Potassium N-bromo-2-nitro-benzene-sulfonamidate monohydrate.

In the title compound, K(+)·C(6)H(4)BrN(2)O(4)S(-)·H(2)O, the K(+) ion is hepta-coordinated by two O atoms from two different water mol-ecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzene-sulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzene-sulfonamidate anions. The S-N distance of 1.576 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by inter-molecular 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 = 337.20

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 1.06

2236 reflections

152 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −1.21 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042080/zl2509sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042080/zl2509Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

K+·C6H4BrN2O4S−·H2O	F(000) = 664
Mr = 337.20	Dx = 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

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	Rint = 0.042
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→12
Tmin = 0.234, Tmax = 0.428	k = −16→11
3896 measured reflections	l = −6→8

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(Fo2) + (0.0909P)2 + 0.1082P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
2236 reflections	Δρmax = 0.79 e Å−3
152 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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—K1iv	3.018 (4)
Br1—N1	1.910 (4)	O3—K1iv	2.877 (4)
Br1—K1	3.6829 (12)	O3—K1v	3.081 (4)
K1—O5	2.743 (4)	O5—K1v	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—K1iv	120.16 (18)
O5i—K1—O2ii	84.62 (11)	K1ii—O2—K1iv	105.16 (10)
O1—K1—O2ii	93.37 (11)	N2—O3—K1iv	135.6 (3)
O5—K1—O3iii	117.39 (11)	N2—O3—K1v	123.6 (3)
O5i—K1—O3iii	70.94 (11)	K1iv—O3—K1v	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—K1v	112.63 (13)
O5—K1—O3i	67.90 (10)	K1—O5—H51	104 (4)
O5i—K1—O3i	109.52 (11)	K1v—O5—H51	108 (4)
O1—K1—O3i	60.50 (9)	K1—O5—H52	118 (4)
O2ii—K1—O3i	143.02 (10)	K1v—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—K1iv	156.5 (3)
S1—C1—C2—C3	175.3 (3)	C2—N2—O3—K1iv	−22.1 (5)
C6—C1—C2—N2	176.0 (4)	O4—N2—O3—K1v	−35.7 (5)
S1—C1—C2—N2	−6.8 (6)	C2—N2—O3—K1v	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)	K1iv—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)	K1iv—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)	K1iv—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—K1v	140.66 (16)
O5—K1—O1—S1	−120.6 (3)	O1—K1—O5—K1v	−38.60 (13)
O5i—K1—O1—S1	−122.5 (3)	O2ii—K1—O5—K1v	−133.34 (15)
O2ii—K1—O1—S1	−38.5 (3)	O3iii—K1—O5—K1v	79.80 (16)
O3iii—K1—O1—S1	123.5 (2)	O2iii—K1—O5—K1v	172.23 (12)
O2iii—K1—O1—S1	34.2 (3)	O3i—K1—O5—K1v	23.55 (11)
O3i—K1—O1—S1	169.1 (3)	Br1—K1—O5—K1v	−54.17 (18)
Br1—K1—O1—S1	45.8 (2)

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···Br1vi	0.84 (2)	2.85 (4)	3.509 (4)	137 (4)

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) ; (ii) .