Aqua-bis-(3-fluoro-benzoato-κO)(1,10-phenanthroline-κN,N')copper(II).

In the title compound, [Cu(C(7)H(4)FO(2))(2)(C(12)H(8)N(2))(H(2)O)], the coordination around the Cu(II) atom is square-pyramidal. The equatorial positions are occupied by two N atoms from a 1,10-phenanthroline ligand [Cu-N = 2.008 (3) and 2.019 (3) Å] and two O atoms from 3-fluoro-benzoate ligands and a water mol-ecule [Cu-O = 1.950 (2) and 1.978 (2) Å]. One O atom from another 3-fluoro-benzoate ligand occupies the apical positon [Cu-O = 2.210 (2) Å]. Hydrogen bonds occur between coordinated water mol-ecules and benzoate ligands, while O-H⋯O, C-H⋯O, C-H⋯F and π-π stacking [centroid-centroid distance = 3.731 (2) Å] inter-actions consolidate the crystal packing.

Related literature

A number of copper SOD mimetics (SOD = superoxide dismutase) have been shown to possess anti­tumor activity and have been proposed as a new class of potential anti­cancer agents, see: Devereux et al. (2007 ▶). Phen­oxy­alkanoic acids inter­act with n class="Chemical">Cu(II) ions to form complexes which have been shown to have diverse stereochemistries, see: Smith et al. (1981 ▶, 1982 ▶). For the structures of similar coordination compounds, see: Liu et al. (2009 ▶); Zhu & Xiao (2006 ▶).

Experimental

Crystal data

[Cu(n class="CellLine">C7H4FO2)2(C12H8N2)(H2O)]

M = 539.96

Triclinic,

a = 9.9914 (8) Å

b = 10.7258 (9) Å

c = 11.6166 (10) Å

α = 73.208 (1)°

β = 70.082 (1)°

γ = 86.293 (1)°

V = 1119.74 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 295 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.782, T max = 0.860

5876 measured reflections

3972 independent reflections

2924 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.03

3972 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.99 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012220/hg5016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012220/hg5016Isup2.hkl

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

[Cu(C7H4FO2)2(C12H8N2)(H2O)]	Z = 2
Mr = 539.96	F(000) = 550
Triclinic, P1	Dx = 1.602 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9914 (8) Å	Cell parameters from 2269 reflections
b = 10.7258 (9) Å	θ = 2.4–23.9°
c = 11.6166 (10) Å	µ = 1.04 mm−1
α = 73.208 (1)°	T = 295 K
β = 70.082 (1)°	Block, blue
γ = 86.293 (1)°	0.25 × 0.20 × 0.15 mm
V = 1119.74 (16) Å3

Bruker APEXII CCD diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	2924 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→10
Tmin = 0.782, Tmax = 0.860	k = −12→12
5876 measured reflections	l = −13→9

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0675P)2] where P = (Fo2 + 2Fc2)/3
3972 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.99 e Å−3
0 restraints	Δρmin = −0.47 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
C1	−0.1039 (5)	0.3825 (4)	0.2313 (4)	0.0699 (13)
H1	−0.1100	0.2939	0.2400	0.084*
C2	−0.2204 (5)	0.4403 (6)	0.2961 (5)	0.0823 (15)
H2	−0.3030	0.3900	0.3478	0.099*
C3	−0.2174 (5)	0.5693 (5)	0.2861 (4)	0.0766 (14)
H3	−0.2971	0.6075	0.3301	0.092*
C4	−0.0929 (4)	0.6439 (4)	0.2089 (4)	0.0575 (10)
C5	−0.0752 (5)	0.7814 (5)	0.1881 (4)	0.0686 (12)
H5	−0.1507	0.8262	0.2288	0.082*
C6	0.0486 (5)	0.8471 (4)	0.1106 (4)	0.0610 (11)
H6	0.0569	0.9360	0.0995	0.073*
C7	0.1661 (4)	0.7829 (3)	0.0457 (4)	0.0460 (9)
C8	0.2980 (4)	0.8451 (3)	−0.0358 (4)	0.0503 (9)
H8	0.3121	0.9341	−0.0512	0.060*
C9	0.4045 (4)	0.7747 (3)	−0.0918 (3)	0.0487 (9)
H9	0.4912	0.8159	−0.1471	0.058*
C10	0.3850 (4)	0.6403 (3)	−0.0670 (3)	0.0423 (8)
H10	0.4601	0.5931	−0.1045	0.051*
C11	0.1545 (4)	0.6493 (3)	0.0640 (3)	0.0400 (8)
C12	0.0226 (4)	0.5790 (4)	0.1455 (3)	0.0456 (9)
C13	0.2143 (4)	0.2156 (3)	0.3195 (3)	0.0470 (9)
C14	0.2732 (4)	0.1690 (3)	0.4278 (3)	0.0432 (8)
C15	0.2137 (4)	0.0593 (4)	0.5261 (3)	0.0516 (9)
H15	0.1346	0.0157	0.5289	0.062*
C16	0.2740 (5)	0.0158 (4)	0.6198 (4)	0.0584 (11)
C17	0.3895 (4)	0.0746 (4)	0.6215 (4)	0.0569 (10)
H17	0.4276	0.0405	0.6864	0.068*
C18	0.4494 (5)	0.1861 (4)	0.5246 (4)	0.0603 (11)
H18	0.5270	0.2299	0.5241	0.072*
C19	0.3909 (4)	0.2315 (4)	0.4279 (4)	0.0538 (10)
H19	0.4316	0.3056	0.3615	0.065*
C20	0.4248 (4)	0.2594 (3)	−0.1064 (4)	0.0503 (9)
C21	0.5686 (4)	0.2694 (4)	−0.2072 (4)	0.0514 (10)
C22	0.6404 (5)	0.3875 (4)	−0.2736 (4)	0.0632 (11)
H22	0.6000	0.4637	−0.2567	0.076*
C23	0.7713 (5)	0.3922 (5)	−0.3647 (4)	0.0757 (14)
C24	0.8378 (6)	0.2835 (5)	−0.3942 (5)	0.0802 (14)
H24	0.9261	0.2901	−0.4580	0.096*
C25	0.7682 (6)	0.1643 (5)	−0.3252 (5)	0.0765 (14)
H25	0.8108	0.0883	−0.3406	0.092*
C26	0.6352 (5)	0.1575 (4)	−0.2331 (4)	0.0640 (12)
H26	0.5893	0.0765	−0.1876	0.077*
Cu1	0.20778 (5)	0.38751 (4)	0.05953 (4)	0.04433 (19)
F1	0.2173 (4)	−0.0908 (3)	0.7161 (3)	0.1306 (14)
F3	0.8389 (4)	0.5091 (3)	−0.4302 (3)	0.1242 (13)
N1	0.2605 (3)	0.5780 (3)	0.0096 (3)	0.0395 (7)
N2	0.0190 (3)	0.4496 (3)	0.1555 (3)	0.0498 (8)
O1	0.1097 (3)	0.1514 (3)	0.3257 (3)	0.0654 (8)
O2	0.2767 (3)	0.3139 (2)	0.2280 (2)	0.0486 (6)
O3	0.3809 (3)	0.3625 (2)	−0.0732 (2)	0.0494 (6)
O4	0.3565 (3)	0.1534 (3)	−0.0605 (3)	0.0765 (9)
O1W	0.1185 (3)	0.2161 (2)	0.0909 (3)	0.0591 (7)
H1W	0.1159	0.1795	0.1675	0.089*
H2W	0.1895	0.1784	0.0524	0.089*

	U11	U22	U33	U12	U13	U23
C1	0.053 (3)	0.068 (3)	0.073 (3)	−0.016 (2)	−0.019 (2)	0.006 (2)
C2	0.044 (3)	0.104 (4)	0.071 (3)	−0.013 (3)	−0.004 (2)	0.001 (3)
C3	0.048 (3)	0.104 (4)	0.062 (3)	0.004 (3)	−0.005 (2)	−0.015 (3)
C4	0.045 (2)	0.076 (3)	0.052 (2)	0.007 (2)	−0.017 (2)	−0.020 (2)
C5	0.065 (3)	0.079 (3)	0.077 (3)	0.022 (2)	−0.028 (3)	−0.043 (3)
C6	0.070 (3)	0.055 (2)	0.074 (3)	0.018 (2)	−0.035 (2)	−0.033 (2)
C7	0.059 (2)	0.0390 (19)	0.050 (2)	0.0075 (17)	−0.0283 (19)	−0.0163 (17)
C8	0.069 (3)	0.0305 (18)	0.055 (2)	−0.0027 (18)	−0.028 (2)	−0.0089 (17)
C9	0.054 (2)	0.0401 (19)	0.047 (2)	−0.0096 (17)	−0.0141 (18)	−0.0052 (17)
C10	0.048 (2)	0.0339 (18)	0.042 (2)	−0.0013 (15)	−0.0135 (17)	−0.0069 (15)
C11	0.042 (2)	0.0411 (19)	0.0388 (19)	0.0018 (15)	−0.0186 (16)	−0.0084 (16)
C12	0.043 (2)	0.051 (2)	0.041 (2)	0.0009 (17)	−0.0171 (17)	−0.0057 (17)
C13	0.052 (2)	0.040 (2)	0.046 (2)	0.0026 (17)	−0.0149 (18)	−0.0108 (18)
C14	0.050 (2)	0.0377 (18)	0.0373 (19)	0.0029 (16)	−0.0101 (16)	−0.0094 (15)
C15	0.062 (3)	0.047 (2)	0.044 (2)	−0.0095 (18)	−0.0163 (19)	−0.0093 (18)
C16	0.080 (3)	0.045 (2)	0.040 (2)	−0.009 (2)	−0.020 (2)	0.0035 (18)
C17	0.068 (3)	0.057 (2)	0.046 (2)	0.001 (2)	−0.025 (2)	−0.0077 (19)
C18	0.067 (3)	0.059 (2)	0.049 (2)	−0.002 (2)	−0.020 (2)	−0.007 (2)
C19	0.059 (2)	0.047 (2)	0.046 (2)	−0.0093 (18)	−0.0140 (19)	−0.0020 (18)
C20	0.062 (3)	0.042 (2)	0.057 (2)	0.0039 (18)	−0.032 (2)	−0.0160 (19)
C21	0.068 (3)	0.044 (2)	0.055 (2)	0.0104 (19)	−0.030 (2)	−0.0217 (19)
C22	0.077 (3)	0.055 (2)	0.054 (3)	0.012 (2)	−0.015 (2)	−0.021 (2)
C23	0.080 (3)	0.069 (3)	0.062 (3)	0.005 (3)	−0.007 (3)	−0.016 (3)
C24	0.084 (4)	0.096 (4)	0.066 (3)	0.024 (3)	−0.024 (3)	−0.038 (3)
C25	0.092 (4)	0.075 (3)	0.085 (4)	0.027 (3)	−0.041 (3)	−0.049 (3)
C26	0.079 (3)	0.055 (2)	0.077 (3)	0.011 (2)	−0.039 (3)	−0.034 (2)
Cu1	0.0507 (3)	0.0328 (3)	0.0478 (3)	−0.00640 (18)	−0.0178 (2)	−0.00571 (19)
F1	0.169 (3)	0.110 (2)	0.103 (2)	−0.072 (2)	−0.081 (2)	0.043 (2)
F3	0.113 (3)	0.091 (2)	0.110 (3)	−0.0060 (19)	0.029 (2)	−0.018 (2)
N1	0.0405 (16)	0.0362 (15)	0.0383 (16)	−0.0007 (13)	−0.0112 (13)	−0.0076 (13)
N2	0.0462 (19)	0.0481 (18)	0.0471 (18)	−0.0098 (14)	−0.0152 (15)	0.0005 (14)
O1	0.0704 (19)	0.0583 (16)	0.0621 (18)	−0.0245 (14)	−0.0326 (16)	0.0093 (14)
O2	0.0559 (16)	0.0416 (13)	0.0425 (14)	−0.0088 (11)	−0.0175 (12)	0.0004 (12)
O3	0.0595 (16)	0.0316 (12)	0.0563 (16)	0.0019 (11)	−0.0172 (13)	−0.0142 (12)
O4	0.076 (2)	0.0439 (15)	0.110 (3)	−0.0078 (15)	−0.0196 (18)	−0.0350 (17)
O1W	0.0714 (19)	0.0472 (14)	0.0597 (17)	−0.0153 (13)	−0.0244 (15)	−0.0100 (13)

C1—N2	1.347 (5)	C15—H15	0.9300
C1—C2	1.374 (6)	C16—F1	1.338 (4)
C1—H1	0.9300	C16—C17	1.359 (6)
C2—C3	1.357 (7)	C17—C18	1.383 (5)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.395 (6)	C18—C19	1.391 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C12	1.404 (5)	C19—H19	0.9300
C4—C5	1.437 (6)	C20—O4	1.243 (4)
C5—C6	1.350 (6)	C20—O3	1.277 (4)
C5—H5	0.9300	C20—C21	1.500 (5)
C6—C7	1.419 (5)	C21—C22	1.375 (5)
C6—H6	0.9300	C21—C26	1.394 (5)
C7—C11	1.393 (5)	C22—C23	1.367 (6)
C7—C8	1.407 (5)	C22—H22	0.9300
C8—C9	1.354 (5)	C23—F3	1.347 (5)
C8—H8	0.9300	C23—C24	1.376 (6)
C9—C10	1.398 (5)	C24—C25	1.379 (7)
C9—H9	0.9300	C24—H24	0.9300
C10—N1	1.340 (4)	C25—C26	1.384 (6)
C10—H10	0.9300	C25—H25	0.9300
C11—N1	1.351 (4)	C26—H26	0.9300
C11—C12	1.438 (5)	Cu1—O3	1.950 (2)
C12—N2	1.360 (5)	Cu1—O1W	1.978 (2)
C13—O1	1.259 (4)	Cu1—N1	2.008 (3)
C13—O2	1.272 (4)	Cu1—N2	2.019 (3)
C13—C14	1.510 (5)	Cu1—O2	2.210 (2)
C14—C15	1.376 (5)	O1W—H1W	0.8545
C14—C19	1.392 (5)	O1W—H2W	0.8462
C15—C16	1.373 (5)
N2—C1—C2	122.3 (4)	C18—C17—H17	120.7
N2—C1—H1	118.9	C17—C18—C19	118.6 (4)
C2—C1—H1	118.9	C17—C18—H18	120.7
C3—C2—C1	121.2 (4)	C19—C18—H18	120.7
C3—C2—H2	119.4	C18—C19—C14	121.7 (3)
C1—C2—H2	119.4	C18—C19—H19	119.1
C2—C3—C4	119.0 (4)	C14—C19—H19	119.1
C2—C3—H3	120.5	O4—C20—O3	124.3 (4)
C4—C3—H3	120.5	O4—C20—C21	118.9 (3)
C3—C4—C12	117.0 (4)	O3—C20—C21	116.8 (3)
C3—C4—C5	125.0 (4)	C22—C21—C26	118.1 (4)
C12—C4—C5	118.0 (4)	C22—C21—C20	121.5 (3)
C6—C5—C4	121.5 (4)	C26—C21—C20	120.4 (4)
C6—C5—H5	119.3	C23—C22—C21	119.6 (4)
C4—C5—H5	119.3	C23—C22—H22	120.2
C5—C6—C7	121.2 (4)	C21—C22—H22	120.2
C5—C6—H6	119.4	F3—C23—C22	118.7 (4)
C7—C6—H6	119.4	F3—C23—C24	118.0 (4)
C11—C7—C8	116.4 (3)	C22—C23—C24	123.4 (5)
C11—C7—C6	119.4 (4)	C23—C24—C25	117.3 (5)
C8—C7—C6	124.2 (4)	C23—C24—H24	121.3
C9—C8—C7	119.7 (3)	C25—C24—H24	121.3
C9—C8—H8	120.2	C24—C25—C26	120.2 (4)
C7—C8—H8	120.2	C24—C25—H25	119.9
C8—C9—C10	120.4 (3)	C26—C25—H25	119.9
C8—C9—H9	119.8	C25—C26—C21	121.4 (4)
C10—C9—H9	119.8	C25—C26—H26	119.3
N1—C10—C9	121.5 (3)	C21—C26—H26	119.3
N1—C10—H10	119.2	O3—Cu1—O1W	94.85 (10)
C9—C10—H10	119.2	O3—Cu1—N1	90.11 (10)
N1—C11—C7	124.4 (3)	O1W—Cu1—N1	165.91 (11)
N1—C11—C12	115.9 (3)	O3—Cu1—N2	164.15 (11)
C7—C11—C12	119.7 (3)	O1W—Cu1—N2	90.67 (12)
N2—C12—C4	123.9 (3)	N1—Cu1—N2	81.29 (11)
N2—C12—C11	115.9 (3)	O3—Cu1—O2	99.65 (10)
C4—C12—C11	120.2 (4)	O1W—Cu1—O2	91.54 (10)
O1—C13—O2	125.3 (3)	N1—Cu1—O2	100.63 (10)
O1—C13—C14	117.2 (3)	N2—Cu1—O2	95.04 (11)
O2—C13—C14	117.5 (3)	C10—N1—C11	117.6 (3)
C15—C14—C19	118.9 (4)	C10—N1—Cu1	128.7 (2)
C15—C14—C13	119.7 (3)	C11—N1—Cu1	113.7 (2)
C19—C14—C13	121.4 (3)	C1—N2—C12	116.6 (4)
C16—C15—C14	118.3 (4)	C1—N2—Cu1	130.3 (3)
C16—C15—H15	120.8	C12—N2—Cu1	113.0 (2)
C14—C15—H15	120.8	C13—O2—Cu1	121.4 (2)
F1—C16—C17	117.1 (4)	C20—O3—Cu1	129.5 (2)
F1—C16—C15	119.0 (4)	Cu1—O1W—H1W	100.5
C17—C16—C15	123.9 (4)	Cu1—O1W—H2W	100.5
C16—C17—C18	118.6 (4)	H1W—O1W—H2W	98.7
C16—C17—H17	120.7
N2—C1—C2—C3	0.4 (8)	F3—C23—C24—C25	179.2 (5)
C1—C2—C3—C4	−0.3 (8)	C22—C23—C24—C25	−1.4 (8)
C2—C3—C4—C12	0.2 (7)	C23—C24—C25—C26	1.8 (7)
C2—C3—C4—C5	179.1 (5)	C24—C25—C26—C21	−0.3 (7)
C3—C4—C5—C6	−179.3 (4)	C22—C21—C26—C25	−1.6 (6)
C12—C4—C5—C6	−0.4 (6)	C20—C21—C26—C25	−179.6 (4)
C4—C5—C6—C7	0.4 (7)	C9—C10—N1—C11	−1.0 (5)
C5—C6—C7—C11	−1.1 (6)	C9—C10—N1—Cu1	−179.8 (3)
C5—C6—C7—C8	−179.7 (4)	C7—C11—N1—C10	−0.1 (5)
C11—C7—C8—C9	0.3 (5)	C12—C11—N1—C10	179.9 (3)
C6—C7—C8—C9	179.0 (4)	C7—C11—N1—Cu1	178.9 (3)
C7—C8—C9—C10	−1.3 (6)	C12—C11—N1—Cu1	−1.1 (4)
C8—C9—C10—N1	1.7 (6)	O3—Cu1—N1—C10	−12.2 (3)
C8—C7—C11—N1	0.4 (5)	O1W—Cu1—N1—C10	−123.0 (5)
C6—C7—C11—N1	−178.4 (3)	N2—Cu1—N1—C10	−178.9 (3)
C8—C7—C11—C12	−179.6 (3)	O2—Cu1—N1—C10	87.6 (3)
C6—C7—C11—C12	1.7 (5)	O3—Cu1—N1—C11	168.9 (2)
C3—C4—C12—N2	0.0 (6)	O1W—Cu1—N1—C11	58.1 (5)
C5—C4—C12—N2	−179.0 (4)	N2—Cu1—N1—C11	2.3 (2)
C3—C4—C12—C11	179.9 (4)	O2—Cu1—N1—C11	−91.2 (2)
C5—C4—C12—C11	0.9 (6)	C2—C1—N2—C12	−0.2 (6)
N1—C11—C12—N2	−1.7 (5)	C2—C1—N2—Cu1	175.7 (3)
C7—C11—C12—N2	178.3 (3)	C4—C12—N2—C1	0.0 (5)
N1—C11—C12—C4	178.4 (3)	C11—C12—N2—C1	−179.9 (3)
C7—C11—C12—C4	−1.6 (5)	C4—C12—N2—Cu1	−176.5 (3)
O1—C13—C14—C15	1.1 (5)	C11—C12—N2—Cu1	3.5 (4)
O2—C13—C14—C15	−176.9 (3)	O3—Cu1—N2—C1	123.0 (4)
O1—C13—C14—C19	178.3 (4)	O1W—Cu1—N2—C1	12.5 (4)
O2—C13—C14—C19	0.3 (5)	N1—Cu1—N2—C1	−179.2 (4)
C19—C14—C15—C16	−0.4 (5)	O2—Cu1—N2—C1	−79.1 (4)
C13—C14—C15—C16	176.9 (3)	O3—Cu1—N2—C12	−61.0 (5)
C14—C15—C16—F1	−180.0 (4)	O1W—Cu1—N2—C12	−171.6 (3)
C14—C15—C16—C17	−0.1 (6)	N1—Cu1—N2—C12	−3.2 (2)
F1—C16—C17—C18	−179.0 (4)	O2—Cu1—N2—C12	96.8 (2)
C15—C16—C17—C18	1.1 (7)	O1—C13—O2—Cu1	−0.4 (5)
C16—C17—C18—C19	−1.6 (6)	C14—C13—O2—Cu1	177.4 (2)
C17—C18—C19—C14	1.1 (6)	O3—Cu1—O2—C13	−118.2 (3)
C15—C14—C19—C18	−0.1 (6)	O1W—Cu1—O2—C13	−23.0 (3)
C13—C14—C19—C18	−177.4 (3)	N1—Cu1—O2—C13	149.9 (3)
O4—C20—C21—C22	171.0 (4)	N2—Cu1—O2—C13	67.8 (3)
O3—C20—C21—C22	−9.2 (5)	O4—C20—O3—Cu1	3.8 (6)
O4—C20—C21—C26	−11.0 (6)	C21—C20—O3—Cu1	−176.0 (2)
O3—C20—C21—C26	168.8 (3)	O1W—Cu1—O3—C20	−10.8 (3)
C26—C21—C22—C23	1.9 (6)	N1—Cu1—O3—C20	−177.6 (3)
C20—C21—C22—C23	179.9 (4)	N2—Cu1—O3—C20	−120.8 (4)
C21—C22—C23—F3	179.0 (4)	O2—Cu1—O3—C20	81.6 (3)
C21—C22—C23—C24	−0.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1	0.85	1.75	2.585 (4)	163
O1W—H2W···O4	0.85	1.80	2.612 (4)	161
C10—H10···O3	0.93	2.53	3.005 (4)	112
C1—H1···F1i	0.93	2.33	3.213 (6)	158.
C8—H8···O4ii	0.93	2.39	3.309 (4)	171.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1	0.85	1.75	2.585 (4)	163
O1W—H2W⋯O4	0.85	1.80	2.612 (4)	161
C10—H10⋯O3	0.93	2.53	3.005 (4)	112
C1—H1⋯F1i	0.93	2.33	3.213 (6)	158
C8—H8⋯O4ii	0.93	2.39	3.309 (4)	171

Symmetry codes: (i) ; (ii) .