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The title compound, [Cu(C8H4O4)(C5H6N2)2]n, exhibits a polymeric zigzag chain structure extended along the c axis in the solid state. Each CuII ion is located on a crystallographic center of symmetry and is coordinated by two N [Cu—N = 1.993 (3) Å] and two O [Cu—O = 1.952 (2) Å] atoms in a distorted square-planar geometry. Weak C—H...O inter­actions contribute to the crystal packing stability.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042109/cv2291sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042109/cv2291Isup2.hkl
Contains datablock I

CCDC reference: 660732

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.135
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.14 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) 2.00 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 40
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

In the title compound, (I) (Fig. 1), the copper(II) centers are bridged by the carboxylate groups of o-phthalate ligiands and saturated by two 1-vinylimidazole ligands. Each CuII ion is located on a crystallographic center of symmetry being coordinated by two N [Cu—N 1.993 (3) Å] and two O [Cu—O 1.952 (2) Å] atoms in a distorted square-planar geometry. All these values agree well with those observed in [Cu(phthalato)(1-methylimidazole)2] (Baca et al., 2004), where CuII ions have a distorted tetrahedral environment. Each o-phthalate dianion acts as a bidentate ligand to bridge two CuII ions through two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 7.231 (6) Å.

In the crystal, weak C—H···O (Table 1) interactions contribute to the crystal packing stability.

Related literature top

In the corresponding compound [Cu(phthalato)(1-methylimidazole)2] (Baca et al., 2004), CuII ions have a distorted tetrahedral environment.

Experimental top

The reaction of CuCl2.2H2O(0.85 g, 5 mmol) with o-phthalic acid (0.83 g, 5 mmol) in an aqueous-alcohol(3:1) solution(40 ml) at 363 K for 30 min produced a blue solution, to which 1-vinylimidazole (0.94 g, 10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 333 K. Blue crystals were obtained after a few days.

Refinement top

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

Structure description top

In the title compound, (I) (Fig. 1), the copper(II) centers are bridged by the carboxylate groups of o-phthalate ligiands and saturated by two 1-vinylimidazole ligands. Each CuII ion is located on a crystallographic center of symmetry being coordinated by two N [Cu—N 1.993 (3) Å] and two O [Cu—O 1.952 (2) Å] atoms in a distorted square-planar geometry. All these values agree well with those observed in [Cu(phthalato)(1-methylimidazole)2] (Baca et al., 2004), where CuII ions have a distorted tetrahedral environment. Each o-phthalate dianion acts as a bidentate ligand to bridge two CuII ions through two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 7.231 (6) Å.

In the crystal, weak C—H···O (Table 1) interactions contribute to the crystal packing stability.

In the corresponding compound [Cu(phthalato)(1-methylimidazole)2] (Baca et al., 2004), CuII ions have a distorted tetrahedral environment.

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. A portion of polymeric chain in (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme [symmetry codes: (A) -x, -y, -z; (B) x + 1/2, y + 1/2, z; (C) x + 1/2, y + 1/2, z - 1].
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis. Dashed lines denote hydrogen bonds.
catena-Poly[[bis(1-vinyl-1H-imidazole-κN3)copper(II)]-µ-phthalato-κ2O:O'] top
Crystal data top
[Cu(C8H4O4)(C5H6N2)2]F(000) = 852
Mr = 415.90Dx = 1.537 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3318 reflections
a = 16.527 (3) Åθ = 2.5–25.1°
b = 8.1800 (16) ŵ = 1.25 mm1
c = 14.463 (3) ÅT = 293 K
β = 113.19 (3)°Block, blue
V = 1797.3 (7) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
1768 independent reflections
Radiation source: fine-focus sealed tube1344 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
thin–slice ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2020
Tmin = 0.706, Tmax = 0.885k = 010
3525 measured reflectionsl = 1717
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0844P)2 + 0.9237P]
where P = (Fo2 + 2Fc2)/3
1768 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.75 e Å3
40 restraintsΔρmin = 0.63 e Å3
Crystal data top
[Cu(C8H4O4)(C5H6N2)2]V = 1797.3 (7) Å3
Mr = 415.90Z = 4
Monoclinic, C2/cMo Kα radiation
a = 16.527 (3) ŵ = 1.25 mm1
b = 8.1800 (16) ÅT = 293 K
c = 14.463 (3) Å0.30 × 0.20 × 0.10 mm
β = 113.19 (3)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
1768 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1344 reflections with I > 2σ(I)
Tmin = 0.706, Tmax = 0.885Rint = 0.023
3525 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04840 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.00Δρmax = 0.75 e Å3
1768 reflectionsΔρmin = 0.63 e Å3
124 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
Cu0.00000.00000.00000.0333 (2)
O10.06590 (16)0.0922 (3)0.14946 (17)0.0480 (6)
O20.01489 (15)0.2039 (3)0.07497 (16)0.0423 (5)
N10.11711 (18)0.0724 (4)0.0994 (2)0.0431 (6)
C60.1839 (3)0.1421 (6)0.0812 (3)0.0679 (12)
H6A0.18180.16660.01750.081*
C10.0087 (3)0.6538 (5)0.1984 (3)0.0627 (11)
H1A0.01560.75190.16370.075*
C20.0155 (3)0.5079 (4)0.1493 (3)0.0486 (9)
H2B0.02530.50850.08140.058*
C30.00809 (19)0.3593 (4)0.1982 (2)0.0341 (7)
C40.0211 (2)0.2048 (4)0.1387 (2)0.0375 (7)
C50.1469 (2)0.0592 (5)0.1980 (3)0.0478 (8)
H5A0.11530.01480.23280.057*
N20.22960 (19)0.1189 (4)0.2419 (2)0.0533 (8)
C70.2538 (3)0.1709 (7)0.1679 (3)0.0728 (13)
H7A0.30740.21690.17520.087*
C80.2838 (3)0.1327 (6)0.3459 (3)0.0695 (12)
H8A0.34220.16380.36390.083*
C90.2577 (4)0.1057 (9)0.4147 (4)0.107 (2)
H9C0.19970.07450.39900.128*
H9A0.29630.11680.48160.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0317 (3)0.0411 (4)0.0270 (3)0.0012 (2)0.0114 (2)0.0024 (2)
O10.0608 (15)0.0420 (14)0.0393 (13)0.0160 (11)0.0178 (11)0.0031 (10)
O20.0444 (12)0.0481 (14)0.0360 (11)0.0018 (10)0.0176 (10)0.0065 (10)
N10.0390 (14)0.0504 (16)0.0354 (14)0.0037 (13)0.0098 (11)0.0025 (13)
C60.050 (2)0.103 (3)0.047 (2)0.020 (2)0.0159 (17)0.002 (2)
C10.090 (3)0.038 (2)0.070 (3)0.0032 (19)0.042 (3)0.0090 (18)
C20.059 (2)0.045 (2)0.046 (2)0.0037 (16)0.0252 (18)0.0069 (15)
C30.0355 (15)0.0318 (16)0.0368 (16)0.0003 (12)0.0161 (13)0.0005 (13)
C40.0365 (15)0.0401 (17)0.0311 (15)0.0041 (13)0.0082 (13)0.0012 (13)
C50.0463 (19)0.0520 (19)0.0411 (17)0.0077 (16)0.0129 (15)0.0031 (16)
N20.0452 (16)0.063 (2)0.0390 (15)0.0081 (14)0.0029 (13)0.0029 (14)
C70.048 (2)0.105 (4)0.063 (2)0.026 (2)0.0194 (19)0.000 (2)
C80.052 (2)0.090 (3)0.052 (2)0.018 (2)0.0054 (19)0.002 (2)
C90.084 (4)0.165 (6)0.061 (3)0.039 (4)0.017 (3)0.019 (4)
Geometric parameters (Å, º) top
Cu—O21.952 (2)C2—C31.387 (4)
Cu—O2i1.952 (2)C2—H2B0.9300
Cu—N1i1.993 (3)C3—C3ii1.415 (6)
Cu—N11.993 (3)C3—C41.496 (4)
O1—C41.228 (4)C5—N21.351 (4)
O2—C41.280 (4)C5—H5A0.9300
N1—C51.317 (4)N2—C71.351 (5)
N1—C61.358 (5)N2—C81.420 (5)
C6—C71.350 (6)C7—H7A0.9300
C6—H6A0.9300C8—C91.250 (7)
C1—C21.371 (5)C8—H8A0.9300
C1—C1ii1.405 (8)C9—H9C0.9300
C1—H1A0.9300C9—H9A0.9300
O2—Cu—O2i180.00 (13)C2—C3—C4118.9 (3)
O2—Cu—N1i91.21 (11)C3ii—C3—C4122.22 (16)
O2i—Cu—N1i88.79 (11)O1—C4—O2124.1 (3)
O2—Cu—N188.79 (11)O1—C4—C3121.2 (3)
O2i—Cu—N191.21 (11)O2—C4—C3114.6 (3)
N1i—Cu—N1180.0 (2)N1—C5—N2110.9 (3)
C4—O2—Cu114.3 (2)N1—C5—H5A124.5
C5—N1—C6105.0 (3)N2—C5—H5A124.5
C5—N1—Cu126.9 (2)C7—N2—C5107.6 (3)
C6—N1—Cu128.1 (2)C7—N2—C8123.6 (3)
C7—C6—N1110.9 (4)C5—N2—C8128.8 (3)
C7—C6—H6A124.6C6—C7—N2105.6 (3)
N1—C6—H6A124.6C6—C7—H7A127.2
C2—C1—C1ii119.4 (2)N2—C7—H7A127.2
C2—C1—H1A120.3C9—C8—N2123.8 (4)
C1ii—C1—H1A120.3C9—C8—H8A118.1
C1—C2—C3121.7 (4)N2—C8—H8A118.1
C1—C2—H2B119.2C8—C9—H9C120.0
C3—C2—H2B119.2C8—C9—H9A120.0
C2—C3—C3ii118.8 (2)H9C—C9—H9A120.0
N1i—Cu—O2—C484.6 (2)C2—C3—C4—O1135.5 (3)
N1—Cu—O2—C495.4 (2)C3ii—C3—C4—O142.0 (5)
O2—Cu—N1—C544.5 (3)C2—C3—C4—O242.0 (4)
O2i—Cu—N1—C5135.5 (3)C3ii—C3—C4—O2140.5 (4)
O2—Cu—N1—C6133.9 (4)C6—N1—C5—N20.3 (5)
O2i—Cu—N1—C646.1 (4)Cu—N1—C5—N2179.1 (3)
C5—N1—C6—C70.1 (5)N1—C5—N2—C70.6 (5)
Cu—N1—C6—C7178.7 (3)N1—C5—N2—C8177.6 (4)
C1ii—C1—C2—C31.9 (8)N1—C6—C7—N20.4 (6)
C1—C2—C3—C3ii0.9 (6)C5—N2—C7—C60.6 (5)
C1—C2—C3—C4176.6 (4)C8—N2—C7—C6177.7 (4)
Cu—O2—C4—O14.0 (4)C7—N2—C8—C9169.9 (6)
Cu—O2—C4—C3178.59 (18)C5—N2—C8—C98.1 (9)
Symmetry codes: (i) x, y, z; (ii) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1ii0.932.333.243 (5)167
C6—H6A···O1i0.932.503.158 (5)128
C8—H8A···O2iii0.932.433.342 (6)168
C9—H9C···O1ii0.932.453.349 (8)162
Symmetry codes: (i) x, y, z; (ii) x, y, z+1/2; (iii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Cu(C8H4O4)(C5H6N2)2]
Mr415.90
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)16.527 (3), 8.1800 (16), 14.463 (3)
β (°) 113.19 (3)
V3)1797.3 (7)
Z4
Radiation typeMo Kα
µ (mm1)1.25
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.706, 0.885
No. of measured, independent and
observed [I > 2σ(I)] reflections
3525, 1768, 1344
Rint0.023
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.136, 1.00
No. of reflections1768
No. of parameters124
No. of restraints40
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.75, 0.63

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1i0.932.333.243 (5)167
C6—H6A···O1ii0.932.503.158 (5)128
C8—H8A···O2iii0.932.433.342 (6)168
C9—H9C···O1i0.932.453.349 (8)162
Symmetry codes: (i) x, y, z+1/2; (ii) x, y, z; (iii) x+1/2, y+1/2, z+1/2.
 

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