catena-Poly[3,3'-diethyl-1,1'-(propane-1,3-di-yl)di(1H-imidazol-3-ium) [silver(I)-di-μ-iodido-silver(I)-di-μ-iodido]].

The title compound, {(C(13)H(22)N(4))[Ag(2)I(4)]}(n), was prepared by reaction of 1,3-bis-(N-ethyl-imidazolium-1-yl)propane iodide with silver (I) oxide. In the 3,3'-diethyl-1,1'-(propane-1,3-di-yl)di(1H-imidazol-3-ium) cation, the dihedral angle between the imidazole rings is 49.3 (1)°. In the [Ag(2)I(4)](2-) anion, each Ag(I) atom is bonded to three iodide anions, the two Ag(I) atoms and two of the iodides forming Ag(2)I(2) square-planar (r.m.s. deviation = 0.01 Å) units·The remaining two iodides, which are placed on opposite sides of the square, together with their centrosymmetric counterparts, link the square-planar Ag(2)I(2) units into {[Ag(2)I(4)](2-)}(n) polymeric chains via Ag-I bonds.

Related literature

For background to the chemistry of imidazolium compounds, see: Wasserscheid & Keim (2000 ▶); Migowski & Dupont (2007 ▶). For some applications of imidazolium salts, see: Leclercq & Schmitzer (2009 ▶); Petkovic et al. (2011 ▶); Chen et al. (2006 ▶). For other polymeric chain structures formed via Ag—I bonds, see: Chen & Liu (2003 ▶).

Experimental

Crystal data

(C13H22N4)[Ag2I4]

M = 957.69

Triclinic,

a = 9.1202 (18) Å

b = 11.543 (2) Å

c = 12.158 (2) Å

α = 74.677 (3)°

β = 70.566 (3)°

γ = 79.903 (3)°

V = 1158.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 7.02 mm−1

T = 296 K

0.25 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.987

5868 measured reflections

4008 independent reflections

3692 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.04

4008 reflections

211 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020715/lr2057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020715/lr2057Isup2.hkl

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

(C13H22N4)[Ag2I4]	Z = 2
Mr = 957.69	F(000) = 868
Triclinic, P1	Dx = 2.745 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1202 (18) Å	Cell parameters from 5325 reflections
b = 11.543 (2) Å	θ = 2.3–27.9°
c = 12.158 (2) Å	µ = 7.02 mm−1
α = 74.677 (3)°	T = 296 K
β = 70.566 (3)°	Block, light yellow
γ = 79.903 (3)°	0.25 × 0.24 × 0.22 mm
V = 1158.7 (4) Å3

Bruker APEXII CCD area-detector diffractometer	4008 independent reflections
Radiation source: fine-focus sealed tube	3692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
phi and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.932, Tmax = 0.987	k = −13→13
5868 measured reflections	l = −14→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0283P)2 + 2.6676P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4008 reflections	Δρmax = 1.05 e Å−3
211 parameters	Δρmin = −0.86 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00298 (17)

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.

	x	y	z	Uiso*/Ueq
Ag1	0.49679 (5)	0.38435 (5)	0.12441 (5)	0.06103 (15)
Ag2	0.51160 (6)	0.13741 (5)	0.37420 (5)	0.06227 (15)
I1	0.60326 (4)	0.13113 (3)	0.12542 (3)	0.04516 (12)
I2	0.40256 (4)	0.38216 (3)	0.37820 (3)	0.05260 (12)
I3	0.75335 (4)	0.51943 (3)	−0.02697 (3)	0.04661 (12)
I4	0.71765 (4)	0.03787 (3)	0.51764 (3)	0.05221 (13)
N1	0.0416 (6)	0.6747 (4)	0.6691 (4)	0.0537 (11)
N2	−0.0555 (5)	0.7953 (4)	0.7900 (4)	0.0409 (9)
N3	0.0591 (6)	1.1532 (4)	0.7756 (4)	0.0520 (11)
N4	0.2501 (5)	1.2543 (4)	0.7546 (4)	0.0494 (11)
C1	0.0810 (13)	0.6785 (8)	0.4606 (7)	0.112 (3)
H1A	−0.0160	0.7252	0.4568	0.169*
H1B	0.1122	0.6284	0.4034	0.169*
H1C	0.1598	0.7318	0.4426	0.169*
C2	0.0617 (12)	0.6051 (7)	0.5769 (7)	0.091 (3)
H2A	0.1523	0.5465	0.5756	0.109*
H2B	−0.0290	0.5611	0.5993	0.109*
C3	−0.0752 (7)	0.7562 (5)	0.7026 (5)	0.0535 (14)
H3	−0.1577	0.7820	0.6704	0.064*
C4	0.0778 (6)	0.7339 (5)	0.8119 (6)	0.0527 (14)
H4	0.1185	0.7415	0.8701	0.063*
C5	0.1395 (7)	0.6616 (5)	0.7360 (6)	0.0570 (15)
H5	0.2323	0.6115	0.7297	0.068*
C6	−0.1652 (7)	0.8773 (6)	0.8592 (6)	0.0639 (17)
H6A	−0.2207	0.8311	0.9368	0.077*
H6B	−0.2414	0.9173	0.8182	0.077*
C7	−0.0831 (8)	0.9726 (6)	0.8771 (6)	0.0601 (15)
H7A	−0.1545	1.0129	0.9378	0.072*
H7B	0.0059	0.9340	0.9042	0.072*
C8	−0.0296 (8)	1.0630 (6)	0.7621 (6)	0.0629 (16)
H8A	−0.1194	1.1045	0.7374	0.076*
H8B	0.0367	1.0218	0.7004	0.076*
C9	−0.0017 (7)	1.2409 (5)	0.8407 (5)	0.0556 (14)
H9	−0.1052	1.2541	0.8859	0.067*
C10	0.1163 (7)	1.3039 (5)	0.8267 (5)	0.0576 (15)
H10	0.1090	1.3694	0.8598	0.069*
C11	0.2117 (7)	1.1627 (5)	0.7253 (5)	0.0525 (13)
H11	0.2805	1.1133	0.6774	0.063*
C12	0.4114 (8)	1.2921 (7)	0.7163 (6)	0.0737 (19)
H12A	0.4710	1.2680	0.6421	0.088*
H12B	0.4052	1.3794	0.7009	0.088*
C13	0.4953 (7)	1.2391 (7)	0.8069 (7)	0.0719 (19)
H13A	0.4354	1.2606	0.8814	0.108*
H13B	0.5956	1.2697	0.7797	0.108*
H13C	0.5089	1.1529	0.8181	0.108*

	U11	U22	U33	U12	U13	U23
Ag1	0.0493 (3)	0.0654 (3)	0.0668 (3)	−0.0107 (2)	−0.0207 (2)	−0.0044 (2)
Ag2	0.0636 (3)	0.0600 (3)	0.0629 (3)	−0.0068 (2)	−0.0189 (2)	−0.0128 (2)
I1	0.0412 (2)	0.0478 (2)	0.0471 (2)	−0.00823 (15)	−0.01187 (15)	−0.01073 (15)
I2	0.0532 (2)	0.0519 (2)	0.0513 (2)	−0.00460 (17)	−0.01208 (17)	−0.01417 (17)
I3	0.03871 (19)	0.0443 (2)	0.0542 (2)	−0.00964 (14)	−0.01653 (15)	0.00034 (16)
I4	0.0522 (2)	0.0540 (2)	0.0524 (2)	−0.01805 (17)	−0.01913 (17)	−0.00228 (17)
N1	0.059 (3)	0.051 (3)	0.051 (3)	−0.009 (2)	−0.016 (2)	−0.010 (2)
N2	0.033 (2)	0.043 (2)	0.048 (2)	−0.0121 (18)	−0.0158 (18)	−0.0016 (19)
N3	0.058 (3)	0.045 (2)	0.054 (3)	−0.011 (2)	−0.010 (2)	−0.017 (2)
N4	0.057 (3)	0.047 (2)	0.045 (3)	−0.014 (2)	−0.017 (2)	−0.004 (2)
C1	0.199 (11)	0.081 (6)	0.066 (5)	−0.043 (6)	−0.034 (6)	−0.019 (4)
C2	0.138 (8)	0.065 (4)	0.083 (5)	−0.014 (5)	−0.037 (5)	−0.027 (4)
C3	0.057 (3)	0.056 (3)	0.059 (3)	−0.012 (3)	−0.035 (3)	−0.004 (3)
C4	0.044 (3)	0.054 (3)	0.067 (4)	−0.011 (3)	−0.031 (3)	−0.002 (3)
C5	0.039 (3)	0.053 (3)	0.080 (4)	−0.008 (3)	−0.021 (3)	−0.010 (3)
C6	0.042 (3)	0.074 (4)	0.070 (4)	−0.021 (3)	0.003 (3)	−0.021 (3)
C7	0.063 (4)	0.064 (4)	0.054 (3)	−0.009 (3)	−0.011 (3)	−0.021 (3)
C8	0.075 (4)	0.060 (4)	0.063 (4)	−0.016 (3)	−0.027 (3)	−0.014 (3)
C9	0.051 (3)	0.057 (3)	0.059 (3)	−0.005 (3)	−0.009 (3)	−0.024 (3)
C10	0.071 (4)	0.052 (3)	0.055 (3)	−0.009 (3)	−0.018 (3)	−0.019 (3)
C11	0.058 (3)	0.044 (3)	0.053 (3)	−0.001 (3)	−0.014 (3)	−0.013 (3)
C12	0.073 (5)	0.084 (5)	0.064 (4)	−0.034 (4)	−0.019 (3)	−0.002 (4)
C13	0.050 (4)	0.093 (5)	0.074 (4)	−0.005 (3)	−0.023 (3)	−0.018 (4)

Ag1—I3i	2.8383 (7)	C1—H1C	0.9600
Ag1—I3	2.8618 (7)	C2—H2A	0.9700
Ag1—I2	2.9089 (9)	C2—H2B	0.9700
Ag1—I1	2.9120 (8)	C3—H3	0.9300
Ag2—I2	2.8333 (8)	C4—C5	1.327 (9)
Ag2—I4	2.8735 (7)	C4—H4	0.9300
Ag2—I1	2.8749 (8)	C5—H5	0.9300
Ag2—I4ii	2.9054 (8)	C6—C7	1.529 (8)
I3—Ag1i	2.8383 (7)	C6—H6A	0.9700
I4—Ag2ii	2.9054 (7)	C6—H6B	0.9700
N1—C3	1.322 (8)	C7—C8	1.495 (9)
N1—C5	1.362 (7)	C7—H7A	0.9700
N1—C2	1.491 (8)	C7—H7B	0.9700
N2—C3	1.332 (7)	C8—H8A	0.9700
N2—C4	1.366 (7)	C8—H8B	0.9700
N2—C6	1.460 (7)	C9—C10	1.342 (8)
N3—C11	1.332 (7)	C9—H9	0.9300
N3—C9	1.376 (7)	C10—H10	0.9300
N3—C8	1.496 (7)	C11—H11	0.9300
N4—C11	1.333 (7)	C12—C13	1.488 (10)
N4—C10	1.376 (7)	C12—H12A	0.9700
N4—C12	1.495 (8)	C12—H12B	0.9700
C1—C2	1.415 (11)	C13—H13A	0.9600
C1—H1A	0.9600	C13—H13B	0.9600
C1—H1B	0.9600	C13—H13C	0.9600
I3i—Ag1—I3	105.33 (2)	C5—C4—H4	125.8
I3i—Ag1—I2	111.08 (2)	N2—C4—H4	125.8
I3—Ag1—I2	116.87 (2)	C4—C5—N1	107.1 (5)
I3i—Ag1—I1	115.75 (2)	C4—C5—H5	126.4
I3—Ag1—I1	106.74 (2)	N1—C5—H5	126.4
I2—Ag1—I1	101.418 (18)	N2—C6—C7	112.2 (5)
I2—Ag2—I4	112.83 (2)	N2—C6—H6A	109.2
I2—Ag2—I1	104.221 (19)	C7—C6—H6A	109.2
I4—Ag2—I1	121.64 (2)	N2—C6—H6B	109.2
I2—Ag2—I4ii	117.25 (2)	C7—C6—H6B	109.2
I4—Ag2—I4ii	98.81 (2)	H6A—C6—H6B	107.9
I1—Ag2—I4ii	102.35 (2)	C8—C7—C6	110.0 (5)
Ag2—I1—Ag1	76.825 (17)	C8—C7—H7A	109.7
Ag2—I2—Ag1	77.525 (17)	C6—C7—H7A	109.7
Ag1i—I3—Ag1	74.67 (2)	C8—C7—H7B	109.7
Ag2—I4—Ag2ii	81.19 (2)	C6—C7—H7B	109.7
C3—N1—C5	108.4 (5)	H7A—C7—H7B	108.2
C3—N1—C2	126.4 (6)	C7—C8—N3	111.0 (5)
C5—N1—C2	125.2 (6)	C7—C8—H8A	109.4
C3—N2—C4	107.0 (5)	N3—C8—H8A	109.4
C3—N2—C6	126.4 (5)	C7—C8—H8B	109.4
C4—N2—C6	126.1 (5)	N3—C8—H8B	109.4
C11—N3—C9	108.1 (5)	H8A—C8—H8B	108.0
C11—N3—C8	125.4 (5)	C10—C9—N3	107.2 (5)
C9—N3—C8	126.4 (5)	C10—C9—H9	126.4
C11—N4—C10	107.7 (5)	N3—C9—H9	126.4
C11—N4—C12	124.9 (5)	C9—C10—N4	107.9 (5)
C10—N4—C12	127.4 (5)	C9—C10—H10	126.1
C2—C1—H1A	109.5	N4—C10—H10	126.1
C2—C1—H1B	109.5	N3—C11—N4	109.1 (5)
H1A—C1—H1B	109.5	N3—C11—H11	125.4
C2—C1—H1C	109.5	N4—C11—H11	125.4
H1A—C1—H1C	109.5	C13—C12—N4	113.0 (6)
H1B—C1—H1C	109.5	C13—C12—H12A	109.0
C1—C2—N1	113.4 (6)	N4—C12—H12A	109.0
C1—C2—H2A	108.9	C13—C12—H12B	109.0
N1—C2—H2A	108.9	N4—C12—H12B	109.0
C1—C2—H2B	108.9	H12A—C12—H12B	107.8
N1—C2—H2B	108.9	C12—C13—H13A	109.5
H2A—C2—H2B	107.7	C12—C13—H13B	109.5
N1—C3—N2	109.0 (5)	H13A—C13—H13B	109.5
N1—C3—H3	125.5	C12—C13—H13C	109.5
N2—C3—H3	125.5	H13A—C13—H13C	109.5
C5—C4—N2	108.4 (5)	H13B—C13—H13C	109.5
I2—Ag2—I1—Ag1	0.813 (16)	C6—N2—C3—N1	−174.1 (5)
I4—Ag2—I1—Ag1	−127.96 (2)	C3—N2—C4—C5	1.8 (6)
I4ii—Ag2—I1—Ag1	123.43 (2)	C6—N2—C4—C5	175.1 (5)
I3i—Ag1—I1—Ag2	−121.10 (2)	N2—C4—C5—N1	−2.1 (7)
I3—Ag1—I1—Ag2	122.05 (2)	C3—N1—C5—C4	1.6 (7)
I2—Ag1—I1—Ag2	−0.783 (16)	C2—N1—C5—C4	−176.6 (6)
I4—Ag2—I2—Ag1	133.12 (2)	C3—N2—C6—C7	−137.1 (6)
I1—Ag2—I2—Ag1	−0.811 (16)	C4—N2—C6—C7	50.9 (8)
I4ii—Ag2—I2—Ag1	−113.07 (2)	N2—C6—C7—C8	72.4 (7)
I3i—Ag1—I2—Ag2	124.36 (2)	C6—C7—C8—N3	−176.8 (5)
I3—Ag1—I2—Ag2	−114.78 (3)	C11—N3—C8—C7	111.0 (7)
I1—Ag1—I2—Ag2	0.792 (16)	C9—N3—C8—C7	−69.5 (8)
I3i—Ag1—I3—Ag1i	0.0	C11—N3—C9—C10	1.0 (7)
I2—Ag1—I3—Ag1i	−123.85 (3)	C8—N3—C9—C10	−178.5 (6)
I1—Ag1—I3—Ag1i	123.56 (3)	N3—C9—C10—N4	−0.8 (7)
I2—Ag2—I4—Ag2ii	124.61 (3)	C11—N4—C10—C9	0.3 (7)
I1—Ag2—I4—Ag2ii	−110.47 (3)	C12—N4—C10—C9	−178.5 (6)
I4ii—Ag2—I4—Ag2ii	0.0	C9—N3—C11—N4	−0.8 (7)
C3—N1—C2—C1	63.8 (11)	C8—N3—C11—N4	178.7 (5)
C5—N1—C2—C1	−118.4 (9)	C10—N4—C11—N3	0.3 (6)
C5—N1—C3—N2	−0.4 (6)	C12—N4—C11—N3	179.2 (5)
C2—N1—C3—N2	177.7 (6)	C11—N4—C12—C13	−95.5 (8)
C4—N2—C3—N1	−0.8 (6)	C10—N4—C12—C13	83.2 (8)