Potassium N-bromo-4-chloro­benzene­sulfonamidate monohydrate

Gowda, B.T.; Foro, S.; Shakuntala, K.

doi:10.1107/S1600536811023610

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m962

doi:10.1107/S1600536811023610

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Potassium N-bromo-4-chlorobenzenesulfonamidate monohydrate

B. Thimme Gowda,^a ^* Sabine Foro ^b and K. Shakuntala ^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 June 2011; accepted 16 June 2011; online 22 June 2011)

In the structure of the title compound, K⁺·C₆H₄BrClNO₂S⁻·H₂O, the K⁺ cation is heptacoordinated. 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 intermolecular 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 , 2011a ,b ); 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_r = 326.64
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.156
S = 1.19
2147 reflections
134 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.22 e Å⁻³
Δρ_min = −0.95 e Å⁻³

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

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811023610/ds2118sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811023610/ds2118Isup3.cml

checkCIF report

Comment top

To explore the effect of substitution and replacing sodium ion by potassium ion in the solid state structures of N-chloroarylsulfonamides (Gowda et al., 2007; 2011a,b; Usha & Gowda, 2006), in the present work, the structure of potassium N-bromo-4-chloro- benzenesulfonamidate monohydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chloro- benzenesulfonamidate sesquihydrate(II)(Gowda et al., 2011b), potassium N,4-dichloro-benzenesulfonamidate monohydrate (III) (Gowda et al., 2011a), sodium N-bromo-4-chloro- benzenesulfonamidate sesquihydrate (IV)(Gowda et al., 2007) and other sodium N-chloro-arylsulfonamdes (George et al., 2000; Olmstead & Power, 1986). In particular, there is no interaction between the nitrogen and potassium atom in the molecule. Further, K⁺ is hepta co-ordinated in contrast to hexa co-ordination with Na⁺

K⁺ hepta coordination involves two O atoms from water molecules, four sulfonyl O atoms of N-bromo-4-chlorobenzenesulfonamide anions and one Br, in contrast to octahedral coordination of Na⁺ in (IV) by three O atoms of water molecules and by three sulfonyl O atoms of N-bromo-4-chloro- benzenesulfonamide anions (Gowda et al., 2007).

The S—N distance of N1—S1, 1.584 (6) Å is consistent with an S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II), 1.588 (2)Å in (III), and N1—S1, 1.574 (5)Å and N2—S2 1.579 (4)Å in (IV).

K⁺ ion coordination in the structure gives rise to several hydrogen bonding between coordinated water molecules and nitrogen atoms. The packing diagram consists of a two-dimensional polymeric layer running parallel to the b-axis (Fig. 2). The molecular packing is stabilized by O3—H31···N1 and O3—H32···N1 hydrogen bonds (Table 1).

Related literature top

For our study of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda et al. (2007, 2011a,b); 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 top

The title compound was prepared similar to the literature method (Gowda & Usha, 2003). The purity of the compound was checked by determining its melting point (184 ° C). It was characterized by recording its infrared and NMR spectra.

Yellow prisms of the title compound used in 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 RED (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⁺. Displacement ellipsoids are drawn at the 50% probability level. 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-4-chlorobenzenesulfonamidate monohydrate top

Crystal data top

K⁺·C₆H₄BrClNO₂S⁻·H₂O	F(000) = 640
M_r = 326.64	D_x = 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

Data collection top

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 monochromator	R_int = 0.035
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −19→17
T_min = 0.298, T_max = 0.333	k = −5→12
3796 measured reflections	l = −8→6

Refinement top

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(F_o²) + (0.0614P)² + 8.645P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max = 0.014
2147 reflections	Δρ_max = 1.22 e Å⁻³
134 parameters	Δρ_min = −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)

Crystal data top

K⁺·C₆H₄BrClNO₂S⁻·H₂O	V = 1058.73 (17) Å³
M_r = 326.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.596 (1) Å	µ = 4.70 mm⁻¹
b = 10.188 (1) Å	T = 293 K
c = 6.7649 (7) Å	0.34 × 0.34 × 0.30 mm
β = 99.947 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2147 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1984 reflections with I > 2σ(I)
T_min = 0.298, T_max = 0.333	R_int = 0.035
3796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 1.22 e Å⁻³
2147 reflections	Δρ_min = −0.95 e Å⁻³
134 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

Br1—N1	1.897 (5)	O2—K1ⁱⁱ	2.784 (5)
Br1—K1	3.5001 (16)	O2—K1^vi	2.827 (5)
K1—O1ⁱ	2.704 (5)	O3—K1ⁱ	2.818 (6)
K1—O2ⁱⁱ	2.784 (5)	O3—K1^v	3.295 (6)
K1—O3	2.799 (5)	O3—H31	0.82 (2)
K1—O3ⁱⁱⁱ	2.818 (6)	O3—H32	0.82 (2)
K1—O2^iv	2.827 (5)	C1—C6	1.356 (9)
K1—O1	2.855 (5)	C1—C2	1.382 (9)
K1—O3^v	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—O2^iv	88.05 (16)	S1—O2—K1^vi	133.0 (3)
O2ⁱⁱ—K1—O2^iv	99.40 (13)	K1ⁱⁱ—O2—K1^vi	80.60 (12)
O3—K1—O2^iv	66.52 (15)	K1—O3—K1ⁱ	99.95 (16)
O3ⁱⁱⁱ—K1—O2^iv	143.94 (16)	K1—O3—K1^v	72.59 (13)
O1ⁱ—K1—O1	87.38 (13)	K1ⁱ—O3—K1^v	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)	K1^v—O3—H31	82 (6)
O2^iv—K1—O1	139.19 (15)	K1—O3—H32	110 (6)
O1ⁱ—K1—O3^v	148.56 (15)	K1ⁱ—O3—H32	102 (6)
O2ⁱⁱ—K1—O3^v	60.31 (15)	K1^v—O3—H32	125 (6)
O3—K1—O3^v	107.41 (13)	H31—O3—H32	98 (9)
O3ⁱⁱⁱ—K1—O3^v	127.12 (10)	S1—N1—Br1	109.5 (3)
O2^iv—K1—O3^v	67.58 (15)	S1—N1—K1	83.6 (2)
O1—K1—O3^v	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)
O2^iv—K1—N1	103.80 (15)	C1—C2—H2	120.6
O1—K1—N1	46.50 (13)	C3—C2—H2	120.6
O3^v—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)
O2^iv—K1—Br1	80.94 (11)	C3—C4—Cl1	118.4 (6)
O1—K1—Br1	59.70 (10)	C4—C5—C6	118.8 (7)
O3^v—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—K1^v	125.32 (11)
N1—Br1—K1—O2ⁱⁱ	39.8 (2)	O2^iv—K1—O3—K1^v	−55.11 (13)
N1—Br1—K1—O3	141.5 (3)	O1—K1—O3—K1^v	149.3 (3)
N1—Br1—K1—O3ⁱⁱⁱ	−47.2 (2)	O3^v—K1—O3—K1^v	0.0
N1—Br1—K1—O2^iv	136.1 (2)	N1—K1—O3—K1^v	9.7 (4)
N1—Br1—K1—O1	−55.1 (2)	Br1—K1—O3—K1^v	−60.9 (2)
N1—Br1—K1—O3^v	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)
O2^iv—K1—O1—S1	64.8 (4)	O2^iv—K1—N1—S1	−157.0 (2)
O3^v—K1—O1—S1	−0.1 (3)	O1—K1—N1—S1	−9.74 (19)
N1—K1—O1—S1	11.4 (2)	O3^v—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)
O2^iv—K1—O1—K1ⁱⁱⁱ	−152.3 (2)	O2^iv—K1—N1—Br1	−44.9 (2)
O3^v—K1—O1—K1ⁱⁱⁱ	142.81 (15)	O1—K1—N1—Br1	102.4 (2)
N1—K1—O1—K1ⁱⁱⁱ	154.3 (3)	O3^v—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—K1^vi	66.9 (5)	O1—S1—C1—C2	168.8 (5)
N1—S1—O2—K1^vi	−166.1 (4)	N1—S1—C1—C2	45.1 (6)
C1—S1—O2—K1^vi	−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)
O2^iv—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)
O3^v—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—K1^v	−148.04 (15)	C4—C5—C6—C1	−0.2 (11)
O2ⁱⁱ—K1—O3—K1^v	52.01 (12)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+3/2, z+1/2; (iv) x, y, z−1; (v) −x+1, −y+1, −z−1; (vi) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^v	0.82 (2)	2.25 (5)	3.005 (8)	152 (8)
O3—H32···N1^vii	0.82 (2)	2.16 (3)	2.967 (8)	166 (9)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₄BrClNO₂S⁻·H₂O
M_r	326.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.596 (1), 10.188 (1), 6.7649 (7)
β (°)	99.947 (9)
V (Å³)	1058.73 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.70
Crystal size (mm)	0.34 × 0.34 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.298, 0.333
No. of measured, independent and observed [I > 2σ(I)] reflections	3796, 2147, 1984
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.156, 1.19
No. of reflections	2147
No. of parameters	134
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.22, −0.95

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

Acknowledgements

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

References

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