Tris(2,2′-bipyridine-κ²N,N′)copper(II) bis­(tetra­fluoridoborate)

The Cu atom in the title salt, [Cu(C₁₀H₈N₂)₃](BF₄)₂, has an elongated octa­hedral coordination geometry. Three F atoms of one anion are disordered over two positions with a site occupancy ratio of 3:2.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.061
• wR factor = 0.160
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         B2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         B1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      23.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The crystal structure of tris(2,2'-bipyridine)copper diperchlorate (Anderson, 1972; Liu et al., 1991; Majumdar et al., 1998; Pavlishchuk et al., 1999) and tris(2,2'-bipyridine)copper bis(tetraphenylborate) (Murphy et al., 2006) have been reported previously. We have reported the bis(hexafluoridophosphorate) salt (Wang et al., 2007), and continue our work with the bis(tetrafluoridoborate) salt.

The geometry of the copper atom is an elongated octahedron as the structure has four nearly identical Cu–N bonds and two somewhat longer ones that are trans to each other. The three 2,2'-bipyridine rings are bent, with dihedral angles of 11.2 (3)° (between C1 to C5 and N1 ring and C6 to C10 N2 ring), 31.0 (3)° (between C11 to C15 and N3 ring and C16 to C20 N4 ring) and 14.6 (3)° (between C21 to C25 and N5 ring and C26 to C30 N6 ring).

Related literature

For the diperchlorate salt, see: Anderson (1972); Liu et al. (1991); Majumdar et al. (1998) and Pavlishchuk et al. (1999). For the bis(tetraphenylborate) salt, see Murphy et al. (2006) and for the bis(hexafluoridophosphorate) salt, see Wang et al. (2007).

S2. Experimental

The compound was obtained by refluxing Cu(NO₃)₂.3H₂O (0.121 g, 0.5 mmol) and 2,2'-bipyridine (0.234 g, 1.5 mmol) in a mixture of 80 ml e thanol and 20 ml water for 1 h in the presence of excess NaBF₄. The mixture was concentrated to nearly 5 ml. The blue product was recrystallized from a 3/1 methanol water mixture and the pure compound isolated in 90% yield. CH&N elemental analysis. Calculated for C₃₀H₂₄CuN₆F₁₂P₂: C 51.06, H 3.43, N 11.91%; found: C 51.04, H 3.49, N 11.86%.

S3. Refinement

The non-hydrogen atoms were refined anisotropically, whereas the H atoms were placed in geometrically idealized positions (C—H = 0.93 Å) and refined as riding atoms, with U_iso(H) = 1.2U_eq(C). F5, F6 and F7 atoms of one tetrafluoridoborate anion are refined over two sites with 0.60 (2): 0.40 (2) site occupancy factors.

Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. Molecular plot, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and the H atoms are shown as small spheres of arbitrary radii.

Tris(2,2'-bipyridine-κ²N,N')copper(II) bis(tetrafluoridoborate)

Crystal data

[Cu(C10H8N2)3](BF4)2	Z = 2
Mr = 705.71	F(000) = 714
Triclinic, P1	Dx = 1.521 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.911 (2) Å	Cell parameters from 6691 reflections
b = 10.851 (2) Å	θ = 3.0–27.5°
c = 18.482 (4) Å	µ = 0.79 mm^−1
α = 100.88 (3)°	T = 291 K
β = 90.26 (2)°	Block, blue
γ = 98.08 (3)°	0.20 × 0.12 × 0.10 mm
V = 1541.8 (6) Å^3

Data collection

Rigaku Mercury CCD area-detector diffractometer	5276 independent reflections
Radiation source: Rigaku rotating anode	4853 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
Detector resolution: 14.6199 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→11
Tmin = 0.858, Tmax = 0.925	l = −21→20
13060 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0929P)^2 + 0.8259P] where P = (Fo^2 + 2Fc^2)/3
5276 reflections	(Δ/σ)max = 0.001
452 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

Special details

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.49537 (4)	0.26462 (3)	0.260441 (19)	0.04188 (18)
B1	0.2081 (7)	0.8226 (4)	0.0862 (3)	0.0713 (13)
B2	0.2989 (5)	0.2751 (4)	0.5691 (2)	0.0572 (10)
C1	0.5758 (5)	0.1204 (3)	0.37557 (18)	0.0532 (8)
C2	0.6673 (6)	0.0615 (4)	0.4203 (2)	0.0726 (12)
H2	0.6203	−0.0149	0.4328	0.087*
C3	0.8288 (7)	0.1186 (5)	0.4456 (2)	0.0807 (13)
H3	0.8921	0.0805	0.4754	0.097*
C4	0.8971 (6)	0.2322 (5)	0.4268 (2)	0.0715 (11)
H4	1.0058	0.2719	0.4436	0.086*
C5	0.7991 (5)	0.2847 (4)	0.3825 (2)	0.0637 (9)
H5	0.8433	0.3618	0.3701	0.076*
C6	0.4003 (5)	0.0685 (3)	0.34619 (18)	0.0543 (8)
C7	0.2992 (7)	−0.0319 (4)	0.3697 (2)	0.0774 (12)
H7	0.3426	−0.0721	0.4044	0.093*
C8	0.1369 (7)	−0.0708 (5)	0.3416 (3)	0.0882 (15)
H8	0.0683	−0.1367	0.3576	0.106*
C9	0.0756 (6)	−0.0124 (4)	0.2897 (3)	0.0788 (13)
H9	−0.0350	−0.0381	0.2701	0.095*
C10	0.1788 (5)	0.0845 (4)	0.2669 (2)	0.0642 (9)
H10	0.1369	0.1236	0.2313	0.077*
C11	0.2700 (4)	0.4602 (3)	0.26873 (18)	0.0466 (7)
C12	0.1730 (5)	0.5511 (4)	0.3006 (2)	0.0668 (10)
H12	0.1169	0.5945	0.2713	0.080*
C13	0.1602 (6)	0.5772 (4)	0.3762 (2)	0.0747 (12)
H13	0.0949	0.6379	0.3984	0.090*
C14	0.2444 (5)	0.5126 (4)	0.4179 (2)	0.0650 (10)
H14	0.2368	0.5287	0.4689	0.078*
C15	0.3399 (4)	0.4240 (3)	0.38420 (18)	0.0519 (8)
H15	0.3972	0.3808	0.4131	0.062*
C16	0.2887 (4)	0.4245 (3)	0.18751 (18)	0.0464 (7)
C17	0.2861 (5)	0.5112 (4)	0.1416 (2)	0.0602 (9)
H17	0.2694	0.5942	0.1602	0.072*
C18	0.3090 (6)	0.4708 (4)	0.0674 (2)	0.0727 (11)
H18	0.3097	0.5273	0.0352	0.087*
C19	0.3305 (5)	0.3482 (4)	0.0413 (2)	0.0692 (11)
H19	0.3437	0.3193	−0.0088	0.083*
C20	0.3323 (5)	0.2684 (4)	0.0904 (2)	0.0611 (9)
H20	0.3480	0.1848	0.0725	0.073*
C21	0.7564 (4)	0.3415 (4)	0.16426 (18)	0.0511 (8)
C22	0.8481 (5)	0.4169 (5)	0.1212 (2)	0.0709 (11)
H22	0.9015	0.3802	0.0795	0.085*
C23	0.8595 (6)	0.5468 (5)	0.1406 (3)	0.0787 (13)
H23	0.9201	0.5987	0.1120	0.094*
C24	0.7813 (6)	0.5986 (4)	0.2022 (3)	0.0747 (12)
H24	0.7909	0.6862	0.2167	0.090*
C25	0.6873 (5)	0.5201 (3)	0.2430 (2)	0.0582 (9)
H25	0.6340	0.5560	0.2849	0.070*
C26	0.7395 (4)	0.2022 (4)	0.14967 (17)	0.0507 (8)
C27	0.8424 (5)	0.1326 (5)	0.1022 (2)	0.0754 (12)
H27	0.9284	0.1734	0.0773	0.090*
C28	0.8152 (7)	0.0010 (5)	0.0924 (3)	0.0868 (14)
H28	0.8822	−0.0473	0.0606	0.104*
C29	0.6890 (6)	−0.0562 (4)	0.1299 (2)	0.0748 (12)
H29	0.6687	−0.1441	0.1241	0.090*
C30	0.5918 (5)	0.0179 (3)	0.1767 (2)	0.0598 (9)
H30	0.5053	−0.0220	0.2017	0.072*
F1	0.2206 (7)	0.8026 (3)	0.15562 (17)	0.1338 (15)
F2	0.0550 (4)	0.7601 (3)	0.05207 (18)	0.1028 (10)
F3	0.3345 (5)	0.7722 (4)	0.0444 (2)	0.1279 (13)
F4	0.2193 (4)	0.9489 (2)	0.08575 (18)	0.0921 (8)
F5	0.4322 (11)	0.2699 (7)	0.6125 (7)	0.113 (4)	0.60 (2)
F6	0.312 (2)	0.2132 (10)	0.5016 (4)	0.141 (6)	0.60 (2)
F8	0.2847 (5)	0.3995 (3)	0.5705 (2)	0.1150 (11)
F7	0.1557 (11)	0.2347 (11)	0.5970 (10)	0.160 (7)	0.60 (2)
N1	0.6436 (4)	0.2301 (3)	0.35638 (15)	0.0523 (7)
N2	0.3391 (4)	0.1247 (3)	0.29465 (16)	0.0521 (7)
N3	0.3538 (3)	0.3971 (2)	0.31056 (14)	0.0451 (6)
N4	0.3126 (4)	0.3045 (3)	0.16283 (15)	0.0516 (7)
N5	0.6716 (3)	0.3931 (3)	0.22333 (14)	0.0468 (6)
N6	0.6162 (3)	0.1444 (3)	0.18753 (14)	0.0467 (6)
F5'	0.4303 (17)	0.2429 (13)	0.5288 (12)	0.134 (7)	0.40 (2)
F6'	0.167 (2)	0.1857 (13)	0.5369 (11)	0.138 (8)	0.40 (2)
F7'	0.316 (3)	0.2394 (10)	0.6360 (4)	0.128 (9)	0.40 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0510 (3)	0.0333 (2)	0.0445 (3)	0.00823 (16)	0.01055 (16)	0.01354 (16)
B1	0.096 (3)	0.044 (2)	0.073 (3)	0.012 (2)	−0.005 (3)	0.008 (2)
B2	0.055 (2)	0.056 (2)	0.063 (3)	0.0074 (18)	−0.0015 (19)	0.0168 (19)
C1	0.081 (2)	0.0435 (17)	0.0424 (17)	0.0206 (16)	0.0174 (16)	0.0167 (14)
C2	0.103 (3)	0.064 (2)	0.067 (2)	0.034 (2)	0.019 (2)	0.036 (2)
C3	0.100 (3)	0.093 (3)	0.066 (3)	0.046 (3)	0.006 (2)	0.032 (2)
C4	0.072 (2)	0.088 (3)	0.061 (2)	0.024 (2)	−0.0003 (19)	0.023 (2)
C5	0.071 (2)	0.063 (2)	0.059 (2)	0.0103 (19)	0.0011 (18)	0.0181 (18)
C6	0.083 (2)	0.0375 (16)	0.0451 (17)	0.0098 (16)	0.0228 (16)	0.0129 (13)
C7	0.115 (4)	0.055 (2)	0.068 (3)	0.003 (2)	0.023 (2)	0.0326 (19)
C8	0.109 (4)	0.064 (3)	0.087 (3)	−0.017 (3)	0.027 (3)	0.022 (2)
C9	0.078 (3)	0.065 (3)	0.083 (3)	−0.014 (2)	0.015 (2)	0.003 (2)
C10	0.069 (2)	0.053 (2)	0.068 (2)	0.0019 (18)	0.0092 (19)	0.0074 (17)
C11	0.0481 (16)	0.0438 (17)	0.0495 (17)	0.0097 (13)	0.0006 (13)	0.0106 (14)
C12	0.074 (2)	0.062 (2)	0.069 (2)	0.0321 (19)	−0.0023 (19)	0.0069 (19)
C13	0.083 (3)	0.071 (3)	0.071 (3)	0.036 (2)	0.010 (2)	−0.002 (2)
C14	0.080 (2)	0.061 (2)	0.053 (2)	0.017 (2)	0.0138 (18)	0.0059 (17)
C15	0.0611 (19)	0.0512 (19)	0.0445 (17)	0.0114 (15)	0.0068 (15)	0.0091 (14)
C16	0.0474 (16)	0.0443 (17)	0.0488 (17)	0.0084 (13)	−0.0015 (13)	0.0112 (13)
C17	0.073 (2)	0.051 (2)	0.062 (2)	0.0183 (17)	−0.0029 (18)	0.0205 (16)
C18	0.093 (3)	0.077 (3)	0.058 (2)	0.019 (2)	−0.001 (2)	0.033 (2)
C19	0.081 (3)	0.080 (3)	0.047 (2)	0.013 (2)	−0.0019 (18)	0.0147 (19)
C20	0.080 (2)	0.052 (2)	0.0491 (19)	0.0117 (18)	−0.0048 (17)	0.0046 (16)
C21	0.0464 (16)	0.066 (2)	0.0421 (16)	0.0014 (15)	−0.0028 (13)	0.0187 (15)
C22	0.063 (2)	0.090 (3)	0.061 (2)	−0.013 (2)	0.0065 (18)	0.032 (2)
C23	0.075 (3)	0.087 (3)	0.078 (3)	−0.020 (2)	−0.004 (2)	0.049 (3)
C24	0.074 (3)	0.056 (2)	0.096 (3)	−0.0113 (19)	−0.018 (2)	0.033 (2)
C25	0.060 (2)	0.0474 (19)	0.067 (2)	−0.0014 (15)	−0.0043 (17)	0.0173 (16)
C26	0.0502 (17)	0.065 (2)	0.0389 (16)	0.0119 (15)	0.0017 (13)	0.0117 (14)
C27	0.064 (2)	0.103 (4)	0.060 (2)	0.021 (2)	0.0202 (19)	0.014 (2)
C28	0.094 (3)	0.092 (4)	0.075 (3)	0.043 (3)	0.017 (2)	−0.004 (3)
C29	0.101 (3)	0.059 (2)	0.066 (2)	0.032 (2)	0.006 (2)	0.0024 (19)
C30	0.078 (2)	0.0463 (19)	0.057 (2)	0.0190 (17)	0.0064 (18)	0.0067 (16)
F1	0.258 (5)	0.0714 (19)	0.0760 (19)	0.036 (2)	−0.022 (2)	0.0164 (15)
F2	0.103 (2)	0.094 (2)	0.105 (2)	−0.0224 (17)	0.0018 (17)	0.0294 (17)
F3	0.118 (3)	0.106 (3)	0.162 (3)	0.048 (2)	0.024 (2)	0.006 (2)
F4	0.110 (2)	0.0504 (13)	0.119 (2)	0.0081 (13)	0.0053 (17)	0.0272 (14)
F5	0.099 (5)	0.083 (4)	0.160 (9)	0.015 (3)	−0.059 (5)	0.029 (4)
F6	0.228 (17)	0.131 (8)	0.069 (4)	0.072 (10)	0.017 (6)	−0.005 (4)
F8	0.160 (3)	0.0683 (18)	0.127 (3)	0.0292 (19)	−0.006 (2)	0.0337 (17)
F7	0.088 (5)	0.144 (8)	0.277 (18)	0.016 (5)	0.080 (9)	0.114 (9)
N1	0.0717 (18)	0.0419 (14)	0.0486 (15)	0.0124 (13)	0.0089 (13)	0.0185 (12)
N2	0.0644 (17)	0.0405 (14)	0.0538 (16)	0.0104 (13)	0.0135 (13)	0.0125 (12)
N3	0.0511 (14)	0.0392 (13)	0.0465 (14)	0.0067 (11)	0.0038 (11)	0.0120 (11)
N4	0.0642 (17)	0.0432 (15)	0.0487 (15)	0.0112 (13)	−0.0019 (13)	0.0096 (12)
N5	0.0517 (14)	0.0453 (15)	0.0451 (14)	0.0034 (12)	−0.0015 (11)	0.0156 (11)
N6	0.0523 (14)	0.0466 (15)	0.0426 (14)	0.0109 (12)	0.0047 (11)	0.0096 (11)
F5'	0.090 (7)	0.138 (9)	0.160 (17)	0.014 (6)	0.058 (9)	−0.001 (8)
F6'	0.132 (12)	0.125 (10)	0.152 (14)	−0.037 (8)	−0.069 (11)	0.054 (10)
F7'	0.26 (3)	0.068 (6)	0.056 (4)	0.037 (9)	−0.016 (7)	0.010 (4)

Geometric parameters (Å, º)

Cu1—N2	2.019 (3)	C11—C16	1.491 (4)
Cu1—N6	2.032 (3)	C12—C13	1.379 (6)
Cu1—N3	2.034 (3)	C12—H12	0.9300
Cu1—N5	2.044 (3)	C13—C14	1.364 (6)
Cu1—N1	2.239 (3)	C13—H13	0.9300
Cu1—N4	2.445 (3)	C14—C15	1.365 (5)
B1—F1	1.346 (6)	C14—H14	0.9300
B1—F4	1.362 (5)	C15—N3	1.345 (4)
B1—F3	1.378 (6)	C15—H15	0.9300
B1—F2	1.388 (6)	C16—N4	1.336 (4)
B2—F7	1.301 (7)	C16—C17	1.382 (5)
B2—F6	1.312 (8)	C17—C18	1.381 (6)
B2—F5'	1.330 (10)	C17—H17	0.9300
B2—F5	1.336 (7)	C18—C19	1.361 (6)
B2—F8	1.366 (5)	C18—H18	0.9300
B2—F6'	1.370 (11)	C19—C20	1.369 (6)
B2—F7'	1.376 (9)	C19—H19	0.9300
C1—N1	1.346 (4)	C20—N4	1.338 (5)
C1—C2	1.392 (5)	C20—H20	0.9300
C1—C6	1.482 (5)	C21—N5	1.355 (4)
C2—C3	1.377 (7)	C21—C22	1.383 (5)
C2—H2	0.9300	C21—C26	1.471 (5)
C3—C4	1.381 (7)	C22—C23	1.378 (7)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.375 (6)	C23—C24	1.362 (7)
C4—H4	0.9300	C23—H23	0.9300
C5—N1	1.334 (5)	C24—C25	1.385 (6)
C5—H5	0.9300	C24—H24	0.9300
C6—N2	1.346 (5)	C25—N5	1.345 (4)
C6—C7	1.397 (5)	C25—H25	0.9300
C7—C8	1.362 (7)	C26—N6	1.354 (4)
C7—H7	0.9300	C26—C27	1.390 (5)
C8—C9	1.366 (7)	C27—C28	1.390 (7)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.371 (6)	C28—C29	1.363 (7)
C9—H9	0.9300	C28—H28	0.9300
C10—N2	1.347 (5)	C29—C30	1.379 (6)
C10—H10	0.9300	C29—H29	0.9300
C11—N3	1.351 (4)	C30—N6	1.335 (5)
C11—C12	1.381 (5)	C30—H30	0.9300
N2—Cu1—N6	94.42 (11)	C13—C12—C11	119.5 (4)
N2—Cu1—N3	91.40 (11)	C13—C12—H12	120.3
N6—Cu1—N3	165.91 (11)	C11—C12—H12	120.3
N2—Cu1—N5	173.96 (11)	C14—C13—C12	119.1 (4)
N6—Cu1—N5	80.24 (11)	C14—C13—H13	120.4
N3—Cu1—N5	94.44 (11)	C12—C13—H13	120.4
N2—Cu1—N1	77.41 (12)	C13—C14—C15	119.5 (4)
N6—Cu1—N1	92.18 (11)	C13—C14—H14	120.3
N3—Cu1—N1	101.62 (11)	C15—C14—H14	120.3
N5—Cu1—N1	99.84 (11)	N3—C15—C14	122.3 (3)
N2—Cu1—N4	99.54 (12)	N3—C15—H15	118.9
N6—Cu1—N4	92.01 (10)	C14—C15—H15	118.9
N3—Cu1—N4	74.35 (10)	N4—C16—C17	122.7 (3)
N5—Cu1—N4	83.56 (10)	N4—C16—C11	115.4 (3)
N1—Cu1—N4	175.00 (10)	C17—C16—C11	121.9 (3)
F1—B1—F4	110.8 (4)	C18—C17—C16	118.0 (4)
F1—B1—F3	110.2 (5)	C18—C17—H17	121.0
F4—B1—F3	109.9 (5)	C16—C17—H17	121.0
F1—B1—F2	110.8 (5)	C19—C18—C17	119.9 (4)
F4—B1—F2	109.4 (4)	C19—C18—H18	120.1
F3—B1—F2	105.6 (4)	C17—C18—H18	120.1
F7—B2—F6	111.1 (8)	C18—C19—C20	118.5 (4)
F7—B2—F5'	146.0 (9)	C18—C19—H19	120.8
F6—B2—F5'	46.2 (6)	C20—C19—H19	120.8
F7—B2—F5	111.1 (7)	N4—C20—C19	123.3 (4)
F6—B2—F5	112.0 (7)	N4—C20—H20	118.3
F5'—B2—F5	69.5 (8)	C19—C20—H20	118.3
F7—B2—F8	102.1 (5)	N5—C21—C22	121.1 (4)
F6—B2—F8	111.6 (5)	N5—C21—C26	115.0 (3)
F5'—B2—F8	109.9 (7)	C22—C21—C26	123.9 (4)
F5—B2—F8	108.5 (5)	C23—C22—C21	119.3 (4)
F7—B2—F6'	50.8 (7)	C23—C22—H22	120.3
F6—B2—F6'	60.3 (8)	C21—C22—H22	120.3
F5'—B2—F6'	102.3 (10)	C24—C23—C22	119.4 (4)
F5—B2—F6'	132.7 (8)	C24—C23—H23	120.3
F8—B2—F6'	117.7 (8)	C22—C23—H23	120.3
F7—B2—F7'	65.3 (9)	C23—C24—C25	119.7 (4)
F6—B2—F7'	130.9 (6)	C23—C24—H24	120.2
F5'—B2—F7'	107.9 (10)	C25—C24—H24	120.2
F5—B2—F7'	45.8 (7)	N5—C25—C24	121.4 (4)
F8—B2—F7'	117.0 (5)	N5—C25—H25	119.3
F6'—B2—F7'	100.7 (9)	C24—C25—H25	119.3
N1—C1—C2	121.1 (4)	N6—C26—C27	121.2 (4)
N1—C1—C6	115.7 (3)	N6—C26—C21	114.9 (3)
C2—C1—C6	123.3 (3)	C27—C26—C21	123.9 (4)
C3—C2—C1	118.7 (4)	C28—C27—C26	119.1 (4)
C3—C2—H2	120.7	C28—C27—H27	120.4
C1—C2—H2	120.7	C26—C27—H27	120.4
C2—C3—C4	120.1 (4)	C29—C28—C27	119.1 (4)
C2—C3—H3	119.9	C29—C28—H28	120.4
C4—C3—H3	119.9	C27—C28—H28	120.4
C5—C4—C3	117.9 (4)	C28—C29—C30	119.1 (4)
C5—C4—H4	121.1	C28—C29—H29	120.4
C3—C4—H4	121.1	C30—C29—H29	120.4
N1—C5—C4	123.0 (4)	N6—C30—C29	122.9 (4)
N1—C5—H5	118.5	N6—C30—H30	118.5
C4—C5—H5	118.5	C29—C30—H30	118.5
N2—C6—C7	120.1 (4)	C5—N1—C1	119.2 (3)
N2—C6—C1	116.2 (3)	C5—N1—Cu1	128.7 (2)
C7—C6—C1	123.6 (4)	C1—N1—Cu1	110.2 (2)
C8—C7—C6	119.8 (4)	C6—N2—C10	119.4 (3)
C8—C7—H7	120.1	C6—N2—Cu1	118.0 (2)
C6—C7—H7	120.1	C10—N2—Cu1	122.6 (3)
C7—C8—C9	119.5 (4)	C15—N3—C11	118.6 (3)
C7—C8—H8	120.2	C15—N3—Cu1	122.2 (2)
C9—C8—H8	120.2	C11—N3—Cu1	119.2 (2)
C8—C9—C10	119.3 (4)	C16—N4—C20	117.6 (3)
C8—C9—H9	120.3	C16—N4—Cu1	102.3 (2)
C10—C9—H9	120.3	C20—N4—Cu1	125.5 (2)
N2—C10—C9	121.8 (4)	C25—N5—C21	118.9 (3)
N2—C10—H10	119.1	C25—N5—Cu1	126.4 (2)
C9—C10—H10	119.1	C21—N5—Cu1	113.6 (2)
N3—C11—C12	121.0 (3)	C30—N6—C26	118.5 (3)
N3—C11—C16	115.9 (3)	C30—N6—Cu1	126.8 (2)
C12—C11—C16	123.1 (3)	C26—N6—Cu1	114.6 (2)