2,2′-(p-Phenyl­ene)bis­(4,5-dihydro-1H-imidazol-3-ium) bis­(3-nitro­benzoate)

Song, X.-M.; Li, J.-J.; Liu, X.-H.; Ren, C.-X.; Shang, S.-M.

doi:10.1107/S1600536810053341

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o263

doi:10.1107/S1600536810053341

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2,2′-(p-Phenylene)bis(4,5-dihydro-1H-imidazol-3-ium) bis(3-nitrobenzoate)

Xiu-Mei Song,^a Jun-Jun Li,^b Xin-Hua Liu,^a Chun-Xia Ren ^a ^* and Shao-Ming Shang ^a ^*

^aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China, and ^bCollege of Pharmacy, GuangDong Pharmaceutical University, Guangzhou, Guangdong Province 510006, People's Republic of China
^*Correspondence e-mail: chunxiaren@yahoo.com.cn, smshang@126.com

(Received 6 December 2010; accepted 19 December 2010; online 8 January 2011)

In the title compound, C₁₂H₁₆N₄⁺·2C₇H₄NO₄⁻, the complete 2,2′-(p-phenylene)bis(4,5-dihydro-1H-imidazol-3-ium) (bib) dication is generated by crystallographic inversion symmetry. The bib cations reside on crystallographic inversion centers, which coincide with the centroids of the respective benzene rings. In the cation, the imidazole ring adopts an envelop conformation with the flap atom displaced by 0.082 (3) Å from the plane through the other ring atoms. In the crystal, the cations and anions are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the a axis. C—H⋯O interactions also occur. Weak π–π contacts between the imidazole rings of bib and between the benzene rings of NB [centroid–centroid distances = 3.501 (1) and 3.281 (2) Å, respectively] may further stabilize the structure.

Related literature

For general background to supramolecular interactions, see: Jeffrey (1997 ). For the structures of metal complexes with imidazole ligands reported by our group, see: Ren, Ye, He et al. (2004 ); Ren, Ye, Zhu et al. (2004 ); Ren et al. (2007 , 2009 ).

Experimental

Crystal data

C₁₂H₁₆N₄²⁺·2C₇H₄NO₄⁻
M_r = 548.51
Triclinic, $[P \overline 1]$
a = 6.9882 (12) Å
b = 7.4165 (12) Å
c = 13.233 (2) Å
α = 81.343 (3)°
β = 82.443 (3)°
γ = 62.699 (2)°
V = 600.96 (17) Å³
Z = 1
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 273 K
0.67 × 0.55 × 0.42 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.927, T_max = 0.953
3714 measured reflections
2575 independent reflections
1676 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.151
S = 1.07
2575 reflections
181 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.48	3.283 (3)	144
N1—H1⋯O1ⁱⁱ	0.86	1.97	2.763 (3)	153
N2—H2⋯O2ⁱⁱⁱ	0.86	1.80	2.646 (3)	166
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) x+1, y-1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536810053341/ds2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053341/ds2078Isup2.hkl

checkCIF report

Comment top

Attention has been recently focused on the use of supramolecular interactions, such as hydrogen bonding and π-π interactions, in the controlled assembly of supramolecular architectures (Jeffrey, 1997). Hydrogen bonds often play a dominant role in crystal engineering because of their combine strength with directionality. We have reported several complexes having an imidazole entity, and have concluded that hydrogen bonding involving this group influences the geometry around the metal atom and the crystallization mechanism (Ren, Ye, He et al., 2004; Ren, Ye, Zhu et al., 2004; Ren, et al., 2007; Ren, et al., 2009). As a further contribution to this field, we describe herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one-half of 1,4-bis(4,5-dihydro-H,4H–imidazol-2-yl)benzene (bib) cation and one 3-nitrobenzoate (NB) anion. In the bib molecule, the imidazole ring A (N1/N2/C1—C3) adopts an envelop conformation with atom C4 displaced by 0.082 (3)/A from the plane of the other ring atoms. Rings B (C4/C5/C6/C4'/C5'/C6') [symmetry code ('): 3 - x,-y,-z] are, of course, planar and they are oriented at a dihedral angle of 96.6/%.

In the crystal structure, the bib and NB ligands are joined together through hydrogen bonds between the carboxy oxygen in NB and nitrogen atom in bib to give a macrocycle N1—H1···O1 and N2—H2···O2 with the hydrogen bond geometry given in Table 1, and a face-to-face intracyclic π-π interaction at 3.50 (1) /A. Each bib group also features another macrocycles, resulting in 1-D chains running along the a axis. As illustracted in Fig. 2, the adjacent NB ligands are furthermore linked in the antiparallel alignment with offset along the bc plane by π-π contacts (3.28 (1)/A) in a 3-D structure (Fig. 2). Weak intermolecular C—H···O contacts contribute to the stability of the layered structure (Table 1).

Related literature top

For general background to supramolecular interactions, see: Jeffrey (1997). For the structures of related metal complexes with imidazole ligands reported by our group, see: Ren, Ye, He et al. (2004); Ren, Ye, Zhu et al. (2004); Ren et al. (2007, 2009).

Experimental top

All the reagents and solvents employed were commercially available and used as received without further purification.

Syntheses of 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene: a mixture of 1,4-Benzenedicarboxylic acid (2.31 g, 13.9 mmol), ethylenediamine (3.70 ml, 50 mmol), ethylenediamine dihydrochloride(6.64 g, 50 mmol) and toluene-p-sulfonic acid (0.208 g, 1.09 mmol) in ethyleneglycol (20 ml) was refluxed at 198/%C for 3 h. Then about half of the ethylene glycol solvent was then slowly removed by distillation at 120 /%C. The residue was dissolved in a mixture of water (40 ml) and concentrated hydrochloric acid (11 M, 3 ml). The addition of 50% aqueous sodium hydroxide gave a yellow precipitate that was recrystallized by methonal (yield 83% based on 1,4-benzenedicarboxylic acid (ca 2.50 g). Calc. for C₁₂H₁₄N₄: C 67.27; H 6.59; N 26.15%. Found: C 66.98; H 6.92; N 26.08%. IR (KBr, cm^-1): 3188(m), 2936(m), 2866(m), 1606(s), 1532(s), 1466(s), 1345(m), 1270(s), 1191(w), 1080(w), 981(m), 855(m).

Syntheses of the title compound: to a solution of 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene (0.0109 g, 0.05 mmol) in methonal (1 ml), an acetonitrile solution (1 ml) of 3-nitrobenzoic acid (0.0069 g, 0.06 mmol) was added and stirred 10 min at room temperature. The solution was allowed at room temperature in 10 ml diethyl diether for 25 h by slow evaporation. Colorless prismatic crystals of the title compound were obtained, which were collected by filtration, washed with water and dried in vacuum desiccator over silica gel (0.0095 g, 41%). IR (KBr,cm^-1): 3436(s), 3080(w), 2924(m), 1618(s), 1560(m), 1524(s), 1383(s), 1370(s), 1351(s), 1282(m), 720(m), 696(w).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 structure of the title complex 1,4-bis(4,5-dihydro-H,4H-imidazol-2-yl)benzene bis(3-nitrobenzoate) showing 30° probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound viewed along the baxis. H atoms not involved in hydrogen bonding are omitted for clarity.

2,2'-(p-Phenylene)bis(4,5-dihydro-1H-imidazol-3-ium) bis(3-nitrobenzoate) top

Crystal data top

C₁₂H₁₆N₄²⁺·2C₇H₄NO₄⁻	V = 600.96 (17) Å³
M_r = 548.51	Z = 1
Triclinic, P1	F(000) = 286
Hall symbol: -P 1	D_x = 1.516 Mg m⁻³
a = 6.9882 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4165 (12) Å	µ = 0.12 mm⁻¹
c = 13.233 (2) Å	T = 273 K
α = 81.343 (3)°	Block, colorless
β = 82.443 (3)°	0.67 × 0.55 × 0.42 mm
γ = 62.699 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2575 independent reflections
Radiation source: fine-focus sealed tube	1676 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
T_min = 0.927, T_max = 0.953	k = −9→9
3714 measured reflections	l = −16→8

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0613P)² + 0.1694P] where P = (F_o² + 2F_c²)/3
2575 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₂H₁₆N₄²⁺·2C₇H₄NO₄⁻	γ = 62.699 (2)°
M_r = 548.51	V = 600.96 (17) Å³
Triclinic, P1	Z = 1
a = 6.9882 (12) Å	Mo Kα radiation
b = 7.4165 (12) Å	µ = 0.12 mm⁻¹
c = 13.233 (2) Å	T = 273 K
α = 81.343 (3)°	0.67 × 0.55 × 0.42 mm
β = 82.443 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2575 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1676 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.953	R_int = 0.016
3714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
2575 reflections	Δρ_min = −0.28 e Å⁻³
181 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 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.

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

	x	y	z	U_iso*/U_eq
C1	0.7607 (4)	0.1903 (4)	0.18562 (17)	0.0483 (6)
H1A	0.7398	0.2592	0.2458	0.058*
H1B	0.6839	0.1075	0.1981	0.058*
C2	0.6871 (4)	0.3430 (3)	0.09029 (18)	0.0492 (6)
H2A	0.5961	0.3147	0.0521	0.059*
H2B	0.6093	0.4820	0.1083	0.059*
C3	1.0544 (3)	0.1481 (3)	0.07401 (15)	0.0383 (5)
C4	1.2831 (3)	0.0707 (3)	0.03509 (15)	0.0373 (5)
C5	1.3404 (3)	0.1420 (3)	−0.06192 (15)	0.0414 (5)
H5	1.2337	0.2373	−0.1034	0.050*
C6	1.5554 (4)	0.0716 (3)	−0.09660 (15)	0.0416 (5)
H6	1.5925	0.1195	−0.1615	0.050*
C7	0.1900 (4)	0.5421 (5)	0.2448 (2)	0.0620 (8)
C8	0.2163 (3)	0.3932 (3)	0.33993 (16)	0.0437 (5)
C9	0.1925 (4)	0.2191 (4)	0.33805 (19)	0.0529 (6)
H9	0.1691	0.1887	0.2765	0.064*
C10	0.2027 (4)	0.0885 (4)	0.4264 (2)	0.0639 (7)
H10	0.1849	−0.0275	0.4239	0.077*
C11	0.2391 (4)	0.1307 (4)	0.5170 (2)	0.0620 (7)
H11	0.2445	0.0452	0.5769	0.074*
C12	0.2671 (3)	0.3009 (4)	0.51797 (16)	0.0507 (6)
C13	0.2561 (3)	0.4345 (3)	0.43168 (17)	0.0462 (5)
H13	0.2750	0.5497	0.4350	0.055*
N1	0.8925 (3)	0.3081 (3)	0.03187 (14)	0.0482 (5)
H1	0.9055	0.3822	−0.0226	0.058*
N2	0.9901 (3)	0.0671 (3)	0.15833 (13)	0.0438 (5)
H2	1.0721	−0.0439	0.1930	0.053*
N3	0.3060 (4)	0.3471 (5)	0.61616 (18)	0.0776 (8)
O1	0.1555 (3)	0.4959 (3)	0.16467 (14)	0.0884 (7)
O2	0.2025 (3)	0.7013 (3)	0.25649 (18)	0.0916 (8)
O3	0.3241 (4)	0.5037 (6)	0.6153 (2)	0.1100 (10)
O4	0.3135 (4)	0.2288 (5)	0.69216 (16)	0.1205 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0495 (13)	0.0543 (13)	0.0410 (12)	−0.0242 (11)	−0.0023 (10)	−0.0025 (10)
C2	0.0456 (13)	0.0468 (12)	0.0473 (13)	−0.0152 (10)	−0.0034 (10)	−0.0009 (10)
C3	0.0477 (12)	0.0387 (10)	0.0286 (10)	−0.0187 (9)	−0.0089 (9)	−0.0010 (8)
C4	0.0446 (12)	0.0356 (10)	0.0298 (10)	−0.0160 (9)	−0.0068 (8)	−0.0011 (8)
C5	0.0472 (12)	0.0380 (11)	0.0323 (11)	−0.0142 (9)	−0.0099 (9)	0.0053 (8)
C6	0.0516 (13)	0.0424 (11)	0.0273 (10)	−0.0197 (10)	−0.0045 (9)	0.0040 (8)
C7	0.0410 (13)	0.0717 (18)	0.0494 (16)	−0.0137 (12)	−0.0021 (11)	0.0233 (13)
C8	0.0359 (11)	0.0477 (12)	0.0367 (12)	−0.0129 (9)	−0.0031 (9)	0.0074 (9)
C9	0.0513 (14)	0.0599 (15)	0.0463 (14)	−0.0226 (11)	−0.0085 (11)	−0.0052 (11)
C10	0.0610 (16)	0.0510 (14)	0.080 (2)	−0.0292 (13)	−0.0097 (14)	0.0104 (13)
C11	0.0513 (15)	0.0686 (17)	0.0530 (16)	−0.0235 (13)	−0.0059 (12)	0.0225 (13)
C12	0.0350 (12)	0.0701 (16)	0.0336 (12)	−0.0131 (11)	−0.0033 (9)	−0.0013 (11)
C13	0.0362 (11)	0.0487 (12)	0.0484 (13)	−0.0153 (10)	−0.0014 (9)	−0.0037 (10)
N1	0.0481 (11)	0.0478 (10)	0.0372 (10)	−0.0146 (9)	−0.0047 (8)	0.0072 (8)
N2	0.0464 (10)	0.0434 (10)	0.0365 (10)	−0.0181 (8)	−0.0060 (8)	0.0062 (8)
N3	0.0438 (13)	0.124 (2)	0.0481 (14)	−0.0212 (14)	−0.0029 (10)	−0.0174 (15)
O1	0.0837 (14)	0.1023 (16)	0.0365 (10)	−0.0115 (12)	−0.0080 (9)	0.0177 (10)
O2	0.0766 (14)	0.0759 (14)	0.1167 (19)	−0.0418 (12)	−0.0346 (12)	0.0561 (13)
O3	0.0816 (17)	0.173 (3)	0.0934 (19)	−0.0593 (18)	0.0042 (13)	−0.0671 (19)
O4	0.0984 (18)	0.183 (3)	0.0363 (12)	−0.0305 (18)	−0.0134 (11)	0.0122 (15)

Geometric parameters (Å, º) top

C1—N2	1.462 (3)	C7—O2	1.257 (4)
C1—C2	1.531 (3)	C7—C8	1.514 (3)
C1—H1A	0.9700	C8—C9	1.380 (3)
C1—H1B	0.9700	C8—C13	1.387 (3)
C2—N1	1.468 (3)	C9—C10	1.388 (3)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—C11	1.367 (4)
C3—N2	1.312 (3)	C10—H10	0.9300
C3—N1	1.317 (3)	C11—C12	1.366 (4)
C3—C4	1.476 (3)	C11—H11	0.9300
C4—C6ⁱ	1.393 (3)	C12—C13	1.380 (3)
C4—C5	1.394 (3)	C12—N3	1.481 (3)
C5—C6	1.383 (3)	C13—H13	0.9300
C5—H5	0.9300	N1—H1	0.8600
C6—C4ⁱ	1.393 (3)	N2—H2	0.8600
C6—H6	0.9300	N3—O4	1.221 (3)
C7—O1	1.246 (4)	N3—O3	1.222 (4)

N2—C1—C2	102.53 (17)	C9—C8—C13	118.9 (2)
N2—C1—H1A	111.3	C9—C8—C7	120.8 (2)
C2—C1—H1A	111.3	C13—C8—C7	120.2 (2)
N2—C1—H1B	111.3	C8—C9—C10	121.2 (2)
C2—C1—H1B	111.3	C8—C9—H9	119.4
H1A—C1—H1B	109.2	C10—C9—H9	119.4
N1—C2—C1	102.37 (17)	C11—C10—C9	119.9 (2)
N1—C2—H2A	111.3	C11—C10—H10	120.1
C1—C2—H2A	111.3	C9—C10—H10	120.1
N1—C2—H2B	111.3	C12—C11—C10	118.7 (2)
C1—C2—H2B	111.3	C12—C11—H11	120.7
H2A—C2—H2B	109.2	C10—C11—H11	120.7
N2—C3—N1	111.85 (19)	C11—C12—C13	122.8 (2)
N2—C3—C4	122.98 (18)	C11—C12—N3	118.7 (2)
N1—C3—C4	125.13 (18)	C13—C12—N3	118.4 (3)
C6ⁱ—C4—C5	119.30 (19)	C12—C13—C8	118.5 (2)
C6ⁱ—C4—C3	119.93 (18)	C12—C13—H13	120.7
C5—C4—C3	120.75 (18)	C8—C13—H13	120.7
C6—C5—C4	120.20 (19)	C3—N1—C2	110.95 (18)
C6—C5—H5	119.9	C3—N1—H1	124.5
C4—C5—H5	119.9	C2—N1—H1	124.5
C5—C6—C4ⁱ	120.50 (19)	C3—N2—C1	111.14 (17)
C5—C6—H6	119.7	C3—N2—H2	124.4
C4ⁱ—C6—H6	119.7	C1—N2—H2	124.4
O1—C7—O2	127.2 (2)	O4—N3—O3	124.9 (3)
O1—C7—C8	117.2 (3)	O4—N3—C12	117.8 (3)
O2—C7—C8	115.6 (3)	O3—N3—C12	117.3 (3)

Symmetry code: (i) −x+3, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱⁱ	0.93	2.48	3.283 (3)	144
N1—H1···O1ⁱⁱⁱ	0.86	1.97	2.763 (3)	153
N2—H2···O2^iv	0.86	1.80	2.646 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₄²⁺·2C₇H₄NO₄⁻
M_r	548.51
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	6.9882 (12), 7.4165 (12), 13.233 (2)
α, β, γ (°)	81.343 (3), 82.443 (3), 62.699 (2)
V (Å³)	600.96 (17)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.67 × 0.55 × 0.42

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.927, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	3714, 2575, 1676
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.151, 1.07
No. of reflections	2575
No. of parameters	181
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), 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
C6—H6···O2ⁱ	0.93	2.48	3.283 (3)	144
N1—H1···O1ⁱⁱ	0.86	1.97	2.763 (3)	153
N2—H2···O2ⁱⁱⁱ	0.86	1.80	2.646 (3)	166

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

Acknowledgements

This work was generously supported by the National Natural Science Foundation of China (No. 20701016).

References

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Volume 67| Part 2| February 2011| Page o263

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

2,2′-(p-Phenyl­ene)bis­­(4,5-di­hydro-1H-imidazol-3-ium) bis­­(3-nitro­benzoate)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-(p-Phenylene)bis(4,5-dihydro-1H-imidazol-3-ium) bis(3-nitrobenzoate)