(Penta-fluoro-propionato-κO)tetra-kis-(trimethyl-phosphine oxide-κO)copper(II) penta-fluoro-propionate.

The title compound, [Cu(C(3)F(5)O(2))(C(3)H(9)OP)(4)](C(3)F(5)O(2)), comprises a cationic Cu(II) complex and a disordered penta-fluoro-propionate counter-ion. The metal atom has a distorted square-pyramidal coordination environment formed by four O atoms originating from trimethyl-phosphine oxide mol-ecules and the remaining one belonging to the monodentate penta-fluoro-propionate anion, which is situated in the basal plane of the pyramid. The mol-ecules are held together in the crystal by a net of weak C-H⋯O and C-H⋯F hydrogen bonds. The counter anion is disordered over two sets of sites in a 0.629 (5):0.371 (5) ratio.

Related literature

For our previous studies on metal complexes suitable for chemical vapour deposition (CVD), see: Szymańska et al. (2007 ▶, 2009 ▶); Piszczek et al. (2008 ▶). For crystal structures of metal complexes with trimethyl­phosphine oxide ligands involving metal ions from the first transition series, see: Hill et al. (2003 ▶) for Sc(III); Johnson & Bergman (2001 ▶) for Ti(III); Veige et al. (2003 ▶) for V(III); Cotton et al. (1991 ▶) for Fe(II); Edelmann & Behrens (1986 ▶) for Co(II); Klein et al. (1999 ▶) for Ni(II); Hlavinka & Hagadorn (2005 ▶) for Zn(II). For crystallographic data on CuII complexes with a penta­fluoro­propionate ligand, see: Jiang et al. (1998 ▶); Zhang et al. (1999 ▶).

Experimental

Crystal data

[Cu(C3F5O2)(C3H9OP)4](C3F5O2)

M = 757.89

Triclinic,

a = 9.5955 (8) Å

b = 12.2627 (11) Å

c = 14.1848 (12) Å

α = 82.720 (2)°

β = 80.501 (1)°

γ = 82.899 (2)°

V = 1623.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.96 mm−1

T = 100 K

0.48 × 0.17 × 0.03 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.655, T max = 0.972

10254 measured reflections

7148 independent reflections

6207 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.07

7148 reflections

416 parameters

33 restraints

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031114/hp2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031114/hp2011Isup2.hkl

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

[Cu(C3F5O2)(C3H9OP)4](C3F5O2)	Z = 2
Mr = 757.89	F(000) = 774
Triclinic, P1	Dx = 1.550 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5955 (8) Å	Cell parameters from 5155 reflections
b = 12.2627 (11) Å	θ = 2.2–28.1°
c = 14.1848 (12) Å	µ = 0.96 mm−1
α = 82.720 (2)°	T = 100 K
β = 80.501 (1)°	Plate, colorless
γ = 82.899 (2)°	0.48 × 0.17 × 0.03 mm
V = 1623.9 (2) Å3

Bruker APEX CCD area-detector diffractometer	7148 independent reflections
Radiation source: fine-focus sealed tube	6207 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→12
Tmin = 0.655, Tmax = 0.972	k = −12→15
10254 measured reflections	l = −12→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0677P)2 + 1.8569P] where P = (Fo2 + 2Fc2)/3
7148 reflections	(Δ/σ)max = 0.004
416 parameters	Δρmax = 1.33 e Å−3
33 restraints	Δρmin = −0.64 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)
Cu1	0.08108 (3)	0.78725 (2)	0.19051 (2)	0.01610 (10)
P1	0.24449 (7)	0.85300 (5)	−0.01852 (5)	0.01593 (14)
F1	−0.1350 (2)	0.6864 (2)	−0.05341 (14)	0.0504 (6)
O1	0.18617 (19)	0.87540 (15)	0.08413 (13)	0.0192 (4)
C1	0.3916 (3)	0.9301 (2)	−0.0631 (2)	0.0219 (5)
H1B	0.3621	1.0088	−0.0583	0.033*
H1C	0.4253	0.9186	−0.1305	0.033*
H1A	0.4683	0.9053	−0.0251	0.033*
P2	0.25316 (7)	0.53881 (6)	0.24912 (5)	0.02095 (16)
F2	−0.3344 (2)	0.76050 (17)	0.0154 (2)	0.0551 (7)
O2	0.2545 (2)	0.65462 (16)	0.20071 (14)	0.0241 (4)
C2	0.1173 (3)	0.8928 (2)	−0.09896 (19)	0.0216 (5)
H2A	0.0808	0.9706	−0.0950	0.032*
H2C	0.0386	0.8467	−0.0810	0.032*
H2B	0.1628	0.8829	−0.1649	0.032*
P3	0.23148 (7)	0.95789 (6)	0.28343 (5)	0.02113 (16)
F3	−0.3038 (4)	0.5932 (3)	0.17037 (17)	0.0865 (11)
O3	0.1153 (2)	0.88590 (17)	0.28130 (14)	0.0239 (4)
C3	0.3067 (3)	0.7111 (2)	−0.0298 (2)	0.0241 (6)
H3B	0.2287	0.6654	−0.0061	0.036*
H3C	0.3841	0.6884	0.0081	0.036*
H3A	0.3416	0.7017	−0.0975	0.036*
P4	−0.15738 (7)	0.75219 (6)	0.37572 (5)	0.02040 (16)
F4	−0.3406 (2)	0.54896 (16)	0.03595 (14)	0.0372 (4)
O4	−0.0456 (2)	0.71361 (15)	0.29524 (14)	0.0219 (4)
C4	0.4003 (3)	0.4476 (3)	0.2000 (2)	0.0311 (7)
H4C	0.4893	0.4776	0.2029	0.047*
H4A	0.3931	0.4405	0.1330	0.047*
H4B	0.3988	0.3747	0.2374	0.047*
F5	−0.1333 (3)	0.51630 (18)	0.0786 (2)	0.0734 (9)
O5	−0.00828 (19)	0.71780 (16)	0.09965 (14)	0.0210 (4)
C5	0.0986 (3)	0.4756 (3)	0.2401 (3)	0.0339 (7)
H5A	0.0134	0.5217	0.2659	0.051*
H5C	0.1016	0.4023	0.2769	0.051*
H5B	0.0959	0.4681	0.1724	0.051*
O6	−0.1970 (2)	0.84408 (17)	0.12865 (17)	0.0327 (5)
C6	0.2642 (4)	0.5320 (3)	0.3743 (2)	0.0373 (8)
H6A	0.1857	0.5805	0.4053	0.056*
H6B	0.3548	0.5561	0.3822	0.056*
H6C	0.2581	0.4558	0.4040	0.056*
C7	0.4043 (3)	0.8860 (3)	0.2605 (2)	0.0337 (7)
H7B	0.4105	0.8184	0.3052	0.050*
H7C	0.4752	0.9333	0.2695	0.050*
H7A	0.4224	0.8668	0.1943	0.050*
C8	0.2270 (3)	1.0803 (2)	0.2011 (2)	0.0285 (6)
H8B	0.1326	1.1216	0.2115	0.043*
H8A	0.2473	1.0603	0.1351	0.043*
H8C	0.2987	1.1262	0.2113	0.043*
C9	0.2105 (4)	1.0049 (3)	0.3994 (2)	0.0371 (8)
H9B	0.1156	1.0445	0.4138	0.056*
H9C	0.2826	1.0547	0.4003	0.056*
H9A	0.2218	0.9413	0.4479	0.056*
C10	−0.2257 (3)	0.8943 (3)	0.3576 (2)	0.0297 (6)
H10B	−0.1475	0.9407	0.3488	0.045*
H10C	−0.2944	0.9133	0.4138	0.045*
H10A	−0.2728	0.9067	0.3003	0.045*
C11	−0.0891 (3)	0.7320 (3)	0.4869 (2)	0.0317 (7)
H11A	−0.0069	0.7738	0.4812	0.048*
H11C	−0.0601	0.6532	0.5025	0.048*
H11B	−0.1629	0.7579	0.5379	0.048*
C12	−0.3045 (3)	0.6728 (3)	0.3907 (2)	0.0308 (7)
H12C	−0.2711	0.5940	0.4011	0.046*
H12A	−0.3503	0.6869	0.3329	0.046*
H12B	−0.3730	0.6938	0.4464	0.046*
C13	−0.1330 (3)	0.7628 (2)	0.0938 (2)	0.0221 (5)
C14	−0.2120 (3)	0.7015 (2)	0.0332 (2)	0.0238 (6)
C15	−0.2495 (4)	0.5889 (3)	0.0808 (2)	0.0369 (8)
O7A	0.4474 (9)	0.8498 (7)	0.7251 (5)	0.0477 (17)	0.629 (5)
O8A	0.5882 (6)	0.7691 (6)	0.6074 (5)	0.0323 (13)	0.629 (5)
C16A	0.4755 (7)	0.8008 (5)	0.6533 (5)	0.021 (2)	0.629 (5)
C17A	0.3420 (5)	0.7754 (4)	0.6121 (4)	0.0329 (9)	0.629 (5)
F6A	0.2231 (3)	0.8483 (2)	0.6315 (2)	0.0347 (8)	0.629 (5)
F7A	0.3679 (4)	0.7818 (4)	0.5132 (2)	0.0379 (9)	0.629 (5)
C18A	0.2969 (6)	0.6623 (4)	0.6453 (4)	0.0372 (10)	0.629 (5)
F8A	0.2645 (6)	0.6562 (5)	0.7412 (3)	0.0703 (16)	0.629 (5)
F9A	0.1885 (4)	0.6422 (4)	0.6027 (4)	0.0480 (12)	0.629 (5)
F10A	0.3998 (4)	0.5841 (3)	0.6197 (4)	0.0678 (16)	0.629 (5)
O7B	0.4232 (16)	0.8398 (13)	0.7137 (9)	0.052 (4)*	0.371 (5)
O8B	0.5843 (13)	0.8011 (11)	0.5898 (11)	0.071 (6)	0.371 (5)
C16B	0.4611 (9)	0.7981 (10)	0.6411 (8)	0.035 (6)*	0.371 (5)
C17B	0.3690 (6)	0.7217 (6)	0.6021 (4)	0.041 (2)*	0.371 (5)
F7B	0.3527 (9)	0.7481 (6)	0.5070 (4)	0.053 (3)*	0.371 (5)
F6B	0.4318 (6)	0.6141 (5)	0.6041 (5)	0.0376 (18)*	0.371 (5)
C18B	0.2217 (7)	0.7160 (6)	0.6562 (4)	0.046 (2)*	0.371 (5)
F8B	0.1567 (7)	0.8193 (4)	0.6525 (4)	0.0486 (17)*	0.371 (5)
F9B	0.1530 (7)	0.6463 (5)	0.6187 (4)	0.0319 (19)*	0.371 (5)
F10B	0.2208 (7)	0.6733 (6)	0.7469 (4)	0.0378 (18)*	0.371 (5)

	U11	U22	U33	U12	U13	U23
Cu1	0.01510 (16)	0.01617 (17)	0.01697 (17)	−0.00428 (12)	−0.00109 (11)	−0.00082 (12)
P1	0.0158 (3)	0.0150 (3)	0.0169 (3)	−0.0026 (2)	−0.0013 (2)	−0.0017 (2)
F1	0.0599 (14)	0.0691 (15)	0.0299 (10)	−0.0364 (12)	−0.0006 (9)	−0.0139 (10)
O1	0.0221 (9)	0.0172 (9)	0.0179 (9)	−0.0055 (7)	0.0004 (7)	−0.0017 (7)
C1	0.0181 (12)	0.0232 (13)	0.0236 (13)	−0.0048 (10)	−0.0008 (10)	−0.0002 (11)
P2	0.0181 (3)	0.0204 (3)	0.0220 (3)	0.0000 (3)	−0.0013 (2)	0.0024 (3)
F2	0.0481 (12)	0.0329 (11)	0.0966 (19)	0.0074 (9)	−0.0504 (13)	−0.0130 (11)
O2	0.0189 (9)	0.0232 (10)	0.0273 (10)	−0.0015 (8)	−0.0017 (8)	0.0053 (8)
C2	0.0213 (12)	0.0226 (13)	0.0213 (13)	−0.0041 (11)	−0.0044 (10)	−0.0008 (10)
P3	0.0221 (3)	0.0230 (4)	0.0199 (3)	−0.0078 (3)	−0.0044 (3)	−0.0015 (3)
F3	0.148 (3)	0.096 (2)	0.0307 (12)	−0.097 (2)	0.0034 (15)	−0.0048 (13)
O3	0.0256 (10)	0.0268 (10)	0.0204 (9)	−0.0106 (8)	0.0011 (8)	−0.0057 (8)
C3	0.0280 (14)	0.0170 (13)	0.0253 (14)	0.0011 (11)	0.0004 (11)	−0.0047 (10)
P4	0.0184 (3)	0.0224 (3)	0.0199 (3)	−0.0047 (3)	0.0007 (2)	−0.0025 (3)
F4	0.0430 (11)	0.0317 (10)	0.0440 (11)	−0.0200 (9)	−0.0147 (9)	−0.0053 (8)
O4	0.0207 (9)	0.0191 (9)	0.0235 (10)	−0.0036 (7)	0.0035 (7)	−0.0007 (7)
C4	0.0251 (14)	0.0303 (16)	0.0333 (16)	0.0069 (12)	−0.0011 (12)	0.0002 (13)
F5	0.0782 (18)	0.0247 (11)	0.134 (3)	−0.0036 (11)	−0.0712 (19)	−0.0002 (13)
O5	0.0186 (9)	0.0223 (10)	0.0232 (9)	−0.0063 (8)	−0.0033 (7)	−0.0020 (7)
C5	0.0250 (14)	0.0236 (15)	0.054 (2)	−0.0052 (12)	−0.0060 (14)	−0.0057 (14)
O6	0.0338 (11)	0.0214 (10)	0.0461 (13)	0.0031 (9)	−0.0157 (10)	−0.0088 (9)
C6	0.0400 (18)	0.045 (2)	0.0225 (15)	0.0030 (15)	−0.0028 (13)	0.0042 (13)
C7	0.0243 (14)	0.0352 (17)	0.0403 (18)	−0.0036 (13)	−0.0085 (13)	0.0055 (14)
C8	0.0299 (15)	0.0247 (15)	0.0313 (15)	−0.0071 (12)	−0.0065 (12)	0.0019 (12)
C9	0.050 (2)	0.0398 (18)	0.0264 (16)	−0.0216 (16)	−0.0047 (14)	−0.0079 (13)
C10	0.0279 (14)	0.0259 (15)	0.0324 (16)	0.0015 (12)	0.0018 (12)	−0.0050 (12)
C11	0.0315 (15)	0.0391 (18)	0.0253 (15)	−0.0034 (13)	−0.0051 (12)	−0.0055 (13)
C12	0.0236 (14)	0.0383 (17)	0.0307 (16)	−0.0140 (13)	0.0073 (11)	−0.0090 (13)
C13	0.0235 (13)	0.0191 (13)	0.0255 (14)	−0.0069 (11)	−0.0078 (10)	0.0009 (10)
C14	0.0246 (13)	0.0229 (14)	0.0261 (14)	−0.0043 (11)	−0.0096 (11)	−0.0013 (11)
C15	0.054 (2)	0.0300 (17)	0.0333 (17)	−0.0229 (16)	−0.0176 (15)	0.0027 (13)
O7A	0.059 (4)	0.062 (4)	0.029 (3)	−0.007 (3)	−0.003 (2)	−0.032 (2)
O8A	0.030 (2)	0.030 (4)	0.036 (3)	−0.0178 (18)	0.0070 (18)	−0.001 (2)
C16A	0.023 (3)	0.028 (4)	0.015 (3)	−0.0121 (19)	−0.003 (2)	−0.0083 (18)
C17A	0.038 (2)	0.027 (2)	0.0363 (18)	0.0004 (15)	−0.007 (2)	−0.0156 (17)
F6A	0.0312 (16)	0.0262 (15)	0.0452 (17)	0.0042 (12)	−0.0056 (13)	−0.0053 (13)
F7A	0.045 (2)	0.049 (2)	0.0245 (14)	−0.0102 (17)	−0.0080 (12)	−0.0096 (13)
C18A	0.036 (3)	0.0291 (18)	0.050 (2)	−0.0039 (18)	−0.016 (2)	−0.0034 (19)
F8A	0.058 (3)	0.108 (4)	0.0394 (17)	−0.005 (3)	−0.0178 (19)	0.025 (2)
F9A	0.0239 (19)	0.071 (3)	0.055 (2)	−0.023 (2)	−0.0081 (18)	−0.007 (2)
F10A	0.046 (2)	0.0196 (18)	0.151 (5)	0.0063 (18)	−0.048 (3)	−0.025 (2)
O8B	0.092 (9)	0.038 (8)	0.069 (9)	−0.038 (6)	0.058 (7)	−0.016 (6)

Cu1—O1	1.9535 (18)	O6—C13	1.220 (4)
Cu1—O4	1.9582 (18)	C6—H6A	0.9800
Cu1—O3	1.965 (2)	C6—H6B	0.9800
Cu1—O5	1.9863 (19)	C6—H6C	0.9800
Cu1—O2	2.1876 (19)	C7—H7B	0.9800
P1—O1	1.5176 (19)	C7—H7C	0.9800
P1—C1	1.780 (3)	C7—H7A	0.9800
P1—C3	1.786 (3)	C8—H8B	0.9800
P1—C2	1.789 (3)	C8—H8A	0.9800
F1—C14	1.346 (4)	C8—H8C	0.9800
C1—H1B	0.9800	C9—H9B	0.9800
C1—H1C	0.9800	C9—H9C	0.9800
C1—H1A	0.9800	C9—H9A	0.9800
P2—O2	1.498 (2)	C10—H10B	0.9800
P2—C5	1.786 (3)	C10—H10C	0.9800
P2—C6	1.787 (3)	C10—H10A	0.9800
P2—C4	1.792 (3)	C11—H11A	0.9800
F2—C14	1.345 (3)	C11—H11C	0.9800
C2—H2A	0.9800	C11—H11B	0.9800
C2—H2C	0.9800	C12—H12C	0.9800
C2—H2B	0.9800	C12—H12A	0.9800
P3—O3	1.511 (2)	C12—H12B	0.9800
P3—C7	1.779 (3)	C13—C14	1.549 (4)
P3—C8	1.782 (3)	C14—C15	1.516 (4)
P3—C9	1.784 (3)	O7A—C16A	1.222 (8)
F3—C15	1.296 (4)	O8A—C16A	1.213 (9)
C3—H3B	0.9800	C16A—C17A	1.572 (8)
C3—H3C	0.9800	C17A—F6A	1.373 (6)
C3—H3A	0.9800	C17A—F7A	1.378 (6)
P4—O4	1.5116 (19)	C17A—C18A	1.499 (6)
P4—C12	1.782 (3)	C18A—F10A	1.328 (6)
P4—C11	1.783 (3)	C18A—F9A	1.348 (5)
P4—C10	1.787 (3)	C18A—F8A	1.339 (7)
F4—C15	1.334 (4)	O7B—C16B	1.191 (14)
C4—H4C	0.9800	O8B—C16B	1.285 (14)
C4—H4A	0.9800	C16B—C17B	1.569 (8)
C4—H4B	0.9800	C17B—F6B	1.379 (6)
F5—C15	1.337 (5)	C17B—F7B	1.378 (6)
O5—C13	1.265 (3)	C17B—C18B	1.498 (6)
C5—H5A	0.9800	C18B—F10B	1.325 (7)
C5—H5C	0.9800	C18B—F9B	1.349 (5)
C5—H5B	0.9800	C18B—F8B	1.339 (7)
O1—Cu1—O4	172.44 (8)	P3—C7—H7A	109.5
O1—Cu1—O3	90.48 (8)	H7B—C7—H7A	109.5
O4—Cu1—O3	88.42 (8)	H7C—C7—H7A	109.5
O1—Cu1—O5	91.12 (8)	P3—C8—H8B	109.5
O4—Cu1—O5	87.71 (8)	P3—C8—H8A	109.5
O3—Cu1—O5	162.51 (8)	H8B—C8—H8A	109.5
O1—Cu1—O2	94.54 (7)	P3—C8—H8C	109.5
O4—Cu1—O2	92.99 (7)	H8B—C8—H8C	109.5
O3—Cu1—O2	102.55 (8)	H8A—C8—H8C	109.5
O5—Cu1—O2	94.69 (8)	P3—C9—H9B	109.5
O1—P1—C1	109.87 (12)	P3—C9—H9C	109.5
O1—P1—C3	113.30 (12)	H9B—C9—H9C	109.5
C1—P1—C3	106.69 (13)	P3—C9—H9A	109.5
O1—P1—C2	112.92 (12)	H9B—C9—H9A	109.5
C1—P1—C2	106.63 (13)	H9C—C9—H9A	109.5
C3—P1—C2	107.03 (14)	P4—C10—H10B	109.5
P1—O1—Cu1	131.81 (11)	P4—C10—H10C	109.5
P1—C1—H1B	109.5	H10B—C10—H10C	109.5
P1—C1—H1C	109.5	P4—C10—H10A	109.5
H1B—C1—H1C	109.5	H10B—C10—H10A	109.5
P1—C1—H1A	109.5	H10C—C10—H10A	109.5
H1B—C1—H1A	109.5	P4—C11—H11A	109.5
H1C—C1—H1A	109.5	P4—C11—H11C	109.5
O2—P2—C5	113.83 (14)	H11A—C11—H11C	109.5
O2—P2—C6	111.92 (15)	P4—C11—H11B	109.5
C5—P2—C6	106.86 (17)	H11A—C11—H11B	109.5
O2—P2—C4	112.71 (13)	H11C—C11—H11B	109.5
C5—P2—C4	105.21 (16)	P4—C12—H12C	109.5
C6—P2—C4	105.69 (16)	P4—C12—H12A	109.5
P2—O2—Cu1	130.30 (11)	H12C—C12—H12A	109.5
P1—C2—H2A	109.5	P4—C12—H12B	109.5
P1—C2—H2C	109.5	H12C—C12—H12B	109.5
H2A—C2—H2C	109.5	H12A—C12—H12B	109.5
P1—C2—H2B	109.5	O6—C13—O5	129.8 (3)
H2A—C2—H2B	109.5	O6—C13—C14	117.6 (2)
H2C—C2—H2B	109.5	O5—C13—C14	112.6 (2)
O3—P3—C7	112.50 (14)	F2—C14—F1	105.9 (3)
O3—P3—C8	114.19 (13)	F2—C14—C15	106.8 (3)
C7—P3—C8	107.45 (15)	F1—C14—C15	107.2 (3)
O3—P3—C9	109.04 (14)	F2—C14—C13	111.1 (2)
C7—P3—C9	108.03 (18)	F1—C14—C13	111.7 (2)
C8—P3—C9	105.23 (16)	C15—C14—C13	113.7 (2)
P3—O3—Cu1	133.98 (12)	F3—C15—F4	109.1 (3)
P1—C3—H3B	109.5	F3—C15—F5	107.2 (3)
P1—C3—H3C	109.5	F4—C15—F5	107.2 (3)
H3B—C3—H3C	109.5	F3—C15—C14	111.1 (3)
P1—C3—H3A	109.5	F4—C15—C14	111.5 (3)
H3B—C3—H3A	109.5	F5—C15—C14	110.6 (3)
H3C—C3—H3A	109.5	O8A—C16A—O7A	131.6 (7)
O4—P4—C12	109.79 (13)	O8A—C16A—C17A	114.0 (6)
O4—P4—C11	110.73 (13)	O7A—C16A—C17A	114.5 (6)
C12—P4—C11	107.01 (16)	F6A—C17A—F7A	104.2 (4)
O4—P4—C10	114.59 (13)	F6A—C17A—C18A	106.1 (4)
C12—P4—C10	107.08 (16)	F7A—C17A—C18A	105.5 (4)
C11—P4—C10	107.30 (16)	F6A—C17A—C16A	114.6 (4)
P4—O4—Cu1	134.85 (12)	F7A—C17A—C16A	111.0 (4)
P2—C4—H4C	109.5	C18A—C17A—C16A	114.4 (4)
P2—C4—H4A	109.5	F10A—C18A—F9A	103.9 (4)
H4C—C4—H4A	109.5	F10A—C18A—F8A	110.5 (5)
P2—C4—H4B	109.5	F9A—C18A—F8A	112.9 (5)
H4C—C4—H4B	109.5	F10A—C18A—C17A	111.3 (5)
H4A—C4—H4B	109.5	F9A—C18A—C17A	111.9 (4)
C13—O5—Cu1	111.38 (18)	F8A—C18A—C17A	106.5 (5)
P2—C5—H5A	109.5	O7B—C16B—O8B	125.4 (8)
P2—C5—H5C	109.5	O7B—C16B—C17B	123.0 (9)
H5A—C5—H5C	109.5	O8B—C16B—C17B	111.4 (9)
P2—C5—H5B	109.5	F6B—C17B—F7B	102.7 (4)
H5A—C5—H5B	109.5	F6B—C17B—C18B	106.1 (5)
H5C—C5—H5B	109.5	F7B—C17B—C18B	105.6 (5)
P2—C6—H6A	109.5	F6B—C17B—C16B	111.5 (5)
P2—C6—H6B	109.5	F7B—C17B—C16B	115.0 (5)
H6A—C6—H6B	109.5	C18B—C17B—C16B	114.9 (4)
P2—C6—H6C	109.5	F10B—C18B—F9B	103.9 (5)
H6A—C6—H6C	109.5	F10B—C18B—F8B	110.0 (5)
H6B—C6—H6C	109.5	F9B—C18B—F8B	112.8 (5)
P3—C7—H7B	109.5	F10B—C18B—C17B	112.6 (5)
P3—C7—H7C	109.5	F9B—C18B—C17B	110.3 (4)
H7B—C7—H7C	109.5	F8B—C18B—C17B	107.3 (5)
C1—P1—O1—Cu1	−154.13 (15)	F1—C14—C15—F3	169.7 (3)
C3—P1—O1—Cu1	−34.9 (2)	C13—C14—C15—F3	45.8 (4)
C2—P1—O1—Cu1	86.98 (17)	F2—C14—C15—F4	44.8 (4)
O3—Cu1—O1—P1	166.61 (16)	F1—C14—C15—F4	−68.4 (4)
O5—Cu1—O1—P1	−30.81 (16)	C13—C14—C15—F4	167.7 (3)
O2—Cu1—O1—P1	63.98 (16)	F2—C14—C15—F5	164.0 (3)
C5—P2—O2—Cu1	37.4 (2)	F1—C14—C15—F5	50.8 (3)
C6—P2—O2—Cu1	−83.9 (2)	C13—C14—C15—F5	−73.1 (3)
C4—P2—O2—Cu1	157.08 (16)	O8A—C16A—C17A—F6A	−151.9 (6)
O1—Cu1—O2—P2	−163.26 (16)	O7A—C16A—C17A—F6A	27.5 (8)
O4—Cu1—O2—P2	16.18 (17)	O8A—C16A—C17A—F7A	−34.2 (7)
O3—Cu1—O2—P2	105.23 (16)	O7A—C16A—C17A—F7A	145.2 (7)
O5—Cu1—O2—P2	−71.76 (17)	O8A—C16A—C17A—C18A	85.1 (7)
C7—P3—O3—Cu1	−49.3 (2)	O7A—C16A—C17A—C18A	−95.4 (7)
C8—P3—O3—Cu1	73.5 (2)	F6A—C17A—C18A—F10A	172.6 (4)
C9—P3—O3—Cu1	−169.11 (19)	F7A—C17A—C18A—F10A	62.4 (5)
O1—Cu1—O3—P3	−28.23 (18)	C16A—C17A—C18A—F10A	−60.0 (6)
O4—Cu1—O3—P3	159.25 (18)	F6A—C17A—C18A—F9A	56.9 (6)
O5—Cu1—O3—P3	−123.5 (2)	F7A—C17A—C18A—F9A	−53.3 (6)
O2—Cu1—O3—P3	66.53 (18)	C16A—C17A—C18A—F9A	−175.7 (5)
C12—P4—O4—Cu1	140.10 (18)	F6A—C17A—C18A—F8A	−66.8 (5)
C11—P4—O4—Cu1	−102.0 (2)	F7A—C17A—C18A—F8A	−177.1 (4)
C10—P4—O4—Cu1	19.6 (2)	C16A—C17A—C18A—F8A	60.5 (6)
O3—Cu1—O4—P4	41.48 (18)	O7B—C16B—C17B—F6B	−113.4 (14)
O5—Cu1—O4—P4	−121.46 (18)	O8B—C16B—C17B—F6B	61.0 (11)
O2—Cu1—O4—P4	143.97 (17)	O7B—C16B—C17B—F7B	130.3 (14)
O1—Cu1—O5—C13	−99.79 (18)	O8B—C16B—C17B—F7B	−55.4 (12)
O4—Cu1—O5—C13	72.74 (18)	O7B—C16B—C17B—C18B	7.4 (16)
O3—Cu1—O5—C13	−4.6 (4)	O8B—C16B—C17B—C18B	−178.3 (10)
O2—Cu1—O5—C13	165.56 (18)	F6B—C17B—C18B—F10B	60.9 (6)
Cu1—O5—C13—O6	6.3 (4)	F7B—C17B—C18B—F10B	169.4 (6)
Cu1—O5—C13—C14	−173.07 (17)	C16B—C17B—C18B—F10B	−62.8 (8)
O6—C13—C14—F2	10.4 (4)	F6B—C17B—C18B—F9B	−54.7 (6)
O5—C13—C14—F2	−170.1 (2)	F7B—C17B—C18B—F9B	53.8 (7)
O6—C13—C14—F1	128.4 (3)	C16B—C17B—C18B—F9B	−178.4 (6)
O5—C13—C14—F1	−52.1 (3)	F6B—C17B—C18B—F8B	−177.9 (5)
O6—C13—C14—C15	−110.1 (3)	F7B—C17B—C18B—F8B	−69.4 (6)
O5—C13—C14—C15	69.4 (3)	C16B—C17B—C18B—F8B	58.4 (7)
F2—C14—C15—F3	−77.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O5	0.98	2.57	3.265 (3)	128
C5—H5A···O4	0.98	2.42	3.204 (4)	136
C10—H10B···O3i	0.98	2.58	3.266 (4)	127
C1—H1A···F2ii	0.98	2.52	3.392 (3)	149
C1—H1B···O6iii	0.98	2.47	3.265 (3)	138
C4—H4A···F4iv	0.98	2.51	3.482 (3)	170
C4—H4C···F3ii	0.98	2.53	3.478 (5)	163
C9—H9A···F7A	0.98	2.44	3.322 (6)	150
C11—H11B···O8Av	0.98	2.42	3.289 (7)	147
C12—H12B···O8Av	0.98	2.52	3.388 (8)	147

Cu1—O1	1.9535 (18)
Cu1—O4	1.9582 (18)
Cu1—O3	1.965 (2)
Cu1—O5	1.9863 (19)
Cu1—O2	2.1876 (19)

O1—Cu1—O4	172.44 (8)
O1—Cu1—O3	90.48 (8)
O4—Cu1—O3	88.42 (8)
O1—Cu1—O5	91.12 (8)
O4—Cu1—O5	87.71 (8)
O3—Cu1—O5	162.51 (8)
O1—Cu1—O2	94.54 (7)
O4—Cu1—O2	92.99 (7)
O3—Cu1—O2	102.55 (8)
O5—Cu1—O2	94.69 (8)

Table 2

Geometry of selected hydrogen bonds (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O5	0.98	2.57	3.265 (3)	128
C5—H5A⋯O4	0.98	2.42	3.204 (4)	136
C10—H10B⋯O3	0.98	2.58	3.266 (4)	127
C1—H1A⋯F2i	0.98	2.52	3.392 (3)	149
C1—H1B⋯O6ii	0.98	2.47	3.265 (3)	138
C4—H4A⋯F4iii	0.98	2.51	3.482 (3)	170
C4—H4C⋯F3i	0.98	2.53	3.478 (5)	163
C9—H9A⋯F7A	0.98	2.44	3.322 (6)	150
C11—H11B⋯O8Aiv	0.98	2.42	3.289 (7)	147
C12—H12B⋯O8Aiv	0.98	2.52	3.388 (8)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .