1-{[4-(4-{[(2-Oxidonaphthalen-1-yl)methyl­idene]aza­nium­yl}phen­oxy)phen­yl]iminiumylmeth­yl}naphthalen-2-olate

Djahida Haffar; Djamel Daoud; Tahar Douadi; Leila Bouzidi; Salah Chafaa

doi:10.1107/S1600536813007307

. 2013 Mar 23;69(Pt 4):o581–o582. doi: 10.1107/S1600536813007307

1-{[4-(4-{[(2-Oxidonaphthalen-1-yl)methylidene]azaniumyl}phenoxy)phenyl]iminiumylmethyl}naphthalen-2-olate

Djahida Haffar ^a, Djamel Daoud ^a, Tahar Douadi ^a, Leila Bouzidi ^a, Salah Chafaa ^a,^*

PMCID: PMC3629627 PMID: 23634114

Abstract

The title Schiff base compound, C₃₄H₂₄N₂O₃, was prepared by a condensation reaction of bifunctional aromatic diamine (4,4′-diaminodiphenyl ether) with hydroxynaphtaldehyde. The asymmetric unit contains two independent molecules with similar conformations. The compound contains a central oxygen bridge and two functionalized [(E)-(phenyliminio)methyl]naphthalen-2-olate units. The dihedral angles between the benzene rings linking to the central O atom are 74.64 (19) and 69.85 (18)° in the two independent molecules. Intramolecular O—H⋯O hydrogen bonding occurs between the protonated imino N atoms and deprotonated hydroxy O atoms in both molecules. In the crystal, weak C—H⋯O hydrogen bonds are observed.

Related literature

For biological and pharmacological activities of Schiff base compounds and their derivatives, see: Khandar et al. (2005 ▶); Chen et al. (2006 ▶); Kidwai et al. (2000 ▶); de Souza et al. (2005 ▶). For their application in water treatments, see: Izatt et al. (1995 ▶); Kalcher et al. (1995 ▶); Gilmartin & Hart (1995 ▶) and as corrosion inhibitors, see: Ahamad et al. (2010 ▶); Negm et al. (2010 ▶); Zhenlan et al., (2002 ▶). For crystallographic studies of related compounds, see: Girija et al. (2004 ▶); Djamel et al. (2011 ▶); Gowda et al. (2007 ▶). For the synthesis, see: Issaadi et al. (2005 ▶); Ghames et al. (2006 ▶). graphic file with name e-69-0o581-scheme1.jpg

Experimental

Crystal data

C₃₄H₂₄N₂O₃
M _r = 508.55
Triclinic,
a = 5.292 (1) Å
b = 20.203 (1) Å
c = 23.863 (1) Å
α = 87.853 (10)°
β = 86.457 (10)°
γ = 85.26 (1)°
V = 2536.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.5 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
15547 measured reflections
9159 independent reflections
4705 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.218
S = 1.02
9159 reflections
706 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: COLLECT (Nonius, 1999) ▶; cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); 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.^{(33.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007307/xu5684sup1.cif

e-69-0o581-sup1.cif^{(33.2KB, cif)}

Click here for additional data file.^{(438.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007307/xu5684Isup2.hkl

e-69-0o581-Isup2.hkl^{(438.9KB, hkl)}

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—H1A⋯O2	0.86	1.83	2.533 (4)	138
N2—H2⋯O3	0.86	1.82	2.530 (4)	138
N3—H3⋯O5	0.86	1.84	2.543 (4)	138
N4—H4A⋯O6	0.86	1.82	2.522 (4)	138
C20—H20⋯O2ⁱ	0.93	2.46	3.236 (5)	141
C46—H46⋯O3	0.93	2.37	3.085 (5)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Lahcene Ouahab for the data collection at the Centre de Diffractométrie de l’Université de Rennes 1 CDiFX.

supplementary crystallographic information

Comment

The most common method for preparation of Schiff base ligands is reacting stoichiometric amounts of a diamine and an aldehyde in various solvents. The reaction is carried out under stirring at reflux as described in the literature. These types of schiff bases with different coordinating sites may have wide application in the field of water treatment as they have a great capacity for complexation of transition metals (Izatt et al., 1995, Kalcher et al., 1995, Gilmartin et al., 1995). They also serve as intermediates in certain enzymatic reactions and are also found in proteins that form the connective tissue (Khandar et al., 2005, Chen et al., 2006) and in the pharmaceutical field (Souza et al., 2005, Kidwai et al., 2000). Their use as corrosion inhibitors (Ahamad et al., 2010, Negm et al., 2010, Zhenlan et al., 2002) reveal their importance. Synthesized the compound,C34H24N2O3 is a condensation product of hydroxynaphtaldehyde with bifunctional aromatic diamine as shown in Fig (1). All the molecule are found in a single assymetric unit although, the oxygene atom is connecting the tow[(E)-(phenyliminio)methyl]naphthalen-2-olate units in (1) have the bond angle (C15—O1—C18) is equal to 116.3 (3)° and the dihedral angle of 75.5° between the planes defined as O(1)—C(18)—C(19)—C(20)—C(21)—C(22)—C(23) and O(1)—C(12)—C(13)—C(14)—C(15)—C(16)—C(17). In molecule (2) the bond angle (C15—O1—C18) is equal to 116.3 (3)° and the dihedral angle of 69.8° is found between the planes defined as O(4)—C(46)—C(47)—C(48)—C(49)—C(50)—C(51) and O(4)—C(52)—C(53)—C(54)—C(55)—C(56)—C(57). The bond angle between each imine phenyl plane and the attached hydroxynaphtaldehyde plane are 125.3 (3)° for C(1)—N(1)—C(12) and 126.0 (3)° for C(24)—N(2)—C(21). The bond lengths C(12)—N(1), C(1)—N(1), C(1)—C(2), C(15)—O(1).. and bond angles C(1)—N(1)—C(12), N(1)—C(1)—C(2), C(1)—C(2)—C(3), N(1)—C(12)—C(13) of one [(E)-(phenyliminio)methyl]naphthalen -2-olate moity are similar to the corresponding ones C(21)—N(2), C(24)—N(2), C(24)—C(25), C(18)—O(1) and C(24)—N(2)—C(21), N(2)—C(24)—C(25), C(24)—C(25)—C(26), N(2)—C(21)—C(22) of the second [(E)-(phenyliminio)methyl]naphthalen-2-olate. The bond distances shown in table 3 indicate that the C(1)—N(1) imine (C=N) bond length of 1.306 (4) Å agree with similar double bond usualy observed in related compounds (Girija et al., 2004, Djamel et al., 2011) but much shorter than single C—N 1.418 (4) Å of C(12)—N(1) (Gowda et al., 2007) and for the molecule (2) the bond lengths C=N C(58)—N(4) is 1.295 (4) Å and bond single C(55)—N(4) is 1.410 (4) Å.

Experimental

4,4'-Iminiomethylnaphthalen-2-olate[(E)-phenoxyphenyl] was prepared in proper literature (Issaadi et al., 2005; Ghames et al., 2006) by a condensation in ethanol (20 mL) of 2-hydroxy-1-naphthaldehyde (0.344 g, 2 mmol) with 4,4'-diaminodiphenyl ether (0.202 g, 1 mmol). The solution was stirred and refluxed for 4 h. The yellow precipitate was filtered, washed by a amount of ethanol and dried in vacuum. A single-crystal suitable for an X-ray structural analysis was obtained by slowly evaporation from dichloromethane-ethanol (1:1) solution at room temperature.