Crystal structure of (E)-1-{[(3,5-di­methyl­phen­yl)imino]­meth­yl}naphthalen-2-ol

Ahmed M Abu-Dief; Mohammed S M Abdelbaky; Santiago Garcia-Granda

doi:10.1107/S2056989015011548

. 2015 Jun 20;71(Pt 7):o496–o497. doi: 10.1107/S2056989015011548

Crystal structure of (E)-1-{[(3,5-dimethylphenyl)imino]methyl}naphthalen-2-ol

Ahmed M Abu-Dief ^a,^‡, Mohammed S M Abdelbaky ^b, Santiago Garcia-Granda ^b,^*

PMCID: PMC4518976 PMID: 26279928

Abstract

The title compound, C₁₉H₁₇NO, has an E conformation about the N=C bond. The molecule is relatively planar, with the benzene ring and naphthalene ring plane being inclined to one another by 4.28 (10)°. There is an intramolecular O—H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains propagating along [100]. Within the chains there are π–π interactions involving the benzene ring and the naphthalene ring system of an adjacent molecule [inter-centroid distance = 3.6405 (14) Å].

Keywords: crystal structure, Schiff base, naphthalen-2-ol, imino, hydrogen bonding

Related literature

For the diverse applications and biological activities of Schiff bases, see: Schiff (1864 ▸); Dutta & Das (1988 ▸); Chandra & Sangeetika (2004 ▸); Cozzi (2004 ▸). For the biological activity and optical properties of Schiff bases derived from 2-hydroxynapthaldehyde, see: Abdel-Rahman et al. (2013a ▸,b ▸, 2014 ▸); Abu-Dief et al. (2013 ▸). graphic file with name e-71-0o496-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₇NO
M _r = 275.33
Orthorhombic,
a = 6.2463 (2) Å
b = 10.2438 (3) Å
c = 23.0533 (8) Å
V = 1475.08 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.73 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▸) T _min = 0.915, T _max = 0.94
8103 measured reflections
2834 independent reflections
1422 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.121
S = 1.09
1649 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▸); program(s) used to solve structure: SIR2011 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011548/su5133sup1.cif

e-71-0o496-sup1.cif^{(71.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011548/su5133Isup2.hkl

e-71-0o496-Isup2.hkl^{(133KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015011548/su5133Isup3.cml

Click here for additional data file.^{(2.6MB, tif)}

. DOI: 10.1107/S2056989015011548/su5133fig1.tif

A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O—H⋯N hydrogen bond is shown as a dashed line (see Table 1 for details).

Click here for additional data file.^{(1.9MB, tif)}

b . DOI: 10.1107/S2056989015011548/su5133fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). H atoms not involved in these interactions have been omitted for clarity.

CCDC reference: 1406684

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.78	2.523(3)	149
C13H13O1ⁱ	0.93	2.62	3.492(3)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Spanish Ministerio de Economía y Competitividad (MAT2013-40950-R and FPI grants: BES-2011-046948 to author MSMA) and the ERDF for financial support.

supplementary crystallographic information

S1. Structural commentary

Schiff bases, known as anils, imines or azomethines, have recently received considerable attention due to their good performance in coordination chemistry, unique anti-bacterial, anti-cancer, and herbicidal applications (Schiff, 1864; Abdel-Rahman et al., 2013a,b,2014; Dutta & Das,1988). Studies showed that the presence of a lone pair of electrons in an sp² hybridized orbital of the nitrogen atom of the azomethine group is of considerable chemical and biological importance (Chandra & Sangeetika, 2004; Cozzi, 2004). In continuation of our interest in the chemical, herbicidal and biological properties of Schiff bases we synthesized the title compound as a potential anti-bacterial agent.

The title compound, has an E conformation about the N1═C11 bond, as illustrated in Fig. 1. The molecule is relatively planar with the benzene ring (C12—C17) and the naphthalene plane (C1—C10) being inclined to one another by 4.31 (10) °. There is an intramolecular O—H···N hydrogen bond generating an S(6) ring motif (Table 1 and Fig. 1).

In the crystal, molecules are linked via C—H···O hydrogen bonds (Table 1) forming chains propagating along [100], as shown in Fig. 2. Within the chains there are π-π interactions involving the naphthalene ring system and the benzene ring of an adjacent molecule [Cg1···Cg3ⁱ = 3.6405 (14) Å; Cg1 and Cg3 are the centroids of rings C1—C4/C9/C10 and C12—C17; symmetry code: (i) x - 1, y, z].

S2. Synthesis and crystallization

The title compound was prepared by treating 3,5-dimethylaniline (0.38 ml, 3 mmol) in 30 ml of dry ethanol with 2-hydroxynapthaldehyde (0.52 g, 3 mmol) with vigorous stirring at 343 K for 2 h. The reaction mixture was then left to stand at room temperature for 30 min. The yellow crystals were collected and washed several times in ethanol.

S3. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. All the H atoms were positioned geometrically and refined using a riding model: O—H = 0.82 Å, C—H = 0.93 - 9.96 Å with U_iso(H) = 1.5U_eq(O,C) for hydroxyl and methyl H atoms and 1.2U_eq(C) for other H atoms. In the final cycles of refinement, in the absence of significant anomalous scattering effects, 1185 Friedel pairs were merged and Δf ' set to zero.