9-(4-Fluoro­phen­yl)-3,3,6,6-tetra­methyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione

Tang, Z.; Liu, C.; Wu, S.; Hao, W.

doi:10.1107/S1600536808027256

Volume 64
Part 9
Page o1844
September 2008

Received 20 August 2008
Accepted 24 August 2008
Online 30 August 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.052
wR = 0.152
Data-to-parameter ratio = 15.0
Details

9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Ziqiang Tang,^a ^* Changning Liu,^a Shanshan Wu ^b and Wenjuan Hao ^b

^aSchool of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221006, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
Correspondence e-mail: laotu2001@263.net

The title compound, C₃₀H₃₂FNO₂, was synthesized by the reaction of dimedone with 4-fluorobenzaldehyde and p-toluidine in water. The dihydropyridine and both of the cyclohexenone rings are not planar and have flattened boat conformations. The dihedral angle between the planar aromatic rings is 15.33 (3)°. In the crystal structure, intermolecular C-HO hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Wysocka-Skrzela & Ledochowski (1976); Nasim & Brychcy (1979); Thull & Testa, (1994); Reil et al. (1994); Mandi et al. (1994). For related literature, see: Tu et al. (2004). For ring puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₃₀H₃₂FNO₂
M_r = 457.58
Monoclinic, P 2₁ /n
a = 15.1533 (15) Å
b = 10.9643 (12) Å
c = 16.1053 (15) Å
= 102.317 (2)°
V = 2614.2 (5) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 298 (2) K
0.37 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.984
13238 measured reflections
4605 independent reflections
2277 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.152
S = 1.02
4605 reflections
307 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15O1ⁱ	0.93	2.45	3.336 (3)	159
Symmetry code: (i) -x+2, -y+1, -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: 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: HK2514 ).

Acknowledgements

We thank the Foundation of Xuzhou Institute of Technology (grant No. XKY2007241) for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Mandi, Y., Regely, K., Ocsovszky, I., Barbe, J., Galy, J. P. & Molnar, J. (1994). Anticancer Res. 14, 2633-2636.
Nasim, A. & Brychcy, T. (1979). Mutat. Res. 65, 261-288.
Reil, E., Scoll, M., Masson, K. & Oettmeier, W. (1994). Biochem. Soc. Trans. 22, s62.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Thull, U. & Testa, B. (1994). Biochem. Pharmacol. 47, 2307-2310.
Tu, S. J., Miao, C. B., Gao, Y., Fang, F., Zhuang, Q. Y., Feng, Y. J. & Shi, D. Q. (2004). Synlett, 2, 255-258.
Wysocka-Skrzela, B. & Ledochowski, A. (1976). Rocz. Chem. 50, 127-131.

organic compounds