Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldithio)-1,4,5,8-tetra­thia­fulvalene-6-carboxyl­ate

Hou, R.; Li, B.; Yin, B.; Wu, L.

doi:10.1107/S1600536809013154

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1057

doi:10.1107/S1600536809013154

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Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldithio)-1,4,5,8-tetrathiafulvalene-6-carboxylate

Rui-bin Hou,^a Bao Li,^b 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 Structures and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: zqcong@ybu.edu.cn

(Received 20 March 2009; accepted 7 April 2009; online 18 April 2009)

In the title molecule, C₁₆H₂₀O₅S₆, the two five-membered rings form a dihedral angle of 4.7 (3)°. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds, which link the molecules into chains propagating in [1 $[\overline{1}]$ 0], and π–π interactions, indicated by the short distances [3.756 (5) Å] between the centroids of five-membered rings from molecules related by translation along the b axis.

Related literature

For background to tetrathiafulvalene derivatives, see Hansen et al. (1992 ); Trippé et al. (2002 ). For details of the synthesis, see Liu et al. (2000 ).

Experimental

Crystal data

C₁₆H₂₀O₅S₆
M_r = 484.68
Monoclinic, C c
a = 22.604 (5) Å
b = 5.2048 (10) Å
c = 17.801 (4) Å
β = 90.65 (3)°
V = 2094.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 291 K
0.20 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.876, T_max = 0.923
9505 measured reflections
4254 independent reflections
3370 reflections with I > 2σ(I)
R_int = 0.101

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.172
S = 0.96
4254 reflections
245 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), 1855 Friedel pairs
Flack parameter: −0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.35	3.127 (7)	141
Symmetry code: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536809013154/cv2536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013154/cv2536Isup2.hkl

checkCIF report

Comment top

Cation sensors based on tetrathiafulvalene (TTF) derivatives have currently attracted widespread attention because such molecules show electrochemical recognition of various metal cations (Trippé et al., 2002). We incorporated TTF with a 15-membered O, S hybrid crown ether to synthesize the title compound because it should be able to bind lithium ion (Hansen et al., 1992). We report herein the synthesis and structure of the title compound, (I).

The molecular structure of (I),C₁₆H₂₀O₅S₆, is shown in Fig.1. Every molecule contains one TTF moiety and one dithia-15-crown-5 ring.TTF moiety is composed of two nearly coplanar five-membered rings with a dehedral angle of 4.68 (27) °. The dithia-15-crown-5 ring adopt a twiste conformation and situated almost perpendicular to TTF moiety. Owing to the absence of strong hydrogen bond donors, the crystal packing is stabilized by weak C—H···O hydrogen bonds, involving the O atoms of the crown ether as acceptors, and the methyl C—H groups as donors (Table 1). The crystal packing exhibits also π–π interactions, proved by short distance Cg1···Cg2ⁱⁱ of 3.756 (5) Å, where Cg1 and Cg2 are centroids of S1/C3/C4/S2/C5 and S3/C6/S4/C7/C8 rings, respectively [symmetry code: (ii) x, 1+y, z].

Related literature top

For background to tetrathiafulvalene derivatives, see Hansen et al. (1992); Trippé et al. (2002). For details of the synthesis, see Liu et al. (2000).

Experimental top

6,7-Dimethoxycarbonyl-2,3- bis(3',6',9'-trioxoundecylthio)-1,4,5,8-tetrathiafulvalene (Liu et al., 2000) (500 mg, 0.92 mmol) were dissovled in DMF (40 ml), LiBr (0.91 g, 10.5 mmol) and a drop of water was added. The mixture was heated at 80 °C for 2 h. After cooling to room temperature, saturated aqueous sodium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO₄) and then concentrated under reduced pressure. The resulting red oil was purified by column chromatography [silica gel, eluent CH₂Cl₂-AcOEt (4: 1 v/v)] to afford the title compound as a red solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of dichloromethane-n-hexane solution 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 molecular structure of (I) with the atom numbering. Displacement ellipsoids are drawn at the 30% probalility level. H atoms omitted for clarity.

Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldithio)-1,4,5,8- tetrathiafulvalene-6-carboxylate top

Crystal data top

C₁₆H₂₀O₅S₆	F(000) = 1008
M_r = 484.68	D_x = 1.537 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 7343 reflections
a = 22.604 (5) Å	θ = 3.4–27.1°
b = 5.2048 (10) Å	µ = 0.68 mm⁻¹
c = 17.801 (4) Å	T = 291 K
β = 90.65 (3)°	Block, red
V = 2094.1 (7) Å³	0.20 × 0.13 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
ω scans	θ_max = 27.5°, θ_min = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→28
T_min = 0.876, T_max = 0.923	k = −6→6
9505 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.0878P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
4254 reflections	Δρ_max = 0.49 e Å⁻³
245 parameters	Δρ_min = −0.46 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1855 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.12 (12)

Crystal data top

C₁₆H₂₀O₅S₆	V = 2094.1 (7) Å³
M_r = 484.68	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 22.604 (5) Å	µ = 0.68 mm⁻¹
b = 5.2048 (10) Å	T = 291 K
c = 17.801 (4) Å	0.20 × 0.13 × 0.12 mm
β = 90.65 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4254 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3370 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.923	R_int = 0.101
9505 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.172	Δρ_max = 0.49 e Å⁻³
S = 0.96	Δρ_min = −0.46 e Å⁻³
4254 reflections	Absolute structure: Flack (1983), 1855 Friedel pairs
245 parameters	Absolute structure parameter: −0.12 (12)
2 restraints

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	0.4826 (4)	1.8931 (13)	0.5758 (4)	0.0638 (17)
H1A	0.4419	1.8858	0.5598	0.096*
H1B	0.5076	1.8546	0.5340	0.096*
H1C	0.4915	2.0622	0.5942	0.096*
C2	0.4534 (3)	1.7154 (11)	0.6912 (3)	0.0426 (12)
C3	0.4679 (2)	1.5069 (10)	0.7458 (3)	0.0388 (11)
C4	0.4324 (2)	1.4479 (11)	0.8031 (3)	0.0413 (11)
H4	0.3979	1.5404	0.8115	0.050*
C5	0.5199 (2)	1.1345 (9)	0.8157 (3)	0.0368 (10)
C6	0.5581 (2)	0.9558 (10)	0.8382 (3)	0.0392 (11)
C7	0.6165 (2)	0.6004 (9)	0.9111 (3)	0.0361 (10)
C8	0.6520 (2)	0.6615 (10)	0.8524 (3)	0.0405 (11)
C9	0.7699 (3)	0.7676 (12)	0.8282 (3)	0.0507 (13)
H9A	0.8086	0.7011	0.8154	0.061*
H9B	0.7580	0.8888	0.7895	0.061*
C10	0.7740 (3)	0.9042 (10)	0.9022 (3)	0.0438 (12)
H10A	0.7372	0.9930	0.9122	0.053*
H10B	0.7813	0.7818	0.9423	0.053*
C11	0.8288 (3)	1.2375 (11)	0.9635 (4)	0.0546 (15)
H11A	0.7901	1.2783	0.9834	0.066*
H11B	0.8474	1.3978	0.9492	0.066*
C12	0.8653 (3)	1.1139 (13)	1.0241 (4)	0.0609 (16)
H12A	0.9037	1.0707	1.0039	0.073*
H12B	0.8715	1.2373	1.0643	0.073*
C13	0.7993 (3)	0.9435 (13)	1.1131 (4)	0.0578 (15)
H13A	0.7692	1.0616	1.0949	0.069*
H13B	0.8202	1.0245	1.1547	0.069*
C14	0.7710 (3)	0.7016 (13)	1.1390 (4)	0.0606 (16)
H14A	0.8020	0.5776	1.1497	0.073*
H14B	0.7511	0.7368	1.1858	0.073*
C15	0.6760 (3)	0.7176 (13)	1.0822 (3)	0.0577 (16)
H15A	0.6784	0.8429	1.0420	0.069*
H15B	0.6677	0.8086	1.1284	0.069*
C16	0.6266 (3)	0.5309 (13)	1.0653 (3)	0.0519 (14)
H16A	0.5894	0.6240	1.0649	0.062*
H16B	0.6250	0.4058	1.1056	0.062*
O1	0.49274 (19)	1.7087 (8)	0.6344 (2)	0.0524 (10)
O2	0.4141 (2)	1.8633 (9)	0.6967 (2)	0.0571 (11)
O3	0.82120 (18)	1.0828 (8)	0.8984 (2)	0.0526 (10)
O4	0.8395 (2)	0.8877 (8)	1.0548 (2)	0.0560 (10)
O5	0.7302 (2)	0.5875 (8)	1.0894 (2)	0.0587 (11)
S1	0.53276 (5)	1.3254 (3)	0.73569 (7)	0.0415 (3)
S2	0.45240 (6)	1.1969 (3)	0.86052 (7)	0.0456 (3)
S3	0.62439 (6)	0.8944 (3)	0.78907 (7)	0.0453 (3)
S4	0.54731 (6)	0.7502 (3)	0.91476 (7)	0.0417 (3)
S5	0.71732 (7)	0.5055 (3)	0.83051 (8)	0.0492 (4)
S6	0.63337 (7)	0.3600 (3)	0.97634 (7)	0.0486 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.081 (5)	0.063 (4)	0.047 (3)	−0.001 (4)	0.006 (3)	0.016 (3)
C2	0.043 (3)	0.044 (3)	0.040 (3)	−0.004 (2)	−0.003 (2)	−0.004 (2)
C3	0.031 (3)	0.049 (3)	0.036 (3)	0.000 (2)	0.0000 (19)	0.000 (2)
C4	0.028 (3)	0.050 (3)	0.046 (3)	−0.001 (2)	0.005 (2)	−0.005 (2)
C5	0.032 (3)	0.042 (2)	0.037 (3)	−0.002 (2)	0.0045 (19)	−0.0003 (19)
C6	0.044 (3)	0.038 (2)	0.035 (2)	−0.013 (2)	0.005 (2)	−0.0006 (18)
C7	0.038 (3)	0.033 (2)	0.038 (2)	−0.005 (2)	0.002 (2)	−0.0025 (18)
C8	0.045 (3)	0.038 (2)	0.038 (3)	−0.006 (2)	0.006 (2)	−0.0047 (19)
C9	0.046 (3)	0.064 (3)	0.042 (3)	0.000 (3)	0.014 (2)	0.004 (2)
C10	0.039 (3)	0.044 (3)	0.049 (3)	−0.002 (2)	0.011 (2)	0.003 (2)
C11	0.048 (3)	0.043 (3)	0.074 (4)	−0.003 (3)	0.021 (3)	−0.001 (3)
C12	0.049 (4)	0.062 (4)	0.072 (4)	−0.008 (3)	0.008 (3)	0.001 (3)
C13	0.058 (4)	0.063 (4)	0.053 (3)	−0.005 (3)	0.007 (3)	−0.009 (3)
C14	0.065 (4)	0.070 (4)	0.047 (3)	−0.009 (3)	−0.003 (3)	0.007 (3)
C15	0.071 (4)	0.061 (3)	0.042 (3)	0.011 (3)	0.006 (3)	−0.006 (3)
C16	0.048 (3)	0.071 (4)	0.038 (3)	0.003 (3)	0.018 (2)	0.006 (2)
O1	0.050 (2)	0.060 (2)	0.048 (2)	0.014 (2)	0.0091 (18)	0.0153 (18)
O2	0.050 (2)	0.064 (2)	0.058 (3)	0.024 (2)	0.0010 (19)	0.0008 (19)
O3	0.043 (2)	0.058 (2)	0.057 (2)	−0.007 (2)	0.0155 (18)	0.0001 (18)
O4	0.061 (3)	0.052 (2)	0.054 (2)	0.006 (2)	0.0100 (19)	0.0062 (17)
O5	0.056 (3)	0.062 (2)	0.058 (3)	−0.001 (2)	0.001 (2)	−0.0022 (19)
S1	0.0371 (7)	0.0476 (7)	0.0400 (6)	0.0027 (6)	0.0104 (5)	0.0065 (5)
S2	0.0393 (7)	0.0540 (7)	0.0439 (7)	−0.0046 (6)	0.0138 (5)	0.0040 (6)
S3	0.0413 (7)	0.0513 (7)	0.0436 (7)	0.0017 (6)	0.0109 (5)	0.0095 (5)
S4	0.0392 (7)	0.0459 (7)	0.0403 (6)	−0.0028 (5)	0.0083 (5)	0.0052 (5)
S5	0.0482 (8)	0.0440 (7)	0.0557 (9)	0.0045 (6)	0.0117 (6)	−0.0058 (6)
S6	0.0592 (9)	0.0414 (7)	0.0452 (7)	−0.0013 (6)	0.0026 (6)	0.0061 (5)

Geometric parameters (Å, º) top

C1—O1	1.434 (7)	C10—O3	1.418 (7)
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C11—O3	1.420 (7)
C2—O2	1.182 (7)	C11—C12	1.496 (10)
C2—O1	1.354 (7)	C11—H11A	0.9700
C2—C3	1.491 (7)	C11—H11B	0.9700
C3—C4	1.342 (7)	C12—O4	1.425 (8)
C3—S1	1.754 (5)	C12—H12A	0.9700
C4—S2	1.716 (6)	C12—H12B	0.9700
C4—H4	0.9300	C13—O4	1.418 (7)
C5—C6	1.328 (7)	C13—C14	1.487 (9)
C5—S2	1.761 (5)	C13—H13A	0.9700
C5—S1	1.763 (5)	C13—H13B	0.9700
C6—S4	1.752 (5)	C14—O5	1.403 (8)
C6—S3	1.772 (6)	C14—H14A	0.9700
C7—C8	1.362 (7)	C14—H14B	0.9700
C7—S6	1.747 (5)	C15—O5	1.404 (8)
C7—S4	1.749 (6)	C15—C16	1.507 (10)
C8—S5	1.733 (6)	C15—H15A	0.9700
C8—S3	1.765 (6)	C15—H15B	0.9700
C9—C10	1.498 (8)	C16—S6	1.824 (6)
C9—S5	1.811 (6)	C16—H16A	0.9700
C9—H9A	0.9700	C16—H16B	0.9700
C9—H9B	0.9700

O1—C1—H1A	109.5	C12—C11—H11B	108.8
O1—C1—H1B	109.5	H11A—C11—H11B	107.7
H1A—C1—H1B	109.5	O4—C12—C11	114.1 (5)
O1—C1—H1C	109.5	O4—C12—H12A	108.7
H1A—C1—H1C	109.5	C11—C12—H12A	108.7
H1B—C1—H1C	109.5	O4—C12—H12B	108.7
O2—C2—O1	125.4 (5)	C11—C12—H12B	108.7
O2—C2—C3	125.5 (6)	H12A—C12—H12B	107.6
O1—C2—C3	109.1 (5)	O4—C13—C14	109.6 (5)
C4—C3—C2	122.2 (5)	O4—C13—H13A	109.8
C4—C3—S1	117.6 (4)	C14—C13—H13A	109.8
C2—C3—S1	120.2 (4)	O4—C13—H13B	109.8
C3—C4—S2	118.1 (4)	C14—C13—H13B	109.8
C3—C4—H4	121.0	H13A—C13—H13B	108.2
S2—C4—H4	121.0	O5—C14—C13	116.4 (5)
C6—C5—S2	123.8 (4)	O5—C14—H14A	108.2
C6—C5—S1	121.7 (4)	C13—C14—H14A	108.2
S2—C5—S1	114.4 (3)	O5—C14—H14B	108.2
C5—C6—S4	124.5 (4)	C13—C14—H14B	108.2
C5—C6—S3	121.9 (4)	H14A—C14—H14B	107.3
S4—C6—S3	113.6 (3)	O5—C15—C16	110.5 (5)
C8—C7—S6	123.4 (4)	O5—C15—H15A	109.5
C8—C7—S4	117.4 (4)	C16—C15—H15A	109.5
S6—C7—S4	118.9 (3)	O5—C15—H15B	109.5
C7—C8—S5	125.0 (4)	C16—C15—H15B	109.5
C7—C8—S3	116.3 (4)	H15A—C15—H15B	108.1
S5—C8—S3	118.3 (3)	C15—C16—S6	114.7 (4)
C10—C9—S5	111.8 (4)	C15—C16—H16A	108.6
C10—C9—H9A	109.3	S6—C16—H16A	108.6
S5—C9—H9A	109.3	C15—C16—H16B	108.6
C10—C9—H9B	109.3	S6—C16—H16B	108.6
S5—C9—H9B	109.3	H16A—C16—H16B	107.6
H9A—C9—H9B	107.9	C2—O1—C1	115.2 (5)
O3—C10—C9	107.9 (4)	C10—O3—C11	114.6 (4)
O3—C10—H10A	110.1	C13—O4—C12	112.3 (5)
C9—C10—H10A	110.1	C14—O5—C15	114.9 (5)
O3—C10—H10B	110.1	C3—S1—C5	94.3 (2)
C9—C10—H10B	110.1	C4—S2—C5	95.4 (2)
H10A—C10—H10B	108.4	C8—S3—C6	95.9 (3)
O3—C11—C12	113.9 (5)	C7—S4—C6	96.3 (3)
O3—C11—H11A	108.8	C8—S5—C9	102.3 (3)
C12—C11—H11A	108.8	C7—S6—C16	102.0 (3)
O3—C11—H11B	108.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.35	3.127 (7)	141

Symmetry code: (i) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀O₅S₆
M_r	484.68
Crystal system, space group	Monoclinic, Cc
Temperature (K)	291
a, b, c (Å)	22.604 (5), 5.2048 (10), 17.801 (4)
β (°)	90.65 (3)
V (Å³)	2094.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.20 × 0.13 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.876, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	9505, 4254, 3370
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.172, 0.96
No. of reflections	4254
No. of parameters	245
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.46
Absolute structure	Flack (1983), 1855 Friedel pairs
Absolute structure parameter	−0.12 (12)

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
C4—H4···O3ⁱ	0.93	2.35	3.127 (7)	141.4

Symmetry code: (i) x−1/2, y+1/2, 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 Programme of Higher Education (grant No. 20060184001) and the Open Project of the State Key Laboratory of Supramolecular Structures and Materials, Jilin University.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hansen, T. K., Jørgensen, T., Stein, P. C. & Becher, J. (1992). J. Org. Chem. 57, 6403–6409. CrossRef CAS Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Liu, S. G., Liu, H. Y., Bandyopadhyay, K., Gao, Z. Q. & Echegoyen, L. (2000). J. Org. Chem. 65, 3292–3298. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trippé, G., Levillain, E., Le Derf, F., Gorgues, A., Sallé, M., Jeppesen, J. O., Nielsen, K. & Becher, J. (2002). Org. Lett. 4, 2461–2464. Web of Science PubMed Google Scholar

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Volume 65| Part 5| May 2009| Page o1057

doi:10.1107/S1600536809013154

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

Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldi­thio)-1,4,5,8-tetra­thia­fulvalene-6-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2,3-(3,6,9-trioxaundecane-1,11-diyldithio)-1,4,5,8-tetrathiafulvalene-6-carboxylate