Crystal structure of 1,1′-{(dodecane-1,12-di­yl)bis­[(aza­niumylyl­idene)methanylyl­idene]}bis­(naphthalen-2-olate)

Kamel Ouari; Moufida Merzougui; Sabrina Bendia; Corinne Bailly

doi:10.1107/S2056989015007938

. 2015 Apr 25;71(Pt 5):o351–o352. doi: 10.1107/S2056989015007938

Crystal structure of 1,1′-{(dodecane-1,12-diyl)bis[(azaniumylylidene)methanylylidene]}bis(naphthalen-2-olate)

Kamel Ouari ^a,^*, Moufida Merzougui ^a, Sabrina Bendia ^a, Corinne Bailly ^b

PMCID: PMC4420129 PMID: 25995943

Abstract

The title compound, C₃₄H₄₀N₂O₂, exists in an extended conformation and has crystallographically imposed centrosymmetry. The crystal packing can be described as being composed of parallel layers stacked along [010]. The zwitterionic structure is stabilized by an intramolecular N—H⋯O hydrogen-bond interaction.

Keywords: crystal structure; 1,12-diaminododecane; 2-hydroxy-1-naphthaldehyde; hydrogen bonds

Related literature

The compound is synthesized using two procedures, the ultrasound and the conventional methods. We found that the ultrasound irradiation method is more convenient and efficient. For conventional synthesis of similar compounds, see: Ouari et al. (2015a ▸); Mohammadi & Rastegari (2012 ▸); Bhowmik et al. (2011 ▸). For ultrasonic synthesis of similar compounds, see: Rayati & Abdolalian (2013 ▸); Khan et al. (2014 ▸); Kanagarajan et al. (2011 ▸). For related crystal structures, see: Ouari et al. (2010 ▸, 2015b ▸); Popović et al. (2001 ▸); Friscic et al. (1998 ▸); Bi et al. (2012 ▸); Temel et al. (2010 ▸). For their applications, see: Köse et al. (2015 ▸); Grivani et al. (2013 ▸); Amin et al. (2010 ▸); Panneerselvam et al. (2009 ▸); Nasr et al. (2009 ▸); Nejo et al. (2009 ▸); Taha et al. (2012 ▸).

Experimental

Crystal data

C₃₄H₄₀N₂O₂
M _r = 508.68
Monoclinic,
a = 54.400 (5) Å
b = 4.7465 (4) Å
c = 10.7022 (9) Å
β = 96.318 (2)°
V = 2746.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.50 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T _min = 0.682, T _max = 0.746
17506 measured reflections
3271 independent reflections
2313 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.125
S = 1.04
3271 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015007938/mw2131sup1.cif

e-71-0o351-sup1.cif^{(551KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007938/mw2131Isup2.hkl

e-71-0o351-Isup2.hkl^{(179.7KB, hkl)}

Click here for additional data file.^{(916KB, tif)}

. DOI: 10.1107/S2056989015007938/mw2131fig1.tif

The title compound with atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.

Click here for additional data file.^{(1.4MB, tif)}

c . DOI: 10.1107/S2056989015007938/mw2131fig2.tif

Crystal packing of the title compound viewed along the c axis.

CCDC reference: 1032833

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1NO1	0.94(2)	1.75(2)	2.5498(18)	140.6(19)

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Acknowledgments

The authors gratefully acknowledge the financial support from The Algerian Ministry of Higher Education and Scientific Research. They also acknowledge the help of Dr Jean WEISS from CLAC laboratory at the University of Strasbourg, France.

supplementary crystallographic information

S0.1. Synthesis and crystallization

Ultrasonication method

A reaction flask containing 0.344g (2mmol) of 2-hydroxy-1-naphthaldehyde and 0.508g (1mmol) of 1,12-diaminododecane, mixed and ground to a fine powder in a mortar, was immersed in an ultrasonic bath containing water at a temperature of 50 °C. The reaction mixture was exposed to ultrasound irradiation for 40 min. Upon completion, based on TLC analysis (silica gel, CH₂Cl₂/MeOH, 9.5/0.5, V/V) the product was washed with methanol (3 x 3 mL) and diethyl ether (3 x 3 mL) and filtered. Single crystals, suitable for X-ray diffraction, were obtained after 2 days of crystallization from DMSO/MeOH.

Color: Yellow, Yield: 88 %, mp: 148°C. Analysis calculated for C₃₄H₄₀N₂O₂: C, 80.27; H, 7.92; N, 5.50%; found: C, 80.06; H, 7.80; N, 5.78%.

Conventional method

To a solution of 0.172 g (1mmol) of 2-hydroxy-1-naphthaldehyde in 5 mL of methanol was added 0.254 g (0.5 mmol) of 1,2-diaminododecane dissolved in 5 mL of the same solvent.The mixture was stirred and refluxed for 3 hours under a nitrogen atmosphere. At completion, based on TLC analysis, the resulting compound was filtered and washed with methanol and diethyl ether to afford pure product in 62% yield.

S0.2. Refinement

The iminium H atom was located from a difference Fourier map and refined isotropically. C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 Å (CH) or 0.99 Å (CH₂) with Uiso(H) = 1.2Ueq (C—Har.).

S1. Results and discussion

Schiff base ligands can be easily synthesized using conventional or ultrasonic irradiation methods by reacting primary amines and carbonyl compounds in which the azomethine bond is formed and they can used to form complexes (Ouari et al., 2015a., Mohammadi et al., 2012; Bhowmik et al., 2011., Grivani et al., 2013; Nejo et al., 2009., Rayati et al., 2013., Khan et al., 2014., Kanagarajan et al., 2011).

The synthesis via ultrasound irradiation is an efficient, fast, high yielding method and is a more economical synthetic process for the preparation of the Schiff base compound than the conventional method.

The azomethine group >C=N of the Schiff base can form stable metal complexes by coordinating through the nitrogen atom (Ouari et al., 2015b., Ouari et al., 2010 ). Schiff base ligands have many applications including anti-microbial agents (Köse et al., 2015., Taha et al.;2012., Panneerselvam et al., 2009), anti-tumor agents, (Nasr et al., 2009) and as xanthine oxidase inhibitors (Amin et al., 2010).

This compound crystallized in the monoclinic space group C2/c, whereas the related compounds(C₂₆H₂₄N₂O₂, C₂₈H₂₈N₂O₂) (Friscic et al., 1998), (C₂₈H₂₆N₂O₂) (Bi et al., 2012) and (C₂₈H₂₀N₂O₂—CHCL₃) (Popović et al., 2001) crystallized in the orthorhombic space groups Pbca, Pbcn, P2₁2₁2₁, and P2₁2₁2₁, respectively. The hydrogen atom in the title compound is located on the nitrogen atom (Fig.1). The C1—O1 bond length of 1.2802 (19)Å indicates double-bond character while the N1—C11 bond length of 1.2994 (19)Å indicates single-bond character thus confirming the zwitterionic formulation. Similar results have been reported (Temel et al., 2010]. The crystal packing can be described as parallel chains along the c axis (Fig. 2). It is stabilized by intramolecular N—H···O hydrogen bonding (Table 1) and by weak intermolecular C—H···π ring interactions. These interactions link the molecules within the layers and also link the layers together thereby reinforcing the cohesion of the ionic structure.