(8-Amino­quinoline-κ2N,N′)bis­(1,1,1,5,5,5-hexa­fluoro­pentane-2,4-dionato-κ2O,O′)cobalt(II)

Harding, D.J.; Sertphon, D.; Harding, P.

doi:10.1107/S1600536812011312

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m450

doi:10.1107/S1600536812011312

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(8-Aminoquinoline-κ²N,N′)bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-κ²O,O′)cobalt(II)

David J. Harding,^a ^* Darunee Sertphon ^a and Phimphaka Harding ^a

^aMolecular Technology Research Unit, Department of Chemistry, Walailak University, Thasala, Nakhon Si Thammarat 80161, Thailand
^*Correspondence e-mail: hdavid@wu.ac.th

(Received 9 March 2012; accepted 15 March 2012; online 21 March 2012)

In the title compound, [Co(C₅HF₆O₂)₂(C₉H₈N₂)], the Co^II centre exhibits a pseudooctahedral coordination geometry, comprising two N-atom donors from the bidentate aminoquinoline 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_r = 617.22
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.05
5113 reflections
399 parameters
54 restraints
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.55 e Å⁻³

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) -x, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011312/bg2451sup1.cif

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

checkCIF report

Comment top

Metal β-diketonates can serve as excellent building blocks in the formation of supramolecular networks. For instance, the use of hydrogen-bonding ligands allows isolation of linear chains (Aakeröy et al., 2004,2005). In this paper we report the synthesis and structure of [Co(hfac)₂(NH₂-quin)] (hfac = 1,1,1,5,5,5-hexafluoropentane-2,4-dionato; NH₂-quin = 8-aminoquinoline).

The reaction of [Co(hfac)₂(H₂O)₂] with 8-aminoquinoline in THF yields [Co(hfac)₂(NH₂-quin)] 1 which crystallizes from CH₂Cl₂/hexanes in the space group P1 (Figure 1). The cobalt metal centre is six-coordinate with a distorted octahedral geometry, the hfac ligands adopting a cis arrangement enforced by the chelating NH₂-quin ligand. The compound is isostructural with [Ni(hfac)₂(NH₂-quin)] (Sertphon et al., 2011). The Co—N and Co—O bond lengths (Table 1) are comparable with those reported in trans-[M(hfac)₂(py-CH=CH—C₆F₄Br)₂] (Aakeröy et al., 2007) and [Co(hfac)₂(ppa^Br)] {ppa^Br = 4-bromophenyl(2-pyridylmethylidene)amine, Harding et al., 2010}. The β-diketonate ligands exhibit a planar coordination mode in which the angles between the planes defined by the Co and oxygen atoms and the carbon and oxygen atoms of the β-diketonate ligand are 1.7° and 7.6°. Similarly, in trans-[M(hfac)₂(py-CH=CH—C₆F₄Br)₂] (M = Co, Cu) the β-diketonate ligands are also planar (Aakeröy et al., 2007).

The packing in the structure involves two sets of N–H···O interactions between the amino protons of the NH₂-quin ligand and the coordinated O atoms of the β-diketonate forming discrete dimers {N2—H2A···O2 = 2.135 (2) Å, N2—H2B···O2 2.557 (2) Å, Figure 2 & Table 2}. Similar interactions are also found in [Ni(dbm)₂(dmae)] (dmae = dimethylaminoethylamine) and appear to be a feature of these types of compounds (Harding et al., 2009). In addition, there is a π-π interaction between the quinolyl rings of neighbouring NH₂-quin ligands as shown in Figure 3 {Cg1—Cg1ⁱ = 3.472 (2) Å where Cg1 is the centroid of the ring C11—C15,N1; i = symmetry code = -x, 1 - y, 2 - z}. The hydrogen bonds mentioned above combine with the π-π interactions to form one-dimensional chains.

Related literature top

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

Experimental top

To a deep orange red solution of [Co(hfac)₂(H₂O)₂] (1.0300 g, 2 mmol) in THF (10 ml) was added 8-aminoquinoline (0.2884 g, 2 mmol) giving a red-brown solution which was stirred for 2 hr. After evaporating to low volume (ca. 2 ml), hexane (3 ml) was added giving an orange precipitate which was filtered and washed with hexanes (2×4 ml) and air dried giving orange microcrystals, 0.8794 g (71%). X-ray quality crystals were grown by layering a CH₂Cl₂ solution with hexane (10 ml) leading to orange crystals after 2 days. IR in KBr disc ν_C=O 1642 cm^-1. UV-Vis (in CH₂Cl₂, ε mol.dm^-3cm^-1) 406sh (340), 416sh (300), 505 (120). C₁₉H₁₀Co F₁₂N₂O₄; calc. C 37.0, H 1.6, N 4.5; found C 36.8, H 1.5, N 4.3.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); 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).

Figures top

	Fig. 1. The molecular structure of (1) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing in (1) showing the N—H···O hydrogen bonding interactions forming dimers. Only selected atoms are labelled for clairty. [Symmetry codes: (i) -x, -y, 1 - z].
	Fig. 3. The molecular packing in (1) showing the π···π interactions between the quinolyl ring. Only selected atoms are labelled for clairty. [Symmetry codes: (i) -x, 1 - y, 2 - z].

(8-Aminoquinoline-κ²N,N')bis(1,1,1,5,5,5-hexafluoropentane- 2,4-dionato-κ²O,O')cobalt(II) top

Crystal data top

[Co(C₅HF₆O₂)₂(C₉H₈N₂)]	Z = 2
M_r = 617.22	F(000) = 610
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0369P)² + 0.8282P] where P = (F_o² + 2F_c²)/3
5113 reflections	(Δ/σ)_max = 0.001
399 parameters	Δρ_max = 0.79 e Å⁻³
54 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Co(C₅HF₆O₂)₂(C₉H₈N₂)]	γ = 95.202 (1)°
M_r = 617.22	V = 1111.40 (9) Å³
Triclinic, P1	Z = 2
a = 9.6102 (4) Å	Mo Kα radiation
b = 10.2681 (5) Å	µ = 0.90 mm⁻¹
c = 12.4154 (6) Å	T = 100 K
α = 114.149 (1)°	0.29 × 0.18 × 0.16 mm
β = 90.927 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5113 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	4735 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.746	R_int = 0.010
10217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	54 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.05	Δρ_max = 0.79 e Å⁻³
5113 reflections	Δρ_min = −0.55 e Å⁻³
399 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₅HF₆O₂)₂(C₉H₈N₂)]
M_r	617.22
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6102 (4), 10.2681 (5), 12.4154 (6)
α, β, γ (°)	114.149 (1), 90.927 (1), 95.202 (1)
V (Å³)	1111.40 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.29 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.682, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10217, 5113, 4735
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.078, 1.05
No. of reflections	5113
No. of parameters	399
No. of restraints	54
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.55

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.90	2.135	3.024 (2)	169
N2—H2B···O4ⁱ	0.90	2.557	3.069 (2)	117

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

The authors gratefully acknowledge the Royal Society of Chemistry for a JWT Jones Travelling Fellowship and a Research Fund award (both to DJH) which partially funded this research. A research grant from Walailak University (grant No. WU53204 to PH) is also acknowledged. Finally, the National Science and Technology Development Agency is thanked for a scholarship (awarded to DS).

References

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