[(4-Bromo-phen-yl)(2-pyridyl-methyl-idene)amine-κN,N']bis-(1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionato-κO,O')cobalt(II).

In the title complex, [Co(C(5)HF(6)O(2))(2)(C(12)H(9)BrN(2))], the Co(II) atom exhibits a pseudo-octa-hedral coordination geometry, comprising two N-donor atoms from a bidentate chelate (4-bromo-phen-yl)(2-pyridyl-methyl-idene)amine (ppa(Br)) ligand [Co-N = 2.098 (2) and 2.209 (2) Å] and four O-donor atoms from two bidentate chelate 1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionate (hfac) ligands [Co-O range = 2.0452 (19)-2.0796 (19) Å]. The packing of the structure involves weak π-π inter-actions between the pyridyl and benzene rings of neighbouring ppa(Br) ligands [centroid-centroid distance = 3.928 (2) Å] and inter-actions between the Br atom on the ppa(Br) ligand and the hfac ligand [Br⋯C = 3.531 (2) Å].

Related literature

For a review of halogen bonding, see: Corradi et al. (2000 ▶); Walsh et al. (2001 ▶); Liantonio et al. (2003 ▶). For an introduction to crystal engineering, see: Braga et al. (2002 ▶). For related structures, see: Harding, Harding, Sophonrat & Adams (2010 ▶); Harding, Harding, Tinpun et al. (2010 ▶); Aäkeroy et al. (2004 ▶, 2007 ▶). For a description of the Cambridge Structural database, see: Allen et al. (2002 ▶).

Experimental

Crystal data

[Co(C5HF6O2)2(C12H9BrN2)]

M = 734.17

Triclinic,

a = 8.3568 (2) Å

b = 10.9420 (2) Å

c = 14.8151 (3) Å

α = 74.042 (1)°

β = 86.510 (1)°

γ = 77.080 (1)°

V = 1269.51 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.37 mm−1

T = 150 K

0.60 × 0.30 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.330, T max = 0.932

21525 measured reflections

5176 independent reflections

4508 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.08

5176 reflections

379 parameters

H-atom parameters constrained

Δρmax = 1.23 e Å−3

Δρmin = −0.91 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032757/zs2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032757/zs2056Isup2.hkl

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

[Co(C5HF6O2)2(C12H9BrN2)]	Z = 2
Mr = 734.17	F(000) = 718
Triclinic, P1	Dx = 1.921 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3568 (2) Å	Cell parameters from 9953 reflections
b = 10.9420 (2) Å	θ = 2.9–32.8°
c = 14.8151 (3) Å	µ = 2.37 mm−1
α = 74.042 (1)°	T = 150 K
β = 86.510 (1)°	Plate, orange
γ = 77.080 (1)°	0.60 × 0.30 × 0.03 mm
V = 1269.51 (5) Å3

Bruker SMART CCD area-detector diffractometer	5176 independent reflections
Radiation source: fine-focus sealed tube	4508 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
Tmin = 0.330, Tmax = 0.932	k = −13→13
21525 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0399P)2 + 2.417P] where P = (Fo2 + 2Fc2)/3
5176 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 1.23 e Å−3
0 restraints	Δρmin = −0.91 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.24966 (4)	0.40512 (3)	1.12788 (2)	0.02627 (10)
C1	0.4059 (3)	0.3017 (3)	1.0652 (2)	0.0190 (6)
C2	0.4540 (4)	0.1698 (3)	1.1069 (2)	0.0234 (6)
H2	0.4096	0.1318	1.1659	0.028*
C3	0.5671 (4)	0.0937 (3)	1.0621 (2)	0.0220 (6)
H3	0.6002	0.0028	1.0903	0.026*
C4	0.6331 (3)	0.1491 (3)	0.97587 (19)	0.0165 (5)
C5	0.5813 (3)	0.2824 (3)	0.93439 (19)	0.0198 (6)
H5	0.6237	0.3208	0.8750	0.024*
C6	0.4680 (4)	0.3591 (3)	0.9796 (2)	0.0218 (6)
H6	0.4337	0.4500	0.9519	0.026*
C7	0.8328 (3)	−0.0354 (3)	0.96759 (19)	0.0182 (5)
H7	0.8186	−0.0694	1.0331	0.022*
C8	0.9486 (3)	−0.1115 (3)	0.91526 (19)	0.0172 (5)
C9	1.0341 (4)	−0.2363 (3)	0.9576 (2)	0.0221 (6)
H9	1.0201	−0.2753	1.0225	0.027*
C10	1.1404 (4)	−0.3031 (3)	0.9032 (2)	0.0240 (6)
H10	1.1991	−0.3896	0.9301	0.029*
C11	1.1601 (4)	−0.2431 (3)	0.8099 (2)	0.0242 (6)
H11	1.2336	−0.2869	0.7718	0.029*
C12	1.0707 (4)	−0.1171 (3)	0.7723 (2)	0.0217 (6)
H12	1.0847	−0.0757	0.7078	0.026*
C13	0.8228 (4)	0.1729 (3)	0.5708 (2)	0.0215 (6)
C14	0.9068 (4)	0.2216 (3)	0.4767 (2)	0.0322 (7)
C15	0.6657 (4)	0.1503 (3)	0.5689 (2)	0.0258 (6)
H15	0.6125	0.1698	0.5102	0.031*
C16	0.5849 (4)	0.0998 (3)	0.6508 (2)	0.0246 (6)
C17	0.4252 (4)	0.0581 (4)	0.6393 (2)	0.0361 (8)
C18	0.7556 (4)	0.4215 (3)	0.6922 (2)	0.0223 (6)
C19	0.6383 (5)	0.5432 (3)	0.6348 (3)	0.0414 (9)
C20	0.9177 (4)	0.4284 (3)	0.7033 (2)	0.0231 (6)
H20	0.9542	0.5051	0.6707	0.028*
C21	1.0267 (4)	0.3261 (3)	0.7608 (2)	0.0203 (6)
C22	1.1961 (4)	0.3521 (3)	0.7732 (3)	0.0330 (8)
Co1	0.82077 (4)	0.13568 (3)	0.77538 (2)	0.01482 (10)
F1	0.3604 (3)	0.1057 (3)	0.55597 (18)	0.0696 (8)
F2	0.4576 (3)	−0.0730 (2)	0.65283 (19)	0.0578 (7)
F3	0.3172 (3)	0.0779 (3)	0.70502 (19)	0.0578 (7)
F4	0.9544 (4)	0.3293 (3)	0.47281 (18)	0.0768 (10)
F5	0.8123 (3)	0.2441 (3)	0.40289 (14)	0.0636 (8)
F6	1.0401 (3)	0.1358 (2)	0.46507 (15)	0.0508 (6)
F7	0.5963 (6)	0.5260 (3)	0.5585 (3)	0.130 (2)
F8	0.5029 (3)	0.5703 (2)	0.6848 (3)	0.0862 (11)
F9	0.6978 (3)	0.64976 (19)	0.61453 (18)	0.0505 (6)
F10	1.2729 (3)	0.3815 (4)	0.6912 (2)	0.0974 (13)
F11	1.1845 (4)	0.4500 (3)	0.8083 (3)	0.1054 (15)
F12	1.2953 (2)	0.25146 (19)	0.82617 (16)	0.0406 (5)
N1	0.7503 (3)	0.0775 (2)	0.92465 (16)	0.0159 (5)
N2	0.9660 (3)	−0.0524 (2)	0.82359 (16)	0.0171 (5)
O1	0.9099 (2)	0.15687 (19)	0.64017 (13)	0.0195 (4)
O2	0.6285 (2)	0.07571 (19)	0.73472 (14)	0.0207 (4)
O3	0.6895 (2)	0.32603 (18)	0.72450 (13)	0.0194 (4)
O4	1.0045 (2)	0.21558 (18)	0.80721 (13)	0.0192 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.02487 (16)	0.02549 (16)	0.02822 (17)	−0.00312 (12)	0.00920 (12)	−0.01065 (12)
C1	0.0152 (13)	0.0234 (14)	0.0211 (14)	−0.0036 (11)	0.0022 (11)	−0.0116 (11)
C2	0.0295 (16)	0.0212 (14)	0.0213 (14)	−0.0111 (12)	0.0086 (12)	−0.0061 (12)
C3	0.0280 (15)	0.0158 (13)	0.0219 (14)	−0.0066 (12)	0.0031 (12)	−0.0036 (11)
C4	0.0159 (13)	0.0189 (13)	0.0166 (13)	−0.0056 (11)	−0.0007 (10)	−0.0061 (10)
C5	0.0201 (14)	0.0212 (14)	0.0152 (13)	−0.0026 (11)	0.0008 (11)	−0.0021 (11)
C6	0.0222 (14)	0.0179 (13)	0.0214 (14)	0.0010 (11)	−0.0018 (11)	−0.0026 (11)
C7	0.0207 (14)	0.0194 (13)	0.0140 (13)	−0.0048 (11)	−0.0011 (11)	−0.0032 (10)
C8	0.0172 (13)	0.0169 (13)	0.0179 (13)	−0.0040 (11)	−0.0035 (10)	−0.0044 (10)
C9	0.0240 (15)	0.0202 (14)	0.0192 (14)	−0.0010 (12)	−0.0058 (11)	−0.0026 (11)
C10	0.0232 (15)	0.0190 (13)	0.0269 (15)	0.0036 (12)	−0.0074 (12)	−0.0063 (12)
C11	0.0207 (14)	0.0244 (14)	0.0270 (15)	0.0004 (12)	−0.0010 (12)	−0.0102 (12)
C12	0.0224 (14)	0.0227 (14)	0.0195 (14)	−0.0036 (12)	−0.0001 (11)	−0.0057 (11)
C13	0.0279 (15)	0.0176 (13)	0.0181 (14)	−0.0028 (12)	0.0005 (12)	−0.0050 (11)
C14	0.0380 (19)	0.0381 (18)	0.0193 (15)	−0.0089 (15)	0.0039 (13)	−0.0058 (13)
C15	0.0278 (16)	0.0287 (15)	0.0206 (15)	−0.0050 (13)	−0.0044 (12)	−0.0060 (12)
C16	0.0245 (15)	0.0239 (14)	0.0269 (16)	−0.0075 (12)	−0.0044 (12)	−0.0065 (12)
C17	0.0330 (18)	0.050 (2)	0.0322 (18)	−0.0197 (16)	−0.0029 (15)	−0.0127 (16)
C18	0.0281 (16)	0.0191 (14)	0.0175 (14)	−0.0024 (12)	−0.0025 (12)	−0.0030 (11)
C19	0.041 (2)	0.0228 (16)	0.054 (2)	−0.0067 (15)	−0.0224 (18)	0.0045 (16)
C20	0.0279 (15)	0.0195 (14)	0.0218 (14)	−0.0095 (12)	0.0018 (12)	−0.0025 (11)
C21	0.0216 (14)	0.0208 (14)	0.0206 (14)	−0.0074 (11)	0.0005 (11)	−0.0069 (11)
C22	0.0295 (17)	0.0220 (15)	0.048 (2)	−0.0120 (14)	−0.0081 (15)	−0.0028 (14)
Co1	0.01588 (19)	0.01408 (18)	0.01382 (18)	−0.00367 (14)	−0.00033 (14)	−0.00219 (14)
F1	0.0544 (16)	0.104 (2)	0.0513 (15)	−0.0445 (16)	−0.0281 (12)	0.0049 (14)
F2	0.0614 (16)	0.0504 (14)	0.0774 (18)	−0.0309 (12)	0.0001 (13)	−0.0281 (13)
F3	0.0297 (11)	0.0890 (19)	0.0739 (17)	−0.0283 (12)	0.0120 (11)	−0.0436 (15)
F4	0.141 (3)	0.0613 (16)	0.0414 (14)	−0.0620 (18)	0.0404 (16)	−0.0119 (12)
F5	0.0408 (13)	0.118 (2)	0.0176 (10)	−0.0071 (14)	−0.0015 (9)	−0.0019 (12)
F6	0.0361 (12)	0.0704 (16)	0.0345 (12)	0.0019 (11)	0.0130 (9)	−0.0088 (11)
F7	0.238 (5)	0.0398 (15)	0.102 (3)	0.010 (2)	−0.137 (3)	−0.0037 (16)
F8	0.0272 (13)	0.0385 (14)	0.159 (3)	0.0060 (11)	0.0007 (16)	0.0188 (17)
F9	0.0464 (13)	0.0239 (10)	0.0674 (16)	−0.0076 (9)	−0.0113 (11)	0.0128 (10)
F10	0.0476 (16)	0.158 (3)	0.0688 (19)	−0.062 (2)	−0.0036 (14)	0.031 (2)
F11	0.0547 (17)	0.0586 (17)	0.230 (4)	0.0108 (14)	−0.065 (2)	−0.088 (2)
F12	0.0260 (10)	0.0309 (10)	0.0644 (14)	−0.0070 (8)	−0.0163 (10)	−0.0077 (10)
N1	0.0160 (11)	0.0154 (11)	0.0174 (11)	−0.0043 (9)	−0.0008 (9)	−0.0055 (9)
N2	0.0179 (11)	0.0164 (11)	0.0174 (11)	−0.0047 (9)	−0.0002 (9)	−0.0040 (9)
O1	0.0210 (10)	0.0214 (10)	0.0155 (9)	−0.0057 (8)	0.0001 (8)	−0.0031 (8)
O2	0.0224 (10)	0.0206 (10)	0.0195 (10)	−0.0090 (8)	−0.0007 (8)	−0.0025 (8)
O3	0.0192 (10)	0.0179 (9)	0.0194 (10)	−0.0035 (8)	−0.0010 (8)	−0.0026 (8)
O4	0.0209 (10)	0.0181 (9)	0.0190 (10)	−0.0064 (8)	−0.0022 (8)	−0.0031 (8)

Br1—C1	1.902 (3)	C14—F6	1.322 (4)
C1—C6	1.378 (4)	C14—F5	1.322 (4)
C1—C2	1.382 (4)	C15—C16	1.391 (4)
C2—C3	1.379 (4)	C15—H15	0.9500
C2—H2	0.9500	C16—O2	1.256 (4)
C3—C4	1.394 (4)	C16—C17	1.537 (4)
C3—H3	0.9500	C17—F1	1.300 (4)
C4—C5	1.397 (4)	C17—F3	1.316 (4)
C4—N1	1.429 (3)	C17—F2	1.358 (4)
C5—C6	1.388 (4)	C18—O3	1.255 (4)
C5—H5	0.9500	C18—C20	1.396 (4)
C6—H6	0.9500	C18—C19	1.534 (4)
C7—N1	1.284 (4)	C19—F7	1.278 (5)
C7—C8	1.461 (4)	C19—F9	1.321 (4)
C7—H7	0.9500	C19—F8	1.336 (5)
C8—N2	1.349 (4)	C20—C21	1.387 (4)
C8—C9	1.384 (4)	C20—H20	0.9500
C9—C10	1.385 (4)	C21—O4	1.264 (3)
C9—H9	0.9500	C21—C22	1.537 (4)
C10—C11	1.375 (4)	C22—F11	1.296 (4)
C10—H10	0.9500	C22—F12	1.308 (4)
C11—C12	1.392 (4)	C22—F10	1.332 (5)
C11—H11	0.9500	Co1—O2	2.0452 (19)
C12—N2	1.335 (4)	Co1—O4	2.0639 (19)
C12—H12	0.9500	Co1—O1	2.0644 (19)
C13—O1	1.246 (3)	Co1—O3	2.0796 (19)
C13—C15	1.392 (4)	Co1—N2	2.098 (2)
C13—C14	1.537 (4)	Co1—N1	2.209 (2)
C14—F4	1.312 (4)
C6—C1—C2	121.5 (3)	F1—C17—F2	104.7 (3)
C6—C1—Br1	119.8 (2)	F3—C17—F2	103.7 (3)
C2—C1—Br1	118.7 (2)	F1—C17—C16	114.6 (3)
C3—C2—C1	119.3 (3)	F3—C17—C16	112.2 (3)
C3—C2—H2	120.4	F2—C17—C16	109.1 (3)
C1—C2—H2	120.4	O3—C18—C20	128.0 (3)
C2—C3—C4	120.5 (3)	O3—C18—C19	113.7 (3)
C2—C3—H3	119.7	C20—C18—C19	118.3 (3)
C4—C3—H3	119.7	F7—C19—F9	108.7 (4)
C3—C4—C5	119.2 (3)	F7—C19—F8	108.4 (4)
C3—C4—N1	124.2 (2)	F9—C19—F8	104.6 (3)
C5—C4—N1	116.6 (2)	F7—C19—C18	111.1 (3)
C6—C5—C4	120.3 (3)	F9—C19—C18	114.0 (3)
C6—C5—H5	119.9	F8—C19—C18	109.6 (3)
C4—C5—H5	119.9	C21—C20—C18	121.5 (3)
C1—C6—C5	119.2 (3)	C21—C20—H20	119.3
C1—C6—H6	120.4	C18—C20—H20	119.3
C5—C6—H6	120.4	O4—C21—C20	129.1 (3)
N1—C7—C8	119.7 (2)	O4—C21—C22	115.2 (3)
N1—C7—H7	120.1	C20—C21—C22	115.7 (3)
C8—C7—H7	120.1	F11—C22—F12	108.3 (3)
N2—C8—C9	122.5 (3)	F11—C22—F10	106.4 (4)
N2—C8—C7	115.7 (2)	F12—C22—F10	105.6 (3)
C9—C8—C7	121.7 (3)	F11—C22—C21	111.6 (3)
C10—C9—C8	118.5 (3)	F12—C22—C21	113.1 (3)
C10—C9—H9	120.7	F10—C22—C21	111.3 (3)
C8—C9—H9	120.7	O2—Co1—O4	173.89 (8)
C11—C10—C9	119.3 (3)	O2—Co1—O1	87.88 (8)
C11—C10—H10	120.3	O4—Co1—O1	89.87 (8)
C9—C10—H10	120.3	O2—Co1—O3	87.74 (8)
C10—C11—C12	119.0 (3)	O4—Co1—O3	86.41 (8)
C10—C11—H11	120.5	O1—Co1—O3	85.05 (8)
C12—C11—H11	120.5	O2—Co1—N2	94.96 (8)
N2—C12—C11	122.3 (3)	O4—Co1—N2	90.82 (8)
N2—C12—H12	118.9	O1—Co1—N2	92.91 (8)
C11—C12—H12	118.9	O3—Co1—N2	176.56 (8)
O1—C13—C15	128.6 (3)	O2—Co1—N1	91.80 (8)
O1—C13—C14	113.3 (3)	O4—Co1—N1	91.41 (8)
C15—C13—C14	118.1 (3)	O1—Co1—N1	169.94 (8)
F4—C14—F6	106.5 (3)	O3—Co1—N1	104.98 (8)
F4—C14—F5	107.8 (3)	N2—Co1—N1	77.10 (9)
F6—C14—F5	106.3 (3)	C7—N1—C4	119.2 (2)
F4—C14—C13	111.0 (3)	C7—N1—Co1	111.94 (18)
F6—C14—C13	111.4 (3)	C4—N1—Co1	128.79 (17)
F5—C14—C13	113.5 (3)	C12—N2—C8	118.4 (2)
C16—C15—C13	121.6 (3)	C12—N2—Co1	126.20 (19)
C16—C15—H15	119.2	C8—N2—Co1	115.41 (18)
C13—C15—H15	119.2	C13—O1—Co1	123.71 (19)
O2—C16—C15	129.1 (3)	C16—O2—Co1	123.95 (19)
O2—C16—C17	114.0 (3)	C18—O3—Co1	123.68 (19)
C15—C16—C17	116.7 (3)	C21—O4—Co1	122.51 (18)
F1—C17—F3	111.6 (3)
C6—C1—C2—C3	0.2 (4)	C5—C4—N1—C7	162.6 (3)
Br1—C1—C2—C3	179.9 (2)	C3—C4—N1—Co1	163.1 (2)
C1—C2—C3—C4	0.4 (4)	C5—C4—N1—Co1	−15.6 (3)
C2—C3—C4—C5	−1.1 (4)	O2—Co1—N1—C7	97.18 (19)
C2—C3—C4—N1	−179.8 (3)	O4—Co1—N1—C7	−88.02 (19)
C3—C4—C5—C6	1.4 (4)	O1—Co1—N1—C7	9.2 (6)
N1—C4—C5—C6	−179.8 (2)	O3—Co1—N1—C7	−174.68 (18)
C2—C1—C6—C5	0.1 (4)	N2—Co1—N1—C7	2.50 (18)
Br1—C1—C6—C5	−179.7 (2)	O2—Co1—N1—C4	−84.5 (2)
C4—C5—C6—C1	−0.9 (4)	O4—Co1—N1—C4	90.3 (2)
N1—C7—C8—N2	3.1 (4)	O1—Co1—N1—C4	−172.5 (4)
N1—C7—C8—C9	−176.7 (3)	O3—Co1—N1—C4	3.6 (2)
N2—C8—C9—C10	−0.5 (4)	N2—Co1—N1—C4	−179.2 (2)
C7—C8—C9—C10	179.2 (3)	C11—C12—N2—C8	0.8 (4)
C8—C9—C10—C11	1.2 (4)	C11—C12—N2—Co1	−178.8 (2)
C9—C10—C11—C12	−0.9 (4)	C9—C8—N2—C12	−0.5 (4)
C10—C11—C12—N2	−0.2 (4)	C7—C8—N2—C12	179.8 (2)
O1—C13—C14—F4	−55.7 (4)	C9—C8—N2—Co1	179.2 (2)
C15—C13—C14—F4	125.5 (3)	C7—C8—N2—Co1	−0.6 (3)
O1—C13—C14—F6	62.7 (4)	O2—Co1—N2—C12	88.0 (2)
C15—C13—C14—F6	−116.0 (3)	O4—Co1—N2—C12	−90.1 (2)
O1—C13—C14—F5	−177.3 (3)	O1—Co1—N2—C12	−0.2 (2)
C15—C13—C14—F5	3.9 (4)	N1—Co1—N2—C12	178.7 (2)
O1—C13—C15—C16	−2.0 (5)	O2—Co1—N2—C8	−91.62 (19)
C14—C13—C15—C16	176.6 (3)	O4—Co1—N2—C8	90.35 (19)
C13—C15—C16—O2	5.1 (5)	O1—Co1—N2—C8	−179.74 (19)
C13—C15—C16—C17	−170.3 (3)	N1—Co1—N2—C8	−0.91 (18)
O2—C16—C17—F1	166.4 (3)	C15—C13—O1—Co1	−16.6 (4)
C15—C16—C17—F1	−17.5 (5)	C14—C13—O1—Co1	164.79 (19)
O2—C16—C17—F3	37.7 (4)	O2—Co1—O1—C13	23.0 (2)
C15—C16—C17—F3	−146.2 (3)	O4—Co1—O1—C13	−151.3 (2)
O2—C16—C17—F2	−76.6 (4)	O3—Co1—O1—C13	−64.9 (2)
C15—C16—C17—F2	99.4 (3)	N2—Co1—O1—C13	117.9 (2)
O3—C18—C19—F7	−67.9 (5)	N1—Co1—O1—C13	111.4 (5)
C20—C18—C19—F7	112.6 (4)	C15—C16—O2—Co1	11.3 (4)
O3—C18—C19—F9	168.8 (3)	C17—C16—O2—Co1	−173.2 (2)
C20—C18—C19—F9	−10.7 (5)	O1—Co1—O2—C16	−20.5 (2)
O3—C18—C19—F8	51.9 (4)	O3—Co1—O2—C16	64.7 (2)
C20—C18—C19—F8	−127.5 (3)	N2—Co1—O2—C16	−113.2 (2)
O3—C18—C20—C21	−5.0 (5)	N1—Co1—O2—C16	169.6 (2)
C19—C18—C20—C21	174.4 (3)	C20—C18—O3—Co1	−16.7 (4)
C18—C20—C21—O4	2.5 (5)	C19—C18—O3—Co1	163.9 (2)
C18—C20—C21—C22	−174.7 (3)	O2—Co1—O3—C18	−150.4 (2)
O4—C21—C22—F11	−118.6 (4)	O4—Co1—O3—C18	27.8 (2)
C20—C21—C22—F11	59.0 (4)	O1—Co1—O3—C18	−62.3 (2)
O4—C21—C22—F12	3.9 (4)	N1—Co1—O3—C18	118.3 (2)
C20—C21—C22—F12	−178.4 (3)	C20—C21—O4—Co1	21.0 (4)
O4—C21—C22—F10	122.6 (3)	C22—C21—O4—Co1	−161.8 (2)
C20—C21—C22—F10	−59.7 (4)	O1—Co1—O4—C21	55.7 (2)
C8—C7—N1—C4	177.8 (2)	O3—Co1—O4—C21	−29.4 (2)
C8—C7—N1—Co1	−3.7 (3)	N2—Co1—O4—C21	148.6 (2)
C3—C4—N1—C7	−18.7 (4)	N1—Co1—O4—C21	−134.3 (2)