4,5-Dihydro-cyclo-penta-[b]thio-phen-6-one.

The title compound, C(7)H(6)OS, crystallizes with two similar mol-ecules, 1 and 2, in the asymmetric unit. Both mol-ecules are essentially planar with r.m.s. deviations of 0.0193 and 0.0107 Å for the planes through the nine non-H atoms of mol-ecules 1 and 2, respectively. The thio-phene and 4,5-dihydro-cyclo-penta-dienone rings are inclined at 2.40 (13)° in 1 and 0.64 (13)° in 2. In the crystal structure π-π [3.6542 (17) Å] and C-H⋯π contacts stack the mol-ecules into columns in an inverse fashion along the b axis. An extensive series of C-H⋯O hydrogen bonds links the columns, generating an extended network structure.

Related literature

For low band-gap and fluorescent applications of conjugated thio­phene vinyl­ene oligomers, see: Blanchard et al. (1997 ▶, 1998a ▶,b ▶, 2006 ▶). For control of the band-gap in the corres­ponding polymers, see: Roncali et al. (1994 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Chang et al. (2004 ▶); Bonini et al. (2004 ▶). For the synthetic route to the starting material, methyl 6-oxo-5,6-dihydro-4H-cyclo­penta­[b]thio­phene-5-carboxyl­ate, see: Cai et al. (2002 ▶); More & Finney (2002 ▶); Yang (2009 ▶).

Experimental

Crystal data

C7H6OS

M = 138.18

Triclinic,

a = 6.6133 (9) Å

b = 7.4894 (11) Å

c = 13.3213 (16) Å

α = 83.247 (8)°

β = 86.097 (7)°

γ = 71.363 (8)°

V = 620.54 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 92 K

0.55 × 0.28 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.617, T max = 0.745

5251 measured reflections

1522 independent reflections

1264 reflections with I > 2σ(I)

R int = 0.040

θmax = 22.1°

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.11

1522 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: APEX2 (Bruker, 2011 ▶) and SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056042/tk5042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056042/tk5042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056042/tk5042Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H6OS	Z = 4
Mr = 138.18	F(000) = 288
Triclinic, P1	Dx = 1.479 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6133 (9) Å	Cell parameters from 1413 reflections
b = 7.4894 (11) Å	θ = 3.1–22.0°
c = 13.3213 (16) Å	µ = 0.42 mm−1
α = 83.247 (8)°	T = 92 K
β = 86.097 (7)°	Rectangular plate, yellow
γ = 71.363 (8)°	0.55 × 0.28 × 0.02 mm
V = 620.54 (14) Å3

Bruker APEXII CCD area-detector diffractometer	1522 independent reflections
Radiation source: fine-focus sealed tube	1264 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 22.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −6→6
Tmin = 0.617, Tmax = 0.745	k = −7→7
5251 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0126P] where P = (Fo2 + 2Fc2)/3
1522 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.46716 (12)	0.59750 (11)	0.65016 (6)	0.0210 (3)
C12	0.6994 (5)	0.5881 (4)	0.5819 (2)	0.0205 (8)
H12	0.7031	0.6465	0.5148	0.025*
C13	0.8795 (5)	0.4873 (4)	0.6343 (2)	0.0196 (8)
H13	1.0213	0.4668	0.6078	0.024*
C14	0.9491 (5)	0.3065 (4)	0.8221 (2)	0.0193 (8)
H14A	1.0453	0.3705	0.8447	0.023*
H14B	1.0345	0.1774	0.8064	0.023*
C15	0.7725 (5)	0.2999 (4)	0.9031 (2)	0.0196 (8)
H15A	0.7831	0.1670	0.9267	0.023*
H15B	0.7872	0.3637	0.9619	0.023*
C16	0.5581 (5)	0.4015 (4)	0.8544 (2)	0.0195 (8)
O1	0.3814 (3)	0.4238 (3)	0.89458 (15)	0.0248 (6)
C17	0.6113 (5)	0.4662 (4)	0.7517 (2)	0.0176 (8)
C18	0.8269 (5)	0.4181 (4)	0.7325 (2)	0.0165 (7)
S2	0.47328 (13)	0.09696 (11)	0.12918 (6)	0.0222 (3)
C22	0.2153 (5)	0.2131 (4)	0.0920 (2)	0.0228 (8)
H22	0.1814	0.2782	0.0266	0.027*
C23	0.0655 (5)	0.2020 (4)	0.1654 (2)	0.0223 (8)
H23	−0.0840	0.2574	0.1574	0.027*
C24	0.0802 (5)	0.0432 (4)	0.3591 (2)	0.0198 (8)
H24A	−0.0149	−0.0345	0.3558	0.024*
H24B	0.0024	0.1568	0.3937	0.024*
C25	0.2881 (5)	−0.0727 (4)	0.4135 (2)	0.0185 (8)
H25A	0.3004	−0.0146	0.4749	0.022*
H25B	0.2877	−0.2040	0.4339	0.022*
C26	0.4739 (5)	−0.0725 (4)	0.3396 (2)	0.0170 (8)
O2	0.6635 (3)	−0.1458 (3)	0.35756 (15)	0.0232 (6)
C27	0.3776 (5)	0.0332 (4)	0.2462 (2)	0.0181 (8)
C28	0.1598 (5)	0.0976 (4)	0.2551 (2)	0.0181 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0114 (5)	0.0241 (6)	0.0242 (5)	−0.0009 (4)	−0.0045 (4)	−0.0007 (4)
C12	0.0189 (19)	0.0248 (19)	0.0193 (17)	−0.0099 (15)	−0.0005 (14)	0.0000 (14)
C13	0.0099 (18)	0.0216 (18)	0.0250 (19)	−0.0011 (14)	0.0014 (14)	−0.0048 (14)
C14	0.0125 (18)	0.0215 (19)	0.0229 (18)	−0.0037 (14)	−0.0018 (14)	−0.0020 (14)
C15	0.0166 (19)	0.0200 (18)	0.0207 (17)	−0.0040 (14)	−0.0017 (14)	−0.0011 (14)
C16	0.016 (2)	0.0171 (19)	0.0265 (18)	−0.0050 (15)	−0.0030 (16)	−0.0075 (14)
O1	0.0106 (14)	0.0311 (14)	0.0318 (13)	−0.0052 (10)	0.0044 (11)	−0.0061 (10)
C17	0.0100 (18)	0.0170 (18)	0.0236 (17)	−0.0007 (14)	−0.0049 (13)	−0.0014 (14)
C18	0.0117 (18)	0.0167 (17)	0.0217 (18)	−0.0041 (13)	0.0000 (13)	−0.0049 (14)
S2	0.0177 (6)	0.0271 (6)	0.0217 (5)	−0.0079 (4)	0.0016 (4)	−0.0014 (4)
C22	0.023 (2)	0.0224 (19)	0.0212 (18)	−0.0055 (15)	−0.0037 (15)	0.0044 (14)
C23	0.0154 (19)	0.0226 (19)	0.0283 (19)	−0.0038 (15)	−0.0057 (16)	−0.0032 (15)
C24	0.0124 (18)	0.0219 (18)	0.0239 (18)	−0.0038 (14)	−0.0001 (14)	−0.0025 (14)
C25	0.0167 (19)	0.0197 (18)	0.0176 (17)	−0.0037 (14)	−0.0044 (14)	0.0013 (14)
C26	0.015 (2)	0.0152 (17)	0.0217 (18)	−0.0043 (14)	−0.0002 (14)	−0.0057 (13)
O2	0.0094 (14)	0.0281 (14)	0.0284 (13)	−0.0010 (10)	−0.0032 (10)	−0.0003 (10)
C27	0.0125 (19)	0.0203 (19)	0.0222 (17)	−0.0049 (14)	0.0008 (14)	−0.0064 (14)
C28	0.0138 (18)	0.0189 (18)	0.0221 (18)	−0.0047 (14)	−0.0013 (14)	−0.0052 (14)

S1—C12	1.716 (3)	S2—C27	1.716 (3)
S1—C17	1.723 (3)	S2—C22	1.726 (3)
C12—C13	1.375 (4)	C22—C23	1.359 (4)
C12—H12	0.9500	C22—H22	0.9500
C13—C18	1.412 (4)	C23—C28	1.413 (4)
C13—H13	0.9500	C23—H23	0.9500
C14—C18	1.497 (4)	C24—C28	1.506 (4)
C14—C15	1.543 (4)	C24—C25	1.547 (4)
C14—H14A	0.9900	C24—H24A	0.9900
C14—H14B	0.9900	C24—H24B	0.9900
C15—C16	1.526 (4)	C25—C26	1.522 (4)
C15—H15A	0.9900	C25—H25A	0.9900
C15—H15B	0.9900	C25—H25B	0.9900
C16—O1	1.221 (4)	C26—O2	1.225 (4)
C16—C17	1.456 (4)	C26—C27	1.461 (4)
C17—C18	1.368 (4)	C27—C28	1.366 (4)
C12—S1—C17	90.47 (15)	C27—S2—C22	89.93 (15)
C13—C12—S1	113.1 (2)	C23—C22—S2	113.3 (2)
C13—C12—H12	123.5	C23—C22—H22	123.3
S1—C12—H12	123.5	S2—C22—H22	123.3
C12—C13—C18	111.3 (3)	C22—C23—C28	111.6 (3)
C12—C13—H13	124.3	C22—C23—H23	124.2
C18—C13—H13	124.3	C28—C23—H23	124.2
C18—C14—C15	103.4 (2)	C28—C24—C25	103.1 (2)
C18—C14—H14A	111.1	C28—C24—H24A	111.1
C15—C14—H14A	111.1	C25—C24—H24A	111.1
C18—C14—H14B	111.1	C28—C24—H24B	111.1
C15—C14—H14B	111.1	C25—C24—H24B	111.1
H14A—C14—H14B	109.0	H24A—C24—H24B	109.1
C16—C15—C14	107.4 (2)	C26—C25—C24	107.4 (2)
C16—C15—H15A	110.2	C26—C25—H25A	110.2
C14—C15—H15A	110.2	C24—C25—H25A	110.2
C16—C15—H15B	110.2	C26—C25—H25B	110.2
C14—C15—H15B	110.2	C24—C25—H25B	110.2
H15A—C15—H15B	108.5	H25A—C25—H25B	108.5
O1—C16—C17	128.2 (3)	O2—C26—C27	128.6 (3)
O1—C16—C15	126.6 (3)	O2—C26—C25	125.8 (3)
C17—C16—C15	105.1 (3)	C27—C26—C25	105.6 (3)
C18—C17—C16	112.5 (3)	C28—C27—C26	112.0 (3)
C18—C17—S1	112.4 (2)	C28—C27—S2	112.9 (2)
C16—C17—S1	135.1 (2)	C26—C27—S2	135.1 (2)
C17—C18—C13	112.7 (3)	C27—C28—C23	112.3 (3)
C17—C18—C14	111.5 (3)	C27—C28—C24	111.8 (3)
C13—C18—C14	135.8 (3)	C23—C28—C24	135.8 (3)

Cg1 and Cg4 are the centroids of the S1,C12,C13,C17,C18 and S2,C22,C23,C27,C28 thiophene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.99	2.52	3.473 (4)	160.
C15—H15B···O1ii	0.99	2.59	3.489 (3)	151.
C12—H12···O2iii	0.95	2.43	3.370 (4)	168.
C13—H13···O2iv	0.95	2.65	3.275 (4)	124.
C23—H23···O1v	0.95	2.62	3.425 (4)	143.
C24—H24A···O2vi	0.99	2.52	3.480 (4)	164.
C25—H25A···O2vii	0.99	2.71	3.704 (3)	180.
C25—H25B···Cg1viii	0.99	2.79	3.561 (3)	135
C15—H15A···Cg4iii	0.99	2.84	3.571 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the S1,C12,C13,C17,C18 and S2,C22,C23,C27,C28 thio­phene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.99	2.52	3.473 (4)	160
C15—H15B⋯O1ii	0.99	2.59	3.489 (3)	151
C12—H12⋯O2iii	0.95	2.43	3.370 (4)	168
C13—H13⋯O2iv	0.95	2.65	3.275 (4)	124
C23—H23⋯O1v	0.95	2.62	3.425 (4)	143
C24—H24A⋯O2vi	0.99	2.52	3.480 (4)	164
C25—H25A⋯O2vii	0.99	2.71	3.704 (3)	180
C25—H25B⋯Cg1viii	0.99	2.79	3.561 (3)	135
C15—H15A⋯Cg4iii	0.99	2.84	3.571 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .