(E)-1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-phenyl­prop-2-en-1-one

Hoong-Kun Fun; Madhukar Hemamalini; Poovan Shanmugavelan; Alagusundaram Ponnuswamy; Rathinavel Jagatheesan

doi:10.1107/S1600536811037871

. 2011 Sep 30;67(Pt 10):o2707. doi: 10.1107/S1600536811037871

(E)-1-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-phenylprop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Poovan Shanmugavelan ^b, Alagusundaram Ponnuswamy ^b, Rathinavel Jagatheesan ^c

PMCID: PMC3201398 PMID: 22065569

Abstract

The asymmetric unit of the title compound, C₁₉H₁₇N₃O, contains two independent molecules. In one molecule, the essentially planar triazole ring [maximum deviation = 0.003 (2) Å] forms dihedral angles of 5.57 (12) and 87.51 (12)° with the two phenyl rings, while in the other molecule [maximum deviation in triazole ring = 0.001 (2) Å] these angles are 1.55 (10) and 82.73 (11)°. The dihedral angles between the two phenyl rings in the two molecules are 87.77 (13) and 81.22 (11)°. In the crystal, the independent molecules are connected via a weak C—H⋯N hydrogen bond, forming dimers. Further stabilization is provided by weak C—H⋯π interactions.

Related literature

For applications of 1,2,3-triazole compounds, see: Banerjee et al. (1996) ▶; Laliberte et al. (1967 ▶); Suwa et al. (1984 ▶). For applications of chalcones, see: Ballesteros et al. (1995 ▶); Kothari et al. (1999 ▶); Nagaraj & Reddy (2007 ▶).

Experimental

Crystal data

C₁₉H₁₇N₃O
M _r = 303.36
Monoclinic,
a = 12.3117 (14) Å
b = 13.8016 (15) Å
c = 19.312 (2) Å
β = 99.665 (2)°
V = 3235.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.46 × 0.33 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.965, T _max = 0.991
32508 measured reflections
9403 independent reflections
4890 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.219
S = 1.03
9403 reflections
417 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037871/lh5335sup1.cif

e-67-o2707-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037871/lh5335Isup2.hkl

e-67-o2707-Isup2.hkl^{(450.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037871/lh5335Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C14A–C19A and C14B–C19B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13A—H13A⋯N1Bⁱ	0.97	2.50	3.453 (3)	166
C1B—H1BA⋯Cg1ⁱⁱ	0.93	2.97	3.893 (3)	174
C13B—H13C⋯Cg2ⁱⁱⁱ	0.97	2.61	3.528 (2)	159

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Organic compounds, having the 1,2,3-triazole nucleus, may induce antiviral, agonist, antibacterial, antimicrobial, anti-HIV, anticonvulsants and anti-allergic properties. In addition, compounds having 1,2,3-triazole group have found industrial application as dyes, corrosion inhibitors, sensors and photo-stabilizers (Banerjee et al., 1996; Laliberte et al., 1967; Suwa et al., 1984). The chalcone skeleton is a unique template for synthesizing various heterocyclic compounds. The compounds with the backbone of chalcones were associated with different biological activities like cardiovascular, antispasmodic, anthelmintics, antiulcer, anti-inflammatory, antiviral, antiallergic, fungicidal, bactericidal, insecticidal, antitumor, herbicidal, anticancer, antitubercular and anti-HIV (Ballesteros et al., 1995; Kothari et al., 1999; Nagaraj & Reddy, 2007) properties. Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants, and have also been shown to display a diverse array of pharmacological activities. The presence of a reactive α, β-unsaturated keto function in chalcones is found to be responsible for their activities.

The asymmetric unit of the title compound, (I), contains two crystallographically independent (E)-1-(1-benzyl-5-methyl-1H- 1,2,3-triazol-4-yl)-3-phenylprop-2-en-1-one molecules (A & B) as shown in Fig. 1. The triazole (N1A–N3A/C10A/C11A):(N1B–N3B/C10B/C11B) units are essentially planar, with maximum deviations of 0.003 (2) Å for atom C10A and 0.001 (2) Å for atom C11B. In molecule A the essentially planar triazole ring forms dihedral angles of 5.57 (12) and 87.51 (12)° with the two phenyl rings while in molecule B these angles are 1.55 (10) and 82.73 (11)°. The dihedral angles between the two phenyl(C1A–C6A/C14A–C19A): (C1B–C6B/C14B–C19B) rings in the independent molecules are 87.77 (13)° and 81.22 (11)° respectively.

In the crystal, (Fig. 2), two independent molecules are connected via intermolecular C—H···N hydrogen bonds (Table 1), forming dimers. Furthermore, the crystal structure is stabilized by weak C—H···π interactions involving the Cg1 (C14A–C19A) and Cg1 (C14B–C19B) rings.

Experimental

A mixture of 4-acetyl-1-benzyl-5-methyl-1,2,3-triazole (0.20g, 0.93mmol) and benzaldehyde (0.98 g, 0.93 mmol) was stirred in ethanol (2–3 ml) and then 50% sodium hydroxide solution (0.5 ml) was added to it. The mixture was stirred for 3 minutes at room temperature and poured onto excess of crushed ice and neutralized with dilute hydrochloric acid. 1-Benzyl-5-methyl-1,2,3-triazol-4-yl-3-phenylprop-2-en-1-one precipitated as solid, which were filtered and recrystallized from ethanol. Yield: 0.27g (97%). M.p. 157–158°C.