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The title compound, 2C5H6N+·[C6H4(COO)2S]22- or 2C5H6N+·C14H8O4S22-, has a twofold axis of symmetry passing through the centre of the S-S bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013545/wn6110sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013545/wn6110Isup2.hkl
Contains datablock I

CCDC reference: 193789

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.071
  • wR factor = 0.185
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: XPREP in SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
2C5H6N+·C14H8O4S22F(000) = 968
Mr = 464.54Dx = 1.350 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 8.0936 (4) ÅCell parameters from 1954 reflections
b = 12.9825 (6) Åθ = 1.9–25.0°
c = 21.9157 (10) ŵ = 0.27 mm1
β = 96.882 (1)°T = 293 K
V = 2286.20 (19) Å3Rectangular, yellow
Z = 40.68 × 0.48 × 0.30 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1406 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
φ and ω scansh = 99
3703 measured reflectionsk = 1510
1980 independent reflectionsl = 2125
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters not refined
S = 1.15 w = 1/[σ2(Fo2) + (0.0504P)2 + 6.9607P]
where P = (Fo2 + 2Fc2)/3
1980 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.29 e Å3
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
S0.03728 (16)0.10521 (9)0.29678 (5)0.0583 (4)
O20.1335 (5)0.0964 (3)0.41821 (15)0.0838 (11)
C10.0795 (5)0.2199 (3)0.39083 (19)0.0511 (10)
O10.0294 (5)0.1798 (3)0.49322 (14)0.0903 (12)
C20.0896 (5)0.2023 (3)0.32677 (18)0.0491 (10)
C30.2003 (6)0.2618 (3)0.2881 (2)0.0629 (12)
H3A0.20990.25120.24590.075*
C70.0388 (6)0.1595 (4)0.4350 (2)0.0604 (12)
C60.1797 (6)0.2944 (4)0.4132 (2)0.0668 (13)
H6A0.17280.30530.45530.080*
N0.2398 (6)0.0688 (4)0.56874 (18)0.0800 (13)
H0A0.17100.10550.54490.096*
C40.2958 (7)0.3362 (4)0.3117 (2)0.0749 (14)
H4A0.36640.37650.28500.090*
C120.3266 (8)0.0048 (5)0.5467 (3)0.0906 (17)
H12A0.31110.01670.50450.109*
C50.2892 (7)0.3524 (4)0.3742 (2)0.0783 (15)
H5A0.35700.40130.38970.094*
C90.3702 (8)0.0277 (6)0.6683 (3)0.097 (2)
H9A0.38170.03970.71040.117*
C100.4600 (8)0.0467 (6)0.6436 (3)0.105 (2)
H10A0.53660.08500.66920.126*
C80.2611 (8)0.0847 (6)0.6284 (3)0.098 (2)
H8A0.20000.13660.64440.117*
C110.4408 (8)0.0661 (5)0.5829 (3)0.100 (2)
H11A0.50060.11780.56600.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0789 (8)0.0502 (7)0.0468 (6)0.0117 (6)0.0113 (5)0.0035 (5)
O20.099 (3)0.096 (3)0.0537 (19)0.044 (2)0.0023 (18)0.0004 (18)
C10.051 (2)0.051 (2)0.051 (2)0.001 (2)0.0053 (19)0.0029 (19)
O10.110 (3)0.117 (3)0.0429 (18)0.036 (2)0.0024 (18)0.0061 (19)
C20.055 (2)0.044 (2)0.049 (2)0.0014 (19)0.0064 (19)0.0016 (18)
C30.076 (3)0.057 (3)0.052 (3)0.012 (2)0.005 (2)0.000 (2)
C70.066 (3)0.067 (3)0.047 (2)0.006 (3)0.004 (2)0.000 (2)
C60.075 (3)0.068 (3)0.058 (3)0.011 (3)0.008 (2)0.010 (2)
N0.084 (3)0.107 (4)0.046 (2)0.004 (3)0.005 (2)0.007 (2)
C40.079 (3)0.067 (3)0.075 (3)0.025 (3)0.005 (3)0.005 (3)
C120.098 (4)0.096 (4)0.075 (4)0.002 (4)0.001 (3)0.002 (3)
C50.083 (4)0.075 (3)0.078 (4)0.027 (3)0.010 (3)0.011 (3)
C90.088 (4)0.136 (6)0.063 (3)0.001 (4)0.013 (3)0.001 (4)
C100.086 (4)0.119 (6)0.106 (5)0.008 (4)0.006 (4)0.022 (5)
C80.088 (4)0.136 (6)0.066 (3)0.005 (4)0.002 (3)0.014 (4)
C110.094 (5)0.112 (5)0.093 (5)0.007 (4)0.001 (4)0.004 (4)
Geometric parameters (Å, º) top
S—C21.799 (4)C6—C51.378 (7)
S—Si2.067 (2)N—C81.314 (6)
O2—C71.208 (5)N—C121.313 (7)
C1—C61.389 (6)C4—C51.381 (7)
C1—C21.415 (6)C12—C111.394 (8)
C1—C71.499 (6)C9—C101.360 (9)
O1—C71.313 (5)C9—C81.380 (8)
C2—C31.391 (6)C10—C111.343 (9)
C3—C41.376 (6)
C2—S—Si104.52 (14)O1—C7—C1114.5 (4)
C6—C1—C2119.7 (4)C5—C6—C1121.5 (5)
C6—C1—C7119.4 (4)C8—N—C12117.9 (5)
C2—C1—C7120.9 (4)C3—C4—C5121.6 (5)
C3—C2—C1118.1 (4)N—C12—C11123.6 (6)
C3—C2—S121.4 (3)C6—C5—C4118.4 (5)
C1—C2—S120.5 (3)C10—C9—C8117.4 (6)
C4—C3—C2120.7 (4)C11—C10—C9121.6 (7)
O2—C7—O1123.0 (4)N—C8—C9123.0 (6)
O2—C7—C1122.4 (4)C10—C11—C12116.5 (7)
C2—S—Si—C2i87.3 (3)
Symmetry code: (i) x, y, z+1/2.
 

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