Sodium 4,N-dichloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Jyothi, K.; Foro, S.; Kožíšek, J.; Fuess, H.

doi:10.1107/S1600536807023033

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Sodium 4,N-dichlorobenzenesulfonamidate sesquihydrate

B. T. Gowda, K. Jyothi, S. Foro, J. Kozísek and H. Fuess

The structure of the title compound, Na^+.C₆H₄Cl₂NO₂S^-·1.5H₂O, resembles the structures of the sodium salts of N-chlorobenzenesulfonamide, N-chloro-4-methylbenzenesulfonamide and N-chloro-2-methyl-4-chlorobenzenesulfonamide. There are two formula units per asymmetric unit. There is no interaction between N and Na, and the Na⁺ cation is attached to three O atoms from water molecules and three sulfonyl O atoms of three different 4,N-dichlorobenzenesulfonamide anions. There are several hydrogen bonds. The S-N distances of 1.584 (5) and 1.590 (5) Å are consistent with an S=N double bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023033/bt2356sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023033/bt2356Isup2.hkl Contains datablock I

CCDC reference: 650621

checkCIF report

Key indicators

Single-crystal X-ray study
T = 303 K
Mean (C-C) = 0.010 Å
R factor = 0.068
wR factor = 0.140
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H42O   ..  S2      ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H51O   ..  CL2     ..       2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H61O   ..  O2      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H62O   ..  S1      ..       3.00 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         86
            S2  -O2  -NA2 -O7    -81.80  1.50   1.555   1.555   1.555   3.455
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         87
            NA1 -O2  -NA2 -O7    108.50  1.40   3.465   1.555   1.555   3.455
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.842(19) ......       2.11 su-Ra
              O4   -H41O    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.841(19) ......       2.11 su-Ra
              O4   -H42O    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.848(19) ......       2.11 su-Ra
              O5   -H51O    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.861(19) ......       2.11 su-Ra
              O5   -H52O    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(5), Rep     0.86(2) ......       2.50 su-Ra
              O6   -H62O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.842(19) ......       2.11 su-Ra
              O4   -H41O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.841(19) ......       2.11 su-Ra
              O4   -H42O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.841(19) ......       2.11 su-Ra
              O4   -H42O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.848(19) ......       2.11 su-Ra
              O5   -H51O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.848(19) ......       2.11 su-Ra
              O5   -H51O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.861(19) ......       2.11 su-Ra
              O5   -H52O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.861(19) ......       2.11 su-Ra
              O5   -H52O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(5), Rep     0.86(2) ......       2.50 su-Ra
              O6   -H62O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(5), Rep     0.86(2) ......       2.50 su-Ra
              O6   -H62O    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.70(5), Rep     2.70(2) ......       2.50 su-Ra
              H41O -CL1     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.00(5), Rep     2.00(2) ......       2.50 su-Ra
              H62O -N1      1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.33 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               4281
           Count of symmetry unique reflns         2504
           Completeness (_total/calc)            170.97%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1777
           Fraction of Friedel pairs measured     0.710
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  28 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

  19 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of arylsulfonamides and their N-halo compounds is of interest as they show distinct physical, chemical and biological properties. Many of these compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. Thus N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2002; Gowda, D'Souza & Fuess 2003; Gowda, D'Souza & Kumar, 2003; Gowda, Jyothi et al., 2003; Gowda & Shetty 2004; Gowda & Kumar, 2003; Gowda et al., 2005; Gowda et al., 2007). In the present work, the structure of the sodium salt of N-chloro, 4-chlorobenzenesulfonamde has been determined to explore the effect substituent on the solid state structures of sulfonamides and N-halo arylsulfonamides. The structure (Fig. 1) resembles those of the sodium salts of N-chlorobenzenesulfonamde (George et al., 2000), N-chloro-4-methylbenzenesulfonamde (Olmstead & Power, 1986) and N-chloro-2-methyl-4-chlorobenzenesulfonamde (Gowda et al., 2007). There is no interaction between the nitrogen and sodium atoms in the molecule, and Na+ is attached to one of the sulfonyl O atoms. Na+ coordination sphere involves oxygen from waters of crystallization and neighbouring molecules. Na+ ion coordination in the structure is also similar giving rise to several hydrogen bonding between water hydrogen, oxygen and other atoms in the molecule as shown in Figures 2 and 3. The S—N distances of 1.584 (5)Å and 1.590 (5)Å are in agreement with those of similar compounds, consistent with a S—N double bond.

Related literature top

For related literature, see: George et al. (2000); Gowda & Kumar (2003); Gowda & Shetty (2004); Gowda et al. (2002, 2005, 2007); Gowda, D'Souza & Fuess (2003); Gowda, D'Souza & Kumar (2003); Gowda, Jyothi, Kozisek & Fuess (2003); Olmstead & Power (1986).

Experimental top

The title compound was prepared according to the literature method (Gowda, D'Souza & Fuess 2003; Gowda, D'Souza & Kumar, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR and NQR spectra. Single crystals of the title compound were obtained from a slow evaporation of its chloroform solution and used for X-ray diffraction studies at room temperature.

Structure description top

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. ORTEP view of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the axis b.
	Fig. 3. Typical Hydrogen bond bridges observed in the title compound.

Sodium 4,N-dichlorobenzenesulfonamidate sesquihydrate top

Crystal data top

Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	F(000) = 1112
M_r = 275.09	D_x = 1.732 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3193 reflections
a = 6.7041 (4) Å	θ = 3.4–25.5°
b = 10.4763 (8) Å	µ = 0.84 mm⁻¹
c = 30.037 (2) Å	T = 303 K
V = 2109.6 (2) Å³	Laminar, colourless
Z = 8	0.30 × 0.12 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	4281 independent reflections
Radiation source: fine-focus sealed tube	2959 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 4.1°
Absorption correction: analytical CrysAlis RED (Oxford Diffraction, 2002)	h = −8→5
T_min = 0.865, T_max = 0.962	k = −12→13
14393 measured reflections	l = −37→37

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.039
4281 reflections	Δρ_max = 0.41 e Å⁻³
280 parameters	Δρ_min = −0.33 e Å⁻³
9 restraints	Absolute structure: Flack (1983), 1777 Friedel pairs'
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.22 (12)

Crystal data top

Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O	V = 2109.6 (2) Å³
M_r = 275.09	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7041 (4) Å	µ = 0.84 mm⁻¹
b = 10.4763 (8) Å	T = 303 K
c = 30.037 (2) Å	0.30 × 0.12 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	4281 independent reflections
Absorption correction: analytical CrysAlis RED (Oxford Diffraction, 2002)	2959 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.962	R_int = 0.079
14393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.140	Δρ_max = 0.41 e Å⁻³
S = 1.10	Δρ_min = −0.33 e Å⁻³
4281 reflections	Absolute structure: Flack (1983), 1777 Friedel pairs'
280 parameters	Absolute structure parameter: 0.22 (12)
9 restraints

Special details top

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
C1	0.2166 (9)	0.6230 (6)	0.1339 (2)	0.0233 (15)
C2	0.1376 (9)	0.5182 (7)	0.1569 (2)	0.0363 (17)
H2	0.1420	0.4366	0.1448	0.044*
C3	0.0543 (10)	0.5394 (8)	0.1977 (2)	0.045 (2)
H3	−0.0031	0.4715	0.2130	0.054*
C4	0.0533 (10)	0.6565 (8)	0.2162 (2)	0.0388 (18)
C5	0.1311 (11)	0.7599 (8)	0.1944 (3)	0.048 (2)
H5	0.1280	0.8402	0.2076	0.058*
C6	0.2147 (10)	0.7438 (6)	0.1525 (2)	0.0376 (18)
H6	0.2684	0.8129	0.1372	0.045*
C7	0.2101 (9)	0.4255 (6)	−0.1317 (2)	0.0219 (14)
C8	0.2049 (11)	0.5461 (7)	−0.1490 (2)	0.0412 (18)
H8	0.2560	0.6134	−0.1323	0.049*
C9	0.1272 (10)	0.5704 (7)	−0.1899 (3)	0.042 (2)
H9	0.1270	0.6528	−0.2015	0.050*
C10	0.0489 (10)	0.4707 (8)	−0.2138 (2)	0.0407 (19)
C11	0.0500 (11)	0.3466 (7)	−0.1974 (2)	0.0390 (18)
H11	−0.0017	0.2797	−0.2141	0.047*
C12	0.1303 (9)	0.3247 (6)	−0.1551 (2)	0.0326 (17)
H12	0.1298	0.2431	−0.1430	0.039*
N1	0.4918 (6)	0.4958 (5)	0.08230 (17)	0.0320 (13)
N2	0.5112 (7)	0.4835 (5)	−0.07515 (16)	0.0275 (12)
O1	0.1710 (6)	0.5457 (4)	0.05205 (13)	0.0322 (11)
O2	0.1801 (6)	0.4532 (4)	−0.04620 (14)	0.0345 (11)
O3	0.3891 (7)	0.7264 (4)	0.06666 (15)	0.0413 (13)
O4	0.8701 (7)	0.7723 (4)	0.04198 (15)	0.0366 (12)
H41O	0.839 (10)	0.724 (4)	0.0632 (14)	0.044*
H42O	0.915 (9)	0.842 (3)	0.0521 (18)	0.044*
O5	−0.2356 (6)	0.5018 (6)	0.00285 (14)	0.0383 (11)
H51O	−0.306 (7)	0.487 (7)	−0.0200 (10)	0.046*
H52O	−0.319 (6)	0.510 (7)	0.0245 (11)	0.046*
O6	0.3547 (7)	0.2708 (4)	0.03900 (16)	0.0398 (12)
H61O	0.376 (10)	0.204 (3)	0.0553 (18)	0.048*
H62O	0.411 (9)	0.332 (4)	0.0535 (18)	0.048*
O7	0.3489 (6)	0.2636 (4)	−0.07503 (14)	0.0346 (11)
S1	0.3222 (2)	0.60178 (14)	0.08011 (5)	0.0255 (4)
S2	0.3159 (2)	0.39894 (14)	−0.07852 (5)	0.0241 (4)
Cl1	0.6828 (3)	0.54516 (18)	0.11769 (6)	0.0432 (5)
Cl2	0.6858 (3)	0.43230 (17)	−0.11428 (6)	0.0436 (5)
Cl3	−0.0432 (3)	0.6788 (3)	0.26962 (6)	0.0706 (7)
Cl4	−0.0464 (3)	0.4965 (2)	−0.26702 (6)	0.0584 (6)
Na1	0.5463 (4)	0.8486 (2)	0.01367 (8)	0.0327 (6)
Na2	0.0289 (4)	0.3492 (2)	0.01858 (8)	0.0336 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.021 (3)	0.023 (4)	0.026 (3)	−0.007 (3)	−0.003 (3)	−0.003 (3)
C2	0.041 (4)	0.033 (4)	0.035 (4)	0.004 (3)	0.008 (3)	−0.002 (3)
C3	0.038 (4)	0.061 (6)	0.036 (4)	−0.001 (4)	0.011 (4)	0.012 (4)
C4	0.025 (4)	0.071 (6)	0.021 (4)	−0.004 (4)	0.006 (3)	−0.013 (4)
C5	0.056 (5)	0.049 (5)	0.039 (5)	−0.003 (4)	0.001 (4)	−0.020 (4)
C6	0.044 (4)	0.028 (4)	0.041 (4)	0.003 (4)	0.014 (4)	−0.002 (3)
C7	0.015 (3)	0.027 (4)	0.023 (3)	0.012 (3)	−0.001 (3)	0.002 (3)
C8	0.047 (4)	0.037 (4)	0.039 (4)	−0.004 (4)	−0.010 (4)	0.003 (3)
C9	0.040 (4)	0.042 (4)	0.043 (5)	−0.008 (4)	−0.015 (4)	0.021 (4)
C10	0.023 (3)	0.066 (6)	0.033 (4)	0.009 (4)	−0.002 (3)	0.020 (4)
C11	0.049 (4)	0.039 (4)	0.030 (4)	−0.003 (4)	−0.016 (4)	−0.009 (3)
C12	0.038 (4)	0.026 (4)	0.034 (4)	−0.003 (3)	−0.001 (3)	−0.007 (3)
N1	0.027 (3)	0.038 (3)	0.031 (3)	−0.001 (3)	−0.007 (2)	−0.005 (3)
N2	0.025 (3)	0.035 (3)	0.022 (3)	0.001 (2)	0.004 (2)	−0.005 (3)
O1	0.029 (2)	0.041 (3)	0.027 (2)	0.006 (2)	−0.008 (2)	−0.004 (2)
O2	0.035 (2)	0.045 (3)	0.023 (2)	0.004 (2)	0.011 (2)	0.001 (2)
O3	0.059 (3)	0.031 (3)	0.034 (3)	−0.010 (2)	0.006 (2)	0.004 (2)
O4	0.039 (3)	0.027 (3)	0.044 (3)	−0.002 (2)	0.003 (2)	−0.005 (2)
O5	0.029 (2)	0.054 (3)	0.031 (3)	0.004 (3)	−0.002 (2)	−0.002 (2)
O6	0.040 (3)	0.031 (3)	0.049 (3)	0.006 (3)	−0.002 (2)	0.000 (2)
O7	0.049 (3)	0.028 (2)	0.027 (2)	0.003 (2)	−0.005 (2)	−0.003 (2)
S1	0.0274 (9)	0.0283 (9)	0.0206 (8)	0.0012 (8)	−0.0010 (8)	0.0019 (7)
S2	0.0274 (9)	0.0252 (9)	0.0198 (8)	−0.0001 (8)	−0.0027 (8)	0.0005 (7)
Cl1	0.0306 (9)	0.0603 (12)	0.0386 (10)	−0.0009 (9)	−0.0082 (9)	0.0034 (10)
Cl2	0.0330 (10)	0.0552 (11)	0.0426 (11)	0.0059 (9)	0.0097 (9)	0.0101 (9)
Cl3	0.0490 (11)	0.128 (2)	0.0349 (11)	−0.0072 (13)	0.0123 (11)	−0.0199 (13)
Cl4	0.0469 (10)	0.0969 (17)	0.0313 (10)	0.0015 (12)	−0.0133 (10)	0.0145 (11)
Na1	0.0331 (14)	0.0343 (15)	0.0307 (14)	−0.0085 (13)	0.0027 (13)	0.0041 (12)
Na2	0.0316 (14)	0.0309 (15)	0.0384 (15)	−0.0046 (13)	0.0013 (13)	0.0051 (12)

Geometric parameters (Å, º) top

C1—C6	1.382 (9)	O2—S2	1.447 (4)
C1—C2	1.401 (9)	O2—Na2	2.450 (5)
C1—S1	1.779 (6)	O2—Na1ⁱ	2.464 (5)
C2—C3	1.363 (9)	O3—S1	1.438 (5)
C2—H2	0.9300	O3—Na1	2.298 (5)
C3—C4	1.348 (10)	O4—Na1ⁱⁱ	2.407 (5)
C3—H3	0.9300	O4—Na1	2.465 (5)
C4—C5	1.369 (10)	O4—H41O	0.842 (19)
C4—Cl3	1.745 (7)	O4—H42O	0.841 (19)
C5—C6	1.389 (10)	O5—Na2	2.433 (5)
C5—H5	0.9300	O5—Na1ⁱ	2.505 (5)
C6—H6	0.9300	O5—H51O	0.848 (19)
C7—C8	1.366 (9)	O5—H52O	0.861 (19)
C7—C12	1.377 (8)	O6—Na2	2.413 (5)
C7—S2	1.770 (6)	O6—Na2ⁱⁱⁱ	2.437 (6)
C8—C9	1.360 (9)	O6—H61O	0.87 (2)
C8—H8	0.9300	O6—H62O	0.86 (2)
C9—C10	1.372 (10)	O7—S2	1.439 (4)
C9—H9	0.9300	O7—Na2ⁱⁱⁱ	2.393 (5)
C10—C11	1.391 (9)	Na1—O4ⁱ	2.407 (5)
C10—Cl4	1.742 (7)	Na1—O1ⁱⁱ	2.413 (5)
C11—C12	1.397 (9)	Na1—O2ⁱⁱ	2.464 (5)
C11—H11	0.9300	Na1—O5ⁱⁱ	2.505 (5)
C12—H12	0.9300	Na1—Na2ⁱⁱ	3.313 (3)
N1—S1	1.590 (5)	Na1—Na1ⁱ	4.022 (3)
N1—Cl1	1.743 (5)	Na1—Na1ⁱⁱ	4.022 (3)
N2—S2	1.584 (5)	Na2—O7^iv	2.393 (5)
N2—Cl2	1.743 (5)	Na2—O6^iv	2.437 (6)
O1—S1	1.443 (4)	Na2—Na1ⁱ	3.313 (3)
O1—Na1ⁱ	2.413 (5)	Na2—Na2^iv	4.100 (3)
O1—Na2	2.481 (5)	Na2—Na2ⁱⁱⁱ	4.100 (3)

C6—C1—C2	121.0 (6)	O2—S2—C7	107.0 (3)
C6—C1—S1	119.0 (5)	N2—S2—C7	107.5 (3)
C2—C1—S1	120.0 (5)	O3—Na1—O4ⁱ	87.87 (18)
C3—C2—C1	118.1 (7)	O3—Na1—O1ⁱⁱ	168.82 (19)
C3—C2—H2	121.0	O4ⁱ—Na1—O1ⁱⁱ	80.99 (17)
C1—C2—H2	121.0	O3—Na1—O2ⁱⁱ	111.21 (17)
C4—C3—C2	121.4 (7)	O4ⁱ—Na1—O2ⁱⁱ	153.84 (19)
C4—C3—H3	119.3	O1ⁱⁱ—Na1—O2ⁱⁱ	79.13 (16)
C2—C3—H3	119.3	O3—Na1—O4	89.11 (18)
C3—C4—C5	121.4 (6)	O4ⁱ—Na1—O4	120.08 (15)
C3—C4—Cl3	120.2 (6)	O1ⁱⁱ—Na1—O4	97.22 (17)
C5—C4—Cl3	118.4 (6)	O2ⁱⁱ—Na1—O4	79.37 (16)
C4—C5—C6	119.5 (7)	O3—Na1—O5ⁱⁱ	98.04 (18)
C4—C5—H5	120.3	O4ⁱ—Na1—O5ⁱⁱ	79.73 (17)
C6—C5—H5	120.3	O1ⁱⁱ—Na1—O5ⁱⁱ	79.17 (16)
C1—C6—C5	118.7 (7)	O2ⁱⁱ—Na1—O5ⁱⁱ	79.97 (17)
C1—C6—H6	120.6	O4—Na1—O5ⁱⁱ	159.34 (19)
C5—C6—H6	120.6	O3—Na1—Na2ⁱⁱ	135.94 (16)
C8—C7—C12	120.3 (6)	O4ⁱ—Na1—Na2ⁱⁱ	106.41 (15)
C8—C7—S2	119.9 (5)	O1ⁱⁱ—Na1—Na2ⁱⁱ	48.27 (12)
C12—C7—S2	119.7 (5)	O2ⁱⁱ—Na1—Na2ⁱⁱ	47.43 (11)
C9—C8—C7	121.8 (7)	O4—Na1—Na2ⁱⁱ	116.21 (14)
C9—C8—H8	119.1	O5ⁱⁱ—Na1—Na2ⁱⁱ	46.95 (13)
C7—C8—H8	119.1	O3—Na1—Na1ⁱ	58.21 (13)
C8—C9—C10	118.5 (7)	O4ⁱ—Na1—Na1ⁱ	34.82 (13)
C8—C9—H9	120.8	O1ⁱⁱ—Na1—Na1ⁱ	110.94 (14)
C10—C9—H9	120.8	O2ⁱⁱ—Na1—Na1ⁱ	144.81 (14)
C9—C10—C11	121.6 (6)	O4—Na1—Na1ⁱ	129.66 (16)
C9—C10—Cl4	120.1 (6)	O5ⁱⁱ—Na1—Na1ⁱ	69.65 (13)
C11—C10—Cl4	118.2 (6)	Na2ⁱⁱ—Na1—Na1ⁱ	113.68 (9)
C10—C11—C12	118.6 (7)	O3—Na1—Na1ⁱⁱ	103.73 (16)
C10—C11—H11	120.7	O4ⁱ—Na1—Na1ⁱⁱ	89.82 (15)
C12—C11—H11	120.7	O1ⁱⁱ—Na1—Na1ⁱⁱ	77.28 (12)
C7—C12—C11	119.2 (6)	O2ⁱⁱ—Na1—Na1ⁱⁱ	102.14 (12)
C7—C12—H12	120.4	O4—Na1—Na1ⁱⁱ	33.89 (11)
C11—C12—H12	120.4	O5ⁱⁱ—Na1—Na1ⁱⁱ	155.46 (15)
S1—N1—Cl1	110.1 (3)	Na2ⁱⁱ—Na1—Na1ⁱⁱ	117.42 (9)
S2—N2—Cl2	109.9 (3)	Na1ⁱ—Na1—Na1ⁱⁱ	112.90 (12)
S1—O1—Na1ⁱ	122.3 (3)	O7^iv—Na2—O6	96.20 (18)
S1—O1—Na2	147.6 (3)	O7^iv—Na2—O5	95.44 (17)
Na1ⁱ—O1—Na2	85.19 (15)	O6—Na2—O5	158.84 (19)
S2—O2—Na2	128.2 (3)	O7^iv—Na2—O6^iv	90.36 (17)
S2—O2—Na1ⁱ	145.7 (3)	O6—Na2—O6^iv	116.01 (15)
Na2—O2—Na1ⁱ	84.77 (15)	O5—Na2—O6^iv	81.49 (18)
S1—O3—Na1	147.5 (3)	O7^iv—Na2—O2	172.32 (18)
Na1ⁱⁱ—O4—Na1	111.29 (19)	O6—Na2—O2	88.76 (17)
Na1ⁱⁱ—O4—H41O	109 (4)	O5—Na2—O2	81.69 (16)
Na1—O4—H41O	104 (5)	O6^iv—Na2—O2	82.19 (17)
Na1ⁱⁱ—O4—H42O	122 (4)	O7^iv—Na2—O1	108.44 (17)
Na1—O4—H42O	99 (5)	O6—Na2—O1	80.31 (16)
H41O—O4—H42O	110 (3)	O5—Na2—O1	79.27 (17)
Na2—O5—Na1ⁱ	84.24 (14)	O6^iv—Na2—O1	154.16 (19)
Na2—O5—H51O	116 (5)	O2—Na2—O1	78.11 (16)
Na1ⁱ—O5—H51O	112 (4)	O7^iv—Na2—Na1ⁱ	134.19 (15)
Na2—O5—H52O	113 (4)	O6—Na2—Na1ⁱ	111.57 (14)
Na1ⁱ—O5—H52O	125 (4)	O5—Na2—Na1ⁱ	48.80 (13)
H51O—O5—H52O	106 (3)	O6^iv—Na2—Na1ⁱ	107.62 (15)
Na2—O6—Na2ⁱⁱⁱ	115.42 (19)	O2—Na2—Na1ⁱ	47.80 (12)
Na2—O6—H61O	125 (4)	O1—Na2—Na1ⁱ	46.54 (11)
Na2ⁱⁱⁱ—O6—H61O	84 (5)	O7^iv—Na2—Na2^iv	61.98 (12)
Na2—O6—H62O	106 (4)	O6—Na2—Na2^iv	129.55 (16)
Na2ⁱⁱⁱ—O6—H62O	122 (5)	O5—Na2—Na2^iv	71.60 (13)
H61O—O6—H62O	104 (3)	O6^iv—Na2—Na2^iv	32.11 (12)
S2—O7—Na2ⁱⁱⁱ	128.0 (3)	O2—Na2—Na2^iv	110.35 (15)
O3—S1—O1	115.1 (3)	O1—Na2—Na2^iv	147.69 (13)
O3—S1—N1	115.0 (3)	Na1ⁱ—Na2—Na2^iv	115.72 (10)
O1—S1—N1	104.0 (3)	O7^iv—Na2—Na2ⁱⁱⁱ	110.76 (15)
O3—S1—C1	105.4 (3)	O6—Na2—Na2ⁱⁱⁱ	32.47 (11)
O1—S1—C1	107.6 (3)	O5—Na2—Na2ⁱⁱⁱ	151.17 (16)
N1—S1—C1	109.5 (3)	O6^iv—Na2—Na2ⁱⁱⁱ	86.37 (15)
O7—S2—O2	115.8 (3)	O2—Na2—Na2ⁱⁱⁱ	70.77 (12)
O7—S2—N2	114.8 (3)	O1—Na2—Na2ⁱⁱⁱ	102.54 (11)
O2—S2—N2	104.9 (3)	Na1ⁱ—Na2—Na2ⁱⁱⁱ	112.10 (9)
O7—S2—C7	106.4 (3)	Na2^iv—Na2—Na2ⁱⁱⁱ	109.70 (12)

C6—C1—C2—C3	1.7 (10)	S1—O3—Na1—O2ⁱⁱ	−157.2 (5)
S1—C1—C2—C3	−178.6 (5)	S1—O3—Na1—O4	−78.9 (6)
C1—C2—C3—C4	−2.3 (10)	S1—O3—Na1—O5ⁱⁱ	120.5 (5)
C2—C3—C4—C5	1.8 (11)	S1—O3—Na1—Na2ⁱⁱ	152.8 (5)
C2—C3—C4—Cl3	−176.7 (5)	S1—O3—Na1—Na1ⁱ	60.6 (5)
C3—C4—C5—C6	−0.7 (11)	S1—O3—Na1—Na1ⁱⁱ	−48.1 (6)
Cl3—C4—C5—C6	177.9 (5)	Na1ⁱⁱ—O4—Na1—O3	116.7 (2)
C2—C1—C6—C5	−0.6 (10)	Na1ⁱⁱ—O4—Na1—O4ⁱ	29.7 (2)
S1—C1—C6—C5	179.7 (5)	Na1ⁱⁱ—O4—Na1—O1ⁱⁱ	−54.1 (2)
C4—C5—C6—C1	0.1 (11)	Na1ⁱⁱ—O4—Na1—O2ⁱⁱ	−131.5 (2)
C12—C7—C8—C9	−1.9 (11)	Na1ⁱⁱ—O4—Na1—O5ⁱⁱ	−132.5 (5)
S2—C7—C8—C9	179.2 (6)	Na1ⁱⁱ—O4—Na1—Na2ⁱⁱ	−100.81 (19)
C7—C8—C9—C10	1.2 (11)	Na1ⁱⁱ—O4—Na1—Na1ⁱ	70.9 (3)
C8—C9—C10—C11	−0.8 (11)	Na2ⁱⁱⁱ—O6—Na2—O7^iv	119.6 (2)
C8—C9—C10—Cl4	−178.3 (6)	Na2ⁱⁱⁱ—O6—Na2—O5	−117.4 (5)
C9—C10—C11—C12	1.0 (11)	Na2ⁱⁱⁱ—O6—Na2—O6^iv	26.1 (2)
Cl4—C10—C11—C12	178.6 (5)	Na2ⁱⁱⁱ—O6—Na2—O2	−54.6 (2)
C8—C7—C12—C11	2.1 (10)	Na2ⁱⁱⁱ—O6—Na2—O1	−132.7 (2)
S2—C7—C12—C11	−179.0 (5)	Na2ⁱⁱⁱ—O6—Na2—Na1ⁱ	−97.6 (2)
C10—C11—C12—C7	−1.7 (10)	Na2ⁱⁱⁱ—O6—Na2—Na2^iv	61.1 (3)
Na1—O3—S1—O1	−64.0 (6)	Na1ⁱ—O5—Na2—O7^iv	147.92 (16)
Na1—O3—S1—N1	56.9 (6)	Na1ⁱ—O5—Na2—O6	24.8 (6)
Na1—O3—S1—C1	177.6 (5)	Na1ⁱ—O5—Na2—O6^iv	−122.54 (16)
Na1ⁱ—O1—S1—O3	1.5 (4)	Na1ⁱ—O5—Na2—O2	−39.25 (15)
Na2—O1—S1—O3	145.6 (5)	Na1ⁱ—O5—Na2—O1	40.13 (15)
Na1ⁱ—O1—S1—N1	−125.2 (3)	Na1ⁱ—O5—Na2—Na2^iv	−154.02 (14)
Na2—O1—S1—N1	18.9 (5)	Na1ⁱ—O5—Na2—Na2ⁱⁱⁱ	−56.4 (3)
Na1ⁱ—O1—S1—C1	118.7 (3)	S2—O2—Na2—O7^iv	−81.8 (15)
Na2—O1—S1—C1	−97.2 (5)	Na1ⁱ—O2—Na2—O7^iv	108.5 (14)
Cl1—N1—S1—O3	56.3 (4)	S2—O2—Na2—O6	48.6 (3)
Cl1—N1—S1—O1	−176.9 (3)	Na1ⁱ—O2—Na2—O6	−121.07 (17)
Cl1—N1—S1—C1	−62.1 (4)	S2—O2—Na2—O5	−150.3 (3)
C6—C1—S1—O3	0.2 (6)	Na1ⁱ—O2—Na2—O5	39.99 (16)
C2—C1—S1—O3	−179.5 (5)	S2—O2—Na2—O6^iv	−67.8 (3)
C6—C1—S1—O1	−123.1 (5)	Na1ⁱ—O2—Na2—O6^iv	122.47 (17)
C2—C1—S1—O1	57.2 (6)	S2—O2—Na2—O1	129.0 (3)
C6—C1—S1—N1	124.5 (5)	Na1ⁱ—O2—Na2—O1	−40.71 (14)
C2—C1—S1—N1	−55.3 (6)	S2—O2—Na2—Na1ⁱ	169.7 (4)
Na2ⁱⁱⁱ—O7—S2—O2	−70.9 (4)	S2—O2—Na2—Na2^iv	−83.5 (3)
Na2ⁱⁱⁱ—O7—S2—N2	51.7 (4)	Na1ⁱ—O2—Na2—Na2^iv	106.77 (14)
Na2ⁱⁱⁱ—O7—S2—C7	170.4 (3)	S2—O2—Na2—Na2ⁱⁱⁱ	21.0 (3)
Na2—O2—S2—O7	7.5 (4)	Na1ⁱ—O2—Na2—Na2ⁱⁱⁱ	−148.67 (15)
Na1ⁱ—O2—S2—O7	169.1 (4)	S1—O1—Na2—O7^iv	75.7 (5)
Na2—O2—S2—N2	−120.1 (3)	Na1ⁱ—O1—Na2—O7^iv	−134.14 (17)
Na1ⁱ—O2—S2—N2	41.4 (5)	S1—O1—Na2—O6	−17.7 (5)
Na2—O2—S2—C7	125.9 (3)	Na1ⁱ—O1—Na2—O6	132.51 (17)
Na1ⁱ—O2—S2—C7	−72.5 (5)	S1—O1—Na2—O5	167.9 (5)
Cl2—N2—S2—O7	54.2 (4)	Na1ⁱ—O1—Na2—O5	−41.93 (15)
Cl2—N2—S2—O2	−177.6 (3)	S1—O1—Na2—O6^iv	−149.6 (4)
Cl2—N2—S2—C7	−64.0 (4)	Na1ⁱ—O1—Na2—O6^iv	0.6 (5)
C8—C7—S2—O7	−164.6 (6)	S1—O1—Na2—O2	−108.4 (5)
C12—C7—S2—O7	16.5 (6)	Na1ⁱ—O1—Na2—O2	41.73 (15)
C8—C7—S2—O2	71.0 (6)	S1—O1—Na2—Na1ⁱ	−150.2 (6)
C12—C7—S2—O2	−107.9 (5)	S1—O1—Na2—Na2^iv	142.2 (4)
C8—C7—S2—N2	−41.2 (6)	Na1ⁱ—O1—Na2—Na2^iv	−67.7 (3)
C12—C7—S2—N2	139.9 (5)	S1—O1—Na2—Na2ⁱⁱⁱ	−41.5 (5)
S1—O3—Na1—O4ⁱ	41.2 (6)	Na1ⁱ—O1—Na2—Na2ⁱⁱⁱ	108.68 (13)
S1—O3—Na1—O1ⁱⁱ	45.8 (14)

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) x+1/2, −y+1/2, −z; (iv) 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
O4—H41O···Cl1	0.84 (2)	2.70 (2)	3.523 (5)	167 (5)
O4—H42O···N2ⁱⁱ	0.84 (2)	2.06 (2)	2.903 (7)	177 (7)
O4—H42O···S2ⁱⁱ	0.84 (2)	2.91 (4)	3.633 (5)	145 (6)
O5—H51O···N2^v	0.85 (2)	2.06 (2)	2.899 (6)	170 (7)
O5—H51O···Cl2^v	0.85 (2)	2.89 (3)	3.631 (5)	147 (4)
O5—H52O···N1^v	0.86 (2)	2.16 (2)	3.006 (6)	169 (7)
O5—H52O···Cl1^v	0.86 (2)	2.82 (3)	3.522 (5)	139 (4)
O6—H61O···Cl2^iv	0.87 (2)	2.61 (5)	3.305 (5)	138 (6)
O6—H61O···O2ⁱⁱⁱ	0.87 (2)	2.63 (6)	3.212 (6)	125 (6)
O6—H62O···N1	0.86 (2)	2.00 (2)	2.845 (7)	167 (6)
O6—H62O···S1	0.86 (2)	3.00 (4)	3.687 (5)	138 (5)

Symmetry codes: (ii) x+1/2, −y+3/2, −z; (iii) x+1/2, −y+1/2, −z; (iv) x−1/2, −y+1/2, −z; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	Na⁺·C₆H₄Cl₂NO₂S⁻·1.5H₂O
M_r	275.09
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	303
a, b, c (Å)	6.7041 (4), 10.4763 (8), 30.037 (2)
V (Å³)	2109.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.30 × 0.12 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Analytical CrysAlis RED (Oxford Diffraction, 2002)
T_min, T_max	0.865, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	14393, 4281, 2959
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.140, 1.10
No. of reflections	4281
No. of parameters	280
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.33
Absolute structure	Flack (1983), 1777 Friedel pairs'
Absolute structure parameter	0.22 (12)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41O···Cl1	0.842 (19)	2.70 (2)	3.523 (5)	167 (5)
O4—H42O···N2ⁱ	0.841 (19)	2.06 (2)	2.903 (7)	177 (7)
O4—H42O···S2ⁱ	0.841 (19)	2.91 (4)	3.633 (5)	145 (6)
O5—H51O···N2ⁱⁱ	0.848 (19)	2.06 (2)	2.899 (6)	170 (7)
O5—H51O···Cl2ⁱⁱ	0.848 (19)	2.89 (3)	3.631 (5)	147 (4)
O5—H52O···N1ⁱⁱ	0.861 (19)	2.16 (2)	3.006 (6)	169 (7)
O5—H52O···Cl1ⁱⁱ	0.861 (19)	2.82 (3)	3.522 (5)	139 (4)
O6—H61O···Cl2ⁱⁱⁱ	0.87 (2)	2.61 (5)	3.305 (5)	138 (6)
O6—H61O···O2^iv	0.87 (2)	2.63 (6)	3.212 (6)	125 (6)
O6—H62O···N1	0.86 (2)	2.00 (2)	2.845 (7)	167 (6)
O6—H62O···S1	0.86 (2)	3.00 (4)	3.687 (5)	138 (5)

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, −z; (iv) x+1/2, −y+1/2, −z.

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