3,3′-Diethyl-1,1′-[anthracene-9,10-diylbis(oxyethyl­ene)]diimidazolium diiodide

Hou, Y.

doi:10.1107/S1600536809038379

organic compounds

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Volume 65| Part 10| October 2009| Page o2593

doi:10.1107/S1600536809038379

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3,3′-Diethyl-1,1′-[anthracene-9,10-diylbis(oxyethylene)]diimidazolium diiodide

Yanhui Hou ^a ^*

^aSchool of Materials Science and Engineering, Tianjin Polytechnic University, No. 63 Chenglin Road, Tianjin 300160, People's Republic of China
^*Correspondence e-mail: houyh1977@163.com

(Received 11 September 2009; accepted 22 September 2009; online 30 September 2009)

In the title centrosymmetric compound, C₂₈H₃₂N₄O₂²⁺ 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 ( $[\overline{1}]$ 01) by C—H⋯I hydrogen bonds and π–π interactions 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

C₂₈H₃₂N₄O₂²⁺·2I⁻
M_r = 710.38
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.102
S = 1.07
2603 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) x, y+1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038379/ci2907sup1.cif

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

checkCIF report

Comment top

As ancillary ligands, N-heterocyclic carbenes (NHCs) have received considerable attention due to their strong σ-donor ability, and are attractive alternatives to the widely utilized phosphine ligands in metal coordination chemistry (Bourissou et al., 2000; Herrmann & Kocher, 1997). A number of N-heterocyclic carbene transition metal complexes have been synthesized and isolated, and some of them have been successfully applied as homogeneous catalysts (Cavell & McGuinness, 2004; Baker et al., 2004; Melaiye et al., 2004). Herein, the synthesis and crystal structure of a new biscarbene analogue, (I), is reported.

The asymmetric unit contains one-half of the cation and a iodide anion. The cation of (I) lies across a crystallographic inversion centre (Fig. 1). The two imidazole ring planes are approximately perpendicular to the central anthracene ring system, the dihedral angle between them being 86.6 (2)°.

In the crystal, the ionic units are linked via C—H···I interactions. In addition, the anthracene ring system and imidazole rings of two adjacent molecules are stacked, with a centroid-to-centroid separation of 3.717 (3) Å indicating weak π-π interactions. The C—H···I and π-π interactions link ionic units into a two-dimensional network parallel to the (101) [Fig.2].

Related literature top

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 top

A mixture of 1,2-bis(2-chloroethoxy)anthracene (6.7 g, 20 mmol) and 1-ethylimidazole (4.22 g, 44 mmol) was refluxed in THF (100 ml) for 24 h, giving a pale yellow precipitate, which was filtered and washed with THF and recrystallized from methanol and ethyl ether. The obtained solid was dissolved in methanol (200 ml) and an aqueous solution of NH₄I (4.64 g, 32 mmol) was added to the solution. The precipitate formed was collected by filtration and recrystallized from CH₃CN and diethyl ether (1:6 v/v) to give the title compound (yield 95%). Analysis found: C 32.49, H 3.22, N 5.36%; calculated for C₂₈H₃₂N₄O₂I₂: C 32.64, H 3.13, N, 5.44%. ¹H NMR (300 M, d₆-DMSO): δ 9.51 (s, 2 H), 8.03 (s, 2 H), 7.97 (s, 2 H), 7.89–7.86 (m, 4 H), 7.55–7.51 (m, 4 H), 4.85 (t, J = 4.5 Hz, 4 H), 4.49 (t, J = 4.3 Hz, 4 H), 4.35 (q, J = 7.4 Hz, 4 H), 1.51 (t, J = 7.3 Hz, 6 H) p.p.m..

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 cation of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labeled with the suffix A are generated by the symmetry operation (1-x, 1-y, -z).
	Fig. 2. The packing diagram of (I). Dashed lines indicate C—H···I interactions.

3,3'-Diethyl-1,1'-[anthracene-9,10-diylbis(oxyethylene)]diimidazolium diiodide top

Crystal data top

C₂₈H₃₂N₄O₂²⁺·2I⁻	F(000) = 700
M_r = 710.38	D_x = 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

Data collection top

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

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0505P)²] where P = (F_o² + 2F_c²)/3
2603 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₈H₃₂N₄O₂²⁺·2I⁻	V = 1485.3 (3) Å³
M_r = 710.38	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4733 (13) Å	µ = 2.15 mm⁻¹
b = 10.6692 (12) Å	T = 298 K
c = 13.1553 (15) Å	0.24 × 0.22 × 0.22 mm
β = 112.725 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2603 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1989 reflections with I > 2σ(I)
T_min = 0.627, T_max = 0.650	R_int = 0.035
8914 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	Δρ_max = 0.81 e Å⁻³
2603 reflections	Δρ_min = −0.27 e Å⁻³
163 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

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···I1^iv	0.93	3.05	3.957 (6)	167

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

Experimental details

Crystal data
Chemical formula	C₂₈H₃₂N₄O₂²⁺·2I⁻
M_r	710.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.4733 (13), 10.6692 (12), 13.1553 (15)
β (°)	112.725 (2)
V (Å³)	1485.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.24 × 0.22 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.627, 0.650
No. of measured, independent and observed [I > 2σ(I)] reflections	8914, 2603, 1989
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 1.07
No. of reflections	2603
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.27

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Startup Fund for PhDs of Natural Scientific Research of Tianjin Polytechnic University (grant No. 029312).

References

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

3,3′-Di­ethyl-1,1′-[anthracene-9,10-diylbis(oxyethyl­ene)]diimidazolium diiodide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-Diethyl-1,1′-[anthracene-9,10-diylbis(oxyethylene)]diimidazolium diiodide