9-Allyl-9H-fluoren-9-ol

Kyle S Knight; Harvey B Wood

doi:10.1107/S1600536814010290

. 2014 May 17;70(Pt 6):o677. doi: 10.1107/S1600536814010290

9-Allyl-9H-fluoren-9-ol

Kyle S Knight ^a,^*, Harvey B Wood ^a

PMCID: PMC4051071 PMID: 24940257

Abstract

The asymmetric unit of the title compound, C₁₆H₁₄O, contains two independent molecules differing in the orientations of the allyl groups; the corresponding O—C—C(H₂)—C(H) torsion angles are −61.01 (13) and −177.43 (10)°. In the crystal, O—H⋯O hydrogen bonds link four molecules into a centrosymmetric tetramer, in which each hydroxy group acts as a donor and an acceptor of hydrogen bonds.

Related literature

For the use of the title compound in the synthesis of spirocyclic ethers via alkene metathesis, see: Brahma et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₄O
M _r = 222.27
Triclinic,
a = 9.3789 (15) Å
b = 12.2809 (18) Å
c = 12.936 (2) Å
α = 63.995 (4)°
β = 68.803 (4)°
γ = 69.887 (4)°
V = 1217.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.8 × 0.7 × 0.51 mm

Data collection

Bruker APEXII CCD diffractometer
23092 measured reflections
4262 independent reflections
3749 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.02
4262 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814010290/cv5454sup1.cif

e-70-0o677-sup1.cif^{(681.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010290/cv5454Isup2.hkl

e-70-0o677-Isup2.hkl^{(233.8KB, hkl)}

Click here for additional data file.^{(2KB, cdx)}

Supporting information file. DOI: 10.1107/S1600536814010290/cv5454Isup3.cdx

Click here for additional data file.^{(4.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814010290/cv5454Isup4.cml

CCDC reference: 1001420

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.95	2.7709 (13)	165
O2—H2A⋯O1	0.84	1.93	2.7558 (15)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

Acknowledgements are made to the National Science Foundation MRI Program (CHE-0951711) and the Grote Chemistry Fund at the University of Tennessee at Chattanooga for their generous support of our work.

supplementary crystallographic information

1. Comment

The homoallylic alcohol, 9-allylfluoren-9-ol, crystallizes as two symmetrically distinct molecules. The molecules are linked by a square shaped hydrogen bonding network in which symmetrically equivalent and inequivalent molecules occupy alternating positions in the corners, and each hydroxyl group acts as a donor and an acceptor to adjacent molecules. In the crystal, there is t-stacking between alternating rows of symmetrically inequivalent molecules. In one molecule the O—C—C-alkene bond, O2—C20—C19—C18, is anti with a torsion angle of -177.43 (10)° while in the other symmetrically inequivalent structure, the analogous torsion, O1—C5—C6—C7, is gauche and has a torsion angle of -61.01 (13)°.

2. Experimental

The title compound was prepared by addition of a 1.0 M solution of allylmagnesium chloride (0.012 mol) in tetrahydrofuran to a solution of fluorenone (0.010 mol) at 0°C. The reaction was quenched by the addition of 1.0 M HCl, extracted into diethyl ether and concentrated on a rotary evaporator. Suitable crystals were obtained by recrystallization from methanol.