6,7-Bis(methyl-sulfan-yl)-2,3-[(3,6,9-trioxaundecane-1,11-di-yl)bis-(sulfanediylmethyl-ene)]-1,4,5,8-tetra-thia-fulvalene.

In the title compound, C(18)H(26)O(3)S(8), the two five-membered rings exhibit envelope conformations. The two S atoms in the 17-membered macrocycle deviate from the plane of the fused five-membered ring by 1.429 (3) and -1.434 (3) Å in opposite directions.

Related literature

For background to dithia­crown ether annulated tetra­thia­fulvalenes, see: Otsubo & Ogura (1985 ▶); Moore et al. (2000 ▶). For details of the synthesis, see: Chen et al. (2005 ▶). For a related structure, see Hou et al. (2009 ▶).

Experimental

Crystal data

C18H26O3S8

M = 546.87

Triclinic,

a = 9.715 (5) Å

b = 11.585 (7) Å

c = 12.548 (5) Å

α = 98.37 (2)°

β = 112.112 (18)°

γ = 103.94 (2)°

V = 1225.3 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 290 K

0.13 × 0.11 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.909, T max = 0.922

12067 measured reflections

5535 independent reflections

4519 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.09

5535 reflections

264 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.84 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/S160053681001192X/cv2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001192X/cv2706Isup2.hkl

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

C18H26O3S8	Z = 2
Mr = 546.87	F(000) = 572
Triclinic, P1	Dx = 1.482 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.715 (5) Å	Cell parameters from 8201 reflections
b = 11.585 (7) Å	θ = 3.1–27.5°
c = 12.548 (5) Å	µ = 0.75 mm−1
α = 98.37 (2)°	T = 290 K
β = 112.112 (18)°	Block, yellow
γ = 103.94 (2)°	0.13 × 0.11 × 0.11 mm
V = 1225.3 (11) Å3

Rigaku R-AXIS RAPID diffractometer	5535 independent reflections
Radiation source: fine-focus sealed tube	4519 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→11
Tmin = 0.909, Tmax = 0.922	k = −14→15
12067 measured reflections	l = −15→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.6546P] where P = (Fo2 + 2Fc2)/3
5535 reflections	(Δ/σ)max = 0.004
264 parameters	Δρmax = 1.19 e Å−3
0 restraints	Δρmin = −0.84 e Å−3

Experimental. (See detailed section in the paper)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.8329 (4)	0.2619 (3)	−0.0795 (3)	0.0673 (8)
H1A	0.9100	0.3281	−0.0122	0.101*
H1B	0.8797	0.2016	−0.0963	0.101*
H1C	0.7472	0.2243	−0.0620	0.101*
C2	0.6741 (3)	0.4211 (2)	−0.1600 (2)	0.0461 (6)
C3	0.6468 (3)	0.6002 (2)	−0.0284 (2)	0.0378 (5)
C4	0.6879 (3)	0.7034 (2)	0.0568 (2)	0.0375 (5)
C5	0.8608 (3)	0.9048 (2)	0.2248 (2)	0.0377 (5)
C6	1.0049 (3)	0.9939 (2)	0.3263 (2)	0.0453 (6)
H6A	1.0222	0.9641	0.3970	0.054*
H6B	0.9875	1.0724	0.3417	0.054*
C7	1.1338 (4)	1.0744 (4)	0.1696 (3)	0.0672 (9)
H7A	1.1946	1.0522	0.1287	0.081*
H7B	1.0238	1.0324	0.1167	0.081*
C8	1.1631 (4)	1.2111 (4)	0.1912 (4)	0.0809 (11)
H8A	1.2668	1.2551	0.2548	0.097*
H8B	1.1577	1.2362	0.1197	0.097*
C9	1.0704 (4)	1.3669 (3)	0.2552 (3)	0.0717 (9)
H9A	1.0745	1.4025	0.1906	0.086*
H9B	1.1688	1.4080	0.3253	0.086*
C10	0.9373 (4)	1.3834 (3)	0.2801 (3)	0.0631 (8)
H10A	0.9445	1.4696	0.2948	0.076*
H10B	0.8383	1.3365	0.2124	0.076*
C11	0.8268 (4)	1.3533 (3)	0.4170 (3)	0.0631 (8)
H11A	0.7245	1.3175	0.3497	0.076*
H11B	0.8427	1.4396	0.4478	0.076*
C12	0.8366 (4)	1.2872 (3)	0.5112 (3)	0.0684 (9)
H12A	0.9438	1.3157	0.5724	0.082*
H12B	0.7701	1.3060	0.5479	0.082*
C13	0.6293 (4)	1.0953 (3)	0.4346 (3)	0.0646 (8)
H13A	0.5700	1.1524	0.4205	0.077*
H13B	0.6215	1.0642	0.5006	0.077*
C14	0.5624 (4)	0.9902 (3)	0.3249 (3)	0.0579 (7)
H14A	0.4659	0.9349	0.3191	0.070*
H14B	0.6358	0.9445	0.3335	0.070*
C15	0.7020 (3)	1.0495 (2)	0.1709 (2)	0.0424 (5)
H15A	0.6948	1.0792	0.1011	0.051*
H15B	0.7895	1.1095	0.2398	0.051*
C16	0.7328 (3)	0.9291 (2)	0.1574 (2)	0.0369 (5)
C17	0.5549 (3)	0.4512 (3)	−0.2335 (2)	0.0542 (7)
C18	0.2899 (5)	0.2958 (4)	−0.4241 (4)	0.0993 (14)
H18A	0.3042	0.2321	−0.3839	0.149*
H18B	0.2354	0.2598	−0.5086	0.149*
H18C	0.2296	0.3380	−0.3983	0.149*
O1	1.0472 (3)	1.2390 (2)	0.2231 (2)	0.0649 (6)
O2	0.9459 (2)	1.3412 (2)	0.38150 (17)	0.0585 (5)
O3	0.7891 (2)	1.1573 (2)	0.46389 (19)	0.0605 (5)
S1	0.76152 (11)	0.32107 (7)	−0.20652 (7)	0.0659 (2)
S2	0.75246 (8)	0.49614 (6)	−0.00808 (5)	0.04786 (17)
S3	0.85994 (8)	0.75086 (6)	0.19036 (5)	0.04658 (17)
S4	1.18116 (8)	1.01831 (8)	0.30089 (7)	0.0583 (2)
S5	0.52206 (8)	1.03736 (6)	0.18849 (6)	0.04905 (17)
S6	0.57706 (7)	0.80320 (6)	0.04603 (6)	0.04656 (17)
S7	0.48777 (8)	0.55840 (7)	−0.16902 (6)	0.05239 (18)
S8	0.47241 (13)	0.40014 (12)	−0.39012 (7)	0.0970 (4)

	U11	U22	U33	U12	U13	U23
C1	0.070 (2)	0.0609 (19)	0.077 (2)	0.0254 (16)	0.0397 (18)	0.0044 (16)
C2	0.0520 (15)	0.0406 (13)	0.0391 (12)	−0.0002 (11)	0.0261 (11)	−0.0012 (10)
C3	0.0382 (12)	0.0360 (12)	0.0364 (11)	0.0085 (9)	0.0153 (9)	0.0096 (9)
C4	0.0378 (12)	0.0352 (11)	0.0389 (11)	0.0118 (9)	0.0159 (9)	0.0096 (9)
C5	0.0369 (12)	0.0373 (12)	0.0380 (11)	0.0115 (9)	0.0178 (10)	0.0038 (9)
C6	0.0406 (13)	0.0497 (14)	0.0390 (12)	0.0129 (11)	0.0150 (10)	0.0013 (10)
C7	0.0522 (17)	0.100 (3)	0.0579 (17)	0.0260 (17)	0.0347 (15)	0.0127 (17)
C8	0.059 (2)	0.110 (3)	0.091 (3)	0.019 (2)	0.0487 (19)	0.045 (2)
C9	0.078 (2)	0.0544 (18)	0.069 (2)	−0.0044 (16)	0.0316 (17)	0.0209 (15)
C10	0.081 (2)	0.0383 (14)	0.0566 (16)	0.0106 (14)	0.0199 (15)	0.0147 (12)
C11	0.0613 (19)	0.0534 (17)	0.0645 (18)	0.0204 (15)	0.0203 (15)	0.0021 (14)
C12	0.064 (2)	0.081 (2)	0.0460 (15)	0.0117 (17)	0.0222 (14)	−0.0003 (14)
C13	0.0501 (16)	0.091 (2)	0.0611 (18)	0.0179 (16)	0.0329 (14)	0.0263 (17)
C14	0.0535 (17)	0.0573 (17)	0.078 (2)	0.0194 (14)	0.0388 (15)	0.0305 (15)
C15	0.0411 (13)	0.0337 (12)	0.0526 (14)	0.0112 (10)	0.0212 (11)	0.0106 (10)
C16	0.0335 (11)	0.0338 (11)	0.0437 (12)	0.0084 (9)	0.0193 (10)	0.0076 (9)
C17	0.0500 (15)	0.0618 (17)	0.0353 (12)	−0.0017 (13)	0.0199 (12)	−0.0028 (11)
C18	0.090 (3)	0.098 (3)	0.070 (2)	0.000 (2)	0.016 (2)	0.008 (2)
O1	0.0606 (13)	0.0569 (12)	0.0870 (15)	0.0080 (10)	0.0468 (12)	0.0237 (11)
O2	0.0605 (12)	0.0613 (12)	0.0532 (11)	0.0206 (10)	0.0208 (10)	0.0212 (9)
O3	0.0486 (11)	0.0760 (14)	0.0617 (12)	0.0191 (10)	0.0265 (10)	0.0257 (11)
S1	0.0891 (6)	0.0546 (4)	0.0623 (4)	0.0167 (4)	0.0508 (4)	−0.0005 (3)
S2	0.0601 (4)	0.0414 (3)	0.0366 (3)	0.0208 (3)	0.0156 (3)	0.0012 (2)
S3	0.0475 (4)	0.0435 (3)	0.0412 (3)	0.0221 (3)	0.0095 (3)	0.0030 (2)
S4	0.0325 (3)	0.0715 (5)	0.0582 (4)	0.0171 (3)	0.0114 (3)	0.0018 (3)
S5	0.0395 (3)	0.0518 (4)	0.0557 (4)	0.0219 (3)	0.0173 (3)	0.0103 (3)
S6	0.0351 (3)	0.0367 (3)	0.0556 (4)	0.0113 (2)	0.0094 (3)	0.0050 (3)
S7	0.0433 (4)	0.0610 (4)	0.0404 (3)	0.0105 (3)	0.0102 (3)	0.0091 (3)
S8	0.0877 (7)	0.1331 (10)	0.0378 (4)	−0.0061 (6)	0.0267 (4)	−0.0001 (5)

C1—S1	1.790 (4)	C10—O2	1.408 (3)
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C11—O2	1.415 (4)
C2—C17	1.341 (4)	C11—C12	1.485 (5)
C2—S1	1.748 (3)	C11—H11A	0.9700
C2—S2	1.753 (3)	C11—H11B	0.9700
C3—C4	1.345 (3)	C12—O3	1.425 (4)
C3—S2	1.750 (3)	C12—H12A	0.9700
C3—S7	1.753 (2)	C12—H12B	0.9700
C4—S6	1.746 (2)	C13—O3	1.420 (4)
C4—S3	1.756 (2)	C13—C14	1.503 (5)
C5—C16	1.337 (3)	C13—H13A	0.9700
C5—C6	1.492 (3)	C13—H13B	0.9700
C5—S3	1.770 (3)	C14—S5	1.803 (3)
C6—S4	1.821 (3)	C14—H14A	0.9700
C6—H6A	0.9700	C14—H14B	0.9700
C6—H6B	0.9700	C15—C16	1.496 (3)
C7—C8	1.504 (5)	C15—S5	1.818 (3)
C7—S4	1.798 (4)	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700
C7—H7B	0.9700	C16—S6	1.767 (3)
C8—O1	1.419 (4)	C17—S8	1.761 (3)
C8—H8A	0.9700	C17—S7	1.765 (3)
C8—H8B	0.9700	C18—S8	1.742 (5)
C9—O1	1.416 (4)	C18—H18A	0.9600
C9—C10	1.487 (5)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700
S1—C1—H1A	109.5	O2—C11—H11B	110.3
S1—C1—H1B	109.5	C12—C11—H11B	110.3
H1A—C1—H1B	109.5	H11A—C11—H11B	108.6
S1—C1—H1C	109.5	O3—C12—C11	111.5 (2)
H1A—C1—H1C	109.5	O3—C12—H12A	109.3
H1B—C1—H1C	109.5	C11—C12—H12A	109.3
C17—C2—S1	124.5 (2)	O3—C12—H12B	109.3
C17—C2—S2	116.3 (2)	C11—C12—H12B	109.3
S1—C2—S2	119.01 (17)	H12A—C12—H12B	108.0
C4—C3—S2	121.99 (19)	O3—C13—C14	109.6 (2)
C4—C3—S7	124.10 (19)	O3—C13—H13A	109.7
S2—C3—S7	113.89 (13)	C14—C13—H13A	109.7
C3—C4—S6	123.71 (19)	O3—C13—H13B	109.7
C3—C4—S3	122.82 (19)	C14—C13—H13B	109.7
S6—C4—S3	113.46 (13)	H13A—C13—H13B	108.2
C16—C5—C6	126.9 (2)	C13—C14—S5	114.0 (2)
C16—C5—S3	116.77 (18)	C13—C14—H14A	108.8
C6—C5—S3	116.37 (18)	S5—C14—H14A	108.8
C5—C6—S4	114.01 (17)	C13—C14—H14B	108.8
C5—C6—H6A	108.7	S5—C14—H14B	108.8
S4—C6—H6A	108.7	H14A—C14—H14B	107.7
C5—C6—H6B	108.7	C16—C15—S5	112.39 (16)
S4—C6—H6B	108.7	C16—C15—H15A	109.1
H6A—C6—H6B	107.6	S5—C15—H15A	109.1
C8—C7—S4	115.4 (2)	C16—C15—H15B	109.1
C8—C7—H7A	108.4	S5—C15—H15B	109.1
S4—C7—H7A	108.4	H15A—C15—H15B	107.9
C8—C7—H7B	108.4	C5—C16—C15	127.2 (2)
S4—C7—H7B	108.4	C5—C16—S6	116.68 (18)
H7A—C7—H7B	107.5	C15—C16—S6	115.94 (18)
O1—C8—C7	108.5 (3)	C2—C17—S8	124.0 (2)
O1—C8—H8A	110.0	C2—C17—S7	117.57 (19)
C7—C8—H8A	110.0	S8—C17—S7	118.18 (19)
O1—C8—H8B	110.0	S8—C18—H18A	109.5
C7—C8—H8B	110.0	S8—C18—H18B	109.5
H8A—C8—H8B	108.4	H18A—C18—H18B	109.5
O1—C9—C10	108.2 (2)	S8—C18—H18C	109.5
O1—C9—H9A	110.1	H18A—C18—H18C	109.5
C10—C9—H9A	110.1	H18B—C18—H18C	109.5
O1—C9—H9B	110.1	C9—O1—C8	113.5 (3)
C10—C9—H9B	110.1	C10—O2—C11	114.0 (2)
H9A—C9—H9B	108.4	C13—O3—C12	113.9 (3)
O2—C10—C9	107.8 (3)	C2—S1—C1	101.77 (14)
O2—C10—H10A	110.2	C3—S2—C2	95.28 (13)
C9—C10—H10A	110.2	C4—S3—C5	94.67 (11)
O2—C10—H10B	110.2	C7—S4—C6	103.95 (13)
C9—C10—H10B	110.2	C14—S5—C15	102.32 (13)
H10A—C10—H10B	108.5	C4—S6—C16	94.86 (12)
O2—C11—C12	107.1 (3)	C3—S7—C17	94.12 (13)
O2—C11—H11A	110.3	C18—S8—C17	102.48 (18)
C12—C11—H11A	110.3