13-[4,5-Bis(methyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-6-oxa-3,9,12,14-tetra-thia-bicyclo-[9.3.0]tetra-dec-1(11)-ene.

In the title mol-ecule, C(14)H(18)OS(8), one O atom, two S atoms and six C atoms form an 11-membered ring with a chair-like conformation; the planes of the two five-membered rings connected by a carbon-carbon double bond form a dihedral angle of 29.97 (11)°. In the crystal, pairs of weak inter-molecular C-H⋯S hydrogen bonds link two mol-ecules into inversion dimers.

Related literature

For background to crown ether-annulated 1,3-dithiol-2-thio­nes, see: Hansen et al. (1993 ▶). For the synthesis, see: Chen et al. (2005 ▶). For a related structure, see: Hou et al. (2009 ▶)

Experimental

Crystal data

C14H18OS8

M = 458.76

Triclinic,

a = 8.4542 (17) Å

b = 10.158 (2) Å

c = 13.612 (3) Å

α = 105.00 (3)°

β = 97.83 (3)°

γ = 112.22 (3)°

V = 1008.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.88 mm−1

T = 291 K

0.14 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.886, T max = 0.901

9961 measured reflections

4572 independent reflections

3655 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.170

S = 1.10

4572 reflections

210 parameters

18 restraints

H-atom parameters constrained

Δρmax = 1.09 e Å−3

Δρmin = −0.64 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/S1600536809037301/ng2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037301/ng2642Isup2.hkl

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

C14H18OS8	Z = 2
Mr = 458.76	F(000) = 476
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4542 (17) Å	Cell parameters from 8201 reflections
b = 10.158 (2) Å	θ = 3.1–27.5°
c = 13.612 (3) Å	µ = 0.88 mm−1
α = 105.00 (3)°	T = 291 K
β = 97.83 (3)°	Block, yellow
γ = 112.22 (3)°	0.14 × 0.12 × 0.12 mm
V = 1008.8 (3) Å3

Rigaku R-AXIS RAPID diffractometer	4572 independent reflections
Radiation source: fine-focus sealed tube	3655 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.886, Tmax = 0.901	k = −11→13
9961 measured reflections	l = −17→17

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0884P)2 + 0.6622P] where P = (Fo2 + 2Fc2)/3
4572 reflections	(Δ/σ)max = 0.016
210 parameters	Δρmax = 1.09 e Å−3
18 restraints	Δρmin = −0.64 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	0.0932 (11)	0.6629 (10)	0.3460 (6)	0.147 (3)
H1A	0.1923	0.7484	0.3443	0.220*
H1B	0.0094	0.6954	0.3720	0.220*
H1C	0.0378	0.5904	0.2761	0.220*
C2	0.3190 (6)	0.5333 (5)	0.3702 (3)	0.0698 (11)
C3	0.4341 (5)	0.4102 (4)	0.2243 (3)	0.0507 (7)
C4	0.4512 (4)	0.3545 (3)	0.1275 (2)	0.0461 (7)
C5	0.3940 (4)	0.2608 (3)	−0.0741 (2)	0.0413 (6)
C6	0.2894 (5)	0.2050 (4)	−0.1861 (3)	0.0525 (8)
H6A	0.3691	0.2087	−0.2314	0.063*
H6B	0.2366	0.2724	−0.1949	0.063*
C7	0.2424 (8)	−0.0950 (6)	−0.2145 (6)	0.1025 (17)
H7A	0.3145	−0.0519	−0.1423	0.123*
H7B	0.1583	−0.1969	−0.2240	0.123*
C8	0.3534 (6)	−0.1067 (5)	−0.2800 (5)	0.0943 (17)
H8A	0.2905	−0.1288	−0.3517	0.113*
H8B	0.3794	−0.1915	−0.2786	0.113*
C9	0.6658 (6)	0.0075 (5)	−0.2091 (4)	0.0740 (12)
H9A	0.7526	0.0358	−0.2487	0.089*
H9B	0.6321	−0.0978	−0.2166	0.089*
C10	0.7491 (5)	0.1017 (4)	−0.0953 (3)	0.0649 (10)
H10A	0.8265	0.0635	−0.0660	0.078*
H10B	0.6563	0.0882	−0.0589	0.078*
C11	0.7040 (4)	0.3605 (4)	−0.0996 (3)	0.0469 (7)
H11A	0.7589	0.4682	−0.0874	0.056*
H11B	0.6438	0.3094	−0.1740	0.056*
C12	0.5700 (4)	0.3284 (3)	−0.0371 (2)	0.0407 (6)
C13	0.4928 (6)	0.6013 (4)	0.4070 (3)	0.0661 (10)
C14	0.7619 (13)	0.8815 (12)	0.4955 (7)	0.176 (4)
H14A	0.8239	0.8368	0.4545	0.264*
H14B	0.8442	0.9598	0.5587	0.264*
H14C	0.7053	0.9239	0.4552	0.264*
O1	0.5140 (4)	0.0229 (3)	−0.2531 (2)	0.0707 (7)
S1	0.1683 (2)	0.5780 (2)	0.43099 (13)	0.1162 (6)
S2	0.22953 (15)	0.37585 (11)	0.25246 (8)	0.0674 (3)
S3	0.26931 (11)	0.23691 (10)	0.01898 (7)	0.0513 (2)
S4	0.11564 (12)	0.01405 (12)	−0.22817 (9)	0.0704 (3)
S5	0.87487 (12)	0.30094 (10)	−0.06741 (8)	0.0602 (3)
S6	0.65644 (11)	0.38520 (10)	0.10015 (6)	0.0504 (2)
S7	0.61409 (14)	0.52278 (11)	0.33593 (7)	0.0619 (3)
S8	0.6096 (2)	0.74971 (15)	0.52682 (9)	0.1030 (5)

	U11	U22	U33	U12	U13	U23
C1	0.123 (4)	0.173 (5)	0.156 (5)	0.087 (4)	0.053 (4)	0.031 (4)
C2	0.087 (3)	0.059 (2)	0.060 (2)	0.022 (2)	0.044 (2)	0.0171 (18)
C3	0.062 (2)	0.0419 (16)	0.0491 (17)	0.0220 (15)	0.0185 (14)	0.0151 (13)
C4	0.0529 (18)	0.0395 (15)	0.0474 (16)	0.0223 (13)	0.0130 (13)	0.0134 (13)
C5	0.0474 (16)	0.0328 (13)	0.0428 (15)	0.0202 (12)	0.0075 (12)	0.0091 (11)
C6	0.0540 (19)	0.0458 (17)	0.0492 (17)	0.0240 (15)	−0.0016 (14)	0.0069 (14)
C7	0.090 (3)	0.068 (3)	0.143 (4)	0.032 (2)	0.033 (3)	0.029 (3)
C8	0.068 (3)	0.057 (2)	0.122 (4)	0.027 (2)	0.009 (3)	−0.017 (3)
C9	0.065 (2)	0.053 (2)	0.098 (3)	0.0339 (19)	0.016 (2)	0.005 (2)
C10	0.063 (2)	0.0484 (19)	0.089 (3)	0.0315 (18)	0.0179 (19)	0.0217 (19)
C11	0.0480 (17)	0.0389 (15)	0.0520 (17)	0.0195 (13)	0.0122 (13)	0.0119 (13)
C12	0.0467 (16)	0.0331 (13)	0.0423 (15)	0.0210 (12)	0.0087 (12)	0.0083 (11)
C13	0.089 (3)	0.0504 (19)	0.0500 (19)	0.019 (2)	0.0335 (19)	0.0126 (16)
C14	0.172 (5)	0.168 (5)	0.142 (5)	0.025 (4)	0.065 (4)	0.040 (4)
O1	0.0666 (17)	0.0519 (15)	0.090 (2)	0.0287 (13)	0.0162 (14)	0.0151 (14)
S1	0.1153 (12)	0.1136 (11)	0.1043 (11)	0.0336 (9)	0.0798 (10)	0.0109 (9)
S2	0.0694 (6)	0.0561 (5)	0.0642 (6)	0.0132 (5)	0.0322 (5)	0.0144 (4)
S3	0.0450 (4)	0.0472 (4)	0.0537 (5)	0.0173 (3)	0.0116 (3)	0.0093 (3)
S4	0.0446 (5)	0.0586 (6)	0.0766 (7)	0.0161 (4)	0.0007 (4)	−0.0092 (5)
S5	0.0433 (5)	0.0514 (5)	0.0791 (6)	0.0218 (4)	0.0133 (4)	0.0108 (4)
S6	0.0480 (4)	0.0542 (5)	0.0435 (4)	0.0262 (4)	0.0036 (3)	0.0059 (3)
S7	0.0723 (6)	0.0586 (5)	0.0457 (5)	0.0226 (5)	0.0151 (4)	0.0123 (4)
S8	0.1440 (13)	0.0685 (7)	0.0543 (6)	0.0108 (8)	0.0411 (7)	0.0005 (5)

C1—S1	1.794 (9)	C8—O1	1.405 (6)
C1—H1A	0.9600	C8—H8A	0.9700
C1—H1B	0.9600	C8—H8B	0.9700
C1—H1C	0.9600	C9—O1	1.421 (5)
C2—C13	1.319 (7)	C9—C10	1.495 (6)
C2—S1	1.744 (4)	C9—H9A	0.9700
C2—S2	1.768 (4)	C9—H9B	0.9700
C3—C4	1.344 (5)	C10—S5	1.798 (4)
C3—S2	1.747 (4)	C10—H10A	0.9700
C3—S7	1.756 (4)	C10—H10B	0.9700
C4—S3	1.747 (3)	C11—C12	1.498 (4)
C4—S6	1.753 (3)	C11—S5	1.809 (3)
C5—C12	1.335 (4)	C11—H11A	0.9700
C5—C6	1.496 (4)	C11—H11B	0.9700
C5—S3	1.762 (3)	C12—S6	1.763 (3)
C6—S4	1.814 (4)	C13—S8	1.752 (4)
C6—H6A	0.9700	C13—S7	1.765 (4)
C6—H6B	0.9700	C14—S8	1.665 (9)
C7—C8	1.397 (8)	C14—H14A	0.9600
C7—S4	1.833 (6)	C14—H14B	0.9600
C7—H7A	0.9700	C14—H14C	0.9600
C7—H7B	0.9700
S1—C1—H1A	109.5	C10—C9—H9A	108.9
S1—C1—H1B	109.5	O1—C9—H9B	108.9
H1A—C1—H1B	109.5	C10—C9—H9B	108.9
S1—C1—H1C	109.5	H9A—C9—H9B	107.7
H1A—C1—H1C	109.5	C9—C10—S5	116.1 (3)
H1B—C1—H1C	109.5	C9—C10—H10A	108.3
C13—C2—S1	125.9 (3)	S5—C10—H10A	108.3
C13—C2—S2	117.2 (3)	C9—C10—H10B	108.3
S1—C2—S2	116.8 (3)	S5—C10—H10B	108.3
C4—C3—S2	123.3 (3)	H10A—C10—H10B	107.4
C4—C3—S7	123.7 (3)	C12—C11—S5	113.4 (2)
S2—C3—S7	112.98 (18)	C12—C11—H11A	108.9
C3—C4—S3	122.6 (3)	S5—C11—H11A	108.9
C3—C4—S6	123.2 (3)	C12—C11—H11B	108.9
S3—C4—S6	114.08 (18)	S5—C11—H11B	108.9
C12—C5—C6	127.3 (3)	H11A—C11—H11B	107.7
C12—C5—S3	116.9 (2)	C5—C12—C11	127.1 (3)
C6—C5—S3	115.8 (2)	C5—C12—S6	117.2 (2)
C5—C6—S4	113.5 (3)	C11—C12—S6	115.7 (2)
C5—C6—H6A	108.9	C2—C13—S8	125.2 (3)
S4—C6—H6A	108.9	C2—C13—S7	116.7 (3)
C5—C6—H6B	108.9	S8—C13—S7	117.7 (3)
S4—C6—H6B	108.9	S8—C14—H14A	109.5
H6A—C6—H6B	107.7	S8—C14—H14B	109.5
C8—C7—S4	119.7 (5)	H14A—C14—H14B	109.5
C8—C7—H7A	107.4	S8—C14—H14C	109.5
S4—C7—H7A	107.4	H14A—C14—H14C	109.5
C8—C7—H7B	107.4	H14B—C14—H14C	109.5
S4—C7—H7B	107.4	C8—O1—C9	114.7 (4)
H7A—C7—H7B	106.9	C2—S1—C1	100.8 (3)
C7—C8—O1	114.6 (4)	C3—S2—C2	94.04 (19)
C7—C8—H8A	108.6	C4—S3—C5	94.20 (15)
O1—C8—H8A	108.6	C6—S4—C7	102.0 (2)
C7—C8—H8B	108.6	C10—S5—C11	102.29 (17)
O1—C8—H8B	108.6	C4—S6—C12	93.92 (15)
H8A—C8—H8B	107.6	C3—S7—C13	94.02 (19)
O1—C9—C10	113.4 (3)	C14—S8—C13	104.6 (3)
O1—C9—H9A	108.9

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S2i	0.97	3.00	3.793 (6)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯S2i	0.97	3.00	3.793 (6)	140

Symmetry code: (i) .