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

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ISSN: 2056-9890

[1,3-Bis(di­phenyl­phosphan­yl)propane-κ2P,P′](1,10-phenanthroline-κ2N,N′)copper(I) perchlorate

aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, bResearch Center for Import–Export Chemicals Safety of General Administration of Quality Supervision, Inspection and Quarantine of the People's Republic of China (AQSIQ), Chinese Academy of Inspection and Quarantine, Beijing 100123, People's Republic of China, and cKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Capital Normal University, Beijing 100048, People's Republic of China
*Correspondence e-mail: jinqh204@163.com

(Received 22 September 2011; accepted 1 November 2011; online 9 November 2011)

The title compound, [Cu(C12H8N2)(C27H26P2)]ClO4, crystallizes with two CuI complex cations and two perchlorate anions in the asymmetric unit. Each CuI cation is four-coordinated by two P atoms of a 1,3-bis­(diphenyl­phosphan­yl)propane mol­ecule and two N atoms of a 1,10-phenanthroline ligand, with a coordination geometry that can be considered as distorted tetra­hedral. The crystal studied was twinned with a twin ratio of 0.786 (2):0.214 (2).

Related literature

For related structures, see: Abakumov et al. (1998[Abakumov, G. A., Cherkasov, V. K., Krashilina, A. V., Eremenko, I. L. & Nefedov, S. E. (1998). Russ. Chem. Bull. 11, 2333-2340.]); Saito et al. (2006[Saito, K., Arai, T., Takahashi, N., Tsukuda, T. & Tsubomura, T. (2006). Dalton Trans. pp. 4444-4448.]); Fournier et al. (2004[Fournier, E., Sicard, S., Decken, A. & Harvey, P. D. (2004). Inorg. Chem. 43, 1491-1501.]); Affandi et al. (1997[Affandi, D., Price, S. J. B., Effendy, H., Harvey, P. J., Healy, P. C., Ruch, B. E. & White, A. H. (1997). J. Chem. Soc. Dalton Trans. pp. 1411-1420.]); Jin et al. (2009[Jin, Q. H., Chen, L. M., Li, P. Z., Deng, S. F. & Wang, R. (2009). Inorg. Chim. Acta, 362, 5224-5230.]); Alanidis et al. (2002[Alanidis, P., Cox, P. J., Divanidis, S. & Tsipis, A. C. (2002). Inorg. Chem. 41, 6875-6886.]). Potential twinning was indicated by PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and confirmed using ROTAX (Parson & Gould, 2001[Parson, S. & Gould, B. (2001). ROTAX. University of Edinburgh, Scotland.]) as included in the WinGX suite (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C12H8N2)(C27H26P2)]ClO4

  • Mr = 755.61

  • Monoclinic, C c

  • a = 16.6548 (15) Å

  • b = 12.9238 (12) Å

  • c = 32.936 (3) Å

  • β = 90.126 (1)°

  • V = 7089.2 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.83 mm−1

  • T = 298 K

  • 0.45 × 0.40 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.708, Tmax = 0.852

  • 10139 measured reflections

  • 10139 independent reflections

  • 8324 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.074

  • S = 0.91

  • 10139 reflections

  • 884 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.27 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6243 Friedel pairs

  • Flack parameter: −0.009 (12)

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

There has been an increasing interest in the photophysics and photochemistry of CuI complexes in the last few decades. Especially CuIcomplexes of mixed ligand phosphines and 1,10-phenanthroline (phen) have been often used as interesting emitters. Among the diphosphine ligands known in the literature, 1,3-Bis(diphenylphosphanyl) propane (dppp) is extensively studied since dppp is a very efficient bidentate ligand to lock one metal atom (Abakumov et al.,1998;Saito et al.,2006;Fournier et al.,2004; Affandi et al.,1997). As a part of the extension of our study on photophysical properties of copper(I) complexes with ligands containing phosphine and nitrogen atoms(Jin et al., 2009), we synthesized a new complex with the formula [Cu(dppp)(phen)] + (ClO4)- .

The bond distances, bond and torsion angles in the two CuI complex moieties present in the asymmetric units are quite similar, in fact the two molecules can be almost perfectly overlayed, Mercury (Macrae et al., 2008). Each copper(I) cation is four-coordinated by two phosphorus atoms from dppp, and two nitrogen atoms from phen. The angles P—Cu—P, N—P—N and P—Cu—N are in the range of 104.71 (12)°-105.03 (12)°, 81.0 (4)°-81.2 (4) and 108.7 (3)°-124.1 (3)°, respectively, which confirms the distorted tetrahedral environment around both of the copper(I) cations (Fig. 1).

Related literature top

For related structures, see: Abakumov et al. (1998); Saito et al. (2006); Fournier et al. (2004); Affandi et al. (1997); Jin et al. (2009); Alanidis et al. (2002). Potential twinning was indicated by PLATON (Spek, 2009) and confirmed using ROTAX (Parson & Gould, 2001) as included in the WinGX suite (Farrugia, 1999).

Experimental top

A mixture of Cu(ClO4)2(55.58 mg, 0.15 mmol) and Cu (9.53 mg, 0.15 mmol) were stirred in a solution of CH3CN(15 ml) and CH2Cl2(5 ml), after half one hour the blue solution became colorless,and then 1,10-phen (39.6 mg, 0.3 mmol) and dppp (123.73 mg, 0.3 mmol) were added and the solution stirred for 3 h. The yellow filtrate was allowed to stand at room temperature for several days and yellow crystal of the title complex [Cu(dppp)(phen)](ClO4) were obtained. Crystals suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.

Refinement top

Metal atom were located from the E-maps and other non-hydrogen atoms were located in successive difference Fourier syntheses. H atoms were geometrically positioned and refined in the riding model approximation, with C—H =0.93 and 0.97 Å for aromatic and methylene respectively and Uiso(H)=1.2Ueq(C).

Potential twinning was indicates by PLATON (Spek, 2009) and confirmed using ROTAX program (Parson & Gould, 2001) as included in the WINGX suite (Farrugia, 1999). Refinements were done using the twining matrix [-1 0 0, 0 -1 0, 0 0 1], which gave a twin ratio of 0.786:0.214 (2).

Structure description top

There has been an increasing interest in the photophysics and photochemistry of CuI complexes in the last few decades. Especially CuIcomplexes of mixed ligand phosphines and 1,10-phenanthroline (phen) have been often used as interesting emitters. Among the diphosphine ligands known in the literature, 1,3-Bis(diphenylphosphanyl) propane (dppp) is extensively studied since dppp is a very efficient bidentate ligand to lock one metal atom (Abakumov et al.,1998;Saito et al.,2006;Fournier et al.,2004; Affandi et al.,1997). As a part of the extension of our study on photophysical properties of copper(I) complexes with ligands containing phosphine and nitrogen atoms(Jin et al., 2009), we synthesized a new complex with the formula [Cu(dppp)(phen)] + (ClO4)- .

The bond distances, bond and torsion angles in the two CuI complex moieties present in the asymmetric units are quite similar, in fact the two molecules can be almost perfectly overlayed, Mercury (Macrae et al., 2008). Each copper(I) cation is four-coordinated by two phosphorus atoms from dppp, and two nitrogen atoms from phen. The angles P—Cu—P, N—P—N and P—Cu—N are in the range of 104.71 (12)°-105.03 (12)°, 81.0 (4)°-81.2 (4) and 108.7 (3)°-124.1 (3)°, respectively, which confirms the distorted tetrahedral environment around both of the copper(I) cations (Fig. 1).

For related structures, see: Abakumov et al. (1998); Saito et al. (2006); Fournier et al. (2004); Affandi et al. (1997); Jin et al. (2009); Alanidis et al. (2002). Potential twinning was indicated by PLATON (Spek, 2009) and confirmed using ROTAX (Parson & Gould, 2001) as included in the WinGX suite (Farrugia, 1999).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the structure of one of the two geometrically equivalent CuI complex and perchlorate moieties present in the asymmetric unit. Atoms are displayed as elliposoids at the 50% probability level
[1,3-Bis(diphenylphosphanyl)propane-κ2P,P'](1,10- phenanthroline-κ2N,N')copper(I) perchlorate top
Crystal data top
[Cu(C12H8N2)(C27H26P2)]ClO4F(000) = 3120
Mr = 755.61Dx = 1.417 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 6082 reflections
a = 16.6548 (15) Åθ = 2.7–23.6°
b = 12.9238 (12) ŵ = 0.83 mm1
c = 32.936 (3) ÅT = 298 K
β = 90.126 (1)°Block, yellow
V = 7089.2 (11) Å30.45 × 0.40 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
10139 independent reflections
Radiation source: fine-focus sealed tube8324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
phi and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.708, Tmax = 0.852k = 1512
10139 measured reflectionsl = 3929
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0325P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
10139 reflectionsΔρmax = 0.34 e Å3
884 parametersΔρmin = 0.27 e Å3
2 restraintsAbsolute structure: Flack (1983), 6243 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.009 (12)
Crystal data top
[Cu(C12H8N2)(C27H26P2)]ClO4V = 7089.2 (11) Å3
Mr = 755.61Z = 8
Monoclinic, CcMo Kα radiation
a = 16.6548 (15) ŵ = 0.83 mm1
b = 12.9238 (12) ÅT = 298 K
c = 32.936 (3) Å0.45 × 0.40 × 0.20 mm
β = 90.126 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
10139 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8324 reflections with I > 2σ(I)
Tmin = 0.708, Tmax = 0.852Rint = 0.035
10139 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.074Δρmax = 0.34 e Å3
S = 0.91Δρmin = 0.27 e Å3
10139 reflectionsAbsolute structure: Flack (1983), 6243 Friedel pairs
884 parametersAbsolute structure parameter: 0.009 (12)
2 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cu10.42671 (4)0.72241 (5)0.39790 (2)0.03690 (17)
P10.47763 (8)0.69379 (10)0.45975 (5)0.0357 (3)
P20.53343 (9)0.75548 (11)0.35901 (5)0.0358 (3)
N10.3358 (2)0.8312 (3)0.40279 (14)0.0331 (11)
N20.3362 (2)0.6372 (3)0.37241 (14)0.0364 (11)
C10.3335 (3)0.9226 (4)0.42048 (19)0.0427 (15)
H10.38170.94980.43010.051*
C20.2656 (4)0.9803 (4)0.4258 (2)0.0503 (16)
H20.26841.04490.43810.060*
C30.1945 (4)0.9425 (5)0.4130 (2)0.0557 (18)
H30.14750.97960.41750.067*
C40.1917 (3)0.8466 (4)0.3927 (2)0.0436 (15)
C50.2645 (3)0.7929 (4)0.38937 (17)0.0321 (13)
C60.2653 (3)0.6905 (4)0.37148 (16)0.0293 (12)
C70.1941 (3)0.6499 (4)0.35579 (19)0.0421 (14)
C80.1975 (4)0.5513 (5)0.33929 (19)0.0517 (17)
H80.15200.52240.32740.062*
C90.2677 (4)0.4965 (5)0.34041 (19)0.0537 (17)
H90.27050.42990.32980.064*
C100.3341 (3)0.5427 (4)0.3576 (2)0.0458 (15)
H100.38110.50400.35890.055*
C110.1204 (4)0.8038 (6)0.3764 (2)0.0555 (18)
H110.07230.84010.37820.067*
C120.1220 (4)0.7101 (5)0.3581 (2)0.0579 (18)
H120.07500.68400.34680.069*
C130.5725 (3)0.7652 (4)0.46446 (18)0.0426 (15)
H13A0.56120.83880.46440.051*
H13B0.59730.74820.49030.051*
C140.6319 (3)0.7406 (4)0.43006 (18)0.0445 (15)
H14A0.62900.66720.42420.053*
H14B0.68580.75520.43970.053*
C150.6180 (3)0.8006 (4)0.39041 (19)0.0405 (15)
H15A0.66660.79680.37430.049*
H15B0.60920.87280.39710.049*
C160.5047 (3)0.5636 (4)0.47674 (18)0.0370 (13)
C170.5514 (4)0.5449 (5)0.5100 (2)0.0589 (19)
H170.57100.60060.52490.071*
C180.5701 (5)0.4464 (6)0.5221 (2)0.073 (2)
H180.60060.43560.54540.087*
C190.5437 (4)0.3635 (5)0.4995 (2)0.065 (2)
H190.55850.29640.50660.077*
C200.4961 (4)0.3805 (5)0.4671 (2)0.066 (2)
H200.47640.32440.45250.079*
C210.4760 (4)0.4798 (4)0.4552 (2)0.0502 (16)
H210.44310.49020.43270.060*
C220.4171 (4)0.7430 (4)0.50179 (19)0.0451 (15)
C230.4487 (5)0.7817 (6)0.5368 (2)0.081 (2)
H230.50390.78250.54090.097*
C240.3961 (7)0.8204 (8)0.5666 (3)0.111 (3)
H240.41780.84680.59050.133*
C250.3168 (7)0.8208 (6)0.5621 (3)0.092 (3)
H250.28360.84740.58220.111*
C260.2863 (5)0.7821 (6)0.5281 (3)0.074 (2)
H260.23080.78050.52470.088*
C270.3352 (4)0.7439 (5)0.4974 (2)0.0580 (18)
H270.31210.71870.47370.070*
C280.5713 (3)0.6449 (4)0.33030 (18)0.0392 (14)
C290.6472 (3)0.6057 (5)0.33432 (19)0.0494 (16)
H290.68270.63450.35300.059*
C300.6710 (4)0.5227 (6)0.3103 (2)0.0642 (19)
H300.72220.49540.31370.077*
C310.6204 (5)0.4803 (5)0.2818 (3)0.075 (2)
H310.63760.42590.26550.090*
C320.5451 (5)0.5189 (6)0.2779 (3)0.080 (2)
H320.51040.49060.25870.096*
C330.5195 (4)0.5999 (5)0.3019 (2)0.0556 (17)
H330.46730.62470.29920.067*
C340.5288 (3)0.8567 (4)0.32093 (17)0.0371 (13)
C350.4785 (4)0.9415 (5)0.3279 (2)0.0510 (16)
H350.44740.94350.35130.061*
C360.4743 (4)1.0228 (5)0.3005 (2)0.0625 (19)
H360.44061.07880.30550.075*
C370.5199 (5)1.0202 (6)0.2660 (2)0.065 (2)
H370.51841.07550.24800.077*
C380.5679 (5)0.9367 (6)0.2580 (2)0.066 (2)
H380.59730.93470.23410.079*
C390.5731 (4)0.8553 (5)0.28510 (19)0.0485 (16)
H390.60630.79930.27940.058*
Cu20.67768 (4)0.02367 (5)0.12969 (2)0.03601 (16)
P30.78350 (8)0.00721 (11)0.16949 (5)0.0354 (3)
P40.73055 (8)0.05612 (10)0.06834 (5)0.0343 (3)
N30.5868 (2)0.1137 (3)0.15442 (14)0.0351 (11)
N40.5858 (2)0.0825 (3)0.12632 (14)0.0336 (11)
C400.5885 (3)0.2093 (4)0.16869 (18)0.0414 (14)
H400.63700.24500.16850.050*
C410.5204 (4)0.2587 (4)0.1840 (2)0.0505 (16)
H410.52380.32580.19400.061*
C420.4494 (4)0.2076 (5)0.18395 (19)0.0511 (17)
H420.40370.23990.19410.061*
C430.4444 (3)0.1067 (4)0.16880 (18)0.0380 (14)
C440.5157 (3)0.0626 (4)0.15437 (16)0.0302 (12)
C450.5148 (3)0.0407 (4)0.13846 (16)0.0301 (13)
C460.4417 (3)0.0937 (4)0.13530 (19)0.0428 (15)
C470.4435 (4)0.1931 (5)0.1176 (2)0.0525 (17)
H470.39630.23050.11400.063*
C480.5143 (4)0.2330 (5)0.1061 (2)0.0564 (18)
H480.51630.29910.09490.068*
C490.5841 (3)0.1769 (4)0.11057 (18)0.0440 (15)
H490.63210.20660.10220.053*
C500.3722 (4)0.0494 (5)0.1668 (2)0.0542 (18)
H500.32520.07760.17730.065*
C510.3705 (4)0.0462 (5)0.1498 (2)0.0545 (18)
H510.32190.08110.14750.065*
C520.8703 (3)0.0452 (4)0.13890 (17)0.0394 (15)
H52A0.91800.03840.15560.047*
H52B0.86460.11790.13210.047*
C530.8841 (3)0.0152 (5)0.09922 (18)0.0445 (15)
H53A0.87930.08860.10500.053*
H53B0.93870.00270.09020.053*
C540.8272 (3)0.0116 (4)0.06470 (18)0.0422 (15)
H54A0.81760.08560.06480.051*
H54B0.85240.00610.03910.051*
C550.8147 (3)0.1043 (4)0.19919 (18)0.0423 (14)
C560.8901 (4)0.1481 (6)0.1967 (2)0.068 (2)
H560.92820.12030.17920.081*
C570.9094 (6)0.2339 (7)0.2204 (3)0.091 (3)
H570.96020.26320.21880.109*
C580.8531 (8)0.2749 (7)0.2460 (3)0.103 (4)
H580.86580.33300.26140.124*
C590.7787 (6)0.2317 (6)0.2492 (3)0.093 (3)
H590.74140.25960.26710.112*
C600.7588 (4)0.1459 (5)0.2258 (2)0.064 (2)
H600.70800.11640.22790.077*
C610.7826 (3)0.1098 (4)0.20750 (18)0.0385 (14)
C620.8327 (4)0.1084 (5)0.24078 (19)0.0491 (16)
H620.86500.05080.24530.059*
C630.8363 (5)0.1901 (6)0.2676 (2)0.067 (2)
H630.87100.18790.28980.080*
C640.7881 (5)0.2751 (6)0.2614 (2)0.068 (2)
H640.79030.33080.27930.081*
C650.7364 (4)0.2776 (5)0.2286 (2)0.0592 (18)
H650.70330.33460.22460.071*
C660.7341 (3)0.1953 (4)0.2019 (2)0.0488 (15)
H660.69930.19750.17980.059*
C670.7561 (3)0.1873 (4)0.05374 (17)0.0358 (13)
C680.7223 (3)0.2701 (4)0.0740 (2)0.0491 (16)
H680.68630.25760.09500.059*
C690.7408 (4)0.3720 (5)0.0637 (2)0.0631 (19)
H690.71840.42690.07800.076*
C700.7919 (5)0.3897 (5)0.0327 (2)0.070 (2)
H700.80380.45760.02550.084*
C710.8261 (5)0.3114 (6)0.0119 (2)0.076 (2)
H710.86170.32560.00910.091*
C720.8081 (4)0.2100 (5)0.0217 (2)0.0622 (19)
H720.83080.15630.00680.075*
C730.6754 (4)0.0081 (4)0.02457 (19)0.0439 (15)
C740.5942 (4)0.0083 (5)0.0283 (2)0.065 (2)
H740.56870.00700.05260.078*
C750.5490 (6)0.0481 (7)0.0045 (3)0.093 (3)
H750.49430.06020.00160.112*
C760.5865 (8)0.0689 (6)0.0407 (4)0.110 (4)
H760.55740.09580.06240.132*
C770.6654 (6)0.0500 (7)0.0445 (3)0.108 (4)
H770.69050.06160.06920.129*
C780.7092 (5)0.0140 (6)0.0124 (2)0.082 (3)
H780.76410.00410.01570.099*
Cl10.62460 (9)0.52007 (15)0.14978 (6)0.0629 (5)
O10.6741 (3)0.4530 (4)0.1715 (2)0.100 (2)
O20.5784 (3)0.4606 (6)0.1222 (2)0.123 (3)
O30.6722 (4)0.5902 (4)0.1281 (2)0.107 (2)
O40.5722 (4)0.5705 (7)0.1754 (2)0.158 (3)
Cl20.37682 (10)0.22630 (15)0.38519 (5)0.0607 (5)
O50.4267 (3)0.2954 (4)0.36355 (18)0.0923 (18)
O60.3291 (4)0.1696 (6)0.3587 (2)0.140 (3)
O70.4233 (3)0.1602 (4)0.41025 (18)0.0929 (19)
O80.3269 (4)0.2849 (6)0.4107 (3)0.143 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0283 (3)0.0425 (4)0.0398 (4)0.0013 (3)0.0002 (3)0.0015 (4)
P10.0346 (8)0.0400 (8)0.0326 (9)0.0008 (6)0.0026 (7)0.0021 (7)
P20.0309 (7)0.0416 (9)0.0349 (9)0.0024 (6)0.0016 (7)0.0027 (7)
N10.033 (3)0.030 (2)0.036 (3)0.0017 (19)0.001 (2)0.002 (2)
N20.034 (3)0.036 (3)0.038 (3)0.002 (2)0.003 (2)0.005 (2)
C10.041 (3)0.036 (3)0.051 (4)0.003 (3)0.004 (3)0.002 (3)
C20.059 (4)0.033 (3)0.059 (4)0.005 (3)0.009 (3)0.006 (3)
C30.044 (4)0.043 (4)0.080 (5)0.020 (3)0.004 (4)0.005 (3)
C40.033 (3)0.046 (4)0.052 (4)0.010 (3)0.003 (3)0.010 (3)
C50.034 (3)0.027 (3)0.036 (4)0.004 (2)0.003 (3)0.012 (2)
C60.025 (3)0.039 (3)0.023 (3)0.006 (2)0.000 (2)0.007 (2)
C70.037 (3)0.047 (4)0.042 (4)0.011 (3)0.003 (3)0.005 (3)
C80.044 (4)0.065 (5)0.046 (4)0.024 (3)0.007 (3)0.007 (3)
C90.068 (5)0.045 (4)0.048 (4)0.014 (3)0.006 (4)0.015 (3)
C100.046 (4)0.032 (3)0.060 (4)0.002 (3)0.010 (3)0.005 (3)
C110.032 (3)0.071 (5)0.063 (5)0.000 (3)0.001 (3)0.010 (4)
C120.035 (3)0.074 (5)0.065 (5)0.010 (3)0.019 (3)0.010 (4)
C130.051 (4)0.042 (3)0.035 (4)0.007 (3)0.000 (3)0.010 (3)
C140.038 (3)0.051 (4)0.045 (4)0.005 (3)0.009 (3)0.004 (3)
C150.032 (3)0.044 (4)0.046 (4)0.002 (3)0.003 (3)0.000 (3)
C160.032 (3)0.041 (3)0.038 (4)0.005 (2)0.003 (3)0.009 (3)
C170.079 (5)0.044 (4)0.054 (5)0.001 (3)0.023 (4)0.003 (3)
C180.095 (6)0.067 (5)0.056 (5)0.003 (4)0.019 (4)0.014 (4)
C190.075 (5)0.035 (4)0.084 (6)0.003 (3)0.003 (4)0.011 (4)
C200.076 (5)0.050 (4)0.072 (6)0.011 (4)0.002 (4)0.010 (4)
C210.056 (4)0.048 (4)0.047 (4)0.009 (3)0.007 (3)0.001 (3)
C220.056 (4)0.037 (3)0.042 (4)0.005 (3)0.013 (3)0.002 (3)
C230.070 (5)0.113 (7)0.061 (5)0.016 (5)0.014 (4)0.040 (5)
C240.134 (9)0.134 (8)0.065 (6)0.023 (7)0.030 (6)0.054 (6)
C250.126 (8)0.071 (5)0.079 (7)0.008 (5)0.066 (7)0.011 (5)
C260.078 (5)0.069 (5)0.074 (6)0.028 (4)0.033 (5)0.023 (5)
C270.062 (4)0.064 (4)0.048 (4)0.023 (3)0.017 (4)0.020 (3)
C280.032 (3)0.041 (3)0.044 (4)0.000 (2)0.001 (3)0.007 (3)
C290.044 (4)0.063 (4)0.041 (4)0.012 (3)0.006 (3)0.000 (3)
C300.055 (4)0.073 (5)0.064 (5)0.031 (4)0.010 (4)0.004 (4)
C310.089 (6)0.058 (5)0.078 (6)0.019 (4)0.018 (5)0.012 (4)
C320.077 (5)0.079 (5)0.083 (6)0.002 (4)0.007 (5)0.037 (5)
C330.043 (4)0.058 (4)0.066 (5)0.001 (3)0.004 (3)0.014 (3)
C340.031 (3)0.050 (4)0.030 (3)0.003 (3)0.004 (3)0.002 (3)
C350.044 (3)0.058 (4)0.051 (4)0.002 (3)0.002 (3)0.011 (3)
C360.060 (4)0.054 (4)0.073 (6)0.011 (3)0.014 (4)0.014 (4)
C370.086 (5)0.054 (5)0.054 (5)0.008 (4)0.021 (4)0.019 (4)
C380.092 (5)0.069 (5)0.036 (4)0.020 (4)0.001 (4)0.014 (4)
C390.051 (4)0.051 (4)0.044 (4)0.000 (3)0.002 (3)0.003 (3)
Cu20.0270 (3)0.0389 (4)0.0421 (4)0.0016 (3)0.0033 (3)0.0024 (4)
P30.0292 (7)0.0399 (9)0.0371 (9)0.0026 (6)0.0015 (7)0.0000 (7)
P40.0314 (8)0.0373 (8)0.0342 (9)0.0001 (6)0.0001 (7)0.0036 (6)
N30.030 (3)0.035 (3)0.040 (3)0.0040 (19)0.006 (2)0.001 (2)
N40.034 (3)0.029 (2)0.038 (3)0.0022 (19)0.006 (2)0.002 (2)
C400.041 (3)0.038 (3)0.046 (4)0.001 (3)0.001 (3)0.003 (3)
C410.060 (4)0.030 (3)0.061 (5)0.015 (3)0.004 (4)0.007 (3)
C420.044 (4)0.062 (4)0.048 (4)0.023 (3)0.015 (3)0.004 (3)
C430.034 (3)0.043 (3)0.037 (4)0.015 (3)0.008 (3)0.003 (3)
C440.027 (3)0.034 (3)0.030 (3)0.002 (2)0.000 (2)0.003 (2)
C450.028 (3)0.033 (3)0.030 (3)0.002 (2)0.007 (3)0.006 (2)
C460.035 (3)0.043 (4)0.051 (4)0.003 (3)0.000 (3)0.008 (3)
C470.039 (4)0.052 (4)0.066 (5)0.018 (3)0.004 (3)0.000 (3)
C480.061 (4)0.038 (3)0.070 (5)0.011 (3)0.005 (4)0.015 (3)
C490.041 (3)0.037 (3)0.053 (4)0.000 (3)0.003 (3)0.011 (3)
C500.032 (3)0.070 (5)0.060 (5)0.013 (3)0.004 (3)0.005 (4)
C510.031 (4)0.067 (5)0.065 (5)0.009 (3)0.000 (3)0.008 (4)
C520.035 (3)0.050 (4)0.033 (4)0.003 (2)0.011 (3)0.004 (3)
C530.029 (3)0.066 (4)0.038 (4)0.007 (3)0.006 (3)0.003 (3)
C540.045 (3)0.048 (4)0.034 (4)0.008 (3)0.002 (3)0.001 (3)
C550.043 (4)0.045 (3)0.040 (4)0.004 (3)0.011 (3)0.002 (3)
C560.068 (5)0.081 (5)0.054 (5)0.021 (4)0.003 (4)0.004 (4)
C570.104 (8)0.092 (6)0.077 (6)0.048 (6)0.025 (6)0.007 (6)
C580.174 (11)0.063 (6)0.073 (7)0.029 (7)0.056 (7)0.012 (5)
C590.132 (8)0.060 (5)0.088 (7)0.028 (6)0.030 (6)0.022 (5)
C600.066 (5)0.059 (4)0.068 (5)0.013 (4)0.009 (4)0.016 (4)
C610.037 (3)0.039 (3)0.040 (4)0.013 (3)0.009 (3)0.003 (3)
C620.059 (4)0.048 (4)0.040 (4)0.015 (3)0.002 (3)0.003 (3)
C630.091 (6)0.070 (5)0.039 (4)0.025 (4)0.004 (4)0.001 (4)
C640.083 (5)0.074 (5)0.046 (5)0.026 (4)0.025 (4)0.020 (4)
C650.062 (4)0.047 (4)0.069 (5)0.004 (3)0.025 (4)0.014 (4)
C660.042 (3)0.054 (4)0.051 (4)0.008 (3)0.001 (3)0.003 (3)
C670.035 (3)0.037 (3)0.035 (3)0.003 (2)0.006 (3)0.002 (2)
C680.050 (4)0.043 (4)0.054 (4)0.007 (3)0.007 (3)0.001 (3)
C690.088 (5)0.042 (4)0.060 (5)0.010 (4)0.008 (4)0.005 (3)
C700.101 (6)0.047 (4)0.062 (5)0.007 (4)0.004 (5)0.009 (4)
C710.108 (6)0.057 (5)0.063 (5)0.012 (4)0.035 (5)0.001 (4)
C720.080 (5)0.049 (4)0.057 (5)0.008 (4)0.029 (4)0.002 (3)
C730.051 (4)0.034 (3)0.047 (4)0.004 (3)0.012 (3)0.000 (3)
C740.068 (5)0.072 (5)0.056 (5)0.021 (4)0.013 (4)0.018 (4)
C750.088 (6)0.081 (6)0.110 (8)0.035 (5)0.062 (6)0.022 (6)
C760.142 (10)0.063 (5)0.126 (10)0.011 (6)0.089 (9)0.038 (6)
C770.130 (9)0.116 (7)0.077 (6)0.057 (7)0.051 (7)0.053 (5)
C780.072 (5)0.116 (7)0.059 (5)0.028 (5)0.018 (5)0.033 (5)
Cl10.0366 (9)0.0854 (12)0.0668 (12)0.0051 (9)0.0085 (9)0.0126 (10)
O10.057 (3)0.109 (4)0.135 (5)0.005 (3)0.022 (4)0.045 (4)
O20.078 (4)0.180 (7)0.112 (6)0.049 (4)0.034 (4)0.016 (5)
O30.088 (4)0.074 (3)0.159 (6)0.000 (3)0.036 (4)0.036 (4)
O40.126 (6)0.231 (9)0.118 (6)0.085 (6)0.056 (5)0.002 (6)
Cl20.0373 (9)0.0942 (13)0.0507 (11)0.0079 (9)0.0045 (8)0.0133 (10)
O50.048 (3)0.132 (5)0.096 (4)0.019 (3)0.001 (3)0.042 (4)
O60.120 (5)0.199 (7)0.101 (6)0.088 (5)0.054 (5)0.025 (5)
O70.090 (4)0.084 (3)0.104 (5)0.013 (3)0.039 (4)0.023 (3)
O80.082 (5)0.202 (7)0.146 (7)0.051 (5)0.053 (5)0.027 (6)
Geometric parameters (Å, º) top
Cu1—N22.046 (4)P3—C551.817 (6)
Cu1—N12.073 (4)P3—C611.823 (6)
Cu1—P22.2344 (16)P3—C521.831 (6)
Cu1—P12.2355 (16)P4—C671.813 (5)
P1—C161.830 (6)P4—C731.817 (6)
P1—C221.829 (6)P4—C541.836 (5)
P1—C131.836 (5)N3—C401.322 (6)
P2—C341.813 (6)N3—C441.355 (6)
P2—C281.826 (6)N4—C491.327 (6)
P2—C151.841 (6)N4—C451.361 (6)
N1—C11.317 (7)C40—C411.396 (8)
N1—C51.360 (6)C40—H400.9300
N2—C101.315 (6)C41—C421.355 (8)
N2—C61.367 (6)C41—H410.9300
C1—C21.367 (7)C42—C431.399 (8)
C1—H10.9300C42—H420.9300
C2—C31.347 (8)C43—C441.403 (7)
C2—H20.9300C43—C501.413 (8)
C3—C41.408 (8)C44—C451.433 (7)
C3—H30.9300C45—C461.401 (7)
C4—C51.402 (7)C46—C471.411 (8)
C4—C111.417 (8)C46—C511.418 (8)
C5—C61.449 (7)C47—C481.343 (8)
C6—C71.395 (7)C47—H470.9300
C7—C81.387 (8)C48—C491.377 (7)
C7—C121.433 (8)C48—H480.9300
C8—C91.367 (9)C49—H490.9300
C8—H80.9300C50—C511.357 (9)
C9—C101.378 (8)C50—H500.9300
C9—H90.9300C51—H510.9300
C10—H100.9300C52—C531.541 (8)
C11—C121.351 (9)C52—H52A0.9700
C11—H110.9300C52—H52B0.9700
C12—H120.9300C53—C541.519 (8)
C13—C141.539 (8)C53—H53A0.9700
C13—H13A0.9700C53—H53B0.9700
C13—H13B0.9700C54—H54A0.9700
C14—C151.536 (8)C54—H54B0.9700
C14—H14A0.9700C55—C561.380 (8)
C14—H14B0.9700C55—C601.388 (9)
C15—H15A0.9700C56—C571.392 (10)
C15—H15B0.9700C56—H560.9300
C16—C171.363 (8)C57—C581.367 (14)
C16—C211.379 (8)C57—H570.9300
C17—C181.370 (9)C58—C591.363 (13)
C17—H170.9300C58—H580.9300
C18—C191.376 (10)C59—C601.392 (10)
C18—H180.9300C59—H590.9300
C19—C201.346 (9)C60—H600.9300
C19—H190.9300C61—C661.381 (8)
C20—C211.384 (8)C61—C621.377 (8)
C20—H200.9300C62—C631.379 (9)
C21—H210.9300C62—H620.9300
C22—C231.361 (9)C63—C641.375 (10)
C22—C271.372 (8)C63—H630.9300
C23—C241.409 (11)C64—C651.379 (10)
C23—H230.9300C64—H640.9300
C24—C251.328 (12)C65—C661.382 (8)
C24—H240.9300C65—H650.9300
C25—C261.326 (12)C66—H660.9300
C25—H250.9300C67—C681.382 (8)
C26—C271.390 (10)C67—C721.396 (8)
C26—H260.9300C68—C691.394 (8)
C27—H270.9300C68—H680.9300
C28—C291.369 (7)C69—C701.352 (10)
C28—C331.397 (8)C69—H690.9300
C29—C301.390 (9)C70—C711.348 (10)
C29—H290.9300C70—H700.9300
C30—C311.375 (10)C71—C721.384 (9)
C30—H300.9300C71—H710.9300
C31—C321.356 (10)C72—H720.9300
C31—H310.9300C73—C741.375 (8)
C32—C331.382 (9)C73—C781.372 (9)
C32—H320.9300C74—C751.411 (10)
C33—H330.9300C74—H740.9300
C34—C391.393 (8)C75—C761.375 (14)
C34—C351.400 (8)C75—H750.9300
C35—C361.387 (8)C76—C771.343 (13)
C35—H350.9300C76—H760.9300
C36—C371.367 (10)C77—C781.365 (10)
C36—H360.9300C77—H770.9300
C37—C381.369 (10)C78—H780.9300
C37—H370.9300Cl1—O41.379 (6)
C38—C391.382 (9)Cl1—O11.392 (5)
C38—H380.9300Cl1—O31.401 (6)
C39—H390.9300Cl1—O21.416 (6)
Cu2—N42.058 (4)Cl2—O61.388 (6)
Cu2—N32.077 (4)Cl2—O51.414 (5)
Cu2—P32.2302 (16)Cl2—O81.406 (7)
Cu2—P42.2457 (17)Cl2—O71.417 (5)
N2—Cu1—N181.93 (17)C55—P3—C61102.1 (3)
N2—Cu1—P2117.00 (14)C55—P3—C52106.5 (3)
N1—Cu1—P2119.79 (13)C61—P3—C52101.0 (2)
N2—Cu1—P1124.23 (14)C55—P3—Cu2113.53 (18)
N1—Cu1—P1108.49 (14)C61—P3—Cu2121.72 (19)
P2—Cu1—P1104.68 (6)C52—P3—Cu2110.39 (18)
C16—P1—C22103.0 (3)C67—P4—C73103.2 (3)
C16—P1—C13103.0 (3)C67—P4—C54102.8 (3)
C22—P1—C13103.7 (3)C73—P4—C54103.1 (3)
C16—P1—Cu1121.58 (19)C67—P4—Cu2120.40 (19)
C22—P1—Cu1115.1 (2)C73—P4—Cu2116.8 (2)
C13—P1—Cu1108.6 (2)C54—P4—Cu2108.4 (2)
C34—P2—C28102.7 (3)C40—N3—C44118.3 (4)
C34—P2—C15101.0 (3)C40—N3—Cu2130.3 (4)
C28—P2—C15105.9 (3)C44—N3—Cu2111.3 (3)
C34—P2—Cu1120.14 (19)C49—N4—C45117.5 (4)
C28—P2—Cu1115.02 (18)C49—N4—Cu2130.5 (4)
C15—P2—Cu1110.3 (2)C45—N4—Cu2111.5 (3)
C1—N1—C5116.4 (5)N3—C40—C41122.6 (5)
C1—N1—Cu1131.6 (4)N3—C40—H40118.7
C5—N1—Cu1111.4 (3)C41—C40—H40118.7
C10—N2—C6116.0 (5)C42—C41—C40119.2 (5)
C10—N2—Cu1132.1 (4)C42—C41—H41120.4
C6—N2—Cu1111.9 (3)C40—C41—H41120.4
N1—C1—C2124.8 (5)C41—C42—C43120.3 (5)
N1—C1—H1117.6C41—C42—H42119.8
C2—C1—H1117.6C43—C42—H42119.8
C3—C2—C1119.3 (5)C44—C43—C42116.8 (5)
C3—C2—H2120.4C44—C43—C50119.5 (5)
C1—C2—H2120.4C42—C43—C50123.7 (5)
C2—C3—C4119.7 (5)N3—C44—C43122.8 (5)
C2—C3—H3120.2N3—C44—C45117.6 (4)
C4—C3—H3120.2C43—C44—C45119.6 (5)
C5—C4—C3116.5 (5)N4—C45—C46122.6 (5)
C5—C4—C11120.1 (6)N4—C45—C44117.9 (4)
C3—C4—C11123.4 (6)C46—C45—C44119.4 (5)
N1—C5—C4123.3 (5)C45—C46—C47117.2 (5)
N1—C5—C6117.1 (4)C45—C46—C51119.3 (5)
C4—C5—C6119.6 (5)C47—C46—C51123.5 (5)
N2—C6—C7123.5 (5)C48—C47—C46119.1 (5)
N2—C6—C5117.4 (4)C48—C47—H47120.4
C7—C6—C5119.0 (5)C46—C47—H47120.4
C8—C7—C6117.1 (5)C47—C48—C49120.6 (6)
C8—C7—C12123.7 (5)C47—C48—H48119.7
C6—C7—C12119.2 (5)C49—C48—H48119.7
C9—C8—C7120.1 (5)N4—C49—C48122.9 (5)
C9—C8—H8120.0N4—C49—H49118.5
C7—C8—H8120.0C48—C49—H49118.5
C8—C9—C10118.2 (5)C51—C50—C43120.8 (6)
C8—C9—H9120.9C51—C50—H50119.6
C10—C9—H9120.9C43—C50—H50119.6
N2—C10—C9125.1 (6)C50—C51—C46121.2 (6)
N2—C10—H10117.5C50—C51—H51119.4
C9—C10—H10117.5C46—C51—H51119.4
C12—C11—C4120.1 (6)C53—C52—P3116.8 (4)
C12—C11—H11119.9C53—C52—H52A108.1
C4—C11—H11119.9P3—C52—H52A108.1
C11—C12—C7121.9 (6)C53—C52—H52B108.1
C11—C12—H12119.1P3—C52—H52B108.1
C7—C12—H12119.1H52A—C52—H52B107.3
C14—C13—P1112.9 (4)C54—C53—C52115.1 (5)
C14—C13—H13A109.0C54—C53—H53A108.5
P1—C13—H13A109.0C52—C53—H53A108.5
C14—C13—H13B109.0C54—C53—H53B108.5
P1—C13—H13B109.0C52—C53—H53B108.5
H13A—C13—H13B107.8H53A—C53—H53B107.5
C13—C14—C15115.2 (5)C53—C54—P4112.9 (4)
C13—C14—H14A108.5C53—C54—H54A109.0
C15—C14—H14A108.5P4—C54—H54A109.0
C13—C14—H14B108.5C53—C54—H54B109.0
C15—C14—H14B108.5P4—C54—H54B109.0
H14A—C14—H14B107.5H54A—C54—H54B107.8
C14—C15—P2115.6 (4)C56—C55—C60119.4 (6)
C14—C15—H15A108.4C56—C55—P3123.6 (5)
P2—C15—H15A108.4C60—C55—P3117.0 (5)
C14—C15—H15B108.4C55—C56—C57120.1 (8)
P2—C15—H15B108.4C55—C56—H56119.9
H15A—C15—H15B107.5C57—C56—H56119.9
C17—C16—C21118.1 (5)C58—C57—C56119.8 (8)
C17—C16—P1123.3 (4)C58—C57—H57120.1
C21—C16—P1118.6 (5)C56—C57—H57120.1
C16—C17—C18121.8 (6)C59—C58—C57120.9 (8)
C16—C17—H17119.1C59—C58—H58119.5
C18—C17—H17119.1C57—C58—H58119.5
C17—C18—C19119.6 (7)C58—C59—C60119.9 (9)
C17—C18—H18120.2C58—C59—H59120.0
C19—C18—H18120.2C60—C59—H59120.0
C20—C19—C18119.2 (6)C55—C60—C59119.9 (7)
C20—C19—H19120.4C55—C60—H60120.1
C18—C19—H19120.4C59—C60—H60120.1
C19—C20—C21121.2 (6)C66—C61—C62118.1 (6)
C19—C20—H20119.4C66—C61—P3119.7 (5)
C21—C20—H20119.4C62—C61—P3122.1 (5)
C20—C21—C16119.9 (6)C61—C62—C63121.7 (6)
C20—C21—H21120.0C61—C62—H62119.1
C16—C21—H21120.0C63—C62—H62119.1
C23—C22—C27117.9 (6)C64—C63—C62119.5 (7)
C23—C22—P1123.8 (5)C64—C63—H63120.3
C27—C22—P1118.2 (5)C62—C63—H63120.3
C22—C23—C24118.8 (8)C63—C64—C65119.9 (7)
C22—C23—H23120.6C63—C64—H64120.1
C24—C23—H23120.6C65—C64—H64120.1
C25—C24—C23122.9 (9)C66—C65—C64119.9 (7)
C25—C24—H24118.6C66—C65—H65120.1
C23—C24—H24118.6C64—C65—H65120.1
C24—C25—C26118.2 (8)C61—C66—C65121.0 (6)
C24—C25—H25120.9C61—C66—H66119.5
C26—C25—H25120.9C65—C66—H66119.5
C25—C26—C27121.6 (8)C68—C67—C72117.2 (5)
C25—C26—H26119.2C68—C67—P4119.9 (5)
C27—C26—H26119.2C72—C67—P4122.9 (5)
C22—C27—C26120.7 (7)C69—C68—C67121.5 (6)
C22—C27—H27119.7C69—C68—H68119.3
C26—C27—H27119.7C67—C68—H68119.3
C29—C28—C33118.7 (6)C70—C69—C68119.0 (6)
C29—C28—P2124.0 (5)C70—C69—H69120.5
C33—C28—P2117.3 (4)C68—C69—H69120.5
C28—C29—C30119.7 (6)C69—C70—C71121.6 (7)
C28—C29—H29120.2C69—C70—H70119.2
C30—C29—H29120.2C71—C70—H70119.2
C31—C30—C29121.4 (6)C70—C71—C72120.0 (7)
C31—C30—H30119.3C70—C71—H71120.0
C29—C30—H30119.3C72—C71—H71120.0
C32—C31—C30118.9 (7)C71—C72—C67120.7 (6)
C32—C31—H31120.5C71—C72—H72119.6
C30—C31—H31120.5C67—C72—H72119.6
C31—C32—C33120.7 (7)C74—C73—C78116.9 (6)
C31—C32—H32119.6C74—C73—P4118.6 (5)
C33—C32—H32119.6C78—C73—P4124.5 (5)
C32—C33—C28120.5 (6)C73—C74—C75120.8 (8)
C32—C33—H33119.7C73—C74—H74119.6
C28—C33—H33119.7C75—C74—H74119.6
C39—C34—C35117.8 (5)C76—C75—C74119.5 (9)
C39—C34—P2123.7 (4)C76—C75—H75120.2
C35—C34—P2118.4 (5)C74—C75—H75120.2
C36—C35—C34121.1 (7)C77—C76—C75119.3 (9)
C36—C35—H35119.5C77—C76—H76120.3
C34—C35—H35119.5C75—C76—H76120.3
C37—C36—C35119.6 (6)C76—C77—C78120.9 (10)
C37—C36—H36120.2C76—C77—H77119.6
C35—C36—H36120.2C78—C77—H77119.6
C36—C37—C38120.4 (6)C77—C78—C73122.5 (8)
C36—C37—H37119.8C77—C78—H78118.7
C38—C37—H37119.8C73—C78—H78118.7
C37—C38—C39120.7 (7)O4—Cl1—O1110.8 (5)
C37—C38—H38119.6O4—Cl1—O3111.5 (5)
C39—C38—H38119.6O1—Cl1—O3109.2 (3)
C38—C39—C34120.3 (6)O4—Cl1—O2107.8 (5)
C38—C39—H39119.8O1—Cl1—O2108.1 (4)
C34—C39—H39119.8O3—Cl1—O2109.4 (5)
N4—Cu2—N381.48 (16)O6—Cl2—O5110.7 (4)
N4—Cu2—P3119.94 (13)O6—Cl2—O8108.8 (5)
N3—Cu2—P3116.47 (13)O5—Cl2—O8108.1 (4)
N4—Cu2—P4111.65 (14)O6—Cl2—O7111.0 (4)
N3—Cu2—P4122.40 (13)O5—Cl2—O7110.7 (3)
P3—Cu2—P4104.56 (6)O8—Cl2—O7107.5 (4)
N2—Cu1—P1—C1646.7 (3)N4—Cu2—P3—C55135.9 (3)
N1—Cu1—P1—C16139.5 (2)N3—Cu2—P3—C5540.4 (3)
P2—Cu1—P1—C1691.6 (2)P4—Cu2—P3—C5598.0 (2)
N2—Cu1—P1—C2278.7 (2)N4—Cu2—P3—C6113.3 (3)
N1—Cu1—P1—C2214.1 (2)N3—Cu2—P3—C6182.2 (3)
P2—Cu1—P1—C22143.1 (2)P4—Cu2—P3—C61139.4 (2)
N2—Cu1—P1—C13165.7 (2)N4—Cu2—P3—C52104.6 (2)
N1—Cu1—P1—C13101.5 (2)N3—Cu2—P3—C52159.9 (2)
P2—Cu1—P1—C1327.4 (2)P4—Cu2—P3—C5221.5 (2)
N2—Cu1—P2—C3478.5 (3)N4—Cu2—P4—C67138.2 (2)
N1—Cu1—P2—C3417.8 (3)N3—Cu2—P4—C6744.6 (2)
P1—Cu1—P2—C34139.7 (2)P3—Cu2—P4—C6790.7 (2)
N2—Cu1—P2—C2845.0 (2)N4—Cu2—P4—C7311.8 (2)
N1—Cu1—P2—C28141.3 (2)N3—Cu2—P4—C7381.8 (2)
P1—Cu1—P2—C2896.8 (2)P3—Cu2—P4—C73142.9 (2)
N2—Cu1—P2—C15164.7 (2)N4—Cu2—P4—C54104.1 (2)
N1—Cu1—P2—C1599.0 (2)N3—Cu2—P4—C54162.3 (2)
P1—Cu1—P2—C1522.9 (2)P3—Cu2—P4—C5427.1 (2)
N2—Cu1—N1—C1173.6 (6)N4—Cu2—N3—C40178.7 (5)
P2—Cu1—N1—C169.8 (6)P3—Cu2—N3—C4059.5 (5)
P1—Cu1—N1—C150.2 (5)P4—Cu2—N3—C4071.0 (5)
N2—Cu1—N1—C52.9 (4)N4—Cu2—N3—C442.6 (4)
P2—Cu1—N1—C5119.5 (3)P3—Cu2—N3—C44121.9 (3)
P1—Cu1—N1—C5120.6 (3)P4—Cu2—N3—C44107.7 (3)
N1—Cu1—N2—C10179.4 (6)N3—Cu2—N4—C49175.9 (5)
P2—Cu1—N2—C1061.2 (6)P3—Cu2—N4—C4968.3 (5)
P1—Cu1—N2—C1072.5 (6)P4—Cu2—N4—C4954.4 (5)
N1—Cu1—N2—C60.3 (4)N3—Cu2—N4—C454.2 (4)
P2—Cu1—N2—C6119.7 (3)P3—Cu2—N4—C45119.9 (3)
P1—Cu1—N2—C6106.6 (3)P4—Cu2—N4—C45117.4 (3)
C5—N1—C1—C20.5 (9)C44—N3—C40—C410.6 (8)
Cu1—N1—C1—C2170.9 (5)Cu2—N3—C40—C41179.3 (4)
N1—C1—C2—C31.2 (10)N3—C40—C41—C420.6 (9)
C1—C2—C3—C42.9 (10)C40—C41—C42—C430.0 (9)
C2—C3—C4—C53.8 (9)C41—C42—C43—C440.6 (9)
C2—C3—C4—C11176.6 (6)C41—C42—C43—C50178.4 (6)
C1—N1—C5—C41.6 (8)C40—N3—C44—C430.0 (8)
Cu1—N1—C5—C4173.9 (4)Cu2—N3—C44—C43178.9 (4)
C1—N1—C5—C6177.3 (5)C40—N3—C44—C45179.5 (5)
Cu1—N1—C5—C65.0 (6)Cu2—N3—C44—C450.6 (6)
C3—C4—C5—N13.3 (9)C42—C43—C44—N30.5 (8)
C11—C4—C5—N1177.1 (6)C50—C43—C44—N3178.4 (5)
C3—C4—C5—C6175.7 (5)C42—C43—C44—C45180.0 (5)
C11—C4—C5—C64.0 (9)C50—C43—C44—C451.1 (8)
C10—N2—C6—C70.4 (8)C49—N4—C45—C460.7 (8)
Cu1—N2—C6—C7179.7 (4)Cu2—N4—C45—C46173.6 (4)
C10—N2—C6—C5177.0 (5)C49—N4—C45—C44178.2 (5)
Cu1—N2—C6—C52.3 (6)Cu2—N4—C45—C445.2 (6)
N1—C5—C6—N25.1 (7)N3—C44—C45—N43.2 (7)
C4—C5—C6—N2173.9 (5)C43—C44—C45—N4177.3 (5)
N1—C5—C6—C7177.4 (5)N3—C44—C45—C46175.7 (5)
C4—C5—C6—C73.6 (8)C43—C44—C45—C463.8 (8)
N2—C6—C7—C82.1 (8)N4—C45—C46—C471.8 (8)
C5—C6—C7—C8179.4 (5)C44—C45—C46—C47177.0 (5)
N2—C6—C7—C12176.8 (5)N4—C45—C46—C51178.1 (5)
C5—C6—C7—C120.6 (8)C44—C45—C46—C513.1 (8)
C6—C7—C8—C92.8 (9)C45—C46—C47—C482.1 (9)
C12—C7—C8—C9176.0 (6)C51—C46—C47—C48177.8 (6)
C7—C8—C9—C101.0 (9)C46—C47—C48—C491.4 (10)
C6—N2—C10—C92.4 (9)C45—N4—C49—C480.2 (9)
Cu1—N2—C10—C9178.4 (5)Cu2—N4—C49—C48171.2 (5)
C8—C9—C10—N21.8 (10)C47—C48—C49—N40.2 (10)
C5—C4—C11—C121.2 (10)C44—C43—C50—C512.4 (9)
C3—C4—C11—C12178.4 (7)C42—C43—C50—C51176.4 (6)
C4—C11—C12—C72.0 (11)C43—C50—C51—C463.2 (10)
C8—C7—C12—C11176.5 (7)C45—C46—C51—C500.4 (9)
C6—C7—C12—C112.3 (10)C47—C46—C51—C50179.5 (7)
C16—P1—C13—C1476.4 (5)C55—P3—C52—C5382.1 (5)
C22—P1—C13—C14176.5 (4)C61—P3—C52—C53171.6 (4)
Cu1—P1—C13—C1453.7 (4)Cu2—P3—C52—C5341.5 (5)
P1—C13—C14—C1582.3 (5)P3—C52—C53—C5474.9 (6)
C13—C14—C15—P276.0 (6)C52—C53—C54—P482.3 (6)
C34—P2—C15—C14171.4 (4)C67—P4—C54—C5374.0 (5)
C28—P2—C15—C1481.8 (5)C73—P4—C54—C53179.0 (4)
Cu1—P2—C15—C1443.3 (5)Cu2—P4—C54—C5354.5 (4)
C22—P1—C16—C1764.1 (6)C61—P3—C55—C56106.5 (6)
C13—P1—C16—C1743.5 (6)C52—P3—C55—C561.0 (6)
Cu1—P1—C16—C17165.2 (5)Cu2—P3—C55—C56120.7 (5)
C22—P1—C16—C21115.1 (5)C61—P3—C55—C6073.1 (5)
C13—P1—C16—C21137.3 (5)C52—P3—C55—C60178.5 (5)
Cu1—P1—C16—C2115.6 (6)Cu2—P3—C55—C6059.8 (5)
C21—C16—C17—C180.4 (10)C60—C55—C56—C570.7 (10)
P1—C16—C17—C18179.6 (6)P3—C55—C56—C57179.7 (6)
C16—C17—C18—C192.1 (12)C55—C56—C57—C580.3 (12)
C17—C18—C19—C203.6 (12)C56—C57—C58—C591.2 (14)
C18—C19—C20—C212.6 (11)C57—C58—C59—C601.2 (14)
C19—C20—C21—C160.1 (11)C56—C55—C60—C590.8 (10)
C17—C16—C21—C201.4 (9)P3—C55—C60—C59179.6 (6)
P1—C16—C21—C20179.4 (5)C58—C59—C60—C550.2 (12)
C16—P1—C22—C2380.0 (6)C55—P3—C61—C66154.9 (5)
C13—P1—C22—C2327.1 (7)C52—P3—C61—C6695.3 (5)
Cu1—P1—C22—C23145.5 (6)Cu2—P3—C61—C6627.1 (5)
C16—P1—C22—C27102.0 (5)C55—P3—C61—C6229.3 (5)
C13—P1—C22—C27150.9 (5)C52—P3—C61—C6280.5 (5)
Cu1—P1—C22—C2732.5 (5)Cu2—P3—C61—C62157.0 (4)
C27—C22—C23—C240.0 (11)C66—C61—C62—C631.2 (9)
P1—C22—C23—C24178.1 (7)P3—C61—C62—C63174.7 (5)
C22—C23—C24—C250.1 (15)C61—C62—C63—C640.7 (10)
C23—C24—C25—C260.6 (16)C62—C63—C64—C650.4 (10)
C24—C25—C26—C271.3 (13)C63—C64—C65—C660.8 (10)
C23—C22—C27—C260.7 (9)C62—C61—C66—C650.7 (9)
P1—C22—C27—C26178.9 (5)P3—C61—C66—C65175.3 (5)
C25—C26—C27—C221.4 (11)C64—C65—C66—C610.3 (9)
C34—P2—C28—C29107.9 (5)C73—P4—C67—C68112.9 (5)
C15—P2—C28—C292.3 (6)C54—P4—C67—C68140.1 (5)
Cu1—P2—C28—C29119.8 (5)Cu2—P4—C67—C6819.6 (5)
C34—P2—C28—C3370.6 (5)C73—P4—C67—C7265.6 (6)
C15—P2—C28—C33176.1 (5)C54—P4—C67—C7241.4 (6)
Cu1—P2—C28—C3361.8 (5)Cu2—P4—C67—C72162.0 (5)
C33—C28—C29—C300.0 (9)C72—C67—C68—C691.7 (9)
P2—C28—C29—C30178.4 (5)P4—C67—C68—C69179.7 (5)
C28—C29—C30—C311.6 (11)C67—C68—C69—C701.3 (10)
C29—C30—C31—C321.6 (12)C68—C69—C70—C710.9 (11)
C30—C31—C32—C330.2 (13)C69—C70—C71—C721.1 (13)
C31—C32—C33—C281.3 (13)C70—C71—C72—C671.6 (12)
C29—C28—C33—C321.4 (10)C68—C67—C72—C711.9 (10)
P2—C28—C33—C32177.2 (6)P4—C67—C72—C71179.7 (6)
C28—P2—C34—C3921.5 (5)C67—P4—C73—C74109.9 (5)
C15—P2—C34—C3987.7 (5)C54—P4—C73—C74143.4 (5)
Cu1—P2—C34—C39150.8 (4)Cu2—P4—C73—C7424.7 (5)
C28—P2—C34—C35159.0 (4)C67—P4—C73—C7870.6 (6)
C15—P2—C34—C3591.8 (5)C54—P4—C73—C7836.2 (6)
Cu1—P2—C34—C3529.7 (5)Cu2—P4—C73—C78154.9 (5)
C39—C34—C35—C361.5 (9)C78—C73—C74—C751.3 (10)
P2—C34—C35—C36178.0 (5)P4—C73—C74—C75178.3 (5)
C34—C35—C36—C370.0 (10)C73—C74—C75—C761.2 (12)
C35—C36—C37—C381.8 (10)C74—C75—C76—C770.6 (14)
C36—C37—C38—C392.1 (11)C75—C76—C77—C782.3 (15)
C37—C38—C39—C340.6 (10)C76—C77—C78—C732.3 (14)
C35—C34—C39—C381.2 (9)C74—C73—C78—C770.4 (11)
P2—C34—C39—C38178.3 (5)P4—C73—C78—C77180.0 (6)

Experimental details

Crystal data
Chemical formula[Cu(C12H8N2)(C27H26P2)]ClO4
Mr755.61
Crystal system, space groupMonoclinic, Cc
Temperature (K)298
a, b, c (Å)16.6548 (15), 12.9238 (12), 32.936 (3)
β (°) 90.126 (1)
V3)7089.2 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.83
Crystal size (mm)0.45 × 0.40 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.708, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
10139, 10139, 8324
Rint0.035
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.074, 0.91
No. of reflections10139
No. of parameters884
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.27
Absolute structureFlack (1983), 6243 Friedel pairs
Absolute structure parameter0.009 (12)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No.21171119), the CAIQ Basic Research Program (No. 2010 J K022), the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901, the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality and the State Key Laboratory of Functional Materials for Informatics, Shanghai Institute of Microsystem and Information Technology, Chinese Academy of Sciences.

References

First citationAbakumov, G. A., Cherkasov, V. K., Krashilina, A. V., Eremenko, I. L. & Nefedov, S. E. (1998). Russ. Chem. Bull. 11, 2333–2340.  Google Scholar
First citationAffandi, D., Price, S. J. B., Effendy, H., Harvey, P. J., Healy, P. C., Ruch, B. E. & White, A. H. (1997). J. Chem. Soc. Dalton Trans. pp. 1411–1420.  CSD CrossRef Web of Science Google Scholar
First citationAlanidis, P., Cox, P. J., Divanidis, S. & Tsipis, A. C. (2002). Inorg. Chem. 41, 6875–6886.  Web of Science PubMed Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFournier, E., Sicard, S., Decken, A. & Harvey, P. D. (2004). Inorg. Chem. 43, 1491–1501.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationJin, Q. H., Chen, L. M., Li, P. Z., Deng, S. F. & Wang, R. (2009). Inorg. Chim. Acta, 362, 5224–5230.  Web of Science CSD CrossRef CAS Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationParson, S. & Gould, B. (2001). ROTAX. University of Edinburgh, Scotland.  Google Scholar
First citationSaito, K., Arai, T., Takahashi, N., Tsukuda, T. & Tsubomura, T. (2006). Dalton Trans. pp. 4444–4448.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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