9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

Asad, M.; Oo, C.-W.; Osman, H.; Fun, H.-K.; Arshad, S.

doi:10.1107/S1600536811051749

Volume 68
Part 1
Page o38
January 2012

Received 25 November 2011
Accepted 1 December 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.052
wR = 0.150
Data-to-parameter ratio = 22.4
Details

9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

Mohammad Asad,^a Chuan-Wei Oo,^a ⁺ Hasnah Osman,^a Hoong-Kun Fun ^b ^*⁺⁺ and Suhana Arshad ^b

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₆H₂₅FO₅, the terminal cyclohexane rings of the xanthene ring system adopt half-boat conformations. The 4H-chromene ring make a dihedral angle of 87.94 (5)° with the xanthene ring system and its carbonyl O atom lies above the xanthene O atom. In the crystal, molecules are linked into ribbons propagating along the a-axis direction by C-HO hydrogen bonds. Aromatic [pi] - [pi] stacking interactions [centroid-centroid distance = 3.7367 (12) Å] also occur.

Related literature

For a related structure and background to the properties and applications of xanthene derivatives, see: Mehdi et al. (2011). For ring conformations, see: Cremer & Pople (1975). For reference bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₆H₂₅FO₅
M_r = 436.46
Monoclinic, P 2₁ /c
a = 6.9475 (8) Å
b = 18.596 (2) Å
c = 17.559 (2) Å
= 93.658 (2)°
V = 2264.0 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.51 × 0.38 × 0.24 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.954, T_max = 0.978
21143 measured reflections
6574 independent reflections
4315 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.150
S = 1.03
6574 reflections
293 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15BO4ⁱ	0.97	2.44	3.3487 (19)	156
C18-H18AO5ⁱ	0.97	2.45	3.3821 (19)	162
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6535 ).

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grants (1001/PFIZIK/811160) and (203/PKIMIA/6711179). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. MA also thanks Universiti Sains Malaysia for the award of a post-doctoral fellowship.

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 (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719-o1720.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds