4,4′-Oxybis{N-[(E)-quinolin-2-yl­methyl­idene]aniline}

Daoud Djamel; Douadi Tahar; Haffar Djahida; Hammani Hanane; Chafaa Salah

doi:10.1107/S1600536811012955

. 2011 Apr 13;67(Pt 5):o1119–o1120. doi: 10.1107/S1600536811012955

4,4′-Oxybis{N-[(E)-quinolin-2-ylmethylidene]aniline}

Daoud Djamel ^a,^*, Douadi Tahar ^a, Haffar Djahida ^a, Hammani Hanane ^a, Chafaa Salah ^a

PMCID: PMC3089181 PMID: 21754434

Abstract

The title Schiff base compound, C₃₂H₂₂N₄O, was prepared by a reaction of 4,4′-diaminodiphenyl ether and 2-quinolinecarboxaldehyde. The molecule consists of two 4-{N-[(E)-quinolin-2-ylmethylidene]amino}phenyl units linked by an oxygen bridge. The dihedral angles between two benzene rings and between the two quinoline ring systems are 53.81 (7) and 42.56 (4)°, respectively. Intermolecular C—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For the biological and pharmacological activity of quinolines and their derivatives, see: Kidwai et al. (2000 ▶); Souza (2005 ▶); Musiol et al. (2006 ▶); Gómez-Barrio et al. (2006 ▶); Vinsova et al. (2008 ▶); Jain et al. (2005 ▶); Chen et al. (2006 ▶). For applications of Schiff base compounds formed by aromatic diamine and a quinolinealdehyde, see: Izatt et al. (1995 ▶); Kalcher et al. (1995 ▶); Gilmartin & Hart (1995 ▶); Ahamad et al. (2010 ▶); Negm et al. (2010 ▶). For related structures, see: Girija et al. (2004 ▶); Gowda et al. (2007 ▶). For the synthesis, see: Issaadi et al. (2005 ▶); Ghames et al. (2006 ▶); Kaabi et al. (2007 ▶).

Experimental

Crystal data

C₃₂H₂₂N₄O
M _r = 478.54
Monoclinic,
a = 17.4533 (7) Å
b = 5.0836 (2) Å
c = 26.817 (1) Å
β = 92.839 (1)°
V = 2376.43 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.05 × 0.05 mm

Data collection

Bruker APEXII diffractometer
20425 measured reflections
5473 independent reflections
4143 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.150
S = 1.1
5473 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012955/xu5181sup1.cif

e-67-o1119-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012955/xu5181Isup2.hkl

e-67-o1119-Isup2.hkl^{(262.6KB, 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
C28—H28⋯N3ⁱ	0.93	2.57	3.434 (2)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Quinolines and their derivatives are often used for designing of many synthetic compounds with diverse pharmacological and medicinal proprieties. Literature survey reveled that substituted quinolines possess diverse chemotherapeutic activities such as antibacterial (Kidwai et al., 2000), antimalarial (Souza et al., 2005), antifungal (Musiol et al., 2006), antiparasitical (Gómez-Barrio et al., 2006), antimycobacterial (Vinsova et al., 2008), antileishmanial (Jain et al., 2005), and anti-inflammatory behavior (Chen et al., 2006). Schiff base compounds are typically formed by condensation of an aromatic diamine and a quinolinealdehyde. These kinds of compounds have a wide variety of applications in many fields. For example in water treatment, 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 their use as corrosion inhibitors, (Ahamad et al., 2010; Negm et al., 2010) reveal their importance.

The compound, C₃₂H₂₂N₄O prepared is a condensation product of quinolinealdehyde with bifunctional aromatic diamine as shown in Fig (1). All the molecule is found in a single asymmetric unit although, the two 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl moieties are related by a pseudo mirror plane. A dihedral angle of 53.15° is found between the planes defined as (O(1)—C(17)—C(18)—C(19)—C(20)—C(21)—C(22) and O(1)—C(11)—C(12)—C(13)—C(14)—C(15)—C(16). Whereas the dihedral angle between each imine phenyl plane and the attached quinolinecarboxy plane are 8.33° for C(10)—N(2)—C(11) and 17.74° for C(25)—N(1)—C(20). The bond lengths N(2)—C(10), N(2)—C(11), O(1)—C(14).. and bond angles C(10)—N(2)—C(11), C(16)—C(11)—N(2), C(9)—N(3)—C(1), N(3)—C(1)—C(2) of one 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl moiety are similar the corresponding ones N(1)—C(25), N(1)—C20), O(1)—C(17).. and C(25)—N(1)—C(20), C(19)—C(20)—N(1), C(26)—N(4)—C(30, N(4)—C(30)—C(31)..of the second 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl. The bond distances shown in table 3 indicate that the N(1)—C(25) imine (C=N) bond length of 1.268 (17) A agree with similar double bond usually observed in related compounds (Girija et al., 2004) but much shorter than single C—N 1.4175 (16) A of N(1)—C(20) (Gowda et al., 2007).

Experimental

The studied Schiff base compound was synthesized in proper literature (Issaadi et al., 2005; Ghames et al., 2006; Kaabi et al., 2007). by reacting the mixture of 4,4'-diaminodiphenyl ether (0.4 mg, 0.002 mol) and 2-quinolinecarboxaldehyde (0.64 mg, 0.004 mol) in 20 ml of boiling ethanol for 5 h, after completion of the reaction the separated solid was filtered, washed with alcohol, and finally recrystallized from ethanol and dried under vacuum. The single crystals suitable for X-ray analysis were obtained by slow evaporation from ethanol-dichloromethane (1:1).