4,6,7,9,10,12,13,15-Octa-hydro-2H-1,3-dithiolo[4,5-i][1,4,7,12]dioxadithia-cyclo-tetra-decine-2-thione.

In the title mol-ecule, C(11)H(16)O(2)S(5), the two S atoms from the macrocycle are situated on opposite sides of the mean plane of the five-membered ring, deviating from it by 1.288 (3) and 1.728 (3) Å. In the crystal, weak inter-molecular C-H⋯S and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (100). The crystal studied was a racemic twin.

Related literature

For crown ether annulated 1,3-dithiol-2-thio­nes, see: Hansen et al. (1992 ▶); Trippé et al. (2002 ▶). For details of the synthesis, see: Chen et al. (2005 ▶). For a related structure, see: Hou et al. (2009 ▶)

Experimental

Crystal data

C11H16O2S5

M = 340.54

Monoclinic,

a = 8.9201 (18) Å

b = 8.5317 (17) Å

c = 10.128 (2) Å

β = 97.00 (3)°

V = 765.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 291 K

0.13 × 0.12 × 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

7527 measured reflections

3221 independent reflections

3100 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.06

3221 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶); 1359 Friedel pairs

Flack parameter: 0.42 (9)

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/S1600536809029468/cv2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029468/cv2592Isup2.hkl

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

C11H16O2S5	F(000) = 356
Mr = 340.54	Dx = 1.478 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7211 reflections
a = 8.9201 (18) Å	θ = 3.1–27.5°
b = 8.5317 (17) Å	µ = 0.75 mm−1
c = 10.128 (2) Å	T = 291 K
β = 97.00 (3)°	Block, yellow
V = 765.0 (3) Å3	0.13 × 0.12 × 0.11 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	3221 independent reflections
Radiation source: fine-focus sealed tube	3100 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.909, Tmax = 0.922	k = −11→10
7527 measured reflections	l = −13→11

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1939P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3221 reflections	Δρmax = 0.58 e Å−3
164 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983); 1359 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.42 (9)

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	0.9104 (3)	0.5403 (4)	1.0514 (2)	0.0344 (5)
C2	0.6930 (2)	0.4126 (3)	0.8914 (2)	0.0264 (5)
C3	0.5748 (3)	0.2952 (3)	0.8447 (2)	0.0342 (5)
H3A	0.6206	0.1920	0.8492	0.041*
H3B	0.5391	0.3164	0.7521	0.041*
C4	0.3178 (3)	0.4733 (4)	0.8901 (3)	0.0406 (6)
H4A	0.2524	0.4990	0.9568	0.049*
H4B	0.3929	0.5556	0.8915	0.049*
C5	0.2242 (3)	0.4741 (4)	0.7555 (3)	0.0445 (7)
H5A	0.1638	0.3795	0.7439	0.053*
H5B	0.1566	0.5637	0.7482	0.053*
C6	0.2480 (3)	0.4848 (4)	0.5262 (3)	0.0426 (6)
H6A	0.1704	0.5650	0.5179	0.051*
H6B	0.2005	0.3842	0.5047	0.051*
C7	0.3637 (3)	0.5190 (4)	0.4329 (3)	0.0418 (6)
H7A	0.3150	0.5253	0.3421	0.050*
H7B	0.4128	0.6185	0.4558	0.050*
C8	0.5855 (3)	0.4162 (4)	0.3590 (3)	0.0427 (7)
H8A	0.5382	0.4495	0.2722	0.051*
H8B	0.6331	0.3156	0.3480	0.051*
C9	0.7060 (3)	0.5337 (4)	0.4090 (3)	0.0470 (7)
H9A	0.6589	0.6351	0.4175	0.056*
H9B	0.7765	0.5438	0.3438	0.056*
C10	0.6889 (3)	0.5696 (4)	0.6801 (2)	0.0381 (6)
H10A	0.6885	0.6826	0.6690	0.046*
H10B	0.5861	0.5322	0.6586	0.046*
C11	0.7448 (2)	0.5293 (3)	0.8207 (2)	0.0290 (5)
O1	0.3233 (2)	0.4825 (3)	0.65686 (18)	0.0432 (5)
O2	0.4715 (2)	0.3969 (2)	0.44464 (17)	0.0385 (4)
S1	1.03598 (9)	0.58767 (12)	1.17933 (8)	0.0558 (2)
S2	0.78149 (7)	0.39272 (8)	1.05411 (6)	0.03282 (15)
S3	0.41352 (8)	0.29178 (9)	0.93755 (8)	0.04456 (18)
S4	0.80970 (8)	0.48036 (12)	0.56811 (7)	0.0539 (2)
S5	0.89230 (7)	0.64009 (8)	0.90156 (7)	0.03733 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0240 (11)	0.0456 (15)	0.0325 (11)	0.0034 (10)	−0.0003 (9)	−0.0064 (11)
C2	0.0195 (10)	0.0336 (13)	0.0252 (10)	0.0033 (8)	−0.0005 (8)	−0.0022 (9)
C3	0.0310 (12)	0.0346 (13)	0.0356 (12)	0.0012 (10)	−0.0020 (9)	−0.0022 (11)
C4	0.0330 (13)	0.0503 (17)	0.0400 (13)	0.0006 (12)	0.0105 (10)	−0.0063 (12)
C5	0.0259 (12)	0.0616 (19)	0.0473 (15)	0.0072 (12)	0.0094 (11)	0.0041 (14)
C6	0.0275 (13)	0.0597 (19)	0.0388 (13)	0.0049 (12)	−0.0030 (10)	0.0054 (13)
C7	0.0369 (14)	0.0520 (17)	0.0346 (12)	0.0011 (12)	−0.0028 (11)	0.0071 (12)
C8	0.0417 (15)	0.0582 (19)	0.0283 (11)	−0.0032 (13)	0.0048 (10)	0.0000 (12)
C9	0.0413 (15)	0.069 (2)	0.0313 (12)	−0.0104 (14)	0.0065 (11)	0.0044 (13)
C10	0.0318 (13)	0.0507 (16)	0.0315 (12)	0.0060 (11)	0.0028 (10)	0.0054 (11)
C11	0.0184 (10)	0.0390 (13)	0.0292 (11)	0.0012 (9)	0.0020 (8)	−0.0002 (10)
O1	0.0233 (8)	0.0716 (14)	0.0349 (9)	0.0071 (9)	0.0045 (7)	0.0047 (9)
O2	0.0346 (10)	0.0433 (11)	0.0377 (9)	−0.0016 (8)	0.0049 (7)	0.0018 (9)
S1	0.0336 (4)	0.0887 (7)	0.0416 (4)	−0.0110 (4)	−0.0092 (3)	−0.0101 (4)
S2	0.0298 (3)	0.0407 (3)	0.0267 (3)	−0.0002 (2)	−0.0015 (2)	0.0031 (2)
S3	0.0319 (3)	0.0508 (4)	0.0507 (4)	−0.0110 (3)	0.0041 (3)	0.0134 (3)
S4	0.0314 (3)	0.0975 (7)	0.0325 (3)	0.0086 (4)	0.0027 (3)	−0.0032 (4)
S5	0.0254 (3)	0.0466 (4)	0.0399 (3)	−0.0089 (3)	0.0031 (2)	0.0025 (3)

C1—S1	1.656 (3)	C6—H6A	0.9700
C1—S2	1.708 (3)	C6—H6B	0.9700
C1—S5	1.730 (3)	C7—O2	1.413 (4)
C2—C11	1.341 (4)	C7—H7A	0.9700
C2—C3	1.489 (3)	C7—H7B	0.9700
C2—S2	1.747 (2)	C8—O2	1.424 (3)
C3—S3	1.812 (3)	C8—C9	1.511 (4)
C3—H3A	0.9700	C8—H8A	0.9700
C3—H3B	0.9700	C8—H8B	0.9700
C4—C5	1.510 (4)	C9—S4	1.815 (3)
C4—S3	1.805 (3)	C9—H9A	0.9700
C4—H4A	0.9700	C9—H9B	0.9700
C4—H4B	0.9700	C10—C11	1.490 (3)
C5—O1	1.414 (3)	C10—S4	1.824 (3)
C5—H5A	0.9700	C10—H10A	0.9700
C5—H5B	0.9700	C10—H10B	0.9700
C6—O1	1.409 (3)	C11—S5	1.741 (2)
C6—C7	1.510 (4)
S1—C1—S2	124.03 (17)	C6—C7—H7A	110.0
S1—C1—S5	123.24 (18)	O2—C7—H7B	110.0
S2—C1—S5	112.70 (14)	C6—C7—H7B	110.0
C11—C2—C3	127.4 (2)	H7A—C7—H7B	108.4
C11—C2—S2	115.48 (18)	O2—C8—C9	113.8 (2)
C3—C2—S2	117.08 (18)	O2—C8—H8A	108.8
C2—C3—S3	114.98 (18)	C9—C8—H8A	108.8
C2—C3—H3A	108.5	O2—C8—H8B	108.8
S3—C3—H3A	108.5	C9—C8—H8B	108.8
C2—C3—H3B	108.5	H8A—C8—H8B	107.7
S3—C3—H3B	108.5	C8—C9—S4	113.3 (2)
H3A—C3—H3B	107.5	C8—C9—H9A	108.9
C5—C4—S3	115.9 (2)	S4—C9—H9A	108.9
C5—C4—H4A	108.3	C8—C9—H9B	108.9
S3—C4—H4A	108.3	S4—C9—H9B	108.9
C5—C4—H4B	108.3	H9A—C9—H9B	107.7
S3—C4—H4B	108.3	C11—C10—S4	110.08 (18)
H4A—C4—H4B	107.4	C11—C10—H10A	109.6
O1—C5—C4	108.3 (2)	S4—C10—H10A	109.6
O1—C5—H5A	110.0	C11—C10—H10B	109.6
C4—C5—H5A	110.0	S4—C10—H10B	109.6
O1—C5—H5B	110.0	H10A—C10—H10B	108.2
C4—C5—H5B	110.0	C2—C11—C10	125.7 (2)
H5A—C5—H5B	108.4	C2—C11—S5	116.22 (18)
O1—C6—C7	107.8 (2)	C10—C11—S5	118.0 (2)
O1—C6—H6A	110.1	C6—O1—C5	113.3 (2)
C7—C6—H6A	110.1	C7—O2—C8	113.1 (2)
O1—C6—H6B	110.1	C1—S2—C2	98.09 (12)
C7—C6—H6B	110.1	C4—S3—C3	103.16 (13)
H6A—C6—H6B	108.5	C9—S4—C10	99.88 (14)
O2—C7—C6	108.3 (2)	C1—S5—C11	97.47 (13)
O2—C7—H7A	110.0

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1i	0.97	2.86	3.695 (3)	145
C10—H10A···O2ii	0.97	2.51	3.317 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1i	0.97	2.86	3.695 (3)	145
C10—H10A⋯O2ii	0.97	2.51	3.317 (3)	140

Symmetry codes: (i) ; (ii) .