Molecular and crystal structure of hexa(phenylthio)-1,3-butadiene at 87 K
Abstract
The crystal structure of hexa(phenylthio)-l,3-butadiene, C40H30S6, was studied by X-ray diffraction at 87 K. The space group is monoclinic, Ia, a = 13.947(2) Å, b = 22.254(4) Å, c = 11.610(2) Å, β = 106.54(1)° and Z = 4. Intensity data were collected with MoKα radiation to (sin θ)/λ < 0.705 Å−1. The structure was solved by direct methods. Refinement based on 4920 |Fo| converged at Rw = 0.032.
The central bond of the butadienyl core, 1.472(4) Å, is comparable to the single bond of unconjugated 1,3-butadiene, whereas the two double bonds, 1.353(5) Å and 1.371(5) Å, are longer than expected for a C(sp2) = C(sp2) bond. This may be attributed in part to hybridization changes caused by the S atoms. The large torsion angle over the central bond C1–C2–C3–C4 = −66.8(4)°, reflects the accommodation of this fragment to a highly crowded intramolecular environment. All phenyl rings have intramolecular contacts within van der Waals radii with at least one other ring and one of the butadiene carbon atoms. The sulfur atoms are engaged in an inner loop of short 1,n S···S contacts in the range 3.070(3) Å −3.429(4) Å for n ≥ 3. Averaged deviations from 120° in the ipso, 0.5(1)°, and ortho, −0.5(1)°, positions of the six phenyl rings show that the S atoms serve as electronegative substituents attracting electron density from the rings.
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