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The title compound, C17H10S4, has two independent mol­ecules in the asymmetric unit. In both mol­ecules, the fused heterocycle is almost planar and the phenyl groups make dihedral angles of 42.88 (9) and 52.79 (8)° with the fused heterocycle in one mol­ecule, and angles of 40.62 (9) and 52.28 (8)° in the other. The crystal packing is governed by short intermolecular S...S interactions, the shortest contact being 3.333 (1) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010988/fr1332sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010988/fr1332Isup2.hkl
Contains datablock I

CCDC reference: 173396

Comment top

It has recently been discovered that Lawesson's reagent (LR), (I), could be used to construct 1,4-dithiine (III) and/or thiophene heterocycles from 1,8-diketones (II) (Öztürk, 1996). The possible mechanism of this reaction involves a nine-membered-ring intermediate which then rearranges to the six-membered dithiine ring. In-situ loss of an S atom from the 1,4-dithiine ring leads to the formation of a thiophene. The dithiine/thiophene ratio depends on the electron-withdrawing or electron-releasing nature of the aromatic (Ar) substituent. While electron-donating groups make the loss of the S atom easier, electron-withdrawing groups make it harder.

Our previous and ongoing studies indicated that when the corresponding 1,8-diketone is treated with LR, dithiine (V) is obtained as a minor product (Öztürk, 1996; Öztürk & Türksoy,1999). On the other hand, when the phenyl group of the 1,8-diketone is replaced by para-methoxyphenyl, thiophene rather than dithiine becomes a major product (Öztürk & Wallis, 1996).

In an effort to obtain new diphenyl-substituted dithiine (VIII) and thiophene (IX) heterocycles, which are useful building blocks for organic conducting/superconducting materials, the tetraphenyl-1,8-diketone (VII) was reacted overnight with LR in refluxing toluene under a nitrogen atmosphere. In accordance with the results obtained previously (Lee et al., 1998), no product containing dithiine ring (VIII) was obtained. Diphenylthiophene (IX) was isolated as the sole product and its the X-ray crystal structure is reported here.

Compound (IX) crystallizes in P21/c and has two crystallographically independent molecules in the asymmetric unit, labelled A and B (Fig. 1). Interatomic distances and angles are very similar in both molecules. The fused heterocyle in the molecules is nearly planar; the best planes of the two five-membered rings (thiophene and dithiole) form dihedral angles of 4.77 (8)° in molecule A and 5.35 (8)° in molecule B. These values are comparable with those found in 6-(4-methoxyphenyl)thieno[2,3-d][1,3]dithiole-2-thione [4.2 (1)°; Öztürk & Wallis, 1996]. The phenyl groups in (IX) are essentially planar, the maximum deviations being 0.007 (2) Å (C17A in molecule A) and -0.008 (3) Å (C15B in molecule B). The dihedral angles between the phenyl groups (C6—C11 and C12—C17) and the fused heterocycle are 42.88 (9) and 52.79 (8)°, while the dihedral angle between these two phenyl rings is 55.05 (11)° for molecule A; these values are slightly less, 40.62 (9), 52.28 (8) and 52.75 (11)°, respectively, for molecule B. The terminal CS double bond [mean 1.648 (2) Å] is quite similar to that of other structures including 1,3-thiole-2-thione (Öztürk & Wallis, 1996; Parvez et al., 1996; Lee & Noh, 1998). There is a marked asymmetry in the thiophene and dithiole rings. The S4—C5 bond distance [1.742 (2) in molecule A and 1.744 (2) Å in molecule B] is longer than the S4—C3 bond distance [1.709 (2) and 1.710 (2) Å for molecules A and B, respectively]. The mean bond angle at the S4 atom, 91.29 (8)°, is significantly smaller than the angles at the S2 and S3 atoms, which have mean values of 96.57 (8) and 95.89 (8)°, respectively.

As usual in this type of compound, packing appears to be governed by S···S interactions. Some intermolecular S···S contact distances are S1A···S3Ai 3.333 (1), S1A···S4Ai 3.372 (1), S1A···S1Aii 3.555 (1), S2A···S3Ai 3.427 (1), S1B···S3Biii 3.344 (1), S1B···S4Biii 3.355 (1), S1B···S1Biv 3.570 (1) and S2B···S3Biii 3.447 (1) Å and contribute to the formation of chains along the b direction [symmetry codes: (i) 2 - x, 1/2 + y, 3/2 - z; (ii) 2 - x, 1 - y, 2 - z; (iii) 1 - x, 1/2 + y, 3/2 - z; (iv) 1 - x, 1 - y, 2 - z]. These chains, in turn, are held together by van der Waals interactions.

Experimental top

For the preparation of 5,6-diphenylthieno[2,3-d][1,3]dithiole-2-thione, (IX), a solution of 1,8-diketone (VII) (0.5 g, 0.85 mmol) and Lawesson's reagent, (I) (0.4 g, 0.99 mmol), in dry toluene (25 ml) was refluxed overnight under a nitrogen atmosphere. The solvent was evaporated and the residue purified by column chromatography, eluting with hexane–dichloromethane (2:1) (m.p. 429–430 K; 0.087 g, 30%). 1H NMR (200 MHz, CDCl3): δ 7.5 (10H, m); 13C NMR (50.32 Hz, CDCl3): δ 207 (CS), 143.8, 140.7, 133.9, 132.6, 129.06, 129, 128.9, 128.8, 128.7, 128.6, 128.5, 128.4; m/z (EI): 342 (M+); m/z (HRMS): 341.9665, C17H10S4 requires 341.9684; UV (CH3CN, nm) 392.

Refinement top

Ring H atoms were placed geometrically 0.93 Å from their parent atoms. For all H atoms, a riding model was used with Ueq(H) = 1.3Ueq(C).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1993); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1965) drawing of the asymmetric unit, showing the atomic numbering scheme and displacement ellipsoids at the 40% probability level.
(I) top
Crystal data top
C17H10S4Z = 8
Mr = 342.53Dx = 1.475 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 23.441 (3) Åθ = 11–18°
b = 10.1303 (14) ŵ = 0.60 mm1
c = 13.5222 (17) ÅT = 295 K
β = 73.822 (10)°Prismatic, yellow
V = 3083.9 (7) Å30.45 × 0.24 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 27.9°
ω/2θ scansh = 2930
Absorption correction: ψ scans
?
k = 130
Tmin = 0.840, Tmax = 0.913l = 017
7317 measured reflections3 standard reflections every 120 min
7013 independent reflections intensity decay: 1%
Rint = 0.052
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6458P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.25 e Å3
5657 reflectionsΔρmin = 0.36 e Å3
379 parameters
Crystal data top
C17H10S4V = 3083.9 (7) Å3
Mr = 342.53Z = 8
Monoclinic, P21/cMo Kα radiation
a = 23.441 (3) ŵ = 0.60 mm1
b = 10.1303 (14) ÅT = 295 K
c = 13.5222 (17) Å0.45 × 0.24 × 0.15 mm
β = 73.822 (10)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
7013 independent reflections
Absorption correction: ψ scans
?
Rint = 0.052
Tmin = 0.840, Tmax = 0.9133 standard reflections every 120 min
7317 measured reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.033379 parameters
wR(F2) = 0.099H-atom parameters constrained
S = 1.07Δρmax = 0.25 e Å3
5657 reflectionsΔρmin = 0.36 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1B0.50369 (3)0.53071 (5)0.86838 (4)0.04845 (13)
S2B0.57143 (2)0.59604 (4)0.65119 (3)0.04058 (11)
S3B0.50855 (2)0.34501 (5)0.69854 (3)0.04335 (12)
S4B0.55851 (2)0.27183 (5)0.46669 (4)0.04114 (12)
C1B0.52733 (8)0.49398 (18)0.74491 (13)0.0379 (4)
C2B0.57625 (7)0.49098 (17)0.54740 (13)0.0348 (3)
C3B0.54640 (8)0.37370 (17)0.57138 (13)0.0371 (4)
C4B0.61036 (7)0.50075 (17)0.44220 (13)0.0344 (3)
C5B0.60535 (8)0.38760 (17)0.38906 (13)0.0362 (4)
C6B0.63262 (8)0.35034 (19)0.28076 (14)0.0399 (4)
C7B0.63742 (9)0.4395 (2)0.20093 (15)0.0520 (5)
C8B0.66253 (11)0.4001 (3)0.09952 (17)0.0712 (8)
C9B0.68258 (11)0.2717 (4)0.0778 (2)0.0805 (9)
C10B0.67725 (10)0.1837 (3)0.1558 (2)0.0732 (8)
C11B0.65316 (9)0.2219 (2)0.25695 (18)0.0549 (5)
C12B0.64641 (8)0.61904 (17)0.40010 (13)0.0370 (4)
C13B0.62091 (9)0.74387 (19)0.41810 (16)0.0476 (4)
C14B0.65410 (12)0.8545 (2)0.3772 (2)0.0626 (6)
C15B0.71170 (12)0.8422 (2)0.31945 (18)0.0657 (7)
C16B0.73771 (10)0.7195 (3)0.30280 (17)0.0604 (6)
C17B0.70551 (9)0.6074 (2)0.34248 (15)0.0475 (5)
S1A0.99807 (2)0.52535 (5)0.87090 (4)0.04715 (13)
S2A0.92916 (2)0.59254 (4)0.72136 (4)0.04177 (12)
S3A0.98892 (2)0.33786 (5)0.70942 (4)0.04403 (12)
S4A0.93756 (2)0.26740 (5)0.52675 (4)0.04269 (12)
C1A0.97276 (8)0.48848 (18)0.77214 (13)0.0379 (4)
C2A0.92288 (8)0.48705 (17)0.62322 (13)0.0357 (4)
C3A0.95101 (8)0.36829 (18)0.61904 (14)0.0383 (4)
C4A0.88889 (7)0.50013 (17)0.55104 (13)0.0356 (4)
C5A0.89233 (8)0.38637 (17)0.49395 (14)0.0372 (4)
C6A0.86478 (8)0.35182 (19)0.41155 (14)0.0395 (4)
C7A0.86338 (9)0.4415 (2)0.33425 (15)0.0485 (5)
C8A0.83780 (11)0.4050 (3)0.25713 (17)0.0648 (7)
C9A0.81401 (10)0.2808 (3)0.2562 (2)0.0733 (8)
C10A0.81575 (11)0.1919 (3)0.3316 (2)0.0719 (7)
C11A0.84075 (10)0.2267 (2)0.40930 (19)0.0566 (5)
C12A0.85495 (8)0.62124 (17)0.54314 (13)0.0359 (4)
C13A0.79560 (8)0.6164 (2)0.54386 (16)0.0457 (4)
C14A0.76500 (9)0.7322 (3)0.53773 (17)0.0575 (6)
C15A0.79301 (11)0.8517 (2)0.52922 (18)0.0599 (6)
C16A0.85175 (11)0.8584 (2)0.52745 (18)0.0566 (5)
C17A0.88251 (8)0.74364 (19)0.53548 (16)0.0442 (4)
H7B0.62390.52560.21520.062*
H8B0.66590.46010.04610.085*
H9B0.69970.24580.01000.097*
H10B0.68990.09710.14090.088*
H11B0.65060.16130.30970.066*
H13B0.58170.75320.45750.057*
H14B0.63690.93780.38920.075*
H15B0.73340.91680.29140.079*
H16B0.77720.71160.26460.073*
H17B0.72330.52470.33060.057*
H7A0.87950.52540.33420.058*
H8A0.83670.46500.20560.078*
H9A0.79680.25740.20450.088*
H10A0.80010.10780.33060.086*
H11A0.84150.16590.46050.068*
H13A0.77630.53540.54850.055*
H14A0.72510.72840.53940.069*
H15A0.77220.92860.52460.072*
H16A0.87090.93960.52090.068*
H17A0.92210.74880.53570.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1B0.0433 (9)0.0329 (8)0.0373 (9)0.0007 (7)0.0108 (7)0.0038 (7)
C2B0.0395 (9)0.0283 (8)0.0359 (8)0.0021 (7)0.0096 (7)0.0010 (7)
C3B0.0412 (9)0.0329 (8)0.0353 (8)0.0004 (7)0.0077 (7)0.0043 (7)
C4B0.0356 (8)0.0298 (8)0.0372 (8)0.0012 (7)0.0091 (7)0.0007 (7)
C5B0.0384 (9)0.0329 (9)0.0373 (9)0.0015 (7)0.0102 (7)0.0015 (7)
C6B0.0361 (9)0.0439 (10)0.0398 (9)0.0051 (8)0.0105 (7)0.0059 (7)
C7B0.0532 (11)0.0619 (13)0.0428 (10)0.0021 (9)0.0165 (9)0.0090 (10)
C8B0.0641 (14)0.109 (2)0.0409 (11)0.0038 (13)0.0156 (10)0.0283 (15)
C9B0.0546 (14)0.127 (3)0.0511 (14)0.0361 (16)0.0005 (11)0.0231 (16)
C10B0.0508 (12)0.0800 (18)0.0786 (17)0.0392 (15)0.0014 (12)0.0019 (12)
C11B0.0503 (11)0.0504 (12)0.0588 (13)0.0135 (10)0.0065 (10)0.0014 (9)
C12B0.0432 (9)0.0335 (9)0.0355 (8)0.0026 (7)0.0128 (7)0.0060 (7)
C13B0.0529 (11)0.0360 (10)0.0554 (12)0.0054 (8)0.0178 (9)0.0023 (8)
C14B0.0859 (17)0.0368 (11)0.0727 (15)0.0117 (10)0.0346 (13)0.0134 (11)
C15B0.0864 (17)0.0590 (15)0.0557 (13)0.0169 (11)0.0262 (12)0.0389 (13)
C16B0.0550 (12)0.0750 (16)0.0465 (11)0.0014 (11)0.0061 (9)0.0261 (12)
C17B0.0460 (10)0.0499 (11)0.0446 (10)0.0055 (9)0.0092 (8)0.0081 (9)
S1B0.0676 (3)0.0414 (3)0.0342 (2)0.00136 (19)0.0107 (2)0.0042 (2)
S2B0.0507 (3)0.0296 (2)0.0388 (2)0.00354 (17)0.00803 (19)0.00255 (18)
S3B0.0531 (3)0.0361 (2)0.0366 (2)0.00123 (18)0.00529 (19)0.0094 (2)
S4B0.0496 (3)0.0326 (2)0.0391 (2)0.00266 (17)0.00897 (19)0.00859 (18)
C1A0.0428 (9)0.0328 (9)0.0406 (9)0.0021 (7)0.0159 (7)0.0027 (7)
C2A0.0408 (9)0.0283 (8)0.0414 (9)0.0005 (7)0.0172 (7)0.0007 (7)
C3A0.0435 (9)0.0331 (8)0.0431 (9)0.0030 (7)0.0200 (8)0.0034 (7)
C4A0.0365 (8)0.0314 (8)0.0411 (9)0.0009 (7)0.0147 (7)0.0019 (7)
C5A0.0388 (9)0.0324 (9)0.0431 (9)0.0007 (7)0.0162 (7)0.0006 (7)
C6A0.0364 (9)0.0418 (10)0.0416 (9)0.0089 (8)0.0127 (7)0.0017 (7)
C7A0.0482 (10)0.0553 (12)0.0430 (10)0.0020 (9)0.0144 (8)0.0030 (9)
C8A0.0587 (13)0.094 (2)0.0452 (12)0.0089 (12)0.0206 (10)0.0163 (13)
C9A0.0543 (13)0.110 (2)0.0621 (15)0.0371 (16)0.0272 (11)0.0067 (14)
C10A0.0614 (14)0.0755 (17)0.0821 (18)0.0310 (15)0.0254 (13)0.0113 (13)
C11A0.0599 (13)0.0499 (12)0.0643 (14)0.0083 (10)0.0242 (11)0.0070 (10)
C12A0.0401 (9)0.0341 (9)0.0351 (8)0.0002 (7)0.0132 (7)0.0035 (7)
C13A0.0411 (9)0.0499 (11)0.0487 (11)0.0061 (9)0.0164 (8)0.0027 (8)
C14A0.0462 (11)0.0772 (16)0.0544 (12)0.0111 (11)0.0231 (9)0.0203 (11)
C15A0.0698 (14)0.0534 (13)0.0595 (13)0.0013 (10)0.0232 (11)0.0268 (11)
C16A0.0683 (14)0.0353 (10)0.0642 (14)0.0050 (9)0.0154 (11)0.0082 (10)
C17A0.0434 (10)0.0349 (9)0.0551 (11)0.0031 (8)0.0151 (8)0.0015 (8)
S1A0.0638 (3)0.0412 (3)0.0447 (3)0.0017 (2)0.0287 (2)0.0038 (2)
S2A0.0531 (3)0.0295 (2)0.0502 (3)0.00560 (18)0.0267 (2)0.00322 (19)
S3A0.0552 (3)0.0345 (2)0.0506 (3)0.00347 (19)0.0283 (2)0.0091 (2)
S4A0.0529 (3)0.0320 (2)0.0487 (3)0.00797 (19)0.0231 (2)0.00772 (19)
Geometric parameters (Å, º) top
C1A—S1A1.6482 (18)C1B—S1B1.6485 (18)
C1A—S2A1.7374 (18)C1B—S2B1.7359 (18)
C1A—S3A1.7355 (19)C1B—S3B1.7373 (19)
C2A—S2A1.7417 (17)C2B—S2B1.7398 (17)
C2A—C3A1.365 (2)C2B—C3B1.371 (2)
C2A—C4A1.428 (2)C2B—C4B1.428 (2)
C3A—S3A1.7274 (18)C3B—S3B1.7257 (18)
C3A—S4A1.7090 (18)C3B—S4B1.7104 (18)
C4A—C5A1.377 (2)C4B—C5B1.375 (2)
C5A—S4A1.7420 (18)C5B—S4B1.7437 (18)
C4A—C12A1.482 (2)C4B—C12B1.485 (2)
C5A—C6A1.477 (2)C5B—C6B1.474 (2)
C6A—C11A1.390 (3)C6B—C7B1.388 (3)
C6A—C7A1.392 (3)C6B—C11B1.393 (3)
C7A—C8A1.390 (3)C7B—C8B1.392 (3)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.377 (4)C8B—C9B1.387 (4)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.369 (4)C9B—C10B1.359 (4)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.384 (3)C10B—C11B1.382 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—H11A0.9300C11B—H11B0.9300
C12A—C17A1.389 (3)C12B—C13B1.391 (3)
C12A—C13A1.389 (3)C12B—C17B1.392 (3)
C13A—C14A1.390 (3)C13B—C14B1.389 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.367 (4)C14B—C15B1.364 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.372 (3)C15B—C16B1.375 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.388 (3)C16B—C17B1.386 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
S1A—C1A—S3A121.08 (11)S1B—C1B—S2B124.66 (11)
S1A—C1A—S2A124.54 (11)S1B—C1B—S3B120.93 (11)
S2A—C1A—S3A114.37 (10)S2B—C1B—S3B114.40 (10)
C3A—C2A—C4A114.11 (15)C3B—C2B—C4B113.76 (15)
C3A—C2A—S2A115.45 (13)C3B—C2B—S2B115.17 (13)
C4A—C2A—S2A130.22 (13)C4B—C2B—S2B130.82 (13)
C2A—C3A—S4A111.83 (13)C2B—C3B—S4B111.78 (13)
C2A—C3A—S3A117.75 (14)C2B—C3B—S3B117.93 (13)
S4A—C3A—S3A130.24 (11)S4B—C3B—S3B130.07 (11)
C5A—C4A—C2A110.42 (15)C5B—C4B—C2B110.92 (15)
C5A—C4A—C12A126.95 (16)C5B—C4B—C12B126.48 (15)
C2A—C4A—C12A122.62 (15)C2B—C4B—C12B122.59 (15)
C4A—C5A—C6A130.66 (16)C4B—C5B—C6B130.99 (16)
C4A—C5A—S4A112.40 (13)C4B—C5B—S4B112.16 (13)
C6A—C5A—S4A116.94 (13)C6B—C5B—S4B116.85 (13)
C11A—C6A—C7A118.93 (18)C7B—C6B—C11B118.68 (19)
C5A—C6A—C11A119.82 (18)C7B—C6B—C5B121.65 (18)
C7A—C6A—C5A121.23 (17)C5B—C6B—C11B119.65 (18)
C8A—C7A—C6A119.7 (2)C6B—C7B—C8B120.0 (2)
C8A—C7A—H7A120.2C6B—C7B—H7B120.0
C6A—C7A—H7A120.2C8B—C7B—H7B120.0
C7A—C8A—C9A120.6 (2)C7B—C8B—C9B120.2 (2)
C9A—C8A—H8A119.7C9B—C8B—H8B119.9
C7A—C8A—H8A119.7C7B—C8B—H8B119.9
C10A—C9A—C8A119.9 (2)C10B—C9B—C8B119.9 (2)
C10A—C9A—H9A120.1C10B—C9B—H9B120.0
C8A—C9A—H9A120.1C8B—C9B—H9B120.0
C9A—C10A—C11A120.3 (2)C9B—C10B—C11B120.5 (3)
C9A—C10A—H10A119.8C9B—C10B—H10B119.7
C11A—C10A—H10A119.8C11B—C10B—H10B119.7
C10A—C11A—C6A120.6 (2)C10B—C11B—C6B120.6 (2)
C10A—C11A—H11A119.7C10B—C11B—H11B119.7
C6A—C11A—H11A119.7C6B—C11B—H11B119.7
C17A—C12A—C13A118.45 (17)C13B—C12B—C17B119.13 (17)
C17A—C12A—C4A119.77 (15)C13B—C12B—C4B119.70 (16)
C13A—C12A—C4A121.78 (17)C17B—C12B—C4B121.16 (17)
C14A—C13A—C12A120.13 (19)C12B—C13B—C14B119.9 (2)
C14A—C13A—H13A119.9C12B—C13B—H13B120.1
C12A—C13A—H13A119.9C14B—C13B—H13B120.1
C15A—C14A—C13A120.62 (19)C15B—C14B—C13B120.6 (2)
C15A—C14A—H14A119.7C15B—C14B—H14B119.7
C13A—C14A—H14A119.7C13B—C14B—H14B119.7
C14A—C15A—C16A120.07 (19)C14B—C15B—C16B119.9 (2)
C14A—C15A—H15A120.0C14B—C15B—H15B120.0
C16A—C15A—H15A120.0C16B—C15B—H15B120.0
C15A—C16A—C17A119.9 (2)C15B—C16B—C17B120.6 (2)
C15A—C16A—H16A120.1C15B—C16B—H16B119.7
C17A—C16A—H16A120.1C17B—C16B—H16B119.7
C12A—C17A—C16A120.82 (18)C16B—C17B—C12B119.8 (2)
C12A—C17A—H17A119.6C16B—C17B—H17B120.1
C16A—C17A—H17A119.6C12B—C17B—H17B120.1
C1A—S2A—C2A96.47 (8)C1B—S2B—C2B96.67 (8)
C1A—S3A—C3A95.95 (8)C1B—S3B—C3B95.84 (8)
C3A—S4A—C5A91.22 (8)C3B—S4B—C5B91.37 (8)
C4B—C2B—C3B—S4B0.3 (2)C4A—C2A—C3A—S4A0.2 (2)
S2B—C2B—C3B—S4B175.14 (9)S2A—C2A—C3A—S4A175.37 (10)
C4B—C2B—C3B—S3B174.82 (13)C4A—C2A—C3A—S3A175.41 (13)
S2B—C2B—C3B—S3B0.0 (2)S2A—C2A—C3A—S3A0.3 (2)
C3B—C2B—C4B—C5B0.4 (2)C3A—C2A—C4A—C5A0.6 (2)
S2B—C2B—C4B—C5B173.40 (14)S2A—C2A—C4A—C5A173.65 (14)
C3B—C2B—C4B—C12B179.56 (16)C3A—C2A—C4A—C12A179.94 (16)
S2B—C2B—C4B—C12B5.8 (3)S2A—C2A—C4A—C12A5.7 (3)
C2B—C4B—C5B—C6B178.87 (18)C2A—C4A—C5A—C6A179.35 (18)
C12B—C4B—C5B—C6B0.3 (3)C12A—C4A—C5A—C6A0.1 (3)
C2B—C4B—C5B—S4B0.92 (19)C2A—C4A—C5A—S4A1.16 (19)
C12B—C4B—C5B—S4B179.96 (14)C12A—C4A—C5A—S4A179.56 (14)
C4B—C5B—C6B—C7B41.6 (3)C4A—C5A—C6A—C11A138.1 (2)
S4B—C5B—C6B—C7B138.63 (16)S4A—C5A—C6A—C11A42.4 (2)
C4B—C5B—C6B—C11B139.7 (2)C4A—C5A—C6A—C7A43.2 (3)
S4B—C5B—C6B—C11B40.1 (2)S4A—C5A—C6A—C7A136.28 (16)
C11B—C6B—C7B—C8B0.2 (3)C11A—C6A—C7A—C8A0.4 (3)
C5B—C6B—C7B—C8B178.93 (19)C5A—C6A—C7A—C8A179.13 (18)
C6B—C7B—C8B—C9B0.3 (3)C6A—C7A—C8A—C9A0.2 (3)
C7B—C8B—C9B—C10B0.5 (4)C7A—C8A—C9A—C10A0.3 (4)
C8B—C9B—C10B—C11B1.4 (4)C8A—C9A—C10A—C11A0.7 (4)
C9B—C10B—C11B—C6B1.5 (4)C9A—C10A—C11A—C6A0.5 (4)
C7B—C6B—C11B—C10B0.7 (3)C7A—C6A—C11A—C10A0.1 (3)
C5B—C6B—C11B—C10B178.06 (19)C5A—C6A—C11A—C10A178.8 (2)
C5B—C4B—C12B—C13B131.2 (2)C5A—C4A—C12A—C17A130.8 (2)
C2B—C4B—C12B—C13B49.8 (2)C2A—C4A—C12A—C17A49.9 (3)
C5B—C4B—C12B—C17B48.7 (3)C5A—C4A—C12A—C13A49.6 (3)
C2B—C4B—C12B—C17B130.33 (19)C2A—C4A—C12A—C13A129.60 (19)
C17B—C12B—C13B—C14B1.1 (3)C17A—C12A—C13A—C14A0.4 (3)
C4B—C12B—C13B—C14B178.71 (19)C4A—C12A—C13A—C14A179.11 (18)
C12B—C13B—C14B—C15B0.2 (3)C12A—C13A—C14A—C15A1.1 (3)
C13B—C14B—C15B—C16B1.1 (4)C13A—C14A—C15A—C16A0.5 (4)
C14B—C15B—C16B—C17B1.3 (4)C14A—C15A—C16A—C17A0.7 (4)
C15B—C16B—C17B—C12B0.3 (3)C13A—C12A—C17A—C16A0.8 (3)
C13B—C12B—C17B—C16B0.9 (3)C4A—C12A—C17A—C16A179.66 (19)
C4B—C12B—C17B—C16B178.94 (18)C15A—C16A—C17A—C12A1.4 (3)
S1B—C1B—S2B—C2B179.91 (12)S1A—C1A—S2A—C2A179.07 (12)
S3B—C1B—S2B—C2B0.26 (12)S3A—C1A—S2A—C2A0.56 (12)
C3B—C2B—S2B—C1B0.16 (15)C3A—C2A—S2A—C1A0.49 (16)
C4B—C2B—S2B—C1B173.57 (17)C4A—C2A—S2A—C1A174.70 (17)
C2B—C3B—S3B—C1B0.16 (16)C2A—C3A—S3A—C1A0.12 (17)
S4B—C3B—S3B—C1B173.94 (14)S4A—C3A—S3A—C1A174.80 (14)
S1B—C1B—S3B—C3B179.92 (12)S1A—C1A—S3A—C3A179.20 (12)
S2B—C1B—S3B—C3B0.26 (12)S2A—C1A—S3A—C3A0.45 (12)
C2B—C3B—S4B—C5B0.71 (15)C2A—C3A—S4A—C5A0.73 (15)
S3B—C3B—S4B—C5B173.68 (14)S3A—C3A—S4A—C5A174.19 (15)
C4B—C5B—S4B—C3B0.95 (15)C4A—C5A—S4A—C3A1.10 (15)
C6B—C5B—S4B—C3B178.87 (14)C6A—C5A—S4A—C3A179.33 (15)

Experimental details

Crystal data
Chemical formulaC17H10S4
Mr342.53
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)23.441 (3), 10.1303 (14), 13.5222 (17)
β (°) 73.822 (10)
V3)3083.9 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.60
Crystal size (mm)0.45 × 0.24 × 0.15
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scans
Tmin, Tmax0.840, 0.913
No. of measured, independent and
observed (?) reflections
7317, 7013, 5657
Rint0.052
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.099, 1.07
No. of reflections5657
No. of parameters379
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.36

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1993), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1965), PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
C1A—S1A1.6482 (18)C1B—S1B1.6485 (18)
C1A—S2A1.7374 (18)C1B—S2B1.7359 (18)
C1A—S3A1.7355 (19)C1B—S3B1.7373 (19)
C2A—S2A1.7417 (17)C2B—S2B1.7398 (17)
C2A—C3A1.365 (2)C2B—C3B1.371 (2)
C2A—C4A1.428 (2)C2B—C4B1.428 (2)
C3A—S3A1.7274 (18)C3B—S3B1.7257 (18)
C3A—S4A1.7090 (18)C3B—S4B1.7104 (18)
C4A—C5A1.377 (2)C4B—C5B1.375 (2)
C5A—S4A1.7420 (18)C5B—S4B1.7437 (18)
S2A—C1A—S3A114.37 (10)S2B—C1B—S3B114.40 (10)
C2A—C3A—S3A117.75 (14)C2B—C3B—S3B117.93 (13)
C2A—C4A—C12A122.62 (15)C2B—C4B—C12B122.59 (15)
C4A—C5A—C6A130.66 (16)C4B—C5B—C6B130.99 (16)
C4A—C5A—S4A112.40 (13)C4B—C5B—S4B112.16 (13)
C5A—C6A—C11A119.82 (18)C5B—C6B—C11B119.65 (18)
C7A—C8A—C9A120.6 (2)C7B—C8B—C9B120.2 (2)
C9A—C10A—C11A120.3 (2)C9B—C10B—C11B120.5 (3)
C1A—S2A—C2A96.47 (8)C1B—S2B—C2B96.67 (8)
C1A—S3A—C3A95.95 (8)C1B—S3B—C3B95.84 (8)
C3A—S4A—C5A91.22 (8)C3B—S4B—C5B91.37 (8)
 

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