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In the title complex, (C24H20P)2[Cu(C3S5)2], the CuII ion is coordinated by four S atoms from two 2-thioxo-1,3-dithiole-4,5-dithiol­ate ligands in a distorted planar geometry. The anion possesses C2 symmetry with the metal ion lying on a twofold axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046290/hy2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046290/hy2027Isup2.hkl
Contains datablock I

CCDC reference: 630010

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.047
  • wR factor = 0.137
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: WinGX (Farrugia,1999).

bis(tetraphenylphosphonium) bis(2-thioxo-1,3-dithiole-4,5-dithiolato)cuprate(II) top
Crystal data top
(C24H20P)2[Cu(C3S5)2]F(000) = 2332
Mr = 1134.94Dx = 1.436 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 38 reflections
a = 20.255 (3) Åθ = 4.7–12.5°
b = 12.6669 (17) ŵ = 0.91 mm1
c = 20.499 (2) ÅT = 295 K
β = 93.772 (10)°Prism, dark red
V = 5248.2 (12) Å30.36 × 0.34 × 0.30 mm
Z = 4
Data collection top
Bruker P4
diffractometer
3172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω scansh = 241
Absorption correction: ψ scan
(XSCANS; Bruker,1996)
k = 151
Tmin = 0.710, Tmax = 0.765l = 2525
6171 measured reflections3 standard reflections every 97 reflections
5167 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0617P)2 + 1.9578P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5167 reflectionsΔρmax = 0.41 e Å3
304 parametersΔρmin = 0.56 e Å3
1 restraintExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (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
C10.6646 (2)0.4692 (3)0.9726 (2)0.0538 (11)
C20.56219 (19)0.5035 (3)0.88999 (19)0.0454 (10)
C30.61538 (19)0.5208 (3)0.85513 (19)0.0448 (10)
C40.6268 (2)0.1882 (5)0.8584 (3)0.0752 (15)
H40.67120.20350.85430.090*
C50.5802 (2)0.2542 (4)0.8311 (3)0.0696 (14)
H50.59260.31240.80710.083*
C60.5131 (2)0.2344 (4)0.8393 (2)0.0590 (12)
H60.48080.27960.82100.071*
C70.4955 (2)0.1473 (3)0.8745 (2)0.0501 (10)
C80.5438 (2)0.0788 (4)0.8997 (3)0.0749 (15)
H80.53190.01840.92200.090*
C90.6103 (2)0.0999 (5)0.8918 (3)0.0824 (17)
H90.64300.05450.90900.099*
C100.4001 (2)0.1600 (3)0.9755 (2)0.0479 (10)
C110.4520 (2)0.1991 (4)1.0166 (2)0.0603 (12)
H110.49460.20361.00240.072*
C120.4388 (3)0.2313 (4)1.0795 (2)0.0724 (14)
H120.47290.25801.10730.087*
C130.3769 (3)0.2243 (4)1.1006 (2)0.0717 (14)
H130.36910.24441.14300.086*
C140.3258 (3)0.1879 (4)1.0596 (3)0.0720 (14)
H140.28330.18471.07410.086*
C150.3368 (2)0.1562 (4)0.9977 (2)0.0595 (12)
H150.30180.13190.97020.071*
C160.39723 (19)0.0171 (3)0.8806 (2)0.0491 (10)
C170.3675 (2)0.0773 (4)0.9259 (2)0.0607 (12)
H170.35270.04580.96320.073*
C180.3593 (3)0.1852 (4)0.9161 (3)0.0717 (15)
H180.34050.22610.94770.086*
C190.3783 (3)0.2305 (4)0.8615 (3)0.0825 (17)
H190.37150.30250.85490.099*
C200.4076 (3)0.1720 (5)0.8149 (3)0.0813 (17)
H200.42040.20440.77710.098*
C210.4181 (2)0.0639 (4)0.8242 (2)0.0694 (14)
H210.43870.02410.79320.083*
C220.3529 (2)0.1981 (4)0.8436 (2)0.0508 (11)
C230.3504 (2)0.3067 (4)0.8533 (2)0.0612 (12)
H230.37960.33870.88410.073*
C240.3047 (2)0.3664 (4)0.8173 (3)0.0762 (16)
H240.30320.43910.82320.091*
C250.2609 (2)0.3176 (6)0.7724 (3)0.0845 (18)
H250.23010.35830.74790.101*
C260.2619 (2)0.2117 (5)0.7632 (3)0.0764 (16)
H260.23150.18030.73330.092*
C270.3080 (2)0.1506 (4)0.7983 (2)0.0632 (13)
H270.30900.07790.79180.076*
P10.41176 (5)0.12196 (9)0.89291 (5)0.0461 (3)
S10.71469 (6)0.44289 (12)1.03735 (7)0.0756 (4)
S20.57977 (5)0.46807 (11)0.97176 (5)0.0593 (3)
S30.69188 (5)0.50274 (10)0.89724 (6)0.0570 (3)
S40.48114 (5)0.50977 (10)0.85744 (5)0.0526 (3)
S50.61057 (5)0.55640 (10)0.77355 (5)0.0582 (3)
Cu10.50000.53565 (6)0.75000.0440 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (3)0.048 (3)0.057 (3)0.007 (2)0.004 (2)0.003 (2)
C20.042 (2)0.052 (3)0.042 (2)0.0049 (19)0.0000 (18)0.0052 (19)
C30.042 (2)0.046 (2)0.045 (2)0.0084 (19)0.0018 (18)0.0023 (19)
C40.048 (3)0.098 (4)0.080 (4)0.004 (3)0.011 (3)0.000 (3)
C50.062 (3)0.066 (3)0.084 (4)0.015 (3)0.029 (3)0.004 (3)
C60.063 (3)0.050 (3)0.063 (3)0.005 (2)0.003 (2)0.005 (2)
C70.046 (2)0.051 (3)0.053 (2)0.006 (2)0.001 (2)0.004 (2)
C80.064 (3)0.073 (4)0.088 (4)0.002 (3)0.007 (3)0.027 (3)
C90.053 (3)0.111 (5)0.084 (4)0.007 (3)0.007 (3)0.017 (4)
C100.052 (2)0.039 (2)0.052 (2)0.001 (2)0.003 (2)0.002 (2)
C110.048 (3)0.057 (3)0.075 (3)0.002 (2)0.007 (2)0.006 (3)
C120.086 (3)0.064 (3)0.064 (3)0.001 (3)0.021 (3)0.015 (3)
C130.092 (4)0.064 (3)0.059 (3)0.006 (3)0.006 (3)0.009 (3)
C140.073 (3)0.071 (4)0.073 (3)0.007 (3)0.018 (3)0.010 (3)
C150.051 (3)0.065 (3)0.063 (3)0.007 (2)0.009 (2)0.009 (2)
C160.042 (2)0.050 (3)0.054 (2)0.000 (2)0.0030 (19)0.004 (2)
C170.072 (3)0.046 (3)0.064 (3)0.005 (2)0.000 (2)0.002 (2)
C180.076 (4)0.050 (3)0.087 (4)0.014 (3)0.009 (3)0.006 (3)
C190.080 (4)0.054 (3)0.108 (5)0.000 (3)0.032 (4)0.010 (3)
C200.077 (4)0.077 (4)0.089 (4)0.010 (3)0.007 (3)0.038 (3)
C210.068 (3)0.076 (4)0.064 (3)0.012 (3)0.006 (3)0.016 (3)
C220.042 (2)0.060 (3)0.050 (2)0.009 (2)0.0017 (19)0.011 (2)
C230.051 (3)0.061 (3)0.072 (3)0.001 (2)0.001 (2)0.011 (3)
C240.057 (3)0.067 (4)0.106 (4)0.005 (3)0.020 (3)0.025 (3)
C250.045 (3)0.110 (5)0.099 (4)0.009 (3)0.007 (3)0.045 (4)
C260.039 (3)0.114 (5)0.074 (3)0.007 (3)0.009 (2)0.027 (3)
C270.050 (3)0.076 (3)0.063 (3)0.010 (3)0.001 (2)0.010 (3)
P10.0393 (6)0.0470 (6)0.0516 (6)0.0061 (5)0.0003 (5)0.0037 (5)
S10.0562 (7)0.0977 (11)0.0699 (8)0.0153 (7)0.0189 (6)0.0261 (8)
S20.0443 (6)0.0877 (9)0.0455 (6)0.0039 (6)0.0001 (5)0.0108 (6)
S30.0389 (6)0.0737 (8)0.0581 (7)0.0078 (6)0.0001 (5)0.0057 (6)
S40.0377 (5)0.0731 (8)0.0471 (6)0.0032 (5)0.0025 (4)0.0048 (6)
S50.0510 (6)0.0801 (9)0.0434 (6)0.0155 (6)0.0035 (5)0.0053 (6)
Cu10.0452 (4)0.0435 (4)0.0429 (4)0.0000.0008 (3)0.000
Geometric parameters (Å, º) top
C1—S11.650 (4)C14—H140.9300
C1—S21.717 (4)C15—H150.9300
C1—S31.728 (4)C16—C171.370 (6)
C2—C31.349 (5)C16—C211.391 (6)
C2—S41.733 (4)C16—P11.801 (4)
C2—S21.749 (4)C17—C181.390 (6)
C3—S51.728 (4)C17—H170.9300
C3—S31.739 (4)C18—C191.336 (7)
C4—C51.354 (7)C18—H180.9300
C4—C91.364 (7)C19—C201.374 (8)
C4—H40.9300C19—H190.9300
C5—C61.402 (6)C20—C211.396 (7)
C5—H50.9300C20—H200.9300
C6—C71.378 (6)C21—H210.9300
C6—H60.9300C22—C231.391 (6)
C7—C81.383 (6)C22—C271.393 (6)
C7—P11.791 (4)C22—P11.794 (4)
C8—C91.393 (6)C23—C241.372 (6)
C8—H80.9300C23—H230.9300
C9—H90.9300C24—C251.382 (7)
C10—C151.389 (6)C24—H240.9300
C10—C111.394 (6)C25—C261.355 (8)
C10—P11.791 (4)C25—H250.9300
C11—C121.394 (6)C26—C271.379 (6)
C11—H110.9300C26—H260.9300
C12—C131.356 (7)C27—H270.9300
C12—H120.9300S4—Cu12.2837 (11)
C13—C141.369 (7)S5—Cu12.2751 (11)
C13—H130.9300Cu1—S5i2.2751 (11)
C14—C151.363 (6)Cu1—S4i2.2837 (11)
S1—C1—S2124.7 (3)C16—C17—H17119.9
S1—C1—S3123.6 (3)C18—C17—H17119.9
S2—C1—S3111.8 (2)C19—C18—C17120.4 (5)
C3—C2—S4123.9 (3)C19—C18—H18119.8
C3—C2—S2115.5 (3)C17—C18—H18119.8
S4—C2—S2120.6 (2)C18—C19—C20120.7 (5)
C2—C3—S5124.0 (3)C18—C19—H19119.7
C2—C3—S3115.6 (3)C20—C19—H19119.7
S5—C3—S3120.4 (2)C19—C20—C21120.3 (5)
C5—C4—C9121.7 (5)C19—C20—H20119.8
C5—C4—H4119.1C21—C20—H20119.8
C9—C4—H4119.1C16—C21—C20118.6 (5)
C4—C5—C6119.6 (5)C16—C21—H21120.7
C4—C5—H5120.2C20—C21—H21120.7
C6—C5—H5120.2C23—C22—C27119.6 (4)
C7—C6—C5119.5 (5)C23—C22—P1118.7 (3)
C7—C6—H6120.2C27—C22—P1121.6 (4)
C5—C6—H6120.2C24—C23—C22119.9 (5)
C6—C7—C8119.8 (4)C24—C23—H23120.1
C6—C7—P1122.4 (3)C22—C23—H23120.1
C8—C7—P1117.7 (3)C23—C24—C25119.5 (5)
C7—C8—C9120.1 (5)C23—C24—H24120.3
C7—C8—H8120.0C25—C24—H24120.3
C9—C8—H8120.0C26—C25—C24121.3 (5)
C4—C9—C8119.1 (5)C26—C25—H25119.3
C4—C9—H9120.4C24—C25—H25119.3
C8—C9—H9120.4C25—C26—C27120.0 (5)
C15—C10—C11119.4 (4)C25—C26—H26120.0
C15—C10—P1118.8 (3)C27—C26—H26120.0
C11—C10—P1121.7 (3)C26—C27—C22119.6 (5)
C12—C11—C10118.6 (4)C26—C27—H27120.2
C12—C11—H11120.7C22—C27—H27120.2
C10—C11—H11120.7C7—P1—C10109.7 (2)
C13—C12—C11121.0 (5)C7—P1—C22112.9 (2)
C13—C12—H12119.5C10—P1—C22105.3 (2)
C11—C12—H12119.5C7—P1—C16107.1 (2)
C12—C13—C14120.3 (5)C10—P1—C16111.4 (2)
C12—C13—H13119.9C22—P1—C16110.5 (2)
C14—C13—H13119.9C1—S2—C298.5 (2)
C15—C14—C13120.4 (5)C1—S3—C398.6 (2)
C15—C14—H14119.8C2—S4—Cu199.41 (14)
C13—C14—H14119.8C3—S5—Cu199.63 (13)
C14—C15—C10120.4 (4)S5i—Cu1—S5166.73 (7)
C14—C15—H15119.8S5i—Cu1—S4i92.10 (4)
C10—C15—H15119.8S5—Cu1—S4i89.80 (4)
C17—C16—C21119.8 (4)S5i—Cu1—S489.80 (4)
C17—C16—P1121.6 (3)S5—Cu1—S492.10 (4)
C21—C16—P1118.5 (4)S4i—Cu1—S4163.49 (7)
C16—C17—C18120.2 (5)
S4—C2—C3—S52.3 (6)C8—C7—P1—C22167.3 (4)
S2—C2—C3—S5179.9 (2)C6—C7—P1—C16137.8 (4)
S4—C2—C3—S3176.5 (2)C8—C7—P1—C1645.4 (4)
S2—C2—C3—S31.1 (5)C15—C10—P1—C7173.9 (4)
C9—C4—C5—C62.6 (8)C11—C10—P1—C72.2 (4)
C4—C5—C6—C70.6 (7)C15—C10—P1—C2252.2 (4)
C5—C6—C7—C82.0 (7)C11—C10—P1—C22123.9 (4)
C5—C6—C7—P1174.8 (4)C15—C10—P1—C1667.7 (4)
C6—C7—C8—C92.6 (8)C11—C10—P1—C16116.2 (4)
P1—C7—C8—C9174.3 (4)C23—C22—P1—C769.0 (4)
C5—C4—C9—C82.0 (9)C27—C22—P1—C7114.1 (4)
C7—C8—C9—C40.7 (8)C23—C22—P1—C1050.6 (4)
C15—C10—C11—C121.2 (7)C27—C22—P1—C10126.3 (4)
P1—C10—C11—C12177.3 (4)C23—C22—P1—C16171.1 (3)
C10—C11—C12—C130.4 (8)C27—C22—P1—C165.9 (4)
C11—C12—C13—C141.7 (8)C17—C16—P1—C7132.8 (4)
C12—C13—C14—C151.3 (8)C21—C16—P1—C746.0 (4)
C13—C14—C15—C100.4 (8)C17—C16—P1—C1012.9 (4)
C11—C10—C15—C141.6 (7)C21—C16—P1—C10165.9 (4)
P1—C10—C15—C14177.8 (4)C17—C16—P1—C22103.8 (4)
C21—C16—C17—C181.3 (7)C21—C16—P1—C2277.4 (4)
P1—C16—C17—C18177.5 (4)S1—C1—S2—C2179.4 (3)
C16—C17—C18—C192.4 (8)S3—C1—S2—C20.0 (3)
C17—C18—C19—C201.6 (8)C3—C2—S2—C10.7 (4)
C18—C19—C20—C210.2 (8)S4—C2—S2—C1176.9 (3)
C17—C16—C21—C200.5 (7)S1—C1—S3—C3179.0 (3)
P1—C16—C21—C20179.3 (4)S2—C1—S3—C30.4 (3)
C19—C20—C21—C161.2 (8)C2—C3—S3—C10.9 (4)
C27—C22—C23—C241.3 (7)S5—C3—S3—C1179.8 (3)
P1—C22—C23—C24178.4 (3)C3—C2—S4—Cu15.2 (4)
C22—C23—C24—C250.9 (7)S2—C2—S4—Cu1172.2 (2)
C23—C24—C25—C260.3 (8)C2—C3—S5—Cu18.4 (4)
C24—C25—C26—C271.1 (8)S3—C3—S5—Cu1170.4 (2)
C25—C26—C27—C220.6 (7)C3—S5—Cu1—S5i106.61 (14)
C23—C22—C27—C260.6 (7)C3—S5—Cu1—S4i155.06 (15)
P1—C22—C27—C26177.5 (3)C3—S5—Cu1—S48.54 (15)
C6—C7—P1—C10101.2 (4)C2—S4—Cu1—S5i174.58 (15)
C8—C7—P1—C1075.6 (4)C2—S4—Cu1—S57.71 (15)
C6—C7—P1—C2215.9 (5)C2—S4—Cu1—S4i88.69 (14)
Symmetry code: (i) x+1, y, z+3/2.
 

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