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The structure of bis­[4,5-ethyl­enedi­thio-2-(4,5-ethyl­enedi­thio-1,3-diselena­cyclo­pent-4-en-2-yl­idene)-1,3-diselena­cyclo­pent-4-enium] bis(μ-1,2,5-thia­diazo­le-3,4-di­thiol­ato-κ3S4,S5:S4)bis[(1,2,5-thia­diazo­le-3,4-di­thiol­ato-κ2S4,S5)­iron(III)], (BETS)2[Fe(tdas)2]2 [BETS is alternatively called bis­(ethyl­enedi­thio)­tetraselenafulvalenium] or (C10H8S4Se4)2[{Fe(C2N2S3)2}2], consists of segregated columns of dimers of BETS and columns of dimers of [Fe(tdas)2]. Each dimer displays inversion symmetry. Numerous chalcogen–chalcogen contacts are observed within and between the columns, producing a network of interactions responsible for the metal-like behaviour of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010200330X/jz1495sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010200330X/jz1495Isup2.hkl
Contains datablock I

CCDC reference: 184470

Computing details top

Data collection: IPDS (Stoe & Cie, 1996); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

bis[4,5-ethylenedithio-2-(4,5-ethylenedithio-1,3-diselenacyclopent-4-en-2- ylidene)-1,3-diselenacyclopent-4-enium] bis(µ-1,2,5-thiadiazole-3,4-dithiolato-κ3S4,S5:S4)- bis[(1,2,5-thiadiazole-3,4-dithiolato-κ2S4,S5)iron(III)] top
Crystal data top
(C10H8S4Se4)[Fe2(C2N2S3)4]Z = 1
Mr = 1849.06F(000) = 884
Triclinic, P1Dx = 2.488 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5466 (12) ÅCell parameters from 8000 reflections
b = 12.1018 (16) Åθ = 2–25.9°
c = 12.9993 (16) ŵ = 7.37 mm1
α = 109.293 (14)°T = 160 K
β = 99.966 (16)°Block, black
γ = 95.14 (1)°0.15 × 0.12 × 0.10 mm
V = 1234.2 (3) Å3
Data collection top
Stoe IPDS
diffractometer
4503 independent reflections
Radiation source: fine-focus sealed tube3449 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
φ scansθmax = 26.1°, θmin = 2.0°
Absorption correction: part of the refinement model (ΔF)
(Parkin et al., 1995) Cubic fit to sinθ/λ with 24 parameters. Correction applied to the full data set.
h = 1010
Tmin = 0.429, Tmax = 0.478k = 1414
13154 measured reflectionsl = 015
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: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0374P)2]
where P = (Fo2 + 2Fc2)/3
4503 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.82 e Å3
Special details top

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS) equipped with an Oxford Cryosystems cooler device. The crystal-to-detector distance was 70 mm. 135 exposures (5 min per exposure) were obtained with 0 < φ < 270° and with the crystals rotated through 2° in φ. Crystal decay was monitored by measuring 200 reflections per image.

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
Se10.10529 (5)0.38166 (4)0.21999 (4)0.01394 (12)
Se20.34615 (5)0.37223 (3)0.42946 (4)0.01019 (11)
Se30.00052 (5)0.63386 (4)0.38264 (4)0.01563 (12)
Se40.24385 (5)0.62543 (3)0.59168 (4)0.01130 (11)
S10.16674 (15)0.14254 (11)0.06888 (11)0.0257 (3)
S20.43263 (13)0.13689 (9)0.30128 (10)0.0164 (3)
S40.16678 (14)0.85778 (10)0.74588 (11)0.0193 (3)
S30.10301 (14)0.86119 (9)0.51426 (11)0.0204 (3)
C10.1935 (5)0.4515 (3)0.3735 (4)0.0102 (9)
C20.1507 (5)0.5537 (3)0.4395 (4)0.0115 (9)
C30.2142 (5)0.2510 (3)0.2024 (4)0.0126 (10)
C40.3173 (5)0.2458 (3)0.2917 (4)0.0109 (9)
C50.0238 (5)0.7563 (3)0.5211 (4)0.0137 (10)
C60.1257 (5)0.7522 (3)0.6105 (4)0.0122 (10)
C70.3525 (6)0.0824 (4)0.0700 (4)0.0207 (11)
H7A0.34600.02040.00350.025*
H7B0.44190.14610.08140.025*
C80.3886 (6)0.0297 (4)0.1601 (4)0.0190 (11)
H8A0.48180.01250.14900.023*
H8B0.29510.02960.15150.023*
C90.0451 (6)0.9745 (4)0.6518 (5)0.0251 (12)
H9A0.06381.05170.64530.030*
H9B0.11580.95680.69900.030*
C100.1282 (6)0.9863 (4)0.7102 (5)0.0236 (12)
H10A0.15371.05750.77910.028*
H10B0.19970.99760.66090.028*
Fe110.58858 (7)0.53843 (5)0.12290 (5)0.00994 (15)
S110.67885 (14)0.36917 (9)0.12074 (10)0.0163 (3)
S120.92605 (14)0.25783 (10)0.12913 (11)0.0213 (3)
S130.69297 (12)0.54212 (9)0.02362 (10)0.0112 (2)
S140.60282 (14)0.73501 (9)0.16334 (10)0.0155 (3)
S150.53959 (13)0.55249 (9)0.28927 (10)0.0139 (2)
S160.39416 (16)0.87059 (10)0.42992 (11)0.0227 (3)
N110.8512 (4)0.2466 (3)0.0236 (3)0.0185 (9)
N120.8626 (4)0.3795 (3)0.1349 (4)0.0192 (9)
N130.4192 (4)0.7342 (3)0.4201 (3)0.0170 (9)
N140.4709 (5)0.8780 (3)0.3240 (3)0.0197 (9)
C110.7752 (5)0.3375 (4)0.0097 (4)0.0156 (10)
C120.7827 (5)0.4137 (4)0.0544 (4)0.0128 (10)
C130.4846 (5)0.6922 (3)0.3339 (4)0.0113 (9)
C140.5145 (5)0.7748 (4)0.2784 (4)0.0123 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0144 (2)0.0144 (2)0.0123 (3)0.00383 (16)0.00031 (18)0.00459 (17)
Se20.0102 (2)0.0106 (2)0.0098 (2)0.00003 (15)0.00195 (17)0.00415 (16)
Se30.0142 (2)0.0163 (2)0.0155 (3)0.00454 (17)0.00081 (19)0.00504 (18)
Se40.0099 (2)0.0115 (2)0.0126 (3)0.00051 (15)0.00286 (17)0.00456 (17)
S10.0254 (6)0.0258 (6)0.0149 (7)0.0111 (5)0.0057 (5)0.0039 (5)
S20.0185 (6)0.0148 (5)0.0148 (6)0.0065 (4)0.0020 (5)0.0034 (4)
S40.0209 (6)0.0168 (5)0.0174 (7)0.0025 (4)0.0064 (5)0.0016 (5)
S30.0193 (6)0.0152 (5)0.0295 (8)0.0076 (4)0.0071 (5)0.0092 (5)
C10.0038 (18)0.014 (2)0.014 (2)0.0009 (15)0.0001 (17)0.0085 (17)
C20.009 (2)0.0103 (19)0.015 (3)0.0021 (15)0.0023 (18)0.0044 (17)
C30.013 (2)0.011 (2)0.014 (3)0.0008 (16)0.0050 (18)0.0049 (17)
C40.010 (2)0.0086 (19)0.013 (2)0.0018 (15)0.0048 (18)0.0027 (17)
C50.009 (2)0.0088 (19)0.025 (3)0.0024 (15)0.0066 (19)0.0067 (18)
C60.011 (2)0.0099 (19)0.015 (3)0.0018 (16)0.0048 (18)0.0031 (17)
C70.022 (2)0.024 (2)0.017 (3)0.0116 (19)0.008 (2)0.004 (2)
C80.027 (3)0.010 (2)0.017 (3)0.0018 (18)0.005 (2)0.0007 (18)
C90.028 (3)0.019 (2)0.028 (3)0.0059 (19)0.013 (2)0.004 (2)
C100.024 (2)0.013 (2)0.031 (3)0.0016 (18)0.010 (2)0.003 (2)
Fe110.0098 (3)0.0112 (3)0.0099 (3)0.0004 (2)0.0027 (2)0.0053 (2)
S110.0209 (6)0.0176 (5)0.0154 (6)0.0065 (4)0.0071 (5)0.0099 (4)
S120.0189 (6)0.0214 (6)0.0239 (7)0.0064 (4)0.0098 (5)0.0048 (5)
S130.0101 (5)0.0126 (5)0.0123 (6)0.0007 (4)0.0047 (4)0.0055 (4)
S140.0226 (6)0.0111 (5)0.0142 (6)0.0026 (4)0.0088 (5)0.0052 (4)
S150.0214 (6)0.0137 (5)0.0107 (6)0.0039 (4)0.0061 (5)0.0082 (4)
S160.0338 (7)0.0173 (6)0.0221 (7)0.0083 (5)0.0156 (6)0.0078 (5)
N110.0159 (19)0.0179 (19)0.021 (2)0.0064 (15)0.0055 (17)0.0048 (16)
N120.0163 (19)0.0186 (19)0.020 (2)0.0014 (15)0.0081 (17)0.0024 (16)
N130.019 (2)0.0163 (18)0.019 (2)0.0008 (15)0.0099 (18)0.0088 (16)
N140.029 (2)0.0166 (19)0.016 (2)0.0042 (16)0.0069 (18)0.0076 (16)
C110.010 (2)0.016 (2)0.017 (3)0.0002 (17)0.0012 (19)0.0019 (18)
C120.0075 (19)0.013 (2)0.015 (3)0.0027 (16)0.0017 (18)0.0038 (17)
C130.009 (2)0.012 (2)0.011 (2)0.0030 (16)0.0004 (18)0.0052 (17)
C140.014 (2)0.011 (2)0.014 (3)0.0030 (16)0.0033 (19)0.0085 (17)
Geometric parameters (Å, º) top
Se1—C31.875 (4)C9—H9A0.9900
Se1—C11.875 (4)C9—H9B0.9900
Se2—C11.873 (4)C10—H10A0.9900
Se2—C41.892 (4)C10—H10B0.9900
Se3—C21.872 (4)Fe11—S152.2282 (15)
Se3—C51.880 (5)Fe11—S112.2460 (12)
Se4—C21.870 (5)Fe11—S142.2473 (12)
Se4—C61.883 (4)Fe11—S132.2500 (14)
S1—C31.748 (4)Fe11—S13i2.4656 (12)
S1—C71.804 (5)S11—C111.735 (5)
S2—C41.739 (4)S12—N121.634 (4)
S2—C81.815 (5)S12—N111.650 (5)
S4—C61.753 (4)S13—C121.753 (4)
S4—C101.806 (5)S13—Fe11i2.4656 (12)
S3—C51.755 (4)S14—C141.737 (5)
S3—C91.810 (5)S15—C131.734 (4)
C1—C21.374 (6)S16—N141.648 (5)
C3—C41.353 (6)S16—N131.650 (4)
C5—C61.345 (7)N11—C111.316 (5)
C7—C81.509 (7)N12—C121.321 (6)
C7—H7A0.9900N13—C131.311 (6)
C7—H7B0.9900N14—C141.311 (6)
C8—H8A0.9900C11—C121.437 (7)
C8—H8B0.9900C13—C141.442 (6)
C9—C101.513 (7)
Se1···S11ii3.622 (1)Se4···S15iii3.519 (1)
Se3···S15ii3.850 (1)S2···S16iii3.585 (2)
Se2···S15iii3.399 (1)Se1···S13i3.624 (2)
Se4···S11iii3.660 (2)
C3—Se1—C193.91 (18)S3—C9—H9B108.6
C1—Se2—C493.82 (18)H9A—C9—H9B107.6
C2—Se3—C593.52 (19)C9—C10—S4112.0 (3)
C2—Se4—C693.60 (18)C9—C10—H10A109.2
C3—S1—C799.4 (2)S4—C10—H10A109.2
C4—S2—C8103.8 (2)C9—C10—H10B109.2
C6—S4—C1098.5 (2)S4—C10—H10B109.2
C5—S3—C9103.8 (2)H10A—C10—H10B107.9
C2—C1—Se2122.7 (3)S15—Fe11—S1185.95 (5)
C2—C1—Se1122.5 (3)S15—Fe11—S1491.82 (5)
Se2—C1—Se1114.8 (2)S11—Fe11—S14156.47 (5)
C1—C2—Se4122.3 (3)S15—Fe11—S13167.46 (5)
C1—C2—Se3122.5 (3)S11—Fe11—S1392.48 (5)
Se4—C2—Se3115.2 (2)S14—Fe11—S1384.66 (5)
C4—C3—S1125.5 (3)S15—Fe11—S13i93.89 (5)
C4—C3—Se1119.1 (3)S11—Fe11—S13i99.56 (4)
S1—C3—Se1115.4 (2)S14—Fe11—S13i103.96 (5)
C3—C4—S2129.5 (3)S13—Fe11—S13i98.64 (4)
C3—C4—Se2118.2 (3)C11—S11—Fe11102.66 (16)
S2—C4—Se2112.3 (2)N12—S12—N1199.2 (2)
C6—C5—S3128.6 (4)C12—S13—Fe11102.29 (17)
C6—C5—Se3119.0 (3)C12—S13—Fe11i101.60 (13)
S3—C5—Se3112.4 (3)Fe11—S13—Fe11i81.36 (4)
C5—C6—S4126.2 (3)C14—S14—Fe11101.42 (14)
C5—C6—Se4118.6 (3)C13—S15—Fe11101.75 (17)
S4—C6—Se4115.1 (2)N14—S16—N1398.9 (2)
C8—C7—S1112.5 (4)C11—N11—S12107.1 (3)
C8—C7—H7A109.1C12—N12—S12106.2 (3)
S1—C7—H7A109.1C13—N13—S16106.5 (3)
C8—C7—H7B109.1C14—N14—S16106.8 (3)
S1—C7—H7B109.1N11—C11—C12112.8 (4)
H7A—C7—H7B107.8N11—C11—S11125.6 (4)
C7—C8—S2114.5 (3)C12—C11—S11121.6 (3)
C7—C8—H8A108.6N12—C12—C11114.8 (4)
S2—C8—H8A108.6N12—C12—S13124.2 (4)
C7—C8—H8B108.6C11—C12—S13121.0 (4)
S2—C8—H8B108.6N13—C13—C14114.2 (4)
H8A—C8—H8B107.6N13—C13—S15124.9 (4)
C10—C9—S3114.8 (3)C14—C13—S15120.8 (4)
C10—C9—H9A108.6N14—C14—C13113.6 (4)
S3—C9—H9A108.6N14—C14—S14125.8 (4)
C10—C9—H9B108.6C13—C14—S14120.6 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1.
 

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