(Z)-1-(2,4-Difluoro­phen­yl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Cong-Yan Yan; Guang-Zhou Wang; Cheng-He Zhou

doi:10.1107/S1600536809029821

. 2009 Jul 31;65(Pt 8):o2054. doi: 10.1107/S1600536809029821

(Z)-1-(2,4-Difluorophenyl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Cong-Yan Yan ^a, Guang-Zhou Wang ^a, Cheng-He Zhou ^a,^*

PMCID: PMC2977445 PMID: 21583716

Abstract

In the title molecule, C₁₇H₁₁F₂N₃O, the triazole ring makes dihedral angles of 83.00 (5) and 16.63 (5)°, respectively, with the phenyl and benzene rings. Weak intermolecular C—H⋯F and C—H⋯N interactions contribute to the crystal packing.

Related literature

For details of the synthesis, see: Wang et al. (2009 ▶). For the pharmacological activity of chalcones, see: Reichwald et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₁F₂N₃O
M _r = 311.29
Monoclinic,
a = 11.7595 (16) Å
b = 7.5800 (10) Å
c = 17.068 (2) Å
β = 108.067 (2)°
V = 1446.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.25 × 0.21 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.973, T _max = 0.985
10616 measured reflections
2681 independent reflections
1940 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.101
S = 1.02
2681 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT-Plus (Bruker, 1997 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029821/cv2596sup1.cif

e-65-o2054-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029821/cv2596Isup2.hkl

e-65-o2054-Isup2.hkl^{(131.7KB, 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
C12—H12⋯N3ⁱ	0.93	2.68	3.540 (2)	154
C17—H17⋯F1ⁱⁱ	0.93	2.62	3.280 (2)	128

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

Acknowledgments

We thank the Southwest University (grant Nos. SWUB2006018 & XSGX0602) and Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

supplementary crystallographic information

Comment

Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants. Chalcones exhibit a variety of beneficial pharmacological activities such as antitumor, antibacterial, antifungal, antiinflammatory, antimalarial, antivirus and so on (Reichwald et al., 2008). In view of the therapeutic potentials of chalcones, we synthesized the title compound (I). Herewith we report its crystal structure.

In (I) (Fig. 1), the triazole ring makes the dihedral angles of 83.00 (5)° and 16.63 (5)°, respectively, with the phenyl and benzene rings. Weak intermolecular C—H···F and C—H···N interactions (Table 1) contribute to the crystal packing stability.

Experimental

Compound (I) was synthesized according to the procedure of Wang et al. (2009). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of ethyl acetate and petroleum ether by slow evaporation at room temperature.