organic compounds
The title compound, C15H16O2S2, was prepared by the Lewis acid-catalysed reaction of 5-methylresorcinol with α-chloro-α-(methylsulfanyl)acetone. In the crystal structure, aromatic π–π stacking interactions are not observed between adjacent molecules, because of steric hindrance induced by the five methyl groups in the molecule.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032338/bh2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032338/bh2032Isup2.hkl |
CCDC reference: 620645
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.067
- wR factor = 0.167
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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.
2,4,7-Trimethyl-3,8-bis(methylsulfanyl)benzo[1,2 - b:5,6 - b']difuran top
Crystal data top
C15H16O2S2 | Z = 2 |
Mr = 292.40 | F(000) = 308 |
Triclinic, P1 | Dx = 1.342 Mg m−3 |
Hall symbol: -P 1 | Melting point = 375–377 K |
a = 7.7512 (6) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.8886 (8) Å | Cell parameters from 36 reflections |
c = 10.6471 (9) Å | θ = 8.7–14.0° |
α = 72.280 (8)° | µ = 0.36 mm−1 |
β = 71.435 (8)° | T = 298 K |
γ = 74.554 (7)° | Block, colourless |
V = 723.8 (1) Å3 | 0.32 × 0.25 × 0.23 mm |
Data collection top
Stoe Stadi-4 four-circle diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 2.1° |
Graphite monochromator | h = −9→10 |
ω/2θ scans | k = −11→12 |
3302 measured reflections | l = 0→13 |
3302 independent reflections | 3 standard reflections every 60 min |
2226 reflections with I > 2σ(I) | intensity decay: 2.4% |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.6399P] where P = (Fo2 + 2Fc2)/3 |
3302 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.26936 (15) | 0.03713 (12) | 1.20429 (10) | 0.0603 (3) | |
S2 | 0.25350 (16) | 0.24649 (12) | 0.47260 (10) | 0.0610 (3) | |
O1 | 0.2492 (3) | 0.0872 (2) | 0.8271 (2) | 0.0454 (6) | |
O2 | 0.2396 (4) | 0.5819 (3) | 0.6067 (2) | 0.0533 (6) | |
C1 | 0.2538 (5) | 0.0115 (4) | 0.9594 (3) | 0.0457 (8) | |
C2 | 0.2548 (5) | 0.1000 (4) | 1.0343 (3) | 0.0452 (8) | |
C3 | 0.2508 (4) | 0.2452 (4) | 0.9452 (3) | 0.0421 (7) | |
C4 | 0.2500 (5) | 0.3831 (4) | 0.9608 (3) | 0.0456 (8) | |
C5 | 0.2445 (5) | 0.4987 (4) | 0.8479 (4) | 0.0496 (8) | |
H5 | 0.2426 | 0.5911 | 0.8536 | 0.060* | |
C6 | 0.2419 (5) | 0.4757 (4) | 0.7265 (3) | 0.0458 (8) | |
C7 | 0.2442 (5) | 0.5141 (4) | 0.5094 (4) | 0.0501 (9) | |
C8 | 0.2478 (5) | 0.3710 (4) | 0.5627 (3) | 0.0472 (8) | |
C9 | 0.2456 (4) | 0.3435 (4) | 0.7058 (3) | 0.0413 (7) | |
C10 | 0.2481 (4) | 0.2286 (4) | 0.8201 (3) | 0.0408 (7) | |
C11 | 0.2545 (6) | −0.1454 (4) | 0.9912 (4) | 0.0596 (10) | |
H11A | 0.2826 | −0.1916 | 1.0776 | 0.089* | |
H11B | 0.3465 | −0.1867 | 0.9213 | 0.089* | |
H11C | 0.1348 | −0.1595 | 0.9954 | 0.089* | |
C12 | 0.0290 (7) | 0.0804 (6) | 1.2948 (4) | 0.0790 (14) | |
H12A | −0.0191 | 0.1805 | 1.2606 | 0.118* | |
H12B | 0.0192 | 0.0623 | 1.3904 | 0.118* | |
H12C | −0.0409 | 0.0214 | 1.2814 | 0.118* | |
C13 | 0.2546 (6) | 0.4082 (4) | 1.0926 (4) | 0.0583 (10) | |
H13A | 0.2434 | 0.5098 | 1.0827 | 0.087* | |
H13B | 0.3698 | 0.3573 | 1.1139 | 0.087* | |
H13C | 0.1536 | 0.3736 | 1.1649 | 0.087* | |
C14 | 0.2479 (6) | 0.6085 (5) | 0.3708 (4) | 0.0627 (11) | |
H14A | 0.3598 | 0.6472 | 0.3347 | 0.094* | |
H14B | 0.1428 | 0.6863 | 0.3756 | 0.094* | |
H14C | 0.2434 | 0.5531 | 0.3122 | 0.094* | |
C15 | 0.4977 (7) | 0.1847 (6) | 0.4163 (6) | 0.1006 (19) | |
H15A | 0.5560 | 0.2653 | 0.3615 | 0.151* | |
H15B | 0.5205 | 0.1159 | 0.3632 | 0.151* | |
H15C | 0.5476 | 0.1398 | 0.4941 | 0.151* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0710 (7) | 0.0648 (6) | 0.0474 (5) | −0.0144 (5) | −0.0272 (5) | −0.0027 (4) |
S2 | 0.0747 (7) | 0.0744 (7) | 0.0467 (5) | −0.0288 (5) | −0.0154 (5) | −0.0202 (5) |
O1 | 0.0522 (14) | 0.0439 (13) | 0.0439 (13) | −0.0121 (11) | −0.0130 (11) | −0.0129 (10) |
O2 | 0.0650 (17) | 0.0475 (14) | 0.0475 (14) | −0.0157 (12) | −0.0140 (12) | −0.0080 (11) |
C1 | 0.0412 (19) | 0.046 (2) | 0.0464 (19) | −0.0076 (15) | −0.0106 (15) | −0.0070 (15) |
C2 | 0.0462 (19) | 0.049 (2) | 0.0417 (18) | −0.0078 (15) | −0.0143 (15) | −0.0099 (15) |
C3 | 0.0410 (18) | 0.0457 (19) | 0.0406 (17) | −0.0091 (14) | −0.0106 (14) | −0.0111 (14) |
C4 | 0.0453 (19) | 0.051 (2) | 0.0434 (19) | −0.0081 (16) | −0.0098 (15) | −0.0188 (16) |
C5 | 0.055 (2) | 0.045 (2) | 0.053 (2) | −0.0107 (16) | −0.0125 (17) | −0.0183 (16) |
C6 | 0.050 (2) | 0.0423 (19) | 0.0445 (18) | −0.0094 (15) | −0.0119 (15) | −0.0088 (15) |
C7 | 0.053 (2) | 0.058 (2) | 0.0418 (19) | −0.0141 (17) | −0.0129 (16) | −0.0113 (16) |
C8 | 0.049 (2) | 0.057 (2) | 0.0388 (18) | −0.0146 (16) | −0.0105 (15) | −0.0126 (15) |
C9 | 0.0416 (18) | 0.0452 (19) | 0.0389 (16) | −0.0108 (14) | −0.0104 (14) | −0.0105 (14) |
C10 | 0.0400 (18) | 0.0425 (18) | 0.0414 (17) | −0.0106 (14) | −0.0077 (14) | −0.0127 (14) |
C11 | 0.065 (3) | 0.046 (2) | 0.067 (2) | −0.0103 (18) | −0.018 (2) | −0.0112 (18) |
C12 | 0.089 (3) | 0.104 (4) | 0.043 (2) | −0.037 (3) | −0.006 (2) | −0.012 (2) |
C13 | 0.074 (3) | 0.060 (2) | 0.049 (2) | −0.014 (2) | −0.0190 (19) | −0.0202 (18) |
C14 | 0.070 (3) | 0.065 (3) | 0.048 (2) | −0.019 (2) | −0.0178 (19) | 0.0002 (18) |
C15 | 0.083 (4) | 0.106 (4) | 0.126 (5) | −0.032 (3) | 0.008 (3) | −0.070 (4) |
Geometric parameters (Å, º) top
S1—C2 | 1.755 (3) | C7—C14 | 1.483 (5) |
S1—C12 | 1.807 (5) | C8—C9 | 1.459 (5) |
S2—C8 | 1.761 (4) | C9—C10 | 1.391 (4) |
S2—C15 | 1.789 (5) | C11—H11A | 0.9600 |
O1—C10 | 1.375 (4) | C11—H11B | 0.9600 |
O1—C1 | 1.386 (4) | C11—H11C | 0.9600 |
O2—C7 | 1.382 (4) | C12—H12A | 0.9600 |
O2—C6 | 1.386 (4) | C12—H12B | 0.9600 |
C1—C2 | 1.355 (5) | C12—H12C | 0.9600 |
C1—C11 | 1.482 (5) | C13—H13A | 0.9600 |
C2—C3 | 1.459 (5) | C13—H13B | 0.9600 |
C3—C10 | 1.399 (4) | C13—H13C | 0.9600 |
C3—C4 | 1.420 (5) | C14—H14A | 0.9600 |
C4—C5 | 1.387 (5) | C14—H14B | 0.9600 |
C4—C13 | 1.511 (5) | C14—H14C | 0.9600 |
C5—C6 | 1.385 (5) | C15—H15A | 0.9600 |
C5—H5 | 0.9300 | C15—H15B | 0.9600 |
C6—C9 | 1.382 (5) | C15—H15C | 0.9600 |
C7—C8 | 1.351 (5) | ||
C2—S1—C12 | 100.96 (19) | O1—C10—C3 | 111.2 (3) |
C8—S2—C15 | 101.0 (2) | C9—C10—C3 | 122.5 (3) |
C10—O1—C1 | 106.0 (3) | C1—C11—H11A | 109.5 |
C7—O2—C6 | 106.7 (3) | C1—C11—H11B | 109.5 |
C2—C1—O1 | 111.3 (3) | H11A—C11—H11B | 109.5 |
C2—C1—C11 | 133.1 (3) | C1—C11—H11C | 109.5 |
O1—C1—C11 | 115.6 (3) | H11A—C11—H11C | 109.5 |
C1—C2—C3 | 107.1 (3) | H11B—C11—H11C | 109.5 |
C1—C2—S1 | 122.9 (3) | S1—C12—H12A | 109.5 |
C3—C2—S1 | 130.0 (3) | S1—C12—H12B | 109.5 |
C10—C3—C4 | 120.6 (3) | H12A—C12—H12B | 109.5 |
C10—C3—C2 | 104.4 (3) | S1—C12—H12C | 109.5 |
C4—C3—C2 | 135.0 (3) | H12A—C12—H12C | 109.5 |
C5—C4—C3 | 117.3 (3) | H12B—C12—H12C | 109.5 |
C5—C4—C13 | 119.5 (3) | C4—C13—H13A | 109.5 |
C3—C4—C13 | 123.3 (3) | C4—C13—H13B | 109.5 |
C6—C5—C4 | 119.6 (3) | H13A—C13—H13B | 109.5 |
C6—C5—H5 | 120.2 | C4—C13—H13C | 109.5 |
C4—C5—H5 | 120.2 | H13A—C13—H13C | 109.5 |
C9—C6—C5 | 125.3 (3) | H13B—C13—H13C | 109.5 |
C9—C6—O2 | 109.9 (3) | C7—C14—H14A | 109.5 |
C5—C6—O2 | 124.8 (3) | C7—C14—H14B | 109.5 |
C8—C7—O2 | 111.1 (3) | H14A—C14—H14B | 109.5 |
C8—C7—C14 | 133.3 (3) | C7—C14—H14C | 109.5 |
O2—C7—C14 | 115.7 (3) | H14A—C14—H14C | 109.5 |
C7—C8—C9 | 106.5 (3) | H14B—C14—H14C | 109.5 |
C7—C8—S2 | 125.2 (3) | S2—C15—H15A | 109.5 |
C9—C8—S2 | 128.2 (3) | S2—C15—H15B | 109.5 |
C6—C9—C10 | 114.8 (3) | H15A—C15—H15B | 109.5 |
C6—C9—C8 | 105.8 (3) | S2—C15—H15C | 109.5 |
C10—C9—C8 | 139.4 (3) | H15A—C15—H15C | 109.5 |
O1—C10—C9 | 126.3 (3) | H15B—C15—H15C | 109.5 |
C3—C10—O1—C1 | −0.3 (3) | C9—C6—O2—C7 | −0.7 (4) |
C4—C2—C3—C10 | 179.8 (6) | C6—C9—C8—C7 | −0.4 (4) |
C10—O1—C1—C2 | 0.2 (4) | C6—O2—C7—C8 | 0.5 (4) |
C2—C3—C10—O1 | 0.3 (4) | C8—C9—C6—O2 | 0.7 (4) |
O1—C1—C2—C3 | −0.1 (4) | O2—C7—C8—C9 | −0.1 (4) |