3-(3-Fluoro­benz­yl)isochroman-1-one

Tariq Mahmood Babar; Ghulam Qadeer; Nasim Hasan Rama; Javeed Akhtar; Madeleine Helliwell

doi:10.1107/S1600536809003304

. 2009 Jan 31;65(Pt 2):o418. doi: 10.1107/S1600536809003304

3-(3-Fluorobenzyl)isochroman-1-one

Tariq Mahmood Babar ^a, Ghulam Qadeer ^a,^*, Nasim Hasan Rama ^a, Javeed Akhtar ^b, Madeleine Helliwell ^b

PMCID: PMC2968246 PMID: 21582007

Abstract

In the molecule of the title compound, C₁₆H₁₃FO₂, the aromatic rings are oriented at a dihedral angle of 74.46 (4)°. The heterocyclic ring adopts a twisted conformation. In the crystal structure, there is a weak C—H⋯π interaction.

Related literature

For related structures, see: Schmalle et al. (1982 ▶); Schnebel et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C₁₆H₁₃FO₂
M _r = 256.26
Monoclinic,
a = 12.6154 (16) Å
b = 7.6918 (10) Å
c = 13.0532 (17) Å
β = 103.705 (2)°
V = 1230.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 (2) K
0.50 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6739 measured reflections
2501 independent reflections
1805 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.096
S = 0.93
2501 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003304/hk2616sup1.cif

e-65-0o418-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003304/hk2616Isup2.hkl

e-65-0o418-Isup2.hkl^{(122.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1ⁱ	0.95	2.95	3.806 (3)	151

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

The title compound was prepared in order to evalute its potential as antibacterial and antifungal agents. The CCDC search (Allen, 2002) showed that the crystal structures of rac-exo-tricarbonyl-(h6-3-phenyl isochromanone)chromium (Schnebel et al., 2003) and 3,4-dihydro-8-hydroxy-3-(4-hydroxyphenyl)isocoumarin (Schmalle et al., 1982) have been reported, which have close resemblance as far as isochromane and attached phenyl ring is considered. We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3–C8) and C (C11–C16) are, of course, planar, and they are oriented at a dihedral angle of 74.46 (4)°. Ring B (O1/C1–C3/C8/C9) is not planar, having total puckering amplitude, Q_T, of 0.467 (3) Å and twisted conformation [φ = -105.12 (3)° and θ = 118.02 (3)°] (Cremer & Pople, 1975).

In the crystal structure, there is a C—H···π interaction (Table 1).

Experimental

As shown in Scheme 2, a mixture of homophthalic acid (1.98 g, 11.0 mmol) and 2-(3-fluorophenyl) acetyl chloride (7.91 g, 46 mmol) was heated under reflux at 473 K. After concentration, the residue was chromatographed on silica gel column using petroleum ether (333–353 K) to give 3-(3-fluorobenzyl)-1H-isochromen-1-one. 2-(3-(3-fluorophenyl)-2-oxopropyl)benzoic acid was obtained by refluxing a solution of 3-(3-fluorobenzyl)-1H-isochromen-1-one (3.6 g, 15.9 mmol) in ethanol (200 ml) and potassium hydroxide (5%,200 ml) for 6 h. NaBH4 (1.6 g) was added to a solution of 2-(3-(3-fluorophenyl)-2-oxopropyl)benzoic acid (4.23 g, 17.8 mmol) in sodium hydroxide (1%, 180 ml), and the resulting solution was stirred overnight at room temperature. After being acidified with HCl, the whole mixture was extracted with dichloromethane (2 × 15 ml). Usual work-up gave crude racemic hydroxy-acid, 2-(3-(3-fluorophenyl)-2-hydroxy propyl)benzoic acid, which was dissolved in acetic anhydride (5 ml) and heated under reflux for 2 h to get the title compound (yield; 81%, m.p, 374–375 °). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol.