4,6,7,9,10,12,13,15,16,18-Decahydro-1,3-dithiolo[4,5-l][1,4,7,10,15]trioxadithia-cyclo-hepta-decine-2-thione.

The title compound, C(13)H(20)O(3)S(5), is bis-ected by a crystallographic twofold rotation axis, which relates the two halves of the mol-ecule to one another: one S, one C and one O atom lie on the axis. The thione S atom lies in the plane of the five-membered rings with an r.m.s. deviation of 0.0042 (5) Å. Parts of the 17-membered macrocycle were refined using a two-part disorder model [occupancies of 0.553 (14) and 0.447 (14)]. There are no noteworthy inter-molecular inter-actions.

Related literature

Thia­crown ether annulated 1,3-dithiol-2-thione is a key inter­mediate of the crown ether-bearing redox-active tetra­thia­fulvalene moiety, see: 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

C13H20O3S5

M = 384.59

Monoclinic,

a = 14.040 (3) Å

b = 13.616 (3) Å

c = 10.004 (2) Å

β = 110.89 (3)°

V = 1786.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 290 K

0.13 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.920, T max = 0.926

8683 measured reflections

2054 independent reflections

1795 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.05

2054 reflections

116 parameters

31 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 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/S1600536810016946/nk2030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016946/nk2030Isup2.hkl

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

C13H20O3S5	F(000) = 808
Mr = 384.59	Dx = 1.430 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7120 reflections
a = 14.040 (3) Å	θ = 3.0–27.5°
b = 13.616 (3) Å	µ = 0.65 mm−1
c = 10.004 (2) Å	T = 290 K
β = 110.89 (3)°	Block, yellow
V = 1786.6 (6) Å3	0.13 × 0.13 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2054 independent reflections
Radiation source: fine-focus sealed tube	1795 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→17
Tmin = 0.920, Tmax = 0.926	k = −15→17
8683 measured reflections	l = −12→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.730P] where P = (Fo2 + 2Fc2)/3
2054 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.38 e Å−3
31 restraints	Δρmin = −0.40 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	Occ. (<1)
S1	0.0000	−0.12281 (6)	0.2500	0.0692 (3)
S2	0.05129 (4)	0.06857 (4)	0.14909 (6)	0.04829 (17)
S3	0.17462 (5)	0.26384 (5)	0.11969 (8)	0.0693 (2)
O1	0.17749 (17)	0.40044 (19)	0.3861 (3)	0.1067 (8)
O2	0.0000	0.5091 (3)	0.2500	0.1381 (16)
C1	0.0000	−0.0016 (2)	0.2500	0.0456 (6)
C2	0.02260 (13)	0.18371 (13)	0.2012 (2)	0.0390 (4)
C3	0.04873 (15)	0.27043 (15)	0.1292 (2)	0.0493 (5)
H3A	0.0440	0.3295	0.1807	0.059*
H3B	−0.0010	0.2757	0.0330	0.059*
C4	0.25511 (19)	0.2730 (2)	0.3037 (4)	0.0816 (9)
H4A	0.2278	0.2308	0.3594	0.098*
H4B	0.3221	0.2481	0.3138	0.098*
C5	0.2672 (2)	0.3743 (2)	0.3658 (4)	0.0896 (10)
H5A	0.3238	0.3758	0.4564	0.108*
H5B	0.2813	0.4205	0.3013	0.108*
C6	0.1737 (6)	0.4901 (6)	0.4396 (11)	0.092 (2)	0.553 (14)
H6A	0.2409	0.5199	0.4753	0.111*	0.553 (14)
H6B	0.1473	0.4868	0.5169	0.111*	0.553 (14)
C7	0.1044 (10)	0.5461 (6)	0.3178 (12)	0.099 (3)	0.553 (14)
H7A	0.1004	0.6126	0.3501	0.118*	0.553 (14)
H7B	0.1351	0.5497	0.2451	0.118*	0.553 (14)
C6'	0.1649 (8)	0.5194 (7)	0.3562 (16)	0.083 (3)	0.447 (14)
H6'1	0.2130	0.5549	0.4360	0.100*	0.447 (14)
H6'2	0.1785	0.5356	0.2703	0.100*	0.447 (14)
C7'	0.0574 (11)	0.5476 (8)	0.3385 (11)	0.092 (3)	0.447 (14)
H7'1	0.0459	0.5333	0.4266	0.110*	0.447 (14)
H7'2	0.0491	0.6178	0.3219	0.110*	0.447 (14)

	U11	U22	U33	U12	U13	U23
S1	0.0894 (6)	0.0347 (4)	0.0982 (7)	0.000	0.0513 (5)	0.000
S2	0.0524 (3)	0.0401 (3)	0.0612 (3)	0.00140 (19)	0.0310 (2)	−0.0020 (2)
S3	0.0700 (4)	0.0671 (4)	0.0918 (5)	−0.0035 (3)	0.0543 (4)	0.0127 (3)
O1	0.0793 (14)	0.1025 (17)	0.142 (2)	−0.0370 (13)	0.0438 (14)	−0.0511 (16)
O2	0.110 (3)	0.067 (2)	0.225 (5)	0.000	0.044 (3)	0.000
C1	0.0432 (13)	0.0374 (13)	0.0576 (15)	0.000	0.0199 (12)	0.000
C2	0.0321 (8)	0.0354 (9)	0.0478 (9)	−0.0004 (6)	0.0123 (7)	0.0006 (7)
C3	0.0459 (10)	0.0444 (10)	0.0561 (11)	−0.0011 (8)	0.0165 (9)	0.0090 (9)
C4	0.0423 (12)	0.0699 (17)	0.122 (2)	−0.0026 (11)	0.0168 (14)	0.0213 (16)
C5	0.0518 (15)	0.086 (2)	0.115 (2)	−0.0222 (13)	0.0109 (15)	0.0036 (18)
C6	0.109 (5)	0.077 (4)	0.080 (5)	−0.023 (3)	0.021 (3)	−0.014 (3)
C7	0.112 (5)	0.054 (3)	0.126 (5)	−0.018 (4)	0.038 (5)	−0.010 (3)
C6'	0.092 (5)	0.063 (5)	0.100 (7)	−0.029 (4)	0.043 (5)	−0.029 (5)
C7'	0.108 (7)	0.081 (5)	0.094 (5)	−0.003 (5)	0.045 (5)	−0.037 (4)

S1—C1	1.650 (3)	C3—H3B	0.9700
S2—C1	1.7231 (16)	C4—C5	1.497 (4)
S2—C2	1.7440 (18)	C4—H4A	0.9700
S3—C4	1.788 (3)	C4—H4B	0.9700
S3—C3	1.806 (2)	C5—H5A	0.9700
O1—C6	1.342 (7)	C5—H5B	0.9700
O1—C5	1.391 (4)	C6—C7	1.472 (14)
O1—C6'	1.645 (12)	C6—H6A	0.9700
O2—C7'	1.095 (11)	C6—H6B	0.9700
O2—C7'i	1.095 (11)	C7—H7A	0.9700
O2—C7	1.467 (11)	C7—H7B	0.9700
O2—C7i	1.467 (11)	C6'—C7'	1.506 (15)
C1—S2i	1.7231 (16)	C6'—H6'1	0.9700
C2—C2i	1.340 (4)	C6'—H6'2	0.9700
C2—C3	1.495 (3)	C7'—H7'1	0.9700
C3—H3A	0.9700	C7'—H7'2	0.9700
C1—S2—C2	97.69 (10)	O1—C5—H5B	109.9
C4—S3—C3	102.32 (13)	C4—C5—H5B	109.9
C6—O1—C5	117.2 (4)	H5A—C5—H5B	108.3
C6—O1—C6'	32.8 (4)	O1—C6—C7	104.4 (8)
C5—O1—C6'	105.6 (4)	O1—C6—H6A	110.9
C7'—O2—C7'i	122.7 (13)	C7—C6—H6A	110.9
C7'—O2—C7	30.3 (5)	O1—C6—H6B	110.9
C7'i—O2—C7	122.3 (7)	C7—C6—H6B	110.9
C7'—O2—C7i	122.3 (7)	H6A—C6—H6B	108.9
C7'i—O2—C7i	30.3 (5)	O2—C7—C6	117.5 (8)
C7—O2—C7i	139.8 (8)	O2—C7—H7A	107.9
S1—C1—S2i	123.68 (8)	C6—C7—H7A	107.9
S1—C1—S2	123.68 (8)	O2—C7—H7B	107.9
S2i—C1—S2	112.65 (15)	C6—C7—H7B	107.9
C2i—C2—C3	127.72 (11)	H7A—C7—H7B	107.2
C2i—C2—S2	115.95 (6)	C7'—C6'—O1	108.1 (8)
C3—C2—S2	116.30 (14)	C7'—C6'—H6'1	110.1
C2—C3—S3	113.52 (14)	O1—C6'—H6'1	110.1
C2—C3—H3A	108.9	C7'—C6'—H6'2	110.1
S3—C3—H3A	108.9	O1—C6'—H6'2	110.1
C2—C3—H3B	108.9	H6'1—C6'—H6'2	108.4
S3—C3—H3B	108.9	O2—C7'—C6'	113.0 (9)
H3A—C3—H3B	107.7	O2—C7'—C7'i	28.7 (6)
C5—C4—S3	115.3 (2)	C6'—C7'—C7'i	125.7 (13)
C5—C4—H4A	108.4	O2—C7'—H7'1	109.0
S3—C4—H4A	108.4	C6'—C7'—H7'1	109.0
C5—C4—H4B	108.4	C7'i—C7'—H7'1	118.7
S3—C4—H4B	108.4	O2—C7'—H7'2	109.0
H4A—C4—H4B	107.5	C6'—C7'—H7'2	109.0
O1—C5—C4	108.8 (2)	C7'i—C7'—H7'2	80.4
O1—C5—H5A	109.9	H7'1—C7'—H7'2	107.8
C4—C5—H5A	109.9