catena-Poly[(dichloridozinc)-μ-4,4′-bis­[(1H-imidazol-1-yl)meth­yl]biphenyl-κ2N3:N3′]

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

doi:10.1107/S1600536812014043

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m576

doi:10.1107/S1600536812014043

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catena-Poly[(dichloridozinc)-μ-4,4′-bis[(1H-imidazol-1-yl)methyl]biphenyl-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 Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 20 March 2012; accepted 31 March 2012; online 13 April 2012)

In the title compound, [ZnCl₂(C₂₀H₁₈N₄)]_n, the Zn^II ion lies on a twofold rotation axis and is four-coordinated in a tetrahedral geometry defined by two Cl anions and two N atoms from two 4,4′-bis[(imidazol-1-yl)methyl]biphenyl ligands. The mid-point of the ligand is located on an inversion center, and shows a trans conformation. The ligands link the Zn^II ions, forming a chain structure along [10-1].

Related literature

For the synthesis of the ligand, see: Zhu et al. (2002 ).

Experimental

Crystal data

[ZnCl₂(C₂₀H₁₈N₄)]
M_r = 450.67
Monoclinic, C 2/c
a = 22.837 (5) Å
b = 5.9004 (12) Å
c = 16.012 (3) Å
β = 117.08 (3)°
V = 1921.0 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 293 K
0.36 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.601, T_max = 0.765
8827 measured reflections
2204 independent reflections
1890 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.07
2204 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—Cl1	2.2349 (9)
Zn1—N1	2.0224 (16)

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014043/hy2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014043/hy2529Isup2.hkl

checkCIF report

Comment top

N-containing ligands with an arene center have been widely used as building blocks for constructing inorganic-organic supramolecular architectures. Herein, we report the title compound constructed from 4,4'-(dimethylenebiphenyl)diimidazole and ZnCl₂.

In the title compound, the Zn^II ion lies on a twofold rotation axis and is four-coordinated in a tetrahedral environment defined by two Cl anions and two N atoms from two ligands (Fig. 1, Table 1). The mid-point of the ligand is located in an inversion center. The ligands showing a trans conformation link the Zn^II ions into a chain structure along [1 0 1] (Fig. 2).

Related literature top

For the synthesis of the ligand, see: Zhu et al. (2002).

Experimental top

The 4,4'-(dimethylenebiphenyl)diimidazol ligand was synthesized followed the reference method (Zhu et al., 2002). ZnCl₂ (0.140 g, 1 mmol) and ligand (0.32 g, 1 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 (yield: 35% 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing displacement ellipsoids at the 50% probability level. [Symmetry codes: (i) -x, y, 1/2-z; (ii) 1/2-x, -1/2-y, -z.]
	Fig. 2. A partial packing view, showing the chain structure along [1 0 1].

catena-Poly[(dichloridozinc)-µ-4,4'-bis[(1H-imidazol-1- yl)methyl]biphenyl-κ²N³:N^3'] top

Crystal data top

[ZnCl₂(C₂₀H₁₈N₄)]	F(000) = 920
M_r = 450.67	D_x = 1.558 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7615 reflections
a = 22.837 (5) Å	θ = 3.6–27.5°
b = 5.9004 (12) Å	µ = 1.57 mm⁻¹
c = 16.012 (3) Å	T = 293 K
β = 117.08 (3)°	Block, colorless
V = 1921.0 (9) Å³	0.36 × 0.20 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2204 independent reflections
Radiation source: fine-focus sealed tube	1890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scan	θ_max = 27.5°, θ_min = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −29→26
T_min = 0.601, T_max = 0.765	k = −7→7
8827 measured reflections	l = −20→20

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0483P)² + 0.6927P] where P = (F_o² + 2F_c²)/3
2204 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[ZnCl₂(C₂₀H₁₈N₄)]	V = 1921.0 (9) Å³
M_r = 450.67	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.837 (5) Å	µ = 1.57 mm⁻¹
b = 5.9004 (12) Å	T = 293 K
c = 16.012 (3) Å	0.36 × 0.20 × 0.18 mm
β = 117.08 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2204 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1890 reflections with I > 2σ(I)
T_min = 0.601, T_max = 0.765	R_int = 0.027
8827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.07	Δρ_max = 0.32 e Å⁻³
2204 reflections	Δρ_min = −0.24 e Å⁻³
123 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	0.02165 (11)	0.3388 (4)	0.10470 (15)	0.0471 (5)
H1	−0.0130	0.4089	0.0544	0.057*
C2	0.05856 (10)	0.1682 (4)	0.09746 (15)	0.0456 (5)
H2	0.0543	0.1002	0.0426	0.055*
C3	0.09174 (10)	0.2535 (3)	0.24453 (14)	0.0392 (4)
H3	0.1152	0.2508	0.3096	0.047*
C4	0.15012 (12)	−0.0734 (4)	0.21863 (17)	0.0494 (5)
H4A	0.1281	−0.2080	0.2249	0.059*
H4B	0.1856	−0.0379	0.2800	0.059*
C5	0.17867 (10)	−0.1230 (3)	0.15169 (14)	0.0389 (4)
C6	0.16437 (12)	−0.3221 (4)	0.10166 (18)	0.0502 (5)
H6	0.1358	−0.4253	0.1077	0.060*
C7	0.19175 (12)	−0.3717 (4)	0.04240 (18)	0.0499 (5)
H7	0.1810	−0.5075	0.0093	0.060*
C8	0.23486 (8)	−0.2230 (3)	0.03141 (12)	0.0317 (4)
C9	0.24832 (10)	−0.0205 (4)	0.08169 (15)	0.0440 (5)
H9	0.2766	0.0840	0.0756	0.053*
C10	0.22065 (11)	0.0283 (4)	0.14005 (16)	0.0482 (5)
H10	0.2303	0.1653	0.1722	0.058*
Cl1	−0.07645 (3)	0.79888 (10)	0.12779 (4)	0.05314 (16)
N1	0.04281 (8)	0.3932 (3)	0.19687 (12)	0.0385 (4)
N2	0.10332 (8)	0.1157 (3)	0.18714 (12)	0.0366 (3)
Zn1	0.0000	0.61108 (5)	0.2500	0.03718 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0445 (10)	0.0614 (13)	0.0393 (11)	0.0076 (10)	0.0223 (9)	0.0016 (9)
C2	0.0460 (10)	0.0579 (12)	0.0390 (10)	−0.0028 (10)	0.0247 (9)	−0.0125 (9)
C3	0.0477 (10)	0.0418 (10)	0.0378 (10)	0.0014 (9)	0.0280 (8)	−0.0045 (8)
C4	0.0707 (14)	0.0445 (11)	0.0551 (13)	0.0143 (10)	0.0479 (11)	0.0067 (9)
C5	0.0459 (10)	0.0392 (10)	0.0435 (10)	0.0063 (8)	0.0307 (9)	0.0010 (8)
C6	0.0615 (13)	0.0434 (10)	0.0690 (15)	−0.0130 (10)	0.0500 (12)	−0.0104 (10)
C7	0.0638 (13)	0.0412 (11)	0.0669 (14)	−0.0164 (10)	0.0491 (12)	−0.0197 (10)
C8	0.0333 (8)	0.0326 (9)	0.0358 (9)	−0.0002 (7)	0.0214 (7)	−0.0040 (7)
C9	0.0530 (11)	0.0374 (10)	0.0573 (13)	−0.0125 (9)	0.0388 (10)	−0.0123 (9)
C10	0.0639 (13)	0.0397 (10)	0.0576 (13)	−0.0078 (10)	0.0422 (11)	−0.0151 (10)
Cl1	0.0633 (3)	0.0527 (3)	0.0479 (3)	0.0107 (3)	0.0292 (3)	0.0057 (2)
N1	0.0449 (9)	0.0399 (8)	0.0424 (9)	0.0015 (7)	0.0302 (7)	−0.0015 (7)
N2	0.0424 (8)	0.0382 (8)	0.0400 (8)	0.0005 (7)	0.0281 (7)	−0.0036 (6)
Zn1	0.0457 (2)	0.03405 (18)	0.0461 (2)	0.000	0.03332 (15)	0.000

Geometric parameters (Å, º) top

C1—C2	1.352 (3)	C5—C10	1.383 (3)
C1—N1	1.366 (3)	C6—C7	1.385 (3)
C1—H1	0.9300	C6—H6	0.9300
C2—N2	1.366 (3)	C7—C8	1.389 (3)
C2—H2	0.9300	C7—H7	0.9300
C3—N1	1.317 (3)	C8—C9	1.395 (3)
C3—N2	1.340 (2)	C8—C8ⁱ	1.491 (3)
C3—H3	0.9300	C9—C10	1.376 (3)
C4—N2	1.467 (3)	C9—H9	0.9300
C4—C5	1.515 (3)	C10—H10	0.9300
C4—H4A	0.9700	Zn1—Cl1	2.2349 (9)
C4—H4B	0.9700	Zn1—N1	2.0224 (16)
C5—C6	1.375 (3)

C2—C1—N1	109.87 (19)	C8—C7—H7	119.3
C2—C1—H1	125.1	C7—C8—C9	116.80 (16)
N1—C1—H1	125.1	C7—C8—C8ⁱ	121.6 (2)
C1—C2—N2	106.02 (18)	C9—C8—C8ⁱ	121.6 (2)
C1—C2—H2	127.0	C10—C9—C8	121.50 (18)
N2—C2—H2	127.0	C10—C9—H9	119.3
N1—C3—N2	111.25 (18)	C8—C9—H9	119.3
N1—C3—H3	124.4	C9—C10—C5	121.18 (19)
N2—C3—H3	124.4	C9—C10—H10	119.4
N2—C4—C5	112.62 (17)	C5—C10—H10	119.4
N2—C4—H4A	109.1	C3—N1—C1	105.60 (16)
C5—C4—H4A	109.1	C3—N1—Zn1	126.82 (14)
N2—C4—H4B	109.1	C1—N1—Zn1	127.08 (14)
C5—C4—H4B	109.1	C3—N2—C2	107.25 (16)
H4A—C4—H4B	107.8	C3—N2—C4	124.48 (18)
C6—C5—C10	117.91 (18)	C2—N2—C4	127.82 (17)
C6—C5—C4	120.83 (18)	N1—Zn1—N1ⁱⁱ	101.05 (9)
C10—C5—C4	121.25 (18)	N1—Zn1—Cl1ⁱⁱ	110.42 (5)
C5—C6—C7	121.24 (19)	N1ⁱⁱ—Zn1—Cl1ⁱⁱ	106.35 (5)
C5—C6—H6	119.4	N1—Zn1—Cl1	106.35 (5)
C7—C6—H6	119.4	N1ⁱⁱ—Zn1—Cl1	110.42 (5)
C6—C7—C8	121.37 (18)	Cl1ⁱⁱ—Zn1—Cl1	120.56 (4)
C6—C7—H7	119.3

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₂₀H₁₈N₄)]
M_r	450.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.837 (5), 5.9004 (12), 16.012 (3)
β (°)	117.08 (3)
V (Å³)	1921.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.36 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.601, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	8827, 2204, 1890
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.07
No. of reflections	2204
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

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

Selected bond lengths (Å) top

Zn1—Cl1

2.2349 (9)

Zn1—N1

2.0224 (16)

Acknowledgements

This work was supported in part by the NSFC (Nos. 51143002, 21072049, 21072050, 21110402016 and 21074031), the CPDF (No. 201104456), the HLJNSF of Heilongjiang (Nos. E201118, E201144), the Abroad Person with Ability Foundation of Heilongjiang Province (No. 2010td03) and the Innovation Fellowship Foundation of Heilongjiang University (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
Zhu, H.-F., Zhao, W., Okamura, T., Fei, B.-L., Sun, W.-Y. & Ueyama, N. (2002). New J. Chem. 26, 1277–1279. Web of Science CSD CrossRef CAS Google Scholar

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