1-(Thio­phen-3-yl)ethanone

The structure of the title compound, C₆H₆OS, 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...[pi] 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...[pi] inter­actions and S...O contacts.

Computing details

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

Crystal data

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) Å^3	Columnar, colourless
Z = 8	0.42 × 0.28 × 0.15 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0332P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (10)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Cg1 is the centroid of the thiophene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1^i	0.93	2.94	3.660 (3)	136
C5—H5···Cg1^ii	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.