6-Fluoro­indan-1-one

Benjamin R Slaw; Joseph M Tanski

doi:10.1107/S1600536814015049

. 2014 Jul 2;70(Pt 8):o841. doi: 10.1107/S1600536814015049

6-Fluoroindan-1-one

Benjamin R Slaw ^a, Joseph M Tanski ^a,^*

PMCID: PMC4158499 PMID: 25249894

Abstract

The title compound, C₉H₇FO, crystallizes with two independent molecules in the asymmetric unit, in which corresponding bond lengths are the same within experimental error. The five-membered ring in each molecule is almost planar, with r.m.s. deviations of 0.016 and 0.029 Å. In the crystal, molecules form sheets parallel to (1 0 0) via C—H⋯O and C—H⋯F interactions with F⋯F contacts [3.1788 (16) and 3.2490 (16) Å] between the sheets.

Keywords: crystal structure

Related literature

For the synthesis of 6-fluoroindan-1-one, see: Cui et al. (2004 ▶) and for its use in synthesis, see: Musso et al. (2003 ▶); Ślusarczyk et al. (2007 ▶); Yin et al. (2013 ▶). For the structure of the parent comound, 1-indanone, see: Morin et al. (1974 ▶) and Ruiz et al. (2004 ▶), the later containing a detailed analysis of the hydrogen bonding. For a related isomeric structure, 5-fluoroindan-1-one, see: Garcia et al. (1995 ▶). For more information on C—H⋯X interactions, see Desiraju & Steiner (1999 ▶) and on fluorine–fluorine interactions in the solid state, see: Baker et al. (2012 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C₉H₇FO
M _r = 150.15
Monoclinic,
a = 7.1900 (4) Å
b = 12.4811 (6) Å
c = 15.8685 (8) Å
β = 99.453 (1)°
V = 1404.69 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 125 K
0.37 × 0.26 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T _min = 0.91, T _max = 1.00
22840 measured reflections
4298 independent reflections
3345 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.121
S = 1.03
4298 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015049/kj2241sup1.cif

e-70-0o841-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015049/kj2241Isup2.hkl

e-70-0o841-Isup2.hkl^{(235.8KB, hkl)}

Click here for additional data file.^{(2.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015049/kj2241Isup3.cml

CCDC reference: 1010372

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
C5—H5⋯O1ⁱ	0.95	2.47	3.3873 (14)	161
C14—H14⋯O2ⁱⁱ	0.95	2.65	3.5107 (14)	150
C2—H2B⋯F2ⁱⁱⁱ	0.99	2.46	3.2062 (13)	132
C6—H6⋯O2^iv	0.95	2.65	3.5338 (14)	154
C11—H11B⋯O1^v	0.99	2.52	3.3348 (13)	140
C15—H15⋯F1^vi	0.95	2.52	3.3664 (13)	148

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

supplementary crystallographic information

S1. Comment

The titular compound 6-fluoroindan-1-one may be synthesized by the Tb(OTf)₃-catalyzed cyclization of 3-(4-fluorophenyl)propanoic acid (Cui et al., 2004). The substance has found laboratory applications in the synthesis of α-arylated compounds (Yin et al., 2013), the synthesis of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate, a potent muscle relaxant derivative (Musso et al., 2003), and in the creation of methylene-bridged biologically active pteridine derivatives for potential hepatitis C treatments (Ślusarczyk et al., 2007). The crystal structure of the parent compound, 1-indanone, has been reported previously (Morin et al., 1974; Ruiz et al., 2004), as has the structure of an isomer of the title compound, 5-fluoroindan-1-one (Garcia et al., 1995).

The titular compound crystallizes with two molecules of 6-fluoroindan-1-one in the asymmetric unit (Figure 1). The carbonyl C—O bond lengths of 1.2172 (13) and 1.2179 (13) Å, as for the other bond lengths, are the same within the experimental error between the two independent molecules. These carbonyl C—O bond lengths are similar to those found in the structure of the parent comound, 1-indanone, 1.217 (2) Å (Ruiz et al., 2004), and in the structure of the isomeric compound 5-fluoroindan-1-one, 1.218 (2) Å (Garcia et al.,1995). The C—F bond lengths in 6-fluoroindan-1-one, 1.3592 (12) and 1.3596 (11) Å, are also very similar to that found in the structure of the isomeric compound 5-fluoroindan-1-one, 1.354 (2) Å.

The molecules pack together in the solid state to form a two-dimensional sheet parallel to the 1 0 0 plane via several intermolecular C—H···O and C—F···H interactions (Figure 2, Table 2) measuring slightly less than the sum of the van der Waals radii (Bondi, 1964). The oxygen atom in each independent molecule forms two C—H···O interactions, while each independent molecule also forms one C—F···H interaction. For a discussion of C—H···X interactions, see Desiraju & Steiner (1999). There are also two long F···F interactions linking the two-dimensional sheets, (Figure 3, Table 1), which are somewhat longer than the sum of the van der Waals radii, 2.94 Å (Bondi, 1964). For a discussion of fluorine-fluorine interactions, which can vary widely in their metrical parameters and strength, see Baker et al. (2012).

S2. Experimental

Crystalline 6-fluoroindan-1-one (I) was purchased from Aldrich Chemical Company, USA.