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In the title complex, (C8H20N)2[Cu(C3S5)2], each Cu atom is tetracoordinated by four dmit S atoms (dmit is 2-thio­xo-1,3-di­thiole-4,5-di­thiol­ate), forming a slightly distorted square-planar arrangement. The average Cu-S bond length is a little larger than the sum of the single-bond covalent radii. The S-Cu-S bond angles for the vicinal S atoms are somewhat larger than the typical right angle and the other two angles are much smaller than 180°. The [Cu(dmit)2]2- anions and tetraethyl­ammonium counter-cations form a layered arrangement in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008159/hb6163sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008159/hb6163Isup2.hkl
Contains datablock I

CCDC reference: 270331

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.019 Å
  • R factor = 0.051
  • wR factor = 0.118
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found




Alert level B PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 19
Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C19
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.99 From the CIF: _reflns_number_total 3797 Count of symmetry unique reflns 3565 Completeness (_total/calc) 106.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 232 Fraction of Friedel pairs measured 0.065 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(tetraethylammonium) bis(2-thioxo-1,3-dithiole-4,5-dithiolato)copper(II) top
Crystal data top
(C8H20N)2[Cu(C3S5)2]F(000) = 1500
Mr = 716.70Dx = 1.455 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 36 reflections
a = 26.880 (4) Åθ = 10.3–12.5°
b = 8.0090 (11) ŵ = 1.32 mm1
c = 18.294 (3) ÅT = 293 K
β = 123.836 (8)°Plate, black
V = 3271.4 (8) Å30.43 × 0.41 × 0.02 mm
Z = 4
Data collection top
Bruker P4
diffractometer
2119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 27.0°, θmin = 2.3°
ω scansh = 134
Absorption correction: ψ scan
(XSCANS; Bruker, 1996)
k = 110
Tmin = 0.50, Tmax = 0.97l = 2319
4357 measured reflections3 standard reflections every 97 reflections
3797 independent reflections intensity decay: none
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0434P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118(Δ/σ)max < 0.001
S = 0.95Δρmax = 0.37 e Å3
3797 reflectionsΔρmin = 0.38 e Å3
325 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
14 restraintsExtinction coefficient: 0.00184 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 232 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6834 (4)0.2494 (13)0.5018 (6)0.053 (2)
C20.7324 (5)0.0068 (12)0.4749 (7)0.053 (3)
C30.7692 (5)0.1227 (12)0.4898 (6)0.052 (3)
C40.9375 (4)0.3520 (12)0.4757 (6)0.044 (2)
C50.9223 (4)0.4637 (11)0.5162 (5)0.042 (2)
C61.0067 (4)0.6065 (14)0.5062 (6)0.061 (3)
C70.7412 (6)0.2230 (15)0.6821 (8)0.079 (4)
H7A0.74330.17400.63540.095*
H7B0.70850.30280.65500.095*
C80.7255 (7)0.0850 (16)0.7233 (10)0.107 (5)
H8A0.68650.04170.68030.161*
H8B0.72560.12940.77220.161*
H8C0.75450.00300.74350.161*
C90.7957 (5)0.4116 (15)0.8105 (7)0.074 (3)
H9A0.83410.46550.84900.089*
H9B0.79040.33250.84590.089*
C100.7472 (6)0.5433 (16)0.7770 (9)0.089 (4)
H10A0.74340.57790.82400.133*
H10B0.70980.49780.72990.133*
H10C0.75760.63780.75590.133*
C110.8503 (6)0.1996 (17)0.7910 (8)0.091 (4)
H11A0.84500.12900.82920.109*
H11B0.88640.26480.82780.109*
C120.8582 (7)0.0884 (18)0.7295 (10)0.113 (5)
H12A0.89100.01290.76400.170*
H12B0.86640.15720.69440.170*
H12C0.82220.02580.69170.170*
C130.8046 (4)0.4336 (13)0.6831 (6)0.060 (3)
H13A0.80770.36770.64120.072*
H13B0.76870.50110.64990.072*
C140.8582 (5)0.5487 (15)0.7310 (8)0.078 (4)
H14A0.86110.61190.68890.118*
H14B0.89400.48370.76670.118*
H14C0.85360.62350.76780.118*
C150.9990 (5)0.0007 (18)0.7083 (9)0.093 (5)
H15A0.99480.07070.66230.111*
H15B0.96590.07910.68080.111*
C160.9943 (7)0.1066 (18)0.7726 (11)0.115 (5)
H16A0.95900.17480.74080.172*
H16B0.99190.03600.81300.172*
H16C1.02900.17690.80470.172*
C171.0623 (5)0.2250 (13)0.8132 (6)0.060 (3)
H17A1.10120.27810.84080.073*
H17B1.06120.16770.85900.073*
C181.0149 (6)0.3593 (16)0.7749 (10)0.106 (5)
H18A1.02270.43620.82040.159*
H18B0.97620.30930.75020.159*
H18C1.01560.41790.72960.159*
C191.1107 (5)0.0189 (14)0.8000 (7)0.060 (3)
H19A1.14660.04660.82110.072*
H19B1.11230.05950.85120.072*
C201.1123 (6)0.1664 (16)0.7511 (9)0.102 (5)
H20A1.14570.23610.79080.154*
H20B1.11620.12870.70470.154*
H20C1.07580.22890.72630.154*
C211.0563 (6)0.1830 (15)0.6724 (7)0.081 (4)
H21A1.05740.09750.63580.097*
H21B1.01910.24400.63640.097*
C221.1083 (7)0.3030 (16)0.7026 (10)0.105 (5)
H22A1.11100.32980.65370.158*
H22B1.14490.25140.74820.158*
H22C1.10170.40330.72480.158*
N10.7977 (4)0.3159 (10)0.7416 (5)0.053 (2)
N21.0567 (4)0.0970 (11)0.7488 (5)0.059 (2)
S10.64091 (14)0.3720 (4)0.5184 (2)0.0739 (9)
S20.67048 (13)0.0389 (4)0.4788 (2)0.0637 (7)
S30.74482 (12)0.3173 (3)0.50325 (18)0.0589 (7)
S40.74722 (12)0.2118 (3)0.4620 (2)0.0612 (7)
S50.83679 (13)0.1080 (3)0.49924 (19)0.0586 (7)
S60.90315 (13)0.1579 (3)0.43952 (19)0.0615 (7)
S70.87215 (12)0.4287 (3)0.54429 (18)0.0572 (7)
S80.99263 (12)0.4123 (4)0.45915 (18)0.0631 (8)
S90.96196 (12)0.6522 (4)0.54297 (18)0.0624 (7)
S101.05620 (15)0.7410 (5)0.5117 (2)0.0915 (11)
Cu10.83932 (5)0.17145 (14)0.48493 (6)0.0507 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (6)0.048 (5)0.051 (6)0.009 (5)0.026 (5)0.001 (5)
C20.050 (6)0.044 (6)0.058 (6)0.006 (5)0.025 (5)0.000 (5)
C30.061 (6)0.044 (6)0.058 (6)0.010 (5)0.036 (6)0.001 (5)
C40.047 (5)0.041 (5)0.041 (5)0.002 (5)0.023 (5)0.002 (4)
C50.034 (5)0.043 (5)0.033 (5)0.002 (5)0.008 (4)0.006 (4)
C60.051 (7)0.071 (8)0.049 (6)0.013 (6)0.020 (6)0.001 (6)
C70.102 (10)0.074 (8)0.076 (8)0.001 (8)0.060 (8)0.000 (7)
C80.136 (14)0.075 (9)0.138 (13)0.019 (10)0.093 (12)0.001 (9)
C90.068 (8)0.096 (9)0.060 (7)0.014 (7)0.037 (6)0.019 (7)
C100.087 (9)0.095 (10)0.098 (9)0.001 (9)0.061 (8)0.017 (8)
C110.088 (9)0.116 (11)0.076 (8)0.060 (9)0.050 (7)0.045 (8)
C120.123 (9)0.105 (8)0.125 (9)0.041 (7)0.077 (7)0.014 (7)
C130.056 (7)0.066 (7)0.047 (6)0.008 (6)0.023 (5)0.003 (5)
C140.078 (9)0.086 (9)0.072 (8)0.008 (8)0.042 (7)0.002 (7)
C150.050 (7)0.094 (10)0.085 (9)0.008 (8)0.008 (7)0.026 (8)
C160.092 (8)0.106 (8)0.146 (10)0.012 (7)0.067 (7)0.012 (7)
C170.063 (7)0.062 (7)0.053 (6)0.004 (6)0.030 (6)0.007 (5)
C180.092 (10)0.086 (10)0.116 (12)0.025 (8)0.044 (10)0.016 (9)
C190.051 (6)0.061 (7)0.058 (6)0.006 (6)0.023 (6)0.003 (6)
C200.075 (9)0.091 (11)0.114 (11)0.013 (8)0.036 (8)0.023 (9)
C210.085 (9)0.084 (9)0.053 (6)0.029 (8)0.025 (6)0.028 (7)
C220.118 (12)0.100 (12)0.118 (11)0.005 (10)0.078 (10)0.033 (9)
N10.047 (5)0.058 (5)0.051 (4)0.015 (5)0.024 (4)0.005 (5)
N20.046 (5)0.062 (6)0.045 (4)0.013 (5)0.011 (4)0.002 (5)
S10.072 (2)0.073 (2)0.083 (2)0.0134 (17)0.0473 (18)0.0065 (17)
S20.0545 (16)0.0547 (16)0.0771 (18)0.0008 (15)0.0336 (15)0.0046 (17)
S30.0602 (17)0.0401 (14)0.0748 (19)0.0004 (14)0.0365 (15)0.0093 (14)
S40.0534 (16)0.0411 (15)0.0809 (19)0.0038 (13)0.0324 (15)0.0080 (14)
S50.0653 (17)0.0386 (12)0.081 (2)0.0045 (14)0.0463 (16)0.0055 (14)
S60.076 (2)0.0484 (15)0.0716 (18)0.0095 (15)0.0480 (17)0.0126 (14)
S70.0607 (16)0.0487 (16)0.0685 (16)0.0138 (14)0.0398 (15)0.0142 (14)
S80.0596 (17)0.0710 (19)0.0632 (17)0.0045 (15)0.0370 (15)0.0041 (15)
S90.0614 (17)0.0583 (18)0.0699 (17)0.0186 (15)0.0381 (15)0.0160 (15)
S100.087 (3)0.109 (3)0.090 (2)0.043 (2)0.056 (2)0.018 (2)
Cu10.0531 (7)0.0400 (6)0.0526 (7)0.0053 (7)0.0256 (7)0.0014 (7)
Geometric parameters (Å, º) top
C1—S11.658 (10)C13—N11.514 (12)
C1—S31.724 (10)C13—H13A0.9700
C1—S21.725 (10)C13—H13B0.9700
C2—C31.353 (12)C14—H14A0.9600
C2—S41.736 (10)C14—H14B0.9600
C2—S21.744 (11)C14—H14C0.9600
C3—S51.730 (10)C15—N21.506 (15)
C3—S31.761 (10)C15—C161.519 (18)
C4—C51.360 (12)C15—H15A0.9700
C4—S81.738 (9)C15—H15B0.9700
C4—S61.740 (9)C16—H16A0.9600
C5—S71.713 (10)C16—H16B0.9600
C5—S91.754 (9)C16—H16C0.9600
C6—S101.672 (10)C17—N21.505 (12)
C6—S91.711 (10)C17—C181.509 (14)
C6—S81.715 (11)C17—H17A0.9700
C7—N11.485 (14)C17—H17B0.9700
C7—C81.523 (16)C18—H18A0.9600
C7—H7A0.9700C18—H18B0.9600
C7—H7B0.9700C18—H18C0.9600
C8—H8A0.9600C19—C201.497 (15)
C8—H8B0.9600C19—N21.527 (13)
C8—H8C0.9600C19—H19A0.9700
C9—N11.503 (13)C19—H19B0.9700
C9—C101.516 (15)C20—H20A0.9600
C9—H9A0.9700C20—H20B0.9600
C9—H9B0.9700C20—H20C0.9600
C10—H10A0.9600C21—C221.524 (17)
C10—H10B0.9600C21—N21.553 (13)
C10—H10C0.9600C21—H21A0.9700
C11—N11.504 (13)C21—H21B0.9700
C11—C121.539 (16)C22—H22A0.9600
C11—H11A0.9700C22—H22B0.9600
C11—H11B0.9700C22—H22C0.9600
C12—H12A0.9600S4—Cu12.292 (3)
C12—H12B0.9600S5—Cu12.259 (3)
C12—H12C0.9600S6—Cu12.288 (3)
C13—C141.512 (14)S7—Cu12.266 (3)
S1—C1—S3124.2 (6)C16—C15—H15B108.6
S1—C1—S2123.9 (6)H15A—C15—H15B107.6
S3—C1—S2111.9 (5)C15—C16—H16A109.5
C3—C2—S4123.7 (7)C15—C16—H16B109.5
C3—C2—S2116.0 (7)H16A—C16—H16B109.5
S4—C2—S2120.1 (6)C15—C16—H16C109.5
C2—C3—S5125.3 (7)H16A—C16—H16C109.5
C2—C3—S3114.8 (7)H16B—C16—H16C109.5
S5—C3—S3119.8 (6)N2—C17—C18115.6 (9)
C5—C4—S8117.1 (7)N2—C17—H17A108.4
C5—C4—S6122.5 (7)C18—C17—H17A108.4
S8—C4—S6120.4 (6)N2—C17—H17B108.4
C4—C5—S7125.5 (7)C18—C17—H17B108.4
C4—C5—S9113.5 (7)H17A—C17—H17B107.5
S7—C5—S9120.9 (6)C17—C18—H18A109.5
S10—C6—S9123.3 (7)C17—C18—H18B109.5
S10—C6—S8124.0 (6)H18A—C18—H18B109.5
S9—C6—S8112.6 (6)C17—C18—H18C109.5
N1—C7—C8117.0 (11)H18A—C18—H18C109.5
N1—C7—H7A108.1H18B—C18—H18C109.5
C8—C7—H7A108.1C20—C19—N2116.5 (9)
N1—C7—H7B108.1C20—C19—H19A108.2
C8—C7—H7B108.1N2—C19—H19A108.2
H7A—C7—H7B107.3C20—C19—H19B108.2
C7—C8—H8A109.5N2—C19—H19B108.2
C7—C8—H8B109.5H19A—C19—H19B107.3
H8A—C8—H8B109.5C19—C20—H20A109.5
C7—C8—H8C109.5C19—C20—H20B109.5
H8A—C8—H8C109.5H20A—C20—H20B109.5
H8B—C8—H8C109.5C19—C20—H20C109.5
N1—C9—C10116.1 (9)H20A—C20—H20C109.5
N1—C9—H9A108.3H20B—C20—H20C109.5
C10—C9—H9A108.3C22—C21—N2114.2 (9)
N1—C9—H9B108.3C22—C21—H21A108.7
C10—C9—H9B108.3N2—C21—H21A108.7
H9A—C9—H9B107.4C22—C21—H21B108.7
C9—C10—H10A109.5N2—C21—H21B108.7
C9—C10—H10B109.5H21A—C21—H21B107.6
H10A—C10—H10B109.5C21—C22—H22A109.5
C9—C10—H10C109.5C21—C22—H22B109.5
H10A—C10—H10C109.5H22A—C22—H22B109.5
H10B—C10—H10C109.5C21—C22—H22C109.5
N1—C11—C12112.7 (10)H22A—C22—H22C109.5
N1—C11—H11A109.1H22B—C22—H22C109.5
C12—C11—H11A109.1C7—N1—C9111.7 (8)
N1—C11—H11B109.1C7—N1—C11111.5 (9)
C12—C11—H11B109.1C9—N1—C11105.9 (8)
H11A—C11—H11B107.8C7—N1—C13105.9 (8)
C11—C12—H12A109.5C9—N1—C13110.6 (8)
C11—C12—H12B109.5C11—N1—C13111.4 (8)
H12A—C12—H12B109.5C17—N2—C15111.2 (9)
C11—C12—H12C109.5C17—N2—C19106.7 (7)
H12A—C12—H12C109.5C15—N2—C19111.0 (9)
H12B—C12—H12C109.5C17—N2—C21110.5 (8)
C14—C13—N1115.0 (9)C15—N2—C21107.2 (9)
C14—C13—H13A108.5C19—N2—C21110.4 (8)
N1—C13—H13A108.5C1—S2—C298.5 (5)
C14—C13—H13B108.5C1—S3—C398.4 (5)
N1—C13—H13B108.5C2—S4—Cu198.5 (4)
H13A—C13—H13B107.5C3—S5—Cu198.8 (4)
C13—C14—H14A109.5C4—S6—Cu199.6 (3)
C13—C14—H14B109.5C5—S7—Cu199.6 (3)
H14A—C14—H14B109.5C6—S8—C497.8 (5)
C13—C14—H14C109.5C6—S9—C599.0 (5)
H14A—C14—H14C109.5S5—Cu1—S7150.94 (12)
H14B—C14—H14C109.5S5—Cu1—S694.14 (10)
N2—C15—C16114.6 (10)S7—Cu1—S692.66 (10)
N2—C15—H15A108.6S5—Cu1—S493.53 (10)
C16—C15—H15A108.6S7—Cu1—S493.00 (10)
N2—C15—H15B108.6S6—Cu1—S4153.19 (11)
S4—C2—C3—S50.4 (13)C3—C2—S2—C10.2 (9)
S2—C2—C3—S5174.0 (6)S4—C2—S2—C1174.8 (6)
S4—C2—C3—S3178.4 (6)S1—C1—S3—C3175.7 (7)
S2—C2—C3—S34.1 (10)S2—C1—S3—C35.4 (6)
S8—C4—C5—S7176.6 (5)C2—C3—S3—C15.8 (9)
S6—C4—C5—S74.6 (11)S5—C3—S3—C1172.3 (6)
S8—C4—C5—S90.7 (9)C3—C2—S4—Cu12.6 (9)
S6—C4—C5—S9178.1 (5)S2—C2—S4—Cu1171.6 (5)
C8—C7—N1—C964.1 (13)C2—C3—S5—Cu12.1 (9)
C8—C7—N1—C1154.1 (13)S3—C3—S5—Cu1175.9 (5)
C8—C7—N1—C13175.4 (10)C5—C4—S6—Cu11.6 (8)
C10—C9—N1—C760.6 (13)S8—C4—S6—Cu1179.6 (5)
C10—C9—N1—C11177.8 (10)C4—C5—S7—Cu14.5 (8)
C10—C9—N1—C1357.0 (12)S9—C5—S7—Cu1178.3 (4)
C12—C11—N1—C757.2 (14)S10—C6—S8—C4178.8 (7)
C12—C11—N1—C9178.9 (10)S9—C6—S8—C41.5 (6)
C12—C11—N1—C1360.8 (13)C5—C4—S8—C60.5 (8)
C14—C13—N1—C7176.8 (9)S6—C4—S8—C6179.3 (6)
C14—C13—N1—C955.6 (11)S10—C6—S9—C5179.2 (6)
C14—C13—N1—C1161.8 (12)S8—C6—S9—C51.8 (6)
C18—C17—N2—C1562.3 (13)C4—C5—S9—C61.6 (7)
C18—C17—N2—C19176.6 (10)S7—C5—S9—C6175.9 (6)
C18—C17—N2—C2156.5 (13)C3—S5—Cu1—S799.9 (4)
C16—C15—N2—C1765.2 (14)C3—S5—Cu1—S6157.0 (4)
C16—C15—N2—C1953.4 (14)C3—S5—Cu1—S42.7 (4)
C16—C15—N2—C21174.0 (11)C5—S7—Cu1—S5105.9 (3)
C20—C19—N2—C17174.9 (10)C5—S7—Cu1—S62.4 (3)
C20—C19—N2—C1553.7 (13)C5—S7—Cu1—S4151.4 (3)
C20—C19—N2—C2165.0 (13)C4—S6—Cu1—S5152.6 (3)
C22—C21—N2—C1751.9 (13)C4—S6—Cu1—S70.9 (3)
C22—C21—N2—C15173.1 (10)C4—S6—Cu1—S4101.2 (4)
C22—C21—N2—C1965.9 (12)C2—S4—Cu1—S52.9 (4)
S1—C1—S2—C2177.5 (7)C2—S4—Cu1—S7148.8 (4)
S3—C1—S2—C23.7 (6)C2—S4—Cu1—S6109.3 (4)
 

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