2,5-Bis(1,3-dithiol-2-yl-idene)-1,3-dithiol-ane-4-thione.

The asymmetric unit of the title compound, C(9)H(4)S(7), contains two independent mol-ecules, in one of which the central five-membered ring is disordered over two orientations in a 0.924 (3):0.076 (3) ratio. The mol-ecular skeleton is almost planar: the average distance of the atoms from their mean plane is 0.128 (7) Å in the ordered mol-ecule, and 0.088 (5) and 0.123 (2) Å in the major and minor disorder components, respectively. The ordered and disordered mol-ecules form separate columns by stacking along the b axis. Adjacent columns inter-act via short S⋯S [3.33 (2), 3.434 (3), 3.444 (2), 3.503 (2), 3.519 (3) and 3.53 (4) Å] and S⋯H [2.814 (2), 2.87 (7), 2.92 (2), 2.9269 (18), 2.93 (2), 2.94 (2), 2.939 (2), 2.967 (2) and 2.974 (1) Å] contacts.

Related literature

For background to 2,5-di(1,3-dithiol-2-yl­idene)-1,3-dithiol­ane-4-thione derivatives, see: Iwamatsu et al. (1999 ▶, 2000 ▶); Wang et al. (2005 ▶, 2007 ▶); Hiraoka et al. (2005 ▶); Fujiwara et al. (2006 ▶, 2007 ▶); Ueda & Yoza (2009a ▶,b ▶,c ▶). For the synthesis, see: Ueda et al. (2010 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C9H4S7

M = 336.54

Monoclinic,

a = 17.669 (5) Å

b = 3.9110 (11) Å

c = 18.380 (5) Å

β = 108.177 (4)°

V = 1206.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.27 mm−1

T = 93 K

0.09 × 0.02 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.894, T max = 0.975

6965 measured reflections

4975 independent reflections

3396 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.107

S = 0.98

4975 reflections

344 parameters

421 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.52 e Å−3

Absolute structure: Flack (1983 ▶), 1849 Friedel pairs

Flack parameter: −0.18 (18)

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XCIF (Bruker, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051518/fy2030sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051518/fy2030Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051518/fy2030Isup3.cml

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

C9H4S7	F(000) = 680
Mr = 336.54	Dx = 1.852 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 17.669 (5) Å	Cell parameters from 794 reflections
b = 3.9110 (11) Å	θ = 2.3–23.9°
c = 18.380 (5) Å	µ = 1.27 mm−1
β = 108.177 (4)°	T = 93 K
V = 1206.8 (6) Å3	Needle, black
Z = 4	0.09 × 0.02 × 0.02 mm

Bruker APEXII CCD area-detector diffractometer	4975 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	3396 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.054
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 1.9°
phi and ω scans	h = −22→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→4
Tmin = 0.894, Tmax = 0.975	l = −22→23
6965 measured reflections

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)] = 0.061	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0283P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.002
4975 reflections	Δρmax = 0.63 e Å−3
344 parameters	Δρmin = −0.52 e Å−3
421 restraints	Absolute structure: Flack (1983), 1849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.18 (18)

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	Occ. (<1)
C4	0.3976 (4)	0.7807 (19)	0.2942 (4)	0.0247 (17)
C5	0.5339 (4)	1.060 (2)	0.3647 (4)	0.035 (2)
H5A	0.5870	1.1430	0.3772	0.042*
C6	0.4937 (4)	1.091 (2)	0.4121 (5)	0.035 (2)
H6A	0.5160	1.1990	0.4604	0.043*
C7	0.1148 (4)	0.3154 (18)	0.1591 (4)	0.0190 (16)
C8	−0.0317 (4)	0.151 (2)	0.1023 (4)	0.0244 (17)
H8A	−0.0815	0.0767	0.0685	0.029*
C9	−0.0268 (4)	0.277 (2)	0.1707 (4)	0.0251 (18)
H9A	−0.0718	0.2915	0.1884	0.030*
C10	0.3122 (4)	0.6221 (18)	0.8314 (3)	0.0139 (14)
C11	0.3743 (4)	0.922 (2)	0.9615 (4)	0.0238 (17)
H11A	0.3839	1.0134	1.0115	0.029*
C12	0.4298 (4)	0.941 (2)	0.9257 (4)	0.0248 (17)
H12A	0.4792	1.0526	0.9490	0.030*
C13	0.1820 (4)	0.1225 (19)	0.5609 (4)	0.0154 (15)
C14	0.1298 (4)	−0.035 (2)	0.4192 (4)	0.0195 (16)
H14A	0.0971	−0.1098	0.3703	0.023*
C15	0.2009 (4)	0.085 (2)	0.4285 (3)	0.0205 (17)
H15A	0.2218	0.1003	0.3868	0.025*
C4A	0.3347 (6)	0.633 (2)	0.2437 (4)	0.0190 (17)	0.924 (3)
C5A	0.1947 (5)	0.384 (2)	0.1739 (4)	0.0155 (15)	0.924 (3)
C6A	0.2391 (6)	0.323 (3)	0.1228 (5)	0.021 (2)	0.924 (3)
C4B	0.191 (4)	0.346 (17)	0.181 (4)	0.018 (4)	0.076 (3)
C5B	0.335 (6)	0.59 (2)	0.248 (3)	0.023 (4)	0.076 (3)
C6B	0.331 (2)	0.485 (10)	0.173 (3)	0.023 (3)	0.076 (3)
C4C	0.2640 (3)	0.4578 (17)	0.7717 (3)	0.0170 (15)
C5C	0.1960 (3)	0.1937 (16)	0.6374 (3)	0.0151 (15)
C6C	0.1387 (3)	0.1573 (17)	0.6762 (3)	0.0158 (15)
S4	0.48789 (12)	0.8603 (6)	0.27620 (13)	0.0385 (6)
S5	0.39615 (10)	0.9263 (6)	0.38449 (10)	0.0270 (5)
S6	0.05349 (11)	0.1230 (5)	0.07570 (9)	0.0211 (4)
S7	0.06754 (10)	0.4126 (5)	0.22574 (9)	0.0201 (4)
S8	0.28575 (11)	0.7290 (5)	0.91400 (10)	0.0219 (5)
S9	0.40896 (10)	0.7580 (5)	0.83649 (10)	0.0225 (5)
S10	0.09618 (10)	−0.0554 (5)	0.49847 (9)	0.0189 (4)
S11	0.25580 (10)	0.2146 (5)	0.51919 (9)	0.0204 (4)
S1A	0.2450 (5)	0.5721 (17)	0.2628 (3)	0.0191 (11)	0.924 (3)
S2A	0.33680 (13)	0.4760 (6)	0.15541 (12)	0.0277 (6)	0.924 (3)
S3A	0.20601 (13)	0.1459 (6)	0.03754 (11)	0.0275 (6)	0.924 (3)
S1B	0.246 (6)	0.52 (2)	0.268 (3)	0.015 (6)	0.076 (3)
S2B	0.242 (2)	0.312 (11)	0.114 (2)	0.021 (4)	0.076 (3)
S3B	0.4040 (14)	0.512 (7)	0.1345 (13)	0.026 (6)	0.076 (3)
S1C	0.28927 (10)	0.3657 (5)	0.68923 (9)	0.0193 (4)
S2C	0.16991 (10)	0.3150 (5)	0.76938 (9)	0.0193 (4)
S3C	0.04904 (10)	−0.0125 (5)	0.64141 (10)	0.0211 (5)

	U11	U22	U33	U12	U13	U23
C4	0.025 (3)	0.021 (4)	0.032 (4)	−0.001 (3)	0.014 (3)	0.000 (3)
C5	0.021 (4)	0.028 (5)	0.055 (5)	−0.001 (3)	0.012 (3)	−0.006 (4)
C6	0.024 (4)	0.028 (5)	0.048 (4)	−0.006 (3)	0.002 (3)	−0.004 (4)
C7	0.026 (3)	0.013 (4)	0.017 (3)	0.005 (3)	0.004 (3)	0.000 (3)
C8	0.027 (4)	0.018 (4)	0.022 (3)	−0.004 (3)	−0.001 (3)	−0.001 (3)
C9	0.026 (3)	0.026 (4)	0.025 (4)	0.000 (3)	0.011 (3)	−0.002 (3)
C10	0.016 (3)	0.010 (3)	0.014 (3)	0.002 (3)	0.003 (3)	0.000 (3)
C11	0.028 (4)	0.021 (4)	0.017 (3)	0.003 (3)	−0.001 (3)	−0.002 (3)
C12	0.022 (3)	0.020 (4)	0.022 (3)	−0.002 (3)	−0.009 (3)	0.000 (3)
C13	0.017 (3)	0.010 (3)	0.020 (3)	−0.002 (3)	0.006 (3)	−0.002 (3)
C14	0.020 (3)	0.022 (4)	0.013 (3)	−0.001 (3)	0.000 (3)	−0.001 (3)
C15	0.026 (4)	0.025 (4)	0.012 (3)	0.004 (3)	0.008 (3)	0.003 (3)
C4A	0.020 (3)	0.015 (4)	0.024 (3)	0.000 (3)	0.009 (3)	0.002 (3)
C5A	0.022 (3)	0.015 (3)	0.011 (3)	0.003 (3)	0.008 (3)	0.003 (3)
C6A	0.033 (3)	0.015 (4)	0.014 (4)	0.008 (3)	0.007 (3)	0.000 (3)
C4B	0.025 (5)	0.016 (6)	0.015 (5)	0.004 (5)	0.006 (5)	0.001 (5)
C5B	0.024 (6)	0.020 (6)	0.026 (6)	0.000 (5)	0.010 (5)	0.001 (5)
C6B	0.027 (5)	0.021 (5)	0.024 (5)	0.002 (5)	0.010 (4)	0.001 (5)
C4C	0.012 (3)	0.018 (4)	0.018 (3)	−0.002 (3)	0.001 (3)	−0.003 (3)
C5C	0.012 (3)	0.017 (4)	0.012 (3)	−0.001 (3)	−0.002 (3)	0.000 (3)
C6C	0.019 (3)	0.015 (4)	0.012 (3)	−0.002 (3)	0.004 (3)	−0.001 (3)
S4	0.0305 (11)	0.0339 (16)	0.0588 (14)	−0.0056 (11)	0.0250 (11)	−0.0026 (12)
S5	0.0204 (10)	0.0262 (12)	0.0319 (11)	0.0003 (9)	0.0046 (9)	−0.0031 (10)
S6	0.0292 (11)	0.0190 (11)	0.0142 (9)	−0.0007 (9)	0.0053 (8)	−0.0010 (9)
S7	0.0263 (10)	0.0191 (11)	0.0157 (9)	−0.0017 (9)	0.0075 (8)	−0.0033 (9)
S8	0.0256 (10)	0.0229 (12)	0.0175 (9)	0.0008 (9)	0.0073 (8)	−0.0053 (9)
S9	0.0188 (10)	0.0243 (12)	0.0231 (10)	−0.0012 (9)	0.0047 (8)	−0.0029 (9)
S10	0.0190 (9)	0.0192 (11)	0.0162 (9)	−0.0016 (9)	0.0023 (8)	−0.0002 (9)
S11	0.0201 (10)	0.0231 (12)	0.0176 (9)	−0.0038 (9)	0.0052 (8)	−0.0013 (8)
S1A	0.0212 (12)	0.020 (3)	0.0185 (13)	−0.0022 (18)	0.0095 (12)	−0.0003 (15)
S2A	0.0320 (12)	0.0275 (14)	0.0304 (12)	−0.0002 (11)	0.0197 (10)	−0.0006 (11)
S3A	0.0421 (14)	0.0252 (14)	0.0197 (11)	0.0054 (11)	0.0162 (10)	−0.0023 (10)
S1B	0.015 (7)	0.016 (8)	0.017 (8)	0.000 (7)	0.007 (6)	−0.002 (7)
S2B	0.030 (6)	0.018 (6)	0.016 (6)	0.007 (5)	0.008 (5)	0.004 (5)
S3B	0.027 (8)	0.029 (9)	0.025 (8)	0.009 (7)	0.010 (6)	−0.002 (7)
S1C	0.0158 (9)	0.0238 (12)	0.0174 (9)	−0.0032 (8)	0.0040 (7)	−0.0057 (8)
S2C	0.0171 (9)	0.0224 (12)	0.0178 (9)	0.0004 (8)	0.0047 (8)	−0.0012 (8)
S3C	0.0156 (9)	0.0243 (12)	0.0218 (9)	−0.0010 (8)	0.0035 (8)	0.0004 (9)

C4—C4A	1.336 (11)	C13—C5C	1.378 (8)
C4—C5B	1.38 (9)	C13—S10	1.736 (7)
C4—S4	1.756 (7)	C13—S11	1.744 (6)
C4—S5	1.763 (7)	C14—C15	1.302 (8)
C5—C6	1.292 (9)	C14—S10	1.739 (6)
C5—S4	1.758 (8)	C14—H14A	0.9500
C5—H5A	0.9500	C15—S11	1.723 (7)
C6—S5	1.759 (7)	C15—H15A	0.9500
C6—H6A	0.9500	C4A—S1A	1.743 (6)
C7—C4B	1.28 (6)	C4A—S2A	1.746 (7)
C7—C5A	1.377 (9)	C5A—C6A	1.418 (9)
C7—S7	1.727 (6)	C5A—S1A	1.761 (6)
C7—S6	1.748 (7)	C6A—S3A	1.646 (9)
C8—C9	1.327 (9)	C6A—S2A	1.747 (10)
C8—S6	1.726 (7)	C4B—S2B	1.743 (10)
C8—H8A	0.9500	C4B—S1B	1.745 (10)
C9—S7	1.742 (7)	C5B—C6B	1.417 (11)
C9—H9A	0.9500	C5B—S1B	1.761 (10)
C10—C4C	1.326 (8)	C6B—S3B	1.649 (11)
C10—S9	1.765 (6)	C6B—S2B	1.744 (11)
C10—S8	1.772 (6)	C4C—S2C	1.741 (6)
C11—C12	1.343 (8)	C4C—S1C	1.747 (6)
C11—S8	1.712 (7)	C5C—C6C	1.415 (7)
C11—H11A	0.9500	C5C—S1C	1.760 (6)
C12—S9	1.721 (7)	C6C—S3C	1.652 (6)
C12—H12A	0.9500	C6C—S2C	1.740 (6)
C4A—C4—S4	123.6 (5)	C4—C4A—S2A	122.9 (7)
C5B—C4—S4	125 (3)	S1A—C4A—S2A	115.1 (5)
C4A—C4—S5	122.7 (5)	C7—C5A—C6A	125.6 (7)
C5B—C4—S5	121 (3)	C7—C5A—S1A	117.0 (6)
S4—C4—S5	113.6 (4)	C6A—C5A—S1A	117.4 (5)
C6—C5—S4	118.2 (6)	C5A—C6A—S3A	126.5 (8)
C6—C5—H5A	120.9	C5A—C6A—S2A	114.1 (6)
S4—C5—H5A	120.9	S3A—C6A—S2A	119.4 (6)
C5—C6—S5	117.8 (7)	C7—C4B—S2B	120 (5)
C5—C6—H6A	121.1	C7—C4B—S1B	123 (5)
S5—C6—H6A	121.1	S2B—C4B—S1B	114.8 (9)
C4B—C7—S7	117 (3)	C4—C5B—C6B	123 (7)
C5A—C7—S7	120.7 (5)	C4—C5B—S1B	123 (4)
C4B—C7—S6	128 (3)	C6B—C5B—S1B	113 (5)
C5A—C7—S6	125.0 (5)	C5B—C6B—S3B	126 (5)
S7—C7—S6	114.3 (4)	C5B—C6B—S2B	118 (5)
C9—C8—S6	119.1 (6)	S3B—C6B—S2B	116 (3)
C9—C8—H8A	120.4	C10—C4C—S2C	122.5 (4)
S6—C8—H8A	120.4	C10—C4C—S1C	123.1 (4)
C8—C9—S7	115.5 (5)	S2C—C4C—S1C	114.4 (3)
C8—C9—H9A	122.2	C13—C5C—C6C	124.4 (5)
S7—C9—H9A	122.2	C13—C5C—S1C	118.0 (4)
C4C—C10—S9	123.5 (4)	C6C—C5C—S1C	117.5 (4)
C4C—C10—S8	123.4 (5)	C5C—C6C—S3C	126.5 (5)
S9—C10—S8	113.2 (4)	C5C—C6C—S2C	113.8 (4)
C12—C11—S8	117.7 (5)	S3C—C6C—S2C	119.6 (3)
C12—C11—H11A	121.2	C4—S4—C5	95.2 (4)
S8—C11—H11A	121.2	C6—S5—C4	95.2 (4)
C11—C12—S9	118.2 (6)	C8—S6—C7	94.7 (3)
C11—C12—H12A	120.9	C7—S7—C9	96.2 (3)
S9—C12—H12A	120.9	C11—S8—C10	95.6 (3)
C5C—C13—S10	126.7 (5)	C12—S9—C10	95.3 (3)
C5C—C13—S11	119.1 (5)	C13—S10—C14	94.6 (3)
S10—C13—S11	114.3 (4)	C15—S11—C13	95.3 (3)
C15—C14—S10	118.4 (5)	C4A—S1A—C5A	95.6 (3)
C15—C14—H14A	120.8	C6A—S2A—C4A	97.7 (5)
S10—C14—H14A	120.8	C4B—S1B—C5B	98 (2)
C14—C15—S11	117.5 (5)	C6B—S2B—C4B	96 (3)
C14—C15—H15A	121.3	C4C—S1C—C5C	95.7 (3)
S11—C15—H15A	121.3	C6C—S2C—C4C	98.3 (3)
C4—C4A—S1A	122.0 (5)