(2E,7E)-2,7-Bis[(thio-phen-2-yl)methyl-idene]cyclo-hepta-none.

The whole molecule of the title compound, C17H16OS2, is generated by two-fold rotational symmetry. The carbonyl C and O atoms of the cycloheptanone ring lie on the twofold rotation axis which bisects the opposite -CH2-CH2- bond of the ring. The mol-ecule exists in an E,E conformation with respect to the C=C double bond. The cyclo-hepta-none ring exhibits a twisted chair conformation and its mean plane makes a dihedral angle of 50.12 (19)° with the planes of the thio-phene rings. The two S atoms are in an anti arrangement with respect the carbonyl O atom and the dihedral angle between the two thio-phene ring planes is 69.38 (7)°. In the molecule, there are two intramolecular C-H⋯S hydrogen bond, forming S(6) ring motifs. In the crystal, inversion dimers are generated via pairs of C-H⋯O hydrogen bonds. These dimers are inter-connected by another inter-action of the same kind with a neighbouring mol-ecule, forming a mol-ecular chain along the c-axis direction.

Related literature

For applications of thio­phene derivatives in conducting polymers and biology, see: Kolodziejczyk et al. (2013 ▶); Mishra et al. (2011 ▶). For the synthesis of related compounds, see: Alkskas et al. (2013 ▶). For related structures, see: Liang et al. (2007 ▶); Layana et al. (2014 ▶).

Experimental

Crystal data

C17H16OS2

M = 300.44

Orthorhombic,

a = 16.383 (2) Å

b = 11.6119 (14) Å

c = 7.8213 (7) Å

V = 1487.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.873, T max = 0.933

4249 measured reflections

1296 independent reflections

970 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.162

S = 1.03

1296 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814011866/zl2588sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011866/zl2588Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011866/zl2588Isup3.cml

CCDC reference: 1004531

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H16OS2	F(000) = 632
Mr = 300.44	Dx = 1.341 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1331 reflections
a = 16.383 (2) Å	θ = 2.5–28.4°
b = 11.6119 (14) Å	µ = 0.35 mm−1
c = 7.8213 (7) Å	T = 296 K
V = 1487.9 (3) Å3	Block, colorless
Z = 4	0.40 × 0.25 × 0.20 mm

Bruker APEXII CCD diffractometer	1296 independent reflections
Radiation source: fine-focus sealed tube	970 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 2.5°
ω and φ scan	h = −19→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −12→13
Tmin = 0.873, Tmax = 0.933	l = −9→5
4249 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0941P)2 + 0.5613P] where P = (Fo2 + 2Fc2)/3
1296 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.33 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
C1	0.6448 (2)	0.2975 (4)	0.3099 (5)	0.0826 (12)
H1	0.6039	0.2459	0.3403	0.099*
C2	0.6311 (2)	0.3968 (4)	0.2293 (5)	0.0817 (11)
H2	0.5793	0.4217	0.1976	0.098*
C3	0.70218 (17)	0.4600 (3)	0.1968 (4)	0.0570 (8)
H3	0.7028	0.5309	0.1413	0.068*
C4	0.77149 (18)	0.4051 (2)	0.2567 (3)	0.0541 (7)
C5	0.85397 (16)	0.4491 (2)	0.2406 (3)	0.0503 (7)
H5	0.8575	0.5190	0.1831	0.060*
C6	0.92557 (17)	0.4079 (2)	0.2929 (3)	0.0502 (7)
C7	0.9388 (2)	0.2988 (3)	0.3929 (4)	0.0635 (8)
H7A	0.8902	0.2839	0.4604	0.076*
H7B	0.9836	0.3112	0.4719	0.076*
C8	0.9573 (2)	0.1929 (3)	0.2876 (5)	0.0744 (9)
H8A	0.9180	0.1876	0.1952	0.089*
H8B	0.9508	0.1252	0.3589	0.089*
C9	1.0000	0.4747 (3)	0.2500	0.0527 (10)
O1	1.0000	0.5804 (2)	0.2500	0.0718 (9)
S1	0.74489 (6)	0.27612 (8)	0.35060 (12)	0.0737 (4)

	U11	U22	U33	U12	U13	U23
C1	0.087 (3)	0.077 (3)	0.083 (2)	−0.033 (2)	0.035 (2)	−0.0259 (19)
C2	0.064 (2)	0.088 (3)	0.093 (3)	−0.0080 (18)	0.0067 (18)	−0.036 (2)
C3	0.0537 (18)	0.0508 (16)	0.0664 (18)	−0.0055 (12)	−0.0001 (14)	−0.0088 (13)
C4	0.0653 (19)	0.0458 (15)	0.0511 (15)	−0.0061 (13)	0.0077 (13)	−0.0088 (13)
C5	0.0605 (18)	0.0406 (14)	0.0497 (15)	−0.0045 (12)	0.0015 (12)	0.0009 (12)
C6	0.0611 (18)	0.0449 (15)	0.0447 (14)	0.0029 (12)	−0.0001 (12)	−0.0012 (11)
C7	0.076 (2)	0.0562 (18)	0.0583 (17)	0.0009 (15)	−0.0001 (15)	0.0126 (14)
C8	0.095 (3)	0.0469 (16)	0.081 (2)	−0.0040 (16)	0.0034 (19)	0.0095 (15)
C9	0.060 (2)	0.047 (2)	0.051 (2)	0.000	−0.0125 (18)	0.000
O1	0.0603 (18)	0.0437 (16)	0.111 (3)	0.000	−0.0167 (16)	0.000
S1	0.0880 (7)	0.0573 (6)	0.0757 (6)	−0.0154 (4)	0.0209 (4)	0.0017 (4)

C1—C2	1.333 (5)	C6—C9	1.484 (3)
C1—S1	1.689 (4)	C6—C7	1.504 (4)
C1—H1	0.9300	C7—C8	1.511 (4)
C2—C3	1.400 (5)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.384 (4)	C8—C8i	1.517 (7)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.450 (4)	C8—H8B	0.9700
C4—S1	1.724 (3)	C9—O1	1.227 (5)
C5—C6	1.332 (4)	C9—C6i	1.484 (3)
C5—H5	0.9300
C2—C1—S1	112.4 (3)	C9—C6—C7	116.1 (2)
C2—C1—H1	123.8	C6—C7—C8	115.5 (3)
S1—C1—H1	123.8	C6—C7—H7A	108.4
C1—C2—C3	113.5 (3)	C8—C7—H7A	108.4
C1—C2—H2	123.3	C6—C7—H7B	108.4
C3—C2—H2	123.3	C8—C7—H7B	108.4
C4—C3—C2	112.3 (3)	H7A—C7—H7B	107.5
C4—C3—H3	123.9	C7—C8—C8i	113.4 (2)
C2—C3—H3	123.9	C7—C8—H8A	108.9
C3—C4—C5	124.9 (3)	C8i—C8—H8A	108.9
C3—C4—S1	109.7 (2)	C7—C8—H8B	108.9
C5—C4—S1	125.4 (2)	C8i—C8—H8B	108.9
C6—C5—C4	131.8 (3)	H8A—C8—H8B	107.7
C6—C5—H5	114.1	O1—C9—C6	121.53 (16)
C4—C5—H5	114.1	O1—C9—C6i	121.53 (16)
C5—C6—C9	117.8 (2)	C6—C9—C6i	116.9 (3)
C5—C6—C7	126.1 (3)	C1—S1—C4	92.15 (18)
S1—C1—C2—C3	0.1 (4)	C9—C6—C7—C8	−86.3 (3)
C1—C2—C3—C4	−0.2 (4)	C6—C7—C8—C8i	73.2 (4)
C2—C3—C4—C5	179.5 (3)	C5—C6—C9—O1	36.8 (3)
C2—C3—C4—S1	0.2 (3)	C7—C6—C9—O1	−143.08 (18)
C3—C4—C5—C6	178.9 (3)	C5—C6—C9—C6i	−143.2 (3)
S1—C4—C5—C6	−2.0 (4)	C7—C6—C9—C6i	36.92 (18)
C4—C5—C6—C9	178.3 (2)	C2—C1—S1—C4	0.0 (3)
C4—C5—C6—C7	−1.8 (5)	C3—C4—S1—C1	−0.1 (2)
C5—C6—C7—C8	93.8 (4)	C5—C4—S1—C1	−179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.97	2.53	3.205 (3)	126
C7—H7B···O1ii	0.97	2.53	3.282 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1	0.97	2.53	3.205 (3)	126
C7—H7B⋯O1i	0.97	2.53	3.282 (3)	135

Symmetry code: (i) .