2-(4-Fluoro­phen­yl)-2H-chromen-4(3H)-one

Michał Wera; Andriy G Chalyi; Alexander D Roshal; Jerzy Błażejowski

doi:10.1107/S160053681105464X

. 2012 Jan 7;68(Pt 2):o253–o254. doi: 10.1107/S160053681105464X

2-(4-Fluorophenyl)-2H-chromen-4(3H)-one

Michał Wera ^a, Andriy G Chalyi ^b, Alexander D Roshal ^b, Jerzy Błażejowski ^a,^*

PMCID: PMC3274947 PMID: 22346900

Abstract

In the crystal structure of the title compound, C₁₅H₁₁FO₂, molecules form inversion dimers through pairs of weak C—H⋯O hydrogen bonds. Dimers oriented in parallel, linked by C—H⋯π contacts, are arranged in columns along the b axis. The fluorophenyl ring and the benzene ring of the 2H-chromen-4(3H)-one unit are inclined to one another by 70.41 (16)°. They are respectively parallel in a given column or almost perpendicular [oriented at an angle of 87.8 (1)°] in neighbouring (inversely oriented) columns, forming a herringbone pattern.

Related literature

For general background to flavanones, see: Grayer & Veitch (2006 ▶); Nijveldt et al. (2001 ▶). For related structures, see: Białońska et al. (2007a ▶,b ▶). For intermolecular interactions, see: Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Aitmambetov & Kubzheterova (2002 ▶); Chen et al. (2011 ▶); Wera et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₁FO₂
M _r = 242.24
Monoclinic,
a = 11.7896 (13) Å
b = 5.2309 (8) Å
c = 19.740 (3) Å
β = 91.630 (11)°
V = 1216.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.6 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.919, T _max = 0.953
7630 measured reflections
2163 independent reflections
1080 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.160
S = 1.01
2163 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105464X/xu5408sup1.cif

e-68-0o253-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105464X/xu5408Isup2.hkl

e-68-0o253-Isup2.hkl^{(106.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681105464X/xu5408Isup3.cml

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

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

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O11ⁱ	0.98	2.48	3.280 (4)	139
C3—H3A⋯Cg1ⁱⁱ	0.97	2.78	3.695 (3)	157

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This study was financed by the State Funds for Scientific Research (grant DS/8220–4-0087–1). MW acknowledges financial support from the European Social Fund within the project "Educators for the elite – integrated training program for PhD students, post-docs and professors as academic teachers at the University of Gdańsk" and the Human Capital Operational Program Action 4.1.1, Improving the quality on offer at tertiary educational institutions. This publication reflects the views only of the authors: the sponsor cannot be held responsible for any use which may be made of the information contained therein.

supplementary crystallographic information

Comment

Flavanones [derivatives of 2-phenyl-2H-chromen-4(3H)-one] appear in numerous natural systems where they fulfil a beneficial role due to their antioxidant features (Nijveldt et al., 2001; Grayer & Veitch, 2006). Here we present the structure of 2-(4-fluorophenyl)-2H-chromen-4(3H)-one, a flavanone that was obtained during the synthesis of a related flavonol (Wera et al., 2010).

In the title compound (Fig. 1), the bond lengths and angles characterizing the geometry of the 2-phenyl-2H-chromen-4(3H)-one (flavanone) moiety are typical of this group of compounds (Białońska et al., 2007a,b). With respective average deviations from planarity of 0.0103 (2)° and 0.0040 (2)°, the Cg1 and Cg2 benzene ring systems are oriented at a dihedral angle of 70.4 (1)° (in the case of 6-hydroxy-2-phenyl-2H-chromen-4(3H)-one and 2-(4-hydroxyphenyl)-2H-chromen-4(3H)-one this angle is equal to 74.4 (1)° (Białońska et al., 2007a) and 74.8 (1)° (Białońska et al., 2007b) respectively). The crystal structure data indicate that the 2H-chromen-4(3H)-one moiety is non-planar [average deviation from planarity: 0.1857 (2) mainly within the O1/C2–C4/C9/C10/O11 fragment, since the average deviation from planarity of the C5–C10 ring is 0.0103 (2)]. It is mainly the C2 atom that deviates from planarity, since the average deviation from planarity of the O1/C3–C10/C11 fragment is equal to 0.0368 (2).

In the crystal structure, the inversely oriented molecules form dimers through a pair of intermolecular C–H···O (Novoa et al., 2006) interactions (Table 1, Fig. 2). Dimers oriented in parallel, linked by C–H···π (Takahashi et al., 2001) contacts (Table 1, Fig. 2), are arranged in columns along the b axis (Fig. 3) that are dispersively stabilized in the crystal lattice. The adjacent Cg1 and Cg2 benzene rings are parallel in a given column or oriented at an angle of 87.8 (1)° in the two neighbouring, inversely oriented, columns, forming a herringbone pattern.

Experimental

The title compound was synthesized following a procedure described elsewhere (Aitmambetov & Kubzheterova, 2002; Chen et al., 2011). Briefly, 3-(4-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one was synthesized first by the condensation (with removal of H₂O) of 1-(2-hydroxyphenyl)ethanone with 4-fluorobenzaldehyde in methanol/50% aqueous NaOH (1/1 v/v), then precipitated by neutralizing the reaction mixture with aqueous HCl, and finally separated by filtration (Wera et al., 2010). The product thus obtained was subjected to cyclization in triethylamine/ethanol solution (by refluxing for 2–3 h). The reactant mixture was poured into cold HCl-acidified water which caused the precipitation of 2-(4-fluorophenyl)-2H-chromen-4(3H)-one. The filtered product was purified chromatographically (Silica Gel, chloroform/methanol, 20/1 v/v), and colorless crystals suitable for X-ray investigations were grown from absolute ethanol (m.p. = 351–353 K; lit. 352–353 K (Chen et al., 2011)).