(2E)-3-(4-Fluoro­phen­yl)-1-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one

Bakr F Abdel-Wahab; Hanan A Mohamed; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813008246

. 2013 Apr 5;69(Pt 5):o638. doi: 10.1107/S1600536813008246

(2E)-3-(4-Fluorophenyl)-1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one¹

Bakr F Abdel-Wahab ^a, Hanan A Mohamed ^a, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3647839 PMID: 23723805

Abstract

With respect to the triazole ring in the title compound, C₁₉H₁₆FN₃O, the p-tolyl ring is inclined [dihedral angle = 51.79 (11)°], whereas the chalcone residue is almost coplanar [O—C—C—N and C—C—C—C torsion angles = −178.71 (19) and 178.42 (18)°, respectively]. The conformation about the C=C bond [1.328 (3) Å] is E, and the triazole methyl group and the carbonyl O atom are syn. In the crystal, centrosymmetrically related molecules are connected by π–π interactions between the triazole and p-tolyl rings [centroid–centroid distance = 3.6599 (12) Å] and these are linked into a three-dimensional architecture by C—H⋯N and C—H⋯π interactions.

Related literature

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012 ▶); Singh et al. (2012 ▶). For a related structure, see: Abdel-Wahab et al. (2013 ▶). graphic file with name e-69-0o638-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₆FN₃O
M _r = 321.35
Triclinic,
a = 6.2890 (5) Å
b = 10.8874 (8) Å
c = 11.9691 (9) Å
α = 101.144 (7)°
β = 92.634 (6)°
γ = 91.634 (6)°
V = 802.65 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.35 × 0.35 × 0.35 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.887, T _max = 1.000
6854 measured reflections
3697 independent reflections
2308 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.139
S = 1.03
3697 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(19.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008246/hb7061sup1.cif

e-69-0o638-sup1.cif^{(19.7KB, cif)}

Click here for additional data file.^{(177.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008246/hb7061Isup2.hkl

e-69-0o638-Isup2.hkl^{(177.5KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813008246/hb7061Isup3.cml

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

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

Cg1 is the centroid of the C13–C18 benzene

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯N3ⁱ	0.96	2.49	3.399 (3)	158
C2—H2⋯Cg1ⁱⁱ	0.93	2.91	3.650 (2)	138

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

Acknowledgments

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR–MOHE/SC/03).

supplementary crystallographic information

Comment

Chalcone derivatives exhibit a range of biological activities (Abdel-Wahab et al., 2012; Singh et al., 2012) and in this connection, the title compound was synthesized and characterized crystallographically.

In (I), the p-tolyl ring attached to the triazole ring is inclined, forming a dihedral angle of 51.79 (11)°. By contrast, the chalcone residue is co-planar as seen in the values of the O1—C9—C10—N3 and C7—C8—C9—C10 torsion angles of -178.71 (19) and 178.42 (18)°, respectively. This co-planarity extends to include the terminal fluorobenzene ring [C6—C1—C7—C8 = 4.2 (3)°]. The conformation about the C7═C8 bond [1.328 (3) Å] is E, and the triazole-methyl and carbonyl-O1 substituents are syn. The conformation with respect to the triazole ring and chalcone residue resembles that found in a related compound (Abdel-Wahab et al., 2013).

In the crystal structure, centrosymmetrically related molecules are connected by π—π interactions between the triazole and p-tolyl rings [inter-centroid distance = 3.6599 (12) Å, angle of inclination = 2.30 (11)° for symmetry operation: 1 - x, 1 - y, 2 - z]. The dimeric aggregates are connected into a three-dimensional architecture by C—H···N and C—H···π interactions, Fig. 2 and Table 1.

Experimental

The title compound was prepared following the reported method (Abdel-Wahab et al., 2012). Colourless blocks were obtained from its DMF solution by slow evaporation at room temperature.