1,3-Dimethyl-5,6,7,8-tetra-hydro-4H-cyclo-hepta-[c]thio-phene-4,8-dione.

In the title compound, C(11)H(12)O(2)S, the C and S atoms of the central thio-phene and the methyl groups, and the two carbonyl groups of the cyclo-hepta-nedione are almost coplanar [maximum deviation from the mean plane = 0.221 (2) Å]. The packing is stabilized by π-π inter-actions between the conjugated thio-phenes, the shortest centroid-centroid distance between thio-phene rings being 3.9759 (10) Å.

Related literature

The title compound was obtained as the product of our ongoing research of conjugated thio­phenes for electronic devices and dye-sensitized solar cells (DSSCs). For applications of conjugated thio­phenes, see: Amaresh et al. (2002 ▶); Nielsen & Bjonholm (2004 ▶). For related structures, see: Dufresne et al. (2007 ▶); Kuroda et al. (2005 ▶).

Experimental

Crystal data

C11H12O2S

M = 208.27

Orthorhombic,

a = 15.9875 (6) Å

b = 7.6354 (3) Å

c = 16.9963 (6) Å

V = 2074.75 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.920, T max = 0.951

15732 measured reflections

1822 independent reflections

1430 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.02

1822 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047331/vm2059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047331/vm2059Isup2.hkl

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

C11H12O2S	F(000) = 880
Mr = 208.27	Dx = 1.333 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4563 reflections
a = 15.9875 (6) Å	θ = 2.4–22.2°
b = 7.6354 (3) Å	µ = 0.28 mm−1
c = 16.9963 (6) Å	T = 298 K
V = 2074.75 (13) Å3	Block, yellow
Z = 8	0.30 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	1822 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2σ(I)
graphite	Rint = 0.034
phi and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→19
Tmin = 0.920, Tmax = 0.951	k = −9→8
15732 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.5349P] where P = (Fo2 + 2Fc2)/3
1822 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.29 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	0.20027 (4)	0.11743 (8)	0.72032 (3)	0.0670 (2)
C2	0.35875 (12)	0.1124 (2)	0.70942 (10)	0.0496 (5)
C3	0.32681 (12)	0.1405 (2)	0.63092 (10)	0.0493 (5)
C1	0.29639 (14)	0.0980 (3)	0.76406 (11)	0.0575 (5)
C9	0.37901 (14)	0.1832 (3)	0.56162 (11)	0.0614 (5)
O2	0.35621 (12)	0.1474 (2)	0.49522 (8)	0.0898 (6)
C4	0.24140 (14)	0.1457 (2)	0.62814 (11)	0.0557 (5)
O1	0.47614 (12)	0.0907 (2)	0.79362 (10)	0.0882 (5)
C5	0.44794 (14)	0.0756 (3)	0.72741 (12)	0.0593 (5)
C6	0.50182 (13)	0.0112 (3)	0.66046 (14)	0.0688 (6)
H6A	0.4706	−0.0746	0.6303	0.083*
H6B	0.5508	−0.0467	0.6819	0.083*
C11	0.18386 (16)	0.1778 (3)	0.55955 (15)	0.0779 (7)
H11A	0.2030	0.2778	0.5305	0.117*
H11B	0.1282	0.1991	0.5785	0.117*
H11C	0.1836	0.0768	0.5259	0.117*
C10	0.30152 (17)	0.0610 (4)	0.85104 (12)	0.0842 (7)
H10A	0.3411	−0.0312	0.8602	0.126*
H10B	0.2475	0.0258	0.8700	0.126*
H10C	0.3192	0.1648	0.8782	0.126*
C8	0.45990 (15)	0.2776 (3)	0.57771 (14)	0.0766 (7)
H8A	0.4501	0.3667	0.6174	0.092*
H8B	0.4778	0.3364	0.5300	0.092*
C7	0.53003 (16)	0.1575 (3)	0.60577 (16)	0.0838 (7)
H7A	0.5568	0.1056	0.5601	0.101*
H7B	0.5716	0.2277	0.6328	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0548 (4)	0.0684 (4)	0.0779 (4)	0.0012 (3)	0.0116 (3)	−0.0081 (3)
C2	0.0545 (12)	0.0435 (10)	0.0509 (10)	0.0014 (8)	−0.0025 (8)	−0.0017 (8)
C3	0.0536 (12)	0.0423 (10)	0.0520 (10)	0.0016 (8)	−0.0011 (8)	−0.0048 (8)
C1	0.0666 (14)	0.0511 (12)	0.0549 (11)	0.0028 (9)	0.0053 (9)	−0.0034 (8)
C9	0.0753 (15)	0.0547 (12)	0.0542 (12)	0.0090 (11)	0.0068 (10)	0.0051 (9)
O2	0.1081 (14)	0.1103 (15)	0.0510 (9)	0.0094 (11)	0.0021 (8)	0.0020 (8)
C4	0.0569 (13)	0.0482 (11)	0.0620 (11)	0.0026 (9)	−0.0061 (9)	−0.0085 (8)
O1	0.0824 (12)	0.1029 (13)	0.0792 (11)	0.0074 (10)	−0.0269 (9)	0.0002 (9)
C5	0.0603 (13)	0.0496 (11)	0.0679 (12)	−0.0008 (10)	−0.0089 (10)	0.0025 (9)
C6	0.0524 (13)	0.0577 (13)	0.0962 (16)	0.0081 (10)	−0.0042 (11)	−0.0077 (11)
C11	0.0685 (15)	0.0810 (16)	0.0841 (16)	0.0095 (12)	−0.0247 (12)	−0.0115 (13)
C10	0.105 (2)	0.0922 (17)	0.0554 (13)	0.0103 (15)	0.0135 (12)	0.0038 (12)
C8	0.0785 (16)	0.0637 (14)	0.0875 (16)	−0.0077 (13)	0.0204 (13)	0.0109 (12)
C7	0.0628 (15)	0.0810 (17)	0.1076 (18)	−0.0070 (13)	0.0210 (14)	−0.0048 (14)

S1—C4	1.713 (2)	C6—H6A	0.9700
S1—C1	1.714 (2)	C6—H6B	0.9700
C2—C1	1.367 (3)	C11—H11A	0.9600
C2—C3	1.445 (2)	C11—H11B	0.9600
C2—C5	1.485 (3)	C11—H11C	0.9600
C3—C4	1.367 (3)	C10—H10A	0.9600
C3—C9	1.480 (3)	C10—H10B	0.9600
C1—C10	1.507 (3)	C10—H10C	0.9600
C9—O2	1.217 (2)	C8—C7	1.525 (4)
C9—C8	1.506 (3)	C8—H8A	0.9700
C4—C11	1.505 (3)	C8—H8B	0.9700
O1—C5	1.218 (2)	C7—H7A	0.9700
C5—C6	1.509 (3)	C7—H7B	0.9700
C6—C7	1.521 (3)
C4—S1—C1	93.64 (10)	C4—C11—H11A	109.5
C1—C2—C3	112.43 (18)	C4—C11—H11B	109.5
C1—C2—C5	123.04 (18)	H11A—C11—H11B	109.5
C3—C2—C5	123.89 (17)	C4—C11—H11C	109.5
C4—C3—C2	112.91 (17)	H11A—C11—H11C	109.5
C4—C3—C9	121.98 (17)	H11B—C11—H11C	109.5
C2—C3—C9	124.64 (18)	C1—C10—H10A	109.5
C2—C1—C10	129.9 (2)	C1—C10—H10B	109.5
C2—C1—S1	110.63 (15)	H10A—C10—H10B	109.5
C10—C1—S1	119.38 (16)	C1—C10—H10C	109.5
O2—C9—C3	121.3 (2)	H10A—C10—H10C	109.5
O2—C9—C8	122.2 (2)	H10B—C10—H10C	109.5
C3—C9—C8	116.45 (18)	C9—C8—C7	113.58 (19)
C3—C4—C11	129.9 (2)	C9—C8—H8A	108.8
C3—C4—S1	110.39 (14)	C7—C8—H8A	108.8
C11—C4—S1	119.62 (18)	C9—C8—H8B	108.8
O1—C5—C2	121.9 (2)	C7—C8—H8B	108.8
O1—C5—C6	121.1 (2)	H8A—C8—H8B	107.7
C2—C5—C6	117.02 (17)	C6—C7—C8	114.50 (19)
C5—C6—C7	113.00 (18)	C6—C7—H7A	108.6
C5—C6—H6A	109.0	C8—C7—H7A	108.6
C7—C6—H6A	109.0	C6—C7—H7B	108.6
C5—C6—H6B	109.0	C8—C7—H7B	108.6
C7—C6—H6B	109.0	H7A—C7—H7B	107.6
H6A—C6—H6B	107.8
C1—C2—C3—C4	−0.3 (2)	C9—C3—C4—C11	5.3 (3)
C5—C2—C3—C4	170.75 (18)	C2—C3—C4—S1	0.23 (19)
C1—C2—C3—C9	171.89 (18)	C9—C3—C4—S1	−172.24 (14)
C5—C2—C3—C9	−17.0 (3)	C1—S1—C4—C3	−0.06 (15)
C3—C2—C1—C10	177.1 (2)	C1—S1—C4—C11	−177.88 (17)
C5—C2—C1—C10	5.9 (3)	C1—C2—C5—O1	−26.3 (3)
C3—C2—C1—S1	0.3 (2)	C3—C2—C5—O1	163.48 (19)
C5—C2—C1—S1	−170.90 (15)	C1—C2—C5—C6	151.22 (19)
C4—S1—C1—C2	−0.14 (16)	C3—C2—C5—C6	−19.0 (3)
C4—S1—C1—C10	−177.35 (18)	O1—C5—C6—C7	−103.5 (2)
C4—C3—C9—O2	−34.1 (3)	C2—C5—C6—C7	78.9 (2)
C2—C3—C9—O2	154.3 (2)	O2—C9—C8—C7	−102.1 (3)
C4—C3—C9—C8	144.01 (19)	C3—C9—C8—C7	79.8 (2)
C2—C3—C9—C8	−27.6 (3)	C5—C6—C7—C8	−49.7 (3)
C2—C3—C4—C11	177.76 (19)	C9—C8—C7—C6	−37.6 (3)