Buy article online - an online subscription or single-article purchase is required to access this article.
The structure of the title compound, C
6H
6OS, 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
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
interactions and S
O contacts.
Supporting information
CCDC reference: 833419
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
1-(Thiophen-3-yl)ethanone
top
Crystal data top
C6H6OS | F(000) = 528 |
Mr = 126.17 | Dx = 1.380 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6176 reflections |
a = 14.592 (3) Å | θ = 2.7–25.4° |
b = 5.5108 (11) Å | µ = 0.42 mm−1 |
c = 15.106 (3) Å | T = 290 K |
V = 1214.7 (4) Å3 | Columnar, colourless |
Z = 8 | 0.42 × 0.28 × 0.15 mm |
Data collection top
Oxford Diffraction Xcalibur3 CCD diffractometer | 1106 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 683 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 25.4°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008) | h = −15→17 |
Tmin = 0.966, Tmax = 1.000 | k = −6→6 |
6176 measured reflections | l = −11→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1106 reflections | Δρmax = 0.16 e Å−3 |
82 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (10) |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.92563 (12) | 0.2250 (3) | −0.04321 (12) | 0.0603 (6) | |
C4 | 0.92740 (17) | 0.3294 (5) | 0.14413 (17) | 0.0433 (7) | |
H4 | 0.9613 | 0.4460 | 0.1140 | 0.052* | |
C3 | 0.88361 (15) | 0.1309 (4) | 0.10297 (15) | 0.0343 (6) | |
C2 | 0.83774 (17) | −0.0081 (5) | 0.16404 (17) | 0.0435 (7) | |
H2 | 0.8046 | −0.1466 | 0.1494 | 0.052* | |
C6 | 0.88753 (16) | 0.0838 (5) | 0.00646 (16) | 0.0405 (7) | |
C7 | 0.84392 (18) | −0.1416 (5) | −0.02909 (17) | 0.0581 (8) | |
H7A | 0.8451 | −0.1379 | −0.0926 | 0.087* | |
H7B | 0.7816 | −0.1507 | −0.0090 | 0.087* | |
H7C | 0.8771 | −0.2810 | −0.0084 | 0.087* | |
S1 | 0.84751 (8) | 0.0981 (2) | 0.26867 (6) | 0.0473 (4) | 0.848 (3) |
C5 | 0.9139 (7) | 0.3296 (19) | 0.2339 (6) | 0.057 (2) | 0.848 (3) |
H5 | 0.9388 | 0.4454 | 0.2717 | 0.069* | 0.848 (3) |
S1A | 0.9185 (11) | 0.365 (3) | 0.2463 (9) | 0.0473 (4) | 0.152 (3) |
C5A | 0.845 (2) | 0.045 (6) | 0.242 (2) | 0.057 (2) | 0.152 (3) |
H5A | 0.8225 | −0.0415 | 0.2898 | 0.069* | 0.152 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0786 (14) | 0.0623 (13) | 0.0401 (11) | −0.0135 (12) | 0.0037 (10) | 0.0080 (10) |
C4 | 0.0449 (17) | 0.0409 (17) | 0.0440 (17) | −0.0057 (13) | 0.0027 (12) | 0.0019 (13) |
C3 | 0.0344 (13) | 0.0334 (14) | 0.0349 (13) | 0.0027 (13) | −0.0004 (11) | 0.0023 (12) |
C2 | 0.0431 (16) | 0.0435 (15) | 0.0438 (15) | −0.0028 (14) | 0.0038 (13) | 0.0035 (13) |
C6 | 0.0377 (14) | 0.0458 (18) | 0.0381 (15) | 0.0073 (15) | −0.0036 (11) | −0.0004 (14) |
C7 | 0.0660 (18) | 0.0569 (18) | 0.0514 (16) | −0.0047 (17) | −0.0009 (15) | −0.0115 (15) |
S1 | 0.0531 (5) | 0.0553 (7) | 0.0335 (5) | 0.0005 (6) | 0.0032 (5) | 0.0035 (5) |
C5 | 0.063 (3) | 0.052 (5) | 0.057 (5) | −0.005 (3) | −0.008 (3) | −0.009 (3) |
S1A | 0.0531 (5) | 0.0553 (7) | 0.0335 (5) | 0.0005 (6) | 0.0032 (5) | 0.0035 (5) |
C5A | 0.063 (3) | 0.052 (5) | 0.057 (5) | −0.005 (3) | −0.008 (3) | −0.009 (3) |
Geometric parameters (Å, º) top
O1—C6 | 1.215 (3) | C2—H2 | 0.9300 |
C4—C5 | 1.371 (9) | C6—C7 | 1.496 (3) |
C4—C3 | 1.411 (3) | C7—H7A | 0.9600 |
C4—S1A | 1.561 (14) | C7—H7B | 0.9600 |
C4—H4 | 0.9300 | C7—H7C | 0.9600 |
C3—C2 | 1.373 (3) | S1—C5 | 1.686 (11) |
C3—C6 | 1.482 (3) | C5—H5 | 0.9300 |
C2—C5A | 1.22 (3) | S1A—C5A | 2.06 (4) |
C2—S1 | 1.691 (3) | C5A—H5A | 0.9300 |
| | | |
C5—C4—C3 | 111.8 (5) | C3—C6—C7 | 118.8 (2) |
C3—C4—S1A | 119.6 (7) | C6—C7—H7A | 109.5 |
C5—C4—H4 | 124.1 | C6—C7—H7B | 109.5 |
C3—C4—H4 | 124.1 | H7A—C7—H7B | 109.5 |
S1A—C4—H4 | 116.3 | C6—C7—H7C | 109.5 |
C2—C3—C4 | 110.9 (2) | H7A—C7—H7C | 109.5 |
C2—C3—C6 | 125.6 (2) | H7B—C7—H7C | 109.5 |
C4—C3—C6 | 123.5 (2) | C5—S1—C2 | 91.1 (3) |
C5A—C2—C3 | 118.1 (16) | C4—C5—S1 | 112.9 (5) |
C3—C2—S1 | 113.2 (2) | C4—C5—H5 | 123.5 |
C5A—C2—H2 | 118.4 | S1—C5—H5 | 123.5 |
C3—C2—H2 | 123.4 | C4—S1A—C5A | 84.5 (12) |
S1—C2—H2 | 123.4 | C2—C5A—S1A | 107 (2) |
O1—C6—C3 | 120.8 (2) | C2—C5A—H5A | 126.7 |
O1—C6—C7 | 120.3 (2) | S1A—C5A—H5A | 126.7 |
| | | |
C5—C4—C3—C2 | 0.9 (6) | C4—C3—C6—C7 | 175.8 (2) |
S1A—C4—C3—C2 | −0.3 (8) | C5A—C2—S1—C5 | 141 (15) |
C5—C4—C3—C6 | −179.3 (5) | C3—C2—S1—C5 | −0.5 (4) |
S1A—C4—C3—C6 | 179.5 (8) | C3—C4—C5—S1 | −1.3 (8) |
C4—C3—C2—C5A | −4.6 (18) | S1A—C4—C5—S1 | 171 (9) |
C6—C3—C2—C5A | 175.6 (18) | C2—S1—C5—C4 | 1.0 (7) |
C4—C3—C2—S1 | −0.1 (3) | C5—C4—S1A—C5A | −5 (7) |
C6—C3—C2—S1 | −179.93 (19) | C3—C4—S1A—C5A | 2.7 (13) |
C2—C3—C6—O1 | 175.8 (2) | C3—C2—C5A—S1A | 6 (2) |
C4—C3—C6—O1 | −4.0 (4) | S1—C2—C5A—S1A | −34 (13) |
C2—C3—C6—C7 | −4.4 (4) | C4—S1A—C5A—C2 | −5 (2) |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the thiophene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg1i | 0.93 | 2.94 | 3.660 (3) | 136 |
C5—H5···Cg1ii | 0.93 | 2.99 | 3.755 (10) | 141 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+2, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.