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Acta Cryst. (2007). E63, m1647-m1648    [ doi:10.1107/S1600536807024531 ]

Sodium N-bromo-4-chlorobenzenesulfonamidate sesquihydrate

B. T. Gowda, J. Kozísek, M. Tokarcík and H. Fuess

Abstract top

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.

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.

Refinement top

H atoms bonded to C were positioned geometrically and refined using a riding model with C—H = 0.93Å and with Uiso(H) = 1.2 Ueq(C). H atoms of water molecules (O3w, O4w, O7w) were visible in difference map and were subsequently treated as riding with Uiso(H) = 1.2 Ueq(O) and with the O—H bond length restrained to 0.82 (2) Å and the H···H distance restrained to 1.35 (2) Å.

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
[Figure 1] 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.
[Figure 2] 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−.1.5H2OF(000) = 1256
Mr = 319.54Dx = 1.978 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2831 reflections
a = 6.7510 (7) Åθ = 2.5–26.4°
b = 10.495 (1) ŵ = 4.3 mm−1
c = 30.286 (3) ÅT = 300 K
V = 2145.8 (4) Å3Block, yellow
Z = 80.52 × 0.32 × 0.11 mm
Data collection top
Xcalibur System, Oxford Diffraction
diffractometer		4156 independent reflections
Radiation source: fine-focus sealed tube3782 reflections with I > 2σ(I)
graphiteRint = 0.043
Rotation method data acquisition using ω and phi scansθmax = 26.0°, θmin = 5.1°
Absorption correction: analytical
(Clark & Reid, 1995)		h = −8→5
Tmin = 0.186, Tmax = 0.543k = −12→12
13453 measured reflectionsl = −36→37
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0395P)2 + 5.8841P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.011
4156 reflectionsΔρmax = 0.51 e Å−3
280 parametersΔρmin = −0.63 e Å−3
9 restraintsAbsolute structure: Flack (1983), 1739 Friedel Pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.025 (12)
Crystal data top
Na+.C6H4BrClNO2S−.1.5H2OV = 2145.8 (4) Å3
Mr = 319.54Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 6.7510 (7) ŵ = 4.3 mm−1
b = 10.495 (1) ÅT = 300 K
c = 30.286 (3) Å0.52 × 0.32 × 0.11 mm
Data collection top
Xcalibur System, Oxford Diffraction
diffractometer		3782 reflections with I > 2σ(I)
Absorption correction: analytical
(Clark & Reid, 1995)		Rint = 0.043
Tmin = 0.186, Tmax = 0.543θmax = 26.0°
13453 measured reflectionsStandard reflections: 0
4156 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Δρmax = 0.51 e Å−3
S = 1.06Δρmin = −0.63 e Å−3
4156 reflectionsAbsolute structure: Flack (1983), 1739 Friedel Pairs
280 parametersFlack 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
xyzUiso*/Ueq
C10.2141 (8)0.1181 (5)0.13313 (16)0.0231 (11)
C20.2041 (11)0.2388 (6)0.1520 (2)0.0425 (15)
H20.25130.30930.13670.051*
C30.1235 (10)0.2537 (8)0.1939 (2)0.0488 (18)
H30.11680.33380.20690.059*
C40.0532 (9)0.1474 (8)0.2159 (2)0.0429 (16)
C50.0622 (10)0.0286 (7)0.1971 (2)0.0433 (16)
H50.0144−0.04170.21240.052*
C60.1412 (9)0.0129 (6)0.15574 (18)0.0340 (14)
H60.1461−0.06760.14290.041*
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)
H8−0.3697−0.24750.14590.039*
C9−0.4532 (9)−0.3576 (7)0.1977 (2)0.0391 (14)
H9−0.5053−0.29250.21500.047*
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)
H11−0.3856−0.66050.19900.050*
C12−0.3020 (10)−0.5526 (5)0.1466 (2)0.0378 (13)
H12−0.2519−0.61840.12930.045*
N10.4811 (6)−0.0033 (5)0.08062 (15)0.0296 (10)
N2−0.0030 (6)−0.4826 (4)0.07372 (14)0.0254 (10)
O10.1630 (6)0.0484 (4)0.05138 (11)0.0298 (9)
O20.3802 (7)0.2285 (4)0.06782 (13)0.0379 (10)
O3W0.8614 (6)0.2759 (4)0.04069 (14)0.0346 (10)
H310.843 (10)0.219 (4)0.0589 (14)0.041*
H320.914 (9)0.337 (4)0.0526 (16)0.041*
O4W0.2557 (6)0.4969 (4)−0.00286 (12)0.0322 (9)
H410.164 (6)0.489 (5)0.0146 (16)0.039*
H420.312 (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)
O7W0.3480 (6)−0.2262 (4)0.03649 (13)0.0341 (9)
H710.344 (10)−0.284 (4)0.0549 (14)0.041*
H720.394 (9)−0.162 (3)0.0481 (16)0.041*
Na10.5364 (3)0.3495 (2)0.01446 (7)0.0302 (5)
Na20.0188 (3)−0.1502 (2)0.01942 (8)0.0319 (5)
S10.3149 (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)
Br10.68840 (9)0.04232 (6)0.119227 (19)0.03784 (16)
Br20.18659 (9)−0.42882 (6)0.11598 (2)0.03978 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.023 (3)0.029 (3)0.017 (2)0.001 (2)0.001 (2)−0.0003 (19)
C20.058 (4)0.033 (3)0.037 (3)0.000 (3)0.008 (3)−0.003 (3)
C30.047 (4)0.055 (4)0.044 (4)−0.008 (3)0.011 (3)−0.017 (3)
C40.019 (3)0.075 (5)0.035 (3)−0.004 (3)0.003 (3)−0.012 (3)
C50.042 (4)0.059 (4)0.029 (3)−0.008 (3)0.005 (3)0.008 (3)
C60.047 (4)0.029 (3)0.026 (3)0.001 (3)0.003 (2)0.004 (2)
C70.019 (2)0.029 (3)0.019 (2)0.004 (2)−0.002 (2)0.0020 (18)
C80.039 (3)0.030 (3)0.029 (3)0.002 (2)0.008 (2)0.001 (2)
C90.031 (3)0.049 (4)0.037 (3)−0.002 (3)0.015 (3)−0.008 (3)
C100.027 (3)0.055 (4)0.034 (3)−0.005 (3)0.006 (3)0.010 (3)
C110.042 (4)0.041 (4)0.042 (4)0.005 (3)0.005 (3)0.014 (3)
C120.039 (3)0.033 (3)0.042 (3)0.003 (3)0.010 (3)0.001 (2)
N10.024 (2)0.035 (3)0.030 (2)0.005 (2)−0.006 (2)−0.006 (2)
N20.024 (2)0.027 (2)0.026 (2)0.0013 (19)0.0013 (18)−0.0009 (18)
O10.030 (2)0.041 (2)0.0191 (17)0.0012 (19)−0.0054 (16)−0.0017 (15)
O20.054 (3)0.027 (2)0.033 (2)−0.0097 (19)0.0062 (19)0.0076 (17)
O3W0.034 (2)0.030 (2)0.040 (2)−0.0001 (18)0.0043 (19)0.0009 (18)
O4W0.026 (2)0.039 (2)0.033 (2)−0.0042 (16)0.0051 (15)−0.0017 (18)
O50.032 (2)0.033 (2)0.0204 (17)−0.0013 (19)−0.0038 (17)0.0014 (15)
O60.050 (2)0.0195 (18)0.030 (2)−0.0041 (19)0.003 (2)0.0057 (15)
O7W0.037 (2)0.026 (2)0.039 (2)0.0002 (19)0.0000 (19)0.0008 (17)
Na10.0320 (11)0.0309 (11)0.0276 (11)−0.0076 (10)−0.0022 (10)0.0050 (9)
Na20.0282 (11)0.0319 (12)0.0355 (12)−0.0040 (9)−0.0018 (10)0.0061 (10)
S10.0246 (6)0.0272 (6)0.0193 (6)−0.0005 (6)0.0002 (6)0.0011 (5)
S20.0237 (6)0.0235 (6)0.0195 (6)−0.0003 (6)0.0000 (6)0.0011 (5)
Cl10.0539 (11)0.135 (2)0.0328 (9)−0.0077 (13)0.0146 (9)−0.0199 (11)
Cl20.0530 (10)0.0954 (15)0.0317 (8)0.0015 (11)0.0123 (8)0.0159 (9)
Br10.0294 (3)0.0519 (4)0.0323 (3)−0.0022 (3)−0.0069 (3)0.0015 (3)
Br20.0297 (3)0.0512 (4)0.0385 (3)−0.0043 (3)−0.0080 (3)0.0075 (3)
Geometric parameters (Å, °) top
C1—C61.389 (8)O2—S11.446 (4)
C1—C21.392 (8)O2—Na12.311 (4)
C1—S11.764 (5)O3W—Na1ii2.433 (5)
C2—C31.387 (9)O3W—Na12.458 (5)
C2—H20.9300O3W—H310.82 (5)
C3—C41.384 (10)O3W—H320.82 (5)
C3—H30.9300O4W—Na2ii2.448 (5)
C4—C51.373 (10)O4W—Na12.502 (5)
C4—Cl11.733 (6)O4W—H410.82 (5)
C5—C61.370 (8)O4W—H420.82 (5)
C5—H50.9300O5—S21.448 (4)
C6—H60.9300O5—Na1iii2.453 (4)
C7—C81.363 (7)O5—Na2iv2.474 (4)
C7—C121.387 (7)O6—S21.440 (4)
C7—S21.783 (5)O6—Na22.414 (4)
C8—C91.392 (8)O7W—Na22.417 (5)
C8—H80.9300O7W—Na2v2.425 (5)
C9—C101.368 (9)O7W—H710.82 (5)
C9—H90.9300O7W—H720.82 (5)
C10—C111.348 (9)Na1—O1ii2.420 (4)
C10—Cl21.738 (6)Na1—O3Wi2.433 (5)
C11—C121.396 (9)Na1—O5vi2.453 (4)
C11—H110.9300Na1—Na2ii3.321 (3)
C12—H120.9300Na1—Na1i4.065 (3)
N1—S11.574 (5)Na1—Na1ii4.065 (3)
N1—Br11.885 (4)Na2—O7Wiv2.425 (5)
N2—S21.579 (4)Na2—O4Wi2.448 (5)
N2—Br21.896 (4)Na2—O5v2.474 (4)
O1—S11.450 (4)Na2—Na1i3.321 (3)
O1—Na1i2.420 (4)Na2—Na2iv4.143 (3)
O1—Na22.495 (4)Na2—Na2v4.143 (3)
C6—C1—C2120.2 (5)O3Wi—Na1—Na2ii106.53 (13)
C6—C1—S1120.8 (4)O5vi—Na1—Na2ii47.90 (10)
C2—C1—S1119.0 (4)O3W—Na1—Na2ii115.51 (13)
C3—C2—C1119.8 (6)O4W—Na1—Na2ii47.19 (11)
C3—C2—H2120.1O2—Na1—Na1i59.27 (12)
C1—C2—H2120.1O1ii—Na1—Na1i110.07 (13)
C4—C3—C2119.0 (7)O3Wi—Na1—Na1i33.98 (11)
C4—C3—H3120.5O5vi—Na1—Na1i144.99 (13)
C2—C3—H3120.5O3W—Na1—Na1i130.49 (14)
C5—C4—C3121.1 (6)O4W—Na1—Na1i69.12 (10)
C5—C4—Cl1120.0 (6)Na2ii—Na1—Na1i113.08 (8)
C3—C4—Cl1118.9 (6)O2—Na1—Na1ii104.32 (15)
C6—C5—C4120.4 (6)O1ii—Na1—Na1ii75.93 (11)
C6—C5—H5119.8O3Wi—Na1—Na1ii88.71 (14)
C4—C5—H5119.8O5vi—Na1—Na1ii102.68 (11)
C5—C6—C1119.5 (6)O3W—Na1—Na1ii33.58 (10)
C5—C6—H6120.2O4W—Na1—Na1ii154.36 (13)
C1—C6—H6120.2Na2ii—Na1—Na1ii116.84 (8)
C8—C7—C12121.0 (5)Na1i—Na1—Na1ii112.28 (11)
C8—C7—S2121.2 (4)O6—Na2—O7W99.72 (16)
C12—C7—S2117.8 (4)O6—Na2—O7Wiv88.60 (15)
C7—C8—C9119.4 (6)O7W—Na2—O7Wiv114.21 (13)
C7—C8—H8120.3O6—Na2—O4Wi94.98 (16)
C9—C8—H8120.3O7W—Na2—O4Wi158.08 (16)
C10—C9—C8119.3 (6)O7Wiv—Na2—O4Wi82.15 (15)
C10—C9—H9120.4O6—Na2—O5v170.44 (17)
C8—C9—H9120.4O7W—Na2—O5v86.71 (15)
C11—C10—C9122.0 (6)O7Wiv—Na2—O5v82.29 (15)
C11—C10—Cl2119.5 (5)O4Wi—Na2—O5v80.98 (14)
C9—C10—Cl2118.4 (5)O6—Na2—O1110.10 (15)
C10—C11—C12119.5 (6)O7W—Na2—O180.45 (15)
C10—C11—H11120.3O7Wiv—Na2—O1154.57 (17)
C12—C11—H11120.3O4Wi—Na2—O179.27 (14)
C7—C12—C11118.8 (6)O5v—Na2—O177.79 (14)
C7—C12—H12120.6O6—Na2—Na1i134.52 (13)
C11—C12—H12120.6O7W—Na2—Na1i110.29 (12)
S1—N1—Br1111.2 (3)O7Wiv—Na2—Na1i108.04 (13)
S2—N2—Br2109.6 (2)O4Wi—Na2—Na1i48.57 (11)
S1—O1—Na1i124.5 (2)O5v—Na2—Na1i47.35 (10)
S1—O1—Na2145.9 (2)O1—Na2—Na1i46.54 (10)
Na1i—O1—Na284.99 (14)O6—Na2—Na2iv61.57 (11)
S1—O2—Na1145.0 (3)O7W—Na2—Na2iv130.01 (14)
Na1ii—O3W—Na1112.44 (17)O4Wi—Na2—Na2iv71.51 (10)
Na2ii—O4W—Na184.24 (14)O5v—Na2—Na2iv108.88 (13)
S2—O5—Na1iii145.1 (2)O1—Na2—Na2iv148.22 (12)
S2—O5—Na2iv128.6 (2)Na1i—Na2—Na2iv114.96 (8)
Na1iii—O5—Na2iv84.75 (14)O6—Na2—Na2v112.02 (14)
S2—O6—Na2126.9 (2)O7Wiv—Na2—Na2v85.34 (14)
Na2—O7W—Na2v117.67 (17)O4Wi—Na2—Na2v149.90 (14)
O2—Na1—O1ii168.85 (17)O5v—Na2—Na2v70.25 (11)
O2—Na1—O3Wi87.76 (16)O1—Na2—Na2v102.39 (11)
O1ii—Na1—O3Wi81.10 (15)Na1i—Na2—Na2v111.32 (8)
O2—Na1—O5vi110.88 (16)Na2iv—Na2—Na2v109.12 (11)
O1ii—Na1—O5vi79.65 (14)O2—S1—O1115.1 (2)
O3Wi—Na1—O5vi154.43 (17)O2—S1—N1115.6 (3)
O2—Na1—O3W90.50 (17)O1—S1—N1104.1 (2)
O1ii—Na1—O3W95.20 (15)O2—S1—C1104.9 (2)
O3Wi—Na1—O3W119.04 (13)O1—S1—C1107.9 (2)
O5vi—Na1—O3W79.47 (15)N1—S1—C1109.1 (2)
O2—Na1—O4W98.09 (16)O6—S2—O5115.2 (2)
O1ii—Na1—O4W79.67 (14)O6—S2—N2115.8 (3)
O3Wi—Na1—O4W79.78 (15)O5—S2—N2104.6 (2)
O5vi—Na1—O4W80.34 (14)O6—S2—C7106.2 (2)
O3W—Na1—O4W159.76 (16)O5—S2—C7107.0 (2)
O2—Na1—Na2ii136.25 (15)N2—S2—C7107.5 (2)
O1ii—Na1—Na2ii48.47 (11)
C6—C1—C2—C30.9 (10)Na2v—O7W—Na2—Na1i−97.92 (19)
S1—C1—C2—C3179.4 (5)Na2v—O7W—Na2—Na2iv56.0 (2)
C1—C2—C3—C4−0.4 (11)S1—O1—Na2—O674.8 (4)
C2—C3—C4—C50.0 (10)Na1i—O1—Na2—O6−132.98 (15)
C2—C3—C4—Cl1178.3 (5)S1—O1—Na2—O7W−22.1 (4)
C3—C4—C5—C6−0.1 (10)Na1i—O1—Na2—O7W130.08 (15)
Cl1—C4—C5—C6−178.4 (5)S1—O1—Na2—O7Wiv−150.0 (4)
C4—C5—C6—C10.6 (10)Na1i—O1—Na2—O7Wiv2.2 (4)
C2—C1—C6—C5−1.0 (9)S1—O1—Na2—O4Wi166.2 (4)
S1—C1—C6—C5−179.5 (5)Na1i—O1—Na2—O4Wi−41.57 (13)
C12—C7—C8—C90.1 (9)S1—O1—Na2—O5v−110.8 (4)
S2—C7—C8—C9179.3 (5)Na1i—O1—Na2—O5v41.41 (14)
C7—C8—C9—C100.5 (9)S1—O1—Na2—Na1i−152.2 (5)
C8—C9—C10—C11−0.7 (10)S1—O1—Na2—Na2iv143.0 (3)
C8—C9—C10—Cl2177.4 (5)Na1i—O1—Na2—Na2iv−64.8 (3)
C9—C10—C11—C120.3 (10)S1—O1—Na2—Na2v−44.5 (4)
Cl2—C10—C11—C12−177.8 (5)Na1i—O1—Na2—Na2v107.73 (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—N157.1 (6)
C10—C11—C12—C70.3 (10)Na1—O2—S1—C1177.3 (5)
S1—O2—Na1—O1ii41.3 (13)Na1i—O1—S1—O24.2 (4)
S1—O2—Na1—O3Wi39.5 (5)Na2—O1—S1—O2149.9 (4)
S1—O2—Na1—O5vi−158.4 (5)Na1i—O1—S1—N1−123.3 (3)
S1—O2—Na1—O3W−79.5 (5)Na2—O1—S1—N122.4 (5)
S1—O2—Na1—O4W118.9 (5)Na1i—O1—S1—C1120.9 (3)
S1—O2—Na1—Na2ii151.3 (4)Na2—O1—S1—C1−93.4 (4)
S1—O2—Na1—Na1i59.1 (5)Br1—N1—S1—O256.7 (3)
S1—O2—Na1—Na1ii−48.6 (5)Br1—N1—S1—O1−176.1 (2)
Na1ii—O3W—Na1—O2115.7 (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—O3Wi28.02 (19)C2—C1—S1—O23.5 (6)
Na1ii—O3W—Na1—O5vi−133.1 (2)C6—C1—S1—O158.8 (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—Na1i67.4 (2)C2—C1—S1—N1127.8 (5)
Na2ii—O4W—Na1—O2149.64 (15)Na2—O6—S2—O5−74.1 (4)
Na2ii—O4W—Na1—O1ii−41.42 (13)Na2—O6—S2—N248.4 (4)
Na2ii—O4W—Na1—O3Wi−124.13 (15)Na2—O6—S2—C7167.6 (3)
Na2ii—O4W—Na1—O5vi39.70 (13)Na1iii—O5—S2—O6170.2 (4)
Na2ii—O4W—Na1—O3W35.4 (5)Na2iv—O5—S2—O610.4 (4)
Na2ii—O4W—Na1—Na1i−157.71 (13)Na1iii—O5—S2—N241.9 (5)
Na2ii—O4W—Na1—Na1ii−59.5 (3)Na2iv—O5—S2—N2−117.9 (3)
S2—O6—Na2—O7W−66.0 (3)Na1iii—O5—S2—C7−72.0 (4)
S2—O6—Na2—O7Wiv48.3 (3)Na2iv—O5—S2—C7128.2 (3)
S2—O6—Na2—O4Wi130.3 (3)Br2—N2—S2—O655.0 (3)
S2—O6—Na2—O1−149.4 (3)Br2—N2—S2—O5−177.0 (2)
S2—O6—Na2—Na1i162.5 (2)Br2—N2—S2—C7−63.5 (3)
S2—O6—Na2—Na2iv64.4 (3)C8—C7—S2—O613.9 (6)
S2—O6—Na2—Na2v−36.1 (3)C12—C7—S2—O6−166.9 (5)
Na2v—O7W—Na2—O6116.8 (2)C8—C7—S2—O5−109.7 (5)
Na2v—O7W—Na2—O7Wiv23.96 (18)C12—C7—S2—O569.6 (5)
Na2v—O7W—Na2—O4Wi−111.8 (4)C8—C7—S2—N2138.4 (5)
Na2v—O7W—Na2—O5v−56.06 (19)C12—C7—S2—N2−42.3 (6)
Na2v—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, °) top
D—H···AD—HH···AD···AD—H···A
O3W—H31···Br10.82 (4)2.81 (5)3.610 (4)167 (6)
O3W—H32···N2vi0.82 (5)2.08 (4)2.875 (6)166 (5)
O4W—H41···N2vii0.82 (4)2.14 (5)2.911 (6)158 (4)
O4W—H42···O7Wvii0.82 (4)2.46 (4)3.202 (6)152 (5)
O7W—H71···Br20.82 (4)2.62 (5)3.392 (4)157 (6)
O7W—H72···N10.82 (4)2.02 (4)2.840 (6)174 (5)
C2—H2···Br2vii0.932.853.657 (6)146
Symmetry codes: (vi) x+1, y+1, z; (vii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3W—H31···Br10.82 (4)2.81 (5)3.610 (4)167 (6)
O3W—H32···N2i0.82 (5)2.08 (4)2.875 (6)166 (5)
O4W—H41···N2ii0.82 (4)2.14 (5)2.911 (6)158 (4)
O4W—H42···O7Wii0.82 (4)2.46 (4)3.202 (6)152 (5)
O7W—H71···Br20.82 (4)2.62 (5)3.392 (4)157 (6)
O7W—H72···N10.82 (4)2.02 (4)2.840 (6)174 (5)
C2—H2···Br2ii0.932.853.657 (6)146
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
Acknowledgements top

BTG gratefully thanks the Alexander von Humboldt Foundation, Bonn, Germany for extensions of his research fellowship. JK and MT thank the Grant Agency of the Slovak Republic (grant No. 1/2449/05).

references
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