Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812042456/nc2295sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536812042456/nc2295Isup2.hkl |
CCDC reference: 909731
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.093
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.438 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C12 H12 Br2 Cl4 K2 N2 O7 S2 Atom count from _chemical_formula_moiety:C6 H6 Br1 Cl2 K1 N1 O3.5 S1 PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension . 2 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ ? PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 8.36 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.35 Ratio PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
The title compound was prepared by a method similar to the one described by Gowda & Mahadevappa (Gowda & Mahadevappa, 1983). 2 g of 2,4-dichlorobenzenesulfonamide 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-2,4-dichlorobenzenesulfonamide 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 (203–205° C) and estimating, iodometrically, the amount of active bromine present in it. It was further characterized from its infrared spectrum.
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.
H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The H atoms bound to O atoms were located in difference map and later restrained to O—H = 0.82 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom.
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).
K+·C6H3BrCl2NO2S−·1.5H2O | F(000) = 1448 |
Mr = 740.18 | Dx = 1.975 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2489 reflections |
a = 12.5263 (7) Å | θ = 3.0–27.7° |
b = 6.7638 (4) Å | µ = 4.22 mm−1 |
c = 29.703 (2) Å | T = 293 K |
β = 98.352 (5)° | Prism, yellow |
V = 2489.9 (3) Å3 | 0.32 × 0.32 × 0.28 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 2535 independent reflections |
Radiation source: fine-focus sealed tube | 2204 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Rotation method data acquisition using ω scans. | θmax = 26.4°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −15→13 |
Tmin = 0.345, Tmax = 0.384 | k = −8→5 |
4960 measured reflections | l = −37→22 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0429P)2 + 8.3581P] where P = (Fo2 + 2Fc2)/3 |
2535 reflections | (Δ/σ)max = 0.001 |
150 parameters | Δρmax = 0.76 e Å−3 |
3 restraints | Δρmin = −0.65 e Å−3 |
K+·C6H3BrCl2NO2S−·1.5H2O | V = 2489.9 (3) Å3 |
Mr = 740.18 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.5263 (7) Å | µ = 4.22 mm−1 |
b = 6.7638 (4) Å | T = 293 K |
c = 29.703 (2) Å | 0.32 × 0.32 × 0.28 mm |
β = 98.352 (5)° |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 2535 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2204 reflections with I > 2σ(I) |
Tmin = 0.345, Tmax = 0.384 | Rint = 0.014 |
4960 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 3 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.76 e Å−3 |
2535 reflections | Δρmin = −0.65 e Å−3 |
150 parameters |
Experimental. 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0780 (3) | 0.4566 (5) | 0.11591 (11) | 0.0271 (7) | |
C2 | 0.1438 (3) | 0.3775 (5) | 0.08637 (12) | 0.0317 (7) | |
C3 | 0.1538 (3) | 0.4716 (6) | 0.04598 (12) | 0.0392 (9) | |
H3 | 0.1980 | 0.4192 | 0.0264 | 0.047* | |
C4 | 0.0974 (3) | 0.6446 (6) | 0.03496 (13) | 0.0426 (9) | |
C5 | 0.0320 (3) | 0.7248 (6) | 0.06337 (14) | 0.0447 (9) | |
H5 | −0.0056 | 0.8413 | 0.0556 | 0.054* | |
C6 | 0.0228 (3) | 0.6302 (5) | 0.10361 (13) | 0.0367 (8) | |
H6 | −0.0214 | 0.6841 | 0.1230 | 0.044* | |
Br1 | −0.11245 (3) | 0.10625 (6) | 0.130655 (14) | 0.04440 (14) | |
Cl1 | 0.21550 (9) | 0.15999 (15) | 0.09788 (4) | 0.0485 (3) | |
Cl2 | 0.10726 (10) | 0.7571 (2) | −0.01671 (4) | 0.0650 (4) | |
K1 | 0.34306 (6) | 0.13766 (12) | 0.23492 (3) | 0.0366 (2) | |
N1 | 0.0277 (2) | 0.1274 (4) | 0.16389 (10) | 0.0319 (6) | |
O1 | 0.1712 (2) | 0.3416 (4) | 0.19584 (8) | 0.0386 (6) | |
O2 | −0.0093 (2) | 0.4804 (4) | 0.18845 (8) | 0.0383 (6) | |
O3 | 0.2037 (2) | −0.1486 (4) | 0.19206 (10) | 0.0426 (6) | |
H31 | 0.234 (3) | −0.195 (7) | 0.1725 (12) | 0.051* | |
H32 | 0.155 (3) | −0.088 (6) | 0.1774 (14) | 0.051* | |
O4 | 0.5000 | 0.4277 (6) | 0.2500 | 0.0471 (10) | |
H41 | 0.490 (4) | 0.502 (6) | 0.2710 (11) | 0.056* | |
S1 | 0.06429 (7) | 0.34987 (12) | 0.16983 (3) | 0.02745 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0271 (16) | 0.0256 (16) | 0.0280 (16) | −0.0039 (13) | 0.0014 (12) | −0.0003 (13) |
C2 | 0.0261 (16) | 0.0319 (18) | 0.0371 (18) | −0.0031 (14) | 0.0042 (14) | 0.0000 (15) |
C3 | 0.0350 (19) | 0.048 (2) | 0.0364 (19) | −0.0108 (17) | 0.0109 (15) | −0.0008 (17) |
C4 | 0.040 (2) | 0.048 (2) | 0.038 (2) | −0.0161 (18) | −0.0006 (16) | 0.0113 (17) |
C5 | 0.047 (2) | 0.036 (2) | 0.050 (2) | 0.0043 (18) | 0.0016 (18) | 0.0116 (18) |
C6 | 0.0359 (19) | 0.0322 (18) | 0.041 (2) | 0.0040 (15) | 0.0036 (15) | 0.0029 (15) |
Br1 | 0.0342 (2) | 0.0494 (3) | 0.0498 (2) | −0.00725 (17) | 0.00672 (16) | −0.01193 (18) |
Cl1 | 0.0484 (6) | 0.0376 (5) | 0.0645 (7) | 0.0110 (4) | 0.0250 (5) | 0.0029 (5) |
Cl2 | 0.0592 (7) | 0.0857 (9) | 0.0483 (6) | −0.0170 (6) | 0.0024 (5) | 0.0322 (6) |
K1 | 0.0312 (4) | 0.0354 (4) | 0.0423 (4) | 0.0051 (3) | 0.0021 (3) | −0.0034 (3) |
N1 | 0.0307 (15) | 0.0279 (15) | 0.0373 (16) | 0.0006 (12) | 0.0060 (12) | 0.0047 (12) |
O1 | 0.0373 (14) | 0.0399 (14) | 0.0353 (14) | 0.0026 (11) | −0.0064 (11) | 0.0010 (11) |
O2 | 0.0444 (15) | 0.0387 (14) | 0.0339 (13) | 0.0094 (12) | 0.0130 (11) | −0.0046 (11) |
O3 | 0.0475 (17) | 0.0380 (15) | 0.0434 (16) | 0.0052 (12) | 0.0099 (13) | 0.0004 (12) |
O4 | 0.073 (3) | 0.031 (2) | 0.041 (2) | 0.000 | 0.022 (2) | 0.000 |
S1 | 0.0302 (4) | 0.0260 (4) | 0.0260 (4) | 0.0028 (3) | 0.0033 (3) | 0.0000 (3) |
C1—C6 | 1.384 (5) | K1—O3 | 2.788 (3) |
C1—C2 | 1.395 (5) | K1—O1iii | 2.895 (3) |
C1—S1 | 1.787 (3) | K1—O2iii | 3.045 (3) |
C2—C3 | 1.380 (5) | K1—S1iii | 3.4910 (12) |
C2—Cl1 | 1.732 (4) | N1—S1 | 1.575 (3) |
C3—C4 | 1.381 (6) | O1—S1 | 1.447 (3) |
C3—H3 | 0.9300 | O1—K1ii | 2.895 (3) |
C4—C5 | 1.370 (6) | O2—S1 | 1.443 (3) |
C4—Cl2 | 1.734 (4) | O2—K1iv | 2.683 (2) |
C5—C6 | 1.375 (5) | O2—K1ii | 3.045 (3) |
C5—H5 | 0.9300 | O3—K1iii | 2.740 (3) |
C6—H6 | 0.9300 | O3—H31 | 0.802 (19) |
Br1—N1 | 1.890 (3) | O3—H32 | 0.808 (19) |
K1—O1 | 2.675 (3) | O4—K1v | 2.767 (3) |
K1—O2i | 2.683 (2) | O4—H41 | 0.820 (19) |
K1—O3ii | 2.740 (3) | S1—K1ii | 3.4910 (12) |
K1—O4 | 2.767 (3) | ||
C6—C1—C2 | 118.5 (3) | O3—K1—K1v | 130.38 (6) |
C6—C1—S1 | 118.0 (3) | O1iii—K1—K1v | 90.06 (6) |
C2—C1—S1 | 123.4 (3) | O2iii—K1—K1v | 43.27 (5) |
C3—C2—C1 | 120.4 (3) | S1iii—K1—K1v | 66.97 (2) |
C3—C2—Cl1 | 117.0 (3) | O1—K1—K1iii | 94.01 (7) |
C1—C2—Cl1 | 122.6 (3) | O2i—K1—K1iii | 103.41 (6) |
C2—C3—C4 | 119.3 (4) | O3ii—K1—K1iii | 93.78 (7) |
C2—C3—H3 | 120.4 | O4—K1—K1iii | 157.36 (5) |
C4—C3—H3 | 120.4 | O3—K1—K1iii | 38.92 (6) |
C5—C4—C3 | 121.4 (4) | O1iii—K1—K1iii | 38.01 (5) |
C5—C4—Cl2 | 119.8 (3) | O2iii—K1—K1iii | 84.35 (5) |
C3—C4—Cl2 | 118.8 (3) | S1iii—K1—K1iii | 61.08 (2) |
C4—C5—C6 | 118.9 (4) | K1v—K1—K1iii | 120.90 (2) |
C4—C5—H5 | 120.5 | O1—K1—K1ii | 41.78 (6) |
C6—C5—H5 | 120.5 | O2i—K1—K1ii | 149.20 (6) |
C5—C6—C1 | 121.5 (4) | O3ii—K1—K1ii | 39.74 (6) |
C5—C6—H6 | 119.2 | O4—K1—K1ii | 78.55 (6) |
C1—C6—H6 | 119.2 | O3—K1—K1ii | 108.70 (7) |
O1—K1—O2i | 123.54 (8) | O1iii—K1—K1ii | 107.85 (6) |
O1—K1—O3ii | 79.66 (9) | O2iii—K1—K1ii | 117.01 (6) |
O2i—K1—O3ii | 149.20 (9) | S1iii—K1—K1ii | 113.48 (3) |
O1—K1—O4 | 102.28 (8) | K1v—K1—K1ii | 120.90 (2) |
O2i—K1—O4 | 80.66 (7) | K1iii—K1—K1ii | 104.55 (3) |
O3ii—K1—O4 | 74.11 (7) | S1—N1—Br1 | 111.33 (16) |
O1—K1—O3 | 75.45 (8) | S1—O1—K1 | 151.14 (16) |
O2i—K1—O3 | 85.56 (9) | S1—O1—K1ii | 101.80 (13) |
O3ii—K1—O3 | 122.44 (5) | K1—O1—K1ii | 100.21 (8) |
O4—K1—O3 | 161.68 (7) | S1—O2—K1iv | 165.01 (16) |
O1—K1—O1iii | 122.42 (5) | S1—O2—K1ii | 95.45 (12) |
O2i—K1—O1iii | 102.09 (8) | K1iv—O2—K1ii | 85.68 (7) |
O3ii—K1—O1iii | 76.13 (8) | K1iii—O3—K1 | 101.34 (10) |
O4—K1—O1iii | 119.42 (6) | K1iii—O3—H31 | 123 (4) |
O3—K1—O1iii | 75.21 (8) | K1—O3—H31 | 106 (4) |
O1—K1—O2iii | 157.55 (8) | K1iii—O3—H32 | 117 (4) |
O2i—K1—O2iii | 78.37 (9) | K1—O3—H32 | 106 (3) |
O3ii—K1—O2iii | 78.12 (8) | H31—O3—H32 | 102 (5) |
O4—K1—O2iii | 74.58 (7) | K1—O4—K1v | 89.71 (12) |
O3—K1—O2iii | 114.43 (8) | K1—O4—H41 | 112 (3) |
O1iii—K1—O2iii | 48.19 (7) | K1v—O4—H41 | 119 (3) |
O1—K1—S1iii | 142.27 (7) | O2—S1—O1 | 114.34 (16) |
O2i—K1—S1iii | 91.31 (6) | O2—S1—N1 | 115.83 (16) |
O3ii—K1—S1iii | 74.74 (7) | O1—S1—N1 | 104.73 (16) |
O4—K1—S1iii | 96.86 (5) | O2—S1—C1 | 104.25 (15) |
O3—K1—S1iii | 95.47 (7) | O1—S1—C1 | 107.00 (16) |
O1iii—K1—S1iii | 23.94 (5) | N1—S1—C1 | 110.46 (16) |
O2iii—K1—S1iii | 24.30 (5) | O2—S1—K1ii | 60.25 (11) |
O1—K1—K1v | 145.05 (6) | O1—S1—K1ii | 54.26 (11) |
O2i—K1—K1v | 51.05 (6) | N1—S1—K1ii | 132.87 (12) |
O3ii—K1—K1v | 98.18 (7) | C1—S1—K1ii | 115.93 (11) |
O4—K1—K1v | 45.15 (6) | ||
C6—C1—C2—C3 | 0.3 (5) | S1iii—K1—O3—K1iii | 26.89 (8) |
S1—C1—C2—C3 | −177.6 (3) | K1v—K1—O3—K1iii | 91.14 (10) |
C6—C1—C2—Cl1 | −179.3 (3) | K1ii—K1—O3—K1iii | −90.17 (8) |
S1—C1—C2—Cl1 | 2.9 (4) | O1—K1—O4—K1v | −165.19 (7) |
C1—C2—C3—C4 | −0.3 (5) | O2i—K1—O4—K1v | −42.70 (6) |
Cl1—C2—C3—C4 | 179.3 (3) | O3ii—K1—O4—K1v | 119.46 (7) |
C2—C3—C4—C5 | 0.1 (6) | O3—K1—O4—K1v | −84.4 (3) |
C2—C3—C4—Cl2 | −178.0 (3) | O1iii—K1—O4—K1v | 55.99 (7) |
C3—C4—C5—C6 | 0.0 (6) | O2iii—K1—O4—K1v | 37.71 (5) |
Cl2—C4—C5—C6 | 178.1 (3) | S1iii—K1—O4—K1v | 47.51 (2) |
C4—C5—C6—C1 | −0.1 (6) | K1iii—K1—O4—K1v | 59.77 (14) |
C2—C1—C6—C5 | −0.1 (5) | K1ii—K1—O4—K1v | 160.16 (4) |
S1—C1—C6—C5 | 177.9 (3) | K1iv—O2—S1—O1 | −89.2 (6) |
O2i—K1—O1—S1 | 77.2 (4) | K1ii—O2—S1—O1 | 4.50 (17) |
O3ii—K1—O1—S1 | −124.9 (3) | K1iv—O2—S1—N1 | 32.8 (7) |
O4—K1—O1—S1 | 164.0 (3) | K1ii—O2—S1—N1 | 126.44 (14) |
O3—K1—O1—S1 | 2.7 (3) | K1iv—O2—S1—C1 | 154.3 (6) |
O1iii—K1—O1—S1 | −58.8 (3) | K1ii—O2—S1—C1 | −111.99 (12) |
O2iii—K1—O1—S1 | −116.7 (3) | K1iv—O2—S1—K1ii | −93.7 (6) |
S1iii—K1—O1—S1 | −77.2 (4) | K1—O1—S1—O2 | 134.2 (3) |
K1v—K1—O1—S1 | 145.6 (3) | K1ii—O1—S1—O2 | −4.81 (18) |
K1iii—K1—O1—S1 | −31.8 (3) | K1—O1—S1—N1 | 6.3 (4) |
K1ii—K1—O1—S1 | −139.2 (4) | K1ii—O1—S1—N1 | −132.65 (13) |
O2i—K1—O1—K1ii | −143.58 (9) | K1—O1—S1—C1 | −111.0 (3) |
O3ii—K1—O1—K1ii | 14.32 (8) | K1ii—O1—S1—C1 | 110.07 (14) |
O4—K1—O1—K1ii | −56.74 (8) | K1—O1—S1—K1ii | 139.0 (4) |
O3—K1—O1—K1ii | 141.96 (10) | Br1—N1—S1—O2 | 52.7 (2) |
O1iii—K1—O1—K1ii | 80.46 (13) | Br1—N1—S1—O1 | 179.61 (16) |
O2iii—K1—O1—K1ii | 22.6 (2) | Br1—N1—S1—C1 | −65.5 (2) |
S1iii—K1—O1—K1ii | 62.01 (13) | Br1—N1—S1—K1ii | 125.06 (12) |
K1v—K1—O1—K1ii | −75.18 (13) | C6—C1—S1—O2 | 1.3 (3) |
K1iii—K1—O1—K1ii | 107.44 (7) | C2—C1—S1—O2 | 179.2 (3) |
O1—K1—O3—K1iii | −115.86 (10) | C6—C1—S1—O1 | −120.2 (3) |
O2i—K1—O3—K1iii | 117.79 (9) | C2—C1—S1—O1 | 57.7 (3) |
O3ii—K1—O3—K1iii | −48.49 (13) | C6—C1—S1—N1 | 126.4 (3) |
O4—K1—O3—K1iii | 159.0 (2) | C2—C1—S1—N1 | −55.8 (3) |
O1iii—K1—O3—K1iii | 14.03 (8) | C6—C1—S1—K1ii | −62.2 (3) |
O2iii—K1—O3—K1iii | 42.71 (11) | C2—C1—S1—K1ii | 115.6 (3) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, y+1/2, z; (v) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···Br1i | 0.80 (2) | 2.78 (2) | 3.550 (3) | 160 (4) |
O3—H32···N1 | 0.81 (2) | 2.15 (3) | 2.917 (4) | 158 (5) |
O4—H41···N1ii | 0.82 (2) | 2.16 (2) | 2.957 (3) | 165 (5) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | K+·C6H3BrCl2NO2S−·1.5H2O |
Mr | 740.18 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.5263 (7), 6.7638 (4), 29.703 (2) |
β (°) | 98.352 (5) |
V (Å3) | 2489.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.22 |
Crystal size (mm) | 0.32 × 0.32 × 0.28 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.345, 0.384 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4960, 2535, 2204 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.093, 1.09 |
No. of reflections | 2535 |
No. of parameters | 150 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.76, −0.65 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···Br1i | 0.802 (19) | 2.78 (2) | 3.550 (3) | 160 (4) |
O3—H32···N1 | 0.808 (19) | 2.15 (3) | 2.917 (4) | 158 (5) |
O4—H41···N1ii | 0.820 (19) | 2.16 (2) | 2.957 (3) | 165 (5) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, −z+1/2. |
The present work was undertaken in order to explore the effect of replacing sodium ion by potassium ion on the solid state structures of metal salts of N-haloarylsulfonamidates (Gowda et al., 2007, 2011a,b). As part of this work, the structure of potassium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (I) has been determined (Fig. 1). The structure of (I) resembles those of potassium N-bromo-2-chlorobenzenesulfonamidate sesquihydrate (II) (Gowda et al., 2011a), potassium N-bromo-4-chlorobenzenesulfonamidate sesquihydrate (III) (Gowda et al., 2011b), sodium N-bromo-2,4-dichlorobenzenesulfonamidate sesquihydrate (IV) (Gowda et al., 2007) and other sodium N-chloro-arylsulfonamidates (George et al., 2000; Olmstead & Power, 1986).
In the title compound, K+ ion is hepta coordinated by three O atoms from water molecules and four sulfonyl O atoms of three different N-bromo-2,4-dichlorobenzenesulfonamide anions. The replacement of Na+ by K+ changes co-ordination from hexa to hepta in the structure (Gowda et al., 2007) and other parameters.
The S—N distance of 1.575 (3) Å is consistent with a S—N double bond and is in agreement with the observed values of 1.582 (4) Å in (II), 1.584 (6) Å in (III) and 1.590 (6) Å in (IV).
The asymmetric unit of (I) consists of one potassium cation, one N-bromo-2,4-dichlorobenzenesulfonamidate anion and one water molecule in general position and and one water molecule located on a twofold rotation axis.
In the crystal structure the anions are linked by intermolecular O—H···Br and O—H···N hydrogen bonding into layers, that are parallel to the ac plane (Fig. 2 and Table 1).