metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Potassium N-bromo-2-nitro­benzene­sulfonamidate monohydrate

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 4 October 2012; accepted 8 October 2012; online 13 October 2012)

In the title compound, K+·C6H4BrN2O4S·H2O, the K+ ion is hepta-coordinated by two O atoms from two different water mol­ecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzene­sulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzene­sulfonamidate anions. The S—N distance of 1.576 (4) Å is consistent with an S=N double bond. The crystal structure is stabilized by inter­molecular O—H⋯N and O—H⋯Br hydrogen bonds which link the molecules into polymeric layers running parallel to the bc plane.

Related literature

For the preparation of metal salts of N-haloaryl­sulfonamides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]); Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.]). For studies on the effect of substituents and metal ions on the structures of N-haloaryl­sulfonamides, see: George et al. (2000[George, E., Vivekanandan, S. & Sivakumar, K. (2000). Acta Cryst. C56, 1208-1209.]); Gowda et al. (2011a[Gowda, B. T., Foro, S. & Shakuntala, K. (2011a). Acta Cryst. E67, m926.],b[Gowda, B. T., Foro, S. & Shakuntala, K. (2011b). Acta Cryst. E67, m1015.]); Olmstead & Power (1986[Olmstead, M. M. & Power, P. P. (1986). Inorg. Chem. 25, 4057-4058.]). For positioning of water H atoms, see: Nardelli (1999[Nardelli, M. (1999). J. Appl. Cryst. 32, 563-571.]).

[Scheme 1]

Experimental

Crystal data
  • K+·C6H4BrN2O4S·H2O

  • Mr = 337.20

  • Monoclinic, P 21 /c

  • a = 13.034 (2) Å

  • b = 12.815 (2) Å

  • c = 6.7741 (9) Å

  • β = 100.65 (1)°

  • V = 1112.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.27 mm−1

  • T = 293 K

  • 0.48 × 0.48 × 0.24 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.234, Tmax = 0.428

  • 3896 measured reflections

  • 2236 independent reflections

  • 1847 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.145

  • S = 1.06

  • 2236 reflections

  • 152 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.79 e Å−3

  • Δρmin = −1.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H51⋯N1i 0.84 (2) 2.13 (3) 2.926 (5) 157 (5)
O5—H52⋯Br1ii 0.84 (2) 2.85 (4) 3.509 (4) 137 (4)
Symmetry codes: (i) -x, -y, -z+1; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the present work, to explore the effect of substituents on the crystal structures of metal salts of N-haloarylsulfonamidates (George et al., 2000; Gowda et al., 2011a,b; Olmstead & Power, 1986), the crystal structure of potassium N-bromo-2-nitro-benzenesulfonamidate monohydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chloro-benzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011a), potassium N-bromo-2-methyl-benzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), and sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).

In the title compound (I), the K+ ion is hepta coordinated by two O atoms from two different water molecules, three sulfonyl O atoms from three N-bromo-2-nitro-benzenesulfonamidate anions and two nitro O atoms from two N-bromo-2-nitro-benzenesulfonamidate anions (Fig 2.). This is in contrast to K+ ion hepta coordination by three O atoms from water molecules and by four sulfonyl O atoms of three N-bromo-2-chloro-benzenesulfonamide anions in (II) and three N-bromo-2-methyl-benzenesulfonamide anions in (III).

The S—N distance of 1.576 (4) Å in (I) is consistent with an S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II) and 1.577 (5) Å in (III).

The packing diagram consists of a two-dimensional polymeric layer running parallel to the bc plane (Fig. 2). The molecular packing is stabilized by O5—H51···N1 and O5—H52···Br1 hydrogen bonds (Table 1).

Related literature top

For the preparation of metal salts of N-haloarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006). For studies on the effect of substituents and metal ions on the structures of N-haloarylsulfonamides, see: George et al. (2000); Gowda et al. (2011a,b); Olmstead & Power (1986). For positioning of water H atoms, see: Nardelli (1999).

Experimental top

The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda & Mahadevappa, 1983) and Usha & Gowda (Usha & Gowda, 2006). 2 g of 2-nitrobenzenesulfonamide was dissolved with stirring in 40 ml of 5M KOH at room temperature. The resultant solution was cooled in ice and 4 ml of liquid bromine was added drop wise with constant stirring. The resultant potassium salt of N-bromo-2-nitro-benzenesulfonamidate monohydrate was filtered under suction, washed quickly with a minimum quantity of ice cold water. The purity of the compound was checked by determining its melting point (175–177°C) and estimating, iodometrically, the amount of active bromine present in it. It was further characterized from its infrared spectrum. The characteristic absorptions observed are 3624.3, 3333.0, 3192.2, 2978.1, 2922.2, 2075.4, 1626.0, 1602.9, 1477.5, 1452.4, 1242.2, 1122.6, 1060.9, 937.4, 817.8, 686.7, 640.4, 578.6, 549.6, 524.6 and 470.6 cm-1.

Prism like yellow single crystals of the title compound used in the X-ray diffraction studies were obtained from its aqueous solution at room temperature.

Refinement top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The O-bound H atoms were located in a difference map and were refined with restrained geometry (Nardelli, 1999), viz. O—H distances were restrained to 0.85 (2) Å and the H—H distance was restrained to 1.365 Å, thus leading to the angle of 107°. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom. The residual electron-density features are located in the region of Br1. The highest peak and the deepest hole are 0.80 and 0.84 Å from Br1, respectivily.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme for the asymmetric unit and extended to show the coordination geometry for the K+ ion. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Bridging of potassium cations, N-bromo-2-nitro-benzenesulfonamidate anions and water molecules in the structure of the title compound.
[Figure 3] Fig. 3. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
Potassium N-bromo-2-nitrobenzenesulfonamidate monohydrate top
Crystal data top
K+·C6H4BrN2O4S·H2OF(000) = 664
Mr = 337.20Dx = 2.014 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2399 reflections
a = 13.034 (2) Åθ = 3.1–27.8°
b = 12.815 (2) ŵ = 4.27 mm1
c = 6.7741 (9) ÅT = 293 K
β = 100.65 (1)°Prism, yellow
V = 1112.0 (3) Å30.48 × 0.48 × 0.24 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
2236 independent reflections
Radiation source: fine-focus sealed tube1847 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Rotation method data acquisition using ω scans.θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1612
Tmin = 0.234, Tmax = 0.428k = 1611
3896 measured reflectionsl = 68
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0909P)2 + 0.1082P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
2236 reflectionsΔρmax = 0.79 e Å3
152 parametersΔρmin = 1.21 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.082 (5)
Crystal data top
K+·C6H4BrN2O4S·H2OV = 1112.0 (3) Å3
Mr = 337.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.034 (2) ŵ = 4.27 mm1
b = 12.815 (2) ÅT = 293 K
c = 6.7741 (9) Å0.48 × 0.48 × 0.24 mm
β = 100.65 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
2236 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1847 reflections with I > 2σ(I)
Tmin = 0.234, Tmax = 0.428Rint = 0.042
3896 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0533 restraints
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.79 e Å3
2236 reflectionsΔρmin = 1.21 e Å3
152 parameters
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
C10.2873 (3)0.0123 (3)0.3340 (6)0.0272 (9)
C20.3529 (3)0.0693 (3)0.3079 (6)0.0271 (8)
C30.4505 (3)0.0546 (4)0.2573 (6)0.0346 (10)
H30.49300.11130.24300.042*
C40.4833 (4)0.0463 (4)0.2286 (7)0.0419 (11)
H40.54880.05830.19750.050*
C50.4173 (4)0.1291 (4)0.2469 (7)0.0425 (11)
H50.43770.19660.22210.051*
C60.3214 (4)0.1127 (3)0.3015 (7)0.0368 (10)
H60.27910.16950.31670.044*
Br10.24804 (4)0.10055 (4)0.78959 (7)0.0470 (3)
K10.09562 (9)0.13045 (8)0.88211 (15)0.0418 (3)
N10.1510 (3)0.1035 (3)0.5411 (6)0.0384 (9)
N20.3214 (3)0.1792 (3)0.3257 (5)0.0316 (8)
O10.1685 (3)0.0941 (2)0.5295 (5)0.0395 (8)
O20.0840 (3)0.0085 (2)0.2371 (5)0.0442 (8)
O30.2363 (3)0.2061 (3)0.2308 (5)0.0454 (8)
O40.3826 (3)0.2369 (3)0.4304 (6)0.0520 (9)
S10.16307 (8)0.00155 (7)0.41728 (15)0.0294 (3)
O50.0180 (3)0.2758 (3)0.6363 (6)0.0494 (9)
H510.066 (3)0.240 (3)0.566 (7)0.059*
H520.044 (4)0.326 (3)0.689 (8)0.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.027 (2)0.0276 (19)0.0253 (18)0.0017 (17)0.0016 (16)0.0018 (16)
C20.026 (2)0.0279 (18)0.0271 (18)0.0015 (17)0.0053 (16)0.0028 (16)
C30.032 (2)0.042 (2)0.032 (2)0.000 (2)0.0101 (18)0.0059 (19)
C40.036 (3)0.054 (3)0.038 (2)0.014 (2)0.015 (2)0.001 (2)
C50.047 (3)0.036 (2)0.045 (3)0.020 (2)0.012 (2)0.003 (2)
C60.041 (3)0.030 (2)0.040 (2)0.0028 (19)0.009 (2)0.0020 (18)
Br10.0516 (4)0.0461 (4)0.0432 (4)0.0034 (2)0.0087 (2)0.0096 (2)
K10.0378 (6)0.0498 (6)0.0380 (5)0.0041 (5)0.0076 (4)0.0024 (5)
N10.036 (2)0.034 (2)0.047 (2)0.0106 (16)0.0122 (19)0.0010 (16)
N20.032 (2)0.0279 (17)0.0369 (18)0.0005 (15)0.0100 (16)0.0052 (15)
O10.046 (2)0.0313 (15)0.0463 (18)0.0007 (13)0.0206 (16)0.0100 (13)
O20.0293 (17)0.0527 (19)0.0465 (18)0.0035 (15)0.0039 (15)0.0014 (16)
O30.045 (2)0.0325 (17)0.0564 (19)0.0096 (15)0.0025 (16)0.0113 (15)
O40.048 (2)0.0379 (17)0.070 (2)0.0146 (16)0.0112 (19)0.0130 (17)
S10.0254 (6)0.0274 (5)0.0360 (5)0.0033 (4)0.0069 (4)0.0032 (4)
O50.043 (2)0.0443 (19)0.063 (2)0.0011 (16)0.0146 (18)0.0010 (17)
Geometric parameters (Å, º) top
C1—C21.383 (6)K1—O2ii2.806 (3)
C1—C61.391 (5)K1—O3iii2.877 (4)
C1—S11.815 (4)K1—O2iii3.018 (4)
C2—C31.390 (6)K1—O3i3.081 (4)
C2—N21.479 (5)K1—H513.06 (5)
C3—C41.386 (6)N1—S11.576 (4)
C3—H30.9300N2—O41.215 (5)
C4—C51.385 (7)N2—O31.225 (5)
C4—H40.9300O1—S11.437 (3)
C5—C61.384 (7)O2—S11.448 (3)
C5—H50.9300O2—K1ii2.806 (3)
C6—H60.9300O2—K1iv3.018 (4)
Br1—N11.910 (4)O3—K1iv2.877 (4)
Br1—K13.6829 (12)O3—K1v3.081 (4)
K1—O52.743 (4)O5—K1v2.746 (4)
K1—O5i2.746 (4)O5—H510.844 (19)
K1—O12.768 (3)O5—H520.841 (19)
C2—C1—C6117.1 (4)O2iii—K1—O3i141.88 (10)
C2—C1—S1126.2 (3)O5—K1—Br1133.65 (9)
C6—C1—S1116.7 (3)O5i—K1—Br1145.95 (9)
C1—C2—C3123.0 (4)O1—K1—Br155.66 (7)
C1—C2—N2121.5 (4)O2ii—K1—Br187.19 (8)
C3—C2—N2115.4 (4)O3iii—K1—Br197.38 (7)
C4—C3—C2118.7 (4)O2iii—K1—Br176.67 (7)
C4—C3—H3120.6O3i—K1—Br196.72 (7)
C2—C3—H3120.6O5—K1—H5115.6 (6)
C5—C4—C3119.3 (4)O5i—K1—H5181.7 (9)
C5—C4—H4120.4O1—K1—H5177.0 (10)
C3—C4—H4120.4O2ii—K1—H5168.0 (7)
C6—C5—C4120.9 (4)O3iii—K1—H51132.2 (6)
C6—C5—H5119.5O2iii—K1—H51134.5 (10)
C4—C5—H5119.5O3i—K1—H5180.1 (8)
C5—C6—C1120.9 (4)Br1—K1—H51125.1 (8)
C5—C6—H6119.5S1—N1—Br1109.8 (2)
C1—C6—H6119.5O4—N2—O3124.7 (4)
N1—Br1—K182.87 (12)O4—N2—C2117.7 (4)
O5—K1—O5i77.92 (8)O3—N2—C2117.6 (3)
O5—K1—O179.82 (11)S1—O1—K1127.53 (18)
O5i—K1—O1157.72 (11)S1—O2—K1ii134.68 (19)
O5—K1—O2ii82.86 (11)S1—O2—K1iv120.16 (18)
O5i—K1—O2ii84.62 (11)K1ii—O2—K1iv105.16 (10)
O1—K1—O2ii93.37 (11)N2—O3—K1iv135.6 (3)
O5—K1—O3iii117.39 (11)N2—O3—K1v123.6 (3)
O5i—K1—O3iii70.94 (11)K1iv—O3—K1v100.02 (11)
O1—K1—O3iii119.80 (11)O1—S1—O2117.1 (2)
O2ii—K1—O3iii142.64 (11)O1—S1—N1115.2 (2)
O5—K1—O2iii141.57 (11)O2—S1—N1105.8 (2)
O5i—K1—O2iii69.28 (11)O1—S1—C1105.67 (19)
O1—K1—O2iii131.59 (10)O2—S1—C1105.7 (2)
O2ii—K1—O2iii74.84 (10)N1—S1—C1106.5 (2)
O3iii—K1—O2iii70.30 (9)K1—O5—K1v112.63 (13)
O5—K1—O3i67.90 (10)K1—O5—H51104 (4)
O5i—K1—O3i109.52 (11)K1v—O5—H51108 (4)
O1—K1—O3i60.50 (9)K1—O5—H52118 (4)
O2ii—K1—O3i143.02 (10)K1v—O5—H52104 (4)
O3iii—K1—O3i73.50 (8)H51—O5—H52110 (3)
C6—C1—C2—C31.9 (6)O4—N2—O3—K1iv156.5 (3)
S1—C1—C2—C3175.3 (3)C2—N2—O3—K1iv22.1 (5)
C6—C1—C2—N2176.0 (4)O4—N2—O3—K1v35.7 (5)
S1—C1—C2—N26.8 (6)C2—N2—O3—K1v145.7 (3)
C1—C2—C3—C41.0 (6)K1—O1—S1—O2102.7 (3)
N2—C2—C3—C4177.0 (4)K1—O1—S1—N122.6 (3)
C2—C3—C4—C51.3 (7)K1—O1—S1—C1139.9 (2)
C3—C4—C5—C62.8 (7)K1ii—O2—S1—O1114.6 (3)
C4—C5—C6—C11.8 (8)K1iv—O2—S1—O165.8 (3)
C2—C1—C6—C50.5 (7)K1ii—O2—S1—N115.4 (3)
S1—C1—C6—C5177.0 (4)K1iv—O2—S1—N1164.3 (2)
N1—Br1—K1—O528.49 (17)K1ii—O2—S1—C1128.1 (3)
N1—Br1—K1—O5i124.97 (19)K1iv—O2—S1—C151.6 (2)
N1—Br1—K1—O147.15 (14)Br1—N1—S1—O146.5 (3)
N1—Br1—K1—O2ii48.87 (14)Br1—N1—S1—O2177.5 (2)
N1—Br1—K1—O3iii168.38 (14)Br1—N1—S1—C170.3 (2)
N1—Br1—K1—O2iii123.95 (13)C2—C1—S1—O124.4 (4)
N1—Br1—K1—O3i94.22 (13)C6—C1—S1—O1152.8 (3)
K1—Br1—N1—S163.0 (2)C2—C1—S1—O2100.4 (4)
C1—C2—N2—O4131.2 (4)C6—C1—S1—O282.4 (4)
C3—C2—N2—O450.8 (5)C2—C1—S1—N1147.4 (4)
C1—C2—N2—O350.2 (5)C6—C1—S1—N129.8 (4)
C3—C2—N2—O3127.9 (4)O5i—K1—O5—K1v140.66 (16)
O5—K1—O1—S1120.6 (3)O1—K1—O5—K1v38.60 (13)
O5i—K1—O1—S1122.5 (3)O2ii—K1—O5—K1v133.34 (15)
O2ii—K1—O1—S138.5 (3)O3iii—K1—O5—K1v79.80 (16)
O3iii—K1—O1—S1123.5 (2)O2iii—K1—O5—K1v172.23 (12)
O2iii—K1—O1—S134.2 (3)O3i—K1—O5—K1v23.55 (11)
O3i—K1—O1—S1169.1 (3)Br1—K1—O5—K1v54.17 (18)
Br1—K1—O1—S145.8 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y, z+1; (iii) x, y, z+1; (iv) x, y, z1; (v) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H51···N1ii0.84 (2)2.13 (3)2.926 (5)157 (5)
O5—H52···Br1vi0.84 (2)2.85 (4)3.509 (4)137 (4)
Symmetry codes: (ii) x, y, z+1; (vi) x, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaK+·C6H4BrN2O4S·H2O
Mr337.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.034 (2), 12.815 (2), 6.7741 (9)
β (°) 100.65 (1)
V3)1112.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)4.27
Crystal size (mm)0.48 × 0.48 × 0.24
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.234, 0.428
No. of measured, independent and
observed [I > 2σ(I)] reflections
3896, 2236, 1847
Rint0.042
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.145, 1.06
No. of reflections2236
No. of parameters152
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.79, 1.21

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···AD—HH···AD···AD—H···A
O5—H51···N1i0.844 (19)2.13 (3)2.926 (5)157 (5)
O5—H52···Br1ii0.841 (19)2.85 (4)3.509 (4)137 (4)
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z+3/2.
 

Acknowledgements

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

References

First citationGeorge, E., Vivekanandan, S. & Sivakumar, K. (2000). Acta Cryst. C56, 1208–1209.  Web of Science CSD CrossRef CAS IUCr Journals
First citationGowda, B. T., Foro, S. & Shakuntala, K. (2011a). Acta Cryst. E67, m926.  Web of Science CSD CrossRef IUCr Journals
First citationGowda, B. T., Foro, S. & Shakuntala, K. (2011b). Acta Cryst. E67, m1015.  Web of Science CSD CrossRef IUCr Journals
First citationGowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359–362.  CrossRef PubMed CAS Web of Science
First citationNardelli, M. (1999). J. Appl. Cryst. 32, 563–571.  Web of Science CrossRef CAS IUCr Journals
First citationOlmstead, M. M. & Power, P. P. (1986). Inorg. Chem. 25, 4057–4058.  CSD CrossRef CAS Web of Science
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationUsha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359.  Web of Science CrossRef CAS

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