(Acetato-κO,O')bis-(1,10-phenanthroline-κN,N')copper(II) trifluoro-acetate tetra-hydrate.

In the title compound, [Cu(CH(3)CO(2))(C(12)H(8)N(2))(2)](CF(3)CO(2))·4H(2)O, the Cu(II) atom shows a distorted octa-hedral coordination with four N atoms [Cu-N = 2.015 (3)-2.244 (3) Å] from the two phenanthroline ligands and two O atoms from the acetate [Cu-O = 1.953 (3) and 2.764 (3) Å]. Strong inter-molecular O-H⋯O hydrogen-bonding inter-actions consolidate the crystal packing. The F atoms of the anion are disordered over two positions in a 0.5233 (3):0.4767 (3) ratio.

Related literature

For metal–n class="Chemical">1,10-phenanthroline complexes with carboxyl­ates, see: Sun et al. (2007 ▶); Liu et al. (2009 ▶).

Experimental

Crystal data

[Cu(C2H3O2)(n class="CellLine">C12H8N2)2](C2F3O2)·4H2O

M = 668.08

Triclinic,

a = 8.9019 (7) Å

b = 11.6662 (9) Å

c = 15.698 (1) Å

α = 101.619 (1)°

β = 101.512 (1)°

γ = 108.514 (1)°

V = 1451.98 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.28 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.801, T max = 0.859

7689 measured reflections

5112 independent reflections

4389 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.159

S = 1.02

5112 reflections

425 parameters

103 restraints

H-atom parameters constrained

Δρmax = 1.04 e Å−3

Δρmin = −0.87 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024359/ez2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024359/ez2212Isup2.hkl

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

[Cu(C2H3O2)(C12H8N2)2](C2F3O2)·4H2O	Z = 2
Mr = 668.08	F(000) = 686
Triclinic, P1	Dx = 1.528 Mg m−3
a = 8.9019 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6662 (9) Å	Cell parameters from 4430 reflections
c = 15.698 (1) Å	θ = 2.5–27.8°
α = 101.619 (1)°	µ = 0.83 mm−1
β = 101.512 (1)°	T = 293 K
γ = 108.514 (1)°	Block, blue
V = 1451.98 (19) Å3	0.28 × 0.25 × 0.19 mm

Bruker SMART APEX diffractometer	5112 independent reflections
Radiation source: fine-focus sealed tube	4389 reflections with I > 2σ(I)
graphite	Rint = 0.043
phi and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.801, Tmax = 0.859	k = −13→13
7689 measured reflections	l = −18→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.108P)2 + 0.7243P] where P = (Fo2 + 2Fc2)/3
5112 reflections	(Δ/σ)max = 0.002
425 parameters	Δρmax = 1.04 e Å−3
103 restraints	Δρmin = −0.86 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	0.70769 (5)	0.42710 (4)	0.71713 (3)	0.0397 (2)
F1	0.083 (2)	0.9968 (17)	0.6171 (10)	0.133 (4)	0.52 (2)
F2	0.138 (2)	0.8377 (11)	0.5566 (10)	0.118 (4)	0.52 (2)
F3	0.3252 (15)	1.0243 (15)	0.6021 (9)	0.121 (4)	0.52 (2)
F1'	0.0317 (13)	0.9385 (17)	0.5837 (12)	0.120 (4)	0.48 (2)
F2'	0.206 (2)	0.8680 (17)	0.5546 (10)	0.117 (4)	0.48 (2)
F3'	0.263 (2)	1.0720 (11)	0.6148 (9)	0.116 (4)	0.48 (2)
N1	0.5545 (4)	0.3202 (3)	0.5937 (2)	0.0432 (8)
N2	0.5668 (4)	0.5324 (3)	0.6982 (2)	0.0440 (8)
N3	0.6031 (4)	0.3667 (3)	0.8268 (2)	0.0439 (8)
N4	0.8712 (4)	0.5606 (3)	0.8296 (2)	0.0428 (8)
O1	0.8368 (4)	0.3195 (3)	0.7158 (2)	0.0491 (7)
O2	0.9846 (4)	0.4555 (4)	0.6563 (2)	0.0676 (9)
O3	0.1324 (9)	0.8811 (7)	0.7380 (5)	0.146 (2)
O4	0.3983 (7)	0.9689 (5)	0.7462 (4)	0.1105 (16)
O5	0.7803 (6)	0.8614 (5)	0.9518 (4)	0.1055 (15)
H5A	0.8130	0.8679	0.9051	0.127*
H5B	0.8480	0.9207	0.9978	0.127*
O6	0.7421 (6)	0.0847 (4)	0.7568 (4)	0.0954 (14)
H6A	0.7587	0.1508	0.7392	0.115*
H6B	0.6419	0.0542	0.7570	0.115*
O7	0.5361 (8)	0.9627 (7)	0.9249 (4)	0.139 (2)
H7A	0.6116	0.9327	0.9256	0.166*
H7B	0.5276	0.9963	0.8818	0.166*
O8	0.9949 (10)	1.0217 (8)	0.8494 (5)	0.176 (3)
H8A	0.8909	0.9997	0.8294	0.211*
H8B	1.0276	0.9799	0.8113	0.211*
C1	0.9569 (5)	0.3597 (5)	0.6812 (3)	0.0505 (10)
C2	1.0606 (7)	0.2817 (6)	0.6725 (4)	0.0720 (15)
H2A	1.0192	0.2109	0.6951	0.108*
H2B	1.1731	0.3315	0.7071	0.108*
H2C	1.0556	0.2522	0.6099	0.108*
C3	1.0023 (6)	0.6569 (4)	0.8305 (3)	0.0539 (11)
H3	1.0226	0.6644	0.7757	0.065*
C4	1.1096 (6)	0.7466 (4)	0.9102 (4)	0.0624 (13)
H4	1.1998	0.8126	0.9082	0.075*
C5	1.0821 (6)	0.7371 (4)	0.9907 (3)	0.0583 (12)
H5	1.1533	0.7966	1.0444	0.070*
C6	0.9449 (5)	0.6366 (4)	0.9928 (3)	0.0497 (10)
C7	0.8417 (5)	0.5507 (4)	0.9101 (3)	0.0402 (9)
C8	0.6997 (5)	0.4478 (4)	0.9087 (3)	0.0401 (9)
C9	0.6667 (6)	0.4339 (4)	0.9899 (3)	0.0511 (11)
C10	0.5254 (7)	0.3300 (5)	0.9842 (4)	0.0659 (14)
H10	0.4985	0.3174	1.0368	0.079*
C11	0.4303 (7)	0.2496 (5)	0.9031 (4)	0.0676 (14)
H11	0.3378	0.1809	0.8992	0.081*
C12	0.4720 (6)	0.2712 (4)	0.8253 (3)	0.0544 (11)
H12	0.4047	0.2153	0.7694	0.065*
C13	0.7751 (7)	0.5228 (5)	1.0731 (3)	0.0633 (13)
H13	0.7536	0.5136	1.1274	0.076*
C14	0.9071 (7)	0.6189 (5)	1.0746 (3)	0.0627 (13)
H14	0.9755	0.6753	1.1301	0.075*
C15	0.5530 (6)	0.2158 (4)	0.5418 (3)	0.0566 (11)
H15	0.6303	0.1826	0.5631	0.068*
C16	0.4407 (7)	0.1531 (5)	0.4566 (3)	0.0685 (14)
H16	0.4453	0.0806	0.4214	0.082*
C17	0.3246 (7)	0.1982 (6)	0.4250 (3)	0.0719 (16)
H17	0.2476	0.1556	0.3687	0.086*
C18	0.3210 (5)	0.3089 (5)	0.4771 (3)	0.0568 (12)
C19	0.4408 (5)	0.3674 (4)	0.5617 (3)	0.0446 (9)
C20	0.4465 (5)	0.4808 (4)	0.6192 (3)	0.0435 (9)
C21	0.3284 (5)	0.5328 (5)	0.5919 (3)	0.0549 (11)
C22	0.3376 (7)	0.6413 (6)	0.6535 (4)	0.0709 (15)
H22	0.2617	0.6788	0.6392	0.085*
C23	0.4577 (8)	0.6925 (5)	0.7343 (4)	0.0720 (15)
H23	0.4622	0.7637	0.7757	0.086*
C24	0.5729 (6)	0.6375 (5)	0.7545 (3)	0.0585 (12)
H24	0.6565	0.6751	0.8090	0.070*
C25	0.2096 (6)	0.4726 (6)	0.5058 (4)	0.0689 (16)
H25	0.1326	0.5073	0.4870	0.083*
C26	0.2068 (6)	0.3658 (7)	0.4505 (4)	0.0698 (16)
H26	0.1285	0.3295	0.3941	0.084*
C27	0.2466 (9)	0.9333 (5)	0.7120 (4)	0.0738 (16)
C28	0.1951 (7)	0.9529 (5)	0.6193 (4)	0.0709 (14)

	U11	U22	U33	U12	U13	U23
Cu1	0.0400 (3)	0.0424 (3)	0.0318 (3)	0.0131 (2)	0.0061 (2)	0.0079 (2)
F1	0.127 (8)	0.135 (8)	0.138 (8)	0.076 (6)	−0.004 (6)	0.033 (6)
F2	0.108 (8)	0.122 (6)	0.075 (5)	−0.001 (6)	0.009 (6)	0.010 (5)
F3	0.109 (7)	0.130 (7)	0.119 (6)	0.005 (6)	0.049 (5)	0.070 (6)
F1'	0.071 (6)	0.127 (8)	0.130 (8)	0.013 (6)	0.004 (5)	0.032 (6)
F2'	0.118 (8)	0.148 (8)	0.071 (5)	0.060 (7)	0.024 (6)	−0.015 (6)
F3'	0.127 (8)	0.102 (7)	0.094 (6)	0.006 (6)	0.018 (6)	0.050 (5)
N1	0.0406 (18)	0.0477 (19)	0.0347 (17)	0.0091 (15)	0.0117 (14)	0.0089 (15)
N2	0.0454 (19)	0.0455 (19)	0.0408 (18)	0.0165 (15)	0.0121 (15)	0.0125 (15)
N3	0.0445 (19)	0.0401 (18)	0.0436 (19)	0.0126 (15)	0.0115 (15)	0.0108 (15)
N4	0.0416 (18)	0.0445 (18)	0.0366 (17)	0.0123 (15)	0.0057 (14)	0.0110 (15)
O1	0.0505 (17)	0.0550 (17)	0.0462 (16)	0.0231 (14)	0.0162 (13)	0.0159 (14)
O2	0.072 (2)	0.080 (2)	0.066 (2)	0.0317 (19)	0.0306 (18)	0.038 (2)
O3	0.175 (6)	0.155 (6)	0.132 (5)	0.042 (5)	0.091 (5)	0.077 (5)
O4	0.098 (4)	0.090 (3)	0.113 (4)	0.023 (3)	−0.004 (3)	0.020 (3)
O5	0.093 (3)	0.131 (4)	0.099 (3)	0.045 (3)	0.031 (3)	0.038 (3)
O6	0.090 (3)	0.075 (3)	0.127 (4)	0.027 (2)	0.034 (3)	0.044 (3)
O7	0.136 (5)	0.190 (6)	0.109 (4)	0.102 (5)	0.023 (4)	0.029 (4)
O8	0.203 (8)	0.259 (9)	0.161 (7)	0.159 (7)	0.096 (6)	0.099 (7)
C1	0.051 (2)	0.068 (3)	0.034 (2)	0.025 (2)	0.0098 (18)	0.016 (2)
C2	0.076 (3)	0.102 (4)	0.062 (3)	0.053 (3)	0.032 (3)	0.030 (3)
C3	0.051 (3)	0.051 (2)	0.051 (3)	0.009 (2)	0.008 (2)	0.018 (2)
C4	0.047 (3)	0.045 (3)	0.074 (3)	0.004 (2)	0.001 (2)	0.012 (2)
C5	0.053 (3)	0.048 (3)	0.052 (3)	0.015 (2)	−0.007 (2)	−0.003 (2)
C6	0.052 (2)	0.052 (2)	0.042 (2)	0.026 (2)	0.0027 (19)	0.0063 (19)
C7	0.044 (2)	0.043 (2)	0.0327 (19)	0.0205 (18)	0.0040 (16)	0.0087 (16)
C8	0.045 (2)	0.044 (2)	0.038 (2)	0.0233 (18)	0.0126 (17)	0.0132 (17)
C9	0.062 (3)	0.062 (3)	0.046 (2)	0.036 (2)	0.023 (2)	0.021 (2)
C10	0.075 (3)	0.078 (4)	0.068 (3)	0.035 (3)	0.041 (3)	0.037 (3)
C11	0.066 (3)	0.060 (3)	0.083 (4)	0.019 (3)	0.036 (3)	0.029 (3)
C12	0.054 (3)	0.044 (2)	0.061 (3)	0.012 (2)	0.020 (2)	0.014 (2)
C13	0.086 (4)	0.079 (4)	0.036 (2)	0.043 (3)	0.022 (2)	0.017 (2)
C14	0.075 (3)	0.078 (3)	0.033 (2)	0.039 (3)	0.005 (2)	0.004 (2)
C15	0.058 (3)	0.053 (3)	0.048 (3)	0.010 (2)	0.018 (2)	0.004 (2)
C16	0.070 (3)	0.063 (3)	0.049 (3)	0.005 (3)	0.020 (2)	−0.003 (2)
C17	0.056 (3)	0.086 (4)	0.034 (2)	−0.008 (3)	0.005 (2)	−0.002 (2)
C18	0.041 (2)	0.078 (3)	0.037 (2)	0.001 (2)	0.0096 (18)	0.019 (2)
C19	0.034 (2)	0.056 (2)	0.038 (2)	0.0049 (18)	0.0116 (16)	0.0184 (19)
C20	0.036 (2)	0.055 (2)	0.042 (2)	0.0124 (18)	0.0152 (17)	0.0231 (19)
C21	0.043 (2)	0.071 (3)	0.064 (3)	0.022 (2)	0.022 (2)	0.039 (3)
C22	0.066 (3)	0.079 (4)	0.096 (4)	0.043 (3)	0.035 (3)	0.050 (3)
C23	0.086 (4)	0.062 (3)	0.083 (4)	0.041 (3)	0.032 (3)	0.022 (3)
C24	0.068 (3)	0.056 (3)	0.055 (3)	0.029 (2)	0.017 (2)	0.013 (2)
C25	0.039 (2)	0.108 (5)	0.071 (3)	0.024 (3)	0.015 (2)	0.056 (4)
C26	0.037 (2)	0.115 (5)	0.047 (3)	0.010 (3)	0.005 (2)	0.038 (3)
C27	0.094 (4)	0.050 (3)	0.073 (4)	0.018 (3)	0.036 (3)	0.010 (3)
C28	0.069 (3)	0.065 (3)	0.074 (4)	0.015 (3)	0.028 (3)	0.020 (3)

Cu1—O1	1.953 (3)	C4—H4	0.9300
Cu1—N1	2.015 (3)	C5—C6	1.410 (7)
Cu1—N4	2.022 (3)	C5—H5	0.9300
Cu1—N2	2.037 (3)	C6—C7	1.397 (6)
Cu1—N3	2.244 (3)	C6—C14	1.428 (7)
F1—C28	1.256 (11)	C7—C8	1.433 (6)
F2—C28	1.367 (12)	C8—C9	1.392 (6)
F3—C28	1.308 (10)	C9—C10	1.415 (7)
F1'—C28	1.393 (12)	C9—C13	1.425 (7)
F2'—C28	1.311 (12)	C10—C11	1.343 (8)
F3'—C28	1.351 (11)	C10—H10	0.9301
N1—C15	1.317 (6)	C11—C12	1.392 (7)
N1—C19	1.357 (5)	C11—H11	0.9300
N2—C24	1.337 (6)	C12—H12	0.9300
N2—C20	1.344 (5)	C13—C14	1.334 (8)
N3—C12	1.326 (6)	C13—H13	0.9300
N3—C8	1.357 (5)	C14—H14	0.9300
N4—C3	1.333 (6)	C15—C16	1.389 (7)
N4—C7	1.361 (5)	C15—H15	0.9300
O1—C1	1.294 (5)	C16—C17	1.355 (8)
O2—C1	1.226 (6)	C16—H16	0.9300
O3—C27	1.202 (8)	C17—C18	1.396 (8)
O4—C27	1.245 (8)	C17—H17	0.9300
O5—H5A	0.8500	C18—C19	1.406 (6)
O5—H5B	0.8500	C18—C26	1.422 (8)
O6—H6A	0.8501	C19—C20	1.423 (6)
O6—H6B	0.8500	C20—C21	1.410 (6)
O7—H7A	0.8500	C21—C22	1.397 (8)
O7—H7B	0.8501	C21—C25	1.419 (7)
O8—H8A	0.8500	C22—C23	1.363 (8)
O8—H8B	0.8500	C22—H22	0.9300
C1—C2	1.494 (7)	C23—C24	1.391 (7)
C2—H2A	0.9600	C23—H23	0.9300
C2—H2B	0.9600	C24—H24	0.9300
C2—H2C	0.9600	C25—C26	1.356 (8)
C3—C4	1.390 (7)	C25—H25	0.9300
C3—H3	0.9300	C26—H26	0.9300
C4—C5	1.353 (8)	C27—C28	1.521 (9)
O1—Cu1—N1	91.55 (13)	C14—C13—C9	121.3 (4)
O1—Cu1—N4	93.66 (13)	C14—C13—H13	119.3
N1—Cu1—N4	169.21 (13)	C9—C13—H13	119.4
O1—Cu1—N2	171.51 (12)	C13—C14—C6	121.3 (4)
N1—Cu1—N2	81.21 (14)	C13—C14—H14	119.2
N4—Cu1—N2	92.78 (14)	C6—C14—H14	119.6
O1—Cu1—N3	93.94 (12)	N1—C15—C16	122.8 (5)
N1—Cu1—N3	110.64 (13)	N1—C15—H15	118.5
N4—Cu1—N3	78.44 (13)	C16—C15—H15	118.7
N2—Cu1—N3	92.75 (13)	C17—C16—C15	119.6 (5)
C15—N1—C19	117.9 (4)	C17—C16—H16	120.2
C15—N1—Cu1	129.2 (3)	C15—C16—H16	120.2
C19—N1—Cu1	112.9 (3)	C16—C17—C18	120.0 (4)
C24—N2—C20	118.2 (4)	C16—C17—H17	120.1
C24—N2—Cu1	129.2 (3)	C18—C17—H17	120.0
C20—N2—Cu1	112.5 (3)	C17—C18—C19	116.7 (5)
C12—N3—C8	117.7 (4)	C17—C18—C26	124.9 (5)
C12—N3—Cu1	132.8 (3)	C19—C18—C26	118.4 (5)
C8—N3—Cu1	109.5 (2)	N1—C19—C18	123.0 (4)
C3—N4—C7	118.3 (4)	N1—C19—C20	116.5 (4)
C3—N4—Cu1	125.3 (3)	C18—C19—C20	120.5 (4)
C7—N4—Cu1	116.4 (3)	N2—C20—C21	123.5 (4)
C1—O1—Cu1	110.9 (3)	N2—C20—C19	116.9 (4)
H5A—O5—H5B	109.6	C21—C20—C19	119.6 (4)
H6A—O6—H6B	109.6	C22—C21—C20	116.4 (4)
H7A—O7—H7B	109.8	C22—C21—C25	124.8 (5)
H8A—O8—H8B	108.6	C20—C21—C25	118.8 (5)
O2—C1—O1	122.5 (4)	C23—C22—C21	120.3 (5)
O2—C1—C2	121.4 (4)	C23—C22—H22	119.8
O1—C1—C2	116.0 (4)	C21—C22—H22	119.9
C1—C2—H2A	109.0	C22—C23—C24	119.6 (5)
C1—C2—H2B	109.7	C22—C23—H23	120.1
H2A—C2—H2B	109.5	C24—C23—H23	120.3
C1—C2—H2C	109.8	N2—C24—C23	122.0 (5)
H2A—C2—H2C	109.5	N2—C24—H24	119.3
H2B—C2—H2C	109.5	C23—C24—H24	118.7
N4—C3—C4	122.7 (4)	C26—C25—C21	121.3 (5)
N4—C3—H3	118.7	C26—C25—H25	119.6
C4—C3—H3	118.7	C21—C25—H25	119.2
C5—C4—C3	119.5 (5)	C25—C26—C18	121.4 (5)
C5—C4—H4	120.3	C25—C26—H26	119.1
C3—C4—H4	120.2	C18—C26—H26	119.5
C4—C5—C6	119.7 (4)	O3—C27—O4	130.9 (7)
C4—C5—H5	120.2	O3—C27—C28	113.8 (7)
C6—C5—H5	120.1	O4—C27—C28	115.2 (6)
C7—C6—C5	117.6 (4)	F1—C28—F3	113.6 (9)
C7—C6—C14	118.9 (4)	F1—C28—F2'	127.6 (11)
C5—C6—C14	123.5 (4)	F3—C28—F2'	81.4 (9)
N4—C7—C6	122.2 (4)	F1—C28—F3'	74.3 (9)
N4—C7—C8	118.1 (3)	F3—C28—F3'	40.5 (6)
C6—C7—C8	119.6 (4)	F2'—C28—F3'	113.5 (10)
N3—C8—C9	122.7 (4)	F1—C28—F2	110.5 (9)
N3—C8—C7	117.6 (3)	F3—C28—F2	106.9 (8)
C9—C8—C7	119.7 (4)	F2'—C28—F2	26.1 (8)
C8—C9—C10	117.2 (4)	F3'—C28—F2	132.9 (10)
C8—C9—C13	119.1 (4)	F1—C28—F1'	30.7 (7)
C10—C9—C13	123.7 (4)	F3—C28—F1'	126.8 (10)
C11—C10—C9	120.0 (5)	F2'—C28—F1'	99.2 (9)
C11—C10—H10	120.0	F3'—C28—F1'	96.1 (9)
C9—C10—H10	120.0	F2—C28—F1'	79.8 (9)
C10—C11—C12	119.0 (5)	F1—C28—C27	109.3 (8)
C10—C11—H11	120.3	F3—C28—C27	109.3 (8)
C12—C11—H11	120.7	F2'—C28—C27	112.0 (9)
N3—C12—C11	123.4 (5)	F3'—C28—C27	115.4 (7)
N3—C12—H12	118.3	F2—C28—C27	107.1 (8)
C11—C12—H12	118.3	F1'—C28—C27	119.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5	0.85	1.95	2.787 (8)	168
O7—H7B···O4	0.85	2.11	2.854 (8)	145
O6—H6A···O1	0.85	2.00	2.844 (5)	170
O6—H6B···O4i	0.85	2.03	2.881 (7)	175
O8—H8B···O3ii	0.85	2.03	2.868 (10)	171
O8—H8A···O6iii	0.85	2.17	2.809 (9)	132

Cu1—O1	1.953 (3)
Cu1—N1	2.015 (3)
Cu1—N4	2.022 (3)
Cu1—N2	2.037 (3)
Cu1—N3	2.244 (3)

O1—Cu1—N1	91.55 (13)
O1—Cu1—N4	93.66 (13)
N1—Cu1—N4	169.21 (13)
O1—Cu1—N2	171.51 (12)
N1—Cu1—N2	81.21 (14)
N4—Cu1—N2	92.78 (14)
O1—Cu1—N3	93.94 (12)
N1—Cu1—N3	110.64 (13)
N4—Cu1—N3	78.44 (13)
N2—Cu1—N3	92.75 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O5	0.85	1.95	2.787 (8)	168
O7—H7B⋯O4	0.85	2.11	2.854 (8)	145
O6—H6A⋯O1	0.85	2.00	2.844 (5)	170
O6—H6B⋯O4i	0.85	2.03	2.881 (7)	175
O8—H8B⋯O3ii	0.85	2.03	2.868 (10)	171
O8—H8A⋯O6iii	0.85	2.17	2.809 (9)	132

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