(E)-N-[3-(Imidazol-1-yl)-1-phenyl­propyl­idene]hydroxyl­amine

Hoong-Kun Fun; Ching Kheng Quah; Mohamed I Attia; Maha S Almutairi; Soraya W Ghoneim

doi:10.1107/S1600536812004266

. 2012 Feb 10;68(Pt 3):o627. doi: 10.1107/S1600536812004266

(E)-N-[3-(Imidazol-1-yl)-1-phenylpropylidene]hydroxylamine

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Mohamed I Attia ^b,^¶, Maha S Almutairi ^b, Soraya W Ghoneim ^b

PMCID: PMC3295422 PMID: 22412533

Abstract

The title compound, C₁₂H₁₃N₃O, exists in an E configuration with respect to the C=N bond [1.285 (2) Å]. The imidazole ring forms a dihedral angle of 75.97 (10)° with the phenyl ring. In the crystal, molecules are linked via O—H⋯N and C—H⋯N hydrogen bonds into sheets lying parallel to (001). The crystal structure also features C—H⋯π interactions.

Related literature

For general background to and the pharmacological activities of the title compound, see: Weinberg (1996 ▶); Wildfeuer et al. (1998 ▶); Georgopapadakou (1998 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₂H₁₃N₃O
M _r = 215.25
Monoclinic,
a = 8.0990 (1) Å
b = 14.0513 (2) Å
c = 9.9771 (2) Å
β = 93.058 (1)°
V = 1133.79 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.35 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.972, T _max = 0.991
12642 measured reflections
3300 independent reflections
2653 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.138
S = 1.13
3300 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004266/hb6619sup1.cif

e-68-0o627-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004266/hb6619Isup2.hkl

e-68-0o627-Isup2.hkl^{(161.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812004266/hb6619Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N3ⁱ	0.90 (3)	1.82 (3)	2.712 (2)	176 (3)
C2—H2A⋯N1ⁱⁱ	0.95	2.56	3.477 (2)	162
C12—H12A⋯Cg1ⁱⁱⁱ	0.95	2.74	3.558 (2)	145

Open in a new tab

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

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for a Research University Grant (grant No. 1001/PFIZIK/811160). This research project was supported by a grant from the research center of the center of female scientific and medical colleges in King Saud University.

supplementary crystallographic information

Comment

A significant increase in fungal infections has been observed over the past three decades. Many reports of invasive topical and systemic infections caused by the opportunistic pathogen Candida species are always associated with the use of broad-spectrum antibiotics, immunosuppressive agents, anticancer and anti-AIDS drugs (Weinberg, 1996). One of the major problems in the treatment of Candida infections is the spread of antifungal drug resistance mainly in patients chronically subjected to antimycotic therapy such as HIV-infected patients (Wildfeuer et al., 1998; Georgopapadakou, 1998). Azoles are commonly used as antifungal agent specially for Candida infections as many marketed drugs contain the azole moiety. The title compound contains the azole moiety and it was prepared to test its antifungal potential and will be further elaborated to other azole-containing new bioactive chemical entities.

In the title compound, Fig.1, the imidazole ring (N2/N3/C10-C12, maximum deviation of 0.001 (2) Å at atoms N3, C11 and C12) forms a dihedral angle of 75.97 (10)° with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound exists in trans configuration with respect to the C7═N1 bond [1.285 (2) Å].

In the crystal structure, Fig. 2, molecules are linked via intermolecular O1–H1O1···N3 and C2–H2A···N1 hydrogen bonds (Table 1) into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C12–H12A···Cg1ⁱⁱⁱ (Table 1) interactions, where Cg1 is the centroid of C1-C6 phenyl ring.

Experimental

A mixture of 3-(1H-imidazol-1-yl)-1-phenylpropan-1-one (0.02 g, 0.1 mmol), hydroxylamine hydrochloride (0.14 g, 0.2 mol), and KOH (0.112 g, 0.2 mmol) in ethanol (10 ml) was refluxed under stirring for 18h. The reaction mixture was allowed to cool to room temperature and the insolubles were removed by filtration. The filtrate was evaporated under vacuum and the residue was suspended in water (10 ml), filtered, dried and recrystallized from ethanol to yield colourless blocks of the title compound.