3-Phenyl­coumarin

Maria J Matos; Lourdes Santana; Eugenio Uriarte

doi:10.1107/S1600536812034277

. 2012 Aug 4;68(Pt 9):o2645. doi: 10.1107/S1600536812034277

3-Phenylcoumarin

Maria J Matos ^a,^*, Lourdes Santana ^a, Eugenio Uriarte ^a

PMCID: PMC3435673 PMID: 22969544

Abstract

In the title compound, C₁₅H₁₀O₂, a 3-phenyl derivative of the coumarin (also known as 2H-chromen-2-one or 2H-1-benzopyran-2-one) scaffold, the C_p—C_p—C_c—C_c torsion angle between the coumarin (c) ring system and the phenyl (p) ring is −47.6 (2)°.

Related literature

For the synthesis of the title compound, see: Matos, Santana et al.. et al. (2011 ▶); Matos, Terán et al.. et al. (2011 ▶). For examples of biological activity of coumarin derivatives, see: Borges et al. (2009 ▶); Matos et al. (2009 ▶, 2010 ▶); Matos, Santana et al.. et al. (2011 ▶); Matos, Terán et al.. et al. (2011 ▶); Viña, Matos, Ferino et al. (2012 ▶); Viña, Matos Yáñez et al. (2012 ▶). graphic file with name e-68-o2645-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₀O₂
M _r = 222.23
Monoclinic,
a = 18.469 (4) Å
b = 5.9596 (12) Å
c = 19.274 (4) Å
β = 99.079 (3)°
V = 2094.9 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.27 × 0.22 × 0.09 mm

Data collection

Bruker SMART CCD 1000 diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.876, T _max = 1
9021 measured reflections
1924 independent reflections
1492 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.104
S = 1.03
1924 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034277/zj2091sup1.cif

e-68-o2645-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034277/zj2091Isup2.hkl

e-68-o2645-Isup2.hkl^{(92.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034277/zj2091Isup3.cml

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

Acknowledgments

This work was supported by funds from the Xunta da Galicia (09CSA030203PR), the Ministerio de Sanidad y Consumo (PS09/00501) and the Fundação para a Ciência e Tecnologia (SFRH/BD/61262/2009).

supplementary crystallographic information

Comment

Coumarin derivatives are very interesting molecules due to the biological properties that they may display (Borges et al. 2009; Matos et al. 2009, 2010; Matos, Santana et al.., 2011; Matos, Terán et al.., 2011). The title structure is a 3-phenyl coumarin derivative that posses one aromatic ring linked at that position. Therefore, the X-ray analysis of this compound (figure 1) aims to contribute to the elucidation of structural requirements needed to understand the partial planarity of the compound (coumarin nucleus) and the torsion of the 3-phenyl ring. From the single-crystal diffraction measurements one can conclude that the experimental bond lengths are within normal values with the average the molecule bond lengths. The planarity of the coumarin moiety is also evident by the torsion angles values between their carbons. Also, the angle C5—C6—C7—C8 is from -47.6 (2)°, typical of the torsion permitted by the rotation of the 3-phenyl ring. Packing diagram of the structure allows the interpretation of the spatial orientation of the molecules (figure 2).

Experimental

3-Phenylcoumarin was prepared according to the protocol described by Matos, Santana et al.. et al. (2011) and Matos, Terán et al.. et al. (2011). Perkin reaction gave the desired coumarin derivative. A solution of 2-hydroxybenzaldehyde (0.9 g, 7.37 mmol) and the phenylacetic acid (1.25 g, 9.21 mmol) in dimethyl sulfoxide (15 ml) was prepared. Dicyclohexylcarbodiimide (DCC, 2.37 g, 11.50 mmol) was added, and the mixture was heated at 110 °C for 24 h. Ice (100 ml) and acetic acid (10 ml) were added to the reaction mixture. After keeping it at room temperature for 2 h, the mixture was extracted with ether (3 x 25 ml). The organic layer was extracted with sodium bicarbonate solution (50 ml, 5%) and then water (20 ml). The solvent was evaporated under vacuum, and the dry residue was purified by flash chromatography (hexane/ethyl acetate 9:1). A white solid was obtained in a yield of 67% (1.1 g). Suitable crystals for X-ray studies were grown from slow evaporation from acetone/ethanol: Mp. 131–132 °C; ¹H NMR (300 MHz, CDCl₃): δ 7.34–7.54 (5H, m, 6-H, 8-H, 9-H, 11-H, 13-H), 7.56–7.66 (2H, m, 10-H, 12-H), 7.72–7.80 (2H, m, 5-H, 7-H), 7.90 (1H, s, 4-H); ¹³C NMR (75.47 MHz, CDCl₃): δ 116.5, 119.7, 124.5, 127.9, 128.4, 128.5, 128.5, 128.9, 131.4, 134.7, 139.9, 153.5, 160.6; DEPT: 116.5, 124.5, 127.9, 128.4, 128.5, 128.5, 131.4, 139.9; MS m/z 223 ([M + 1]⁺, 16), 222 (M⁺, 100). Anal. Calcd for C₁₅H₁₀O₂: C, 81.07; H, 4.54. Found: C, 81.02; H, 4.52.