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The bonding in the C—C—C—Sthione fragment of the title mol­ecule, C9H8N2S5, is highly conjugated. Owing to strong S...S [3.4842 (4) Å] and S...N [3.1223 (13) and 3.1425 (14) Å] inter­molecular inter­actions, a kind of one-dimensional double mol­ecular chain can be found along the a direction of the unit cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044078/im2033sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044078/im2033Isup2.hkl
Contains datablock I

CCDC reference: 663766

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.086
  • Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.92 PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 6.15 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.63 su
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.915 Tmax scaled 0.915 Tmin scaled 0.755
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The rapid progress of molecular conductors or superconductors in the past three decades has been triggered by the successful syntheses of novel and useful organic donors. The synthesis of TTF (C6S4H4, tetrathiafulvalene) in 1970 and BEDT-TTF (C10S8H8, bis(ethylenedithio)-tetrathiafulvalene) in the late 1970 s have resulted in more than one hundred TTF-based organic superconductors, such as κ-(BEDT-TTF)2Cu[N(CN)2]Br with Tc = 11.6 K at ambient pressure (Kini et al., 1991). One kind of promising donors for new molecular conductors still seem to be multi-sulfur heterocyclic compounds with more sulfur atoms fused into the TTF skeleton, such as BEDT-TTP (C14S12H8, 2,5-bis(4,5-ethylenedithio-1,3-dithiol-2-ylidene) -1,3,4,6-tetrathiapentalene) and similar donors (Mori et al., 1995). In the course of exploring some derivatives of BEDT-TTP, we obtained their precursor 4,5-bis(2'-cyanoethylsulfanyl)-[1,3]-dithiole-2-thione (I) (Figure 1) and determined its structure (Yu et al., 2003). Here we report the structure and synthesis of its isomer: 4,5-bis(2'-cyanoethylsulfanyl)-[1,2]-dithiole-3-thione (II).

As shown in Figure 2, the five-membered 1,2-dithiole ring is basically planar and the plane (plane 1) can be extended to three peripheral sulfur atoms (S3, S4 and S5) and the C4 atom. Of these nine atoms, S4 shows the biggest deviation from the plane, 0.051 (1) Å. Four atoms (C4, C5, C6 and N1) of one side-chain of the molecule are within the second plane (Plane 2) and the five atoms (S5, C6, C7, C8 and N2) of the other side-chain are arranged in the third plane (Plane 3). The dihedral angels between these planes are 71.6 (1)° (between planes 1 and 2), 84.0 (1)° (1 and 3), and 56.7 (1)° (2 and 3).

The bonding in the C1—C2—C3—S3 fragment of the 1,2-isomer is highly conjugated with the bond lengths being 1.384 (2), 1.430 (2) and 1.661 (1) Å for the C1—C2, C2—C3 and terminal C3—S3 bonds, respectively. The π-conjugation may involve three more atoms (S1, S2 and S4) because of the "conjugated" bond lengths C1—S1 (1.725 (1) Å), C3—S2 (1.733 (1) Å), and C1—S4 (1.737 (1) Å). However, the π-conjugation is not circular because the S1—S2 bond length (2.0702 (5) Å) is indicative for a single bond. By comparison, the conjugation in (I) is not very significant because of the double CC (1.346 (1) Å) and the terminal double CS bond (1.644 (1) Å).

As shown in Figure 3, in the crystal of (II) each molecule participates in six strong S···S and S···N intermolecular interactions with its three neighbours. Three of these six contacts are symmetrically independent, viz. S4···S5A (-x, -y, 1 - z) of 3.484 (2) Å, S1···N1B (1 + x, y, z) of 3.112 (2) and S2···N1B (1 + x, y, z) of 3.142 (2) Å. These contacts are significantly shorter than the standard intermolecular (van der Waals) contact distances S···S of 3.60 Å and S···N of 3.45 Å (Rowland & Taylor, 1996). These intermolecular interactions help to form a kind of supramolecular planar moiety involving 20 atoms: nine from the main molecular plane (Plane 1) of the concerned molecule, another nine from the main plane of the adjacent molecule (-x, -y, 1 - z) and two N1 atoms from other two molecules. Furthermore, due to these S···S and S···N interactions, a kind of one-dimensional double chain of molecules can be found along the a-direction. By comparison, there are no short S···S contacts in the crystal of (I), corresponding to the relatively strong intermolecular interactions of (II).

Related literature top

For related literature, see: Mori et al. (1995); Rowland & Taylor (1996); Yu et al. (2003).

For related literature, see: Kini et al. (1990).

Experimental top

The title compound has been synthesized by the route shown in the Scheme. 3-Bromo-propionitrile (12.5 ml, 0.15 mmol) was added to a stirred 200 ml acetone solution containing (Bu4N)2[Zn(dmit)2] (28.5 g, 0.030 mmol). After reacting for 12 h at 320 K, the solvent was removed. The residue was dissolved in 250 ml CH2Cl2, and 200 ml water was added. After being stirred overnight and the water layer removed, 100 ml CH3OH was added into the CH2Cl2 solution. Needle-shaped orange crystals of (4,5-bis(2'-cyanoethylsulfanyl)-[1,3]-dithiole-2-thione) (I) formed quickly when most of the CH2Cl2 had evaporated. The solvent remaining in the mother-liquor was removed, the residual mixture which contained both (I) and (II), was separated by column chromatography on silica gel (eluent CH2Cl2). The yields based on (Bu4N)2[Zn(dmit)2] for (I) and (II) were 81% and 9%, respectively. The orange (I) moved faster in the column (Rf = 1/2), followed by 4,5-bis(2'-cyanoethylsulfanyl)-[1,2]-dithiole-3-thion (II) of the same colour (Rf = 0.3), indicating higher polarity of (II). When most of the CH2Cl2 evaporated, platelet crystals of (II) have been obtained with the m.p. of 438–440 K.

Refinement top

All H atoms were located in a difference Fourier map and refined in isotropic approximation without constraints, C—H distances 0.92 (2) to 0.98 (2) Å.

Structure description top

The rapid progress of molecular conductors or superconductors in the past three decades has been triggered by the successful syntheses of novel and useful organic donors. The synthesis of TTF (C6S4H4, tetrathiafulvalene) in 1970 and BEDT-TTF (C10S8H8, bis(ethylenedithio)-tetrathiafulvalene) in the late 1970 s have resulted in more than one hundred TTF-based organic superconductors, such as κ-(BEDT-TTF)2Cu[N(CN)2]Br with Tc = 11.6 K at ambient pressure (Kini et al., 1991). One kind of promising donors for new molecular conductors still seem to be multi-sulfur heterocyclic compounds with more sulfur atoms fused into the TTF skeleton, such as BEDT-TTP (C14S12H8, 2,5-bis(4,5-ethylenedithio-1,3-dithiol-2-ylidene) -1,3,4,6-tetrathiapentalene) and similar donors (Mori et al., 1995). In the course of exploring some derivatives of BEDT-TTP, we obtained their precursor 4,5-bis(2'-cyanoethylsulfanyl)-[1,3]-dithiole-2-thione (I) (Figure 1) and determined its structure (Yu et al., 2003). Here we report the structure and synthesis of its isomer: 4,5-bis(2'-cyanoethylsulfanyl)-[1,2]-dithiole-3-thione (II).

As shown in Figure 2, the five-membered 1,2-dithiole ring is basically planar and the plane (plane 1) can be extended to three peripheral sulfur atoms (S3, S4 and S5) and the C4 atom. Of these nine atoms, S4 shows the biggest deviation from the plane, 0.051 (1) Å. Four atoms (C4, C5, C6 and N1) of one side-chain of the molecule are within the second plane (Plane 2) and the five atoms (S5, C6, C7, C8 and N2) of the other side-chain are arranged in the third plane (Plane 3). The dihedral angels between these planes are 71.6 (1)° (between planes 1 and 2), 84.0 (1)° (1 and 3), and 56.7 (1)° (2 and 3).

The bonding in the C1—C2—C3—S3 fragment of the 1,2-isomer is highly conjugated with the bond lengths being 1.384 (2), 1.430 (2) and 1.661 (1) Å for the C1—C2, C2—C3 and terminal C3—S3 bonds, respectively. The π-conjugation may involve three more atoms (S1, S2 and S4) because of the "conjugated" bond lengths C1—S1 (1.725 (1) Å), C3—S2 (1.733 (1) Å), and C1—S4 (1.737 (1) Å). However, the π-conjugation is not circular because the S1—S2 bond length (2.0702 (5) Å) is indicative for a single bond. By comparison, the conjugation in (I) is not very significant because of the double CC (1.346 (1) Å) and the terminal double CS bond (1.644 (1) Å).

As shown in Figure 3, in the crystal of (II) each molecule participates in six strong S···S and S···N intermolecular interactions with its three neighbours. Three of these six contacts are symmetrically independent, viz. S4···S5A (-x, -y, 1 - z) of 3.484 (2) Å, S1···N1B (1 + x, y, z) of 3.112 (2) and S2···N1B (1 + x, y, z) of 3.142 (2) Å. These contacts are significantly shorter than the standard intermolecular (van der Waals) contact distances S···S of 3.60 Å and S···N of 3.45 Å (Rowland & Taylor, 1996). These intermolecular interactions help to form a kind of supramolecular planar moiety involving 20 atoms: nine from the main molecular plane (Plane 1) of the concerned molecule, another nine from the main plane of the adjacent molecule (-x, -y, 1 - z) and two N1 atoms from other two molecules. Furthermore, due to these S···S and S···N interactions, a kind of one-dimensional double chain of molecules can be found along the a-direction. By comparison, there are no short S···S contacts in the crystal of (I), corresponding to the relatively strong intermolecular interactions of (II).

For related literature, see: Mori et al. (1995); Rowland & Taylor (1996); Yu et al. (2003).

For related literature, see: Kini et al. (1990).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Reaction scheme for the formation of the title compound.
[Figure 2] Fig. 2. Molecular structure of the title compound. Displacement ellipsoid are drawn at the 50% probability level.
[Figure 3] Fig. 3. Packing of (II) in the crystal structure showing one-dimensional double molecular chain structure by short S···S and S···N intermolecular interactions. [Symmetry code: (A) -x, -y, 1 - z; (B) 1 + x, y, z]
4,5-Bis(2-cyanoethylsulfanyl)-1,2-dithiole-3-thione top
Crystal data top
C9H8N2S5Z = 2
Mr = 304.47F(000) = 312
Triclinic, P1Dx = 1.605 Mg m3
Hall symbol: -P 1Melting point: 439(1) K
a = 8.0216 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9771 (3) ÅCell parameters from 4653 reflections
c = 9.4799 (5) Åθ = 2.3–35.5°
α = 91.251 (3)°µ = 0.89 mm1
β = 112.426 (2)°T = 120 K
γ = 92.418 (2)°Platelet, orange
V = 629.93 (5) Å30.40 × 0.35 × 0.10 mm
Data collection top
Rigaku R-AXIS SPIDER IP
diffractometer
3811 independent reflections
Radiation source: fine-focus sealed tube3721 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 10.00 pixels mm-1θmax = 30.5°, θmin = 2.3°
wide ω scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
k = 1212
Tmin = 0.825, Tmax = 1.000l = 1313
12836 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.086All H-atom parameters refined
S = 1.10 w = 1/[σ2(Fo2) + (0.0355P)2 + 0.1882P]
where P = (Fo2 + 2Fc2)/3
3811 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C9H8N2S5γ = 92.418 (2)°
Mr = 304.47V = 629.93 (5) Å3
Triclinic, P1Z = 2
a = 8.0216 (4) ÅMo Kα radiation
b = 8.9771 (3) ŵ = 0.89 mm1
c = 9.4799 (5) ÅT = 120 K
α = 91.251 (3)°0.40 × 0.35 × 0.10 mm
β = 112.426 (2)°
Data collection top
Rigaku R-AXIS SPIDER IP
diffractometer
3811 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
3721 reflections with I > 2σ(I)
Tmin = 0.825, Tmax = 1.000Rint = 0.040
12836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.086All H-atom parameters refined
S = 1.10Δρmax = 0.57 e Å3
3811 reflectionsΔρmin = 0.30 e Å3
177 parameters
Special details top

Experimental. scan: Number of images: 41 Slice: 51.0000 - 175.0000 Image width: 3.0000 Exp time: 300.0000 Rotation axis: Omega Omega: 0.0000 Chi: 0.0000 Phi: 0.0000 XTD: 127.4000 2theta: -0.0164 scan: Number of images: 40 Slice: 20.0000 - 140.0000 Image width: 3.0000 Exp time: 300.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 127.4000 2theta: -0.0164 scan: Number of images: 40 Slice: 20.0000 - 140.0000 Image width: 3.0000 Exp time: 300.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 180.0000 XTD: 127.4000 2theta: -0.0164

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
xyzUiso*/Ueq
S30.78564 (4)0.08290 (4)0.87088 (4)0.02157 (9)
S10.46153 (4)0.27359 (4)0.42090 (4)0.01932 (8)
S20.71016 (4)0.23908 (4)0.59050 (4)0.01981 (9)
S40.11016 (4)0.14093 (4)0.42447 (4)0.01854 (8)
S50.32847 (4)0.01628 (4)0.74868 (4)0.01852 (8)
C30.63223 (17)0.13923 (14)0.70953 (15)0.0171 (2)
C10.34299 (16)0.17310 (14)0.50870 (15)0.0169 (2)
C20.43995 (16)0.11596 (14)0.64918 (14)0.0167 (2)
C40.04858 (18)0.23962 (16)0.24812 (15)0.0198 (2)
H4'0.132 (3)0.221 (2)0.206 (2)0.023 (4)*
H40.060 (3)0.193 (2)0.187 (3)0.031 (5)*
C50.02689 (19)0.40643 (16)0.26544 (18)0.0234 (3)
H5'0.137 (3)0.454 (2)0.342 (3)0.030 (5)*
H50.002 (3)0.452 (2)0.170 (3)0.029 (5)*
C60.12281 (19)0.43476 (16)0.31424 (17)0.0235 (3)
C70.24831 (17)0.17041 (16)0.82867 (16)0.0205 (2)
H7'0.189 (3)0.240 (2)0.749 (2)0.029 (5)*
H70.159 (3)0.127 (2)0.863 (3)0.030 (5)*
C80.40294 (19)0.25499 (18)0.95806 (19)0.0251 (3)
H8'0.488 (3)0.300 (2)0.924 (3)0.032 (5)*
H80.460 (3)0.189 (3)1.034 (3)0.051 (7)*
C90.33548 (19)0.37807 (17)1.02277 (17)0.0244 (3)
N10.23980 (19)0.45526 (17)0.35162 (18)0.0316 (3)
N20.27916 (19)0.47209 (17)1.07180 (17)0.0312 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S30.01647 (14)0.02912 (18)0.01666 (17)0.00163 (12)0.00343 (12)0.00306 (13)
S10.01699 (14)0.02243 (16)0.01872 (16)0.00061 (11)0.00692 (12)0.00612 (12)
S20.01538 (14)0.02338 (17)0.02032 (17)0.00245 (11)0.00665 (12)0.00366 (12)
S40.01426 (13)0.02114 (16)0.01837 (16)0.00064 (11)0.00410 (12)0.00548 (12)
S50.01756 (14)0.01897 (16)0.01959 (16)0.00034 (11)0.00763 (12)0.00545 (12)
C30.0164 (5)0.0181 (5)0.0166 (5)0.0002 (4)0.0062 (4)0.0010 (4)
C10.0157 (5)0.0171 (5)0.0176 (6)0.0005 (4)0.0062 (4)0.0025 (4)
C20.0149 (5)0.0184 (6)0.0169 (6)0.0004 (4)0.0063 (4)0.0033 (4)
C40.0185 (5)0.0234 (6)0.0157 (6)0.0003 (5)0.0045 (5)0.0032 (5)
C50.0220 (6)0.0237 (6)0.0278 (7)0.0039 (5)0.0127 (5)0.0091 (5)
C60.0241 (6)0.0220 (6)0.0246 (7)0.0036 (5)0.0090 (5)0.0078 (5)
C70.0172 (5)0.0247 (6)0.0209 (6)0.0018 (5)0.0085 (5)0.0045 (5)
C80.0211 (6)0.0266 (7)0.0260 (7)0.0028 (5)0.0071 (5)0.0006 (5)
C90.0241 (6)0.0281 (7)0.0212 (6)0.0015 (5)0.0086 (5)0.0058 (5)
N10.0296 (6)0.0359 (7)0.0335 (7)0.0053 (5)0.0161 (6)0.0080 (6)
N20.0331 (7)0.0340 (7)0.0291 (7)0.0037 (5)0.0147 (6)0.0017 (6)
Geometric parameters (Å, º) top
C1—C21.3837 (19)C4—H40.92 (2)
C2—C31.4298 (16)C5—C61.4715 (19)
S1—C11.7248 (12)C5—H5'0.98 (2)
S1—S22.0702 (5)C5—H50.96 (2)
S2—C31.7328 (13)C6—N11.143 (2)
S3—C31.6613 (14)C7—C81.529 (2)
S4—C11.7366 (13)C7—H7'0.98 (2)
S4—C41.8153 (14)C7—H70.96 (2)
S5—C21.7616 (12)C8—C91.471 (2)
S5—C71.8178 (15)C8—H8'0.94 (2)
C4—C51.527 (2)C8—H80.93 (3)
C4—H4'0.920 (19)C9—N21.144 (2)
C1—S1—S293.66 (5)C6—C5—H5'107.4 (12)
C3—S2—S197.63 (5)C4—C5—H5'110.3 (13)
C1—S4—C4103.36 (6)C6—C5—H5107.9 (13)
C2—S5—C7100.01 (6)C4—C5—H5109.9 (13)
C2—C3—S3129.80 (10)H5'—C5—H5109.5 (17)
C2—C3—S2112.88 (10)N1—C6—C5179.28 (17)
S3—C3—S2117.31 (7)C8—C7—S5111.61 (9)
C2—C1—S1117.78 (9)C8—C7—H7'109.0 (12)
C2—C1—S4120.33 (9)S5—C7—H7'109.6 (12)
S1—C1—S4121.88 (8)C8—C7—H7112.2 (13)
C1—C2—C3117.97 (11)S5—C7—H7105.9 (13)
C1—C2—S5120.60 (9)H7—C7—H7108.5 (17)
C3—C2—S5121.43 (10)C9—C8—C7110.91 (12)
C5—C4—S4114.45 (10)C9—C8—H8'105.7 (13)
C5—C4—H4'112.1 (12)C7—C8—H8'111.8 (14)
S4—C4—H4'108.1 (13)C9—C8—H8109.7 (16)
C5—C4—H4109.8 (14)C7—C8—H8109.0 (16)
S4—C4—H4103.3 (14)H8'—C8—H8110 (2)
H4'—C4—H4108.5 (18)N2—C9—C8178.41 (15)
C6—C5—C4111.76 (11)
C1—S1—S2—C32.15 (6)S3—C3—C2—C1178.61 (11)
S1—S2—C3—C21.46 (10)S2—C3—C2—C10.17 (17)
S1—S2—C3—S3179.59 (7)S3—C3—C2—S50.80 (19)
S2—S1—C1—C22.73 (11)S2—C3—C2—S5179.58 (7)
S2—S1—C1—S4176.32 (8)C7—S5—C2—C178.86 (12)
C4—S4—C1—C2179.01 (11)C7—S5—C2—C3101.74 (12)
C4—S4—C1—S11.97 (10)C1—S4—C4—C583.02 (10)
S1—C1—C2—C32.27 (18)S4—C4—C5—C663.92 (14)
S4—C1—C2—C3176.80 (10)C2—S5—C7—C872.34 (11)
S1—C1—C2—S5178.32 (7)S5—C7—C8—C9179.28 (10)
S4—C1—C2—S52.62 (17)

Experimental details

Crystal data
Chemical formulaC9H8N2S5
Mr304.47
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)8.0216 (4), 8.9771 (3), 9.4799 (5)
α, β, γ (°)91.251 (3), 112.426 (2), 92.418 (2)
V3)629.93 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.89
Crystal size (mm)0.40 × 0.35 × 0.10
Data collection
DiffractometerRigaku R-AXIS SPIDER IP
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.825, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
12836, 3811, 3721
Rint0.040
(sin θ/λ)max1)0.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.086, 1.10
No. of reflections3811
No. of parameters177
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.57, 0.30

Computer programs: CrystalClear (Rigaku, 2007), SHELXTL (Bruker, 2000).

Selected bond lengths (Å) top
C1—C21.3837 (19)S2—C31.7328 (13)
C2—C31.4298 (16)S3—C31.6613 (14)
S1—C11.7248 (12)S4—C11.7366 (13)
S1—S22.0702 (5)S5—C21.7616 (12)
 

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