(1S*,3S*,8S*,10S*)-10-Fluoro-15-oxa­tetra­cyclo­[6.6.1.01,10.03,8]penta­deca-5,12-dien-3-ol

Mehta, G.; Sen, S.

doi:10.1107/S1600536811026857

Volume 67
Part 8
Page o1985
August 2011

Received 23 June 2011
Accepted 5 July 2011
Online 9 July 2011

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 15.8
Details

(1S,3S,8S,10S)-10-Fluoro-15-oxatetracyclo[6.6.1.0^1,10.0^3,8]pentadeca-5,12-dien-3-ol

Goverdhan Mehta ^a ^* and Saikat Sen ^a

^aDepartment of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Correspondence e-mail: gmsc@uohyd.ernet.in

The title compound, C₁₄H₁₇FO₂, was obtained from anti-4a,9a:8a,10a-diepoxy-1,4,4a,5,8,8a,9,9a,10,10a-decahydroanthracene via tandem hydrogen-fluoride-mediated epoxide ring-opening and transannular oxacyclization. With the two cyclohexene rings folded towards the oxygen bridge, the title tetracyclic fluoroalcohol molecule displays a conformation reminiscent of a pagoda. The crystal packing is effected via intermolecular O-HO hydrogen bonds, which link the molecules into a zigzag chain along the b axis.

Related literature

For applications of organofluorine compounds as pharmaceuticals, see: Kirsch (2004); Bégué & Bonnet-Delpon (2006); Müller et al. (2007). For the use of diethylaminosulfur trifluoride, 1-chloromethyl-4-fluorodiazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) and pyridinium poly(hydrogen fluoride) as reagents for selective introduction of C-F bonds, see: Middleton (1975); Olah et al. (1979); Banks et al. (1992). For the preparation of the title compound, see: Mehta et al. (2007); Mehta & Sen (2010).

Experimental

Crystal data

C₁₄H₁₇FO₂
M_r = 236.28
Monoclinic, P 2₁ /c
a = 8.1603 (6) Å
b = 10.9148 (8) Å
c = 13.5558 (10) Å
= 96.285 (3)°
V = 1200.13 (15) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 291 K
0.26 × 0.22 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.976, T_max = 0.989
10752 measured reflections
2454 independent reflections
2038 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.113
S = 1.03
2454 reflections
155 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	2.14	2.9554 (14)	177
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2740 ).

Acknowledgements

We thank the Department of Science and Technology (DST), India, for the CCD facility at the Indian Institute of Science (IISc), Bangalore. GM thanks the Council for Scientific and Industrial Research (CSIR), India, for research support and the award of a Bhatnagar Fellowship.

References

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