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The title compound, [Cu2(C2H3O2)4(C7H7N)2], consists of centrosymmetric dinuclear units, in which four acetate groups bridge the two Cu atoms and a 4-vinyl­pyridine neutral ligand occupies the axial position of each Cu atom, coordinated to it through the pyridine N atom. Each Cu atom has a distorted octa­hedral coordination. Weak C—H...O inter­actions contribute to the crystal packing stability.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042328/hg2288sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042328/hg2288Isup2.hkl
Contains datablock I

CCDC reference: 663549

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.061
  • wR factor = 0.182
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.16 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu (2) 2.12 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The title compound,(I), (Fig. 1), consists of centrosymmetric dinuclear units, in which four acetate groups bridge the two copper atoms and a 4-vinylpyridine neutral ligand occupies the axis position of each copper atom, coordinated to them through the pyridine nitrogen atom. Each copper atom has a distorted square-planar pyramidal coordination, with four oxygen atoms in a plane. The distances for Cu—O1, O2, O3 and O4 are 1.979 (4), 1.969 (4), 1.971 (4) and 1.977 (5) Å, respectively. The fifth coordination position is occupied by the pyridine nitrogen, N, of a ligand molecule at 2.178 (5) Å. All these values agree well with those observed in [Cu2(υ-OOCCH3)4(PhNHpy)2] (PhNHpy is 2-anilinopyridine) (Seco et al., 2002). The copper atom rises from the basal plane to the apical N atom by 0.217 (1) Å. The Cu···Cu separation is 2.6405 (14) Å. Weak intramolecular C—H···O interactions contribute to the crystal packing stability.

Related literature top

For related literature, see: Seco et al. (2002).

Experimental top

A solution of 4-vinylpyridine (1.05 g, 10 mmol) in alcohol (10 ml) was added to Cu(OAc)2.H2O (2.00 g, 10 mmol) in alcohol (40 ml). The solution was stirred during 2 h and a precipitate was formed. The blue precipitate was filtered off, washed with alcohol and dried in vacuo over CaCO3. Blue crystals were obtained from recrystallization in alcohol after a few days.

Refinement top

H atoms were positioned geometrically (C—H = 0.93 Å or 0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 or 1.5 times Ueq(C).

Structure description top

The title compound,(I), (Fig. 1), consists of centrosymmetric dinuclear units, in which four acetate groups bridge the two copper atoms and a 4-vinylpyridine neutral ligand occupies the axis position of each copper atom, coordinated to them through the pyridine nitrogen atom. Each copper atom has a distorted square-planar pyramidal coordination, with four oxygen atoms in a plane. The distances for Cu—O1, O2, O3 and O4 are 1.979 (4), 1.969 (4), 1.971 (4) and 1.977 (5) Å, respectively. The fifth coordination position is occupied by the pyridine nitrogen, N, of a ligand molecule at 2.178 (5) Å. All these values agree well with those observed in [Cu2(υ-OOCCH3)4(PhNHpy)2] (PhNHpy is 2-anilinopyridine) (Seco et al., 2002). The copper atom rises from the basal plane to the apical N atom by 0.217 (1) Å. The Cu···Cu separation is 2.6405 (14) Å. Weak intramolecular C—H···O interactions contribute to the crystal packing stability.

For related literature, see: Seco et al. (2002).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme, hydrogen atoms were omitted for clarity.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis.
Tetra-µ-acetato-κ8O:O'-bis[(4-vinylpyridine-κN)copper(II)](Cu—Cu) top
Crystal data top
C22H26Cu2N2O8F(000) = 588
Mr = 573.53Dx = 1.520 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3329 reflections
a = 10.696 (2) Åθ = 2.5–25.1°
b = 12.830 (3) ŵ = 1.74 mm1
c = 9.4820 (19) ÅT = 293 K
β = 105.65 (3)°Block, blue
V = 1253.0 (5) Å30.30 × 0.20 × 0.10 mm
Z = 2
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2358 independent reflections
Radiation source: fine-focus sealed tube1830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
thin–slice ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1312
Tmin = 0.623, Tmax = 0.845k = 015
2455 measured reflectionsl = 011
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1P)2 + 3P]
where P = (Fo2 + 2Fc2)/3
2358 reflections(Δ/σ)max = 0.002
144 parametersΔρmax = 1.47 e Å3
1 restraintΔρmin = 1.13 e Å3
Crystal data top
C22H26Cu2N2O8V = 1253.0 (5) Å3
Mr = 573.53Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.696 (2) ŵ = 1.74 mm1
b = 12.830 (3) ÅT = 293 K
c = 9.4820 (19) Å0.30 × 0.20 × 0.10 mm
β = 105.65 (3)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2358 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1830 reflections with I > 2σ(I)
Tmin = 0.623, Tmax = 0.845Rint = 0.013
2455 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0611 restraint
wR(F2) = 0.182H-atom parameters constrained
S = 1.01Δρmax = 1.47 e Å3
2358 reflectionsΔρmin = 1.13 e Å3
144 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
Cu0.40251 (7)0.02266 (5)0.05538 (7)0.0441 (3)
O10.3606 (5)0.1277 (3)0.0336 (5)0.0612 (11)
O20.4745 (5)0.1639 (3)0.0554 (5)0.0630 (12)
O30.3013 (5)0.0430 (4)0.1496 (5)0.0641 (12)
O40.5344 (5)0.0066 (4)0.2417 (5)0.0663 (12)
N0.2542 (5)0.0760 (4)0.1573 (5)0.0508 (11)
C10.0518 (10)0.2562 (8)0.4014 (10)0.101
H1A0.02690.29110.43450.121*
H1B0.12330.27740.43210.121*
C20.0617 (10)0.1780 (8)0.3125 (10)0.100
H2A0.13860.14120.27710.120*
C30.0585 (7)0.1517 (7)0.2715 (8)0.074 (2)
C40.1672 (8)0.2085 (5)0.2806 (8)0.0677 (19)
H4A0.17740.27360.32510.081*
C50.2638 (6)0.1679 (5)0.2221 (7)0.0562 (15)
H5A0.33820.20730.22930.067*
C60.1465 (7)0.0221 (6)0.1532 (8)0.0691 (19)
H6A0.13870.04370.11060.083*
C70.0486 (8)0.0551 (8)0.2057 (9)0.083 (2)
H7A0.02430.01360.19780.099*
C80.6099 (8)0.3033 (6)0.0297 (10)0.082 (2)
H8A0.58590.33360.11110.123*
H8B0.56590.33910.05870.123*
H8C0.70200.30930.04480.123*
C90.5718 (6)0.1895 (5)0.0165 (7)0.0501 (14)
C100.7308 (8)0.0547 (7)0.4061 (7)0.080 (2)
H10A0.81050.01620.42460.121*
H10B0.74960.12790.41610.121*
H10C0.68420.03430.47520.121*
C110.6490 (7)0.0322 (4)0.2527 (7)0.0563 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0535 (4)0.0386 (4)0.0448 (4)0.0010 (3)0.0212 (3)0.0026 (3)
O10.076 (3)0.044 (2)0.074 (3)0.012 (2)0.038 (2)0.001 (2)
O20.073 (3)0.042 (2)0.085 (3)0.007 (2)0.041 (3)0.000 (2)
O30.066 (3)0.073 (3)0.051 (2)0.012 (2)0.011 (2)0.004 (2)
O40.085 (3)0.069 (3)0.045 (2)0.011 (3)0.017 (2)0.004 (2)
N0.054 (3)0.052 (3)0.049 (3)0.000 (2)0.019 (2)0.001 (2)
C10.1010.1010.1010.0000.0270.000
C20.1000.1000.1000.0000.0270.000
C30.067 (4)0.107 (7)0.058 (4)0.029 (4)0.034 (3)0.028 (4)
C40.099 (5)0.048 (4)0.068 (4)0.020 (4)0.043 (4)0.010 (3)
C50.061 (4)0.053 (4)0.063 (4)0.000 (3)0.030 (3)0.008 (3)
C60.064 (4)0.074 (5)0.077 (5)0.020 (4)0.033 (4)0.018 (4)
C70.066 (4)0.103 (7)0.091 (6)0.009 (4)0.043 (4)0.003 (5)
C80.089 (5)0.047 (4)0.120 (7)0.016 (4)0.047 (5)0.002 (4)
C90.061 (4)0.039 (3)0.056 (3)0.004 (3)0.024 (3)0.007 (3)
C100.104 (6)0.073 (5)0.051 (4)0.021 (4)0.002 (4)0.001 (3)
C110.083 (5)0.034 (3)0.046 (3)0.006 (3)0.006 (3)0.001 (2)
Geometric parameters (Å, º) top
Cu—O21.969 (4)C3—C71.379 (12)
Cu—O31.971 (4)C4—C51.399 (9)
Cu—O41.977 (5)C4—H4A0.9300
Cu—O11.979 (4)C5—H5A0.9300
Cu—N2.178 (5)C6—C71.343 (10)
Cu—Cui2.6405 (14)C6—H6A0.9300
O1—C9i1.251 (7)C7—H7A0.9300
O2—C91.238 (7)C8—C91.511 (9)
O3—C11i1.240 (8)C8—H8A0.9600
O4—C111.246 (9)C8—H8B0.9600
N—C51.320 (8)C8—H8C0.9600
N—C61.335 (8)C9—O1i1.251 (7)
C1—C21.296 (8)C10—C111.509 (8)
C1—H1A0.9300C10—H10A0.9600
C1—H1B0.9300C10—H10B0.9600
C2—C31.479 (12)C10—H10C0.9600
C2—H2A0.9300C11—O3i1.240 (8)
C3—C41.355 (11)
O2—Cu—O389.4 (2)C3—C4—C5119.2 (7)
O2—Cu—O489.4 (2)C3—C4—H4A120.4
O3—Cu—O4167.5 (2)C5—C4—H4A120.4
O2—Cu—O1167.15 (17)N—C5—C4122.9 (6)
O3—Cu—O188.7 (2)N—C5—H5A118.5
O4—Cu—O189.7 (2)C4—C5—H5A118.5
O2—Cu—N92.43 (19)N—C6—C7125.4 (8)
O3—Cu—N97.14 (19)N—C6—H6A117.3
O4—Cu—N95.30 (19)C7—C6—H6A117.3
O1—Cu—N100.41 (19)C6—C7—C3118.6 (8)
O2—Cu—Cui81.48 (13)C6—C7—H7A120.7
O3—Cu—Cui85.37 (14)C3—C7—H7A120.7
O4—Cu—Cui82.19 (15)C9—C8—H8A109.5
O1—Cu—Cui85.69 (13)C9—C8—H8B109.5
N—Cu—Cui173.42 (15)H8A—C8—H8B109.5
C9i—O1—Cu121.3 (4)C9—C8—H8C109.5
C9—O2—Cu127.2 (4)H8A—C8—H8C109.5
C11i—O3—Cu121.6 (4)H8B—C8—H8C109.5
C11—O4—Cu125.0 (4)O2—C9—O1i124.3 (6)
C5—N—C6115.7 (6)O2—C9—C8117.5 (6)
C5—N—Cu120.8 (4)O1i—C9—C8118.2 (6)
C6—N—Cu123.4 (5)C11—C10—H10A109.5
C2—C1—H1A120.0C11—C10—H10B109.5
C2—C1—H1B120.0H10A—C10—H10B109.5
H1A—C1—H1B120.0C11—C10—H10C109.5
C1—C2—C3115.1 (10)H10A—C10—H10C109.5
C1—C2—H2A122.5H10B—C10—H10C109.5
C3—C2—H2A122.5O3i—C11—O4125.8 (6)
C4—C3—C7118.1 (7)O3i—C11—C10118.6 (7)
C4—C3—C2130.7 (9)O4—C11—C10115.6 (6)
C7—C3—C2111.0 (8)
O2—Cu—O1—C9i4.5 (12)O4—Cu—N—C573.6 (5)
O3—Cu—O1—C9i86.0 (5)O1—Cu—N—C5164.3 (5)
O4—Cu—O1—C9i81.6 (5)O2—Cu—N—C6160.8 (6)
N—Cu—O1—C9i177.0 (5)O3—Cu—N—C671.1 (6)
Cui—Cu—O1—C9i0.6 (5)O4—Cu—N—C6109.6 (6)
O3—Cu—O2—C987.1 (6)O1—Cu—N—C618.9 (6)
O4—Cu—O2—C980.5 (6)C1—C2—C3—C418.3 (14)
O1—Cu—O2—C95.7 (12)C1—C2—C3—C7166.1 (9)
N—Cu—O2—C9175.8 (5)C7—C3—C4—C50.6 (11)
Cui—Cu—O2—C91.7 (5)C2—C3—C4—C5174.6 (7)
O2—Cu—O3—C11i80.3 (5)C6—N—C5—C41.4 (9)
O4—Cu—O3—C11i4.3 (13)Cu—N—C5—C4175.7 (5)
O1—Cu—O3—C11i87.0 (5)C3—C4—C5—N0.2 (10)
N—Cu—O3—C11i172.7 (5)C5—N—C6—C71.8 (12)
Cui—Cu—O3—C11i1.2 (5)Cu—N—C6—C7175.2 (7)
O2—Cu—O4—C1181.0 (5)N—C6—C7—C31.0 (14)
O3—Cu—O4—C113.6 (13)C4—C3—C7—C60.3 (12)
O1—Cu—O4—C1186.1 (5)C2—C3—C7—C6175.8 (8)
N—Cu—O4—C11173.4 (5)Cu—O2—C9—O1i1.8 (10)
Cui—Cu—O4—C110.4 (5)Cu—O2—C9—C8178.7 (5)
O2—Cu—N—C516.0 (5)Cu—O4—C11—O3i0.4 (10)
O3—Cu—N—C5105.7 (5)Cu—O4—C11—C10177.7 (5)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O20.932.543.083 (8)118

Experimental details

Crystal data
Chemical formulaC22H26Cu2N2O8
Mr573.53
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.696 (2), 12.830 (3), 9.4820 (19)
β (°) 105.65 (3)
V3)1253.0 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.74
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.623, 0.845
No. of measured, independent and
observed [I > 2σ(I)] reflections
2455, 2358, 1830
Rint0.013
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.182, 1.01
No. of reflections2358
No. of parameters144
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.47, 1.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001) and local programs.

Selected geometric parameters (Å, º) top
Cu—O21.969 (4)Cu—O11.979 (4)
Cu—O31.971 (4)Cu—N2.178 (5)
Cu—O41.977 (5)Cu—Cui2.6405 (14)
O2—Cu—O389.4 (2)O1—Cu—N100.41 (19)
O3—Cu—O4167.5 (2)O2—Cu—Cui81.48 (13)
O3—Cu—O188.7 (2)O3—Cu—Cui85.37 (14)
O4—Cu—O189.7 (2)O4—Cu—Cui82.19 (15)
O2—Cu—N92.43 (19)O1—Cu—Cui85.69 (13)
O3—Cu—N97.14 (19)N—Cu—Cui173.42 (15)
O4—Cu—N95.30 (19)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O20.932.543.083 (8)118
 

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