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The title complex, [Cu2(C20H16F2N4O2)(CH4O)2](ClO4)2, was synthesized by cyclo-condensation between ethyl­enediamine and 2,6-diformyl-4-fluoro­phenol in the presence of CuII ions. This dinuclear copper complex is centrosymmetric. Both Cu atoms are in a distorted tetra­hedral geometry, coordinated by three O atoms and two N atoms. The two Cu atoms are bridged by two endogenous phenol O atoms, with a Cu...Cu distance of 2.8998 (7) Å. In the crystal structure, the perchlorate ions link the macrocycles through inter- and intra­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047009/hg2298sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047009/hg2298Isup2.hkl
Contains datablock I

CCDC reference: 667102

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.086
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O2 .. 11.82 su
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C10 .. 2.97 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (3) 2.93
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Since the Robson-style homodinuclear macrocyclic complexes were synthesized via template condensation, there has been an increasing interest in the research of these complexes (Pilkington & Robson, 1970; Aono et al., 1997). In the past, most of these complexes were synthesized by cyclocondensation between 2,6-diformyl-4-R-phenol (R = CH3, Cl, Br, CH3O, n-butyl) and alkylenediamine by stepwise template reaction (Gou & Fenton, 1994; Adams et al., 1995). But only a few crystal structures of the complexes with fluorophenyl substituents have been published (Chen et al., 2005; Chen et al., 2007). In this paper, we report the synthesis and crystal structure of the title complex with fluorophenyl substituents.

The crystal structure of the title complex is shown in Fig. 1. Selected bond distances and angles relevant to the coordination geometries of copper atoms are listed in Table 1. Each copper atom is coordinated by two endogenous phenolic O atoms, two azomethine nitrogen atoms and one oxygen atom from methanol molecule. The coordination polyhedron of each CuII can be described as distorted tetragonal pyramid. The deviation of Cu1 and Cu1* from the mean plane of atoms N1, N2, O1, O1* [mean deviation = 0.0182 (3) Å] and N1*, N2*, O1, O1* [mean deviation = 0.0182 (3) Å] are 0.1713 (3)Å and -0.1714 (3) Å, respectively. The two atom groups O1, O1*, Cu1, Cu1* and N1, N2, N1*, N2* are almost coplanar with the dihedral angle of the two planes 7.0 (3)°. The parallelogram formed by atoms N1, N2, N1*, N2* approximates a rectangle with the angle of N1—N2—N1* 89.7 (3)°. The Cu···Cu distance is 2.8998 (7) Å. The Cu—N bond lengths are 1.886 (2) and 1.885 (2) Å. the Cu—O bondlengths to the methanol molecule are both 2.364 (2) Å, which is much longer than those for the phenolic O atoms [1.8905 (17)Å and 1.9021 (17) Å]. The crystal structure of is stabilized by intramolecular and intermolecular hydrogen bonds of types O—H···O and C—H···O, where O atoms belong to methanol molecules or perchlorate ions.

Related literature top

For related literature, see: Adams et al. (1995); Aono et al. (1997); Bruker (2000); Chen et al. (2005, 2007); Gou & Fenton (1994); Pilkington & Robson (1970); Taniguchi (1984).

Experimental top

2, 6-Diformyl-4-fluorophenol was prepared according to the literature method of Taniguchi (1984). To a solution of 2, 6-diformyl-4-fluorophenol (0.6 mmol, 0.101 g) in absolute methanol (10 ml) was added methanol solution (10 ml) of Cu(OAc)2H2O (0.3 mmol, 0.06 g). The solution was stirred vigorously while a methanol solution (10 ml) containing ethylenediamine (0.6 mmol, 0.036 g) was added dropwise over a period of 2 h. The mixture was still stirred for 12 h at room temperature. Then, the Cu(ClO4)26H2O (0.3 mmol, 0.111 g) was added to the solution and stirred for 6 h at room temperature. The dark-green block-shaped crystals suitable for X-ray diffraction were obtained by slow diffusion of ethyl acetate into the mother solution over a period of three weeks.

Refinement top

All H atoms for C—H distances were placed in calculated positions in the range 0.93–0.97 Å, and included in the refinement in the riding-model approximation, with U(H) set to 1.2–1.5Ueq(C). The methanol H atom was located in a difference Fourier map, and was refined with an O–H distance restraint of 0.808 Å; its temperature factor was set to 1.5Ueq(O).

Structure description top

Since the Robson-style homodinuclear macrocyclic complexes were synthesized via template condensation, there has been an increasing interest in the research of these complexes (Pilkington & Robson, 1970; Aono et al., 1997). In the past, most of these complexes were synthesized by cyclocondensation between 2,6-diformyl-4-R-phenol (R = CH3, Cl, Br, CH3O, n-butyl) and alkylenediamine by stepwise template reaction (Gou & Fenton, 1994; Adams et al., 1995). But only a few crystal structures of the complexes with fluorophenyl substituents have been published (Chen et al., 2005; Chen et al., 2007). In this paper, we report the synthesis and crystal structure of the title complex with fluorophenyl substituents.

The crystal structure of the title complex is shown in Fig. 1. Selected bond distances and angles relevant to the coordination geometries of copper atoms are listed in Table 1. Each copper atom is coordinated by two endogenous phenolic O atoms, two azomethine nitrogen atoms and one oxygen atom from methanol molecule. The coordination polyhedron of each CuII can be described as distorted tetragonal pyramid. The deviation of Cu1 and Cu1* from the mean plane of atoms N1, N2, O1, O1* [mean deviation = 0.0182 (3) Å] and N1*, N2*, O1, O1* [mean deviation = 0.0182 (3) Å] are 0.1713 (3)Å and -0.1714 (3) Å, respectively. The two atom groups O1, O1*, Cu1, Cu1* and N1, N2, N1*, N2* are almost coplanar with the dihedral angle of the two planes 7.0 (3)°. The parallelogram formed by atoms N1, N2, N1*, N2* approximates a rectangle with the angle of N1—N2—N1* 89.7 (3)°. The Cu···Cu distance is 2.8998 (7) Å. The Cu—N bond lengths are 1.886 (2) and 1.885 (2) Å. the Cu—O bondlengths to the methanol molecule are both 2.364 (2) Å, which is much longer than those for the phenolic O atoms [1.8905 (17)Å and 1.9021 (17) Å]. The crystal structure of is stabilized by intramolecular and intermolecular hydrogen bonds of types O—H···O and C—H···O, where O atoms belong to methanol molecules or perchlorate ions.

For related literature, see: Adams et al. (1995); Aono et al. (1997); Bruker (2000); Chen et al. (2005, 2007); Gou & Fenton (1994); Pilkington & Robson (1970); Taniguchi (1984).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. A view of the title complex, showing the labeling of the non-H atoms and 30% probability ellipsoids. H atoms have been omitted. Atoms marked with an asterisk(*) are at the symmetry-generated position (Symmetry code for primed atoms: -x, -y, 1 - z).
[µ-10,21-Difluoro-3,6,14,17-tetrazatricyclo[17.3.1.18,12]tetracosa-\1(23),2,6,8,10,12 (24),13,17,19,21-decaene-23,24-diolato-\k4N3,N6,O23,O24:κ4N14,N17,O23,O24]bis[methanolcopper(II)] bis(perchlorate) top
Crystal data top
[Cu2(C20H16F2N4O2)(CH4O)2](ClO4)2Z = 1
Mr = 772.43F(000) = 390
Triclinic, P1Dx = 1.889 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8124 (13) ÅCell parameters from 1982 reflections
b = 8.4132 (15) Åθ = 2.5–29.0°
c = 10.8144 (18) ŵ = 1.85 mm1
α = 103.127 (3)°T = 296 K
β = 96.272 (3)°Block, blue
γ = 97.569 (3)°0.20 × 0.20 × 0.10 mm
V = 679.0 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2633 independent reflections
Radiation source: fine-focus sealed tube2268 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ and ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.709, Tmax = 0.837k = 109
3953 measured reflectionsl = 1311
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0487P)2 + 0.1892P]
where P = (Fo2 + 2Fc2)/3
2633 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
[Cu2(C20H16F2N4O2)(CH4O)2](ClO4)2γ = 97.569 (3)°
Mr = 772.43V = 679.0 (2) Å3
Triclinic, P1Z = 1
a = 7.8124 (13) ÅMo Kα radiation
b = 8.4132 (15) ŵ = 1.85 mm1
c = 10.8144 (18) ÅT = 296 K
α = 103.127 (3)°0.20 × 0.20 × 0.10 mm
β = 96.272 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2633 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2268 reflections with I > 2σ(I)
Tmin = 0.709, Tmax = 0.837Rint = 0.011
3953 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.31 e Å3
2633 reflectionsΔρmin = 0.24 e Å3
203 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.01488 (4)0.09325 (4)0.37234 (3)0.04503 (13)
C10.2955 (3)0.1735 (3)0.5123 (2)0.0370 (5)
C20.3570 (3)0.3063 (3)0.6204 (2)0.0354 (5)
C30.5275 (3)0.3910 (3)0.6307 (2)0.0420 (6)
H30.57190.47990.70030.050*
C40.6272 (3)0.3414 (3)0.5374 (3)0.0442 (6)
C50.5696 (3)0.2153 (3)0.4317 (2)0.0417 (6)
H50.64210.18830.37000.050*
C60.4006 (3)0.1256 (3)0.4157 (2)0.0358 (5)
C70.3459 (3)0.0089 (3)0.2995 (2)0.0390 (5)
H70.42480.02650.24120.047*
C80.1400 (4)0.2311 (3)0.1512 (2)0.0459 (6)
H8A0.23960.27600.11970.055*
H8B0.08600.18230.08690.055*
C90.0077 (3)0.3705 (3)0.1745 (2)0.0432 (6)
H9A0.06610.42790.09460.052*
H9B0.06940.44980.20560.052*
C100.2534 (3)0.3680 (3)0.2794 (2)0.0386 (5)
H100.30240.46450.21790.046*
C110.0536 (4)0.2138 (4)0.2389 (4)0.0703 (9)
H11A0.00620.28640.32100.105*
H11B0.13550.26490.19470.105*
H11C0.03910.19240.18910.105*
Cl20.37721 (9)0.23525 (8)0.03502 (6)0.04801 (18)
F10.7932 (2)0.4251 (2)0.54902 (17)0.0679 (5)
N10.1980 (3)0.1037 (2)0.27212 (19)0.0394 (5)
N20.1008 (3)0.2997 (2)0.27003 (18)0.0368 (4)
O10.1343 (2)0.0926 (2)0.49992 (17)0.0534 (5)
O20.1394 (3)0.0628 (2)0.25626 (19)0.0533 (5)
O30.2525 (4)0.0916 (3)0.0236 (3)0.0959 (9)
O40.4365 (3)0.2247 (4)0.0854 (2)0.0825 (7)
O50.2965 (4)0.3775 (3)0.0673 (3)0.0877 (8)
O60.5174 (3)0.2428 (3)0.1313 (2)0.0847 (8)
H20.178 (6)0.007 (5)0.185 (2)0.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0476 (2)0.0403 (2)0.03627 (19)0.00728 (14)0.01882 (14)0.01080 (13)
C10.0417 (13)0.0348 (12)0.0315 (12)0.0000 (10)0.0084 (10)0.0038 (10)
C20.0400 (12)0.0314 (12)0.0326 (12)0.0025 (10)0.0041 (10)0.0056 (9)
C30.0412 (13)0.0396 (13)0.0391 (13)0.0004 (11)0.0001 (11)0.0036 (11)
C40.0329 (12)0.0492 (15)0.0474 (15)0.0003 (11)0.0016 (11)0.0111 (12)
C50.0363 (12)0.0491 (15)0.0408 (14)0.0062 (11)0.0098 (10)0.0119 (11)
C60.0395 (12)0.0365 (12)0.0322 (12)0.0049 (10)0.0085 (10)0.0089 (10)
C70.0430 (13)0.0401 (13)0.0355 (13)0.0083 (11)0.0170 (10)0.0065 (10)
C80.0538 (15)0.0460 (14)0.0324 (13)0.0045 (12)0.0163 (11)0.0045 (11)
C90.0511 (14)0.0359 (13)0.0363 (13)0.0047 (11)0.0125 (11)0.0056 (10)
C100.0480 (14)0.0310 (12)0.0316 (12)0.0035 (10)0.0026 (10)0.0001 (9)
C110.0641 (19)0.063 (2)0.089 (3)0.0053 (16)0.0208 (18)0.0283 (19)
Cl20.0509 (4)0.0473 (4)0.0397 (4)0.0023 (3)0.0051 (3)0.0021 (3)
F10.0386 (8)0.0844 (13)0.0654 (11)0.0136 (8)0.0076 (8)0.0003 (9)
N10.0470 (11)0.0349 (11)0.0326 (10)0.0030 (9)0.0131 (9)0.0008 (8)
N20.0432 (11)0.0340 (10)0.0295 (10)0.0037 (9)0.0090 (8)0.0002 (8)
O10.0478 (10)0.0536 (11)0.0412 (10)0.0181 (9)0.0211 (8)0.0163 (8)
O20.0550 (11)0.0431 (11)0.0543 (12)0.0014 (9)0.0079 (9)0.0001 (9)
O30.0901 (18)0.0763 (18)0.103 (2)0.0284 (14)0.0149 (16)0.0088 (15)
O40.0919 (18)0.113 (2)0.0528 (13)0.0309 (16)0.0281 (13)0.0240 (14)
O50.0994 (18)0.0747 (17)0.0813 (17)0.0365 (15)0.0077 (15)0.0065 (13)
O60.0933 (18)0.0789 (17)0.0677 (16)0.0063 (14)0.0271 (14)0.0115 (13)
Geometric parameters (Å, º) top
Cu1—N21.885 (2)C8—N11.473 (3)
Cu1—N11.886 (2)C8—C91.543 (4)
Cu1—O11.8905 (17)C8—H8A0.9700
Cu1—O1i1.9021 (17)C8—H8B0.9700
Cu1—O22.364 (2)C9—N21.479 (3)
Cu1—Cu1i2.8998 (7)C9—H9A0.9700
C1—O11.327 (3)C9—H9B0.9700
C1—C21.409 (3)C10—N21.278 (3)
C1—C61.418 (3)C10—C2i1.465 (3)
C2—C31.406 (3)C10—H100.9300
C2—C10i1.465 (3)C11—O21.418 (4)
C3—C41.366 (4)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.359 (4)C11—H11C0.9600
C4—F11.370 (3)Cl2—O61.411 (2)
C5—C61.404 (3)Cl2—O41.417 (2)
C5—H50.9300Cl2—O51.417 (2)
C6—C71.467 (3)Cl2—O31.421 (3)
C7—N11.279 (3)O1—Cu1i1.9022 (17)
C7—H70.9300O2—H20.810 (10)
N2—Cu1—N190.13 (8)C9—C8—H8A109.8
N2—Cu1—O1169.19 (9)N1—C8—H8B109.8
N1—Cu1—O194.42 (8)C9—C8—H8B109.8
N2—Cu1—O1i93.32 (8)H8A—C8—H8B108.2
N1—Cu1—O1i167.69 (9)N2—C9—C8109.70 (19)
O1—Cu1—O1i80.26 (8)N2—C9—H9A109.7
N2—Cu1—O294.58 (8)C8—C9—H9A109.7
N1—Cu1—O295.01 (8)N2—C9—H9B109.7
O1—Cu1—O294.78 (8)C8—C9—H9B109.7
O1i—Cu1—O296.48 (8)H9A—C9—H9B108.2
N2—Cu1—Cu1i132.72 (6)N2—C10—C2i125.1 (2)
N1—Cu1—Cu1i133.72 (6)N2—C10—H10117.5
O1—Cu1—Cu1i40.28 (5)C2i—C10—H10117.5
O1i—Cu1—Cu1i39.98 (5)O2—C11—H11A109.5
O2—Cu1—Cu1i97.38 (5)O2—C11—H11B109.5
O1—C1—C2119.1 (2)H11A—C11—H11B109.5
O1—C1—C6119.2 (2)O2—C11—H11C109.5
C2—C1—C6121.7 (2)H11A—C11—H11C109.5
C3—C2—C1118.1 (2)H11B—C11—H11C109.5
C3—C2—C10i117.1 (2)O6—Cl2—O4110.58 (16)
C1—C2—C10i124.8 (2)O6—Cl2—O5109.79 (16)
C4—C3—C2119.3 (2)O4—Cl2—O5109.75 (16)
C4—C3—H3120.4O6—Cl2—O3109.72 (18)
C2—C3—H3120.4O4—Cl2—O3107.74 (18)
C5—C4—C3123.6 (2)O5—Cl2—O3109.22 (18)
C5—C4—F1117.9 (2)C7—N1—C8124.5 (2)
C3—C4—F1118.5 (2)C7—N1—Cu1126.02 (17)
C4—C5—C6120.0 (2)C8—N1—Cu1109.37 (15)
C4—C5—H5120.0C10—N2—C9124.4 (2)
C6—C5—H5120.0C10—N2—Cu1125.07 (17)
C5—C6—C1117.4 (2)C9—N2—Cu1110.53 (15)
C5—C6—C7117.4 (2)C1—O1—Cu1130.12 (15)
C1—C6—C7125.2 (2)C1—O1—Cu1i128.21 (16)
N1—C7—C6125.0 (2)Cu1—O1—Cu1i99.74 (8)
N1—C7—H7117.5C11—O2—Cu1119.82 (19)
C6—C7—H7117.5C11—O2—H2105 (4)
N1—C8—C9109.45 (19)Cu1—O2—H2110 (4)
N1—C8—H8A109.8
O1—C1—C2—C3179.4 (2)C2i—C10—N2—C9174.9 (2)
C6—C1—C2—C30.2 (4)C2i—C10—N2—Cu16.7 (3)
O1—C1—C2—C10i2.3 (4)C8—C9—N2—C10155.9 (2)
C6—C1—C2—C10i176.8 (2)C8—C9—N2—Cu122.7 (2)
C1—C2—C3—C40.6 (4)N1—Cu1—N2—C10174.2 (2)
C10i—C2—C3—C4177.9 (2)O1—Cu1—N2—C1070.8 (5)
C2—C3—C4—C51.6 (4)O1i—Cu1—N2—C1017.6 (2)
C2—C3—C4—F1179.9 (2)O2—Cu1—N2—C1079.2 (2)
C3—C4—C5—C61.6 (4)Cu1i—Cu1—N2—C1025.3 (2)
F1—C4—C5—C6179.9 (2)N1—Cu1—N2—C94.38 (17)
C4—C5—C6—C10.7 (4)O1—Cu1—N2—C9110.6 (4)
C4—C5—C6—C7179.9 (2)O1i—Cu1—N2—C9163.80 (16)
O1—C1—C6—C5179.4 (2)O2—Cu1—N2—C999.42 (16)
C2—C1—C6—C50.2 (3)Cu1i—Cu1—N2—C9156.14 (13)
O1—C1—C6—C70.2 (4)C2—C1—O1—Cu1177.49 (18)
C2—C1—C6—C7178.9 (2)C6—C1—O1—Cu13.3 (4)
C5—C6—C7—N1178.6 (2)C2—C1—O1—Cu1i16.6 (3)
C1—C6—C7—N12.3 (4)C6—C1—O1—Cu1i164.21 (18)
N1—C8—C9—N235.4 (3)N2—Cu1—O1—C1110.7 (4)
C6—C7—N1—C8175.7 (2)N1—Cu1—O1—C14.0 (2)
C6—C7—N1—Cu10.6 (4)O1i—Cu1—O1—C1164.9 (3)
C9—C8—N1—C7152.6 (2)O2—Cu1—O1—C199.4 (2)
C9—C8—N1—Cu131.5 (2)Cu1i—Cu1—O1—C1164.9 (3)
N2—Cu1—N1—C7168.4 (2)N2—Cu1—O1—Cu1i54.2 (4)
O1—Cu1—N1—C71.8 (2)N1—Cu1—O1—Cu1i168.81 (10)
O1i—Cu1—N1—C762.0 (5)O1i—Cu1—O1—Cu1i0.0
O2—Cu1—N1—C797.0 (2)O2—Cu1—O1—Cu1i95.78 (9)
Cu1i—Cu1—N1—C78.2 (3)N2—Cu1—O2—C11144.7 (2)
N2—Cu1—N1—C815.90 (17)N1—Cu1—O2—C1154.2 (2)
O1—Cu1—N1—C8173.91 (17)O1—Cu1—O2—C1140.7 (2)
O1i—Cu1—N1—C8122.3 (4)O1i—Cu1—O2—C11121.4 (2)
O2—Cu1—N1—C878.71 (17)Cu1i—Cu1—O2—C1181.1 (2)
Cu1i—Cu1—N1—C8176.09 (13)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O6ii0.932.583.456 (4)156
C7—H7···O4iii0.932.533.364 (3)150
C5—H5···O2iv0.932.433.319 (3)161
C3—H3···O5v0.932.563.431 (4)156
C9—H9A···O5vi0.972.523.321 (4)140
O2—H2···O4vi0.81 (1)2.57 (4)3.195 (3)135 (4)
O2—H2···O3vi0.81 (1)2.20 (2)2.993 (4)166 (5)
Symmetry codes: (ii) x1, y1, z; (iii) x+1, y, z; (iv) x+1, y, z; (v) x+1, y+1, z+1; (vi) x, y, z.

Experimental details

Crystal data
Chemical formula[Cu2(C20H16F2N4O2)(CH4O)2](ClO4)2
Mr772.43
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.8124 (13), 8.4132 (15), 10.8144 (18)
α, β, γ (°)103.127 (3), 96.272 (3), 97.569 (3)
V3)679.0 (2)
Z1
Radiation typeMo Kα
µ (mm1)1.85
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.709, 0.837
No. of measured, independent and
observed [I > 2σ(I)] reflections
3953, 2633, 2268
Rint0.011
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.086, 1.07
No. of reflections2633
No. of parameters203
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.24

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O6i0.932.583.456 (4)156
C7—H7···O4ii0.932.533.364 (3)150
C5—H5···O2iii0.932.433.319 (3)161
C3—H3···O5iv0.932.563.431 (4)156
C9—H9A···O5v0.972.523.321 (4)140
O2—H2···O4v0.810 (10)2.57 (4)3.195 (3)135 (4)
O2—H2···O3v0.810 (10)2.199 (16)2.993 (4)166 (5)
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x, y, z.
 

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