2,3-[(3,6-Dioxaoctane-1,8-diyl)bis(sul-fanediylmethylene)]-6,7-bis(methylsulfanyl)-1,4,5,8-tetra-thia-fulvalene.

In the title mol-ecule, C(16)H(22)S(8)O(2), two S atoms, two O atoms and ten C atoms form a 14-membered ring with a boat conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into dimers which are further connected into a chain along the a axis by C-H⋯S hydrogen bonds.

Related literature

Over the past three decades, chemical groups such as crown ethers have been extensively modified on the tetra­thia­fulvalene (TTF) skeleton, see: Jeppesen & Becher (2003 ▶). For details of the synthesis, see: Chen et al. (2005 ▶). For a related structure, see: Hou et al. (2009 ▶).

Experimental

Crystal data

C16H22O2S8

M = 502.82

Triclinic,

a = 9.1748 (18) Å

b = 10.177 (2) Å

c = 14.273 (3) Å

α = 98.49 (3)°

β = 105.58 (3)°

γ = 113.33 (3)°

V = 1129.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.80 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 = 0.896, T max = 0.910

8752 measured reflections

3948 independent reflections

3345 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.128

S = 1.17

3948 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.47 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 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/S1600536809041804/hg2569sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041804/hg2569Isup2.hkl

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

C16H22O2S8	Z = 2
Mr = 502.82	F(000) = 524
Triclinic, P1	Dx = 1.479 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1748 (18) Å	Cell parameters from 9031 reflections
b = 10.177 (2) Å	θ = 3.1–27.5°
c = 14.273 (3) Å	µ = 0.80 mm−1
α = 98.49 (3)°	T = 291 K
β = 105.58 (3)°	Block, yellow
γ = 113.33 (3)°	0.14 × 0.12 × 0.12 mm
V = 1129.1 (4) Å3

Rigaku R-AXIS RAPID diffractometer	3948 independent reflections
Radiation source: fine-focus sealed tube	3345 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.896, Tmax = 0.910	k = −12→12
8752 measured reflections	l = −16→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0734P)2 + 0.3957P] where P = (Fo2 + 2Fc2)/3
3948 reflections	(Δ/σ)max = 0.011
237 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.47 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	1.3188 (5)	1.3283 (5)	1.4807 (3)	0.0753 (11)
H1A	1.3746	1.2709	1.4639	0.113*
H1B	1.3938	1.4078	1.5421	0.113*
H1C	1.2897	1.3696	1.4264	0.113*
C2	1.0102 (4)	1.0784 (3)	1.3801 (2)	0.0407 (6)
C3	0.9324 (3)	0.8957 (3)	1.2084 (2)	0.0391 (6)
C4	0.9441 (3)	0.8476 (3)	1.1199 (2)	0.0385 (6)
C5	1.0573 (4)	0.8202 (3)	0.9740 (2)	0.0390 (6)
C6	1.1888 (4)	0.8549 (3)	0.9252 (2)	0.0468 (7)
H6A	1.2329	0.9591	0.9262	0.056*
H6B	1.1347	0.7950	0.8548	0.056*
C7	1.2681 (5)	0.6217 (4)	0.9544 (3)	0.0651 (9)
H7A	1.3327	0.5927	1.0056	0.078*
H7B	1.1542	0.5855	0.9562	0.078*
C8	1.2573 (7)	0.5487 (5)	0.8545 (4)	0.0880 (13)
H8A	1.3674	0.5934	0.8475	0.106*
H8B	1.2227	0.4433	0.8467	0.106*
C9	1.0860 (8)	0.4660 (7)	0.6849 (4)	0.1128 (19)
H9A	1.1787	0.4945	0.6595	0.135*
H9B	1.0565	0.3662	0.6920	0.135*
C10	0.9459 (9)	0.4676 (9)	0.6175 (4)	0.131 (3)
H10A	0.8974	0.3828	0.5580	0.157*
H10B	0.9870	0.5570	0.5958	0.157*
C11	0.7180 (7)	0.3431 (5)	0.6827 (4)	0.0914 (14)
H11A	0.7741	0.2801	0.6902	0.110*
H11B	0.6044	0.2836	0.6321	0.110*
C12	0.7074 (4)	0.4011 (4)	0.7818 (3)	0.0623 (9)
H12A	0.8214	0.4560	0.8325	0.075*
H12B	0.6441	0.3173	0.8033	0.075*
C13	0.7897 (4)	0.7058 (4)	0.8160 (2)	0.0529 (7)
H13A	0.8643	0.7022	0.7798	0.063*
H13B	0.7503	0.7771	0.7975	0.063*
C14	0.8897 (4)	0.7596 (3)	0.9285 (2)	0.0396 (6)
C15	0.8397 (4)	1.0198 (3)	1.3351 (2)	0.0443 (6)
C16	0.5893 (6)	1.1099 (6)	1.2868 (4)	0.0912 (14)
H16A	0.6654	1.1911	1.2698	0.137*
H16B	0.5123	1.1380	1.3080	0.137*
H16C	0.5258	1.0238	1.2283	0.137*
O1	1.1364 (5)	0.5674 (4)	0.7799 (2)	0.0980 (10)
O2	0.8095 (6)	0.4633 (5)	0.6516 (3)	0.1180 (14)
S1	1.12983 (11)	1.21034 (9)	1.49854 (6)	0.0562 (2)
S2	1.10990 (9)	0.99321 (8)	1.32208 (5)	0.0452 (2)
S3	1.13813 (9)	0.87356 (9)	1.10784 (5)	0.0456 (2)
S4	1.36459 (10)	0.82043 (9)	0.98642 (7)	0.0545 (2)
S5	0.60655 (10)	0.52141 (11)	0.77587 (7)	0.0664 (3)
S6	0.76769 (9)	0.74362 (8)	1.00707 (5)	0.0456 (2)
S7	0.74108 (9)	0.86596 (9)	1.22600 (6)	0.0486 (2)
S8	0.71029 (12)	1.06618 (12)	1.38866 (7)	0.0675 (3)

	U11	U22	U33	U12	U13	U23
C1	0.062 (2)	0.072 (3)	0.051 (2)	0.0072 (19)	0.0037 (16)	−0.0007 (18)
C2	0.0527 (16)	0.0355 (14)	0.0323 (14)	0.0190 (12)	0.0161 (12)	0.0072 (11)
C3	0.0420 (14)	0.0340 (14)	0.0362 (14)	0.0157 (12)	0.0118 (11)	0.0049 (11)
C4	0.0411 (14)	0.0338 (14)	0.0360 (14)	0.0174 (11)	0.0103 (11)	0.0037 (11)
C5	0.0522 (16)	0.0361 (14)	0.0335 (14)	0.0279 (13)	0.0129 (12)	0.0057 (11)
C6	0.0524 (16)	0.0505 (17)	0.0488 (17)	0.0315 (14)	0.0221 (13)	0.0149 (14)
C7	0.082 (2)	0.054 (2)	0.076 (2)	0.0400 (19)	0.037 (2)	0.0251 (18)
C8	0.121 (4)	0.068 (3)	0.091 (3)	0.057 (3)	0.046 (3)	0.013 (2)
C9	0.122 (4)	0.122 (4)	0.080 (3)	0.051 (4)	0.046 (3)	−0.016 (3)
C10	0.187 (6)	0.230 (8)	0.069 (3)	0.164 (6)	0.076 (4)	0.046 (4)
C11	0.117 (4)	0.077 (3)	0.089 (3)	0.063 (3)	0.030 (3)	0.008 (2)
C12	0.0570 (19)	0.054 (2)	0.062 (2)	0.0141 (16)	0.0183 (16)	0.0165 (17)
C13	0.0618 (18)	0.0575 (19)	0.0353 (16)	0.0327 (16)	0.0074 (13)	0.0055 (14)
C14	0.0506 (15)	0.0340 (14)	0.0346 (14)	0.0240 (12)	0.0116 (12)	0.0046 (11)
C15	0.0539 (16)	0.0419 (16)	0.0398 (15)	0.0208 (13)	0.0233 (13)	0.0099 (12)
C16	0.073 (3)	0.117 (4)	0.094 (3)	0.062 (3)	0.026 (2)	0.014 (3)
O1	0.123 (3)	0.077 (2)	0.0679 (19)	0.0270 (19)	0.0434 (18)	−0.0154 (15)
O2	0.174 (4)	0.173 (4)	0.125 (3)	0.139 (3)	0.107 (3)	0.092 (3)
S1	0.0735 (5)	0.0488 (5)	0.0330 (4)	0.0198 (4)	0.0176 (4)	0.0014 (3)
S2	0.0465 (4)	0.0487 (4)	0.0353 (4)	0.0234 (3)	0.0099 (3)	0.0029 (3)
S3	0.0433 (4)	0.0557 (5)	0.0351 (4)	0.0277 (3)	0.0082 (3)	0.0015 (3)
S4	0.0418 (4)	0.0531 (5)	0.0658 (5)	0.0231 (4)	0.0160 (4)	0.0109 (4)
S5	0.0432 (4)	0.0805 (6)	0.0507 (5)	0.0237 (4)	0.0052 (3)	−0.0148 (4)
S6	0.0404 (4)	0.0461 (4)	0.0384 (4)	0.0164 (3)	0.0089 (3)	−0.0005 (3)
S7	0.0433 (4)	0.0459 (4)	0.0454 (4)	0.0121 (3)	0.0176 (3)	0.0029 (3)
S8	0.0690 (5)	0.0832 (7)	0.0609 (6)	0.0388 (5)	0.0379 (4)	0.0115 (5)

C1—S1	1.786 (4)	C9—C10	1.391 (8)
C1—H1A	0.9600	C9—O1	1.410 (5)
C1—H1B	0.9600	C9—H9A	0.9700
C1—H1C	0.9600	C9—H9B	0.9700
C2—C15	1.351 (4)	C10—O2	1.448 (6)
C2—S1	1.741 (3)	C10—H10A	0.9700
C2—S2	1.760 (3)	C10—H10B	0.9700
C3—C4	1.335 (4)	C11—O2	1.394 (6)
C3—S7	1.753 (3)	C11—C12	1.493 (6)
C3—S2	1.759 (3)	C11—H11A	0.9700
C4—S6	1.753 (3)	C11—H11B	0.9700
C4—S3	1.753 (3)	C12—S5	1.802 (4)
C5—C14	1.327 (4)	C12—H12A	0.9700
C5—C6	1.500 (4)	C12—H12B	0.9700
C5—S3	1.763 (3)	C13—C14	1.506 (4)
C6—S4	1.809 (3)	C13—S5	1.828 (4)
C6—H6A	0.9700	C13—H13A	0.9700
C6—H6B	0.9700	C13—H13B	0.9700
C7—C8	1.465 (6)	C14—S6	1.767 (3)
C7—S4	1.782 (4)	C15—S8	1.744 (3)
C7—H7A	0.9700	C15—S7	1.760 (3)
C7—H7B	0.9700	C16—S8	1.806 (5)
C8—O1	1.411 (6)	C16—H16A	0.9600
C8—H8A	0.9700	C16—H16B	0.9600
C8—H8B	0.9700	C16—H16C	0.9600
S1—C1—H1A	109.5	O2—C10—H10A	107.7
S1—C1—H1B	109.5	C9—C10—H10B	107.7
H1A—C1—H1B	109.5	O2—C10—H10B	107.7
S1—C1—H1C	109.5	H10A—C10—H10B	107.1
H1A—C1—H1C	109.5	O2—C11—C12	109.1 (4)
H1B—C1—H1C	109.5	O2—C11—H11A	109.9
C15—C2—S1	124.6 (2)	C12—C11—H11A	109.9
C15—C2—S2	116.2 (2)	O2—C11—H11B	109.9
S1—C2—S2	118.48 (17)	C12—C11—H11B	109.9
C4—C3—S7	124.5 (2)	H11A—C11—H11B	108.3
C4—C3—S2	123.0 (2)	C11—C12—S5	113.1 (3)
S7—C3—S2	112.44 (15)	C11—C12—H12A	109.0
C3—C4—S6	123.6 (2)	S5—C12—H12A	108.9
C3—C4—S3	122.6 (2)	C11—C12—H12B	108.9
S6—C4—S3	113.75 (15)	S5—C12—H12B	109.0
C14—C5—C6	127.7 (3)	H12A—C12—H12B	107.8
C14—C5—S3	116.9 (2)	C14—C13—S5	113.2 (2)
C6—C5—S3	115.3 (2)	C14—C13—H13A	108.9
C5—C6—S4	113.8 (2)	S5—C13—H13A	108.9
C5—C6—H6A	108.8	C14—C13—H13B	108.9
S4—C6—H6A	108.8	S5—C13—H13B	108.9
C5—C6—H6B	108.8	H13A—C13—H13B	107.7
S4—C6—H6B	108.8	C5—C14—C13	127.3 (3)
H6A—C6—H6B	107.7	C5—C14—S6	117.3 (2)
C8—C7—S4	114.3 (3)	C13—C14—S6	115.4 (2)
C8—C7—H7A	108.7	C2—C15—S8	124.2 (2)
S4—C7—H7A	108.7	C2—C15—S7	116.8 (2)
C8—C7—H7B	108.7	S8—C15—S7	118.15 (17)
S4—C7—H7B	108.7	S8—C16—H16A	109.5
H7A—C7—H7B	107.6	S8—C16—H16B	109.5
O1—C8—C7	108.0 (3)	H16A—C16—H16B	109.5
O1—C8—H8A	110.1	S8—C16—H16C	109.5
C7—C8—H8A	110.1	H16A—C16—H16C	109.5
O1—C8—H8B	110.1	H16B—C16—H16C	109.5
C7—C8—H8B	110.1	C9—O1—C8	110.0 (4)
H8A—C8—H8B	108.4	C11—O2—C10	121.3 (4)
C10—C9—O1	108.7 (5)	C2—S1—C1	102.60 (16)
C10—C9—H9A	109.9	C3—S2—C2	94.09 (13)
O1—C9—H9A	109.9	C4—S3—C5	94.92 (13)
C10—C9—H9B	109.9	C7—S4—C6	102.45 (18)
O1—C9—H9B	109.9	C12—S5—C13	101.68 (16)
H9A—C9—H9B	108.3	C4—S6—C14	94.74 (13)
C9—C10—O2	118.5 (4)	C3—S7—C15	93.90 (14)
C9—C10—H10A	107.7	C15—S8—C16	101.88 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···S5i	0.97	2.94	3.762 (5)	143
C1—H1C···O2ii	0.96	2.49	3.379 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯S5i	0.97	2.94	3.762 (5)	143
C1—H1C⋯O2ii	0.96	2.49	3.379 (6)	154

Symmetry codes: (i) ; (ii) .