1-{2-Hy­droxy-6-[3-(pyrrol-1-yl)prop­oxy]phen­yl}ethanone

Ali Ourari; Djouhra Aggoun; Sofiane Bouacida

doi:10.1107/S1600536812010641

. 2012 Mar 17;68(Pt 4):o1083. doi: 10.1107/S1600536812010641

1-{2-Hydroxy-6-[3-(pyrrol-1-yl)propoxy]phenyl}ethanone

Ali Ourari ^a, Djouhra Aggoun ^a, Sofiane Bouacida ^b,^*

PMCID: PMC3344038 PMID: 22589947

Abstract

In the title compound, C₁₅H₁₇NO₃, the mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. The molecule contains an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯π interactions link the molecules into chains along [010].

Related literature

For the synthesis and applications of similar compounds and their derivatives, see: Wu & Lu (2003 ▶); Saraswat et al. (2006 ▶); Smith et al. (2003 ▶); Dong et al. (2010 ▶); Deronzier & Moutet (1996 ▶); MacDearmid (2001 ▶); Srinivasan et al. (1986 ▶); Coche-Guerente et al. (1995 ▶); Ourari et al. (2008 ▶); Khedkar & Radhakrishnan (1997 ▶); Huo et al. (1999 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₃
M _r = 259.3
Triclinic,
a = 7.741 (2) Å
b = 9.230 (1) Å
c = 10.464 (1) Å
α = 71.63 (2)°
β = 75.222 (1)°
γ = 82.081 (1)°
V = 684.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.15 × 0.08 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
4238 measured reflections
2586 independent reflections
1995 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.128
S = 1.05
2586 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010641/lh5428sup1.cif

e-68-o1083-sup1.cif^{(22KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010641/lh5428Isup2.hkl

e-68-o1083-Isup2.hkl^{(124.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010641/lh5428Isup3.cml

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

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

Cg is is the centroid of the N1/C12–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.98 (2)	1.578 (19)	2.498 (2)	153.4 (18)
C5—H5⋯Cgⁱ	0.93	2.90	3.641 (2)	138
C11—H11B⋯Cgⁱⁱ	0.97	2.74	3.3973 (19)	125

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

Acknowledgments

The authors thank the Algerian Ministère de l’Enseignement Supérieur et de la Recherche Scientifique for financial support and Professor L. Ouahab (Laboratoire des Sciences Chimiques, Rennes1 France) for helpful discussions.

supplementary crystallographic information

Comment

The synthesis of new derivatives containing both a pyrrole ring and salicyaldehyde moiety is of a great interest since they are currently used as precursors for chelating agents especially those of Schiff bases (Wu et al., 2003; Saraswat et al., 2006) and oximes (Smith et al., 2003; Dong et al., 2010). These compounds may also be involved in the elaboration of modified electrodes by anodic (Deronzier & Moutet, 1996) or by chemical oxidation (MacDearmid et al., 2001). These types of materials can be applied in catalysis, electrocatalysis and sensors (Srinivasan et al., 1986; Coche-Guerente et al., 1995; Ourari et al., 2008). The synthesis of new salicylaldehyde derivatives containing electropolymerizable units can be considered as the main source of a functionalized conducting π-conjugated polymers such as as those of polypyrrole and polyaniline (Khedkar et al., 1997; Huo et al., 1999).

We report herein the crystal structure of the title compound. The molecular structure is shown in Fig. 1. The mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. There is an intramolecular O—H···O hydrogen bond present. In the crystal, there are weak C—H···π interactions (Table 1) which form chains of dimers along [010] (Fig. 2).

Experimental

A solution of 152 mg (1 mmol) of 2,6-dihydroxyacetophenone was added to a solution containing 187 mg (1 mmol) of 1-bromopropyl-3-N-pyrrol and 181 mg (1.7 mmol) of potassium carbonate under argon atmosphere. The mixture was refluxed for 45 h and was allowed to stand at room temperature. After extraction by dichloromethane and purification by chromatography on silica gel using dichloromethane as eluent. Thus, 153 mg of pure compound (I) was recovered, corresponding to the yield of 59%. The suitable single crystals were then obtained from dichloromethane solution by slow evaporation.