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

The title polymeric compound, [Cu(2)I(2)(C(8)H(7)N(3))(2)](n) [C(8)H(7)N(3) = 3-(1H-imidazol-2-yl)pyridine (HIPy), where HIPy comes from the in situ deca-rboxylation of 2-(pyridin-3-yl)-1H-imidazole-4,5-dicarb-oxy-lic acid (H(3)PyIDC)], was obtained under solvo-thermal conditions. Each Cu(I) cation is in a distorted tetra-hedral coordination environment defined by two iodide anions and two nitro-gen 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, inter-molecular N-H⋯I hydrogen bonds and weak π-π stacking inter-actions [centroid⋯centroid distances of 3.809 (4) Å, an inter-planar separation of 3.345 (3) Å and a ring slippage of 1.822 Å] between pyridyl rings link the chains into a two-dimensional supra-molecular 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 = 671.22

Triclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.06

1682 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.69 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033605/zl2401sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu2I2(C8H7N3)2]	Z = 1
Mr = 671.22	F(000) = 316
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0418P)2 + 0.3135P] where P = (Fo2 + 2Fc2)/3
1682 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .