Potassium N-bromo-2-methyl­benzene­sulfonamidate sesquihydrate

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

doi:10.1107/S1600536811025153

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1015

doi:10.1107/S1600536811025153

Open

access

Potassium N-bromo-2-methylbenzenesulfonamidate 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 1 June 2011; accepted 26 June 2011; online 2 July 2011)

In the structure of the title compound, K⁺·C₇H₇BrNO₂S⁻·1.5H₂O, the K⁺ ion is heptacoordinated by three O atoms from water molecules and by four sulfonyl O atoms of N-bromo-2-methylbenzenesulfonamide anions. The S—N distance of 1.577 (5) Å is consistent with an S=N double bond. The crystal structure comprises sheets in the ac plane which are further stabilized by O—H⋯Br and O—H⋯N hydrogen bonds.

Related literature

For the preparation of N-bromoarylsulfonamides, see: Usha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda & Kumar (2003 ); Gowda et al. (2009 , 2011 ); Usha & Gowda (2006). For related structures, see: George et al. (2000 ); Olmstead & Power (1986 ).

Experimental

Crystal data

K⁺·C₇H₇BrNO₂S⁻·1.5H₂O
M_r = 315.23
Orthorhombic, F d d 2
a = 12.271 (2) Å
b = 55.017 (6) Å
c = 6.904 (1) Å
V = 4661.0 (11) Å³
Z = 16
Mo Kα radiation
μ = 4.05 mm⁻¹
T = 293 K
0.42 × 0.42 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.281, T_max = 0.376
7816 measured reflections
2358 independent reflections
2140 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.112
S = 1.13
2358 reflections
142 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.57 e Å⁻³
Absolute structure: Flack (1983 ), 1060 Friedel pairs
Flack parameter: −0.002 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Br1ⁱ	0.81 (2)	2.79 (2)	3.600 (5)	173 (7)
O3—H32⋯N1ⁱⁱ	0.81 (2)	2.19 (4)	2.933 (7)	154 (7)
O4—H41⋯N1ⁱⁱⁱ	0.80 (2)	2.28 (5)	2.993 (6)	149 (8)
Symmetry codes: (i) -x, -y, z; (ii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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/S1600536811025153/ci5191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025153/ci5191Isup2.hkl

checkCIF report

Comment top

To explore the substituent effects and the effect of replacing sodium ion by potassium ion on the solid state structures of N-halo-arylsulfonamidates (Gowda & Kumar, 2003; Gowda et al., 2009, 2011; Usha & Gowda, 2006), in the present work, the structure of potassium N-bromo-2-methyl-benzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011), sodium N-chloro-2-methyl- benzenesulfonamidate sesquihydrate (III) (Gowda et al., 2009), 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 by four sulfonyl O atoms of N-bromo-2-methyl- benzenesulfonamide anions. The replacement of Na⁺ ion by K⁺ ion changes co-ordination from hexa to hepta in the metal co-ordination (Gowda et al., 2009) and other parameters.

The S—N distance of 1.577 (5) Å is consistent with an S—N double bond and is in agreement with the observed values of 1.582 (4)Å in (II) and 1.590 (2) Å in (III).

The packing consists of two-dimensional polymeric layers running parallel to the ac plane (Fig. 2). The molecular packing is stabilized by O3—H31···Br1, O3—H32···N1 and O4—H41···N1 hydrogen bonds (Table 1).

Related literature top

For the preparation of N-bromoarylsulfonamides, see: Usha & Gowda (2006). For our studies of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda & Kumar (2003); Gowda et al. (2009, 2011); Usha & Gowda (2006). 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⁺ cation. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii. Symmetry codes: (i) 1/2-x, -y, 1/2+z and (ii) -x,-y,z.
	Fig. 2. Molecular packing of the title compound with hydrogen bonds shown as dashed lines.

Potassium N-bromo-2-methylbenzenesulfonamidate sesquihydrate top

Crystal data top

K⁺·C₇H₇BrNO₂S⁻·1.5H₂O	F(000) = 2512
M_r = 315.23	D_x = 1.797 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 5298 reflections
a = 12.271 (2) Å	θ = 2.8–27.9°
b = 55.017 (6) Å	µ = 4.05 mm⁻¹
c = 6.904 (1) Å	T = 293 K
V = 4661.0 (11) Å³	Prism, yellow
Z = 16	0.42 × 0.42 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2358 independent reflections
Radiation source: fine-focus sealed tube	2140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→15
T_min = 0.281, T_max = 0.376	k = −61→68
7816 measured reflections	l = −8→8

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0467P)² + 17.9942P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.002
2358 reflections	Δρ_max = 0.68 e Å⁻³
142 parameters	Δρ_min = −0.57 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.002 (14)

Crystal data top

K⁺·C₇H₇BrNO₂S⁻·1.5H₂O	V = 4661.0 (11) Å³
M_r = 315.23	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 12.271 (2) Å	µ = 4.05 mm⁻¹
b = 55.017 (6) Å	T = 293 K
c = 6.904 (1) Å	0.42 × 0.42 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2358 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2140 reflections with I > 2σ(I)
T_min = 0.281, T_max = 0.376	R_int = 0.047
7816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0467P)² + 17.9942P] where P = (F_o² + 2F_c²)/3
S = 1.13	Δρ_max = 0.68 e Å⁻³
2358 reflections	Δρ_min = −0.57 e Å⁻³
142 parameters	Absolute structure: Flack (1983), 1060 Friedel pairs
4 restraints	Absolute structure parameter: −0.002 (14)

Special details top

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	−0.06968 (5)	0.066623 (13)	0.49885 (10)	0.0532 (2)
K1	0.15329 (9)	−0.00653 (2)	1.01716 (18)	0.0354 (3)
S1	0.09151 (10)	0.04335 (2)	0.73436 (19)	0.0285 (3)
O1	0.0096 (3)	0.03331 (7)	0.8626 (6)	0.0411 (10)
O2	0.1906 (3)	0.02885 (7)	0.7241 (7)	0.0395 (9)
O3	0.2761 (4)	−0.03137 (8)	0.7404 (8)	0.0441 (10)
H31	0.234 (5)	−0.0403 (11)	0.683 (9)	0.053*
H32	0.314 (5)	−0.0400 (11)	0.807 (9)	0.053*
O4	0.0000	0.0000	1.3142 (9)	0.0507 (17)
H41	0.031 (6)	0.0087 (12)	1.388 (9)	0.061*
N1	0.0555 (3)	0.04649 (9)	0.5166 (7)	0.0361 (11)
C1	0.1275 (5)	0.07197 (11)	0.8363 (8)	0.0334 (12)
C2	0.2037 (4)	0.08730 (11)	0.7475 (11)	0.0401 (13)
C3	0.2281 (6)	0.10908 (13)	0.8424 (12)	0.0561 (19)
H3	0.2786	0.1196	0.7877	0.067*
C4	0.1789 (6)	0.11525 (14)	1.0151 (14)	0.070 (2)
H4	0.1968	0.1298	1.0760	0.084*
C5	0.1040 (7)	0.10007 (15)	1.0968 (12)	0.064 (2)
H5	0.0700	0.1045	1.2120	0.077*
C6	0.0784 (5)	0.07831 (11)	1.0103 (10)	0.0427 (14)
H6	0.0284	0.0679	1.0680	0.051*
C7	0.2617 (6)	0.08176 (15)	0.5606 (11)	0.0579 (19)
H7A	0.2225	0.0889	0.4546	0.070*
H7B	0.2656	0.0645	0.5428	0.070*
H7C	0.3341	0.0884	0.5651	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0458 (3)	0.0596 (4)	0.0542 (4)	0.0077 (3)	−0.0059 (3)	0.0155 (4)
K1	0.0369 (6)	0.0350 (7)	0.0342 (6)	0.0050 (5)	−0.0057 (6)	−0.0007 (5)
S1	0.0349 (6)	0.0215 (6)	0.0292 (6)	0.0011 (5)	0.0023 (6)	0.0019 (5)
O1	0.047 (2)	0.035 (3)	0.041 (2)	−0.0050 (19)	0.0112 (18)	0.0067 (19)
O2	0.044 (2)	0.032 (2)	0.043 (2)	0.0123 (18)	0.007 (2)	0.008 (2)
O3	0.054 (2)	0.036 (2)	0.042 (2)	0.0000 (19)	−0.003 (2)	−0.002 (2)
O4	0.078 (5)	0.042 (4)	0.032 (3)	−0.018 (3)	0.000	0.000
N1	0.041 (2)	0.037 (3)	0.031 (2)	0.006 (2)	−0.006 (2)	−0.008 (2)
C1	0.038 (3)	0.031 (3)	0.031 (3)	0.006 (2)	−0.009 (2)	0.002 (2)
C2	0.040 (3)	0.032 (3)	0.048 (3)	−0.001 (2)	−0.009 (3)	0.005 (3)
C3	0.063 (4)	0.035 (4)	0.070 (5)	−0.010 (3)	−0.023 (4)	0.003 (4)
C4	0.084 (5)	0.044 (5)	0.081 (6)	0.001 (4)	−0.030 (5)	−0.024 (4)
C5	0.089 (6)	0.051 (5)	0.053 (4)	0.021 (4)	−0.011 (4)	−0.016 (4)
C6	0.054 (3)	0.042 (3)	0.032 (3)	0.012 (3)	−0.007 (3)	−0.011 (3)
C7	0.065 (4)	0.057 (5)	0.051 (4)	−0.020 (4)	−0.001 (3)	0.008 (3)

Geometric parameters (Å, º) top

Br1—N1	1.897 (4)	O3—H31	0.81 (2)
K1—O2ⁱ	2.687 (4)	O3—H32	0.81 (2)
K1—O1ⁱⁱ	2.703 (4)	O4—K1ⁱⁱ	2.806 (5)
K1—O3ⁱ	2.734 (5)	O4—H41	0.80 (2)
K1—O3	2.791 (5)	C1—C6	1.388 (9)
K1—O4	2.806 (5)	C1—C2	1.401 (8)
K1—O2	2.845 (4)	C2—C3	1.398 (9)
K1—O1	3.009 (4)	C2—C7	1.505 (10)
K1—S1	3.4522 (17)	C3—C4	1.379 (12)
K1—H32	3.06 (7)	C3—H3	0.93
K1—H41	3.08 (7)	C4—C5	1.364 (12)
S1—O1	1.448 (4)	C4—H4	0.93
S1—O2	1.456 (4)	C5—C6	1.375 (10)
S1—N1	1.577 (5)	C5—H5	0.93
S1—C1	1.780 (6)	C6—H6	0.93
O1—K1ⁱⁱ	2.703 (4)	C7—H7A	0.96
O2—K1ⁱⁱⁱ	2.687 (4)	C7—H7B	0.96
O3—K1ⁱⁱⁱ	2.734 (5)	C7—H7C	0.96

O2ⁱ—K1—O1ⁱⁱ	119.23 (13)	O1—S1—C1	105.5 (3)
O2ⁱ—K1—O3ⁱ	79.79 (13)	O2—S1—C1	107.3 (3)
O1ⁱⁱ—K1—O3ⁱ	150.77 (14)	N1—S1—C1	110.4 (3)
O2ⁱ—K1—O3	75.84 (15)	O1—S1—K1	60.24 (17)
O1ⁱⁱ—K1—O3	82.08 (13)	O2—S1—K1	53.75 (17)
O3ⁱ—K1—O3	126.03 (8)	N1—S1—K1	133.49 (18)
O2ⁱ—K1—O4	98.51 (14)	C1—S1—K1	115.16 (18)
O1ⁱⁱ—K1—O4	82.10 (12)	S1—O1—K1ⁱⁱ	164.2 (3)
O3ⁱ—K1—O4	72.71 (11)	S1—O1—K1	95.1 (2)
O3—K1—O4	157.69 (11)	K1ⁱⁱ—O1—K1	84.04 (11)
O2ⁱ—K1—O2	125.18 (8)	S1—O2—K1ⁱⁱⁱ	150.7 (3)
O1ⁱⁱ—K1—O2	102.19 (14)	S1—O2—K1	101.9 (2)
O3ⁱ—K1—O2	80.10 (15)	K1ⁱⁱⁱ—O2—K1	100.39 (12)
O3—K1—O2	76.18 (13)	K1ⁱⁱⁱ—O3—K1	100.59 (15)
O4—K1—O2	122.68 (10)	K1ⁱⁱⁱ—O3—H31	113 (5)
O2ⁱ—K1—O1	159.94 (13)	K1—O3—H31	107 (5)
O1ⁱⁱ—K1—O1	79.85 (15)	K1ⁱⁱⁱ—O3—H32	126 (5)
O3ⁱ—K1—O1	80.21 (13)	K1—O3—H32	102 (5)
O3—K1—O1	115.48 (14)	H31—O3—H32	107 (7)
O4—K1—O1	76.89 (11)	K1ⁱⁱ—O4—K1	86.09 (18)
O2—K1—O1	48.96 (11)	K1ⁱⁱ—O4—H41	135 (6)
O2ⁱ—K1—S1	145.14 (11)	K1—O4—H41	103 (6)
O1ⁱⁱ—K1—S1	92.72 (10)	S1—N1—Br1	110.7 (3)
O3ⁱ—K1—S1	77.42 (11)	C6—C1—C2	121.1 (6)
O3—K1—S1	96.92 (11)	C6—C1—S1	117.2 (5)
O4—K1—S1	99.45 (7)	C2—C1—S1	121.7 (5)
O2—K1—S1	24.37 (8)	C3—C2—C1	117.0 (7)
O1—K1—S1	24.70 (8)	C3—C2—C7	118.3 (6)
O2ⁱ—K1—H32	61.2 (8)	C1—C2—C7	124.7 (6)
O1ⁱⁱ—K1—H32	87.8 (13)	C4—C3—C2	121.5 (7)
O3ⁱ—K1—H32	121.4 (13)	C4—C3—H3	119.2
O3—K1—H32	15.0 (7)	C2—C3—H3	119.2
O4—K1—H32	148.7 (11)	C5—C4—C3	120.1 (7)
O2—K1—H32	88.3 (10)	C5—C4—H4	119.9
O1—K1—H32	130.3 (7)	C3—C4—H4	119.9
S1—K1—H32	110.6 (9)	C4—C5—C6	120.5 (8)
O2ⁱ—K1—H41	91.7 (14)	C4—C5—H5	119.7
O1ⁱⁱ—K1—H41	96.7 (8)	C6—C5—H5	119.7
O3ⁱ—K1—H41	58.6 (8)	C5—C6—C1	119.7 (7)
O3—K1—H41	164.7 (15)	C5—C6—H6	120.1
O4—K1—H41	14.6 (7)	C1—C6—H6	120.1
O2—K1—H41	118.9 (14)	C2—C7—H7A	109.5
O1—K1—H41	79.1 (15)	C2—C7—H7B	109.5
S1—K1—H41	98.4 (15)	H7A—C7—H7B	109.5
H32—K1—H41	150.4 (17)	C2—C7—H7C	109.5
O1—S1—O2	113.6 (3)	H7A—C7—H7C	109.5
O1—S1—N1	115.5 (3)	H7B—C7—H7C	109.5
O2—S1—N1	104.4 (3)

O2ⁱ—K1—S1—O1	−144.3 (3)	C1—S1—O2—K1	108.9 (2)
O1ⁱⁱ—K1—S1—O1	58.28 (18)	O2ⁱ—K1—O2—S1	−151.27 (18)
O3ⁱ—K1—S1—O1	−93.9 (2)	O1ⁱⁱ—K1—O2—S1	69.0 (3)
O3—K1—S1—O1	140.6 (2)	O3ⁱ—K1—O2—S1	−81.3 (3)
O4—K1—S1—O1	−24.2 (2)	O3—K1—O2—S1	147.5 (3)
O2—K1—S1—O1	172.3 (3)	O4—K1—O2—S1	−19.4 (3)
O2ⁱ—K1—S1—O2	43.4 (2)	O1—K1—O2—S1	4.25 (18)
O1ⁱⁱ—K1—S1—O2	−114.0 (3)	O2ⁱ—K1—O2—K1ⁱⁱⁱ	48.0 (2)
O3ⁱ—K1—S1—O2	93.8 (3)	O1ⁱⁱ—K1—O2—K1ⁱⁱⁱ	−91.81 (15)
O3—K1—S1—O2	−31.7 (3)	O3ⁱ—K1—O2—K1ⁱⁱⁱ	117.89 (15)
O4—K1—S1—O2	163.5 (3)	O3—K1—O2—K1ⁱⁱⁱ	−13.25 (13)
O1—K1—S1—O2	−172.3 (3)	O4—K1—O2—K1ⁱⁱⁱ	179.83 (12)
O2ⁱ—K1—S1—N1	117.7 (3)	O1—K1—O2—K1ⁱⁱⁱ	−156.5 (2)
O1ⁱⁱ—K1—S1—N1	−39.8 (3)	S1—K1—O2—K1ⁱⁱⁱ	−160.8 (3)
O3ⁱ—K1—S1—N1	168.0 (3)	O2ⁱ—K1—O3—K1ⁱⁱⁱ	−119.35 (16)
O3—K1—S1—N1	42.6 (3)	O1ⁱⁱ—K1—O3—K1ⁱⁱⁱ	117.72 (16)
O4—K1—S1—N1	−122.2 (3)	O3ⁱ—K1—O3—K1ⁱⁱⁱ	−53.5 (3)
O2—K1—S1—N1	74.2 (3)	O4—K1—O3—K1ⁱⁱⁱ	162.9 (3)
O1—K1—S1—N1	−98.1 (3)	O2—K1—O3—K1ⁱⁱⁱ	13.02 (13)
O2ⁱ—K1—S1—C1	−50.1 (3)	O1—K1—O3—K1ⁱⁱⁱ	42.99 (18)
O1ⁱⁱ—K1—S1—C1	152.4 (2)	S1—K1—O3—K1ⁱⁱⁱ	25.92 (13)
O3ⁱ—K1—S1—C1	0.2 (2)	O2ⁱ—K1—O4—K1ⁱⁱ	−161.43 (10)
O3—K1—S1—C1	−125.3 (2)	O1ⁱⁱ—K1—O4—K1ⁱⁱ	−42.89 (9)
O4—K1—S1—C1	70.0 (2)	O3ⁱ—K1—O4—K1ⁱⁱ	122.12 (11)
O2—K1—S1—C1	−93.6 (3)	O3—K1—O4—K1ⁱⁱ	−88.1 (4)
O1—K1—S1—C1	94.1 (3)	O2—K1—O4—K1ⁱⁱ	56.56 (13)
O2—S1—O1—K1ⁱⁱ	−79.2 (10)	O1—K1—O4—K1ⁱⁱ	38.46 (9)
N1—S1—O1—K1ⁱⁱ	41.3 (10)	S1—K1—O4—K1ⁱⁱ	48.57 (3)
C1—S1—O1—K1ⁱⁱ	163.5 (9)	O1—S1—N1—Br1	57.7 (3)
K1—S1—O1—K1ⁱⁱ	−86.0 (9)	O2—S1—N1—Br1	−176.9 (2)
O2—S1—O1—K1	6.8 (3)	C1—S1—N1—Br1	−61.9 (3)
N1—S1—O1—K1	127.3 (2)	K1—S1—N1—Br1	129.90 (18)
C1—S1—O1—K1	−110.5 (2)	O1—S1—C1—C6	2.8 (5)
O2ⁱ—K1—O1—S1	76.8 (5)	O2—S1—C1—C6	−118.6 (5)
O1ⁱⁱ—K1—O1—S1	−120.32 (14)	N1—S1—C1—C6	128.3 (4)
O3ⁱ—K1—O1—S1	81.2 (2)	K1—S1—C1—C6	−61.2 (5)
O3—K1—O1—S1	−44.2 (2)	O1—S1—C1—C2	−178.5 (5)
O4—K1—O1—S1	155.5 (2)	O2—S1—C1—C2	60.1 (5)
O2—K1—O1—S1	−4.20 (18)	N1—S1—C1—C2	−53.1 (5)
O2ⁱ—K1—O1—K1ⁱⁱ	−119.1 (4)	K1—S1—C1—C2	117.5 (4)
O1ⁱⁱ—K1—O1—K1ⁱⁱ	43.81 (17)	C6—C1—C2—C3	0.3 (8)
O3ⁱ—K1—O1—K1ⁱⁱ	−114.72 (14)	S1—C1—C2—C3	−178.4 (5)
O3—K1—O1—K1ⁱⁱ	119.90 (14)	C6—C1—C2—C7	179.3 (6)
O4—K1—O1—K1ⁱⁱ	−40.36 (9)	S1—C1—C2—C7	0.6 (8)
O2—K1—O1—K1ⁱⁱ	159.9 (2)	C1—C2—C3—C4	−0.3 (10)
S1—K1—O1—K1ⁱⁱ	164.1 (3)	C7—C2—C3—C4	−179.4 (7)
O1—S1—O2—K1ⁱⁱⁱ	131.3 (5)	C2—C3—C4—C5	−0.5 (11)
N1—S1—O2—K1ⁱⁱⁱ	4.7 (6)	C3—C4—C5—C6	1.3 (12)
C1—S1—O2—K1ⁱⁱⁱ	−112.5 (5)	C4—C5—C6—C1	−1.3 (11)
K1—S1—O2—K1ⁱⁱⁱ	138.6 (6)	C2—C1—C6—C5	0.6 (9)
O1—S1—O2—K1	−7.3 (3)	S1—C1—C6—C5	179.3 (5)
N1—S1—O2—K1	−133.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Br1ⁱⁱ	0.81 (2)	2.79 (2)	3.600 (5)	173 (7)
O3—H32···N1ⁱ	0.81 (2)	2.19 (4)	2.933 (7)	154 (7)
O4—H41···N1^iv	0.80 (2)	2.28 (5)	2.993 (6)	149 (8)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₇H₇BrNO₂S⁻·1.5H₂O
M_r	315.23
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	293
a, b, c (Å)	12.271 (2), 55.017 (6), 6.904 (1)
V (Å³)	4661.0 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	4.05
Crystal size (mm)	0.42 × 0.42 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.281, 0.376
No. of measured, independent and observed [I > 2σ(I)] reflections	7816, 2358, 2140
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.112, 1.13
No. of reflections	2358
No. of parameters	142
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0467P)² + 17.9942P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.57
Absolute structure	Flack (1983), 1060 Friedel pairs
Absolute structure parameter	−0.002 (14)

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	0.81 (2)	2.79 (2)	3.600 (5)	173 (7)
O3—H32···N1ⁱⁱ	0.81 (2)	2.19 (4)	2.933 (7)	154 (7)
O4—H41···N1ⁱⁱⁱ	0.80 (2)	2.28 (5)	2.993 (6)	149 (8)

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

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

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
George, E., Vivekanandan, S. & Sivakumar, K. (2000). Acta Cryst. C56, 1208–1209. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, m700. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Shakuntala, K. (2011). Acta Cryst. E67, m926. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. 26, 403–425. CAS Google Scholar
Olmstead, M. M. & Power, P. P. (1986). Inorg. Chem. 25, 4057–4058. CSD CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359. Web of Science CrossRef CAS Google Scholar