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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1106.
Published online 2008 August 6. doi:  10.1107/S1600536808023982
PMCID: PMC2960729

Poly[zinc(II)-[μ-1,4-bis­(imidazol-1-yl­methyl)benzene]-μ-4,4′-oxydibenzoato]

Abstract

In the title compound, [Zn(C14H8O5)(C14H14N4)]n, the coordination polyhedron around each ZnII atom is a distorted tetra­hedron. The ligands bridge the Zn atoms to form a two-dimensional (4,4)-network.

Related literature

For related literature, see Batten & Robson (1998 [triangle]); Ma et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1106-scheme1.jpg

Experimental

Crystal data

  • [Zn(C14H8O5)(C14H14N4)]
  • M r = 559.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1106-efi5.jpg
  • a = 6.1608 (9) Å
  • b = 25.811 (4) Å
  • c = 16.185 (3) Å
  • β = 92.503 (2)°
  • V = 2571.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.00 mm−1
  • T = 293 (2) K
  • 0.33 × 0.25 × 0.19 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.718, T max = 0.826
  • 14194 measured reflections
  • 5057 independent reflections
  • 3906 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.159
  • S = 1.07
  • 5057 reflections
  • 343 parameters
  • H-atom parameters constrained
  • Δρmax = 1.43 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023982/bt2755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023982/bt2755Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author thanks Beihua University for supporting this work.

supplementary crystallographic information

Comment

Metal–organic frameworks is currently of great interest because of their interesting structures and potential applications. As a good candidate for rigid rod-like spacers in the construction of metal–organic polymers, 4,4'-bipyridine has been relatively well known and has shown hundreds of interesting supramolecular architectures (Batten & Robson, 1998). However, the flexible ligands such as 1,4-bis(imidazol-1-ylmethyl)benzene (L) has not been well explored to date (Ma et al., 2003). In this work, I selected 4,4'-oxybis(benzoic acid) (H2oba) and L as linkers, generating a new coordination polymer, [Zn(oba)(L)], (I), which is reported here.

In compound (I) each ZnII atom is four-coordinated by two N atoms from one L ligand, and two O atoms from two oba carboxylate anions in a distorted tetrahedral coordination sphere (Fig. 1). The two neighbouring ZnII atoms are bridged by the oba and L ligands to form a two-dimensional (4,4) network (Fig. 2).

Experimental

A mixture of H2oba (0.5 mmol), L (0.5 mmol), NaOH (1 mmol) and ZnCl2.6H2O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20 ml Teflon-lined autoclave. Upon heating at 170°C for one week, the autoclave was slowly cooled to room temperature. The crystals were collected, washed with deionized water and dried.

Refinement

H atoms were generated geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.
The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) -1 - x, 1/2 + y, 1/2 - z; (ii) x, 1/2 - y, 1/2 + z.
Fig. 2.
View of the chain structure of (I).

Crystal data

[Zn(C14H8O5)(C14H14N4)]F000 = 1152
Mr = 559.87Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5057 reflections
a = 6.1608 (9) Åθ = 1.9–26.1º
b = 25.811 (4) ŵ = 1.00 mm1
c = 16.185 (3) ÅT = 293 (2) K
β = 92.503 (2)ºBlock, colourless
V = 2571.2 (7) Å30.33 × 0.25 × 0.19 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer5057 independent reflections
Radiation source: fine-focus sealed tube3906 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 293(2) Kθmax = 26.1º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 1998)h = −7→6
Tmin = 0.718, Tmax = 0.826k = −31→27
14194 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.159  w = 1/[σ2(Fo2) + (0.0761P)2 + 2.2361P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
5057 reflectionsΔρmax = 1.43 e Å3
343 parametersΔρmin = −0.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C10.1661 (7)0.04984 (15)0.0495 (3)0.0273 (9)
H10.05250.02750.06030.033*
C20.3029 (7)0.04487 (16)−0.0136 (3)0.0284 (9)
H20.30040.0190−0.05370.034*
C30.3919 (7)0.11368 (15)0.0599 (3)0.0281 (9)
H30.46430.14340.07840.034*
C40.6352 (8)0.09401 (17)−0.0563 (3)0.0384 (11)
H4A0.61210.0764−0.10890.046*
H4B0.76230.0789−0.02830.046*
C50.6768 (7)0.15040 (16)−0.0719 (3)0.0312 (10)
C60.5194 (8)0.18139 (19)−0.1091 (3)0.0416 (12)
H60.38610.1668−0.12510.050*
C70.5531 (8)0.23363 (19)−0.1233 (3)0.0440 (12)
H70.44250.2537−0.14760.053*
C80.7516 (7)0.25584 (16)−0.1014 (3)0.0274 (9)
C90.9128 (7)0.22467 (18)−0.0648 (3)0.0355 (11)
H91.04790.2388−0.05020.043*
C100.8738 (8)0.17265 (18)−0.0500 (3)0.0379 (11)
H100.98280.1524−0.02490.045*
C110.8036 (7)0.31222 (17)−0.1168 (3)0.0333 (10)
H11A0.87590.3266−0.06750.040*
H11B0.90320.3145−0.16140.040*
C120.4828 (8)0.36811 (18)−0.0836 (3)0.0393 (12)
H120.50950.3720−0.02690.047*
C130.3094 (8)0.38615 (17)−0.1294 (3)0.0349 (11)
H130.19680.4057−0.10910.042*
C140.5102 (7)0.34527 (16)−0.2128 (3)0.0272 (9)
H140.56390.3306−0.26030.033*
C15−0.2311 (7)0.04825 (15)0.2220 (3)0.0269 (9)
C16−0.3735 (7)0.01450 (15)0.2723 (3)0.0272 (9)
C17−0.5687 (7)−0.00464 (16)0.2373 (3)0.0312 (10)
H17−0.60760.00320.18260.037*
C18−0.7053 (7)−0.03508 (17)0.2825 (3)0.0332 (10)
H18−0.8353−0.04750.25870.040*
C19−0.6446 (7)−0.04668 (15)0.3635 (3)0.0301 (10)
C20−0.4550 (8)−0.02835 (16)0.4000 (3)0.0322 (10)
H20−0.4174−0.03660.45470.039*
C21−0.3190 (7)0.00262 (16)0.3547 (3)0.0305 (10)
H21−0.19100.01550.37950.037*
C22−0.8501 (7)−0.12400 (15)0.3885 (3)0.0291 (9)
C23−0.7128 (7)−0.15793 (17)0.3502 (3)0.0370 (11)
H23−0.5768−0.14710.33440.044*
C24−0.7814 (7)−0.20848 (16)0.3356 (3)0.0350 (11)
H24−0.6888−0.23180.31110.042*
C25−0.9857 (7)−0.22472 (15)0.3571 (3)0.0268 (9)
C26−1.0669 (7)−0.27912 (16)0.3427 (3)0.0294 (10)
C27−1.1208 (7)−0.18936 (16)0.3946 (3)0.0333 (10)
H27−1.2587−0.19970.40900.040*
C28−1.0534 (7)−0.13930 (17)0.4106 (3)0.0340 (10)
H28−1.1446−0.11610.43600.041*
N10.2223 (6)0.09330 (12)0.0948 (2)0.0258 (8)
N20.4459 (6)0.08575 (13)−0.0061 (2)0.0270 (8)
N30.6107 (6)0.34292 (13)−0.1381 (2)0.0281 (8)
N40.3250 (6)0.37110 (13)−0.2109 (2)0.0282 (8)
O1−0.0854 (5)0.07421 (11)0.26198 (18)0.0326 (7)
O2−0.2634 (5)0.05027 (12)0.14567 (18)0.0353 (7)
O3−1.2588 (5)−0.28926 (12)0.3550 (2)0.0393 (8)
O4−0.9314 (5)−0.31274 (11)0.31674 (19)0.0331 (7)
O5−0.7843 (5)−0.07438 (11)0.41306 (19)0.0380 (8)
Zn10.09373 (8)0.120902 (17)0.19746 (3)0.02586 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.028 (2)0.022 (2)0.032 (2)−0.0029 (17)−0.0013 (18)−0.0012 (17)
C20.030 (2)0.026 (2)0.029 (2)0.0022 (18)−0.0012 (18)−0.0039 (17)
C30.032 (2)0.020 (2)0.032 (2)0.0034 (17)0.0039 (19)−0.0014 (17)
C40.039 (3)0.028 (2)0.049 (3)0.004 (2)0.023 (2)0.004 (2)
C50.036 (3)0.029 (2)0.030 (2)0.0011 (19)0.011 (2)0.0031 (18)
C60.030 (3)0.042 (3)0.052 (3)−0.008 (2)−0.004 (2)0.011 (2)
C70.032 (3)0.040 (3)0.059 (3)−0.003 (2)−0.005 (2)0.021 (2)
C80.026 (2)0.031 (2)0.026 (2)0.0028 (18)0.0033 (17)0.0044 (17)
C90.025 (2)0.038 (3)0.044 (3)0.001 (2)−0.003 (2)0.001 (2)
C100.032 (3)0.035 (3)0.047 (3)0.008 (2)−0.001 (2)0.008 (2)
C110.024 (2)0.037 (3)0.038 (3)−0.0009 (19)−0.0014 (19)0.005 (2)
C120.052 (3)0.035 (3)0.031 (2)0.001 (2)0.003 (2)−0.003 (2)
C130.040 (3)0.029 (2)0.036 (3)0.003 (2)0.010 (2)−0.0047 (19)
C140.026 (2)0.029 (2)0.027 (2)0.0018 (18)0.0003 (18)0.0035 (17)
C150.027 (2)0.017 (2)0.037 (3)0.0043 (17)0.0066 (19)0.0005 (17)
C160.032 (2)0.018 (2)0.033 (2)0.0043 (17)0.0065 (19)−0.0012 (17)
C170.040 (3)0.026 (2)0.028 (2)−0.0034 (19)0.000 (2)0.0000 (18)
C180.030 (3)0.032 (2)0.037 (3)−0.009 (2)−0.001 (2)−0.0031 (19)
C190.040 (3)0.016 (2)0.034 (2)−0.0043 (18)0.009 (2)−0.0005 (17)
C200.048 (3)0.024 (2)0.025 (2)−0.001 (2)0.003 (2)0.0018 (17)
C210.032 (2)0.025 (2)0.033 (2)−0.0044 (18)−0.0035 (19)−0.0005 (18)
C220.041 (3)0.021 (2)0.026 (2)−0.0033 (19)0.0050 (19)0.0005 (17)
C230.031 (3)0.033 (2)0.048 (3)−0.011 (2)0.013 (2)0.000 (2)
C240.035 (3)0.024 (2)0.047 (3)0.0005 (19)0.019 (2)−0.0029 (19)
C250.028 (2)0.022 (2)0.031 (2)−0.0032 (17)0.0027 (18)0.0014 (17)
C260.035 (3)0.021 (2)0.032 (2)−0.0009 (18)0.0055 (19)0.0008 (17)
C270.030 (2)0.027 (2)0.043 (3)−0.0020 (19)0.009 (2)−0.0003 (19)
C280.036 (3)0.025 (2)0.042 (3)0.0024 (19)0.013 (2)−0.0013 (19)
N10.030 (2)0.0206 (17)0.0268 (18)0.0008 (15)0.0026 (15)−0.0004 (14)
N20.029 (2)0.0230 (18)0.0299 (18)0.0035 (15)0.0051 (15)0.0005 (14)
N30.029 (2)0.0268 (19)0.0286 (19)−0.0002 (15)0.0015 (16)0.0065 (15)
N40.030 (2)0.0240 (18)0.0303 (19)0.0032 (15)0.0033 (15)0.0039 (15)
O10.0351 (18)0.0278 (16)0.0354 (17)−0.0094 (13)0.0073 (14)0.0003 (13)
O20.0397 (19)0.0369 (18)0.0300 (17)−0.0037 (14)0.0068 (14)0.0024 (13)
O30.0345 (19)0.0294 (17)0.055 (2)−0.0072 (14)0.0087 (16)−0.0032 (15)
O40.0340 (18)0.0234 (15)0.0426 (18)−0.0012 (13)0.0088 (14)−0.0021 (13)
O50.053 (2)0.0251 (16)0.0375 (18)−0.0140 (14)0.0200 (16)−0.0062 (13)
Zn10.0284 (3)0.0203 (3)0.0292 (3)−0.0010 (2)0.0048 (2)−0.00183 (19)

Geometric parameters (Å, °)

C1—C21.357 (6)C15—O21.243 (5)
C1—N11.376 (5)C15—O11.274 (5)
C1—H10.9300C15—C161.502 (6)
C2—N21.377 (5)C16—C211.395 (6)
C2—H20.9300C16—C171.397 (6)
C3—N11.319 (5)C17—C181.383 (6)
C3—N21.342 (5)C17—H170.9300
C3—H30.9300C18—C191.381 (6)
C4—N21.466 (5)C18—H180.9300
C4—C51.501 (6)C19—C201.370 (6)
C4—H4A0.9700C19—O51.398 (5)
C4—H4B0.9700C20—C211.389 (6)
C5—C61.375 (6)C20—H200.9300
C5—C101.375 (6)C21—H210.9300
C6—C71.385 (6)C22—C281.375 (6)
C6—H60.9300C22—C231.383 (6)
C7—C81.383 (6)C22—O51.396 (5)
C7—H70.9300C23—C241.389 (6)
C8—C91.390 (6)C23—H230.9300
C8—C111.513 (6)C24—C251.385 (6)
C9—C101.387 (6)C24—H240.9300
C9—H90.9300C25—C271.392 (6)
C10—H100.9300C25—C261.505 (6)
C11—N31.457 (5)C26—O31.236 (5)
C11—H11A0.9700C26—O41.288 (5)
C11—H11B0.9700C27—C281.378 (6)
C12—C131.356 (7)C27—H270.9300
C12—N31.372 (6)C28—H280.9300
C12—H120.9300N1—Zn12.002 (3)
C13—N41.383 (5)N4—Zn1i2.021 (4)
C13—H130.9300O1—Zn11.965 (3)
C14—N41.323 (5)O4—Zn1ii1.992 (3)
C14—N31.336 (5)Zn1—O4iii1.992 (3)
C14—H140.9300Zn1—N4iv2.021 (4)
C2—C1—N1109.1 (4)C16—C17—H17119.3
C2—C1—H1125.4C19—C18—C17118.6 (4)
N1—C1—H1125.4C19—C18—H18120.7
C1—C2—N2106.1 (4)C17—C18—H18120.7
C1—C2—H2126.9C20—C19—C18121.6 (4)
N2—C2—H2126.9C20—C19—O5117.7 (4)
N1—C3—N2110.8 (4)C18—C19—O5120.5 (4)
N1—C3—H3124.6C19—C20—C21119.6 (4)
N2—C3—H3124.6C19—C20—H20120.2
N2—C4—C5112.3 (3)C21—C20—H20120.2
N2—C4—H4A109.1C20—C21—C16120.3 (4)
C5—C4—H4A109.1C20—C21—H21119.8
N2—C4—H4B109.1C16—C21—H21119.8
C5—C4—H4B109.1C28—C22—C23121.1 (4)
H4A—C4—H4B107.9C28—C22—O5116.5 (4)
C6—C5—C10117.9 (4)C23—C22—O5122.2 (4)
C6—C5—C4121.0 (4)C22—C23—C24118.9 (4)
C10—C5—C4121.1 (4)C22—C23—H23120.5
C5—C6—C7122.1 (4)C24—C23—H23120.5
C5—C6—H6119.0C25—C24—C23121.0 (4)
C7—C6—H6119.0C25—C24—H24119.5
C8—C7—C6119.9 (4)C23—C24—H24119.5
C8—C7—H7120.1C24—C25—C27118.6 (4)
C6—C7—H7120.1C24—C25—C26122.9 (4)
C7—C8—C9118.5 (4)C27—C25—C26118.5 (4)
C7—C8—C11123.2 (4)O3—C26—O4123.3 (4)
C9—C8—C11118.3 (4)O3—C26—C25119.1 (4)
C10—C9—C8120.5 (4)O4—C26—C25117.6 (4)
C10—C9—H9119.7C28—C27—C25121.0 (4)
C8—C9—H9119.7C28—C27—H27119.5
C5—C10—C9121.2 (4)C25—C27—H27119.5
C5—C10—H10119.4C22—C28—C27119.4 (4)
C9—C10—H10119.4C22—C28—H28120.3
N3—C11—C8112.7 (4)C27—C28—H28120.3
N3—C11—H11A109.1C3—N1—C1106.4 (3)
C8—C11—H11A109.1C3—N1—Zn1124.3 (3)
N3—C11—H11B109.1C1—N1—Zn1129.2 (3)
C8—C11—H11B109.1C3—N2—C2107.5 (3)
H11A—C11—H11B107.8C3—N2—C4126.4 (4)
C13—C12—N3105.8 (4)C2—N2—C4125.8 (4)
C13—C12—H12127.1C14—N3—C12107.7 (4)
N3—C12—H12127.1C14—N3—C11125.4 (4)
C12—C13—N4109.9 (4)C12—N3—C11126.2 (4)
C12—C13—H13125.1C14—N4—C13105.0 (4)
N4—C13—H13125.1C14—N4—Zn1i128.0 (3)
N4—C14—N3111.6 (4)C13—N4—Zn1i126.5 (3)
N4—C14—H14124.2C15—O1—Zn1116.9 (3)
N3—C14—H14124.2C26—O4—Zn1ii106.7 (3)
O2—C15—O1124.1 (4)C22—O5—C19119.0 (3)
O2—C15—C16119.5 (4)O1—Zn1—O4iii107.32 (12)
O1—C15—C16116.4 (4)O1—Zn1—N1118.32 (13)
C21—C16—C17118.5 (4)O4iii—Zn1—N1115.16 (13)
C21—C16—C15121.6 (4)O1—Zn1—N4iv93.85 (13)
C17—C16—C15119.9 (4)O4iii—Zn1—N4iv109.34 (13)
C18—C17—C16121.3 (4)N1—Zn1—N4iv110.68 (14)
C18—C17—H17119.3

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x−1, y−1/2, −z+1/2; (iii) −x−1, y+1/2, −z+1/2; (iv) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2755).

References

  • Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed.37, 1460–1494.
  • Bruker (1998). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem.42, 7531–7534. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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