Potassium N-bromo-2-chloro­benzene­sulfonamidate sesquihydrate

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

doi:10.1107/S1600536811022136

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m926

doi:10.1107/S1600536811022136

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Potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate

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 29 May 2011; accepted 7 June 2011; online 18 June 2011)

In the structure of the title compound, K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O, the K⁺ ion is heptacoordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-bromo-2-chlorobenzenesulfonamidate anions. The S—N distance of 1.582 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by intermolecular O—H⋯Br and O—H⋯N hydrogen bonds. The asymmetric unit consits of one potassium cation, one N-bromo-2-chlorobenzenesulfonamidate anion and one water molecule in general positions and one water molecule 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_r = 335.65
Orthorhombic, F d d 2
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) 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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.067
S = 1.06
1909 reflections
141 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ), 671 Friedel pairs
Flack parameter: 0.019 (9)

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

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536811022136/nc2232sup1.cif

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

checkCIF report

Comment top

To explore the effect of replacing sodium by potassium on the solid state structures of N-haloarylsulfonamidates (Gowda et al., 2011a,b), the structure of potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of I resembles those of sodium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011b), sodium N-chloro-2-chloro- benzenesulfonamidate sesquihydrate (III)(Gowda et al., 2010), potassium N-chloro-4-chloro-benzenesulfonamidate monohydrate (IV)(Gowda et al., 2011a), and other sodium N-chloro- arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the structure of the title compound the K⁺ ion is hepta coordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-bromo-2-chloro-benzenesulfonamide anions. The replacement of Na⁺ by K⁺ changes the coordination from hexa to hepta coordination (Gowda et al., 2011b).

The S—N distance of 1.582 (4)Å is consistent with an S—N double bond and is in agreement with the observed values of 1.579 (6) Å in (II), 1.588 (2) Å in (III) and 1.588 (2) Å in (IV)

In the crystal structure two-dimensional polymeric layer are found that are located parallel to the ac plane (Fig. 2). The molecular packing is stabilized by O3—H31···N1, O3—H32···Br1 and O4—H41···N1 hydrogen bonds (Table 1).

Related literature top

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 top

The title compound was prepared according to the literature method (Usha & Gowda, 2006). The purity of the compound was checked by determining its melting point (176 °). 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⁺. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii. Symmetry codes: (i) x +1/2, y , z -1/2; (ii) - x +1/2, - y , z -1/2".
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate top

Crystal data top

K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O	F(000) = 2640
M_r = 335.65	D_x = 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

Data collection top

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 monochromator	R_int = 0.026
Rotation method data acquisition using ω scans.	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→15
T_min = 0.244, T_max = 0.468	k = −56→64
4075 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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0419P)² + 7.9401P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
1909 reflections	Δρ_max = 0.42 e Å⁻³
141 parameters	Δρ_min = −0.52 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 671 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.019 (9)

Crystal data top

K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O	V = 4461.3 (11) Å³
M_r = 335.65	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 12.343 (2) Å	µ = 4.47 mm⁻¹
b = 52.066 (6) Å	T = 293 K
c = 6.942 (1) Å	0.44 × 0.40 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1909 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1841 reflections with I > 2σ(I)
T_min = 0.244, T_max = 0.468	R_int = 0.026
4075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	Δρ_max = 0.42 e Å⁻³
S = 1.06	Δρ_min = −0.52 e Å⁻³
1909 reflections	Absolute structure: Flack (1983), 671 Friedel pairs
141 parameters	Absolute structure parameter: 0.019 (9)
4 restraints

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—K1^iv	3.008 (3)
C5—C6	1.365 (6)	O2—S1	1.431 (3)
C5—H5	0.9300	O2—K1^iv	2.803 (3)
C6—H6	0.9300	O3—K1^iv	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—K1^v	2.788 (3)
K1—O3	2.689 (3)	O4—H41	0.819 (19)
K1—O4	2.788 (3)	S1—K1^iv	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—K1^iv	93.13 (13)
C1—C6—H6	119.8	K1ⁱⁱⁱ—O1—K1^iv	85.96 (7)
O2—K1—O1ⁱ	124.89 (9)	S1—O2—K1	149.8 (2)
O2—K1—O3	76.94 (8)	S1—O2—K1^iv	102.12 (15)
O1ⁱ—K1—O3	149.87 (9)	K1—O2—K1^iv	103.41 (8)
O2—K1—O4	100.27 (10)	K1—O3—K1^iv	102.72 (8)
O1ⁱ—K1—O4	82.02 (8)	K1—O3—H31	122 (4)
O3—K1—O4	72.95 (7)	K1^iv—O3—H31	92 (4)
O2—K1—O3ⁱⁱ	77.62 (10)	K1—O3—H32	106 (4)
O1ⁱ—K1—O3ⁱⁱ	83.23 (9)	K1^iv—O3—H32	118 (4)
O3—K1—O3ⁱⁱ	124.66 (5)	H31—O3—H32	116 (5)
O4—K1—O3ⁱⁱ	160.21 (6)	K1—O4—K1^v	87.96 (13)
O2—K1—O2ⁱⁱ	123.44 (5)	K1—O4—H41	117 (4)
O1ⁱ—K1—O2ⁱⁱ	98.26 (9)	K1^v—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—K1^iv	53.61 (12)
O3ⁱⁱ—K1—O1ⁱⁱ	113.00 (8)	O1—S1—K1^iv	61.92 (11)
O2ⁱⁱ—K1—O1ⁱⁱ	49.09 (7)	N1—S1—K1^iv	135.78 (10)
O2—K1—S1ⁱⁱ	143.01 (7)	C1—S1—K1^iv	111.69 (11)

C6—C1—C2—C3	−1.1 (5)	O1ⁱ—K1—O4—K1^v	−41.28 (6)
S1—C1—C2—C3	−178.8 (3)	O3—K1—O4—K1^v	121.76 (7)
C6—C1—C2—Cl1	178.7 (3)	O3ⁱⁱ—K1—O4—K1^v	−83.5 (3)
S1—C1—C2—Cl1	0.9 (5)	O2ⁱⁱ—K1—O4—K1^v	53.47 (8)
C1—C2—C3—C4	0.8 (6)	O1ⁱⁱ—K1—O4—K1^v	36.50 (6)
Cl1—C2—C3—C4	−178.9 (3)	S1ⁱⁱ—K1—O4—K1^v	46.24 (2)
C2—C3—C4—C5	−0.2 (7)	K1—O2—S1—O1	139.5 (3)
C3—C4—C5—C6	−0.2 (7)	K1^iv—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)	K1^iv—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)	K1^iv—O2—S1—C1	105.67 (15)
O3—K1—O2—S1	−131.4 (3)	K1—O2—S1—K1^iv	147.2 (4)
O4—K1—O2—S1	159.0 (3)	K1ⁱⁱⁱ—O1—S1—O2	−79.1 (7)
O3ⁱⁱ—K1—O2—S1	−1.0 (3)	K1^iv—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)	K1^iv—O1—S1—N1	130.04 (12)
S1ⁱⁱ—K1—O2—S1	−80.6 (3)	K1ⁱⁱⁱ—O1—S1—C1	166.2 (6)
O1ⁱ—K1—O2—K1^iv	−141.38 (9)	K1^iv—O1—S1—C1	−107.68 (12)
O3—K1—O2—K1^iv	15.65 (9)	K1ⁱⁱⁱ—O1—S1—K1^iv	−86.2 (6)
O4—K1—O2—K1^iv	−53.99 (9)	Br1—N1—S1—O2	−177.66 (15)
O3ⁱⁱ—K1—O2—K1^iv	146.08 (11)	Br1—N1—S1—O1	54.1 (2)
O2ⁱⁱ—K1—O2—K1^iv	86.54 (16)	Br1—N1—S1—C1	−63.8 (2)
O1ⁱⁱ—K1—O2—K1^iv	24.1 (3)	Br1—N1—S1—K1^iv	129.71 (11)
S1ⁱⁱ—K1—O2—K1^iv	66.47 (16)	C2—C1—S1—O2	60.1 (3)
O2—K1—O3—K1^iv	−15.68 (9)	C6—C1—S1—O2	−117.8 (3)
O1ⁱ—K1—O3—K1^iv	124.69 (15)	C2—C1—S1—O1	−178.6 (3)
O4—K1—O3—K1^iv	89.55 (10)	C6—C1—S1—O1	3.6 (3)
O3ⁱⁱ—K1—O3—K1^iv	−80.34 (16)	C2—C1—S1—N1	−53.3 (3)
O2ⁱⁱ—K1—O3—K1^iv	−142.87 (10)	C6—C1—S1—N1	128.9 (3)
O1ⁱⁱ—K1—O3—K1^iv	167.49 (10)	C2—C1—S1—K1^iv	116.6 (3)
S1ⁱⁱ—K1—O3—K1^iv	−167.32 (9)	C6—C1—S1—K1^iv	−61.2 (3)
O2—K1—O4—K1^v	−165.44 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1^iv	0.80 (2)	2.16 (2)	2.937 (4)	164 (5)
O3—H32···Br1^vi	0.80 (2)	2.83 (3)	3.574 (3)	156 (4)
O4—H41···N1^vii	0.82 (2)	2.13 (3)	2.905 (4)	157 (5)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₄BrClNO₂S⁻·1.5H₂O
M_r	335.65
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	12.343 (2), 52.066 (6), 6.942 (1)
V (Å³)	4461.3 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	4.47
Crystal size (mm)	0.44 × 0.40 × 0.20

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	0.244, 0.468
No. of measured, independent and observed [I > 2σ(I)] reflections	4075, 1909, 1841
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.067, 1.06
No. of reflections	1909
No. of parameters	141
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.52
Absolute structure	Flack (1983), 671 Friedel pairs
Absolute structure parameter	0.019 (9)

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	0.804 (19)	2.16 (2)	2.937 (4)	164 (5)
O3—H32···Br1ⁱⁱ	0.796 (19)	2.83 (3)	3.574 (3)	156 (4)
O4—H41···N1ⁱⁱⁱ	0.819 (19)	2.13 (3)	2.905 (4)	157 (5)

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

Acknowledgements

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

References

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