Potassium N-bromo-2-nitro­benzene­sulfonamidate monohydrate

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

doi:10.1107/S1600536812042080

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1358

doi:10.1107/S1600536812042080

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Potassium N-bromo-2-nitrobenzenesulfonamidate monohydrate

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 4 October 2012; accepted 8 October 2012; online 13 October 2012)

In the title compound, K⁺·C₆H₄BrN₂O₄S⁻·H₂O, the K⁺ ion is hepta-coordinated by two O atoms from two different water molecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzenesulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzenesulfonamidate anions. The S—N distance of 1.576 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by intermolecular O—H⋯N and O—H⋯Br hydrogen bonds which link the molecules into polymeric layers running parallel to the bc plane.

Related literature

For the preparation of metal salts of N-haloarylsulfonamides, see: Gowda & Mahadevappa (1983 ); Usha & Gowda (2006 ). For studies on the effect of substituents and metal ions on the structures of N-haloarylsulfonamides, see: George et al. (2000 ); Gowda et al. (2011a ,b ); Olmstead & Power (1986 ). For positioning of water H atoms, see: Nardelli (1999 ).

Experimental

Crystal data

K⁺·C₆H₄BrN₂O₄S⁻·H₂O
M_r = 337.20
Monoclinic, P 2₁ /c
a = 13.034 (2) Å
b = 12.815 (2) Å
c = 6.7741 (9) Å
β = 100.65 (1)°
V = 1112.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.27 mm⁻¹
T = 293 K
0.48 × 0.48 × 0.24 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 = 0.234, T_max = 0.428
3896 measured reflections
2236 independent reflections
1847 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.145
S = 1.06
2236 reflections
152 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −1.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯N1ⁱ	0.84 (2)	2.13 (3)	2.926 (5)	157 (5)
O5—H52⋯Br1ⁱⁱ	0.84 (2)	2.85 (4)	3.509 (4)	137 (4)
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536812042080/zl2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042080/zl2509Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042080/zl2509Isup3.cml

checkCIF report

Comment top

In the present work, to explore the effect of substituents on the crystal structures of metal salts of N-haloarylsulfonamidates (George et al., 2000; Gowda et al., 2011a,b; Olmstead & Power, 1986), the crystal structure of potassium N-bromo-2-nitro-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., 2011a), potassium N-bromo-2-methyl-benzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), and sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the title compound (I), the K⁺ ion is hepta coordinated by two O atoms from two different water molecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzenesulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzenesulfonamidate anions (Fig 2.). This is in contrast to K⁺ ion hepta coordination by three O atoms from water molecules and by four sulfonyl O atoms of three N-bromo-2-chloro-benzenesulfonamide anions in (II) and three N-bromo-2-methyl-benzenesulfonamide anions in (III).

The S—N distance of 1.576 (4) Å in (I) is consistent with an S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II) and 1.577 (5) Å in (III).

The packing diagram consists of a two-dimensional polymeric layer running parallel to the bc plane (Fig. 2). The molecular packing is stabilized by O5—H51···N1 and O5—H52···Br1 hydrogen bonds (Table 1).

Related literature top

For the preparation of metal salts of N-haloarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006). For studies on the effect of substituents and metal ions on the structures of N-haloarylsulfonamides, see: George et al. (2000); Gowda et al. (2011a,b); Olmstead & Power (1986). For positioning of water H atoms, see: Nardelli (1999).

Experimental top

The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda & Mahadevappa, 1983) and Usha & Gowda (Usha & Gowda, 2006). 2 g of 2-nitrobenzenesulfonamide 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-nitro-benzenesulfonamidate monohydrate 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 (175–177°C) and estimating, iodometrically, the amount of active bromine present in it. It was further characterized from its infrared spectrum. The characteristic absorptions observed are 3624.3, 3333.0, 3192.2, 2978.1, 2922.2, 2075.4, 1626.0, 1602.9, 1477.5, 1452.4, 1242.2, 1122.6, 1060.9, 937.4, 817.8, 686.7, 640.4, 578.6, 549.6, 524.6 and 470.6 cm^-1.

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⁺ ion. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Bridging of potassium cations, N-bromo-2-nitro-benzenesulfonamidate anions and water molecules in the structure of the title compound.
	Fig. 3. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Potassium N-bromo-2-nitrobenzenesulfonamidate monohydrate top

Crystal data top

K⁺·C₆H₄BrN₂O₄S⁻·H₂O	F(000) = 664
M_r = 337.20	D_x = 2.014 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2399 reflections
a = 13.034 (2) Å	θ = 3.1–27.8°
b = 12.815 (2) Å	µ = 4.27 mm⁻¹
c = 6.7741 (9) Å	T = 293 K
β = 100.65 (1)°	Prism, yellow
V = 1112.0 (3) Å³	0.48 × 0.48 × 0.24 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2236 independent reflections
Radiation source: fine-focus sealed tube	1847 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Rotation method data acquisition using ω scans.	θ_max = 26.4°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→12
T_min = 0.234, T_max = 0.428	k = −16→11
3896 measured reflections	l = −6→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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0909P)² + 0.1082P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
2236 reflections	Δρ_max = 0.79 e Å⁻³
152 parameters	Δρ_min = −1.21 e Å⁻³
3 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: 0.082 (5)

Crystal data top

K⁺·C₆H₄BrN₂O₄S⁻·H₂O	V = 1112.0 (3) Å³
M_r = 337.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.034 (2) Å	µ = 4.27 mm⁻¹
b = 12.815 (2) Å	T = 293 K
c = 6.7741 (9) Å	0.48 × 0.48 × 0.24 mm
β = 100.65 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2236 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1847 reflections with I > 2σ(I)
T_min = 0.234, T_max = 0.428	R_int = 0.042
3896 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	3 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.79 e Å⁻³
2236 reflections	Δρ_min = −1.21 e Å⁻³
152 parameters

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
C1	0.2873 (3)	−0.0123 (3)	0.3340 (6)	0.0272 (9)
C2	0.3529 (3)	0.0693 (3)	0.3079 (6)	0.0271 (8)
C3	0.4505 (3)	0.0546 (4)	0.2573 (6)	0.0346 (10)
H3	0.4930	0.1113	0.2430	0.042*
C4	0.4833 (4)	−0.0463 (4)	0.2286 (7)	0.0419 (11)
H4	0.5488	−0.0583	0.1975	0.050*
C5	0.4173 (4)	−0.1291 (4)	0.2469 (7)	0.0425 (11)
H5	0.4377	−0.1966	0.2221	0.051*
C6	0.3214 (4)	−0.1127 (3)	0.3015 (7)	0.0368 (10)
H6	0.2791	−0.1695	0.3167	0.044*
Br1	0.24804 (4)	−0.10055 (4)	0.78959 (7)	0.0470 (3)
K1	0.09562 (9)	0.13045 (8)	0.88211 (15)	0.0418 (3)
N1	0.1510 (3)	−0.1035 (3)	0.5411 (6)	0.0384 (9)
N2	0.3214 (3)	0.1792 (3)	0.3257 (5)	0.0316 (8)
O1	0.1685 (3)	0.0941 (2)	0.5295 (5)	0.0395 (8)
O2	0.0840 (3)	−0.0085 (2)	0.2371 (5)	0.0442 (8)
O3	0.2363 (3)	0.2061 (3)	0.2308 (5)	0.0454 (8)
O4	0.3826 (3)	0.2369 (3)	0.4304 (6)	0.0520 (9)
S1	0.16307 (8)	−0.00155 (7)	0.41728 (15)	0.0294 (3)
O5	−0.0180 (3)	0.2758 (3)	0.6363 (6)	0.0494 (9)
H51	−0.066 (3)	0.240 (3)	0.566 (7)	0.059*
H52	−0.044 (4)	0.326 (3)	0.689 (8)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.027 (2)	0.0276 (19)	0.0253 (18)	0.0017 (17)	0.0016 (16)	−0.0018 (16)
C2	0.026 (2)	0.0279 (18)	0.0271 (18)	0.0015 (17)	0.0053 (16)	0.0028 (16)
C3	0.032 (2)	0.042 (2)	0.032 (2)	0.000 (2)	0.0101 (18)	0.0059 (19)
C4	0.036 (3)	0.054 (3)	0.038 (2)	0.014 (2)	0.015 (2)	0.001 (2)
C5	0.047 (3)	0.036 (2)	0.045 (3)	0.020 (2)	0.012 (2)	−0.003 (2)
C6	0.041 (3)	0.030 (2)	0.040 (2)	0.0028 (19)	0.009 (2)	−0.0020 (18)
Br1	0.0516 (4)	0.0461 (4)	0.0432 (4)	−0.0034 (2)	0.0087 (2)	0.0096 (2)
K1	0.0378 (6)	0.0498 (6)	0.0380 (5)	0.0041 (5)	0.0076 (4)	−0.0024 (5)
N1	0.036 (2)	0.034 (2)	0.047 (2)	−0.0106 (16)	0.0122 (19)	0.0010 (16)
N2	0.032 (2)	0.0279 (17)	0.0369 (18)	−0.0005 (15)	0.0100 (16)	0.0052 (15)
O1	0.046 (2)	0.0313 (15)	0.0463 (18)	−0.0007 (13)	0.0206 (16)	−0.0100 (13)
O2	0.0293 (17)	0.0527 (19)	0.0465 (18)	−0.0035 (15)	−0.0039 (15)	−0.0014 (16)
O3	0.045 (2)	0.0325 (17)	0.0564 (19)	0.0096 (15)	0.0025 (16)	0.0113 (15)
O4	0.048 (2)	0.0379 (17)	0.070 (2)	−0.0146 (16)	0.0112 (19)	−0.0130 (17)
S1	0.0254 (6)	0.0274 (5)	0.0360 (5)	−0.0033 (4)	0.0069 (4)	−0.0032 (4)
O5	0.043 (2)	0.0443 (19)	0.063 (2)	−0.0011 (16)	0.0146 (18)	0.0010 (17)

Geometric parameters (Å, º) top

C1—C2	1.383 (6)	K1—O2ⁱⁱ	2.806 (3)
C1—C6	1.391 (5)	K1—O3ⁱⁱⁱ	2.877 (4)
C1—S1	1.815 (4)	K1—O2ⁱⁱⁱ	3.018 (4)
C2—C3	1.390 (6)	K1—O3ⁱ	3.081 (4)
C2—N2	1.479 (5)	K1—H51	3.06 (5)
C3—C4	1.386 (6)	N1—S1	1.576 (4)
C3—H3	0.9300	N2—O4	1.215 (5)
C4—C5	1.385 (7)	N2—O3	1.225 (5)
C4—H4	0.9300	O1—S1	1.437 (3)
C5—C6	1.384 (7)	O2—S1	1.448 (3)
C5—H5	0.9300	O2—K1ⁱⁱ	2.806 (3)
C6—H6	0.9300	O2—K1^iv	3.018 (4)
Br1—N1	1.910 (4)	O3—K1^iv	2.877 (4)
Br1—K1	3.6829 (12)	O3—K1^v	3.081 (4)
K1—O5	2.743 (4)	O5—K1^v	2.746 (4)
K1—O5ⁱ	2.746 (4)	O5—H51	0.844 (19)
K1—O1	2.768 (3)	O5—H52	0.841 (19)

C2—C1—C6	117.1 (4)	O2ⁱⁱⁱ—K1—O3ⁱ	141.88 (10)
C2—C1—S1	126.2 (3)	O5—K1—Br1	133.65 (9)
C6—C1—S1	116.7 (3)	O5ⁱ—K1—Br1	145.95 (9)
C1—C2—C3	123.0 (4)	O1—K1—Br1	55.66 (7)
C1—C2—N2	121.5 (4)	O2ⁱⁱ—K1—Br1	87.19 (8)
C3—C2—N2	115.4 (4)	O3ⁱⁱⁱ—K1—Br1	97.38 (7)
C4—C3—C2	118.7 (4)	O2ⁱⁱⁱ—K1—Br1	76.67 (7)
C4—C3—H3	120.6	O3ⁱ—K1—Br1	96.72 (7)
C2—C3—H3	120.6	O5—K1—H51	15.6 (6)
C5—C4—C3	119.3 (4)	O5ⁱ—K1—H51	81.7 (9)
C5—C4—H4	120.4	O1—K1—H51	77.0 (10)
C3—C4—H4	120.4	O2ⁱⁱ—K1—H51	68.0 (7)
C6—C5—C4	120.9 (4)	O3ⁱⁱⁱ—K1—H51	132.2 (6)
C6—C5—H5	119.5	O2ⁱⁱⁱ—K1—H51	134.5 (10)
C4—C5—H5	119.5	O3ⁱ—K1—H51	80.1 (8)
C5—C6—C1	120.9 (4)	Br1—K1—H51	125.1 (8)
C5—C6—H6	119.5	S1—N1—Br1	109.8 (2)
C1—C6—H6	119.5	O4—N2—O3	124.7 (4)
N1—Br1—K1	82.87 (12)	O4—N2—C2	117.7 (4)
O5—K1—O5ⁱ	77.92 (8)	O3—N2—C2	117.6 (3)
O5—K1—O1	79.82 (11)	S1—O1—K1	127.53 (18)
O5ⁱ—K1—O1	157.72 (11)	S1—O2—K1ⁱⁱ	134.68 (19)
O5—K1—O2ⁱⁱ	82.86 (11)	S1—O2—K1^iv	120.16 (18)
O5ⁱ—K1—O2ⁱⁱ	84.62 (11)	K1ⁱⁱ—O2—K1^iv	105.16 (10)
O1—K1—O2ⁱⁱ	93.37 (11)	N2—O3—K1^iv	135.6 (3)
O5—K1—O3ⁱⁱⁱ	117.39 (11)	N2—O3—K1^v	123.6 (3)
O5ⁱ—K1—O3ⁱⁱⁱ	70.94 (11)	K1^iv—O3—K1^v	100.02 (11)
O1—K1—O3ⁱⁱⁱ	119.80 (11)	O1—S1—O2	117.1 (2)
O2ⁱⁱ—K1—O3ⁱⁱⁱ	142.64 (11)	O1—S1—N1	115.2 (2)
O5—K1—O2ⁱⁱⁱ	141.57 (11)	O2—S1—N1	105.8 (2)
O5ⁱ—K1—O2ⁱⁱⁱ	69.28 (11)	O1—S1—C1	105.67 (19)
O1—K1—O2ⁱⁱⁱ	131.59 (10)	O2—S1—C1	105.7 (2)
O2ⁱⁱ—K1—O2ⁱⁱⁱ	74.84 (10)	N1—S1—C1	106.5 (2)
O3ⁱⁱⁱ—K1—O2ⁱⁱⁱ	70.30 (9)	K1—O5—K1^v	112.63 (13)
O5—K1—O3ⁱ	67.90 (10)	K1—O5—H51	104 (4)
O5ⁱ—K1—O3ⁱ	109.52 (11)	K1^v—O5—H51	108 (4)
O1—K1—O3ⁱ	60.50 (9)	K1—O5—H52	118 (4)
O2ⁱⁱ—K1—O3ⁱ	143.02 (10)	K1^v—O5—H52	104 (4)
O3ⁱⁱⁱ—K1—O3ⁱ	73.50 (8)	H51—O5—H52	110 (3)

C6—C1—C2—C3	−1.9 (6)	O4—N2—O3—K1^iv	156.5 (3)
S1—C1—C2—C3	175.3 (3)	C2—N2—O3—K1^iv	−22.1 (5)
C6—C1—C2—N2	176.0 (4)	O4—N2—O3—K1^v	−35.7 (5)
S1—C1—C2—N2	−6.8 (6)	C2—N2—O3—K1^v	145.7 (3)
C1—C2—C3—C4	1.0 (6)	K1—O1—S1—O2	102.7 (3)
N2—C2—C3—C4	−177.0 (4)	K1—O1—S1—N1	−22.6 (3)
C2—C3—C4—C5	1.3 (7)	K1—O1—S1—C1	−139.9 (2)
C3—C4—C5—C6	−2.8 (7)	K1ⁱⁱ—O2—S1—O1	−114.6 (3)
C4—C5—C6—C1	1.8 (8)	K1^iv—O2—S1—O1	65.8 (3)
C2—C1—C6—C5	0.5 (7)	K1ⁱⁱ—O2—S1—N1	15.4 (3)
S1—C1—C6—C5	−177.0 (4)	K1^iv—O2—S1—N1	−164.3 (2)
N1—Br1—K1—O5	−28.49 (17)	K1ⁱⁱ—O2—S1—C1	128.1 (3)
N1—Br1—K1—O5ⁱ	124.97 (19)	K1^iv—O2—S1—C1	−51.6 (2)
N1—Br1—K1—O1	−47.15 (14)	Br1—N1—S1—O1	−46.5 (3)
N1—Br1—K1—O2ⁱⁱ	48.87 (14)	Br1—N1—S1—O2	−177.5 (2)
N1—Br1—K1—O3ⁱⁱⁱ	−168.38 (14)	Br1—N1—S1—C1	70.3 (2)
N1—Br1—K1—O2ⁱⁱⁱ	123.95 (13)	C2—C1—S1—O1	−24.4 (4)
N1—Br1—K1—O3ⁱ	−94.22 (13)	C6—C1—S1—O1	152.8 (3)
K1—Br1—N1—S1	63.0 (2)	C2—C1—S1—O2	100.4 (4)
C1—C2—N2—O4	131.2 (4)	C6—C1—S1—O2	−82.4 (4)
C3—C2—N2—O4	−50.8 (5)	C2—C1—S1—N1	−147.4 (4)
C1—C2—N2—O3	−50.2 (5)	C6—C1—S1—N1	29.8 (4)
C3—C2—N2—O3	127.9 (4)	O5ⁱ—K1—O5—K1^v	140.66 (16)
O5—K1—O1—S1	−120.6 (3)	O1—K1—O5—K1^v	−38.60 (13)
O5ⁱ—K1—O1—S1	−122.5 (3)	O2ⁱⁱ—K1—O5—K1^v	−133.34 (15)
O2ⁱⁱ—K1—O1—S1	−38.5 (3)	O3ⁱⁱⁱ—K1—O5—K1^v	79.80 (16)
O3ⁱⁱⁱ—K1—O1—S1	123.5 (2)	O2ⁱⁱⁱ—K1—O5—K1^v	172.23 (12)
O2ⁱⁱⁱ—K1—O1—S1	34.2 (3)	O3ⁱ—K1—O5—K1^v	23.55 (11)
O3ⁱ—K1—O1—S1	169.1 (3)	Br1—K1—O5—K1^v	−54.17 (18)
Br1—K1—O1—S1	45.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···N1ⁱⁱ	0.84 (2)	2.13 (3)	2.926 (5)	157 (5)
O5—H52···Br1^vi	0.84 (2)	2.85 (4)	3.509 (4)	137 (4)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₆H₄BrN₂O₄S⁻·H₂O
M_r	337.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.034 (2), 12.815 (2), 6.7741 (9)
β (°)	100.65 (1)
V (Å³)	1112.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.27
Crystal size (mm)	0.48 × 0.48 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.234, 0.428
No. of measured, independent and observed [I > 2σ(I)] reflections	3896, 2236, 1847
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.145, 1.06
No. of reflections	2236
No. of parameters	152
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)	0.79, −1.21

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
O5—H51···N1ⁱ	0.844 (19)	2.13 (3)	2.926 (5)	157 (5)
O5—H52···Br1ⁱⁱ	0.841 (19)	2.85 (4)	3.509 (4)	137 (4)

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

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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