Potassium N-bromo-2,4-dichloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Foro, S.; Spandana, H.S.

doi:10.1107/S1600536812042456

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1368

doi:10.1107/S1600536812042456

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Potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate

B. Thimme Gowda,^a ^* Sabine Foro ^b and H. S. Spandana ^a

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 2 October 2012; accepted 10 October 2012; online 20 October 2012)

The asymmetric unit of the title salt, K⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O, 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-dichlorobenzenesulfonamide 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_r = 740.18
Monoclinic, C 2/c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.093
S = 1.09
2535 reflections
150 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.65 e Å⁻³

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) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042456/nc2295sup1.cif

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

checkCIF report

Comment top

The present work was undertaken in order to explore the effect of replacing sodium ion by potassium ion on the solid state structures of metal salts of N-haloarylsulfonamidates (Gowda et al., 2007, 2011a,b). As part of this work, the structure of potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011a), potassium N-bromo-4-chlorobenzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), sodium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (IV) (Gowda et al., 2007) and other sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the title compound, K⁺ ion is hepta coordinated by three O atoms from water molecules and four sulfonyl O atoms of three different N-bromo-2,4-dichlorobenzenesulfonamide anions. The replacement of Na⁺ by K⁺ changes co-ordination from hexa to hepta in the structure (Gowda et al., 2007) and other parameters.

The S—N distance of 1.575 (3) Å is consistent with a S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II), 1.584 (6) Å in (III) and 1.590 (6) Å in (IV).

The asymmetric unit of (I) consists of one potassium cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion and one water molecule in general position and and one water molecule located on a twofold rotation axis.

In the crystal structure the anions are linked by intermolecular O—H···Br and O—H···N hydrogen bonding into layers, that are parallel to the ac plane (Fig. 2 and Table 1).

Related literature top

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 top

The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda & Mahadevappa, 1983). 2 g of 2,4-dichlorobenzenesulfonamide was dissolved with stirring in 40 ml of 5M KOH at room temperature. The resultant solution was cooled in ice and 4 ml of liquid bromine was added drop wise with constant stirring. The resultant potassium salt of N-bromo-2,4-dichlorobenzenesulfonamide was filtered under suction, washed quickly with a minimum quantity of ice cold water. The purity of the compound was checked by determining its melting point (203–205° C) and estimating, iodometrically, the amount of active bromine present in it. It was further characterized from its infrared spectrum.

Prism like yellow single crystals of the title compound used in the X-ray diffraction studies were obtained from its aqueous solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme for the asymmetric unit and extended to show the coordination geometry for the K⁺. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate top

Crystal data top

K⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O	F(000) = 1448
M_r = 740.18	D_x = 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

Data collection top

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	R_int = 0.014
Rotation method data acquisition using ω scans.	θ_max = 26.4°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→13
T_min = 0.345, T_max = 0.384	k = −8→5
4960 measured reflections	l = −37→22

Refinement top

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(F_o²) + (0.0429P)² + 8.3581P] where P = (F_o² + 2F_c²)/3
2535 reflections	(Δ/σ)_max = 0.001
150 parameters	Δρ_max = 0.76 e Å⁻³
3 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

K⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O	V = 2489.9 (3) Å³
M_r = 740.18	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.5263 (7) Å	µ = 4.22 mm⁻¹
b = 6.7638 (4) Å	T = 293 K
c = 29.703 (2) Å	0.32 × 0.32 × 0.28 mm
β = 98.352 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2535 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2204 reflections with I > 2σ(I)
T_min = 0.345, T_max = 0.384	R_int = 0.014
4960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	3 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.76 e Å⁻³
2535 reflections	Δρ_min = −0.65 e Å⁻³
150 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—K1^iv	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—K1^v	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—K1^v	130.38 (6)
C6—C1—S1	118.0 (3)	O1ⁱⁱⁱ—K1—K1^v	90.06 (6)
C2—C1—S1	123.4 (3)	O2ⁱⁱⁱ—K1—K1^v	43.27 (5)
C3—C2—C1	120.4 (3)	S1ⁱⁱⁱ—K1—K1^v	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)	K1^v—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)	K1^v—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—K1^iv	165.01 (16)
O1—K1—O1ⁱⁱⁱ	122.42 (5)	S1—O2—K1ⁱⁱ	95.45 (12)
O2ⁱ—K1—O1ⁱⁱⁱ	102.09 (8)	K1^iv—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—K1^v	89.71 (12)
O3—K1—O2ⁱⁱⁱ	114.43 (8)	K1—O4—H41	112 (3)
O1ⁱⁱⁱ—K1—O2ⁱⁱⁱ	48.19 (7)	K1^v—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—K1^v	145.05 (6)	O1—S1—K1ⁱⁱ	54.26 (11)
O2ⁱ—K1—K1^v	51.05 (6)	N1—S1—K1ⁱⁱ	132.87 (12)
O3ⁱⁱ—K1—K1^v	98.18 (7)	C1—S1—K1ⁱⁱ	115.93 (11)
O4—K1—K1^v	45.15 (6)

C6—C1—C2—C3	0.3 (5)	S1ⁱⁱⁱ—K1—O3—K1ⁱⁱⁱ	26.89 (8)
S1—C1—C2—C3	−177.6 (3)	K1^v—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—K1^v	−165.19 (7)
C1—C2—C3—C4	−0.3 (5)	O2ⁱ—K1—O4—K1^v	−42.70 (6)
Cl1—C2—C3—C4	179.3 (3)	O3ⁱⁱ—K1—O4—K1^v	119.46 (7)
C2—C3—C4—C5	0.1 (6)	O3—K1—O4—K1^v	−84.4 (3)
C2—C3—C4—Cl2	−178.0 (3)	O1ⁱⁱⁱ—K1—O4—K1^v	55.99 (7)
C3—C4—C5—C6	0.0 (6)	O2ⁱⁱⁱ—K1—O4—K1^v	37.71 (5)
Cl2—C4—C5—C6	178.1 (3)	S1ⁱⁱⁱ—K1—O4—K1^v	47.51 (2)
C4—C5—C6—C1	−0.1 (6)	K1ⁱⁱⁱ—K1—O4—K1^v	59.77 (14)
C2—C1—C6—C5	−0.1 (5)	K1ⁱⁱ—K1—O4—K1^v	160.16 (4)
S1—C1—C6—C5	177.9 (3)	K1^iv—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)	K1^iv—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)	K1^iv—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)	K1^iv—O2—S1—K1ⁱⁱ	−93.7 (6)
S1ⁱⁱⁱ—K1—O1—S1	−77.2 (4)	K1—O1—S1—O2	134.2 (3)
K1^v—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)
K1^v—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)

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, y+1/2, z; (v) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₃BrCl₂NO₂S⁻·1.5H₂O
M_r	740.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.5263 (7), 6.7638 (4), 29.703 (2)
β (°)	98.352 (5)
V (Å³)	2489.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.22
Crystal size (mm)	0.32 × 0.32 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.345, 0.384
No. of measured, independent and observed [I > 2σ(I)] reflections	4960, 2535, 2204
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.093, 1.09
No. of reflections	2535
No. of parameters	150
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.65

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Br1ⁱ	0.802 (19)	2.78 (2)	3.550 (3)	160 (4)
O3—H32···N1	0.808 (19)	2.15 (3)	2.917 (4)	158 (5)
O4—H41···N1ⁱⁱ	0.820 (19)	2.16 (2)	2.957 (3)	165 (5)

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a one-time grant to Faculty/Professors under UGC–BSR.

References

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