Abstract
C32H20O2S2, monoclinic, P21/c (no. 14), a = 10.2763(8) Å, b = 19.9178(15) Å, c = 11.8597(10) Å, β = 92.828(3)°, V = 2424.3(3) Å3, Z = 4, Rgt(F) = 0.069, wR(F2) = 0.1782, T = 293(2).
The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Yellow plate |
| Size: | 0.49 × 0.45 × 0.06 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 2.5 cm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| 2θmax, completeness: | 55°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 46788, 5560, 0.170 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3412 |
| N(param)refined: | 325 |
| Programs: | SHELX [10], Bruker programs [11] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| S1 | −0.64720(8) | −0.43422(4) | −0.07815(7) | 0.0413(2) |
| S2 | −0.44743(9) | −0.41162(4) | −0.26422(7) | 0.0433(2) |
| O1 | −0.7921(2) | −0.48721(12) | 0.10123(18) | 0.0521(6) |
| O2 | −0.2912(3) | −0.41789(12) | −0.4521(2) | 0.0663(8) |
| C1 | −0.6988(3) | −0.51734(13) | −0.0661(2) | 0.0334(7) |
| C2 | −0.6380(3) | −0.56051(13) | −0.1372(2) | 0.0293(6) |
| C3 | −0.5453(3) | −0.52560(13) | −0.2022(2) | 0.0301(6) |
| C4 | −0.4518(3) | −0.54316(14) | −0.2842(2) | 0.0307(6) |
| C5 | −0.3930(3) | −0.48624(14) | −0.3250(3) | 0.0361(7) |
| C6 | −0.5461(3) | −0.45701(14) | −0.1818(2) | 0.0343(7) |
| C7 | −0.7937(3) | −0.52680(15) | 0.0222(2) | 0.0356(7) |
| C8 | −0.8903(3) | −0.58276(15) | 0.0159(2) | 0.0361(7) |
| C9 | −0.9256(4) | −0.61272(18) | 0.1150(3) | 0.0505(9) |
| H9A | −0.8905 | −0.5973 | 0.1840 | 0.061* |
| C10 | −1.0123(4) | −0.6652(2) | 0.1117(4) | 0.0638(11) |
| H10A | −1.0338 | −0.6862 | 0.1784 | 0.077* |
| C11 | −1.0673(4) | −0.6867(2) | 0.0105(4) | 0.0642(11) |
| H11A | −1.1254 | −0.7225 | 0.0087 | 0.077* |
| C12 | −1.0369(3) | −0.65568(19) | −0.0888(3) | 0.0560(9) |
| H12A | −1.0761 | −0.6695 | −0.1572 | 0.067* |
| C13 | −0.9479(3) | −0.60387(16) | −0.0853(3) | 0.0428(8) |
| H13A | −0.9264 | −0.5830 | −0.1520 | 0.051* |
| C14 | −0.6686(3) | −0.63324(13) | −0.1498(2) | 0.0287(6) |
| C15 | −0.6580(3) | −0.67707(14) | −0.0595(2) | 0.0353(7) |
| H15A | −0.6261 | −0.6618 | 0.0106 | 0.042* |
| C16 | −0.6947(3) | −0.74371(16) | −0.0728(3) | 0.0458(8) |
| H16A | −0.6859 | −0.7732 | −0.0121 | 0.055* |
| C17 | −0.7439(4) | −0.76592(15) | −0.1757(3) | 0.0482(9) |
| H17A | −0.7713 | −0.8102 | −0.1839 | 0.058* |
| C18 | −0.7531(3) | −0.72332(16) | −0.2667(3) | 0.0473(9) |
| H18A | −0.7850 | −0.7389 | −0.3366 | 0.057* |
| C19 | −0.7147(3) | −0.65718(14) | −0.2541(2) | 0.0356(7) |
| H19A | −0.7199 | −0.6285 | −0.3160 | 0.043* |
| C20 | −0.4207(3) | −0.61329(14) | −0.3135(2) | 0.0330(7) |
| C21 | −0.3739(3) | −0.65675(15) | −0.2294(3) | 0.0427(8) |
| H21A | −0.3627 | −0.6413 | −0.1556 | 0.051* |
| C22 | −0.3439(4) | −0.72208(17) | −0.2536(4) | 0.0604(11) |
| H22A | −0.3137 | −0.7508 | −0.1962 | 0.073* |
| C23 | −0.3583(4) | −0.74463(19) | −0.3611(5) | 0.0722(13) |
| H23A | −0.3367 | −0.7888 | −0.3775 | 0.087* |
| C24 | −0.4043(4) | −0.7031(2) | −0.4462(4) | 0.0688(13) |
| H24A | −0.4150 | −0.7193 | −0.5196 | 0.083* |
| C25 | −0.4349(3) | −0.63694(18) | −0.4229(3) | 0.0481(9) |
| H25A | −0.4649 | −0.6085 | −0.4808 | 0.058* |
| C26 | −0.2978(3) | −0.47437(16) | −0.4119(3) | 0.0417(8) |
| C27 | −0.2109(3) | −0.52829(15) | −0.4511(3) | 0.0397(7) |
| C28 | −0.1951(4) | −0.5342(2) | −0.5657(3) | 0.0621(11) |
| H28A | −0.2404 | −0.5059 | −0.6161 | 0.074* |
| C29 | −0.1123(5) | −0.5820(2) | −0.6048(4) | 0.0841(15) |
| H29A | −0.1038 | −0.5869 | −0.6820 | 0.101* |
| C30 | −0.0423(5) | −0.6222(2) | −0.5311(4) | 0.0796(14) |
| H30A | 0.0144 | −0.6541 | −0.5583 | 0.096* |
| C31 | −0.0553(4) | −0.6158(2) | −0.4162(4) | 0.0646(11) |
| H31A | −0.0069 | −0.6430 | −0.3660 | 0.078* |
| C32 | −0.1408(3) | −0.56885(16) | −0.3761(3) | 0.0458(8) |
| H32A | −0.1509 | −0.5647 | −0.2989 | 0.055* |
Source of material
The synthesis of 1,1′-(3,4-diphenylthieno[2,3-b]thiophene-2,5-diyl)bis[1-phenyl-methanone] was carried out using 1,3-diphenyl-1,3-propanedione (1.0 g, 4.46 mmol) and anhydrous potassium carbonate (2.46 g, 17.83 mmol) dissolved in 7 mL N,N-dimethylformamide (DMF), and was stirred vigorously at room temperature for 5 min. Carbon disulfide (0.3 mL, 4.9 mmol) was added with continued stirring for 30 min. The reaction mixture was cooled in an ice bath for 10 min, where 2-chloro-1-phenylethanone (1.1 mL, 9.36 mmol) was introduced dropwise. The reaction mixture was stirred vigorously at room temperature for another 3 h. The precipitates were collected after adding 10 mL of distilled water. The crude reaction mixture was purified by flash chromatography eluting with 20% ethyl acetate/hexanes to provide 1.56 g of the product (70% yield) [1], [2], [3]. The title compound was crystallized from ethanol; whereupon yellow crystals were obtained.
The title compound was characterized by 1H-NMR, 13C-NMR, and single-crystal X-ray diffraction. 1H-NMR (800 MHz, DMSO-6, δ): 7.44 (d, 4H), 7.32 (t, 2H), 7.13 (t, 4H), 6.80 (t, 4H), 6.68 (d, 4H), 6.63 (t, 2H); 13C-NMR (DMSO-6, δ): 190.02, 145.44, 144.02, 141.60, 140.85, 137.20, 132.56, 132.21, 129.73, 129.02, 127.81, 126.87, 126.66.
Experimental details
Hydrogen atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).
Discussion
Some thienothiophenes compounds are known for their importance in pharmaceutical applications because of their biological activities, such as anticancer, antioxidant, antimicrobial, antitumor and others [4], [5], [6], [7], [8], [9]. The bioactivity and pharmacological activities for the prepared compound are part of an ongoing study in our laboratories.
The asymmetric unit of the title structure contains only one independent molecule. The dihedral angle between the two thiophene rings is 3.97(4)°. The planes of the phenyl groups (C14—C19) and (C20—C25) make dihedral angle with the mean plane of thieno[2,3-b]thiophene equal to 59.31° and 59.60°, respectively. The molecules were packed in the crystal structure without any hydrogen bonds.
Acknowledgement
This work was sponsored by National Center for Petrochemical Technology (NCPT) at KingAbdulaziz City for Science and Technology (KACST) in Saudi Arabia (Grant No. 33–781).
References
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©2017 Rashid Altamimi et al., published by De Gruyter.
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