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In the centrosymmetric mol­ecule of the title compound, C14H14O2S2, the benzo[1,2-b:4,5-b′]difuran group is almost planar. The structure is stabilized by aromatic π–π stacking and —CH2—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021611/hk2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021611/hk2047Isup2.hkl
Contains datablock I

CCDC reference: 613717

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.147
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED32 (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

2,6-Dimethyl-3,7-bis(methylsulfanyl)benzo[1,2 - b:4,5 - b']difuran top
Crystal data top
C14H14O2S2Z = 1
Mr = 278.37F(000) = 146
Triclinic, P1Dx = 1.384 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 5.2073 (5) ÅCell parameters from 29 reflections
b = 8.2548 (6) Åθ = 9.5–10.9°
c = 8.5234 (6) ŵ = 0.39 mm1
α = 105.616 (6)°T = 298 K
β = 98.690 (7)°Prism, colorless
γ = 103.564 (6)°0.50 × 0.31 × 0.29 mm
V = 333.91 (5) Å3
Data collection top
Stoe Stadi-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 66
ω/2–θ scansk = 1010
1530 measured reflectionsl = 011
1530 independent reflections3 standard reflections every 60 min
1339 reflections with I > 2σ(I) intensity decay: 1.6%
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0799P)2 + 0.3086P]
where P = (Fo2 + 2Fc2)/3
1530 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.41 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
S10.69578 (13)0.44296 (8)0.20744 (9)0.0479 (3)
O10.3839 (3)0.0308 (2)0.2344 (2)0.0409 (4)
C10.0568 (5)0.1670 (3)0.0343 (3)0.0378 (5)
H10.08980.27290.05730.045*
C20.1767 (5)0.0291 (3)0.1131 (3)0.0360 (5)
C30.2385 (5)0.1336 (3)0.0827 (3)0.0354 (5)
C40.4998 (5)0.2346 (3)0.1951 (3)0.0380 (5)
C50.5758 (5)0.1314 (3)0.2821 (3)0.0396 (5)
C60.8191 (5)0.1595 (4)0.4122 (4)0.0508 (6)
H6A0.80400.05620.44590.061*
H6B0.83330.25800.50720.061*
H6C0.97800.18230.36800.061*
C70.4906 (7)0.5804 (4)0.2864 (4)0.0602 (8)
H7A0.58000.70030.29850.072*
H7B0.46550.57110.39330.072*
H7C0.31720.54290.20950.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0395 (4)0.0336 (4)0.0666 (5)0.0045 (2)0.0132 (3)0.0144 (3)
O10.0454 (9)0.0345 (8)0.0432 (9)0.0115 (7)0.0057 (7)0.0153 (7)
C10.0449 (13)0.0269 (10)0.0428 (12)0.0086 (9)0.0119 (10)0.0132 (9)
C20.0413 (12)0.0312 (11)0.0369 (11)0.0108 (9)0.0107 (9)0.0118 (9)
C30.0396 (11)0.0274 (10)0.0384 (11)0.0077 (9)0.0117 (9)0.0093 (8)
C40.0392 (11)0.0308 (11)0.0424 (12)0.0076 (9)0.0120 (9)0.0100 (9)
C50.0398 (12)0.0360 (12)0.0399 (12)0.0109 (9)0.0092 (9)0.0069 (9)
C60.0462 (14)0.0536 (15)0.0510 (15)0.0174 (12)0.0060 (11)0.0143 (12)
C70.0611 (18)0.0392 (14)0.078 (2)0.0173 (13)0.0151 (15)0.0120 (13)
Geometric parameters (Å, º) top
S1—C41.749 (2)C3—C41.452 (3)
S1—C71.805 (3)C4—C51.357 (3)
O1—C21.383 (3)C5—C61.479 (3)
O1—C51.383 (3)C6—H6A0.9600
C1—C21.385 (3)C6—H6B0.9600
C1—C3i1.397 (3)C6—H6C0.9600
C1—H10.9300C7—H7A0.9600
C2—C31.408 (3)C7—H7B0.9600
C3—C1i1.397 (3)C7—H7C0.9600
C4—S1—C7102.1 (1)C4—C5—C6132.6 (2)
C2—O1—C5106.8 (2)O1—C5—C6116.3 (2)
C2—C1—C3i114.4 (2)C5—C6—H6A109.5
C2—C1—H1122.8C5—C6—H6B109.5
C3i—C1—H1122.8H6A—C6—H6B109.5
O1—C2—C1124.8 (2)C5—C6—H6C109.5
O1—C2—C3109.8 (2)H6A—C6—H6C109.5
C1—C2—C3125.4 (2)H6B—C6—H6C109.5
C1i—C3—C2120.3 (2)S1—C7—H7A109.5
C1i—C3—C4134.5 (2)S1—C7—H7B109.5
C2—C3—C4105.2 (2)H7A—C7—H7B109.5
C5—C4—C3107.0 (2)S1—C7—H7C109.5
C5—C4—S1125.5 (2)H7A—C7—H7C109.5
C3—C4—S1127.3 (2)H7B—C7—H7C109.5
C4—C5—O1111.2 (2)
C3—C2—O1—C50.6 (2)C5—C4—C3—C20.0 (3)
C2—O1—C5—C40.6 (3)C4—C3—C2—O10.4 (2)
O1—C5—C4—C30.3 (2)
Symmetry code: (i) x, y, z.
 

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