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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024531/bt2373sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024531/bt2373Isup2.hkl
Contains datablock I

CCDC reference: 614774

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](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.

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.

Structure description 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.

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).

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 m3
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 mm1
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)
Graphite monochromatorRint = 0.043
Rotation method data acquisition using ω and phi scansθmax = 26.0°, θmin = 5.1°
Absorption correction: analytical
(Clark & Reid, 1995)
h = 85
Tmin = 0.186, Tmax = 0.543k = 1212
13453 measured reflectionsl = 3637
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 Å3
280 parametersΔρmin = 0.63 e Å3
9 restraintsAbsolute structure: Flack (1983), 1739 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure 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 mm1
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
4156 independent reflections
Absorption correction: analytical
(Clark & Reid, 1995)
3782 reflections with I > 2σ(I)
Tmin = 0.186, Tmax = 0.543Rint = 0.043
13453 measured 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 Å3
S = 1.06Δρmin = 0.63 e Å3
4156 reflectionsAbsolute structure: Flack (1983), 1739 Friedel Pairs
280 parametersAbsolute 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
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)
H50.01440.04170.21240.052*
C60.1412 (9)0.0129 (6)0.15574 (18)0.0340 (14)
H60.14610.06760.14290.041*
C70.2985 (8)0.4278 (5)0.13144 (16)0.0223 (10)
C80.3727 (9)0.3308 (6)0.15638 (19)0.0327 (13)
H80.36970.24750.14590.039*
C90.4532 (9)0.3576 (7)0.1977 (2)0.0391 (14)
H90.50530.29250.21500.047*
C100.4546 (9)0.4807 (7)0.2125 (2)0.0388 (15)
C110.3822 (10)0.5776 (7)0.1881 (2)0.0415 (16)
H110.38560.66050.19900.050*
C120.3020 (10)0.5526 (5)0.1466 (2)0.0378 (13)
H120.25190.61840.12930.045*
N10.4811 (6)0.0033 (5)0.08062 (15)0.0296 (10)
N20.0030 (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*
O50.3324 (6)0.4527 (4)0.04617 (11)0.0285 (8)
O60.1679 (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)
S20.1963 (2)0.39892 (11)0.07809 (4)0.0222 (2)
Cl10.0412 (3)0.1656 (3)0.26874 (6)0.0739 (7)
Cl20.5467 (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, º) 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—Na1i97.92 (19)
S1—C1—C2—C3179.4 (5)Na2v—O7W—Na2—Na2iv56.0 (2)
C1—C2—C3—C40.4 (11)S1—O1—Na2—O674.8 (4)
C2—C3—C4—C50.0 (10)Na1i—O1—Na2—O6132.98 (15)
C2—C3—C4—Cl1178.3 (5)S1—O1—Na2—O7W22.1 (4)
C3—C4—C5—C60.1 (10)Na1i—O1—Na2—O7W130.08 (15)
Cl1—C4—C5—C6178.4 (5)S1—O1—Na2—O7Wiv150.0 (4)
C4—C5—C6—C10.6 (10)Na1i—O1—Na2—O7Wiv2.2 (4)
C2—C1—C6—C51.0 (9)S1—O1—Na2—O4Wi166.2 (4)
S1—C1—C6—C5179.5 (5)Na1i—O1—Na2—O4Wi41.57 (13)
C12—C7—C8—C90.1 (9)S1—O1—Na2—O5v110.8 (4)
S2—C7—C8—C9179.3 (5)Na1i—O1—Na2—O5v41.41 (14)
C7—C8—C9—C100.5 (9)S1—O1—Na2—Na1i152.2 (5)
C8—C9—C10—C110.7 (10)S1—O1—Na2—Na2iv143.0 (3)
C8—C9—C10—Cl2177.4 (5)Na1i—O1—Na2—Na2iv64.8 (3)
C9—C10—C11—C120.3 (10)S1—O1—Na2—Na2v44.5 (4)
Cl2—C10—C11—C12177.8 (5)Na1i—O1—Na2—Na2v107.73 (12)
C8—C7—C12—C110.4 (10)Na1—O2—S1—O164.3 (6)
S2—C7—C12—C11179.7 (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—O5vi158.4 (5)Na1i—O1—S1—N1123.3 (3)
S1—O2—Na1—O3W79.5 (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—C193.4 (4)
S1—O2—Na1—Na1i59.1 (5)Br1—N1—S1—O256.7 (3)
S1—O2—Na1—Na1ii48.6 (5)Br1—N1—S1—O1176.1 (2)
Na1ii—O3W—Na1—O2115.7 (2)Br1—N1—S1—C161.1 (3)
Na1ii—O3W—Na1—O1ii54.67 (19)C6—C1—S1—O2178.1 (5)
Na1ii—O3W—Na1—O3Wi28.02 (19)C2—C1—S1—O23.5 (6)
Na1ii—O3W—Na1—O5vi133.1 (2)C6—C1—S1—O158.8 (5)
Na1ii—O3W—Na1—O4W128.8 (4)C2—C1—S1—O1119.7 (5)
Na1ii—O3W—Na1—Na2ii100.70 (17)C6—C1—S1—N153.7 (5)
Na1ii—O3W—Na1—Na1i67.4 (2)C2—C1—S1—N1127.8 (5)
Na2ii—O4W—Na1—O2149.64 (15)Na2—O6—S2—O574.1 (4)
Na2ii—O4W—Na1—O1ii41.42 (13)Na2—O6—S2—N248.4 (4)
Na2ii—O4W—Na1—O3Wi124.13 (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—Na1i157.71 (13)Na1iii—O5—S2—N241.9 (5)
Na2ii—O4W—Na1—Na1ii59.5 (3)Na2iv—O5—S2—N2117.9 (3)
S2—O6—Na2—O7W66.0 (3)Na1iii—O5—S2—C772.0 (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—O1149.4 (3)Br2—N2—S2—O5177.0 (2)
S2—O6—Na2—Na1i162.5 (2)Br2—N2—S2—C763.5 (3)
S2—O6—Na2—Na2iv64.4 (3)C8—C7—S2—O613.9 (6)
S2—O6—Na2—Na2v36.1 (3)C12—C7—S2—O6166.9 (5)
Na2v—O7W—Na2—O6116.8 (2)C8—C7—S2—O5109.7 (5)
Na2v—O7W—Na2—O7Wiv23.96 (18)C12—C7—S2—O569.6 (5)
Na2v—O7W—Na2—O4Wi111.8 (4)C8—C7—S2—N2138.4 (5)
Na2v—O7W—Na2—O5v56.06 (19)C12—C7—S2—N242.3 (6)
Na2v—O7W—Na2—O1134.2 (2)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y+1/2, z; (iii) x1, y1, z; (iv) x1/2, y1/2, z; (v) x+1/2, y1/2, z; (vi) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) 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.

Experimental details

Crystal data
Chemical formulaNa+.C6H4BrClNO2S.1.5H2O
Mr319.54
Crystal system, space groupOrthorhombic, P212121
Temperature (K)300
a, b, c (Å)6.7510 (7), 10.495 (1), 30.286 (3)
V3)2145.8 (4)
Z8
Radiation typeMo Kα
µ (mm1)4.3
Crystal size (mm)0.52 × 0.32 × 0.11
Data collection
DiffractometerXcalibur System, Oxford Diffraction
Absorption correctionAnalytical
(Clark & Reid, 1995)
Tmin, Tmax0.186, 0.543
No. of measured, independent and
observed [I > 2σ(I)] reflections
13453, 4156, 3782
Rint0.043
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.103, 1.06
No. of reflections4156
No. of parameters280
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.63
Absolute structureFlack (1983), 1739 Friedel Pairs
Absolute structure parameter0.025 (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···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···Br2ii0.93002.85003.657 (6)146.00
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z.
 

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