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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
CCDC reference: 193789
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
Crystal data top
2C5H6N+·C14H8O4S22− | F(000) = 968 |
Mr = 464.54 | Dx = 1.350 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0936 (4) Å | Cell parameters from 1954 reflections |
b = 12.9825 (6) Å | θ = 1.9–25.0° |
c = 21.9157 (10) Å | µ = 0.27 mm−1 |
β = 96.882 (1)° | T = 293 K |
V = 2286.20 (19) Å3 | Rectangular, yellow |
Z = 4 | 0.68 × 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 tube | Rint = 0.035 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
φ and ω scans | h = −9→9 |
3703 measured reflections | k = −15→10 |
1980 independent reflections | l = −21→25 |
Refinement top
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-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 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S | 0.03728 (16) | 0.10521 (9) | 0.29678 (5) | 0.0583 (4) | |
O2 | 0.1335 (5) | 0.0964 (3) | 0.41821 (15) | 0.0838 (11) | |
C1 | −0.0795 (5) | 0.2199 (3) | 0.39083 (19) | 0.0511 (10) | |
O1 | 0.0294 (5) | 0.1798 (3) | 0.49322 (14) | 0.0903 (12) | |
C2 | −0.0896 (5) | 0.2023 (3) | 0.32677 (18) | 0.0491 (10) | |
C3 | −0.2003 (6) | 0.2618 (3) | 0.2881 (2) | 0.0629 (12) | |
H3A | −0.2099 | 0.2512 | 0.2459 | 0.075* | |
C7 | 0.0388 (6) | 0.1595 (4) | 0.4350 (2) | 0.0604 (12) | |
C6 | −0.1797 (6) | 0.2944 (4) | 0.4132 (2) | 0.0668 (13) | |
H6A | −0.1728 | 0.3053 | 0.4553 | 0.080* | |
N | 0.2398 (6) | 0.0688 (4) | 0.56874 (18) | 0.0800 (13) | |
H0A | 0.1710 | 0.1055 | 0.5449 | 0.096* | |
C4 | −0.2958 (7) | 0.3362 (4) | 0.3117 (2) | 0.0749 (14) | |
H4A | −0.3664 | 0.3765 | 0.2850 | 0.090* | |
C12 | 0.3266 (8) | −0.0048 (5) | 0.5467 (3) | 0.0906 (17) | |
H12A | 0.3111 | −0.0167 | 0.5045 | 0.109* | |
C5 | −0.2892 (7) | 0.3524 (4) | 0.3742 (2) | 0.0783 (15) | |
H5A | −0.3570 | 0.4013 | 0.3897 | 0.094* | |
C9 | 0.3702 (8) | 0.0277 (6) | 0.6683 (3) | 0.097 (2) | |
H9A | 0.3817 | 0.0397 | 0.7104 | 0.117* | |
C10 | 0.4600 (8) | −0.0467 (6) | 0.6436 (3) | 0.105 (2) | |
H10A | 0.5366 | −0.0850 | 0.6692 | 0.126* | |
C8 | 0.2611 (8) | 0.0847 (6) | 0.6284 (3) | 0.098 (2) | |
H8A | 0.2000 | 0.1366 | 0.6444 | 0.117* | |
C11 | 0.4408 (8) | −0.0661 (5) | 0.5829 (3) | 0.100 (2) | |
H11A | 0.5006 | −0.1178 | 0.5660 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0789 (8) | 0.0502 (7) | 0.0468 (6) | 0.0117 (6) | 0.0113 (5) | 0.0035 (5) |
O2 | 0.099 (3) | 0.096 (3) | 0.0537 (19) | 0.044 (2) | −0.0023 (18) | 0.0004 (18) |
C1 | 0.051 (2) | 0.051 (2) | 0.051 (2) | 0.001 (2) | 0.0053 (19) | −0.0029 (19) |
O1 | 0.110 (3) | 0.117 (3) | 0.0429 (18) | 0.036 (2) | 0.0024 (18) | −0.0061 (19) |
C2 | 0.055 (2) | 0.044 (2) | 0.049 (2) | 0.0014 (19) | 0.0064 (19) | −0.0016 (18) |
C3 | 0.076 (3) | 0.057 (3) | 0.052 (3) | 0.012 (2) | −0.005 (2) | 0.000 (2) |
C7 | 0.066 (3) | 0.067 (3) | 0.047 (2) | 0.006 (3) | 0.004 (2) | 0.000 (2) |
C6 | 0.075 (3) | 0.068 (3) | 0.058 (3) | 0.011 (3) | 0.008 (2) | −0.010 (2) |
N | 0.084 (3) | 0.107 (4) | 0.046 (2) | −0.004 (3) | −0.005 (2) | 0.007 (2) |
C4 | 0.079 (3) | 0.067 (3) | 0.075 (3) | 0.025 (3) | −0.005 (3) | 0.005 (3) |
C12 | 0.098 (4) | 0.096 (4) | 0.075 (4) | 0.002 (4) | −0.001 (3) | −0.002 (3) |
C5 | 0.083 (4) | 0.075 (3) | 0.078 (4) | 0.027 (3) | 0.010 (3) | −0.011 (3) |
C9 | 0.088 (4) | 0.136 (6) | 0.063 (3) | −0.001 (4) | −0.013 (3) | 0.001 (4) |
C10 | 0.086 (4) | 0.119 (6) | 0.106 (5) | −0.008 (4) | −0.006 (4) | 0.022 (5) |
C8 | 0.088 (4) | 0.136 (6) | 0.066 (3) | 0.005 (4) | −0.002 (3) | −0.014 (4) |
C11 | 0.094 (5) | 0.112 (5) | 0.093 (5) | −0.007 (4) | 0.001 (4) | 0.004 (4) |
Geometric parameters (Å, º) top
S—C2 | 1.799 (4) | C6—C5 | 1.378 (7) |
S—Si | 2.067 (2) | N—C8 | 1.314 (6) |
O2—C7 | 1.208 (5) | N—C12 | 1.313 (7) |
C1—C6 | 1.389 (6) | C4—C5 | 1.381 (7) |
C1—C2 | 1.415 (6) | C12—C11 | 1.394 (8) |
C1—C7 | 1.499 (6) | C9—C10 | 1.360 (9) |
O1—C7 | 1.313 (5) | C9—C8 | 1.380 (8) |
C2—C3 | 1.391 (6) | C10—C11 | 1.343 (9) |
C3—C4 | 1.376 (6) | | |
| | | |
C2—S—Si | 104.52 (14) | O1—C7—C1 | 114.5 (4) |
C6—C1—C2 | 119.7 (4) | C5—C6—C1 | 121.5 (5) |
C6—C1—C7 | 119.4 (4) | C8—N—C12 | 117.9 (5) |
C2—C1—C7 | 120.9 (4) | C3—C4—C5 | 121.6 (5) |
C3—C2—C1 | 118.1 (4) | N—C12—C11 | 123.6 (6) |
C3—C2—S | 121.4 (3) | C6—C5—C4 | 118.4 (5) |
C1—C2—S | 120.5 (3) | C10—C9—C8 | 117.4 (6) |
C4—C3—C2 | 120.7 (4) | C11—C10—C9 | 121.6 (7) |
O2—C7—O1 | 123.0 (4) | N—C8—C9 | 123.0 (6) |
O2—C7—C1 | 122.4 (4) | C10—C11—C12 | 116.5 (7) |
| | | |
C2—S—Si—C2i | 87.3 (3) | | |
Symmetry code: (i) −x, y, −z+1/2. |
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