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Acta Cryst. (2007). E63, m2874    [ doi:10.1107/S160053680705355X ]

catena-Poly[[bis(1-vinylimidazole-[kappa]N3)zinc(II)]-[mu]-phthalato-[kappa]2O1:O2\]

R.-X. Li, S.-X. Li, Q.-Y. Wu, G.-Y. Liu and F.-Q. Liu

Abstract top

The title compound, [Zn(C8H4O4)(C5H6N2)2]n, in the solid state comprises polymeric zigzag chains extending along the c axis. Each ZnII ion is coordinated by two N [Zn-N = 1.991 (6) and 2.031 (5) Å] and two O [Zn-O = 1.912 (5) and 1.965 (5) Å] atoms in a distorted tetrahedral geometry. Weak C-H...O interactions contribute to the crystal packing stability.

Comment top

In the title compound, (I) (Fig. 1), the zinc(II) centers are bridged by the carboxylate group of o-phthalate and saturated by 1-vinylimidazole. Each ZnII ion is coordinated by two N [Zn—N1 = 1.993 (3) Å, Zn—N3 = 2.031 (5) Å] and two O [Zn—O2 = 1.912 (5) Å, Zn—O3 = 1.965 (5) Å] atoms in a distorted tetrahedral geometry. All these values agree well with those observed in [Zn(phthalato)(1-H-imidazole)2] (Liu et al., 2002), where ZnII ions also have a distorted tetrahedral environment. Each o-phthalate in (I) dianion acts as a bidentate ligand to bridge two ZnII ions through the two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 7.1397 (18) Å.

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

Related literature top

In the corresponding compound [Zn(phthalato)(1-H-imidazole)2] the ZnII ions have a distorted tetrahedral environment (Liu et al., 2002).

Experimental top

The reaction of ZnCl2 (0.68 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 minutes 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. Colourless 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).

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 the polymeric chain in the title compound showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (A) x,-y + 1/2,z + 1/2].
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis.
catena-Poly[[bis(1-vinylimidazole-κN3)zinc(II)]-µ-phthalato-κ2O1:O2] top
Crystal data top
[Zn(C8H4O4)(C5H6N2)2]F000 = 856
Mr = 417.72Dx = 1.461 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3025 reflections
a = 8.4110 (17) Åθ = 2.5–25.1º
b = 16.329 (3) ŵ = 1.32 mm−1
c = 14.083 (3) ÅT = 293 (2) K
β = 100.87 (3)ºBlock, colourless
V = 1899.5 (7) Å30.40 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3678 independent reflections
Radiation source: fine-focus sealed tube2090 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.015
T = 293(2) Kθmax = 26.0º
thin–slice ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −10→10
Tmin = 0.620, Tmax = 0.879k = 0→20
3729 measured reflectionsl = 0→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.1041P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3678 reflectionsΔρmax = 1.03 e Å−3
190 parametersΔρmin = −1.09 e Å−3
133 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C8H4O4)(C5H6N2)2]V = 1899.5 (7) Å3
Mr = 417.72Z = 4
Monoclinic, P21/cMo Kα
a = 8.4110 (17) ŵ = 1.32 mm−1
b = 16.329 (3) ÅT = 293 (2) K
c = 14.083 (3) Å0.40 × 0.10 × 0.10 mm
β = 100.87 (3)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3678 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2090 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.879Rint = 0.015
3729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045133 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.08Δρmax = 1.03 e Å−3
3678 reflectionsΔρmin = −1.09 e Å−3
190 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
Zn0.11543 (10)0.21386 (5)0.54220 (5)0.0456 (3)
O10.0879 (6)0.1714 (3)0.2024 (3)0.0524 (12)
O20.2671 (6)0.2117 (3)0.1147 (3)0.0608 (14)
O30.2286 (6)0.1414 (3)0.4655 (3)0.0570 (14)
O40.2799 (7)0.2508 (3)0.3833 (3)0.0567 (14)
N1−0.0828 (8)0.2607 (4)0.4605 (4)0.0562 (16)
N2−0.2745 (10)0.2885 (5)0.3388 (6)0.087 (2)
N30.0464 (7)0.1306 (3)0.6335 (4)0.0459 (13)
N40.0425 (8)0.0561 (4)0.7615 (5)0.059
C10.5666 (14)0.0239 (7)0.2496 (8)0.105
H1A0.6262−0.00930.21560.125*
C20.4515 (10)0.0729 (5)0.1993 (6)0.068 (2)
H2A0.43530.07300.13220.082*
C30.3591 (8)0.1219 (4)0.2441 (4)0.0469 (16)
C40.3852 (8)0.1234 (4)0.3456 (5)0.0452 (16)
C50.5051 (10)0.0725 (5)0.3981 (6)0.064 (2)
H5A0.52270.07270.46530.077*
C60.5999 (12)0.0208 (6)0.3497 (7)0.087 (3)
H6A0.6798−0.01320.38340.104*
C70.2259 (8)0.1715 (4)0.1859 (4)0.0422 (16)
C80.2909 (8)0.1767 (5)0.3999 (5)0.0439 (16)
C9−0.1283 (10)0.2505 (5)0.3651 (6)0.067 (2)
H9A−0.07130.22290.32450.080*
C10−0.3184 (13)0.3235 (7)0.4126 (7)0.089
H10A−0.41290.35300.41280.107*
C11−0.1980 (14)0.3083 (7)0.4892 (8)0.099
H11A−0.19460.32750.55170.119*
C12−0.3286 (13)0.2862 (6)0.2280 (8)0.101
H12A−0.28620.24670.19220.121*
C13−0.4307 (12)0.3378 (7)0.1850 (8)0.101
H13A−0.47340.37740.22050.121*
H13B−0.46250.33590.11810.121*
C140.0926 (8)0.1266 (4)0.7271 (5)0.0464 (16)
H14A0.15200.16690.76490.056*
C15−0.0419 (11)0.0139 (6)0.6833 (6)0.080
H15A−0.0898−0.03730.68480.097*
C16−0.0421 (10)0.0598 (5)0.6052 (6)0.064
H16A−0.09270.04680.54250.077*
C170.0665 (12)0.0246 (7)0.8540 (7)0.087
H17A0.0191−0.02570.86260.105*
C180.1471 (12)0.0584 (6)0.9271 (7)0.090 (3)
H18A0.19640.10870.92140.108*
H18B0.15790.03330.98730.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0559 (5)0.0507 (5)0.0273 (4)0.0043 (4)0.0006 (3)−0.0008 (4)
O10.057 (3)0.051 (3)0.048 (3)0.003 (3)0.007 (2)0.011 (2)
O20.068 (3)0.073 (4)0.041 (3)0.007 (3)0.008 (2)0.016 (3)
O30.086 (4)0.054 (3)0.035 (3)0.009 (3)0.020 (3)0.005 (2)
O40.085 (4)0.044 (3)0.040 (3)0.016 (3)0.010 (3)−0.003 (2)
N10.061 (4)0.063 (4)0.041 (3)−0.003 (3)0.001 (3)0.004 (3)
N20.079 (5)0.084 (5)0.080 (4)0.001 (4)−0.031 (4)0.010 (4)
N30.055 (3)0.047 (3)0.037 (3)0.006 (3)0.009 (3)−0.002 (2)
N40.0590.0590.0590.0000.0110.000
C10.1050.1050.1050.0000.0200.000
C20.092 (6)0.069 (5)0.048 (4)0.016 (4)0.022 (4)0.004 (4)
C30.056 (4)0.052 (4)0.032 (3)−0.002 (3)0.005 (3)0.001 (3)
C40.056 (4)0.045 (4)0.034 (3)0.000 (3)0.006 (3)0.007 (3)
C50.074 (5)0.062 (5)0.052 (4)0.018 (4)0.001 (4)0.014 (3)
C60.077 (6)0.098 (6)0.084 (5)0.031 (5)0.013 (4)0.008 (5)
C70.051 (4)0.040 (4)0.031 (3)−0.001 (3)−0.002 (3)−0.001 (3)
C80.043 (4)0.050 (4)0.031 (3)0.001 (3)−0.010 (3)−0.004 (3)
C90.063 (4)0.074 (5)0.059 (4)−0.014 (4)−0.001 (4)0.009 (4)
C100.0890.0890.0890.0000.0170.000
C110.0990.0990.0990.0000.0190.000
C120.1010.1010.1010.0000.0190.000
C130.1010.1010.1010.0000.0190.000
C140.061 (4)0.042 (3)0.037 (3)0.006 (3)0.012 (3)0.002 (3)
C150.0800.0800.0800.0000.0150.000
C160.0640.0640.0640.0000.0120.000
C170.0870.0870.0870.0000.0160.000
C180.103 (8)0.082 (7)0.082 (7)0.005 (6)0.009 (6)0.010 (6)
Geometric parameters (Å, °) top
Zn—O2i1.912 (5)C3—C41.406 (8)
Zn—O31.965 (5)C3—C71.495 (7)
Zn—N11.991 (6)C4—C51.404 (9)
Zn—N32.031 (5)C4—C81.483 (9)
O1—C71.226 (8)C5—C61.420 (11)
O2—C71.299 (8)C5—H5A0.9300
O2—Znii1.912 (5)C6—H6A0.9300
O3—C81.282 (8)C9—H9A0.9300
O4—C81.232 (8)C10—C111.356 (14)
N1—C91.335 (9)C10—H10A0.9300
N1—C111.363 (12)C11—H11A0.9300
N2—C101.299 (12)C12—C131.272 (8)
N2—C91.365 (11)C12—H12A0.9300
N2—C121.541 (12)C13—H13A0.9300
N3—C141.303 (8)C13—H13B0.9300
N3—C161.392 (9)C14—H14A0.9300
N4—C141.348 (9)C15—C161.330 (11)
N4—C151.377 (10)C15—H15A0.9300
N4—C171.379 (10)C16—H16A0.9300
C1—C21.350 (13)C17—C181.250 (12)
C1—C61.385 (12)C17—H17A0.9300
C1—H1A0.9300C18—H18A0.9300
C2—C31.351 (10)C18—H18B0.9300
C2—H2A0.9300
O2i—Zn—O3109.4 (2)C5—C6—H6A121.8
O2i—Zn—N1117.8 (3)O1—C7—O2123.2 (6)
O3—Zn—N1110.7 (2)O1—C7—C3122.2 (6)
O2i—Zn—N3109.3 (2)O2—C7—C3114.6 (6)
O3—Zn—N399.9 (2)O4—C8—O3123.5 (7)
N1—Zn—N3108.4 (2)O4—C8—C4120.5 (6)
C7—O2—Znii119.0 (4)O3—C8—C4116.0 (6)
C8—O3—Zn115.6 (4)N1—C9—N2106.8 (8)
C9—N1—C11106.5 (8)N1—C9—H9A126.6
C9—N1—Zn125.7 (6)N2—C9—H9A126.6
C11—N1—Zn127.8 (6)N2—C10—C11105.9 (10)
C10—N2—C9111.1 (8)N2—C10—H10A127.0
C10—N2—C12138.3 (9)C11—C10—H10A127.0
C9—N2—C12110.1 (9)C10—C11—N1109.5 (10)
C14—N3—C16106.9 (6)C10—C11—H11A125.3
C14—N3—Zn127.4 (5)N1—C11—H11A125.3
C16—N3—Zn125.2 (5)C13—C12—N2120.6 (11)
C14—N4—C15106.8 (7)C13—C12—H12A119.7
C14—N4—C17131.2 (8)N2—C12—H12A119.7
C15—N4—C17122.0 (8)C12—C13—H13A120.0
C2—C1—C6122.9 (11)C12—C13—H13B120.0
C2—C1—H1A118.6H13A—C13—H13B120.0
C6—C1—H1A118.6N3—C14—N4110.6 (6)
C3—C2—C1121.7 (8)N3—C14—H14A124.7
C3—C2—H2A119.2N4—C14—H14A124.7
C1—C2—H2A119.2C16—C15—N4107.5 (9)
C2—C3—C4119.4 (6)C16—C15—H15A126.3
C2—C3—C7120.1 (6)N4—C15—H15A126.3
C4—C3—C7120.4 (6)C15—C16—N3108.3 (8)
C3—C4—C5118.9 (7)C15—C16—H16A125.9
C3—C4—C8122.5 (6)N3—C16—H16A125.9
C5—C4—C8118.5 (6)C18—C17—N4124.9 (10)
C4—C5—C6120.8 (7)C18—C17—H17A117.5
C4—C5—H5A119.6N4—C17—H17A117.5
C6—C5—H5A119.6C17—C18—H18A120.0
C1—C6—C5116.3 (9)C17—C18—H18B120.0
C1—C6—H6A121.8H18A—C18—H18B120.0
O2i—Zn—O3—C8−64.4 (5)C2—C3—C7—O2−47.7 (9)
N1—Zn—O3—C867.0 (5)C4—C3—C7—O2134.8 (7)
N3—Zn—O3—C8−179.0 (5)Zn—O3—C8—O4−1.2 (9)
O2i—Zn—N1—C9121.9 (6)Zn—O3—C8—C4176.4 (4)
O3—Zn—N1—C9−5.0 (7)C3—C4—C8—O4−52.7 (10)
N3—Zn—N1—C9−113.5 (7)C5—C4—C8—O4127.3 (7)
O2i—Zn—N1—C11−58.4 (8)C3—C4—C8—O3129.7 (7)
O3—Zn—N1—C11174.7 (7)C5—C4—C8—O3−50.4 (9)
N3—Zn—N1—C1166.2 (8)C11—N1—C9—N2−3.2 (10)
O2i—Zn—N3—C140.9 (6)Zn—N1—C9—N2176.6 (5)
O3—Zn—N3—C14115.7 (6)C10—N2—C9—N12.0 (11)
N1—Zn—N3—C14−128.6 (6)C12—N2—C9—N1175.0 (7)
O2i—Zn—N3—C16−169.2 (5)C9—N2—C10—C110.1 (12)
O3—Zn—N3—C16−54.5 (6)C12—N2—C10—C11−169.9 (11)
N1—Zn—N3—C1661.3 (6)N2—C10—C11—N1−2.1 (12)
C6—C1—C2—C3−0.8 (13)C9—N1—C11—C103.4 (11)
C1—C2—C3—C41.3 (10)Zn—N1—C11—C10−176.4 (6)
C1—C2—C3—C7−176.2 (8)C10—N2—C12—C1312.3 (19)
C2—C3—C4—C5−1.1 (10)C9—N2—C12—C13−157.8 (10)
C7—C3—C4—C5176.3 (7)C16—N3—C14—N41.4 (8)
C2—C3—C4—C8178.8 (7)Zn—N3—C14—N4−170.2 (4)
C7—C3—C4—C8−3.7 (10)C15—N4—C14—N3−0.5 (9)
C3—C4—C5—C60.5 (12)C17—N4—C14—N3177.9 (8)
C8—C4—C5—C6−179.4 (8)C14—N4—C15—C16−0.8 (10)
C2—C1—C6—C50.2 (15)C17—N4—C15—C16−179.3 (8)
C4—C5—C6—C1−0.1 (14)N4—C15—C16—N31.6 (10)
Znii—O2—C7—O18.7 (9)C14—N3—C16—C15−1.9 (9)
Znii—O2—C7—C3−173.8 (4)Zn—N3—C16—C15169.9 (6)
C2—C3—C7—O1129.9 (8)C14—N4—C17—C18−1.1 (17)
C4—C3—C7—O1−47.6 (10)C15—N4—C17—C18177.0 (11)
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.513.435 (10)170
C14—H14A···O4i0.932.253.166 (8)167
C18—H18A···O4i0.932.493.405 (11)169
Symmetry codes: (i) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.513.435 (10)170
C14—H14A···O4i0.932.253.166 (8)167
C18—H18A···O4i0.932.493.405 (11)169
Symmetry codes: (i) x, −y+1/2, z+1/2.
Acknowledgements top

This work was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B12).

references
References top

Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.

Liu, Q. Y., Liu, P., Wang, J. & Chen, Y. (2002). Chin. J. Struct. Chem. 21, 509–512.

Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.