Sodium N-bromo-2-chloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Foro, S.; Shakuntala, K.

doi:10.1107/S160053681102071X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m870

doi:10.1107/S160053681102071X

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Sodium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate

B. Thimme Gowda,^a ^* Sabine Foro ^b and K. Shakuntala ^a

^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 19 May 2011; accepted 30 May 2011; online 11 June 2011)

In the title compound, Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O, one water molecule has crystallographically imposed twofold symmetry. The Na⁺ cation shows a pseudo-octahedral coordination provided by three O atoms of water molecules and three sulfonyl O atoms of different N-bromo-2-chlorobenzenesulfonamidate anions. The S—N distance of 1.579 (6) Å is consistent with an S=N double-bond character. The crystal structure is stabilized by O—H⋯Br, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For background to the chemistry of N-haloarylsulfonamides, see: Gowda & Shetty (2004 ); Usha & Gowda (2006 ). For our study of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda, Kožíšek et al. (2007 ); Gowda, Usha et al. (2007 ). For related structures, see: George et al. (2000 ); Olmstead & Power (1986 ). For an isostructural compound, see: Gowda et al. (2010 ).

Experimental

Crystal data

Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O
M_r = 319.53
Monoclinic, C 2/c
a = 11.200 (2) Å
b = 6.728 (1) Å
c = 28.304 (3) Å
β = 100.94 (1)°
V = 2094.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 4.41 mm⁻¹
T = 293 K
0.34 × 0.30 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.316, T_max = 0.578
7442 measured reflections
2147 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.128
S = 1.25
2147 reflections
141 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.27 e Å⁻³
Δρ_min = −1.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯Br1ⁱ	0.82 (2)	2.70 (2)	3.518 (5)	171 (8)
O3—H32⋯N1	0.81 (2)	2.21 (5)	2.934 (7)	149 (8)
O3—H32⋯O2	0.81 (2)	2.51 (5)	3.232 (7)	148 (8)
O4—H41⋯N1ⁱⁱ	0.82 (2)	2.20 (3)	3.002 (7)	168 (8)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S160053681102071X/rz2602sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102071X/rz2602Isup2.hkl

checkCIF report

Comment top

The chemistry of N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda & Shetty, 2004; Usha & Gowda, 2006). In the present work, as a part of exploring the substituent effects on the crystal structures of N-haloarylsulfonamidates, the structure of sodium N-bromo-2-chlorobenzenesulfonamidate (I) has been determined (Fig. 1). The structure of (I) resembles those of sodium N-bromo-benzenesulfonamidate (II) (Gowda, Usha et al., 2007), sodium i>N-bromo-4-chlorobenzenesulfonamidate (III) (Gowda, Kožíšek et al., 2007) and other sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986), and is isostructural with the previously reported N-chloro-2-chloro-benzenesulfonamidate (Gowda et al., 2010) (IV).

In the title compound, one water molecule (O4) has crystallographically imposed twofold axis. The sodium ion shows octahedral coordination by three O atoms of water molecules and by three sulfonyl O atoms of three different N-bromo-2-chloro-benzenesulfonamide anions.

There is no interaction between the N and Na atoms in the molecule. The S—N distance of N1—S1, 1.579 (6)Å is consistent with a S—N double bond and is in agreement with the observed values of 1.578 (4)Å in (II), 1.588 (2) Å in (IV), and N1—S1, 1.574 (5)Å and N2—S2 1.579 (4)Å in (III).

The crystal packing consists of a two-dimensional polymeric layers running parallel to the ac plane (Fig. 2). The molecular packing is stabilized by O3—H31···Br1, O3—H32···N1, O3—H32···O2 and O4—H41···N1 hydrogen bonds (Table 1).

Related literature top

For background to the chemistry of N-haloarylsulfonamides, see: Gowda & Shetty (2004); Usha & Gowda (2006). For our study of the effect of substituents on the structures of N-haloarylsulfonamides, see: Gowda, Kožíšek et al. (2007); Gowda, Usha et al. (2007). For related structures, see: George et al. (2000); Olmstead & Power (1986). For an isostructural compound, see: Gowda et al. (2010). [Please check added text]

Experimental top

The title compound was prepared according to the literature method (Usha & Gowda, 2006). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Prism like yellow single crystals of the title compound used in X-ray diffraction studies were obtained from slow evaporation of its aqueous solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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. The molecular structure of the title compound, showing the asymmetric unit extended to show the coordination geometry for the Na⁺ ion. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii (symmetry codes: (i) x + 1/2, y - 1/2, z; (ii) -x + 2, y, -z + 3/2; (iii) -x + 5/2, y - 1/2, -z + 3/2).
	Fig. 2. Crystal packing of the title compound with hydrogen bonding shown as dashed lines.

Sodium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate top

Crystal data top

Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O	F(000) = 1256
M_r = 319.53	D_x = 2.027 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4107 reflections
a = 11.200 (2) Å	θ = 2.9–27.8°
b = 6.728 (1) Å	µ = 4.41 mm⁻¹
c = 28.304 (3) Å	T = 293 K
β = 100.94 (1)°	Prism, yellow
V = 2094.0 (5) Å³	0.34 × 0.30 × 0.14 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector	2147 independent reflections
Radiation source: fine-focus sealed tube	1955 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
T_min = 0.316, T_max = 0.578	k = −8→7
7442 measured reflections	l = −35→35

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ²(F_o²) + (0.0182P)² + 43.7119P] where P = (F_o² + 2F_c²)/3
2147 reflections	(Δ/σ)_max = 0.001
141 parameters	Δρ_max = 2.27 e Å⁻³
4 restraints	Δρ_min = −1.19 e Å⁻³

Crystal data top

Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O	V = 2094.0 (5) Å³
M_r = 319.53	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.200 (2) Å	µ = 4.41 mm⁻¹
b = 6.728 (1) Å	T = 293 K
c = 28.304 (3) Å	0.34 × 0.30 × 0.14 mm
β = 100.94 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector	2147 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1955 reflections with I > 2σ(I)
T_min = 0.316, T_max = 0.578	R_int = 0.018
7442 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	4 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ²(F_o²) + (0.0182P)² + 43.7119P] where P = (F_o² + 2F_c²)/3
2147 reflections	Δρ_max = 2.27 e Å⁻³
141 parameters	Δρ_min = −1.19 e Å⁻³

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) 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
C1	0.8143 (5)	−0.3307 (9)	0.6083 (2)	0.0205 (12)
C2	0.6903 (6)	−0.3509 (11)	0.5927 (2)	0.0311 (14)
H2	0.6375	−0.3101	0.6125	0.037*
C3	0.6437 (7)	−0.4309 (13)	0.5480 (3)	0.0433 (19)
H3	0.5600	−0.4409	0.5377	0.052*
C4	0.7209 (8)	−0.4957 (12)	0.5187 (3)	0.044 (2)
H4	0.6892	−0.5508	0.4888	0.053*
C5	0.8449 (8)	−0.4791 (11)	0.5336 (3)	0.0374 (17)
H5	0.8971	−0.5243	0.5140	0.045*
C6	0.8919 (6)	−0.3942 (9)	0.5782 (2)	0.0249 (13)
Br1	0.88260 (6)	0.14784 (10)	0.62206 (2)	0.0312 (2)
N1	0.9583 (5)	−0.0535 (8)	0.66407 (18)	0.0247 (11)
Na1	1.1437 (2)	−0.5132 (4)	0.73529 (9)	0.0303 (6)
O1	0.7549 (4)	−0.1730 (8)	0.68272 (16)	0.0324 (11)
O2	0.9370 (4)	−0.3782 (7)	0.69654 (15)	0.0286 (10)
O3	1.2055 (4)	−0.1890 (8)	0.70471 (17)	0.0335 (11)
H31	1.246 (5)	−0.241 (12)	0.687 (2)	0.040*
H32	1.1325 (19)	−0.199 (12)	0.695 (2)	0.040*
O4	1.0000	−0.7830 (10)	0.7500	0.0336 (16)
H41	0.979 (7)	−0.861 (9)	0.728 (2)	0.040*
S1	0.86584 (13)	−0.2281 (2)	0.66713 (5)	0.0198 (3)
Cl1	1.04842 (16)	−0.3824 (3)	0.59503 (7)	0.0414 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (3)	0.017 (3)	0.021 (3)	0.001 (2)	0.003 (2)	0.002 (2)
C2	0.026 (3)	0.033 (4)	0.033 (3)	0.004 (3)	0.003 (3)	0.000 (3)
C3	0.030 (4)	0.050 (5)	0.045 (4)	−0.004 (4)	−0.007 (3)	−0.009 (4)
C4	0.056 (5)	0.043 (5)	0.027 (4)	−0.005 (4)	−0.009 (3)	−0.010 (3)
C5	0.055 (5)	0.032 (4)	0.028 (4)	−0.001 (3)	0.017 (3)	−0.005 (3)
C6	0.030 (3)	0.020 (3)	0.026 (3)	0.000 (3)	0.009 (3)	0.002 (2)
Br1	0.0358 (4)	0.0245 (3)	0.0342 (4)	0.0033 (3)	0.0092 (3)	0.0072 (3)
N1	0.022 (3)	0.025 (3)	0.025 (3)	0.003 (2)	0.001 (2)	0.002 (2)
Na1	0.0299 (14)	0.0312 (14)	0.0320 (14)	0.0047 (11)	0.0114 (11)	−0.0007 (11)
O1	0.030 (2)	0.040 (3)	0.030 (2)	0.001 (2)	0.0131 (19)	−0.006 (2)
O2	0.033 (2)	0.028 (2)	0.023 (2)	0.002 (2)	0.0021 (18)	0.0075 (19)
O3	0.027 (2)	0.039 (3)	0.034 (3)	0.002 (2)	0.006 (2)	−0.003 (2)
O4	0.044 (4)	0.024 (4)	0.030 (4)	0.000	0.000 (3)	0.000
S1	0.0209 (7)	0.0215 (7)	0.0170 (7)	0.0005 (6)	0.0038 (5)	0.0002 (6)
Cl1	0.0280 (8)	0.0478 (11)	0.0522 (11)	0.0018 (8)	0.0174 (8)	−0.0107 (9)

Geometric parameters (Å, º) top

C1—C2	1.382 (9)	Na1—O3ⁱⁱⁱ	2.459 (5)
C1—C6	1.393 (8)	Na1—O3	2.493 (6)
C1—S1	1.793 (6)	Na1—O4	2.512 (6)
C2—C3	1.383 (10)	Na1—O2	2.534 (5)
C2—H2	0.9300	Na1—S1ⁱⁱ	3.381 (3)
C3—C4	1.378 (12)	Na1—H32	2.40 (9)
C3—H3	0.9300	O1—S1	1.444 (5)
C4—C5	1.378 (11)	O1—Na1^iv	2.371 (5)
C4—H4	0.9300	O2—S1	1.448 (5)
C5—C6	1.396 (9)	O2—Na1ⁱⁱ	2.455 (5)
C5—H5	0.9300	O3—Na1^v	2.459 (5)
C6—Cl1	1.729 (7)	O3—H31	0.82 (2)
Br1—N1	1.893 (5)	O3—H32	0.81 (2)
N1—S1	1.579 (6)	O4—Na1ⁱⁱ	2.512 (6)
Na1—O1ⁱ	2.371 (5)	O4—H41	0.82 (2)
Na1—O2ⁱⁱ	2.455 (5)	S1—Na1ⁱⁱ	3.381 (3)

C2—C1—C6	118.6 (6)	O2ⁱⁱ—Na1—S1ⁱⁱ	22.28 (11)
C2—C1—S1	117.5 (5)	O3ⁱⁱⁱ—Na1—S1ⁱⁱ	80.37 (14)
C6—C1—S1	123.9 (5)	O3—Na1—S1ⁱⁱ	80.85 (13)
C1—C2—C3	120.9 (6)	O4—Na1—S1ⁱⁱ	98.86 (11)
C1—C2—H2	119.6	O2—Na1—S1ⁱⁱ	88.99 (13)
C3—C2—H2	119.6	O1ⁱ—Na1—H32	94.9 (14)
C4—C3—C2	120.2 (7)	O2ⁱⁱ—Na1—H32	93.2 (15)
C4—C3—H3	119.9	O3ⁱⁱⁱ—Na1—H32	136.1 (7)
C2—C3—H3	119.9	O3—Na1—H32	19.0 (5)
C5—C4—C3	120.1 (7)	O4—Na1—H32	137.7 (5)
C5—C4—H4	120.0	O2—Na1—H32	61.1 (5)
C3—C4—H4	120.0	S1ⁱⁱ—Na1—H32	83.3 (15)
C4—C5—C6	119.7 (7)	S1—O1—Na1^iv	153.3 (3)
C4—C5—H5	120.2	S1—O2—Na1ⁱⁱ	117.7 (3)
C6—C5—H5	120.2	S1—O2—Na1	149.0 (3)
C1—C6—C5	120.5 (6)	Na1ⁱⁱ—O2—Na1	88.25 (17)
C1—C6—Cl1	122.4 (5)	Na1^v—O3—Na1	112.4 (2)
C5—C6—Cl1	117.1 (5)	Na1^v—O3—H31	104 (5)
S1—N1—Br1	110.3 (3)	Na1—O3—H31	94 (6)
O1ⁱ—Na1—O2ⁱⁱ	167.5 (2)	Na1^v—O3—H32	142 (5)
O1ⁱ—Na1—O3ⁱⁱⁱ	80.89 (18)	Na1—O3—H32	74 (6)
O2ⁱⁱ—Na1—O3ⁱⁱⁱ	86.70 (18)	H31—O3—H32	112 (4)
O1ⁱ—Na1—O3	88.03 (19)	Na1—O4—Na1ⁱⁱ	87.5 (3)
O2ⁱⁱ—Na1—O3	96.71 (18)	Na1—O4—H41	116 (6)
O3ⁱⁱⁱ—Na1—O3	117.45 (15)	Na1ⁱⁱ—O4—H41	119 (6)
O1ⁱ—Na1—O4	101.87 (19)	O1—S1—O2	114.5 (3)
O2ⁱⁱ—Na1—O4	78.11 (16)	O1—S1—N1	115.9 (3)
O3ⁱⁱⁱ—Na1—O4	85.18 (16)	O2—S1—N1	104.8 (3)
O3—Na1—O4	156.70 (19)	O1—S1—C1	103.8 (3)
O1ⁱ—Na1—O2	115.86 (19)	O2—S1—C1	108.1 (3)
O2ⁱⁱ—Na1—O2	76.42 (19)	N1—S1—C1	109.5 (3)
O3ⁱⁱⁱ—Na1—O2	157.31 (19)	O1—S1—Na1ⁱⁱ	74.5 (2)
O3—Na1—O2	80.02 (17)	N1—S1—Na1ⁱⁱ	126.1 (2)
O4—Na1—O2	76.68 (15)	C1—S1—Na1ⁱⁱ	119.0 (2)
O1ⁱ—Na1—S1ⁱⁱ	150.64 (16)

C6—C1—C2—C3	−0.5 (10)	O1ⁱ—Na1—O4—Na1ⁱⁱ	−152.81 (18)
S1—C1—C2—C3	−179.3 (6)	O2ⁱⁱ—Na1—O4—Na1ⁱⁱ	39.93 (12)
C1—C2—C3—C4	1.4 (12)	O3ⁱⁱⁱ—Na1—O4—Na1ⁱⁱ	127.57 (16)
C2—C3—C4—C5	−0.7 (13)	O3—Na1—O4—Na1ⁱⁱ	−39.3 (4)
C3—C4—C5—C6	−0.8 (12)	O2—Na1—O4—Na1ⁱⁱ	−38.72 (11)
C2—C1—C6—C5	−1.0 (10)	S1ⁱⁱ—Na1—O4—Na1ⁱⁱ	48.11 (6)
S1—C1—C6—C5	177.7 (5)	Na1^iv—O1—S1—O2	73.2 (8)
C2—C1—C6—Cl1	−178.1 (5)	Na1^iv—O1—S1—N1	−49.0 (8)
S1—C1—C6—Cl1	0.6 (8)	Na1^iv—O1—S1—C1	−169.1 (7)
C4—C5—C6—C1	1.6 (11)	Na1^iv—O1—S1—Na1ⁱⁱ	74.1 (7)
C4—C5—C6—Cl1	178.9 (6)	Na1ⁱⁱ—O2—S1—O1	1.2 (4)
O1ⁱ—Na1—O2—S1	−74.9 (6)	Na1—O2—S1—O1	−142.6 (5)
O2ⁱⁱ—Na1—O2—S1	107.4 (5)	Na1ⁱⁱ—O2—S1—N1	129.4 (3)
O3ⁱⁱⁱ—Na1—O2—S1	150.4 (5)	Na1—O2—S1—N1	−14.4 (6)
O3—Na1—O2—S1	8.0 (6)	Na1ⁱⁱ—O2—S1—C1	−113.9 (3)
O4—Na1—O2—S1	−171.8 (6)	Na1—O2—S1—C1	102.3 (6)
S1ⁱⁱ—Na1—O2—S1	88.9 (6)	Na1—O2—S1—Na1ⁱⁱ	−143.8 (7)
O1ⁱ—Na1—O2—Na1ⁱⁱ	136.66 (17)	Br1—N1—S1—O1	−57.6 (4)
O2ⁱⁱ—Na1—O2—Na1ⁱⁱ	−41.0 (2)	Br1—N1—S1—O2	175.1 (3)
O3ⁱⁱⁱ—Na1—O2—Na1ⁱⁱ	2.0 (6)	Br1—N1—S1—C1	59.4 (4)
O3—Na1—O2—Na1ⁱⁱ	−140.47 (18)	Br1—N1—S1—Na1ⁱⁱ	−146.92 (16)
O4—Na1—O2—Na1ⁱⁱ	39.77 (14)	C2—C1—S1—O1	−5.0 (6)
S1ⁱⁱ—Na1—O2—Na1ⁱⁱ	−59.58 (15)	C6—C1—S1—O1	176.3 (5)
O1ⁱ—Na1—O3—Na1^v	−108.3 (2)	C2—C1—S1—O2	117.0 (5)
O2ⁱⁱ—Na1—O3—Na1^v	60.1 (2)	C6—C1—S1—O2	−61.7 (6)
O3ⁱⁱⁱ—Na1—O3—Na1^v	−29.7 (2)	C2—C1—S1—N1	−129.4 (5)
O4—Na1—O3—Na1^v	135.6 (4)	C6—C1—S1—N1	51.9 (6)
O2—Na1—O3—Na1^v	135.0 (2)	C2—C1—S1—Na1ⁱⁱ	74.7 (5)
S1ⁱⁱ—Na1—O3—Na1^v	44.40 (17)	C6—C1—S1—Na1ⁱⁱ	−103.9 (5)

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+2, y, −z+3/2; (iii) −x+5/2, y−1/2, −z+3/2; (iv) x−1/2, y+1/2, z; (v) −x+5/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Br1ⁱ	0.82 (2)	2.70 (2)	3.518 (5)	171 (8)
O3—H32···N1	0.81 (2)	2.21 (5)	2.934 (7)	149 (8)
O3—H32···O2	0.81 (2)	2.51 (5)	3.232 (7)	148 (8)
O4—H41···N1^vi	0.82 (2)	2.20 (3)	3.002 (7)	168 (8)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O
M_r	319.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	11.200 (2), 6.728 (1), 28.304 (3)
β (°)	100.94 (1)
V (Å³)	2094.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.41
Crystal size (mm)	0.34 × 0.30 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.316, 0.578
No. of measured, independent and observed [I > 2σ(I)] reflections	7442, 2147, 1955
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.128, 1.25
No. of reflections	2147
No. of parameters	141
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0182P)² + 43.7119P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.27, −1.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), 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···Br1ⁱ	0.82 (2)	2.70 (2)	3.518 (5)	171 (8)
O3—H32···N1	0.81 (2)	2.21 (5)	2.934 (7)	149 (8)
O3—H32···O2	0.81 (2)	2.51 (5)	3.232 (7)	148 (8)
O4—H41···N1ⁱⁱ	0.82 (2)	2.20 (3)	3.002 (7)	168 (8)

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

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for the grant under theUGC-BSR one time grant to Faculty/Professors.

References

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