catena-Poly[[di­chlorido­mercury(II)]-μ-1,4-bis­[2-(pyridin-4-yl)ethyn­yl]benzene-κ2N:N′]

Wang, B.; Li, M.; Xie, Y.

doi:10.1107/S1600536814010228

metal-organic compounds

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catena-Poly[[dichloridomercury(II)]-μ-1,4-bis[2-(pyridin-4-yl)ethynyl]benzene-κ²N:N′]

Bin Wang,^a Ming Li ^a ^* and Ya-bo Xie ^b

^aState Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qing Dao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, College of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100124, People's Republic of China
^*Correspondence e-mail: wangbin_01@yeah.net

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 5 May 2014; accepted 6 May 2014; online 10 May 2014)

In the polymeric title compound, [HgCl₂(C₂₀H₁₂N₂)]_n, the Hg^II atom is located on a twofold rotation axis and the benzene ring of the bidentate bridging 1,4-bis[2-(pyridin-4-yl)ethynyl]benzene (L) ligand is located about a twofold rotation axis. The Hg^II atom is coordinated by two N atoms of two different L ligands and by two chloride ions in a distorted tetrahedral geometry. The dihedral angle between the coordinating pyridine and the benzene ring is 12.8 (2)°. The result of the bridging is the formation of a zigzag chain running parallel to [102]. The chains pack with no specific intermolecular interactions between them.

CCDC reference: 1001220

Related literature

For examples of 1,4-bis[2-(pyridin-4-yl)ethynyl]benzene-containing polymers, see: Yamada et al. (2011 ). For examples of Hg-containing polymers, see: Xie & Wu (2007 ). For the synthesis of the ligand, see: Fasina et al. (2004 ).

Experimental

Crystal data

[HgCl₂(C₂₀H₁₂N₂)]
M_r = 551.81
Monoclinic, P 2/c
a = 12.285 (3) Å
b = 4.8482 (10) Å
c = 15.271 (3) Å
β = 98.00 (3)°
V = 900.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 8.85 mm⁻¹
T = 173 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1995 ) T_min = 0.222, T_max = 0.243
4238 measured reflections
1585 independent reflections
1512 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 0.92
1585 reflections
114 parameters
H-atom parameters constrained
Δρ_max = 2.15 e Å⁻³
Δρ_min = −1.73 e Å⁻³

Table 1
Selected bond lengths (Å)

Hg1—Cl1ⁱ	2.3719 (12)
Hg1—Cl1	2.3719 (12)
Hg1—N1ⁱ	2.412 (3)
Hg1—N1	2.412 (3)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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

CCDC reference: 1001220

Crystal structure: contains datablocks 1, I. DOI: 10.1107/S1600536814010228/tk5312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010228/tk5312Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010228/tk5312Isup3.cdx

checkCIF report

Structural commentary top

Recently, a large number of coordination polymers assembled from pyridyl-based ligands have been extensively investigated. Most of these coordination polymers are constructed from 4,4'-bipyridyl but other examples of bridging ligands are known, such as with 1,4-bis(pyridin-4-ylethynyl)benzene (Yamada et al., 2011). Mercury coordination polymers are known (Xie et al., 2007)

In this work, an linear pyridyl-based ligand, 1,4-bis(pyridin-4-ylethynyl)benzene, was employed to react with HgCl₂ to afford the title complex, [Hg(C₂₀H₁₂N₂₎Cl_2]]_n (I). In I, the Hg(II) center is coordinated by two N atoms of two different 1,4-bis(pyridin-4-ylethynyl)benzene ligands and two chloride ions in a distorted tetrahedral geometry (Fig. 1). The Hg(II) centers are linked by 1,4-bis(pyridin-4-ylethynyl)benzene ligands to form a one-dimensional zigzag chain and the chain is parallel to [102] (Fig. 2). The dihedral angles between coordinated pyridine rings and benzene ring are ca. 12.8 (2)°.

Synthesis and crystallization top

The ligand 1,4-bis(pyridin-4-ylethynyl)benzene (bpyb) was synthesized from the reaction between 4-(prop-1-yn-1-yl)pyridine and 1,4-diiodobenzene following the reported procedure (Fasina et al., 2004). A methanol (3 ml) solution of HgCl₂ (0.1 mmol, 27 mg) was layered upon a chloroform solution (3 ml) of bpyp (0.2 mmol, 56 mg). After three days, colourless crystals of the title complex suitable for X-ray analysis were obtained.

Refinement top

Hydrogen atoms were included in calculated positions and treated as riding on their parent C atoms with C—H = 0.95Å and U_iso(H) = 1.2U_eq(C). The maximum and minimum residual electron density peaks of 2.15 and 1.73 eÅ^-3, respectively, were located 0.93 Å and 1.00 Å from the Hg atom.

Related literature top

For examples of 1,4-bis[2-(pyridin-4-yl)ethynyl]benzene-containing polymers, see: Yamada et al. (2011). For examples of Hg-containing polymers, see: Xie & Wu (2007). For the synthesis of the ligand, see: Fasina et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 coordination mode of the title complex, with displacement ellipsoids drawn at the 50% probability level. All H atoms have been omitted for clarity. [Symmetry codes: (#1) -x+1, y, -z+1/2; (#2) -x, -y+3, z+1.]
	Fig. 2. The zigzag chain of the complex. View down the c axis, with displacement ellipsoids drawn at the 50% probability level. All hydrogen atoms are omitted for clarity.

catena-Poly[[dichloridomercury(II)]-µ-1,4-bis[2-(pyridin-4-yl)ethynyl]benzene-κ²N:N'] top

Crystal data top

[HgCl₂(C₂₀H₁₂N₂)]	Z = 2
M_r = 551.81	F(000) = 520
Monoclinic, P2/c	D_x = 2.035 Mg m⁻³
a = 12.285 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 4.8482 (10) Å	µ = 8.85 mm⁻¹
c = 15.271 (3) Å	T = 173 K
β = 98.00 (3)°	Block, colourless
V = 900.7 (3) Å³	0.18 × 0.16 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1585 independent reflections
Radiation source: fine-focus sealed tube	1512 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and phi scan	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	h = −11→14
T_min = 0.222, T_max = 0.243	k = −5→5
4238 measured reflections	l = −18→17

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0394P)² + 2.093P] where P = (F_o² + 2F_c²)/3
1585 reflections	(Δ/σ)_max < 0.001
114 parameters	Δρ_max = 2.15 e Å⁻³
0 restraints	Δρ_min = −1.73 e Å⁻³

Crystal data top

[HgCl₂(C₂₀H₁₂N₂)]	V = 900.7 (3) Å³
M_r = 551.81	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 12.285 (3) Å	µ = 8.85 mm⁻¹
b = 4.8482 (10) Å	T = 173 K
c = 15.271 (3) Å	0.18 × 0.16 × 0.16 mm
β = 98.00 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1585 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	1512 reflections with I > 2σ(I)
T_min = 0.222, T_max = 0.243	R_int = 0.033
4238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 0.92	Δρ_max = 2.15 e Å⁻³
1585 reflections	Δρ_min = −1.73 e Å⁻³
114 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Hg1	0.5000	−0.01536 (4)	0.2500	0.01426 (13)
Cl1	0.61049 (9)	−0.1178 (2)	0.38614 (6)	0.0215 (3)
C6	0.1775 (4)	0.9118 (11)	0.3998 (3)	0.0188 (9)
C5	0.3948 (4)	0.3872 (9)	0.3923 (3)	0.0178 (9)
H5	0.4536	0.3071	0.4310	0.021*
C3	0.2446 (3)	0.7051 (9)	0.3688 (3)	0.0161 (9)
C2	0.2249 (4)	0.6136 (9)	0.2821 (3)	0.0193 (9)
H2	0.1656	0.6871	0.2425	0.023*
C7	0.1230 (4)	1.0887 (10)	0.4276 (3)	0.0179 (9)
C8	0.0599 (3)	1.2960 (8)	0.4641 (3)	0.0156 (8)
C4	0.3310 (4)	0.5860 (11)	0.4251 (3)	0.0196 (9)
H4	0.3457	0.6411	0.4853	0.024*
C1	0.2929 (4)	0.4134 (11)	0.2537 (3)	0.0197 (9)
H1	0.2795	0.3527	0.1940	0.024*
C10	0.1000 (4)	1.4112 (11)	0.5461 (3)	0.0205 (9)
H10	0.1682	1.3511	0.5772	0.025*
C9	−0.0398 (4)	1.3864 (10)	0.4180 (3)	0.0197 (9)
H9	−0.0665	1.3092	0.3619	0.024*
N1	0.3772 (3)	0.3030 (7)	0.3080 (2)	0.0141 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.01265 (19)	0.01679 (18)	0.01374 (17)	0.000	0.00326 (11)	0.000
Cl1	0.0189 (6)	0.0284 (7)	0.0167 (5)	0.0057 (4)	0.0013 (4)	0.0040 (4)
C6	0.018 (3)	0.019 (2)	0.020 (2)	−0.001 (2)	0.0039 (19)	0.0006 (19)
C5	0.014 (2)	0.020 (2)	0.018 (2)	0.0032 (18)	0.0009 (17)	−0.0011 (17)
C3	0.016 (2)	0.015 (2)	0.018 (2)	−0.0011 (17)	0.0063 (16)	−0.0011 (16)
C2	0.018 (2)	0.020 (3)	0.019 (2)	0.0059 (19)	0.0012 (18)	0.0001 (18)
C7	0.018 (3)	0.020 (2)	0.016 (2)	−0.002 (2)	0.0014 (18)	0.0005 (19)
C8	0.017 (2)	0.015 (2)	0.0162 (19)	−0.0015 (17)	0.0068 (16)	0.0019 (16)
C4	0.018 (3)	0.023 (2)	0.018 (2)	0.001 (2)	0.0053 (18)	−0.005 (2)
C1	0.020 (3)	0.024 (2)	0.017 (2)	0.002 (2)	0.0060 (19)	−0.0011 (19)
C10	0.019 (3)	0.022 (2)	0.020 (2)	0.004 (2)	0.0039 (19)	0.002 (2)
C9	0.020 (2)	0.021 (2)	0.018 (2)	0.0003 (19)	0.0041 (18)	−0.0036 (18)
N1	0.0115 (18)	0.0172 (18)	0.0145 (16)	−0.0012 (14)	0.0053 (13)	−0.0004 (14)

Geometric parameters (Å, º) top

Hg1—Cl1ⁱ	2.3719 (12)	C2—H2	0.9500
Hg1—Cl1	2.3719 (12)	C7—C8	1.428 (6)
Hg1—N1ⁱ	2.412 (3)	C8—C9	1.396 (6)
Hg1—N1	2.412 (3)	C8—C10	1.397 (6)
C6—C7	1.202 (8)	C4—H4	0.9500
C6—C3	1.420 (6)	C1—N1	1.344 (6)
C5—N1	1.339 (5)	C1—H1	0.9500
C5—C4	1.380 (7)	C10—C9ⁱⁱ	1.386 (7)
C5—H5	0.9500	C10—H10	0.9500
C3—C2	1.385 (6)	C9—C10ⁱⁱ	1.386 (7)
C3—C4	1.395 (6)	C9—H9	0.9500
C2—C1	1.389 (7)

Cl1ⁱ—Hg1—Cl1	155.82 (6)	C9—C8—C7	120.7 (4)
Cl1ⁱ—Hg1—N1ⁱ	97.08 (8)	C10—C8—C7	119.2 (4)
Cl1—Hg1—N1ⁱ	98.33 (8)	C5—C4—C3	119.1 (4)
Cl1ⁱ—Hg1—N1	98.33 (8)	C5—C4—H4	120.4
Cl1—Hg1—N1	97.08 (8)	C3—C4—H4	120.4
N1ⁱ—Hg1—N1	100.42 (16)	N1—C1—C2	122.1 (4)
C7—C6—C3	178.3 (5)	N1—C1—H1	119.0
N1—C5—C4	122.5 (4)	C2—C1—H1	119.0
N1—C5—H5	118.7	C9ⁱⁱ—C10—C8	119.8 (4)
C4—C5—H5	118.7	C9ⁱⁱ—C10—H10	120.1
C2—C3—C4	118.3 (4)	C8—C10—H10	120.1
C2—C3—C6	120.8 (4)	C10ⁱⁱ—C9—C8	120.1 (4)
C4—C3—C6	120.9 (4)	C10ⁱⁱ—C9—H9	120.0
C3—C2—C1	119.3 (4)	C8—C9—H9	120.0
C3—C2—H2	120.3	C5—N1—C1	118.6 (4)
C1—C2—H2	120.3	C5—N1—Hg1	121.5 (3)
C6—C7—C8	177.8 (5)	C1—N1—Hg1	119.7 (3)
C9—C8—C10	120.1 (4)

C4—C3—C2—C1	−1.6 (7)	C4—C5—N1—C1	−1.0 (7)
C6—C3—C2—C1	179.3 (5)	C4—C5—N1—Hg1	174.6 (4)
N1—C5—C4—C3	−0.1 (8)	C2—C1—N1—C5	0.8 (7)
C2—C3—C4—C5	1.4 (7)	C2—C1—N1—Hg1	−174.9 (4)
C6—C3—C4—C5	−179.5 (5)	Cl1ⁱ—Hg1—N1—C5	168.6 (3)
C3—C2—C1—N1	0.6 (8)	Cl1—Hg1—N1—C5	7.3 (3)
C9—C8—C10—C9ⁱⁱ	0.7 (8)	N1ⁱ—Hg1—N1—C5	−92.5 (3)
C7—C8—C10—C9ⁱⁱ	179.7 (5)	Cl1ⁱ—Hg1—N1—C1	−15.8 (3)
C10—C8—C9—C10ⁱⁱ	−0.7 (8)	Cl1—Hg1—N1—C1	−177.1 (3)
C7—C8—C9—C10ⁱⁱ	−179.7 (5)	N1ⁱ—Hg1—N1—C1	83.0 (3)

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

Selected bond lengths (Å) top

Hg1—Cl1ⁱ	2.3719 (12)	Hg1—N1ⁱ	2.412 (3)
Hg1—Cl1	2.3719 (12)	Hg1—N1	2.412 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

The authors achnowledge Qing Dao University of Science and Technology and Beijing University of Technology for supporting this work.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fasina, T. M., Collings, J. C., Lydon, D. P., Albesa-Jove, D., Batsanov, A. S., Howard, J. A. K., Nguyen, P., Bruce, M., Scott, A. J., Clegg, W., Watt, S. W., Viney, C. & Marder, T. B. (2004). J. Mater. Chem. 14, 2395–2404. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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doi:10.1107/S1600536814010228

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