(8-Amino-quinoline-κ(2)N,N')bis-(1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionato-κ(2)O,O')cobalt(II).

In the title compound, [Co(C(5)HF(6)O(2))(2)(C(9)H(8)N(2))], the Co(II) centre exhibits a pseudooctahedral coordination geometry, comprising two N-atom donors from the bidentate amino-quinoline ligand and four O-atom donor atoms from two bidentate chelating 1,1,1,5,5,5-hexafluoropentane-2,4-dionate ligands. In the crystal, molecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers. These dimers are further connected through π-π interactions between neighbouring quinoline rings [centroid-centroid distance = 3.472 (2) Å], and stack along the c axis.

Related literature

For related structures, see: Sertphon et al. (2011 ▶); Aakeröy et al. (2004 ▶, 2005 ▶, 2007 ▶); Harding et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

[Co(C5HF6O2)2(C9H8N2)]

M = 617.22

Triclinic,

a = 9.6102 (4) Å

b = 10.2681 (5) Å

c = 12.4154 (6) Å

α = 114.149 (1)°

β = 90.927 (1)°

γ = 95.202 (1)°

V = 1111.40 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 100 K

0.29 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.682, T max = 0.746

10217 measured reflections

5113 independent reflections

4735 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.05

5113 reflections

399 parameters

54 restraints

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011312/bg2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011312/bg2451Isup2.hkl

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

[Co(C5HF6O2)2(C9H8N2)]	Z = 2
Mr = 617.22	F(000) = 610
Triclinic, P1	Dx = 1.844 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6102 (4) Å	Cell parameters from 6750 reflections
b = 10.2681 (5) Å	θ = 2.7–27.6°
c = 12.4154 (6) Å	µ = 0.90 mm−1
α = 114.149 (1)°	T = 100 K
β = 90.927 (1)°	Prism, orange
γ = 95.202 (1)°	0.29 × 0.18 × 0.16 mm
V = 1111.40 (9) Å3

Bruker APEXII CCD area-detector diffractometer	5113 independent reflections
Radiation source: fine-focus sealed tube	4735 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
φ and ω scans	θmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.682, Tmax = 0.746	k = −13→13
10217 measured reflections	l = −15→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.8282P] where P = (Fo2 + 2Fc2)/3
5113 reflections	(Δ/σ)max = 0.001
399 parameters	Δρmax = 0.79 e Å−3
54 restraints	Δρmin = −0.55 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	Occ. (<1)
Co1	0.12629 (2)	0.20101 (2)	0.679585 (17)	0.01788 (7)
O1	0.17857 (12)	0.15131 (12)	0.82150 (10)	0.0233 (2)
O2	0.23066 (12)	0.02680 (12)	0.57507 (10)	0.0226 (2)
O3	0.30314 (12)	0.34361 (12)	0.71520 (10)	0.0220 (2)
O4	0.08649 (12)	0.23137 (11)	0.52671 (9)	0.0206 (2)
N1	0.00333 (14)	0.36365 (14)	0.78304 (11)	0.0194 (3)
N2	−0.07051 (15)	0.07814 (14)	0.66194 (12)	0.0228 (3)
H2A	−0.1131	0.0575	0.5909	0.027*
H2B	−0.0573	−0.0051	0.6667	0.027*
C18	−0.27315 (19)	0.0996 (2)	0.78771 (16)	0.0305 (4)
H18	−0.2966	0.0007	0.7528	0.037*
C8	0.26994 (16)	0.41960 (17)	0.55914 (14)	0.0210 (3)
H8	0.3061	0.4845	0.5294	0.025*
C13	−0.16746 (19)	0.5479 (2)	0.94323 (14)	0.0289 (4)
H13	−0.2230	0.6101	0.9972	0.035*
C6	0.33529 (16)	0.41998 (16)	0.66082 (13)	0.0195 (3)
C1	0.24544 (17)	0.05082 (17)	0.81746 (14)	0.0228 (3)
C9	0.15234 (16)	0.32484 (16)	0.50105 (13)	0.0187 (3)
C3	0.30849 (18)	−0.04772 (18)	0.72205 (15)	0.0262 (3)
H3	0.3610	−0.1127	0.7344	0.031*
C19	−0.15744 (17)	0.15903 (18)	0.75482 (14)	0.0225 (3)
C10	0.09259 (17)	0.33064 (17)	0.38720 (14)	0.0224 (3)
C11	0.03646 (18)	0.50439 (17)	0.83206 (14)	0.0232 (3)
H11	0.1197	0.5415	0.8131	0.028*
C4	0.29504 (17)	−0.05146 (17)	0.60907 (14)	0.0225 (3)
C14	−0.20721 (17)	0.39818 (19)	0.89415 (14)	0.0250 (3)
C7	0.46039 (17)	0.53403 (19)	0.71976 (15)	0.0250 (3)
C2	0.2559 (2)	0.0349 (2)	0.93543 (17)	0.0350 (4)
C12	−0.04797 (19)	0.60071 (18)	0.91146 (15)	0.0279 (4)
H12	−0.0223	0.6992	0.9418	0.033*
C16	−0.32669 (19)	0.3335 (2)	0.92501 (16)	0.0319 (4)
H16	−0.3849	0.3903	0.9800	0.038*
C17	−0.35721 (19)	0.1878 (2)	0.87441 (17)	0.0349 (4)
H17	−0.4344	0.1461	0.8974	0.042*
C5	0.3599 (2)	−0.1715 (2)	0.50891 (17)	0.0334 (4)
C15	−0.11961 (16)	0.30965 (17)	0.81087 (13)	0.0206 (3)
F1A	0.1331 (3)	0.0212 (7)	0.9737 (4)	0.0637 (14)	0.70 (2)
F2A	0.3201 (4)	0.1603 (4)	1.0201 (3)	0.0529 (8)	0.70 (2)
F3A	0.3336 (7)	−0.0600 (6)	0.9363 (4)	0.0808 (18)	0.70 (2)
F1B	0.232 (2)	0.1358 (14)	1.0254 (6)	0.114 (7)	0.30 (2)
F2B	0.3649 (9)	−0.0234 (15)	0.9466 (11)	0.076 (4)	0.30 (2)
F3B	0.1601 (11)	−0.0845 (17)	0.9226 (9)	0.086 (5)	0.30 (2)
F4A	0.4341 (13)	−0.2489 (11)	0.5421 (3)	0.050 (2)	0.57 (3)
F5A	0.4082 (15)	−0.1279 (15)	0.4265 (11)	0.0323 (15)	0.57 (3)
F6A	0.2463 (6)	−0.2711 (5)	0.4388 (4)	0.0334 (10)	0.57 (3)
F4B	0.4928 (14)	−0.1892 (18)	0.5544 (7)	0.048 (3)	0.43 (3)
F5B	0.426 (2)	−0.1294 (19)	0.4389 (17)	0.042 (3)	0.43 (3)
F6B	0.2903 (18)	−0.2858 (7)	0.4676 (15)	0.061 (4)	0.43 (3)
F7	0.55505 (16)	0.48660 (17)	0.76660 (18)	0.0789 (6)
F8	0.52320 (13)	0.58172 (16)	0.64755 (11)	0.0496 (4)
F9	0.41614 (15)	0.64738 (15)	0.80499 (13)	0.0618 (4)
F10	0.15304 (14)	0.43584 (13)	0.36377 (11)	0.0434 (3)
F11	−0.04305 (12)	0.34529 (16)	0.39296 (11)	0.0457 (3)
F12	0.10584 (16)	0.20821 (13)	0.29438 (10)	0.0489 (3)

	U11	U22	U33	U12	U13	U23
Co1	0.02444 (12)	0.01408 (11)	0.01511 (11)	0.00426 (8)	0.00061 (7)	0.00557 (8)
O1	0.0310 (6)	0.0218 (5)	0.0190 (5)	0.0071 (5)	0.0003 (4)	0.0095 (4)
O2	0.0300 (6)	0.0178 (5)	0.0196 (5)	0.0071 (4)	0.0017 (4)	0.0064 (4)
O3	0.0248 (5)	0.0212 (5)	0.0212 (5)	0.0030 (4)	−0.0018 (4)	0.0100 (4)
O4	0.0269 (6)	0.0169 (5)	0.0177 (5)	0.0031 (4)	−0.0005 (4)	0.0068 (4)
N1	0.0253 (6)	0.0176 (6)	0.0142 (6)	0.0049 (5)	−0.0014 (5)	0.0049 (5)
N2	0.0294 (7)	0.0173 (6)	0.0196 (6)	0.0025 (5)	−0.0008 (5)	0.0055 (5)
C18	0.0303 (9)	0.0332 (9)	0.0310 (9)	−0.0003 (7)	−0.0017 (7)	0.0172 (8)
C8	0.0225 (7)	0.0219 (7)	0.0210 (7)	0.0029 (6)	0.0012 (6)	0.0110 (6)
C13	0.0335 (9)	0.0317 (9)	0.0170 (7)	0.0169 (7)	−0.0017 (6)	0.0030 (6)
C6	0.0191 (7)	0.0189 (7)	0.0203 (7)	0.0062 (5)	0.0025 (5)	0.0070 (6)
C1	0.0257 (8)	0.0223 (7)	0.0232 (8)	0.0021 (6)	−0.0014 (6)	0.0125 (6)
C9	0.0228 (7)	0.0177 (7)	0.0168 (7)	0.0076 (6)	0.0020 (5)	0.0070 (6)
C3	0.0313 (8)	0.0231 (8)	0.0277 (8)	0.0100 (6)	0.0005 (7)	0.0125 (7)
C19	0.0253 (8)	0.0244 (8)	0.0179 (7)	0.0023 (6)	−0.0027 (6)	0.0090 (6)
C10	0.0280 (8)	0.0194 (7)	0.0205 (7)	0.0019 (6)	−0.0027 (6)	0.0091 (6)
C11	0.0295 (8)	0.0186 (7)	0.0196 (7)	0.0046 (6)	−0.0033 (6)	0.0057 (6)
C4	0.0250 (8)	0.0170 (7)	0.0244 (8)	0.0042 (6)	0.0012 (6)	0.0071 (6)
C14	0.0267 (8)	0.0329 (9)	0.0159 (7)	0.0110 (7)	−0.0016 (6)	0.0090 (6)
C7	0.0239 (8)	0.0281 (8)	0.0244 (8)	0.0001 (6)	−0.0025 (6)	0.0129 (7)
C2	0.0400 (10)	0.0456 (11)	0.0310 (9)	0.0172 (9)	0.0071 (8)	0.0246 (9)
C12	0.0376 (9)	0.0198 (8)	0.0211 (8)	0.0104 (7)	−0.0054 (7)	0.0020 (6)
C16	0.0266 (8)	0.0496 (11)	0.0229 (8)	0.0130 (8)	0.0036 (7)	0.0164 (8)
C17	0.0257 (8)	0.0539 (12)	0.0338 (10)	0.0032 (8)	0.0041 (7)	0.0269 (9)
C5	0.0448 (11)	0.0257 (9)	0.0312 (9)	0.0176 (8)	0.0076 (8)	0.0102 (7)
C15	0.0239 (7)	0.0238 (8)	0.0144 (7)	0.0058 (6)	−0.0024 (6)	0.0076 (6)
F1A	0.0482 (12)	0.110 (4)	0.061 (2)	−0.0003 (16)	0.0112 (12)	0.065 (3)
F2A	0.0699 (18)	0.0644 (15)	0.0221 (12)	0.0077 (14)	−0.0076 (11)	0.0157 (10)
F3A	0.152 (5)	0.079 (2)	0.0424 (16)	0.088 (3)	0.032 (2)	0.0407 (16)
F1B	0.246 (19)	0.101 (8)	0.030 (3)	0.134 (11)	0.048 (7)	0.039 (4)
F2B	0.030 (3)	0.172 (11)	0.080 (6)	0.022 (4)	0.001 (3)	0.102 (7)
F3B	0.082 (5)	0.130 (10)	0.068 (5)	−0.056 (6)	−0.024 (4)	0.078 (6)
F4A	0.064 (4)	0.047 (3)	0.0371 (13)	0.041 (3)	−0.0028 (15)	0.0078 (14)
F5A	0.038 (3)	0.038 (3)	0.0217 (16)	0.015 (2)	0.0063 (17)	0.0102 (15)
F6A	0.0388 (19)	0.0193 (12)	0.0317 (15)	0.0012 (11)	0.0010 (11)	0.0006 (9)
F4B	0.054 (4)	0.061 (5)	0.039 (2)	0.042 (4)	0.014 (2)	0.022 (3)
F5B	0.038 (5)	0.030 (3)	0.048 (7)	0.000 (3)	0.019 (4)	0.006 (3)
F6B	0.070 (6)	0.0170 (18)	0.072 (5)	−0.001 (2)	0.028 (5)	−0.004 (2)
F7	0.0507 (8)	0.0669 (10)	0.1391 (16)	−0.0257 (7)	−0.0618 (10)	0.0715 (11)
F8	0.0389 (7)	0.0730 (9)	0.0362 (6)	−0.0255 (6)	−0.0048 (5)	0.0285 (6)
F9	0.0531 (8)	0.0427 (7)	0.0511 (8)	−0.0181 (6)	0.0182 (6)	−0.0156 (6)
F10	0.0575 (7)	0.0416 (7)	0.0393 (6)	−0.0161 (6)	−0.0194 (5)	0.0301 (6)
F11	0.0288 (6)	0.0768 (9)	0.0450 (7)	0.0097 (6)	−0.0045 (5)	0.0380 (7)
F12	0.0936 (10)	0.0337 (6)	0.0180 (5)	0.0232 (6)	−0.0031 (6)	0.0060 (5)

Co1—O3	2.0549 (11)	C3—H3	0.9300
Co1—O4	2.0805 (11)	C19—C15	1.420 (2)
Co1—O2	2.0875 (11)	C10—F10	1.3182 (19)
Co1—O1	2.0906 (11)	C10—F11	1.325 (2)
Co1—N1	2.1183 (13)	C10—F12	1.3315 (19)
Co1—N2	2.1318 (14)	C11—C12	1.408 (2)
O1—C1	1.2487 (19)	C11—H11	0.9300
O2—C4	1.2515 (19)	C4—C5	1.538 (2)
O3—C6	1.2500 (19)	C14—C16	1.411 (3)
O4—C9	1.2529 (19)	C14—C15	1.415 (2)
N1—C11	1.323 (2)	C7—F7	1.303 (2)
N1—C15	1.369 (2)	C7—F8	1.316 (2)
N2—C19	1.446 (2)	C7—F9	1.323 (2)
N2—H2A	0.9000	C2—F1B	1.215 (7)
N2—H2B	0.9000	C2—F3A	1.284 (4)
C18—C19	1.368 (2)	C2—F2B	1.285 (9)
C18—C17	1.412 (3)	C2—F1A	1.296 (3)
C18—H18	0.9300	C2—F2A	1.367 (4)
C8—C9	1.394 (2)	C2—F3B	1.417 (8)
C8—C6	1.399 (2)	C12—H12	0.9300
C8—H8	0.9300	C16—C17	1.365 (3)
C13—C12	1.358 (3)	C16—H16	0.9300
C13—C14	1.415 (3)	C17—H17	0.9300
C13—H13	0.9300	C5—F6B	1.202 (8)
C6—C7	1.539 (2)	C5—F5B	1.271 (18)
C1—C3	1.396 (2)	C5—F4A	1.293 (4)
C1—C2	1.541 (2)	C5—F5A	1.346 (13)
C9—C10	1.543 (2)	C5—F6A	1.427 (5)
C3—C4	1.391 (2)	C5—F4B	1.445 (10)
O3—Co1—O4	88.59 (4)	O2—C4—C3	128.69 (15)
O3—Co1—O2	92.89 (5)	O2—C4—C5	113.84 (14)
O4—Co1—O2	86.96 (4)	C3—C4—C5	117.38 (15)
O3—Co1—O1	91.57 (5)	C16—C14—C13	123.78 (16)
O4—Co1—O1	173.56 (4)	C16—C14—C15	118.94 (16)
O2—Co1—O1	86.60 (4)	C13—C14—C15	117.26 (16)
O3—Co1—N1	92.56 (5)	F7—C7—F8	107.38 (16)
O4—Co1—N1	93.50 (5)	F7—C7—F9	107.93 (17)
O2—Co1—N1	174.54 (5)	F8—C7—F9	106.06 (15)
O1—Co1—N1	92.92 (5)	F7—C7—C6	111.98 (14)
O3—Co1—N2	171.64 (5)	F8—C7—C6	113.86 (14)
O4—Co1—N2	93.30 (5)	F9—C7—C6	109.31 (14)
O2—Co1—N2	95.34 (5)	F1B—C2—F3A	122.2 (5)
O1—Co1—N2	87.47 (5)	F1B—C2—F2B	113.4 (8)
N1—Co1—N2	79.21 (5)	F1B—C2—F1A	65.7 (9)
C1—O1—Co1	126.51 (11)	F3A—C2—F1A	112.9 (3)
C4—O2—Co1	127.00 (11)	F2B—C2—F1A	127.6 (5)
C6—O3—Co1	125.51 (10)	F3A—C2—F2A	103.7 (3)
C9—O4—Co1	124.61 (10)	F2B—C2—F2A	86.9 (6)
C11—N1—C15	118.09 (14)	F1A—C2—F2A	104.3 (3)
C11—N1—Co1	128.77 (12)	F1B—C2—F3B	108.0 (7)
C15—N1—Co1	112.72 (10)	F3A—C2—F3B	75.6 (6)
C19—N2—Co1	109.49 (10)	F2B—C2—F3B	94.7 (7)
C19—N2—H2A	109.8	F1A—C2—F3B	46.1 (6)
Co1—N2—H2A	109.8	F2A—C2—F3B	141.1 (4)
C19—N2—H2B	109.8	F1B—C2—C1	118.3 (3)
Co1—N2—H2B	109.8	F3A—C2—C1	115.0 (2)
H2A—N2—H2B	108.2	F2B—C2—C1	112.9 (5)
C19—C18—C17	120.25 (17)	F1A—C2—C1	111.35 (18)
C19—C18—H18	119.9	F2A—C2—C1	108.60 (19)
C17—C18—H18	119.9	F3B—C2—C1	106.4 (3)
C9—C8—C6	122.01 (15)	C13—C12—C11	119.11 (16)
C9—C8—H8	119.0	C13—C12—H12	120.4
C6—C8—H8	119.0	C11—C12—H12	120.4
C12—C13—C14	119.87 (15)	C17—C16—C14	120.24 (17)
C12—C13—H13	120.1	C17—C16—H16	119.9
C14—C13—H13	120.1	C14—C16—H16	119.9
O3—C6—C8	129.11 (15)	C16—C17—C18	120.95 (17)
O3—C6—C7	113.78 (13)	C16—C17—H17	119.5
C8—C6—C7	117.03 (14)	C18—C17—H17	119.5
O1—C1—C3	129.16 (15)	F6B—C5—F5B	118.2 (12)
O1—C1—C2	113.85 (15)	F6B—C5—F4A	78.3 (6)
C3—C1—C2	116.98 (15)	F5B—C5—F4A	110.8 (13)
O4—C9—C8	129.33 (14)	F6B—C5—F5A	113.3 (10)
O4—C9—C10	113.31 (13)	F4A—C5—F5A	118.9 (8)
C8—C9—C10	117.35 (14)	F5B—C5—F6A	105.6 (9)
C4—C3—C1	121.85 (15)	F4A—C5—F6A	103.5 (4)
C4—C3—H3	119.1	F5A—C5—F6A	98.0 (6)
C1—C3—H3	119.1	F6B—C5—F4B	108.7 (5)
C18—C19—C15	119.70 (16)	F5B—C5—F4B	88.6 (12)
C18—C19—N2	123.99 (15)	F5A—C5—F4B	98.1 (7)
C15—C19—N2	116.28 (14)	F6A—C5—F4B	132.8 (5)
F10—C10—F11	107.19 (14)	F6B—C5—C4	115.5 (4)
F10—C10—F12	107.37 (14)	F5B—C5—C4	113.9 (9)
F11—C10—F12	106.61 (14)	F4A—C5—C4	115.3 (2)
F10—C10—C9	114.31 (13)	F5A—C5—C4	111.8 (6)
F11—C10—C9	110.84 (13)	F6A—C5—C4	106.6 (3)
F12—C10—C9	110.16 (13)	F4B—C5—C4	107.9 (4)
N1—C11—C12	123.29 (16)	N1—C15—C14	122.25 (15)
N1—C11—H11	118.4	N1—C15—C19	117.98 (14)
C12—C11—H11	118.4	C14—C15—C19	119.76 (15)
O3—Co1—O1—C1	−93.11 (14)	Co1—O2—C4—C5	179.71 (11)
O2—Co1—O1—C1	−0.30 (13)	C1—C3—C4—O2	0.7 (3)
N1—Co1—O1—C1	174.25 (14)	C1—C3—C4—C5	−175.65 (16)
N2—Co1—O1—C1	95.20 (14)	C12—C13—C14—C16	177.71 (16)
O3—Co1—O2—C4	88.38 (13)	C12—C13—C14—C15	−1.2 (2)
O4—Co1—O2—C4	176.82 (13)	O3—C6—C7—F7	36.9 (2)
O1—Co1—O2—C4	−3.02 (13)	C8—C6—C7—F7	−145.89 (17)
N2—Co1—O2—C4	−90.15 (14)	O3—C6—C7—F8	159.01 (15)
O4—Co1—O3—C6	9.12 (12)	C8—C6—C7—F8	−23.8 (2)
O2—Co1—O3—C6	96.00 (12)	O3—C6—C7—F9	−82.60 (18)
O1—Co1—O3—C6	−177.32 (12)	C8—C6—C7—F9	94.57 (18)
N1—Co1—O3—C6	−84.33 (12)	O1—C1—C2—F1B	−17.8 (13)
O3—Co1—O4—C9	−8.77 (12)	C3—C1—C2—F1B	163.1 (13)
O2—Co1—O4—C9	−101.74 (12)	O1—C1—C2—F3A	−174.6 (4)
N1—Co1—O4—C9	83.71 (12)	C3—C1—C2—F3A	6.3 (4)
N2—Co1—O4—C9	163.08 (12)	O1—C1—C2—F2B	−153.5 (7)
O3—Co1—N1—C11	8.91 (13)	C3—C1—C2—F2B	27.4 (7)
O4—Co1—N1—C11	−79.83 (13)	O1—C1—C2—F1A	55.3 (4)
O1—Co1—N1—C11	100.61 (13)	C3—C1—C2—F1A	−123.8 (3)
N2—Co1—N1—C11	−172.53 (14)	O1—C1—C2—F2A	−59.0 (3)
O3—Co1—N1—C15	−163.40 (10)	C3—C1—C2—F2A	121.9 (2)
O4—Co1—N1—C15	107.86 (10)	O1—C1—C2—F3B	103.9 (8)
O1—Co1—N1—C15	−71.70 (10)	C3—C1—C2—F3B	−75.2 (8)
N2—Co1—N1—C15	15.16 (10)	C14—C13—C12—C11	−1.6 (2)
O4—Co1—N2—C19	−111.13 (10)	N1—C11—C12—C13	2.2 (2)
O2—Co1—N2—C19	161.62 (10)	C13—C14—C16—C17	−179.35 (16)
O1—Co1—N2—C19	75.27 (10)	C15—C14—C16—C17	−0.4 (2)
N1—Co1—N2—C19	−18.19 (10)	C14—C16—C17—C18	−2.2 (3)
Co1—O3—C6—C8	−6.4 (2)	C19—C18—C17—C16	1.4 (3)
Co1—O3—C6—C7	170.37 (10)	O2—C4—C5—F6B	−95.2 (13)
C9—C8—C6—O3	−0.8 (3)	C3—C4—C5—F6B	81.7 (13)
C9—C8—C6—C7	−177.45 (14)	O2—C4—C5—F5B	46.3 (10)
Co1—O1—C1—C3	3.9 (3)	C3—C4—C5—F5B	−136.8 (10)
Co1—O1—C1—C2	−175.04 (11)	O2—C4—C5—F4A	176.1 (8)
Co1—O4—C9—C8	5.7 (2)	C3—C4—C5—F4A	−7.1 (8)
Co1—O4—C9—C10	−175.38 (9)	O2—C4—C5—F5A	36.2 (6)
C6—C8—C9—O4	1.1 (3)	C3—C4—C5—F5A	−146.9 (6)
C6—C8—C9—C10	−177.80 (14)	O2—C4—C5—F6A	−69.7 (3)
O1—C1—C3—C4	−4.7 (3)	C3—C4—C5—F6A	107.2 (3)
C2—C1—C3—C4	174.23 (17)	O2—C4—C5—F4B	143.0 (7)
C17—C18—C19—C15	1.9 (2)	C3—C4—C5—F4B	−40.1 (7)
C17—C18—C19—N2	−176.04 (15)	C11—N1—C15—C14	−3.4 (2)
Co1—N2—C19—C18	−162.39 (13)	Co1—N1—C15—C14	169.82 (11)
Co1—N2—C19—C15	19.57 (16)	C11—N1—C15—C19	177.73 (14)
O4—C9—C10—F10	174.74 (14)	Co1—N1—C15—C19	−9.06 (16)
C8—C9—C10—F10	−6.2 (2)	C16—C14—C15—N1	−175.13 (14)
O4—C9—C10—F11	53.48 (18)	C13—C14—C15—N1	3.9 (2)
C8—C9—C10—F11	−127.44 (16)	C16—C14—C15—C19	3.7 (2)
O4—C9—C10—F12	−64.27 (18)	C13—C14—C15—C19	−177.28 (14)
C8—C9—C10—F12	114.81 (16)	C18—C19—C15—N1	174.41 (14)
C15—N1—C11—C12	0.3 (2)	N2—C19—C15—N1	−7.5 (2)
Co1—N1—C11—C12	−171.68 (12)	C18—C19—C15—C14	−4.5 (2)
Co1—O2—C4—C3	3.3 (3)	N2—C19—C15—C14	173.64 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.90	2.14	3.024 (2)	169
N2—H2B···O4i	0.90	2.56	3.069 (2)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.90	2.14	3.024 (2)	169
N2—H2B⋯O4i	0.90	2.56	3.069 (2)	117

Symmetry code: (i) .