8)	K1v—K1—K1ii	120.90 (2)
O2i—K1—O4	80.66 (7)	K1iii—K1—K1ii	104.55 (3)
O3ii—K1—O4	74.11 (7)	S1—N1—Br1	111.33 (16)
O1—K1—O3	75.45 (8)	S1—O1—K1	151.14 (16)
O2i—K1—O3	85.56 (9)	S1—O1—K1ii	101.80 (13)
O3ii—K1—O3	122.44 (5)	K1—O1—K1ii	100.21 (8)
O4—K1—O3	161.68 (7)	S1—O2—K1iv	165.01 (16)
O1—K1—O1iii	122.42 (5)	S1—O2—K1ii	95.45 (12)
O2i—K1—O1iii	102.09 (8)	K1iv—O2—K1ii	85.68 (7)
O3ii—K1—O1iii	76.13 (8)	K1iii—O3—K1	101.34 (10)
O4—K1—O1iii	119.42 (6)	K1iii—O3—H31	123 (4)
O3—K1—O1iii	75.21 (8)	K1—O3—H31	106 (4)
O1—K1—O2iii	157.55 (8)	K1iii—O3—H32	117 (4)
O2i—K1—O2iii	78.37 (9)	K1—O3—H32	106 (3)
O3ii—K1—O2iii	78.12 (8)	H31—O3—H32	102 (5)
O4—K1—O2iii	74.58 (7)	K1—O4—K1v	89.71 (12)
O3—K1—O2iii	114.43 (8)	K1—O4—H41	112 (3)
O1iii—K1—O2iii	48.19 (7)	K1v—O4—H41	119 (3)
O1—K1—S1iii	142.27 (7)	O2—S1—O1	114.34 (16)
O2i—K1—S1iii	91.31 (6)	O2—S1—N1	115.83 (16)
O3ii—K1—S1iii	74.74 (7)	O1—S1—N1	104.73 (16)
O4—K1—S1iii	96.86 (5)	O2—S1—C1	104.25 (15)
O3—K1—S1iii	95.47 (7)	O1—S1—C1	107.00 (16)
O1iii—K1—S1iii	23.94 (5)	N1—S1—C1	110.46 (16)
O2iii—K1—S1iii	24.30 (5)	O2—S1—K1ii	60.25 (11)
O1—K1—K1v	145.05 (6)	O1—S1—K1ii	54.26 (11)
O2i—K1—K1v	51.05 (6)	N1—S1—K1ii	132.87 (12)
O3ii—K1—K1v	98.18 (7)	C1—S1—K1ii	115.93 (11)
O4—K1—K1v	45.15 (6)
C6—C1—C2—C3	0.3 (5)	S1iii—K1—O3—K1iii	26.89 (8)
S1—C1—C2—C3	−177.6 (3)	K1v—K1—O3—K1iii	91.14 (10)
C6—C1—C2—Cl1	−179.3 (3)	K1ii—K1—O3—K1iii	−90.17 (8)
S1—C1—C2—Cl1	2.9 (4)	O1—K1—O4—K1v	−165.19 (7)
C1—C2—C3—C4	−0.3 (5)	O2i—K1—O4—K1v	−42.70 (6)
Cl1—C2—C3—C4	179.3 (3)	O3ii—K1—O4—K1v	119.46 (7)
C2—C3—C4—C5	0.1 (6)	O3—K1—O4—K1v	−84.4 (3)
C2—C3—C4—Cl2	−178.0 (3)	O1iii—K1—O4—K1v	55.99 (7)
C3—C4—C5—C6	0.0 (6)	O2iii—K1—O4—K1v	37.71 (5)
Cl2—C4—C5—C6	178.1 (3)	S1iii—K1—O4—K1v	47.51 (2)
C4—C5—C6—C1	−0.1 (6)	K1iii—K1—O4—K1v	59.77 (14)
C2—C1—C6—C5	−0.1 (5)	K1ii—K1—O4—K1v	160.16 (4)
S1—C1—C6—C5	177.9 (3)	K1iv—O2—S1—O1	−89.2 (6)
O2i—K1—O1—S1	77.2 (4)	K1ii—O2—S1—O1	4.50 (17)
O3ii—K1—O1—S1	−124.9 (3)	K1iv—O2—S1—N1	32.8 (7)
O4—K1—O1—S1	164.0 (3)	K1ii—O2—S1—N1	126.44 (14)
O3—K1—O1—S1	2.7 (3)	K1iv—O2—S1—C1	154.3 (6)
O1iii—K1—O1—S1	−58.8 (3)	K1ii—O2—S1—C1	−111.99 (12)
O2iii—K1—O1—S1	−116.7 (3)	K1iv—O2—S1—K1ii	−93.7 (6)
S1iii—K1—O1—S1	−77.2 (4)	K1—O1—S1—O2	134.2 (3)
K1v—K1—O1—S1	145.6 (3)	K1ii—O1—S1—O2	−4.81 (18)
K1iii—K1—O1—S1	−31.8 (3)	K1—O1—S1—N1	6.3 (4)
K1ii—K1—O1—S1	−139.2 (4)	K1ii—O1—S1—N1	−132.65 (13)
O2i—K1—O1—K1ii	−143.58 (9)	K1—O1—S1—C1	−111.0 (3)
O3ii—K1—O1—K1ii	14.32 (8)	K1ii—O1—S1—C1	110.07 (14)
O4—K1—O1—K1ii	−56.74 (8)	K1—O1—S1—K1ii	139.0 (4)
O3—K1—O1—K1ii	141.96 (10)	Br1—N1—S1—O2	52.7 (2)
O1iii—K1—O1—K1ii	80.46 (13)	Br1—N1—S1—O1	179.61 (16)
O2iii—K1—O1—K1ii	22.6 (2)	Br1—N1—S1—C1	−65.5 (2)
S1iii—K1—O1—K1ii	62.01 (13)	Br1—N1—S1—K1ii	125.06 (12)
K1v—K1—O1—K1ii	−75.18 (13)	C6—C1—S1—O2	1.3 (3)
K1iii—K1—O1—K1ii	107.44 (7)	C2—C1—S1—O2	179.2 (3)
O1—K1—O3—K1iii	−115.86 (10)	C6—C1—S1—O1	−120.2 (3)
O2i—K1—O3—K1iii	117.79 (9)	C2—C1—S1—O1	57.7 (3)
O3ii—K1—O3—K1iii	−48.49 (13)	C6—C1—S1—N1	126.4 (3)
O4—K1—O3—K1iii	159.0 (2)	C2—C1—S1—N1	−55.8 (3)
O1iii—K1—O3—K1iii	14.03 (8)	C6—C1—S1—K1ii	−62.2 (3)
O2iii—K1—O3—K1iii	42.71 (11)	C2—C1—S1—K1ii	115.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Br1i	0.80 (2)	2.78 (2)	3.550 (3)	160 (4)
O3—H32···N1	0.81 (2)	2.15 (3)	2.917 (4)	158 (5)
O4—H41···N1ii	0.82 (2)	2.16 (2)	2.957 (3)	165 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Br1i	0.80 (2)	2.78 (2)	3.550 (3)	160 (4)
O3—H32⋯N1	0.81 (2)	2.15 (3)	2.917 (4)	158 (5)
O4—H41⋯N1ii	0.82 (2)	2.16 (2)	2.957 (3)	165 (5)

Symmetry codes: (i) ; (ii) .