Copper(II) bis­(4,4,4-tri­fluoro-1-phenyl­butane-1,3-dionate) complexes with pyridin-2-one, 3-hy­droxy­pyridine and 3-hy­droxy­pyridin-2-one ligands: mol­ecular structures and hydrogen-bonded networks

Copper(II) bis­(4,4,4-tri­fluoro-1-phenyl­butane-1,3-dionate) complexes with pyri­din-2-one (pyon), 3-hy­droxy­pyridine (hpy) and 3-hy­droxy­pyridin-2-one (hpyon) were prepared and the solid-state structures of (pyridin-2-one-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ²O,O′)copper(II), [Cu(C₁₀H₆F₃O₂)₂(C₅H₅NO)] or [Cu(tfpb-κ²O,O′)₂(pyon-κO)], (I), bis­(pyridin-3-ol-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ²O,O′)copper(II), [Cu(C₁₀H₆F₃O₂)₂(C₅H₅NO)₂] or [Cu(tfpb-κ²O,O′)₂(hpy-κO)₂], (II), and bis­(3-hy­droxy­pyridin-2-one-κO)bis­(4,4,4-tri­fluoro-3-oxo-1-phenyl­butan-1-olato-κ²O,O′)copper(II), [Cu(C₁₀H₆F₃O₂)₂(C₅H₅NO₂)₂] or [Cu(tfpb-κ²O,O′)₂(hpyon-κO)₂], (III), were determined by single-crystal X-ray analysis. The coordination of the metal centre is square pyramidal and displays a rare example of a mutual cis arrangement of the β-diketonate ligands in (I) and a trans-octa­hedral arrangement in (II) and (III). Complex (II) presents the first crystallographic evidence of κO-monodentate hpy ligation to the transition metal enabling the pyridine N atom to participate in a two-dimensional hydrogen-bonded network through O—H...N inter­actions, forming a graph-set motif R₂²(7) through a C—H...O inter­action. Complex (III) presents the first crystallographic evidence of monodentate coordination of the neutral hpyon ligand to a metal centre and a two-dimensional hydrogen-bonded network is formed through N—H...O inter­actions facilitated by C—H...O inter­actions, forming the graph-set motifs R₂²(8) and R₂²(7).

Computing details

Data collection: CrysAlis PRO (Agilent, 2013) for (I), (II); KappaCCD Reference Manual (Nonius, 1998) for (III). Cell refinement: CrysAlis PRO (Agilent, 2013) for (I), (II); DENZO-SMN (Otwinowski & Minor, 1997) for (III). Data reduction: CrysAlis PRO (Agilent, 2013) for (I), (II); DENZO-SMN (Otwinowski & Minor, 1997) for (III). For all structures, program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

(Pyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ²O,O')copper(II) (I)

Crystal data

[Cu(C10H6F3O2)2(C5H5NO)]	Z = 2
Mr = 588.93	F(000) = 594
Triclinic, P1	Dx = 1.563 Mg m^−3
a = 10.5928 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7082 (5) Å	Cell parameters from 3680 reflections
c = 12.4943 (6) Å	θ = 3.2–30.3°
α = 69.019 (4)°	µ = 0.95 mm^−1
β = 71.705 (4)°	T = 293 K
γ = 88.110 (3)°	Prism, green
V = 1251.32 (11) Å^3	0.30 × 0.10 × 0.07 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	5718 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3312 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.046
Detector resolution: 10.4933 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −10→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −13→13
Tmin = 0.624, Tmax = 1.000	l = −15→16
11601 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
5718 reflections	Δρmax = 0.40 e Å^−3
343 parameters	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cu1	0.58853 (3)	0.39870 (4)	0.28948 (4)	0.05204 (15)
F1	0.7402 (3)	0.0908 (3)	0.1205 (3)	0.1212 (10)
F2	0.8231 (3)	0.0208 (3)	0.2596 (3)	0.1413 (12)
F3	0.9421 (3)	0.1394 (3)	0.0819 (3)	0.1255 (10)
F4	0.1793 (2)	0.2241 (2)	0.3400 (3)	0.1066 (8)
F5	0.1644 (2)	0.1643 (2)	0.5245 (2)	0.1124 (9)
F6	0.06941 (19)	0.3330 (2)	0.4445 (2)	0.0961 (8)
N1	0.5596 (2)	0.6869 (2)	−0.0643 (2)	0.0499 (6)
H1	0.5235	0.6300	−0.0826	0.060*
O1	0.6654 (2)	0.2525 (2)	0.2415 (2)	0.0591 (6)
O2	0.76087 (19)	0.4821 (2)	0.2586 (2)	0.0583 (6)
O3	0.41156 (19)	0.30902 (19)	0.34400 (19)	0.0541 (5)
O4	0.52249 (19)	0.5380 (2)	0.35046 (19)	0.0545 (5)
O5	0.5752 (2)	0.5152 (2)	0.0993 (2)	0.0584 (6)
C1	0.8260 (4)	0.1249 (4)	0.1643 (4)	0.0781 (11)
C2	0.7895 (3)	0.2491 (3)	0.1970 (3)	0.0560 (8)
C3	0.8926 (3)	0.3370 (3)	0.1784 (3)	0.0613 (9)
H3	0.9792	0.3208	0.1414	0.074*
C4	0.8749 (3)	0.4497 (3)	0.2118 (3)	0.0525 (8)
C5	0.9900 (3)	0.5387 (3)	0.1952 (3)	0.0533 (8)
C6	0.9665 (4)	0.6400 (4)	0.2407 (3)	0.0709 (10)
H6	0.8793	0.6522	0.2799	0.085*
C7	1.0708 (4)	0.7240 (4)	0.2290 (4)	0.0854 (12)
H7	1.0537	0.7927	0.2592	0.102*
C8	1.1995 (4)	0.7048 (4)	0.1723 (4)	0.0861 (12)
H8	1.2702	0.7603	0.1644	0.103*
C9	1.2235 (4)	0.6046 (5)	0.1279 (4)	0.0941 (13)
H9	1.3111	0.5921	0.0898	0.113*
C10	1.1208 (3)	0.5213 (4)	0.1382 (3)	0.0724 (10)
H10	1.1390	0.4533	0.1070	0.087*
C11	0.1793 (3)	0.2699 (4)	0.4254 (4)	0.0683 (10)
C12	0.3065 (3)	0.3571 (3)	0.3913 (3)	0.0502 (8)
C13	0.2941 (3)	0.4714 (3)	0.4176 (3)	0.0570 (8)
H13	0.2087	0.4913	0.4534	0.068*
C14	0.4030 (3)	0.5607 (3)	0.3934 (3)	0.0462 (7)
C15	0.3829 (3)	0.6878 (3)	0.4162 (3)	0.0495 (7)
C16	0.4935 (3)	0.7720 (3)	0.3902 (3)	0.0637 (9)
H16	0.5785	0.7467	0.3611	0.076*
C17	0.4796 (4)	0.8934 (3)	0.4069 (4)	0.0750 (11)
H17	0.5550	0.9486	0.3895	0.090*
C18	0.3563 (4)	0.9318 (4)	0.4486 (3)	0.0749 (11)
H18	0.3470	1.0140	0.4586	0.090*
C19	0.2452 (4)	0.8493 (4)	0.4762 (4)	0.0778 (11)
H19	0.1607	0.8750	0.5064	0.093*
C20	0.2580 (3)	0.7281 (3)	0.4595 (3)	0.0660 (10)
H20	0.1821	0.6733	0.4774	0.079*
C21	0.5976 (3)	0.6387 (3)	0.0357 (3)	0.0502 (8)
C22	0.6599 (4)	0.7356 (4)	0.0596 (3)	0.0750 (11)
H22	0.6900	0.7090	0.1262	0.090*
C23	0.6764 (5)	0.8672 (4)	−0.0134 (4)	0.0991 (15)
H23	0.7182	0.9297	0.0033	0.119*
C24	0.6310 (5)	0.9095 (4)	−0.1134 (4)	0.0935 (14)
H24	0.6401	0.9999	−0.1623	0.112*
C25	0.5740 (4)	0.8173 (3)	−0.1376 (3)	0.0690 (10)
H25	0.5445	0.8430	−0.2045	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0426 (2)	0.0611 (3)	0.0610 (3)	0.00950 (17)	−0.01601 (19)	−0.0334 (2)
F1	0.131 (2)	0.120 (2)	0.165 (3)	0.0308 (16)	−0.056 (2)	−0.107 (2)
F2	0.229 (3)	0.0756 (16)	0.110 (2)	0.0676 (19)	−0.050 (2)	−0.0320 (16)
F3	0.0998 (19)	0.119 (2)	0.153 (2)	0.0148 (15)	0.0152 (17)	−0.0934 (19)
F4	0.0747 (16)	0.122 (2)	0.144 (2)	−0.0157 (13)	−0.0264 (15)	−0.0798 (19)
F5	0.0900 (17)	0.0710 (15)	0.122 (2)	−0.0129 (12)	−0.0116 (15)	0.0091 (15)
F6	0.0464 (12)	0.0781 (14)	0.160 (2)	0.0045 (10)	−0.0219 (13)	−0.0490 (15)
N1	0.0537 (16)	0.0483 (15)	0.0504 (17)	−0.0024 (11)	−0.0140 (13)	−0.0231 (13)
O1	0.0504 (14)	0.0620 (13)	0.0724 (16)	0.0105 (10)	−0.0180 (12)	−0.0353 (12)
O2	0.0413 (13)	0.0721 (14)	0.0750 (16)	0.0135 (10)	−0.0200 (11)	−0.0424 (13)
O3	0.0460 (13)	0.0568 (13)	0.0636 (15)	0.0059 (10)	−0.0129 (11)	−0.0310 (11)
O4	0.0430 (13)	0.0653 (13)	0.0643 (15)	0.0055 (10)	−0.0128 (11)	−0.0382 (12)
O5	0.0709 (15)	0.0520 (13)	0.0585 (15)	−0.0022 (10)	−0.0279 (12)	−0.0208 (11)
C1	0.084 (3)	0.071 (3)	0.083 (3)	0.024 (2)	−0.017 (3)	−0.042 (2)
C2	0.058 (2)	0.061 (2)	0.051 (2)	0.0155 (17)	−0.0154 (17)	−0.0255 (17)
C3	0.050 (2)	0.076 (2)	0.060 (2)	0.0141 (17)	−0.0098 (17)	−0.0344 (19)
C4	0.0450 (19)	0.066 (2)	0.049 (2)	0.0126 (15)	−0.0172 (16)	−0.0232 (17)
C5	0.046 (2)	0.068 (2)	0.0418 (19)	0.0055 (15)	−0.0144 (16)	−0.0152 (16)
C6	0.051 (2)	0.088 (3)	0.078 (3)	0.0015 (18)	−0.0122 (19)	−0.043 (2)
C7	0.075 (3)	0.092 (3)	0.099 (3)	−0.005 (2)	−0.025 (3)	−0.048 (3)
C8	0.059 (3)	0.101 (3)	0.091 (3)	−0.019 (2)	−0.019 (2)	−0.029 (3)
C9	0.050 (3)	0.116 (4)	0.109 (4)	−0.001 (2)	−0.008 (2)	−0.047 (3)
C10	0.045 (2)	0.090 (3)	0.080 (3)	0.0023 (19)	−0.0092 (19)	−0.038 (2)
C11	0.054 (2)	0.055 (2)	0.086 (3)	0.0018 (17)	−0.013 (2)	−0.023 (2)
C12	0.0449 (19)	0.0501 (18)	0.051 (2)	0.0030 (14)	−0.0146 (16)	−0.0140 (16)
C13	0.0424 (19)	0.0543 (19)	0.070 (2)	0.0063 (14)	−0.0087 (16)	−0.0257 (17)
C14	0.0454 (19)	0.0537 (18)	0.0390 (18)	0.0097 (14)	−0.0129 (14)	−0.0175 (15)
C15	0.054 (2)	0.0523 (18)	0.0429 (18)	0.0076 (15)	−0.0147 (15)	−0.0196 (15)
C16	0.057 (2)	0.065 (2)	0.075 (3)	0.0066 (17)	−0.0193 (19)	−0.0336 (19)
C17	0.081 (3)	0.065 (2)	0.088 (3)	−0.0017 (19)	−0.030 (2)	−0.035 (2)
C18	0.100 (3)	0.061 (2)	0.081 (3)	0.022 (2)	−0.039 (2)	−0.038 (2)
C19	0.079 (3)	0.070 (2)	0.090 (3)	0.027 (2)	−0.020 (2)	−0.043 (2)
C20	0.054 (2)	0.066 (2)	0.085 (3)	0.0127 (16)	−0.0174 (19)	−0.040 (2)
C21	0.0498 (19)	0.0538 (19)	0.049 (2)	−0.0002 (15)	−0.0106 (16)	−0.0256 (17)
C22	0.100 (3)	0.068 (2)	0.069 (3)	−0.009 (2)	−0.042 (2)	−0.026 (2)
C23	0.151 (4)	0.068 (3)	0.095 (3)	−0.023 (3)	−0.060 (3)	−0.030 (3)
C24	0.153 (4)	0.051 (2)	0.083 (3)	−0.012 (2)	−0.054 (3)	−0.016 (2)
C25	0.092 (3)	0.057 (2)	0.060 (2)	−0.0014 (18)	−0.030 (2)	−0.0181 (19)

Geometric parameters (Å, º)

Cu1—O1	1.938 (2)	C8—C9	1.358 (5)
Cu1—O2	1.923 (2)	C8—H8	0.9300
Cu1—O3	1.936 (2)	C9—C10	1.375 (5)
Cu1—O4	1.9251 (19)	C9—H9	0.9300
Cu1—O5	2.302 (2)	C10—H10	0.9300
F1—C1	1.318 (4)	C11—C12	1.519 (4)
F2—C1	1.300 (4)	C12—C13	1.369 (4)
F3—C1	1.304 (4)	C13—C14	1.409 (4)
F4—C11	1.324 (4)	C13—H13	0.9300
F5—C11	1.313 (4)	C14—C15	1.483 (4)
F6—C11	1.326 (4)	C15—C20	1.382 (4)
N1—C25	1.350 (4)	C15—C16	1.383 (4)
N1—C21	1.352 (4)	C16—C17	1.384 (4)
N1—H1	0.8600	C16—H16	0.9300
O1—C2	1.262 (3)	C17—C18	1.356 (5)
O2—C4	1.263 (3)	C17—H17	0.9300
O3—C12	1.273 (3)	C18—C19	1.371 (5)
O4—C14	1.263 (3)	C18—H18	0.9300
O5—C21	1.260 (3)	C19—C20	1.382 (4)
C1—C2	1.530 (4)	C19—H19	0.9300
C2—C3	1.373 (4)	C20—H20	0.9300
C3—C4	1.401 (4)	C21—C22	1.411 (4)
C3—H3	0.9300	C22—C23	1.358 (5)
C4—C5	1.488 (4)	C22—H22	0.9300
C5—C6	1.377 (4)	C23—C24	1.399 (5)
C5—C10	1.386 (4)	C23—H23	0.9300
C6—C7	1.386 (5)	C24—C25	1.341 (5)
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.372 (5)	C25—H25	0.9300
C7—H7	0.9300
O1—Cu1—O5	91.53 (8)	C5—C10—H10	120.1
O2—Cu1—O1	92.59 (9)	F5—C11—F4	106.6 (3)
O2—Cu1—O3	172.09 (9)	F5—C11—F6	106.9 (3)
O2—Cu1—O4	83.96 (8)	F4—C11—F6	105.8 (3)
O2—Cu1—O5	95.61 (8)	F5—C11—C12	111.2 (3)
O3—Cu1—O1	90.14 (8)	F4—C11—C12	112.2 (3)
O4—Cu1—O3	92.59 (8)	F6—C11—C12	113.8 (3)
O3—Cu1—O5	91.73 (8)	O3—C12—C13	129.3 (3)
O4—Cu1—O1	173.55 (9)	O3—C12—C11	113.3 (3)
O4—Cu1—O5	94.23 (8)	C13—C12—C11	117.4 (3)
C25—N1—C21	125.1 (3)	C12—C13—C14	123.8 (3)
C25—N1—H1	117.5	C12—C13—H13	118.1
C21—N1—H1	117.5	C14—C13—H13	118.1
C2—O1—Cu1	122.8 (2)	O4—C14—C13	122.2 (3)
C4—O2—Cu1	128.5 (2)	O4—C14—C15	116.4 (3)
C12—O3—Cu1	122.78 (19)	C13—C14—C15	121.4 (3)
C14—O4—Cu1	128.72 (19)	C20—C15—C16	118.1 (3)
C21—O5—Cu1	130.60 (19)	C20—C15—C14	122.9 (3)
F2—C1—F3	108.4 (3)	C16—C15—C14	118.9 (3)
F2—C1—F1	105.4 (4)	C15—C16—C17	120.9 (3)
F3—C1—F1	105.0 (4)	C15—C16—H16	119.5
F2—C1—C2	111.1 (3)	C17—C16—H16	119.5
F3—C1—C2	114.4 (3)	C18—C17—C16	120.1 (4)
F1—C1—C2	112.0 (3)	C18—C17—H17	119.9
O1—C2—C3	129.4 (3)	C16—C17—H17	119.9
O1—C2—C1	113.2 (3)	C17—C18—C19	119.9 (3)
C3—C2—C1	117.4 (3)	C17—C18—H18	120.0
C2—C3—C4	123.8 (3)	C19—C18—H18	120.0
C2—C3—H3	118.1	C18—C19—C20	120.4 (3)
C4—C3—H3	118.1	C18—C19—H19	119.8
O2—C4—C3	122.6 (3)	C20—C19—H19	119.8
O2—C4—C5	115.5 (3)	C15—C20—C19	120.5 (3)
C3—C4—C5	122.0 (3)	C15—C20—H20	119.8
C6—C5—C10	118.6 (3)	C19—C20—H20	119.8
C6—C5—C4	119.1 (3)	O5—C21—N1	119.3 (3)
C10—C5—C4	122.3 (3)	O5—C21—C22	125.5 (3)
C5—C6—C7	121.1 (3)	N1—C21—C22	115.2 (3)
C5—C6—H6	119.5	C23—C22—C21	120.8 (3)
C7—C6—H6	119.5	C23—C22—H22	119.6
C8—C7—C6	119.4 (4)	C21—C22—H22	119.6
C8—C7—H7	120.3	C22—C23—C24	120.5 (4)
C6—C7—H7	120.3	C22—C23—H23	119.7
C9—C8—C7	119.9 (4)	C24—C23—H23	119.7
C9—C8—H8	120.0	C25—C24—C23	118.7 (4)
C7—C8—H8	120.0	C25—C24—H24	120.6
C8—C9—C10	121.2 (4)	C23—C24—H24	120.6
C8—C9—H9	119.4	C24—C25—N1	119.7 (3)
C10—C9—H9	119.4	C24—C25—H25	120.2
C9—C10—C5	119.9 (4)	N1—C25—H25	120.2
C9—C10—H10	120.1
Cu1—O1—C2—C3	3.2 (5)	F5—C11—C12—C13	−102.3 (4)
Cu1—O1—C2—C1	−179.1 (2)	F4—C11—C12—C13	138.4 (3)
F2—C1—C2—O1	−80.2 (4)	F6—C11—C12—C13	18.4 (5)
F3—C1—C2—O1	156.6 (3)	O3—C12—C13—C14	0.8 (6)
F1—C1—C2—O1	37.4 (5)	C11—C12—C13—C14	178.8 (3)
F2—C1—C2—C3	97.9 (4)	Cu1—O4—C14—C13	8.4 (4)
F3—C1—C2—C3	−25.3 (5)	Cu1—O4—C14—C15	−171.08 (19)
F1—C1—C2—C3	−144.6 (4)	C12—C13—C14—O4	−3.6 (5)
O1—C2—C3—C4	2.3 (6)	C12—C13—C14—C15	175.8 (3)
C1—C2—C3—C4	−175.4 (3)	O4—C14—C15—C20	178.0 (3)
Cu1—O2—C4—C3	−3.0 (5)	C13—C14—C15—C20	−1.5 (5)
Cu1—O2—C4—C5	177.45 (19)	O4—C14—C15—C16	−0.2 (4)
C2—C3—C4—O2	−2.5 (5)	C13—C14—C15—C16	−179.7 (3)
C2—C3—C4—C5	177.0 (3)	C20—C15—C16—C17	−0.1 (5)
O2—C4—C5—C6	5.9 (4)	C14—C15—C16—C17	178.2 (3)
C3—C4—C5—C6	−173.6 (3)	C15—C16—C17—C18	−0.4 (6)
O2—C4—C5—C10	−175.9 (3)	C16—C17—C18—C19	1.1 (6)
C3—C4—C5—C10	4.6 (5)	C17—C18—C19—C20	−1.3 (6)
C10—C5—C6—C7	0.7 (5)	C16—C15—C20—C19	−0.1 (5)
C4—C5—C6—C7	179.0 (3)	C14—C15—C20—C19	−178.4 (3)
C5—C6—C7—C8	−0.8 (6)	C18—C19—C20—C15	0.8 (6)
C6—C7—C8—C9	0.3 (7)	Cu1—O5—C21—N1	−168.01 (18)
C7—C8—C9—C10	0.2 (7)	Cu1—O5—C21—C22	11.5 (5)
C8—C9—C10—C5	−0.2 (6)	C25—N1—C21—O5	177.8 (3)
C6—C5—C10—C9	−0.2 (5)	C25—N1—C21—C22	−1.8 (4)
C4—C5—C10—C9	−178.4 (3)	O5—C21—C22—C23	−178.3 (4)
Cu1—O3—C12—C13	−2.7 (5)	N1—C21—C22—C23	1.2 (5)
Cu1—O3—C12—C11	179.2 (2)	C21—C22—C23—C24	0.5 (7)
F5—C11—C12—O3	76.0 (4)	C22—C23—C24—C25	−1.7 (7)
F4—C11—C12—O3	−43.2 (4)	C23—C24—C25—N1	1.1 (6)
F6—C11—C12—O3	−163.3 (3)	C21—N1—C25—C24	0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5^i	0.86	2.01	2.861 (3)	172
C20—H20···F6^ii	0.93	2.53	3.297 (4)	140

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

Bis(pyridin-3-ol-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ²O,O')copper(II) (II)

Crystal data

[Cu(C10H6F3O2)2(C5H5NO)2]	F(000) = 694
Mr = 684.03	Dx = 1.517 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.0085 (3) Å	Cell parameters from 3917 reflections
b = 14.1540 (5) Å	θ = 3.1–73.9°
c = 11.2503 (3) Å	µ = 1.78 mm^−1
β = 110.022 (4)°	T = 293 K
V = 1497.40 (9) Å^3	Prism, green
Z = 2	0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3056 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2620 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.4933 pixels mm^-1	θmax = 74.7°, θmin = 4.7°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −17→16
Tmin = 0.598, Tmax = 1.000	l = −14→12
9185 measured reflections

Refinement

Refinement on F^2	79 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0947P)^2 + 0.4325P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3056 reflections	Δρmax = 0.36 e Å^−3
236 parameters	Δρmin = −0.41 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.0000	0.0000	0.0000	0.04884 (19)
O1	0.1295 (2)	−0.00417 (12)	0.17135 (17)	0.0593 (4)
O2	0.14105 (17)	−0.04725 (12)	−0.06650 (14)	0.0542 (4)
O3	−0.0495 (2)	−0.17394 (13)	0.04118 (16)	0.0709 (5)
H3A	−0.062 (4)	−0.190 (3)	0.107 (2)	0.106*
N1	−0.0919 (3)	−0.30935 (16)	−0.23815 (18)	0.0648 (5)
F1A	0.3127 (19)	0.0286 (12)	0.3949 (10)	0.184 (8)	0.59 (4)
F2A	0.4555 (18)	−0.074 (2)	0.3789 (15)	0.175 (7)	0.59 (4)
F3A	0.257 (3)	−0.116 (2)	0.3860 (13)	0.187 (7)	0.59 (4)
F1B	0.348 (2)	0.0289 (9)	0.3999 (13)	0.120 (5)	0.41 (4)
F2B	0.425 (3)	−0.1074 (16)	0.383 (2)	0.145 (8)	0.41 (4)
F3B	0.2202 (19)	−0.0888 (18)	0.4060 (14)	0.135 (5)	0.41 (4)
C1	0.3169 (4)	−0.0539 (4)	0.3451 (4)	0.1034 (14)
C2	0.2469 (3)	−0.0467 (2)	0.2023 (2)	0.0650 (6)
C3	0.3157 (3)	−0.0851 (2)	0.1273 (3)	0.0726 (7)
H3	0.4023	−0.1153	0.1659	0.087*
C4	0.2613 (2)	−0.08066 (17)	−0.0050 (2)	0.0549 (5)
C5	0.3461 (3)	−0.1165 (2)	−0.0825 (3)	0.0704 (7)
C6	0.2776 (4)	−0.1348 (2)	−0.2099 (3)	0.0820 (8)
H6	0.1795	−0.1274	−0.2448	0.098*
C7	0.3538 (5)	−0.1643 (3)	−0.2868 (4)	0.1048 (10)
H7	0.3071	−0.1760	−0.3724	0.126*
C8	0.4972 (5)	−0.1757 (4)	−0.2346 (5)	0.1203 (12)
H8	0.5486	−0.1964	−0.2846	0.144*
C9	0.5661 (5)	−0.1569 (4)	−0.1096 (6)	0.1233 (13)
H9	0.6645	−0.1631	−0.0768	0.148*
C10	0.4925 (4)	−0.1284 (3)	−0.0283 (5)	0.1014 (10)
H10	0.5400	−0.1180	0.0575	0.122*
C11	−0.0666 (3)	−0.23974 (17)	−0.1548 (2)	0.0579 (5)
H11	−0.0403	−0.1812	−0.1771	0.069*
C12	−0.0775 (3)	−0.24977 (16)	−0.0357 (2)	0.0544 (5)
C13	−0.1180 (4)	−0.3357 (2)	−0.0039 (3)	0.0785 (8)
H13	−0.1260	−0.3454	0.0752	0.094*
C14	−0.1466 (5)	−0.4077 (2)	−0.0917 (3)	0.0984 (10)
H14	−0.1758	−0.4665	−0.0729	0.118*
C15	−0.1317 (5)	−0.3921 (2)	−0.2072 (3)	0.0907 (9)
H15	−0.1503	−0.4413	−0.2654	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0547 (3)	0.0562 (3)	0.0366 (3)	0.00421 (18)	0.01693 (19)	−0.00072 (16)
O1	0.0645 (10)	0.0693 (11)	0.0413 (8)	0.0057 (8)	0.0145 (7)	−0.0052 (6)
O2	0.0619 (9)	0.0586 (9)	0.0461 (8)	0.0057 (7)	0.0236 (7)	0.0035 (7)
O3	0.1194 (15)	0.0592 (9)	0.0471 (8)	−0.0208 (10)	0.0455 (9)	−0.0097 (7)
N1	0.1027 (15)	0.0562 (11)	0.0481 (9)	−0.0071 (10)	0.0421 (10)	−0.0053 (8)
F1A	0.122 (6)	0.307 (18)	0.082 (4)	0.083 (8)	−0.020 (4)	−0.105 (7)
F2A	0.098 (5)	0.305 (19)	0.074 (5)	0.079 (9)	−0.032 (3)	−0.059 (9)
F3A	0.209 (12)	0.286 (16)	0.054 (4)	0.016 (11)	0.030 (5)	0.059 (7)
F1B	0.118 (8)	0.118 (8)	0.077 (5)	−0.001 (6)	−0.027 (5)	−0.036 (5)
F2B	0.173 (19)	0.152 (11)	0.067 (5)	0.084 (10)	−0.013 (8)	0.001 (6)
F3B	0.131 (7)	0.220 (12)	0.048 (4)	−0.014 (7)	0.023 (4)	0.003 (6)
C1	0.094 (2)	0.141 (4)	0.0528 (18)	0.032 (3)	−0.0031 (17)	−0.014 (2)
C2	0.0656 (14)	0.0714 (16)	0.0482 (12)	0.0046 (12)	0.0066 (10)	−0.0077 (11)
C3	0.0641 (14)	0.0820 (18)	0.0620 (14)	0.0186 (13)	0.0092 (12)	−0.0082 (13)
C4	0.0569 (12)	0.0509 (12)	0.0596 (12)	0.0013 (9)	0.0235 (10)	−0.0024 (10)
C5	0.0742 (14)	0.0598 (13)	0.0906 (17)	0.0045 (11)	0.0454 (13)	−0.0088 (12)
C6	0.1052 (19)	0.0756 (17)	0.0837 (17)	0.0127 (15)	0.0563 (15)	−0.0017 (14)
C7	0.139 (2)	0.094 (2)	0.110 (2)	0.014 (2)	0.080 (2)	−0.0074 (18)
C8	0.129 (3)	0.113 (3)	0.155 (3)	0.014 (2)	0.094 (2)	−0.017 (2)
C9	0.093 (2)	0.123 (3)	0.175 (3)	0.012 (2)	0.072 (2)	−0.022 (3)
C10	0.0732 (16)	0.101 (2)	0.139 (3)	0.0080 (15)	0.0488 (18)	−0.025 (2)
C11	0.0856 (14)	0.0530 (11)	0.0444 (11)	−0.0060 (11)	0.0343 (10)	−0.0022 (9)
C12	0.0783 (13)	0.0510 (11)	0.0434 (10)	−0.0039 (10)	0.0332 (9)	−0.0039 (8)
C13	0.137 (2)	0.0607 (14)	0.0575 (13)	−0.0161 (15)	0.0589 (14)	−0.0044 (11)
C14	0.182 (3)	0.0616 (15)	0.0744 (16)	−0.0310 (18)	0.0732 (18)	−0.0105 (13)
C15	0.164 (3)	0.0604 (14)	0.0671 (15)	−0.0230 (16)	0.0643 (16)	−0.0167 (12)

Geometric parameters (Å, º)

Cu1—O1	1.9204 (18)	C4—C5	1.499 (3)
Cu1—O1^i	1.9204 (18)	C5—C6	1.385 (5)
Cu1—O2	1.9296 (15)	C5—C10	1.391 (4)
Cu1—O2^i	1.9296 (15)	C6—C7	1.399 (5)
Cu1—O3	2.5841 (18)	C6—H6	0.9300
O1—C2	1.259 (3)	C7—C8	1.362 (7)
O2—C4	1.257 (3)	C7—H7	0.9300
O3—C12	1.346 (3)	C8—C9	1.364 (7)
O3—H3A	0.821 (10)	C8—H8	0.9300
N1—C15	1.322 (4)	C9—C10	1.415 (6)
N1—C11	1.323 (3)	C9—H9	0.9300
F1A—C1	1.302 (14)	C10—H10	0.9300
F2A—C1	1.339 (16)	C11—C12	1.389 (3)
F3A—C1	1.243 (18)	C11—H11	0.9300
F1B—C1	1.312 (12)	C12—C13	1.367 (4)
F2B—C1	1.27 (2)	C13—C14	1.380 (4)
F3B—C1	1.45 (2)	C13—H13	0.9300
C1—C2	1.520 (4)	C14—C15	1.376 (4)
C2—C3	1.371 (4)	C14—H14	0.9300
C3—C4	1.400 (4)	C15—H15	0.9300
C3—H3	0.9300
O1—Cu1—O1^i	180.0	O2—C4—C5	115.7 (2)
O1—Cu1—O2	92.68 (7)	C3—C4—C5	120.7 (2)
O1^i—Cu1—O2	87.32 (7)	C6—C5—C10	120.4 (3)
O1—Cu1—O2^i	87.32 (7)	C6—C5—C4	119.1 (3)
O1^i—Cu1—O2^i	92.68 (7)	C10—C5—C4	120.5 (3)
O2—Cu1—O2^i	180.0	C5—C6—C7	120.9 (4)
O1—Cu1—O3	84.01 (7)	C5—C6—H6	119.5
O1^i—Cu1—O3	95.99 (7)	C7—C6—H6	119.5
O2—Cu1—O3	87.12 (7)	C8—C7—C6	119.1 (4)
O2^i—Cu1—O3	92.88 (7)	C8—C7—H7	120.4
C2—O1—Cu1	122.51 (16)	C6—C7—H7	120.4
C4—O2—Cu1	127.33 (15)	C7—C8—C9	120.5 (4)
C12—O3—Cu1	130.93 (13)	C7—C8—H8	119.8
C12—O3—H3A	107 (3)	C9—C8—H8	119.8
Cu1—O3—H3A	121 (3)	C8—C9—C10	122.1 (4)
C15—N1—C11	118.4 (2)	C8—C9—H9	118.9
F3A—C1—F1A	112.7 (13)	C10—C9—H9	118.9
F2B—C1—F1B	109.8 (13)	C5—C10—C9	117.0 (4)
F3A—C1—F2A	109.1 (11)	C5—C10—H10	121.5
F1A—C1—F2A	104.8 (10)	C9—C10—H10	121.5
F2B—C1—F3B	105.5 (15)	N1—C11—C12	123.3 (2)
F1B—C1—F3B	99.8 (10)	N1—C11—H11	118.4
F3A—C1—C2	109.4 (7)	C12—C11—H11	118.4
F2B—C1—C2	115.3 (12)	O3—C12—C13	123.8 (2)
F1A—C1—C2	108.9 (7)	O3—C12—C11	118.1 (2)
F1B—C1—C2	112.7 (7)	C13—C12—C11	118.1 (2)
F2A—C1—C2	111.9 (9)	C12—C13—C14	118.5 (2)
F3B—C1—C2	112.4 (7)	C12—C13—H13	120.7
O1—C2—C3	129.6 (2)	C14—C13—H13	120.7
O1—C2—C1	111.9 (3)	C15—C14—C13	119.7 (3)
C3—C2—C1	118.5 (3)	C15—C14—H14	120.2
C2—C3—C4	122.8 (2)	C13—C14—H14	120.2
C2—C3—H3	118.6	N1—C15—C14	122.0 (3)
C4—C3—H3	118.6	N1—C15—H15	119.0
O2—C4—C3	123.6 (2)	C14—C15—H15	119.0
Cu1—O1—C2—C3	10.0 (5)	C3—C4—C5—C6	162.8 (3)
Cu1—O1—C2—C1	−170.1 (3)	O2—C4—C5—C10	160.7 (3)
F3A—C1—C2—O1	76.3 (18)	C3—C4—C5—C10	−19.2 (5)
F2B—C1—C2—O1	170.2 (17)	C10—C5—C6—C7	−0.8 (5)
F1A—C1—C2—O1	−47.3 (10)	C4—C5—C6—C7	177.1 (3)
F1B—C1—C2—O1	−62.6 (12)	C5—C6—C7—C8	0.5 (6)
F2A—C1—C2—O1	−162.7 (15)	C6—C7—C8—C9	−1.2 (8)
F3B—C1—C2—O1	49.2 (12)	C7—C8—C9—C10	2.2 (8)
F3A—C1—C2—C3	−103.8 (18)	C6—C5—C10—C9	1.7 (6)
F2B—C1—C2—C3	−9.9 (17)	C4—C5—C10—C9	−176.2 (4)
F1A—C1—C2—C3	132.6 (10)	C8—C9—C10—C5	−2.4 (8)
F1B—C1—C2—C3	117.3 (11)	C15—N1—C11—C12	1.1 (5)
F2A—C1—C2—C3	17.3 (16)	Cu1—O3—C12—C13	−172.0 (2)
F3B—C1—C2—C3	−130.8 (11)	Cu1—O3—C12—C11	7.0 (4)
O1—C2—C3—C4	1.0 (6)	N1—C11—C12—O3	−179.9 (3)
C1—C2—C3—C4	−178.9 (4)	N1—C11—C12—C13	−0.8 (4)
Cu1—O2—C4—C3	−3.0 (4)	O3—C12—C13—C14	178.7 (3)
Cu1—O2—C4—C5	177.12 (17)	C11—C12—C13—C14	−0.4 (5)
C2—C3—C4—O2	−5.1 (5)	C12—C13—C14—C15	1.1 (7)
C2—C3—C4—C5	174.9 (3)	C11—N1—C15—C14	−0.4 (6)
O2—C4—C5—C6	−17.2 (4)	C13—C14—C15—N1	−0.7 (7)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1^ii	0.82 (1)	1.87 (2)	2.669 (2)	165 (4)
C15—H15···O2^iii	0.93	2.44	3.339 (3)	163

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

Bis(3-hydroxypyridin-2-one-κO)bis(4,4,4-trifluoro-3-oxo-1-phenylbutan-1-olato-κ²O,O')copper(II) (III)

Crystal data

[Cu(C10H6F3O2)2(C5H5NO2)2]	Z = 1
Mr = 716.03	F(000) = 363
Triclinic, P1	Dx = 1.639 Mg m^−3
a = 7.5950 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6764 (4) Å	Cell parameters from 3204 reflections
c = 10.7507 (4) Å	θ = 1.0–27.5°
α = 108.710 (2)°	µ = 0.85 mm^−1
β = 101.727 (2)°	T = 293 K
γ = 93.650 (2)°	Block, green
V = 725.61 (5) Å^3	0.25 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3300 independent reflections
Radiation source: fine-focus sealed tube	2905 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 0.055 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.860, Tmax = 1.000	l = −13→13
5704 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.3054P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3300 reflections	Δρmax = 0.30 e Å^−3
243 parameters	Δρmin = −0.41 e Å^−3

Special details

Experimental. 185 frames in 4 sets of ω scans. Rotation/frame = 2.0 °. Crystal-detector distance = 25.0 mm. Measuring time = 20 s/°.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.0000	0.0000	0.03159 (11)
F1A	0.0866 (12)	−0.4652 (6)	−0.3582 (8)	0.0752 (17)	0.70 (3)
F2A	0.2240 (12)	−0.3169 (12)	−0.4232 (7)	0.081 (2)	0.70 (3)
F3A	−0.0052 (11)	−0.2623 (14)	−0.3483 (10)	0.082 (2)	0.70 (3)
F1B	0.044 (4)	−0.447 (3)	−0.3514 (16)	0.099 (6)	0.30 (3)
F2B	0.240 (3)	−0.345 (2)	−0.4194 (19)	0.080 (5)	0.30 (3)
F3B	0.027 (4)	−0.235 (4)	−0.359 (2)	0.107 (8)	0.30 (3)
O1	0.49487 (17)	−0.15660 (13)	0.07642 (12)	0.0332 (3)
O2	0.34867 (18)	−0.12645 (14)	−0.17153 (12)	0.0349 (3)
O3	0.23113 (18)	0.05953 (15)	0.10040 (13)	0.0369 (3)
O4	0.4467 (2)	0.07809 (19)	0.35085 (14)	0.0486 (4)
H4	0.4806	0.0951	0.2889	0.073*
N1	−0.0005 (2)	−0.07098 (18)	0.13890 (16)	0.0376 (4)
H1	−0.0672	−0.0750	0.0626	0.045*
C1	0.1407 (3)	−0.3234 (2)	−0.3307 (2)	0.0412 (4)
C2	0.2618 (2)	−0.25088 (19)	−0.18802 (17)	0.0323 (4)
C3	0.2636 (3)	−0.3231 (2)	−0.09762 (19)	0.0391 (4)
H3	0.1823	−0.4088	−0.1226	0.047*
C4	0.3834 (2)	−0.27387 (18)	0.03228 (17)	0.0306 (4)
C5	0.3844 (3)	−0.36172 (19)	0.12376 (19)	0.0335 (4)
C6	0.4900 (3)	−0.3036 (2)	0.2549 (2)	0.0416 (4)
H6	0.5594	−0.2115	0.2838	0.050*
C7	0.4934 (4)	−0.3812 (3)	0.3432 (2)	0.0543 (6)
H7	0.5647	−0.3415	0.4310	0.065*
C8	0.3902 (4)	−0.5179 (3)	0.3004 (3)	0.0591 (6)
H8	0.3925	−0.5705	0.3593	0.071*
C9	0.2853 (4)	−0.5760 (3)	0.1720 (3)	0.0614 (7)
H9	0.2160	−0.6680	0.1441	0.074*
C10	0.2804 (4)	−0.4995 (2)	0.0826 (2)	0.0496 (5)
H10	0.2078	−0.5400	−0.0048	0.059*
C11	0.1710 (2)	0.00097 (19)	0.17594 (17)	0.0309 (4)
C12	0.2756 (3)	0.0047 (2)	0.30454 (18)	0.0355 (4)
C13	0.2041 (3)	−0.0627 (3)	0.3800 (2)	0.0455 (5)
H13	0.2740	−0.0601	0.4627	0.055*
C14	0.0255 (3)	−0.1360 (3)	0.3337 (2)	0.0527 (6)
H14	−0.0234	−0.1830	0.3846	0.063*
C15	−0.0745 (3)	−0.1373 (3)	0.2139 (2)	0.0485 (5)
H15	−0.1939	−0.1836	0.1828	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03573 (18)	0.02923 (16)	0.02486 (16)	−0.00841 (12)	−0.00491 (12)	0.01239 (12)
F1A	0.107 (4)	0.036 (2)	0.051 (2)	−0.018 (3)	−0.027 (2)	0.0059 (15)
F2A	0.082 (4)	0.113 (4)	0.027 (2)	−0.045 (3)	0.001 (2)	0.014 (2)
F3A	0.052 (2)	0.089 (5)	0.068 (3)	0.016 (2)	−0.0214 (19)	0.001 (2)
F1B	0.109 (9)	0.116 (11)	0.039 (5)	−0.098 (8)	−0.024 (5)	0.028 (6)
F2B	0.061 (6)	0.117 (9)	0.033 (6)	0.022 (7)	0.009 (4)	−0.013 (5)
F3B	0.129 (15)	0.082 (9)	0.052 (6)	0.041 (11)	−0.063 (8)	−0.008 (5)
O1	0.0356 (7)	0.0311 (6)	0.0289 (6)	−0.0064 (5)	−0.0037 (5)	0.0137 (5)
O2	0.0380 (7)	0.0346 (6)	0.0273 (6)	−0.0093 (5)	−0.0025 (5)	0.0130 (5)
O3	0.0363 (7)	0.0423 (7)	0.0332 (7)	−0.0001 (6)	0.0009 (5)	0.0202 (6)
O4	0.0398 (8)	0.0713 (10)	0.0288 (7)	−0.0107 (7)	−0.0038 (6)	0.0199 (7)
N1	0.0310 (8)	0.0487 (9)	0.0329 (8)	0.0016 (7)	−0.0009 (6)	0.0198 (7)
C1	0.0431 (11)	0.0397 (10)	0.0317 (10)	−0.0091 (8)	−0.0022 (8)	0.0093 (8)
C2	0.0319 (9)	0.0329 (8)	0.0251 (8)	−0.0059 (7)	−0.0002 (7)	0.0067 (7)
C3	0.0426 (11)	0.0348 (9)	0.0331 (9)	−0.0135 (8)	−0.0012 (8)	0.0122 (8)
C4	0.0330 (9)	0.0289 (8)	0.0297 (9)	0.0000 (7)	0.0064 (7)	0.0112 (7)
C5	0.0383 (10)	0.0305 (8)	0.0357 (9)	0.0043 (7)	0.0119 (8)	0.0147 (7)
C6	0.0500 (12)	0.0419 (10)	0.0353 (10)	0.0008 (9)	0.0073 (9)	0.0190 (8)
C7	0.0705 (16)	0.0587 (13)	0.0404 (12)	0.0072 (12)	0.0104 (11)	0.0279 (11)
C8	0.0861 (19)	0.0537 (13)	0.0563 (14)	0.0127 (13)	0.0259 (13)	0.0379 (12)
C9	0.0871 (19)	0.0386 (11)	0.0649 (16)	−0.0043 (11)	0.0202 (14)	0.0275 (11)
C10	0.0680 (15)	0.0344 (10)	0.0457 (12)	−0.0062 (10)	0.0101 (11)	0.0173 (9)
C11	0.0316 (9)	0.0328 (8)	0.0269 (8)	0.0048 (7)	0.0019 (7)	0.0114 (7)
C12	0.0333 (9)	0.0443 (10)	0.0257 (8)	0.0028 (8)	0.0006 (7)	0.0121 (8)
C13	0.0400 (11)	0.0685 (14)	0.0327 (10)	0.0056 (10)	0.0034 (8)	0.0272 (10)
C14	0.0415 (11)	0.0796 (16)	0.0490 (12)	0.0016 (11)	0.0098 (10)	0.0400 (12)
C15	0.0341 (10)	0.0678 (14)	0.0486 (12)	−0.0018 (10)	0.0052 (9)	0.0310 (11)

Geometric parameters (Å, º)

Cu1—O2^i	1.9315 (12)	C3—C4	1.416 (2)
Cu1—O1	1.9434 (11)	C3—H3	0.9300
Cu1—O2	1.9315 (12)	C4—C5	1.491 (2)
Cu1—O1^i	1.9434 (11)	C5—C6	1.386 (3)
Cu1—O3	2.5127 (14)	C5—C10	1.394 (3)
F1A—C1	1.325 (5)	C6—C7	1.385 (3)
F2A—C1	1.297 (6)	C6—H6	0.9300
F3A—C1	1.297 (10)	C7—C8	1.381 (3)
F1B—C1	1.292 (12)	C7—H7	0.9300
F2B—C1	1.308 (15)	C8—C9	1.361 (4)
F3B—C1	1.31 (2)	C8—H8	0.9300
O1—C4	1.264 (2)	C9—C10	1.385 (3)
O2—C2	1.277 (2)	C9—H9	0.9300
O3—C11	1.266 (2)	C10—H10	0.9300
O4—C12	1.355 (2)	C11—C12	1.436 (2)
O4—H4	0.8200	C12—C13	1.361 (3)
N1—C11	1.355 (2)	C13—C14	1.403 (3)
N1—C15	1.360 (2)	C13—H13	0.9300
N1—H1	0.8600	C14—C15	1.351 (3)
C1—C2	1.531 (2)	C14—H14	0.9300
C2—C3	1.366 (2)	C15—H15	0.9300
O1^i—Cu1—O3	97.30 (5)	O1—C4—C5	116.62 (16)
O1—Cu1—O3	82.70 (5)	C3—C4—C5	120.47 (16)
O2^i—Cu1—O2	180.00 (6)	C6—C5—C10	118.77 (17)
O2^i—Cu1—O1	88.07 (5)	C6—C5—C4	119.01 (16)
O2—Cu1—O1	91.93 (5)	C10—C5—C4	122.22 (18)
O2^i—Cu1—O1^i	91.93 (5)	C7—C6—C5	120.7 (2)
O2—Cu1—O1^i	88.07 (5)	C7—C6—H6	119.6
O2—Cu1—O3	92.53 (5)	C5—C6—H6	119.6
O2^i—Cu1—O3	87.47 (5)	C8—C7—C6	119.6 (2)
O1—Cu1—O1^i	180.0	C8—C7—H7	120.2
C4—O1—Cu1	127.16 (11)	C6—C7—H7	120.2
C2—O2—Cu1	123.14 (11)	C9—C8—C7	120.2 (2)
C12—O4—H4	109.5	C9—C8—H8	119.9
C11—N1—C15	124.59 (16)	C7—C8—H8	119.9
C11—N1—H1	117.7	C8—C9—C10	120.8 (2)
C15—N1—H1	117.7	C8—C9—H9	119.6
F2A—C1—F3A	107.4 (7)	C10—C9—H9	119.6
F1B—C1—F2B	108.5 (13)	C9—C10—C5	119.9 (2)
F1B—C1—F3B	106.5 (14)	C9—C10—H10	120.1
F2B—C1—F3B	106.1 (16)	C5—C10—H10	120.1
F2A—C1—F1A	105.9 (5)	O3—C11—N1	121.10 (16)
F3A—C1—F1A	106.6 (6)	O3—C11—C12	123.72 (17)
F1B—C1—C2	115.2 (7)	N1—C11—C12	115.18 (16)
F2A—C1—C2	112.2 (4)	O4—C12—C13	120.18 (17)
F3A—C1—C2	112.1 (5)	O4—C12—C11	118.92 (16)
F2B—C1—C2	109.7 (9)	C13—C12—C11	120.89 (18)
F3B—C1—C2	110.3 (9)	C12—C13—C14	120.31 (18)
F1A—C1—C2	112.3 (3)	C12—C13—H13	119.8
O2—C2—C3	129.03 (16)	C14—C13—H13	119.8
O2—C2—C1	112.62 (15)	C15—C14—C13	119.0 (2)
C3—C2—C1	118.35 (16)	C15—C14—H14	120.5
C2—C3—C4	123.16 (17)	C13—C14—H14	120.5
C2—C3—H3	118.4	C14—C15—N1	120.0 (2)
C4—C3—H3	118.4	C14—C15—H15	120.0
O1—C4—C3	122.91 (16)	N1—C15—H15	120.0
Cu1—O2—C2—C3	−4.2 (3)	O1—C4—C5—C10	−173.96 (18)
Cu1—O2—C2—C1	175.55 (12)	C3—C4—C5—C10	5.3 (3)
F1B—C1—C2—O2	−177.4 (18)	C10—C5—C6—C7	0.4 (3)
F2A—C1—C2—O2	45.2 (7)	C4—C5—C6—C7	179.44 (19)
F3A—C1—C2—O2	−75.7 (6)	C5—C6—C7—C8	−0.1 (4)
F2B—C1—C2—O2	59.8 (12)	C6—C7—C8—C9	−0.2 (4)
F3B—C1—C2—O2	−57 (2)	C7—C8—C9—C10	0.1 (4)
F1A—C1—C2—O2	164.4 (5)	C8—C9—C10—C5	0.2 (4)
F1B—C1—C2—C3	2.4 (18)	C6—C5—C10—C9	−0.5 (3)
F2A—C1—C2—C3	−134.9 (6)	C4—C5—C10—C9	−179.5 (2)
F3A—C1—C2—C3	104.1 (6)	C15—N1—C11—O3	179.61 (19)
F2B—C1—C2—C3	−120.4 (12)	C15—N1—C11—C12	−0.3 (3)
F3B—C1—C2—C3	123 (2)	O3—C11—C12—O4	1.9 (3)
F1A—C1—C2—C3	−15.8 (5)	N1—C11—C12—O4	−178.15 (17)
O2—C2—C3—C4	−6.7 (4)	O3—C11—C12—C13	−178.84 (19)
C1—C2—C3—C4	173.51 (18)	N1—C11—C12—C13	1.1 (3)
Cu1—O1—C4—C3	13.0 (3)	O4—C12—C13—C14	178.6 (2)
Cu1—O1—C4—C5	−167.84 (12)	C11—C12—C13—C14	−0.6 (3)
C2—C3—C4—O1	2.0 (3)	C12—C13—C14—C15	−0.6 (4)
C2—C3—C4—C5	−177.11 (18)	C13—C14—C15—N1	1.4 (4)
O1—C4—C5—C6	7.1 (3)	C11—N1—C15—C14	−0.9 (4)
C3—C4—C5—C6	−173.70 (18)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^i	0.82	2.06	2.8380 (19)	160
O4—H4···O3	0.82	2.39	2.7970 (18)	111
N1—H1···O3^ii	0.86	1.99	2.842 (2)	173
C15—H15···O1^iii	0.93	2.48	3.271 (2)	143
C9—H9···O3^iv	0.93	2.54	3.338 (3)	144

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