13-[4,5-Bis(methyl­sulfan­yl)-1,3-dithiol-2-yl­idene]-6-oxa-3,9,12,14-tetra­thia­bicyclo­[9.3.0]tetra­dec-1(11)-ene

Hou, R.-B.; Li, B.; Che, T.; Yin, B.-Z.; Wu, L.-X.

doi:10.1107/S1600536809037301

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2538

doi:10.1107/S1600536809037301

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13-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-oxa-3,9,12,14-tetrathiabicyclo[9.3.0]tetradec-1(11)-ene

Rui-Bin Hou,^a Bao Li,^b Tie Che,^a Bing-Zhu Yin ^a ^* and Li-Xin Wu ^b

^aKey Laboratory of Organism Functional Factors of Changbai Mountain, Yanbian University, Ministry of Education, Yanji 133002, People's Republic of China, and ^bState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: zqcong@ybu.edu.cn

(Received 14 September 2009; accepted 15 September 2009; online 26 September 2009)

In the title molecule, C₁₄H₁₈OS₈, 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 intermolecular C—H⋯S hydrogen bonds link two molecules 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_r = 458.76
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.170
S = 1.10
4572 reflections
210 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.64 e Å⁻³

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) -x, -y, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037301/ng2642sup1.cif

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

checkCIF report

Comment top

Tetrathiafulvalene (TTF) derivatives with a fused crown ether ring have received much attention as component molecules for cation sensors (Hansen et al., 1993). We are incorporated TTF with a sulfur hybrid crown ether to synthesize the title compound

The molecule structure of tiltle compound, (I), C₁₄H₁₈S₈O, as shown in Fig. 1, all bond lengths and angles are normal and comparable with the related structure (Hou et al., 2009). In the crystal, weak intermolecular C—H···S hydrogen bonds (Table 1) link the molecules into dimer.

Related literature top

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 top

The title compound, (I), was prepared according to literature (Chen et al.,2005) and the single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric of title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.

13-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-oxa-3,9,12,14- tetrathiabicyclo[9.3.0]tetradec-1(11)-ene top

Crystal data top

C₁₄H₁₈OS₈	Z = 2
M_r = 458.76	F(000) = 476
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0884P)² + 0.6622P] where P = (F_o² + 2F_c²)/3
4572 reflections	(Δ/σ)_max = 0.016
210 parameters	Δρ_max = 1.09 e Å⁻³
18 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₄H₁₈OS₈	γ = 112.22 (3)°
M_r = 458.76	V = 1008.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.4542 (17) Å	Mo Kα radiation
b = 10.158 (2) Å	µ = 0.88 mm⁻¹
c = 13.612 (3) Å	T = 291 K
α = 105.00 (3)°	0.14 × 0.12 × 0.12 mm
β = 97.83 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4572 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3655 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.901	R_int = 0.032
9961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	18 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.10	Δρ_max = 1.09 e Å⁻³
4572 reflections	Δρ_min = −0.64 e Å⁻³
210 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈OS₈
M_r	458.76
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.4542 (17), 10.158 (2), 13.612 (3)
α, β, γ (°)	105.00 (3), 97.83 (3), 112.22 (3)
V (Å³)	1008.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.14 × 0.12 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.886, 0.901
No. of measured, independent and observed [I > 2σ(I)] reflections	9961, 4572, 3655
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.170, 1.10
No. of reflections	4572
No. of parameters	210
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.64

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S2ⁱ	0.97	3.00	3.793 (6)	140.0

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010), the Specialized Research Fund for the Doctoral Programm of Higher Education (grant No. 2006184001) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

References

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2538

doi:10.1107/S1600536809037301

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

13-[4,5-Bis(methyl­sulfan­yl)-1,3-di­thiol-2-yl­­idene]-6-oxa-3,9,12,14-tetra­thia­bi­cyclo­[9.3.0]tetra­dec-1(11)-ene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

13-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-oxa-3,9,12,14-tetrathiabicyclo[9.3.0]tetradec-1(11)-ene