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Acta Cryst. (2007). E63, m1839-m1840    [ doi:10.1107/S1600536807027067 ]

catena-Poly[[bis(benzene-1,3-dicarboxylato-[kappa]2O,O')zinc(II)]-[mu]-4,4'-bipyridine-[kappa]2N:N']

X.-M. Li, Y.-H. Dong, Q.-W. Wang and B. Liu

Abstract top

In the title compound, [Zn(C8H5O4)2(C10H8N2)]n, the ZnII atom lies on a twofold rotation axis, and is coordinated by two N atoms of two 4,4'-bipyridine ligands and two carboxylate groups, each in a chelating mode, from two isophthalate ligands. The 4,4'-bipyridine ligand, located on an inversion center, bridges the ZnII atoms, forming a one-dimensional zigzag chain structure. O-H...O hydrogen bonds and [pi]-[pi] stacking interactions [with a shortest atom-to-atom distance of 3.41 (1) Å] are observed between the chains.

Comment top

Metal-organic complexes with a variety of supramolecular architectures have attracted increasing interest because of their novel topologies and potential applications as functional materials (Eddaoudi et al., 2001). Recently, a successful strategy for preparing these materials has been the assembly reaction between transition metal ions and two types of ligands, one acts as a terminal ligand and the other acts as a bridging ligand. In this respect, diverse dicarboxylates with various oriented carboxyl groups have been utilized to build coordination polymers. These ligands are able to bridge metal centers in different modes and also produce either linear or zigzag polymeric chains (Chen & Liu, 2002; Groeneman et al., 1999; Li et al., 2006). In this work, we use isophthalic acid as a terminal ligand and 4,4'-bipyridine (bpy) as a bridging ligand, generating a new compound, (I), under hydrothermal condition.

Selected bond lengths and angles for (I) are given in Table 1. In compound (I), the ZnII atom lying on a twofold rotation axis is six-coordinated by two N atoms from two bpy ligands, and two carboxylate groups, each in a chelating mode, from two isophthalate ligands (Fig. 1). The bpy ligand located on an inversion center bridges the ZnII atoms, forming a one-dimensional zigzag chain structure. It is noteworthy that there exist π-π interactions, with the shortest atom-to-atom distance of 3.41 (1) Å, and O—H···O hydrogen bonds (Table 2, Fig. 2) between the isophthalate ligands in the neighboring chains, which lead to a three-dimensional supramolecular network.

Related literature top

For general background, see: Eddaoudi et al. (2001). For related structures, see: Chen & Liu (2002); Groeneman et al. (1999); Li et al. (2006).

Experimental top

Compound (I) was prepared from a mixture of Zn(NO3)2·6H2O (0.119 g, 0.4 mmol), isophthalic acid (0.134 g, 0.8 mmol), bpy (0.070 g, 0.4 mmol) and H2O (18 ml) in a 30 ml Teflon-lined autoclave under autogenous pressure at 423 K for 7 d. After cooling to room temperature, colorless crystals suitable for X-ray structure analysis were obtained. Analysis, calculated for C26H18N2O8Zn: C 64.7, H 2.7, N 5.8%; found: C 64.5, H 2.6, N 5.7%.

Refinement top

All H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H= 0.93Å and Uiso(H) = 1.2Ueq(C) and with O—H = 0.82Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), together with symmetry-related atoms to complete the Zn coordination. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1 − x, y, 3/2 − z, (ii) 1/2 − x, −1/2 − y, 1 − z.]
[Figure 2] Fig. 2. View of the chain structure in (I).
catena-Poly[[bis(benzene-1,3-dicarboxylato-κ2O,O')zinc(II)]- µ-4,4'-bipyridine-κ2N:N'] top
Crystal data top
[Zn(C8H5O4)2(C10H8N2)]F000 = 1128
Mr = 551.79Dx = 1.520 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2132 reflections
a = 20.940 (3) Åθ = 2.4–26.1º
b = 9.6078 (12) ŵ = 1.07 mm−1
c = 14.7942 (19) ÅT = 292 (2) K
β = 125.884 (2)ºBlock, colorless
V = 2411.4 (6) Å30.12 × 0.09 × 0.05 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2385 independent reflections
Radiation source: fine-focus sealed tube2096 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 292(2) Kθmax = 26.1º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→24
Tmin = 0.890, Tmax = 0.951k = −11→11
6569 measured reflectionsl = −18→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)] = 0.033H-atom parameters constrained
wR(F2) = 0.091  w = 1/[σ2(Fo2) + (0.0583P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2385 reflectionsΔρmax = 0.39 e Å−3
168 parametersΔρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C8H5O4)2(C10H8N2)]V = 2411.4 (6) Å3
Mr = 551.79Z = 4
Monoclinic, C2/cMo Kα
a = 20.940 (3) ŵ = 1.07 mm−1
b = 9.6078 (12) ÅT = 292 (2) K
c = 14.7942 (19) Å0.12 × 0.09 × 0.05 mm
β = 125.884 (2)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2385 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2096 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.951Rint = 0.041
6569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033168 parameters
wR(F2) = 0.091H-atom parameters constrained
S = 1.04Δρmax = 0.39 e Å−3
2385 reflectionsΔρmin = −0.39 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50000.12559 (3)0.75000.03382 (14)
C20.32554 (15)−0.1920 (3)0.64815 (19)0.0543 (6)
H2A0.3122−0.24830.68590.065*
O20.39232 (9)0.29538 (15)0.71869 (12)0.0433 (4)
O10.49428 (9)0.19702 (15)0.86982 (13)0.0461 (4)
C50.36932 (14)−0.0250 (2)0.54810 (19)0.0533 (6)
H5A0.38390.03270.51250.064*
O40.25572 (10)0.67575 (18)0.91871 (14)0.0606 (5)
H40.21650.72500.88090.091*
O30.22568 (15)0.6223 (2)0.75308 (18)0.1004 (9)
N10.40947 (9)−0.01606 (16)0.65816 (14)0.0362 (4)
C30.28368 (11)−0.20154 (19)0.53335 (16)0.0338 (4)
C100.38715 (12)0.5013 (2)1.02708 (18)0.0437 (5)
H10A0.37720.55121.07140.052*
C130.26886 (15)0.6106 (2)0.8536 (2)0.0487 (6)
C60.43472 (12)0.27635 (19)0.82190 (17)0.0357 (4)
C120.46543 (13)0.3362 (2)1.00919 (18)0.0423 (5)
H12A0.50820.27561.04250.051*
C70.41740 (12)0.35150 (19)0.89450 (17)0.0339 (4)
C80.35402 (12)0.4413 (2)0.84621 (17)0.0381 (5)
H8A0.32130.45140.76910.046*
C90.33852 (12)0.5171 (2)0.91158 (18)0.0396 (5)
C110.44993 (14)0.4114 (3)1.07490 (19)0.0494 (6)
H11A0.48250.40051.15200.059*
C40.30732 (15)−0.1149 (2)0.4840 (2)0.0531 (6)
H4A0.2813−0.11720.40710.064*
C10.38671 (15)−0.0992 (3)0.70599 (19)0.0542 (6)
H1A0.4137−0.09440.78300.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0357 (2)0.0348 (2)0.0313 (2)0.0000.01984 (17)0.000
C20.0657 (15)0.0592 (14)0.0373 (12)−0.0254 (12)0.0298 (12)−0.0015 (11)
O20.0557 (9)0.0459 (8)0.0385 (8)−0.0018 (7)0.0334 (8)−0.0011 (6)
O10.0466 (9)0.0489 (8)0.0476 (9)0.0067 (7)0.0303 (8)−0.0040 (7)
C50.0570 (14)0.0655 (15)0.0377 (12)−0.0221 (12)0.0278 (12)−0.0006 (11)
O40.0575 (10)0.0744 (11)0.0521 (11)0.0161 (9)0.0334 (9)−0.0125 (9)
O30.126 (2)0.138 (2)0.0536 (13)0.0874 (16)0.0614 (14)0.0386 (13)
N10.0377 (9)0.0369 (8)0.0344 (9)−0.0025 (7)0.0214 (8)−0.0009 (7)
C30.0372 (10)0.0340 (10)0.0331 (10)−0.0006 (8)0.0223 (9)−0.0016 (8)
C100.0488 (12)0.0509 (12)0.0411 (12)−0.0074 (10)0.0317 (11)−0.0121 (10)
C130.0633 (16)0.0489 (13)0.0509 (15)0.0122 (11)0.0430 (14)0.0060 (10)
C60.0414 (11)0.0325 (9)0.0422 (12)−0.0063 (8)0.0295 (10)−0.0051 (8)
C120.0412 (12)0.0483 (11)0.0391 (12)0.0013 (9)0.0245 (11)−0.0001 (10)
C70.0370 (11)0.0344 (10)0.0360 (11)−0.0056 (8)0.0246 (10)−0.0030 (8)
C80.0442 (11)0.0422 (11)0.0341 (11)−0.0004 (9)0.0265 (10)−0.0002 (9)
C90.0460 (12)0.0400 (11)0.0423 (12)−0.0028 (9)0.0312 (11)−0.0027 (9)
C110.0483 (13)0.0661 (14)0.0313 (11)−0.0030 (11)0.0218 (11)−0.0053 (10)
C40.0581 (15)0.0672 (15)0.0321 (12)−0.0238 (12)0.0253 (12)−0.0059 (10)
C10.0599 (15)0.0638 (15)0.0282 (11)−0.0242 (12)0.0199 (11)−0.0054 (10)
Geometric parameters (Å, °) top
Zn1—O1i1.9689 (15)C3—C41.377 (3)
Zn1—O11.9689 (15)C3—C3ii1.483 (4)
Zn1—N12.0669 (16)C10—C111.373 (3)
Zn1—N1i2.0669 (16)C10—C91.393 (3)
Zn1—O22.5953 (15)C10—H10A0.9300
C2—C11.372 (3)C13—C91.485 (3)
C2—C31.384 (3)C6—C71.504 (3)
C2—H2A0.9300C12—C71.383 (3)
O2—C61.251 (2)C12—C111.394 (3)
O1—C61.266 (2)C12—H12A0.9300
C5—N11.327 (3)C7—C81.380 (3)
C5—C41.374 (3)C8—C91.392 (3)
C5—H5A0.9300C8—H8A0.9300
O4—C131.307 (3)C11—H11A0.9300
O4—H40.8200C4—H4A0.9300
O3—C131.210 (3)C1—H1A0.9300
N1—C11.327 (3)
O1i—Zn1—O1139.21 (9)O3—C13—O4122.2 (2)
O1i—Zn1—N198.86 (6)O3—C13—C9122.7 (2)
O1—Zn1—N1107.76 (6)O4—C13—C9115.1 (2)
O1i—Zn1—N1i107.76 (6)O2—C6—O1122.22 (18)
O1—Zn1—N1i98.86 (6)O2—C6—C7120.39 (18)
N1—Zn1—N1i97.64 (9)O1—C6—C7117.37 (18)
O1—Zn1—O255.71 (5)C7—C12—C11120.1 (2)
O1i—Zn1—O297.19 (5)C7—C12—H12A119.9
N1—Zn1—O286.01 (6)C11—C12—H12A119.9
N1i—Zn1—O2153.80 (6)C8—C7—C12119.26 (18)
O2i—Zn1—O2102.11 (6)C8—C7—C6119.45 (18)
C1—C2—C3119.8 (2)C12—C7—C6121.25 (19)
C1—C2—H2A120.1C7—C8—C9120.82 (19)
C3—C2—H2A120.1C7—C8—H8A119.6
C6—O1—Zn1105.40 (13)C9—C8—H8A119.6
N1—C5—C4123.4 (2)C8—C9—C10119.66 (19)
N1—C5—H5A118.3C8—C9—C13117.70 (19)
C4—C5—H5A118.3C10—C9—C13122.63 (19)
C13—O4—H4109.5C10—C11—C12120.7 (2)
C5—N1—C1116.62 (18)C10—C11—H11A119.6
C5—N1—Zn1121.76 (14)C12—C11—H11A119.6
C1—N1—Zn1121.57 (14)C5—C4—C3120.1 (2)
C4—C3—C2116.42 (19)C5—C4—H4A119.9
C4—C3—C3ii121.6 (2)C3—C4—H4A119.9
C2—C3—C3ii122.0 (2)N1—C1—C2123.7 (2)
C11—C10—C9119.43 (19)N1—C1—H1A118.2
C11—C10—H10A120.3C2—C1—H1A118.2
C9—C10—H10A120.3
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y−1/2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2iii0.821.972.771 (3)165
Symmetry codes: (iii) −x+1/2, y+1/2, −z+3/2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—O11.9689 (15)Zn1—O22.5953 (15)
Zn1—N12.0669 (16)
O1i—Zn1—O1139.21 (9)O1i—Zn1—O297.19 (5)
O1—Zn1—N1107.76 (6)N1—Zn1—O286.01 (6)
O1—Zn1—N1i98.86 (6)N1i—Zn1—O2153.80 (6)
N1—Zn1—N1i97.64 (9)O2i—Zn1—O2102.11 (6)
Symmetry codes: (i) −x+1, y, −z+3/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2ii0.821.972.771 (3)165
Symmetry codes: (ii) −x+1/2, y+1/2, −z+3/2.
Acknowledgements top

We thank Mr Heng-Qing Jia of Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, for data collection.

references
References top

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Groeneman, R. H., MacGillivray, L. R. & Atwood, J. L. (1999). Inorg. Chem. 38, 208–209.

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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.