Potassium N-bromo-2-methyl-benzene-sulfonamidate sesquihydrate.

In the structure of the title compound, K(+)·C(7)H(7)BrNO(2)S(-)·1.5H(2)O, the K(+) ion is hepta-coordinated by three O atoms from water mol-ecules and by four sulfonyl O atoms of N-bromo-2-methyl-benzene-sulfonamide 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 = 315.23

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.112

S = 1.13

2358 reflections

142 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.57 e Å−3

Absolute structure: Flack (1983 ▶), 1060 Friedel pairs

Flack parameter: −0.002 (14)

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025153/ci5191sup1.cif

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

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

K+·C7H7BrNO2S−·1.5H2O	F(000) = 2512
Mr = 315.23	Dx = 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

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2358 independent reflections
Radiation source: fine-focus sealed tube	2140 reflections with I > 2σ(I)
graphite	Rint = 0.047
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→15
Tmin = 0.281, Tmax = 0.376	k = −61→68
7816 measured reflections	l = −8→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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0467P)2 + 17.9942P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.002
2358 reflections	Δρmax = 0.68 e Å−3
142 parameters	Δρmin = −0.57 e Å−3
4 restraints	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.002 (14)

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
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*

	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)

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)

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···N1iv	0.80 (2)	2.28 (5)	2.993 (6)	149 (8)

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) ; (ii) ; (iii) .