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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 π–π stacking inter­actions [with a shortest atom-to-atom distance of 3.41 (1) Å] are observed between the chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027067/hy2062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027067/hy2062Isup2.hkl
Contains datablock I

CCDC reference: 654723

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 1.94
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

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).

Structure description 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.

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

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)]F(000) = 1128
Mr = 551.79Dx = 1.520 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2132 reflections
a = 20.940 (3) Åθ = 2.4–26.1°
b = 9.6078 (12) ŵ = 1.07 mm1
c = 14.7942 (19) ÅT = 292 K
β = 125.884 (2)°Block, 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)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2524
Tmin = 0.890, Tmax = 0.951k = 1111
6569 measured reflectionsl = 1817
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0583P)2]
where P = (Fo2 + 2Fc2)/3
2385 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
[Zn(C8H5O4)2(C10H8N2)]V = 2411.4 (6) Å3
Mr = 551.79Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.940 (3) ŵ = 1.07 mm1
b = 9.6078 (12) ÅT = 292 K
c = 14.7942 (19) Å0.12 × 0.09 × 0.05 mm
β = 125.884 (2)°
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)] = 0.0330 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.04Δρmax = 0.39 e Å3
2385 reflectionsΔρmin = 0.40 e Å3
168 parameters
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)
H2A0.31220.24830.68590.065*
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)
H4A0.28130.11720.40710.064*
C10.38671 (15)0.0992 (3)0.70599 (19)0.0542 (6)
H1A0.41370.09440.78300.065*
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, º) 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, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2iii0.821.972.771 (3)165
Symmetry code: (iii) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Zn(C8H5O4)2(C10H8N2)]
Mr551.79
Crystal system, space groupMonoclinic, C2/c
Temperature (K)292
a, b, c (Å)20.940 (3), 9.6078 (12), 14.7942 (19)
β (°) 125.884 (2)
V3)2411.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.07
Crystal size (mm)0.12 × 0.09 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.890, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
6569, 2385, 2096
Rint0.041
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.091, 1.04
No. of reflections2385
No. of parameters168
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.40

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) 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 code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2ii0.8201.972.771 (3)165
Symmetry code: (ii) x+1/2, y+1/2, z+3/2.
 

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