4-(1-Methyl­eth­yl)-N-((E)-4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth­oxy}benzyl­idene)aniline

Mehmet Akkurt; Aliasghar Jarrahpour; Mehdi Mohammadi Chermahini; Pezhman Shiri; Muhammad Nawaz Tahir

doi:10.1107/S1600536813000755

. 2013 Jan 19;69(Pt 2):o247. doi: 10.1107/S1600536813000755

4-(1-Methylethyl)-N-((E)-4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzylidene)aniline

Mehmet Akkurt ^a,^*, Aliasghar Jarrahpour ^b, Mehdi Mohammadi Chermahini ^b, Pezhman Shiri ^b, Muhammad Nawaz Tahir ^c,^*

PMCID: PMC3569780 PMID: 23424526

Abstract

In the title compound, C₂₂H₂₄N₄O, the terminal and central benzene rings make dihedral angles of 52.7 (3) and 43.8 (2)°, respectively, with the triazole ring. The dihedral angle between the benzene rings is 8.9 (2)°. The crystal structure features C—H⋯π interactions. The atoms of the terminal propenyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.714 (14):0.286 (14).

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background to the properties of Schiff bases, see: Ajello & Cusmanos (1940 ▶); Dhar & Taploo (1982 ▶); Holla et al. (2005 ▶); Singh et al. (2012 ▶); Supuran et al. (1996 ▶).

Experimental

Crystal data

C₂₂H₂₄N₄O
M _r = 360.45
Monoclinic,
a = 5.5885 (11) Å
b = 8.3929 (18) Å
c = 42.069 (9) Å
β = 92.149 (10)°
V = 1971.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.982, T _max = 0.986
13866 measured reflections
3451 independent reflections
1259 reflections with I > 2σ(I)
R _int = 0.082

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.217
S = 0.96
3451 reflections
256 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

Click here for additional data file.^{(30.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000755/bq2382sup1.cif

e-69-0o247-sup1.cif^{(30.1KB, cif)}

Click here for additional data file.^{(165.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000755/bq2382Isup2.hkl

e-69-0o247-Isup2.hkl^{(165.8KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000755/bq2382Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg3 are the centroids of the N2–N4/C18/C19 1H-1,2,3-triazole and C11–C16 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3ⁱ	0.93	2.96	3.752 (5)	144
C8—H8A⋯Cg1ⁱⁱ	0.96	2.80	3.678 (6)	153

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

Compounds containing an azomethine group (–CH=N–), known as Schiff bases are formed by the condensation of a primary amine with a carbonyl compound. Schiff bases are some of the most widely used organic compounds. They are used as pigments and dyes, catalysts, intermediates in organic synthesis, and as polymer stabilisers (Dhar & Taploo, 1982). In azomethine derivatives, the C=N linkage is essential for biological activity, several azomethines were reported to possess remarkable antibacterial, antifungal, anticancer and diuretic activities (Supuran et al., 1996). Triazoles are also important class of heterocycles because of their varied biological activities (Singh et al., 2012). 1,2,3-triazoles, are five-membered, doubly unsaturated heterocycles, the ring consisting of three sequentially linked nitrogen atoms and two carbon atoms (Ajello & Cusmanos, 1940). The 1,2,3-triazole moiety has several good properties: high chemical stability (hydrolytic, oxidant, and reducing conditions), aromatic character, good hydrogen-bond-accepting ability and this moiety is relatively resistant to metabolic degradation (Holla et al., 2005). Therefore, compound (I), was synthesized and its X-ray studies is reported here.

The C1–C6 and C11–C16 benzene rings of the title compound (I), (Fig. 1), make a dihedral angle of 8.9 (2)° with each other. They form dihedral angles of 52.7 (3) and 43.8 (2) ° with the N2–N4/C18/C19 propenyl ring. The C1—N1—C10—C11, C14—O1—C17—C18 and N4—C20A—C21A—C22A torsion angles are 179.7 (4), -174.2 (3) and 151.9 (14)°, respectively. The values of the bond lengths and bond angles in (I) are normal (Allen et al., 1987).

In the crystal, the molecular packing of (I) is stabilized by C—H···π interactions (Table 1).

Experimental

Reaction of 4-((1-allyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde (1.00 mmol) with 4-isopropylbenzenamine (1.00 mmol) in refluxing ethanol gave the title compound. Recrystallization from ethanol gave colourless crystals in 70% yield. Mp: 119–121 0 C. IR (KBr, cm-1):1620 (C=N). 1H-NMR(250 MHz, CDCl3) δ (p.p.m.): 1.11 (2CH3, d, 6H, J=7.5), 2.75 (CH, m, 1H), 4.87 (d, 2H, J=5), 5.05 (s, 2H), 5.25 (d, 2H, J=10), 5.92 (m, 1H), 6.71–7.07 (aromatic protons, m, 8H), 7.50 (H triazole, s, 1H), 8.13 (HC═N, s, 1H). 13CNMR δ (p.p.m): 23.9 (2CH3), 33.6 (CH), 52.8 (CH2—N), 61.6 (CH2—O), 114.6–145.3 (aromatic carbons and C=C triazole), 158.5 (C=N).