metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Iodido(N-phenyl­thio­urea)bis­­(tri­phenyl­phosphine)copper(I)

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai 90112, Thailand, and bThe School of Chemistry, University of Bristol, Cantock's Close, Bristol BS 1TS, England
*Correspondence e-mail: chaveng.p@psu.ac.th

(Received 28 May 2008; accepted 24 June 2008; online 28 June 2008)

The coordination geometry of the Cu atom in the title compound, [CuI(C7H8N2S)(C18H15P)2], is distorted tetra­hedral; it is coordinated by two triphenyl­phosphine P atoms, one S atom from N-phenyl­thio­urea (ptu) and one I atom. The crystal structure is stabilized by intra- and inter­molecular N—H⋯I and N—H⋯S inter­actions.

Related literature

For related literature, see: Aslanidis et al. (1993[Aslanidis, P., Hadjikakou, S. K., Karagiannidis, P., Gdaniec, M. & Kosturkiewicz, Z. (1993). Polyhedron, 12, 2221-2226.], 1998[Aslanidis, P., Hadjikakou, S. K., Karagiannidis, P. & Cox, P. J. (1998). Inorg. Chim. Acta, 271, 243-247.]); Bowmaker et al. (1987[Bowmaker, G. A., Dyason, J. C., Healy, P. C., Engelhardt, L. M., Pakawatchai, C. & White, A. H. (1987). J. Chem. Soc. Dalton Trans. pp. 1089-1097.]); Cox et al. (1999[Cox, P. J., Aslanidis, P., Karagiannidis, P. & Hadjikakou, S. K. (1999). Polyhedron, 18, 1501-1506.]); Jianping & Kazuyuki (1996[Jianping, L. & Kazuyuki, T. (1996). Polyhedron, 15, 2127-2130.]); Karagiannidis et al. (1990[Karagiannidis, P., Aslanidis, P., Papastefanou, S., Mentzafos, D., Hountas, A. & Terzis, A. (1990). Polyhedron, 9, 981-986.]); Lecomte et al. (1989[Lecomte, C., Skoulika, St., Aslanidis, P., Karagiannidis, P. & Papastefanou, St. (1989). Polyhedron, 8, 1103-1109.]); Skoulika et al. (1991[Skoulika, S., Aubry, A., Karagiannidis, P., Aslanidis, P. & Papastefanou, S. (1991). Inorg. Chim. Acta, 183, 207-211.]).

[Scheme 1]

Experimental

Crystal data
  • [CuI(C7H8N2S)(C18H15P)2]

  • Mr = 867.19

  • Triclinic, [P \overline 1]

  • a = 10.9505 (9) Å

  • b = 18.7294 (15) Å

  • c = 21.3731 (18) Å

  • α = 67.422 (1)°

  • β = 77.215 (1)°

  • γ = 73.224 (1)°

  • V = 3844.9 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.54 mm−1

  • T = 173 (2) K

  • 0.50 × 0.30 × 0.07 mm

Data collection
  • Bruker SMART Platform diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.582, Tmax = 0.898

  • 42789 measured reflections

  • 15698 independent reflections

  • 8887 reflections with I > 2σ(I)

  • Rint = 0.088

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.108

  • S = 0.98

  • 15698 reflections

  • 901 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.74 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1B⋯S2i 0.88 2.58 3.455 (5) 173
N3—H3B⋯S1ii 0.88 2.63 3.396 (5) 146
N2—H2A⋯I1 0.88 2.65 3.511 (5) 166
N4—H4A⋯I2 0.88 2.71 3.567 (4) 165
Symmetry codes: (i) x-1, y+1, z; (ii) x+1, y-1, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Studies of copper(I) complexes with mixed ligand systems containing triphenylphosphine and ligands containing S and N donors, have been increasing because of the versatility of these ligands as well as the different steric characteristics of the phosphine ligands, which can modify the compound geometry (Cox et al., 1999). The title complex, (I), is a monomeric complex which crystallizes in the triclinic system space group P1. The structure consists of two independent [CuI(PPh3)2(ptu)] molecules in the asymmetric unit. The molecules feature a distorted tetrahedral copper(I) center with two triphenylphosphine P atoms, one S atom from ptu ligand and one iodide atom (Figures 1, 2). A distorted tetrahedral geometry is also found in the copper(I) halide complexes with mixed PPh3/sulfur base ligands (Lecomte et al., 1989; Karagiannidis et al., 1990; Skoulika et al., 1991; Jianping & Kazuyuki., 1996; Aslanidis et al., 1998; Cox et al., 1999). The P—Cu—P angle deviates considerably from tetrahedral value at 118.63 (5)° and 122.18 (5)° in molecule A and B, respectively. The Cu—P distances of the molecule A [Cu(1)—P(1), 2.2908 (15)Å and Cu(1)—P(2), 2.3024 (16) Å] and of the molecule B [Cu(2)—P(3), 2.2876 (15)Å and Cu(2)—P(4), 2.2974 (16) Å] are slightly shorter as compared to the observed value for [Cu(PPh3)3I] (Bowmaker et al., 1987). The observed Cu—S distances of 2.4148 (16) and 2.3942 (15) Å in molecule A and B are consistent with the distances usually found for tetrahedrally coordinated copper(I) with thioamide-sulfur donors (Aslanidis et al., 1993). The mean plane of the phenyl ring (C45—C50) of ptu ligand in the molecule B forms a dihedral angle of 83.9 (2)° with one of phenyl ring (C81—C86) of PPh3 molecules. Weak intra-molecular hydrogen bonding between the amide group and iodide atom is observed [N2···I1= 3.511 (5) Å, H2A···I1 = 2.65 Å, N2—H2A···I1 = 166 ° for molecule A and N4···I2 = 3.567 (4) Å, H4A···I2 = 2.71 Å, N4—H4A···I2 = 165 ° for molecule B]. However, only one C—H···π interaction between C-sp2 (C46—H46···π) of the phenyl ring from ptu ligand and the centroid of one phenyl ring (Cg14, C81—C86) of the PPh3 molecules is observed in molecule B. In addition, the weak inter-molecular interactions between the one H atom of NH2 group of ptu ligand of molecule A and the thione-S atom of ptu of molecule B [N1···S2 = 3.455 (5) Å, H1B···S2 = 2.58 Å, N1—H1B···S2 = 173 °] are found and vice versa [N3···S1 = 3.396 (5) Å, H3B···S1 = 2.63 Å, N3—H3B···S1 = 146 °]. The intra- and inter-molecular interactions of this complex are shown in Figure 3.

Related literature top

For related literature, see: Aslanidis et al. (1993, 1998); Bowmaker et al. (1987); Cox et al. (1999); Jianping & Kazuyuki (1996); Karagiannidis et al. (1990); Lecomte et al. (1989); Skoulika et al. (1991).

Experimental top

Triphenylphosphine (0.27 g, 1.05 mmol) was dissolved in 30 cm3 of acetonitrile at 70–75°C. CuI (0.1 g, 0.52 mmol) was added and the mixture was stirred for 2 h. After the formation of a complete clear solution, N-phenylthiourea (0.24 g, 1.57 mmol) was added slowly and the reaction mixture was stirring for 3 h. The resulting clear solution was filtered off and left to evaporate at room temperature. The microcrystalline solid, which deposited upon standing for several days, was filtered off and dried in vacuo. Single crystals suitable for X-ray diffraction studies were obtained by slow evaporation in acetonitrile. The melting point of the complex is 456-457 K. Elemental analysis, calculated for [CuI(PPh3)2(ptu)]: C, 59.55; H, 4.43; N, 3.23; S, 3.70%, found: C, 60.28; H, 4.46; N, 3.56; S, 3.93%.

Refinement top

All H atoms atoms were constrained with a riding model for C-sp2 [C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C)] and for N atoms [N—H = 0.88 Å and with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 2003) and SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the molecule A of [CuI(PPh3)2(ptu)] complex. Thermal ellipsoids are shown at 30% probability level.
[Figure 2] Fig. 2. The molecular structure of the molecule B of [CuI(PPh3)2(ptu)] complex. Thermal ellipsoids are shown at 30% probability level.
[Figure 3] Fig. 3. The intra- and inter-molecular interactions of [CuI(PPh3)2(ptu)] complex.
Iodido(N-phenylthiourea)bis(triphenylphosphine)copper(I) top
Crystal data top
[CuI(C18H15P)2(C7H8N2S)]Z = 4
Mr = 867.19F(000) = 1752
Triclinic, P1Dx = 1.498 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71074 Å
a = 10.9505 (9) ÅCell parameters from 8397 reflections
b = 18.7294 (15) Åθ = 2.4–27.1°
c = 21.3731 (18) ŵ = 1.54 mm1
α = 67.422 (1)°T = 173 K
β = 77.215 (1)°Plate, colorless
γ = 73.224 (1)°0.50 × 0.30 × 0.07 mm
V = 3844.9 (5) Å3
Data collection top
Bruker Platform
diffractometer
15698 independent reflections
Radiation source: sealed X-ray tube8887 reflections with I > 2s(I)
Graphite monochromatorRint = 0.089
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.0°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
k = 2323
Tmin = 0.582, Tmax = 0.898l = 2626
42789 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0284P)2 + 1.9087P]
where P = (Fo2 + 2Fc2)/3
15698 reflections(Δ/σ)max = 0.001
901 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.74 e Å3
Crystal data top
[CuI(C18H15P)2(C7H8N2S)]γ = 73.224 (1)°
Mr = 867.19V = 3844.9 (5) Å3
Triclinic, P1Z = 4
a = 10.9505 (9) ÅMo Kα radiation
b = 18.7294 (15) ŵ = 1.54 mm1
c = 21.3731 (18) ÅT = 173 K
α = 67.422 (1)°0.50 × 0.30 × 0.07 mm
β = 77.215 (1)°
Data collection top
Bruker Platform
diffractometer
15698 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
8887 reflections with I > 2s(I)
Tmin = 0.582, Tmax = 0.898Rint = 0.089
42789 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 0.98Δρmax = 0.82 e Å3
15698 reflectionsΔρmin = 0.74 e Å3
901 parameters
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.

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
Cu10.22484 (6)0.77723 (4)0.37656 (3)0.02320 (17)
Cu20.80632 (6)0.24103 (4)0.10985 (3)0.02128 (16)
I10.46394 (3)0.75683 (2)0.39996 (2)0.02967 (11)
I20.56365 (3)0.26189 (2)0.09357 (2)0.02911 (11)
S10.15450 (14)0.90317 (8)0.28957 (8)0.0300 (4)
S20.86425 (13)0.12053 (8)0.20281 (7)0.0228 (3)
N10.1515 (4)1.0517 (3)0.2712 (2)0.0332 (12)
H1A0.18401.08860.27290.040*
H1B0.07781.06480.25500.040*
N20.3254 (4)0.9573 (3)0.3173 (2)0.0316 (12)
H2A0.36230.90640.33030.038*
N30.8570 (4)0.0299 (2)0.2387 (2)0.0316 (12)
H3A0.83050.06920.23710.038*
H3B0.91340.03960.26620.038*
N40.7271 (4)0.0587 (2)0.1580 (2)0.0267 (11)
H4A0.69800.10890.13460.032*
P10.21516 (14)0.68413 (8)0.33399 (7)0.0217 (3)
P20.11408 (14)0.77457 (8)0.48212 (7)0.0229 (3)
P30.80062 (13)0.33467 (8)0.15518 (7)0.0212 (3)
P40.93858 (14)0.23217 (8)0.01210 (7)0.0214 (3)
C10.2138 (5)0.9760 (3)0.2929 (3)0.0246 (13)
C20.3955 (5)1.0065 (3)0.3258 (3)0.0297 (14)
C30.4523 (5)0.9764 (3)0.3850 (3)0.0332 (15)
H30.43540.92920.42010.040*
C40.5344 (5)1.0157 (3)0.3924 (3)0.0376 (16)
H40.57490.99480.43270.045*
C50.5582 (6)1.0846 (3)0.3425 (3)0.0375 (16)
H50.61501.11110.34800.045*
C60.4991 (6)1.1147 (3)0.2848 (3)0.0366 (16)
H60.51371.16320.25100.044*
C70.4180 (5)1.0764 (3)0.2742 (3)0.0326 (15)
H70.37931.09710.23330.039*
C80.3242 (5)0.6753 (3)0.2570 (3)0.0247 (13)
C90.4422 (6)0.6943 (4)0.2459 (3)0.0379 (16)
H90.45960.71790.27420.045*
C100.5348 (6)0.6796 (4)0.1941 (3)0.0454 (18)
H100.61590.69190.18770.054*
C110.5100 (6)0.6469 (3)0.1513 (3)0.0417 (17)
H110.57360.63640.11570.050*
C120.3918 (6)0.6299 (3)0.1613 (3)0.0363 (15)
H120.37360.60820.13180.044*
C130.2983 (5)0.6438 (3)0.2136 (3)0.0284 (14)
H130.21710.63180.21960.034*
C140.0541 (5)0.7024 (3)0.3118 (3)0.0222 (13)
C150.0182 (5)0.7605 (3)0.2507 (3)0.0262 (13)
H150.08050.78640.21840.031*
C160.1063 (5)0.7808 (3)0.2361 (3)0.0268 (13)
H160.12930.82090.19430.032*
C170.1984 (5)0.7431 (3)0.2824 (3)0.0317 (15)
H170.28410.75690.27200.038*
C180.1649 (5)0.6852 (3)0.3436 (3)0.0301 (14)
H180.22750.65930.37550.036*
C190.0399 (5)0.6652 (3)0.3582 (3)0.0239 (13)
H190.01750.62570.40040.029*
C200.2465 (5)0.5804 (3)0.3896 (3)0.0234 (13)
C210.2035 (5)0.5231 (3)0.3786 (3)0.0267 (13)
H210.15480.53810.34210.032*
C220.2318 (5)0.4449 (3)0.4208 (3)0.0314 (14)
H220.20000.40680.41380.038*
C230.3049 (6)0.4212 (3)0.4727 (3)0.0387 (16)
H230.32550.36680.50060.046*
C240.3487 (6)0.4768 (3)0.4842 (3)0.0395 (16)
H240.39890.46090.52030.047*
C250.3192 (5)0.5558 (3)0.4431 (3)0.0309 (14)
H250.34910.59380.45150.037*
C260.0620 (5)0.7959 (3)0.4911 (3)0.0250 (13)
C270.1209 (5)0.8044 (3)0.4374 (3)0.0298 (14)
H270.07020.80210.39570.036*
C280.2544 (6)0.8164 (4)0.4434 (3)0.0406 (16)
H280.29470.82320.40580.049*
C290.3271 (6)0.8183 (3)0.5047 (3)0.0399 (16)
H290.41780.82530.50970.048*
C300.2687 (6)0.8102 (3)0.5582 (3)0.0383 (16)
H300.31930.81300.59980.046*
C310.1364 (5)0.7979 (3)0.5520 (3)0.0333 (15)
H310.09650.79070.58990.040*
C320.1544 (5)0.6755 (3)0.5464 (3)0.0253 (13)
C330.0754 (6)0.6219 (3)0.5641 (3)0.0368 (16)
H330.00390.63850.54600.044*
C340.1128 (7)0.5448 (4)0.6079 (3)0.0501 (19)
H340.05940.50860.61900.060*
C350.2258 (7)0.5201 (4)0.6355 (3)0.0477 (18)
H350.24910.46740.66640.057*
C360.3056 (7)0.5711 (4)0.6186 (3)0.0454 (17)
H360.38450.55370.63730.054*
C370.2700 (6)0.6486 (3)0.5740 (3)0.0333 (15)
H370.32570.68360.56230.040*
C380.1383 (5)0.8424 (3)0.5191 (3)0.0277 (14)
C390.1311 (6)0.8262 (4)0.5887 (3)0.0401 (16)
H390.12210.77550.62050.048*
C400.1373 (7)0.8861 (4)0.6111 (4)0.055 (2)
H400.12990.87600.65870.066*
C410.1542 (6)0.9597 (4)0.5653 (4)0.054 (2)
H410.15970.99940.58130.065*
C420.1626 (7)0.9743 (4)0.4973 (4)0.056 (2)
H420.17501.02430.46550.067*
C430.1534 (6)0.9167 (4)0.4743 (3)0.0407 (17)
H430.15750.92830.42670.049*
C440.8119 (5)0.0442 (3)0.1994 (3)0.0208 (12)
C450.6767 (5)0.0025 (3)0.1467 (3)0.0239 (13)
C460.6858 (5)0.0049 (3)0.0809 (3)0.0305 (14)
H460.72830.04150.04460.037*
C470.6331 (6)0.0459 (4)0.0672 (3)0.0382 (16)
H470.64040.04450.02160.046*
C480.5700 (6)0.0984 (4)0.1198 (3)0.0386 (16)
H480.53310.13280.11050.046*
C490.5607 (5)0.1007 (3)0.1860 (3)0.0388 (16)
H490.51770.13700.22230.047*
C500.6145 (5)0.0498 (3)0.2000 (3)0.0263 (13)
H500.60820.05140.24550.032*
C510.6712 (5)0.3423 (3)0.2242 (3)0.0246 (13)
C520.6550 (6)0.2738 (3)0.2773 (3)0.0447 (18)
H520.71030.22450.27650.054*
C530.5600 (7)0.2748 (4)0.3319 (3)0.053 (2)
H530.55450.22710.36930.064*
C540.4746 (6)0.3436 (4)0.3325 (4)0.0490 (19)
H540.40530.34360.36820.059*
C550.4896 (6)0.4126 (4)0.2810 (4)0.056 (2)
H550.43210.46120.28180.067*
C560.5880 (6)0.4124 (4)0.2276 (3)0.0464 (18)
H560.59840.46120.19280.056*
C570.9462 (5)0.3192 (3)0.1916 (3)0.0199 (12)
C581.0621 (5)0.2804 (3)0.1645 (3)0.0268 (13)
H581.06290.26100.12930.032*
C591.1759 (6)0.2696 (3)0.1883 (3)0.0349 (15)
H591.25470.24530.16780.042*
C601.1761 (6)0.2939 (3)0.2413 (3)0.0340 (15)
H601.25440.28540.25810.041*
C611.0622 (6)0.3306 (3)0.2698 (3)0.0326 (15)
H611.06210.34660.30700.039*
C620.9478 (6)0.3446 (3)0.2453 (3)0.0271 (13)
H620.87030.37140.26470.033*
C630.7774 (5)0.4363 (3)0.0956 (3)0.0225 (13)
C640.8678 (5)0.4821 (3)0.0775 (3)0.0284 (14)
H640.94380.46190.09900.034*
C650.8473 (6)0.5571 (3)0.0279 (3)0.0356 (15)
H650.91020.58770.01500.043*
C660.7355 (6)0.5873 (3)0.0025 (3)0.0353 (15)
H660.72160.63880.03620.042*
C670.6440 (6)0.5429 (3)0.0158 (3)0.0328 (15)
H670.56670.56400.00460.039*
C680.6657 (6)0.4678 (3)0.0640 (3)0.0289 (14)
H680.60340.43700.07580.035*
C691.1067 (5)0.1898 (3)0.0278 (3)0.0204 (12)
C701.2036 (5)0.2323 (3)0.0020 (3)0.0297 (14)
H701.18600.28280.03680.036*
C711.3245 (6)0.2011 (4)0.0189 (3)0.0370 (16)
H711.38950.23040.00190.044*
C721.3524 (6)0.1279 (4)0.0696 (3)0.0351 (15)
H721.43540.10740.08410.042*
C731.2581 (5)0.0846 (3)0.0989 (3)0.0307 (14)
H731.27670.03380.13310.037*
C741.1364 (5)0.1156 (3)0.0781 (3)0.0273 (13)
H741.07230.08570.09850.033*
C750.9415 (5)0.3227 (3)0.0624 (3)0.0242 (13)
C760.8565 (6)0.3940 (3)0.0611 (3)0.0316 (14)
H760.80080.39630.02060.038*
C770.8536 (7)0.4618 (4)0.1195 (3)0.0461 (18)
H770.79600.51030.11840.055*
C780.9325 (7)0.4593 (4)0.1779 (3)0.0484 (19)
H780.92950.50600.21720.058*
C791.0163 (7)0.3897 (4)0.1803 (3)0.0461 (18)
H791.07160.38840.22110.055*
C801.0202 (6)0.3215 (3)0.1234 (3)0.0366 (15)
H801.07710.27330.12570.044*
C810.9045 (5)0.1720 (3)0.0295 (3)0.0194 (12)
C820.9928 (5)0.1096 (3)0.0451 (3)0.0236 (13)
H821.07590.09250.03080.028*
C830.9595 (6)0.0719 (3)0.0819 (3)0.0313 (14)
H831.02040.02910.09250.038*
C840.8404 (6)0.0960 (3)0.1029 (3)0.0312 (15)
H840.81910.06990.12800.037*
C850.7513 (6)0.1577 (3)0.0879 (3)0.0305 (14)
H850.66880.17460.10280.037*
C860.7827 (5)0.1956 (3)0.0506 (3)0.0287 (14)
H860.72080.23770.03940.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0238 (4)0.0223 (4)0.0256 (4)0.0074 (3)0.0024 (3)0.0092 (3)
Cu20.0239 (4)0.0165 (3)0.0254 (4)0.0047 (3)0.0050 (3)0.0082 (3)
I10.0237 (2)0.0261 (2)0.0380 (3)0.00612 (18)0.00825 (18)0.00693 (19)
I20.0247 (2)0.0208 (2)0.0409 (3)0.00426 (17)0.01189 (18)0.00596 (18)
S10.0375 (9)0.0223 (8)0.0324 (9)0.0072 (7)0.0164 (7)0.0048 (7)
S20.0289 (8)0.0168 (7)0.0249 (8)0.0047 (6)0.0088 (6)0.0070 (6)
N10.035 (3)0.025 (3)0.044 (3)0.006 (2)0.017 (2)0.010 (2)
N20.035 (3)0.020 (3)0.044 (3)0.010 (2)0.012 (3)0.008 (2)
N30.044 (3)0.014 (2)0.040 (3)0.005 (2)0.021 (3)0.004 (2)
N40.030 (3)0.014 (2)0.036 (3)0.001 (2)0.017 (2)0.005 (2)
P10.0254 (8)0.0174 (7)0.0224 (8)0.0066 (7)0.0023 (7)0.0061 (6)
P20.0250 (8)0.0230 (8)0.0232 (8)0.0082 (7)0.0017 (7)0.0095 (7)
P30.0237 (8)0.0158 (7)0.0251 (8)0.0041 (6)0.0041 (7)0.0078 (6)
P40.0250 (8)0.0178 (8)0.0236 (8)0.0061 (6)0.0043 (7)0.0077 (7)
C10.034 (4)0.019 (3)0.019 (3)0.003 (3)0.005 (3)0.005 (3)
C20.028 (3)0.028 (3)0.034 (4)0.004 (3)0.005 (3)0.012 (3)
C30.037 (4)0.028 (3)0.036 (4)0.014 (3)0.009 (3)0.005 (3)
C40.031 (4)0.035 (4)0.050 (4)0.011 (3)0.008 (3)0.015 (3)
C50.040 (4)0.028 (4)0.051 (4)0.016 (3)0.006 (3)0.015 (3)
C60.038 (4)0.023 (3)0.045 (4)0.013 (3)0.004 (3)0.009 (3)
C70.033 (4)0.028 (3)0.033 (4)0.009 (3)0.003 (3)0.005 (3)
C80.027 (3)0.016 (3)0.028 (3)0.006 (3)0.002 (3)0.004 (3)
C90.042 (4)0.045 (4)0.030 (4)0.019 (3)0.009 (3)0.018 (3)
C100.037 (4)0.061 (5)0.047 (4)0.024 (4)0.013 (3)0.030 (4)
C110.057 (5)0.029 (4)0.032 (4)0.006 (3)0.012 (3)0.013 (3)
C120.052 (4)0.025 (3)0.032 (4)0.005 (3)0.004 (3)0.014 (3)
C130.030 (3)0.023 (3)0.032 (4)0.006 (3)0.000 (3)0.011 (3)
C140.025 (3)0.020 (3)0.026 (3)0.002 (3)0.000 (3)0.016 (3)
C150.033 (3)0.023 (3)0.027 (3)0.011 (3)0.001 (3)0.011 (3)
C160.031 (3)0.022 (3)0.027 (3)0.002 (3)0.009 (3)0.009 (3)
C170.023 (3)0.036 (4)0.045 (4)0.001 (3)0.012 (3)0.023 (3)
C180.030 (3)0.030 (3)0.033 (4)0.014 (3)0.003 (3)0.012 (3)
C190.037 (4)0.013 (3)0.019 (3)0.004 (3)0.003 (3)0.003 (2)
C200.020 (3)0.017 (3)0.027 (3)0.002 (2)0.003 (3)0.006 (3)
C210.024 (3)0.019 (3)0.033 (4)0.003 (3)0.001 (3)0.009 (3)
C220.028 (3)0.021 (3)0.043 (4)0.010 (3)0.005 (3)0.011 (3)
C230.043 (4)0.016 (3)0.044 (4)0.003 (3)0.007 (3)0.006 (3)
C240.048 (4)0.029 (4)0.029 (4)0.004 (3)0.010 (3)0.002 (3)
C250.037 (4)0.026 (3)0.028 (3)0.001 (3)0.003 (3)0.011 (3)
C260.021 (3)0.022 (3)0.035 (4)0.006 (3)0.004 (3)0.012 (3)
C270.026 (3)0.033 (3)0.036 (4)0.007 (3)0.002 (3)0.019 (3)
C280.039 (4)0.045 (4)0.044 (4)0.006 (3)0.019 (3)0.016 (3)
C290.025 (4)0.037 (4)0.052 (5)0.008 (3)0.001 (3)0.012 (3)
C300.036 (4)0.041 (4)0.030 (4)0.007 (3)0.001 (3)0.008 (3)
C310.030 (4)0.044 (4)0.029 (4)0.008 (3)0.008 (3)0.014 (3)
C320.026 (3)0.021 (3)0.027 (3)0.005 (3)0.005 (3)0.011 (3)
C330.034 (4)0.026 (3)0.049 (4)0.004 (3)0.000 (3)0.016 (3)
C340.059 (5)0.027 (4)0.058 (5)0.018 (4)0.008 (4)0.010 (4)
C350.057 (5)0.029 (4)0.042 (4)0.007 (4)0.003 (4)0.001 (3)
C360.053 (4)0.038 (4)0.039 (4)0.005 (4)0.016 (3)0.004 (3)
C370.036 (4)0.037 (4)0.031 (4)0.008 (3)0.007 (3)0.014 (3)
C380.027 (3)0.030 (3)0.030 (4)0.009 (3)0.001 (3)0.014 (3)
C390.054 (4)0.037 (4)0.033 (4)0.008 (3)0.014 (3)0.012 (3)
C400.066 (5)0.065 (5)0.051 (5)0.007 (4)0.024 (4)0.035 (4)
C410.044 (4)0.063 (5)0.086 (6)0.008 (4)0.012 (4)0.060 (5)
C420.070 (5)0.046 (5)0.071 (6)0.027 (4)0.007 (4)0.038 (4)
C430.055 (4)0.038 (4)0.037 (4)0.021 (3)0.009 (3)0.022 (3)
C440.018 (3)0.017 (3)0.023 (3)0.003 (2)0.002 (2)0.004 (3)
C450.026 (3)0.017 (3)0.029 (3)0.006 (3)0.006 (3)0.006 (3)
C460.031 (3)0.029 (3)0.029 (4)0.006 (3)0.003 (3)0.009 (3)
C470.040 (4)0.045 (4)0.044 (4)0.010 (3)0.006 (3)0.030 (3)
C480.034 (4)0.038 (4)0.058 (5)0.013 (3)0.011 (3)0.025 (4)
C490.029 (4)0.029 (4)0.057 (5)0.015 (3)0.001 (3)0.010 (3)
C500.027 (3)0.026 (3)0.024 (3)0.006 (3)0.003 (3)0.008 (3)
C510.031 (3)0.018 (3)0.028 (3)0.007 (3)0.006 (3)0.010 (3)
C520.052 (4)0.023 (4)0.051 (4)0.005 (3)0.016 (4)0.019 (3)
C530.070 (5)0.033 (4)0.049 (5)0.023 (4)0.028 (4)0.017 (4)
C540.041 (4)0.046 (5)0.057 (5)0.010 (4)0.018 (4)0.029 (4)
C550.050 (5)0.041 (4)0.057 (5)0.015 (4)0.009 (4)0.023 (4)
C560.058 (5)0.025 (4)0.035 (4)0.008 (3)0.000 (3)0.003 (3)
C570.027 (3)0.013 (3)0.019 (3)0.006 (2)0.004 (2)0.003 (2)
C580.032 (3)0.018 (3)0.031 (3)0.004 (3)0.003 (3)0.012 (3)
C590.024 (3)0.039 (4)0.039 (4)0.003 (3)0.005 (3)0.012 (3)
C600.040 (4)0.026 (3)0.035 (4)0.009 (3)0.020 (3)0.001 (3)
C610.047 (4)0.025 (3)0.025 (3)0.008 (3)0.012 (3)0.004 (3)
C620.038 (4)0.023 (3)0.021 (3)0.010 (3)0.002 (3)0.005 (3)
C630.032 (3)0.018 (3)0.023 (3)0.006 (3)0.006 (3)0.010 (3)
C640.033 (3)0.026 (3)0.027 (3)0.007 (3)0.008 (3)0.007 (3)
C650.033 (4)0.024 (3)0.048 (4)0.012 (3)0.001 (3)0.009 (3)
C660.047 (4)0.017 (3)0.034 (4)0.002 (3)0.004 (3)0.005 (3)
C670.034 (4)0.023 (3)0.039 (4)0.001 (3)0.017 (3)0.007 (3)
C680.041 (4)0.019 (3)0.032 (4)0.010 (3)0.009 (3)0.009 (3)
C690.023 (3)0.024 (3)0.020 (3)0.008 (3)0.002 (2)0.013 (3)
C700.039 (4)0.027 (3)0.032 (4)0.012 (3)0.004 (3)0.015 (3)
C710.034 (4)0.033 (4)0.054 (4)0.015 (3)0.006 (3)0.019 (3)
C720.027 (3)0.044 (4)0.045 (4)0.003 (3)0.014 (3)0.029 (3)
C730.033 (4)0.029 (3)0.030 (4)0.006 (3)0.010 (3)0.015 (3)
C740.035 (4)0.030 (3)0.024 (3)0.011 (3)0.002 (3)0.015 (3)
C750.033 (3)0.022 (3)0.020 (3)0.009 (3)0.007 (3)0.006 (3)
C760.043 (4)0.023 (3)0.030 (4)0.000 (3)0.010 (3)0.013 (3)
C770.073 (5)0.022 (4)0.041 (4)0.006 (3)0.012 (4)0.009 (3)
C780.083 (6)0.025 (4)0.039 (4)0.027 (4)0.014 (4)0.002 (3)
C790.072 (5)0.040 (4)0.027 (4)0.028 (4)0.004 (3)0.007 (3)
C800.054 (4)0.026 (3)0.030 (4)0.009 (3)0.010 (3)0.008 (3)
C810.023 (3)0.016 (3)0.016 (3)0.006 (2)0.003 (2)0.001 (2)
C820.032 (3)0.017 (3)0.025 (3)0.011 (3)0.006 (3)0.005 (3)
C830.048 (4)0.020 (3)0.028 (3)0.011 (3)0.000 (3)0.009 (3)
C840.059 (4)0.018 (3)0.025 (3)0.019 (3)0.010 (3)0.005 (3)
C850.039 (4)0.030 (3)0.026 (3)0.018 (3)0.015 (3)0.000 (3)
C860.041 (4)0.019 (3)0.025 (3)0.011 (3)0.004 (3)0.004 (3)
Geometric parameters (Å, º) top
Cu1—P12.2908 (15)C34—H340.9500
Cu1—P22.3024 (16)C35—C361.373 (8)
Cu1—S12.4148 (16)C35—H350.9500
Cu1—I12.6658 (8)C36—C371.393 (8)
Cu2—P32.2876 (15)C36—H360.9500
Cu2—P42.2974 (16)C37—H370.9500
Cu2—S22.3942 (15)C38—C431.385 (8)
Cu2—I22.6534 (8)C38—C391.387 (7)
S1—C11.701 (5)C39—C401.399 (8)
S2—C441.718 (5)C39—H390.9500
N1—C11.329 (6)C40—C411.388 (9)
N1—H1A0.8800C40—H400.9500
N1—H1B0.8800C41—C421.358 (9)
N2—C11.335 (6)C41—H410.9500
N2—C21.438 (7)C42—C431.381 (8)
N2—H2A0.8800C42—H420.9500
N3—C441.328 (6)C43—H430.9500
N3—H3A0.8800C45—C461.371 (7)
N3—H3B0.8800C45—C501.382 (7)
N4—C441.324 (6)C46—C471.391 (7)
N4—C451.434 (6)C46—H460.9500
N4—H4A0.8800C47—C481.381 (8)
P1—C201.824 (5)C47—H470.9500
P1—C141.830 (5)C48—C491.380 (8)
P1—C81.841 (5)C48—H480.9500
P2—C321.833 (5)C49—C501.402 (7)
P2—C261.834 (5)C49—H490.9500
P2—C381.836 (5)C50—H500.9500
P3—C631.821 (5)C51—C521.376 (7)
P3—C511.824 (6)C51—C561.383 (7)
P3—C571.827 (5)C52—C531.382 (8)
P4—C751.830 (5)C52—H520.9500
P4—C691.833 (5)C53—C541.360 (8)
P4—C811.834 (5)C53—H530.9500
C2—C31.379 (7)C54—C551.363 (9)
C2—C71.396 (7)C54—H540.9500
C3—C41.383 (7)C55—C561.386 (8)
C3—H30.9500C55—H550.9500
C4—C51.373 (8)C56—H560.9500
C4—H40.9500C57—C581.393 (7)
C5—C61.366 (8)C57—C621.407 (7)
C5—H50.9500C58—C591.382 (7)
C6—C71.391 (7)C58—H580.9500
C6—H60.9500C59—C601.374 (7)
C7—H70.9500C59—H590.9500
C8—C91.385 (7)C60—C611.376 (8)
C8—C131.386 (7)C60—H600.9500
C9—C101.381 (8)C61—C621.381 (7)
C9—H90.9500C61—H610.9500
C10—C111.385 (8)C62—H620.9500
C10—H100.9500C63—C641.388 (7)
C11—C121.373 (8)C63—C681.395 (7)
C11—H110.9500C64—C651.387 (7)
C12—C131.388 (7)C64—H640.9500
C12—H120.9500C65—C661.383 (8)
C13—H130.9500C65—H650.9500
C14—C151.391 (7)C66—C671.380 (7)
C14—C191.399 (7)C66—H660.9500
C15—C161.377 (7)C67—C681.377 (7)
C15—H150.9500C67—H670.9500
C16—C171.389 (7)C68—H680.9500
C16—H160.9500C69—C741.392 (7)
C17—C181.384 (8)C69—C701.401 (7)
C17—H170.9500C70—C711.381 (8)
C18—C191.384 (7)C70—H700.9500
C18—H180.9500C71—C721.383 (8)
C19—H190.9500C71—H710.9500
C20—C251.392 (7)C72—C731.387 (8)
C20—C211.402 (7)C72—H720.9500
C21—C221.379 (7)C73—C741.388 (7)
C21—H210.9500C73—H730.9500
C22—C231.370 (8)C74—H740.9500
C22—H220.9500C75—C761.396 (7)
C23—C241.384 (8)C75—C801.398 (7)
C23—H230.9500C76—C771.396 (8)
C24—C251.385 (7)C76—H760.9500
C24—H240.9500C77—C781.361 (8)
C25—H250.9500C77—H770.9500
C26—C271.373 (7)C78—C791.373 (9)
C26—C311.383 (7)C78—H780.9500
C27—C281.398 (8)C79—C801.383 (8)
C27—H270.9500C79—H790.9500
C28—C291.382 (8)C80—H800.9500
C28—H280.9500C81—C821.384 (7)
C29—C301.369 (8)C81—C861.395 (7)
C29—H290.9500C82—C831.398 (7)
C30—C311.384 (8)C82—H820.9500
C30—H300.9500C83—C841.368 (8)
C31—H310.9500C83—H830.9500
C32—C371.393 (7)C84—C851.374 (8)
C32—C331.401 (7)C84—H840.9500
C33—C341.387 (8)C85—C861.399 (7)
C33—H330.9500C85—H850.9500
C34—C351.369 (9)C86—H860.9500
P1—Cu1—P2118.63 (5)C36—C35—H35119.9
P1—Cu1—S1104.71 (6)C35—C36—C37119.6 (6)
P2—Cu1—S1111.08 (6)C35—C36—H36120.2
P1—Cu1—I1110.24 (4)C37—C36—H36120.2
P2—Cu1—I1100.32 (4)C32—C37—C36121.2 (5)
S1—Cu1—I1112.06 (4)C32—C37—H37119.4
P3—Cu2—P4122.18 (5)C36—C37—H37119.4
P3—Cu2—S2101.63 (5)C43—C38—C39118.9 (5)
P4—Cu2—S2109.15 (5)C43—C38—P2116.9 (4)
P3—Cu2—I2104.23 (4)C39—C38—P2124.0 (4)
P4—Cu2—I2109.85 (4)C38—C39—C40118.7 (6)
S2—Cu2—I2109.05 (4)C38—C39—H39120.6
C1—S1—Cu1111.92 (19)C40—C39—H39120.6
C44—S2—Cu2112.02 (19)C41—C40—C39121.5 (6)
C1—N1—H1A120.0C41—C40—H40119.2
C1—N1—H1B120.0C39—C40—H40119.2
H1A—N1—H1B120.0C42—C41—C40119.0 (6)
C1—N2—C2130.9 (5)C42—C41—H41120.5
C1—N2—H2A114.6C40—C41—H41120.5
C2—N2—H2A114.6C41—C42—C43120.3 (7)
C44—N3—H3A120.0C41—C42—H42119.9
C44—N3—H3B120.0C43—C42—H42119.9
H3A—N3—H3B120.0C42—C43—C38121.6 (6)
C44—N4—C45128.0 (4)C42—C43—H43119.2
C44—N4—H4A116.0C38—C43—H43119.2
C45—N4—H4A116.0N4—C44—N3119.9 (5)
C20—P1—C14103.9 (2)N4—C44—S2120.4 (4)
C20—P1—C899.8 (2)N3—C44—S2119.7 (4)
C14—P1—C8104.6 (2)C46—C45—C50120.6 (5)
C20—P1—Cu1117.67 (19)C46—C45—N4118.2 (5)
C14—P1—Cu1110.39 (17)C50—C45—N4121.0 (5)
C8—P1—Cu1118.67 (17)C45—C46—C47120.2 (5)
C32—P2—C26102.7 (2)C45—C46—H46119.9
C32—P2—C38105.0 (3)C47—C46—H46119.9
C26—P2—C38101.0 (2)C48—C47—C46119.9 (6)
C32—P2—Cu1111.06 (17)C48—C47—H47120.1
C26—P2—Cu1117.76 (19)C46—C47—H47120.1
C38—P2—Cu1117.57 (18)C49—C48—C47119.9 (5)
C63—P3—C51102.3 (2)C49—C48—H48120.1
C63—P3—C57104.5 (2)C47—C48—H48120.1
C51—P3—C57104.1 (2)C48—C49—C50120.3 (5)
C63—P3—Cu2115.18 (17)C48—C49—H49119.8
C51—P3—Cu2115.14 (17)C50—C49—H49119.8
C57—P3—Cu2114.08 (17)C45—C50—C49119.1 (5)
C75—P4—C69105.1 (2)C45—C50—H50120.5
C75—P4—C8197.9 (2)C49—C50—H50120.5
C69—P4—C81105.0 (2)C52—C51—C56117.1 (5)
C75—P4—Cu2118.66 (19)C52—C51—P3118.1 (4)
C69—P4—Cu2111.57 (17)C56—C51—P3124.8 (4)
C81—P4—Cu2116.81 (17)C51—C52—C53121.5 (6)
N1—C1—N2119.0 (5)C51—C52—H52119.2
N1—C1—S1121.2 (4)C53—C52—H52119.2
N2—C1—S1119.8 (4)C54—C53—C52120.5 (6)
C3—C2—C7121.0 (5)C54—C53—H53119.8
C3—C2—N2116.3 (5)C52—C53—H53119.8
C7—C2—N2122.4 (5)C53—C54—C55119.1 (6)
C2—C3—C4119.1 (5)C53—C54—H54120.5
C2—C3—H3120.4C55—C54—H54120.5
C4—C3—H3120.4C54—C55—C56120.6 (6)
C5—C4—C3121.1 (6)C54—C55—H55119.7
C5—C4—H4119.5C56—C55—H55119.7
C3—C4—H4119.5C51—C56—C55121.0 (6)
C6—C5—C4119.2 (5)C51—C56—H56119.5
C6—C5—H5120.4C55—C56—H56119.5
C4—C5—H5120.4C58—C57—C62118.1 (5)
C5—C6—C7121.9 (6)C58—C57—P3118.2 (4)
C5—C6—H6119.0C62—C57—P3123.6 (4)
C7—C6—H6119.0C59—C58—C57120.8 (5)
C6—C7—C2117.7 (6)C59—C58—H58119.6
C6—C7—H7121.2C57—C58—H58119.6
C2—C7—H7121.2C60—C59—C58120.5 (6)
C9—C8—C13119.0 (5)C60—C59—H59119.7
C9—C8—P1117.8 (4)C58—C59—H59119.7
C13—C8—P1122.9 (4)C59—C60—C61119.5 (6)
C10—C9—C8120.8 (6)C59—C60—H60120.2
C10—C9—H9119.6C61—C60—H60120.2
C8—C9—H9119.6C60—C61—C62121.0 (5)
C9—C10—C11120.4 (6)C60—C61—H61119.5
C9—C10—H10119.8C62—C61—H61119.5
C11—C10—H10119.8C61—C62—C57120.0 (5)
C12—C11—C10118.7 (6)C61—C62—H62120.0
C12—C11—H11120.7C57—C62—H62120.0
C10—C11—H11120.7C64—C63—C68118.7 (5)
C11—C12—C13121.5 (6)C64—C63—P3123.5 (4)
C11—C12—H12119.2C68—C63—P3117.7 (4)
C13—C12—H12119.2C65—C64—C63120.2 (5)
C8—C13—C12119.6 (5)C65—C64—H64119.9
C8—C13—H13120.2C63—C64—H64119.9
C12—C13—H13120.2C66—C65—C64120.1 (5)
C15—C14—C19118.1 (5)C66—C65—H65120.0
C15—C14—P1120.0 (4)C64—C65—H65120.0
C19—C14—P1121.5 (4)C67—C66—C65120.3 (5)
C16—C15—C14121.0 (5)C67—C66—H66119.9
C16—C15—H15119.5C65—C66—H66119.9
C14—C15—H15119.5C68—C67—C66119.5 (5)
C15—C16—C17120.3 (5)C68—C67—H67120.2
C15—C16—H16119.8C66—C67—H67120.2
C17—C16—H16119.8C67—C68—C63121.2 (5)
C18—C17—C16119.7 (5)C67—C68—H68119.4
C18—C17—H17120.2C63—C68—H68119.4
C16—C17—H17120.2C74—C69—C70118.2 (5)
C17—C18—C19119.9 (5)C74—C69—P4118.2 (4)
C17—C18—H18120.1C70—C69—P4123.1 (4)
C19—C18—H18120.1C71—C70—C69120.4 (5)
C18—C19—C14121.0 (5)C71—C70—H70119.8
C18—C19—H19119.5C69—C70—H70119.8
C14—C19—H19119.5C70—C71—C72120.9 (5)
C25—C20—C21118.2 (5)C70—C71—H71119.5
C25—C20—P1120.0 (4)C72—C71—H71119.5
C21—C20—P1121.7 (4)C71—C72—C73119.4 (5)
C22—C21—C20120.1 (5)C71—C72—H72120.3
C22—C21—H21120.0C73—C72—H72120.3
C20—C21—H21120.0C72—C73—C74119.9 (5)
C23—C22—C21121.2 (5)C72—C73—H73120.1
C23—C22—H22119.4C74—C73—H73120.1
C21—C22—H22119.4C73—C74—C69121.2 (5)
C22—C23—C24119.6 (5)C73—C74—H74119.4
C22—C23—H23120.2C69—C74—H74119.4
C24—C23—H23120.2C76—C75—C80118.3 (5)
C23—C24—C25119.9 (6)C76—C75—P4119.9 (4)
C23—C24—H24120.0C80—C75—P4121.6 (4)
C25—C24—H24120.0C75—C76—C77119.7 (6)
C24—C25—C20121.0 (5)C75—C76—H76120.1
C24—C25—H25119.5C77—C76—H76120.1
C20—C25—H25119.5C78—C77—C76120.8 (6)
C27—C26—C31119.1 (5)C78—C77—H77119.6
C27—C26—P2119.0 (4)C76—C77—H77119.6
C31—C26—P2121.7 (4)C77—C78—C79120.3 (6)
C26—C27—C28120.9 (6)C77—C78—H78119.9
C26—C27—H27119.6C79—C78—H78119.9
C28—C27—H27119.6C78—C79—C80120.1 (6)
C29—C28—C27119.2 (6)C78—C79—H79120.0
C29—C28—H28120.4C80—C79—H79120.0
C27—C28—H28120.4C79—C80—C75120.8 (6)
C30—C29—C28120.1 (6)C79—C80—H80119.6
C30—C29—H29120.0C75—C80—H80119.6
C28—C29—H29120.0C82—C81—C86119.1 (5)
C29—C30—C31120.4 (6)C82—C81—P4124.6 (4)
C29—C30—H30119.8C86—C81—P4116.1 (4)
C31—C30—H30119.8C81—C82—C83119.8 (5)
C26—C31—C30120.4 (5)C81—C82—H82120.1
C26—C31—H31119.8C83—C82—H82120.1
C30—C31—H31119.8C84—C83—C82120.8 (5)
C37—C32—C33117.9 (5)C84—C83—H83119.6
C37—C32—P2121.1 (4)C82—C83—H83119.6
C33—C32—P2120.7 (4)C83—C84—C85120.3 (5)
C34—C33—C32120.2 (6)C83—C84—H84119.9
C34—C33—H33119.9C85—C84—H84119.9
C32—C33—H33119.9C84—C85—C86119.6 (5)
C35—C34—C33120.9 (6)C84—C85—H85120.2
C35—C34—H34119.6C86—C85—H85120.2
C33—C34—H34119.6C81—C86—C85120.4 (5)
C34—C35—C36120.2 (6)C81—C86—H86119.8
C34—C35—H35119.9C85—C86—H86119.8
P1—Cu1—S1—C1155.0 (2)P2—C32—C33—C34174.0 (5)
P2—Cu1—S1—C175.8 (2)C32—C33—C34—C351.1 (10)
I1—Cu1—S1—C135.5 (2)C33—C34—C35—C361.6 (10)
P3—Cu2—S2—C44154.2 (2)C34—C35—C36—C370.9 (10)
P4—Cu2—S2—C4475.5 (2)C33—C32—C37—C360.9 (8)
I2—Cu2—S2—C4444.5 (2)P2—C32—C37—C36174.7 (5)
P2—Cu1—P1—C2049.5 (2)C35—C36—C37—C320.4 (9)
S1—Cu1—P1—C20174.04 (19)C32—P2—C38—C43160.6 (5)
I1—Cu1—P1—C2065.3 (2)C26—P2—C38—C4392.9 (5)
P2—Cu1—P1—C1469.5 (2)Cu1—P2—C38—C4336.6 (5)
S1—Cu1—P1—C1455.1 (2)C32—P2—C38—C3925.2 (6)
I1—Cu1—P1—C14175.77 (19)C26—P2—C38—C3981.3 (6)
P2—Cu1—P1—C8169.8 (2)Cu1—P2—C38—C39149.2 (5)
S1—Cu1—P1—C865.6 (2)C43—C38—C39—C401.0 (9)
I1—Cu1—P1—C855.1 (2)P2—C38—C39—C40173.1 (5)
P1—Cu1—P2—C3252.3 (2)C38—C39—C40—C411.9 (10)
S1—Cu1—P2—C32173.66 (19)C39—C40—C41—C421.1 (11)
I1—Cu1—P2—C3267.70 (19)C40—C41—C42—C430.6 (11)
P1—Cu1—P2—C2665.6 (2)C41—C42—C43—C381.5 (11)
S1—Cu1—P2—C2655.7 (2)C39—C38—C43—C420.6 (9)
I1—Cu1—P2—C26174.36 (19)P2—C38—C43—C42175.1 (5)
P1—Cu1—P2—C38173.2 (2)C45—N4—C44—N32.6 (8)
S1—Cu1—P2—C3865.5 (2)C45—N4—C44—S2177.4 (4)
I1—Cu1—P2—C3853.2 (2)Cu2—S2—C44—N413.3 (5)
P4—Cu2—P3—C6351.5 (2)Cu2—S2—C44—N3166.7 (4)
S2—Cu2—P3—C63173.1 (2)C44—N4—C45—C46125.8 (6)
I2—Cu2—P3—C6373.5 (2)C44—N4—C45—C5057.6 (8)
P4—Cu2—P3—C51170.3 (2)C50—C45—C46—C470.4 (8)
S2—Cu2—P3—C5168.1 (2)N4—C45—C46—C47177.0 (5)
I2—Cu2—P3—C5145.3 (2)C45—C46—C47—C480.7 (9)
P4—Cu2—P3—C5769.39 (19)C46—C47—C48—C490.6 (9)
S2—Cu2—P3—C5752.28 (19)C47—C48—C49—C500.3 (9)
I2—Cu2—P3—C57165.61 (18)C46—C45—C50—C490.1 (8)
P3—Cu2—P4—C7548.3 (2)N4—C45—C50—C49176.6 (5)
S2—Cu2—P4—C75166.35 (19)C48—C49—C50—C450.0 (9)
I2—Cu2—P4—C7574.13 (19)C63—P3—C51—C52176.1 (5)
P3—Cu2—P4—C6974.04 (19)C57—P3—C51—C5275.3 (5)
S2—Cu2—P4—C6944.03 (18)Cu2—P3—C51—C5250.3 (5)
I2—Cu2—P4—C69163.55 (17)C63—P3—C51—C564.5 (6)
P3—Cu2—P4—C81165.18 (19)C57—P3—C51—C56104.1 (5)
S2—Cu2—P4—C8176.8 (2)Cu2—P3—C51—C56130.2 (5)
I2—Cu2—P4—C8142.8 (2)C56—C51—C52—C530.2 (10)
C2—N2—C1—N10.8 (9)P3—C51—C52—C53179.2 (5)
C2—N2—C1—S1179.7 (5)C51—C52—C53—C544.0 (11)
Cu1—S1—C1—N1152.6 (4)C52—C53—C54—C554.9 (11)
Cu1—S1—C1—N228.1 (5)C53—C54—C55—C562.1 (11)
C1—N2—C2—C3139.7 (6)C52—C51—C56—C552.6 (10)
C1—N2—C2—C747.4 (9)P3—C51—C56—C55178.0 (5)
C7—C2—C3—C41.1 (9)C54—C55—C56—C511.7 (11)
N2—C2—C3—C4171.9 (5)C63—P3—C57—C5898.3 (4)
C2—C3—C4—C51.1 (9)C51—P3—C57—C58154.7 (4)
C3—C4—C5—C60.3 (9)Cu2—P3—C57—C5828.3 (4)
C4—C5—C6—C71.8 (9)C63—P3—C57—C6281.5 (5)
C5—C6—C7—C21.8 (9)C51—P3—C57—C6225.6 (5)
C3—C2—C7—C60.3 (9)Cu2—P3—C57—C62151.9 (4)
N2—C2—C7—C6172.9 (5)C62—C57—C58—C592.2 (8)
C20—P1—C8—C999.4 (5)P3—C57—C58—C59177.6 (4)
C14—P1—C8—C9153.3 (4)C57—C58—C59—C603.0 (8)
Cu1—P1—C8—C929.8 (5)C58—C59—C60—C611.4 (8)
C20—P1—C8—C1374.6 (5)C59—C60—C61—C621.0 (8)
C14—P1—C8—C1332.7 (5)C60—C61—C62—C571.8 (8)
Cu1—P1—C8—C13156.3 (4)C58—C57—C62—C610.2 (7)
C13—C8—C9—C102.4 (9)P3—C57—C62—C61180.0 (4)
P1—C8—C9—C10171.8 (5)C51—P3—C63—C64117.5 (5)
C8—C9—C10—C111.4 (10)C57—P3—C63—C649.2 (5)
C9—C10—C11—C120.3 (10)Cu2—P3—C63—C64116.8 (4)
C10—C11—C12—C130.9 (9)C51—P3—C63—C6866.1 (5)
C9—C8—C13—C121.8 (8)C57—P3—C63—C68174.4 (4)
P1—C8—C13—C12172.1 (4)Cu2—P3—C63—C6859.6 (5)
C11—C12—C13—C80.2 (9)C68—C63—C64—C651.1 (8)
C20—P1—C14—C15153.0 (4)P3—C63—C64—C65175.3 (4)
C8—P1—C14—C1548.8 (5)C63—C64—C65—C661.4 (9)
Cu1—P1—C14—C1580.0 (4)C64—C65—C66—C670.4 (9)
C20—P1—C14—C1933.9 (5)C65—C66—C67—C681.0 (9)
C8—P1—C14—C19138.1 (4)C66—C67—C68—C631.3 (9)
Cu1—P1—C14—C1993.2 (4)C64—C63—C68—C670.3 (8)
C19—C14—C15—C160.1 (8)P3—C63—C68—C67176.8 (4)
P1—C14—C15—C16173.3 (4)C75—P4—C69—C74173.9 (4)
C14—C15—C16—C170.6 (8)C81—P4—C69—C7471.1 (4)
C15—C16—C17—C180.6 (8)Cu2—P4—C69—C7456.3 (4)
C16—C17—C18—C190.2 (8)C75—P4—C69—C7014.3 (5)
C17—C18—C19—C140.3 (8)C81—P4—C69—C70117.1 (4)
C15—C14—C19—C180.3 (7)Cu2—P4—C69—C70115.5 (4)
P1—C14—C19—C18173.6 (4)C74—C69—C70—C710.7 (8)
C14—P1—C20—C25146.2 (4)P4—C69—C70—C71171.1 (4)
C8—P1—C20—C25106.0 (5)C69—C70—C71—C720.2 (9)
Cu1—P1—C20—C2523.8 (5)C70—C71—C72—C731.2 (9)
C14—P1—C20—C2136.4 (5)C71—C72—C73—C741.2 (8)
C8—P1—C20—C2171.5 (5)C72—C73—C74—C690.2 (8)
Cu1—P1—C20—C21158.8 (4)C70—C69—C74—C730.7 (8)
C25—C20—C21—C220.9 (8)P4—C69—C74—C73171.5 (4)
P1—C20—C21—C22178.4 (4)C69—P4—C75—C76130.9 (4)
C20—C21—C22—C231.9 (8)C81—P4—C75—C76121.1 (4)
C21—C22—C23—C241.7 (9)Cu2—P4—C75—C765.4 (5)
C22—C23—C24—C250.5 (9)C69—P4—C75—C8054.2 (5)
C23—C24—C25—C200.4 (9)C81—P4—C75—C8053.8 (5)
C21—C20—C25—C240.2 (8)Cu2—P4—C75—C80179.7 (4)
P1—C20—C25—C24177.3 (4)C80—C75—C76—C771.0 (8)
C32—P2—C26—C27115.7 (4)P4—C75—C76—C77176.1 (4)
C38—P2—C26—C27136.1 (4)C75—C76—C77—C780.2 (9)
Cu1—P2—C26—C276.7 (5)C76—C77—C78—C790.0 (10)
C32—P2—C26—C3159.6 (5)C77—C78—C79—C800.5 (10)
C38—P2—C26—C3148.7 (5)C78—C79—C80—C751.4 (9)
Cu1—P2—C26—C31178.1 (4)C76—C75—C80—C791.6 (8)
C31—C26—C27—C281.2 (8)P4—C75—C80—C79176.6 (4)
P2—C26—C27—C28176.6 (4)C75—P4—C81—C82107.0 (5)
C26—C27—C28—C291.1 (9)C69—P4—C81—C821.0 (5)
C27—C28—C29—C301.4 (9)Cu2—P4—C81—C82125.2 (4)
C28—C29—C30—C311.7 (9)C75—P4—C81—C8668.4 (4)
C27—C26—C31—C301.5 (8)C69—P4—C81—C86176.4 (4)
P2—C26—C31—C30176.8 (4)Cu2—P4—C81—C8659.4 (4)
C29—C30—C31—C261.8 (9)C86—C81—C82—C830.6 (8)
C26—P2—C32—C37156.6 (4)P4—C81—C82—C83174.7 (4)
C38—P2—C32—C3751.4 (5)C81—C82—C83—C840.1 (8)
Cu1—P2—C32—C3776.7 (5)C82—C83—C84—C850.1 (8)
C26—P2—C32—C3329.8 (5)C83—C84—C85—C860.4 (8)
C38—P2—C32—C33135.0 (4)C82—C81—C86—C851.1 (8)
Cu1—P2—C32—C3397.0 (4)P4—C81—C86—C85174.6 (4)
C37—C32—C33—C340.1 (8)C84—C85—C86—C811.1 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S2i0.882.583.455 (5)173
N3—H3B···S1ii0.882.633.396 (5)146
N2—H2A···I10.882.653.511 (5)166
N4—H4A···I20.882.713.567 (4)165
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y1, z.

Experimental details

Crystal data
Chemical formula[CuI(C18H15P)2(C7H8N2S)]
Mr867.19
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)10.9505 (9), 18.7294 (15), 21.3731 (18)
α, β, γ (°)67.422 (1), 77.215 (1), 73.224 (1)
V3)3844.9 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.54
Crystal size (mm)0.50 × 0.30 × 0.07
Data collection
DiffractometerBruker Platform
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.582, 0.898
No. of measured, independent and
observed [I > 2s(I)] reflections
42789, 15698, 8887
Rint0.089
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.108, 0.98
No. of reflections15698
No. of parameters901
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.74

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S2i0.882.583.455 (5)173.3
N3—H3B···S1ii0.882.633.396 (5)146.3
N2—H2A···I10.882.653.511 (5)165.6
N4—H4A···I20.882.713.567 (4)164.5
Symmetry codes: (i) x1, y+1, z; (ii) x+1, y1, z.
 

Acknowledgements

We gratefully acknowledge financial assistance from the Center for Innovation in Chemistry: Postgraduate Education and Research Program in Chemistry (PERCH-CIC), Department of Chemistry and Graduate School, Prince of Songkla University.

References

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First citationAslanidis, P., Hadjikakou, S. K., Karagiannidis, P., Gdaniec, M. & Kosturkiewicz, Z. (1993). Polyhedron, 12, 2221–2226.  CSD CrossRef CAS Web of Science Google Scholar
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First citationLecomte, C., Skoulika, St., Aslanidis, P., Karagiannidis, P. & Papastefanou, St. (1989). Polyhedron, 8, 1103–1109.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSkoulika, S., Aubry, A., Karagiannidis, P., Aslanidis, P. & Papastefanou, S. (1991). Inorg. Chim. Acta, 183, 207–211.  CSD CrossRef CAS Web of Science Google Scholar

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