catena-Poly[copper(I)-bis­[μ-3-(1H-imidazol-2-yl)pyridine]-copper(I)-di-μ-iodido]

Zhan, Q.-G.

doi:10.1107/S1600536811033605

metal-organic compounds

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catena-Poly[copper(I)-bis[μ-3-(1H-imidazol-2-yl)pyridine]-copper(I)-di-μ-iodido]

Qing-Guang Zhan ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and, South China Normal University, Key Laboratory of Technology in Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zhanqg2001@yahoo.com.cn

(Received 10 August 2011; accepted 18 August 2011; online 27 August 2011)

The title polymeric compound, [Cu₂I₂(C₈H₇N₃)₂]_n [C₈H₇N₃ = 3-(1H-imidazol-2-yl)pyridine (HIPy), where HIPy comes from the in situ decarboxylation of 2-(pyridin-3-yl)-1H-imidazole-4,5-dicarboxylic acid (H₃PyIDC)], was obtained under solvothermal conditions. Each Cu^I cation is in a distorted tetrahedral coordination environment defined by two iodide anions and two nitrogen atoms from two individual HIPy ligands. Two Cu^I atoms are connected by two HIPy ligands to form a dimer and these dimers are further bridged through the iodide atoms, leading to a chain structure extending parallel to [100]. Moreover, intermolecular N—H⋯I hydrogen bonds and weak π–π stacking interactions [centroid⋯centroid distances of 3.809 (4) Å, an interplanar separation of 3.345 (3) Å and a ring slippage of 1.822 Å] between pyridyl rings link the chains into a two-dimensional supramolecular network in the ac plane.

Related literature

For general background on the decarboxylation of N-heterocyclic carboxylic acid ligands, see: Chen & Tong (2007 ); Sun et al. (2006 ); Yigit et al. (2006 ); Zhong et al. (2010 ).

Experimental

Crystal data

[Cu₂I₂(C₈H₇N₃)₂]
M_r = 671.22
Triclinic, $[P \overline 1]$
a = 8.141 (3) Å
b = 8.306 (3) Å
c = 8.816 (5) Å
α = 114.683 (6)°
β = 101.989 (5)°
γ = 108.258 (4)°
V = 473.1 (4) Å³
Z = 1
Mo Kα radiation
μ = 5.52 mm⁻¹
T = 298 K
0.35 × 0.32 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2004 ) T_min = 0.248, T_max = 0.288
2452 measured reflections
1682 independent reflections
1506 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.06
1682 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯I1ⁱ	0.86	2.83	3.588 (5)	148
Symmetry code: (i) x+1, y+1, z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033605/zl2401sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033605/zl2401Isup2.hkl

checkCIF report

Comment top

In recent years, in situ metal/ligand reactions have been widely investigated for the discovery of new organic reactions, elucidation of reaction mechanisms, as well as generation of novel coordination polymers (Chen et al., 2007). Among them, hydrothermal decarboxylation of N-heterocyclic carboxylic acid ligands has been shown to occur in the presence of metal ions (Sun et al., 2006; Yigit et al., 2006; Zhong et al., 2010). For example, Sun et al. (2006) have synthesized two lanthanide sulfate–carboxylates, [Ln(HIMC)(SO₄)(H₂O)] (Ln = Dy and Eu, HIMC = 4-imidazolecarboxylic acid ), by using in situ decarboxylation of 4,5-imidazoledicarboxylic acid in the presence of Cu(II) ions. However, as far as we know, no decarboxylation based on 2-(pyridin-3-yl)-1H-imidazole-4,5-dicarboxylic acid (H₃PyIDC) under solvothermal reaction conditions has been documented. In this work, we report the synthesis and structure of the polymeric title complex, using H₃PyIDC as one of the starting materials. Under the solvothermal reaction conditions and in the presence of CuI decarboxylation occurs and H₃PyIDC is transformed into HIPy which is incorporated into the polymeric title complex.

The asymmmetric unit of the title compound contains one Cu⁺ cation, one I^- anion and one HIPy neutral ligand. As shown in Fig. 1, the Cu^I cation exhibits a distorted tetrahedral coordination, made up of two iodide anions and two nitrogen atoms from two individual HIPy ligands. The Cu···I bond lengths are 2.7331 (12) and 2.7887 (14) Å.

In the crystal structure, two Cu^I atoms are connected through two HIPy ligands via their N_imidazole and N_pyridyl atoms to form a dimer with a Cu···Cu separation of 5.3621 (21) Å; these dimers are further bridged through the µ₂-I atoms, leading to a 1D chain structure extending parallel to [100] (Fig. 2). Intermolecular N2–H2···I1ⁱⁱⁱ hydrogen bonds between the imidazole N-H groups and the I atoms (Table 1) [symmetry code: (iii) x+1, y+1, z+1] link the chains into a 2D supramolecular network in the ac plane (Fig. 3). The crystal structure is further stabilized by weak slipped π-π stacking interactions between neighbouring pyridyl rings (N3/C4-C8 and N3^v/C4^v-C8^v, symmetry code: (v) 1-x, 2-y, 1-z), with centroid···centroid distances of 3.809 (4) Å, an interplanar separation of 3.345 (3) Å and a ring slippage of 1.822 Å (Fig. 3).

Related literature top

For general background on the decarboxylation of N-heterocyclic carboxylic acid ligands, see: Chen et al. (2007); Sun et al. (2006); Yigit et al. (2006); Zhong et al., (2010).

Experimental top

A mixture of H₃PyIDC (46.6 mg, 0.2 mmol), CuI (38.1 mg, 0.2 mmol), 8 mL EtOH/H₂O (1:1, v/v), and 0.1 mL Et₃N was sealed in a 15mL Teflon-lined stainless steel autoclave, heated at 443 K for 48 h, and then slowly cooled to room temperature at a rate of 273 K/h. Yellow block-shaped crystals of the title compound were isolated, washed with distilled water, and dried in air (yield: 25%). Anal. Calcd. for C₈H₇CuIN₃: C, 28.63, H, 2.10, N, 12.52. Found: C, 28.73, H, 2.05, N, 12.48%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x, -y+1, -z.
	Fig. 2. The crystal packing of the title compound, showing the one-dimensional chain structure extending parallel to [100].
	Fig. 3. A view showing part of the two-dimensional supramolecular network linked by N–H···I hydrogen bonds and weak π-π stacking interactions. Hydrogen bonds and π-π stacking interactions are shown as dashed lines. Symmetry code: (v) 1-x, 2-y, 1-z).

catena-Poly[copper(I)-bis[µ-3-(1H-imidazol-2-yl)pyridine]- copper(I)-di-µ-iodido] top

Crystal data top

[Cu₂I₂(C₈H₇N₃)₂]	Z = 1
M_r = 671.22	F(000) = 316
Triclinic, P1	D_x = 2.356 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.141 (3) Å	Cell parameters from 1252 reflections
b = 8.306 (3) Å	θ = 2.8–26.8°
c = 8.816 (5) Å	µ = 5.52 mm⁻¹
α = 114.683 (6)°	T = 298 K
β = 101.989 (5)°	Block, yellow
γ = 108.258 (4)°	0.35 × 0.32 × 0.30 mm
V = 473.1 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1682 independent reflections
Radiation source: fine-focus sealed tube	1506 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.8°
Absorption correction: multi-scan (APEX2; Bruker, 2004)	h = −8→9
T_min = 0.248, T_max = 0.288	k = −9→5
2452 measured reflections	l = −10→10

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) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0418P)² + 0.3135P] where P = (F_o² + 2F_c²)/3
1682 reflections	(Δ/σ)_max = 0.001
118 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Cu₂I₂(C₈H₇N₃)₂]	γ = 108.258 (4)°
M_r = 671.22	V = 473.1 (4) Å³
Triclinic, P1	Z = 1
a = 8.141 (3) Å	Mo Kα radiation
b = 8.306 (3) Å	µ = 5.52 mm⁻¹
c = 8.816 (5) Å	T = 298 K
α = 114.683 (6)°	0.35 × 0.32 × 0.30 mm
β = 101.989 (5)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1682 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2004)	1506 reflections with I > 2σ(I)
T_min = 0.248, T_max = 0.288	R_int = 0.018
2452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.86 e Å⁻³
1682 reflections	Δρ_min = −0.69 e Å⁻³
118 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
I1	−0.63541 (5)	0.55664 (5)	−0.19170 (4)	0.03979 (15)
Cu1	−0.29230 (10)	0.58503 (11)	−0.03571 (10)	0.0494 (2)
N1	−0.1172 (6)	0.8746 (7)	0.1128 (6)	0.0359 (10)
N2	0.0984 (6)	1.1683 (7)	0.3412 (6)	0.0410 (10)
H2	0.1990	1.2584	0.4362	0.049*
C5	0.2418 (7)	0.9476 (8)	0.4986 (7)	0.0387 (12)
H5	0.2385	1.0553	0.5891	0.046*
C6	0.3354 (7)	0.8513 (9)	0.5428 (7)	0.0398 (12)
H6	0.3934	0.8906	0.6634	0.048*
C7	0.3418 (7)	0.6968 (8)	0.4067 (7)	0.0379 (12)
H7	0.4039	0.6317	0.4384	0.045*
C3	0.0440 (7)	0.9714 (7)	0.2574 (7)	0.0329 (11)
C1	−0.1648 (7)	1.0191 (8)	0.1087 (7)	0.0371 (12)
H1	−0.2713	0.9951	0.0220	0.044*
C2	−0.0336 (8)	1.2007 (8)	0.2495 (7)	0.0414 (13)
H2A	−0.0330	1.3221	0.2781	0.050*
C4	0.1521 (7)	0.8819 (7)	0.3165 (7)	0.0324 (11)
C8	0.1698 (7)	0.7266 (7)	0.1884 (7)	0.0343 (11)
H8	0.1135	0.6846	0.0668	0.041*
N3	0.2635 (6)	0.6336 (6)	0.2299 (6)	0.0364 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0394 (2)	0.0415 (2)	0.0382 (2)	0.02226 (17)	0.01033 (16)	0.01990 (18)
Cu1	0.0506 (4)	0.0349 (4)	0.0442 (4)	0.0235 (3)	0.0051 (3)	0.0086 (3)
N1	0.035 (2)	0.038 (3)	0.037 (2)	0.020 (2)	0.0167 (19)	0.018 (2)
N2	0.039 (2)	0.034 (3)	0.042 (3)	0.015 (2)	0.013 (2)	0.016 (2)
C5	0.036 (3)	0.039 (3)	0.038 (3)	0.016 (2)	0.018 (2)	0.016 (3)
C6	0.039 (3)	0.051 (3)	0.030 (3)	0.021 (3)	0.014 (2)	0.020 (3)
C7	0.034 (3)	0.040 (3)	0.045 (3)	0.017 (2)	0.016 (2)	0.026 (3)
C3	0.033 (3)	0.030 (3)	0.035 (3)	0.016 (2)	0.015 (2)	0.014 (2)
C1	0.039 (3)	0.039 (3)	0.040 (3)	0.023 (3)	0.017 (2)	0.022 (3)
C2	0.053 (3)	0.036 (3)	0.050 (3)	0.028 (3)	0.026 (3)	0.025 (3)
C4	0.030 (2)	0.027 (3)	0.037 (3)	0.013 (2)	0.015 (2)	0.013 (2)
C8	0.033 (3)	0.032 (3)	0.033 (3)	0.018 (2)	0.011 (2)	0.011 (2)
N3	0.033 (2)	0.034 (2)	0.039 (2)	0.017 (2)	0.0118 (19)	0.016 (2)

Geometric parameters (Å, º) top

I1—Cu1	2.7331 (12)	C6—C7	1.368 (8)
I1—Cu1ⁱ	2.7887 (14)	C6—H6	0.9300
Cu1—N1	1.994 (4)	C7—N3	1.345 (7)
Cu1—N3ⁱⁱ	2.030 (4)	C7—H7	0.9300
Cu1—I1ⁱ	2.7887 (14)	C3—C4	1.464 (7)
N1—C3	1.335 (6)	C1—C2	1.353 (7)
N1—C1	1.384 (7)	C1—H1	0.9300
N2—C3	1.348 (7)	C2—H2A	0.9300
N2—C2	1.372 (7)	C4—C8	1.388 (7)
N2—H2	0.8600	C8—N3	1.342 (6)
C5—C6	1.376 (8)	C8—H8	0.9300
C5—C4	1.392 (7)	N3—Cu1ⁱⁱ	2.030 (4)
C5—H5	0.9300

Cu1—I1—Cu1ⁱ	79.47 (3)	N3—C7—H7	118.1
N1—Cu1—N3ⁱⁱ	127.88 (17)	C6—C7—H7	118.1
N1—Cu1—I1	105.56 (12)	N1—C3—N2	110.0 (4)
N3ⁱⁱ—Cu1—I1	106.58 (12)	N1—C3—C4	126.1 (5)
N1—Cu1—I1ⁱ	109.74 (13)	N2—C3—C4	123.8 (4)
N3ⁱⁱ—Cu1—I1ⁱ	103.36 (13)	C2—C1—N1	110.0 (5)
I1—Cu1—I1ⁱ	100.53 (3)	C2—C1—H1	125.0
C3—N1—C1	105.7 (4)	N1—C1—H1	125.0
C3—N1—Cu1	128.9 (4)	C1—C2—N2	105.7 (5)
C1—N1—Cu1	123.9 (3)	C1—C2—H2A	127.2
C3—N2—C2	108.5 (4)	N2—C2—H2A	127.2
C3—N2—H2	125.7	C8—C4—C5	117.6 (5)
C2—N2—H2	125.7	C8—C4—C3	119.7 (5)
C6—C5—C4	119.1 (5)	C5—C4—C3	122.6 (5)
C6—C5—H5	120.4	N3—C8—C4	123.8 (5)
C4—C5—H5	120.4	N3—C8—H8	118.1
C7—C6—C5	119.0 (5)	C4—C8—H8	118.1
C7—C6—H6	120.5	C8—N3—C7	116.6 (4)
C5—C6—H6	120.5	C8—N3—Cu1ⁱⁱ	121.6 (3)
N3—C7—C6	123.8 (5)	C7—N3—Cu1ⁱⁱ	121.8 (4)

Cu1ⁱ—I1—Cu1—N1	−114.10 (13)	C3—N1—C1—C2	−0.1 (6)
Cu1ⁱ—I1—Cu1—N3ⁱⁱ	107.49 (14)	Cu1—N1—C1—C2	167.1 (3)
Cu1ⁱ—I1—Cu1—I1ⁱ	0.0	N1—C1—C2—N2	0.6 (6)
N3ⁱⁱ—Cu1—N1—C3	−78.1 (5)	C3—N2—C2—C1	−1.0 (6)
I1—Cu1—N1—C3	155.6 (4)	C6—C5—C4—C8	−3.0 (7)
I1ⁱ—Cu1—N1—C3	48.1 (4)	C6—C5—C4—C3	177.8 (5)
N3ⁱⁱ—Cu1—N1—C1	117.9 (4)	N1—C3—C4—C8	39.7 (7)
I1—Cu1—N1—C1	−8.4 (4)	N2—C3—C4—C8	−138.2 (5)
I1ⁱ—Cu1—N1—C1	−115.9 (4)	N1—C3—C4—C5	−141.1 (5)
C4—C5—C6—C7	1.7 (8)	N2—C3—C4—C5	41.0 (7)
C5—C6—C7—N3	0.9 (8)	C5—C4—C8—N3	1.9 (7)
C1—N1—C3—N2	−0.6 (5)	C3—C4—C8—N3	−178.9 (4)
Cu1—N1—C3—N2	−166.8 (3)	C4—C8—N3—C7	0.6 (7)
C1—N1—C3—C4	−178.7 (5)	C4—C8—N3—Cu1ⁱⁱ	−177.5 (4)
Cu1—N1—C3—C4	15.0 (7)	C6—C7—N3—C8	−2.1 (7)
C2—N2—C3—N1	1.0 (6)	C6—C7—N3—Cu1ⁱⁱ	176.0 (4)
C2—N2—C3—C4	179.2 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1ⁱⁱⁱ	0.86	2.83	3.588 (5)	148

Symmetry code: (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂I₂(C₈H₇N₃)₂]
M_r	671.22
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.141 (3), 8.306 (3), 8.816 (5)
α, β, γ (°)	114.683 (6), 101.989 (5), 108.258 (4)
V (Å³)	473.1 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	5.52
Crystal size (mm)	0.35 × 0.32 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2004)
T_min, T_max	0.248, 0.288
No. of measured, independent and observed [I > 2σ(I)] reflections	2452, 1682, 1506
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.06
No. of reflections	1682
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.69

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996); PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1ⁱ	0.86	2.83	3.588 (5)	148.3

Symmetry code: (i) x+1, y+1, z+1.

Acknowledgements

The author acknowledges the Young Teacher Training plan of Guangdong Universities (grant No. LYM09053, 2010, 01-2011, 12) for supporting this work.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Chen, X.-M. & Tong, M.-L. (2007). Acc. Chem. Res. 40, 162–170. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-Q., Zhang, J. & Yang, G.-Y. (2006). Chem. Commun. pp. 1947–1949. Web of Science CrossRef Google Scholar
Yigit, M.-V., Wang, Y., Moulton, B. & MacDonald, J.-C. (2006). Cryst. Growth Des. 6, 829–832. Google Scholar
Zhong, D.-C., Lu, W.-G., Jiang, L., Feng, X.-L. & Lu, T.-B. (2010). Cryst. Growth Des. 10, 739–746. Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[copper(I)-bis­­[μ-3-(1H-imidazol-2-yl)pyridine]-copper(I)-di-μ-iodido]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[copper(I)-bis[μ-3-(1H-imidazol-2-yl)pyridine]-copper(I)-di-μ-iodido]