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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m258.
Published online 2010 February 6. doi:  10.1107/S1600536810003892
PMCID: PMC2983726

catena-Poly[[bis­(1-allyl­imidazole)zinc(II)]-μ-phthalato-κ2 O 1:O 2]

Abstract

The structure of the title compound, [Zn(C8H4O4)(C6H8N2)2]n, exhibits polymeric zigzag chains extended along the c axis. The ZnII ion is coordinated by two N [Zn—N = 2.008 (6) and 2.012 (6) Å] and two O [Zn—O = 1.959 (5) and 1.985 (5) Å] atoms in a distorted tetra­hedral geometry. Weak C—H(...)O inter­actions contribute to the crystal packing stability.

Related literature

In the corresponding zinc compounds, [Zn(phthalato)(1-H-vinyl­imidazole)2] (Li et al., 2007a [triangle]) and [Zn(phthalato)(1-H-ethyl­imidazole)2] (Li et al., 2007b [triangle]), the ZnII ions also have a distorted tetra­hedral environment.

An external file that holds a picture, illustration, etc.
Object name is e-66-0m258-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H4O4)(C6H8N2)2]
  • M r = 445.77
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m258-efi1.jpg
  • a = 10.675 (2) Å
  • b = 13.858 (3) Å
  • c = 13.610 (3) Å
  • V = 2013.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.25 mm−1
  • T = 293 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.788, T max = 0.885
  • 3662 measured reflections
  • 3078 independent reflections
  • 2672 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.170
  • S = 1.01
  • 3078 reflections
  • 262 parameters
  • 21 restraints
  • H-atom parameters constrained
  • Δρmax = 0.86 e Å−3
  • Δρmin = −0.94 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1148 Friedel pairs
  • Flack parameter: 0.01 (3)

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003892/hg2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003892/hg2640Isup2.hkl

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

Acknowledgments

This work was supported by the NSF of China (Nos. 20601015, 20871072) and the Doctoral Science Foundation of Shandong Province (No. 2007BS04023).

supplementary crystallographic information

Comment

In the title compound,(I)(Fig. 1), The zinc(II) centers are bridged by the carboxylate group of o-phthalate and saturated by 1-allylimidazole. Each ZnII ion is coordinated by two N [Zn—N2 = 2.012 (6),Zn—N4 = 2.008 (6) Å] and two O [Zn—O2 = 1.959 (5), Zn—O4 = 1.985 (5) Å] atoms in a distorted tetrahedral geometry. All these values agree well with those observed in [Zn(phthalato)(1-H-vinylimidazole)2] (Li et al., 2007a) and [Zn(phthalato)(1-H-ethylimidazole)2] (Li et al., 2007b). Each o-phthalate dianion acts as a bidentate ligand to bridge two ZnII atoms through two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 6.908 (6) Å.In the crystal, Weak C—H···O interactions contribute to the crystal packing stability.

In the corresponding zinc compounds, [Zn(phthalato)(1-H-vinylimidazole)2] (Li, et al., 2007a) and [Zn(phthalato)(1-H-ethylimidazole)2] (Li, et al., 2007b) the ZnII ions have a distorted tetrahedral environment.

Experimental

The reaction of ZnCl2(0.68 g, 5 mmol) with o-phthalic acid (0.83 g, 5 mmol) in an aqueous-methanol(3:1) solution(40 ml) at 363 K for 30 minutes produced a colorless solution, to which 1-allylimidazole (1.08 g,10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 363 K . Colorless crystals were obtained after a few days.

Refinement

H atoms were positioned geometrically(C—H = 0.93-0.97 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.
A portion of the polymeric chain in the title compound showing atomic numbering and 30% probability displacement ellipsoids [symmetry codes: (A) -x+3/2,y,z-1/2.
Fig. 2.
The packing of (I), viewed down the b axis.

Crystal data

[Zn(C8H4O4)(C6H8N2)2]F(000) = 920
Mr = 445.77Dx = 1.471 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3003 reflections
a = 10.675 (2) Åθ = 1.5–25.3°
b = 13.858 (3) ŵ = 1.25 mm1
c = 13.610 (3) ÅT = 293 K
V = 2013.4 (7) Å3Block, colorless
Z = 40.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer3078 independent reflections
Radiation source: fine-focus sealed tube2672 reflections with I > 2σ(I)
graphiteRint = 0.013
thin–slice ω scansθmax = 25.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = 0→12
Tmin = 0.788, Tmax = 0.885k = 0→16
3662 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.170w = 1/[σ2(Fo2) + (0.1P)2 + 1.7P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3078 reflectionsΔρmax = 0.86 e Å3
262 parametersΔρmin = −0.93 e Å3
21 restraintsAbsolute structure: Flack (1983), 1148 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Zn0.80554 (7)0.24867 (6)0.17695 (11)0.0404 (2)
O10.6427 (6)0.2741 (4)0.0031 (4)0.0527 (14)
O20.6618 (4)0.1729 (4)0.1314 (3)0.0460 (12)
O31.0107 (5)0.2747 (4)0.3026 (4)0.0499 (13)
O40.8498 (5)0.1737 (4)0.2963 (3)0.0475 (12)
N11.0272 (6)0.1987 (5)−0.0680 (4)0.0521 (17)
N20.9385 (6)0.2337 (5)0.0733 (4)0.0463 (15)
N30.7033 (6)0.5006 (4)0.3164 (5)0.0510 (16)
N40.7491 (7)0.3801 (4)0.2205 (4)0.0472 (14)
C11.1212 (13)0.2987 (10)−0.2907 (9)0.117 (4)
H1A1.04190.3048−0.31850.140*
H1B1.18730.3358−0.31430.140*
C21.1396 (16)0.2381 (9)−0.2185 (9)0.108 (4)
H2A1.22020.2342−0.19270.130*
C31.0418 (10)0.1747 (7)−0.1742 (6)0.067 (3)
H3A0.96270.1841−0.20790.081*
H3B1.06590.1076−0.18130.081*
C41.1200 (8)0.2010 (7)0.0013 (6)0.064 (2)
H4A1.20480.1897−0.00930.077*
C51.0653 (8)0.2229 (8)0.0875 (6)0.064 (2)
H5A1.10670.22960.14730.077*
C60.9205 (9)0.2199 (6)−0.0230 (6)0.054 (2)
H6A0.84330.2246−0.05420.064*
C70.5349 (13)0.4544 (10)0.4792 (11)0.115 (4)
H7A0.53760.41240.42600.138*
H7B0.48120.44190.53150.138*
C80.6023 (12)0.5264 (10)0.4805 (9)0.103 (4)
H8A0.59440.56490.53610.124*
C90.6961 (9)0.5618 (7)0.4052 (7)0.071 (3)
H9A0.67370.62690.38580.085*
H9B0.77830.56440.43550.085*
C100.6367 (8)0.5131 (6)0.2322 (6)0.057 (2)
H10A0.58240.56360.21770.069*
C110.6646 (7)0.4394 (5)0.1753 (7)0.0564 (19)
H11A0.63150.42920.11300.068*
C120.7688 (8)0.4184 (6)0.3080 (6)0.0504 (19)
H12A0.82030.39240.35630.060*
C130.4530 (7)0.0680 (6)0.0655 (6)0.0515 (19)
H13A0.47380.06410.13170.062*
C140.3601 (8)0.0089 (6)0.0297 (6)0.057 (2)
H14A0.3168−0.03230.07150.068*
C150.3319 (8)0.0118 (6)−0.0695 (7)0.058 (2)
H15A0.2695−0.0281−0.09450.070*
C160.3937 (8)0.0716 (6)−0.1302 (6)0.053 (2)
H16A0.37590.0702−0.19710.064*
C170.4853 (6)0.1368 (5)−0.0948 (5)0.0379 (16)
C180.5166 (6)0.1329 (5)0.0063 (5)0.0386 (15)
C190.6122 (7)0.1995 (6)0.0472 (5)0.0424 (17)
C200.9526 (7)0.2027 (6)0.3316 (5)0.0380 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn0.0443 (4)0.0475 (4)0.0294 (3)0.0011 (4)0.0035 (5)0.0003 (4)
O10.056 (3)0.062 (3)0.041 (3)−0.013 (3)−0.002 (3)0.002 (3)
O20.044 (3)0.065 (4)0.029 (2)0.003 (3)−0.008 (2)−0.002 (2)
O30.051 (3)0.057 (3)0.042 (3)−0.010 (3)0.004 (3)0.005 (3)
O40.045 (3)0.066 (3)0.032 (3)−0.007 (3)−0.008 (2)0.004 (2)
N10.054 (4)0.077 (5)0.026 (3)−0.004 (4)0.012 (3)−0.005 (3)
N20.039 (3)0.070 (4)0.030 (3)0.003 (3)0.008 (3)0.004 (3)
N30.061 (4)0.049 (4)0.044 (3)−0.002 (3)0.002 (3)−0.005 (3)
N40.058 (4)0.043 (3)0.040 (3)0.003 (3)−0.001 (3)−0.011 (3)
C10.112 (8)0.128 (8)0.109 (8)−0.030 (7)−0.019 (7)0.010 (7)
C20.134 (8)0.117 (8)0.072 (7)−0.028 (7)0.021 (7)−0.005 (6)
C30.083 (6)0.081 (6)0.038 (4)−0.016 (5)0.015 (4)−0.009 (4)
C40.047 (5)0.092 (6)0.054 (5)0.012 (5)0.016 (4)−0.014 (5)
C50.048 (5)0.102 (7)0.041 (5)0.006 (5)−0.004 (4)−0.006 (5)
C60.059 (5)0.064 (5)0.038 (4)0.003 (4)−0.002 (4)0.003 (4)
C70.122 (11)0.121 (10)0.101 (10)0.021 (7)0.036 (9)−0.004 (9)
C80.101 (9)0.142 (11)0.067 (7)−0.005 (8)−0.002 (7)−0.042 (8)
C90.082 (7)0.068 (6)0.062 (6)0.007 (5)−0.013 (5)−0.030 (5)
C100.068 (6)0.052 (5)0.052 (5)0.012 (4)−0.006 (4)0.005 (4)
C110.072 (5)0.055 (4)0.042 (4)0.010 (4)−0.007 (5)0.002 (5)
C120.047 (5)0.057 (5)0.047 (4)0.008 (4)−0.004 (4)−0.006 (4)
C130.053 (5)0.062 (5)0.040 (4)0.001 (4)0.012 (4)−0.002 (4)
C140.057 (5)0.052 (5)0.062 (5)−0.010 (4)0.016 (4)0.003 (4)
C150.048 (5)0.039 (4)0.087 (7)−0.009 (4)−0.009 (4)−0.009 (4)
C160.045 (5)0.060 (5)0.054 (5)−0.001 (4)−0.012 (4)−0.003 (4)
C170.031 (4)0.048 (4)0.035 (4)0.007 (3)−0.003 (3)−0.009 (3)
C180.038 (4)0.044 (4)0.034 (3)0.009 (3)0.003 (3)0.003 (3)
C190.032 (4)0.061 (5)0.034 (4)0.011 (4)0.002 (3)−0.011 (4)
C200.045 (4)0.047 (4)0.022 (3)0.004 (4)0.003 (3)−0.007 (3)

Geometric parameters (Å, °)

Zn—O21.959 (5)C5—H5A0.9300
Zn—O41.985 (5)C6—H6A0.9300
Zn—N42.008 (6)C7—C81.230 (17)
Zn—N22.012 (6)C7—H7A0.9300
O1—C191.239 (9)C7—H7B0.9300
O2—C191.316 (9)C8—C91.515 (16)
O3—C201.240 (9)C8—H8A0.9300
O4—C201.263 (9)C9—H9A0.9700
N1—C61.327 (11)C9—H9B0.9700
N1—C41.368 (11)C10—C111.315 (11)
N1—C31.491 (9)C10—H10A0.9300
N2—C61.337 (10)C11—H11A0.9300
N2—C51.376 (11)C12—H12A0.9300
N3—C121.342 (9)C13—C141.374 (11)
N3—C101.359 (10)C13—C181.385 (10)
N3—C91.479 (10)C13—H13A0.9300
N4—C121.320 (10)C14—C151.384 (12)
N4—C111.367 (10)C14—H14A0.9300
C1—C21.308 (9)C15—C161.344 (12)
C1—H1A0.9300C15—H15A0.9300
C1—H1B0.9300C16—C171.416 (11)
C2—C31.492 (16)C16—H16A0.9300
C2—H2A0.9300C17—C181.417 (9)
C3—H3A0.9700C17—C20i1.509 (10)
C3—H3B0.9700C18—C191.483 (10)
C4—C51.346 (11)C20—C17ii1.509 (10)
C4—H4A0.9300
O2—Zn—O499.5 (2)H7A—C7—H7B120.0
O2—Zn—N4110.1 (2)C7—C8—C9129.8 (12)
O4—Zn—N4107.7 (2)C7—C8—H8A115.1
O2—Zn—N2106.0 (2)C9—C8—H8A115.1
O4—Zn—N2110.6 (2)N3—C9—C8113.7 (8)
N4—Zn—N2120.8 (3)N3—C9—H9A108.8
C19—O2—Zn116.2 (5)C8—C9—H9A108.8
C20—O4—Zn110.6 (5)N3—C9—H9B108.8
C6—N1—C4107.3 (6)C8—C9—H9B108.8
C6—N1—C3125.9 (8)H9A—C9—H9B107.7
C4—N1—C3126.7 (7)C11—C10—N3106.2 (7)
C6—N2—C5105.3 (7)C11—C10—H10A126.9
C6—N2—Zn126.9 (6)N3—C10—H10A126.9
C5—N2—Zn127.3 (5)C10—C11—N4110.6 (8)
C12—N3—C10108.0 (7)C10—C11—H11A124.7
C12—N3—C9125.7 (7)N4—C11—H11A124.7
C10—N3—C9126.1 (7)N4—C12—N3109.6 (7)
C12—N4—C11105.6 (7)N4—C12—H12A125.2
C12—N4—Zn125.7 (5)N3—C12—H12A125.2
C11—N4—Zn127.7 (5)C14—C13—C18122.3 (7)
C2—C1—H1A120.0C14—C13—H13A118.8
C2—C1—H1B120.0C18—C13—H13A118.8
H1A—C1—H1B120.0C13—C14—C15119.0 (8)
C1—C2—C3125.2 (15)C13—C14—H14A120.5
C1—C2—H2A117.4C15—C14—H14A120.5
C3—C2—H2A117.4C16—C15—C14120.7 (8)
N1—C3—C2109.5 (8)C16—C15—H15A119.6
N1—C3—H3A109.8C14—C15—H15A119.6
C2—C3—H3A109.8C15—C16—C17121.5 (7)
N1—C3—H3B109.8C15—C16—H16A119.2
C2—C3—H3B109.8C17—C16—H16A119.2
H3A—C3—H3B108.2C16—C17—C18118.0 (7)
C5—C4—N1107.0 (7)C16—C17—C20i117.6 (6)
C5—C4—H4A126.5C18—C17—C20i124.4 (6)
N1—C4—H4A126.5C13—C18—C17118.2 (7)
C4—C5—N2109.2 (8)C13—C18—C19121.6 (7)
C4—C5—H5A125.4C17—C18—C19120.1 (6)
N2—C5—H5A125.4O1—C19—O2123.3 (7)
N1—C6—N2111.1 (8)O1—C19—C18121.3 (6)
N1—C6—H6A124.4O2—C19—C18115.4 (7)
N2—C6—H6A124.4O3—C20—O4124.7 (7)
C8—C7—H7A120.0O3—C20—C17ii118.6 (7)
C8—C7—H7B120.0O4—C20—C17ii116.2 (7)
O4—Zn—O2—C19−175.7 (5)C10—N3—C9—C892.3 (11)
N4—Zn—O2—C1971.4 (5)C7—C8—C9—N32(2)
N2—Zn—O2—C19−60.9 (5)C12—N3—C10—C11−0.7 (10)
O2—Zn—O4—C20171.3 (5)C9—N3—C10—C11−175.6 (8)
N4—Zn—O4—C20−73.9 (5)N3—C10—C11—N4−0.7 (10)
N2—Zn—O4—C2060.1 (5)C12—N4—C11—C101.9 (10)
O2—Zn—N2—C630.4 (7)Zn—N4—C11—C10170.5 (6)
O4—Zn—N2—C6137.3 (6)C11—N4—C12—N3−2.2 (9)
N4—Zn—N2—C6−95.6 (7)Zn—N4—C12—N3−171.2 (5)
O2—Zn—N2—C5−140.5 (7)C10—N3—C12—N41.9 (9)
O4—Zn—N2—C5−33.6 (8)C9—N3—C12—N4176.8 (8)
N4—Zn—N2—C593.5 (8)C18—C13—C14—C152.4 (12)
O2—Zn—N4—C12123.9 (7)C13—C14—C15—C16−0.3 (13)
O4—Zn—N4—C1216.3 (7)C14—C15—C16—C17−3.0 (13)
N2—Zn—N4—C12−112.1 (7)C15—C16—C17—C184.2 (11)
O2—Zn—N4—C11−42.7 (7)C15—C16—C17—C20i−178.6 (8)
O4—Zn—N4—C11−150.2 (7)C14—C13—C18—C17−1.0 (11)
N2—Zn—N4—C1181.4 (7)C14—C13—C18—C19176.9 (7)
C6—N1—C3—C2127.2 (11)C16—C17—C18—C13−2.2 (10)
C4—N1—C3—C2−54.2 (13)C20i—C17—C18—C13−179.2 (7)
C1—C2—C3—N1−119.3 (14)C16—C17—C18—C19179.9 (7)
C6—N1—C4—C50.7 (11)C20i—C17—C18—C192.8 (10)
C3—N1—C4—C5−178.1 (9)Zn—O2—C19—O1−8.2 (9)
N1—C4—C5—N20.4 (12)Zn—O2—C19—C18171.1 (4)
C6—N2—C5—C4−1.4 (11)C13—C18—C19—O1−159.2 (7)
Zn—N2—C5—C4171.1 (7)C17—C18—C19—O118.8 (10)
C4—N1—C6—N2−1.6 (10)C13—C18—C19—O221.6 (10)
C3—N1—C6—N2177.2 (8)C17—C18—C19—O2−160.5 (6)
C5—N2—C6—N11.8 (10)Zn—O4—C20—O37.5 (9)
Zn—N2—C6—N1−170.7 (5)Zn—O4—C20—C17ii−164.5 (4)
C12—N3—C9—C8−81.8 (11)

Symmetry codes: (i) −x+3/2, y, z−1/2; (ii) −x+3/2, y, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···O2i0.972.563.424 (10)148
C5—H5A···O30.932.433.070 (10)126
C6—H6A···O10.932.383.080 (11)132
C9—H9A···O3iii0.972.483.317 (11)144

Symmetry codes: (i) −x+3/2, y, z−1/2; (iii) x−1/2, −y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2640).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
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