3,3'-Diethyl-1,1'-[anthracene-9,10-diylbis(oxyethyl-ene)]diimidazolium diiodide.

In the title centrosymmetric compound, C(28)H(32)N(4)O(2) (2+) 2I(-), the two midazole rings are approximately perpendicular to the central anthracene ring system [dihedral angle = 86.6 (2)°]. The ionic units are linked into a two-dimensional network parallel to (01) by C-H⋯I hydrogen bonds and π-π inter-actions involving the anthracene ring system and imidazole rings [centroid-centroid distance = 3.717 (3) Å].

Related literature

For general background to N-heterocyclic carbenes and their transition metal complexes, see: Bourissou et al. (2000 ▶); Herrmann & Kocher (1997 ▶); Cavell & McGuinness (2004 ▶); Baker et al. (2004 ▶); Melaiye et al. (2004 ▶).

Experimental

Crystal data

C28H32N4O2 2+·2I−

M = 710.38

Monoclinic,

a = 11.4733 (13) Å

b = 10.6692 (12) Å

c = 13.1553 (15) Å

β = 112.725 (2)°

V = 1485.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.15 mm−1

T = 298 K

0.24 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.627, T max = 0.650

8914 measured reflections

2603 independent reflections

1989 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.07

2603 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809038379/ci2907sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038379/ci2907Isup2.hkl

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

C28H32N4O22+·2I−	F(000) = 700
Mr = 710.38	Dx = 1.588 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5650 reflections
a = 11.4733 (13) Å	θ = 0.9–28.4°
b = 10.6692 (12) Å	µ = 2.15 mm−1
c = 13.1553 (15) Å	T = 298 K
β = 112.725 (2)°	Block, colourless
V = 1485.3 (3) Å3	0.24 × 0.22 × 0.22 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2603 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→13
Tmin = 0.627, Tmax = 0.650	k = −12→11
8914 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
2603 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.42215 (3)	0.07079 (3)	0.19395 (3)	0.06624 (18)
O1	0.6771 (3)	0.6579 (3)	0.1484 (2)	0.0520 (8)
N1	0.6819 (4)	0.7779 (4)	0.4677 (3)	0.0628 (11)
N2	0.7451 (3)	0.8096 (3)	0.3355 (3)	0.0503 (9)
C1	0.5148 (7)	0.6942 (7)	0.5210 (6)	0.115 (2)
H1A	0.4719	0.7075	0.5699	0.172*
H1B	0.5544	0.6132	0.5349	0.172*
H1C	0.4550	0.6981	0.4461	0.172*
C2	0.6093 (6)	0.7894 (7)	0.5390 (5)	0.100 (2)
H2A	0.6677	0.7860	0.6155	0.120*
H2B	0.5684	0.8708	0.5266	0.120*
C3	0.6648 (5)	0.8459 (5)	0.3797 (4)	0.0603 (13)
H3A	0.6055	0.9096	0.3527	0.072*
C4	0.7780 (5)	0.6961 (5)	0.4802 (4)	0.0723 (16)
H4A	0.8107	0.6375	0.5365	0.087*
C5	0.8164 (5)	0.7143 (5)	0.3988 (4)	0.0651 (14)
H5A	0.8800	0.6705	0.3868	0.078*
C6	0.7488 (5)	0.8552 (5)	0.2318 (4)	0.0637 (13)
H6A	0.8315	0.8392	0.2307	0.076*
H6B	0.7342	0.9449	0.2258	0.076*
C7	0.6479 (4)	0.7891 (4)	0.1346 (3)	0.0577 (12)
H7A	0.5646	0.8048	0.1345	0.069*
H7B	0.6497	0.8189	0.0656	0.069*
C8	0.5860 (4)	0.5813 (4)	0.0729 (3)	0.0443 (10)
C9	0.4887 (4)	0.5346 (4)	0.0997 (3)	0.0432 (10)
C10	0.4733 (5)	0.5667 (4)	0.1992 (4)	0.0534 (12)
H10A	0.5310	0.6204	0.2495	0.064*
C11	0.3758 (5)	0.5200 (5)	0.2213 (4)	0.0642 (13)
H11A	0.3676	0.5417	0.2867	0.077*
C12	0.2873 (5)	0.4392 (5)	0.1468 (4)	0.0655 (14)
H12A	0.2205	0.4083	0.1628	0.079*
C13	0.2987 (5)	0.4058 (4)	0.0511 (4)	0.0557 (12)
H13A	0.2396	0.3517	0.0027	0.067*
C14	0.6018 (4)	0.5485 (4)	−0.0243 (3)	0.0426 (10)

	U11	U22	U33	U12	U13	U23
I1	0.0748 (3)	0.0667 (3)	0.0669 (2)	0.00388 (17)	0.0379 (2)	0.00174 (16)
O1	0.0521 (18)	0.0522 (19)	0.0433 (16)	−0.0023 (14)	0.0090 (14)	−0.0128 (14)
N1	0.073 (3)	0.064 (3)	0.048 (2)	−0.011 (2)	0.020 (2)	−0.013 (2)
N2	0.051 (2)	0.052 (2)	0.0430 (19)	−0.0073 (18)	0.0127 (18)	−0.0170 (17)
C1	0.124 (6)	0.129 (7)	0.115 (5)	−0.023 (5)	0.072 (5)	−0.023 (5)
C2	0.128 (6)	0.118 (5)	0.076 (4)	−0.036 (4)	0.064 (4)	−0.031 (4)
C3	0.066 (3)	0.056 (3)	0.056 (3)	0.003 (2)	0.020 (3)	−0.012 (2)
C4	0.081 (4)	0.067 (4)	0.047 (3)	0.002 (3)	0.001 (3)	0.005 (3)
C5	0.059 (3)	0.067 (3)	0.055 (3)	0.009 (3)	0.008 (3)	−0.013 (3)
C6	0.081 (4)	0.060 (3)	0.050 (3)	−0.019 (3)	0.025 (2)	−0.011 (2)
C7	0.072 (3)	0.050 (3)	0.045 (2)	−0.005 (2)	0.016 (2)	−0.007 (2)
C8	0.044 (3)	0.045 (2)	0.039 (2)	0.005 (2)	0.0102 (19)	−0.0063 (19)
C9	0.049 (3)	0.043 (2)	0.034 (2)	0.012 (2)	0.0113 (19)	−0.0012 (17)
C10	0.061 (3)	0.055 (3)	0.043 (2)	0.002 (2)	0.018 (2)	−0.007 (2)
C11	0.085 (4)	0.069 (3)	0.050 (3)	0.004 (3)	0.039 (3)	−0.007 (2)
C12	0.067 (3)	0.071 (4)	0.069 (3)	0.003 (3)	0.037 (3)	−0.005 (3)
C13	0.057 (3)	0.052 (3)	0.057 (3)	−0.001 (2)	0.021 (2)	−0.007 (2)
C14	0.043 (2)	0.040 (2)	0.041 (2)	0.0060 (19)	0.0121 (19)	−0.0009 (18)

O1—C8	1.395 (5)	C6—H6A	0.97
O1—C7	1.434 (5)	C6—H6B	0.97
N1—C3	1.315 (6)	C7—H7A	0.97
N1—C4	1.365 (6)	C7—H7B	0.97
N1—C2	1.482 (7)	C8—C9	1.387 (6)
N2—C3	1.323 (6)	C8—C14	1.402 (6)
N2—C5	1.368 (6)	C9—C10	1.428 (6)
N2—C6	1.464 (6)	C9—C14i	1.432 (5)
C1—C2	1.437 (8)	C10—C11	1.355 (7)
C1—H1A	0.96	C10—H10A	0.93
C1—H1B	0.96	C11—C12	1.402 (7)
C1—H1C	0.96	C11—H11A	0.93
C2—H2A	0.97	C12—C13	1.363 (7)
C2—H2B	0.97	C12—H12A	0.93
C3—H3A	0.93	C13—C14i	1.407 (7)
C4—C5	1.321 (7)	C13—H13A	0.93
C4—H4A	0.93	C14—C13i	1.407 (7)
C5—H5A	0.93	C14—C9i	1.432 (5)
C6—C7	1.525 (6)
C8—O1—C7	114.0 (3)	N2—C6—H6B	109.7
C3—N1—C4	107.4 (5)	C7—C6—H6B	109.7
C3—N1—C2	125.7 (5)	H6A—C6—H6B	108.2
C4—N1—C2	127.0 (5)	O1—C7—C6	106.3 (4)
C3—N2—C5	107.7 (4)	O1—C7—H7A	110.5
C3—N2—C6	126.0 (4)	C6—C7—H7A	110.5
C5—N2—C6	126.0 (4)	O1—C7—H7B	110.5
C2—C1—H1A	109.5	C6—C7—H7B	110.5
C2—C1—H1B	109.5	H7A—C7—H7B	108.7
H1A—C1—H1B	109.5	C9—C8—O1	119.0 (4)
C2—C1—H1C	109.5	C9—C8—C14	122.8 (4)
H1A—C1—H1C	109.5	O1—C8—C14	118.0 (4)
H1B—C1—H1C	109.5	C8—C9—C10	122.9 (4)
C1—C2—N1	114.2 (5)	C8—C9—C14i	119.0 (4)
C1—C2—H2A	108.7	C10—C9—C14i	118.1 (4)
N1—C2—H2A	108.7	C11—C10—C9	120.8 (4)
C1—C2—H2B	108.7	C11—C10—H10A	119.6
N1—C2—H2B	108.7	C9—C10—H10A	119.6
H2A—C2—H2B	107.6	C10—C11—C12	120.8 (5)
N1—C3—N2	109.5 (4)	C10—C11—H11A	119.6
N1—C3—H3A	125.3	C12—C11—H11A	119.6
N2—C3—H3A	125.3	C13—C12—C11	120.3 (5)
C5—C4—N1	108.3 (5)	C13—C12—H12A	119.9
C5—C4—H4A	125.8	C11—C12—H12A	119.9
N1—C4—H4A	125.8	C12—C13—C14i	121.2 (4)
C4—C5—N2	107.1 (5)	C12—C13—H13A	119.4
C4—C5—H5A	126.4	C14i—C13—H13A	119.4
N2—C5—H5A	126.4	C8—C14—C13i	123.0 (4)
N2—C6—C7	110.0 (4)	C8—C14—C9i	118.2 (4)
N2—C6—H6A	109.7	C13i—C14—C9i	118.8 (4)
C7—C6—H6A	109.7
C3—N1—C2—C1	102.4 (7)	C7—O1—C8—C9	−91.0 (5)
C4—N1—C2—C1	−77.6 (7)	C7—O1—C8—C14	93.1 (4)
C4—N1—C3—N2	0.6 (5)	O1—C8—C9—C10	3.5 (6)
C2—N1—C3—N2	−179.3 (4)	C14—C8—C9—C10	179.2 (4)
C5—N2—C3—N1	−0.1 (5)	O1—C8—C9—C14i	−177.3 (3)
C6—N2—C3—N1	174.7 (4)	C14—C8—C9—C14i	−1.6 (7)
C3—N1—C4—C5	−0.9 (6)	C8—C9—C10—C11	179.1 (4)
C2—N1—C4—C5	179.0 (5)	C14i—C9—C10—C11	−0.1 (6)
N1—C4—C5—N2	0.8 (6)	C9—C10—C11—C12	−0.2 (8)
C3—N2—C5—C4	−0.5 (5)	C10—C11—C12—C13	0.5 (8)
C6—N2—C5—C4	−175.2 (4)	C11—C12—C13—C14i	−0.4 (7)
C3—N2—C6—C7	−80.2 (6)	C9—C8—C14—C13i	−179.1 (4)
C5—N2—C6—C7	93.6 (5)	O1—C8—C14—C13i	−3.3 (6)
C8—O1—C7—C6	173.3 (4)	C9—C8—C14—C9i	1.6 (6)
N2—C6—C7—O1	−60.2 (5)	O1—C8—C14—C9i	177.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···I1ii	0.93	2.89	3.771 (5)	159
C4—H4A···I1iii	0.93	2.97	3.893 (5)	172
C5—H5A···I1iv	0.93	3.05	3.957 (6)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯I1i	0.93	2.89	3.771 (5)	159
C4—H4A⋯I1ii	0.93	2.97	3.893 (5)	172
C5—H5A⋯I1iii	0.93	3.05	3.957 (6)	167

Symmetry codes: (i) ; (ii) ; (iii) .