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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m1017.
Published online 2009 July 31. doi:  10.1107/S160053680902995X
PMCID: PMC2977430

(μ-Pyridine-2-carbaldehyde azine)bis­[bis­(triphenyl­phosphine-κP)copper(I)] bis­(tetra­fluorido­borate) dichloro­methane disolvate

Abstract

In the centrosymmetric title complex, [Cu2(C12H10N4)(C18H15P)4](BF4)2·2CH2Cl2, the CuI atom adopts a distorted tetra­hedral geometry, defined by two P atoms from two triphenyl­phosphine ligands and two N atoms from a pyridine-2-carbaldehyde azine ligand. The two Cu atoms are bridged by the centrosymmetric pyridine-2-carbaldehyde azine ligand. The F atoms of the tetra­fluorido­borate anion are disordered over two sites [occupancy factors = 0.68 (5) and 0.32 (5)]. The dichloro­methane solvent mol­ecule is disordered over four sites, with occupancy factors of 0.513 (4), 0.173 (5), 0.141 (5) and 0.173 (5).

Related literature

For general background to the use of neutral pyridine-azines in the construction of di-, tri- and polynuclear complexes, see: Tuna et al. (2003 [triangle]); Guo et al. (2002 [triangle]); Hamblin et al. (2002 [triangle]). For related structures, see: Mo et al. (2006 [triangle]); Zhou et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1017-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C12H10N4)(C18H15P)4](BF4)2·2CH2Cl2
  • M r = 1729.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1017-efi1.jpg
  • a = 13.0932 (16) Å
  • b = 27.501 (3) Å
  • c = 13.9033 (18) Å
  • β = 115.117 (2)°
  • V = 4532.9 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.72 mm−1
  • T = 293 K
  • 0.35 × 0.32 × 0.30 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.787, T max = 0.814
  • 24119 measured reflections
  • 7643 independent reflections
  • 3919 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.268
  • S = 0.95
  • 7643 reflections
  • 564 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 1.44 e Å−3
  • Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902995X/hy2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902995X/hy2211Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Key Laboratory of Photochemical Conversion and Optoelectronic Materials, TIPC, CAS, and Jiangxi Provincial Department of Education for financial support of this work. The Materials Chemistry Department of Nanchang Hangkong University is also acknowleged.

supplementary crystallographic information

Comment

Neutral pyridine-azines are excellent bridging ligands in coordination chemistry. They are often used to construct some di-, tri- and polynuclear complexes (Tuna et al., 2003; Guo et al., 2002; Hamblin et al., 2002; Zhou et al., 2006). We describe here the synthesis and structure of a new copper(I) compound with a pyridine-2-carbaldehyde azine ligand.

The molecular structure of the title compound is depicted in Fig. 1. The complex is a centrosymmetric dimer with two CuI atoms bridged by a pyridine-2-carbaldehyde azine ligand. The CuI atom has a distorted tetrahedral geometry with two P atoms from two triphenylphosphine ligands and two N atoms from the bridging pyridine-2-carbaldehyde azine ligand. The bond angles around the Cu atom are in the range of 77.5 (2)° (N1—Cu1—N2) to 124.02 (7) (P1—Cu1—P2)°. The Cu—P [2.2741 (19) and 2.292 (2) Å] and Cu—N [2.061 (6) and 2.175 (5) Å] bond distances (Table 1) are within the normal ranges for analogous complexes (Mo et al., 2006; Zhou et al., 2006).

Experimental

Pyridine-2-carbaldehyde and CuBF4.4CH3CN were prepared by literature method (Mo et al., 2006; Zhou et al., 2006). The title compound was prepared by reacting pyridine-2-carbaldehyde (0.021 g, 0.1 mmol), CuBF4.4CH3CN (0.031 g, 0.1 mmol) and triphenylphosphine (0.052 g, 0.2 mmol) in 30 ml dry dichloromethane under N2 atmosphere. Brown needle crystals suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into the solution of the title compound in dichloromethane (yield 83%).

Refinement

H atoms were positioned geomertrically and treated as riding, with C—H = 0.93 (aromatic) and 0.97 (dichloromethane) Å and with Uiso(H) = 1.2Ueq(C). The tetrafluoroborate anion and dichloromethane solvent molecule are disordered. The tetrafluoroborate anion is splitted into two components with site occupancy factor (SOF) values of 0.68 (5) and 0.32 (5). The dichloromethane molecule is splitted into four components with SOF values of 0.513 (4), 0.173 (5), 0.141 (5) and 0.173 (5), respectively. The disorder of the anion and solvent molecule may cause high value of the weighted R factor for this structure. The highest peak and deepest hole in the final difference map were associated with atom C45 (at distances of 0.78 Å).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms, tetrafluoroborate anion and dichloromethane solvent molecule are omitted for clarity. [Symmetry code: (i) 1 - x, 1 - y, 1 - z.]

Crystal data

[Cu2(C12H10N4)(C18H15P)4](BF4)2·2CH2Cl2F(000) = 1772
Mr = 1729.89Dx = 1.267 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 24119 reflections
a = 13.0932 (16) Åθ = 2.2–25.0°
b = 27.501 (3) ŵ = 0.72 mm1
c = 13.9033 (18) ÅT = 293 K
β = 115.117 (2)°Block, brown
V = 4532.9 (9) Å30.35 × 0.32 × 0.30 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer7643 independent reflections
Radiation source: fine-focus sealed tube3919 reflections with I > 2σ(I)
graphiteRint = 0.063
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = 0→15
Tmin = 0.787, Tmax = 0.814k = 0→32
24119 measured reflectionsl = −16→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.268H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.1662P)2] where P = (Fo2 + 2Fc2)/3
7643 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 1.44 e Å3
2 restraintsΔρmin = −0.62 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Cu10.39337 (7)0.56453 (3)0.34029 (6)0.0439 (3)
F10.9059 (12)0.6834 (11)0.7796 (13)0.130 (8)0.68 (5)
F20.919 (3)0.7544 (5)0.7121 (13)0.151 (10)0.68 (5)
F30.956 (3)0.6852 (17)0.647 (4)0.152 (10)0.68 (5)
F41.077 (2)0.7109 (11)0.806 (2)0.152 (8)0.68 (5)
F1'1.011 (6)0.7535 (15)0.713 (3)0.17 (2)0.32 (5)
F2'1.065 (5)0.684 (2)0.799 (5)0.145 (16)0.32 (5)
F3'0.906 (3)0.721 (2)0.789 (2)0.129 (17)0.32 (5)
F4'0.910 (5)0.685 (3)0.645 (8)0.123 (15)0.32 (5)
N10.4999 (5)0.6178 (2)0.4340 (4)0.0469 (14)
N20.4973 (5)0.52483 (19)0.4841 (4)0.0437 (13)
Cl10.7434 (6)0.1422 (2)0.1283 (7)0.140 (3)0.513 (4)
Cl20.6074 (8)0.2242 (3)0.1389 (9)0.163 (3)0.513 (4)
Cl30.4482 (17)0.2880 (6)0.2405 (19)0.140 (3)0.173 (5)
Cl40.303 (3)0.2584 (14)0.038 (4)0.163 (3)0.173 (5)
Cl50.687 (2)0.2339 (8)0.229 (3)0.140 (3)0.141 (5)
Cl60.846 (3)0.2284 (12)0.451 (3)0.163 (3)0.141 (5)
Cl70.2701 (18)0.2418 (7)0.105 (2)0.140 (3)0.173 (5)
Cl80.473 (2)0.2573 (9)0.090 (2)0.163 (3)0.173 (5)
P10.44194 (15)0.54008 (7)0.20904 (13)0.0438 (5)
P20.21113 (15)0.57584 (7)0.31766 (14)0.0456 (5)
B10.9692 (15)0.7102 (6)0.7357 (12)0.103 (4)
C10.5039 (7)0.6647 (3)0.4100 (7)0.064 (2)
H10.45380.67590.34350.077*
C20.5824 (8)0.6983 (3)0.4827 (8)0.082 (3)
H20.58600.73020.46210.098*
C30.6508 (8)0.6832 (3)0.5813 (8)0.088 (3)
H30.69850.70500.63140.106*
C40.6489 (7)0.6349 (3)0.6066 (7)0.074 (2)
H40.69850.62350.67310.089*
C50.5730 (6)0.6032 (3)0.5329 (6)0.0514 (18)
C60.5683 (6)0.5522 (2)0.5556 (5)0.0482 (17)
H60.61630.53950.62130.058*
C70.3910 (6)0.5791 (3)0.0920 (5)0.0484 (17)
C80.4119 (8)0.6284 (3)0.1071 (6)0.067 (2)
H80.45250.64020.17560.080*
C90.3739 (8)0.6607 (3)0.0231 (7)0.081 (3)
H90.38660.69390.03470.097*
C100.3171 (8)0.6428 (3)−0.0782 (7)0.075 (2)
H100.29020.6640−0.13560.090*
C110.3000 (7)0.5942 (3)−0.0948 (6)0.067 (2)
H110.26360.5824−0.16380.080*
C120.3363 (6)0.5620 (3)−0.0101 (5)0.0536 (18)
H120.32370.5289−0.02240.064*
C130.3871 (6)0.4803 (2)0.1559 (5)0.0468 (17)
C140.4509 (7)0.4451 (3)0.1386 (7)0.065 (2)
H140.52600.45130.15350.079*
C150.4029 (9)0.3994 (3)0.0981 (8)0.085 (3)
H150.44560.37560.08450.101*
C160.2935 (9)0.3901 (3)0.0789 (8)0.083 (3)
H160.26360.35950.05460.100*
C170.2244 (8)0.4257 (3)0.0947 (7)0.073 (2)
H170.14920.41960.07920.087*
C180.2741 (7)0.4699 (3)0.1344 (6)0.060 (2)
H180.23130.49380.14750.072*
C190.5921 (6)0.5342 (3)0.2423 (5)0.0485 (17)
C200.6401 (7)0.5499 (3)0.1748 (6)0.060 (2)
H200.59520.56590.11200.072*
C210.7526 (7)0.5422 (3)0.1992 (7)0.068 (2)
H210.78280.55330.15360.081*
C220.8193 (7)0.5184 (3)0.2904 (7)0.064 (2)
H220.89460.51230.30600.077*
C230.7752 (7)0.5031 (3)0.3599 (7)0.074 (2)
H230.82090.48760.42310.089*
C240.6624 (7)0.5111 (3)0.3344 (6)0.063 (2)
H240.63310.50060.38120.076*
C250.1225 (6)0.5213 (3)0.2757 (6)0.0512 (18)
C260.1505 (7)0.4826 (3)0.3480 (6)0.061 (2)
H260.20640.48640.41670.073*
C270.0942 (7)0.4386 (3)0.3166 (8)0.071 (2)
H270.11400.41280.36410.085*
C280.0077 (7)0.4326 (4)0.2137 (8)0.077 (3)
H28−0.02960.40300.19270.093*
C29−0.0202 (7)0.4710 (3)0.1457 (8)0.072 (2)
H29−0.07810.46780.07790.086*
C300.0366 (6)0.5151 (3)0.1763 (6)0.0582 (19)
H300.01600.54090.12840.070*
C310.1930 (6)0.5960 (3)0.4352 (6)0.0567 (19)
C320.0874 (7)0.5932 (3)0.4398 (7)0.070 (2)
H320.02630.57870.38470.084*
C330.0749 (9)0.6121 (4)0.5264 (7)0.079 (3)
H330.00430.61240.52730.094*
C340.1650 (8)0.6302 (4)0.6095 (7)0.080 (3)
H340.15630.64130.66880.096*
C350.2679 (9)0.6326 (4)0.6087 (7)0.089 (3)
H350.32880.64540.66670.107*
C360.2826 (7)0.6156 (3)0.5201 (6)0.070 (2)
H360.35290.61770.51890.083*
C370.1303 (6)0.6189 (3)0.2139 (6)0.0516 (18)
C380.0403 (8)0.6452 (3)0.2120 (7)0.079 (3)
H380.02290.64370.27020.095*
C39−0.0260 (8)0.6740 (4)0.1252 (8)0.091 (3)
H39−0.08900.69010.12410.109*
C400.0028 (9)0.6785 (3)0.0414 (7)0.082 (3)
H40−0.03940.6984−0.01580.098*
C410.0906 (9)0.6544 (4)0.0423 (7)0.086 (3)
H410.11090.6574−0.01390.104*
C420.1533 (8)0.6240 (3)0.1295 (7)0.075 (3)
H420.21370.60670.12810.090*
C430.709 (2)0.2027 (8)0.109 (2)0.131 (7)0.513 (4)
H43A0.77680.22110.14970.157*0.513 (4)
H43B0.68780.20980.03460.157*0.513 (4)
C440.325 (7)0.255 (3)0.169 (7)0.131 (7)0.173 (5)
H44A0.33410.22140.19240.157*0.173 (5)
H44B0.26180.26900.17800.157*0.173 (5)
C450.798 (7)0.204 (3)0.328 (8)0.131 (7)0.141 (5)
H45A0.77460.17050.33230.157*0.141 (5)
H45B0.86020.20210.30810.157*0.141 (5)
C460.330 (9)0.260 (4)0.020 (11)0.131 (7)0.173 (5)
H46A0.30510.2395−0.04150.157*0.173 (5)
H46B0.30700.2935−0.00350.157*0.173 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0449 (5)0.0480 (5)0.0388 (5)0.0011 (4)0.0178 (4)−0.0006 (4)
F10.133 (10)0.127 (17)0.133 (11)0.000 (9)0.059 (8)0.021 (10)
F20.16 (2)0.080 (8)0.176 (13)0.035 (10)0.036 (12)0.016 (7)
F30.15 (3)0.182 (16)0.139 (15)0.01 (2)0.07 (2)−0.059 (11)
F40.095 (10)0.135 (18)0.157 (12)−0.007 (13)−0.014 (8)−0.005 (15)
F1'0.16 (5)0.14 (3)0.18 (3)−0.01 (3)0.03 (3)0.03 (2)
F2'0.12 (3)0.12 (3)0.16 (3)0.02 (3)0.02 (2)0.01 (3)
F3'0.13 (2)0.13 (4)0.13 (2)0.00 (2)0.059 (16)−0.01 (2)
F4'0.10 (3)0.13 (3)0.14 (3)0.00 (3)0.05 (3)−0.039 (19)
N10.052 (4)0.038 (3)0.050 (3)0.001 (3)0.021 (3)0.000 (3)
N20.047 (3)0.044 (3)0.044 (3)0.006 (3)0.023 (3)0.000 (3)
Cl10.115 (4)0.079 (3)0.200 (6)0.004 (3)0.042 (4)0.054 (4)
Cl20.141 (6)0.136 (6)0.219 (8)0.004 (5)0.083 (6)0.030 (5)
Cl30.115 (4)0.079 (3)0.200 (6)0.004 (3)0.042 (4)0.054 (4)
Cl40.141 (6)0.136 (6)0.219 (8)0.004 (5)0.083 (6)0.030 (5)
Cl50.115 (4)0.079 (3)0.200 (6)0.004 (3)0.042 (4)0.054 (4)
Cl60.141 (6)0.136 (6)0.219 (8)0.004 (5)0.083 (6)0.030 (5)
Cl70.115 (4)0.079 (3)0.200 (6)0.004 (3)0.042 (4)0.054 (4)
Cl80.141 (6)0.136 (6)0.219 (8)0.004 (5)0.083 (6)0.030 (5)
P10.0456 (11)0.0486 (11)0.0392 (9)0.0020 (8)0.0200 (8)0.0000 (8)
P20.0431 (10)0.0539 (11)0.0409 (10)0.0029 (8)0.0190 (8)0.0010 (8)
B10.124 (13)0.080 (10)0.093 (10)0.018 (10)0.033 (10)−0.015 (8)
C10.068 (6)0.052 (5)0.066 (5)0.001 (4)0.022 (4)−0.005 (4)
C20.082 (7)0.052 (5)0.092 (7)−0.011 (5)0.019 (5)0.001 (5)
C30.081 (7)0.064 (6)0.091 (7)−0.014 (5)0.009 (5)−0.014 (5)
C40.067 (6)0.058 (5)0.071 (5)−0.004 (4)0.005 (4)−0.007 (4)
C50.049 (4)0.049 (4)0.056 (4)0.003 (3)0.022 (4)−0.002 (3)
C60.050 (4)0.051 (4)0.042 (4)0.005 (3)0.018 (3)0.000 (3)
C70.049 (4)0.056 (5)0.046 (4)0.005 (3)0.025 (3)0.002 (3)
C80.085 (6)0.062 (5)0.050 (4)−0.004 (5)0.025 (4)0.001 (4)
C90.101 (8)0.062 (6)0.072 (6)0.000 (5)0.029 (5)0.006 (5)
C100.088 (7)0.075 (6)0.061 (5)−0.002 (5)0.030 (5)0.017 (5)
C110.076 (6)0.074 (6)0.052 (5)−0.001 (5)0.028 (4)0.001 (4)
C120.058 (5)0.054 (4)0.047 (4)0.006 (4)0.021 (3)−0.001 (3)
C130.052 (4)0.047 (4)0.050 (4)0.003 (3)0.030 (3)0.001 (3)
C140.063 (5)0.057 (5)0.082 (6)−0.005 (4)0.036 (5)−0.010 (4)
C150.083 (7)0.066 (6)0.107 (8)0.002 (5)0.043 (6)−0.021 (5)
C160.081 (7)0.065 (6)0.104 (7)−0.019 (5)0.039 (6)−0.016 (5)
C170.070 (6)0.074 (6)0.075 (6)−0.016 (5)0.032 (5)−0.016 (5)
C180.063 (5)0.060 (5)0.062 (5)0.005 (4)0.032 (4)−0.007 (4)
C190.051 (4)0.055 (4)0.043 (4)0.000 (3)0.023 (3)−0.001 (3)
C200.052 (5)0.072 (5)0.057 (5)0.003 (4)0.024 (4)0.007 (4)
C210.056 (5)0.086 (6)0.073 (6)−0.009 (5)0.038 (5)−0.003 (5)
C220.050 (5)0.074 (6)0.077 (6)0.003 (4)0.035 (4)−0.007 (5)
C230.052 (5)0.095 (7)0.073 (6)0.021 (5)0.023 (4)0.009 (5)
C240.057 (5)0.077 (6)0.063 (5)0.011 (4)0.033 (4)0.009 (4)
C250.049 (4)0.055 (4)0.057 (4)0.004 (4)0.029 (4)0.003 (3)
C260.062 (5)0.061 (5)0.064 (5)0.004 (4)0.031 (4)0.006 (4)
C270.071 (6)0.066 (6)0.090 (6)0.003 (5)0.048 (5)0.013 (5)
C280.061 (6)0.074 (6)0.099 (7)−0.006 (5)0.036 (5)−0.003 (5)
C290.060 (6)0.077 (6)0.077 (6)−0.011 (5)0.028 (4)−0.009 (5)
C300.055 (5)0.062 (5)0.059 (5)−0.005 (4)0.026 (4)0.002 (4)
C310.054 (5)0.071 (5)0.049 (4)0.011 (4)0.026 (4)0.003 (4)
C320.068 (6)0.087 (6)0.059 (5)0.005 (5)0.030 (4)0.001 (4)
C330.080 (7)0.106 (7)0.070 (6)0.016 (6)0.051 (5)0.005 (5)
C340.079 (7)0.114 (8)0.059 (5)0.015 (6)0.041 (5)−0.005 (5)
C350.085 (7)0.115 (8)0.058 (5)0.007 (6)0.022 (5)−0.021 (5)
C360.061 (5)0.094 (7)0.055 (5)0.000 (5)0.025 (4)−0.010 (4)
C370.052 (5)0.059 (5)0.052 (4)0.004 (4)0.030 (4)0.003 (3)
C380.080 (6)0.095 (7)0.067 (6)0.025 (6)0.037 (5)0.022 (5)
C390.085 (7)0.101 (8)0.085 (7)0.047 (6)0.035 (6)0.026 (6)
C400.083 (7)0.081 (7)0.070 (6)0.017 (5)0.021 (5)0.023 (5)
C410.095 (7)0.102 (8)0.070 (6)0.026 (6)0.042 (5)0.032 (5)
C420.075 (6)0.089 (7)0.068 (5)0.025 (5)0.037 (5)0.019 (5)
C430.114 (17)0.079 (13)0.18 (2)−0.002 (11)0.048 (14)0.025 (14)
C440.114 (17)0.079 (13)0.18 (2)−0.002 (11)0.048 (14)0.025 (14)
C450.114 (17)0.079 (13)0.18 (2)−0.002 (11)0.048 (14)0.025 (14)
C460.114 (17)0.079 (13)0.18 (2)−0.002 (11)0.048 (14)0.025 (14)

Geometric parameters (Å, °)

Cu1—N12.061 (6)C16—C171.412 (12)
Cu1—N22.175 (5)C16—H160.9300
Cu1—P12.2741 (19)C17—C181.379 (11)
Cu1—P22.292 (2)C17—H170.9300
F1—B11.43 (2)C18—H180.9300
F2—B11.35 (2)C19—C241.374 (10)
F3—B11.36 (4)C19—C201.402 (10)
F4—B11.33 (3)C20—C211.379 (11)
F1'—B11.40 (4)C20—H200.9300
F2'—B11.39 (5)C21—C221.364 (12)
F3'—B11.36 (3)C21—H210.9300
F4'—B11.36 (9)C22—C231.385 (12)
N1—C11.338 (9)C22—H220.9300
N1—C51.361 (9)C23—C241.382 (11)
N2—C61.278 (8)C23—H230.9300
N2—N2i1.428 (10)C24—H240.9300
Cl1—C431.72 (2)C25—C301.373 (10)
Cl2—C431.66 (3)C25—C261.402 (10)
Cl3—C441.75 (8)C26—C271.386 (11)
Cl4—C441.72 (9)C26—H260.9300
Cl5—C451.74 (9)C27—C281.407 (13)
Cl6—C451.69 (10)C27—H270.9300
Cl7—C461.75 (12)C28—C291.361 (12)
Cl8—C461.71 (11)C28—H280.9300
P1—C131.820 (7)C29—C301.391 (11)
P1—C71.823 (7)C29—H290.9300
P1—C191.825 (7)C30—H300.9300
P2—C371.819 (7)C31—C361.373 (11)
P2—C311.833 (7)C31—C321.414 (11)
P2—C251.833 (8)C32—C331.384 (11)
C1—C21.432 (11)C32—H320.9300
C1—H10.9300C33—C341.347 (13)
C2—C31.346 (12)C33—H330.9300
C2—H20.9300C34—C351.354 (13)
C3—C41.378 (12)C34—H340.9300
C3—H30.9300C35—C361.404 (11)
C4—C51.391 (10)C35—H350.9300
C4—H40.9300C36—H360.9300
C5—C61.444 (10)C37—C421.338 (11)
C6—H60.9300C37—C381.372 (11)
C7—C121.374 (9)C38—C391.396 (12)
C7—C81.381 (10)C38—H380.9300
C8—C91.380 (11)C39—C401.374 (13)
C8—H80.9300C39—H390.9300
C9—C101.374 (12)C40—C411.322 (13)
C9—H90.9300C40—H400.9300
C10—C111.358 (11)C41—C421.413 (11)
C10—H100.9300C41—H410.9300
C11—C121.386 (10)C42—H420.9300
C11—H110.9300C43—H43A0.9700
C12—H120.9300C43—H43B0.9700
C13—C141.365 (10)C44—H44A0.9700
C13—C181.408 (10)C44—H44B0.9700
C14—C151.412 (11)C45—H45A0.9700
C14—H140.9300C45—H45B0.9700
C15—C161.364 (13)C46—H46A0.9700
C15—H150.9300C46—H46B0.9700
N1—Cu1—N277.5 (2)C21—C20—C19121.6 (7)
N1—Cu1—P1111.87 (17)C21—C20—H20119.2
N2—Cu1—P1108.09 (15)C19—C20—H20119.2
N1—Cu1—P2112.10 (17)C22—C21—C20119.9 (8)
N2—Cu1—P2113.75 (15)C22—C21—H21120.1
P1—Cu1—P2124.02 (7)C20—C21—H21120.1
C1—N1—C5116.9 (6)C21—C22—C23120.1 (8)
C1—N1—Cu1128.0 (5)C21—C22—H22119.9
C5—N1—Cu1115.2 (5)C23—C22—H22119.9
C6—N2—N2i113.5 (7)C24—C23—C22119.3 (8)
C6—N2—Cu1112.5 (4)C24—C23—H23120.4
N2i—N2—Cu1133.9 (6)C22—C23—H23120.4
C13—P1—C7103.8 (3)C19—C24—C23122.2 (8)
C13—P1—C19102.7 (3)C19—C24—H24118.9
C7—P1—C19103.0 (3)C23—C24—H24118.9
C13—P1—Cu1113.3 (2)C30—C25—C26118.7 (7)
C7—P1—Cu1114.9 (2)C30—C25—P2124.0 (6)
C19—P1—Cu1117.4 (2)C26—C25—P2117.1 (6)
C37—P2—C31104.9 (3)C27—C26—C25119.6 (8)
C37—P2—C25101.8 (3)C27—C26—H26120.2
C31—P2—C25103.1 (3)C25—C26—H26120.2
C37—P2—Cu1114.8 (2)C26—C27—C28121.0 (8)
C31—P2—Cu1116.1 (3)C26—C27—H27119.5
C25—P2—Cu1114.5 (2)C28—C27—H27119.5
F4—B1—F2114.7 (17)C29—C28—C27118.5 (9)
F4'—B1—F3'113 (3)C29—C28—H28120.8
F4—B1—F3111 (2)C27—C28—H28120.8
F2—B1—F3112 (2)C28—C29—C30120.9 (9)
F4'—B1—F2'109 (4)C28—C29—H29119.5
F3'—B1—F2'111 (4)C30—C29—H29119.5
F4'—B1—F1'110 (4)C25—C30—C29121.3 (8)
F3'—B1—F1'110 (2)C25—C30—H30119.4
F2'—B1—F1'104 (3)C29—C30—H30119.4
F4—B1—F1108.5 (19)C36—C31—C32118.5 (7)
F2—B1—F1105.0 (17)C36—C31—P2119.9 (6)
F3—B1—F1105 (2)C32—C31—P2121.5 (6)
N1—C1—C2122.5 (8)C33—C32—C31119.9 (8)
N1—C1—H1118.7C33—C32—H32120.1
C2—C1—H1118.7C31—C32—H32120.1
C3—C2—C1119.2 (8)C34—C33—C32120.0 (9)
C3—C2—H2120.4C34—C33—H33120.0
C1—C2—H2120.4C32—C33—H33120.0
C2—C3—C4118.8 (8)C33—C34—C35121.6 (8)
C2—C3—H3120.6C33—C34—H34119.2
C4—C3—H3120.6C35—C34—H34119.2
C3—C4—C5120.1 (8)C34—C35—C36119.9 (9)
C3—C4—H4120.0C34—C35—H35120.1
C5—C4—H4120.0C36—C35—H35120.1
N1—C5—C4122.4 (7)C31—C36—C35120.0 (8)
N1—C5—C6115.5 (6)C31—C36—H36120.0
C4—C5—C6122.1 (7)C35—C36—H36120.0
N2—C6—C5119.1 (6)C42—C37—C38116.0 (7)
N2—C6—H6120.4C42—C37—P2119.4 (6)
C5—C6—H6120.4C38—C37—P2124.4 (6)
C12—C7—C8118.4 (7)C37—C38—C39122.0 (8)
C12—C7—P1123.6 (6)C37—C38—H38119.0
C8—C7—P1118.0 (5)C39—C38—H38119.0
C9—C8—C7121.6 (8)C40—C39—C38119.3 (9)
C9—C8—H8119.2C40—C39—H39120.4
C7—C8—H8119.2C38—C39—H39120.4
C10—C9—C8118.8 (8)C41—C40—C39119.9 (8)
C10—C9—H9120.6C41—C40—H40120.1
C8—C9—H9120.6C39—C40—H40120.1
C11—C10—C9120.3 (8)C40—C41—C42119.4 (9)
C11—C10—H10119.8C40—C41—H41120.3
C9—C10—H10119.8C42—C41—H41120.3
C10—C11—C12120.7 (8)C37—C42—C41123.3 (8)
C10—C11—H11119.6C37—C42—H42118.4
C12—C11—H11119.6C41—C42—H42118.4
C7—C12—C11120.0 (7)Cl2—C43—Cl1119.5 (15)
C7—C12—H12120.0Cl2—C43—H43A107.4
C11—C12—H12120.0Cl1—C43—H43A107.4
C14—C13—C18119.0 (7)Cl2—C43—H43B107.4
C14—C13—P1123.1 (6)Cl1—C43—H43B107.4
C18—C13—P1117.8 (5)H43A—C43—H43B107.0
C13—C14—C15120.0 (8)Cl4—C44—Cl3106 (5)
C13—C14—H14120.0Cl4—C44—H44A110.5
C15—C14—H14120.0Cl3—C44—H44A110.5
C16—C15—C14119.8 (9)Cl4—C44—H44B110.5
C16—C15—H15120.1Cl3—C44—H44B110.5
C14—C15—H15120.1H44A—C44—H44B108.7
C15—C16—C17121.9 (9)Cl6—C45—Cl5116 (5)
C15—C16—H16119.0Cl6—C45—H45A108.4
C17—C16—H16119.0Cl5—C45—H45A108.4
C18—C17—C16116.7 (8)Cl6—C45—H45B108.4
C18—C17—H17121.7Cl5—C45—H45B108.4
C16—C17—H17121.7H45A—C45—H45B107.4
C17—C18—C13122.6 (7)Cl8—C46—Cl7107 (7)
C17—C18—H18118.7Cl8—C46—H46A110.2
C13—C18—H18118.7Cl7—C46—H46A110.2
C24—C19—C20116.9 (7)Cl8—C46—H46B110.2
C24—C19—P1120.1 (5)Cl7—C46—H46B109.0
C20—C19—P1123.0 (6)H46A—C46—H46B108.5
N2—Cu1—N1—C1179.0 (7)C18—C13—C14—C151.0 (12)
P1—Cu1—N1—C174.3 (6)P1—C13—C14—C15179.4 (7)
P2—Cu1—N1—C1−70.2 (7)C13—C14—C15—C16−1.7 (14)
N2—Cu1—N1—C5−2.5 (5)C14—C15—C16—C172.3 (16)
P1—Cu1—N1—C5−107.3 (5)C15—C16—C17—C18−2.3 (15)
P2—Cu1—N1—C5108.3 (5)C16—C17—C18—C131.6 (13)
N1—Cu1—N2—C62.1 (5)C14—C13—C18—C17−1.1 (12)
P1—Cu1—N2—C6111.4 (5)P1—C13—C18—C17−179.6 (6)
P2—Cu1—N2—C6−106.8 (5)C13—P1—C19—C24−79.3 (7)
N1—Cu1—N2—N2i−178.3 (8)C7—P1—C19—C24173.0 (6)
P1—Cu1—N2—N2i−69.1 (7)Cu1—P1—C19—C2445.7 (7)
P2—Cu1—N2—N2i72.8 (7)C13—P1—C19—C2096.9 (7)
N1—Cu1—P1—C13159.0 (3)C7—P1—C19—C20−10.7 (7)
N2—Cu1—P1—C1375.5 (3)Cu1—P1—C19—C20−138.0 (6)
P2—Cu1—P1—C13−61.5 (3)C24—C19—C20—C210.5 (12)
N1—Cu1—P1—C7−81.9 (3)P1—C19—C20—C21−175.9 (6)
N2—Cu1—P1—C7−165.4 (3)C19—C20—C21—C220.7 (13)
P2—Cu1—P1—C757.6 (3)C20—C21—C22—C23−1.8 (13)
N1—Cu1—P1—C1939.4 (3)C21—C22—C23—C241.7 (13)
N2—Cu1—P1—C19−44.0 (3)C20—C19—C24—C23−0.6 (12)
P2—Cu1—P1—C19178.9 (3)P1—C19—C24—C23175.9 (7)
N1—Cu1—P2—C3782.5 (3)C22—C23—C24—C19−0.5 (13)
N2—Cu1—P2—C37168.2 (3)C37—P2—C25—C3015.0 (7)
P1—Cu1—P2—C37−56.9 (3)C31—P2—C25—C30123.6 (7)
N1—Cu1—P2—C31−40.3 (3)Cu1—P2—C25—C30−109.4 (6)
N2—Cu1—P2—C3145.4 (3)C37—P2—C25—C26−169.6 (6)
P1—Cu1—P2—C31−179.7 (3)C31—P2—C25—C26−61.0 (6)
N1—Cu1—P2—C25−160.3 (3)Cu1—P2—C25—C2666.0 (6)
N2—Cu1—P2—C25−74.7 (3)C30—C25—C26—C272.5 (11)
P1—Cu1—P2—C2560.3 (3)P2—C25—C26—C27−173.1 (6)
C5—N1—C1—C21.4 (12)C25—C26—C27—C28−1.4 (12)
Cu1—N1—C1—C2179.8 (7)C26—C27—C28—C29−0.4 (13)
N1—C1—C2—C3−3.8 (15)C27—C28—C29—C301.1 (13)
C1—C2—C3—C44.7 (16)C26—C25—C30—C29−1.9 (11)
C2—C3—C4—C5−3.4 (16)P2—C25—C30—C29173.4 (6)
C1—N1—C5—C4−0.1 (11)C28—C29—C30—C250.1 (13)
Cu1—N1—C5—C4−178.7 (6)C37—P2—C31—C36−110.6 (7)
C1—N1—C5—C6−178.7 (7)C25—P2—C31—C36143.2 (7)
Cu1—N1—C5—C62.6 (8)Cu1—P2—C31—C3617.3 (8)
C3—C4—C5—N11.1 (14)C37—P2—C31—C3267.5 (7)
C3—C4—C5—C6179.6 (8)C25—P2—C31—C32−38.7 (7)
N2i—N2—C6—C5178.9 (6)Cu1—P2—C31—C32−164.6 (6)
Cu1—N2—C6—C5−1.4 (8)C36—C31—C32—C333.0 (13)
N1—C5—C6—N2−0.7 (10)P2—C31—C32—C33−175.1 (7)
C4—C5—C6—N2−179.4 (7)C31—C32—C33—C34−4.6 (14)
C13—P1—C7—C12−6.9 (7)C32—C33—C34—C353.3 (16)
C19—P1—C7—C1299.9 (7)C33—C34—C35—C36−0.5 (16)
Cu1—P1—C7—C12−131.2 (6)C32—C31—C36—C35−0.2 (13)
C13—P1—C7—C8175.2 (6)P2—C31—C36—C35177.9 (7)
C19—P1—C7—C8−78.0 (7)C34—C35—C36—C31−1.1 (15)
Cu1—P1—C7—C850.9 (7)C31—P2—C37—C42159.1 (7)
C12—C7—C8—C93.5 (13)C25—P2—C37—C42−93.7 (7)
P1—C7—C8—C9−178.4 (7)Cu1—P2—C37—C4230.5 (8)
C7—C8—C9—C10−2.1 (15)C31—P2—C37—C38−25.2 (9)
C8—C9—C10—C11−0.8 (15)C25—P2—C37—C3882.0 (8)
C9—C10—C11—C122.0 (14)Cu1—P2—C37—C38−153.8 (7)
C8—C7—C12—C11−2.2 (11)C42—C37—C38—C392.4 (14)
P1—C7—C12—C11179.9 (6)P2—C37—C38—C39−173.3 (8)
C10—C11—C12—C7−0.5 (13)C37—C38—C39—C40−3.5 (16)
C7—P1—C13—C14100.6 (7)C38—C39—C40—C412.0 (16)
C19—P1—C13—C14−6.4 (7)C39—C40—C41—C420.4 (16)
Cu1—P1—C13—C14−134.1 (6)C38—C37—C42—C410.1 (14)
C7—P1—C13—C18−81.0 (6)P2—C37—C42—C41176.1 (8)
C19—P1—C13—C18172.0 (6)C40—C41—C42—C37−1.6 (16)
Cu1—P1—C13—C1844.3 (6)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2211).

References

  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Guo, D., Duan, C., Fang, C. & Meng, Q. (2002). J. Chem. Soc. Dalton Trans. pp. 834–836.
  • Hamblin, J., Jackson, A., Alcock, N. W. & Hannon, M. J. (2002). J. Chem. Soc. Dalton Trans. pp. 1635–1641.
  • Mo, J., Qian, H.-Y., Du, X.-D. & Chen, W. (2006). Acta Cryst. E62, m726–m727.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tuna, F., Hamblin, J., Jackson, A., Clarkson, G., Alcock, N. W. & Hannon, M. J. (2003). Dalton Trans. pp. 2141–2148.
  • Zhou, X., Wu, T. & Li, D. (2006). Inorg. Chim. Acta, 359, 1442–1448.

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