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

Wang, C.; Wen, B.; Sun, Z.-Y.; Yan, P.-F.; Gao, J.-S.

doi:10.1107/S1600536812015395

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m621

doi:10.1107/S1600536812015395

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catena-Poly[(dichloridozinc)-μ-1-{4-[(1H-imidazol-1-yl)methyl]benzyl}-1H-imidazole-κ²N³:N^3′]

Cheng Wang,^a Bo Wen,^b Zhi-Yao Sun,^a Peng-Fei Yan ^a and Jin-Sheng Gao ^b ^*

^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 Zn^II 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 Zn^II 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 ).

Experimental

Crystal data

[ZnCl₂(C₁₄H₁₄N₄)]
M_r = 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 ) T_min = 0.421, T_max = 0.477
15231 measured reflections
1916 independent reflections
1718 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.063
S = 1.08
1916 reflections
96 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536812015395/cv5275sup1.cif

checkCIF report

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 Zn^II ion situated on a twofold rotational axis and one-half ligand L with the benzene ring situated on an inversion center. Each Zn^II 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).

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

	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].
	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:N^3'] top

Crystal data top

[ZnCl₂(C₁₄H₁₄N₄)]	F(000) = 760
M_r = 374.56	D_x = 1.489 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 13075 reflections
a = 11.327 (2) Å	θ = 3.0–27.5°
b = 10.207 (2) Å	µ = 1.79 mm⁻¹
c = 14.452 (3) Å	T = 293 K
V = 1670.8 (6) Å³	Block, colourless
Z = 4	0.58 × 0.55 × 0.49 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1916 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.421, T_max = 0.477	k = −13→13
15231 measured reflections	l = −18→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0339P)² + 0.4633P] where P = (F_o² + 2F_c²)/3
1916 reflections	(Δ/σ)_max = 0.001
96 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[ZnCl₂(C₁₄H₁₄N₄)]	V = 1670.8 (6) Å³
M_r = 374.56	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.327 (2) Å	µ = 1.79 mm⁻¹
b = 10.207 (2) Å	T = 293 K
c = 14.452 (3) Å	0.58 × 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)
T_min = 0.421, T_max = 0.477	R_int = 0.022
15231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.08	Δρ_max = 0.20 e Å⁻³
1916 reflections	Δρ_min = −0.29 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.83519 (13)	0.15817 (15)	0.39823 (10)	0.0350 (3)
H1	0.8723	0.1028	0.4402	0.042*
C2	0.7938 (2)	0.2662 (3)	0.27631 (15)	0.0754 (8)
H2	0.7976	0.3004	0.2168	0.090*
C3	0.7085 (2)	0.2926 (3)	0.33876 (15)	0.0733 (7)
H3	0.6436	0.3472	0.3304	0.088*
C4	0.66639 (15)	0.21680 (18)	0.50158 (12)	0.0458 (4)
H4A	0.6237	0.2983	0.5099	0.055*
H4B	0.7195	0.2065	0.5537	0.055*
C5	0.59983 (16)	−0.0048 (2)	0.55434 (14)	0.0540 (5)
H5	0.6667	−0.0088	0.5916	0.065*
C6	0.57941 (13)	0.10417 (16)	0.50083 (11)	0.0396 (4)
C7	0.47871 (17)	0.1088 (2)	0.44701 (16)	0.0556 (5)
H7	0.4635	0.1826	0.4112	0.067*
Cl1	1.08205 (3)	−0.03773 (4)	0.36609 (3)	0.04045 (11)
N1	0.87372 (11)	0.18141 (14)	0.31401 (9)	0.0391 (3)
N2	0.73601 (11)	0.22419 (13)	0.41575 (9)	0.0374 (3)
Zn1	1.0000	0.07951 (2)	0.2500	0.03065 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0346 (7)	0.0395 (8)	0.0308 (7)	0.0067 (6)	0.0040 (6)	0.0015 (6)
C2	0.0835 (16)	0.0979 (19)	0.0448 (10)	0.0500 (14)	0.0178 (10)	0.0316 (11)
C3	0.0737 (14)	0.0870 (16)	0.0592 (12)	0.0511 (13)	0.0165 (10)	0.0251 (11)
C4	0.0439 (9)	0.0499 (10)	0.0437 (9)	−0.0023 (7)	0.0163 (7)	−0.0125 (8)
C5	0.0408 (9)	0.0609 (12)	0.0603 (11)	−0.0004 (8)	−0.0097 (8)	0.0075 (10)
C6	0.0346 (8)	0.0439 (9)	0.0402 (8)	0.0035 (6)	0.0096 (6)	−0.0074 (7)
C7	0.0489 (10)	0.0507 (11)	0.0674 (13)	0.0018 (8)	−0.0055 (9)	0.0146 (10)
Cl1	0.0367 (2)	0.0478 (2)	0.0369 (2)	0.00320 (16)	−0.00610 (14)	0.00531 (16)
N1	0.0407 (7)	0.0447 (8)	0.0319 (6)	0.0120 (6)	0.0078 (5)	0.0048 (6)
N2	0.0360 (6)	0.0390 (7)	0.0371 (7)	0.0064 (5)	0.0079 (5)	−0.0017 (5)
Zn1	0.02814 (14)	0.03731 (15)	0.02650 (14)	0.000	0.00440 (8)	0.000

Geometric parameters (Å, º) top

C1—N1	1.3146 (19)	C4—H4B	0.9700
C1—N2	1.3343 (19)	C5—C6	1.375 (3)
C1—H1	0.9300	C5—C7ⁱ	1.384 (3)
C2—C3	1.350 (3)	C5—H5	0.9300
C2—N1	1.365 (2)	C6—C7	1.381 (3)
C2—H2	0.9300	C7—C5ⁱ	1.384 (3)
C3—N2	1.350 (2)	C7—H7	0.9300
C3—H3	0.9300	Cl1—Zn1	2.2606 (5)
C4—N2	1.4718 (19)	N1—Zn1	1.9959 (13)
C4—C6	1.514 (2)	Zn1—N1ⁱⁱ	1.9959 (13)
C4—H4A	0.9700	Zn1—Cl1ⁱⁱ	2.2606 (5)

N1—C1—N2	111.35 (14)	C5—C6—C7	118.89 (16)
N1—C1—H1	124.3	C5—C6—C4	120.07 (16)
N2—C1—H1	124.3	C7—C6—C4	121.04 (17)
C3—C2—N1	109.55 (17)	C6—C7—C5ⁱ	120.84 (19)
C3—C2—H2	125.2	C6—C7—H7	119.6
N1—C2—H2	125.2	C5ⁱ—C7—H7	119.6
C2—C3—N2	106.38 (16)	C1—N1—C2	105.29 (14)
C2—C3—H3	126.8	C1—N1—Zn1	124.96 (11)
N2—C3—H3	126.8	C2—N1—Zn1	128.33 (12)
N2—C4—C6	112.43 (13)	C1—N2—C3	107.42 (14)
N2—C4—H4A	109.1	C1—N2—C4	125.82 (14)
C6—C4—H4A	109.1	C3—N2—C4	126.67 (15)
N2—C4—H4B	109.1	N1ⁱⁱ—Zn1—N1	117.19 (8)
C6—C4—H4B	109.1	N1ⁱⁱ—Zn1—Cl1ⁱⁱ	103.09 (4)
H4A—C4—H4B	107.8	N1—Zn1—Cl1ⁱⁱ	108.98 (4)
C6—C5—C7ⁱ	120.26 (17)	N1ⁱⁱ—Zn1—Cl1	108.98 (4)
C6—C5—H5	119.9	N1—Zn1—Cl1	103.09 (4)
C7ⁱ—C5—H5	119.9	Cl1ⁱⁱ—Zn1—Cl1	116.08 (3)

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₄H₁₄N₄)]
M_r	374.56
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	11.327 (2), 10.207 (2), 14.452 (3)
V (Å³)	1670.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.58 × 0.55 × 0.49

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.421, 0.477
No. of measured, independent and observed [I > 2σ(I)] reflections	15231, 1916, 1718
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.063, 1.08
No. of reflections	1916
No. of parameters	96
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CSD CrossRef Google Scholar

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