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The title compound, C10H12S8, crystallizes in a monoclinic space group with one molecule in the asymmetric unit. All bond lengths and angles in the molecule are normal. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031769/cv6415sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031769/cv6415Isup2.hkl
Contains datablock I

CCDC reference: 262447

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.079
  • Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. S6 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. S8 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B .. S1 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10C .. S4 .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B .. S3 .. 2.98 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997–2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97.

4,4',5,5'-Tetrakis(methylsulfanyl)tetrathiafulvalene top
Crystal data top
C10H12S8F(000) = 800
Mr = 388.68Dx = 1.732 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.0010 (2) ÅCell parameters from 19853 reflections
b = 7.0811 (1) Åθ = 3.4–27.5°
c = 15.6584 (3) ŵ = 1.18 mm1
β = 106.213 (1)°T = 296 K
V = 1490.67 (4) Å3Block, orange
Z = 40.45 × 0.35 × 0.27 mm
Data collection top
Nonius KappaCCD
diffractometer
3521 independent reflections
Radiation source: fine-focus sealed tube2515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 9 pixels mm-1θmax = 27.9°, θmin = 3.5°
φ or ω scans?h = 1818
Absorption correction: empirical (using intensity measurements)
(Blessing, 1995)
k = 99
Tmin = 0.620, Tmax = 0.742l = 2020
33274 measured reflections
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0383P)2 + 0.2485P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3521 reflectionsΔρmax = 0.38 e Å3
163 parametersΔρmin = 0.38 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0134 (9)
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
S10.38160 (4)0.56949 (8)0.17051 (4)0.04475 (16)
S20.49020 (4)0.25570 (8)0.24089 (4)0.04678 (16)
S30.26402 (4)0.54055 (9)0.32811 (4)0.04963 (17)
S40.38388 (5)0.23792 (9)0.39745 (4)0.05367 (18)
S50.52939 (5)0.67385 (8)0.07204 (4)0.04526 (16)
S60.64932 (4)0.31553 (8)0.14828 (4)0.04037 (15)
S70.22441 (5)0.62280 (10)0.50320 (5)0.0624 (2)
S80.36593 (6)0.28489 (13)0.58361 (5)0.0795 (3)
C10.40249 (14)0.4084 (3)0.25144 (14)0.0378 (5)
C20.35611 (15)0.3986 (3)0.31602 (14)0.0401 (5)
C30.49566 (14)0.5341 (3)0.14575 (13)0.0343 (4)
C40.54498 (14)0.3898 (3)0.17754 (13)0.0337 (4)
C50.28543 (17)0.4968 (3)0.44257 (16)0.0471 (6)
C60.34107 (18)0.3592 (3)0.47454 (16)0.0488 (6)
C70.5099 (2)0.8795 (3)0.1168 (2)0.0719 (8)
H7A0.52570.98160.08280.108*
H7B0.55150.88680.17690.108*
H7C0.44140.88810.11650.108*
C80.7274 (2)0.2473 (4)0.25400 (17)0.0679 (8)
H8A0.78960.20170.24750.102*
H8B0.69560.14910.27830.102*
H8C0.73920.35420.29330.102*
C90.2912 (2)0.8203 (4)0.51300 (18)0.0623 (7)
H9A0.26660.91110.54710.093*
H9B0.28600.87070.45500.093*
H9C0.35960.79280.54250.093*
C100.4884 (2)0.2056 (5)0.6073 (2)0.0779 (9)
H10A0.50960.15980.66740.117*
H10B0.53070.30780.60040.117*
H10C0.49250.10540.56720.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0437 (3)0.0421 (3)0.0525 (3)0.0093 (2)0.0202 (3)0.0021 (2)
S20.0585 (3)0.0299 (3)0.0651 (4)0.0054 (2)0.0390 (3)0.0040 (2)
S30.0465 (3)0.0511 (3)0.0575 (4)0.0088 (3)0.0248 (3)0.0046 (3)
S40.0653 (4)0.0432 (3)0.0662 (4)0.0076 (3)0.0411 (3)0.0051 (3)
S50.0624 (4)0.0347 (3)0.0429 (3)0.0007 (3)0.0217 (3)0.0032 (2)
S60.0422 (3)0.0404 (3)0.0438 (3)0.0065 (2)0.0208 (2)0.0011 (2)
S70.0638 (4)0.0603 (4)0.0789 (5)0.0079 (3)0.0461 (4)0.0244 (3)
S80.0858 (5)0.1014 (6)0.0674 (5)0.0096 (4)0.0482 (4)0.0213 (4)
C10.0397 (11)0.0308 (10)0.0473 (12)0.0001 (8)0.0191 (10)0.0047 (9)
C20.0407 (11)0.0344 (11)0.0508 (13)0.0006 (9)0.0219 (10)0.0053 (9)
C30.0397 (11)0.0305 (10)0.0351 (11)0.0007 (8)0.0142 (9)0.0025 (8)
C40.0392 (10)0.0292 (10)0.0365 (11)0.0009 (8)0.0170 (9)0.0024 (8)
C50.0480 (13)0.0458 (13)0.0576 (14)0.0058 (11)0.0313 (11)0.0117 (11)
C60.0544 (13)0.0493 (14)0.0538 (14)0.0067 (11)0.0334 (11)0.0038 (11)
C70.094 (2)0.0278 (12)0.107 (2)0.0068 (13)0.0500 (18)0.0045 (13)
C80.0572 (16)0.088 (2)0.0592 (16)0.0287 (14)0.0177 (13)0.0160 (15)
C90.0762 (18)0.0428 (14)0.0710 (17)0.0024 (13)0.0260 (15)0.0058 (12)
C100.084 (2)0.083 (2)0.0621 (17)0.0021 (17)0.0126 (16)0.0018 (16)
Geometric parameters (Å, º) top
S1—C11.669 (2)C1—C21.348 (3)
S1—C31.763 (2)C3—C41.255 (3)
S2—C11.678 (2)C5—C61.261 (3)
S2—C41.703 (2)C7—H7A0.9600
S3—C21.687 (2)C7—H7B0.9600
S3—C51.760 (2)C7—H7C0.9600
S4—C21.672 (2)C8—H8A0.9600
S4—C61.720 (2)C8—H8B0.9600
S5—C71.671 (2)C8—H8C0.9600
S5—C31.6849 (19)C9—H9A0.9600
S6—C41.7305 (19)C9—H9B0.9600
S6—C81.777 (3)C9—H9C0.9600
S7—C91.665 (3)C10—H10A0.9600
S7—C51.697 (2)C10—H10B0.9600
S8—C61.727 (2)C10—H10C0.9600
S8—C101.743 (3)
C1—S1—C395.30 (9)S4—C6—S8121.91 (15)
C1—S2—C499.15 (10)S5—C7—H7A109.5
C2—S3—C595.23 (11)S5—C7—H7B109.5
C2—S4—C698.23 (11)H7A—C7—H7B109.5
C7—S5—C396.58 (12)S5—C7—H7C109.5
C4—S6—C8100.45 (11)H7A—C7—H7C109.5
C9—S7—C597.78 (12)H7B—C7—H7C109.5
C6—S8—C10102.90 (13)S6—C8—H8A109.5
C2—C1—S1125.86 (16)S6—C8—H8B109.5
C2—C1—S2124.06 (17)H8A—C8—H8B109.5
S1—C1—S2110.09 (12)S6—C8—H8C109.5
C1—C2—S4123.30 (16)H8A—C8—H8C109.5
C1—C2—S3126.68 (17)H8B—C8—H8C109.5
S4—C2—S3110.02 (12)S7—C9—H9A109.5
C4—C3—S5121.42 (16)S7—C9—H9B109.5
C4—C3—S1117.39 (16)H9A—C9—H9B109.5
S5—C3—S1120.75 (11)S7—C9—H9C109.5
C3—C4—S2113.43 (16)H9A—C9—H9C109.5
C3—C4—S6123.64 (16)H9B—C9—H9C109.5
S2—C4—S6122.38 (12)S8—C10—H10A109.5
C6—C5—S7122.4 (2)S8—C10—H10B109.5
C6—C5—S3116.81 (18)H10A—C10—H10B109.5
S7—C5—S3120.52 (15)S8—C10—H10C109.5
C5—C6—S4113.89 (19)H10A—C10—H10C109.5
C5—C6—S8124.03 (19)H10B—C10—H10C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···S6i0.962.943.612 (3)128
C9—H9A···S8i0.962.973.535 (3)119
C9—H9B···S1ii0.962.963.653 (3)130
C10—H10C···S4iii0.962.953.625 (3)129
C10—H10B···S3iv0.962.983.783 (3)142
C10—H10B···C2iv0.962.723.546 (4)145
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z+1; (iv) x+1, y+1, z+1.
 

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