1-(Thiophen-3-yl)ethanone

Abstract

The structure of the title compound, C(6)H(6)OS, exhibits a flip-type disorder of the thiophene ring [occupancy ratio = 0.848 (3):0.152 (3)], which is typical for many thiophene derivatives. The puckered thiophene ring is essentially coplanar with the plane formed by the non-H atoms of the acetyl substituent, similar to its simple analogues, i.e. 3-acetyl-2-carboxythiophene, 4-acetyl-3-carboxythiophene and 3,5-diacetyl-2-ethylamino-4-methylthiophene. In the crystal structure, molecules are connected by C-H···π hydrogen bonds, forming a sheet parallel to the (001) plane. Moreover, an inspection of the crystal lattice reveals that there are short S···O contacts connecting the molecules of adjacent sheets. Comparison of the title crystal structure with its simple 3-methoxythiophene analogue shows a close similarity in the herringbone arrangement of molecules and in the presence of C-H···π interactions and S···O contacts.

Thiophene-3-carbonyl Chloride

“…Crystal data for C5H3ClOS, M = 146.59 g mol -1 , colourless prism, crystal dimens × 0.12 × 0.10 mm, orthorhombic, space group Pbca (No. 61), a = 14.8926 (10) In summary, we obtained the X-ray crystal structure of thiophene-3-carbonyl chloride for the first time and found the molecule to exhibit ring flip disorder, as has recently been described for various other thiophene-3-carbonyl derivatives. The factors governing whether or not this phenomenon occurs in a given case are unclear.…”

“…Crystal data for C 5 H 3 ClOS, M = 146.59 g mol -1 , colourless prism, crystal dimensions 0.28 × 0.12 × 0.10 mm, orthorhombic, space group Pbca (No. 61), a = 14.8926 (10), b = 14.4046 (10), c = 5.4564(3) Å, α = β = γ = 90.00 • , V = 1170.52(13) Å 3 , Z = 8, D calc = 1.664 g cm -3 , T = 173 K, R1 = 0.0316, Rw2 = 0.0723 for 1000 reflections with I > 2σ(I), and 98 variables, R int 0.0618, goodness of fit on F 2 1.014. Data have been deposited at the Cambridge Crystallographic Data Centre as CCDC 2079391.…”