Bis(tetra­phenyl­phospho­nium) bis­(2-thioxo-1,3-dithiole-4,5-dithiol­ato)cuprate(II)

In the title complex, (C₂₄H₂₀P)₂[Cu(C₃S₅)₂], the Cu^II 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.

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

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Computing details

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)

Crystal data

(C24H20P)2[Cu(C3S5)2]	F(000) = 2332
Mr = 1134.94	Dx = 1.436 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 38 reflections
a = 20.255 (3) Å	θ = 4.7–12.5°
b = 12.6669 (17) Å	µ = 0.91 mm^−1
c = 20.499 (2) Å	T = 295 K
β = 93.772 (10)°	Prism, dark red
V = 5248.2 (12) Å^3	0.36 × 0.34 × 0.30 mm
Z = 4

Data collection

Bruker P4 diffractometer	3172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω scans	h = −24→1
Absorption correction: ψ scan (XSCANS; Bruker,1996)	k = −15→1
Tmin = 0.710, Tmax = 0.765	l = −25→25
6171 measured reflections	3 standard reflections every 97 reflections
5167 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 1.9578P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5167 reflections	Δρmax = 0.41 e Å^−3
304 parameters	Δρmin = −0.56 e Å^−3
1 restraint	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6646 (2)	0.4692 (3)	0.9726 (2)	0.0538 (11)
C2	0.56219 (19)	0.5035 (3)	0.88999 (19)	0.0454 (10)
C3	0.61538 (19)	0.5208 (3)	0.85513 (19)	0.0448 (10)
C4	0.6268 (2)	0.1882 (5)	0.8584 (3)	0.0752 (15)
H4	0.6712	0.2035	0.8543	0.090*
C5	0.5802 (2)	0.2542 (4)	0.8311 (3)	0.0696 (14)
H5	0.5926	0.3124	0.8071	0.083*
C6	0.5131 (2)	0.2344 (4)	0.8393 (2)	0.0590 (12)
H6	0.4808	0.2796	0.8210	0.071*
C7	0.4955 (2)	0.1473 (3)	0.8745 (2)	0.0501 (10)
C8	0.5438 (2)	0.0788 (4)	0.8997 (3)	0.0749 (15)
H8	0.5319	0.0184	0.9220	0.090*
C9	0.6103 (2)	0.0999 (5)	0.8918 (3)	0.0824 (17)
H9	0.6430	0.0545	0.9090	0.099*
C10	0.4001 (2)	0.1600 (3)	0.9755 (2)	0.0479 (10)
C11	0.4520 (2)	0.1991 (4)	1.0166 (2)	0.0603 (12)
H11	0.4946	0.2036	1.0024	0.072*
C12	0.4388 (3)	0.2313 (4)	1.0795 (2)	0.0724 (14)
H12	0.4729	0.2580	1.1073	0.087*
C13	0.3769 (3)	0.2243 (4)	1.1006 (2)	0.0717 (14)
H13	0.3691	0.2444	1.1430	0.086*
C14	0.3258 (3)	0.1879 (4)	1.0596 (3)	0.0720 (14)
H14	0.2833	0.1847	1.0741	0.086*
C15	0.3368 (2)	0.1562 (4)	0.9977 (2)	0.0595 (12)
H15	0.3018	0.1319	0.9702	0.071*
C16	0.39723 (19)	−0.0171 (3)	0.8806 (2)	0.0491 (10)
C17	0.3675 (2)	−0.0773 (4)	0.9259 (2)	0.0607 (12)
H17	0.3527	−0.0458	0.9632	0.073*
C18	0.3593 (3)	−0.1852 (4)	0.9161 (3)	0.0717 (15)
H18	0.3405	−0.2261	0.9477	0.086*
C19	0.3783 (3)	−0.2305 (4)	0.8615 (3)	0.0825 (17)
H19	0.3715	−0.3025	0.8549	0.099*
C20	0.4076 (3)	−0.1720 (5)	0.8149 (3)	0.0813 (17)
H20	0.4204	−0.2044	0.7771	0.098*
C21	0.4181 (2)	−0.0639 (4)	0.8242 (2)	0.0694 (14)
H21	0.4387	−0.0241	0.7932	0.083*
C22	0.3529 (2)	0.1981 (4)	0.8436 (2)	0.0508 (11)
C23	0.3504 (2)	0.3067 (4)	0.8533 (2)	0.0612 (12)
H23	0.3796	0.3387	0.8841	0.073*
C24	0.3047 (2)	0.3664 (4)	0.8173 (3)	0.0762 (16)
H24	0.3032	0.4391	0.8232	0.091*
C25	0.2609 (2)	0.3176 (6)	0.7724 (3)	0.0845 (18)
H25	0.2301	0.3583	0.7479	0.101*
C26	0.2619 (2)	0.2117 (5)	0.7632 (3)	0.0764 (16)
H26	0.2315	0.1803	0.7333	0.092*
C27	0.3080 (2)	0.1506 (4)	0.7983 (2)	0.0632 (13)
H27	0.3090	0.0779	0.7918	0.076*
P1	0.41176 (5)	0.12196 (9)	0.89291 (5)	0.0461 (3)
S1	0.71469 (6)	0.44289 (12)	1.03735 (7)	0.0756 (4)
S2	0.57977 (5)	0.46807 (11)	0.97176 (5)	0.0593 (3)
S3	0.69188 (5)	0.50274 (10)	0.89724 (6)	0.0570 (3)
S4	0.48114 (5)	0.50977 (10)	0.85744 (5)	0.0526 (3)
S5	0.61057 (5)	0.55640 (10)	0.77355 (5)	0.0582 (3)
Cu1	0.5000	0.53565 (6)	0.7500	0.0440 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.055 (3)	0.048 (3)	0.057 (3)	−0.007 (2)	−0.004 (2)	0.003 (2)
C2	0.042 (2)	0.052 (3)	0.042 (2)	−0.0049 (19)	0.0000 (18)	0.0052 (19)
C3	0.042 (2)	0.046 (2)	0.045 (2)	−0.0084 (19)	−0.0018 (18)	−0.0023 (19)
C4	0.048 (3)	0.098 (4)	0.080 (4)	−0.004 (3)	0.011 (3)	0.000 (3)
C5	0.062 (3)	0.066 (3)	0.084 (4)	−0.015 (3)	0.029 (3)	−0.004 (3)
C6	0.063 (3)	0.050 (3)	0.063 (3)	−0.005 (2)	0.003 (2)	0.005 (2)
C7	0.046 (2)	0.051 (3)	0.053 (2)	−0.006 (2)	0.001 (2)	0.004 (2)
C8	0.064 (3)	0.073 (4)	0.088 (4)	0.002 (3)	0.007 (3)	0.027 (3)
C9	0.053 (3)	0.111 (5)	0.084 (4)	0.007 (3)	0.007 (3)	0.017 (4)
C10	0.052 (2)	0.039 (2)	0.052 (2)	−0.001 (2)	−0.003 (2)	−0.002 (2)
C11	0.048 (3)	0.057 (3)	0.075 (3)	0.002 (2)	−0.007 (2)	−0.006 (3)
C12	0.086 (3)	0.064 (3)	0.064 (3)	−0.001 (3)	−0.021 (3)	−0.015 (3)
C13	0.092 (4)	0.064 (3)	0.059 (3)	0.006 (3)	0.006 (3)	−0.009 (3)
C14	0.073 (3)	0.071 (4)	0.073 (3)	−0.007 (3)	0.018 (3)	−0.010 (3)
C15	0.051 (3)	0.065 (3)	0.063 (3)	−0.007 (2)	0.009 (2)	−0.009 (2)
C16	0.042 (2)	0.050 (3)	0.054 (2)	0.000 (2)	−0.0030 (19)	−0.004 (2)
C17	0.072 (3)	0.046 (3)	0.064 (3)	−0.005 (2)	0.000 (2)	0.002 (2)
C18	0.076 (4)	0.050 (3)	0.087 (4)	−0.014 (3)	−0.009 (3)	0.006 (3)
C19	0.080 (4)	0.054 (3)	0.108 (5)	0.000 (3)	−0.032 (4)	−0.010 (3)
C20	0.077 (4)	0.077 (4)	0.089 (4)	0.010 (3)	−0.007 (3)	−0.038 (3)
C21	0.068 (3)	0.076 (4)	0.064 (3)	−0.012 (3)	0.006 (3)	−0.016 (3)
C22	0.042 (2)	0.060 (3)	0.050 (2)	−0.009 (2)	0.0017 (19)	0.011 (2)
C23	0.051 (3)	0.061 (3)	0.072 (3)	0.001 (2)	0.001 (2)	0.011 (3)
C24	0.057 (3)	0.067 (4)	0.106 (4)	0.005 (3)	0.020 (3)	0.025 (3)
C25	0.045 (3)	0.110 (5)	0.099 (4)	0.009 (3)	0.007 (3)	0.045 (4)
C26	0.039 (3)	0.114 (5)	0.074 (3)	−0.007 (3)	−0.009 (2)	0.027 (3)
C27	0.050 (3)	0.076 (3)	0.063 (3)	−0.010 (3)	0.001 (2)	0.010 (3)
P1	0.0393 (6)	0.0470 (6)	0.0516 (6)	−0.0061 (5)	0.0003 (5)	0.0037 (5)
S1	0.0562 (7)	0.0977 (11)	0.0699 (8)	−0.0153 (7)	−0.0189 (6)	0.0261 (8)
S2	0.0443 (6)	0.0877 (9)	0.0455 (6)	−0.0039 (6)	0.0001 (5)	0.0108 (6)
S3	0.0389 (6)	0.0737 (8)	0.0581 (7)	−0.0078 (6)	0.0001 (5)	0.0057 (6)
S4	0.0377 (5)	0.0731 (8)	0.0471 (6)	0.0032 (5)	0.0025 (4)	0.0048 (6)
S5	0.0510 (6)	0.0801 (9)	0.0434 (6)	−0.0155 (6)	0.0035 (5)	0.0053 (6)
Cu1	0.0452 (4)	0.0435 (4)	0.0429 (4)	0.000	0.0008 (3)	0.000

Geometric parameters (Å, º)

C1—S1	1.650 (4)	C14—H14	0.9300
C1—S2	1.717 (4)	C15—H15	0.9300
C1—S3	1.728 (4)	C16—C17	1.370 (6)
C2—C3	1.349 (5)	C16—C21	1.391 (6)
C2—S4	1.733 (4)	C16—P1	1.801 (4)
C2—S2	1.749 (4)	C17—C18	1.390 (6)
C3—S5	1.728 (4)	C17—H17	0.9300
C3—S3	1.739 (4)	C18—C19	1.336 (7)
C4—C5	1.354 (7)	C18—H18	0.9300
C4—C9	1.364 (7)	C19—C20	1.374 (8)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.402 (6)	C20—C21	1.396 (7)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.378 (6)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.391 (6)
C7—C8	1.383 (6)	C22—C27	1.393 (6)
C7—P1	1.791 (4)	C22—P1	1.794 (4)
C8—C9	1.393 (6)	C23—C24	1.372 (6)
C8—H8	0.9300	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.382 (7)
C10—C15	1.389 (6)	C24—H24	0.9300
C10—C11	1.394 (6)	C25—C26	1.355 (8)
C10—P1	1.791 (4)	C25—H25	0.9300
C11—C12	1.394 (6)	C26—C27	1.379 (6)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.356 (7)	C27—H27	0.9300
C12—H12	0.9300	S4—Cu1	2.2837 (11)
C13—C14	1.369 (7)	S5—Cu1	2.2751 (11)
C13—H13	0.9300	Cu1—S5^i	2.2751 (11)
C14—C15	1.363 (6)	Cu1—S4^i	2.2837 (11)
S1—C1—S2	124.7 (3)	C16—C17—H17	119.9
S1—C1—S3	123.6 (3)	C18—C17—H17	119.9
S2—C1—S3	111.8 (2)	C19—C18—C17	120.4 (5)
C3—C2—S4	123.9 (3)	C19—C18—H18	119.8
C3—C2—S2	115.5 (3)	C17—C18—H18	119.8
S4—C2—S2	120.6 (2)	C18—C19—C20	120.7 (5)
C2—C3—S5	124.0 (3)	C18—C19—H19	119.7
C2—C3—S3	115.6 (3)	C20—C19—H19	119.7
S5—C3—S3	120.4 (2)	C19—C20—C21	120.3 (5)
C5—C4—C9	121.7 (5)	C19—C20—H20	119.8
C5—C4—H4	119.1	C21—C20—H20	119.8
C9—C4—H4	119.1	C16—C21—C20	118.6 (5)
C4—C5—C6	119.6 (5)	C16—C21—H21	120.7
C4—C5—H5	120.2	C20—C21—H21	120.7
C6—C5—H5	120.2	C23—C22—C27	119.6 (4)
C7—C6—C5	119.5 (5)	C23—C22—P1	118.7 (3)
C7—C6—H6	120.2	C27—C22—P1	121.6 (4)
C5—C6—H6	120.2	C24—C23—C22	119.9 (5)
C6—C7—C8	119.8 (4)	C24—C23—H23	120.1
C6—C7—P1	122.4 (3)	C22—C23—H23	120.1
C8—C7—P1	117.7 (3)	C23—C24—C25	119.5 (5)
C7—C8—C9	120.1 (5)	C23—C24—H24	120.3
C7—C8—H8	120.0	C25—C24—H24	120.3
C9—C8—H8	120.0	C26—C25—C24	121.3 (5)
C4—C9—C8	119.1 (5)	C26—C25—H25	119.3
C4—C9—H9	120.4	C24—C25—H25	119.3
C8—C9—H9	120.4	C25—C26—C27	120.0 (5)
C15—C10—C11	119.4 (4)	C25—C26—H26	120.0
C15—C10—P1	118.8 (3)	C27—C26—H26	120.0
C11—C10—P1	121.7 (3)	C26—C27—C22	119.6 (5)
C12—C11—C10	118.6 (4)	C26—C27—H27	120.2
C12—C11—H11	120.7	C22—C27—H27	120.2
C10—C11—H11	120.7	C7—P1—C10	109.7 (2)
C13—C12—C11	121.0 (5)	C7—P1—C22	112.9 (2)
C13—C12—H12	119.5	C10—P1—C22	105.3 (2)
C11—C12—H12	119.5	C7—P1—C16	107.1 (2)
C12—C13—C14	120.3 (5)	C10—P1—C16	111.4 (2)
C12—C13—H13	119.9	C22—P1—C16	110.5 (2)
C14—C13—H13	119.9	C1—S2—C2	98.5 (2)
C15—C14—C13	120.4 (5)	C1—S3—C3	98.6 (2)
C15—C14—H14	119.8	C2—S4—Cu1	99.41 (14)
C13—C14—H14	119.8	C3—S5—Cu1	99.63 (13)
C14—C15—C10	120.4 (4)	S5^i—Cu1—S5	166.73 (7)
C14—C15—H15	119.8	S5^i—Cu1—S4^i	92.10 (4)
C10—C15—H15	119.8	S5—Cu1—S4^i	89.80 (4)
C17—C16—C21	119.8 (4)	S5^i—Cu1—S4	89.80 (4)
C17—C16—P1	121.6 (3)	S5—Cu1—S4	92.10 (4)
C21—C16—P1	118.5 (4)	S4^i—Cu1—S4	163.49 (7)
C16—C17—C18	120.2 (5)
S4—C2—C3—S5	2.3 (6)	C8—C7—P1—C22	−167.3 (4)
S2—C2—C3—S5	179.9 (2)	C6—C7—P1—C16	137.8 (4)
S4—C2—C3—S3	−176.5 (2)	C8—C7—P1—C16	−45.4 (4)
S2—C2—C3—S3	1.1 (5)	C15—C10—P1—C7	173.9 (4)
C9—C4—C5—C6	2.6 (8)	C11—C10—P1—C7	−2.2 (4)
C4—C5—C6—C7	−0.6 (7)	C15—C10—P1—C22	52.2 (4)
C5—C6—C7—C8	−2.0 (7)	C11—C10—P1—C22	−123.9 (4)
C5—C6—C7—P1	174.8 (4)	C15—C10—P1—C16	−67.7 (4)
C6—C7—C8—C9	2.6 (8)	C11—C10—P1—C16	116.2 (4)
P1—C7—C8—C9	−174.3 (4)	C23—C22—P1—C7	−69.0 (4)
C5—C4—C9—C8	−2.0 (9)	C27—C22—P1—C7	114.1 (4)
C7—C8—C9—C4	−0.7 (8)	C23—C22—P1—C10	50.6 (4)
C15—C10—C11—C12	1.2 (7)	C27—C22—P1—C10	−126.3 (4)
P1—C10—C11—C12	177.3 (4)	C23—C22—P1—C16	171.1 (3)
C10—C11—C12—C13	0.4 (8)	C27—C22—P1—C16	−5.9 (4)
C11—C12—C13—C14	−1.7 (8)	C17—C16—P1—C7	132.8 (4)
C12—C13—C14—C15	1.3 (8)	C21—C16—P1—C7	−46.0 (4)
C13—C14—C15—C10	0.4 (8)	C17—C16—P1—C10	12.9 (4)
C11—C10—C15—C14	−1.6 (7)	C21—C16—P1—C10	−165.9 (4)
P1—C10—C15—C14	−177.8 (4)	C17—C16—P1—C22	−103.8 (4)
C21—C16—C17—C18	1.3 (7)	C21—C16—P1—C22	77.4 (4)
P1—C16—C17—C18	−177.5 (4)	S1—C1—S2—C2	179.4 (3)
C16—C17—C18—C19	−2.4 (8)	S3—C1—S2—C2	0.0 (3)
C17—C18—C19—C20	1.6 (8)	C3—C2—S2—C1	−0.7 (4)
C18—C19—C20—C21	0.2 (8)	S4—C2—S2—C1	176.9 (3)
C17—C16—C21—C20	0.5 (7)	S1—C1—S3—C3	−179.0 (3)
P1—C16—C21—C20	179.3 (4)	S2—C1—S3—C3	0.4 (3)
C19—C20—C21—C16	−1.2 (8)	C2—C3—S3—C1	−0.9 (4)
C27—C22—C23—C24	−1.3 (7)	S5—C3—S3—C1	−179.8 (3)
P1—C22—C23—C24	−178.4 (3)	C3—C2—S4—Cu1	5.2 (4)
C22—C23—C24—C25	0.9 (7)	S2—C2—S4—Cu1	−172.2 (2)
C23—C24—C25—C26	0.3 (8)	C2—C3—S5—Cu1	−8.4 (4)
C24—C25—C26—C27	−1.1 (8)	S3—C3—S5—Cu1	170.4 (2)
C25—C26—C27—C22	0.6 (7)	C3—S5—Cu1—S5^i	106.61 (14)
C23—C22—C27—C26	0.6 (7)	C3—S5—Cu1—S4^i	−155.06 (15)
P1—C22—C27—C26	177.5 (3)	C3—S5—Cu1—S4	8.54 (15)
C6—C7—P1—C10	−101.2 (4)	C2—S4—Cu1—S5^i	−174.58 (15)
C8—C7—P1—C10	75.6 (4)	C2—S4—Cu1—S5	−7.71 (15)
C6—C7—P1—C22	15.9 (5)	C2—S4—Cu1—S4^i	88.69 (14)

Symmetry code: (i) −x+1, y, −z+3/2.