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

Wen, Q.-M.; Yin, B.-T.; Yan, C.-Y.; Zhou, C.-H.

doi:10.1107/S1600536812018454

Volume 68
Part 6
Page o1642
June 2012

Received 5 March 2012
Accepted 25 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.118
Data-to-parameter ratio = 10.6
Details

(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 and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
Correspondence e-mail: zhouch@swu.edu.cn

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-HO and C-HN 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, P 2₁ /c
a = 11.217 (2) Å
b = 10.067 (2) Å
c = 15.793 (3) Å
= 94.47 (3)°
V = 1778.0 (6) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.118
S = 1.05
3403 reflections
321 parameters
2 restraints
All H-atom parameters refined
_max = 0.23 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H12O1ⁱ	0.981 (19)	2.435 (19)	3.347 (2)	154.6 (14)
C16-H23N1ⁱⁱ	0.906 (19)	2.525 (19)	3.388 (3)	159.3 (16)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: LH5432 ).

Acknowledgements

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).

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, J.-J., Wang, Y., Zhang, H.-Z., Zhou, C.-H., Geng, R.-X. & Ji, Q.-G. (2011). Chem. J. Chin. Univ. 32, 1970-1985.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Solankee, A., Kapadia, K., Ciric, A., Sokovic, M., Doytchinova, I. & Geronikaki, A. (2010). Eur. J. Med. Chem. 45, 510-518.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113.
Wang, Y. & Zhou, C.-H. (2011). Sci. Sin. Chim, 41, 1429-1456.
Yan, C.-Y., Wang, G.-Z. & Zhou, C.-H. (2009). Acta Cryst. E65, o2054.
Zhou, C.-H. & Wang, Y. (2012). Curr. Med. Chem. 19, 239-280.

organic compounds