Sodium N-chloro-2-methyl­benzene­sulfonamidate sesquihydrate

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

doi:10.1107/S1600536809019989

metal-organic compounds

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Volume 65| Part 6| June 2009| Page m700

doi:10.1107/S1600536809019989

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Sodium N-chloro-2-methylbenzenesulfonamidate sesquihydrate

B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^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 14 May 2009; accepted 26 May 2009; online 29 May 2009)

In the title salt, Na⁺·C₇H₇ClNO₂S⁻·1.5H₂O, one of the water molecules lies on a twofold axis. The sodium ion shows an O₆ octahedral 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_r = 509.32
Monoclinic, C 2
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 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) 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[F² > 2σ(F²)] = 0.023
wR(F²) = 0.061
S = 1.02
1657 reflections
142 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 617 Friedel pairs
Flack parameter: 0.02 (6)

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, y, -z+1; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019989/tk2451sup1.cif

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

checkCIF report

Comment top

The chemistry of N-halo-arylsulfonamides is of interest due to their diverse characteristics (Gowda et al., 2005). In the present work, the structure of sodium N-chloro-2-methyl- benzenesulfonamidate (I) has been determined to explore substituent effects on the solid-state structures of N-halo arylsulfonamidates (Gowda et al., 2007a, b, c). The structure of (I), Fig. 1, resembles the sodium salts of N-chloro-4-chloro-benzenesulfonamidate (Gowda et al., 2007a), N-chloro-2-methyl-4-chloro-benzenesulfonamidate (Gowda et al., 2007b), N-bromo-benzenesulfonamidate (Gowda et al., 2007c), and other sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986). The sodium ion shows octahedral coordination defined by three water-O atoms and by three sulfonyl-O atoms derived from three different anions. There is no interaction between the nitrogen and sodium ions in (I). The N1—S1 distance of 1.5898 (19) Å is consistent with a S—N double bond and is in agreement with those observed with related N-chloro arylsulfonamides. In this description, the negative charge on the anion is distributed over the oxygen atoms. With the association described above for the Na⁺ ion along with N-H···O and O-H···Cl hydrogen bonding, Table 1, the molecular packing comprises layers stacked along the c axis (Fig. 2).

Related literature top

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 top

The purity of the commmercial sample (TCI Chemicals, Tokyo Kasei) was checked and characterized by recording its infrared and NMR spectra and estimating the amount of active chlorine present in it by the iodometric method (Gowda et al., 2005). The single crystals used in X-ray diffraction studies were grown in a water solution of (I) by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (I), extended to show the immediate coordination geometry of the sodium cation. Only atoms comprising the asymmetric unit are labelled. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I) as viewed down the b axis, showing the O3W—H31···Cl1, O3W—H32···N1 and O4W—H41···N1 hydrogen bonds as dashed lines.

Sodium N-chloro-2-methylbenzenesulfonamidate sesquihydrate top

Crystal data top

Na⁺·C₇H₇ClNO₂S⁻·1.5H₂O	F(000) = 524
M_r = 509.32	D_x = 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

Data collection top

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 monochromator	R_int = 0.018
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.3°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −13→12
T_min = 0.776, T_max = 0.954	k = −7→8
3268 measured reflections	l = −16→17

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.041P)² + 0.5427P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.017
1657 reflections	Δρ_max = 0.25 e Å⁻³
142 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 617 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

Crystal data top

Na⁺·C₇H₇ClNO₂S⁻·1.5H₂O	V = 1039.61 (15) Å³
M_r = 509.32	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 11.011 (1) Å	µ = 0.60 mm⁻¹
b = 6.6434 (6) Å	T = 299 K
c = 14.447 (1) Å	0.45 × 0.32 × 0.08 mm
β = 100.350 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1657 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1613 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.954	R_int = 0.018
3268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.16 e Å⁻³
1657 reflections	Absolute structure: Flack (1983), 617 Friedel pairs
142 parameters	Absolute structure parameter: 0.02 (6)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—Na1^iv	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—Na1^iv	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—Na1^v	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)	Na1^iv—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—Na1^v	151.20 (10)
O3—Na1—O2ⁱⁱ	86.05 (6)	Na1ⁱ—O2—Na1^v	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)	Na1^iv—O4—Na1	86.61 (9)
O1—Na1—O2ⁱⁱⁱ	111.58 (6)	Na1^iv—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—Na1^iv	137.40 (5)	C2—C3—H3	118.6
O3—Na1—Na1^iv	112.82 (5)	C3—C4—C5	120.1 (2)
O2ⁱⁱ—Na1—Na1^iv	47.85 (4)	C3—C4—H4	119.9
O4—Na1—Na1^iv	46.69 (4)	C5—C4—H4	119.9
O3ⁱⁱ—Na1—Na1^iv	114.48 (5)	C4—C5—C6	119.3 (2)
O2ⁱⁱⁱ—Na1—Na1^iv	45.53 (4)	C4—C5—H5	120.3
S1ⁱⁱ—Na1—Na1^iv	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
Na1^iv—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—Na1^iv	−41.12 (4)
N1—S1—O1—Na1	48.8 (2)	O3ⁱⁱ—Na1—O4—Na1^iv	44.21 (14)
C1—S1—O1—Na1	169.5 (2)	O2ⁱⁱⁱ—Na1—O4—Na1^iv	39.58 (4)
Na1ⁱ—S1—O1—Na1	−73.0 (2)	S1ⁱⁱ—Na1—O4—Na1^iv	−49.86 (2)
O3—Na1—O1—S1	49.7 (2)	Na1ⁱ—Na1—O4—Na1^iv	−162.08 (4)
O2ⁱⁱ—Na1—O1—S1	51.7 (5)	Na1ⁱⁱ—Na1—O4—Na1^iv	−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)
Na1^iv—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—Na1^v	139.18 (19)	N1—S1—C1—C2	−52.9 (2)
N1—S1—O2—Na1^v	12.9 (2)	Na1ⁱ—S1—C1—C2	102.50 (18)
C1—S1—O2—Na1^v	−103.7 (2)	C6—C1—C2—C3	0.0 (3)
Na1ⁱ—S1—O2—Na1^v	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)
Na1^iv—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—Na1^iv	149.64 (6)	S1—C1—C6—C5	−179.6 (2)
O3—Na1—O4—Na1^iv	−128.06 (5)

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

Hydrogen-bond geometry (Å, º) top

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···N1^vi	0.77 (3)	2.19 (3)	2.951 (3)	168 (3)
O4—H41···N1^vii	0.80 (3)	2.19 (3)	2.989 (2)	176 (3)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₇H₇ClNO₂S⁻·1.5H₂O
M_r	509.32
Crystal system, space group	Monoclinic, C2
Temperature (K)	299
a, b, c (Å)	11.011 (1), 6.6434 (6), 14.447 (1)
β (°)	100.350 (7)
V (Å³)	1039.61 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.45 × 0.32 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.776, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	3268, 1657, 1613
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.061, 1.02
No. of reflections	1657
No. of parameters	142
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16
Absolute structure	Flack (1983), 617 Friedel pairs
Absolute structure parameter	0.02 (6)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), 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
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) −x+1/2, y+1/2, −z+1; (ii) −x+1, y, −z+1; (iii) x−1/2, y+1/2, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

References

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