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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m219.
Published online 2010 January 30. doi:  10.1107/S1600536810002965
PMCID: PMC2979668

[6-(4-Bromo­phen­yl)-2,2′-bipyridine-κ2 N,N′](tricyclo­hexyl­phosphine-κP)copper(I) tetra­fluoridoborate

Abstract

In the title compound, [Cu(C16H11BrN2)(C18H33P)]BF4, the CuI atom is three-coordinated in a distorted trigonal configuration by two N atoms from the 6-(4-bromo­phen­yl)-2,2′-bipyridine ligand and a P atom from the tricyclo­hexyl­phosphine ligand. In addition, a weak anion(...)CuI inter­action with a nearest F(...)Cu separation of 2.696 (5) Å is found.

Related literature

For the rich photophysical properties of opper(I) complexes with diimine and phosphine ligands and their potential applications in organic light-emitting diodes (OLEDs), see: Miller et al. (1999 [triangle]); Zhang et al. (2006 [triangle]). For related structures, see: Wang et al. (2010 [triangle]). For a similar weak anion(...)Cu(I) inter­action, see: Mao et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m219-scheme1.jpg

Experimental

Crystal data

  • [Cu(C16H11BrN2)(C18H33P)]BF4
  • M r = 741.94
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m219-efi1.jpg
  • a = 9.8950 (8) Å
  • b = 20.2114 (17) Å
  • c = 17.3317 (14) Å
  • β = 93.010 (1)°
  • V = 3461.4 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.88 mm−1
  • T = 293 K
  • 0.45 × 0.30 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.514, T max = 0.687
  • 26011 measured reflections
  • 8150 independent reflections
  • 4532 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.151
  • S = 1.02
  • 8150 reflections
  • 398 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002965/hg2631sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002965/hg2631Isup2.hkl

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

supplementary crystallographic information

Comment

Copper(I) complexes with diimine and phosphine ligands have attracted much attention for their rich photophysical properties and potential applications in organic light-emitting diodes (OLEDs) (Miller et al., 1999; Zhang et al., 2006). These complexes are generally four-coordinate. With bulky phosphine ligands such as tricyclohexylphosphine, three-coordinate complexes have been reported (Wang et al., 2010). We reported here a new three-coordinated copper(I) complex of the title compound, (I).

Compound (I)

The crystal structure of (I) is depicted in Fig. 1. The copper(I) atom is three-coordinated in distorted trigonal configurations by two N atoms from 6-(4-bromo)phenyl-2,2'-bipyridine and a P atom from tricyclohexylphosphine. The coordination angles around the copper(I) atom are 80.029 (11) ° (N1—Cu1—N2), 131.74 (8) ° (N1—Cu1—P1) and 129.43 (7) ° (P1—Cu1—N2) respectively. The Cu—P (2.1811 (9) Å) and Cu—N (2.038 (3) and 2.080 (3) Å) distances are within the normal ranges for related complexes (Wang et al., 2010). In addition, weak anion···Cu(I) interaction is founded, as evidenced by the nearest F···Cu separation of 2.696 (5) Å (Cu1—F1) in the title compound. Similar weak anion···Cu(I) interaction was also reported by Mao et al. (2003).

Experimental

The ligand 6-(4-bromo)phenyl-2,2'-bipyridine (L) was prepared by literature method (Wang et al., 2010). A mixture of [Cu(CH3CN)4]BF4 (100 mg, 0.32 mmol) and L (99 mg, 0.32 mmol) in dichloromethane (20 ml) was stirred under nitrogen atmosphere at room temperature for 2 h. Then tricyclohexylphosphine (89 mg, 0.32 mmol) was added kept stirring for 2 h. The solvents were removed and the solid residue was afforded. Yellow single crystals suitable for X-ray diffraction were obtained from the solution of dichloromethane by vapor diffusion with diethyl ether (yield: 82%). Analysis calculated for [Cu(C16H11N2Br)(C18H33P)].(BF4): C 53.38, H 5.93 N 3.77%; Found: C 53.92, H 5.63, 3.57%.

Refinement

All H atoms were positioned geomertrically and treated as riding (C—H = 0.97 Å for cyclohexyl and C—H = 0.93 Å otherwise) with Uiso(H) = 1.2 Ueq(C) of the carrier atom.

Figures

Fig. 1.
: The molecular structure of compound (I). Displacement ellipsoids are drawn at the 30% probability level, and all hydrogen atoms are omitted for clarity.

Crystal data

[Cu(C16H11BrN2)(C18H33P)]BF4F(000) = 1528
Mr = 741.94Dx = 1.424 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 892 reflections
a = 9.8950 (8) Åθ = 2.2–25.8°
b = 20.2114 (17) ŵ = 1.88 mm1
c = 17.3317 (14) ÅT = 293 K
β = 93.010 (1)°Block, yellow
V = 3461.4 (5) Å30.45 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer8150 independent reflections
Radiation source: fine-focus sealed tube4532 reflections with I > 2σ(I)
graphiteRint = 0.043
phi and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −13→13
Tmin = 0.514, Tmax = 0.687k = −26→26
26011 measured reflectionsl = −23→21

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.059P)2 + 1.0457P] where P = (Fo2 + 2Fc2)/3
8150 reflections(Δ/σ)max = 0.012
398 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.70 e Å3

Special details

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)

xyzUiso*/Ueq
Cu10.68710 (4)0.11177 (2)0.13751 (2)0.05341 (15)
P10.77547 (9)0.19570 (4)0.20113 (5)0.0467 (2)
Br10.78459 (6)0.00217 (4)0.49674 (3)0.1190 (3)
N20.4943 (3)0.07131 (12)0.14102 (15)0.0469 (6)
N10.6442 (3)0.09700 (14)0.02248 (16)0.0542 (7)
C10.8915 (5)0.24251 (19)0.1413 (3)0.0848 (14)
H1A0.96640.23410.17920.102*
C20.9125 (5)0.3136 (2)0.1498 (3)0.0845 (13)
H2A0.94890.32180.20200.101*
H2B0.82480.33500.14460.101*
C31.0017 (6)0.3458 (2)0.0961 (4)0.117 (2)
H3A0.94930.38050.07000.140*
H3B1.07300.36750.12720.140*
C41.0649 (6)0.3095 (3)0.0385 (3)0.118 (2)
H4A1.16140.31760.04540.142*
H4B1.03550.3286−0.01100.142*
C51.0469 (5)0.2393 (3)0.0321 (3)0.0971 (16)
H5A1.13550.21890.03820.117*
H5B1.01200.2298−0.02010.117*
C60.9594 (6)0.2066 (2)0.0848 (3)0.1063 (19)
H6A0.89060.18340.05350.128*
H6B1.01350.17310.11210.128*
C70.6381 (3)0.25423 (16)0.22294 (19)0.0517 (8)
H7A0.67890.29520.24350.062*
C80.5519 (4)0.2706 (2)0.1495 (2)0.0724 (11)
H8A0.60810.29200.11270.087*
H8B0.51740.22990.12630.087*
C130.8643 (3)0.17867 (16)0.29569 (18)0.0515 (8)
H13A0.79830.15510.32570.062*
C240.4262 (4)0.07942 (15)0.07240 (19)0.0509 (8)
C280.4265 (3)0.05544 (15)0.2040 (2)0.0510 (8)
C290.5105 (4)0.04185 (16)0.27528 (19)0.0510 (8)
C230.5110 (4)0.09002 (15)0.00546 (19)0.0517 (8)
C330.7185 (4)0.00015 (19)0.3355 (2)0.0668 (10)
H33A0.8025−0.02000.33180.080*
F20.8170 (3)−0.09236 (13)0.17853 (19)0.1044 (9)
C190.7271 (4)0.10229 (19)−0.0355 (2)0.0651 (10)
H19A0.81960.1055−0.02370.078*
C340.6373 (4)0.01317 (17)0.2707 (2)0.0583 (9)
H34A0.66800.00250.22240.070*
C220.4591 (4)0.09145 (17)−0.0705 (2)0.0631 (10)
H22A0.36640.0878−0.08170.076*
C270.2865 (4)0.05087 (18)0.1998 (2)0.0635 (10)
H27A0.24030.04090.24370.076*
C320.6723 (5)0.0178 (2)0.4065 (2)0.0713 (11)
C120.5487 (4)0.22462 (19)0.2837 (2)0.0649 (10)
H12A0.51640.18160.26630.078*
H12B0.60240.21840.33160.078*
C180.9811 (4)0.1305 (2)0.2887 (2)0.0670 (10)
H18A0.94920.09160.26060.080*
H18B1.05080.15110.25960.080*
C140.9064 (5)0.23832 (19)0.3445 (2)0.0720 (11)
H14A0.97280.26390.31810.086*
H14B0.82820.26630.35120.086*
C300.4678 (4)0.05694 (17)0.3477 (2)0.0625 (10)
H30A0.38260.07550.35200.075*
C171.0409 (5)0.1100 (2)0.3669 (2)0.0748 (11)
H17A1.11910.08200.36020.090*
H17B0.97470.08430.39340.090*
C260.2172 (4)0.06113 (19)0.1308 (2)0.0696 (11)
H26A0.12320.05880.12770.084*
C200.6821 (5)0.10323 (18)−0.1120 (2)0.0718 (11)
H20A0.74270.1071−0.15100.086*
F10.8562 (3)0.00766 (13)0.12988 (18)0.1024 (9)
B10.9142 (5)−0.0521 (3)0.1505 (3)0.0689 (12)
C150.9660 (6)0.2171 (2)0.4231 (2)0.0899 (15)
H15A0.99730.25590.45190.108*
H15B0.89630.19600.45180.108*
C310.5477 (5)0.04533 (19)0.4138 (2)0.0697 (11)
H31A0.51740.05600.46210.084*
C250.2863 (4)0.07504 (19)0.0657 (2)0.0656 (10)
H25A0.24000.08130.01820.079*
C210.5465 (5)0.09833 (18)−0.1291 (2)0.0731 (12)
H21A0.51310.0996−0.18030.088*
F41.0131 (3)−0.04289 (16)0.20553 (19)0.1233 (11)
C110.4289 (4)0.2684 (2)0.2986 (3)0.0807 (12)
H11A0.46090.30920.32270.097*
H11B0.37150.24620.33420.097*
F30.9654 (4)−0.07998 (18)0.08765 (19)0.1367 (12)
C161.0830 (5)0.1695 (2)0.4158 (3)0.0908 (14)
H16A1.11480.15480.46680.109*
H16B1.15690.19220.39250.109*
C100.3467 (5)0.2845 (3)0.2250 (3)0.1079 (19)
H10A0.30590.24430.20390.130*
H10B0.27450.31480.23650.130*
C90.4344 (5)0.3154 (3)0.1659 (3)0.0993 (16)
H9A0.46860.35760.18500.119*
H9B0.38050.32340.11840.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0505 (3)0.0598 (3)0.0497 (3)−0.0065 (2)0.00034 (18)−0.00971 (18)
P10.0461 (5)0.0488 (5)0.0448 (5)−0.0027 (4)−0.0008 (4)−0.0016 (4)
Br10.1016 (5)0.1800 (6)0.0738 (4)−0.0118 (4)−0.0103 (3)0.0430 (3)
N20.0463 (16)0.0445 (14)0.0495 (16)−0.0020 (12)−0.0010 (13)−0.0071 (11)
N10.0588 (19)0.0575 (17)0.0464 (15)−0.0013 (14)0.0040 (14)−0.0103 (12)
C10.104 (4)0.055 (2)0.100 (3)−0.006 (2)0.050 (3)0.005 (2)
C20.103 (4)0.061 (2)0.091 (3)−0.020 (2)0.021 (3)0.004 (2)
C30.128 (5)0.071 (3)0.158 (6)−0.007 (3)0.062 (4)0.027 (3)
C40.131 (5)0.112 (4)0.117 (4)−0.028 (4)0.056 (4)0.021 (3)
C50.106 (4)0.097 (4)0.092 (3)0.006 (3)0.043 (3)0.017 (3)
C60.131 (5)0.083 (3)0.111 (4)−0.030 (3)0.065 (4)−0.021 (3)
C70.048 (2)0.0499 (18)0.0562 (19)0.0000 (15)−0.0035 (15)−0.0059 (15)
C80.066 (3)0.086 (3)0.064 (2)0.014 (2)−0.009 (2)−0.004 (2)
C130.053 (2)0.0535 (19)0.0472 (19)−0.0032 (16)−0.0035 (15)−0.0024 (14)
C240.052 (2)0.0411 (17)0.058 (2)0.0029 (15)−0.0029 (16)−0.0088 (14)
C280.051 (2)0.0431 (18)0.060 (2)0.0009 (15)0.0083 (16)−0.0058 (15)
C290.053 (2)0.0465 (18)0.054 (2)−0.0054 (16)0.0124 (16)−0.0032 (14)
C230.059 (2)0.0389 (17)0.056 (2)−0.0003 (15)−0.0055 (17)−0.0051 (14)
C330.059 (2)0.074 (3)0.068 (3)0.0010 (19)0.008 (2)0.0142 (19)
F20.0653 (16)0.0881 (17)0.160 (3)−0.0037 (14)0.0074 (17)0.0175 (17)
C190.069 (3)0.072 (2)0.054 (2)−0.0079 (19)0.0067 (19)−0.0102 (17)
C340.057 (2)0.061 (2)0.058 (2)−0.0032 (18)0.0107 (18)−0.0006 (16)
C220.074 (3)0.057 (2)0.056 (2)0.0006 (18)−0.0167 (19)−0.0014 (16)
C270.053 (2)0.066 (2)0.073 (3)0.0020 (18)0.014 (2)−0.0090 (18)
C320.078 (3)0.078 (3)0.059 (2)−0.014 (2)0.001 (2)0.0165 (19)
C120.063 (2)0.064 (2)0.069 (2)0.0038 (19)0.0127 (19)−0.0100 (18)
C180.063 (3)0.078 (3)0.059 (2)0.012 (2)−0.0071 (19)0.0004 (18)
C140.092 (3)0.061 (2)0.061 (2)0.001 (2)−0.022 (2)−0.0081 (18)
C300.065 (2)0.061 (2)0.063 (2)0.0029 (18)0.0165 (19)−0.0004 (17)
C170.069 (3)0.088 (3)0.067 (3)0.019 (2)−0.006 (2)0.009 (2)
C260.045 (2)0.073 (3)0.091 (3)−0.0029 (19)0.003 (2)−0.006 (2)
C200.101 (4)0.061 (2)0.054 (2)−0.008 (2)0.012 (2)−0.0045 (17)
F10.104 (2)0.0866 (17)0.118 (2)0.0332 (15)0.0251 (17)0.0238 (15)
B10.051 (3)0.076 (3)0.081 (3)0.007 (2)0.009 (2)0.000 (2)
C150.133 (4)0.078 (3)0.055 (2)0.000 (3)−0.028 (3)−0.004 (2)
C310.087 (3)0.071 (2)0.052 (2)−0.008 (2)0.014 (2)0.0030 (18)
C250.055 (2)0.063 (2)0.077 (3)0.0020 (18)−0.0142 (19)−0.0041 (19)
C210.117 (4)0.054 (2)0.046 (2)0.001 (2)−0.012 (2)−0.0041 (16)
F40.099 (2)0.130 (2)0.135 (3)−0.0346 (19)−0.0452 (19)0.0268 (19)
C110.062 (3)0.095 (3)0.085 (3)0.009 (2)0.012 (2)−0.024 (2)
F30.137 (3)0.155 (3)0.121 (3)0.051 (2)0.036 (2)−0.024 (2)
C160.083 (3)0.108 (4)0.077 (3)−0.010 (3)−0.032 (2)0.016 (3)
C100.059 (3)0.156 (5)0.108 (4)0.033 (3)−0.009 (3)−0.044 (4)
C90.086 (4)0.121 (4)0.087 (3)0.047 (3)−0.027 (3)−0.014 (3)

Geometric parameters (Å, °)

Cu1—N12.038 (3)F2—B11.368 (5)
Cu1—N22.080 (3)C19—C201.376 (5)
Cu1—P12.1811 (9)C19—H19A0.9300
P1—C11.848 (4)C34—H34A0.9300
P1—C131.851 (3)C22—C211.375 (6)
P1—C71.855 (3)C22—H22A0.9300
Br1—C321.896 (4)C27—C261.362 (5)
N2—C241.346 (4)C27—H27A0.9300
N2—C281.349 (4)C32—C311.365 (6)
N1—C191.335 (4)C12—C111.512 (5)
N1—C231.342 (4)C12—H12A0.9700
C1—C61.416 (5)C12—H12B0.9700
C1—C21.457 (5)C18—C171.507 (5)
C1—H1A0.9800C18—H18A0.9700
C2—C31.468 (6)C18—H18B0.9700
C2—H2A0.9700C14—C151.518 (5)
C2—H2B0.9700C14—H14A0.9700
C3—C41.412 (7)C14—H14B0.9700
C3—H3A0.9700C30—C311.377 (6)
C3—H3B0.9700C30—H30A0.9300
C4—C51.434 (7)C17—C161.519 (6)
C4—H4A0.9700C17—H17A0.9700
C4—H4B0.9700C17—H17B0.9700
C5—C61.451 (6)C26—C251.380 (5)
C5—H5A0.9700C26—H26A0.9300
C5—H5B0.9700C20—C211.362 (6)
C6—H6A0.9700C20—H20A0.9300
C6—H6B0.9700F1—B11.376 (5)
C7—C121.532 (5)B1—F41.343 (6)
C7—C81.531 (5)B1—F31.349 (5)
C7—H7A0.9800C15—C161.515 (7)
C8—C91.512 (6)C15—H15A0.9700
C8—H8A0.9700C15—H15B0.9700
C8—H8B0.9700C31—H31A0.9300
C13—C141.519 (5)C25—H25A0.9300
C13—C181.520 (5)C21—H21A0.9300
C13—H13A0.9800C11—C101.512 (7)
C24—C251.385 (5)C11—H11A0.9700
C24—C231.483 (5)C11—H11B0.9700
C28—C271.386 (5)C16—H16A0.9700
C28—C291.479 (5)C16—H16B0.9700
C29—C301.379 (5)C10—C91.513 (7)
C29—C341.388 (5)C10—H10A0.9700
C23—C221.389 (5)C10—H10B0.9700
C33—C341.372 (5)C9—H9A0.9700
C33—C321.382 (6)C9—H9B0.9700
C33—H33A0.9300
N1—Cu1—N280.02 (11)C29—C34—H34A119.2
N1—Cu1—P1131.74 (8)C21—C22—C23119.1 (4)
N2—Cu1—P1129.43 (7)C21—C22—H22A120.4
C1—P1—C13108.2 (2)C23—C22—H22A120.4
C1—P1—C7105.74 (18)C26—C27—C28119.5 (4)
C13—P1—C7104.91 (15)C26—C27—H27A120.3
C1—P1—Cu1111.03 (15)C28—C27—H27A120.3
C13—P1—Cu1117.53 (11)C31—C32—C33122.0 (4)
C7—P1—Cu1108.68 (11)C31—C32—Br1119.0 (3)
C24—N2—C28119.8 (3)C33—C32—Br1119.0 (3)
C24—N2—Cu1110.1 (2)C11—C12—C7112.0 (3)
C28—N2—Cu1127.8 (2)C11—C12—H12A109.2
C19—N1—C23118.5 (3)C7—C12—H12A109.2
C19—N1—Cu1128.3 (3)C11—C12—H12B109.2
C23—N1—Cu1112.5 (2)C7—C12—H12B109.2
C6—C1—C2120.3 (4)H12A—C12—H12B107.9
C6—C1—P1117.2 (3)C17—C18—C13111.7 (3)
C2—C1—P1122.5 (3)C17—C18—H18A109.3
C6—C1—H1A90.3C13—C18—H18A109.3
C2—C1—H1A90.3C17—C18—H18B109.3
P1—C1—H1A90.3C13—C18—H18B109.3
C1—C2—C3117.5 (4)H18A—C18—H18B107.9
C1—C2—H2A107.9C15—C14—C13111.0 (3)
C3—C2—H2A107.9C15—C14—H14A109.4
C1—C2—H2B107.9C13—C14—H14A109.4
C3—C2—H2B107.9C15—C14—H14B109.4
H2A—C2—H2B107.2C13—C14—H14B109.4
C4—C3—C2121.4 (4)H14A—C14—H14B108.0
C4—C3—H3A107.0C31—C30—C29122.0 (4)
C2—C3—H3A107.0C31—C30—H30A119.0
C4—C3—H3B107.0C29—C30—H30A119.0
C2—C3—H3B107.0C18—C17—C16111.5 (3)
H3A—C3—H3B106.7C18—C17—H17A109.3
C3—C4—C5120.8 (4)C16—C17—H17A109.3
C3—C4—H4A107.1C18—C17—H17B109.3
C5—C4—H4A107.1C16—C17—H17B109.3
C3—C4—H4B107.1H17A—C17—H17B108.0
C5—C4—H4B107.1C27—C26—C25120.0 (4)
H4A—C4—H4B106.8C27—C26—H26A120.0
C4—C5—C6118.5 (4)C25—C26—H26A120.0
C4—C5—H5A107.7C21—C20—C19118.3 (4)
C6—C5—H5A107.7C21—C20—H20A120.9
C4—C5—H5B107.7C19—C20—H20A120.9
C6—C5—H5B107.7F4—B1—F3109.9 (4)
H5A—C5—H5B107.1F4—B1—F2109.3 (4)
C1—C6—C5121.6 (4)F3—B1—F2109.8 (4)
C1—C6—H6A106.9F4—B1—F1110.0 (4)
C5—C6—H6A106.9F3—B1—F1109.0 (4)
C1—C6—H6B106.9F2—B1—F1108.8 (4)
C5—C6—H6B106.9C16—C15—C14111.5 (4)
H6A—C6—H6B106.7C16—C15—H15A109.3
C12—C7—C8109.8 (3)C14—C15—H15A109.3
C12—C7—P1110.3 (2)C16—C15—H15B109.3
C8—C7—P1110.5 (2)C14—C15—H15B109.3
C12—C7—H7A108.7H15A—C15—H15B108.0
C8—C7—H7A108.7C32—C31—C30118.3 (4)
P1—C7—H7A108.7C32—C31—H31A120.8
C9—C8—C7111.9 (3)C30—C31—H31A120.8
C9—C8—H8A109.2C26—C25—C24118.7 (4)
C7—C8—H8A109.2C26—C25—H25A120.6
C9—C8—H8B109.2C24—C25—H25A120.6
C7—C8—H8B109.2C20—C21—C22119.8 (4)
H8A—C8—H8B107.9C20—C21—H21A120.1
C14—C13—C18111.4 (3)C22—C21—H21A120.1
C14—C13—P1116.7 (2)C12—C11—C10111.9 (3)
C18—C13—P1112.1 (2)C12—C11—H11A109.2
C14—C13—H13A105.1C10—C11—H11A109.2
C18—C13—H13A105.1C12—C11—H11B109.2
P1—C13—H13A105.1C10—C11—H11B109.2
N2—C24—C25121.2 (3)H11A—C11—H11B107.9
N2—C24—C23115.5 (3)C15—C16—C17111.2 (4)
C25—C24—C23123.2 (3)C15—C16—H16A109.4
N2—C28—C27120.7 (3)C17—C16—H16A109.4
N2—C28—C29116.0 (3)C15—C16—H16B109.4
C27—C28—C29123.2 (3)C17—C16—H16B109.4
C30—C29—C34117.7 (3)H16A—C16—H16B108.0
C30—C29—C28122.3 (3)C9—C10—C11111.0 (4)
C34—C29—C28120.0 (3)C9—C10—H10A109.4
N1—C23—C22121.1 (3)C11—C10—H10A109.4
N1—C23—C24115.6 (3)C9—C10—H10B109.4
C22—C23—C24123.3 (3)C11—C10—H10B109.4
C34—C33—C32118.2 (4)H10A—C10—H10B108.0
C34—C33—H33A120.9C10—C9—C8110.7 (4)
C32—C33—H33A120.9C10—C9—H9A109.5
N1—C19—C20123.1 (4)C8—C9—H9A109.5
N1—C19—H19A118.5C10—C9—H9B109.5
C20—C19—H19A118.5C8—C9—H9B109.5
C33—C34—C29121.7 (3)H9A—C9—H9B108.1
C33—C34—H34A119.2
N1—Cu1—P1—C1−29.0 (2)N2—C28—C29—C30147.1 (3)
N2—Cu1—P1—C1−144.6 (2)C27—C28—C29—C30−34.5 (5)
N1—Cu1—P1—C13−154.23 (16)N2—C28—C29—C34−32.6 (4)
N2—Cu1—P1—C1390.12 (16)C27—C28—C29—C34145.7 (3)
N1—Cu1—P1—C786.93 (16)C19—N1—C23—C22−3.1 (5)
N2—Cu1—P1—C7−28.73 (15)Cu1—N1—C23—C22168.3 (3)
N1—Cu1—N2—C24−22.3 (2)C19—N1—C23—C24175.6 (3)
P1—Cu1—N2—C24114.66 (19)Cu1—N1—C23—C24−13.0 (3)
N1—Cu1—N2—C28175.3 (3)N2—C24—C23—N1−6.6 (4)
P1—Cu1—N2—C28−47.8 (3)C25—C24—C23—N1176.2 (3)
N2—Cu1—N1—C19−170.5 (3)N2—C24—C23—C22172.1 (3)
P1—Cu1—N1—C1954.4 (3)C25—C24—C23—C22−5.1 (5)
N2—Cu1—N1—C2319.1 (2)C23—N1—C19—C202.3 (5)
P1—Cu1—N1—C23−115.9 (2)Cu1—N1—C19—C20−167.5 (3)
C13—P1—C1—C6100.5 (5)C32—C33—C34—C29−1.5 (5)
C7—P1—C1—C6−147.6 (4)C30—C29—C34—C33−0.1 (5)
Cu1—P1—C1—C6−29.9 (5)C28—C29—C34—C33179.6 (3)
C13—P1—C1—C2−80.5 (5)N1—C23—C22—C211.8 (5)
C7—P1—C1—C231.5 (5)C24—C23—C22—C21−176.8 (3)
Cu1—P1—C1—C2149.2 (4)N2—C28—C27—C261.4 (5)
C6—C1—C2—C32.2 (8)C29—C28—C27—C26−176.9 (3)
P1—C1—C2—C3−176.8 (4)C34—C33—C32—C312.2 (6)
C1—C2—C3—C4−0.1 (9)C34—C33—C32—Br1−178.5 (3)
C2—C3—C4—C5−1.8 (10)C8—C7—C12—C11−53.4 (4)
C3—C4—C5—C61.6 (10)P1—C7—C12—C11−175.5 (3)
C2—C1—C6—C5−2.5 (9)C14—C13—C18—C1754.7 (4)
P1—C1—C6—C5176.6 (5)P1—C13—C18—C17−172.4 (3)
C4—C5—C6—C10.6 (9)C18—C13—C14—C15−54.7 (5)
C1—P1—C7—C12−170.3 (3)P1—C13—C14—C15174.7 (3)
C13—P1—C7—C12−56.1 (3)C34—C29—C30—C311.0 (5)
Cu1—P1—C7—C1270.4 (3)C28—C29—C30—C31−178.7 (3)
C1—P1—C7—C868.0 (3)C13—C18—C17—C16−54.7 (5)
C13—P1—C7—C8−177.7 (3)C28—C27—C26—C250.9 (6)
Cu1—P1—C7—C8−51.2 (3)N1—C19—C20—C21−0.2 (6)
C12—C7—C8—C955.1 (5)C13—C14—C15—C1655.3 (5)
P1—C7—C8—C9177.0 (3)C33—C32—C31—C30−1.4 (6)
C1—P1—C13—C1462.4 (3)Br1—C32—C31—C30179.4 (3)
C7—P1—C13—C14−50.2 (3)C29—C30—C31—C32−0.3 (6)
Cu1—P1—C13—C14−171.0 (3)C27—C26—C25—C24−1.2 (6)
C1—P1—C13—C18−67.9 (3)N2—C24—C25—C26−0.9 (5)
C7—P1—C13—C18179.6 (3)C23—C24—C25—C26176.1 (3)
Cu1—P1—C13—C1858.8 (3)C19—C20—C21—C22−1.2 (6)
C28—N2—C24—C253.3 (5)C23—C22—C21—C200.4 (5)
Cu1—N2—C24—C25−160.8 (3)C7—C12—C11—C1054.4 (5)
C28—N2—C24—C23−174.0 (3)C14—C15—C16—C17−55.4 (5)
Cu1—N2—C24—C2321.9 (3)C18—C17—C16—C1555.0 (5)
C24—N2—C28—C27−3.5 (5)C12—C11—C10—C9−55.5 (6)
Cu1—N2—C28—C27157.4 (2)C11—C10—C9—C856.5 (6)
C24—N2—C28—C29174.9 (3)C7—C8—C9—C10−57.2 (5)
Cu1—N2—C28—C29−24.2 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2631).

References

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