catena-Poly[[bis­(α-thenoyltrifluoro­acetonato)copper(II)]-μ-1,4-di-4-pyrid­yl-2,3-diazabuta-1,3-diene]

In the one-dimensional title polymer, [Cu(C₈H₄F₃O₂S)₂(C₁₂H₁₀N₄)]_n or [Cu(L)₂(tta)₂] [tta is α-thenoyl­trifluoro­acetonato and L is 1,4-bis­(4-pyrid­yl)-2,3-diaza-1,3-butadiene], Cu²⁺ lies on a center of inversion. It is axially coordinated by two pyridyl N atoms from two different L ligands and equatorially coordinated by four O atoms from two chelating tta ligands. The ligand L propagates the one-dimensional chain structure by serving as a bridging ligand between two Cu octa­hedra via Cu—N coordinate bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C14

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.658     0.830
            Tmin(prime) and Tmax expected:      0.746     0.826
            RR(prime) =      0.877
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C11    -   C12    ...       1.39 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The synthesis of new coordination polymers has interested chemists and materials scientists because of the potential applications of these materials in a variety of areas, including catalysis, optical applications and gas sorption (Atto et al., 1999; Wang et al., 1995; Chen et al., 1998). Our group has been interested in the synthesis of new N,N'-type organic ligands for the construction of new inorganic–organic coordination polymers. To this end, we have been successful in the synthesis of several Schiff base ligands, such as 1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene (L), which have resulted in the generation of many new coordination compounds (Dong et al., 2000; Dong et al., 2000a). The title compound, catena-poly[Cu(L)₂(tta)₂] (tta is α-thenoyltrifluoroacetonato), (I), is a new example of a one-dimensional coordination polymer that uses an N,N'-type Schiff base ligand in its construction.

Compound (I) was prepared by the room temperature layering reaction of Cu(tta)₂ in methylene chloride with the ligand (L) in ethanol. Emerald-green crystals formed upon diffusion of the two solutions into one another over the course of several weeks, and a suitable single-crystal was selected for the structure determination. In (I), Cu²⁺ centers are found in a distorted octahedral coordination environment and they are located on sites of crystallographic inversion symmetry. Consequently, each Cu²⁺ center is coordinated by pairs of symmetry-related ligands. A symmetry-related pair of tta ligands occupies the equatorial positions of Cu²⁺, with each tta ligand coordinated through its O atoms in a bidentate fashion. Two pyridyl N donor atoms, one from each of two different symmetry related L ligands, complete the octahedral coordination sphere by occupying the axial positions. The average Cu—O bond length is 2.085 Å, the Cu—N bond distance is 2.1062 (19) Å, and the intrachain distance between successive Cu centers is approximately 15.4 Å. The Cu—O and Cu—N distances are typical (Yang et al., 2001; Lingafelter & Braun, 1966), and the Cu···Cu distance provides an estimate of the length of L. The octahedrally coordinated Cu²⁺ centers are linked into one-dimensional chains by L, with each N-atom donor of a single L coordinated to two different Cu centers.

The packing arrangement of the one-dimensional chains is shown in Fig. 2, where it can be seen that the chains extend approximately along the body diagonal of the unit cell, in the crystallographic [111] direction.

S2. Experimental

Synthesis of the ligand L was accomplished by minor variation of the published literature procedure, using 4-pyridine carboxaldehyde rather than 3-pyridine carboxaldehyde (Dong et al., 2000b). Cu(tta)₂ was prepared in bulk as follows: thenoyltrifluoroacetone (Htta, 10 mmol) and NaOH (10 mmol) were added to ethanol (50 ml) to deprotonate the tta ligand (tta⁻). Then CuCl₂·2H₂O (5 mmol) was added to the tta⁻ solution to produce Cu(tta)₂ as a light-green precipitate. The precipitate was harvested by vacuum filtration and washed with cold ethanol for use in the next step. The title compound was obtained by slow diffusion of a solution containing L (0.1 mmol) dissolved in ethanol (8 ml) into a solution of Cu(tta)₂ (0.1 mmol) dissolved in methylene chloride (8 ml). Initially, the two solutions were carefully layered, and emerald-green crystals appeared at the interface of the two solutions after several weeks.

S3. Refinement

Non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atoms were placed in geometrically idealized positions and included as riding atoms with C—H distances fixed at 0.93 Å.

Solution of the structure of 1 was routine with one notable exception. The thiophene ring of the tta ligand is disordered; and the disorder is modeled as a two-component rotational disorder about the ipso carbon bond (C10 - C11). Both disorder components lie essentially in the same plane. The geometry of the minor component (C7B - C10B, S1B) was restrained to be similar to that of the major component (C7A - C10A, S1A). The pivot atom C10(A/B) is common to both components, and atoms less than 0.5 Å from their disorder counterparts were assigned equal displacement parameters. The total occupancy was restrained to sum to unity. The final refined occupancies are A/B = 0.773 (3)/0.227 (3).

Computing details

Data collection: SMART (Bruker, 2001 or? 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL V6.1 (Sheldrick, 2000); software used to prepare material for publication: SHELXTL V6.1.

Figures

	Fig. 1. Displacement ellipsoid plot of (I), with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Cu atoms shown in turquoise; O, red; N, blue; F, green; S, yellow; C, black; H atoms are not shown.
	Fig. 2. View of the crystal packing in (I).

(I)

Crystal data

[Cu(C8H4F3O2S)2(C12H10N4)]	Z = 1
Mr = 716.12	F(000) = 361
Triclinic, P1	Dx = 1.603 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6890 (11) Å	Cell parameters from 4033 reflections
b = 9.7518 (13) Å	θ = 2.3–25.1°
c = 10.2035 (13) Å	µ = 0.96 mm^−1
α = 116.398 (2)°	T = 294 K
β = 99.417 (2)°	Prism, green
γ = 97.919 (2)°	0.30 × 0.24 × 0.20 mm
V = 741.99 (17) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.658, Tmax = 0.830	k = −11→11
4780 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.2977P] where P = (Fo^2 + 2Fc^2)/3
2577 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.31 e Å^−3
10 restraints	Δρmin = −0.36 e Å^−3

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. 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.0000	0.03727 (14)
C1	0.2040 (3)	0.5213 (3)	0.1210 (3)	0.0537 (6)
H1	0.1703	0.4159	0.0473	0.064*
C2	0.0957 (3)	0.5909 (3)	0.1978 (3)	0.0548 (6)
H2	−0.0079	0.5327	0.1764	0.066*
C3	0.1425 (3)	0.7480 (3)	0.3069 (3)	0.0481 (5)
C4	0.3022 (3)	0.8251 (3)	0.3399 (3)	0.0531 (6)
H4	0.3406	0.9290	0.4163	0.064*
C5	0.4024 (3)	0.7470 (3)	0.2590 (3)	0.0531 (6)
H5	0.5088	0.8002	0.2829	0.064*
C6	0.0248 (3)	0.8277 (3)	0.3776 (3)	0.0526 (6)
H6	−0.0810	0.7717	0.3509	0.063*
S1A	0.18025 (19)	−0.01533 (17)	−0.17703 (13)	0.0749 (4)	0.773 (3)
C7A	0.0985 (12)	−0.1689 (9)	−0.1537 (10)	0.078 (2)	0.773 (3)
H7A	0.0196	−0.2560	−0.2283	0.093*	0.773 (3)
C8A	0.1589 (10)	−0.1515 (13)	−0.0182 (12)	0.076 (2)	0.773 (3)
H8A	0.1310	−0.2255	0.0132	0.092*	0.773 (3)
C9A	0.2734 (16)	−0.0027 (14)	0.0739 (12)	0.0702 (14)	0.773 (3)
H9A	0.3246	0.0324	0.1745	0.084*	0.773 (3)
C10A	0.2998 (3)	0.0806 (3)	0.0023 (3)	0.0486 (5)	0.773 (3)
S1B	0.2897 (14)	−0.0111 (12)	0.1091 (10)	0.0702 (14)	0.227 (3)
C7B	0.125 (4)	−0.151 (5)	−0.020 (4)	0.076 (2)	0.227 (3)
H7B	0.0665	−0.2268	−0.0045	0.092*	0.227 (3)
C8B	0.089 (5)	−0.140 (4)	−0.146 (3)	0.078 (2)	0.227 (3)
H8B	0.0079	−0.2100	−0.2309	0.093*	0.227 (3)
C9B	0.194 (3)	−0.003 (2)	−0.1318 (15)	0.0749 (4)	0.227 (3)
H9B	0.1883	0.0233	−0.2090	0.090*	0.227 (3)
C10B	0.2998 (3)	0.0806 (3)	0.0023 (3)	0.0486 (5)	0.227 (3)
C11	0.4094 (3)	0.2333 (3)	0.0550 (3)	0.0432 (5)
C12	0.5098 (3)	0.3102 (3)	0.2010 (3)	0.0528 (6)
H12	0.4956	0.2665	0.2640	0.063*
C13	0.6291 (3)	0.4468 (3)	0.2592 (3)	0.0507 (5)
C14	0.7235 (4)	0.5171 (4)	0.4238 (4)	0.0777 (9)
F1	0.6929 (4)	0.4315 (3)	0.4883 (3)	0.1459 (13)
F2	0.6961 (3)	0.6568 (3)	0.5064 (2)	0.1215 (9)
F3	0.8803 (2)	0.5471 (3)	0.4360 (3)	0.1191 (8)
N1	0.3544 (2)	0.5974 (2)	0.1469 (2)	0.0461 (4)
N2	0.0653 (3)	0.9717 (3)	0.4746 (3)	0.0586 (5)
O1	0.4021 (2)	0.28584 (18)	−0.03896 (18)	0.0471 (4)
O2	0.6728 (2)	0.5257 (2)	0.1969 (2)	0.0544 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0385 (2)	0.0342 (2)	0.0402 (2)	0.00695 (15)	0.01063 (15)	0.01903 (16)
C1	0.0480 (13)	0.0381 (12)	0.0639 (15)	0.0050 (10)	0.0066 (11)	0.0190 (11)
C2	0.0432 (12)	0.0442 (14)	0.0679 (15)	0.0033 (10)	0.0087 (11)	0.0229 (12)
C3	0.0486 (12)	0.0441 (13)	0.0490 (12)	0.0064 (10)	0.0076 (10)	0.0229 (11)
C4	0.0530 (13)	0.0442 (13)	0.0484 (12)	0.0027 (11)	0.0088 (10)	0.0143 (11)
C5	0.0448 (12)	0.0497 (14)	0.0526 (13)	0.0011 (10)	0.0054 (10)	0.0191 (11)
C6	0.0475 (13)	0.0500 (15)	0.0565 (14)	0.0065 (10)	0.0110 (11)	0.0244 (12)
S1A	0.0853 (7)	0.0645 (7)	0.0608 (7)	−0.0038 (5)	−0.0058 (6)	0.0322 (7)
C7A	0.073 (2)	0.047 (4)	0.086 (2)	−0.003 (3)	−0.003 (2)	0.022 (3)
C8A	0.073 (5)	0.0621 (19)	0.092 (2)	−0.007 (3)	0.008 (3)	0.0455 (18)
C9A	0.087 (2)	0.0563 (15)	0.077 (4)	−0.0044 (14)	0.010 (3)	0.049 (2)
C10A	0.0486 (12)	0.0464 (13)	0.0533 (13)	0.0116 (10)	0.0130 (10)	0.0260 (11)
S1B	0.087 (2)	0.0563 (15)	0.077 (4)	−0.0044 (14)	0.010 (3)	0.049 (2)
C7B	0.073 (5)	0.0621 (19)	0.092 (2)	−0.007 (3)	0.008 (3)	0.0455 (18)
C8B	0.073 (2)	0.047 (4)	0.086 (2)	−0.003 (3)	−0.003 (2)	0.022 (3)
C9B	0.0853 (7)	0.0645 (7)	0.0608 (7)	−0.0038 (5)	−0.0058 (6)	0.0322 (7)
C10B	0.0486 (12)	0.0464 (13)	0.0533 (13)	0.0116 (10)	0.0130 (10)	0.0260 (11)
C11	0.0433 (11)	0.0423 (12)	0.0526 (12)	0.0143 (9)	0.0187 (10)	0.0266 (10)
C12	0.0536 (13)	0.0546 (15)	0.0569 (14)	0.0055 (11)	0.0096 (11)	0.0358 (12)
C13	0.0443 (12)	0.0549 (14)	0.0573 (13)	0.0116 (11)	0.0115 (10)	0.0311 (12)
C14	0.0652 (18)	0.083 (2)	0.0727 (19)	−0.0088 (16)	−0.0084 (15)	0.0429 (18)
F1	0.160 (2)	0.156 (2)	0.0983 (16)	−0.0595 (19)	−0.0478 (16)	0.0957 (17)
F2	0.141 (2)	0.1082 (18)	0.0659 (12)	0.0149 (16)	0.0045 (13)	0.0114 (12)
F3	0.0629 (12)	0.152 (2)	0.1292 (18)	−0.0043 (13)	−0.0233 (12)	0.0805 (17)
N1	0.0440 (10)	0.0388 (10)	0.0509 (10)	0.0070 (8)	0.0064 (8)	0.0202 (9)
N2	0.0519 (12)	0.0529 (13)	0.0609 (12)	0.0102 (10)	0.0158 (10)	0.0187 (11)
O1	0.0559 (9)	0.0414 (8)	0.0475 (8)	0.0096 (7)	0.0150 (7)	0.0242 (7)
O2	0.0497 (9)	0.0517 (10)	0.0631 (10)	0.0041 (7)	0.0135 (8)	0.0310 (9)

Geometric parameters (Å, º)

Cu1—O1^i	1.9759 (15)	C7A—H7A	0.9300
Cu1—O1	1.9759 (15)	C8A—C9A	1.436 (11)
Cu1—N1^i	2.1062 (19)	C8A—H8A	0.9300
Cu1—N1	2.1062 (19)	C9A—C10A	1.333 (7)
Cu1—O2^i	2.1950 (18)	C9A—H9A	0.9300
Cu1—O2	2.1950 (18)	C10A—C11	1.464 (3)
C1—N1	1.331 (3)	S1B—C7B	1.700 (8)
C1—C2	1.380 (3)	C7B—C8B	1.322 (6)
C1—H1	0.9300	C7B—H7B	0.9300
C2—C3	1.384 (3)	C8B—C9B	1.438 (12)
C2—H2	0.9300	C8B—H8B	0.9300
C3—C4	1.393 (3)	C9B—H9B	0.9300
C3—C6	1.460 (3)	C11—O1	1.270 (3)
C4—C5	1.370 (4)	C11—C12	1.394 (3)
C4—H4	0.9300	C12—C13	1.384 (3)
C5—N1	1.343 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—O2	1.254 (3)
C6—N2	1.261 (3)	C13—C14	1.527 (4)
C6—H6	0.9300	C14—F1	1.299 (4)
S1A—C7A	1.698 (6)	C14—F2	1.326 (4)
S1A—C10A	1.700 (2)	C14—F3	1.327 (4)
C7A—C8A	1.320 (5)	N2—N2^ii	1.404 (4)
O1^i—Cu1—O1	180.0	C7A—C8A—C9A	110.7 (6)
O1^i—Cu1—N1^i	90.97 (7)	C7A—C8A—H8A	124.6
O1—Cu1—N1^i	89.03 (7)	C9A—C8A—H8A	124.6
O1^i—Cu1—N1	89.03 (7)	C10A—C9A—C8A	114.0 (6)
O1—Cu1—N1	90.97 (7)	C10A—C9A—H9A	123.0
N1^i—Cu1—N1	180.0	C8A—C9A—H9A	123.0
O1^i—Cu1—O2^i	88.01 (6)	C9A—C10A—C11	130.4 (5)
O1—Cu1—O2^i	91.99 (6)	C9A—C10A—S1A	110.3 (5)
N1^i—Cu1—O2^i	87.16 (7)	C11—C10A—S1A	119.30 (17)
N1—Cu1—O2^i	92.84 (7)	C8B—C7B—S1B	112.8 (7)
O1^i—Cu1—O2	91.99 (6)	C8B—C7B—H7B	123.6
O1—Cu1—O2	88.01 (6)	S1B—C7B—H7B	123.6
N1^i—Cu1—O2	92.84 (7)	C7B—C8B—C9B	110.7 (9)
N1—Cu1—O2	87.16 (7)	C7B—C8B—H8B	124.6
O2^i—Cu1—O2	180.00 (8)	C9B—C8B—H8B	124.6
N1—C1—C2	123.3 (2)	C8B—C9B—H9B	123.3
N1—C1—H1	118.3	O1—C11—C12	125.2 (2)
C2—C1—H1	118.3	O1—C11—C10A	115.5 (2)
C1—C2—C3	119.5 (2)	C12—C11—C10A	119.25 (19)
C1—C2—H2	120.3	C13—C12—C11	124.9 (2)
C3—C2—H2	120.3	C13—C12—H12	117.6
C2—C3—C4	117.1 (2)	C11—C12—H12	117.6
C2—C3—C6	120.1 (2)	O2—C13—C12	129.5 (2)
C4—C3—C6	122.7 (2)	O2—C13—C14	113.1 (2)
C5—C4—C3	119.6 (2)	C12—C13—C14	117.4 (2)
C5—C4—H4	120.2	F1—C14—F2	107.6 (3)
C3—C4—H4	120.2	F1—C14—F3	108.1 (3)
N1—C5—C4	123.2 (2)	F2—C14—F3	104.3 (3)
N1—C5—H5	118.4	F1—C14—C13	115.2 (3)
C4—C5—H5	118.4	F2—C14—C13	110.2 (3)
N2—C6—C3	120.6 (2)	F3—C14—C13	110.8 (3)
N2—C6—H6	119.7	C1—N1—C5	117.1 (2)
C3—C6—H6	119.7	C1—N1—Cu1	121.50 (16)
C7A—S1A—C10A	92.1 (2)	C5—N1—Cu1	120.86 (16)
C8A—C7A—S1A	112.8 (5)	C6—N2—N2^ii	112.2 (3)
C8A—C7A—H7A	123.6	C11—O1—Cu1	127.61 (15)
S1A—C7A—H7A	123.6	C13—O2—Cu1	117.51 (15)
N1—C1—C2—C3	0.6 (4)	O2—C13—C14—F3	−50.6 (4)
C1—C2—C3—C4	−4.0 (4)	C12—C13—C14—F3	130.0 (3)
C1—C2—C3—C6	173.5 (2)	C2—C1—N1—C5	3.3 (4)
C2—C3—C4—C5	3.6 (4)	C2—C1—N1—Cu1	−168.2 (2)
C6—C3—C4—C5	−173.8 (2)	C4—C5—N1—C1	−3.7 (4)
C3—C4—C5—N1	0.3 (4)	C4—C5—N1—Cu1	167.8 (2)
C2—C3—C6—N2	−178.3 (3)	O1^i—Cu1—N1—C1	144.57 (19)
C4—C3—C6—N2	−1.0 (4)	O1—Cu1—N1—C1	−35.43 (19)
C10A—S1A—C7A—C8A	−0.8 (10)	O2^i—Cu1—N1—C1	56.60 (19)
S1A—C7A—C8A—C9A	2.3 (15)	O2—Cu1—N1—C1	−123.40 (19)
C7A—C8A—C9A—C10A	−3.2 (17)	O1^i—Cu1—N1—C5	−26.58 (19)
C8A—C9A—C10A—C11	−178.1 (8)	O1—Cu1—N1—C5	153.42 (19)
C8A—C9A—C10A—S1A	2.5 (13)	O2^i—Cu1—N1—C5	−114.54 (19)
C7A—S1A—C10A—C9A	−1.0 (9)	O2—Cu1—N1—C5	65.46 (19)
C7A—S1A—C10A—C11	179.5 (5)	C3—C6—N2—N2^ii	177.9 (3)
C9A—C10A—C11—O1	−177.0 (9)	C12—C11—O1—Cu1	−10.6 (3)
S1A—C10A—C11—O1	2.4 (3)	C10A—C11—O1—Cu1	168.33 (14)
C9A—C10A—C11—C12	1.9 (9)	N1^i—Cu1—O1—C11	115.73 (18)
S1A—C10A—C11—C12	−178.67 (19)	N1—Cu1—O1—C11	−64.27 (18)
O1—C11—C12—C13	−7.7 (4)	O2^i—Cu1—O1—C11	−157.15 (18)
C10A—C11—C12—C13	173.5 (2)	O2—Cu1—O1—C11	22.85 (18)
C11—C12—C13—O2	−1.3 (4)	C12—C13—O2—Cu1	22.3 (3)
C11—C12—C13—C14	178.1 (3)	C14—C13—O2—Cu1	−157.1 (2)
O2—C13—C14—F1	−173.7 (3)	O1^i—Cu1—O2—C13	152.88 (18)
C12—C13—C14—F1	6.9 (5)	O1—Cu1—O2—C13	−27.12 (18)
O2—C13—C14—F2	64.4 (3)	N1^i—Cu1—O2—C13	−116.06 (18)
C12—C13—C14—F2	−115.1 (3)	N1—Cu1—O2—C13	63.95 (18)

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