Bis(4-methyl­imidazolium) succinate succinic acid solvate

Guihuan Du; Zuli Liu; Qian Chu; Zhen Li; Suming Zhang

doi:10.1107/S1600536809006205

. 2009 Feb 25;65(Pt 3):o607–o608. doi: 10.1107/S1600536809006205

Bis(4-methylimidazolium) succinate succinic acid solvate

Guihuan Du ^a,^*, Zuli Liu ^a, Qian Chu ^b, Zhen Li ^b, Suming Zhang ^b

PMCID: PMC2968489 PMID: 21582261

Abstract

In the title compound, 2C₄H₇N₂ ⁺·C₄H₄O₄ ²⁻·C₄H₆O₄, the asymmetric unit consists of two 4-methylimidazolium cations, one succinate dianion and one netrual succinic acid molecule and within the latter components, the C—O, C=O and C O bonds are clearly evidenced from their relative distances. In the crystal structure, the individual components are linked by intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to the (101) plane in which R ₃ ³(9), R ₃ ³(12) and R ₄ ⁴(18) hydrogen-bond motifs are present.

Related literature

For general background on co-crystals, see: Aakeröy & Salmon (2005 ▶); Aakeröy et al. (2007 ▶); Childs & Hardcastle (2007 ▶); Childs et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C₄H₇N₂ ⁺·C₄H₄O₄ ²⁻·C₄H₆O₄
M _r = 400.39
Monoclinic,
a = 17.260 (5) Å
b = 14.066 (4) Å
c = 7.761 (2) Å
β = 95.008 (6)°
V = 1877.0 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.30 × 0.10 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.957, T _max = 0.995
20337 measured reflections
4080 independent reflections
2197 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.153
S = 0.95
4080 reflections
273 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006205/lh2776sup1.cif

e-65-0o607-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006205/lh2776Isup2.hkl

e-65-0o607-Isup2.hkl^{(200KB, hkl)}

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

Table 1. Selected bond lengths (Å).

C9—O1	1.235 (2)
C9—O2	1.271 (2)
C12—O4	1.228 (3)
C12—O3	1.276 (2)
C13—O6	1.210 (2)
C13—O5	1.298 (3)
C16—O7	1.207 (2)
C16—O8	1.302 (3)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.96 (2)	1.74 (2)	2.699 (3)	176 (2)
N2—H2A⋯O3	0.97 (2)	1.78 (2)	2.752 (2)	173.0 (19)
N3—H3A⋯O1	1.07 (2)	1.61 (2)	2.673 (2)	170.6 (19)
N4—H4⋯O2ⁱⁱ	0.98 (2)	1.77 (2)	2.745 (2)	178.8 (19)
O5—H5⋯O3	0.98 (3)	1.53 (3)	2.509 (2)	177 (3)
O8—H8⋯O2ⁱⁱⁱ	1.02 (3)	1.50 (3)	2.518 (2)	176 (3)
C2—H2⋯O6	0.93	2.29	3.024 (3)	136
C3—H3⋯O8^iv	0.93	2.43	3.354 (3)	176
C6—H6⋯O5	0.93	2.43	3.346 (3)	169
C7—H7⋯O7^v	0.93	2.29	3.017 (3)	134

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China under grant Nos. 10574047, 10574048 and 20490210. This work was also supported by the National 973 Project under grant. No. 2006CB921605.

supplementary crystallographic information

Comment

In recent years, research on co-crystal or organic salts has been expanded rapidly owing to their potential application in the preparation of active pharmaceutical ingredients (Aakeröy et al., 2007; Childs & Hardcastle, 2007; Childs et al., 2007). In this paper, we report an organic salt formed by 4-methyl-imidazole and succinic acid in 95% methanol solution at room temperature, namely bis(4-methyl-imidazolium) succinicate succinic acid, (I).

In (I), the asymmetric unit is composed of two 4-methylimidazolium cations, one succinicate dianion and one netrual succinic acid molecule. The title compound can be regarded as an organic salt according to the definition of Aakeröy and Salmon (2005). One of the succinnic acid molecules is dually deprotonated, leading to a dianion (Fig. 1) which can be evidenced to an extent by the variations of the carboxyl C-O, C ═O and C ≐O bond distances (Table 1).

In the crystal structure, by a combination of four N-H···O and two O-H···O hydrogen bonds (Table 2) molecules in (I) are linked into a two-dimensional network parallel to the (101) plane (Fig.2) in which R₃³(9), R₃³(12) and R₄⁴(18) hydrogen-bonding motifs are present (Bernstein et al., 1995). Within the network, several weak C-H..O interactions are present. No other interactions, such as C-H···π or π···π are observed in (I).

Experimental

All the reagents and solvents were used as obtained without further purification. A 1:2 molar amounts of succinic acid (0.2 mmol, 23.6 mg) and 4-methyl-imidazole (0.4 mmol, 32.8 mg) were dissolved in 95% methanol (20 ml). The mixture was stirred for half an hour at room temperature and then filtered. The resulting solution was kept in air for one week. Plate crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel.