Sodium N-chloro-2-methyl-benzene-sulfonamidate sesquihydrate.

In the title salt, Na(+)·C(7)H(7)ClNO(2)S(-)·1.5H(2)O, one of the water mol-ecules lies on a twofold axis. The sodium ion shows an O(6) octa-hedral coordination defined by three water O atoms and three sulfonyl O atoms derived from three different anions. The S-N distance of 1.5898 (19) Å is consistent with an S=N double bond. The crystal structure is stabilized by N-H⋯O and O-H⋯Cl hydrogen bonds.

Related literature

For background to N-halo-aryl­sulfonamides, see: Gowda et al. (2005 ▶). For related structures, see: Gowda et al. (2007a ▶,b ▶,c ▶); George et al. (2000 ▶); Olmstead & Power (1986 ▶).

Experimental

Crystal data

Na+·C7H7ClNO2S−·1.5H2O

M = 509.32

Monoclinic,

a = 11.011 (1) Å

b = 6.6434 (6) Å

c = 14.447 (1) Å

β = 100.350 (7)°

V = 1039.61 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 299 K

0.45 × 0.32 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.776, T max = 0.954

3268 measured reflections

1657 independent reflections

1613 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.061

S = 1.02

1657 reflections

142 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 617 Friedel pairs

Flack parameter: 0.02 (6)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S1600536809019989/tk2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019989/tk2451Isup2.hkl

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

Na+·C7H7ClNO2S−·1.5H2O	F(000) = 524
Mr = 509.32	Dx = 1.627 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3049 reflections
a = 11.011 (1) Å	θ = 2.6–27.5°
b = 6.6434 (6) Å	µ = 0.60 mm−1
c = 14.447 (1) Å	T = 299 K
β = 100.350 (7)°	Plate, colourless
V = 1039.61 (15) Å3	0.45 × 0.32 × 0.08 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1657 independent reflections
Radiation source: fine-focus sealed tube	1613 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans	θmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −13→12
Tmin = 0.776, Tmax = 0.954	k = −7→8
3268 measured reflections	l = −16→17

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.041P)2 + 0.5427P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.017
1657 reflections	Δρmax = 0.25 e Å−3
142 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 617 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (6)

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.38269 (5)	0.04628 (9)	0.25363 (4)	0.03904 (16)
S1	0.36260 (4)	0.41295 (8)	0.33507 (3)	0.02316 (13)
Na1	0.14461 (8)	0.19582 (15)	0.47389 (6)	0.0333 (2)
O1	0.24978 (13)	0.3583 (3)	0.36677 (10)	0.0367 (4)
O2	0.43766 (13)	0.5621 (3)	0.39333 (10)	0.0320 (4)
O3	0.29326 (15)	0.3727 (3)	0.59025 (12)	0.0365 (4)
H31	0.258 (3)	0.402 (5)	0.6345 (18)	0.044*
H32	0.354 (3)	0.324 (5)	0.615 (2)	0.044*
O4	0.0000	0.4675 (4)	0.5000	0.0358 (6)
H41	−0.015 (3)	0.534 (5)	0.4534 (18)	0.043*
N1	0.45553 (16)	0.2319 (3)	0.32989 (12)	0.0286 (4)
C1	0.31412 (18)	0.5172 (3)	0.22046 (13)	0.0254 (4)
C2	0.3987 (2)	0.5799 (4)	0.16471 (15)	0.0310 (5)
C3	0.3489 (3)	0.6595 (4)	0.07650 (16)	0.0442 (6)
H3	0.4026	0.7045	0.0380	0.053*
C4	0.2246 (3)	0.6740 (5)	0.04438 (17)	0.0533 (7)
H4	0.1954	0.7255	−0.0153	0.064*
C5	0.1428 (3)	0.6125 (5)	0.10021 (19)	0.0503 (7)
H5	0.0582	0.6233	0.0788	0.060*
C6	0.1876 (2)	0.5343 (4)	0.18857 (16)	0.0367 (5)
H6	0.1328	0.4930	0.2268	0.044*
C7	0.5365 (2)	0.5657 (5)	0.19499 (17)	0.0410 (6)
H7A	0.5600	0.4270	0.2040	0.049*
H7B	0.5610	0.6378	0.2529	0.049*
H7C	0.5763	0.6233	0.1473	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0411 (3)	0.0278 (3)	0.0496 (3)	−0.0037 (2)	0.0118 (2)	−0.0106 (3)
S1	0.0232 (2)	0.0237 (3)	0.0231 (2)	−0.0006 (2)	0.00549 (16)	−0.0007 (2)
Na1	0.0316 (5)	0.0327 (5)	0.0374 (4)	−0.0053 (4)	0.0114 (4)	−0.0002 (4)
O1	0.0316 (8)	0.0456 (12)	0.0360 (8)	−0.0025 (7)	0.0143 (6)	0.0047 (7)
O2	0.0343 (8)	0.0302 (10)	0.0305 (7)	−0.0028 (7)	0.0034 (6)	−0.0084 (6)
O3	0.0270 (8)	0.0421 (12)	0.0396 (8)	0.0008 (7)	0.0040 (6)	−0.0010 (7)
O4	0.0457 (14)	0.0257 (14)	0.0342 (11)	0.000	0.0025 (10)	0.000
N1	0.0262 (9)	0.0240 (11)	0.0342 (9)	−0.0005 (7)	0.0016 (7)	−0.0019 (7)
C1	0.0296 (10)	0.0206 (12)	0.0250 (9)	−0.0003 (9)	0.0024 (7)	−0.0009 (8)
C2	0.0383 (12)	0.0250 (14)	0.0306 (10)	−0.0045 (9)	0.0091 (8)	−0.0017 (9)
C3	0.0646 (17)	0.0364 (17)	0.0332 (11)	−0.0040 (13)	0.0132 (11)	0.0056 (11)
C4	0.076 (2)	0.0450 (18)	0.0334 (12)	0.0053 (15)	−0.0048 (13)	0.0079 (12)
C5	0.0449 (15)	0.0508 (18)	0.0478 (14)	0.0069 (12)	−0.0115 (11)	−0.0001 (12)
C6	0.0319 (11)	0.0337 (14)	0.0432 (11)	0.0019 (10)	0.0033 (9)	0.0007 (11)
C7	0.0357 (12)	0.0449 (17)	0.0457 (12)	−0.0071 (11)	0.0163 (10)	0.0029 (12)

Cl1—N1	1.7491 (19)	O3—H31	0.83 (3)
S1—O1	1.4454 (15)	O3—H32	0.77 (3)
S1—O2	1.4571 (16)	O4—Na1iv	2.480 (2)
S1—N1	1.5898 (19)	O4—H41	0.80 (3)
S1—C1	1.785 (2)	C1—C6	1.391 (3)
S1—Na1i	3.3517 (10)	C1—C2	1.399 (3)
Na1—O1	2.3549 (17)	C2—C3	1.397 (3)
Na1—O3	2.4283 (18)	C2—C7	1.505 (3)
Na1—O2ii	2.4319 (16)	C3—C4	1.367 (4)
Na1—O4	2.480 (2)	C3—H3	0.9300
Na1—O3ii	2.483 (2)	C4—C5	1.375 (4)
Na1—O2iii	2.5266 (16)	C4—H4	0.9300
Na1—S1ii	3.3517 (10)	C5—C6	1.384 (4)
Na1—Na1iv	3.4021 (16)	C5—H5	0.9300
Na1—Na1i	4.0447 (10)	C6—H6	0.9300
Na1—Na1ii	4.0447 (10)	C7—H7A	0.9600
O2—Na1i	2.4319 (16)	C7—H7B	0.9600
O2—Na1v	2.5266 (16)	C7—H7C	0.9600
O3—Na1i	2.483 (2)
O1—S1—O2	114.72 (9)	O3—Na1—Na1ii	88.59 (6)
O1—S1—N1	114.96 (10)	O2ii—Na1—Na1ii	80.53 (5)
O2—S1—N1	103.80 (9)	O4—Na1—Na1ii	158.72 (5)
O1—S1—C1	105.10 (9)	O3ii—Na1—Na1ii	34.12 (4)
O2—S1—C1	108.43 (10)	O2iii—Na1—Na1ii	103.70 (5)
N1—S1—C1	109.72 (9)	S1ii—Na1—Na1ii	58.91 (2)
O1—S1—Na1i	74.39 (7)	Na1iv—Na1—Na1ii	119.16 (2)
N1—S1—Na1i	125.01 (7)	Na1i—Na1—Na1ii	110.42 (4)
C1—S1—Na1i	119.92 (8)	S1—O1—Na1	151.10 (10)
O1—Na1—O3	83.29 (6)	S1—O2—Na1i	116.81 (8)
O1—Na1—O2ii	169.34 (7)	S1—O2—Na1v	151.20 (10)
O3—Na1—O2ii	86.05 (6)	Na1i—O2—Na1v	86.63 (5)
O1—Na1—O4	99.86 (6)	Na1—O3—Na1i	110.90 (7)
O3—Na1—O4	85.06 (6)	Na1—O3—H31	107 (2)
O2ii—Na1—O4	78.79 (5)	Na1i—O3—H31	107 (2)
O1—Na1—O3ii	87.14 (7)	Na1—O3—H32	123 (2)
O3—Na1—O3ii	118.69 (5)	Na1i—O3—H32	105 (2)
O2ii—Na1—O3ii	98.34 (7)	H31—O3—H32	103 (3)
O4—Na1—O3ii	156.00 (6)	Na1iv—O4—Na1	86.61 (9)
O1—Na1—O2iii	111.58 (6)	Na1iv—O4—H41	119 (2)
O3—Na1—O2iii	158.28 (7)	Na1—O4—H41	108 (2)
O2ii—Na1—O2iii	78.57 (6)	S1—N1—Cl1	109.69 (10)
O4—Na1—O2iii	77.02 (5)	C6—C1—C2	121.0 (2)
O3ii—Na1—O2iii	79.06 (6)	C6—C1—S1	116.98 (16)
O1—Na1—S1ii	152.30 (5)	C2—C1—S1	122.02 (15)
O3—Na1—S1ii	79.28 (5)	C3—C2—C1	116.5 (2)
O2ii—Na1—S1ii	22.83 (4)	C3—C2—C7	119.9 (2)
O4—Na1—S1ii	99.90 (4)	C1—C2—C7	123.7 (2)
O3ii—Na1—S1ii	82.61 (5)	C4—C3—C2	122.7 (2)
O2iii—Na1—S1ii	91.68 (5)	C4—C3—H3	118.6
O1—Na1—Na1iv	137.40 (5)	C2—C3—H3	118.6
O3—Na1—Na1iv	112.82 (5)	C3—C4—C5	120.1 (2)
O2ii—Na1—Na1iv	47.85 (4)	C3—C4—H4	119.9
O4—Na1—Na1iv	46.69 (4)	C5—C4—H4	119.9
O3ii—Na1—Na1iv	114.48 (5)	C4—C5—C6	119.3 (2)
O2iii—Na1—Na1iv	45.53 (4)	C4—C5—H5	120.3
S1ii—Na1—Na1iv	69.87 (2)	C6—C5—H5	120.3
O1—Na1—Na1i	54.03 (5)	C5—C6—C1	120.4 (2)
O3—Na1—Na1i	34.99 (5)	C5—C6—H6	119.8
O2ii—Na1—Na1i	115.82 (6)	C1—C6—H6	119.8
O4—Na1—Na1i	74.73 (4)	C2—C7—H7A	109.5
O3ii—Na1—Na1i	126.33 (6)	C2—C7—H7B	109.5
O2iii—Na1—Na1i	144.54 (5)	H7A—C7—H7B	109.5
S1ii—Na1—Na1i	113.86 (3)	C2—C7—H7C	109.5
Na1iv—Na1—Na1i	119.16 (2)	H7A—C7—H7C	109.5
O1—Na1—Na1ii	99.54 (6)	H7B—C7—H7C	109.5
O2—S1—O1—Na1	−71.5 (3)	O2ii—Na1—O4—Na1iv	−41.12 (4)
N1—S1—O1—Na1	48.8 (2)	O3ii—Na1—O4—Na1iv	44.21 (14)
C1—S1—O1—Na1	169.5 (2)	O2iii—Na1—O4—Na1iv	39.58 (4)
Na1i—S1—O1—Na1	−73.0 (2)	S1ii—Na1—O4—Na1iv	−49.86 (2)
O3—Na1—O1—S1	49.7 (2)	Na1i—Na1—O4—Na1iv	−162.08 (4)
O2ii—Na1—O1—S1	51.7 (5)	Na1ii—Na1—O4—Na1iv	−54.89 (12)
O4—Na1—O1—S1	133.4 (2)	O1—S1—N1—Cl1	58.78 (12)
O3ii—Na1—O1—S1	−69.7 (2)	O2—S1—N1—Cl1	−175.11 (9)
O2iii—Na1—O1—S1	−146.7 (2)	C1—S1—N1—Cl1	−59.39 (13)
S1ii—Na1—O1—S1	−1.5 (3)	Na1i—S1—N1—Cl1	146.70 (6)
Na1iv—Na1—O1—S1	166.35 (18)	O1—S1—C1—C6	3.1 (2)
Na1i—Na1—O1—S1	70.6 (2)	O2—S1—C1—C6	−119.99 (19)
Na1ii—Na1—O1—S1	−37.8 (2)	N1—S1—C1—C6	127.3 (2)
O1—S1—O2—Na1i	−2.28 (14)	Na1i—S1—C1—C6	−77.3 (2)
N1—S1—O2—Na1i	−128.55 (10)	O1—S1—C1—C2	−177.07 (18)
C1—S1—O2—Na1i	114.82 (10)	O2—S1—C1—C2	59.8 (2)
O1—S1—O2—Na1v	139.18 (19)	N1—S1—C1—C2	−52.9 (2)
N1—S1—O2—Na1v	12.9 (2)	Na1i—S1—C1—C2	102.50 (18)
C1—S1—O2—Na1v	−103.7 (2)	C6—C1—C2—C3	0.0 (3)
Na1i—S1—O2—Na1v	141.5 (3)	S1—C1—C2—C3	−179.79 (19)
O1—Na1—O3—Na1i	30.30 (8)	C6—C1—C2—C7	179.9 (2)
O2ii—Na1—O3—Na1i	−149.33 (8)	S1—C1—C2—C7	0.2 (3)
O4—Na1—O3—Na1i	−70.26 (7)	C1—C2—C3—C4	−0.9 (4)
O3ii—Na1—O3—Na1i	113.32 (11)	C7—C2—C3—C4	179.1 (3)
O2iii—Na1—O3—Na1i	−104.58 (18)	C2—C3—C4—C5	1.3 (5)
S1ii—Na1—O3—Na1i	−171.33 (7)	C3—C4—C5—C6	−0.6 (5)
Na1iv—Na1—O3—Na1i	−108.70 (6)	C4—C5—C6—C1	−0.3 (5)
Na1ii—Na1—O3—Na1i	130.07 (7)	C2—C1—C6—C5	0.6 (4)
O1—Na1—O4—Na1iv	149.64 (6)	S1—C1—C6—C5	−179.6 (2)
O3—Na1—O4—Na1iv	−128.06 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl1i	0.83 (3)	2.62 (3)	3.4266 (19)	167 (3)
O3—H32···N1vi	0.77 (3)	2.19 (3)	2.951 (3)	168 (3)
O4—H41···N1vii	0.80 (3)	2.19 (3)	2.989 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Cl1i	0.83 (3)	2.62 (3)	3.4266 (19)	167 (3)
O3—H32⋯N1ii	0.77 (3)	2.19 (3)	2.951 (3)	168 (3)
O4—H41⋯N1iii	0.80 (3)	2.19 (3)	2.989 (2)	176 (3)

Symmetry codes: (i) ; (ii) ; (iii) .