1-[4-(1H-imidazol-1-yl)phen­yl]ethanone monohydrate

Halliru Ibrahim; Muhammad D Bala; Bernard Omondi

doi:10.1107/S1600536812029157

. 2012 Jun 30;68(Pt 7):o2305. doi: 10.1107/S1600536812029157

1-[4-(1H-imidazol-1-yl)phenyl]ethanone monohydrate

Halliru Ibrahim ^a, Muhammad D Bala ^a,^*, Bernard Omondi ^a

PMCID: PMC3394079 PMID: 22798944

Abstract

In the crystal structure of the title compound, C₁₁H₁₀N₂O·H₂O, the solvent water molecule links the organic molecules through O—H⋯O and O—H⋯N hydrogen bonds, forming chains that run diagonally across the bc face. These chains are connected to adjacent chains through weak C—H⋯O interactions, resulting in hydrogen-bonded sheets extending along the b and c axes. The sheets are connected along the a axis through π–π interactions, with centroid–centroid distances of 3.7571 (9) and 3.7231 (9) Å.

Related literature

For the synthesis of the title compound, see: Corberán & Peris (2008 ▶). For the structure of imidazole analogues with bonds to the phenyl group via carbon, see: Gayathri et al. (2010 ▶). For the structure of imidazole analogues N-bonded to a phenyl group, see: Zheng et al. (2011 ▶). For structures of other related compounds, see: Ishihara et al. (1992 ▶).

Experimental

Crystal data

C₁₁H₁₀N₂O·H₂O
M _r = 204.23
Triclinic,
a = 6.7599 (6) Å
b = 8.0885 (8) Å
c = 9.7168 (9) Å
α = 90.350 (3)°
β = 106.731 (3)°
γ = 99.486 (3)°
V = 501.03 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.58 × 0.39 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.947, T _max = 0.987
6609 measured reflections
1711 independent reflections
1568 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 1.07
1711 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029157/fj2569sup1.cif

e-68-o2305-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029157/fj2569Isup2.hkl

e-68-o2305-Isup2.hkl^{(82.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029157/fj2569Isup3.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
O1S—H1D⋯O1ⁱ	0.87 (2)	2.00 (2)	2.8610 (14)	174.6 (19)
O1S—H1E⋯N2	0.91 (2)	1.92 (2)	2.8246 (15)	172.1 (16)
C5—H5⋯O1S ⁱⁱ	0.93	2.39	3.3034 (16)	166
C9—H9⋯O1S ⁱⁱ	0.948 (15)	2.345 (15)	3.2677 (16)	164.5 (12)

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

Acknowledgments

We thank the NRF and the University of KwaZulu-Natal for financial support.

supplementary crystallographic information

Comment

The title compound is an intermediate product in the synthetic route to an N-heterocyclic carbene (NHC) chelating ligand bearing a pyridine backbone. The anhydrous form of the compound is available in chemical book database with CAS No. 10041–06-2. Neither structure of the hydrated nor the anhydrous forms of the title compound have been reported. Our synthetic route and the synthons used are different from those reported in the synthesis of the anhydrous form of the title compound. Absolute configuration of the title compound obtained in pure form from column chromatography using hexane:chloroform (6:4) solvent system was assigned by NMR and IR spectroscopy. Monohydrate block crystals of (I) were recrystallized from the same solvent system. The imidazole N(2) – phenyl carbon bond [C(9)—N(2)] is 1.3107 (16) Å. The one molecule of water binds as water of crystallization to the organic molecule, and is a constituent of the asymmetric unit cell. Molecules of (I) are stabilized through an extensive chain of hydrogen bonded network involving neighbouring methoxy (O—H···O) and imidazolium (N—H···O) moieties linked by the water of crystallization. Imidazole analogues of (I) with bonds to the phenyl group via carbon have been reported by Gayathri et al. (2010); while Zheng et al. (2011) have reported imidazole bonded to a phenyl group via nitrogen. Other related compounds have been reported by Ishihara et al. (1992).

Experimental

The compound was synthesized by the modification of the method of Corberán et al. (2008). A 150 ml round bottom flask containing imidazole (0.01 mol, 0.68 g, Fluka AG) with KOH (0.015 mol, 0.84 g, Merck) was stirred at room temperature in DMSO (30 ml, Merck) for 2 h. Thereafter, para-choloroacetophenone (0.01 mol, 1.34 ml, Aldrich) was added dropwise, and then refluxed at 100 °C for 24 h. The reaction mixture was then allowed to cool down to room temperature, washed and diluted with chilled distilled water till it became neutral. Addition of distilled water to the contents of the reaction flask gave a muddy emulsion which took 24 h to partition when extracted with chloroform (6x10 ml). The resulting organic components were dried in anhydrous MgSO₄ and concentrated in vacuo yielding crude dark brown oily liquid (1.694 g). Thin layer chromatography of the crude product showed that it contained the expected product (R_f value 0.45 in ethyl acetate:methanol 4:6 solvent system) contaminated with unreacted imidazole and para-chloroacetophenone. Column chromatography of the crude product using hexane:chlorofom solvent system afforded the title compound as block-shaped light green crystals (0.987 g, 48.4% yield), m.p. = 119–122 °C. ¹H NMR (400 MHz, CDCl₃): 8.09(d), 7.95(s), 7.51(d), 7.35(s), 7.25(s), and 1.62(s). ¹³C NMR (400 MHz, CDCl₃): 196.5 (carbonyl CO), 140.8, 135.8, 135.4, 131.2, 130.4, 120.7, 117.7, 26.61(CH₃). IR (ATR, cm^-1): 1665(C=O), 1606(C=N), 1530(N—C), 956(C=C), 2222(C—H), 814(para substituted benzene), 3202 (water of crystallization absorbance band).