(E)-3-(9-Anthr­yl)-1-(4-fluoro­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Wang, X.-L.; Wang, G.-Z.; Geng, R.-X.; Zhou, C.-H.

doi:10.1107/S1600536809055524

Volume 66
Part 2
Page o320
February 2010

Received 14 December 2009
Accepted 28 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.090
Data-to-parameter ratio = 14.7
Details

(E)-3-(9-Anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Xiao-Ling Wang,^a Guang-Zhou Wang,^a Rong-Xia Geng ^a and Cheng-He Zhou ^a ^*

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

In the title compound, C₂₆H₁₆FN₃O₃, the dihedral angle between the anthryl and fluorophenyl groups is 37.8 (1)°. With respect to the imidazolyl group, the twist angles between the imidazolyl group and the anthryl unit and between the imidazoly group and the fluorophenyl group are 64.4 (1) and 74.5 (1)°, respectively.

Related literature

For general background to chalcone derivatives, see: Detsi et al. (2009). For the synthesis, see: Erhardt et al. (1985); Kranz et al. (1980). For related structures, see: Lu et al. (2009); Wang et al. (2009). For a comment on the molecular shape, see: Hou et al. (2009).

Experimental

Crystal data

C₂₆H₁₆FN₃O₃
M_r = 437.42
Triclinic, $[P \overline 1]$
a = 9.3362 (6) Å
b = 10.9587 (6) Å
c = 11.6018 (5) Å
= 70.371 (5)°
= 88.062 (4)°
= 66.781 (6)°
V = 1020.78 (10) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 173 K
0.49 × 0.41 × 0.30 mm

Data collection

Oxford Diffraction Xcaliber diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.951, T_max = 0.970
8826 measured reflections
4374 independent reflections
3193 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.090
S = 1.01
4374 reflections
298 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.19 e Å^-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2707 ).

Acknowledgements

The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant Nos. 2007BB5369 and 2006BB4341) for financial support.

References

Detsi, A., Majdalani, M., Kontogiorgis, C., Hadjipavlou-Litina, D. & Kefalas, P. (2009). Bioorg. Med. Chem. 17, 8073-8085.
Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). Ger. Patent No. DE3406908.
Hou, G.-G., Ma, J.-P., Sun, T., Dong, Y.-B. & Huang, R.-Q. (2009). Chem. Eur. J. 15, 2261-2265.
Kranz, E., Krämer, W., Büchel, K. H., Brandes, W. & Forhberger, P. E. (1980). Ger. Patent No. DE2832233.
Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396.
Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, G.-Z., Fang, B. & Zhou, C.-H. (2009). Acta Cryst. E65, o2619.

organic compounds