6,6-Dimethyl-2H,5H,6H,7H-1,3-dithiolo[4,5-f][1,5,3]dithia-silepin-2-one.

In the structure of the title compound, C(7)H(10)OS(4)Si, the carbonyl O atom lies in the plane of the five-membered dithiole ring with a deviation of only 0.022 (2) Å. The seven-membered ring adopts a chair conformation. The crystal packing is stabilized by S⋯O [3.096 (4) Å] and S⋯S [3.620 (4) Å] contacts, together with C-H⋯S inter-actions.

Related literature

For silicon-containing tetra­thia­fulvalene (TTF) derivatives as ligands, see: Guyon et al. (2005 ▶), and as precursors for the construction of polymetallic arrays, see: Hameau et al. (2008 ▶). For their use in the preparation of conducting charge-transfer complexes and radical-cation salts, see: Biaso et al. (2007 ▶). For the synthesis, see: Li et al. (2012 ▶). For related structures, see: Arumugam et al. (2011 ▶); Hou et al. (2009 ▶).

Experimental

Crystal data

C7H10OS4Si

M = 266.48

Triclinic,

a = 6.148 (7) Å

b = 8.569 (10) Å

c = 11.846 (14) Å

α = 69.292 (12)°

β = 85.821 (13)°

γ = 83.129 (13)°

V = 579.2 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.88 mm−1

T = 296 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.901, T max = 0.933

4000 measured reflections

2012 independent reflections

1628 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.072

S = 1.01

2012 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011142/sj5206sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011142/sj5206Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011142/sj5206Isup3.cml

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

C7H10OS4Si	Z = 2
Mr = 266.48	F(000) = 276
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Melting point = 325–326 K
a = 6.148 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.569 (10) Å	Cell parameters from 1863 reflections
c = 11.846 (14) Å	θ = 2.6–27.4°
α = 69.292 (12)°	µ = 0.88 mm−1
β = 85.821 (13)°	T = 296 K
γ = 83.129 (13)°	Block, colorless
V = 579.2 (12) Å3	0.12 × 0.10 × 0.08 mm

Bruker APEXII CCD diffractometer	2012 independent reflections
Radiation source: fine-focus sealed tube	1628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→7
Tmin = 0.901, Tmax = 0.933	k = −10→10
4000 measured reflections	l = −14→12

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.027P)2 + 0.3021P] where P = (Fo2 + 2Fc2)/3
2012 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 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	1.2928 (4)	0.0788 (3)	0.3530 (2)	0.0504 (7)
C2	0.9211 (4)	0.2483 (3)	0.2614 (2)	0.0417 (6)
C3	0.9299 (4)	0.2691 (3)	0.3675 (2)	0.0406 (6)
C4	0.7687 (4)	0.5515 (3)	0.0965 (2)	0.0439 (6)
H4A	0.7085	0.6027	0.0167	0.053*
H4B	0.9260	0.5568	0.0873	0.053*
C5	0.7677 (4)	0.5943 (3)	0.3452 (2)	0.0476 (7)
H5A	0.9237	0.6060	0.3372	0.057*
H5B	0.7013	0.6636	0.3904	0.057*
C6	0.7323 (5)	0.8941 (3)	0.1163 (3)	0.0650 (8)
H6A	0.6818	0.9381	0.0351	0.097*
H6B	0.8890	0.8919	0.1147	0.097*
H6C	0.6672	0.9640	0.1601	0.097*
C7	0.3523 (4)	0.6708 (4)	0.2051 (3)	0.0597 (8)
H7A	0.2889	0.7372	0.2519	0.090*
H7B	0.3200	0.5568	0.2443	0.090*
H7C	0.2920	0.7145	0.1261	0.090*
O1	1.4633 (3)	−0.0091 (3)	0.37000 (19)	0.0718 (6)
S1	1.16208 (11)	0.17662 (9)	0.45212 (6)	0.0500 (2)
S2	1.14230 (12)	0.12822 (9)	0.22118 (7)	0.0539 (2)
S3	0.71611 (11)	0.33291 (8)	0.15538 (7)	0.0519 (2)
S4	0.72980 (11)	0.37770 (10)	0.43285 (6)	0.0561 (2)
Si1	0.65327 (11)	0.67844 (9)	0.19121 (7)	0.04113 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0479 (16)	0.0476 (16)	0.0509 (17)	0.0014 (13)	−0.0094 (13)	−0.0116 (13)
C2	0.0408 (14)	0.0361 (14)	0.0462 (15)	−0.0036 (11)	−0.0095 (11)	−0.0106 (12)
C3	0.0349 (13)	0.0416 (14)	0.0396 (14)	−0.0054 (11)	−0.0040 (11)	−0.0063 (12)
C4	0.0450 (15)	0.0410 (15)	0.0408 (15)	0.0001 (11)	−0.0060 (12)	−0.0085 (12)
C5	0.0355 (13)	0.0572 (17)	0.0579 (17)	−0.0006 (12)	0.0021 (12)	−0.0317 (14)
C6	0.0622 (19)	0.0425 (16)	0.087 (2)	−0.0083 (14)	0.0008 (17)	−0.0189 (16)
C7	0.0345 (14)	0.0643 (19)	0.078 (2)	0.0007 (13)	−0.0026 (14)	−0.0239 (17)
O1	0.0599 (13)	0.0760 (15)	0.0739 (15)	0.0266 (11)	−0.0219 (11)	−0.0261 (12)
S1	0.0450 (4)	0.0574 (4)	0.0450 (4)	0.0013 (3)	−0.0140 (3)	−0.0141 (3)
S2	0.0602 (4)	0.0494 (4)	0.0527 (4)	0.0113 (3)	−0.0155 (3)	−0.0214 (3)
S3	0.0549 (4)	0.0422 (4)	0.0610 (5)	−0.0007 (3)	−0.0273 (3)	−0.0176 (3)
S4	0.0457 (4)	0.0701 (5)	0.0429 (4)	0.0004 (3)	0.0075 (3)	−0.0114 (4)
Si1	0.0305 (3)	0.0406 (4)	0.0525 (4)	−0.0031 (3)	0.0015 (3)	−0.0171 (3)

C1—O1	1.200 (3)	C5—S4	1.812 (3)
C1—S1	1.768 (3)	C5—Si1	1.865 (3)
C1—S2	1.767 (3)	C5—H5A	0.9700
C2—C3	1.336 (4)	C5—H5B	0.9700
C2—S2	1.747 (3)	C6—Si1	1.852 (3)
C2—S3	1.749 (3)	C6—H6A	0.9600
C3—S1	1.746 (3)	C6—H6B	0.9600
C3—S4	1.753 (3)	C6—H6C	0.9600
C4—S3	1.813 (3)	C7—Si1	1.853 (3)
C4—Si1	1.873 (3)	C7—H7A	0.9600
C4—H4A	0.9700	C7—H7B	0.9600
C4—H4B	0.9700	C7—H7C	0.9600
O1—C1—S1	125.6 (2)	Si1—C6—H6B	109.5
O1—C1—S2	122.9 (2)	H6A—C6—H6B	109.5
S1—C1—S2	111.47 (17)	Si1—C6—H6C	109.5
C3—C2—S2	116.77 (19)	H6A—C6—H6C	109.5
C3—C2—S3	127.3 (2)	H6B—C6—H6C	109.5
S2—C2—S3	115.90 (16)	Si1—C7—H7A	109.5
C2—C3—S1	117.2 (2)	Si1—C7—H7B	109.5
C2—C3—S4	126.9 (2)	H7A—C7—H7B	109.5
S1—C3—S4	115.92 (16)	Si1—C7—H7C	109.5
S3—C4—Si1	115.17 (15)	H7A—C7—H7C	109.5
S3—C4—H4A	108.5	H7B—C7—H7C	109.5
Si1—C4—H4A	108.5	C3—S1—C1	97.14 (15)
S3—C4—H4B	108.5	C2—S2—C1	97.32 (14)
Si1—C4—H4B	108.5	C2—S3—C4	100.85 (12)
H4A—C4—H4B	107.5	C3—S4—C5	102.02 (14)
S4—C5—Si1	116.21 (14)	C6—Si1—C7	112.72 (14)
S4—C5—H5A	108.2	C6—Si1—C5	107.85 (14)
Si1—C5—H5A	108.2	C7—Si1—C5	108.97 (14)
S4—C5—H5B	108.2	C6—Si1—C4	107.65 (15)
Si1—C5—H5B	108.2	C7—Si1—C4	107.94 (13)
H5A—C5—H5B	107.4	C5—Si1—C4	111.76 (14)
Si1—C6—H6A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···S1i	0.97	2.89	3.673 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯S1i	0.97	2.89	3.673 (5)	138

Symmetry code: (i) .