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

Ourari, A.; Aggoun, D.; Bouacida, S.

doi:10.1107/S1600536812010641

Volume 68
Part 4
Page o1083
April 2012

Received 1 March 2012
Accepted 10 March 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.128
Data-to-parameter ratio = 14.7
Details

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

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

^aLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria, and ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

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-HO hydrogen bond. In the crystal, weak C-H [pi] 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, $[P \overline 1]$
a = 7.741 (2) Å
b = 9.230 (1) Å
c = 10.464 (1) Å
= 71.63 (2)°
= 75.222 (1)°
= 82.081 (1)°
V = 684.7 (2) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.128
S = 1.05
2586 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
O3-H3O2	0.98 (2)	1.578 (19)	2.498 (2)	153.4 (18)
C5-H5Cgⁱ	0.93	2.90	3.641 (2)	138
C11-H11BCgⁱⁱ	0.97	2.74	3.3973 (19)	125
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: LH5428 ).

Acknowledgements

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.

References

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organic compounds