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The title compound, trans-[Cu(C5HF6O2)2(C12H10N2)2], consists of monomeric units built up by a copper metal ion (lying on a center of symmetry) octa­hedrally coordinated by one oxygen-chelating hexa­fluoro­acetyl­acetonate (hfac) group, a nitro­gen-bound 1-(2-pyrid­yl)-2-(4-pyrid­yl)ethyl­ene (2,4-bpye) ligand, and their symmetry equivalents generated by the symmetry center at the metal site. The monomers inter­act with each other through π–π bonding between pyridine rings, and are organized as chains running along [11\overline{1}]. The stabilization of this architecture of chains is associated with a number of weak C—H...F hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048574/dn2091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048574/dn2091Isup2.hkl
Contains datablock I

CCDC reference: 629650

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.010 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.193
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Sheldrick, 2000); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2000) and PLATON (Spek, 2003).

trans-Bis(hexafluoroacetylacetonato-κ2O,O')bis[trans-1-(2-pyridyl)- 2-(4-pyridyl)ethylene-κN4]copper(II) top
Crystal data top
[Cu(C5HF6O2)2(C12H10N2)2]Z = 1
Mr = 842.10F(000) = 423
Triclinic, P1Dx = 1.530 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1513 (18) ÅCell parameters from 25 reflections
b = 10.009 (2) Åθ = 7.5–17.5°
c = 10.424 (2) ŵ = 0.70 mm1
α = 74.23 (3)°T = 295 K
β = 84.12 (3)°Plate, green
γ = 87.98 (3)°0.35 × 0.25 × 0.12 mm
V = 913.9 (3) Å3
Data collection top
Rigaku AFC-6
diffractometer
1907 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω/2θ scansh = 1010
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.80, Tmax = 0.91l = 212
4174 measured reflections3 standard reflections every 150 reflections
3219 independent reflections intensity decay: 2%
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0916P)2 + 1.5666P]
where P = (Fo2 + 2Fc2)/3
3219 reflections(Δ/σ)max < 0.001
306 parametersΔρmax = 0.41 e Å3
224 restraintsΔρmin = 0.48 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.50000.50000.50000.0491 (4)
C10.4159 (7)0.1611 (7)0.8436 (7)0.0622 (16)
H10.46450.12300.91950.075*
C20.4714 (7)0.2770 (7)0.7507 (7)0.0624 (17)
H20.55720.31530.76540.075*
N30.4069 (5)0.3377 (5)0.6388 (5)0.0489 (11)
C40.2822 (6)0.2815 (6)0.6220 (6)0.0557 (15)
H40.23490.32310.54610.067*
C50.2209 (6)0.1658 (7)0.7110 (6)0.0581 (15)
H50.13390.13100.69450.070*
C60.2882 (6)0.0993 (6)0.8268 (6)0.0546 (15)
C70.2331 (7)0.0268 (7)0.9256 (7)0.0623 (16)
H70.28480.05871.00050.075*
C80.1180 (7)0.1006 (7)0.9202 (7)0.0625 (16)
H80.06370.06880.84700.075*
C90.0692 (7)0.2280 (6)1.0202 (6)0.0566 (15)
N100.1496 (7)0.2752 (6)1.1242 (6)0.0770 (16)
C110.1039 (9)0.3920 (9)1.2154 (8)0.087 (2)
H110.15930.42771.28720.105*
C120.0197 (9)0.4618 (8)1.2086 (9)0.083 (2)
H120.04810.54191.27490.100*
C130.1010 (9)0.4111 (8)1.1018 (9)0.085 (2)
H130.18500.45681.09400.102*
C140.0565 (8)0.2929 (7)1.0079 (8)0.0715 (18)
H140.11090.25610.93550.086*
C150.5876 (7)0.7295 (6)0.7783 (6)0.093 (3)
C160.5004 (6)0.6852 (6)0.6789 (6)0.0584 (15)
C170.3788 (7)0.7634 (7)0.6331 (7)0.075 (2)
H170.35730.84330.66090.090*
C180.2870 (6)0.7301 (7)0.5482 (6)0.0588 (16)
C190.1604 (7)0.8327 (6)0.5042 (6)0.082 (2)
O200.5549 (4)0.5799 (4)0.6491 (4)0.0602 (11)
O210.2937 (4)0.6303 (4)0.5009 (4)0.0583 (11)
F220.535 (4)0.663 (3)0.8997 (12)0.210 (12)0.46 (4)
F230.7287 (10)0.705 (3)0.768 (4)0.160 (10)0.46 (4)
F240.571 (3)0.8625 (11)0.768 (3)0.123 (8)0.46 (4)
F22'0.535 (2)0.8339 (18)0.822 (2)0.151 (8)0.54 (4)
F23'0.607 (3)0.6265 (15)0.8846 (14)0.136 (7)0.54 (4)
F24'0.7200 (11)0.765 (2)0.7190 (16)0.112 (6)0.54 (4)
F250.1515 (14)0.9427 (10)0.5496 (12)0.133 (5)0.610 (16)
F260.0329 (8)0.7707 (11)0.5360 (13)0.141 (6)0.610 (16)
F270.1730 (11)0.8803 (10)0.3721 (6)0.112 (4)0.610 (16)
F25'0.1983 (18)0.9551 (11)0.427 (2)0.203 (12)0.390 (16)
F26'0.0879 (15)0.854 (2)0.6136 (9)0.107 (6)0.390 (16)
F27'0.0649 (14)0.7824 (19)0.445 (2)0.127 (7)0.390 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0491 (6)0.0501 (7)0.0520 (7)0.0060 (4)0.0138 (5)0.0182 (5)
C10.058 (4)0.064 (4)0.062 (4)0.003 (3)0.020 (3)0.008 (3)
C20.050 (3)0.069 (4)0.072 (4)0.002 (3)0.023 (3)0.019 (4)
N30.047 (3)0.049 (3)0.051 (3)0.004 (2)0.013 (2)0.012 (2)
C40.051 (3)0.061 (4)0.054 (4)0.002 (3)0.013 (3)0.010 (3)
C50.048 (3)0.068 (4)0.060 (4)0.004 (3)0.015 (3)0.017 (3)
C60.051 (3)0.055 (4)0.058 (4)0.007 (3)0.010 (3)0.015 (3)
C70.055 (4)0.067 (4)0.064 (4)0.006 (3)0.014 (3)0.014 (3)
C80.060 (4)0.067 (4)0.061 (4)0.000 (3)0.011 (3)0.017 (3)
C90.059 (4)0.052 (4)0.058 (4)0.004 (3)0.000 (3)0.015 (3)
N100.075 (4)0.077 (4)0.074 (4)0.007 (3)0.017 (3)0.008 (3)
C110.086 (5)0.088 (6)0.078 (5)0.004 (5)0.017 (4)0.001 (5)
C120.089 (6)0.058 (4)0.089 (6)0.010 (4)0.009 (5)0.004 (4)
C130.071 (5)0.076 (5)0.118 (7)0.017 (4)0.002 (5)0.043 (5)
C140.067 (4)0.070 (5)0.081 (5)0.008 (4)0.010 (4)0.024 (4)
C150.088 (6)0.101 (7)0.109 (7)0.019 (5)0.035 (6)0.055 (6)
C160.062 (4)0.059 (4)0.060 (4)0.005 (3)0.014 (3)0.023 (3)
C170.076 (4)0.076 (5)0.090 (5)0.026 (4)0.026 (4)0.048 (4)
C180.056 (4)0.064 (4)0.058 (4)0.013 (3)0.010 (3)0.021 (3)
C190.080 (5)0.083 (5)0.089 (6)0.024 (4)0.015 (5)0.031 (5)
O200.058 (2)0.060 (3)0.070 (3)0.010 (2)0.019 (2)0.027 (2)
O210.061 (3)0.053 (2)0.063 (3)0.0014 (19)0.012 (2)0.017 (2)
F220.32 (2)0.22 (2)0.112 (13)0.051 (18)0.081 (14)0.049 (13)
F230.132 (13)0.188 (18)0.22 (2)0.089 (12)0.136 (13)0.127 (15)
F240.140 (13)0.118 (11)0.155 (16)0.006 (9)0.046 (11)0.097 (10)
F22'0.158 (13)0.204 (16)0.155 (14)0.077 (12)0.074 (10)0.143 (12)
F23'0.178 (15)0.163 (12)0.065 (8)0.012 (10)0.059 (8)0.009 (7)
F24'0.084 (8)0.133 (12)0.135 (10)0.004 (6)0.051 (7)0.046 (9)
F250.165 (10)0.101 (7)0.164 (10)0.078 (7)0.088 (8)0.069 (7)
F260.063 (5)0.172 (9)0.152 (10)0.023 (5)0.015 (6)0.016 (8)
F270.140 (8)0.086 (7)0.106 (6)0.040 (6)0.043 (6)0.015 (5)
F25'0.153 (15)0.138 (16)0.23 (2)0.063 (12)0.031 (16)0.065 (16)
F26'0.088 (9)0.130 (13)0.124 (11)0.068 (9)0.039 (8)0.068 (10)
F27'0.111 (11)0.159 (12)0.142 (12)0.047 (9)0.082 (9)0.072 (10)
Geometric parameters (Å, º) top
Cu1—N32.006 (5)C11—H110.9300
Cu1—N3i2.006 (5)C12—C131.373 (11)
Cu1—O20i2.042 (4)C12—H120.9300
Cu1—O202.042 (4)C13—C141.359 (10)
Cu1—O21i2.257 (4)C13—H130.9300
Cu1—O212.257 (4)C14—H140.9300
C1—C21.368 (9)C15—F231.306 (5)
C1—C61.390 (8)C15—F22'1.308 (5)
C1—H10.9300C15—F221.309 (5)
C2—N31.345 (7)C15—F241.312 (5)
C2—H20.9300C15—F23'1.315 (5)
N3—C41.338 (7)C15—F24'1.317 (5)
C4—C51.368 (8)C15—C161.534 (8)
C4—H40.9300C16—O201.251 (7)
C5—C61.402 (8)C16—C171.387 (7)
C5—H50.9300C17—C181.390 (7)
C6—C71.463 (9)C17—H170.9300
C7—C81.322 (9)C18—O211.226 (7)
C7—H70.9300C18—C191.541 (8)
C8—C91.461 (9)C19—F25'1.305 (5)
C8—H80.9300C19—F27'1.306 (5)
C9—N101.341 (8)C19—F251.308 (5)
C9—C141.376 (9)C19—F261.310 (5)
N10—C111.339 (9)C19—F26'1.322 (5)
C11—C121.368 (11)C19—F271.323 (5)
N3—Cu1—N3i180.0 (2)C12—C11—H11118.2
N3—Cu1—O20i90.50 (18)C11—C12—C13118.6 (7)
N3i—Cu1—O20i89.50 (18)C11—C12—H12120.7
N3—Cu1—O2089.50 (18)C13—C12—H12120.7
N3i—Cu1—O2090.50 (18)C14—C13—C12118.8 (7)
O20i—Cu1—O20180.000 (1)C14—C13—H13120.6
N3—Cu1—O21i87.49 (16)C12—C13—H13120.6
N3i—Cu1—O21i92.51 (16)C13—C14—C9119.7 (7)
O20i—Cu1—O21i85.89 (15)C13—C14—H14120.1
O20—Cu1—O21i94.11 (15)C9—C14—H14120.1
N3—Cu1—O2192.51 (16)F23—C15—F22107.4 (5)
N3i—Cu1—O2187.49 (16)F23—C15—F24106.9 (5)
O20i—Cu1—O2194.11 (15)F22—C15—F24106.8 (5)
O20—Cu1—O2185.89 (15)F22'—C15—F23'106.6 (5)
O21i—Cu1—O21180.000 (1)F22'—C15—F24'106.7 (5)
C2—C1—C6121.3 (6)F23'—C15—F24'105.8 (5)
C2—C1—H1119.4F23—C15—C16115.6 (11)
C6—C1—H1119.4F22'—C15—C16117.1 (9)
N3—C2—C1122.6 (6)F22—C15—C16108.2 (12)
N3—C2—H2118.7F24—C15—C16111.5 (10)
C1—C2—H2118.7F23'—C15—C16112.1 (8)
C4—N3—C2117.1 (5)F24'—C15—C16107.8 (8)
C4—N3—Cu1121.9 (4)O20—C16—C17129.1 (5)
C2—N3—Cu1121.0 (4)O20—C16—C15112.0 (5)
N3—C4—C5123.2 (5)C17—C16—C15118.8 (5)
N3—C4—H4118.4C16—C17—C18124.2 (6)
C5—C4—H4118.4C16—C17—H17117.9
C4—C5—C6120.6 (6)C18—C17—H17117.9
C4—C5—H5119.7O21—C18—C17128.9 (5)
C6—C5—H5119.7O21—C18—C19114.6 (5)
C1—C6—C5115.2 (6)C17—C18—C19116.6 (5)
C1—C6—C7120.3 (6)F25'—C19—F27'107.6 (5)
C5—C6—C7124.4 (6)F25—C19—F26107.5 (5)
C8—C7—C6127.2 (6)F25'—C19—F26'106.3 (5)
C8—C7—H7116.4F27'—C19—F26'105.8 (5)
C6—C7—H7116.4F25—C19—F27105.7 (4)
C7—C8—C9125.2 (6)F26—C19—F27105.5 (4)
C7—C8—H8117.4F25'—C19—C18116.3 (9)
C9—C8—H8117.4F27'—C19—C18112.5 (8)
N10—C9—C14122.4 (6)F25—C19—C18116.6 (6)
N10—C9—C8117.3 (6)F26—C19—C18111.2 (6)
C14—C9—C8120.3 (6)F26'—C19—C18107.6 (7)
C9—N10—C11116.8 (6)F27—C19—C18109.6 (6)
N10—C11—C12123.6 (7)C16—O20—Cu1126.7 (4)
N10—C11—H11118.2C18—O21—Cu1121.2 (4)
Symmetry code: (i) x+1, y+1, z+1.
 

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