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A new type of thio­phene derivative having α-thio­ketone groups at the 3- and 4-positions, viz. the title compound, C22H20O4S3, has been prepared and studied by NMR spectroscopy and single-crystal X-ray diffraction techniques. The mol­ecule is nearly planar, the dihedral angles between the essentially planar thio­phene and benzene rings being 9.4 (1) and 10.6 (1)°. One of the thio­ketone O atoms is involved in an inter­molecular C—H...O hydrogen-bonding inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105005251/av1231sup1.cif
Contains datablocks global, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105005251/av1231IIIsup2.hkl
Contains datablock III

CCDC reference: 275537

Comment top

Dithieno[3,2 − b;2',3'-d]thiophenes (DTT), which consist of three fused thiophene heterocycles, are important compounds for the synthesis of a wide variety of materials for electronics and optical applications (Kim et al., 2001, 1999; Osterod et al., 2001; Ventelon et al., 1999; Tsivgoulis & Lehn, 1995). Dimeric DTT systems, which have been employed in thin-film transistors, have been shown to have high mobilities and on/off ratios (Sirringhaus et al., 1997; Morrison et al., 1999; Li et al., 1998). Their oxidized dioxide forms demonstrate interesting fluorescence properties and this creates important application opportunities, such as their use as labelling agents in biological systems (Sotgiu et al. 2003; Barbarella, 2002; Barbarella et al., 2001), photovoltaic devices (Catellani et al., 2002) and light-emitting diodes (Gigli et al., 2001). Conducting polymers (Fujitsuka et al., 1996; Lazzaroni et al., 1989; Di Marco et al., 1985), and organic acceptor and donor molecules for the preparation of different cationic radical salts and charge-transfer complexes (Mazaki & Kabayashi, 1992; Yui et al., 1987; Hayashi et al., 1992; Bertinelli et al., 1984), have been prepared.

Although some methods have been developed for the synthesis of the DTT molecule (De Jong & Janssen, 1971; Mazaki & Kabayashi, 1989; Hellberg & Remonen, 1995; Schroth et al., 1997; Frey et al., 2002), new synthetic methods are still required, particularly to functionalize the system. Recently, we have reported an efficient and novel method (Ertas & Ozturk, 2004). During the application of this method to the synthesis of 3,5-di(4-methoxyphenyl)dithieno[3,2 − b;2',3'-d]thiophenes, (I), an intermediate was isolated, namely the title compound, (III), which was obtained in three steps starting from 3,4-dibromothiophene, (II) (scheme). We report here the X-ray single-crystal structure of (III), which has α-thioketones at the 3- and 4- positions of the thiophene ring.

The molecular structure and atom-numbering scheme of (III) are shown in Fig. 1, and the arrangement of the molecules in the unit cell is given in Fig. 2. Selected bond lengths and angles are listed in Table 1. Overall, the molecule is fairly flat; the dihedral angles between the essentially planar thiophene and phenyl rings (C5–C10 and C5'–C10') are 9.4 (1) and 10.6 (1)°, respectively, while the dihedral angle between these two phenyl rings is 2.4 (1)°. The thioketone moieties attached to atoms C2 and C2' of the thiophene ring adopt an extended conformation, with torsion angles close to 0 or 180°: C1—C2—S2—C3 − 0.3 (2) and C1'—C2'—S2'—C3' −2.3 (2)°, C2—S2—C3—C4 − 176.4 (1) and C2'—S2'—C3'—C4' −179.2 (1)°, S2—C3—C4—O1 3.7 (2) and S2'—C3'—C4'—O1' 1.4 (2)°, and C3—C4—C5—C6 1.7 (3) and C3'—C4'—C5'—C6' −9.4 (3)°. The angles between the least-squares planes formed by the thioketone groups (S2/C3/C4/O1 and S2'/C3'/C4'/O1') and the thiophene ring are 7.7 (1) and 0.7 (1)°, respectively. Thus, this part of the molecule is almost coplanar with the thiophene ring.

The S1—C1 and S1'—C1' bond lengths [1.709 (2) and 1.709 (2) Å] are in good agreement with those found for structures containing a thiophene ring (Kazak et al., 2000; Rodinovskaya et al., 2002). In the thioketone parts, the difference between the S2—C2/S2'—C2' bond lengths [1.758 (2) and 1.762 (2) Å, respectively] and the S2—C3/S2'—C3' bond lengths [1.799 (2) and 1.803 (2) Å, respectively] can be attributed to the different hybridization of the Csp3 and Csp2 atoms. Bonds C4—O1 and C4'—O1' are found to have normal double-bond lengths.

There are no intramolecular hydrogen bonds in (III), but the O atoms of the ketone groups are involved in short contacts, forming a five-membered ring-structure (Table 2). The interatomic distances S2···S2' [3.169 (1) Å], S2···O1 [2.783 (2) Å] and S2'···O1' [2.810 (2) Å] also indicate close contacts. There is a C—H···O-type intermolecular hydrogen bond between neighbouring molecules along the b axis. Molecules are stacked along the a direction at a mean interplanar distance of 3.45 Å; no hydrogen bonds are observed between these layers (Fig. 2).

Experimental top

Compound (III) was prepared as follows. To a solution of 3,4-dibromothiophene (0.96 g, 4 mmol) in dry ether (30 ml) was added n-BuLi (1.6 ml, 4 mmol, 2.5 M) by syringe at 351 K under a nitrogen atmosphere. The solution was stirred for 5 min and elemental sulfur (Quantity?) was added portionwise. The solution was then stirred for 15 min and the addition of n-BuLi and elemental S was repeated in the same ratios at the same temperature (351 K). The final solution was stirred for a further 30 min, then 2-bromo-4-methoxyacetophenone (2 g, 9 mmol) was added portionwise and the solution was allowed to come to room temperature. After the addition of ice, the mixture was extracted with ether (3 × 20 ml). The organic layer was dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography, eluting with hexane–ethyl acetate (5:1), to yield the title compound (m.p. 387–388 K, yield 1 g, 58%). 1H NMR (200 MHz, CDCl3, δ, p.p.m.): 7.86 (4H, d, J = 8.3 Hz, Ph), 7.25 (2H, s, thiophene), 6.87 (4H, d, J = 8.3 Hz, Ph), 4.18 (4H, s, SCH2), 3.83 (6H, s, OCH3); 13C NMR (67.8 MHz, CDCl3, δ, p.p.m.): 192.7 (C O), 163.7 (q, C), 132 (q, C), 130.1 (CH), 128.5 (q, C), 127.2 (CH), 113.8 (CH), 55.4 (OCH3), 40.9 (SCH2); m/z (EI): 444 M+.

Refinement top

All H atoms were placed in idealized positions and refined using a riding model, with Uiso(H) = 1.3Ueq(C), and with fixed C—H distances of 0.93 (aromatic), 0.96 (methyl) and 0.97 Å (ethyl).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (III), projected onto the ac plane.
3,4-Bis[(4-methoxybenzoyl)methylsulfanyl]thiophene top
Crystal data top
C22H20O4S3F(000) = 928
Mr = 444.56Dx = 1.427 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.4682 (12) Åθ = 9.7–18.1°
b = 10.9027 (12) ŵ = 0.39 mm1
c = 18.4929 (12) ÅT = 293 K
β = 101.390 (7)°Prism, yellow
V = 2069.1 (4) Å30.6 × 0.6 × 0.48 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.026
non–profiled ω scansθmax = 26.3°, θmin = 2.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 013
Tmin = 0.802, Tmax = 0.837k = 013
4417 measured reflectionsl = 2322
4191 independent reflections3 standard reflections every 120 min
3279 reflections with I > 2σ(I) intensity decay: 8%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.5012P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.18 e Å3
4191 reflectionsΔρmin = 0.26 e Å3
270 parameters
Crystal data top
C22H20O4S3V = 2069.1 (4) Å3
Mr = 444.56Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.4682 (12) ŵ = 0.39 mm1
b = 10.9027 (12) ÅT = 293 K
c = 18.4929 (12) Å0.6 × 0.6 × 0.48 mm
β = 101.390 (7)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3279 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.026
Tmin = 0.802, Tmax = 0.8373 standard reflections every 120 min
4417 measured reflections intensity decay: 8%
4191 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.05Δρmax = 0.18 e Å3
4191 reflectionsΔρmin = 0.26 e Å3
270 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.62116 (18)0.11830 (19)0.02545 (11)0.0472 (5)
H10.54350.13780.05740.057*
C1'0.81939 (19)0.10864 (19)0.06986 (11)0.0472 (5)
H1'0.88940.12120.10870.057*
C20.68510 (17)0.01027 (17)0.02715 (10)0.0393 (4)
C2'0.80141 (17)0.00459 (17)0.02923 (10)0.0386 (4)
C3'1.02794 (17)0.08251 (17)0.11217 (10)0.0413 (4)
H3'A0.99010.0670.15510.05*
H3'B1.070.00780.10050.05*
C30.50187 (17)0.05237 (17)0.14744 (10)0.0415 (4)
H3A0.5210.02620.16750.05*
H3B0.43450.04010.11890.05*
C4'1.12737 (18)0.18475 (17)0.12864 (10)0.0410 (4)
C40.45493 (18)0.14131 (17)0.20929 (10)0.0411 (4)
C5'1.24001 (17)0.16556 (17)0.19009 (10)0.0384 (4)
C50.33199 (18)0.11468 (17)0.26222 (10)0.0405 (4)
C6'1.24802 (18)0.06766 (18)0.23869 (10)0.0424 (4)
H6'1.18240.00890.23130.051*
C60.25499 (19)0.01326 (18)0.25711 (11)0.0474 (5)
H60.28010.04180.21850.057*
C70.14117 (19)0.00821 (18)0.30825 (11)0.0473 (5)
H70.09040.07670.30390.057*
C7'1.35104 (18)0.05527 (18)0.29776 (10)0.0436 (4)
H7'1.35380.01020.33030.052*
C80.10404 (18)0.07341 (19)0.36584 (10)0.0433 (4)
C8'1.45044 (18)0.14174 (17)0.30797 (10)0.0412 (4)
C9'1.44698 (19)0.23751 (18)0.25786 (11)0.0458 (5)
H9'1.51530.29340.26340.055*
C10'1.34270 (19)0.24943 (17)0.20021 (10)0.0425 (4)
H10'1.34050.31440.16740.051*
C100.29290 (19)0.19500 (19)0.32089 (11)0.0475 (5)
H100.34340.26370.32540.057*
C11'1.5535 (2)0.0554 (2)0.42306 (12)0.0679 (7)
H11'A1.6330.06270.4590.102*
H11'B1.54530.02680.40410.102*
H11'C1.48090.07380.44580.102*
C110.0839 (2)0.0439 (2)0.41892 (13)0.0631 (6)
H11C0.1580.03920.45880.095*
H11B0.1130.04960.37290.095*
H11A0.03320.11510.42510.095*
C90.1813 (2)0.1746 (2)0.37212 (11)0.0504 (5)
H90.15720.22890.41120.061*
O1'1.11355 (15)0.27892 (13)0.09311 (8)0.0564 (4)
O10.51783 (14)0.23349 (13)0.21523 (8)0.0559 (4)
O20.00581 (13)0.06345 (14)0.41881 (8)0.0553 (4)
O2'1.55554 (14)0.13925 (13)0.36415 (7)0.0539 (4)
S10.69923 (5)0.21429 (5)0.04195 (3)0.05294 (16)
S2'0.90191 (5)0.12607 (4)0.03525 (3)0.04417 (14)
S20.64629 (5)0.11260 (5)0.08911 (3)0.04645 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0338 (10)0.0548 (12)0.0488 (11)0.0020 (9)0.0019 (8)0.0034 (9)
C1'0.0390 (10)0.0532 (12)0.0446 (10)0.0046 (9)0.0030 (8)0.0031 (9)
C20.0317 (9)0.0433 (10)0.0402 (9)0.0074 (8)0.0010 (7)0.0006 (8)
C2'0.0311 (9)0.0462 (10)0.0362 (9)0.0079 (8)0.0011 (7)0.0033 (8)
C3'0.0355 (9)0.0439 (10)0.0402 (10)0.0066 (8)0.0032 (8)0.0035 (8)
C30.0352 (9)0.0429 (10)0.0421 (10)0.0042 (8)0.0029 (8)0.0021 (8)
C4'0.0408 (10)0.0408 (10)0.0388 (10)0.0059 (8)0.0015 (8)0.0037 (8)
C40.0354 (10)0.0417 (10)0.0432 (10)0.0038 (8)0.0001 (8)0.0011 (8)
C5'0.0364 (9)0.0382 (9)0.0382 (9)0.0009 (8)0.0019 (7)0.0032 (8)
C50.0367 (9)0.0417 (10)0.0402 (10)0.0033 (8)0.0004 (8)0.0014 (8)
C6'0.0350 (9)0.0434 (10)0.0460 (11)0.0071 (8)0.0009 (8)0.0025 (8)
C60.0489 (11)0.0440 (11)0.0434 (10)0.0012 (9)0.0058 (8)0.0084 (8)
C70.0441 (11)0.0451 (11)0.0477 (11)0.0054 (9)0.0030 (9)0.0014 (9)
C7'0.0404 (10)0.0437 (10)0.0432 (10)0.0052 (8)0.0004 (8)0.0057 (8)
C80.0353 (9)0.0525 (11)0.0381 (10)0.0055 (8)0.0022 (8)0.0035 (8)
C8'0.0391 (10)0.0442 (10)0.0370 (9)0.0028 (8)0.0007 (8)0.0045 (8)
C9'0.0463 (11)0.0429 (10)0.0444 (10)0.0133 (9)0.0001 (8)0.0019 (8)
C10'0.0494 (11)0.0358 (9)0.0396 (10)0.0035 (8)0.0023 (8)0.0010 (8)
C100.0430 (11)0.0473 (11)0.0488 (11)0.0024 (9)0.0004 (9)0.0074 (9)
C11'0.0706 (15)0.0718 (15)0.0484 (12)0.0162 (12)0.0197 (11)0.0138 (11)
C110.0432 (12)0.0805 (16)0.0590 (13)0.0087 (11)0.0057 (10)0.0072 (12)
C90.0472 (11)0.0540 (12)0.0453 (11)0.0031 (9)0.0026 (9)0.0129 (9)
O1'0.0605 (9)0.0450 (8)0.0553 (9)0.0030 (7)0.0092 (7)0.0067 (7)
O10.0468 (8)0.0508 (8)0.0634 (9)0.0075 (7)0.0057 (7)0.0077 (7)
O20.0427 (8)0.0661 (9)0.0489 (8)0.0009 (7)0.0110 (6)0.0022 (7)
O2'0.0500 (8)0.0587 (9)0.0439 (8)0.0151 (7)0.0129 (6)0.0048 (6)
S10.0443 (3)0.0519 (3)0.0593 (3)0.0009 (2)0.0022 (2)0.0108 (2)
S2'0.0399 (3)0.0430 (3)0.0429 (3)0.0044 (2)0.0082 (2)0.0024 (2)
S20.0374 (3)0.0450 (3)0.0493 (3)0.0016 (2)0.0099 (2)0.0033 (2)
Geometric parameters (Å, º) top
C1—C21.358 (3)C6'—H6'0.93
C1—S11.707 (2)C6—C71.387 (3)
C1—H10.93C6—H60.93
C1'—C2'1.353 (3)C7—C81.383 (3)
C1'—S11.708 (2)C7—H70.93
C1'—H1'0.93C7'—C8'1.389 (3)
C2—C2'1.439 (2)C7'—H7'0.93
C2—S21.7575 (19)C8—O21.360 (2)
C2'—S2'1.761 (2)C8—C91.386 (3)
C3'—C4'1.514 (3)C8'—O2'1.356 (2)
C3'—S2'1.8024 (17)C8'—C9'1.392 (3)
C3'—H3'A0.97C9'—C10'1.373 (3)
C3'—H3'B0.97C9'—H9'0.93
C3—C41.506 (3)C10'—H10'0.93
C3—S21.7989 (18)C10—C91.369 (3)
C3—H3A0.97C10—H100.93
C3—H3B0.97C11'—O2'1.426 (3)
C4'—O1'1.212 (2)C11'—H11'A0.96
C4'—C5'1.482 (2)C11'—H11'B0.96
C4—O11.218 (2)C11'—H11'C0.96
C4—C51.484 (2)C11—O21.427 (3)
C5'—C6'1.387 (3)C11—H11C0.96
C5'—C10'1.395 (3)C11—H11B0.96
C5—C61.382 (3)C11—H11A0.96
C5—C101.391 (3)C9—H90.93
C6'—C7'1.382 (2)
C2—C1—S1112.43 (14)C8—C7—C6119.29 (18)
C2—C1—H1123.8C8—C7—H7120.4
S1—C1—H1123.8C6—C7—H7120.4
C2'—C1'—S1112.59 (14)C6'—C7'—C8'119.19 (17)
C2'—C1'—H1'123.7C6'—C7'—H7'120.4
S1—C1'—H1'123.7C8'—C7'—H7'120.4
C1—C2—C2'111.76 (17)O2—C8—C7124.91 (18)
C1—C2—S2128.65 (14)O2—C8—C9115.31 (17)
C2'—C2—S2119.54 (14)C7—C8—C9119.78 (17)
C1'—C2'—C2111.79 (17)O2'—C8'—C7'124.27 (17)
C1'—C2'—S2'128.84 (14)O2'—C8'—C9'115.82 (16)
C2—C2'—S2'119.33 (14)C7'—C8'—C9'119.90 (17)
C4'—C3'—S2'109.37 (13)C10'—C9'—C8'120.01 (17)
C4'—C3'—H3'A109.8C10'—C9'—H9'120
S2'—C3'—H3'A109.8C8'—C9'—H9'120
C4'—C3'—H3'B109.8C9'—C10'—C5'121.02 (17)
S2'—C3'—H3'B109.8C9'—C10'—H10'119.5
H3'A—C3'—H3'B108.2C5'—C10'—H10'119.5
C4—C3—S2109.26 (13)C9—C10—C5121.12 (19)
C4—C3—H3A109.8C9—C10—H10119.4
S2—C3—H3A109.8C5—C10—H10119.4
C4—C3—H3B109.8O2'—C11'—H11'A109.5
S2—C3—H3B109.8O2'—C11'—H11'B109.5
H3A—C3—H3B108.3H11'A—C11'—H11'B109.5
O1'—C4'—C5'121.80 (17)O2'—C11'—H11'C109.5
O1'—C4'—C3'120.71 (16)H11'A—C11'—H11'C109.5
C5'—C4'—C3'117.48 (16)H11'B—C11'—H11'C109.5
O1—C4—C5121.05 (17)O2—C11—H11C109.5
O1—C4—C3119.90 (17)O2—C11—H11B109.5
C5—C4—C3119.04 (16)H11C—C11—H11B109.5
C6'—C5'—C10'118.09 (16)O2—C11—H11A109.5
C6'—C5'—C4'122.86 (17)H11C—C11—H11A109.5
C10'—C5'—C4'119.05 (17)H11B—C11—H11A109.5
C6—C5—C10118.10 (17)C10—C9—C8120.21 (18)
C6—C5—C4123.57 (17)C10—C9—H9119.9
C10—C5—C4118.32 (17)C8—C9—H9119.9
C7'—C6'—C5'121.69 (17)C8—O2—C11117.97 (16)
C7'—C6'—H6'119.2C8'—O2'—C11'117.77 (16)
C5'—C6'—H6'119.2C1—S1—C1'91.43 (10)
C5—C6—C7121.49 (18)C2'—S2'—C3'99.89 (9)
C5—C6—H6119.3C2—S2—C399.87 (9)
C7—C6—H6119.3
S1—C1—C2—C2'0.8 (2)C6—C7—C8—O2179.13 (19)
S1—C1—C2—S2176.74 (12)C6—C7—C8—C90.6 (3)
S1—C1'—C2'—C20.0 (2)C6'—C7'—C8'—O2'179.53 (18)
S1—C1'—C2'—S2'177.40 (11)C6'—C7'—C8'—C9'1.7 (3)
C1—C2—C2'—C1'0.5 (2)O2'—C8'—C9'—C10'178.32 (18)
S2—C2—C2'—C1'177.28 (14)C7'—C8'—C9'—C10'2.8 (3)
C1—C2—C2'—S2'178.19 (14)C8'—C9'—C10'—C5'1.0 (3)
S2—C2—C2'—S2'0.4 (2)C6'—C5'—C10'—C9'1.9 (3)
S2'—C3'—C4'—O1'1.4 (2)C4'—C5'—C10'—C9'177.83 (17)
S2'—C3'—C4'—C5'179.45 (13)C6—C5—C10—C90.1 (3)
S2—C3—C4—O13.6 (2)C4—C5—C10—C9179.17 (19)
S2—C3—C4—C5176.38 (14)C5—C10—C9—C80.7 (3)
O1'—C4'—C5'—C6'169.74 (19)O2—C8—C9—C10178.70 (19)
C3'—C4'—C5'—C6'9.4 (3)C7—C8—C9—C101.0 (3)
O1'—C4'—C5'—C10'9.9 (3)C7—C8—O2—C115.3 (3)
C3'—C4'—C5'—C10'170.94 (17)C9—C8—O2—C11174.98 (19)
O1—C4—C5—C6178.31 (19)C7'—C8'—O2'—C11'11.0 (3)
C3—C4—C5—C61.7 (3)C9'—C8'—O2'—C11'170.12 (19)
O1—C4—C5—C102.7 (3)C2—C1—S1—C1'0.68 (17)
C3—C4—C5—C10177.26 (17)C2'—C1'—S1—C10.39 (17)
C10'—C5'—C6'—C7'3.0 (3)C1'—C2'—S2'—C3'2.3 (2)
C4'—C5'—C6'—C7'176.67 (18)C2—C2'—S2'—C3'179.54 (14)
C10—C5—C6—C70.6 (3)C4'—C3'—S2'—C2'179.19 (13)
C4—C5—C6—C7179.57 (18)C1—C2—S2—C30.3 (2)
C5—C6—C7—C80.2 (3)C2'—C2—S2—C3177.04 (14)
C5'—C6'—C7'—C8'1.3 (3)C4—C3—S2—C2176.36 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O10.932.472.778 (2)99
C10—H10···O10.932.532.811 (2)98
C7—H7···O1i0.932.423.343 (2)173
Symmetry code: (i) x+1/2, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC22H20O4S3
Mr444.56
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)10.4682 (12), 10.9027 (12), 18.4929 (12)
β (°) 101.390 (7)
V3)2069.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.6 × 0.6 × 0.48
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.802, 0.837
No. of measured, independent and
observed [I > 2σ(I)] reflections
4417, 4191, 3279
Rint0.026
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.100, 1.05
No. of reflections4191
No. of parameters270
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.26

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1—C21.358 (3)C3—S21.7989 (18)
C1—S11.707 (2)C4'—O1'1.212 (2)
C1'—C2'1.353 (3)C4'—C5'1.482 (2)
C1'—S11.708 (2)C4—O11.218 (2)
C2—C2'1.439 (2)C4—C51.484 (2)
C2—S21.7575 (19)C8—O21.360 (2)
C2'—S2'1.761 (2)C8'—O2'1.356 (2)
C3'—C4'1.514 (3)C11'—O2'1.426 (3)
C3'—S2'1.8024 (17)C11—O21.427 (3)
C3—C41.506 (3)
C2—C1—S1112.43 (14)O2—C8—C9115.31 (17)
C2'—C1'—S1112.59 (14)O2'—C8'—C9'115.82 (16)
C1—C2—S2128.65 (14)C8—O2—C11117.97 (16)
C1'—C2'—S2'128.84 (14)C8'—O2'—C11'117.77 (16)
C4'—C3'—S2'109.37 (13)C1—S1—C1'91.43 (10)
C4—C3—S2109.26 (13)C2'—S2'—C3'99.89 (9)
C10'—C5'—C4'119.05 (17)C2—S2—C399.87 (9)
C10—C5—C4118.32 (17)
S2'—C3'—C4'—O1'1.4 (2)C2—C2'—S2'—C3'179.54 (14)
S2—C3—C4—O13.6 (2)C4'—C3'—S2'—C2'179.19 (13)
O1'—C4'—C5'—C6'169.74 (19)C1—C2—S2—C30.3 (2)
O1—C4—C5—C6178.31 (19)C2'—C2—S2—C3177.04 (14)
C1'—C2'—S2'—C3'2.3 (2)C4—C3—S2—C2176.36 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O10.932.472.778 (2)99
C10'—H10'···O1'0.932.532.811 (2)98
C7—H7···O1i0.932.423.343 (2)173
Symmetry code: (i) x+1/2, y1/2, z1/2.
 

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