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The title mol­ecule, C14H12O4S8, has a U-shaped conformation and its crystal structure feaures short inter­molecular S...S contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007161/tk2005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007161/tk2005Isup2.hkl
Contains datablock I

CCDC reference: 608504

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.026
  • wR factor = 0.060
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.10 Deg.
Author Response: ..The rather low theta full is due to the used apparatus. The Stoe IPDS because of the fixed phi spindle does not allow easy access to the cusp of data along the mount axis. This is an instrumentation-based restriction, which we have little control over.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93
Author Response: ...The rather low theta full is due to the used apparatus. The Stoe IPDS because of the fixed phi spindle does not allow easy access to the cusp of data along the mount axis. This is an instrumentation-based restriction, which we have little control over.

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5745
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 24.10 From the CIF: _diffrn_reflns_theta_full 24.10 From the CIF: _reflns_number_total 2733 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2963 Completeness (_total/calc) 92.24% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.10 Deg. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: IPDS Software (Stoe, 1996); cell refinement: IPDS Software; data reduction: X-RED (Stoe, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4,5;4',5'-bis(dioxane-1,4-diyl-2,3-dithio)tetrathiafulvalene top
Crystal data top
C14H12O4S8Z = 2
Mr = 500.72F(000) = 512
Triclinic, P1Dx = 1.783 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3867 (7) ÅCell parameters from 8000 reflections
b = 11.0716 (13) Åθ = 1.7–26.1°
c = 14.1462 (16) ŵ = 0.98 mm1
α = 106.009 (11)°T = 180 K
β = 90.107 (12)°Plate, orange–yellow
γ = 103.453 (12)°0.5 × 0.3 × 0.02 mm
V = 932.78 (18) Å3
Data collection top
Stoe IPDS
diffractometer
2733 independent reflections
Radiation source: fine-focus sealed tube2225 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ scansθmax = 24.1°, θmin = 2.0°
Absorption correction: multi-scan
(Blessing, 1995)
h = 66
Tmin = 0.712, Tmax = 0.979k = 1212
7398 measured reflectionsl = 1616
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0364P)2]
where P = (Fo2 + 2Fc2)/3
2733 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.28 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
C10.5883 (4)0.07113 (19)0.12969 (15)0.0150 (5)
C20.6865 (4)0.0104 (2)0.21550 (15)0.0164 (5)
C30.5017 (4)0.20101 (19)0.05357 (15)0.0160 (5)
C40.3127 (4)0.2170 (2)0.01319 (15)0.0173 (5)
C50.9444 (4)0.20572 (19)0.33307 (14)0.0140 (5)
C60.7574 (4)0.1947 (2)0.37568 (15)0.0158 (5)
C70.3319 (4)0.4177 (2)0.22100 (16)0.0208 (5)
H70.24010.40780.27260.025*
C80.1844 (4)0.4514 (2)0.14301 (16)0.0210 (5)
H80.06370.52330.17680.025*
C91.1541 (4)0.3042 (2)0.51084 (15)0.0163 (5)
H91.28730.35570.55060.02*
C100.9671 (4)0.3515 (2)0.56182 (15)0.0176 (5)
H101.01080.44630.58010.021*
C110.5316 (4)0.5621 (2)0.19549 (19)0.0303 (6)
H11A0.65130.49310.15940.036*
H11B0.58850.63520.22950.036*
C120.3742 (5)0.6013 (2)0.12472 (19)0.0315 (6)
H12A0.25750.67310.16010.038*
H12B0.44570.62940.0770.038*
C131.1188 (5)0.1488 (2)0.59729 (17)0.0298 (6)
H13A1.24370.20030.64140.036*
H13B1.110.05820.59070.036*
C140.9190 (5)0.1837 (2)0.63898 (18)0.0335 (7)
H14A0.79430.1310.59520.04*
H14B0.90170.1660.70240.04*
O10.4305 (3)0.51882 (15)0.26616 (11)0.0256 (4)
O20.2891 (3)0.49318 (14)0.07471 (11)0.0241 (4)
O31.1416 (3)0.17242 (14)0.50242 (11)0.0214 (4)
O40.9314 (3)0.31811 (15)0.65083 (10)0.0243 (4)
S10.73390 (10)0.11429 (5)0.02499 (4)0.01928 (15)
S20.31341 (10)0.15205 (5)0.11500 (4)0.02103 (15)
S30.96642 (10)0.07803 (5)0.23044 (4)0.01908 (15)
S40.55056 (10)0.05490 (5)0.32345 (4)0.01799 (15)
S50.54342 (11)0.26324 (5)0.17755 (4)0.02258 (16)
S60.07267 (11)0.31886 (6)0.07728 (4)0.02771 (17)
S71.17817 (10)0.32490 (5)0.38831 (4)0.01849 (15)
S80.70916 (10)0.30355 (6)0.48407 (4)0.02335 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0171 (14)0.0120 (10)0.0146 (11)0.0033 (9)0.0020 (9)0.0017 (8)
C20.0169 (15)0.0165 (11)0.0144 (11)0.0023 (9)0.0007 (9)0.0037 (9)
C30.0200 (15)0.0143 (11)0.0126 (11)0.0047 (9)0.0004 (9)0.0018 (9)
C40.0171 (15)0.0173 (11)0.0158 (11)0.0073 (9)0.0029 (9)0.0008 (9)
C50.0164 (15)0.0139 (10)0.0099 (10)0.0020 (9)0.0012 (9)0.0019 (8)
C60.0162 (15)0.0180 (11)0.0121 (11)0.0054 (9)0.0010 (9)0.0013 (9)
C70.0211 (15)0.0210 (12)0.0165 (11)0.0063 (10)0.0047 (10)0.0022 (9)
C80.0130 (15)0.0225 (12)0.0215 (12)0.0032 (10)0.0031 (9)0.0026 (10)
C90.0148 (14)0.0179 (11)0.0120 (11)0.0018 (9)0.0012 (9)0.0008 (9)
C100.0118 (14)0.0215 (12)0.0140 (11)0.0008 (9)0.0021 (9)0.0009 (9)
C110.0236 (18)0.0253 (13)0.0374 (15)0.0124 (11)0.0038 (12)0.0039 (11)
C120.040 (2)0.0194 (12)0.0329 (14)0.0095 (11)0.0054 (12)0.0023 (10)
C130.044 (2)0.0264 (13)0.0207 (12)0.0081 (12)0.0049 (11)0.0089 (10)
C140.0383 (19)0.0385 (15)0.0202 (13)0.0051 (12)0.0001 (11)0.0145 (11)
O10.0260 (11)0.0239 (9)0.0209 (8)0.0067 (7)0.0032 (7)0.0039 (7)
O20.0283 (12)0.0194 (8)0.0231 (8)0.0054 (7)0.0011 (7)0.0038 (7)
O30.0272 (11)0.0180 (8)0.0189 (8)0.0083 (7)0.0008 (7)0.0030 (6)
O40.0235 (11)0.0333 (9)0.0118 (8)0.0040 (7)0.0043 (7)0.0017 (7)
S10.0161 (4)0.0188 (3)0.0168 (3)0.0004 (2)0.0033 (2)0.0017 (2)
S20.0163 (4)0.0255 (3)0.0154 (3)0.0031 (2)0.0037 (2)0.0022 (2)
S30.0169 (4)0.0191 (3)0.0156 (3)0.0022 (2)0.0037 (2)0.0022 (2)
S40.0144 (4)0.0218 (3)0.0135 (3)0.0005 (2)0.0014 (2)0.0012 (2)
S50.0300 (4)0.0211 (3)0.0125 (3)0.0021 (3)0.0045 (2)0.0017 (2)
S60.0139 (4)0.0335 (3)0.0275 (3)0.0095 (3)0.0040 (2)0.0077 (3)
S70.0168 (4)0.0179 (3)0.0154 (3)0.0019 (2)0.0032 (2)0.0012 (2)
S80.0152 (4)0.0311 (3)0.0177 (3)0.0106 (3)0.0008 (2)0.0071 (2)
Geometric parameters (Å, º) top
C1—C21.345 (3)C9—O31.414 (3)
C1—S21.759 (2)C9—C101.519 (3)
C1—S11.763 (2)C9—S71.812 (2)
C2—S31.758 (2)C9—H90.98
C2—S41.766 (2)C10—O41.412 (3)
C3—C41.332 (3)C10—S81.863 (2)
C3—S51.744 (2)C10—H100.98
C3—S11.760 (2)C11—O11.432 (3)
C4—S61.752 (2)C11—C121.497 (4)
C4—S21.756 (2)C11—H11A0.97
C5—C61.334 (3)C11—H11B0.97
C5—S31.757 (2)C12—O21.438 (3)
C5—S71.758 (2)C12—H12A0.97
C6—S81.747 (2)C12—H12B0.97
C6—S41.761 (2)C13—O31.438 (3)
C7—O11.412 (3)C13—C141.494 (4)
C7—C81.520 (3)C13—H13A0.97
C7—S51.862 (2)C13—H13B0.97
C7—H70.98C14—O41.435 (3)
C8—O21.408 (3)C14—H14A0.97
C8—S61.807 (2)C14—H14B0.97
C8—H80.98
C2—C1—S2123.50 (18)O4—C10—H10106.2
C2—C1—S1121.62 (19)C9—C10—H10106.2
S2—C1—S1114.71 (11)S8—C10—H10106.2
C1—C2—S3122.21 (18)O1—C11—C12110.9 (2)
C1—C2—S4123.75 (19)O1—C11—H11A109.5
S3—C2—S4114.00 (11)C12—C11—H11A109.5
C4—C3—S5126.00 (17)O1—C11—H11B109.5
C4—C3—S1117.72 (16)C12—C11—H11B109.5
S5—C3—S1116.24 (13)H11A—C11—H11B108
C3—C4—S6123.41 (16)O2—C12—C11109.4 (2)
C3—C4—S2117.62 (17)O2—C12—H12A109.8
S6—C4—S2118.22 (14)C11—C12—H12A109.8
C6—C5—S3117.34 (16)O2—C12—H12B109.8
C6—C5—S7122.42 (16)C11—C12—H12B109.8
S3—C5—S7119.15 (13)H12A—C12—H12B108.2
C5—C6—S8124.65 (17)O3—C13—C14109.5 (2)
C5—C6—S4117.54 (15)O3—C13—H13A109.8
S8—C6—S4117.67 (13)C14—C13—H13A109.8
O1—C7—C8111.80 (19)O3—C13—H13B109.8
O1—C7—S5109.16 (17)C14—C13—H13B109.8
C8—C7—S5115.07 (14)H13A—C13—H13B108.2
O1—C7—H7106.8O4—C14—C13110.4 (2)
C8—C7—H7106.8O4—C14—H14A109.6
S5—C7—H7106.8C13—C14—H14A109.6
O2—C8—C7112.1 (2)O4—C14—H14B109.6
O2—C8—S6109.16 (14)C13—C14—H14B109.6
C7—C8—S6112.73 (16)H14A—C14—H14B108.1
O2—C8—H8107.5C7—O1—C11112.29 (17)
C7—C8—H8107.5C8—O2—C12110.44 (17)
S6—C8—H8107.5C9—O3—C13110.46 (16)
O3—C9—C10113.11 (18)C10—O4—C14112.40 (16)
O3—C9—S7107.57 (13)C3—S1—C194.21 (11)
C10—C9—S7112.84 (16)C4—S2—C194.44 (10)
O3—C9—H9107.7C5—S3—C293.03 (10)
C10—C9—H9107.7C6—S4—C292.79 (10)
S7—C9—H9107.7C3—S5—C7104.94 (10)
O4—C10—C9112.10 (19)C4—S6—C897.45 (11)
O4—C10—S8110.19 (15)C5—S7—C996.55 (10)
C9—C10—S8115.40 (14)C6—S8—C10104.25 (11)
 

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