1-[4-({4-[(E)-(2-Hy­droxy­naphthalen-1-yl)methyl­idene­amino]­phen­yl}sulfan­yl)phen­yl]ethanone

Rabihe Hebbachi; Hénia Mousser; Abdelhamid Mousser

doi:10.1107/S1600536812049835

. 2012 Dec 12;69(Pt 1):o67–o68. doi: 10.1107/S1600536812049835

1-[4-({4-[(E)-(2-Hydroxynaphthalen-1-yl)methylideneamino]phenyl}sulfanyl)phenyl]ethanone

Rabihe Hebbachi ^a, Hénia Mousser ^b,^*, Abdelhamid Mousser ^a

PMCID: PMC3588383 PMID: 23476448

Abstract

The title Schiff base compound, C₂₅H₁₉NO₂S, crystallizes in a statistically disordered structure comprising keto and enol tautomeric forms. In the enol form, the benzenoid arrangment is promoted by a strong intramolecular O—H⋯N hydrogen bond and adopts an E conformation about the imine bond. In the keto form there is an intramolecular N—H⋯O hydrogen bond. In the crystal, an extended network of C—H⋯O hydrogen bonds stabilizes columns parallel to the c axis, forming large voids (there are four cavities of 108 Å³ per unit cell) with highly disordered residual electron density. The SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155] was used to eliminate the contribution of this electron density from the intensity data, and the solvent-free model was employed for the final refinement. The contribution of this undetermined solvent was ignored in the calculation of the unit-cell characteristics.

Related literature

For related structures, see: Blagus & Kaitner (2011 ▶); Farag et al. (2010 ▶); Venkatachalam et al. (2011 ▶). For background to Schiff bases and their applications, see: Li et al. (2003 ▶); Villar et al. (2004 ▶); Kagkelari et al. (2009 ▶); Ourari et al. (2008 ▶); Zidane et al. (2011 ▶).

Experimental

Crystal data

C₂₅H₁₉NO₂S
M _r = 397.47
Monoclinic,
a = 10.695 (3) Å
b = 44.458 (14) Å
c = 4.4437 (11) Å
β = 99.004 (9)°
V = 2086.8 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 150 K
0.58 × 0.17 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.898, T _max = 0.990
8026 measured reflections
3680 independent reflections
2952 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.125
S = 0.98
3680 reflections
263 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ▶), 1291 Friedel pairs
Flack parameter: −0.06 (10)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file.^{(32.2KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049835/tk5178sup1.cif

e-69-00o67-sup1.cif^{(32.2KB, cif)}

Click here for additional data file.^{(180.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049835/tk5178Isup2.hkl

e-69-00o67-Isup2.hkl^{(180.4KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812049835/tk5178Isup3.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
O1A—H1A⋯N13A	0.84	1.80	2.558 (4)	149
N13B—H13B⋯O1B	0.88	1.85	2.558 (4)	136
C9—H9⋯O28ⁱ	0.95	2.46 (1)	3.398 (4)	168
C19A—H19A⋯O28ⁱ	0.95	2.56 (1)	3.506 (4)	174
C22—H22⋯O1A ⁱⁱ	0.95	2.44 (1)	3.337 (4)	157
C27—H27B⋯O1A ⁱ	0.98	2.49 (1)	3.442 (4)	164

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

Acknowledgments

The authors thank Dr Lahcène Ouahab and Thierry Roisnel from the Institut des Sciences Chimiques de Rennes UMR CNRS 6226 for the data collection and helpful discussions, and the Algerian Ministère de l’Enseignement Supérieur et de la Recherche Scientifique for financial support.

supplementary crystallographic information

Comment

Schiff bases are important compounds owing to their wide range of biological activities and industrial applications (Li et al., 2003; Villar et al., 2004). They have also been used as ligands in coordination chemistry (Kagkelari et al., 2009; Ourari et al. 2008; Zidane et al., 2011). Schiff bases are generally synthesized by nucleophilic condensation of an aromatic amine and a carbonyl compound, followed by the dehydration of the hemiaminal intermediate to generate the imine (Blagus et al., 2011).

In the present paper, we describe the synthesis and structural study of E-2-{[4-(4-acetylphenylsulfanyl)phenyl-amino]methyl} 2-oxo-naphthalene. The titled compound (Fig. 1) crystallizes in a disordered keto–amino tautomer [Csp²—O 1.277 (4) Å]. The C12—N13A bond length [1.334 (4) Å] is longer than C═N but in the same range of those observed in the literature for related compounds (Blagus et al., 2011; Farag et al., 2010; Venkatachalam et al., 2011) in accordance with the observed keto–amino tautomer form. The benzenoid arrangement is promoted by a strong intramolecular hydrogen bond O—H···N [N···O 2.558 (4) Å].

The Schiff base adopts a E conformation about the C12═N13 bond with a C11—C12—N13A—C14A torsion angle = -178.5 (3) Å. The central part of the molecule is planar with a dihedral angle between the benzene and naphthalene rings being less than 1 °. The molecule is twisted around the sulfide atom, so the average dihedral angle between the acetyl phenyl ring and the oxo naphthalen ring system is about 71°. The electron delocalisation between the two sulfur-bound lone pairs and π electrons of the adjacent phenyl rings leads to a slightly tighter Ssp³ angle (C17A—S1—C20 = 104.88 (15)°). The two similar sulfide carbone single bonds [C17A—S1 1.780 (3) Å and C20—S1 1.764 (3) Å] are as expected. The short bond C3—C4 distance [1.354 (5) Å] adjacent to the O1 oxygen atom of the naphthalen core indicates the presence of quinoid effect.

In the crystal, molecules are aligned head to foot along b axis, in columns parallel to [0 0 1] axis and the structure is stabilized by four kinds of C—H···O interactions (Fig. 2, Table 1). This arrangement separates the equivalent groups in columns by 4.444 (1) Å.

The large void channels in the structure (Fig. 3) contains residual electrons density with high disorder. The residual electron density were difficult to model and therefore, the SQUEEZE function of PLATON (Spek, 2009) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was employed for the final refinement. There are four cavities of 108 Å³ per unit cell. PLATON estimated that each cavity contains 12 electrons which may correspond to a solvent molecule.

Experimental

The title Schiff base was prepared by the condensation of 4-amino-4-acetyl diphenylsulfide and 2-hydroxy naphthaldehyde in a 1:1 molar ratio in ethanol solution. The mixture was stirred under reflux three hours. The crystals of title compound crystallized from a mixture of chloroforme/hexane (1/1). The orange needles were collected by filtration and dried in air. Yield: 61%. Melting Point: 451 K.