The title compound, C
20H
18O
2S
2, was obtained from the reaction of 4,4′-biphenol with α-chloro-α-(methylsulfanyl)acetone in the presence of zinc chloride. The interplanar dihedral angle between the two 1-benzofuran groups is 39.2 (2)°. The structure is stabilized by π–π stacking and C—H
π interactions.
Supporting information
CCDC reference: 608497
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.103
- wR factor = 0.214
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.103
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (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.
2,2'-Dimethyl-3,3'-bis(methylsulfanyl)-5,5'-bis(1-benzofuran)
top
Crystal data top
C20H18O2S2 | Z = 2 |
Mr = 354.46 | F(000) = 372 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 7.830 (4) Å | Cell parameters from 32 reflections |
b = 8.695 (3) Å | θ = 9.5–10.5° |
c = 14.046 (6) Å | µ = 0.31 mm−1 |
α = 78.37 (3)° | T = 298 K |
β = 73.94 (4)° | Plate, colourless |
γ = 76.38 (3)° | 0.21 × 0.12 × 0.03 mm |
V = 883.5 (7) Å3 | |
Data collection top
Stoe STADI-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.5° |
Graphite monochromator | h = −9→10 |
ω/2θ scans | k = −10→11 |
4038 measured reflections | l = 0→18 |
4038 independent reflections | 3 standard reflections every 60 min |
1942 reflections with I > 2σ(I) | intensity decay: 3.4% |
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)] = 0.103 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0295P)2 + 2.2293P] where P = (Fo2 + 2Fc2)/3 |
4038 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.26 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 | |
S1 | 0.2924 (2) | 0.6183 (2) | 1.11528 (14) | 0.0584 (5) | |
S2 | 1.1866 (3) | 0.5054 (2) | 0.68479 (16) | 0.0697 (6) | |
O1 | 0.1294 (5) | 1.0868 (5) | 1.0649 (3) | 0.0517 (11) | |
O2 | 0.9996 (6) | 0.7753 (6) | 0.4603 (3) | 0.0646 (13) | |
C1 | 0.2449 (8) | 0.8213 (7) | 1.0696 (5) | 0.0449 (15) | |
C2 | 0.1265 (8) | 0.9348 (8) | 1.1214 (5) | 0.0483 (16) | |
C3 | 0.2531 (8) | 1.0648 (7) | 0.9751 (5) | 0.0443 (15) | |
C4 | 0.2994 (9) | 1.1809 (7) | 0.8969 (5) | 0.0543 (17) | |
H4 | 0.2476 | 1.2882 | 0.8999 | 0.065* | |
C5 | 0.4264 (9) | 1.1323 (8) | 0.8130 (5) | 0.0527 (17) | |
H5 | 0.4619 | 1.2092 | 0.7591 | 0.063* | |
C6 | 0.5037 (7) | 0.9700 (7) | 0.8067 (5) | 0.0427 (15) | |
C7 | 0.4532 (7) | 0.8563 (7) | 0.8878 (5) | 0.0452 (15) | |
H7 | 0.5030 | 0.7486 | 0.8851 | 0.054* | |
C8 | 0.3279 (7) | 0.9035 (7) | 0.9734 (4) | 0.0395 (14) | |
C9 | 0.1869 (10) | 0.5381 (8) | 1.0441 (6) | 0.068 (2) | |
H9A | 0.2046 | 0.4239 | 1.0617 | 0.102* | |
H9B | 0.2397 | 0.5648 | 0.9740 | 0.102* | |
H9C | 0.0596 | 0.5824 | 1.0581 | 0.102* | |
C10 | −0.0008 (9) | 0.9283 (9) | 1.2205 (5) | 0.0628 (19) | |
H10A | −0.1165 | 0.9924 | 1.2148 | 0.094* | |
H10B | 0.0448 | 0.9688 | 1.2654 | 0.094* | |
H10C | −0.0138 | 0.8196 | 1.2461 | 0.094* | |
C11 | 1.0728 (8) | 0.6416 (8) | 0.6027 (5) | 0.0514 (16) | |
C12 | 1.1214 (9) | 0.6555 (8) | 0.5032 (6) | 0.0583 (18) | |
C13 | 0.8696 (9) | 0.8370 (8) | 0.5387 (5) | 0.0510 (16) | |
C14 | 0.7260 (9) | 0.9593 (9) | 0.5303 (5) | 0.0621 (19) | |
H14 | 0.7074 | 1.0119 | 0.4684 | 0.074* | |
C15 | 0.6095 (9) | 1.0006 (8) | 0.6196 (5) | 0.0572 (18) | |
H15 | 0.5098 | 1.0828 | 0.6165 | 0.069* | |
C16 | 0.6343 (8) | 0.9250 (7) | 0.7137 (5) | 0.0456 (15) | |
C17 | 0.7856 (7) | 0.8011 (7) | 0.7179 (4) | 0.0420 (14) | |
H17 | 0.8060 | 0.7485 | 0.7794 | 0.050* | |
C18 | 0.9051 (8) | 0.7575 (7) | 0.6290 (5) | 0.0450 (15) | |
C19 | 1.3003 (12) | 0.6326 (10) | 0.7224 (7) | 0.100 (3) | |
H19A | 1.3666 | 0.5708 | 0.7700 | 0.150* | |
H19B | 1.2123 | 0.7174 | 0.7525 | 0.150* | |
H19C | 1.3823 | 0.6772 | 0.6648 | 0.150* | |
C20 | 1.2725 (10) | 0.5719 (10) | 0.4307 (6) | 0.083 (3) | |
H20A | 1.2608 | 0.6152 | 0.3638 | 0.125* | |
H20B | 1.2690 | 0.4598 | 0.4429 | 0.125* | |
H20C | 1.3855 | 0.5863 | 0.4384 | 0.125* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0642 (12) | 0.0511 (10) | 0.0589 (12) | −0.0045 (9) | −0.0238 (9) | −0.0008 (8) |
S2 | 0.0571 (12) | 0.0593 (12) | 0.0763 (14) | 0.0043 (9) | −0.0111 (10) | 0.0023 (10) |
O1 | 0.046 (3) | 0.048 (3) | 0.063 (3) | −0.002 (2) | −0.016 (2) | −0.016 (2) |
O2 | 0.060 (3) | 0.083 (4) | 0.051 (3) | −0.018 (3) | −0.009 (2) | −0.010 (3) |
C1 | 0.043 (3) | 0.043 (4) | 0.052 (4) | −0.003 (3) | −0.022 (3) | −0.007 (3) |
C2 | 0.044 (4) | 0.054 (4) | 0.057 (4) | −0.011 (3) | −0.024 (3) | −0.011 (3) |
C3 | 0.037 (3) | 0.044 (4) | 0.054 (4) | −0.004 (3) | −0.015 (3) | −0.012 (3) |
C4 | 0.051 (4) | 0.038 (4) | 0.070 (5) | 0.002 (3) | −0.017 (4) | −0.005 (3) |
C5 | 0.050 (4) | 0.045 (4) | 0.062 (4) | −0.009 (3) | −0.020 (3) | 0.003 (3) |
C6 | 0.032 (3) | 0.039 (3) | 0.058 (4) | −0.003 (3) | −0.016 (3) | −0.006 (3) |
C7 | 0.036 (3) | 0.039 (3) | 0.062 (4) | −0.004 (3) | −0.018 (3) | −0.004 (3) |
C8 | 0.032 (3) | 0.043 (4) | 0.044 (4) | 0.000 (3) | −0.015 (3) | −0.007 (3) |
C9 | 0.071 (5) | 0.058 (5) | 0.077 (5) | −0.007 (4) | −0.023 (4) | −0.014 (4) |
C10 | 0.059 (4) | 0.076 (5) | 0.057 (5) | −0.014 (4) | −0.009 (4) | −0.023 (4) |
C11 | 0.043 (4) | 0.057 (4) | 0.049 (4) | −0.011 (3) | −0.003 (3) | −0.007 (3) |
C12 | 0.048 (4) | 0.057 (4) | 0.067 (5) | −0.015 (3) | −0.003 (4) | −0.012 (4) |
C13 | 0.049 (4) | 0.059 (4) | 0.047 (4) | −0.014 (3) | −0.011 (3) | −0.008 (3) |
C14 | 0.064 (5) | 0.081 (5) | 0.043 (4) | −0.016 (4) | −0.023 (4) | 0.006 (4) |
C15 | 0.053 (4) | 0.060 (4) | 0.057 (5) | −0.009 (3) | −0.026 (4) | 0.009 (4) |
C16 | 0.040 (3) | 0.047 (4) | 0.053 (4) | −0.009 (3) | −0.016 (3) | −0.006 (3) |
C17 | 0.041 (3) | 0.038 (3) | 0.044 (4) | −0.005 (3) | −0.013 (3) | 0.003 (3) |
C18 | 0.039 (3) | 0.051 (4) | 0.044 (4) | −0.013 (3) | −0.010 (3) | −0.001 (3) |
C19 | 0.104 (7) | 0.090 (7) | 0.116 (8) | 0.018 (5) | −0.061 (6) | −0.030 (6) |
C20 | 0.067 (5) | 0.096 (6) | 0.083 (6) | −0.015 (5) | 0.003 (4) | −0.034 (5) |
Geometric parameters (Å, º) top
S1—C1 | 1.741 (6) | C9—H9C | 0.9600 |
S1—C9 | 1.783 (7) | C10—H10A | 0.9600 |
S2—C11 | 1.746 (7) | C10—H10B | 0.9600 |
S2—C19 | 1.804 (9) | C10—H10C | 0.9600 |
O1—C3 | 1.378 (7) | C11—C12 | 1.331 (9) |
O1—C2 | 1.399 (7) | C11—C18 | 1.461 (8) |
O2—C13 | 1.377 (8) | C12—C20 | 1.480 (9) |
O2—C12 | 1.398 (8) | C13—C14 | 1.367 (9) |
C1—C2 | 1.359 (8) | C13—C18 | 1.384 (8) |
C1—C8 | 1.450 (8) | C14—C15 | 1.389 (9) |
C2—C10 | 1.471 (9) | C14—H14 | 0.9300 |
C3—C4 | 1.365 (8) | C15—C16 | 1.396 (8) |
C3—C8 | 1.389 (8) | C15—H15 | 0.9300 |
C4—C5 | 1.382 (9) | C16—C17 | 1.407 (8) |
C4—H4 | 0.9300 | C17—C18 | 1.398 (8) |
C5—C6 | 1.409 (8) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.383 (8) | C19—H19B | 0.9600 |
C6—C16 | 1.477 (8) | C19—H19C | 0.9600 |
C7—C8 | 1.390 (8) | C20—H20A | 0.9600 |
C7—H7 | 0.9300 | C20—H20B | 0.9600 |
C9—H9A | 0.9600 | C20—H20C | 0.9600 |
C9—H9B | 0.9600 | | |
| | | |
C1—S1—C9 | 100.8 (3) | S1—C9—H9C | 109.5 |
C11—S2—C19 | 101.4 (4) | H9A—C9—H9C | 109.5 |
C3—O1—C2 | 106.4 (5) | H9B—C9—H9C | 109.5 |
C13—O2—C12 | 106.3 (5) | C2—C10—H10A | 109.5 |
C13—O2—O2i | 64.8 (3) | C2—C10—H10B | 109.5 |
C12—O2—O2i | 128.8 (3) | H10A—C10—H10B | 109.5 |
C2—C1—C8 | 106.9 (5) | C2—C10—H10C | 109.5 |
C2—C1—S1 | 125.3 (5) | H10A—C10—H10C | 109.5 |
C8—C1—S1 | 127.7 (5) | H10B—C10—H10C | 109.5 |
C1—C2—O1 | 110.5 (5) | C12—C11—C18 | 107.1 (6) |
C1—C2—C10 | 133.4 (6) | C12—C11—S2 | 125.7 (5) |
O1—C2—C10 | 116.1 (6) | C18—C11—S2 | 127.2 (5) |
C4—C3—O1 | 126.6 (6) | C11—C12—O2 | 111.0 (6) |
C4—C3—C8 | 123.0 (6) | C11—C12—C20 | 134.0 (7) |
O1—C3—C8 | 110.4 (5) | O2—C12—C20 | 115.0 (6) |
C3—C4—C5 | 117.2 (6) | C14—C13—O2 | 125.8 (6) |
C3—C4—H4 | 121.4 | C14—C13—C18 | 124.1 (6) |
C5—C4—H4 | 121.4 | O2—C13—C18 | 110.1 (6) |
C4—C5—C6 | 122.1 (6) | C13—C14—C15 | 116.1 (6) |
C4—C5—H5 | 119.0 | C14—C15—C16 | 123.3 (6) |
C6—C5—H5 | 119.0 | C15—C16—C17 | 118.1 (6) |
C7—C6—C5 | 118.8 (6) | C15—C16—C6 | 121.4 (6) |
C7—C6—C16 | 121.6 (5) | C17—C16—C6 | 120.5 (5) |
C5—C6—C16 | 119.5 (6) | C18—C17—C16 | 119.6 (6) |
C6—C7—C8 | 119.8 (6) | C13—C18—C17 | 118.7 (6) |
C6—C7—H7 | 120.1 | C13—C18—C11 | 105.4 (6) |
C8—C7—H7 | 120.1 | C17—C18—C11 | 135.8 (6) |
C3—C8—C7 | 119.1 (6) | H19A—C19—H19B | 109.5 |
C3—C8—C1 | 105.8 (5) | H19A—C19—H19C | 109.5 |
C7—C8—C1 | 135.1 (6) | H19B—C19—H19C | 109.5 |
S1—C9—H9A | 109.5 | H20A—C20—H20B | 109.5 |
S1—C9—H9B | 109.5 | H20A—C20—H20C | 109.5 |
H9A—C9—H9B | 109.5 | H20B—C20—H20C | 109.5 |
Symmetry code: (i) x−1, y, z. |