(Z)-1-[4-Fluoro-2-(pyrrolidin-1-yl)phen­yl]-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Qin-Mei Wen; Ben-Tao Yin; Cong-Yan Yan; Cheng-He Zhou

doi:10.1107/S1600536812018454

. 2012 May 5;68(Pt 6):o1642. doi: 10.1107/S1600536812018454

(Z)-1-[4-Fluoro-2-(pyrrolidin-1-yl)phenyl]-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Qin-Mei Wen ^a, Ben-Tao Yin ^a, Cong-Yan Yan ^a, Cheng-He Zhou ^a,^*

PMCID: PMC3379244 PMID: 22719442

Abstract

In the title molecule, C₂₁H₁₉FN₄O, the triazole ring forms dihedral angles of 67.0 (1) and 59.6 (1)° with the phenyl and fluoro-substituted benzene rings, respectively. The dihedral angle between the phenyl ring and the fluoro-substituted benzene ring is 79.1 (1)°. The pyrrolidine ring is in a half-chair conformation. In the crystal, weak C—H⋯O and C—H⋯N hydrogen bonds connect molecules into layers parallel to (001).

Related literature

For clinical uses of triazole compounds, see: Wang & Zhou (2011 ▶); Zhou & Wang (2012 ▶); Chang et al. (2011 ▶). For the synthesis, see: Solankee et al. (2010 ▶). For related structures, see: Wang et al. (2009 ▶); Yan et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₁₉FN₄O
M _r = 362.40
Monoclinic,
a = 11.217 (2) Å
b = 10.067 (2) Å
c = 15.793 (3) Å
β = 94.47 (3)°
V = 1778.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.30 × 0.08 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T _min = 0.973, T _max = 0.997
13447 measured reflections
3403 independent reflections
2341 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.118
S = 1.05
3403 reflections
321 parameters
2 restraints
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018454/lh5432sup1.cif

e-68-o1642-sup1.cif^{(26KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018454/lh5432Isup2.hkl

e-68-o1642-Isup2.hkl^{(166.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018454/lh5432Isup3.cml

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
C5—H12⋯O1ⁱ	0.981 (19)	2.435 (19)	3.347 (2)	154.6 (14)
C16—H23⋯N1ⁱⁱ	0.906 (19)	2.525 (19)	3.388 (3)	159.3 (16)

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

Acknowledgments

This work was partially supported by the Natural Science Foundation of China (21172181) and the Research Funds for the Central Universities, the key program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2011D007, XDJK2012B026).

supplementary crystallographic information

Comment

Chalcones are an important type of biologically active compounds with a diarylenone structural unit (Solankee et al., 2010). Triazole compounds have been shown to have clinical uses (Wang et al., 2011; Zhou et al., 2012; Chang et al., 2011). Our group have been contributing to the research and development of triazolyl chalcones as potential antimicrobial agents. Related structures of triazolylchalcones have alreay been reported (Wang et al., 2009; Yan et al., 2009). Herein we report the crystal structure of the title compound (I).

In the molecular structure (Fig. 1) the triazole ring [N1/N2/N3/C9/C10] forms dihedral angles of 67.0 (1) and 59.6 (1)° with the phenyl [C1-C6] and fluoro-substituted benzene [C12-C17] rings. The dihedral angles between the phenyl and fluoro-substituted bezene rings is 79.1 (1)°. The pyrrolidine ring [N4/C18-C21] is in a half-chair conformation. In the crystal, weak C—H···O and C—H···N hydrogen bonds connect molecules into layers parallel to (001).

Experimental

The title compound (I) was synthesized according to the procedure of Solankee et al. (2010). To a stirring mixture of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (2.23 g, 10 mmol) and benzaldehyde (1.06 g, 10 mmol) in ethanol (20 mL) in the presence of acetic acid (0.08 mL, 1.4 mmol) was added pyrrolidine (0.71 g, 10 mmol). The mixed solution was refluxed until the reaction came to the end (monitored by TLC). Subsequently, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (20 mL) and extracted with water (3 x 20 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce the crude product, which was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (15/1:1/1, V/V) to afford the desired compound. A crystal suitable for X-ray analysis was grown from a solution of (I) in petroleum ether and ethyl acetate by slow evaporation at room temperature.