2,5-Bis(1,3-dithiol-2-yl­idene)-1,3-dithiol­ane-4-thione

Ueda, K.; Suzuki, K.; Kunimoto, K.; Yoza, K.

doi:10.1107/S1600536811051518

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o52

doi:10.1107/S1600536811051518

Open

access

2,5-Bis(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione

Kazumasa Ueda,^a,^b ^* Kenta Suzuki,^b Kei Kunimoto ^b and Kenji Yoza ^c

^aDivision of Basic Engineering, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu, Shizuoka 432-8561, Japan, ^bDepartment of Materials Science and Chemical Engineering, Graduate School of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu, Shizuoka 432-8561, Japan, and ^cBruker AXS Co. Ltd, Moriya-cho 3-9, Kanagawa-ku, Kanagawa, Kanagawa 221-0022, Japan
^*Correspondence e-mail: tkueda@ipc.shizuoka.ac.jp

(Received 12 October 2011; accepted 30 November 2011; online 10 December 2011)

The asymmetric unit of the title compound, C₉H₄S₇, contains two independent molecules, in one of which the central five-membered ring is disordered over two orientations in a 0.924 (3):0.076 (3) ratio. The molecular skeleton is almost planar: the average distance of the atoms from their mean plane is 0.128 (7) Å in the ordered molecule, and 0.088 (5) and 0.123 (2) Å in the major and minor disorder components, respectively. The ordered and disordered molecules form separate columns by stacking along the b axis. Adjacent columns interact 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_r = 336.54
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.107
S = 0.98
4975 reflections
344 parameters
421 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051518/fy2030sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811051518/fy2030Isup3.cml

checkCIF report

Comment top

Donor molecules featuring a skeleton of 2,5-di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-thione (I) and 2,5-di(1,3-dithiol-2-ylidene)-1,3-dithiolane-4-quinone (II) are used for the preparation of charge transfer (CT) complexes with magnetic metal anions (Wang et al., 2005, 2007; Hiraoka et al., 2005; Fujiwara et al., 2006, 2007). In CT salts these molecules can form unique crystal structures with channels in addition to the usual layer stacking structures as a result of intermolecular S···S contacts. Through an investigation of the unique molecular arrangements of the derivatives of (I) and (II) in their crystals, we found that the derivatives of (I) are stacked in the same orientation and the derivatives of (II) are alternately stacked in opposite directions (Ueda & Yoza, 2009a, 2009b, 2009c; Ueda et al., 2010). This result suggests that the stacking orientation of the derivatives is largely influenced by their molecular skeletons. To identify the stacking orientation of skeleton (I), we synthesized (I) and investigated its crystal structure.

The asymmetric unit contains two crystallographically independent molecules. One of the two independent molecules shows orientational disorder in the C=S containing five-membered ring with occupancies of 0.924 (3) (molecule A) and 0.076 (3) (molecule B). The other molecule of the asymmetric unit, molecule C, is ordered. The framework of (I) is almost planar: the mean deviation of the atoms from their mean plane is 0.088 (5) Å for A, 0.123 (2) Å for B and 0.128 (7) Å for C.

In the crystal structure, two different orientations of the molecules are present. Both orientations enclose a dihedral angle of about 27° with the ac plane, but the mean plane of the molecules is nearly parallel either with (011) or with (01–1) (Fig. 2). Molecules with the same orientation form stacks along the b axis. The stacked molecules are separated by interplanar distances greater than 3.54 Å and have a fairly poor overlap. However some effective side-by-side contacts are observed between molecules of adjacent columns (Fig. 3). The interaction between adjacent columns is accomplished through contacts between different sulfur atoms: S9···S3Bⁱ = 3.33 (2) Å [(i): 1–x, 1/2+y, 1–z]; S8···S3Aⁱⁱ = 3.434 (3) Å [(ii): x, 1+y, 1+z]; S6···S6ⁱⁱⁱ = 3.444 (2) Å [(iii):–x, 1/2+y, –z]; S3C···S10ⁱ = 3.503 (2) Å; S4···S9ⁱ = 3.519 (3) Å; S2B···S3A^iv = 3.53 (4) Å [(iv): x, 1+y, z]; and through contacts between sulfur and hydrogen atoms: S2C···H9Aⁱ = 2.814 (2) Å, S1B···H15A = 2.87 (7); S3B···H11A^iv = 2.92 (2) Å; S5···H6Aⁱ = 2.9269 (18) Å; S3B···H11A^v = 2.93 (2) Å [(v): x, y, z–1]; S3B···H12A^vi = 2.94 (2) Å [(vi): 1–x, –1/2+y, 1–z]; S2C···H9A^vii = 2.939 (2)Å [(vii): –x, –1/2+y, 1–z]; S3A···H8Aⁱⁱⁱ = 2.967 (2) Å; S3C···H14A^viii = 2.974 (1) Å [(viii): –x, 1/2+y, 1–z]. These distances are shorter than the sum of corresponding van der Waals radii, i.e., 3.60 Å for S···S and 3.00 Å for S···H (Bondi, 1964).

Related literature top

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 top

Compound (I) was synthesized by a modification of the method used for the preparation of 2-[4,5-bis(ethylsulfanyl)-1,3-dithiol-2-ylidene]-5-(4,5-diiodo-1,3-dithiol-2-ylidene)-1,3-dithiolan-4-thione (Ueda et al., 2010). Bis(tetra-n-butylammonium)bis[2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4,5-bis(thiolate)]zinc (194 mg, 0.170 mmol) reacted with 2-methylsulfanyl-1,3-dihiole-2-ylium tetrafluoroborate (89.3 mg, 0.378 mmol) in THF-DMF (4:1 = v/v) at room temperature under nitrogen, and stirring was carried out for 12 h. After separation of the reaction mixture by column chromatography on silica gel (eluent CS₂) followed by recrystallization from 1:10 CS₂/hexane, (I) was obtained as black needles in 79% yield.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing atom labeling and 50% probability displacement ellipsoids for non-H-atoms.
	Fig. 2. Projection of the crystal packing of (I) down the bc plane.
	Fig. 3. (a) Projection of the crystal packing of molecules A and C in (I) down the ac plane. The S···S and S···H contacts are shown with blue solid lines. (b) Projection of the crystal packing of molecules B and C in (I) down the ac plane. The S···S and S···H contacts are shown with blue solid lines.

(I) top

Crystal data top

C₉H₄S₇	F(000) = 680
M_r = 336.54	D_x = 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

Data collection top

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 monochromator	R_int = 0.054
Detector resolution: 8.333 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
phi and ω scans	h = −22→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→4
T_min = 0.894, T_max = 0.975	l = −22→23
6965 measured reflections

Refinement top

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(F_o²) + (0.0283P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.002
4975 reflections	Δρ_max = 0.63 e Å⁻³
344 parameters	Δρ_min = −0.52 e Å⁻³
421 restraints	Absolute structure: Flack (1983), 1849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.18 (18)

Crystal data top

C₉H₄S₇	V = 1206.8 (6) Å³
M_r = 336.54	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 17.669 (5) Å	µ = 1.27 mm⁻¹
b = 3.9110 (11) Å	T = 93 K
c = 18.380 (5) Å	0.09 × 0.02 × 0.02 mm
β = 108.177 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4975 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3396 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.975	R_int = 0.054
6965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.107	Δρ_max = 0.63 e Å⁻³
S = 0.98	Δρ_min = −0.52 e Å⁻³
4975 reflections	Absolute structure: Flack (1983), 1849 Friedel pairs
344 parameters	Absolute structure parameter: −0.18 (18)
421 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₉H₄S₇
M_r	336.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	93
a, b, c (Å)	17.669 (5), 3.9110 (11), 18.380 (5)
β (°)	108.177 (4)
V (Å³)	1206.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.09 × 0.02 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.894, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6965, 4975, 3396
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.107, 0.98
No. of reflections	4975
No. of parameters	344
No. of restraints	421
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.52
Absolute structure	Flack (1983), 1849 Friedel pairs
Absolute structure parameter	−0.18 (18)

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), XCIF (Bruker, 2010).

References

Bondi, A. (1964). J. Phys. Chem. 68, 441–451. CrossRef CAS Web of Science Google Scholar
Bruker (2010). APEX2, SAINT, XCIF. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T. & Nakazumi, H. (2006). J. Low Temp. Phys. 142, 405–408. Web of Science CSD CrossRef Google Scholar
Fujiwara, H., Wada, K., Hiraoka, T., Hayashi, T., Sugimoto, T., Nakazumi, H., Teramura, M., Yokogawa, K., Yasuzuka, S. & Murata, K. (2007). Multifunctional Conducting Molecular Materials, edited by G. Saito, F. Wudl, R. C. Haddon, K. Tanigaki, T. Enoki, H. E. Katz & M. Maesato, pp. 161–164. Cambridge: RSC Publishing. Google Scholar
Hiraoka, T., Kamada, Y., Matsumoto, T., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Nakazumi, H. & Katori, H. A. (2005). J. Mater. Chem. 15, 3479–3487. Web of Science CSD CrossRef CAS Google Scholar
Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Adachi, T., Fujita, H., Yoshino, H., Mizuno, Y., Murata, K. & Shiro, M. (2000). Inorg. Chem. 39, 3810–3815. CrossRef PubMed CAS Google Scholar
Iwamatsu, M., Kominami, T., Ueda, K., Sugimoto, T., Fujita, H. & Adachi, T. (1999). Chem. Lett. pp. 329–330. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Götingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ueda, K., Suzuki, K., Suzuki, K., Yoza, K. & Ishida, T. (2010). Phys. B (Amsterdam), 405, S69–S74. Web of Science CrossRef CAS Google Scholar
Ueda, K. & Yoza, K. (2009a). Acta Cryst. E65, o2716. Web of Science CrossRef IUCr Journals Google Scholar
Ueda, K. & Yoza, K. (2009b). Acta Cryst. E65, o2831. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ueda, K. & Yoza, K. (2009c). Acta Cryst. E65, o2920. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, M., Fujiwara, H., Sugimoto, T., Noguchi, S. & Ishida, T. (2005). Inorg. Chem. 44, 1184–1186. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wang, M., Xiao, X., Fujiwara, H., Sugimoto, T., Noguchi, S., Ishida, T., Mori, T. & Katori, H. A. (2007). Inorg. Chem. 46, 3049–3056. Web of Science CSD CrossRef PubMed CAS Google Scholar