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Acta Cryst. (2009). E65, m448    [ doi:10.1107/S1600536809010630 ]

Bis[tris(4-fluorophenyl)phosphine-[kappa]P](tropolonato-[kappa]2O,O')copper(I)

G. Steyl

Abstract top

The title compound, [Cu(C7H5O2)(C18H12F3P)2], a copper(I) tris(4-fluorophenyl)phosphine tropolonate derivative, is the first tropolonate complex with fluorinated arylphosphine ligands. The CuI atom has a distorted tetrahedral coordination; the most important geometrical parameters of the molecule are: Cu-P = 2.2377 (10) and 2.2335 (15) Å, Cu-O = 2.084 (2) and 2.082 (2) Å, O-Cu-O = 77.72 (10)°, P-Cu-P = 128.82 (4)° and O-C-C-O = -2.1 (5)°.

Comment top

Tropolone and its derivatives have been of interest ever since their first discovery in the early 1940's (Dewar, 1945); they are known to have applications in pharmacology (Hill & Steyl, 2008) and catalysis (Crous et al., 2005). Recently, reseach in this area has been extended to include phosphine metal complexes and the effect troplonato ligand has on the solid state and chemical behaviour of these complexes (Steyl, 2007; Steyl & Roodt, 2006; Roodt et al., 2003). Only two other examples of copper triphenylphosphine complexes are known to date, which contain a five-membered O,O-bidentate chelating ring system, i.e., the flavonolato and nitrosophenylhydroxylaminato derivatives (Speier et al., 1990; Charalambous et al., 1984). In this paper, the structure of tropolonato-bis[tri(4-fluorophenyl)phosphine]copper(I) complex is reported (Fig. 1).

The Cu—O and Cu—P bond distances are well within normal ranges; the bond angles at the Cu atom show significantly distorted tetrahedral coordination (Table 1). The bidentate bite angle O1—Cu—O2 77.72 (10)° is close to the analogous angles in the previously reported structures (Speier et al., 1990; Charalambous et al., 1984). The phosphine moieties adopt a staggered conformation, the C11—P1—Cu—O1 and C51—P2—Cu—O2 torsion angles being equal to -59.05 (14)° and -49.50 (14)°.

Related literature top

The title compound is structurally related to the flavonolato and nitrosophenylhydroxylaminato derivatives (Speier et al., 1990; Charalambous et al., 1984). For related diketonato complexes, see: Hill & Steyl (2008); Steyl & Roodt (2006); Steyl (2007); Steyl & Hill (2009). For general background, see: Roodt et al. (2003); Crous et al. (2005). For the discovery of tropolone and its derivatives, see: Dewar (1945).

Experimental top

Sodium tropolonate (116 mg, 0.57 mmol) was added to dichloromethane solution (10 ml) of [Cu(P(p-C6H4F)3)2NO3] (396 mg, 0.57 mmol). On slow evaporation of the solvent, crystals suitable for X-Ray structural study were obtained. Yield: 300 mg (74%).

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq of the carrier C atom.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the numbering scheme and atomic displacement ellipsoids at the 50% probability level; hydrogen atoms are omitted for clarity.
Bis[tris(4-fluorophenyl)phosphine-κP](tropolonato- κ2O,O')copper(I) top
Crystal data top
[Cu(C7H5O2)(C18H12F3P)2]Z = 2
Mr = 817.14F(000) = 832
Triclinic, P1Dx = 1.465 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.570 (6) ÅCell parameters from 5934 reflections
b = 11.399 (1) Åθ = 3.1–22.7°
c = 15.861 (1) ŵ = 0.74 mm−1
α = 100.548 (6)°T = 153 K
β = 92.663 (5)°Cuboid, yellow
γ = 98.677 (6)°0.18 × 0.15 × 0.11 mm
V = 1851.9 (11) Å3
Data collection top
Bruker APEXII CCD
diffractometer		7860 independent reflections
Radiation source: fine-focus sealed tube3579 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 512 x 512 pixels mm-1θmax = 27.0°, θmin = 2.3°
φ and ω scansh = −13→7
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		k = −14→14
Tmin = 0.878, Tmax = 0.923l = −20→20
13924 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.76 w = 1/[σ2(Fo2) + (0.0456P)2]
where P = (Fo2 + 2Fc2)/3
7860 reflections(Δ/σ)max = 0.001
487 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
[Cu(C7H5O2)(C18H12F3P)2]γ = 98.677 (6)°
Mr = 817.14V = 1851.9 (11) Å3
Triclinic, P1Z = 2
a = 10.570 (6) ÅMo Kα radiation
b = 11.399 (1) ŵ = 0.74 mm−1
c = 15.861 (1) ÅT = 153 K
α = 100.548 (6)°0.18 × 0.15 × 0.11 mm
β = 92.663 (5)°
Data collection top
Bruker APEXII CCD
diffractometer		7860 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		3579 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.923Rint = 0.049
13924 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.35 e Å−3
S = 0.76Δρmin = −0.34 e Å−3
7860 reflectionsAbsolute structure: ?
487 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Cu0.56504 (4)0.64636 (4)0.25757 (3)0.03356 (14)
P20.46439 (8)0.46425 (8)0.27118 (6)0.0303 (2)
P10.77346 (8)0.70617 (8)0.24545 (6)0.0307 (2)
F20.67563 (19)0.1787 (2)0.50523 (14)0.0597 (6)
F60.4430 (2)0.12081 (19)−0.06083 (13)0.0562 (6)
F31.0479 (2)0.8577 (2)0.59293 (13)0.0562 (6)
F5−0.06950 (19)0.4603 (2)0.36866 (17)0.0719 (8)
F11.0658 (2)0.3574 (2)0.04772 (15)0.0702 (7)
O10.5103 (2)0.7986 (2)0.33161 (15)0.0391 (6)
O20.4337 (2)0.6937 (2)0.17298 (15)0.0411 (6)
F40.8496 (3)1.1318 (2)0.07640 (18)0.0946 (9)
C410.5270 (3)0.3830 (3)0.3488 (2)0.0311 (8)
C210.8670 (3)0.6002 (3)0.1862 (2)0.0327 (9)
C440.6268 (3)0.2484 (3)0.4544 (2)0.0391 (9)
C360.8146 (3)0.7076 (3)0.4198 (2)0.0373 (9)
H360.73800.65000.41060.045*
C560.2024 (3)0.3592 (3)0.2663 (2)0.0359 (9)
H560.22300.28990.22970.043*
C510.2972 (3)0.4595 (3)0.2953 (2)0.0291 (8)
C640.4464 (3)0.1996 (4)0.0155 (2)0.0409 (10)
C350.8778 (3)0.7413 (3)0.5012 (2)0.0425 (10)
H350.84500.70780.54800.051*
C340.9876 (4)0.8233 (4)0.5127 (2)0.0388 (9)
C260.8040 (4)0.4939 (3)0.1368 (2)0.0392 (9)
H260.71300.47680.13520.047*
C110.8064 (3)0.8380 (3)0.1951 (2)0.0301 (8)
C240.9996 (4)0.4386 (4)0.0929 (2)0.0462 (10)
C10.4294 (3)0.8469 (3)0.2931 (2)0.0366 (9)
C450.5071 (3)0.2764 (3)0.4681 (2)0.0429 (10)
H450.45930.25020.51250.051*
C610.4559 (3)0.3533 (3)0.1713 (2)0.0303 (8)
C331.0383 (3)0.8743 (3)0.4477 (2)0.0386 (9)
H331.11560.93100.45810.046*
C320.9748 (3)0.8418 (3)0.3661 (2)0.0323 (9)
H321.00810.87720.32030.039*
C520.2652 (3)0.5610 (3)0.3473 (2)0.0343 (9)
H520.32830.63110.36520.041*
C130.8696 (3)0.9298 (4)0.0745 (3)0.0496 (11)
H130.90180.92470.01920.059*
C160.7705 (3)0.9467 (3)0.2344 (2)0.0410 (10)
H160.73490.95230.28860.049*
C460.4587 (3)0.3450 (3)0.4141 (2)0.0375 (9)
H460.37600.36650.42210.045*
C530.1411 (3)0.5606 (3)0.3732 (2)0.0427 (10)
H530.11920.62860.41040.051*
C650.4357 (3)0.3166 (3)0.0160 (2)0.0412 (10)
H650.42510.3445−0.03640.049*
C540.0521 (3)0.4603 (4)0.3440 (3)0.0456 (11)
C620.4617 (3)0.2325 (3)0.1674 (2)0.0410 (10)
H620.46860.20270.21930.049*
C120.8554 (3)0.8315 (3)0.1148 (2)0.0376 (9)
H120.87960.75790.08700.045*
C30.2929 (3)0.8243 (4)0.1507 (3)0.0510 (11)
H30.27860.77770.09390.061*
C250.8687 (4)0.4115 (3)0.0897 (2)0.0474 (10)
H250.82390.33820.05590.057*
C420.6499 (3)0.3546 (3)0.3411 (2)0.0402 (10)
H420.70050.38350.29890.048*
C70.3872 (4)0.9522 (3)0.3371 (3)0.0502 (11)
H70.43010.98350.39250.060*
C150.7863 (4)1.0465 (4)0.1951 (3)0.0550 (11)
H150.76321.12090.22220.066*
C50.2203 (4)1.0022 (4)0.2396 (4)0.0676 (14)
H50.16081.05660.23810.081*
C310.8621 (3)0.7572 (3)0.3513 (2)0.0298 (8)
C660.4405 (3)0.3943 (3)0.0940 (2)0.0366 (9)
H660.43330.47670.09540.044*
C221.0001 (3)0.6237 (3)0.1867 (2)0.0355 (9)
H221.04570.69670.22040.043*
C140.8356 (4)1.0353 (4)0.1170 (3)0.0567 (12)
C550.0784 (3)0.3600 (4)0.2907 (2)0.0420 (10)
H550.01310.29230.27080.050*
C60.2949 (4)1.0184 (4)0.3146 (3)0.0626 (13)
H60.28211.08450.35760.075*
C430.7001 (3)0.2859 (3)0.3927 (2)0.0448 (10)
H430.78320.26510.38570.054*
C40.2200 (4)0.9173 (5)0.1660 (3)0.0639 (13)
H40.16260.92250.11940.077*
C630.4579 (3)0.1534 (3)0.0893 (3)0.0455 (10)
H630.46300.07030.08680.055*
C231.0675 (4)0.5431 (4)0.1391 (2)0.0415 (10)
H231.15820.56040.13870.050*
C20.3839 (3)0.7860 (4)0.2032 (2)0.0383 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0353 (3)0.0327 (3)0.0323 (3)0.0023 (2)0.0083 (2)0.0066 (2)
P20.0310 (5)0.0316 (6)0.0282 (5)0.0027 (4)0.0064 (4)0.0066 (4)
P10.0349 (5)0.0286 (6)0.0290 (6)0.0035 (4)0.0091 (4)0.0064 (4)
F20.0583 (14)0.0789 (18)0.0545 (15)0.0237 (13)0.0077 (12)0.0347 (13)
F60.0701 (15)0.0490 (15)0.0420 (14)0.0062 (12)0.0095 (11)−0.0088 (11)
F30.0638 (14)0.0660 (16)0.0371 (14)0.0194 (12)−0.0073 (11)0.0010 (11)
F50.0332 (12)0.0780 (19)0.112 (2)0.0122 (12)0.0300 (13)0.0290 (15)
F10.0968 (18)0.0608 (17)0.0609 (17)0.0418 (15)0.0314 (14)0.0017 (13)
O10.0443 (15)0.0395 (16)0.0322 (15)0.0081 (13)0.0057 (12)0.0018 (12)
O20.0529 (16)0.0390 (16)0.0324 (15)0.0106 (13)0.0041 (12)0.0069 (12)
F40.143 (2)0.0567 (18)0.100 (2)0.0193 (17)0.0288 (19)0.0494 (16)
C410.032 (2)0.030 (2)0.029 (2)−0.0021 (16)0.0061 (16)0.0062 (16)
C210.039 (2)0.031 (2)0.030 (2)0.0076 (18)0.0099 (17)0.0068 (17)
C440.041 (2)0.044 (2)0.034 (2)0.0072 (19)−0.0041 (19)0.0148 (19)
C360.035 (2)0.046 (3)0.033 (2)0.0048 (18)0.0100 (18)0.0094 (19)
C560.044 (2)0.032 (2)0.031 (2)0.0059 (19)0.0044 (18)0.0056 (17)
C510.0278 (19)0.035 (2)0.029 (2)0.0097 (17)0.0056 (16)0.0141 (17)
C640.042 (2)0.044 (3)0.032 (2)0.004 (2)0.0090 (18)−0.005 (2)
C350.049 (2)0.055 (3)0.026 (2)0.012 (2)0.0094 (19)0.0115 (19)
C340.042 (2)0.048 (3)0.026 (2)0.017 (2)−0.0014 (19)−0.0015 (19)
C260.049 (2)0.032 (2)0.035 (2)0.0017 (19)0.0091 (19)0.0065 (19)
C110.0290 (19)0.028 (2)0.032 (2)0.0018 (16)0.0037 (16)0.0041 (17)
C240.073 (3)0.039 (3)0.034 (2)0.026 (2)0.022 (2)0.008 (2)
C10.036 (2)0.032 (2)0.042 (3)−0.0027 (18)0.0118 (19)0.0105 (19)
C450.043 (2)0.060 (3)0.030 (2)0.011 (2)0.0101 (18)0.016 (2)
C610.0265 (18)0.033 (2)0.032 (2)0.0024 (16)0.0070 (16)0.0078 (17)
C330.036 (2)0.037 (2)0.039 (3)0.0058 (18)0.0025 (19)−0.0015 (19)
C320.038 (2)0.030 (2)0.030 (2)0.0097 (18)0.0093 (17)0.0033 (17)
C520.029 (2)0.036 (2)0.039 (2)0.0004 (17)0.0070 (17)0.0133 (18)
C130.060 (3)0.051 (3)0.047 (3)0.010 (2)0.016 (2)0.026 (2)
C160.052 (2)0.037 (3)0.032 (2)0.0044 (19)0.0081 (18)0.0023 (19)
C460.031 (2)0.052 (3)0.030 (2)0.0082 (19)0.0069 (17)0.0060 (19)
C530.040 (2)0.041 (3)0.050 (3)0.010 (2)0.014 (2)0.011 (2)
C650.059 (3)0.033 (2)0.030 (2)0.003 (2)0.0049 (19)0.0053 (19)
C540.026 (2)0.057 (3)0.062 (3)0.005 (2)0.013 (2)0.031 (2)
C620.058 (3)0.031 (2)0.038 (2)0.012 (2)0.0065 (19)0.0129 (19)
C120.043 (2)0.033 (2)0.040 (2)0.0082 (18)0.0108 (18)0.0107 (18)
C30.045 (2)0.055 (3)0.056 (3)−0.001 (2)−0.002 (2)0.025 (2)
C250.074 (3)0.022 (2)0.043 (3)0.009 (2)0.010 (2)−0.0016 (18)
C420.031 (2)0.055 (3)0.040 (2)0.0080 (19)0.0123 (18)0.020 (2)
C70.057 (3)0.037 (3)0.055 (3)0.005 (2)0.018 (2)0.005 (2)
C150.080 (3)0.031 (3)0.056 (3)0.012 (2)0.004 (3)0.011 (2)
C50.051 (3)0.051 (3)0.116 (5)0.016 (3)0.033 (3)0.043 (3)
C310.032 (2)0.029 (2)0.029 (2)0.0068 (17)0.0075 (16)0.0047 (16)
C660.046 (2)0.028 (2)0.036 (2)0.0039 (17)0.0038 (18)0.0086 (18)
C220.041 (2)0.031 (2)0.033 (2)0.0043 (18)0.0065 (18)0.0028 (17)
C140.073 (3)0.033 (3)0.071 (3)0.004 (2)0.008 (3)0.032 (2)
C550.031 (2)0.045 (3)0.049 (3)−0.0023 (19)−0.0003 (19)0.014 (2)
C60.064 (3)0.040 (3)0.090 (4)0.016 (2)0.029 (3)0.014 (3)
C430.033 (2)0.058 (3)0.051 (3)0.015 (2)0.011 (2)0.023 (2)
C40.039 (3)0.070 (4)0.095 (4)0.006 (3)0.006 (3)0.049 (3)
C630.061 (3)0.028 (2)0.046 (3)0.005 (2)0.008 (2)0.003 (2)
C230.045 (2)0.050 (3)0.035 (2)0.019 (2)0.0181 (19)0.012 (2)
C20.031 (2)0.044 (3)0.042 (3)0.0002 (19)0.0076 (18)0.016 (2)
Geometric parameters (Å, °) top
Cu—O12.084 (2)C45—H450.9500
Cu—O22.082 (2)C61—C621.378 (4)
Cu—P12.2335 (15)C61—C661.402 (4)
Cu—P22.2377 (10)C33—C321.390 (4)
P2—C511.820 (3)C33—H330.9500
P2—C611.826 (3)C32—C311.396 (4)
P2—C411.827 (3)C32—H320.9500
P1—C111.824 (3)C52—C531.393 (4)
P1—C211.831 (3)C52—H520.9500
P1—C311.835 (3)C13—C141.373 (5)
F2—C441.366 (4)C13—C121.381 (5)
F6—C641.364 (4)C13—H130.9500
F3—C341.359 (4)C16—C151.386 (5)
F5—C541.361 (4)C16—H160.9500
F1—C241.364 (4)C46—H460.9500
O1—C11.275 (4)C53—C541.359 (5)
O2—C21.273 (4)C53—H530.9500
F4—C141.366 (4)C65—C661.378 (5)
C41—C461.386 (4)C65—H650.9500
C41—C421.391 (4)C54—C551.365 (5)
C21—C261.372 (5)C62—C631.388 (5)
C21—C221.391 (4)C62—H620.9500
C44—C431.366 (5)C12—H120.9500
C44—C451.368 (5)C3—C41.395 (6)
C36—C351.386 (5)C3—C21.412 (5)
C36—C311.394 (4)C3—H30.9500
C36—H360.9500C25—H250.9500
C56—C551.385 (5)C42—C431.373 (5)
C56—C511.393 (4)C42—H420.9500
C56—H560.9500C7—C61.392 (5)
C51—C521.389 (4)C7—H70.9500
C64—C651.354 (5)C15—C141.358 (5)
C64—C631.376 (5)C15—H150.9500
C35—C341.359 (5)C5—C61.364 (6)
C35—H350.9500C5—C41.373 (6)
C34—C331.365 (5)C5—H50.9500
C26—C251.376 (5)C66—H660.9500
C26—H260.9500C22—C231.384 (4)
C11—C121.391 (4)C22—H220.9500
C11—C161.396 (5)C55—H550.9500
C24—C231.359 (5)C6—H60.9500
C24—C251.367 (5)C43—H430.9500
C1—C71.418 (5)C4—H40.9500
C1—C21.490 (5)C63—H630.9500
C45—C461.391 (5)C23—H230.9500
O2—Cu—O177.72 (10)C14—C13—H13121.1
O2—Cu—P1117.65 (7)C12—C13—H13121.1
O1—Cu—P1102.97 (7)C15—C16—C11120.7 (4)
O2—Cu—P2100.68 (7)C15—C16—H16119.7
O1—Cu—P2118.07 (7)C11—C16—H16119.7
P1—Cu—P2128.82 (4)C41—C46—C45122.2 (3)
C51—P2—C61103.42 (15)C41—C46—H46118.9
C51—P2—C41102.55 (15)C45—C46—H46118.9
C61—P2—C41101.30 (16)C54—C53—C52118.3 (3)
C51—P2—Cu114.64 (12)C54—C53—H53120.8
C61—P2—Cu111.83 (11)C52—C53—H53120.8
C41—P2—Cu120.92 (11)C64—C65—C66118.6 (3)
C11—P1—C21102.93 (16)C64—C65—H65120.7
C11—P1—C31103.02 (15)C66—C65—H65120.7
C21—P1—C31104.40 (15)C53—C54—F5118.3 (4)
C11—P1—Cu113.85 (11)C53—C54—C55123.3 (3)
C21—P1—Cu119.52 (12)F5—C54—C55118.4 (4)
C31—P1—Cu111.40 (11)C61—C62—C63121.4 (3)
C1—O1—Cu114.7 (2)C61—C62—H62119.3
C2—O2—Cu115.2 (2)C63—C62—H62119.3
C46—C41—C42117.5 (3)C13—C12—C11121.4 (3)
C46—C41—P2124.2 (3)C13—C12—H12119.3
C42—C41—P2118.3 (3)C11—C12—H12119.3
C26—C21—C22117.9 (3)C4—C3—C2132.4 (4)
C26—C21—P1119.2 (3)C4—C3—H3113.8
C22—C21—P1122.9 (3)C2—C3—H3113.8
C43—C44—F2118.1 (3)C24—C25—C26117.9 (4)
C43—C44—C45123.7 (3)C24—C25—H25121.1
F2—C44—C45118.1 (3)C26—C25—H25121.1
C35—C36—C31120.8 (3)C43—C42—C41121.8 (3)
C35—C36—H36119.6C43—C42—H42119.1
C31—C36—H36119.6C41—C42—H42119.1
C55—C56—C51120.2 (3)C6—C7—C1132.2 (4)
C55—C56—H56119.9C6—C7—H7113.9
C51—C56—H56119.9C1—C7—H7113.9
C52—C51—C56119.2 (3)C14—C15—C16118.4 (4)
C52—C51—P2117.3 (3)C14—C15—H15120.8
C56—C51—P2123.5 (3)C16—C15—H15120.8
C65—C64—F6119.8 (3)C6—C5—C4128.3 (4)
C65—C64—C63123.2 (3)C6—C5—H5115.8
F6—C64—C63116.9 (3)C4—C5—H5115.8
C34—C35—C36118.5 (3)C36—C31—C32118.8 (3)
C34—C35—H35120.8C36—C31—P1118.0 (3)
C36—C35—H35120.8C32—C31—P1123.3 (3)
C35—C34—F3118.3 (3)C65—C66—C61120.8 (3)
C35—C34—C33123.0 (3)C65—C66—H66119.6
F3—C34—C33118.8 (3)C61—C66—H66119.6
C21—C26—C25121.9 (4)C23—C22—C21121.4 (3)
C21—C26—H26119.0C23—C22—H22119.3
C25—C26—H26119.0C21—C22—H22119.3
C12—C11—C16118.4 (3)C15—C14—F4119.4 (4)
C12—C11—P1122.3 (3)C15—C14—C13123.4 (4)
C16—C11—P1119.1 (3)F4—C14—C13117.2 (4)
C23—C24—F1118.0 (4)C54—C55—C56118.6 (3)
C23—C24—C25123.1 (4)C54—C55—H55120.7
F1—C24—C25118.9 (4)C56—C55—H55120.7
O1—C1—C7119.4 (4)C5—C6—C7129.3 (4)
O1—C1—C2116.5 (3)C5—C6—H6115.3
C7—C1—C2124.2 (4)C7—C6—H6115.3
C44—C45—C46116.8 (3)C44—C43—C42117.9 (3)
C44—C45—H45121.6C44—C43—H43121.0
C46—C45—H45121.6C42—C43—H43121.0
C62—C61—C66118.3 (3)C5—C4—C3128.5 (4)
C62—C61—P2124.3 (3)C5—C4—H4115.7
C66—C61—P2117.3 (3)C3—C4—H4115.7
C34—C33—C32118.9 (3)C64—C63—C62117.6 (4)
C34—C33—H33120.6C64—C63—H63121.2
C32—C33—H33120.6C62—C63—H63121.2
C33—C32—C31120.1 (3)C24—C23—C22117.8 (3)
C33—C32—H32120.0C24—C23—H23121.1
C31—C32—H32120.0C22—C23—H23121.1
C51—C52—C53120.3 (3)O2—C2—C3119.2 (4)
C51—C52—H52119.8O2—C2—C1115.9 (3)
C53—C52—H52119.8C3—C2—C1124.9 (4)
C14—C13—C12117.8 (4)
O2—Cu—P2—C51−49.50 (14)C56—C51—C52—C532.8 (5)
O1—Cu—P2—C5132.18 (15)P2—C51—C52—C53−175.6 (3)
P1—Cu—P2—C51171.23 (12)C12—C11—C16—C15−1.5 (5)
O2—Cu—P2—C6167.82 (13)P1—C11—C16—C15−175.7 (3)
O1—Cu—P2—C61149.49 (14)C42—C41—C46—C45−2.7 (5)
P1—Cu—P2—C61−71.45 (12)P2—C41—C46—C45175.6 (3)
O2—Cu—P2—C41−173.11 (14)C44—C45—C46—C410.4 (5)
O1—Cu—P2—C41−91.43 (16)C51—C52—C53—C54−2.2 (5)
P1—Cu—P2—C4147.62 (14)F6—C64—C65—C66−179.5 (3)
O2—Cu—P1—C1123.73 (15)C63—C64—C65—C662.1 (6)
O1—Cu—P1—C11−59.05 (14)C52—C53—C54—F5−179.4 (3)
P2—Cu—P1—C11157.35 (12)C52—C53—C54—C550.2 (6)
O2—Cu—P1—C21−98.37 (15)C66—C61—C62—C632.6 (5)
O1—Cu—P1—C21178.85 (14)P2—C61—C62—C63−178.4 (3)
P2—Cu—P1—C2135.25 (15)C14—C13—C12—C111.0 (6)
O2—Cu—P1—C31139.70 (14)C16—C11—C12—C130.5 (5)
O1—Cu—P1—C3156.92 (14)P1—C11—C12—C13174.5 (3)
P2—Cu—P1—C31−86.68 (12)C23—C24—C25—C26−1.2 (6)
O2—Cu—O1—C1−0.8 (2)F1—C24—C25—C26179.0 (3)
P1—Cu—O1—C1115.1 (2)C21—C26—C25—C24−0.2 (6)
P2—Cu—O1—C1−96.5 (2)C46—C41—C42—C433.5 (5)
O1—Cu—O2—C2−0.3 (2)P2—C41—C42—C43−175.0 (3)
P1—Cu—O2—C2−98.7 (2)O1—C1—C7—C6−174.7 (4)
P2—Cu—O2—C2116.4 (2)C2—C1—C7—C64.5 (6)
C51—P2—C41—C46−7.0 (3)C11—C16—C15—C141.0 (6)
C61—P2—C41—C46−113.7 (3)C35—C36—C31—C320.0 (5)
Cu—P2—C41—C46122.1 (3)C35—C36—C31—P1179.3 (3)
C51—P2—C41—C42171.3 (3)C33—C32—C31—C360.6 (5)
C61—P2—C41—C4264.6 (3)C33—C32—C31—P1−178.6 (2)
Cu—P2—C41—C42−59.5 (3)C11—P1—C31—C36150.2 (3)
C11—P1—C21—C26−115.4 (3)C21—P1—C31—C36−102.5 (3)
C31—P1—C21—C26137.3 (3)Cu—P1—C31—C3627.8 (3)
Cu—P1—C21—C2612.0 (3)C11—P1—C31—C32−30.5 (3)
C11—P1—C21—C2262.7 (3)C21—P1—C31—C3276.8 (3)
C31—P1—C21—C22−44.6 (3)Cu—P1—C31—C32−152.9 (2)
Cu—P1—C21—C22−169.9 (2)C64—C65—C66—C61−0.1 (5)
C55—C56—C51—C52−1.4 (5)C62—C61—C66—C65−2.1 (5)
C55—C56—C51—P2176.9 (3)P2—C61—C66—C65178.8 (3)
C61—P2—C51—C52−156.6 (3)C26—C21—C22—C230.0 (5)
C41—P2—C51—C5298.3 (3)P1—C21—C22—C23−178.1 (3)
Cu—P2—C51—C52−34.6 (3)C16—C15—C14—F4178.7 (4)
C61—P2—C51—C5625.0 (3)C16—C15—C14—C130.6 (7)
C41—P2—C51—C56−80.0 (3)C12—C13—C14—C15−1.6 (6)
Cu—P2—C51—C56147.0 (2)C12—C13—C14—F4−179.7 (3)
C31—C36—C35—C34−0.4 (5)C53—C54—C55—C561.2 (6)
C36—C35—C34—F3178.8 (3)F5—C54—C55—C56−179.2 (3)
C36—C35—C34—C330.3 (6)C51—C56—C55—C54−0.6 (5)
C22—C21—C26—C250.7 (5)C4—C5—C6—C7−1.9 (8)
P1—C21—C26—C25178.9 (3)C1—C7—C6—C5−3.0 (7)
C21—P1—C11—C1218.1 (3)F2—C44—C43—C42179.2 (3)
C31—P1—C11—C12126.5 (3)C45—C44—C43—C42−0.7 (6)
Cu—P1—C11—C12−112.7 (3)C41—C42—C43—C44−1.8 (6)
C21—P1—C11—C16−167.9 (3)C6—C5—C4—C32.3 (8)
C31—P1—C11—C16−59.5 (3)C2—C3—C4—C51.9 (7)
Cu—P1—C11—C1661.3 (3)C65—C64—C63—C62−1.6 (6)
Cu—O1—C1—C7−179.0 (2)F6—C64—C63—C62179.9 (3)
Cu—O1—C1—C21.7 (4)C61—C62—C63—C64−0.8 (5)
C43—C44—C45—C461.3 (6)F1—C24—C23—C22−178.3 (3)
F2—C44—C45—C46−178.5 (3)C25—C24—C23—C221.9 (6)
C51—P2—C61—C62−90.2 (3)C21—C22—C23—C24−1.3 (5)
C41—P2—C61—C6215.8 (3)Cu—O2—C2—C3−179.5 (2)
Cu—P2—C61—C62145.9 (3)Cu—O2—C2—C11.3 (4)
C51—P2—C61—C6688.9 (3)C4—C3—C2—O2177.4 (4)
C41—P2—C61—C66−165.1 (2)C4—C3—C2—C1−3.4 (6)
Cu—P2—C61—C66−35.0 (3)O1—C1—C2—O2−2.1 (5)
C35—C34—C33—C320.3 (5)C7—C1—C2—O2178.7 (3)
F3—C34—C33—C32−178.2 (3)O1—C1—C2—C3178.7 (3)
C34—C33—C32—C31−0.8 (5)C7—C1—C2—C3−0.5 (6)
Table 1
Selected geometric parameters (Å, °) top
Cu—O12.084 (2)Cu—P12.2335 (15)
Cu—O22.082 (2)Cu—P22.2377 (10)
O2—Cu—O177.72 (10)O2—Cu—P2100.68 (7)
O2—Cu—P1117.65 (7)O1—Cu—P2118.07 (7)
O1—Cu—P1102.97 (7)P1—Cu—P2128.82 (4)
O2—Cu—P2—C51−49.50 (14)O1—Cu—P1—C11−59.05 (14)
O1—Cu—P2—C5132.18 (15)P2—Cu—P1—C11157.35 (12)
P1—Cu—P2—C51171.23 (12)O2—Cu—P1—C21−98.37 (15)
O2—Cu—P2—C6167.82 (13)O1—Cu—P1—C21178.85 (14)
O1—Cu—P2—C61149.49 (14)P2—Cu—P1—C2135.25 (15)
P1—Cu—P2—C61−71.45 (12)O2—Cu—P1—C31139.70 (14)
O2—Cu—P2—C41−173.11 (14)O1—Cu—P1—C3156.92 (14)
O1—Cu—P2—C41−91.43 (16)P2—Cu—P1—C31−86.68 (12)
P1—Cu—P2—C4147.62 (14)O1—C1—C2—O2−2.1 (5)
O2—Cu—P1—C1123.73 (15)
Acknowledgements top

Financial assistance from the University of the Free State and Professor A. Roodt is gratefully acknowledged. Mr L. Kirsten is acknowledged for the data collection. Part of this material is based on work supported by the South African National Research Foundation (NRF) under grant number GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the NRF.

references
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