Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035830/im2021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035830/im2021Isup2.hkl |
CCDC reference: 657632
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (S-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.037
- wR factor = 0.098
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 29.00 Perc.
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Cl1 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 S1 -K1 -CL1 -C4 -175.12 0.19 1.656 1.555 1.555 4.565 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 S1 -K1 -CL1 -C4 175.12 0.18 1.656 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 28 S1 -K1 -CL1 -K1 0.00 0.00 1.656 1.555 1.555 1.455 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 39 S1 -K1 -CL1 -K1 65.03 0.02 1.656 1.555 1.555 3.667 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 50 S1 -K1 -CL1 -K1 -65.03 0.02 1.656 1.555 1.555 3.657 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.95 Ratio PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.30 Deg. C4 -CL1 -C4 4.565 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.40 Deg. C2 -C1 -C2 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.40 Deg. C6 -C1 -C6 4.565 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 21.80 Deg. C3 -C2 -C3 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 11.50 Deg. C4 -C3 -C4 4.565 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.50 Deg. C2 -C3 -C2 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.90 Deg. C3 -C4 -C3 4.565 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 39.90 Deg. C5 -C4 -C5 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 10.50 Deg. C4 -C5 -C4 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.52 Deg. C6 -C5 -C6 1.555 1.555 4.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.30 Deg. C5 -C6 -C5 1.555 1.555 4.565
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared from 4-chloro-sulfonylchloride prepared as an intermediate compound in the preparation of 4-chloro-benzenesulfonamide (Gowda et al., 2002). 4-Chlorosulfonylchloride was hydrolysed by treating with aqueous KOH to obtain the title compound. The purity of the compound was checked by determining its melting point (Oae et al., 1981) and by recording its infrared spectra. Single crystals of the title compound were obtained from its aqueous solution and used for X-ray diffraction studies at room temperature.
H atoms of the benzene ring were positioned geometrically and refined using a riding model with C—H = 0.93Å and with Uiso(H) = 1.2 Ueq(C). No restraints were applied to non-hydrogen atoms.
As part of a study on the substituent effects on the solid state structures of chemically and biologically significant compounds (Gowda et al., 2003, Gowda, Jyothi et al., 2007; Gowda, Kozisek et al., 2007; Gowda, Nayak et al., 2007), in the present work, the structure of potassium 4-chloro-benzenesulfonate (K4CBS) has been determined. The structure of K4CBS (Fig. 1) resembles that of silver 4-chloro-benzenesulfonate (Ag4CBS) with somewhat different geometric parameters (Bernardinelli et al., 1991). K4CBS crystallizes in monoclinic P21/m space group compared to the monoclinic P21/c space group observed for Ag4CBS ((Bernardinelli et al., 1991). The potassium ion shows hepta coordination with two Chloro ligands and five sulfonato O atoms of four different 4-chloro-benzenesulfonato anions, one of them in a monodentate and three in a bidentate way (Fig. 2). This potassium coordination therefore results in a three dimensional supramolecular structure (Fig. 2). The benzene rings are disordered over two different conformations with site occupation factors of 0.5 each.
For related literature, see: Bernardinelli et al. (1991); Gowda et al. (2002, 2003); Gowda, Jyothi et al. (2007); Gowda, Kožíšek et al. (2007); Gowda, Nayak et al. (2007); Oae et al. (1981).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[K(C6H4ClO3S)] | F(000) = 232 |
Mr = 230.70 | Dx = 1.874 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yb | Cell parameters from 3635 reflections |
a = 6.1688 (6) Å | θ = 2.1–27.4° |
b = 6.813 (1) Å | µ = 1.19 mm−1 |
c = 9.804 (1) Å | T = 303 K |
β = 97.236 (8)° | Prism, colourless |
V = 408.76 (8) Å3 | 0.44 × 0.32 × 0.06 mm |
Z = 2 |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 912 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 799 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.3°, θmin = 3.3° |
Rotation method data acquisition using ω and φ scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −8→8 |
Tmin = 0.623, Tmax = 0.932 | l = −12→12 |
6343 measured reflections |
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) = 0.098 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0419P)2 + 0.7009P] where P = (Fo2 + 2Fc2)/3 |
912 reflections | (Δ/σ)max = 0.003 |
73 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
[K(C6H4ClO3S)] | V = 408.76 (8) Å3 |
Mr = 230.70 | Z = 2 |
Monoclinic, P21/m | Mo Kα radiation |
a = 6.1688 (6) Å | µ = 1.19 mm−1 |
b = 6.813 (1) Å | T = 303 K |
c = 9.804 (1) Å | 0.44 × 0.32 × 0.06 mm |
β = 97.236 (8)° |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 912 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 799 reflections with I > 2σ(I) |
Tmin = 0.623, Tmax = 0.932 | Rint = 0.031 |
6343 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.55 e Å−3 |
912 reflections | Δρmin = −0.53 e Å−3 |
73 parameters |
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 | Occ. (<1) | |
K1 | 0.79613 (14) | 0.2500 | 1.00401 (9) | 0.0328 (3) | |
Cl1 | 0.27258 (19) | 0.2500 | 0.84491 (10) | 0.0466 (3) | |
S1 | 0.29017 (16) | 0.2500 | 0.20716 (9) | 0.0281 (3) | |
O1 | 0.1741 (4) | 0.4253 (3) | 0.15569 (19) | 0.0422 (5) | |
O3 | 0.5178 (5) | 0.2500 | 0.1871 (3) | 0.0492 (9) | |
C1 | 0.2845 (4) | 0.2500 | 0.38707 (19) | 0.0262 (8) | |
C2 | 0.4690 (4) | 0.1982 (4) | 0.4761 (3) | 0.0287 (15) | 0.50 |
H2 | 0.5946 | 0.1567 | 0.4411 | 0.034* | 0.50 |
C3 | 0.4658 (4) | 0.2084 (7) | 0.6175 (2) | 0.034 (2) | 0.50 |
H3 | 0.5892 | 0.1737 | 0.6770 | 0.041* | 0.50 |
C4 | 0.2781 (5) | 0.2704 (8) | 0.6697 (2) | 0.0252 (11) | 0.50 |
C5 | 0.0935 (4) | 0.3223 (7) | 0.5807 (3) | 0.0343 (13) | 0.50 |
H5 | −0.0321 | 0.3638 | 0.6157 | 0.041* | 0.50 |
C6 | 0.0968 (4) | 0.3120 (4) | 0.4394 (3) | 0.0304 (12) | 0.50 |
H6 | −0.0267 | 0.3467 | 0.3798 | 0.037* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.0309 (5) | 0.0356 (5) | 0.0326 (5) | 0.000 | 0.0069 (3) | 0.000 |
Cl1 | 0.0505 (6) | 0.0685 (8) | 0.0223 (5) | 0.000 | 0.0102 (4) | 0.000 |
S1 | 0.0327 (5) | 0.0315 (5) | 0.0200 (4) | 0.000 | 0.0031 (3) | 0.000 |
O1 | 0.0594 (13) | 0.0351 (12) | 0.0305 (10) | 0.0043 (10) | 0.0001 (9) | 0.0074 (9) |
O3 | 0.0364 (16) | 0.083 (3) | 0.0302 (15) | 0.000 | 0.0105 (13) | 0.000 |
C1 | 0.0314 (19) | 0.0275 (19) | 0.0198 (17) | 0.000 | 0.0031 (14) | 0.000 |
C2 | 0.027 (2) | 0.033 (4) | 0.027 (2) | 0.0067 (18) | 0.0070 (18) | −0.0005 (18) |
C3 | 0.033 (2) | 0.040 (7) | 0.029 (2) | 0.008 (2) | −0.0001 (18) | 0.003 (2) |
C4 | 0.035 (2) | 0.019 (3) | 0.0221 (18) | 0.005 (3) | 0.0055 (15) | 0.006 (3) |
C5 | 0.030 (2) | 0.043 (3) | 0.030 (3) | 0.002 (2) | 0.006 (2) | −0.001 (2) |
C6 | 0.028 (2) | 0.030 (3) | 0.032 (3) | 0.0013 (18) | 0.001 (2) | −0.0009 (19) |
K1—O3i | 2.636 (3) | O1—K1xiii | 2.864 (2) |
K1—O1ii | 2.730 (2) | O3—K1xiv | 2.636 (3) |
K1—O1iii | 2.730 (2) | C1—C2 | 1.3900 |
K1—O1iv | 2.864 (2) | C1—C2xi | 1.3900 (15) |
K1—O1v | 2.864 (2) | C1—C6xi | 1.3900 (18) |
K1—Cl1 | 3.4051 (14) | C1—C6 | 1.3900 |
K1—S1iv | 3.4243 (13) | C2—C3 | 1.3900 |
K1—Cl1vi | 3.4967 (14) | C2—C3xi | 1.527 (4) |
K1—Cl1vii | 3.7598 (7) | C2—H2 | 0.9300 |
K1—Cl1viii | 3.7598 (7) | C3—C4xi | 1.3320 (12) |
K1—K1ix | 4.2411 (11) | C3—C4 | 1.3900 |
K1—K1x | 4.2411 (11) | C3—C2xi | 1.527 (3) |
Cl1—C4xi | 1.728 (2) | C3—H3 | 0.9300 |
Cl1—C4 | 1.728 (2) | C4—C3xi | 1.3320 (11) |
Cl1—K1xii | 3.4967 (14) | C4—C5 | 1.3900 |
Cl1—K1vii | 3.7598 (7) | C4—C5xi | 1.485 (4) |
Cl1—K1viii | 3.7598 (7) | C5—C6 | 1.3900 |
S1—O3 | 1.442 (3) | C5—C4xi | 1.485 (4) |
S1—O1xi | 1.450 (2) | C5—C6xi | 1.663 (3) |
S1—O1 | 1.450 (2) | C5—H5 | 0.9300 |
S1—C1 | 1.769 (2) | C6—C5xi | 1.663 (5) |
S1—K1xiii | 3.4243 (13) | C6—H6 | 0.9300 |
O1—K1iii | 2.730 (2) | ||
O3i—K1—O1ii | 119.17 (6) | O1xi—S1—C1 | 106.03 (10) |
O3i—K1—O1iii | 119.17 (5) | O1—S1—C1 | 106.03 (10) |
O1ii—K1—O1iii | 108.27 (9) | O3—S1—K1xiii | 137.00 (13) |
O3i—K1—O1iv | 101.76 (8) | O1xi—S1—K1xiii | 55.48 (9) |
O1ii—K1—O1iv | 121.78 (5) | O1—S1—K1xiii | 55.48 (9) |
O1iii—K1—O1iv | 81.41 (6) | C1—S1—K1xiii | 116.88 (10) |
O3i—K1—O1v | 101.76 (8) | S1—O1—K1iii | 143.24 (13) |
O1ii—K1—O1v | 81.41 (6) | S1—O1—K1xiii | 99.86 (11) |
O1iii—K1—O1v | 121.78 (5) | K1iii—O1—K1xiii | 98.59 (6) |
O1iv—K1—O1v | 49.30 (9) | S1—O3—K1xiv | 145.25 (18) |
O3i—K1—Cl1 | 69.54 (7) | C2—C1—C2xi | 29.4 (2) |
O1ii—K1—Cl1 | 82.28 (5) | C2—C1—C6xi | 110.21 (9) |
O1iii—K1—Cl1 | 82.28 (5) | C2xi—C1—C6xi | 120.00 (7) |
O1iv—K1—Cl1 | 154.30 (5) | C2—C1—C6 | 120.0 |
O1v—K1—Cl1 | 154.30 (5) | C2xi—C1—C6 | 110.21 (10) |
O3i—K1—S1iv | 102.25 (7) | C6xi—C1—C6 | 35.4 (2) |
O1ii—K1—S1iv | 102.38 (5) | C2—C1—S1 | 120.59 (16) |
O1iii—K1—S1iv | 102.38 (5) | C2xi—C1—S1 | 120.59 (16) |
O1iv—K1—S1iv | 24.66 (4) | C6xi—C1—S1 | 119.33 (16) |
O1v—K1—S1iv | 24.66 (4) | C6—C1—S1 | 119.33 (15) |
Cl1—K1—S1iv | 171.79 (4) | C2xi—C2—C1 | 75.3 |
O3i—K1—Cl1vi | 163.75 (8) | C2xi—C2—C3 | 87.1 |
O1ii—K1—Cl1vi | 67.86 (5) | C1—C2—C3 | 120.0 |
O1iii—K1—Cl1vi | 67.86 (5) | C2xi—C2—C3xi | 65.4 (3) |
O1iv—K1—Cl1vi | 63.67 (5) | C1—C2—C3xi | 111.15 (16) |
O1v—K1—Cl1vi | 63.67 (5) | C3—C2—C3xi | 21.8 (3) |
Cl1—K1—Cl1vi | 126.71 (4) | C2xi—C2—H2 | 107.7 |
S1iv—K1—Cl1vi | 61.51 (3) | C1—C2—H2 | 120.0 |
O3i—K1—Cl1vii | 67.43 (2) | C3—C2—H2 | 120.0 |
O1ii—K1—Cl1vii | 168.32 (5) | C3xi—C2—H2 | 124.6 |
O1iii—K1—Cl1vii | 60.71 (5) | C3xi—C3—C4xi | 83.8 (5) |
O1iv—K1—Cl1vii | 62.77 (5) | C3xi—C3—C4 | 72.3 |
O1v—K1—Cl1vii | 107.35 (5) | C4xi—C3—C4 | 11.5 (5) |
Cl1—K1—Cl1vii | 91.89 (2) | C3xi—C3—C2 | 92.9 |
S1iv—K1—Cl1vii | 84.67 (2) | C4xi—C3—C2 | 120.8 |
Cl1vi—K1—Cl1vii | 108.57 (2) | C4—C3—C2 | 120.0 |
O3i—K1—Cl1viii | 67.43 (2) | C3xi—C3—C2xi | 65.4 (2) |
O1ii—K1—Cl1viii | 60.71 (5) | C4xi—C3—C2xi | 114.5 (3) |
O1iii—K1—Cl1viii | 168.32 (5) | C4—C3—C2xi | 108.33 (10) |
O1iv—K1—Cl1viii | 107.35 (5) | C2—C3—C2xi | 27.5 (2) |
O1v—K1—Cl1viii | 62.77 (5) | C3xi—C3—H3 | 104.7 |
Cl1—K1—Cl1viii | 91.89 (2) | C4xi—C3—H3 | 117.9 |
S1iv—K1—Cl1viii | 84.67 (2) | C4—C3—H3 | 120.0 |
Cl1vi—K1—Cl1viii | 108.57 (2) | C2—C3—H3 | 120.0 |
Cl1vii—K1—Cl1viii | 129.93 (4) | C2xi—C3—H3 | 124.9 |
O3i—K1—K1ix | 116.83 (4) | C4xi—C4—C3xi | 96.2 (4) |
O1ii—K1—K1ix | 123.87 (6) | C4xi—C4—C5 | 104.7 |
O1iii—K1—K1ix | 41.89 (5) | C3xi—C4—C5 | 114.44 (14) |
O1iv—K1—K1ix | 39.52 (4) | C4xi—C4—C3 | 72.3 |
O1v—K1—K1ix | 84.18 (5) | C3xi—C4—C3 | 23.9 (4) |
Cl1—K1—K1ix | 121.47 (2) | C5—C4—C3 | 120.0 |
S1iv—K1—K1ix | 61.60 (2) | C4xi—C4—C5xi | 64.8 (3) |
Cl1vi—K1—K1ix | 57.17 (2) | C3xi—C4—C5xi | 117.31 (19) |
Cl1vii—K1—K1ix | 51.400 (19) | C5—C4—C5xi | 39.9 (3) |
Cl1viii—K1—K1ix | 146.26 (4) | C3—C4—C5xi | 105.45 (15) |
O3i—K1—K1x | 116.83 (4) | C4xi—C4—Cl1 | 85.4 (3) |
O1ii—K1—K1x | 41.89 (5) | C3xi—C4—Cl1 | 121.20 (18) |
O1iii—K1—K1x | 123.87 (6) | C5—C4—Cl1 | 121.86 (18) |
O1iv—K1—K1x | 84.18 (5) | C3—C4—Cl1 | 117.62 (19) |
O1v—K1—K1x | 39.52 (4) | C5xi—C4—Cl1 | 116.1 (3) |
Cl1—K1—K1x | 121.47 (2) | C5xi—C5—C4 | 75.3 |
S1iv—K1—K1x | 61.60 (2) | C5xi—C5—C6 | 87.1 |
Cl1vi—K1—K1x | 57.17 (2) | C4—C5—C6 | 120.0 |
Cl1vii—K1—K1x | 146.26 (4) | C5xi—C5—C4xi | 64.8 (4) |
Cl1viii—K1—K1x | 51.400 (19) | C4—C5—C4xi | 10.5 (4) |
K1ix—K1—K1x | 106.88 (4) | C6—C5—C4xi | 117.29 (11) |
C4xi—Cl1—C4 | 9.3 (3) | C5xi—C5—C6xi | 56.61 (17) |
C4xi—Cl1—K1 | 108.62 (11) | C4—C5—C6xi | 106.79 (9) |
C4—Cl1—K1 | 108.62 (11) | C6—C5—C6xi | 30.52 (17) |
C4xi—Cl1—K1xii | 124.49 (12) | C4xi—C5—C6xi | 99.6 (3) |
C4—Cl1—K1xii | 124.49 (11) | C5xi—C5—H5 | 107.7 |
K1—Cl1—K1xii | 126.71 (4) | C4—C5—H5 | 120.0 |
C4xi—Cl1—K1vii | 118.81 (18) | C6—C5—H5 | 120.0 |
C4—Cl1—K1vii | 109.62 (17) | C4xi—C5—H5 | 121.7 |
K1—Cl1—K1vii | 88.11 (2) | C6xi—C5—H5 | 124.9 |
K1xii—Cl1—K1vii | 71.43 (2) | C6xi—C6—C5 | 92.9 |
C4xi—Cl1—K1viii | 109.62 (17) | C6xi—C6—C1 | 72.3 |
C4—Cl1—K1viii | 118.81 (18) | C5—C6—C1 | 120.0 |
K1—Cl1—K1viii | 88.11 (2) | C6xi—C6—C5xi | 56.6 (3) |
K1xii—Cl1—K1viii | 71.43 (2) | C5—C6—C5xi | 36.3 (3) |
K1vii—Cl1—K1viii | 129.93 (4) | C1—C6—C5xi | 103.76 (14) |
O3—S1—O1xi | 113.52 (11) | C6xi—C6—H6 | 104.7 |
O3—S1—O1 | 113.52 (11) | C5—C6—H6 | 120.0 |
O1xi—S1—O1 | 110.91 (18) | C1—C6—H6 | 120.0 |
O3—S1—C1 | 106.12 (15) | C5xi—C6—H6 | 124.6 |
O3i—K1—Cl1—C4xi | −175.12 (19) | S1—C1—C2—C3xi | 154.6 (2) |
O1ii—K1—Cl1—C4xi | −49.98 (19) | C2xi—C2—C3—C3xi | 0.0 |
O1iii—K1—Cl1—C4xi | 59.75 (19) | C1—C2—C3—C3xi | −71.2 |
O1iv—K1—Cl1—C4xi | 110.8 (2) | C2xi—C2—C3—C4xi | 84.5 (5) |
O1v—K1—Cl1—C4xi | −101.0 (2) | C1—C2—C3—C4xi | 13.3 (5) |
S1iv—K1—Cl1—C4xi | −175.12 (19) | C3xi—C2—C3—C4xi | 84.5 (5) |
Cl1vi—K1—Cl1—C4xi | 4.88 (19) | C2xi—C2—C3—C4 | 71.2 |
Cl1vii—K1—Cl1—C4xi | 119.85 (19) | C1—C2—C3—C4 | 0.0 |
Cl1viii—K1—Cl1—C4xi | −110.09 (19) | C3xi—C2—C3—C4 | 71.2 |
K1ix—K1—Cl1—C4xi | 75.22 (19) | C1—C2—C3—C2xi | −71.2 |
K1x—K1—Cl1—C4xi | −65.46 (19) | C3xi—C2—C3—C2xi | 0.0 |
O3i—K1—Cl1—C4 | 175.12 (18) | C3xi—C3—C4—C4xi | 180.0 |
O1ii—K1—Cl1—C4 | −59.75 (19) | C2—C3—C4—C4xi | 97.1 |
O1iii—K1—Cl1—C4 | 49.98 (19) | C2xi—C3—C4—C4xi | 124.51 (19) |
O1iv—K1—Cl1—C4 | 101.0 (2) | C4xi—C3—C4—C3xi | 180.0 |
O1v—K1—Cl1—C4 | −110.8 (2) | C2—C3—C4—C3xi | −82.9 |
S1iv—K1—Cl1—C4 | 175.12 (18) | C2xi—C3—C4—C3xi | −55.49 (19) |
Cl1vi—K1—Cl1—C4 | −4.88 (18) | C3xi—C3—C4—C5 | 82.9 |
Cl1vii—K1—Cl1—C4 | 110.09 (18) | C4xi—C3—C4—C5 | −97.1 |
Cl1viii—K1—Cl1—C4 | −119.85 (18) | C2—C3—C4—C5 | 0.0 |
K1ix—K1—Cl1—C4 | 65.46 (19) | C2xi—C3—C4—C5 | 27.41 (19) |
K1x—K1—Cl1—C4 | −75.22 (19) | C3xi—C3—C4—C5xi | 123.5 (3) |
O3i—K1—Cl1—K1xii | 0.0 | C4xi—C3—C4—C5xi | −56.5 (3) |
O1ii—K1—Cl1—K1xii | 125.13 (5) | C2—C3—C4—C5xi | 40.6 (3) |
O1iii—K1—Cl1—K1xii | −125.13 (5) | C2xi—C3—C4—C5xi | 68.0 (4) |
O1iv—K1—Cl1—K1xii | −74.13 (12) | C3xi—C3—C4—Cl1 | −105.2 (3) |
O1v—K1—Cl1—K1xii | 74.13 (12) | C4xi—C3—C4—Cl1 | 74.8 (3) |
S1iv—K1—Cl1—K1xii | 0.000 (1) | C2—C3—C4—Cl1 | 171.9 (3) |
Cl1vi—K1—Cl1—K1xii | 180.0 | C2xi—C3—C4—Cl1 | −160.7 (4) |
Cl1vii—K1—Cl1—K1xii | −65.031 (18) | K1—Cl1—C4—C4xi | 91.56 (15) |
Cl1viii—K1—Cl1—K1xii | 65.031 (18) | K1xii—Cl1—C4—C4xi | −93.19 (18) |
K1ix—K1—Cl1—K1xii | −109.66 (3) | K1vii—Cl1—C4—C4xi | −173.67 (15) |
K1x—K1—Cl1—K1xii | 109.66 (3) | K1viii—Cl1—C4—C4xi | −6.81 (15) |
O3i—K1—Cl1—K1vii | 65.031 (18) | C4xi—Cl1—C4—C3xi | −94.5 (6) |
O1ii—K1—Cl1—K1vii | −169.83 (5) | K1—Cl1—C4—C3xi | −2.9 (6) |
O1iii—K1—Cl1—K1vii | −60.10 (5) | K1xii—Cl1—C4—C3xi | 172.3 (5) |
O1iv—K1—Cl1—K1vii | −9.10 (11) | K1vii—Cl1—C4—C3xi | 91.9 (6) |
O1v—K1—Cl1—K1vii | 139.16 (12) | K1viii—Cl1—C4—C3xi | −101.3 (6) |
S1iv—K1—Cl1—K1vii | 65.031 (19) | C4xi—Cl1—C4—C5 | 104.46 (18) |
Cl1vi—K1—Cl1—K1vii | −114.969 (18) | K1—Cl1—C4—C5 | −163.98 (18) |
Cl1vii—K1—Cl1—K1vii | 0.0 | K1xii—Cl1—C4—C5 | 11.3 (3) |
Cl1viii—K1—Cl1—K1vii | 130.06 (4) | K1vii—Cl1—C4—C5 | −69.2 (2) |
K1ix—K1—Cl1—K1vii | −44.63 (3) | K1viii—Cl1—C4—C5 | 97.7 (2) |
K1x—K1—Cl1—K1vii | 174.69 (4) | C4xi—Cl1—C4—C3 | −67.25 (16) |
O3i—K1—Cl1—K1viii | −65.031 (18) | K1—Cl1—C4—C3 | 24.3 (2) |
O1ii—K1—Cl1—K1viii | 60.10 (5) | K1xii—Cl1—C4—C3 | −160.44 (14) |
O1iii—K1—Cl1—K1viii | 169.83 (5) | K1vii—Cl1—C4—C3 | 119.08 (18) |
O1iv—K1—Cl1—K1viii | −139.16 (12) | K1viii—Cl1—C4—C3 | −74.1 (2) |
O1v—K1—Cl1—K1viii | 9.10 (11) | C4xi—Cl1—C4—C5xi | 59.0 (4) |
S1iv—K1—Cl1—K1viii | −65.031 (19) | K1—Cl1—C4—C5xi | 150.6 (3) |
Cl1vi—K1—Cl1—K1viii | 114.969 (18) | K1xii—Cl1—C4—C5xi | −34.2 (5) |
Cl1vii—K1—Cl1—K1viii | −130.06 (4) | K1vii—Cl1—C4—C5xi | −114.7 (4) |
Cl1viii—K1—Cl1—K1viii | 0.0 | K1viii—Cl1—C4—C5xi | 52.2 (4) |
K1ix—K1—Cl1—K1viii | −174.69 (4) | C4xi—C4—C5—C5xi | 0.0 |
K1x—K1—Cl1—K1viii | 44.63 (3) | C3xi—C4—C5—C5xi | 104.0 (4) |
O3—S1—O1—K1iii | 12.9 (3) | C3—C4—C5—C5xi | 77.8 |
O1xi—S1—O1—K1iii | −116.33 (19) | Cl1—C4—C5—C5xi | −93.7 (3) |
C1—S1—O1—K1iii | 129.01 (19) | C4xi—C4—C5—C6 | −77.8 |
K1xiii—S1—O1—K1iii | −119.1 (2) | C3xi—C4—C5—C6 | 26.2 (4) |
O3—S1—O1—K1xiii | 131.96 (13) | C3—C4—C5—C6 | 0.0 |
O1xi—S1—O1—K1xiii | 2.75 (18) | C5xi—C4—C5—C6 | −77.8 |
C1—S1—O1—K1xiii | −111.92 (10) | Cl1—C4—C5—C6 | −171.5 (3) |
O1xi—S1—O3—K1xiv | 63.94 (11) | C3xi—C4—C5—C4xi | 104.0 (4) |
O1—S1—O3—K1xiv | −63.94 (11) | C3—C4—C5—C4xi | 77.8 |
C1—S1—O3—K1xiv | 180.0 | C5xi—C4—C5—C4xi | 0.0 |
K1xiii—S1—O3—K1xiv | 0.0 | Cl1—C4—C5—C4xi | −93.7 (3) |
O3—S1—C1—C2 | −17.16 (15) | C4xi—C4—C5—C6xi | −47.66 (15) |
O1xi—S1—C1—C2 | 103.86 (19) | C3xi—C4—C5—C6xi | 56.4 (5) |
O1—S1—C1—C2 | −138.18 (18) | C3—C4—C5—C6xi | 30.14 (15) |
K1xiii—S1—C1—C2 | 162.84 (15) | C5xi—C4—C5—C6xi | −47.66 (15) |
O3—S1—C1—C2xi | 17.16 (13) | Cl1—C4—C5—C6xi | −141.4 (4) |
O1xi—S1—C1—C2xi | 138.18 (16) | C5xi—C5—C6—C6xi | 0.0 |
O1—S1—C1—C2xi | −103.86 (17) | C4—C5—C6—C6xi | 71.2 |
K1xiii—S1—C1—C2xi | −162.84 (13) | C4xi—C5—C6—C6xi | 59.7 (4) |
O3—S1—C1—C6xi | −159.59 (12) | C5xi—C5—C6—C1 | −71.2 |
O1xi—S1—C1—C6xi | −38.57 (16) | C4—C5—C6—C1 | 0.0 |
O1—S1—C1—C6xi | 79.39 (15) | C4xi—C5—C6—C1 | −11.5 (4) |
K1xiii—S1—C1—C6xi | 20.41 (12) | C6xi—C5—C6—C1 | −71.2 |
O3—S1—C1—C6 | 159.59 (15) | C4—C5—C6—C5xi | 71.2 |
O1xi—S1—C1—C6 | −79.39 (17) | C4xi—C5—C6—C5xi | 59.7 (4) |
O1—S1—C1—C6 | 38.57 (18) | C6xi—C5—C6—C5xi | 0.0 |
K1xiii—S1—C1—C6 | −20.41 (15) | C2—C1—C6—C6xi | −82.9 |
C6xi—C1—C2—C2xi | −115.6 (2) | C2xi—C1—C6—C6xi | −113.7 (2) |
C6—C1—C2—C2xi | −77.8 | S1—C1—C6—C6xi | 100.33 (14) |
S1—C1—C2—C2xi | 98.93 (14) | C2—C1—C6—C5 | 0.0 |
C2xi—C1—C2—C3 | 77.8 | C2xi—C1—C6—C5 | −30.8 (2) |
C6xi—C1—C2—C3 | −37.8 (2) | C6xi—C1—C6—C5 | 82.9 |
C6—C1—C2—C3 | 0.0 | S1—C1—C6—C5 | −176.76 (14) |
S1—C1—C2—C3 | 176.72 (14) | C2—C1—C6—C5xi | −35.2 (2) |
C2xi—C1—C2—C3xi | 55.7 (3) | C2xi—C1—C6—C5xi | −66.0 (3) |
C6xi—C1—C2—C3xi | −59.9 (4) | C6xi—C1—C6—C5xi | 47.7 (2) |
C6—C1—C2—C3xi | −22.1 (3) | S1—C1—C6—C5xi | 148.04 (16) |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z+1; (v) x+1, −y+1/2, z+1; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+2; (viii) −x+1, −y, −z+2; (ix) −x+2, −y+1, −z+2; (x) −x+2, −y, −z+2; (xi) x, −y+1/2, z; (xii) x−1, y, z; (xiii) x−1, y, z−1; (xiv) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [K(C6H4ClO3S)] |
Mr | 230.70 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 303 |
a, b, c (Å) | 6.1688 (6), 6.813 (1), 9.804 (1) |
β (°) | 97.236 (8) |
V (Å3) | 408.76 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.19 |
Crystal size (mm) | 0.44 × 0.32 × 0.06 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.623, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6343, 912, 799 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.098, 1.09 |
No. of reflections | 912 |
No. of parameters | 73 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.53 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek 2003) and ORTEP-3 (Farrugia, 1997), SHELXL97.
As part of a study on the substituent effects on the solid state structures of chemically and biologically significant compounds (Gowda et al., 2003, Gowda, Jyothi et al., 2007; Gowda, Kozisek et al., 2007; Gowda, Nayak et al., 2007), in the present work, the structure of potassium 4-chloro-benzenesulfonate (K4CBS) has been determined. The structure of K4CBS (Fig. 1) resembles that of silver 4-chloro-benzenesulfonate (Ag4CBS) with somewhat different geometric parameters (Bernardinelli et al., 1991). K4CBS crystallizes in monoclinic P21/m space group compared to the monoclinic P21/c space group observed for Ag4CBS ((Bernardinelli et al., 1991). The potassium ion shows hepta coordination with two Chloro ligands and five sulfonato O atoms of four different 4-chloro-benzenesulfonato anions, one of them in a monodentate and three in a bidentate way (Fig. 2). This potassium coordination therefore results in a three dimensional supramolecular structure (Fig. 2). The benzene rings are disordered over two different conformations with site occupation factors of 0.5 each.