1-(4-Carb­oxy­phen­yl)-1H-imidazol-3-ium chloride dihydrate

Zhi-Peng Yu; Wen-Qian Geng; Lin Kong; Hong-Ping Zhou

doi:10.1107/S1600536811001838

. 2011 Jan 22;67(Pt 2):o452. doi: 10.1107/S1600536811001838

1-(4-Carboxyphenyl)-1H-imidazol-3-ium chloride dihydrate

Zhi-Peng Yu ^a, Wen-Qian Geng ^a, Lin Kong ^a, Hong-Ping Zhou ^a,^*

PMCID: PMC3051584 PMID: 21523114

Abstract

In the crystal structure of the title compound, C₁₀H₉N₂O₂ ⁺·Cl⁻·2H₂O, the components are linked by O—H⋯O, N—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonds. In the cation, the imidazole ring is oriented at a dihedral angle of 13.67 (17)° with respect to the benzene ring. In the crystal, π–π stacking occurs between nearly parallel benzene rings, which are oriented at a dihedral angle of 3.4 (1)°, the centroid–centroid distance being 3.798 (3) Å.

Related literature

For related imidazole-containing compounds, see: Nyamori & Bala (2008 ▶); Nie et al. (2009 ▶).

Experimental

Crystal data

C₁₀H₉N₂O₂ ⁺·Cl⁻·2H₂O
M _r = 260.67
Orthorhombic,
a = 7.427 (5) Å
b = 17.708 (5) Å
c = 18.748 (5) Å
V = 2465.7 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.912, T _max = 0.940
14555 measured reflections
2165 independent reflections
1515 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.146
S = 0.96
2165 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001838/xu5134sup1.cif

e-67-0o452-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001838/xu5134Isup2.hkl

e-67-0o452-Isup2.hkl^{(106.6KB, hkl)}

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
N2—H2⋯O1ⁱ	0.86	2.21	2.822 (3)	128
N2—H2⋯Cl1ⁱⁱ	0.86	2.62	3.231 (2)	129
O2—H7⋯O4ⁱⁱⁱ	0.82	1.77	2.594 (3)	177
O3—H10⋯Cl1^iv	0.83 (4)	2.36 (4)	3.150 (3)	159 (3)
O3—H11⋯Cl1^v	0.94 (5)	2.22 (5)	3.141 (3)	168 (3)
O4—H12⋯O3	0.76 (4)	1.99 (4)	2.718 (4)	162 (4)
O4—H13⋯Cl1	0.86 (4)	2.22 (4)	3.066 (4)	172 (3)

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

Acknowledgments

This work was supported by grants from the National Natural Science Foundation of China (21071001), the Education Committee of Anhui Province (KJ2009A52, KJ2010A30), the Team for Scientific Innovation Foundation of Anhui Province (2006 K J007TD), the Ministry of Education Person with Ability Foundation of Anhui University, the Science and Technological Fund of Anhui Province for Outstanding Youth (10040606Y22), and the 211 Project of Anhui University.

supplementary crystallographic information

Comment

Imidazol - based materials had been investigated for their electrical and optical properties. Beside, the introduction about the structure of its complex has been reported (Nie et al., 2009). The title molecule that we has designed and synthesized is a good intermediate and penetratingly investigated. In the title molecule(I) (Fig.1), the bond lengths and angles show normal values. The imidazole ring is twisted out of the plane of the center benzene ring at a dihedral angle of 13.67 (17)°. In the title molecule (I) (Fig.2), the neighboring molecules connect through O—H···O, N—H···O, O—H···Cl and N—H···Cl hydrogen bonds (Table 1). π–π stacking is observed between nearly parallel benzene rings, the centroids distance being 3.798 (3) Å.

Experimental

A 150 ml round-bottom flask was charged with a magnetic stirrer and a reflux condenser, iminazole (44 mmol), K₂CO₃ (6.00 g, 43 mmol), 30 ml DMSO and a little Aliquat 336 were added. 4-Fluorobenzaldehyde (4.5 ml, 42 mmol) was added dropwise to the mixture at 363 K and stirred for 15 min. Then the reaction mixture was refluxed for 24 h at 353 K, cooled to room temperature, poured into 150 ml ice-water and filtered. The primrose yellow crude product was obtained, washed with distilled water, and dried in vacuo at room temperature, then purified by recrystallization with ethyl acetate to give the desired analytical pure intermediate products. Intermediate product (12.5 mmol) and 15 ml 20% (wt) NaOH (aq) were added to a round-bottom flask equipped with a magnetic stirrer and a reflux condenser at 333 K for 30 min. Then AgNO₃ (4.00 g, 24 mmol) was added to the mixture group by group. The reaction mixture was refluxed for 24 h at 333 K, cooled to room temperature and filtered. Excessive HCl (1 M) was added to the filtrate and adjust pH to 2, a great deal of sediments were obtained and then filtered. The crude product was recrystallized from ethanol-water solution.