(Z)-4-(2-Hy­droxy­anilino)pent-3-en-2-one

Benghanem Fatiha; Keraghel Saida; Chahmana Safia; Ourari Ali; Brelot Lydia

doi:10.1107/S1600536812027894

. 2012 Jun 23;68(Pt 7):o2188–o2189. doi: 10.1107/S1600536812027894

(Z)-4-(2-Hydroxyanilino)pent-3-en-2-one

Benghanem Fatiha ^a, Keraghel Saida ^a,^*, Chahmana Safia ^a, Ourari Ali ^a, Brelot Lydia ^b

PMCID: PMC3393989 PMID: 22798854

Abstract

In the title compound, C₁₁H₁₃NO₂, the dihedral angle between the planes defined by the 2-hydroxyphenylamino group and the pent-3-en-2-one mean plane [maximum deviations = 0.0275 (19) and 0.054 (2) Å, respectively] is 31.01 (10)°. There are intramolecular bifurcated N—H⋯(O,O) hydrogen bonds involving the amine NH group and the adjacent carbonyl and hydroxy O atoms. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For transition metal complexes of Schiff bases, see: Salavati-Niasari (2006 ▶); Xiong et al. (2007 ▶); Basu et al. (2010 ▶). For the biological activity of Schiff bases, see: Jarrahpour et al. (2007 ▶); El-Masry et al. (2000 ▶); Singh & Dash (1988 ▶). For the use of Schiff bases as intermidiates in many industrial processes, see: Salavati-Niasari & Nezamoddin Mirsattari (2007 ▶); Katsuki (1995 ▶); Ahamad et al. (2010 ▶); Da Silva et al. (2010 ▶); Soltani et al. (2010 ▶). For the tautomeric properties and conformations of the title compound, see: Kabak et al. (1998 ▶). For the photoconductivity of the title compound, see: Parekh et al. (2007 ▶), and for its thermochromic properties, see: Moustakali-Mavridis et al. (1978 ▶); Hadjoudis et al. (1987 ▶). For hydrogen bonding and graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₃NO₂
M _r = 191.22
Orthorhombic,
a = 8.7826 (4) Å
b = 10.3999 (5) Å
c = 11.1827 (3) Å
V = 1021.41 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.50 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
7005 measured reflections
1359 independent reflections
1260 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.126
S = 1.07
1359 reflections
137 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027894/su2455sup1.cif

e-68-o2188-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027894/su2455Isup2.hkl

e-68-o2188-Isup2.hkl^{(65.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027894/su2455Isup3.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
N1—H1N⋯O1	0.96 (3)	2.28 (3)	2.633 (2)	100.9 (18)
N1—H1N⋯O2	0.96 (3)	1.85 (3)	2.641 (2)	139 (2)
O1—H1⋯O2ⁱ	0.93 (3)	1.72 (3)	2.637 (2)	172 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank Professor J. P. Gisselbrecht, Laboratoire d’Electrochimie et de Chimie Physique du Corps Solide, Strasbourg University, France, for his valuable contributions.

supplementary crystallographic information

Comment

Schiff bases have played an important role in the development of coordination chemistry. They have a great capacity for complexation of transition metal (Salavati-Niasari, 2006; Xiong et al., 2007; Basu et al., 2010). A literature survey revealed that this kind of compound possesses diverse biological activities such as antimicrobial (Jarrahpour et al., 2007; El-Masry et al., 2000) and antifungal (Singh & Dash, 1988). They also serve as intermediates in many industrial processes (Salavati-Niasari & Nezamoddin Mirsattari, 2007; Katsuki, 1995) and are used as corrosion inhibitors (Ahamad et al., 2010; Da Silva et al., 2010; Soltani et al., 2010). In order to expand this field of research the title compound, a novel Schiff base derived from a non-aromatic aldehyde, has been synthesized and its crystal structure is reported herein.

The tautomeric properties and conformations of the title compound were investigated by (Kabak et al., 1998). The enol tautomer form of the crystal of the title compound is established by the present crystal structure analysis. The positive photoconductivity of this compound has been studied by (Parekh et al., 2007). The crystal exhibits positive photoconductivity and poor NLO responses, and it is photochromic not thermochromic in the solid state (Moustakali-Mavridis et al., 1978; Hadjoudis et al., 1987).

The molecular structure of the title molecule is shown in Fig. 1. It was prepared by the condensation of acetylacetone and 2-aminophenol and crystallized in the chiral space group P2₁2₁2₁.

The molecule is not planar and the dihedral angle between the two planes defined by O1,C1-C6,N1 and O2,C7-C11 is equal to 31.01 (10) °. The small value of bond N1—C7 (1.346 (2) A°) in comparison to bond N1—C6 (1.416 (3) A°) results in a significant change in the bond angle C7—N1—C6 of 130.76 (17)°. The difference in the C—N bond distances is assumed to be due to the presence of the carbonyl group located at the C10 position. Shortening of the C7—N1 bond length and the large value of the C7—N1—C6 bond angle leads to the existence of an N1—H1···O2 intramolecular hydrogen bond (Table 1) with an S(6) ring motif (Bernstein et al., 1995). The second intramolecular N1-H1···O1 hydrogen bond gives an S(5) ring motif.

In the crystal, molecules are linked via O-H···O hydrogen bonds to form chains propagating along [100] - see Table 1 and Fig. 2.

Experimental

To a ethanol solution (5 ml) of (0.109 g, 1 mmol) of 2-aminophenol was slowly added a ethanol solution (5 ml) of acetylacetone (0.1 g, 1 mmol). The mixture was refluxed with constant stirring under a nitrogen atmosphere for 5 h. The mixture was removed and allowed to cool to rt and the solvent to evaporate slowly. After 20 days yellow crystals of the title compound were obtained. They were washed with ethanol then with diethyl ether.