Sodium N-bromo-4-chloro­benzene­sulfonamidate sesquihydrate

Gowda, B.T.; Kožíšek, J.; Tokarčík, M.; Fuess, H.

doi:10.1107/S1600536807024531

Buy article online - an online subscription or single-article purchase is required to access this article.

Sodium N-bromo-4-chlorobenzenesulfonamidate sesquihydrate

B. T. Gowda, J. Kožíšek, M. Tokarčík and H. Fuess

In the structure of the title compound, Na⁺·C₆H₄BrClNO₂S⁻·1.5H₂O, which crystallizes with two cations, two anions and three water molecules in the asymmetric unit, the sodium ions show octahedral coordination by three O atoms of water molecules and by three sulfonyl O atoms of three different N-bromobenzenesulfonamide anions. The S—N distances [1.574 (5) and 1.579 (4) Å] are consistent with an S=N double bond. The crystal structure is stabilized by O—H

Br, O—H

N, O—H

O and C—H

Br hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024531/bt2373sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024531/bt2373Isup2.hkl Contains datablock I

CCDC reference: 614774

checkCIF report

Key indicators

Single-crystal X-ray study
T = 300 K
Mean (C-C) = 0.009 Å
R factor = 0.045
wR factor = 0.103
Data-to-parameter ratio = 14.8

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
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
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           26.02
           From the CIF: _reflns_number_total               4156
           Count of symmetry unique reflns         2456
           Completeness (_total/calc)            169.22%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1700
           Fraction of Friedel pairs measured     0.692
           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
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The chemistry of N-halo arylsulfonamides is of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2005; Gowda & Shetty, 2004; Usha & Gowda, 2006). In the present work, the structure of sodium N-bromo-4-chlorobenzenesulfonamde has been determined to explore the effect substituent on the solid state structures of sulfonamides and N-halo arylsulfonamides (Gowda et al., 2003; Gowda, Foro et al., 2007; Gowda, Jyothi et al., 2007; Gowda, Kozisek et al., 2007; Gowda, Savitha et al., 2007; Gowda, Srilatha et al., 2007; Gowda, Usha et al., 2007). The structure of of the title compound (Fig. 1) resembles those of sodium N-bromo-benzenesulfonamde (Gowda, Usha et al., 2007) and sodium N-chloro-4-chlorobenzenesulfonamde (Gowda, Jyothi et al., 2007). The sodium ion shows octahedral coordination by three O atoms of water molecules and by three sulfonyl O atoms of three different N-bromobenzenesulfonamide anions. There is no interaction between the nitrogen and sodium atoms in the molecule and there are two molecules in the asymmetric unit. The S—N distances of N1—S1, 1.574 (5)Å and N2—S2 1.579 (4)Å are consistent with a S—N double bond. There are several hydrogen bonds in the crystal structure.

Related literature top

For related literature, see: Gowda & Shetty (2004); Gowda & Usha (2003); Gowda et al. (2005); Gowda, Foro et al. (2007); Gowda, Jyothi, Foro et al. (2007); Gowda, Jyothi, Kozisek et al. (2003); Gowda, Kozisek et al. (2007); Gowda, Savitha et al. (2007); Gowda, Srilatha et al. (2007); Gowda, Usha et al.(2007); Usha & Gowda (2006).

Experimental top

The title compound was prepared according to the literature method (Gowda & Usha, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda & Usha, 2003). Single crystals of the title compound were obtained from its aqueous solution and used for X-ray diffraction studies at room temperature.

Structure description top

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), Diamond (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing diagram of the title compound viewed down the axis a, showing part of the crystal structure stabilized by hydrogen bonds O7w—H72···N1, O3w—H32···N2 and O4w—H41···N2.

Sodium N-Bromo-4-Chlorobenzenesulfonamide sesquihydrate top

Crystal data top

Na⁺.C₆H₄BrClNO₂S⁻.1.5H₂O	F(000) = 1256
M_r = 319.54	D_x = 1.978 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2831 reflections
a = 6.7510 (7) Å	θ = 2.5–26.4°
b = 10.495 (1) Å	µ = 4.3 mm⁻¹
c = 30.286 (3) Å	T = 300 K
V = 2145.8 (4) Å³	Block, yellow
Z = 8	0.52 × 0.32 × 0.11 mm

Data collection top

Xcalibur System, Oxford Diffraction diffractometer	4156 independent reflections
Radiation source: fine-focus sealed tube	3782 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Rotation method data acquisition using ω and phi scans	θ_max = 26.0°, θ_min = 5.1°
Absorption correction: analytical (Clark & Reid, 1995)	h = −8→5
T_min = 0.186, T_max = 0.543	k = −12→12
13453 measured reflections	l = −36→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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0395P)² + 5.8841P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.011
4156 reflections	Δρ_max = 0.51 e Å⁻³
280 parameters	Δρ_min = −0.63 e Å⁻³
9 restraints	Absolute structure: Flack (1983), 1739 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.025 (12)

Crystal data top

Na⁺.C₆H₄BrClNO₂S⁻.1.5H₂O	V = 2145.8 (4) Å³
M_r = 319.54	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7510 (7) Å	µ = 4.3 mm⁻¹
b = 10.495 (1) Å	T = 300 K
c = 30.286 (3) Å	0.52 × 0.32 × 0.11 mm

Data collection top

Xcalibur System, Oxford Diffraction diffractometer	4156 independent reflections
Absorption correction: analytical (Clark & Reid, 1995)	3782 reflections with I > 2σ(I)
T_min = 0.186, T_max = 0.543	R_int = 0.043
13453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	Δρ_max = 0.51 e Å⁻³
S = 1.06	Δρ_min = −0.63 e Å⁻³
4156 reflections	Absolute structure: Flack (1983), 1739 Friedel Pairs
280 parameters	Absolute structure parameter: 0.025 (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	0.2141 (8)	0.1181 (5)	0.13313 (16)	0.0231 (11)
C2	0.2041 (11)	0.2388 (6)	0.1520 (2)	0.0425 (15)
H2	0.2513	0.3093	0.1367	0.051*
C3	0.1235 (10)	0.2537 (8)	0.1939 (2)	0.0488 (18)
H3	0.1168	0.3338	0.2069	0.059*
C4	0.0532 (9)	0.1474 (8)	0.2159 (2)	0.0429 (16)
C5	0.0622 (10)	0.0286 (7)	0.1971 (2)	0.0433 (16)
H5	0.0144	−0.0417	0.2124	0.052*
C6	0.1412 (9)	0.0129 (6)	0.15574 (18)	0.0340 (14)
H6	0.1461	−0.0676	0.1429	0.041*
C7	−0.2985 (8)	−0.4278 (5)	0.13144 (16)	0.0223 (10)
C8	−0.3727 (9)	−0.3308 (6)	0.15638 (19)	0.0327 (13)
H8	−0.3697	−0.2475	0.1459	0.039*
C9	−0.4532 (9)	−0.3576 (7)	0.1977 (2)	0.0391 (14)
H9	−0.5053	−0.2925	0.2150	0.047*
C10	−0.4546 (9)	−0.4807 (7)	0.2125 (2)	0.0388 (15)
C11	−0.3822 (10)	−0.5776 (7)	0.1881 (2)	0.0415 (16)
H11	−0.3856	−0.6605	0.1990	0.050*
C12	−0.3020 (10)	−0.5526 (5)	0.1466 (2)	0.0378 (13)
H12	−0.2519	−0.6184	0.1293	0.045*
N1	0.4811 (6)	−0.0033 (5)	0.08062 (15)	0.0296 (10)
N2	−0.0030 (6)	−0.4826 (4)	0.07372 (14)	0.0254 (10)
O1	0.1630 (6)	0.0484 (4)	0.05138 (11)	0.0298 (9)
O2	0.3802 (7)	0.2285 (4)	0.06782 (13)	0.0379 (10)
O3W	0.8614 (6)	0.2759 (4)	0.04069 (14)	0.0346 (10)
H31	0.843 (10)	0.219 (4)	0.0589 (14)	0.041*
H32	0.914 (9)	0.337 (4)	0.0526 (16)	0.041*
O4W	0.2557 (6)	0.4969 (4)	−0.00286 (12)	0.0322 (9)
H41	0.164 (6)	0.489 (5)	0.0146 (16)	0.039*
H42	0.312 (8)	0.565 (3)	0.0007 (18)	0.039*
O5	−0.3324 (6)	−0.4527 (4)	0.04617 (11)	0.0285 (8)
O6	−0.1679 (7)	−0.2632 (3)	0.07497 (12)	0.0330 (9)
O7W	0.3480 (6)	−0.2262 (4)	0.03649 (13)	0.0341 (9)
H71	0.344 (10)	−0.284 (4)	0.0549 (14)	0.041*
H72	0.394 (9)	−0.162 (3)	0.0481 (16)	0.041*
Na1	0.5364 (3)	0.3495 (2)	0.01446 (7)	0.0302 (5)
Na2	0.0188 (3)	−0.1502 (2)	0.01942 (8)	0.0319 (5)
S1	0.3149 (2)	0.10180 (12)	0.07971 (4)	0.0237 (3)
S2	−0.1963 (2)	−0.39892 (11)	0.07809 (4)	0.0222 (2)
Cl1	−0.0412 (3)	0.1656 (3)	0.26874 (6)	0.0739 (7)
Cl2	−0.5467 (3)	−0.5110 (2)	0.26505 (5)	0.0600 (5)
Br1	0.68840 (9)	0.04232 (6)	0.119227 (19)	0.03784 (16)
Br2	0.18659 (9)	−0.42882 (6)	0.11598 (2)	0.03978 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (3)	0.029 (3)	0.017 (2)	0.001 (2)	0.001 (2)	−0.0003 (19)
C2	0.058 (4)	0.033 (3)	0.037 (3)	0.000 (3)	0.008 (3)	−0.003 (3)
C3	0.047 (4)	0.055 (4)	0.044 (4)	−0.008 (3)	0.011 (3)	−0.017 (3)
C4	0.019 (3)	0.075 (5)	0.035 (3)	−0.004 (3)	0.003 (3)	−0.012 (3)
C5	0.042 (4)	0.059 (4)	0.029 (3)	−0.008 (3)	0.005 (3)	0.008 (3)
C6	0.047 (4)	0.029 (3)	0.026 (3)	0.001 (3)	0.003 (2)	0.004 (2)
C7	0.019 (2)	0.029 (3)	0.019 (2)	0.004 (2)	−0.002 (2)	0.0020 (18)
C8	0.039 (3)	0.030 (3)	0.029 (3)	0.002 (2)	0.008 (2)	0.001 (2)
C9	0.031 (3)	0.049 (4)	0.037 (3)	−0.002 (3)	0.015 (3)	−0.008 (3)
C10	0.027 (3)	0.055 (4)	0.034 (3)	−0.005 (3)	0.006 (3)	0.010 (3)
C11	0.042 (4)	0.041 (4)	0.042 (4)	0.005 (3)	0.005 (3)	0.014 (3)
C12	0.039 (3)	0.033 (3)	0.042 (3)	0.003 (3)	0.010 (3)	0.001 (2)
N1	0.024 (2)	0.035 (3)	0.030 (2)	0.005 (2)	−0.006 (2)	−0.006 (2)
N2	0.024 (2)	0.027 (2)	0.026 (2)	0.0013 (19)	0.0013 (18)	−0.0009 (18)
O1	0.030 (2)	0.041 (2)	0.0191 (17)	0.0012 (19)	−0.0054 (16)	−0.0017 (15)
O2	0.054 (3)	0.027 (2)	0.033 (2)	−0.0097 (19)	0.0062 (19)	0.0076 (17)
O3W	0.034 (2)	0.030 (2)	0.040 (2)	−0.0001 (18)	0.0043 (19)	0.0009 (18)
O4W	0.026 (2)	0.039 (2)	0.033 (2)	−0.0042 (16)	0.0051 (15)	−0.0017 (18)
O5	0.032 (2)	0.033 (2)	0.0204 (17)	−0.0013 (19)	−0.0038 (17)	0.0014 (15)
O6	0.050 (2)	0.0195 (18)	0.030 (2)	−0.0041 (19)	0.003 (2)	0.0057 (15)
O7W	0.037 (2)	0.026 (2)	0.039 (2)	0.0002 (19)	0.0000 (19)	0.0008 (17)
Na1	0.0320 (11)	0.0309 (11)	0.0276 (11)	−0.0076 (10)	−0.0022 (10)	0.0050 (9)
Na2	0.0282 (11)	0.0319 (12)	0.0355 (12)	−0.0040 (9)	−0.0018 (10)	0.0061 (10)
S1	0.0246 (6)	0.0272 (6)	0.0193 (6)	−0.0005 (6)	0.0002 (6)	0.0011 (5)
S2	0.0237 (6)	0.0235 (6)	0.0195 (6)	−0.0003 (6)	0.0000 (6)	0.0011 (5)
Cl1	0.0539 (11)	0.135 (2)	0.0328 (9)	−0.0077 (13)	0.0146 (9)	−0.0199 (11)
Cl2	0.0530 (10)	0.0954 (15)	0.0317 (8)	0.0015 (11)	0.0123 (8)	0.0159 (9)
Br1	0.0294 (3)	0.0519 (4)	0.0323 (3)	−0.0022 (3)	−0.0069 (3)	0.0015 (3)
Br2	0.0297 (3)	0.0512 (4)	0.0385 (3)	−0.0043 (3)	−0.0080 (3)	0.0075 (3)

Geometric parameters (Å, º) top

C1—C6	1.389 (8)	O2—S1	1.446 (4)
C1—C2	1.392 (8)	O2—Na1	2.311 (4)
C1—S1	1.764 (5)	O3W—Na1ⁱⁱ	2.433 (5)
C2—C3	1.387 (9)	O3W—Na1	2.458 (5)
C2—H2	0.9300	O3W—H31	0.82 (5)
C3—C4	1.384 (10)	O3W—H32	0.82 (5)
C3—H3	0.9300	O4W—Na2ⁱⁱ	2.448 (5)
C4—C5	1.373 (10)	O4W—Na1	2.502 (5)
C4—Cl1	1.733 (6)	O4W—H41	0.82 (5)
C5—C6	1.370 (8)	O4W—H42	0.82 (5)
C5—H5	0.9300	O5—S2	1.448 (4)
C6—H6	0.9300	O5—Na1ⁱⁱⁱ	2.453 (4)
C7—C8	1.363 (7)	O5—Na2^iv	2.474 (4)
C7—C12	1.387 (7)	O6—S2	1.440 (4)
C7—S2	1.783 (5)	O6—Na2	2.414 (4)
C8—C9	1.392 (8)	O7W—Na2	2.417 (5)
C8—H8	0.9300	O7W—Na2^v	2.425 (5)
C9—C10	1.368 (9)	O7W—H71	0.82 (5)
C9—H9	0.9300	O7W—H72	0.82 (5)
C10—C11	1.348 (9)	Na1—O1ⁱⁱ	2.420 (4)
C10—Cl2	1.738 (6)	Na1—O3Wⁱ	2.433 (5)
C11—C12	1.396 (9)	Na1—O5^vi	2.453 (4)
C11—H11	0.9300	Na1—Na2ⁱⁱ	3.321 (3)
C12—H12	0.9300	Na1—Na1ⁱ	4.065 (3)
N1—S1	1.574 (5)	Na1—Na1ⁱⁱ	4.065 (3)
N1—Br1	1.885 (4)	Na2—O7W^iv	2.425 (5)
N2—S2	1.579 (4)	Na2—O4Wⁱ	2.448 (5)
N2—Br2	1.896 (4)	Na2—O5^v	2.474 (4)
O1—S1	1.450 (4)	Na2—Na1ⁱ	3.321 (3)
O1—Na1ⁱ	2.420 (4)	Na2—Na2^iv	4.143 (3)
O1—Na2	2.495 (4)	Na2—Na2^v	4.143 (3)

C6—C1—C2	120.2 (5)	O3Wⁱ—Na1—Na2ⁱⁱ	106.53 (13)
C6—C1—S1	120.8 (4)	O5^vi—Na1—Na2ⁱⁱ	47.90 (10)
C2—C1—S1	119.0 (4)	O3W—Na1—Na2ⁱⁱ	115.51 (13)
C3—C2—C1	119.8 (6)	O4W—Na1—Na2ⁱⁱ	47.19 (11)
C3—C2—H2	120.1	O2—Na1—Na1ⁱ	59.27 (12)
C1—C2—H2	120.1	O1ⁱⁱ—Na1—Na1ⁱ	110.07 (13)
C4—C3—C2	119.0 (7)	O3Wⁱ—Na1—Na1ⁱ	33.98 (11)
C4—C3—H3	120.5	O5^vi—Na1—Na1ⁱ	144.99 (13)
C2—C3—H3	120.5	O3W—Na1—Na1ⁱ	130.49 (14)
C5—C4—C3	121.1 (6)	O4W—Na1—Na1ⁱ	69.12 (10)
C5—C4—Cl1	120.0 (6)	Na2ⁱⁱ—Na1—Na1ⁱ	113.08 (8)
C3—C4—Cl1	118.9 (6)	O2—Na1—Na1ⁱⁱ	104.32 (15)
C6—C5—C4	120.4 (6)	O1ⁱⁱ—Na1—Na1ⁱⁱ	75.93 (11)
C6—C5—H5	119.8	O3Wⁱ—Na1—Na1ⁱⁱ	88.71 (14)
C4—C5—H5	119.8	O5^vi—Na1—Na1ⁱⁱ	102.68 (11)
C5—C6—C1	119.5 (6)	O3W—Na1—Na1ⁱⁱ	33.58 (10)
C5—C6—H6	120.2	O4W—Na1—Na1ⁱⁱ	154.36 (13)
C1—C6—H6	120.2	Na2ⁱⁱ—Na1—Na1ⁱⁱ	116.84 (8)
C8—C7—C12	121.0 (5)	Na1ⁱ—Na1—Na1ⁱⁱ	112.28 (11)
C8—C7—S2	121.2 (4)	O6—Na2—O7W	99.72 (16)
C12—C7—S2	117.8 (4)	O6—Na2—O7W^iv	88.60 (15)
C7—C8—C9	119.4 (6)	O7W—Na2—O7W^iv	114.21 (13)
C7—C8—H8	120.3	O6—Na2—O4Wⁱ	94.98 (16)
C9—C8—H8	120.3	O7W—Na2—O4Wⁱ	158.08 (16)
C10—C9—C8	119.3 (6)	O7W^iv—Na2—O4Wⁱ	82.15 (15)
C10—C9—H9	120.4	O6—Na2—O5^v	170.44 (17)
C8—C9—H9	120.4	O7W—Na2—O5^v	86.71 (15)
C11—C10—C9	122.0 (6)	O7W^iv—Na2—O5^v	82.29 (15)
C11—C10—Cl2	119.5 (5)	O4Wⁱ—Na2—O5^v	80.98 (14)
C9—C10—Cl2	118.4 (5)	O6—Na2—O1	110.10 (15)
C10—C11—C12	119.5 (6)	O7W—Na2—O1	80.45 (15)
C10—C11—H11	120.3	O7W^iv—Na2—O1	154.57 (17)
C12—C11—H11	120.3	O4Wⁱ—Na2—O1	79.27 (14)
C7—C12—C11	118.8 (6)	O5^v—Na2—O1	77.79 (14)
C7—C12—H12	120.6	O6—Na2—Na1ⁱ	134.52 (13)
C11—C12—H12	120.6	O7W—Na2—Na1ⁱ	110.29 (12)
S1—N1—Br1	111.2 (3)	O7W^iv—Na2—Na1ⁱ	108.04 (13)
S2—N2—Br2	109.6 (2)	O4Wⁱ—Na2—Na1ⁱ	48.57 (11)
S1—O1—Na1ⁱ	124.5 (2)	O5^v—Na2—Na1ⁱ	47.35 (10)
S1—O1—Na2	145.9 (2)	O1—Na2—Na1ⁱ	46.54 (10)
Na1ⁱ—O1—Na2	84.99 (14)	O6—Na2—Na2^iv	61.57 (11)
S1—O2—Na1	145.0 (3)	O7W—Na2—Na2^iv	130.01 (14)
Na1ⁱⁱ—O3W—Na1	112.44 (17)	O4Wⁱ—Na2—Na2^iv	71.51 (10)
Na2ⁱⁱ—O4W—Na1	84.24 (14)	O5^v—Na2—Na2^iv	108.88 (13)
S2—O5—Na1ⁱⁱⁱ	145.1 (2)	O1—Na2—Na2^iv	148.22 (12)
S2—O5—Na2^iv	128.6 (2)	Na1ⁱ—Na2—Na2^iv	114.96 (8)
Na1ⁱⁱⁱ—O5—Na2^iv	84.75 (14)	O6—Na2—Na2^v	112.02 (14)
S2—O6—Na2	126.9 (2)	O7W^iv—Na2—Na2^v	85.34 (14)
Na2—O7W—Na2^v	117.67 (17)	O4Wⁱ—Na2—Na2^v	149.90 (14)
O2—Na1—O1ⁱⁱ	168.85 (17)	O5^v—Na2—Na2^v	70.25 (11)
O2—Na1—O3Wⁱ	87.76 (16)	O1—Na2—Na2^v	102.39 (11)
O1ⁱⁱ—Na1—O3Wⁱ	81.10 (15)	Na1ⁱ—Na2—Na2^v	111.32 (8)
O2—Na1—O5^vi	110.88 (16)	Na2^iv—Na2—Na2^v	109.12 (11)
O1ⁱⁱ—Na1—O5^vi	79.65 (14)	O2—S1—O1	115.1 (2)
O3Wⁱ—Na1—O5^vi	154.43 (17)	O2—S1—N1	115.6 (3)
O2—Na1—O3W	90.50 (17)	O1—S1—N1	104.1 (2)
O1ⁱⁱ—Na1—O3W	95.20 (15)	O2—S1—C1	104.9 (2)
O3Wⁱ—Na1—O3W	119.04 (13)	O1—S1—C1	107.9 (2)
O5^vi—Na1—O3W	79.47 (15)	N1—S1—C1	109.1 (2)
O2—Na1—O4W	98.09 (16)	O6—S2—O5	115.2 (2)
O1ⁱⁱ—Na1—O4W	79.67 (14)	O6—S2—N2	115.8 (3)
O3Wⁱ—Na1—O4W	79.78 (15)	O5—S2—N2	104.6 (2)
O5^vi—Na1—O4W	80.34 (14)	O6—S2—C7	106.2 (2)
O3W—Na1—O4W	159.76 (16)	O5—S2—C7	107.0 (2)
O2—Na1—Na2ⁱⁱ	136.25 (15)	N2—S2—C7	107.5 (2)
O1ⁱⁱ—Na1—Na2ⁱⁱ	48.47 (11)

C6—C1—C2—C3	0.9 (10)	Na2^v—O7W—Na2—Na1ⁱ	−97.92 (19)
S1—C1—C2—C3	179.4 (5)	Na2^v—O7W—Na2—Na2^iv	56.0 (2)
C1—C2—C3—C4	−0.4 (11)	S1—O1—Na2—O6	74.8 (4)
C2—C3—C4—C5	0.0 (10)	Na1ⁱ—O1—Na2—O6	−132.98 (15)
C2—C3—C4—Cl1	178.3 (5)	S1—O1—Na2—O7W	−22.1 (4)
C3—C4—C5—C6	−0.1 (10)	Na1ⁱ—O1—Na2—O7W	130.08 (15)
Cl1—C4—C5—C6	−178.4 (5)	S1—O1—Na2—O7W^iv	−150.0 (4)
C4—C5—C6—C1	0.6 (10)	Na1ⁱ—O1—Na2—O7W^iv	2.2 (4)
C2—C1—C6—C5	−1.0 (9)	S1—O1—Na2—O4Wⁱ	166.2 (4)
S1—C1—C6—C5	−179.5 (5)	Na1ⁱ—O1—Na2—O4Wⁱ	−41.57 (13)
C12—C7—C8—C9	0.1 (9)	S1—O1—Na2—O5^v	−110.8 (4)
S2—C7—C8—C9	179.3 (5)	Na1ⁱ—O1—Na2—O5^v	41.41 (14)
C7—C8—C9—C10	0.5 (9)	S1—O1—Na2—Na1ⁱ	−152.2 (5)
C8—C9—C10—C11	−0.7 (10)	S1—O1—Na2—Na2^iv	143.0 (3)
C8—C9—C10—Cl2	177.4 (5)	Na1ⁱ—O1—Na2—Na2^iv	−64.8 (3)
C9—C10—C11—C12	0.3 (10)	S1—O1—Na2—Na2^v	−44.5 (4)
Cl2—C10—C11—C12	−177.8 (5)	Na1ⁱ—O1—Na2—Na2^v	107.73 (12)
C8—C7—C12—C11	−0.4 (10)	Na1—O2—S1—O1	−64.3 (6)
S2—C7—C12—C11	−179.7 (5)	Na1—O2—S1—N1	57.1 (6)
C10—C11—C12—C7	0.3 (10)	Na1—O2—S1—C1	177.3 (5)
S1—O2—Na1—O1ⁱⁱ	41.3 (13)	Na1ⁱ—O1—S1—O2	4.2 (4)
S1—O2—Na1—O3Wⁱ	39.5 (5)	Na2—O1—S1—O2	149.9 (4)
S1—O2—Na1—O5^vi	−158.4 (5)	Na1ⁱ—O1—S1—N1	−123.3 (3)
S1—O2—Na1—O3W	−79.5 (5)	Na2—O1—S1—N1	22.4 (5)
S1—O2—Na1—O4W	118.9 (5)	Na1ⁱ—O1—S1—C1	120.9 (3)
S1—O2—Na1—Na2ⁱⁱ	151.3 (4)	Na2—O1—S1—C1	−93.4 (4)
S1—O2—Na1—Na1ⁱ	59.1 (5)	Br1—N1—S1—O2	56.7 (3)
S1—O2—Na1—Na1ⁱⁱ	−48.6 (5)	Br1—N1—S1—O1	−176.1 (2)
Na1ⁱⁱ—O3W—Na1—O2	115.7 (2)	Br1—N1—S1—C1	−61.1 (3)
Na1ⁱⁱ—O3W—Na1—O1ⁱⁱ	−54.67 (19)	C6—C1—S1—O2	−178.1 (5)
Na1ⁱⁱ—O3W—Na1—O3Wⁱ	28.02 (19)	C2—C1—S1—O2	3.5 (6)
Na1ⁱⁱ—O3W—Na1—O5^vi	−133.1 (2)	C6—C1—S1—O1	58.8 (5)
Na1ⁱⁱ—O3W—Na1—O4W	−128.8 (4)	C2—C1—S1—O1	−119.7 (5)
Na1ⁱⁱ—O3W—Na1—Na2ⁱⁱ	−100.70 (17)	C6—C1—S1—N1	−53.7 (5)
Na1ⁱⁱ—O3W—Na1—Na1ⁱ	67.4 (2)	C2—C1—S1—N1	127.8 (5)
Na2ⁱⁱ—O4W—Na1—O2	149.64 (15)	Na2—O6—S2—O5	−74.1 (4)
Na2ⁱⁱ—O4W—Na1—O1ⁱⁱ	−41.42 (13)	Na2—O6—S2—N2	48.4 (4)
Na2ⁱⁱ—O4W—Na1—O3Wⁱ	−124.13 (15)	Na2—O6—S2—C7	167.6 (3)
Na2ⁱⁱ—O4W—Na1—O5^vi	39.70 (13)	Na1ⁱⁱⁱ—O5—S2—O6	170.2 (4)
Na2ⁱⁱ—O4W—Na1—O3W	35.4 (5)	Na2^iv—O5—S2—O6	10.4 (4)
Na2ⁱⁱ—O4W—Na1—Na1ⁱ	−157.71 (13)	Na1ⁱⁱⁱ—O5—S2—N2	41.9 (5)
Na2ⁱⁱ—O4W—Na1—Na1ⁱⁱ	−59.5 (3)	Na2^iv—O5—S2—N2	−117.9 (3)
S2—O6—Na2—O7W	−66.0 (3)	Na1ⁱⁱⁱ—O5—S2—C7	−72.0 (4)
S2—O6—Na2—O7W^iv	48.3 (3)	Na2^iv—O5—S2—C7	128.2 (3)
S2—O6—Na2—O4Wⁱ	130.3 (3)	Br2—N2—S2—O6	55.0 (3)
S2—O6—Na2—O1	−149.4 (3)	Br2—N2—S2—O5	−177.0 (2)
S2—O6—Na2—Na1ⁱ	162.5 (2)	Br2—N2—S2—C7	−63.5 (3)
S2—O6—Na2—Na2^iv	64.4 (3)	C8—C7—S2—O6	13.9 (6)
S2—O6—Na2—Na2^v	−36.1 (3)	C12—C7—S2—O6	−166.9 (5)
Na2^v—O7W—Na2—O6	116.8 (2)	C8—C7—S2—O5	−109.7 (5)
Na2^v—O7W—Na2—O7W^iv	23.96 (18)	C12—C7—S2—O5	69.6 (5)
Na2^v—O7W—Na2—O4Wⁱ	−111.8 (4)	C8—C7—S2—N2	138.4 (5)
Na2^v—O7W—Na2—O5^v	−56.06 (19)	C12—C7—S2—N2	−42.3 (6)
Na2^v—O7W—Na2—O1	−134.2 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H31···Br1	0.82 (4)	2.81 (5)	3.610 (4)	167 (6)
O3W—H32···N2^vi	0.82 (5)	2.08 (4)	2.875 (6)	166 (5)
O4W—H41···N2^vii	0.82 (4)	2.14 (5)	2.911 (6)	158 (4)
O4W—H42···O7W^vii	0.82 (4)	2.46 (4)	3.202 (6)	152 (5)
O7W—H71···Br2	0.82 (4)	2.62 (5)	3.392 (4)	157 (6)
O7W—H72···N1	0.82 (4)	2.02 (4)	2.840 (6)	174 (5)
C2—H2···Br2^vii	0.93	2.85	3.657 (6)	146

Symmetry codes: (vi) x+1, y+1, z; (vii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	Na⁺.C₆H₄BrClNO₂S⁻.1.5H₂O
M_r	319.54
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	300
a, b, c (Å)	6.7510 (7), 10.495 (1), 30.286 (3)
V (Å³)	2145.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.3
Crystal size (mm)	0.52 × 0.32 × 0.11

Data collection
Diffractometer	Xcalibur System, Oxford Diffraction
Absorption correction	Analytical (Clark & Reid, 1995)
T_min, T_max	0.186, 0.543
No. of measured, independent and observed [I > 2σ(I)] reflections	13453, 4156, 3782
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.103, 1.06
No. of reflections	4156
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)	0.51, −0.63
Absolute structure	Flack (1983), 1739 Friedel Pairs
Absolute structure parameter	0.025 (12)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), Diamond (Brandenburg, 2002), SHELXL97, PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H31···Br1	0.82 (4)	2.81 (5)	3.610 (4)	167 (6)
O3W—H32···N2ⁱ	0.82 (5)	2.08 (4)	2.875 (6)	166 (5)
O4W—H41···N2ⁱⁱ	0.82 (4)	2.14 (5)	2.911 (6)	158 (4)
O4W—H42···O7Wⁱⁱ	0.82 (4)	2.46 (4)	3.202 (6)	152 (5)
O7W—H71···Br2	0.82 (4)	2.62 (5)	3.392 (4)	157 (6)
O7W—H72···N1	0.82 (4)	2.02 (4)	2.840 (6)	174 (5)
C2—H2···Br2ⁱⁱ	0.9300	2.8500	3.657 (6)	146.00

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page