4,6,7,9,10,12-Hexahydro-1,3-dithiolo[4,5-f][1,4,9]oxadithia-cyclo-undecine-2-thione.

In the title mol-ecule, C(9)H(12)S(5)O, the five-membered ring and attached S atom are essentially coplanar [mean deviation from the mean plane = 0.020 (1) Å]. The two S atoms belonging to the macrocycle deviate from this plane by 1.005 (1) and 1.337 (2) Å. In the crystal, π-π inter-actions link the mol-ecules into centrosymmetric dimers with a short distance of 3.753 (5) Å between the centroids of the five-membered rings.

Related literature

The title compound was prepared according to Chen et al. (2005 ▶). For background literature concerning crown-ether-annulated 1,3-dithiol-2-thione derivatives, see: Hansen et al. (1992 ▶); Trippé et al. (2002 ▶).

Experimental

Crystal data

C9H12OS5

M = 296.49

Triclinic,

a = 8.3425 (17) Å

b = 8.9611 (18) Å

c = 9.820 (2) Å

α = 98.10 (3)°

β = 106.58 (3)°

γ = 112.74 (3)°

V = 622.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 291 K

0.15 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.877, T max = 0.900

6141 measured reflections

2813 independent reflections

2560 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.106

S = 1.06

2813 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024003/cv2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024003/cv2573Isup2.hkl

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

C9H12OS5	Z = 2
Mr = 296.49	F(000) = 308
Triclinic, P1	Dx = 1.583 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3425 (17) Å	Cell parameters from 5678 reflections
b = 8.9611 (18) Å	θ = 3.4–27.0°
c = 9.820 (2) Å	µ = 0.90 mm−1
α = 98.10 (3)°	T = 291 K
β = 106.58 (3)°	Block, yellow
γ = 112.74 (3)°	0.15 × 0.12 × 0.12 mm
V = 622.2 (2) Å3

Rigaku R-AXIS RAPID diffractometer	2813 independent reflections
Radiation source: fine-focus sealed tube	2560 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.877, Tmax = 0.900	k = −11→11
6141 measured reflections	l = −12→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) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2783P] where P = (Fo2 + 2Fc2)/3
2813 reflections	(Δ/σ)max = 0.003
136 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Experimental. (See detailed section in the paper)

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	0.3295 (3)	0.6916 (3)	0.4927 (2)	0.0376 (4)
C2	0.2130 (3)	0.8764 (2)	0.3463 (2)	0.0300 (4)
C3	0.1113 (3)	0.9792 (2)	0.3073 (2)	0.0354 (4)
H3A	0.1194	1.0051	0.2161	0.042*
H3B	0.1724	1.0851	0.3848	0.042*
C4	−0.2203 (3)	0.6799 (3)	0.1413 (3)	0.0408 (5)
H4A	−0.1445	0.6233	0.1746	0.049*
H4B	−0.3469	0.6075	0.1315	0.049*
C5	−0.2231 (3)	0.6956 (3)	−0.0092 (3)	0.0486 (5)
H5A	−0.2975	0.5852	−0.0811	0.058*
H5B	−0.2805	0.7677	−0.0378	0.058*
C6	−0.0193 (3)	0.6766 (3)	−0.1285 (3)	0.0466 (5)
H6A	−0.1108	0.6664	−0.2208	0.056*
H6B	−0.0423	0.5639	−0.1211	0.056*
C7	0.1742 (3)	0.7686 (3)	−0.1276 (2)	0.0439 (5)
H7A	0.1991	0.8846	−0.1229	0.053*
H7B	0.1754	0.7190	−0.2215	0.053*
C8	0.4004 (3)	0.9279 (2)	0.1782 (2)	0.0367 (4)
H8A	0.5328	1.0056	0.2243	0.044*
H8B	0.3342	0.9920	0.1443	0.044*
C9	0.3363 (2)	0.8552 (2)	0.2922 (2)	0.0294 (4)
O1	−0.0377 (2)	0.7650 (2)	−0.0088 (2)	0.0600 (5)
S1	0.43959 (7)	0.73453 (6)	0.36855 (5)	0.03533 (15)
S2	0.36763 (14)	0.58331 (12)	0.60929 (8)	0.0708 (3)
S3	0.17163 (8)	0.77394 (7)	0.48048 (6)	0.03867 (15)
S4	−0.13328 (7)	0.87314 (7)	0.28369 (6)	0.04162 (16)
S5	0.36387 (8)	0.77082 (7)	0.01819 (6)	0.04019 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (11)	0.0454 (11)	0.0277 (9)	0.0247 (9)	0.0138 (8)	0.0110 (8)
C2	0.0293 (8)	0.0333 (9)	0.0239 (8)	0.0121 (7)	0.0089 (7)	0.0061 (7)
C3	0.0375 (10)	0.0361 (9)	0.0347 (10)	0.0190 (8)	0.0136 (8)	0.0087 (8)
C4	0.0313 (9)	0.0420 (10)	0.0486 (12)	0.0163 (8)	0.0140 (9)	0.0140 (9)
C5	0.0318 (10)	0.0615 (14)	0.0431 (12)	0.0164 (10)	0.0121 (9)	0.0057 (10)
C6	0.0439 (11)	0.0526 (12)	0.0361 (11)	0.0199 (10)	0.0127 (9)	0.0023 (9)
C7	0.0506 (12)	0.0565 (13)	0.0329 (10)	0.0266 (10)	0.0214 (9)	0.0172 (9)
C8	0.0388 (10)	0.0339 (9)	0.0361 (10)	0.0107 (8)	0.0200 (8)	0.0097 (8)
C9	0.0283 (8)	0.0289 (8)	0.0276 (9)	0.0101 (7)	0.0105 (7)	0.0059 (7)
O1	0.0356 (8)	0.0692 (11)	0.0481 (10)	0.0048 (8)	0.0198 (7)	−0.0146 (8)
S1	0.0340 (3)	0.0422 (3)	0.0348 (3)	0.0204 (2)	0.0152 (2)	0.0112 (2)
S2	0.1147 (7)	0.0990 (6)	0.0578 (4)	0.0820 (6)	0.0517 (4)	0.0521 (4)
S3	0.0443 (3)	0.0543 (3)	0.0322 (3)	0.0285 (2)	0.0224 (2)	0.0188 (2)
S4	0.0399 (3)	0.0544 (3)	0.0438 (3)	0.0303 (2)	0.0214 (2)	0.0135 (2)
S5	0.0468 (3)	0.0511 (3)	0.0357 (3)	0.0300 (2)	0.0217 (2)	0.0135 (2)

C1—S2	1.642 (2)	C5—H5A	0.9700
C1—S1	1.726 (2)	C5—H5B	0.9700
C1—S3	1.726 (2)	C6—O1	1.402 (3)
C2—C9	1.346 (3)	C6—C7	1.499 (3)
C2—C3	1.495 (3)	C6—H6A	0.9700
C2—S3	1.7471 (19)	C6—H6B	0.9700
C3—S4	1.814 (2)	C7—S5	1.796 (2)
C3—H3A	0.9700	C7—H7A	0.9700
C3—H3B	0.9700	C7—H7B	0.9700
C4—C5	1.498 (3)	C8—C9	1.497 (3)
C4—S4	1.802 (2)	C8—S5	1.820 (2)
C4—H4A	0.9700	C8—H8A	0.9700
C4—H4B	0.9700	C8—H8B	0.9700
C5—O1	1.426 (3)	C9—S1	1.747 (2)
S2—C1—S1	124.30 (13)	O1—C6—H6A	109.7
S2—C1—S3	123.21 (13)	C7—C6—H6A	109.7
S1—C1—S3	112.49 (12)	O1—C6—H6B	109.7
C9—C2—C3	127.67 (18)	C7—C6—H6B	109.7
C9—C2—S3	115.53 (15)	H6A—C6—H6B	108.2
C3—C2—S3	116.79 (14)	C6—C7—S5	117.34 (17)
C2—C3—S4	112.96 (14)	C6—C7—H7A	108.0
C2—C3—H3A	109.0	S5—C7—H7A	108.0
S4—C3—H3A	109.0	C6—C7—H7B	108.0
C2—C3—H3B	109.0	S5—C7—H7B	108.0
S4—C3—H3B	109.0	H7A—C7—H7B	107.2
H3A—C3—H3B	107.8	C9—C8—S5	114.07 (14)
C5—C4—S4	116.74 (17)	C9—C8—H8A	108.7
C5—C4—H4A	108.1	S5—C8—H8A	108.7
S4—C4—H4A	108.1	C9—C8—H8B	108.7
C5—C4—H4B	108.1	S5—C8—H8B	108.7
S4—C4—H4B	108.1	H8A—C8—H8B	107.6
H4A—C4—H4B	107.3	C2—C9—C8	127.63 (18)
O1—C5—C4	110.55 (19)	C2—C9—S1	116.14 (15)
O1—C5—H5A	109.5	C8—C9—S1	116.20 (14)
C4—C5—H5A	109.5	C6—O1—C5	113.57 (18)
O1—C5—H5B	109.5	C1—S1—C9	97.73 (10)
C4—C5—H5B	109.5	C1—S3—C2	98.01 (10)
H5A—C5—H5B	108.1	C4—S4—C3	102.59 (10)
O1—C6—C7	109.68 (19)	C7—S5—C8	103.70 (11)