Diimidazolium phthalate monohydrate

Chua-Hua Yu

doi:10.1107/S1600536812028619

. 2012 Jun 30;68(Pt 7):o2295. doi: 10.1107/S1600536812028619

Diimidazolium phthalate monohydrate

Chua-Hua Yu ^a,^*

PMCID: PMC3394071 PMID: 22798936

Abstract

In the title compound, 2C₃H₅N₂ ⁺·C₈H₄O₄ ²⁻·H₂O, the cations, anion and water molecule are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

The title compound was synthesized during a search for ferroelectric materials. For background to ferroelectric organic materials with framework structures, see: Zhang et al. (2009 ▶, 2010 ▶); Zhang & Xiong (2012 ▶). For related structures, see: Yu & Zhu (2012 ▶); Zhu & Yu (2011 ▶).

Experimental

Crystal data

2C₃H₅N₂ ⁺·C₈H₄O₄ ²⁻·H₂O
M _r = 320.31
Monoclinic,
a = 9.1250 (18) Å
b = 12.979 (3) Å
c = 13.549 (3) Å
β = 103.85 (3)°
V = 1558.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.26 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.967, T _max = 0.973
15753 measured reflections
3567 independent reflections
2758 reflections with I > 2σ(I)
R _int = 0.044
3 standard reflections every 180 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.141
S = 1.10
3567 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028619/go2058sup1.cif

e-68-o2295-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028619/go2058Isup2.hkl

e-68-o2295-Isup2.hkl^{(174.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028619/go2058Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.96	1.71	2.665 (2)	170
N2—H2A⋯O2ⁱ	0.91	1.75	2.655 (2)	172
N3—H3A⋯O3	0.95	1.80	2.747 (2)	177
N3—H3A⋯O4	0.95	2.56	3.191 (2)	124
N4—H4A⋯O3ⁱⁱ	0.86	1.93	2.774 (2)	168
O1W—H1WA⋯O4	0.86	1.98	2.834 (2)	170
O1W—H1WB⋯O2ⁱⁱⁱ	0.90	1.94	2.8326 (19)	172

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

Acknowledgments

The author thanks the Ordered Matter Science Research Center, Southeast University.

supplementary crystallographic information

Comment

In our search for potential ferroelectric phase change materials, the title compound was synthesized. This search is carried out by measurement of the dielectric constant of compounds on the basis of temperature, for eaxmple, (Zhang, Chen et al., 2009; Zhang, Ye et al., 2010; Zhang & Xiong, 2012), this has been carried out for C₃H₅N₂⁺.C₂HO₄^- (Yu & Zhu, 2012) and C₅H₉N₂⁺.C₈H₅O₄^- (Zhu & Yu, 2011). In the case of the title compound no dielectric anomaly was observed ranging from 130 K to 375 K.

The crystal structure of the title compound contains two protonated imidazolium cations, one phthalate anion, losing two H atoms, and one molecule of water molecule is shown in Fig. 1. The asymmetric unit was selected with the cations, anion and water molecule connected by the intramolecular hydrogen bonds, N1–1A···O1, N3–H3A···O3, N3–H3A···O4 and O1W–H1WA···O4 all of which connect the cations and the water molecule to the anion, Table 1. These units are connected by the intermolecular hydrogen bonds, N2–H2A···O2(-1+x,y,z), N4-H4A···O3(-x+1/2,y-1/2,-z+1/2) and O1W–H1WB···O2(-x+2,-y+1,-z+1), to form a three-dimensional network Table2 and Figure 1.

Experimental

0.83 g (5 mmol) of phthalic acid was added to in 10 ml water which was heated. A few drops of ethanol and 0.68 g (10 mmol) imidazole were added to the solution. The mixture was stirreduntil it reached ambient temperature, the liquid was filtered to give a clear solution. Colourless crystals suitable for X-ray structure analysis were obtained by the slow evaporation of the solution after several days at the ambient temperature.