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ISSN: 2056-9890

catena-Poly[(di­chloridozinc)-μ-1-{4-[(1H-imidazol-1-yl)meth­yl]benz­yl}-1H-imidazole-κ2N3:N3′]

aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, and bEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China
*Correspondence e-mail: hgf1000@163.com

(Received 29 March 2012; accepted 9 April 2012; online 18 April 2012)

The asymmetric unit of the title compound, [ZnCl2(C14H14N4)]n, contains a ZnII ion situated on a twofold rotation axis and one-half of a 1-{4-[(1H-imidazol-1-yl)meth­yl]benz­yl}-1H-imidazole (L) ligand with the benzene ring situated on an inversion center. The ZnII ion is coordinated by two chloride anions and two N atoms from two L ligands in a distorted tetra­hedral geometry. The L ligands bridge ZnCl2 fragments into polymeric chains parallel to [20-1].

Related literature

For the synthesis of the ligand, see: Yang et al. (2006[Yang, J., Ma, J.-F., Liu, Y.-Y., Ma, J.-C., Jia, H.-Q. & Hu, N.-H. (2006). Eur. J. Inorg. Chem. pp. 1208-1215.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnCl2(C14H14N4)]

  • Mr = 374.56

  • Orthorhombic, P b c n

  • a = 11.327 (2) Å

  • b = 10.207 (2) Å

  • c = 14.452 (3) Å

  • V = 1670.8 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.79 mm−1

  • T = 293 K

  • 0.58 × 0.55 × 0.49 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.421, Tmax = 0.477

  • 15231 measured reflections

  • 1916 independent reflections

  • 1718 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.063

  • S = 1.08

  • 1916 reflections

  • 96 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.29 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The synthesis and characterization of coordination networks based on the idea of self-assembly of specifically designed building blocks has been an area of rapid growth in recent years. Herein, we report the title compound constructed by 1-[4-[(1H-imidazol-1-yl)methyl]benzyl] -1H-imidazole and ZnCl2.

The asymmetric unit of the title compound, [ZnCl2L]n (L = 1-[4-[(1H-imidazol-1-yl)methyl]benzyl] -1H-imidazole, C14H14N4), contains a ZnII ion situated on a twofold rotational axis and one-half ligand L with the benzene ring situated on an inversion center. Each ZnII ion is coordinated by two chlorido anions and two N atoms from two ligands L in a distorted tetrahedral geometry (Figure 1). Ligands L bridge ZnCl2 fragments into polymeric chains in [20-1] (Figure 2).

Related literature top

For the synthesis of the ligand, see: Yang et al. (2006).

Experimental top

The 1-[4-[(1H-imidazol-1-yl)methyl]benzyl] -1H-imidazole was synthesized following the reference method (Yang et al., 2006). Synthesis of the title compound: ligand (0.120 g, 0.5 mmol) and ZnCl2 (0.080 g, 0.5 mmol) were dissolved in a mixed solution of 4 mL ethanol and 4 mL water. After stirring, the suspension was sealed in a 18 mL Teflon-lined autoclave and heated at 140 °C for 5 days. After slow cooling to room temperature, colorless block crystals were filtered and washed with distilled water (52% yield based on Zn).

Refinement top

C-bound H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic); C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids at the 50% probability level [symmetry codes: (i) 1-x, -y, 1-z; (ii) 2-x, y, 0.5-z].
[Figure 2] Fig. 2. A portion of the polymeric chain in the title compound. H atoms omitted for clarity.
catena-Poly[(dichloridozinc)-µ-1-{4-[(1H-imidazol-1- yl)methyl]benzyl}-1H-imidazole-κ2N3:N3'] top
Crystal data top
[ZnCl2(C14H14N4)]F(000) = 760
Mr = 374.56Dx = 1.489 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 13075 reflections
a = 11.327 (2) Åθ = 3.0–27.5°
b = 10.207 (2) ŵ = 1.79 mm1
c = 14.452 (3) ÅT = 293 K
V = 1670.8 (6) Å3Block, colourless
Z = 40.58 × 0.55 × 0.49 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1916 independent reflections
Radiation source: fine-focus sealed tube1718 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scanθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1414
Tmin = 0.421, Tmax = 0.477k = 1313
15231 measured reflectionsl = 1816
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0339P)2 + 0.4633P]
where P = (Fo2 + 2Fc2)/3
1916 reflections(Δ/σ)max = 0.001
96 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[ZnCl2(C14H14N4)]V = 1670.8 (6) Å3
Mr = 374.56Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 11.327 (2) ŵ = 1.79 mm1
b = 10.207 (2) ÅT = 293 K
c = 14.452 (3) Å0.58 × 0.55 × 0.49 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1916 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
1718 reflections with I > 2σ(I)
Tmin = 0.421, Tmax = 0.477Rint = 0.022
15231 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.08Δρmax = 0.20 e Å3
1916 reflectionsΔρmin = 0.29 e Å3
96 parameters
Special details top

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 > 2sigma(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
C10.83519 (13)0.15817 (15)0.39823 (10)0.0350 (3)
H10.87230.10280.44020.042*
C20.7938 (2)0.2662 (3)0.27631 (15)0.0754 (8)
H20.79760.30040.21680.090*
C30.7085 (2)0.2926 (3)0.33876 (15)0.0733 (7)
H30.64360.34720.33040.088*
C40.66639 (15)0.21680 (18)0.50158 (12)0.0458 (4)
H4A0.62370.29830.50990.055*
H4B0.71950.20650.55370.055*
C50.59983 (16)0.0048 (2)0.55434 (14)0.0540 (5)
H50.66670.00880.59160.065*
C60.57941 (13)0.10417 (16)0.50083 (11)0.0396 (4)
C70.47871 (17)0.1088 (2)0.44701 (16)0.0556 (5)
H70.46350.18260.41120.067*
Cl11.08205 (3)0.03773 (4)0.36609 (3)0.04045 (11)
N10.87372 (11)0.18141 (14)0.31401 (9)0.0391 (3)
N20.73601 (11)0.22419 (13)0.41575 (9)0.0374 (3)
Zn11.00000.07951 (2)0.25000.03065 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0346 (7)0.0395 (8)0.0308 (7)0.0067 (6)0.0040 (6)0.0015 (6)
C20.0835 (16)0.0979 (19)0.0448 (10)0.0500 (14)0.0178 (10)0.0316 (11)
C30.0737 (14)0.0870 (16)0.0592 (12)0.0511 (13)0.0165 (10)0.0251 (11)
C40.0439 (9)0.0499 (10)0.0437 (9)0.0023 (7)0.0163 (7)0.0125 (8)
C50.0408 (9)0.0609 (12)0.0603 (11)0.0004 (8)0.0097 (8)0.0075 (10)
C60.0346 (8)0.0439 (9)0.0402 (8)0.0035 (6)0.0096 (6)0.0074 (7)
C70.0489 (10)0.0507 (11)0.0674 (13)0.0018 (8)0.0055 (9)0.0146 (10)
Cl10.0367 (2)0.0478 (2)0.0369 (2)0.00320 (16)0.00610 (14)0.00531 (16)
N10.0407 (7)0.0447 (8)0.0319 (6)0.0120 (6)0.0078 (5)0.0048 (6)
N20.0360 (6)0.0390 (7)0.0371 (7)0.0064 (5)0.0079 (5)0.0017 (5)
Zn10.02814 (14)0.03731 (15)0.02650 (14)0.0000.00440 (8)0.000
Geometric parameters (Å, º) top
C1—N11.3146 (19)C4—H4B0.9700
C1—N21.3343 (19)C5—C61.375 (3)
C1—H10.9300C5—C7i1.384 (3)
C2—C31.350 (3)C5—H50.9300
C2—N11.365 (2)C6—C71.381 (3)
C2—H20.9300C7—C5i1.384 (3)
C3—N21.350 (2)C7—H70.9300
C3—H30.9300Cl1—Zn12.2606 (5)
C4—N21.4718 (19)N1—Zn11.9959 (13)
C4—C61.514 (2)Zn1—N1ii1.9959 (13)
C4—H4A0.9700Zn1—Cl1ii2.2606 (5)
N1—C1—N2111.35 (14)C5—C6—C7118.89 (16)
N1—C1—H1124.3C5—C6—C4120.07 (16)
N2—C1—H1124.3C7—C6—C4121.04 (17)
C3—C2—N1109.55 (17)C6—C7—C5i120.84 (19)
C3—C2—H2125.2C6—C7—H7119.6
N1—C2—H2125.2C5i—C7—H7119.6
C2—C3—N2106.38 (16)C1—N1—C2105.29 (14)
C2—C3—H3126.8C1—N1—Zn1124.96 (11)
N2—C3—H3126.8C2—N1—Zn1128.33 (12)
N2—C4—C6112.43 (13)C1—N2—C3107.42 (14)
N2—C4—H4A109.1C1—N2—C4125.82 (14)
C6—C4—H4A109.1C3—N2—C4126.67 (15)
N2—C4—H4B109.1N1ii—Zn1—N1117.19 (8)
C6—C4—H4B109.1N1ii—Zn1—Cl1ii103.09 (4)
H4A—C4—H4B107.8N1—Zn1—Cl1ii108.98 (4)
C6—C5—C7i120.26 (17)N1ii—Zn1—Cl1108.98 (4)
C6—C5—H5119.9N1—Zn1—Cl1103.09 (4)
C7i—C5—H5119.9Cl1ii—Zn1—Cl1116.08 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+1/2.

Experimental details

Crystal data
Chemical formula[ZnCl2(C14H14N4)]
Mr374.56
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)293
a, b, c (Å)11.327 (2), 10.207 (2), 14.452 (3)
V3)1670.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.79
Crystal size (mm)0.58 × 0.55 × 0.49
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.421, 0.477
No. of measured, independent and
observed [I > 2σ(I)] reflections
15231, 1916, 1718
Rint0.022
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.063, 1.08
No. of reflections1916
No. of parameters96
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.29

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The present study was supported by the NSFC (grant Nos. 51143002, 21072049, 21072050, 21110402016 and 21074031), the CPDF (grant No. 201104456), the HLJNSF of Heilongjiang (grant Nos. E201118 and E201144), the Abroad Person with Ability Foundation of Heilongjiang Province (grant No. 2010td03) and the Innovation Fellowship Foundation of Heilongjiang University (grant No. Hdtd2010-11).

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYang, J., Ma, J.-F., Liu, Y.-Y., Ma, J.-C., Jia, H.-Q. & Hu, N.-H. (2006). Eur. J. Inorg. Chem. pp. 1208–1215.  Web of Science CSD CrossRef Google Scholar

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ISSN: 2056-9890
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