Sodium N,2-dichloro-benzene-sulfonamidate sesquihydrate.

In the title compound, Na(+)·C(6)H(4)Cl(2)NO(2)S(-)·1.5H(2)O, one of the water mol-ecules lies on a twofold axis. There is no inter-action between the N atom and the sodium ion. The sodium ion exhibits a pseudo-octa-hedral coordination defined by three water O atoms and three sulfonyl O atoms from three different anions. The S-N distance of 1.588 (2) Å is consistent with an S=N double bond. The crystal structure is stabilized by O-H⋯N and O-H⋯Cl hydrogen bonds.

Related literature

For background to N-haloaryl­sulfonamides, see: Gowda et al. (2005 ▶). For related structures, see: Gowda et al. (2007 ▶, 2009 ▶); George et al. (2000 ▶); Olmstead & Power (1986 ▶).

Experimental

Crystal data

Na+·C6H4Cl2NO2S−·1.5H2O

M = 275.08

Monoclinic,

a = 11.1288 (7) Å

b = 6.6724 (4) Å

c = 28.144 (2) Å

β = 102.274 (6)°

V = 2042.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 299 K

0.46 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.691, T max = 0.794

6590 measured reflections

2076 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.069

S = 1.15

2076 reflections

141 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.28 e Å−3

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 datablocks I, global. DOI: 10.1107/S1600536810009864/bx2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009864/bx2268Isup2.hkl

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

Na+·C6H4Cl2NO2S−·1.5H2O	F(000) = 1112
Mr = 275.08	Dx = 1.789 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2816 reflections
a = 11.1288 (7) Å	θ = 3.0–27.9°
b = 6.6724 (4) Å	µ = 0.87 mm−1
c = 28.144 (2) Å	T = 299 K
β = 102.274 (6)°	Prism, colourless
V = 2042.1 (2) Å3	0.46 × 0.36 × 0.28 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2076 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.691, Tmax = 0.794	k = −8→6
6590 measured reflections	l = −33→35

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0246P)2 + 3.4504P] where P = (Fo2 + 2Fc2)/3
2076 reflections	(Δ/σ)max = 0.006
141 parameters	Δρmax = 0.36 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

Experimental. (CrysAlis RED; Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.31355 (16)	0.8280 (3)	0.10792 (6)	0.0208 (4)
C2	0.39097 (18)	0.8966 (3)	0.07759 (7)	0.0257 (4)
C3	0.3434 (2)	0.9809 (3)	0.03289 (8)	0.0376 (5)
H3	0.3951	1.0261	0.0132	0.045*
C4	0.2181 (2)	0.9965 (4)	0.01810 (8)	0.0454 (6)
H4	0.1843	1.0514	−0.0122	0.054*
C5	0.1413 (2)	0.9312 (4)	0.04792 (9)	0.0431 (6)
H5	0.0566	0.9446	0.0375	0.052*
C6	0.18813 (18)	0.8472 (3)	0.09260 (7)	0.0301 (4)
H6	0.1358	0.8038	0.1122	0.036*
Cl1	0.38325 (5)	0.35684 (8)	0.123234 (19)	0.03468 (14)
Cl2	0.54842 (5)	0.88282 (9)	0.09392 (2)	0.04180 (16)
N1	0.45784 (14)	0.5415 (2)	0.16212 (6)	0.0255 (3)
Na1	0.14395 (7)	0.50352 (13)	0.23560 (3)	0.03065 (19)
O1	0.25555 (13)	0.6627 (2)	0.18286 (5)	0.0329 (3)
O2	0.44039 (12)	0.8680 (2)	0.19636 (5)	0.0295 (3)
O3	0.29191 (13)	0.6793 (2)	0.29703 (5)	0.0333 (3)
H31	0.3538 (18)	0.627 (4)	0.3106 (9)	0.040*
H32	0.258 (2)	0.718 (4)	0.3182 (8)	0.040*
O4	0.0000	0.7742 (3)	0.2500	0.0336 (5)
H41	0.013 (2)	0.852 (3)	0.2729 (7)	0.040*
S1	0.36626 (4)	0.71995 (7)	0.166416 (15)	0.02023 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0244 (9)	0.0166 (8)	0.0201 (8)	0.0008 (7)	0.0022 (7)	−0.0003 (7)
C2	0.0290 (10)	0.0207 (9)	0.0277 (9)	−0.0013 (8)	0.0068 (8)	−0.0009 (8)
C3	0.0540 (14)	0.0311 (11)	0.0293 (11)	−0.0020 (10)	0.0129 (10)	0.0059 (9)
C4	0.0605 (15)	0.0406 (13)	0.0279 (11)	0.0060 (12)	−0.0068 (10)	0.0108 (10)
C5	0.0355 (12)	0.0442 (13)	0.0412 (12)	0.0054 (10)	−0.0106 (9)	0.0065 (11)
C6	0.0239 (9)	0.0331 (11)	0.0310 (10)	0.0007 (8)	0.0008 (8)	0.0010 (9)
Cl1	0.0399 (3)	0.0266 (3)	0.0380 (3)	−0.0038 (2)	0.0092 (2)	−0.0080 (2)
Cl2	0.0281 (3)	0.0487 (3)	0.0520 (3)	−0.0023 (2)	0.0163 (2)	0.0120 (3)
N1	0.0243 (8)	0.0226 (8)	0.0269 (8)	0.0010 (7)	−0.0002 (6)	−0.0014 (7)
Na1	0.0281 (4)	0.0325 (4)	0.0328 (4)	−0.0052 (3)	0.0097 (3)	0.0006 (3)
O1	0.0272 (7)	0.0430 (9)	0.0309 (7)	−0.0009 (6)	0.0116 (6)	0.0065 (7)
O2	0.0295 (7)	0.0308 (8)	0.0252 (7)	−0.0014 (6)	−0.0007 (5)	−0.0081 (6)
O3	0.0245 (7)	0.0408 (9)	0.0333 (8)	0.0014 (7)	0.0035 (6)	−0.0031 (7)
O4	0.0432 (12)	0.0244 (11)	0.0291 (11)	0.000	−0.0015 (9)	0.000
S1	0.0197 (2)	0.0233 (2)	0.0173 (2)	−0.00026 (17)	0.00302 (15)	0.00009 (17)

C1—C6	1.376 (3)	Na1—O2i	2.4710 (15)
C1—C2	1.412 (3)	Na1—O2ii	2.4759 (15)
C1—S1	1.7786 (18)	Na1—O4	2.5035 (18)
C2—C3	1.377 (3)	Na1—O3ii	2.5120 (18)
C2—Cl2	1.717 (2)	Na1—S1ii	3.3661 (9)
C3—C4	1.372 (3)	O1—S1	1.4562 (14)
C3—H3	0.9300	O2—S1	1.4390 (14)
C4—C5	1.389 (4)	O2—Na1iii	2.4710 (15)
C4—H4	0.9300	O2—Na1iv	2.4759 (15)
C5—C6	1.374 (3)	O3—Na1iv	2.5120 (18)
C5—H5	0.9300	O3—H31	0.792 (16)
C6—H6	0.9300	O3—H32	0.811 (16)
Cl1—N1	1.7376 (16)	O4—Na1v	2.5035 (18)
N1—S1	1.5883 (16)	O4—H41	0.814 (16)
Na1—O1	2.3785 (15)	S1—Na1iv	3.3661 (9)
Na1—O3	2.4220 (17)
C6—C1—C2	119.28 (17)	O2ii—Na1—O3ii	98.75 (6)
C6—C1—S1	116.14 (14)	O4—Na1—O3ii	157.17 (5)
C2—C1—S1	124.58 (14)	O1—Na1—S1ii	151.07 (5)
C3—C2—C1	121.30 (19)	O3—Na1—S1ii	79.85 (4)
C3—C2—Cl2	116.02 (16)	O2i—Na1—S1ii	88.45 (4)
C1—C2—Cl2	122.68 (15)	O2ii—Na1—S1ii	22.58 (3)
C4—C3—C2	118.5 (2)	O4—Na1—S1ii	97.97 (3)
C4—C3—H3	120.8	O3ii—Na1—S1ii	82.95 (4)
C2—C3—H3	120.8	S1—O1—Na1	154.80 (9)
C3—C4—C5	120.6 (2)	S1—O2—Na1iii	150.45 (9)
C3—C4—H4	119.7	S1—O2—Na1iv	116.06 (8)
C5—C4—H4	119.7	Na1iii—O2—Na1iv	89.02 (5)
C6—C5—C4	121.3 (2)	Na1—O3—Na1iv	111.04 (6)
C6—C5—H5	119.4	Na1—O3—H31	121.4 (19)
C4—C5—H5	119.4	Na1iv—O3—H31	105.4 (19)
C5—C6—C1	119.1 (2)	Na1—O3—H32	108.9 (19)
C5—C6—H6	120.5	Na1iv—O3—H32	102.1 (19)
C1—C6—H6	120.5	H31—O3—H32	106 (3)
S1—N1—Cl1	110.56 (9)	Na1v—O4—Na1	87.67 (8)
O1—Na1—O3	82.14 (6)	Na1v—O4—H41	109.7 (18)
O1—Na1—O2i	115.80 (6)	Na1—O4—H41	125.3 (18)
O3—Na1—O2i	156.33 (6)	O2—S1—O1	114.36 (9)
O1—Na1—O2ii	168.48 (6)	O2—S1—N1	105.17 (8)
O3—Na1—O2ii	86.38 (6)	O1—S1—N1	115.30 (9)
O2i—Na1—O2ii	75.50 (6)	O2—S1—C1	107.39 (9)
O1—Na1—O4	102.47 (6)	O1—S1—C1	105.41 (8)
O3—Na1—O4	84.05 (5)	N1—S1—C1	108.91 (8)
O2i—Na1—O4	77.23 (5)	O2—S1—Na1iv	41.36 (6)
O2ii—Na1—O4	77.14 (5)	O1—S1—Na1iv	73.08 (6)
O1—Na1—O3ii	85.97 (6)	N1—S1—Na1iv	128.14 (6)
O3—Na1—O3ii	118.37 (5)	C1—S1—Na1iv	117.93 (6)
O2i—Na1—O3ii	79.99 (5)
C6—C1—C2—C3	−0.5 (3)	O2ii—Na1—O4—Na1v	−38.86 (3)
S1—C1—C2—C3	−179.26 (16)	O3ii—Na1—O4—Na1v	43.09 (13)
C6—C1—C2—Cl2	178.96 (16)	S1ii—Na1—O4—Na1v	−47.647 (17)
S1—C1—C2—Cl2	0.2 (2)	Na1iii—O2—S1—O1	141.67 (17)
C1—C2—C3—C4	−0.2 (3)	Na1iv—O2—S1—O1	−3.82 (12)
Cl2—C2—C3—C4	−179.70 (18)	Na1iii—O2—S1—N1	14.2 (2)
C2—C3—C4—C5	0.9 (4)	Na1iv—O2—S1—N1	−131.33 (9)
C3—C4—C5—C6	−0.8 (4)	Na1iii—O2—S1—C1	−101.75 (18)
C4—C5—C6—C1	0.1 (4)	Na1iv—O2—S1—C1	112.77 (9)
C2—C1—C6—C5	0.5 (3)	Na1iii—O2—S1—Na1iv	145.5 (2)
S1—C1—C6—C5	179.42 (17)	Na1—O1—S1—O2	−71.7 (2)
O3—Na1—O1—S1	50.3 (2)	Na1—O1—S1—N1	50.4 (3)
O2i—Na1—O1—S1	−145.9 (2)	Na1—O1—S1—C1	170.6 (2)
O2ii—Na1—O1—S1	45.6 (5)	Na1—O1—S1—Na1iv	−74.3 (2)
O4—Na1—O1—S1	132.4 (2)	Cl1—N1—S1—O2	−175.92 (9)
O3ii—Na1—O1—S1	−69.0 (2)	Cl1—N1—S1—O1	57.14 (12)
S1ii—Na1—O1—S1	−1.5 (3)	Cl1—N1—S1—C1	−61.07 (11)
O1—Na1—O3—Na1iv	31.28 (6)	Cl1—N1—S1—Na1iv	144.96 (6)
O2i—Na1—O3—Na1iv	−109.93 (14)	C6—C1—S1—O2	−118.21 (15)
O2ii—Na1—O3—Na1iv	−149.66 (7)	C2—C1—S1—O2	60.61 (18)
O4—Na1—O3—Na1iv	−72.23 (6)	C6—C1—S1—O1	4.11 (17)
O3ii—Na1—O3—Na1iv	112.35 (9)	C2—C1—S1—O1	−177.07 (16)
S1ii—Na1—O3—Na1iv	−171.45 (6)	C6—C1—S1—N1	128.38 (15)
O1—Na1—O4—Na1v	152.95 (5)	C2—C1—S1—N1	−52.80 (18)
O3—Na1—O4—Na1v	−126.49 (5)	C6—C1—S1—Na1iv	−74.61 (16)
O2i—Na1—O4—Na1v	38.93 (4)	C2—C1—S1—Na1iv	104.21 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···N1vi	0.79 (2)	2.15 (2)	2.926 (2)	166 (3)
O3—H32···Cl1iv	0.81 (2)	2.67 (2)	3.4782 (16)	171 (2)
O4—H41···N1iv	0.81 (2)	2.19 (2)	3.005 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯N1i	0.79 (2)	2.15 (2)	2.926 (2)	166 (3)
O3—H32⋯Cl1ii	0.81 (2)	2.67 (2)	3.4782 (16)	171 (2)
O4—H41⋯N1ii	0.81 (2)	2.19 (2)	3.005 (2)	176 (2)

Symmetry codes: (i) ; (ii) .