Three p-xylene-solvated pseudo­polymorphs of bis­[1,3-bis­(penta­fluoro­phen­yl)propane-1,3-dionato]copper(II)

The Cu²⁺ ions in the title compounds, namely bis­[1,3-bis­(penta­fluoro­phen­yl)propane-1,3-dionato-[kappa]²O,O']copper(II) p-xylene n-solvate, [Cu(C₁₅HF₁₀O₂)₂]·nC₈H₁₀, with n = 1, (I), n = 2, (II), and n = 4, (III), are coordinated by two 1,3-bis­(penta­fluoro­phen­yl)propane-1,3-dionate ligands. The coordination complexes of (I) and (II) have crystallographic inversion symmetry at the Cu atom and the p-xylene molecule in (I) also lies across an inversion centre. The p-xylene mol­ecules in (I) and (II) inter­act with the penta­fluoro­phenyl groups of the complex via arene-perfluoro­arene inter­actions. In the crystal of (III), two of the p-xylene mol­ecules inter­act with the penta­fluoro­phenyl groups via arene-perfluoro­arene inter­actions. The other two p-xylene mol­ecules are located on the CuO₄ coordination plane, forming a uniform cavity produced by metal...[pi] inter­actions.

S1. Introduction

While single crystals of M(dbm)₂ (dbm is di­benzoyl­methane) include no solvent molecules (Vigato et al., 2009; Soldatov et al., 2001), coordination complexes with the fully fluorinated bis­(penta­fluoro­phenyl)­propane-1,3-dione (HL) ligand produced cocrystals, which abundantly take up benzene molecules when crystallized from a benzene/CH₂Cl₂ solvent mixture (Hori & Arii, 2007). For example, single crystals of Cu(L)₂ were obtained as Cu(L)₂·3C₆H₆ with 21 wt% benzene molecules. These high capacities for solvent occlusion are induced by two weak inter­molecular inter­actions, viz. arene–perfluoro­arene and metal···π. The arene–perfluoro­arene inter­action is currently well known as an electrostatic inter­action (Patrick & Prosser, 1960; Williams, 1993), which was observed between the penta­fluoro­phenyl groups of the complex and two benzene molecules. A metal···π inter­action was observed between a Cu²⁺ ion and a benzene molecule. The high encapsulation of aromatic guest molecules into the crystals of the fluorinated complex was also found in the corresponding [Ni₂(L)₄(H₂O)₂] complex, giving the benzene-rich pseudopolymorphs [Ni₂(L)₄(H₂O)₂]·2C₆H₆ and [Ni₂(L)₄(H₂O)₂]·4C₆H₆ (Hori & Mizutani, 2009). Fluorination drastically changes not only the sole structural characteristics and properties, but also the inter­molecular inter­actions to produce molecular recognition events (Reichenbacher et al., 2005; Hori, 2012). As part of a detailed analysis of complexes involving arene–perfluoro­arene inter­actions, we found three pseudopolymorph examples with p-xylene solvation, namely [Cu(L)₂]·C₈H₁₀, (I), [Cu(L)₂]·2C₈H₁₀, (II), and [Cu(L)₂]·4C₈H₁₀, (III), which included the p-xylene at 10.8, 19.9, and 32.3 wt%, respectively. These structures were fully characterized by X-ray crystallographic studies, showing that the guest molecules are stabilized and fixed in an orientation suitable for electrostatic inter­actions with the Cu(L)₂ complex. In this study, the three crystal forms (I)–(III) are compared and discussed in relation to their inter­molecular inter­actions.

S2. Experimental

S2.1. Synthesis and crystallization

The Cu²⁺ complex was prepared according to a previously reported procedure (Hori & Arii, 2007). The complex was crystallized from ethanol with p-xylene to give green block-shaped crystals (I) suitable for X-ray structural analysis. The two kinds of crystals, i.e. (II) and (III), were crystallized from p-xylene/CH₂Cl₂ as green block-shaped crystals. The three crystals were optically indistinguishable.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in geometrically idealized positions and refined as riding, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic, and C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl groups. Tetra­solvate (III) was refined as a racemic twin: Flack parameter = 0.494 (13) (Parsons et al., 2013).

S3. Results and discussion

Concerning the p-xylene encapsulation, the three kinds of crystals (I)–(III) were independently obtained as pseudopolymorphs under different conditions. For example, Cu(L)₂ and excess amounts of p-xylene in ethanol were slowly evaporated to yield the green block-shaped crystal of (I), which grew to a noteworthy large size (one edge> 5 mm). On the other hand, Cu(L)₂ and excess amounts of p-xylene in CH₂Cl₂ (or CHCl₃ or MeOH) were slowly evaporated to give green block-shaped crystal of (II). Evaporation of a solution of Cu(L)₂ in an excess of p-xylene without any solvents also produced crystals of (II). We examined each crystallization at least three times, but never obtained the replaced and mixed crystals between (I) and (II). However, a green block-shaped crystal of (III) was occasionally obtained from CH₂Cl₂, in which crystal (III) was solely obtained as a single component without any admixture of (I) and (II). Unfortunately, crystals of (II) and (III) were optically indistinguishable based on their appearances. The evaporation rates and the starting concentrations showed no relationship with the formation of the pseudopolymorphs. It is noteworthy that crystal (III) was occasionally obtained only in winter, while crystal (II) was obtained throughout the year.

In monosolvate (I), the asymmetric unit contains one half of the coordination complex and one half of a p-xylene molecule (Fig. 1). The complex is centrosymmetric and comprises one Cu²⁺ ion and two L ligands, giving a mononuclear Cu²⁺ complex with a square–planar coordination (Table 2). The p-xylene molecule is located on a crystallographic inversion centre. The penta­fluoro­phenyl groups (ringa A and B) are highly twisted with respect to the coordination plane, as can be gleaned from the respective torsion angles C5—C6—C7—C8 and C8—C9—C10—C15 of -55.0 (3) and 48.7 (3)°.

Disolvate (II) also has one half of the coordination complex in the asymmetric unit and one entire p-xylene molecule, as shown in Fig. 2. The geometry around the metal centre is also square planar (Table 2). The structures of Cu(L)₂ in crystals (I) and (II) are almost the same. The penta­fluoro­phenyl groups (rings D and E) in (II) are also highly twisted with respect to the coordination plane, with torsion angles C5—C6—C7—C8 = 68.39 (17)° and C8—C9—C10—C15 = 66.47 (17)°.

On the other hand, tetra­solvate (III) includes the entire complex, Cu(L)₂, and four p-xylene molecules in the asymmetric unit (Fig. 3). The geometry around the metal centre in (III) is square planar (Table 2). The Cu²⁺ coordination in all three compexes is thus very similar. The penta­fluoro­phenyl groups (rings G, H, I and J) in (III) again show a twisted orientation with respect to the coordination plane [torsion angles C5—C6—C7—C8 = -46.1 (7)°, C8—C9—C10—C15 = -70.5 (6)°, C20—C21—C22—C23 = 45.1 (7)° and C23—C24—C25—C30 = 53.7 (6)°]. The twist angles of rings G and I are very similar, whereas those of rings H and J differ significantly, thus breaking perfect inversion symmetry of complex (III). The structure is thus pseudocentrosymmetric with space group Pn. Because the Flack (1983) parameter refined to a value close to 0.5 [0.494 (13)], the structure is racemically twinned.

The orientations of the penta­fluoro­phenyl groups in (I)–(III) are flexibly twisted and stabilized by the p-xylene molecules through inter­molecular arene–perfluoro­arene inter­actions, as discussed below.

In the crystal structure of (I) (Fig. 4), p-xylene ring C inter­acts closely with penta­fluoro­phenyl ring B^iv [symmetry code: (iv) x-1/2, -y+3/2, -z] of the adjacent complex molecule [CgC···CgB^iv = 3.4747 (12) Å; CgX is the centroid of the ring denoted X]. The corresponding shortest perpendicular distance from the ring centroids to the adjacent planes is 3.3032 (9) Å. The p-xylene molecule further inter­acts with the opposite penta­fluoro­phenyl group [ring B^v; symmetry code: (v) -x+3/2, y+1/2, z] of the complex to give 1:2 sandwich structures through the typical arene–perfluoro­arene inter­actions.

Furthermore, the p-xylene molecule is surrounded by the two coordination CuO₄ sites of Cu(L)₂, but no stacking formation is observed. The inter­molecular distance of C11ⁱ—F6ⁱ···H17ⁱⁱ—C17ⁱⁱ [F6ⁱ···C17ⁱⁱ = 3.239 (3) Å; symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z] is slightly shorter than the standard value, showing that C—F···H inter­actions between the complex and p-xylene molecules dominate the alternate arrangements. Remarkably short inter­molecular distances are observed between pairs of complex molecules, viz. 2.8243 (12) Å for Cu1···F7^iv and 2.8845 (18) Å for O1ⁱ···F7^iv [2.7267 (14) Å between the centroid of Cu1—O1ⁱ—C7ⁱ—C8ⁱ—C9ⁱ—O2ⁱ and F7^iv], showing an inter­action between the metal centre Cu²⁺ (δ⁺) and the fluorine substituent (δ^-).

In the crystal structure of disolvate (II) (Fig. 5), the complex molecules overlap down the a axis, but the shortest inter­molecular metal–metal distance is long [7.5688 (4) Å] because the coordination planes are tilted. This allows the p-xylene molecules to stack alternately with the penta­fluoro­phenyl groups of the complex along the a axis. p-Xylene ring F closely inter­acts with penta­fluoro­phenyl ring D [CgF···CgD = 3.7572 (9) Å]. The corresponding shortest perpendicular distance from the ring centroids to the adjacent planes is 3.5115 (7) Å. Conversely, the p-xylene molecule further inter­acts with adjacent penta­fluoro­phenyl ring D^vi [symmetry code: (vi) x+1, y, z] to give 1:2 sandwich structures through arene–perfluoro­arene inter­actions [CgF···CgD^vi = 3.8175 (9) Å]. The corresponding shortest perpendicular distance from the ring centroids to the adjacent planes is 3.5678 (7) Å. This clearly shows the arene–perfluoro­arene stacking between the complex and p-xylene molecules (Fig. 5). A remarkably short inter­molecular distance of 3.2669 (11) Å is observed between the two complexes, viz. C4—F4···CgE^vii [symmetry code: (vii) -x+1, -y+2, -z+1], indicating C—F···π(C₆F₅) inter­actions (Prasanna & Row, 2000).

In the crystal structure of tetra­solvate (III) (Fig. 6), two kinds of situations are observed for the four p-xylene molecules. p-Xylenes C31–C38 (ring K) and C39–C46 (ring L) closely inter­act with rings H and J of the coordination complex through arene–perfluoro­arene inter­actions, whereas the p-xylenes C47–C54 (ring M) and C55–C62 (ring N) are close to the axial site of the Cu²⁺ ion, where a sufficiently wide cavity exists in the surrounding penta­fluoro­phenyl groups, and the weak metal···π inter­actions are dominant between them. The inter­molecular distances between the two centroids of the penta­fluoro­phenyl groups of the coordination complex and the phenyl­ene ring of p-xylene are 3.662 (3) Å for CgH···CgK^viii [symmetry code: (viii) x-1/2, -y+2, z-1/2], 3.582 (3) Å for CgH···CgL^ix [symmetry code: (ix) x-1/2, -y+1, z-1/2], 3.556 (3) Å for CgJ···CgK^x [symmetry code: (x) x-1, y, z] and 3.618 (3) Å for CgJ···CgL^x. On the other hand, the inter­molecular distances between the centroid of the phenyl­ene ring in p-xylene and the Cu²⁺ ion in the complex are 3.765 Å for CgM^vi···Cu1 and 3.749 Å for CgN···Cu1. The slightly long metal···π distances suggest that p-xylene is large for the Cu²⁺ coordination centre. It is inter­esting that the perfluorinated coordination complex, Cu(L)₂, encapsulates the aromatic guest molecules under different circumstances. The guest encapsulation phenomena should be attributed not only to the cavity effects on the crystal, but also to the fluorination effects of the complex. Accordingly, two kinds of p-xylene molecules produce alternate arrangements between rings K and N and also between rings L and M along the a axis. No remarkable inter­actions between the guest molecules are observed, and each guest molecule inter­acts with the host frameworks of the complex.

Related literature

For related literature, see: Flack (1983); Hori (2012); Hori & Arii (2007); Hori & Mizutani (2009); Parsons et al. (2013); Patrick & Prosser (1960); Prasanna & Row (2000); Reichenbacher et al. (2005); Soldatov et al. (2001); Vigato et al. (2009); Williams (1993).

Computing details

For all compounds, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: Generate Report (Bruker, 2013).

Figures

	Fig. 1. The molecular structure of monosolvate (I) at 120 K, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z.]
	Fig. 2. The molecular structure of disolvate (II) at 120 K, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (iii) -x, -y+1, -z+1.]
	Fig. 3. The molecular structure of tetrasolvate (III) at 100 K, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. A view of part of the crystal structure of (I) along the c axis. [Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z; (iv) x-1/2, -y+3/2, -z; (v) -x+3/2, y+1/2, z.]
	Fig. 5. A view of part of the crystal structure of (II). [Symmetry codes: (iii) -x, -y+1, -z+1; (vi) x+1, y, z; (vii) -x+1, -y+2, -z+1.]
	Fig. 6. A view of part of the crystal structure of (III). [Symmetry codes: (vi) x+1, y, z; (viii) x-1/2, -y+2, z-1/2; (ix) x-1/2, -y+1, z-1/2; (x) x-1, y, z.]

(I) Bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato-κ²O,O']copper(II) p-xylene n-solvate

Crystal data

[Cu(C15HF10O2)2]·C8H10	Dx = 1.866 Mg m^−3
Mr = 976.03	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5529 reflections
a = 11.1299 (10) Å	θ = 2.5–27.9°
b = 13.1194 (12) Å	µ = 0.78 mm^−1
c = 23.797 (2) Å	T = 120 K
V = 3474.7 (5) Å^3	Block, green
Z = 4	0.40 × 0.25 × 0.05 mm
F(000) = 1924

Data collection

Bruker D8 goniometer diffractometer	3967 independent reflections
Radiation source: sealed tube	3079 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −13→14
Tmin = 0.85, Tmax = 0.96	k = −17→8
18319 measured reflections	l = −29→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 2.4502P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3967 reflections	Δρmax = 0.32 e Å^−3
287 parameters	Δρmin = −0.51 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	1.0000	1.0000	0.0000	0.01473 (9)
O1	0.93725 (12)	1.05604 (10)	0.06863 (5)	0.0178 (3)
O2	1.03394 (12)	0.87124 (10)	0.03366 (5)	0.0188 (3)
C1	0.94676 (18)	1.17824 (15)	0.17217 (8)	0.0199 (4)
C2	0.90478 (19)	1.24095 (15)	0.21441 (8)	0.0243 (4)
C3	0.81489 (19)	1.20624 (16)	0.24955 (8)	0.0256 (5)
C4	0.77272 (17)	1.10814 (17)	0.24425 (8)	0.0241 (4)
C5	0.81892 (17)	1.04540 (15)	0.20293 (7)	0.0195 (4)
C6	0.90487 (17)	1.07960 (14)	0.16493 (7)	0.0172 (4)
C7	0.94789 (17)	1.01486 (14)	0.11687 (7)	0.0161 (4)
C8	0.99341 (17)	0.91858 (14)	0.12847 (7)	0.0180 (4)
H8	0.9997	0.8973	0.1665	0.022*
C9	1.03019 (16)	0.85208 (14)	0.08597 (7)	0.0162 (4)
C10	1.06826 (16)	0.74599 (14)	0.10140 (7)	0.0162 (4)
C11	1.17114 (17)	0.70298 (15)	0.07853 (7)	0.0188 (4)
C12	1.20394 (17)	0.60359 (15)	0.08938 (8)	0.0213 (4)
C13	1.13422 (19)	0.54384 (15)	0.12409 (8)	0.0226 (4)
C14	1.03214 (19)	0.58454 (15)	0.14762 (8)	0.0228 (4)
C15	1.00047 (18)	0.68412 (15)	0.13618 (8)	0.0201 (4)
C16	0.5794 (2)	0.93958 (19)	0.03250 (9)	0.0349 (6)
C17	0.4710 (2)	0.9004 (2)	0.01263 (9)	0.0357 (6)
H17	0.4500	0.8318	0.0210	0.043*
C18	0.3935 (2)	0.95941 (19)	−0.01907 (9)	0.0361 (6)
H18	0.3202	0.9306	−0.0320	0.043*
C19	0.6631 (2)	0.8748 (2)	0.06726 (10)	0.0480 (7)
H19A	0.7464	0.8892	0.0566	0.072*
H19B	0.6456	0.8026	0.0606	0.072*
H19C	0.6516	0.8904	0.1072	0.072*
F1	1.03409 (11)	1.21441 (9)	0.13854 (5)	0.0271 (3)
F2	0.95024 (13)	1.33428 (9)	0.22198 (5)	0.0358 (3)
F3	0.77015 (12)	1.26761 (10)	0.28942 (5)	0.0372 (3)
F4	0.68619 (11)	1.07418 (11)	0.27897 (5)	0.0344 (3)
F5	0.77614 (11)	0.95002 (9)	0.19926 (5)	0.0274 (3)
F6	1.24348 (10)	0.75845 (9)	0.04540 (5)	0.0295 (3)
F7	1.30382 (11)	0.56447 (10)	0.06636 (5)	0.0335 (3)
F8	1.16566 (12)	0.44773 (9)	0.13511 (5)	0.0339 (3)
F9	0.96318 (13)	0.52757 (10)	0.18134 (6)	0.0392 (3)
F10	0.89763 (11)	0.71906 (9)	0.15916 (5)	0.0326 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01780 (16)	0.01596 (15)	0.01044 (15)	0.00013 (13)	0.00063 (12)	0.00146 (12)
O1	0.0209 (7)	0.0196 (7)	0.0129 (6)	0.0028 (6)	0.0015 (5)	0.0015 (5)
O2	0.0252 (7)	0.0182 (6)	0.0128 (6)	0.0008 (6)	0.0003 (5)	0.0021 (5)
C1	0.0229 (10)	0.0218 (10)	0.0150 (9)	0.0035 (8)	−0.0003 (8)	0.0035 (8)
C2	0.0348 (12)	0.0200 (10)	0.0182 (9)	0.0074 (9)	−0.0076 (8)	−0.0006 (8)
C3	0.0331 (12)	0.0315 (11)	0.0122 (8)	0.0145 (10)	−0.0034 (8)	−0.0046 (8)
C4	0.0191 (10)	0.0404 (12)	0.0129 (9)	0.0063 (9)	0.0004 (7)	0.0023 (8)
C5	0.0182 (9)	0.0251 (10)	0.0153 (9)	0.0017 (8)	−0.0019 (7)	0.0014 (8)
C6	0.0190 (9)	0.0195 (9)	0.0130 (8)	0.0052 (8)	−0.0014 (7)	0.0014 (7)
C7	0.0146 (9)	0.0194 (9)	0.0142 (8)	−0.0014 (7)	0.0010 (7)	0.0003 (7)
C8	0.0211 (10)	0.0198 (9)	0.0131 (8)	0.0009 (8)	0.0008 (7)	0.0018 (7)
C9	0.0141 (9)	0.0182 (9)	0.0162 (8)	−0.0030 (7)	−0.0006 (7)	0.0029 (7)
C10	0.0188 (9)	0.0171 (9)	0.0128 (8)	−0.0016 (8)	−0.0024 (7)	0.0001 (7)
C11	0.0170 (9)	0.0234 (10)	0.0160 (9)	−0.0026 (8)	−0.0001 (7)	0.0013 (8)
C12	0.0179 (10)	0.0253 (10)	0.0209 (9)	0.0054 (8)	−0.0040 (8)	−0.0050 (8)
C13	0.0302 (11)	0.0160 (9)	0.0214 (9)	0.0035 (9)	−0.0090 (8)	0.0008 (8)
C14	0.0297 (11)	0.0187 (10)	0.0200 (9)	−0.0049 (9)	0.0012 (8)	0.0056 (8)
C15	0.0213 (10)	0.0207 (9)	0.0183 (9)	0.0008 (8)	0.0025 (8)	0.0003 (7)
C16	0.0331 (12)	0.0474 (14)	0.0242 (11)	−0.0127 (11)	0.0125 (9)	−0.0146 (10)
C17	0.0358 (13)	0.0422 (13)	0.0289 (11)	−0.0184 (11)	0.0172 (10)	−0.0143 (10)
C18	0.0304 (12)	0.0480 (14)	0.0299 (11)	−0.0192 (11)	0.0122 (10)	−0.0204 (11)
C19	0.0469 (16)	0.0608 (18)	0.0363 (13)	−0.0142 (14)	0.0060 (12)	−0.0056 (13)
F1	0.0352 (7)	0.0217 (6)	0.0244 (6)	−0.0042 (5)	0.0052 (5)	0.0025 (5)
F2	0.0580 (9)	0.0175 (6)	0.0318 (7)	0.0024 (6)	−0.0036 (6)	−0.0047 (5)
F3	0.0511 (8)	0.0417 (8)	0.0188 (6)	0.0209 (7)	0.0004 (6)	−0.0101 (5)
F4	0.0281 (7)	0.0564 (9)	0.0186 (6)	0.0016 (6)	0.0090 (5)	−0.0018 (6)
F5	0.0279 (7)	0.0303 (7)	0.0242 (6)	−0.0073 (5)	0.0060 (5)	−0.0007 (5)
F6	0.0223 (6)	0.0314 (7)	0.0347 (7)	−0.0007 (5)	0.0112 (5)	0.0071 (6)
F7	0.0223 (6)	0.0351 (7)	0.0429 (7)	0.0125 (6)	0.0028 (5)	−0.0018 (6)
F8	0.0439 (8)	0.0184 (6)	0.0395 (7)	0.0077 (6)	−0.0094 (6)	0.0036 (5)
F9	0.0477 (8)	0.0247 (6)	0.0453 (8)	−0.0042 (6)	0.0158 (7)	0.0154 (6)
F10	0.0306 (7)	0.0261 (6)	0.0409 (7)	0.0027 (5)	0.0201 (6)	0.0071 (6)

Geometric parameters (Å, º)

Cu1—O2	1.9073 (13)	C10—C15	1.383 (3)
Cu1—O2^i	1.9074 (13)	C10—C11	1.388 (3)
Cu1—O1	1.9224 (12)	C11—F6	1.342 (2)
Cu1—O1^i	1.9225 (12)	C11—C12	1.378 (3)
O1—C7	1.274 (2)	C12—F7	1.341 (2)
O2—C9	1.271 (2)	C12—C13	1.378 (3)
C1—F1	1.345 (2)	C13—F8	1.334 (2)
C1—C2	1.380 (3)	C13—C14	1.375 (3)
C1—C6	1.386 (3)	C14—F9	1.339 (2)
C2—F2	1.337 (2)	C14—C15	1.380 (3)
C2—C3	1.381 (3)	C15—F10	1.349 (2)
C3—F3	1.340 (2)	C16—C17	1.395 (3)
C3—C4	1.376 (3)	C16—C18^ii	1.396 (3)
C4—F4	1.345 (2)	C16—C19	1.508 (4)
C4—C5	1.382 (3)	C17—C18	1.383 (4)
C5—F5	1.342 (2)	C17—H17	0.9500
C5—C6	1.391 (3)	C18—C16^ii	1.396 (3)
C6—C7	1.503 (2)	C18—H18	0.9500
C7—C8	1.389 (3)	C19—H19A	0.9800
C8—C9	1.397 (3)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
C9—C10	1.501 (3)
O2—Cu1—O2^i	180.0	C8—C9—C10	119.02 (16)
O2—Cu1—O1	93.09 (5)	C15—C10—C11	116.50 (17)
O2^i—Cu1—O1	86.91 (5)	C15—C10—C9	122.45 (17)
O2—Cu1—O1^i	86.91 (5)	C11—C10—C9	120.95 (16)
O2^i—Cu1—O1^i	93.09 (5)	F6—C11—C12	117.66 (17)
O1—Cu1—O1^i	180.0	F6—C11—C10	120.34 (17)
C7—O1—Cu1	124.71 (12)	C12—C11—C10	121.99 (18)
C9—O2—Cu1	125.46 (12)	F7—C12—C13	119.59 (18)
F1—C1—C2	117.87 (18)	F7—C12—C11	120.33 (18)
F1—C1—C6	119.89 (17)	C13—C12—C11	120.08 (18)
C2—C1—C6	122.21 (18)	F8—C13—C14	120.25 (18)
F2—C2—C1	121.06 (19)	F8—C13—C12	120.50 (18)
F2—C2—C3	119.63 (18)	C14—C13—C12	119.24 (18)
C1—C2—C3	119.32 (19)	F9—C14—C13	120.08 (18)
F3—C3—C4	120.01 (19)	F9—C14—C15	120.02 (19)
F3—C3—C2	119.98 (19)	C13—C14—C15	119.90 (18)
C4—C3—C2	120.00 (18)	F10—C15—C14	117.29 (17)
F4—C4—C3	119.86 (18)	F10—C15—C10	120.41 (17)
F4—C4—C5	120.43 (19)	C14—C15—C10	122.28 (18)
C3—C4—C5	119.71 (18)	C17—C16—C18^ii	117.4 (2)
F5—C5—C4	118.03 (17)	C17—C16—C19	120.8 (2)
F5—C5—C6	120.18 (17)	C18^ii—C16—C19	121.8 (2)
C4—C5—C6	121.77 (19)	C18—C17—C16	121.2 (2)
C1—C6—C5	116.86 (17)	C18—C17—H17	119.4
C1—C6—C7	121.00 (17)	C16—C17—H17	119.4
C5—C6—C7	122.11 (17)	C17—C18—C16^ii	121.4 (2)
O1—C7—C8	126.78 (17)	C17—C18—H18	119.3
O1—C7—C6	114.60 (16)	C16^ii—C18—H18	119.3
C8—C7—C6	118.62 (16)	C16—C19—H19A	109.5
C7—C8—C9	122.08 (17)	C16—C19—H19B	109.5
C7—C8—H8	119.0	H19A—C19—H19B	109.5
C9—C8—H8	119.0	C16—C19—H19C	109.5
O2—C9—C8	126.53 (17)	H19A—C19—H19C	109.5
O2—C9—C10	114.44 (16)	H19B—C19—H19C	109.5
F1—C1—C2—F2	−0.6 (3)	C7—C8—C9—O2	4.3 (3)
C6—C1—C2—F2	177.15 (17)	C7—C8—C9—C10	−174.69 (17)
F1—C1—C2—C3	179.80 (17)	O2—C9—C10—C15	−130.44 (19)
C6—C1—C2—C3	−2.4 (3)	C8—C9—C10—C15	48.7 (3)
F2—C2—C3—F3	2.9 (3)	O2—C9—C10—C11	45.9 (2)
C1—C2—C3—F3	−177.54 (17)	C8—C9—C10—C11	−134.99 (19)
F2—C2—C3—C4	−176.04 (17)	C15—C10—C11—F6	−178.43 (16)
C1—C2—C3—C4	3.6 (3)	C9—C10—C11—F6	5.1 (3)
F3—C3—C4—F4	0.3 (3)	C15—C10—C11—C12	0.5 (3)
C2—C3—C4—F4	179.21 (17)	C9—C10—C11—C12	−175.97 (17)
F3—C3—C4—C5	179.76 (17)	F6—C11—C12—F7	−1.2 (3)
C2—C3—C4—C5	−1.3 (3)	C10—C11—C12—F7	179.76 (17)
F4—C4—C5—F5	−1.0 (3)	F6—C11—C12—C13	178.64 (17)
C3—C4—C5—F5	179.60 (17)	C10—C11—C12—C13	−0.4 (3)
F4—C4—C5—C6	177.32 (17)	F7—C12—C13—F8	0.3 (3)
C3—C4—C5—C6	−2.1 (3)	C11—C12—C13—F8	−179.60 (17)
F1—C1—C6—C5	176.82 (16)	F7—C12—C13—C14	179.86 (17)
C2—C1—C6—C5	−0.9 (3)	C11—C12—C13—C14	0.0 (3)
F1—C1—C6—C7	−5.3 (3)	F8—C13—C14—F9	−0.6 (3)
C2—C1—C6—C7	177.01 (17)	C12—C13—C14—F9	179.84 (18)
F5—C5—C6—C1	−178.57 (16)	F8—C13—C14—C15	179.77 (18)
C4—C5—C6—C1	3.2 (3)	C12—C13—C14—C15	0.2 (3)
F5—C5—C6—C7	3.6 (3)	F9—C14—C15—F10	−1.5 (3)
C4—C5—C6—C7	−174.69 (17)	C13—C14—C15—F10	178.18 (17)
Cu1—O1—C7—C8	−7.8 (3)	F9—C14—C15—C10	−179.65 (18)
Cu1—O1—C7—C6	172.68 (12)	C13—C14—C15—C10	0.0 (3)
C1—C6—C7—O1	−53.2 (2)	C11—C10—C15—F10	−178.48 (16)
C5—C6—C7—O1	124.60 (19)	C9—C10—C15—F10	−2.0 (3)
C1—C6—C7—C8	127.2 (2)	C11—C10—C15—C14	−0.4 (3)
C5—C6—C7—C8	−55.0 (3)	C9—C10—C15—C14	176.09 (18)
O1—C7—C8—C9	−2.5 (3)	C18^ii—C16—C17—C18	−0.1 (3)
C6—C7—C8—C9	177.09 (17)	C19—C16—C17—C18	179.7 (2)
Cu1—O2—C9—C8	4.4 (3)	C16—C17—C18—C16^ii	0.1 (4)
Cu1—O2—C9—C10	−176.49 (11)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+2, −z.

(II) Bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato-κ²O,O']copper(II) p-xylene disolvate

Crystal data

[Cu(C15HF10O2)2]·2C8H10	Z = 1
Mr = 1082.19	F(000) = 539
Triclinic, P1	Dx = 1.717 Mg m^−3
a = 7.5688 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8976 (6) Å	Cell parameters from 8584 reflections
c = 12.2578 (6) Å	θ = 2.4–27.9°
α = 90.7758 (5)°	µ = 0.66 mm^−1
β = 99.1187 (5)°	T = 120 K
γ = 105.8474 (5)°	Prismatic, green
V = 1046.57 (9) Å^3	0.40 × 0.40 × 0.20 mm

Data collection

Bruker D8 goniometer diffractometer	4714 independent reflections
Radiation source: sealed tube	4520 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.018
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −9→9
Tmin = 0.81, Tmax = 0.88	k = −15→15
12038 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0387P)^2 + 0.5676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4714 reflections	Δρmax = 0.35 e Å^−3
324 parameters	Δρmin = −0.50 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	0.5000	0.01409 (7)
O1	0.14839 (13)	0.63204 (8)	0.59651 (8)	0.01741 (19)
O2	0.15820 (13)	0.53465 (8)	0.39122 (8)	0.01758 (19)
C1	0.46491 (18)	0.77779 (12)	0.77070 (11)	0.0174 (3)
C2	0.54627 (19)	0.86513 (13)	0.85354 (11)	0.0212 (3)
C3	0.5452 (2)	0.97902 (13)	0.83293 (12)	0.0242 (3)
C4	0.4664 (2)	1.00451 (12)	0.73052 (13)	0.0236 (3)
C5	0.38986 (19)	0.91660 (12)	0.64841 (11)	0.0195 (3)
C6	0.38537 (17)	0.80111 (11)	0.66666 (11)	0.0153 (2)
C7	0.29598 (17)	0.70464 (11)	0.57786 (10)	0.0149 (2)
C8	0.38151 (18)	0.70311 (12)	0.48517 (11)	0.0180 (3)
H8	0.4935	0.7619	0.4809	0.022*
C9	0.30682 (17)	0.61753 (11)	0.39874 (10)	0.0145 (2)
C10	0.40891 (17)	0.61937 (11)	0.30254 (10)	0.0147 (2)
C11	0.32911 (18)	0.63661 (12)	0.19637 (11)	0.0180 (3)
C12	0.4171 (2)	0.63262 (13)	0.10641 (11)	0.0214 (3)
C13	0.5881 (2)	0.60970 (12)	0.12160 (12)	0.0218 (3)
C14	0.67085 (19)	0.59151 (12)	0.22611 (12)	0.0206 (3)
C15	0.58144 (18)	0.59794 (11)	0.31516 (11)	0.0176 (3)
C16	0.9590 (2)	0.78907 (15)	0.79456 (13)	0.0273 (3)
C17	1.0335 (2)	0.88873 (18)	0.86553 (14)	0.0356 (4)
H17	1.0787	0.8807	0.9410	0.043*
C18	1.0431 (2)	0.99955 (17)	0.82876 (16)	0.0387 (4)
H18	1.0948	1.0658	0.8795	0.046*
C19	0.9785 (2)	1.01581 (15)	0.71881 (15)	0.0327 (4)
C20	0.9046 (2)	0.91619 (14)	0.64705 (14)	0.0288 (3)
H20	0.8600	0.9244	0.5715	0.035*
C21	0.8949 (2)	0.80516 (14)	0.68419 (13)	0.0267 (3)
H21	0.8436	0.7388	0.6335	0.032*
C22	0.9465 (3)	0.66842 (17)	0.83434 (15)	0.0361 (4)
H22A	0.9982	0.6744	0.9134	0.054*
H22B	1.0174	0.6305	0.7930	0.054*
H22C	0.8157	0.6218	0.8225	0.054*
C23	0.9901 (3)	1.13618 (17)	0.6788 (2)	0.0502 (5)
H23A	1.0317	1.1937	0.7421	0.075*
H23B	0.8670	1.1385	0.6411	0.075*
H23C	1.0790	1.1547	0.6272	0.075*
F1	0.46985 (13)	0.66826 (7)	0.79131 (7)	0.02477 (18)
F2	0.62668 (13)	0.84124 (9)	0.95225 (7)	0.0312 (2)
F3	0.62127 (15)	1.06451 (8)	0.91226 (8)	0.0365 (2)
F4	0.46457 (16)	1.11511 (8)	0.71103 (9)	0.0378 (2)
F5	0.31611 (14)	0.94499 (8)	0.54917 (7)	0.0292 (2)
F6	0.16467 (12)	0.66027 (9)	0.17904 (7)	0.0288 (2)
F7	0.33637 (14)	0.64936 (10)	0.00542 (7)	0.0345 (2)
F8	0.67395 (14)	0.60468 (9)	0.03515 (8)	0.0328 (2)
F9	0.83453 (12)	0.56737 (9)	0.24119 (8)	0.0317 (2)
F10	0.66593 (12)	0.58023 (8)	0.41631 (7)	0.0274 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01255 (11)	0.01641 (11)	0.01096 (11)	−0.00086 (8)	0.00396 (8)	−0.00205 (8)
O1	0.0162 (4)	0.0189 (4)	0.0145 (4)	−0.0011 (4)	0.0057 (3)	−0.0031 (4)
O2	0.0154 (4)	0.0209 (5)	0.0136 (4)	−0.0010 (4)	0.0046 (3)	−0.0017 (4)
C1	0.0175 (6)	0.0170 (6)	0.0171 (6)	0.0032 (5)	0.0041 (5)	0.0003 (5)
C2	0.0196 (6)	0.0263 (7)	0.0147 (6)	0.0028 (5)	0.0009 (5)	−0.0024 (5)
C3	0.0239 (7)	0.0212 (7)	0.0219 (7)	−0.0017 (5)	0.0025 (6)	−0.0099 (5)
C4	0.0277 (7)	0.0141 (6)	0.0275 (7)	0.0028 (5)	0.0062 (6)	−0.0011 (5)
C5	0.0205 (6)	0.0190 (6)	0.0178 (6)	0.0035 (5)	0.0028 (5)	0.0019 (5)
C6	0.0135 (6)	0.0160 (6)	0.0149 (6)	0.0006 (5)	0.0045 (5)	−0.0018 (5)
C7	0.0150 (6)	0.0148 (6)	0.0138 (6)	0.0033 (5)	0.0009 (5)	−0.0001 (5)
C8	0.0162 (6)	0.0181 (6)	0.0169 (6)	−0.0015 (5)	0.0058 (5)	−0.0009 (5)
C9	0.0145 (6)	0.0172 (6)	0.0128 (6)	0.0047 (5)	0.0040 (4)	0.0026 (5)
C10	0.0148 (6)	0.0134 (6)	0.0146 (6)	0.0003 (4)	0.0053 (5)	−0.0004 (4)
C11	0.0149 (6)	0.0214 (6)	0.0169 (6)	0.0026 (5)	0.0048 (5)	0.0004 (5)
C12	0.0230 (7)	0.0261 (7)	0.0132 (6)	0.0024 (5)	0.0049 (5)	0.0009 (5)
C13	0.0251 (7)	0.0220 (7)	0.0196 (7)	0.0031 (5)	0.0139 (5)	−0.0011 (5)
C14	0.0172 (6)	0.0192 (6)	0.0278 (7)	0.0054 (5)	0.0106 (5)	0.0028 (5)
C15	0.0184 (6)	0.0170 (6)	0.0172 (6)	0.0036 (5)	0.0048 (5)	0.0032 (5)
C16	0.0190 (7)	0.0402 (9)	0.0247 (7)	0.0116 (6)	0.0039 (6)	−0.0028 (6)
C17	0.0279 (8)	0.0535 (11)	0.0227 (8)	0.0113 (7)	−0.0025 (6)	−0.0076 (7)
C18	0.0294 (8)	0.0424 (10)	0.0376 (9)	0.0055 (7)	−0.0044 (7)	−0.0210 (8)
C19	0.0225 (7)	0.0322 (8)	0.0404 (9)	0.0070 (6)	−0.0010 (7)	−0.0085 (7)
C20	0.0253 (7)	0.0345 (8)	0.0258 (8)	0.0109 (6)	−0.0016 (6)	−0.0044 (6)
C21	0.0244 (7)	0.0320 (8)	0.0235 (7)	0.0098 (6)	0.0004 (6)	−0.0081 (6)
C22	0.0369 (9)	0.0466 (10)	0.0282 (8)	0.0173 (8)	0.0060 (7)	0.0047 (7)
C23	0.0481 (11)	0.0311 (9)	0.0640 (14)	0.0086 (8)	−0.0074 (10)	−0.0082 (9)
F1	0.0342 (5)	0.0189 (4)	0.0204 (4)	0.0082 (3)	0.0006 (3)	0.0019 (3)
F2	0.0349 (5)	0.0371 (5)	0.0156 (4)	0.0060 (4)	−0.0057 (4)	−0.0024 (4)
F3	0.0438 (6)	0.0272 (5)	0.0288 (5)	−0.0014 (4)	−0.0011 (4)	−0.0156 (4)
F4	0.0563 (6)	0.0137 (4)	0.0402 (6)	0.0064 (4)	0.0051 (5)	−0.0010 (4)
F5	0.0399 (5)	0.0241 (4)	0.0216 (4)	0.0093 (4)	−0.0018 (4)	0.0048 (3)
F6	0.0181 (4)	0.0506 (6)	0.0211 (4)	0.0140 (4)	0.0049 (3)	0.0077 (4)
F7	0.0328 (5)	0.0578 (6)	0.0127 (4)	0.0112 (5)	0.0057 (4)	0.0060 (4)
F8	0.0363 (5)	0.0422 (5)	0.0258 (5)	0.0111 (4)	0.0221 (4)	0.0008 (4)
F9	0.0226 (4)	0.0392 (5)	0.0417 (5)	0.0165 (4)	0.0156 (4)	0.0092 (4)
F10	0.0237 (4)	0.0414 (5)	0.0208 (4)	0.0149 (4)	0.0039 (3)	0.0087 (4)

Geometric parameters (Å, º)

Cu1—O2^i	1.9061 (9)	C12—F7	1.3337 (16)
Cu1—O2	1.9061 (9)	C12—C13	1.379 (2)
Cu1—O1	1.9219 (9)	C13—F8	1.3365 (15)
Cu1—O1^i	1.9219 (9)	C13—C14	1.381 (2)
O1—C7	1.2671 (16)	C14—F9	1.3322 (16)
O2—C9	1.2670 (16)	C14—C15	1.3840 (19)
C1—F1	1.3401 (15)	C15—F10	1.3491 (16)
C1—C2	1.3834 (19)	C16—C17	1.390 (2)
C1—C6	1.3868 (19)	C16—C21	1.397 (2)
C2—F2	1.3363 (16)	C16—C22	1.506 (2)
C2—C3	1.384 (2)	C17—C18	1.386 (3)
C3—F3	1.3370 (16)	C17—H17	0.9500
C3—C4	1.377 (2)	C18—C19	1.394 (3)
C4—F4	1.3440 (16)	C18—H18	0.9500
C4—C5	1.378 (2)	C19—C20	1.395 (2)
C5—F5	1.3433 (16)	C19—C23	1.504 (3)
C5—C6	1.3872 (19)	C20—C21	1.390 (2)
C6—C7	1.5061 (17)	C20—H20	0.9500
C7—C8	1.3962 (18)	C21—H21	0.9500
C8—C9	1.3947 (18)	C22—H22A	0.9800
C8—H8	0.9500	C22—H22B	0.9800
C9—C10	1.5061 (17)	C22—H22C	0.9800
C10—C15	1.3832 (18)	C23—H23A	0.9800
C10—C11	1.3878 (18)	C23—H23B	0.9800
C11—F6	1.3351 (16)	C23—H23C	0.9800
C11—C12	1.3821 (19)
O2^i—Cu1—O2	180.0	F7—C12—C11	120.33 (13)
O2^i—Cu1—O1	87.02 (4)	C13—C12—C11	119.49 (13)
O2—Cu1—O1	92.98 (4)	F8—C13—C12	120.08 (13)
O2^i—Cu1—O1^i	92.98 (4)	F8—C13—C14	119.82 (13)
O2—Cu1—O1^i	87.02 (4)	C12—C13—C14	120.10 (12)
O1—Cu1—O1^i	180.00 (6)	F9—C14—C13	120.47 (13)
C7—O1—Cu1	125.65 (8)	F9—C14—C15	120.21 (13)
C9—O2—Cu1	125.98 (8)	C13—C14—C15	119.32 (13)
F1—C1—C2	118.42 (12)	F10—C15—C10	119.99 (12)
F1—C1—C6	119.50 (12)	F10—C15—C14	118.00 (12)
C2—C1—C6	122.04 (13)	C10—C15—C14	122.00 (13)
F2—C2—C1	121.07 (13)	C17—C16—C21	117.23 (16)
F2—C2—C3	119.80 (13)	C17—C16—C22	121.75 (15)
C1—C2—C3	119.13 (13)	C21—C16—C22	121.02 (15)
F3—C3—C4	119.91 (14)	C18—C17—C16	121.55 (16)
F3—C3—C2	120.08 (14)	C18—C17—H17	119.2
C4—C3—C2	120.01 (13)	C16—C17—H17	119.2
F4—C4—C3	119.84 (13)	C17—C18—C19	121.34 (16)
F4—C4—C5	120.26 (13)	C17—C18—H18	119.3
C3—C4—C5	119.90 (13)	C19—C18—H18	119.3
F5—C5—C4	118.22 (12)	C18—C19—C20	117.39 (16)
F5—C5—C6	120.08 (12)	C18—C19—C23	121.31 (16)
C4—C5—C6	121.69 (13)	C20—C19—C23	121.31 (17)
C1—C6—C5	117.20 (12)	C21—C20—C19	121.14 (16)
C1—C6—C7	121.24 (12)	C21—C20—H20	119.4
C5—C6—C7	121.55 (12)	C19—C20—H20	119.4
O1—C7—C8	126.72 (12)	C20—C21—C16	121.36 (15)
O1—C7—C6	115.16 (11)	C20—C21—H21	119.3
C8—C7—C6	118.12 (11)	C16—C21—H21	119.3
C9—C8—C7	121.75 (12)	C16—C22—H22A	109.5
C9—C8—H8	119.1	C16—C22—H22B	109.5
C7—C8—H8	119.1	H22A—C22—H22B	109.5
O2—C9—C8	126.86 (12)	C16—C22—H22C	109.5
O2—C9—C10	114.19 (11)	H22A—C22—H22C	109.5
C8—C9—C10	118.94 (11)	H22B—C22—H22C	109.5
C15—C10—C11	117.23 (12)	C19—C23—H23A	109.5
C15—C10—C9	121.49 (12)	C19—C23—H23B	109.5
C11—C10—C9	121.20 (12)	H23A—C23—H23B	109.5
F6—C11—C12	117.99 (12)	C19—C23—H23C	109.5
F6—C11—C10	120.15 (12)	H23A—C23—H23C	109.5
C12—C11—C10	121.84 (13)	H23B—C23—H23C	109.5
F7—C12—C13	120.17 (12)
F1—C1—C2—F2	−0.6 (2)	C8—C9—C10—C15	66.47 (17)
C6—C1—C2—F2	−178.13 (12)	O2—C9—C10—C11	63.47 (16)
F1—C1—C2—C3	178.87 (12)	C8—C9—C10—C11	−116.96 (14)
C6—C1—C2—C3	1.3 (2)	C15—C10—C11—F6	−178.50 (12)
F2—C2—C3—F3	−1.3 (2)	C9—C10—C11—F6	4.78 (19)
C1—C2—C3—F3	179.25 (13)	C15—C10—C11—C12	0.1 (2)
F2—C2—C3—C4	178.48 (13)	C9—C10—C11—C12	−176.66 (12)
C1—C2—C3—C4	−1.0 (2)	F6—C11—C12—F7	−1.5 (2)
F3—C3—C4—F4	−0.7 (2)	C10—C11—C12—F7	179.88 (13)
C2—C3—C4—F4	179.55 (13)	F6—C11—C12—C13	179.28 (13)
F3—C3—C4—C5	179.31 (13)	C10—C11—C12—C13	0.7 (2)
C2—C3—C4—C5	−0.5 (2)	F7—C12—C13—F8	0.3 (2)
F4—C4—C5—F5	0.7 (2)	C11—C12—C13—F8	179.47 (13)
C3—C4—C5—F5	−179.26 (13)	F7—C12—C13—C14	−179.51 (13)
F4—C4—C5—C6	−178.37 (13)	C11—C12—C13—C14	−0.3 (2)
C3—C4—C5—C6	1.7 (2)	F8—C13—C14—F9	−0.9 (2)
F1—C1—C6—C5	−177.72 (12)	C12—C13—C14—F9	178.85 (13)
C2—C1—C6—C5	−0.2 (2)	F8—C13—C14—C15	179.44 (12)
F1—C1—C6—C7	2.99 (19)	C12—C13—C14—C15	−0.8 (2)
C2—C1—C6—C7	−179.46 (12)	C11—C10—C15—F10	−179.86 (12)
F5—C5—C6—C1	179.62 (12)	C9—C10—C15—F10	−3.15 (19)
C4—C5—C6—C1	−1.3 (2)	C11—C10—C15—C14	−1.19 (19)
F5—C5—C6—C7	−1.10 (19)	C9—C10—C15—C14	175.52 (12)
C4—C5—C6—C7	177.97 (13)	F9—C14—C15—F10	0.63 (19)
Cu1—O1—C7—C8	−0.77 (19)	C13—C14—C15—F10	−179.75 (12)
Cu1—O1—C7—C6	179.54 (8)	F9—C14—C15—C10	−178.06 (12)
C1—C6—C7—O1	67.37 (16)	C13—C14—C15—C10	1.6 (2)
C5—C6—C7—O1	−111.89 (14)	C21—C16—C17—C18	0.3 (2)
C1—C6—C7—C8	−112.35 (15)	C22—C16—C17—C18	−179.39 (16)
C5—C6—C7—C8	68.39 (17)	C16—C17—C18—C19	0.0 (3)
O1—C7—C8—C9	1.0 (2)	C17—C18—C19—C20	−0.3 (3)
C6—C7—C8—C9	−179.35 (12)	C17—C18—C19—C23	−179.65 (18)
Cu1—O2—C9—C8	−2.86 (19)	C18—C19—C20—C21	0.4 (2)
Cu1—O2—C9—C10	176.67 (8)	C23—C19—C20—C21	179.72 (17)
C7—C8—C9—O2	1.0 (2)	C19—C20—C21—C16	−0.1 (2)
C7—C8—C9—C10	−178.49 (12)	C17—C16—C21—C20	−0.2 (2)
O2—C9—C10—C15	−113.10 (14)	C22—C16—C21—C20	179.45 (15)

Symmetry code: (i) −x, −y+1, −z+1.

(III) Bis[1,3-bis(pentafluorophenyl)propane-1,3-dionato-κ²O,O']copper(II) p-xylene tetrasolvate

Crystal data

[Cu(C15HF10O2)2]·4C8H10	F(000) = 1310
Mr = 1294.49	Dx = 1.539 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 13.8034 (16) Å	Cell parameters from 8297 reflections
b = 14.2545 (17) Å	θ = 2.3–27.0°
c = 14.9313 (17) Å	µ = 0.51 mm^−1
β = 108.0612 (13)°	T = 100 K
V = 2793.1 (6) Å^3	Block, green
Z = 2	0.22 × 0.15 × 0.10 mm

Data collection

Bruker D8 goniometer diffractometer	12693 independent reflections
Radiation source: sealed tube	10311 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −17→17
Tmin = 0.91, Tmax = 0.95	k = −18→18
31741 measured reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 0.2568P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.093	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.37 e Å^−3
12693 reflections	Δρmin = −0.39 e Å^−3
793 parameters	Absolute structure: Refined as an inversion twin; 6303 Bijvoet pairs (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.494 (13)
Primary atom site location: structure-invariant direct methods

Special details

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.17563 (6)	0.75464 (4)	0.19831 (6)	0.02026 (11)
O1	0.1062 (3)	0.8731 (2)	0.1724 (2)	0.0205 (7)
O2	0.2610 (3)	0.7822 (2)	0.1220 (2)	0.0226 (7)
O3	0.2451 (3)	0.63676 (19)	0.2239 (2)	0.0219 (7)
O4	0.0897 (2)	0.7262 (2)	0.2742 (2)	0.0215 (7)
C1	−0.0458 (4)	1.0168 (3)	0.1043 (4)	0.0246 (11)
C2	−0.1050 (4)	1.0953 (3)	0.0999 (4)	0.0276 (11)
C3	−0.0621 (4)	1.1826 (3)	0.1042 (4)	0.0304 (12)
C4	0.0391 (4)	1.1907 (3)	0.1087 (4)	0.0303 (12)
C5	0.0955 (4)	1.1111 (3)	0.1107 (4)	0.0253 (11)
C6	0.0562 (4)	1.0217 (3)	0.1088 (3)	0.0198 (10)
C7	0.1192 (4)	0.9343 (3)	0.1152 (3)	0.0194 (10)
C8	0.1838 (4)	0.9277 (3)	0.0602 (3)	0.0206 (10)
H8	0.1817	0.9754	0.0152	0.025*
C9	0.2517 (4)	0.8529 (3)	0.0690 (3)	0.0192 (11)
C10	0.3214 (4)	0.8542 (3)	0.0087 (4)	0.0196 (11)
C11	0.4261 (4)	0.8650 (3)	0.0487 (4)	0.0270 (11)
C12	0.4907 (4)	0.8627 (3)	−0.0053 (4)	0.0298 (11)
C13	0.4523 (4)	0.8471 (3)	−0.0994 (4)	0.0271 (12)
C14	0.3492 (4)	0.8356 (3)	−0.1415 (4)	0.0297 (11)
C15	0.2850 (4)	0.8402 (3)	−0.0871 (4)	0.0256 (11)
C16	0.3974 (4)	0.4942 (3)	0.2927 (3)	0.0229 (10)
C17	0.4566 (4)	0.4159 (4)	0.2940 (4)	0.0285 (12)
C18	0.4146 (4)	0.3288 (3)	0.2882 (4)	0.0286 (12)
C19	0.3136 (5)	0.3185 (3)	0.2816 (4)	0.0289 (12)
C20	0.2548 (4)	0.3976 (3)	0.2809 (3)	0.0229 (11)
C21	0.2948 (4)	0.4874 (3)	0.2850 (3)	0.0198 (10)
C22	0.2317 (3)	0.5739 (3)	0.2786 (3)	0.0192 (10)
C23	0.1634 (4)	0.5788 (3)	0.3309 (3)	0.0228 (11)
H23	0.1622	0.5285	0.3723	0.027*
C24	0.0976 (4)	0.6535 (3)	0.3252 (3)	0.0185 (10)
C25	0.0242 (4)	0.6498 (3)	0.3815 (4)	0.0188 (10)
C26	−0.0789 (4)	0.6637 (3)	0.3400 (3)	0.0239 (10)
C27	−0.1470 (4)	0.6624 (3)	0.3908 (4)	0.0282 (12)
C28	−0.1117 (4)	0.6480 (3)	0.4865 (4)	0.0302 (13)
C29	−0.0102 (4)	0.6333 (3)	0.5295 (4)	0.0334 (13)
C30	0.0561 (4)	0.6337 (3)	0.4770 (4)	0.0282 (12)
C31	0.9933 (4)	0.8872 (3)	0.5385 (4)	0.0338 (13)
C32	1.0225 (4)	0.8861 (3)	0.4584 (4)	0.0346 (13)
H32	1.0928	0.8797	0.4644	0.042*
C33	0.9536 (4)	0.8941 (3)	0.3703 (4)	0.0362 (14)
H33	0.9774	0.8936	0.3170	0.043*
C34	0.8499 (4)	0.9029 (3)	0.3566 (4)	0.0325 (12)
C35	0.8190 (4)	0.9030 (3)	0.4379 (4)	0.0351 (14)
H35	0.7486	0.9089	0.4315	0.042*
C36	0.8882 (4)	0.8948 (4)	0.5268 (4)	0.0361 (14)
H36	0.8650	0.8943	0.5804	0.043*
C37	1.0683 (5)	0.8783 (5)	0.6344 (4)	0.0561 (16)
H37A	1.1084	0.8209	0.6378	0.084*
H37B	1.0321	0.8754	0.6813	0.084*
H37C	1.1139	0.9328	0.6472	0.084*
C38	0.7730 (5)	0.9103 (4)	0.2582 (4)	0.0531 (15)
H38A	0.7904	0.9640	0.2252	0.080*
H38B	0.7045	0.9190	0.2634	0.080*
H38C	0.7748	0.8527	0.2230	0.080*
C39	0.9941 (4)	0.3827 (3)	0.5314 (4)	0.0335 (12)
C40	1.0280 (4)	0.3933 (3)	0.4545 (4)	0.0323 (13)
H40	1.0991	0.3915	0.4633	0.039*
C41	0.9618 (4)	0.4066 (3)	0.3654 (4)	0.0309 (13)
H41	0.9884	0.4129	0.3141	0.037*
C42	0.8585 (4)	0.4109 (3)	0.3484 (4)	0.0312 (12)
C43	0.8225 (4)	0.4007 (3)	0.4255 (4)	0.0341 (13)
H43	0.7513	0.4041	0.4162	0.041*
C44	0.8889 (5)	0.3856 (3)	0.5160 (4)	0.0363 (14)
H44	0.8627	0.3773	0.5673	0.044*
C45	1.0682 (5)	0.3667 (4)	0.6277 (4)	0.0542 (16)
H45A	1.1102	0.3116	0.6265	0.081*
H45B	1.0307	0.3563	0.6728	0.081*
H45C	1.1121	0.4220	0.6468	0.081*
C46	0.7858 (4)	0.4263 (4)	0.2498 (4)	0.0495 (15)
H46A	0.8170	0.4690	0.2153	0.074*
H46B	0.7222	0.4538	0.2538	0.074*
H46C	0.7712	0.3661	0.2166	0.074*
C47	0.8846 (5)	0.6716 (4)	0.0277 (4)	0.0358 (13)
C48	0.8805 (5)	0.5767 (4)	0.0453 (4)	0.0378 (13)
H48	0.8204	0.5517	0.0545	0.045*
C49	0.9605 (5)	0.5173 (4)	0.0502 (4)	0.0390 (14)
H49	0.9547	0.4526	0.0631	0.047*
C50	1.0498 (4)	0.5505 (4)	0.0365 (4)	0.0315 (12)
C51	1.0546 (5)	0.6454 (3)	0.0190 (4)	0.0327 (13)
H51	1.1146	0.6702	0.0096	0.039*
C52	0.9746 (4)	0.7053 (4)	0.0150 (4)	0.0343 (13)
H52	0.9809	0.7702	0.0034	0.041*
C53	0.7969 (5)	0.7352 (4)	0.0211 (5)	0.0483 (16)
H53A	0.7373	0.7142	−0.0301	0.073*
H53B	0.8146	0.7993	0.0084	0.073*
H53C	0.7811	0.7338	0.0807	0.073*
C54	1.1362 (5)	0.4856 (4)	0.0369 (4)	0.0400 (14)
H54A	1.1363	0.4317	0.0776	0.060*
H54B	1.2010	0.5193	0.0608	0.060*
H54C	1.1274	0.4638	−0.0273	0.060*
C55	0.2947 (4)	0.9636 (3)	0.3611 (4)	0.0280 (11)
C56	0.2916 (4)	0.8675 (3)	0.3757 (4)	0.0291 (12)
H56	0.2331	0.8405	0.3861	0.035*
C57	0.3736 (4)	0.8102 (3)	0.3754 (4)	0.0308 (12)
H57	0.3703	0.7448	0.3859	0.037*
C58	0.4600 (4)	0.8478 (3)	0.3599 (4)	0.0328 (13)
C59	0.4625 (5)	0.9432 (4)	0.3456 (4)	0.0367 (13)
H59	0.5213	0.9703	0.3359	0.044*
C60	0.3810 (4)	1.0008 (4)	0.3452 (4)	0.0330 (12)
H60	0.3844	1.0662	0.3339	0.040*
C61	0.2069 (4)	1.0250 (3)	0.3634 (4)	0.0327 (12)
H61A	0.1428	0.9964	0.3254	0.049*
H61B	0.2143	1.0869	0.3376	0.049*
H61C	0.2065	1.0319	0.4285	0.049*
C62	0.5494 (5)	0.7846 (4)	0.3603 (5)	0.0468 (15)
H62A	0.5914	0.8160	0.3270	0.070*
H62B	0.5235	0.7253	0.3286	0.070*
H62C	0.5907	0.7720	0.4254	0.070*
F1	−0.0914 (2)	0.93329 (19)	0.0973 (2)	0.0348 (7)
F2	−0.2039 (2)	1.0869 (2)	0.0913 (2)	0.0403 (8)
F3	−0.1187 (3)	1.2595 (2)	0.0991 (3)	0.0432 (9)
F4	0.0791 (3)	1.2761 (2)	0.1088 (3)	0.0471 (9)
F5	0.1939 (2)	1.12306 (18)	0.1152 (2)	0.0368 (8)
F6	0.4650 (2)	0.8798 (2)	0.14101 (19)	0.0451 (8)
F7	0.5910 (2)	0.8735 (2)	0.0352 (2)	0.0522 (9)
F8	0.5146 (3)	0.8429 (2)	−0.1535 (2)	0.0403 (8)
F9	0.3125 (2)	0.8195 (3)	−0.23473 (19)	0.0515 (8)
F10	0.1851 (2)	0.8272 (3)	−0.1294 (2)	0.0497 (8)
F11	0.4428 (2)	0.57798 (19)	0.3023 (2)	0.0344 (7)
F12	0.5569 (2)	0.4255 (2)	0.3068 (2)	0.0391 (8)
F13	0.4723 (3)	0.25216 (19)	0.2916 (3)	0.0463 (10)
F14	0.2723 (3)	0.2329 (2)	0.2774 (3)	0.0462 (9)
F15	0.1571 (2)	0.38428 (18)	0.2744 (2)	0.0342 (7)
F16	−0.1166 (2)	0.6789 (2)	0.24653 (19)	0.0426 (7)
F17	−0.2469 (2)	0.6749 (2)	0.3476 (2)	0.0486 (8)
F18	−0.1767 (3)	0.6482 (2)	0.5368 (2)	0.0453 (9)
F19	0.0244 (3)	0.6189 (3)	0.6227 (2)	0.0594 (10)
F20	0.1557 (2)	0.6200 (2)	0.5226 (2)	0.0471 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0261 (2)	0.0175 (2)	0.02174 (19)	0.00388 (18)	0.01416 (15)	0.00478 (18)
O1	0.0255 (19)	0.0194 (15)	0.0198 (18)	0.0047 (13)	0.0116 (15)	0.0039 (13)
O2	0.029 (2)	0.0204 (15)	0.0236 (19)	0.0043 (14)	0.0157 (15)	0.0044 (14)
O3	0.0265 (19)	0.0197 (15)	0.0239 (19)	0.0026 (12)	0.0143 (15)	0.0050 (13)
O4	0.0250 (19)	0.0181 (14)	0.0255 (19)	0.0046 (13)	0.0138 (15)	0.0064 (13)
C1	0.032 (3)	0.022 (2)	0.023 (3)	0.0000 (19)	0.013 (2)	0.0006 (18)
C2	0.023 (3)	0.037 (3)	0.024 (3)	0.012 (2)	0.010 (2)	0.003 (2)
C3	0.045 (4)	0.024 (2)	0.024 (3)	0.018 (2)	0.013 (2)	0.003 (2)
C4	0.041 (3)	0.022 (2)	0.027 (3)	0.005 (2)	0.010 (2)	0.001 (2)
C5	0.030 (3)	0.023 (2)	0.026 (3)	0.0012 (19)	0.012 (2)	0.0016 (19)
C6	0.023 (3)	0.023 (2)	0.016 (3)	0.0036 (18)	0.008 (2)	0.0014 (17)
C7	0.025 (3)	0.0142 (19)	0.018 (2)	−0.0035 (17)	0.004 (2)	0.0006 (17)
C8	0.027 (3)	0.018 (2)	0.020 (3)	0.0030 (18)	0.011 (2)	0.0040 (17)
C9	0.021 (3)	0.019 (2)	0.018 (3)	−0.0019 (17)	0.007 (2)	−0.0018 (17)
C10	0.024 (3)	0.015 (2)	0.024 (3)	0.0008 (16)	0.013 (2)	0.0017 (17)
C11	0.030 (3)	0.031 (2)	0.021 (2)	0.000 (2)	0.011 (2)	−0.0011 (19)
C12	0.023 (3)	0.035 (2)	0.034 (3)	0.004 (2)	0.013 (2)	0.001 (2)
C13	0.034 (3)	0.027 (2)	0.030 (3)	0.001 (2)	0.024 (3)	0.0031 (19)
C14	0.033 (3)	0.039 (3)	0.019 (2)	−0.001 (2)	0.011 (2)	−0.001 (2)
C15	0.023 (3)	0.037 (3)	0.018 (2)	−0.0060 (19)	0.008 (2)	0.0021 (19)
C16	0.023 (3)	0.028 (2)	0.018 (3)	0.0032 (19)	0.007 (2)	0.0034 (19)
C17	0.028 (3)	0.042 (3)	0.016 (3)	0.011 (2)	0.007 (2)	0.001 (2)
C18	0.031 (3)	0.035 (3)	0.020 (3)	0.019 (2)	0.010 (2)	0.004 (2)
C19	0.047 (3)	0.017 (2)	0.027 (3)	0.005 (2)	0.016 (2)	0.0041 (19)
C20	0.023 (3)	0.024 (2)	0.024 (3)	0.0049 (18)	0.011 (2)	0.0015 (18)
C21	0.024 (3)	0.021 (2)	0.015 (3)	0.0030 (18)	0.008 (2)	0.0028 (17)
C22	0.016 (2)	0.023 (2)	0.019 (3)	0.0032 (17)	0.006 (2)	−0.0007 (18)
C23	0.032 (3)	0.017 (2)	0.022 (3)	0.0035 (18)	0.013 (2)	0.0070 (18)
C24	0.023 (3)	0.019 (2)	0.016 (3)	−0.0013 (17)	0.008 (2)	−0.0011 (17)
C25	0.025 (3)	0.0140 (19)	0.020 (3)	0.0019 (17)	0.011 (2)	0.0012 (16)
C26	0.028 (3)	0.023 (2)	0.022 (2)	−0.0031 (18)	0.010 (2)	−0.0020 (18)
C27	0.019 (3)	0.031 (2)	0.037 (3)	0.0004 (19)	0.012 (2)	−0.003 (2)
C28	0.034 (3)	0.024 (2)	0.045 (4)	0.000 (2)	0.031 (3)	0.001 (2)
C29	0.044 (3)	0.040 (3)	0.023 (3)	0.005 (2)	0.020 (2)	0.010 (2)
C30	0.026 (3)	0.031 (2)	0.030 (3)	0.007 (2)	0.013 (2)	0.005 (2)
C31	0.023 (3)	0.030 (2)	0.048 (3)	−0.006 (2)	0.011 (2)	−0.001 (2)
C32	0.029 (3)	0.026 (2)	0.054 (4)	−0.002 (2)	0.022 (3)	0.000 (2)
C33	0.039 (3)	0.026 (3)	0.052 (4)	0.000 (2)	0.027 (3)	0.001 (2)
C34	0.036 (3)	0.023 (2)	0.042 (3)	0.003 (2)	0.018 (3)	0.001 (2)
C35	0.029 (3)	0.029 (3)	0.050 (4)	0.002 (2)	0.017 (3)	−0.008 (2)
C36	0.031 (3)	0.037 (3)	0.046 (4)	−0.009 (2)	0.021 (3)	−0.010 (2)
C37	0.044 (3)	0.074 (4)	0.051 (4)	−0.016 (3)	0.015 (3)	0.005 (3)
C38	0.046 (3)	0.060 (4)	0.051 (4)	0.006 (3)	0.012 (3)	0.007 (3)
C39	0.038 (3)	0.021 (2)	0.040 (3)	0.003 (2)	0.010 (3)	0.000 (2)
C40	0.023 (3)	0.031 (3)	0.045 (4)	0.000 (2)	0.013 (3)	0.007 (2)
C41	0.032 (3)	0.025 (2)	0.042 (3)	0.002 (2)	0.022 (3)	0.005 (2)
C42	0.034 (3)	0.027 (2)	0.037 (3)	0.001 (2)	0.018 (2)	0.003 (2)
C43	0.028 (3)	0.031 (3)	0.049 (4)	−0.002 (2)	0.019 (3)	−0.005 (2)
C44	0.049 (4)	0.022 (2)	0.047 (4)	0.000 (2)	0.030 (3)	0.003 (2)
C45	0.063 (4)	0.058 (4)	0.039 (3)	0.003 (3)	0.013 (3)	−0.003 (3)
C46	0.031 (3)	0.066 (4)	0.050 (4)	0.007 (3)	0.010 (3)	0.009 (3)
C47	0.040 (3)	0.041 (3)	0.022 (3)	−0.005 (2)	0.002 (2)	−0.007 (2)
C48	0.030 (3)	0.048 (3)	0.035 (3)	−0.013 (2)	0.010 (3)	−0.003 (2)
C49	0.049 (4)	0.035 (3)	0.034 (3)	−0.012 (2)	0.015 (3)	0.004 (2)
C50	0.038 (3)	0.040 (3)	0.015 (3)	−0.009 (2)	0.006 (2)	0.000 (2)
C51	0.035 (3)	0.040 (3)	0.022 (3)	−0.013 (2)	0.006 (2)	−0.002 (2)
C52	0.041 (3)	0.034 (3)	0.024 (3)	−0.011 (2)	0.006 (2)	−0.005 (2)
C53	0.041 (4)	0.059 (4)	0.041 (3)	0.003 (3)	0.006 (3)	−0.010 (3)
C54	0.051 (4)	0.037 (3)	0.031 (3)	−0.008 (3)	0.013 (3)	0.004 (2)
C55	0.029 (3)	0.035 (3)	0.019 (3)	−0.006 (2)	0.006 (2)	−0.0032 (19)
C56	0.032 (3)	0.035 (3)	0.019 (3)	−0.007 (2)	0.007 (2)	−0.005 (2)
C57	0.040 (3)	0.028 (2)	0.022 (3)	−0.004 (2)	0.007 (2)	−0.0059 (19)
C58	0.029 (3)	0.038 (3)	0.030 (3)	−0.001 (2)	0.008 (2)	−0.010 (2)
C59	0.038 (3)	0.041 (3)	0.034 (3)	−0.008 (2)	0.015 (3)	−0.005 (2)
C60	0.034 (3)	0.036 (3)	0.029 (3)	−0.006 (2)	0.010 (2)	0.003 (2)
C61	0.029 (3)	0.036 (3)	0.031 (3)	−0.001 (2)	0.008 (2)	0.000 (2)
C62	0.042 (4)	0.049 (3)	0.053 (4)	−0.003 (3)	0.020 (3)	−0.013 (3)
F1	0.0287 (17)	0.0303 (15)	0.049 (2)	−0.0016 (12)	0.0168 (15)	0.0003 (13)
F2	0.0270 (18)	0.0545 (19)	0.043 (2)	0.0157 (13)	0.0155 (15)	0.0033 (15)
F3	0.057 (3)	0.0339 (18)	0.042 (2)	0.0280 (14)	0.0208 (19)	0.0054 (13)
F4	0.068 (3)	0.0177 (14)	0.059 (2)	0.0018 (16)	0.0237 (19)	−0.0010 (15)
F5	0.0349 (19)	0.0228 (14)	0.058 (2)	−0.0049 (12)	0.0222 (16)	−0.0023 (13)
F6	0.0291 (16)	0.085 (2)	0.0216 (14)	−0.0025 (15)	0.0076 (12)	−0.0059 (15)
F7	0.0211 (15)	0.091 (2)	0.0463 (19)	−0.0014 (16)	0.0135 (14)	−0.0028 (18)
F8	0.039 (2)	0.0525 (18)	0.041 (2)	0.0020 (14)	0.0307 (16)	0.0015 (14)
F9	0.0469 (19)	0.091 (2)	0.0217 (15)	−0.0092 (17)	0.0177 (14)	−0.0082 (16)
F10	0.0276 (16)	0.096 (2)	0.0263 (16)	−0.0127 (16)	0.0096 (12)	−0.0107 (16)
F11	0.0240 (16)	0.0322 (15)	0.049 (2)	−0.0036 (12)	0.0148 (14)	−0.0014 (14)
F12	0.0205 (16)	0.065 (2)	0.0341 (18)	0.0129 (14)	0.0110 (14)	−0.0022 (15)
F13	0.058 (3)	0.042 (2)	0.041 (2)	0.0328 (15)	0.0189 (19)	0.0037 (13)
F14	0.057 (2)	0.0180 (14)	0.068 (3)	0.0067 (14)	0.025 (2)	0.0039 (15)
F15	0.0298 (17)	0.0219 (13)	0.056 (2)	−0.0019 (12)	0.0207 (15)	−0.0001 (13)
F16	0.0299 (15)	0.072 (2)	0.0256 (15)	0.0038 (15)	0.0079 (12)	0.0014 (15)
F17	0.0236 (16)	0.071 (2)	0.054 (2)	0.0014 (14)	0.0169 (14)	−0.0087 (17)
F18	0.048 (2)	0.0521 (19)	0.053 (2)	0.0003 (14)	0.0421 (19)	0.0033 (15)
F19	0.061 (2)	0.101 (3)	0.0254 (16)	0.0199 (19)	0.0259 (15)	0.0176 (17)
F20	0.0312 (17)	0.089 (2)	0.0211 (15)	0.0173 (16)	0.0087 (12)	0.0095 (15)

Geometric parameters (Å, º)

Cu1—O3	1.913 (3)	C33—C34	1.387 (8)
Cu1—O2	1.917 (3)	C33—H33	0.9500
Cu1—O1	1.921 (3)	C34—C35	1.406 (8)
Cu1—O4	1.921 (3)	C34—C38	1.526 (8)
O1—C7	1.271 (5)	C35—C36	1.379 (8)
O2—C9	1.263 (5)	C35—H35	0.9500
O3—C22	1.263 (5)	C36—H36	0.9500
O4—C24	1.270 (5)	C37—H37A	0.9800
C1—F1	1.336 (5)	C37—H37B	0.9800
C1—C2	1.375 (7)	C37—H37C	0.9800
C1—C6	1.391 (7)	C38—H38A	0.9800
C2—F2	1.336 (6)	C38—H38B	0.9800
C2—C3	1.371 (7)	C38—H38C	0.9800
C3—F3	1.333 (5)	C39—C40	1.374 (8)
C3—C4	1.383 (8)	C39—C44	1.399 (8)
C4—F4	1.337 (6)	C39—C45	1.502 (8)
C4—C5	1.372 (7)	C40—C41	1.375 (8)
C5—F5	1.349 (6)	C40—H40	0.9500
C5—C6	1.383 (6)	C41—C42	1.370 (7)
C6—C7	1.505 (6)	C41—H41	0.9500
C7—C8	1.390 (6)	C42—C43	1.396 (8)
C8—C9	1.399 (6)	C42—C46	1.519 (7)
C8—H8	0.9500	C43—C44	1.395 (8)
C9—C10	1.508 (7)	C43—H43	0.9500
C10—C15	1.375 (7)	C44—H44	0.9500
C10—C11	1.390 (7)	C45—H45A	0.9800
C11—F6	1.332 (6)	C45—H45B	0.9800
C11—C12	1.375 (7)	C45—H45C	0.9800
C12—F7	1.336 (6)	C46—H46A	0.9800
C12—C13	1.358 (8)	C46—H46B	0.9800
C13—F8	1.352 (6)	C46—H46C	0.9800
C13—C14	1.375 (8)	C47—C48	1.382 (7)
C14—F9	1.346 (6)	C47—C52	1.399 (8)
C14—C15	1.377 (7)	C47—C53	1.491 (8)
C15—F10	1.340 (6)	C48—C49	1.375 (8)
C16—F11	1.336 (5)	C48—H48	0.9500
C16—C17	1.379 (7)	C49—C50	1.394 (8)
C16—C21	1.388 (7)	C49—H49	0.9500
C17—F12	1.344 (6)	C50—C51	1.384 (7)
C17—C18	1.362 (7)	C50—C54	1.507 (8)
C18—F13	1.343 (5)	C51—C52	1.381 (8)
C18—C19	1.374 (8)	C51—H51	0.9500
C19—F14	1.340 (5)	C52—H52	0.9500
C19—C20	1.388 (7)	C53—H53A	0.9800
C20—F15	1.336 (5)	C53—H53B	0.9800
C20—C21	1.388 (6)	C53—H53C	0.9800
C21—C22	1.496 (6)	C54—H54A	0.9800
C22—C23	1.400 (6)	C54—H54B	0.9800
C23—C24	1.386 (6)	C54—H54C	0.9800
C23—H23	0.9500	C55—C56	1.390 (7)
C24—C25	1.505 (7)	C55—C60	1.391 (7)
C25—C30	1.376 (7)	C55—C61	1.504 (7)
C25—C26	1.378 (7)	C56—C57	1.396 (7)
C26—F16	1.348 (5)	C56—H56	0.9500
C26—C27	1.379 (7)	C57—C58	1.390 (8)
C27—F17	1.340 (6)	C57—H57	0.9500
C27—C28	1.375 (8)	C58—C59	1.379 (7)
C28—F18	1.337 (6)	C58—C62	1.527 (8)
C28—C29	1.365 (8)	C59—C60	1.391 (8)
C29—F19	1.340 (6)	C59—H59	0.9500
C29—C30	1.377 (7)	C60—H60	0.9500
C30—F20	1.346 (6)	C61—H61A	0.9800
C31—C32	1.376 (8)	C61—H61B	0.9800
C31—C36	1.410 (7)	C61—H61C	0.9800
C31—C37	1.490 (8)	C62—H62A	0.9800
C32—C33	1.368 (8)	C62—H62B	0.9800
C32—H32	0.9500	C62—H62C	0.9800
O3—Cu1—O2	86.38 (14)	C33—C34—C38	121.7 (5)
O3—Cu1—O1	179.80 (19)	C35—C34—C38	121.6 (5)
O2—Cu1—O1	93.42 (13)	C36—C35—C34	121.7 (6)
O3—Cu1—O4	93.40 (14)	C36—C35—H35	119.2
O2—Cu1—O4	179.57 (18)	C34—C35—H35	119.2
O1—Cu1—O4	86.80 (13)	C35—C36—C31	120.3 (6)
C7—O1—Cu1	125.0 (3)	C35—C36—H36	119.8
C9—O2—Cu1	125.0 (3)	C31—C36—H36	119.8
C22—O3—Cu1	126.0 (3)	C31—C37—H37A	109.5
C24—O4—Cu1	124.9 (3)	C31—C37—H37B	109.5
F1—C1—C2	117.5 (5)	H37A—C37—H37B	109.5
F1—C1—C6	119.6 (4)	C31—C37—H37C	109.5
C2—C1—C6	122.7 (4)	H37A—C37—H37C	109.5
F2—C2—C3	119.9 (4)	H37B—C37—H37C	109.5
F2—C2—C1	120.4 (5)	C34—C38—H38A	109.5
C3—C2—C1	119.6 (5)	C34—C38—H38B	109.5
F3—C3—C2	120.5 (5)	H38A—C38—H38B	109.5
F3—C3—C4	119.9 (5)	C34—C38—H38C	109.5
C2—C3—C4	119.6 (4)	H38A—C38—H38C	109.5
F4—C4—C5	121.4 (5)	H38B—C38—H38C	109.5
F4—C4—C3	119.2 (4)	C40—C39—C44	117.7 (6)
C5—C4—C3	119.4 (5)	C40—C39—C45	120.7 (5)
F5—C5—C4	117.0 (4)	C44—C39—C45	121.7 (6)
F5—C5—C6	120.0 (4)	C39—C40—C41	121.8 (5)
C4—C5—C6	123.1 (5)	C39—C40—H40	119.1
C5—C6—C1	115.6 (4)	C41—C40—H40	119.1
C5—C6—C7	123.1 (4)	C42—C41—C40	121.8 (5)
C1—C6—C7	121.2 (4)	C42—C41—H41	119.1
O1—C7—C8	126.8 (4)	C40—C41—H41	119.1
O1—C7—C6	114.3 (4)	C41—C42—C43	117.3 (5)
C8—C7—C6	118.8 (4)	C41—C42—C46	121.6 (5)
C7—C8—C9	122.0 (4)	C43—C42—C46	121.2 (5)
C7—C8—H8	119.0	C44—C43—C42	121.4 (5)
C9—C8—H8	119.0	C44—C43—H43	119.3
O2—C9—C8	127.0 (5)	C42—C43—H43	119.3
O2—C9—C10	115.1 (4)	C43—C44—C39	120.0 (5)
C8—C9—C10	117.9 (4)	C43—C44—H44	120.0
C15—C10—C11	117.3 (5)	C39—C44—H44	120.0
C15—C10—C9	121.6 (5)	C39—C45—H45A	109.5
C11—C10—C9	121.0 (5)	C39—C45—H45B	109.5
F6—C11—C12	118.9 (5)	H45A—C45—H45B	109.5
F6—C11—C10	119.6 (4)	C39—C45—H45C	109.5
C12—C11—C10	121.5 (5)	H45A—C45—H45C	109.5
F7—C12—C13	120.3 (5)	H45B—C45—H45C	109.5
F7—C12—C11	120.1 (5)	C42—C46—H46A	109.5
C13—C12—C11	119.6 (5)	C42—C46—H46B	109.5
F8—C13—C12	120.6 (5)	H46A—C46—H46B	109.5
F8—C13—C14	118.8 (5)	C42—C46—H46C	109.5
C12—C13—C14	120.6 (5)	H46A—C46—H46C	109.5
F9—C14—C13	119.9 (5)	H46B—C46—H46C	109.5
F9—C14—C15	120.9 (5)	C48—C47—C52	116.9 (5)
C13—C14—C15	119.3 (5)	C48—C47—C53	121.8 (6)
F10—C15—C10	120.1 (4)	C52—C47—C53	121.3 (5)
F10—C15—C14	118.1 (5)	C49—C48—C47	122.2 (5)
C10—C15—C14	121.7 (5)	C49—C48—H48	118.9
F11—C16—C17	117.7 (5)	C47—C48—H48	118.9
F11—C16—C21	120.3 (4)	C48—C49—C50	121.1 (5)
C17—C16—C21	122.0 (5)	C48—C49—H49	119.5
F12—C17—C18	120.1 (4)	C50—C49—H49	119.5
F12—C17—C16	119.9 (5)	C51—C50—C49	117.0 (5)
C18—C17—C16	119.9 (5)	C51—C50—C54	121.2 (5)
F13—C18—C17	120.2 (5)	C49—C50—C54	121.8 (5)
F13—C18—C19	119.5 (5)	C52—C51—C50	121.9 (5)
C17—C18—C19	120.3 (4)	C52—C51—H51	119.0
F14—C19—C18	120.6 (4)	C50—C51—H51	119.0
F14—C19—C20	120.0 (5)	C51—C52—C47	120.9 (5)
C18—C19—C20	119.5 (5)	C51—C52—H52	119.6
F15—C20—C19	117.5 (4)	C47—C52—H52	119.6
F15—C20—C21	120.9 (4)	C47—C53—H53A	109.5
C19—C20—C21	121.7 (5)	C47—C53—H53B	109.5
C16—C21—C20	116.7 (4)	H53A—C53—H53B	109.5
C16—C21—C22	120.4 (4)	C47—C53—H53C	109.5
C20—C21—C22	122.8 (4)	H53A—C53—H53C	109.5
O3—C22—C23	125.7 (4)	H53B—C53—H53C	109.5
O3—C22—C21	115.3 (4)	C50—C54—H54A	109.5
C23—C22—C21	119.0 (4)	C50—C54—H54B	109.5
C24—C23—C22	123.1 (4)	H54A—C54—H54B	109.5
C24—C23—H23	118.5	C50—C54—H54C	109.5
C22—C23—H23	118.5	H54A—C54—H54C	109.5
O4—C24—C23	126.7 (5)	H54B—C54—H54C	109.5
O4—C24—C25	114.6 (4)	C56—C55—C60	118.2 (5)
C23—C24—C25	118.7 (4)	C56—C55—C61	120.4 (5)
C30—C25—C26	116.3 (5)	C60—C55—C61	121.4 (5)
C30—C25—C24	122.0 (5)	C55—C56—C57	120.7 (5)
C26—C25—C24	121.6 (5)	C55—C56—H56	119.6
F16—C26—C25	120.1 (4)	C57—C56—H56	119.6
F16—C26—C27	117.4 (4)	C58—C57—C56	120.9 (5)
C25—C26—C27	122.5 (5)	C58—C57—H57	119.6
F17—C27—C28	120.0 (5)	C56—C57—H57	119.6
F17—C27—C26	120.6 (5)	C59—C58—C57	118.0 (5)
C28—C27—C26	119.4 (5)	C59—C58—C62	121.5 (5)
F18—C28—C29	120.4 (5)	C57—C58—C62	120.4 (5)
F18—C28—C27	120.0 (5)	C58—C59—C60	121.6 (5)
C29—C28—C27	119.6 (5)	C58—C59—H59	119.2
F19—C29—C28	119.7 (5)	C60—C59—H59	119.2
F19—C29—C30	120.4 (5)	C59—C60—C55	120.5 (5)
C28—C29—C30	119.9 (5)	C59—C60—H60	119.7
F20—C30—C25	119.8 (5)	C55—C60—H60	119.7
F20—C30—C29	117.9 (5)	C55—C61—H61A	109.5
C25—C30—C29	122.3 (5)	C55—C61—H61B	109.5
C32—C31—C36	117.4 (6)	H61A—C61—H61B	109.5
C32—C31—C37	122.0 (5)	C55—C61—H61C	109.5
C36—C31—C37	120.5 (5)	H61A—C61—H61C	109.5
C33—C32—C31	122.0 (5)	H61B—C61—H61C	109.5
C33—C32—H32	119.0	C58—C62—H62A	109.5
C31—C32—H32	119.0	C58—C62—H62B	109.5
C32—C33—C34	121.8 (6)	H62A—C62—H62B	109.5
C32—C33—H33	119.1	C58—C62—H62C	109.5
C34—C33—H33	119.1	H62A—C62—H62C	109.5
C33—C34—C35	116.7 (6)	H62B—C62—H62C	109.5
F1—C1—C2—F2	1.6 (7)	F15—C20—C21—C16	179.3 (4)
C6—C1—C2—F2	176.8 (5)	C19—C20—C21—C16	−1.8 (7)
F1—C1—C2—C3	−178.2 (5)	F15—C20—C21—C22	−2.6 (7)
C6—C1—C2—C3	−3.0 (8)	C19—C20—C21—C22	176.2 (5)
F2—C2—C3—F3	−0.5 (7)	Cu1—O3—C22—C23	−0.1 (7)
C1—C2—C3—F3	179.3 (5)	Cu1—O3—C22—C21	179.1 (3)
F2—C2—C3—C4	−176.9 (5)	C16—C21—C22—O3	43.8 (6)
C1—C2—C3—C4	2.9 (8)	C20—C21—C22—O3	−134.2 (5)
F3—C3—C4—F4	0.7 (7)	C16—C21—C22—C23	−136.9 (5)
C2—C3—C4—F4	177.1 (5)	C20—C21—C22—C23	45.1 (7)
F3—C3—C4—C5	−177.7 (5)	O3—C22—C23—C24	3.2 (8)
C2—C3—C4—C5	−1.3 (8)	C21—C22—C23—C24	−176.1 (4)
F4—C4—C5—F5	1.7 (7)	Cu1—O4—C24—C23	−4.9 (7)
C3—C4—C5—F5	−179.9 (5)	Cu1—O4—C24—C25	177.3 (3)
F4—C4—C5—C6	−178.7 (5)	C22—C23—C24—O4	−0.4 (8)
C3—C4—C5—C6	−0.2 (8)	C22—C23—C24—C25	177.4 (4)
F5—C5—C6—C1	179.8 (4)	O4—C24—C25—C30	−128.2 (5)
C4—C5—C6—C1	0.2 (7)	C23—C24—C25—C30	53.7 (6)
F5—C5—C6—C7	2.4 (7)	O4—C24—C25—C26	50.7 (6)
C4—C5—C6—C7	−177.2 (5)	C23—C24—C25—C26	−127.3 (5)
F1—C1—C6—C5	176.6 (4)	C30—C25—C26—F16	−179.3 (4)
C2—C1—C6—C5	1.5 (7)	C24—C25—C26—F16	1.7 (6)
F1—C1—C6—C7	−6.0 (7)	C30—C25—C26—C27	0.4 (6)
C2—C1—C6—C7	178.9 (5)	C24—C25—C26—C27	−178.6 (4)
Cu1—O1—C7—C8	0.8 (7)	F16—C26—C27—F17	0.7 (6)
Cu1—O1—C7—C6	−179.3 (3)	C25—C26—C27—F17	−179.0 (4)
C5—C6—C7—O1	134.0 (5)	F16—C26—C27—C28	−179.4 (4)
C1—C6—C7—O1	−43.3 (6)	C25—C26—C27—C28	0.9 (7)
C5—C6—C7—C8	−46.1 (7)	F17—C27—C28—F18	−1.2 (7)
C1—C6—C7—C8	136.6 (5)	C26—C27—C28—F18	178.8 (4)
O1—C7—C8—C9	−6.4 (8)	F17—C27—C28—C29	178.6 (4)
C6—C7—C8—C9	173.7 (4)	C26—C27—C28—C29	−1.4 (7)
Cu1—O2—C9—C8	5.0 (7)	F18—C28—C29—F19	0.0 (7)
Cu1—O2—C9—C10	−174.2 (3)	C27—C28—C29—F19	−179.8 (4)
C7—C8—C9—O2	3.2 (8)	F18—C28—C29—C30	−179.7 (4)
C7—C8—C9—C10	−177.7 (4)	C27—C28—C29—C30	0.5 (7)
O2—C9—C10—C15	108.7 (5)	C26—C25—C30—F20	−179.6 (4)
C8—C9—C10—C15	−70.5 (6)	C24—C25—C30—F20	−0.6 (6)
O2—C9—C10—C11	−68.1 (5)	C26—C25—C30—C29	−1.3 (7)
C8—C9—C10—C11	112.7 (5)	C24—C25—C30—C29	177.8 (4)
C15—C10—C11—F6	179.3 (4)	F19—C29—C30—F20	−0.4 (7)
C9—C10—C11—F6	−3.8 (6)	C28—C29—C30—F20	179.3 (4)
C15—C10—C11—C12	0.5 (7)	F19—C29—C30—C25	−178.9 (4)
C9—C10—C11—C12	177.5 (4)	C28—C29—C30—C25	0.8 (8)
F6—C11—C12—F7	1.2 (7)	C36—C31—C32—C33	1.3 (7)
C10—C11—C12—F7	179.9 (4)	C37—C31—C32—C33	179.9 (5)
F6—C11—C12—C13	179.6 (4)	C31—C32—C33—C34	−0.6 (8)
C10—C11—C12—C13	−1.7 (7)	C32—C33—C34—C35	−0.1 (7)
F7—C12—C13—F8	−0.4 (7)	C32—C33—C34—C38	−179.1 (5)
C11—C12—C13—F8	−178.8 (4)	C33—C34—C35—C36	0.0 (7)
F7—C12—C13—C14	179.7 (5)	C38—C34—C35—C36	179.0 (5)
C11—C12—C13—C14	1.4 (7)	C34—C35—C36—C31	0.8 (8)
F8—C13—C14—F9	0.7 (7)	C32—C31—C36—C35	−1.4 (7)
C12—C13—C14—F9	−179.5 (4)	C37—C31—C36—C35	180.0 (5)
F8—C13—C14—C15	−179.7 (4)	C44—C39—C40—C41	0.1 (7)
C12—C13—C14—C15	0.1 (7)	C45—C39—C40—C41	179.0 (5)
C11—C10—C15—F10	178.5 (4)	C39—C40—C41—C42	0.7 (8)
C9—C10—C15—F10	1.6 (6)	C40—C41—C42—C43	−0.3 (7)
C11—C10—C15—C14	1.0 (7)	C40—C41—C42—C46	179.5 (5)
C9—C10—C15—C14	−175.9 (4)	C41—C42—C43—C44	−0.8 (7)
F9—C14—C15—F10	0.7 (7)	C46—C42—C43—C44	179.4 (5)
C13—C14—C15—F10	−178.9 (4)	C42—C43—C44—C39	1.6 (7)
F9—C14—C15—C10	178.3 (4)	C40—C39—C44—C43	−1.2 (7)
C13—C14—C15—C10	−1.3 (7)	C45—C39—C44—C43	179.9 (5)
F11—C16—C17—F12	1.6 (7)	C52—C47—C48—C49	−0.2 (8)
C21—C16—C17—F12	−176.3 (5)	C53—C47—C48—C49	179.1 (5)
F11—C16—C17—C18	177.5 (5)	C47—C48—C49—C50	−0.6 (9)
C21—C16—C17—C18	−0.4 (7)	C48—C49—C50—C51	0.7 (8)
F12—C17—C18—F13	−2.6 (7)	C48—C49—C50—C54	−177.0 (5)
C16—C17—C18—F13	−178.5 (5)	C49—C50—C51—C52	−0.2 (8)
F12—C17—C18—C19	175.5 (5)	C54—C50—C51—C52	177.6 (5)
C16—C17—C18—C19	−0.3 (7)	C50—C51—C52—C47	−0.6 (8)
F13—C18—C19—F14	−0.8 (8)	C48—C47—C52—C51	0.7 (8)
C17—C18—C19—F14	−178.9 (5)	C53—C47—C52—C51	−178.5 (5)
F13—C18—C19—C20	178.1 (4)	C60—C55—C56—C57	0.7 (7)
C17—C18—C19—C20	0.0 (8)	C61—C55—C56—C57	−178.8 (5)
F14—C19—C20—F15	−1.0 (7)	C55—C56—C57—C58	−0.4 (8)
C18—C19—C20—F15	−180.0 (5)	C56—C57—C58—C59	0.5 (8)
F14—C19—C20—C21	−179.9 (5)	C56—C57—C58—C62	179.6 (5)
C18—C19—C20—C21	1.1 (8)	C57—C58—C59—C60	−1.0 (8)
F11—C16—C21—C20	−176.4 (4)	C62—C58—C59—C60	179.9 (5)
C17—C16—C21—C20	1.5 (7)	C58—C59—C60—C55	1.3 (9)
F11—C16—C21—C22	5.5 (7)	C56—C55—C60—C59	−1.1 (8)
C17—C16—C21—C22	−176.6 (4)	C61—C55—C60—C59	178.4 (5)